NOVEL ANTIVIRAL COMPOUNDS, COMPOSITIONS, AND METHODS OF USE
Compounds are disclosed. Compositions that include the compounds are disclosed. Methods of making and using the compounds are also disclosed.
1 . A compound having the formula:
or salt thereof;
wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 2 R 12 , —SO 2 NHR 12 , —SOR 12 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 1 and R 2 together with the nitrogen to which they are attached form a heterocyclic ring group or salt thereof;
wherein R 3 , R 9 , and R 11 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
wherein R 4 is hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —CN, —NC, —SH, —NO 2 , —NH 2 , PR 2 ,—(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, or salt thereof
wherein R 5 and R 6 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 5 and R 6 together with the carbons to which they are attached form a (C 5 -C 6 ) aryl structure, a (C 3 -C 6 ) heteroaryl structure, a (C 3 -C 6 ) heterocycloalkenyl structure, a (C 4 -C 6 ) cycloalkenyl structure, or salt thereof;
wherein R 7 and R 8 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —C(NH)NH 2 , —C(NH)NHC(NH)NH 2 , —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 7 and R 8 together with the nitrogen to which they are attached form a heterocyclic ring group or salt thereof;
wherein R 10 is hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 14 , —NR 14 R 15 , —NR 14 COR 15 , —CONR 14 R 15 , —CONR 14 , —COOR 14 , —OCOR 14 , —COR 14 , SR 14 , —SO 2 R 14 , —SO 3 R 14 , —SO 2 NR 14 , —SOR 14 , —N 3 , —CN, —NC, —SH, —NO 2 , NH 2 , —PR 2 , —(O)PR 14 R 15 , —PO 3 R 14 R 15 , —OPO 3 R 14 R 15 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, or salt thereof;
wherein R 12 and R 13 are each independently selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
wherein R 14 and R 15 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
and wherein each of said (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, (C 3 -C 6 ) cycloalkyl structure, (C 5 -C 6 ) aryl structure, (C 3 -C 6 ) heteroaryl structure, (C 3 -C 6 ) heterocyclyl structure, (C 3 -C 6 ) heterocycloalkenyl structure, (C 4 -C 6 ) cycloalkenyl structure, heterocyclic ring group, or salt thereof may be independently unsubstituted or substituted with one or more substituents selected from the group consisting of hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, salt thereof, and a combination thereof;
with the proviso that when R 3 , R 10 , and R 11 are hydrogen, and R 9 is —CH 3 , then R 5 is not —CN.
2 . The compound of claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, and fluoro.
3 . The compound of claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , OPO 3 R 12 R 13 , —PO 2 , and salt thereof.
4 . The compound of claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof.
5 . The compound of claim 1 , wherein R 1 and R 2 together with the nitrogen to which they are attached form a heterocyclic ring group or salt thereof.
6 . The compound of claim 1 , wherein R 3 , R 9 , and R 11 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro.
7 . The compound of claim 1 , wherein R 3 , R 9 , and R 11 are each independently selected from the group consisting of —OR 12 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , and salt thereof.
8 . The compound of claim 1 , wherein R 3 , R 9 , and R 11 are each independently selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof.
9 . The compound of claim 1 , wherein R 4 is selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, and fluoro.
10 . The compound of claim 1 , wherein R 4 is selected from the group consisting of —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —PO 3 R 12 R 13 , —PO 2 , and salt thereof.
11 . The compound of claim 1 , wherein R 4 is selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof.
12 . The compound of claim 1 , wherein R 5 and R 6 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, and fluoro.
13 . The compound of claim 1 , wherein R 5 and R 6 are each independently selected from the group consisting of —OR 12 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , and salt thereof.
14 . The compound of claim 1 , wherein R 5 and R 6 are each independently selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof.
15 . The compound of claim 1 , wherein R 5 and R 6 together with the carbons to which they are attached form a (C 5 -C 6 ) aryl structure, a (C 3 -C 6 ) heteroaryl structure, a (C 3 -C 6 ) heterocycloalkenyl structure, a (C 4 -C 6 ) cycloalkenyl structure, or salt thereof.
16 . The compound of claim 1 , wherein R 7 and R 8 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, and fluoro.
17 . The compound of claim 1 , wherein R 7 and R 8 are each independently selected from the group consisting of —C(NH)NH 2 , —C(NH)NHC(NH)NH 2 , —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , and salt thereof.
18 . The compound of claim 1 , wherein R 7 and R 8 are each independently selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof.
19 . The compound of claim 1 , wherein R 7 and R 8 together with the nitrogen to which they are attached form a heterocyclic ring group or salt thereof.
20 . The compound of claim 1 , wherein R 10 is selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, and fluoro.
21 . The compound of claim 1 , wherein R 10 is selected from the group consisting of —OR 14 , —NR 14 R 15 , —NR 14 COR 15 , —CONR 14 R 15 , —CONR 14 , —COOR 14 , —OCOR 14 , —COR 14 , —SR 14 , —SO 2 R 14 , —SO 3 R 14 , —SO 2 NR 14 , —SOR 14 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 14 R 15 , —PO 3 R 14 R 15 , —OPO 3 R 14 R 15 , —PO 2 , and salt thereof.
22 . The compound of claim 1 , wherein R 10 is selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof.
23 . The compound of claim 1 , wherein R 14 and R 15 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, and fluoro.
24 . The compound of claim 1 , wherein R 14 and R 15 are each independently selected from the group consisting of —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , and salt thereof.
25 . The compound of claim 1 , wherein R 14 and R 15 are each independently selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof.
26 . The compound of claim 1 , wherein at least one (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, (C 3 -C 6 ) cycloalkyl structure, (C 5 -C 6 ) aryl structure, (C 3 -C 6 ) heteroaryl structure, (C 3 -C 6 ) heterocyclyl structure, (C 3 -C 6 ) heterocycloalkenyl structure, (C 4 -C 6 ) cycloalkenyl structure, heterocyclic ring group, or salt thereof is substituted with one or more substituents selected from the group consisting of hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, salt thereof, and a combination thereof.
27 . The compound of claim 1 , wherein at least one (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, (C 3 -C 6 ) cycloalkyl structure, (C 5 -C 6 ) aryl structure, (C 3 -C 6 ) heteroaryl structure, (C 3 -C 6 ) heterocyclyl structure, (C 3 -C 6 ) heterocycloalkenyl structure, (C 4 -C 6 ) cycloalkenyl structure, heterocyclic ring group, or salt thereof is not substituted.
28 . The compound of claim 1 , wherein at least one of R 3 , R 10 , or R 11 is not hydrogen.
29 . The compound of claim 1 , wherein R 9 is not —CH 3 .
30 . The compound of claim 1 , wherein at least one of R 1 and R 2 together with the nitrogen to which they are attached, R 7 and R 8 together with the nitrogen to which they are attached, or both independently forms a heterocyclic ring group selected from the group consisting of:
pyrrolyl, 2,3-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl, tetrahydropyrrol-1-yl,
pyrazol-1-yl, 3H-pyrazol-1-yl, 4H-pyrazol-1-yl, 3,4-dihydropyrazol-1-yl,
1,3-isodiazol-1-yl, 3H-(1,3-isodiazol-1-yl), 3,4-dihydro-(1,3-isodiazol-1-yl),
1,2,3-triazol-1-yl, 2H-(1,2,3-triazol-1-yl), 2,3-dihydro(1,2,3-triazol-1-yl), 2,3,4-trihydro(1,2,3-triazol-1-yl),
1,2,3-triazol-2-yl, 1,3-dihydro(1,2,3-triazol-2-yl), 1,3,4-trihydro(1,2,3-triazol-2-yl),
1,2,4-triazol-1-yl, 2H-(1,2,4-triazol-1-yl), 2,3-dihydro(1,2,4-triazol-1-yl), 2,4-dihydro(1,2,4-triazol-1-yl),
1,2,4-triazol-4-yl, 1H-(1,2,4-triazol-4-yl), 1,2-dihydro(1,2,4-triazol-4-yl), 3,5-dihydro(1,2,4-triazol-4-yl),
isoxazol-2-yl, 3H-isoxazol-2-yl, 4H-isoxazol-2-yl,
oxazol-3-yl, 4H-oxazol-3-yl,
thiazol-3-yl, 4H-thiazol-3-yl,
isothiazol-2-yl, 3H-isothiazol-2-yl,
1,2,3-oxadiazol-2-yl, 3H-(1,2,3-oxadiazol-2-yl),
1,2,3-oxadiazol-3-yl, 4H-(1,2,3-oxadiazol-3-yl),
1,2,4-oxidiazol-2-yl, 3H-(1,2,4-oxidiazol-2-yl), 4H-(1,2,4-oxidiazol-2-yl), 5H-(1,2,4-oxidiazol-2-yl),
1,2,4-oxidiazol-4-yl, 3H-(1,2,4-oxidiazol-4-yl),
1,2,5-oxadiazol-2-yl, 4H-(1,2,5-oxadiazol-2-yl),
1,3,4-oxadiazol-3-yl, 4H-(1,3,4-oxadiazol-3-yl),
1,2,3,4-oxatriazol-2-yl, 3H-(1,2,3,4-oxatriazol-2-yl), 5H-(1,2,3,4-oxatriazol-2-yl), 3H-, 4H-(1,2,3,4-oxatriazol-2-yl),
1,2,3,4-oxatriazol-3-yl, 4H-(1,2,3,4-oxatriazol-3-yl),
5H-(1,2,3,5-oxatriazol-2-yl), 3H-,4H-(1,2,3,5-oxatriazol-2-yl),
1,2,3,5-oxatriazol-3-yl, 4H-(1,2,3,5-oxatriazol-3-yl),
1,2,3,5-oxatriazol-5-yl, 4H-(1,2,3,5-oxatriazol-5-yl), 2H-(1,2,3,5-oxatriazol-5-yl), 2H-, 3H-(1,2,3,5-oxatriazol-5-yl),
1,2,3-dioxazol-3-yl, 4H-(1,2,3-dioxazol-3-yl),
1,2,4-dioxazol-4-yl,
1,3,2-dioxazol-2-yl, 4H-(1,3,2-dioxazol-2-yl),
1,3,4-dioxazol-4-yl,
1,2,5-oxathiazol-5-yl, 3H-(1,2,5-oxathiazol-5-yl),
2H-(pyridin-1-yl), 4H-(pyridin-1-yl), 3H-,4H-(pyridin-1-yl), 2H-,5H-(pyridin-1-yl), 3H-,5H-(pyridin-1-yl),
2H-(pyridazin-1-yl), 4H-(pyridazin-1-yl), 6H-(pyridazin-1-yl), 3H-,4H-(pyridazin-1-yl), 4H-,5H-(pyridazin-1-yl), 2H-,5H-(pyridazin-1-yl), 2H-,3H-,6H-(pyridazin-1-yl), 3H-,5H-(pyridazin-1-yl),
2H-(pyrimidin-1-yl), 4H-(pyrimidin-1-yl), 6H-(pyrimidin-1-yl), 3H-,4H-(pyrimidin-1-yl), 4H-,5H-(pyrimidin-1-yl), 2H-,5H-(pyrimidin-1-yl), 2H-,3H-,6H-(pyrimidin-1-yl), 3H-, 5H-(pyrimidin-1-yl),
2H-(pyrazin-1-yl), 4H-(pyrazin-1-yl), 3H-,4H-(pyrazin-1-yl), 2H-,5H-(pyrazin-1-yl), piperazin-1-yl,
2H-(s-triazin-1-yl), 4H-(s-triazin-1-yl), 4H-,5H-(s-triazin-1-yl), 2H-,5H-(s-triazin-1-yl), 3H-,5H-(s-triazin-1-yl),
2H-(as-triazin-1-yl), 4H-(as-triazin-1-yl), 6H-(as-triazin-1-yl), 3H-,4H-(as-triazin-1-yl), 4H-,5H-(as-triazin-1-yl), 2H-,5H-(as-triazin-1-yl), 2H-,3H-,6H-(as-triazin-1-yl), 3H-,5H-(as-triazin-1-yl),
1H-(as-triazin-2-yl), 3H-(as-triazin-2-yl), 5H-,6H-(as-triazin-2-yl), 3H-,6H-(as-triazin-2-yl), 1H-,4H-(as-triazin-2-yl), 5H-(as-triazin-2-yl), 1H-,3H-,5H-(as-triazin-2-yl), 3H-,5H-(as-triazin-2-yl),
1H-(as-triazin-4-yl), 3H-(as-triazin-4-yl), 5H-(as-triazin-4-yl), 3H-,6H-(as-triazin-4-yl), 2H-,5H-(as-triazin-4-yl), 1H-,5H-(as-triazin-4-yl), 1H-,3H-(as-triazin-4-yl), 1H-,3H-,5H-(as-triazin-4-yl),
2H-(v-triazin-1-yl), 4H-(v-triazin-1-yl), 6H-(v-triazin-1-yl), 3H-,4H-(v-triazin-1-yl), 4H-,5H-(v-triazin-1-yl), 2H-,5H-(v-triazin-1-yl), 2H-,3H-,6H-(v-triazin-1-yl), 3H-,5H-(v-triazin-1-yl),
1H-(v-triazin-2-yl), 3H-(v-triazin-2-yl), 3H-,5H-(v-triazin-2-yl), 3H-,6H-(v-triazin-2-yl), 5H-,6H-(v-triazin-2-yl), 5H-(v-triazin-2-yl), 1H-,3H-,5H-(v-triazin-2-yl),
1,2-oxazin-2-yl, 5H-,6H-(1,2-oxazin-2-yl), 3H-,6H-(1,2-oxazin-2-yl), 4H-(1,2-oxazin-2-yl), 3H-,5H-(1,2-oxazin-2-yl),
1,2-oxazin-3-yl, 1H-,4H-(1,2-oxazin-2-yl), 2H-,5H-(1,2-oxazin-2-yl),
1,4-oxazin-4-yl, 5H-(1,4-oxazin-4-yl), morpholin-4-yl,
1,2,4-oxathiazin-4-yl, 5H-(1,2,5-oxathiazin-4-yl),
1,2,5-oxathiazin-5-yl, 3H-(1,2,5-oxathiazin-5-yl),
1,2,6-oxathiazin-6-yl, 3H-(1,2,6-oxathiazin-6-yl), 4H-(1,2,6-oxathiazin-6-yl), 5H-(1,2,6-oxathiazin-6-yl),
1,2,4-oxadiazin-4-yl, 2H-(1,2,4-oxadiazin-4-yl), 5H-(1,2,4-oxadiazin-4-yl), 2H-,5H-(1,2,4-oxadiazin-4-yl),
1,3,5-oxadiazin-3-yl, 4H-(1,3,5-oxadiazin-3-yl),
azepin-1-yl, 2H-,7H-azepin-1-yl, 4H-,6H-azepin-1-yl, 3H-,6H-azepin-1-yl, 4H-,7H-azepin-1-yl, 2H-,4H-,6H-azepin-1-yl,
1,2-diazepin-1-yl, 2H-,7H-(1,2-diazepin-1-yl), 4H-,6H-(1,2-diazepin-1-yl), 3H-,6H-(1,2-diazepin-1-yl), 4H-,7H-(1,2-diazepin-1-yl), 2H-,4H-,6H-(1,2-diazepin-1-yl), 2H-,4H-, 7H-(1,2-diazepin-1-yl), 2H-,4H-,5H-(1,2-diazepin-1-yl), 2H-,5H-(1,2-diazepin-1-yl), 2H-, 3H-(1,2-diazepin-1-yl),
indol-1-yl, 6H-,7H-indol-1-yl, 4H-,7H-indol-1-yl, 4H-,5H-indol-1-yl, 7H-,7 aH-indol-1-yl, 5H-,7aH-indol-1-yl, 5H-,6H-indol-1-yl, 4aH-,7aH-indol-1-yl, 3aH-,6H-indol-1-yl, 3aH-, 4H-indol-1-yl, 4H-,5H-,6H-,7H-indol-1-yl, 5H-,6H-,7H-,7 aH-indol-1-yl, 6H-,7H-,3aH-,7 aH-indol-1-yl, 4H-,7H-,3aH-,7 aH-indol-1-yl, 4H-,5H-,3 aH-,7 aH-indol-1-yl, 4H-,5H-,6H-,3 aH-indol-1-yl,
2H-indol-1-yl, 2H-,4aH-,7aH-indol-1-yl, 2H-,3aH-,6H-indol-1-yl, 2H-,3 aH-,4H-indol-1-yl, 2H-,6H-,7H-,3aH-,7aH-indol-1-yl, 2H-,4H-,7H-,3aH-,7aH-indol-1-yl, 2H-,4H-,5H-, 3aH-,7aH-indol-1-yl, 2H-,4H-,5 H-,6H-,3 aH-indol-1-yl,
2H-,3H-indol-1-yl, 2H-,3H-,6H-,7H-indol-1-yl, 2H-,3H-,4H-,7H-indol-1-yl, 2H-,3H-, 4H-,5H-indol-1-yl, 2H-,3H-,7H-,7 aH-indol-1-yl, 2H-,3H-,5H-,7 aH-indol-1-yl, 2H-,3H-,5H-, 6H-indol-1-yl, 2H-,3H-,4aH—,7 aH-indol-1-yl, 2H-,3H-,3aH-,6H-indol-1-yl, 2H-,3H-,3 aH-, 4H-indol-1-yl, 2H-,3 H-,4H-,5 H-,6H-,7 H-indol-1-yl, 2H-,3 H-,5 H-,6H-,7 H-,7 aH-indol-1-yl, 2H-,3H-,6H-,7H-,3aH-,7aH-indol-1-yl, 2H-,3H-,4H-,7H-,3aH-,7aH-indol-1-yl, 2H-,3H-,4H-, 5H-,3aH-,7 aH-indol-1-yl, 2H-,3H-,4H-,5H-,6H-,3 aH-indol-1-yl,
2-isobenzazol-2-yl, 4H-,5H-(2-isobenzazol-2-yl), 4H-,7H-(2-isobenzazol-2-yl), 1H-, 3H-(2-isobenzazol-2-yl), 1H-,3H-,4H-,5H-(2-isobenzazol-2-yl), 1H-,3H-,4H-,7H-(2-isobenzazol-2-yl), 1H-,3H-,4H-,4aH-,7aH-,7H-(2-isobenzazol-2-yl), 1H-,3H-,4aH-,7aH-(2-isobenzazol-2-yl), 1H-,3H-,5H-,6H-(2-isobenzazol-2-yl), 3H-,4aH-(2-isobenzazol-2-yl), 3H-, 5H-(2-isobenzazol-2-yl), 3H-,7H-(2-isobenzazol-2-yl), 3H-,4aH-,4H-,7aH-,7H-(2-isobenzazol-2-yl), 3H-,4aH-,6H-,7H-(2-isobenzazol-2-yl), 3H-,5H-,6H-,7H-(2-isobenzazol-2-yl), 4H-,4aH-,5H-(2-isobenzazol-2-yl), 1H-,3H-,4aH-,6H-,7H-,7aH-(2-isobenzazol-2-yl), 1H-, 3H-,5H-,6H-,7H-,7aH-(2-isobenzazol-2-yl), 3H-,4H-,4aH-,5H-,6H-,7H-(2-isobenzazol-2-yl), 1H-,3H-,4H-,5H-,6H-,7H-(2-isobenzazol-2-yl), 4H-,5H-,6H-,7H-(2-isobenzazol-2-yl),
1-pyrindin-1-yl, 4H-,5 aH-(1-pyrindin-1-yl), 2H-,5aH-(1-pyrindin-1-yl), 2H-,3H-,4H-, 5aH-(1-pyrindin-1-yl), 2H-,7H-,7 aH-(1-pyrindin-1-yl), 4H-,6H-,7H-,7aH-(1-pyrindin-1-yl), 2H-,3H-,4H-,6H-,7H-,7 aH-(1-pyrindin-1-yl), 2H-,7H-(1-pyrindin-1-yl), 4H-,7H-(1-pyrindin-1-yl), 2H-,3H-,4H-,7H-(1-pyrindin-1-yl), 4H-,5H-,5aH-,7H-,7aH-(1-pyrindin-1-yl), 2H-,3H-, 4H-,5aH-,7H-,7aH-(1-pyrindin-1-yl), 2H-,3H-,4H-,5H-,6H-,7H-,7 aH-(1-pyrindin-1-yl), 2H-, 3H-,4H-,5H-,5aH-,6H-,7H-,7aH-(1-pyrindin-1-yl), 2H-,5H-(1-pyrindin-1-yl), 4H-,5H-(1-pyrindin-1-yl), 2H-,3H-,4H-,5H-(1-pyrindin-1-yl), 2H-,5H-,5aH-,7aH-(1-pyrindin-1-yl), 2H-, 3H-,4H-,5H-,5aH-,7aH-(1-pyrindin-1-yl), 5H-,6H-(1-pyrindin-1-yl), 4H-,5H-,5aH-,6H-(1-pyrindin-1-yl), 2H-,3H-,5H-,6H-(1-pyrindin-1-yl), 2H-,3H-,4H-,5H-,5aH-(1-pyrindin-1-yl), 2H-,6H-(1-pyrindin-1-yl), 4H-,6H-(1-pyrindin-1-yl), 2H-,3H-,4H-,6H-(1-pyrindin-1-yl),
7H-(pyrano[3,4-b]pyrol-1-yl), 5H-(pyrano[3,4-b]pyrol-1-yl), 3aH-(pyrano[3,4-b]pyrol-1-yl), 4H-,5H-,7H-(pyrano[3,4-b]pyrol-1-yl), 5H-,7H-,7aH-(pyrano[3,4-b]pyrol-1-yl), 7H-,3aH-,7aH-(pyrano[3,4-b]pyrol-1-yl), 4H-,5H-,3aH-(pyrano[3,4-b]pyrol-1-yl), 2H-,3aH-(pyrano[3,4-b]pyrol-1-yl), 2H-,7H-,3aH-,7aH-(pyrano[3,4-b]pyrol-1-yl), 2H-,4H-,5H-,3aH-(pyrano[3,4-b]pyrol-1-yl), 2H-,3H-,7H-(pyrano[3,4-b]pyrol-1-yl), 2H-,3H-,5H-(pyrano[3,4-b]pyrol-1-yl), 2H-,3H-,3aH-(pyrano[3,4-b]pyrol-1-yl), 2H-,3H-,4H-,5H-,7H-(pyrano[3,4-b]pyrol-1-yl), 2H-,3H-,5H-,7H-,7aH-(pyrano[3,4-b]pyrol-1-yl), 2H-,3H-,7H-,3aH-,7aH-(pyrano[3,4-b]pyrol-1-yl), 2H-,3H-,4H-,5H-,3aH-(pyrano[3,4-b]pyrol-1-yl),
isoindazol-1-yl, 6H-,7H-isoindazol-1-yl, 4H-,7H-isoindazol-1-yl, 4H-,5H-isoindazol-1-yl, 7H-,7aH-isoindazol-1-yl, 5H-,7aH-isoindazol-1-yl, 5H-,6H-isoindazol-1-yl, 4aH-,7aH-isoindazol-1-yl, 3aH-,6H-isoindazol-1-yl, 3aH-,4H-isoindazol-1-yl, 4H-,5H-,6H-,7H-isoindazol-1-yl, 5H-,6H-,7H-,7aH-isoindazol-1-yl, 6H-,7H-,3aH-,7aH-isoindazol-1-yl, 4H-, 7H-,3aH-,7aH-isoindazol-1-yl, 4H-,5H-,3aH-,7aH-isoindazol-1-yl, 4H-,5H-,6H-,3aH-isoindazol-1-yl,
2H-isoindazol-1-yl, 2H-,4aH-,7 aH-isoindazol-1-yl, 2H-,3aH-,6H-isoindazol-1-yl, 2H-, 3aH-,4H-isoindazol-1-yl, 2H-,6H-,7H-,3aH-,7 aH-isoindazol-1-yl, 2H-,4H-,7H-,3aH-,7 aH-isoindazol-1-yl, 2H-,4H-,5H-,3aH-,7 aH-isoindazol-1-yl, 2H-,4H-,5H-,6H-,3aH-isoindazol-1-yl,
2H-,3H-isoindazol-1-yl, 2H-,3H-,6H-,7H-isoindazol-1-yl, 2H-,3H-,4H-,7H-isoindazol-1-yl, 2H-,3H-,4H-,5H-isoindazol-1-yl, 2H-,3H-,7H-,7aH-isoindazol-1-yl, 2H-,3H-, 5H-,7aH-isoindazol-1-yl, 2H-,3H-,5H-,6H-isoindazol-1-yl, 2H-,3H-,4aH-,7aH-isoindazol-1-yl, 2H-,3H-,3aH-,6H-isoindazol-1-yl, 2H-,3H-,3aH-,4H-isoindazol-1-yl, 2H-,3H-,4H-,5H-, 6H-,7H-isoindazol-1-yl, 2H-,3H-,5H-,6H-,7H-,7aH-isoindazol-1-yl, 2H-,3H-,6H-,7H-,3aH-, 7aH-isoindazol-1-yl, 2H-,3H-,4H-,7H-,3aH-,7 aH-isoindazol-1-yl, 2H-,3H-,4H-,5H-,3aH-, 7 aH-isoindazol-1-yl, 2H-,3H-,4H-,5H-,6H-,3aH-isoindazol-1-yl,
isoindazol-2-yl, 4H-,5H-isoindazol-2-yl, 4H-,7H-isoindazol-2-yl, 1H-,3H-isoindazol-2-yl, 1H-,3H-isoindazol-2-yl, 1H-,3H-,4H-,5H-isoindazol-2-yl, 1H-,3H-,4H-,7H-isoindazol-2-yl, 1H-,3H-,4H-,4aH-,7aH-,7H-isoindazol-2-yl, 1H-,3H-,4aH-,7aH-isoindazol-2-yl, 1H-, 3H-,5H-,6H-isoindazol-2-yl, 3H-,4aH-isoindazol-2-yl, 3H-,5H-isoindazol-2-yl, 3H-,7H-isoindazol-2-yl, 3H-,4aH-,4H-,7aH-,7H-isoindazol-2-yl, 3H-,4aH-,6H-,7H-isoindazol-2-yl, 3H-,5H-,6H-,7H-isoindazol-2-yl, 4H-,4aH-,5H-isoindazol-2-yl, 1H-,3H-,4aH-,6H-,7H-,7aH-isoindazol-2-yl, 1H-,3H-,5H-,6H-,7H-,7aH-isoindazol-2-yl, 3H-,4H-,4aH-,5H-,6H-,7H-isoindazol-2-yl, 1H-,3H-,4H-,5H-,6H-,7H-isoindazol-2-yl, 4H-,5H-,6H-,7H-isoindazol-2-yl, 1H-,3H-,7H-,7aH-isoindazol-2-yl, 1H-,3H-,4H-,4aH-,5H-,6H-isoindazol-2-yl, 1H-,3H-,4H-, 4aH-,5H-,7H-isoindazol-2-yl, 1H-,7aH-isoindazol-2-yl, 1H-,4H-isoindazol-2-yl, 1H-,4H-, 7H-,7aH-isoindazol-2-yl, 1H-,6H-,7H-,7aH-isoindazol-2-yl, 6H-,7H-isoindazol-2-yl, 1H-, 3H-,6H-,7H-isoindazol-2-yl, 1H-,3H-,4aH-,6H-isoindazol-2-yl, 1H-,4H-,5H-,6H-,7H-,7aH-isoindazol-2-yl,
indoxazin-2-yl, 3H-indoxazin-2-yl, 3H-,4H-,5H-indoxazin-2-yl, 3H-,4H-,7H-indoxazin-2-yl, 3H-,4H-,4aH-,7aH-,7H-indoxazin-2-yl, 3H-,4aH-,7aH-indoxazin-2-yl, 3H-, 5H-,6H-indoxazin-2-yl, 3H-,4aH-,6H-,7H-,7aH-indoxazin-2-yl, 3H-,5H-,6H-,7H-,7aH-indoxazin-2-yl, 3H-,4H-,5H-,6H-,7H-indoxazin-2-yl, 3H-,7H-,7aH-indoxazin-2-yl, 3H-,4H-, 4aH-,5H-,6H-indoxazin-2-yl, 3H-,4H-,4aH-,5H-,7H-indoxazin-2-yl, 7aH-indoxazin-2-yl, 4H-indoxazin-2-yl, 4H-,7H-,7aH-indoxazin-2-yl, 6H-,7H-,7aH-indoxazin-2-yl, 3H-,6H-,7H-indoxazin-2-yl, 3H-,4aH-,6H-indoxazin-2-yl, 4H-,5H-,6H-,7H-,7aH-indoxazin-2-yl,
benzoxazol-3-yl, 4H-,5H-benzoxazol-3-yl, 4H-,7H-benzoxazol-3-yl, 4H-,4aH-,7aH-, 7H-benzoxazol-3-yl, 4aH-,7aH-benzoxazol-3-yl, 5H-,6H-benzoxazol-3-yl, 4aH-,6H-,7H-, 7aH-benzoxazol-3-yl, 5H-,6H-,7H-,7aH-benzoxazol-3-yl, 4H-,5H-,6H-,7H-benzoxazol-3-yl, 7H-,7aH-benzoxazol-3-yl, 4H-,4aH-,5H-,6H-benzoxazol-3-yl, 4H-,4aH-,5H-,7H-benzoxazol-3-yl, 3H-,6H-,7H-benzoxazol-3-yl, 4aH-,6H-benzoxazol-3-yl,
anthran-1-yl, 4aH-,7aH-anthran-1-yl, 3aH-,6H-anthran-1-yl, 3aH-,4H-anthran-1-yl, 6H-,7H-,3aH-,7aH-anthran-1-yl, 4H-,7H-,3aH-,7aH-anthran-1-yl, 4H-,5H-,3aH-,7aH-anthran-1-yl, 4H-,5H-,6H-,3aH-anthran-1-yl, 3H-anthran-1-yl, 3H-,6H-,7H-anthran-1-yl, 3H-,4H-,7H-anthran-1-yl, 3H-,4H-,5H-anthran-1-yl, 3H-,7H-,7aH-anthran-1-yl, 3H-,5H-,7aH-anthran-1-yl, 3H-,5H-,6H-anthran-1-yl, 3H-,4aH-,7aH-anthran-1-yl, 3H-,3aH-,6H-anthran-1-yl, 3H-, 3aH-,4H-anthran-1-yl, 3H-,4H-,5H-,6H-,7H-anthran-1-yl, 3H-,5H-,6H-,7H-,7aH-anthran-1-yl, 3H-,6H-,7H-,3aH-,7aH-anthran-1-yl, 3H-,4H-,7H-,3aH-,7aH-anthran-1-yl, 3H-,4H-,5H-, 3aH-,7aH-anthran-1-yl, 3H-,4H-,5H-,6H-,3 aH-anthran-1-yl,
5H-quinol-1-yl, 2H-quinol-1-yl, 4H-,5H-,6H-,7H-,8H-quinol-1-yl, 2H-,5H-,5aH-,6H-, 7H-,8H-,8aH-quinol-1-yl, 2H-,3H-,5H-,6H-,7H-,8H-,8aH-quinol-1-yl, 4H-,5H-,5Ha-,6H-, 7H-,8H-,8aH-quinol-1-yl, 2H-,3H-,4H-,5H-,6H-,7H-,8H-quinol-1-yl, 8 aH-quinol-1-yl, 7H-, 8H-,8 aH-quinol-1-yl, 5H-,8H-,8 aH-quinol-1-yl, 5H-,6H-,8 aH-quinol-1-yl, 5H-,6H-quinol-1-yl, 5H-,6H-,7H-,8H-,8aH-quinol-1-yl, 2H-,7H-,8H-quinol-1-yl, 2H-,5H-,8H-quinol-1-yl, 2H-, 5H-,6H-quinol-1-yl, 2H-,5H-,6H-,7H-,8H-quinol-1-yl, 4H-,7H-,8H-quinol-1-yl, 4H-,5H-,6H-quinol-1-yl, 4H-quinol-1-yl, 2H-,3H-,7H-,8H-,8 aH-quinol-1-yl, 2H-,3H-,5H-,8H-,8 aH-quinol-1-yl, 2H-,3H-,5H-,6H-,8 aH-quinol-1-yl, 2H-,3H-,5H-,6H-,7H-quinol-1-yl, 2H-,3H-, 5H-quinol-1-yl, 2H-,3H-,7H-quinol-1-yl, 2H-,3H-,8 aH-quinol-1-yl, 2H-,6H-,7H-,8H-,8 aH-quinol-1-yl, 2H-,5H-,5 aH-,8H-,8 aH-quinol-1-yl, 2H-,5H-,5 aH-,6H-quinol-1-yl, 2H-,5H-,5 aH-, 6H-,7H-quinol-1-yl, 2H-,5H-,6H-,7H-,8H-quinol-1-yl, 2H-,7H-,8H-quinol-1-yl, 2H-,5H-,6H-quinol-1-yl, 2H-,5 H-,8 H-quinol-1-yl, 2H-,6H-,7 H-quinol-1-yl, 2H-,5aH-,8 aH-quinol-1-yl, 2H-,6H-,8aH-quinol-1-yl, 2H-,5aH-,7H-quinol-1-yl, 4H-,6H-,7H-,8H-,8aH-quinol-1-yl, 4H-, 5H-,5 aH-,8H-,8 aH-quinol-1-yl, 4H-,5H-,5 aH-,6H-quinol-1-yl, 4H-,5H-,5 aH-,6H-,7H-quinol-1-yl, 4H-,5H-,6H-,7H-,8H-quinol-1-yl, 4H-,7H-,8H-quinol-1-yl, 4H-,5H-,6H-quinol-1-yl, 4H-, 5H-,8H-quinol-1-yl, 4H-,6H-,7H-quinol-1-yl, 4H-,5 aH-,8 aH-quinol-1-yl, 2H-,3H-,4H-,7H-, 8H-quinol-1-yl, 2H-,3H-,4H-,5H-,8H-quinol-1-yl, 2H-,3H-,4H-,5H-,6H-quinol-1-yl, 2H-,3H-, 4H-,6H-,7H-quinol-1-yl, 2H-,3H-,4H-,5aH-,8aH-quinol-1-yl, 2H-,3H-,4H-,5H-,8H-quinol-1-yl, 2H-,3H-,4H-,5aH-,7H-quinol-1-yl, 2H-,3H-,4H-,6H-,8aH-quinol-1-yl, 2H-,3H-,4H-,5H-, 6H-quinol-1-yl, 2H-,3H-,4H-,7H-,8H-quinol-1-yl, 4H-,6H-,8aH-quinol-1-yl, 4H-,5aH-,7H-quinol-1-yl,
1H-isoquinol-2-yl, 1H-,5H-,6H-isoquinol-2-yl, 1H-,5H-,8H-isoquinol-2-yl, 1H-,7H-, 8H-isoquinol-2-yl, 1H-,5H-,6H-,7H-,8H-isoquinol-2-yl,
3H-isoquinol-2-yl, 3H-,5H-,6H-isoquinol-2-yl, 3H-,5H-,8H-isoquinol-2-yl, 3H-,7H-, 8H-isoquinol-2-yl, 3H-,5H-,6H-,7H-,8H-isoquinol-2-yl,
5aH-isoquinol-2-yl, 5H-,5aH-,6H-isoquinol-2-yl, 5H-,5aH-,8H-isoquinol-2-yl, 5aH-, 7H-,8H-isoquinol-2-yl, 6H-,7H-,8H-isoquinol-2-yl, 8H-isoquinol-2-yl, 6H-isoquinol-2-yl, 5H-,5aH-,6H-,7H-,8H-isoquinol-2-yl,
3H-,4H-,5aH-isoquinol-2-yl, 3H-,4H-,6H-isoquinol-2-yl, 3H-,4H-,6H-,7H-,8H-isoquinol-2-yl, 3H-,4H-,5aH-,7H-,8H-isoquinol-2-yl, 3H-,4H-,5H-,5aH-,8H-isoquinol-2-yl, 3H-,4H-,5H-,5aH-,6H-isoquinol-2-yl, 3H-,4H-,8H-isoquinol-2-yl, 3H-,4H-,5H-,5aH-,6H-,7H-, 8H-isoquinol-2-yl,
1H-,3H-,8aH-isoquinol-2-yl, 1H-,3H-,7H-isoquinol-2-yl, 1H-,3H-,5H-isoquinol-2-yl, 1H-,3H-,7H-,8H-,8aH-isoquinol-2-yl, 1H-,3H-,5H-,8H-,8aH-isoquinol-2-yl, 1H-,3H-,5H-,6H-, 8aH-isoquinol-2-yl, 1H-,3H-,5H-,6H-,7H-isoquinol-2-yl, 1H-,3H-,5H-,6H-,7H-,8H-,8aH-isoquinol-2-yl,
1H-,3H-,4H-,7H-,8H-isoquinol-2-yl, 1H-,3H-,4H-,7H-,8H-isoquinol-2-yl, 1H-,3H-, 4H-,5H-,8H-isoquinol-2-yl, 1H-,3H-,4H-,5H-,6H-isoquinol-2-yl, 1H-,3H-,4H-,5H-,6H-,7H-, 8H-isoquinol-2-yl,
1H-,5aH-,8aH-isoquinol-2-yl, 1H-,5aH-,7H-isoquinol-2-yl, 1H-,5aH-,7H-,8H-,8aH-isoquinol-2-yl, 1H-,5H-,5aH-,8H-,8aH-isoquinol-2-yl, 1H-,5H-,5aH-,6H-,8aH-isoquinol-2-yl, 1H-,5H-,5aH-,6H-,7H-isoquinol-2-yl, 1H-,6H-,8aH-isoquinol-2-yl, 1H-,8H-,8aH-isoquinol-2-yl, 1H-,6H-,7H-isoquinol-2-yl, 1H-,5H-,5aH-,6H-,7H-,8H-,8aH-isoquinol-2-yl,
1H-,3H-,4H-,5H-,5aH-,6H-,7H-,8H-,8aH-isoquinol-2-yl, 1H-,3H-,4H-,6H-,7H-,8H-, 8aH-isoquinol-2-yl, 1H-,3H-,4H-,5aH-,7H-,8H-,8aH-isoquinol-2-yl, 1H-,3H-,4H-,5H-,5aH-, 8H-,8aH-isoquinol-2-yl, 1H-,3H-,4H-,5H-,5aH-,6H-,8aH-isoquinol-2-yl, 1H-,3H-,4H-,5H-, 5aH-,6H-,7H-isoquinol-2-yl, 1H-,3H-,4H-,5H-,6H-,7H-,8H-isoquinol-2-yl, 1H-,3H-,4H-,7H-, 8H-isoquinol-2-yl, 1H-,3H-,4H-,5H-,8H-isoquinol-2-yl, 1H-,3H-,4H-,6H-,7H-isoquinol-2-yl, 1H-,3H-,4H-,5H-,6H-isoquinol-2-yl, 1H-,3H-,4H-,5aH-,8aH-isoquinol-2-yl, 1H-,3H-,4H-,8H-, 8aH-isoquinol-2-yl, 1H-,3H-,4H-,6H-,8aH-isoquinol-2-yl, 1H-,3H-,4H-,5aH-,7H-isoquinol-2-yl, 1H-,3H-,4H-,5H-,5aH-isoquinol-2-yl,
5H-cinnol-1-yl, 2H-cinnol-1-yl, 4H-,5H-,6H-,7H-,8H-cinnol-1-yl, 2H-,5H-,5aH-,6H-, 7H-,8H-,8aH-cinnol-1-yl, 2H-,3H-,5H-,6H-,7H-,8H-,8aH-cinnol-1-yl, 4H-,5H-,5Ha-,6H-, 7H-,8H-,8aH-cinnol-1-yl, 2H-,3H-,4H-,5H-,6H-,7H-,8H-cinnol-1-yl, 8aH-cinnol-1-yl, 7H-, 8H-,8aH-cinnol-1-yl, 5H-,8H-,8aH-cinnol-1-yl, 5H-,6H-,8aH-cinnol-1-yl, 5H-,6H-cinnol-1-yl, 5H-,6H-,7H-,8H-,8aH-cinnol-1-yl, 2H-,7H-,8H-cinnol-1-yl, 2H-,5H-,8H-cinnol-1-yl, 2H-, 5H-,6H-cinnol-1-yl, 2H-,5H-,6H-,7H-,8H-cinnol-1-yl, 4H-,7H-,8H-cinnol-1-yl, 4H-,5H-,6H-cinnol-1-yl, 4H-cinnol-1-yl, 2H-,3H-,7H-,8H-,8aH-cinnol-1-yl, 2H-,3H-,5H-,8H-,8aH-cinnol-1-yl, 2H-,3H-,5H-,6H-,8aH-cinnol-1-yl, 2H-,3H-,5H-,6H-,7H-cinnol-1-yl, 2H-,3H-,5H-cinnol-1-yl, 2H-,3H-,7H-cinnol-1-yl, 2H-,3H-,8aH-cinnol-1-yl, 2H-,6H-,7H-,8H-,8aH-cinnol-1-yl, 2H-,5H-,5aH-,8H-,8aH-cinnol-1-yl, 2H-,5H-,5aH-,6H-cinnol-1-yl, 2H-,5H-,5aH-,6H-, 7H-cinnol-1-yl, 2H-,5H-,6H-,7H-,8H-cinnol-1-yl, 2H-,7H-,8H-cinnol-1-yl, 2H-,5H-,6H-cinnol-1-yl, 2H-,5H-,8H-cinnol-1-yl, 2H-,6H-,7H-cinnol-1-yl, 2H-,5 aH-,8 aH-cinnol-1-yl, 2H-, 6H-,8aH-cinnol-1-yl, 2H-,5aH-,7H-cinnol-1-yl, 4H-,6H-,7H-,8H-,8aH-cinnol-1-yl, 4H-,5H-, 5aH-,8H-,8aH-cinnol-1-yl, 4H-,5H-,5aH-,6H-cinnol-1-yl, 4H-,5H-,5aH-,6H-,7H-cinnol-1-yl, 4H-,5H-,6H-,7H-,8H-cinnol-1-yl, 4H-,7H-,8H-cinnol-1-yl, 4H-,5H-,6H-cinnol-1-yl, 4H-,5H-, 8H-cinnol-1-yl, 4H-,6H-,7H-cinnol-1-yl, 4H-,5aH-,8aH-cinnol-1-yl, 2H-,3H-,4H-,7H-,8H-cinnol-1-yl, 2H-,3H-,4H-,5H-,8H-cinnol-1-yl, 2H-,3H-,4H-,5H-,6H-cinnol-1-yl, 2H-,3H-,4H-, 6H-,7H-cinnol-1-yl, 2H-,3H-,4H-,5aH—,8aH-cinnol-1-yl, 2H-,3H-,4H-,5H-,8H-cinnol-1-yl, 2H-,3H-,4H-,5aH-,7H-cinnol-1-yl, 2H-,3H-,4H-,6H-,8aH-cinnol-1-yl, 2H-,3H-,4H-,5H-,6H-cinnol-1-yl, 2H-,3H-,4H-,7H-,8H-cinnol-1-yl, 4H-,6H-,8aH-cinnol-1-yl, 4H-,5aH-,7H-cinnol-1-yl,
1H-cinnol-2-yl, 1H-,5H-,6H-cinnol-2-yl, 1H-,5H-,8H-cinnol-2-yl, 1H-,7H-,8H-cinnol-2-yl, 1H-,5H-,6H-,7H-,8H-cinnol-2-yl,
3H-cinnol-2-yl, 3H-,5H-,6H-cinnol-2-yl, 3H-,5H-,8H-cinnol-2-yl, 3H-,7H-,8H-cinnol-2-yl, 3H-,5H-,6H-,7H-,8H-cinnol-2-yl,
5aH-cinnol-2-yl, 5H-,5aH-,6H-cinnol-2-yl, 5H-,5aH-,8H-cinnol-2-yl, 5aH-,7H-,8H-cinnol-2-yl, 6H-,7H-,8H-cinnol-2-yl, 8H-cinnol-2-yl, 6H-cinnol-2-yl, 5H-,5aH-,6H-,7H-,8H-cinnol-2-yl,
3H-,4H-,5aH-cinnol-2-yl, 3H-,4H-,6H-cinnol-2-yl, 3H-,4H-,6H-,7H-,8H-cinnol-2-yl, 3H-,4H-,5aH-,7H-,8H-cinnol-2-yl, 3H-,4H-,5H-,5aH-,8H-cinnol-2-yl, 3H-,4H-,5H-,5aH-,6H-cinnol-2-yl, 3H-,4H-,8H-cinnol-2-yl, 3H-,4H-,5H-,5aH-,6H-,7H-,8H-cinnol-2-yl,
1H-,3H-,8aH-cinnol-2-yl, 1H-,3H-,7H-cinnol-2-yl, 1H-,3H-,5H-cinnol-2-yl, 1H-,3H-, 7H-,8H-,8aH-cinnol-2-yl, 1H-,3H-,5H-,8H-,8aH-cinnol-2-yl, 1H-,3H-,5H-,6H-,8aH-cinnol-2-yl, 1H-,3H-,5H-,6H-,7H-cinnol-2-yl, 1H-,3H-,5H-,6H-,7H-,8H-,8aH-cinnol-2-yl,
1H-,3H-,4H-,7H-,8H-cinnol-2-yl, 1H-,3H-,4H-,7H-,8H-cinnol-2-yl, 1H-,3H-,4H-,5H-, 8H-cinnol-2-yl, 1H-,3H-,4H-,5H-,6H-cinnol-2-yl, 1H-,3H-,4H-,5H-,6H-,7H-,8H-cinnol-2-yl,
1H-,5aH-,8aH-cinnol-2-yl, 1H-,5aH-,7H-cinnol-2-yl, 1H-,5aH-,7H-,8H-,8aH-cinnol-2-yl, 1H-,5H-,5aH-,8H-,8aH-cinnol-2-yl, 1H-,5H-,5aH-,6H-,8aH-cinnol-2-yl, 1H-,5H-,5aH-, 6H-,7H-cinnol-2-yl, 1H-,6H-,8aH-cinnol-2-yl, 1H-,8H-,8aH-cinnol-2-yl, 1H-,6H-,7H-cinnol-2-yl, 1H-,5H-,5aH-,6H-,7H-,8H-,8aH-cinnol-2-yl,
1H-,3H-,4H-,5H-,5aH-,6H-,7H-,8H-,8aH-cinnol-2-yl, 1H-,3H-,4H-,6H-,7H-,8H-,8aH-cinnol-2-yl, 1H-,3H-,4H-,5aH-,7H-,8H-,8aH-cinnol-2-yl, 1H-,3H-,4H-,5H-,5aH-,8H-,8aH-cinnol-2-yl, 1H-,3H-,4H-,5H-,5aH-,6H-,8aH-cinnol-2-yl, 1H-,3H-,4H-,5H-,5aH-,6H-,7H-cinnol-2-yl, 1H-,3H-,4H-,5H-,6H-,7H-,8H-cinnol-2-yl, 1H-,3H-,4H-,7H-,8H-cinnol-2-yl, 1H-, 3H-,4H-,5H-,8H-cinnol-2-yl, 1H-,3H-,4H-,6H-,7H-cinnol-2-yl, 1H-,3H-,4H-,5H-,6H-cinnol-2-yl, 1H-,3H-,4H-,5aH-,8aH-cinnol-2-yl, 1H-,3H-,4H-,8H-,8aH-cinnol-2-yl, 1H-,3H-,4H-, 6H-,8aH-cinnol-2-yl, 1H-,3H-,4H-,5aH-,7H-cinnol-2-yl, 1H-,3H-,4H-,5H-,5aH-cinnol-2-yl,
5H-quinazol-1-yl, 2H-quinazol-1-yl, 4H-,5H-,6H-,7H-,8H-quinazol-1-yl, 2H-,5H-, 5aH-,6H-,7H-,8H-,8aH-quinazol-1-yl, 2H-,3H-,5H-,6H-,7H-,8H-,8aH-quinazol-1-yl, 4H-, 5H-,5Ha-,6H-,7H-,8H-,8 aH-quinazol-1-yl, 2H-,3H-,4H-,5H-,6H-,7H-,8H-quinazol-1-yl, 8 aH-quinazol-1-yl, 7H-,8H-,8aH-quinazol-1-yl, 5H-,8H-,8 aH-quinazol-1-yl, 5H-,6H-,8aH-quinazol-1-yl, 5H-,6H-quinazol-1-yl, 5H-,6H-,7H-,8H-,8aH-quinazol-1-yl, 2H-,7H-,8H-quinazol-1-yl, 2H-,5H-,8H-quinazol-1-yl, 2H-,5H-,6H-quinazol-1-yl, 2H-,5H-,6H-,7H-,8H-quinazol-1-yl, 4H-,7H-,8H-quinazol-1-yl, 4H-,5H-,6H-quinazol-1-yl, 4H-quinazol-1-yl, 2H-, 3H-,7H-,8H-,8aH-quinazol-1-yl, 2H-,3H-,5H-,8H-,8aH-quinazol-1-yl, 2H-,3H-,5H-,6H-, 8aH-quinazol-1-yl, 2H-,3H-,5H-,6H-,7H-quinazol-1-yl, 2H-,3H-,5H-quinazol-1-yl, 2H-,3H-, 7H-quinazol-1-yl, 2H-,3H-,8 aH-quinazol-1-yl, 2H-,6H-,7H-,8H-,8aH-quinazol-1-yl, 2H-,5H-, 5aH-,8H-,8aH-quinazol-1-yl, 2H-,5H-,5 aH-,6H-quinazol-1-yl, 2H-,5H-,5aH-,6H-,7H-quinazol-1-yl, 2H-,5H-,6H-,7H-,8H-quinazol-1-yl, 2H-,7H-,8H-quinazol-1-yl, 2H-,5H-,6H-quinazol-1-yl, 2H-,5H-,8H-quinazol-1-yl, 2H-,6H-,7H-quinazol-1-yl, 2H-,5 aH-,8 aH-quinazol-1-yl, 2H-,6H-,8 aH-quinazol-1-yl, 2H-,5aH-,7H-quinazol-1-yl, 4H-,6H-,7H-,8H-, 8aH-quinazol-1-yl, 4H-,5H-,5aH-,8H-,8aH-quinazol-1-yl, 4H-,5H-,5aH-,6H-quinazol-1-yl, 4H-,5H-,5aH-,6H-,7H-quinazol-1-yl, 4H-,5H-,6H-,7H-,8H-quinazol-1-yl, 4H-,7H-,8H-quinazol-1-yl, 4H-,5H-,6H-quinazol-1-yl, 4H-,5H-,8H-quinazol-1-yl, 4H-,6H-,7H-quinazol-1-yl, 4H-,5aH-,8aH-quinazol-1-yl, 2H-,3H-,4H-,7H-,8H-quinazol-1-yl, 2H-,3H-,4H-,5H-,8H-quinazol-1-yl, 2H-,3H-,4H-,5H-,6H-quinazol-1-yl, 2H-,3H-,4H-,6H-,7H-quinazol-1-yl, 2H-, 3H-,4H-,5aH-,8 aH-quinazol-1-yl, 2H-,3H-,4H-,5H-,8H-quinazol-1-yl, 2H-,3H-,4H-,5aH-, 7H-quinazol-1-yl, 2H-,3H-,4H-,6H-,8 aH-quinazol-1-yl, 2H-,3H-,4H-,5H-,6H-quinazol-1-yl,
2H-,3H-,4H-,7H-,8H-quinazol-1-yl, 4H-,6H-,8 aH-quinazol-1-yl, 4H-,5aH-,7H-quinazol-1-yl, 2H-,4H-,5H-,5aH-,6H-,7H-,8H-quinazol-3-yl, 2H-,4H-,6H-,7H-,8H-quinazol-3-yl, 2H-,4H-,5aH-,7H-,8H-quinazol-3-yl, 2H-,4H-,5H-,5aH-,8H-quinazol-3-yl, 2H-,4H-,5H-,5aH-, 6H-quinazol-3-yl, 2H-,4H-,8H-quinazol-3-yl, 2H-,4H-,6H-quinazol-3-yl, 2H-,4H-,5aH-quinazol-3-yl, 4H-,5H-,5aH-,6H-,7H-,8H-,8aH-quinazol-3-yl, 4H-,6H-,7H-,8H-,8aH-quinazol-3-yl, 4H-,5aH-,7H-,8H-,8aH-quinazol-3-yl, 4H-,5H-,5aH-,8H-,8aH-quinazol-3-yl, H-,5H-,5aH-,6H-,8aH-quinazol-3-yl, 4H-,5H-,5aH-,6H-,7H-quinazol-3-yl, 4H-,6H-,7H-quinazol-3-yl, 4H-,5aH-,7H-quinazol-3-yl, 4H-,5H-,5aH-quinazol-3-yl, 4H-,6H-,8aH-quinazol-3-yl, 4H-,7H-,8aH-quinazol-3-yl, 4H-,5aH-,8aH-quinazol-3-yl, 2H-,5H-,6H-,7H-, 8H-quinazol-3-yl, 2H-,7H-,8H-quinazol-3-yl, 2H-,5H-,8H-quinazol-3-yl, 2H-,5H-,6H-quinazol-3-yl, 2H-quinazol-3-yl, 5H-,6H-,7H-,8H-,8aH-quinazol-3-yl, 7H-,8H-,8aH-quinazol-3-yl, 5H-,8H-,8aH-quinazol-3-yl, 5H-,6H-,8aH-quinazol-3-yl, 5H-,6H-,7H-quinazol-3-yl, 6H-quinazol-3-yl, 5H-quinazol-3-yl, 8aH-quinazol-3-yl, 4H-,5H-,6H-,7H-,8H-quinazol-3-yl, 4H-,7H-,8H-quinazol-3-yl, 4H-,5H-,8H-quinazol-3-yl, 4H-,5H-,6H-quinazol-3-yl, 4H-quinazol-3-yl, 1H-,2H-,5H-,6H-,7H-,8H-,8aH-quinazol-3-yl, 1H-,2H-,4H-,5H-,6H-, 7H-,8H-quinazol-3-yl, 1H-,2H-,7H-,8H-,8aH-quinazol-3-yl, 1H-,2H-,5H-,8H-,8aH-quinazol-3-yl, 1H-,2H-,5H-,6H-,8aH-quinazol-3-yl, 1H-,2H-,5H-,6H-,7H-quinazol-3-yl, 1H-,2H-,5H-quinazol-3-yl, 1H-,2H-,7H-quinazol-3-yl, 1H-,2H-,8aH-quinazol-3-yl, 1H-,2H-,4H-,7H-,8H-quinazol-3-yl, 1H-,2H-,4H-,5H-,8H-quinazol-3-yl, 1H-,2H-,4H-,5H-,6H-quinazol-3-yl, 1H-, 2H-,4H-,6H-,7H-quinazol-3-yl, 1H-,2H-,4H-,5aH-,8aH-quinazol-3-yl, 1H-,2H-,4H-,5H-,8H-quinazol-3-yl, 1H-,2H-,4H-,5aH-,7H-quinazol-3-yl, 1H-,2H-,4H-,6H-,8aH-quinazol-3-yl, 1H-, 2H-,4H-,5H-,6H-quinazol-3-yl, 1H-,2H-,4H-,7H-,8H-quinazol-3-yl,
5H-naphthyridin-1-yl, 2H-naphthyridin-1-yl, 4H-,5H-,6H-,7H-,8H-naphthyridin-1-yl, 2H-,5H-,5aH-,6H-,7H-,8H-,8aH-naphthyridin-1-yl, 2H-,3H-,5H-,6H-,7H-,8H-,8 aH-naphthyridin-1-yl, 4H-,5H-,5Ha-,6H-,7H-,8H-,8 aH-naphthyridin-1-yl, 2H-,3H-,4H-,5H-,6H-, 7H-,8H-naphthyridin-1-yl, 8 aH-naphthyridin-1-yl, 7H-,8H-,8 aH-naphthyridin-1-yl, 5H-,8H-, 8 aH-naphthyridin-1-yl, 5H-,6H-,8 aH-naphthyridin-1-yl, 5H-,6H-naphthyridin-1-yl, 5H-,6H-, 7H-,8H-,8 aH-naphthyridin-1-yl, 2H-,7H-,8H-naphthyridin-1-yl, 2H-,5H-,8H-naphthyridin-1-yl, 2H-,5H-,6H-naphthyridin-1-yl, 2H-,5H-,6H-,7H-,8H-naphthyridin-1-yl, 4H-,7H-,8H-naphthyridin-1-yl, 4H-,5H-,6H-naphthyridin-1-yl, 4H-naphthyridin-1-yl, 2H-,3H-,7H-,8H-, 8 aH-naphthyridin-1-yl, 2H-,3H-,5H-,8H-,8 aH-naphthyridin-1-yl, 2H-,3H-,5H-,6H-,8 aH-naphthyridin-1-yl, 2H-,3H-,5H-,6H-,7H-naphthyridin-1-yl, 2H-,3H-,5H-naphthyridin-1-yl, 2H-,3H-,7H-naphthyridin-1-yl, 2H-,3H-,8 aH-naphthyridin-1-yl, 2H-,6H-,7H-,8H-,8 aH-naphthyridin-1-yl, 2H-,5H-,5aH-,8H-,8 aH-naphthyridin-1-yl, 2H-,5H-,5aH-,6H-naphthyridin-1-yl, 2H-,5H-,5aH-,6H-,7H-naphthyridin-1-yl, 2H-,5H-,6H-,7H-,8H-naphthyridin-1-yl, 2H-, 7H-,8H-naphthyridin-1-yl, 2H-,5H-,6H-naphthyridin-1-yl, 2H-,5H-,8H-naphthyridin-1-yl, 2H-,6H-,7H-naphthyridin-1-yl, 2H-,5 aH-,8 aH-naphthyridin-1-yl, 2H-,6H-,8 aH-naphthyridin-1-yl, 2H-,5aH-,7H-naphthyridin-1-yl, 4H-,6H-,7H-,8H-,8 aH-naphthyridin-1-yl, 4H-,5H-,5aH-, 8H-,8aH-naphthyridin-1-yl, 4H-,5H-,5aH-,6H-naphthyridin-1-yl, 4H-,5H-,5aH-,6H-,7H-naphthyridin-1-yl, 4H-,5H-,6H-,7H-,8H-naphthyridin-1-yl, 4H-,7H-,8H-naphthyridin-1-yl, 4H-,5H-,6H-naphthyridin-1-yl, 4H-,5H-,8H-naphthyridin-1-yl, 4H-,6H-,7H-naphthyridin-1-yl, 4H-,5aH-,8 aH-naphthyridin-1-yl, 2H-,3H-,4H-,7H-,8H-naphthyridin-1-yl, 2H-,3H-,4H-, 5H-,8H-naphthyridin-1-yl, 2H-,3H-,4H-,5H-,6H-naphthyridin-1-yl, 2H-,3H-,4H-,6H-,7H-naphthyridin-1-yl, 2H-,3H-,4H-,5aH-,8 aH-naphthyridin-1-yl, 2H-,3H-,4H-,5H-,8H-naphthyridin-1-yl, 2H-,3H-,4H-,5aH-,7H-naphthyridin-1-yl, 2H-,3H-,4H-,6H-,8 aH-naphthyridin-1-yl, 2H-,3 H-,4H-,5 H-,6H-naphthyridin-1-yl, 2H-,3 H-,4H-,7 H-,8 H-naphthyridin-1-yl, 4H-,6H-,8 aH-naphthyridin-1-yl, 4H-,5aH-,7 H-naphthyridin-1-yl,
5H-pyrido[3,4-b]pyridin-1-yl, 2H-pyrido[3,4-b]pyridin-1-yl, 4H-,5H-,6H-,7H-,8H-pyrido[3,4-b]pyridin-1-yl, 2H-,5H-,5aH-,6H-,7H-,8H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-, 3H-,5H-,6H-,7H-,8H-,8aH-pyrido[3,4-b]pyridin-1-yl, 4H-,5H-,5Ha-,6H-,7H-,8H-,8aH-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,6H-,7H-,8H-pyrido[3,4-b]pyridin-1-yl, 8 aH-pyrido[3,4-b]pyridin-1-yl, 7H-,8H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 5H-,8H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 5 H-,6H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 5 H-,6H-pyrido[3,4-b]pyridin-1-yl, 5H-,6H-,7H-,8H-,8aH-pyrido[3,4-b]pyridin-1-yl, 2H-,7H-,8H-pyrido[3,4-b]pyridin-1-yl, 2H-, 5H-,8H-pyrido[3,4-b]pyridin-1-yl, 2H-,5H-,6H-pyrido[3,4-b]pyridin-1-yl, 2H-,5H-,6H-,7H-, 8H-pyrido[3,4-b]pyridin-1-yl, 4H-,7H-,8H-pyrido[3,4-b]pyridin-1-yl, 4H-,5H-,6H-pyrido[3,4-b]pyridin-1-yl, 4H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,7H-,8H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,5H-,8H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,5H-,6H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,5H-,6H-,7H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,5H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,7H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-,6H-,7H-,8H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-,5H-,5aH-,8H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-,5H-,5aH-,6H-pyrido[3,4-b]pyridin-1-yl, 2H-,5H-,5aH-,6H-, 7H-pyrido[3,4-b]pyridin-1-yl, 2H-,5H-,6H-,7H-,8H-pyrido[3,4-b]pyridin-1-yl, 2H-,7H-,8H-pyrido[3,4-b]pyridin-1-yl, 2H-,5H-,6H-pyrido[3,4-b]pyridin-1-yl, 2H-,5H-,8H-pyrido[3,4-b]pyridin-1-yl, 2H-,6H-,7H-pyrido[3,4-b]pyridin-1-yl, 2H-,5aH-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-,6H-,8aH-pyrido[3,4-b]pyridin-1-yl, 2H-,5aH-,7H-pyrido[3,4-b]pyridin-1-yl, 4H-,6H-, 7H-,8H-,8aH-pyrido[3,4-b]pyridin-1-yl, 4H-,5 H-,5 aH-,8 H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 4H-,5H-,5 aH-,6H-pyrido[3,4-b]pyridin-1-yl, 4H-,5H-,5 aH-,6H-,7 H-pyrido[3,4-b]pyridin-1-yl, 4H-,5H-,6H-,7H-,8H-pyrido[3,4-b]pyridin-1-yl, 4H-,7H-,8H-pyrido[3,4-b]pyridin-1-yl, 4H-, 5H-,6H-pyrido[3,4-b]pyridin-1-yl, 4H-,5H-,8H-pyrido[3,4-b]pyridin-1-yl, 4H-,6H-,7H-pyrido[3,4-b]pyridin-1-yl, 4H-,5aH-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-,7H-,8H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,8H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-,5H-, 6H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-,6H-,7H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-, 5aH-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,8H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-,5aH-,7H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-,6H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,6H-pyrido[3,4-b]pyridin-1-yl, 2H-,3H-,4H-,7H-,8H-pyrido[3,4-b]pyridin-1-yl, 4H-,6H-,8 aH-pyrido[3,4-b]pyridin-1-yl, 4H-,5aH-,7H-pyrido[3,4-b]pyridin-1-yl,
2H-,3H-,4H-,5H-,5aH-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 2H-,3H-,4H-,5H-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 2H-,3H-,4H-,5aH-,8H-pyrido[3,4-b]pyridin-7-yl, 2H-,3H-,4H-,5H-, 5aH-,6H-pyrido[3,4-b]pyridin-7-yl, 3H-,4H-,5H-,5aH-,6H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 3H-,4H-,6H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 3H-,4H-,5aH-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 3H-,4H-,5H-,5aH-,6H-,8aH-pyrido[3,4-b]pyridin-7-yl, 3H-,4H-,5H-,5aH-,6H-pyrido[3,4-b]pyridin-7-yl, 3H-,4H-,6H-pyrido[3,4-b]pyridin-7-yl, 3H-,4H-,5aH-pyrido[3,4-b]pyridin-7-yl, 4H-,5H-,5aH-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 4H-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 4H-,8H-pyrido[3,4-b]pyridin-7-yl, 3H-,4H-,5H-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 3H-,4H-,8H-pyrido[3,4-b]pyridin-7-yl, 2H-,5H-,5aH-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 2H-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 2H-,8H-pyrido[3,4-b]pyridin-7-yl, 3H-,5H-,6H-,8H-, 8aH-pyrido[3,4-b]pyridin-7-yl, 3H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 3H-pyrido[3,4-b]pyridin-7-yl, 5H-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 8H-pyrido[3,4-b]pyridin-7-yl, 1H-,4H-, 5H-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,5H-,5aH-,6H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,3H-,5H-,6H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 1H-,4H-,5H-,5Ha-, 6H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,3H-,4H-,5H-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 1H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 1H-,5H-,6H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,8H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,5H-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 1H-,4H-,8H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,3H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 1H-, 2H-,3H-,5H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,3H-,5H-,6H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,3H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,6H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,5H-,5aH-,6H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,5H-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,8H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,6H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-, 5aH-pyrido[3,4-b]pyridin-7-yl, 1H-,4H-,6H-,8H-,8aH-pyrido[3,4-b]pyridin-7-yl, 1H-,4H-, 5H-,5aH-,6H-pyrido[3,4-b]pyridin-7-yl, 1H-,4H-,5H-,6H-,8H-pyrido[3,4-b]pyridin-7-yl, 1H-, 4H-,8H-pyrido[3,4-b]pyridin-7-yl, 1H-,4H-,6H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,3H-,4H-, 8H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,3H-,4H-,6H-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,3H-, 4H-,5aH-,8aH-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,3H-,4H-,5aH-pyrido[3,4-b]pyridin-7-yl, 1H-,2H-,3H-,4H-,8H-pyrido[3,4-b]pyridin-7-yl, 1H-,4H-,5aH-pyrido[3,4-b]pyridin-7-yl,
5H-pyrido[3,2-b]pyridin-1-yl, 2H-pyrido[3,2-b]pyridin-1-yl, 4H-,5H-,6H-,7H-,8H-pyrido[3,2-b]pyridin-1-yl, 2H-,5H-,5aH-,6H-,7H-,8H-,8aH-pyrido[3,2-b]pyridin-1-yl, 2H-, 3H-,5H-,6H-,7H-,8H-,8aH-pyrido[3,2-b]pyridin-1-yl, 4H-,5H-,5Ha-,6H-,7H-,8H-,8aH-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,6H-,7H-,8H-pyrido[3,2-b]pyridin-1-yl, 8aH-pyrido[3,2-b]pyridin-1-yl, 7H-,8H-,8aH-pyrido[3,2-b]pyridin-1-yl, 5H-,8H-,8aH-pyrido[3,2-b]pyridin-1-yl, 5H-,6H-,8 aH-pyrido[3,2-b]pyridin-1-yl, 5H-,6H-pyrido[3,2-b]pyridin-1-yl, 5H-,6H-,7H-,8H-,8aH-pyrido[3,2-b]pyridin-1-yl, 2H-,7H-,8H-pyrido[3,2-b]pyridin-1-yl, 2H-, 5H-,8H-pyrido[3,2-b]pyridin-1-yl, 2H-,5H-,6H-pyrido[3,2-b]pyridin-1-yl, 2H-,5H-,6H-,7H-, 8H-pyrido[3,2-b]pyridin-1-yl, 4H-,7H-,8H-pyrido[3,2-b]pyridin-1-yl, 4H-,5H-,6H-pyrido[3,2-b]pyridin-1-yl, 4H-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,7H-,8H-,8 aH-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,5H-,8H-,8 aH-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,5H-,6H-,8 aH-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,5H-,6H-,7H-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,5H-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,7H-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,8 aH-pyrido[3,2-b]pyridin-1-yl, 2H-,6H-,7H-,8H-,8 aH-pyrido[3,2-b]pyridin-1-yl, 2H-,5H-,5aH-,8H-,8 aH-pyrido[3,2-b]pyridin-1-yl, 2H-,5H-,5aH-,6H-pyrido[3,2-b]pyridin-1-yl, 2H-,5H-,5aH-,6H-, 7H-pyrido[3,2-b]pyridin-1-yl, 2H-,5H-,6H-,7H-,8H-pyrido[3,2-b]pyridin-1-yl, 2H-,7H-,8H-pyrido[3,2-b]pyridin-1-yl, 2H-,5H-,6H-pyrido[3,2-b]pyridin-1-yl, 2H-,5H-,8H-pyrido[3,2-b]pyridin-1-yl, 2H-,6H-,7H-pyrido[3,2-b]pyridin-1-yl, 2H-,5aH-,8 aH-pyrido[3,2-b]pyridin-1-yl, 2H-,6H-,8aH-pyrido[3,2-b]pyridin-1-yl, 2H-,5aH-,7H-pyrido[3,2-b]pyridin-1-yl, 4H-,6H-, 7H-,8H-,8aH-pyrido[3,2-b]pyridin-1-yl, 4H-,5 H-,5aH-,8 H-,8 aH-pyrido[3,2-b]pyridin-1-yl, 4H-,5H-,5aH-,6H-pyrido[3,2-b]pyridin-1-yl, 4H-,5H-,5aH-,6H-,7H-pyrido[3,2-b]pyridin-1-yl, 4H-,5H-,6H-,7H-,8H-pyrido[3,2-b]pyridin-1-yl, 4H-,7H-,8H-pyrido[3,2-b]pyridin-1-yl, 4H-, 5H-,6H-pyrido[3,2-b]pyridin-1-yl, 4H-,5H-,8H-pyrido[3,2-b]pyridin-1-yl, 4H-,6H-,7H-pyrido[3,2-b]pyridin-1-yl, 4H-,5aH-,8 aH-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,4H-,7H-,8H-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,8H-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,4H-,5H-, 6H-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,4H-,6H-,7H-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,4H-, 5aH-,8 aH-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,8H-pyrido[3,2-b]pyridin-1-yl, 2H-, 3H-,4H-,5aH-,7H-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,4H-,6H-,8 aH-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,6H-pyrido[3,2-b]pyridin-1-yl, 2H-,3H-,4H-,7H-,8H-pyrido[3,2-b]pyridin-1-yl, 4H-,6H-,8 aH-pyrido[3,2-b]pyridin-1-yl, 4H-,5aH-,7H-pyrido[3,2-b]pyridin-1-yl,
5H-pyrido[4,3-b]pyridin-1-yl, 2H-pyrido[4,3-b]pyridin-1-yl, 4H-,5H-,6H-,7H-,8H-pyrido[4,3-b]pyridin-1-yl, 2H-,5H-,5aH-,6H-,7H-,8H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-, 3H-,5H-,6H-,7H-,8H-,8aH-pyrido[4,3-b]pyridin-1-yl, 4H-,5H-,5Ha-,6H-,7H-,8H-,8aH-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,6H-,7H-,8H-pyrido[4,3-b]pyridin-1-yl, 8 aH-pyrido[4,3-b]pyridin-1-yl, 7H-,8H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 5H-,8H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 5 H-,6H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 5 H-,6H-pyrido[4,3-b]pyridin-1-yl, 5H-,6H-,7H-,8H-,8aH-pyrido[4,3-b]pyridin-1-yl, 2H-,7H-,8H-pyrido[4,3-b]pyridin-1-yl, 2H-, 5H-,8H-pyrido[4,3-b]pyridin-1-yl, 2H-,5H-,6H-pyrido[4,3-b]pyridin-1-yl, 2H-,5H-,6H-,7H-, 8H-pyrido[4,3-b]pyridin-1-yl, 4H-,7H-,8H-pyrido[4,3-b]pyridin-1-yl, 4H-,5H-,6H-pyrido[4,3-b]pyridin-1-yl, 4H-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,7H-,8H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,5H-,8H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,5H-,6H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,5H-,6H-,7H-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,5H-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,7H-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-,6H-,7H-,8H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-,5H-,5aH-,8H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-,5H-,5aH-,6H-pyrido[4,3-b]pyridin-1-yl, 2H-,5H-,5aH-,6H-, 7H-pyrido[4,3-b]pyridin-1-yl, 2H-,5H-,6H-,7H-,8H-pyrido[4,3-b]pyridin-1-yl, 2H-,7H-,8H-pyrido[4,3-b]pyridin-1-yl, 2H-,5H-,6H-pyrido[4,3-b]pyridin-1-yl, 2H-,5H-,8H-pyrido[4,3-b]pyridin-1-yl, 2H-,6H-,7H-pyrido[4,3-b]pyridin-1-yl, 2H-,5aH-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-,6H-,8aH-pyrido[4,3-b]pyridin-1-yl, 2H-,5aH-,7H-pyrido[4,3-b]pyridin-1-yl, 4H-,6H-, 7H-,8H-,8aH-pyrido[4,3-b]pyridin-1-yl, 4H-,5 H-,5aH-,8 H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 4H-,5H-,5 aH-,6H-pyrido[4,3-b]pyridin-1-yl, 4H-,5H-,5 aH-,6H-,7 H-pyrido[4,3-b]pyridin-1-yl, 4H-,5H-,6H-,7H-,8H-pyrido[4,3-b]pyridin-1-yl, 4H-,7H-,8H-pyrido[4,3-b]pyridin-1-yl, 4H-, 5H-,6H-pyrido[4,3-b]pyridin-1-yl, 4H-,5H-,8H-pyrido[4,3-b]pyridin-1-yl, 4H-,6H-,7H-pyrido[4,3-b]pyridin-1-yl, 4H-,5aH-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,4H-,7H-,8H-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,8H-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,4H-,5H-, 6H-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,4H-,6H-,7H-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,4H-, 5aH-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,8H-pyrido[4,3-b]pyridin-1-yl, 2H-, 3H-,4H-,5aH-,7H-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,4H-,6H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,4H-,5H-,6H-pyrido[4,3-b]pyridin-1-yl, 2H-,3H-,4H-,7H-,8H-pyrido[4,3-b]pyridin-1-yl, 4H-,6H-,8 aH-pyrido[4,3-b]pyridin-1-yl, 4H-,5aH-,7H-pyrido[4,3-b]pyridin-1-yl,
2H-,3H-,4H-,5H-,5aH-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 2H-,3H-,4H-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 2H-,3H-,4H-,5H-,5aH-,7H-pyrido[4,3-b]pyridin-6-yl, 2H-,3H-,4H-pyrido[4,3-b]pyridin-6-yl, 3H-,4H-,5H-,5aH-,7H-,8H-,8aH-pyrido[4,3-b]pyridin-6-yl, 3H-, 4H-,7H-,8H-,8aH-pyrido[4,3-b]pyridin-6-yl, 3H-,4H-,5H-,5aH-,7H-,8aH-pyrido[4,3-b]pyridin-6-yl, 3H-,4H-,5H-,5aH-,7H-pyrido[4,3-b]pyridin-6-yl, 3H-,4H-,7H-pyrido[4,3-b]pyridin-6-yl, 3H-,4H-,8aH-pyrido[4,3-b]pyridin-6-yl, 4H-,5H-,5aH-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 4H-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 4H-,5H-pyrido[4,3-b]pyridin-6-yl, 4H-pyrido[4,3-b]pyridin-6-yl, 3H-,4H-,5H-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 3H-,4H-,5H-pyrido[4,3-b]pyridin-6-yl, 2H-,5H-,5aH-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 2H-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 2H-,5H-pyrido[4,3-b]pyridin-6-yl, 2H-pyrido[4,3-b]pyridin-6-yl, 3H-,5H-,7H-,8H-,8aH-pyrido[4,3-b]pyridin-6-yl, 3H-,5H-,8aH-pyrido[4,3-b]pyridin-6-yl, 3H-, 5H-pyrido[4,3-b]pyridin-6-yl, 5H-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 5H-pyrido[4,3-b]pyridin-6-yl, 1H-,4H-,5H-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,3H-,5H-,7H-,8H-, 8aH-pyrido[4,3-b]pyridin-6-yl, 1H-,4H-,5H-,5Ha-,7H-,8H-,8aH-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,3H-,4H-,5H-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 1H-,5H-,8aH-pyrido[4,3-b]pyridin-6-yl, 1H-,5H-pyrido[4,3-b]pyridin-6-yl, 1H-,5H-,7H-,8H-,8aH-pyrido[4,3-b]pyridin-6-yl, 1H-, 2H-,5H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,5H-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 1H-,4H-, 5H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,3H-,5H-,8aH-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,3H-, 5H-,7H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,7H-,8H-,8aH-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-, 5H-,5aH-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,5H-,5aH-,7H-pyrido[4,3-b]pyridin-6-yl, 1H-, 2H-,5H-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,5H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-, 5H-,8H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,7H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,8aH-pyrido[4,3-b]pyridin-6-yl, 1H-,4H-,7H-,8H-,8aH-pyrido[4,3-b]pyridin-6-yl, 1H-,4H-,5H-, 5aH-pyrido[4,3-b]pyridin-6-yl, 1H-,4H-,5H-,5aH-,7H-pyrido[4,3-b]pyridin-6-yl, 1H-,4H-, 5H-,7H-,8H-pyrido[4,3-b]pyridin-6-yl, 1H-,4H-,5H-pyrido[4,3-b]pyridin-6-yl, 1H-,4H-,7H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,3H-,4H-,5H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,3H-,4H-, 7H-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,3H-,4H-,8aH-pyrido[4,3-b]pyridin-6-yl, 1H-,2H-,3H-, 4H-,5H-pyrido[4,3-b]pyridin-6-yl, 1H-,4H-,8aH-pyrido[4,3-b]pyridin-6-yl,
2H-,4H-(1,3-benzoxazin-3-yl), 2H-,4H-,5H-,8H-(1,3-benzoxazin-3-yl), 2H-,4H-,7H-, 8H-(1,3-benzoxazin-3-yl), 2H-,4H-,5H-,6H-(1,3-benzoxazin-3-yl), 2H-,4H-,5H-,6H-,7H-, 8H-(1,3-benzoxazin-3-yl), 2H-,8aH-(1,3-benzoxazin-3-yl), 2H-,5H-(1,3-benzoxazin-3-yl), 2H-,5H-,6H-,7H-(1,3-benzoxazin-3-yl), 2H-,5H-,8H-,8aH-(1,3-benzoxazin-3-yl), 2H-,7H-, 8H-,8aH-(1,3-benzoxazin-3-yl), 2H-,7H-,8H-,8aH-(1,3-benzoxazin-3-yl), 2H-,7H-(1,3-benzoxazin-3-yl), 2H-,5H-,6H-,7H-,8H-,8aH-(1,3-benzoxazin-3-yl), 2H-,4H-,5aH-,8aH-(1,3-benzoxazin-3-yl), 2H-,4H-,5aH-,7H-(1,3-benzoxazin-3-yl), 2H-,4H-,6H-(1,3-benzoxazin-3-yl), 2H-,4H-,6H-,7H-,8H-,8aH-(1,3-benzoxazin-3-yl), 2H-,4H-,5aH-,7H-,8H-,8aH-(1,3-benzoxazin-3-yl), 2H-,4H-,5H-,5aH-,8H-,8aH-1,3-benzoxazin-3-yl), 2H-,4H-,5H-,5aH-,6H-, 8aH-(1,3-benzoxazin-3-yl), 2H-,4H-,5H-,5aH-,6H-,7H-(1,3-benzoxazin-3-yl), 2H-,4H-,5H-, 5aH-,6H-,7H-,8H-,8aH-(1,3-benzoxazin-3-yl),
5H-,5aH-,6H-,7H-,8H-,8aH-(1,4-benzoxazin-4-yl), 6H-,7H-,8H-,8aH-(1,4-benzoxazin-4-yl), 5aH-,7H-,8H-,8aH-(1,4-benzoxazin-4-yl), 5H-,5aH-,8H-,8aH-(1,4-benzoxazin-4-yl), 5H-,5aH-,6H-,8aH-(1,4-benzoxazin-4-yl), 5H-,5aH-,6H-,7H-(1,4-benzoxazin-4-yl), 5aH-,7H-(1,4-benzoxazin-4-yl), 6H-,8aH-(1,4-benzoxazin-4-yl), 8H-,8aH-(1,4-benzoxazin-4-yl), 5H-,5aH-(1,4-benzoxazin-4-yl), 2H-,3H-,5H-,6H-,7H-,8H-(1,4-benzoxazin-4-yl), 2H-,3H-,7H-,8H-(1,4-benzoxazin-4-yl), 2H-,3H-,5H-,8H-(1,4-benzoxazin-4-yl), 2H-,3H-,5H-,6H-(1,4-benzoxazin-4-yl), 5H-,6H-,7H-,8H-(1,4-benzoxazin-4-yl), 7H-, 8H-(1,4-benzoxazin-4-yl), 5H-,8H-(1,4-benzoxazin-4-yl), 5H-,6H-(1,4-benzoxazin-4-yl), 1,4-benzoxazin-4-yl, 2H-,3H-,5H-,5aH-,6H-,7H-,8H-,8aH-(1,4-benzoxazin-4-yl), 2H-,3H-, 6H-,7H-,8H-,8aH-(1,4-benzoxazin-4-yl), 2H-,3H-,5aH-,7H-,8H-,8aH-(1,4-benzoxazin-4-yl), 2H-,3H-,5H-,5aH-,8H-,8aH-(1,4-benzoxazin-4-yl), 2H-,3H-,5H-,5aH-,6H-,8H-(1,4-benzoxazin-4-yl), 2H-,3H-,5H-,5aH-,6H-,7H-(1,4-benzoxazin-4-yl), 2H-,3H-,6H-,7H-(1,4-benzoxazin-4-yl), 2H-,3H-,5aH-,7H-(1,4-benzoxazin-4-yl), 2H-,3H-,5H-,5aH-(1,4-benzoxazin-4-yl), 2H-,3H-,6H-,8aH-(1,4-benzoxazin-4-yl), 2H-,3H-,8H-,8aH-(1,4-benzoxazin-4-yl),
5H-,5aH-,6H-,7H-,8H-,8aH-(2,3-benzoxazin-3-yl), 5aH-,7H-,8H-(2,3-benzoxazin-3-yl), 5H-,8H-(2,3-benzoxazin-3-yl), 5H-,6H-(2,3-benzoxazin-3-yl), 2,3-benzoxazin-3-yl, 1H-, 4H-,5H-,6H-,7H-,8H-(2,3-benzoxazin-3-yl), 1H-,4H-,7H-,8H-(2,3-benzoxazin-3-yl), 1H-, 4H-,5H-,8H-(2,3-benzoxazin-3-yl), 1H-,4H-,5H-,6H-(2,3-benzoxazin-3-yl), 1H-,4H-(2,3-benzoxazin-3-yl), 4H-,6H-,7H-,8H-(2,3-benzoxazin-3-yl), 4H-,7H-,8H-(2,3-benzoxazin-3-yl), 4H-,5H-,8H-(2,3-benzoxazin-3-yl), 4H-,5H-,6H-(2,3-benzoxazin-3-yl), 4H-,5H-,5aH-,6H-, 7H-,8H-,8aH-(2,3-benzoxazin-3-yl), 4H-,8H-(2,3-benzoxazin-3-yl), 4H-,6H-(2,3-benzoxazin-3-yl), 4H-,5aH-(2,3-benzoxazin-3-yl), 1H-,5H-,6H-,7H-,8H-,8aH-(2,3-benzoxazin-3-yl), 1H-,7H-,8H-,8aH-(2,3-benzoxazin-3-yl), 1H-,5H-,7H-,8H-,8aH-(2,3-benzoxazin-3-yl), 1H-,5H-,6H-,8aH-(2,3-benzoxazin-3-yl), 1H-,5H-,6H-,7H-(2,3-benzoxazin-3-yl), 1H-,8aH-(2,3-benzoxazin-3-yl), 1H-,7H-(2,3-benzoxazin-3-yl), 1H-,5H-(2,3-benzoxazin-3-yl), 1H-,4H-,5H-,5aH-,6H-,7H-,8H-,8aH-(2,3-benzoxazin-3-yl), 1H-,4H-, 6H-,7H-,8H-,8aH-(2,3-benzoxazin-3-yl), 1H-,4H-,5aH-,7H-,8H-,8aH-(2,3-benzoxazin-3-yl), 1H-,4H-,5H-,5aH-,8H-,8aH-(2,3-benzoxazin-3-yl), 1H-,4H-,5H-,5aH-,6H-,8aH-(2,3-benzoxazin-3-yl), 1H-,4H-,5H-,5aH-,6H-,7H-(2,3-benzoxazin-3-yl), 1H-,4H-,6H-,7H-(2,3-benzoxazin-3-yl), 1H-,4H-,5aH-,7H-(2,3-benzoxazin-3-yl), 1H-,4H-,5H-,5aH-(2,3-benzoxazin-3-yl), 1H-,4H-,6H-,8aH-(2,3-benzoxazin-3-yl), 1H-,4H-,8H-,8aH-(2,3-benzoxazin-3-yl),
3,1-benzoxazin-1-yl, 2H-,5H-,6H-,7H-,8H-,8aH-(3,1-benzoxazin-1-yl), 2H-,4H-,5H-, 6H-,7H-,8H-(3,1-benzoxazin-1-yl), 2H-,7H-,8H-,8aH-(3,1-benzoxazin-1-yl), 2H-,5H-,8H-, 8aH-(3,1-benzoxazin-1-yl), 2H-,5H-,6H-,8aH-(3,1-benzoxazin-1-yl), 2H-,5H-,6H-,7H-(3,1-benzoxazin-1-yl), 2H-,5H-(3,1-benzoxazin-1-yl), 2H-,7H-(3,1-benzoxazin-1-yl), 2H-,8 aH-(3,1-benzoxazin-1-yl), 2H-,4H-,7H-,8H-(3,1-benzoxazin-1-yl), 2H-,4H-,5H-,8H-(3,1-benzoxazin-1-yl), 2H-,4H-,5H-,6H-(3,1-benzoxazin-1-yl), 2H-,4H-,6H-,7H-(3,1-benzoxazin-1-yl), 2H-,4H-,5 aH-,8aH-(3,1-benz oxazin-1-yl), 2H-,4H-,5H-,8H-(3,1-benzoxazin-1-yl), 2H-, 4H-,5 aH-,7H-(3,1-benzoxazin-1-yl), 2H-,4H-,6H-,8aH-(3,1-benzoxazin-1-yl), 2H-,4H-,5H-, 6H-(3,1-benzoxazin-1-yl), 2H-,4H-,7H-,8H-(3,1-benzoxazin-1-yl),
1,2-benzisoxazin-2-yl, 5H-,6H-(1,2-benzisoxazin-2-yl), 5H-,8H-(1,2-benzisoxazin-2-yl), 7H-,8H-(1,2-benzisoxazin-2-yl), 5H-,6H-,7H-,8H-(1,2-benzisoxazin-2-yl),
3H-,8aH-(1,2-benzisoxazin-2-yl), 3H-,7H-(1,2-benzisoxazin-2-yl), 3H-,5H-(1,2-benzisoxazin-2-yl), 3H-,7H-,8H-,8aH-(1,2-benzisoxazin-2-yl), 3H-,5H-,8H-,8aH-(1,2-benzisoxazin-2-yl), 3H-,5H-,6H-,8aH-(1,2-benzisoxazin-2-yl), 3H-,5H-,6H-,7H-(1,2-benzisoxazin-2-yl), 3H-,5H-,6H-,7H-,8H-,8aH-(1,2-benzisoxazin-2-yl),
3H-,4H-,7H-,8H-(1,2-benzisoxazin-2-yl), 3H-,4H-,7H-,8H-(1,2-benzisoxazin-2-yl), 3H-,4H-,5H-,8H-(1,2-benzisoxazin-2-yl), 3H-,4H-,5H-,6H-(1,2-benzisoxazin-2-yl), 3H-,4H-, 5H-,6H-,7H-,8H-(1,2-benzisoxazin-2-yl),
5aH-,8aH-(1,2-benzisoxazin-2-yl), 5aH-,7H-(1,2-benzisoxazin-2-yl), 5aH-,7H-,8H-, 8aH-(1,2-benzisoxazin-2-yl), 5H-,5aH-,8H-,8aH-(1,2-benzisoxazin-2-yl), 5H-,5aH-,6H-, 8aH-(1,2-benzisoxazin-2-yl), 5H-,5aH-,6H-,7H-(1,2-benzisoxazin-2-yl), 6H-,8aH-(1,2-benzisoxazin-2-yl), 8H-,8aH-(1,2-benzisoxazin-2-yl), 6H-,7H-(1,2-benzisoxazin-2-yl), 5H-, 5aH-,6H-,7H-,8H-,8aH-(1,2-benzisoxazin-2-yl),
3H-,4H-,5H-,5aH-,6H-,7H-,8H-,8aH-(1,2-benzisoxazin-2-yl), 3H-,4H-,6H-,7H-,8H-, 8aH-(1,2-benzisoxazin-2-yl), 3H-,4H-,5aH-,7H-,8H-,8aH-(1,2-benzisoxazin-2-yl), 3H-,4H-, 5H-,5aH-,8H-,8aH-(1,2-benzisoxazin-2-yl), 3H-,4H-,5H-,5aH-,6H-,8aH-(1,2-benzisoxazin-2-yl), 3H-,4H-,5H-,5aH-,6H-,7H-(1,2-benzisoxazin-2-yl), 3H-,4H-,5H-,6H-,7H-,8H-(1,2-benzisoxazin-2-yl), 3H-,4H-,7H-,8H-(1,2-benzisoxazin-2-yl), 3H-,4H-,5H-,8H-(1,2-benzisoxazin-2-yl), 3H-,4H-,6H-,7H-(1,2-benzisoxazin-2-yl), 3H-,4H-,5H-,6H-(1,2-benzisoxazin-2-yl), 3H-,4H-,5aH-,8aH-(1,2-benzisoxazin-2-yl), 3H-,4H-,8H-,8aH-(1,2-benzisoxazin-2-yl), 3H-,4H-,6H-,8aH-(1,2-benzisoxazin-2-yl), 3H-,4H-,5aH-,7H-(1,2-benzisoxazin-2-yl), 3H-,4H-,5H-,5aH-(1,2-benzisoxazin-2-yl),
purin-1-yl, purin-3-yl, purin-7-yl, purin-9-yl, or hydro compound thereof,
carbazol-9-yl, or hydro compound thereof,
and salt thereof.
31 . The compound of claim 1 , wherein one or more heterocyclic ring group formed by one or both of R 1 and R 2 together with the nitrogen to which they are attached and R 7 and R 8 together with the nitrogen to which they are attached is independently unsubstituted or substituted with one or more substitutents selected from the group consisting of hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , CONHR 12 , COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, salt thereof, and a combination thereof.
32 . The compound of claim 1 , wherein one or more of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is independently a (C 3 -C 25 ) heterocyclyl selected from the group consisting of furan, thiophene, pyrrole, isopyrrole, pyrazole, isodiazole, triazole, dithole, oxathole, isoxazole, thiazole, isothiazole, oxadiazole, dioxazole, oxathiazole, oxathiole, pyran, pyridine, pyridazine, pyrimidine, pyrazine, piperazine, morpholino, triazine, oxazine, isoxazine, oxathiazine, azepine, oxepin, thiepin, diazepine, benzofuran, isobenzofuran, thionaphthene, isothionaphthene, indole, isbenzazole, pyrindine, pyrano[3,4-b]pyrrole, isoindazole, indoxazine, benzoxazole, anthranil, benzopyran, quinoline, isoquinoline, cinnoline, quinazoline, nahthyridine, pyrido[3,4-b]pyridine, pyrido[3,2-b]pyridine, pyrido[4,3-b-]pyridine, benzoxazine, carbazole, xanthene, acridine, purine, hydro compound thereof, and salt thereof.
33 . A composition, comprising at least one pharmaceutically acceptable carrier and at least one compound having the following formula:
or salt thereof;
wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —NR 12 COR 13 , —CONR 12 R 13 , CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 NHR 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 1 and R 2 together with the nitrogen to which they are attached form a heterocyclic ring group or salt thereof;
wherein R 3 , R 9 , and R 11 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
wherein R 4 is hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , — 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —CN, —NC, —SH, —NO 2 , —NH 2 , PR 2 ,—(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, or salt thereof
wherein R 5 and R 6 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 5 and R 6 together with the carbons to which they are attached form a (C 5 -C 6 ) aryl structure, a (C 3 -C 6 ) heteroaryl structure, a (C 3 -C 6 ) heterocycloalkenyl structure, a (C 4 -C 6 ) cycloalkenyl structure, or salt thereof;
wherein R 7 and R 8 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —C(NH)NH 2 , —C(NH)NHC(NH)NH 2 , —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 7 and R 8 together with the nitrogen to which they are attached form a heterocyclic ring group or salt thereof;
wherein R 10 is hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 14 , —NR 14 R 15 , —NR 14 COR 15 , —CONR 14 R 15 , —CONR 14 , —COOR 14 , —OCOR 14 , —COR 14 , —SR 14 , —SO 2 R 14 , —SO 3 R 14 , —SO 2 NR 14 , —SOR 14 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 14 R 15 , —PO 3 R 14 R 15 , OPO 3 R 14 R 15 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, or salt thereof;
wherein R 12 and R 13 are each independently selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
wherein R 14 and R 15 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
and wherein each of said (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, (C 3 -C 6 ) cycloalkyl structure, (C 5 -C 6 ) aryl structure, (C 3 -C 6 ) heteroaryl structure, (C 3 -C 6 ) heterocyclyl structure, (C 3 -C 6 ) heterocycloalkenyl structure, (C 4 -C 6 ) cycloalkenyl structure, heterocyclic ring group, or salt thereof may be independently unsubstituted or substituted with one or more substituents selected from the group consisting of hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, salt thereof, and a combination thereof.
34 . The composition of claim 33 , wherein when R 3 , R 10 , and R 11 are hydrogen, and R 9 is —CH 3 , then R 5 is not —CN.
35 . A composition, comprising:
at least one inhibitor selected from the group consisting of Nucleoside analog Reverse Transcriptase inhibitor (NRTi), —Non-Nucleoside analog Reverse Transcriptase inhibitor (NNRTi), Protease inhibitor (Pi), Cell Entry inhibitor (Ci), and a combination thereof; and
at least one compound having the following formula:
or salt thereof;
wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 NHR 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 1 and R 2 together with the nitrogen to which they are attached form a heterocyclic ring group or salt thereof;
wherein R 3 , R 9 , and R 11 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
wherein R 4 is hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 ,—(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, or salt thereof
wherein R 5 and R 6 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 5 and R 6 together with the carbons to which they are attached form a (C 5 -C 6 ) aryl structure, a (C 3 -C 6 ) heteroaryl structure, a (C 3 -C 6 ) heterocycloalkenyl structure, a (C 4 -C 6 ) cycloalkenyl structure, or salt thereof;
wherein R 7 and R 8 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —C(NH)NH 2 , C(NH)NHC(NH)NH 2 , —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 7 and R 8 together with the nitrogen to which they are attached form a heterocyclic ring group or salt thereof;
wherein R 10 is hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 14 , NR 14 R 15 , —NR 14 COR 15 , —CONR 14 R 15 , —CONR 14 , —COOR 14 , —OCOR 14 , —COR 14 , SR 14 , —SO 2 R 14 , —SO 3 R 14 , —SO 2 NR 14 , —SOR 14 , —N 3 , —CN, —NC, —SH, —NO 2 , NH 2 , —PR 2 , —(O)PR 14 R 15 , —PO 3 R 14 R 15 , —OPO 3 R 14 R 15 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, or salt thereof;
wherein R 12 and R 13 are each independently selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
wherein R 14 and R 15 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
and wherein each of said (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, (C 3 -C 6 ) cycloalkyl structure, (C 5 -C 6 ) aryl structure, (C 3 -C 6 ) heteroaryl structure, (C 3 -C 6 ) heterocyclyl structure, (C 3 -C 6 ) heterocycloalkenyl structure, (C 4 -C 6 ) cycloalkenyl structure, heterocyclic ring group, or salt thereof may be independently unsubstituted or substituted with one or more substituents selected from the group consisting of hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, salt thereof, and a combination thereof.
36 . The composition of claim 35 , wherein when R 3 , R 10 , and R 11 are hydrogen, and R 9 is —CH 3 , then R 5 is not —CN.
37 . The composition of claim 35 , wherein the inhibitor is a Nucleoside analog Reverse Transcriptase inhibitor (NRTi).
38 . The composition of claim 35 , wherein the inhibitor is a Nucleoside analog Reverse Transcriptase inhibitor (NRTi) selected from the group consisting of AZT, 3TC, FTC, ABC, ddC, ZDV, TDF, ddI, DFC, DAPD, alovidine, elvucitabine, D4T, RCV, Beta-L-Fd4C, and a combination thereof.
39 . The composition of claim 35 , wherein the inhibitor is a Non-Nucleoside analog Reverse Transcriptase inhibitor (NNRTi).
40 . The composition of claim 35 , wherein the inhibitor is a Non-Nucleoside analog Reverse Transcriptase inhibitor (NNRTi) selected from the group consisting of DLV, EFV, NVP, calanolide A, etravirine, TMC-278, BMS-561390, capravirine, and a combination thereof.
41 . The composition of claim 35 , wherein the inhibitor is a Protease inhibitor (Pi).
42 . The composition of claim 35 , wherein the inhibitor is a Protease inhibitor (Pi) selected from the group consisting of APV, TPV, IDV, SQV, LPV, FPV, RTV, ATZ, —NFV, brecanavir, darunavir, PPL-100, L-756423, RO033-4649, and a combination thereof.
43 . The composition of claim 35 , wherein the inhibitor is a Cell Entry inhibitor (Ci).
44 . The composition of claim 35 , wherein the inhibitor is a Cell Entry inhibitor (Ci) selected from the group consisting of Fuzeon, ENF, aplaviroc, maraviroc, vicriviroc, T-1249, PRO-542, TNX-355, SCH-C, PRO-140, SP-01A, SP-10, TNX-355, and a combination thereof.
45 . The composition of claim 35 , further comprising a pharmaceutically acceptable carrier.
46 . A method for treating a known or suspected malady, in an animal, selected from the group consisting of HIV infection, hepatitis C, hepatitis B, hepatitis delta, influenza, herpes, adenovirus, papillomavirus, parvovirus, measles, bird flu, and a combination thereof, comprising administering, to the animal,
at least one compound having the following formula:
or salt thereof;
wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 1 and R 2 together with the nitrogen to which they are attached form a heterocyclic ring group or salt thereof;
wherein R 3 , R 9 , and R 11 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
wherein R 4 is hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, or salt thereof
wherein R 5 and R 6 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ), perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 5 and R 6 together with the carbons to which they are attached form a (C 5 -C 6 ) aryl structure, a (C 3 -C 6 ) heteroaryl structure, a (C 3 -C 6 ) heterocycloalkenyl structure, a (C 4 -C 6 ) cycloalkenyl structure, or salt thereof;
wherein R 7 and R 8 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —C(NH)NH 2 , —C(NH)NHC(NH)NH 2 , —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
or wherein R 7 and R 8 together with the nitrogen to which they are attached form a heterocyclic ring group or salt thereof;
wherein R 10 is hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 14 , —NR 14 R 15 , —NR 14 COR 15 , —CONR 14 R 15 , —CONR 14 , —COOR 14 , —OCOR 14 , —COR 14 , —SR 14 , —SO 2 R 14 , —SO 3 R 14 , —SO 2 NR 14 , —SOR 14 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 14 R 15 , —PO 3 R 14 R 15 , —OPO 3 R 14 R 15 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, or salt thereof;
wherein R 12 and R 13 are each independently selected from the group consisting of (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
wherein R 14 and R 15 are each independently selected from the group consisting of hydrogen, hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 , —(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, and salt thereof;
and wherein each of said (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, (C 3 -C 6 ) cycloalkyl structure, (C 5 -C 6 ) aryl structure, (C 3 -C 6 ) heteroaryl structure, (C 3 -C 6 ) heterocyclyl structure, (C 3 -C 6 ) heterocycloalkenyl structure, (C 4 -C 6 ) cycloalkenyl structure, heterocyclic ring group, or salt thereof may be independently unsubstituted or substituted with one or more substituents selected from the group consisting of hydroxyl, halo, bromo, chloro, iodo, fluoro, —OR 12 , —NR 12 R 13 , —NR 12 COR 13 , —CONR 12 R 13 , —CONHR 12 , —COOR 12 , —OCOR 12 , —COR 12 , —SR 12 , —SO 2 R 12 , —SO 3 R 12 , —SO 2 NHR 12 , —SOR 12 , —N 3 , —CN, —NC, —SH, —NO 2 , —NH 2 , —PR 2 ,—(O)PR 12 R 13 , —PO 3 R 12 R 13 , —OPO 3 R 12 R 13 , —PO 2 , (C 1 -C 20 ) alkyl, phenyl, (C 3 -C 20 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C 3 -C 25 ) heteroaryl, (C 3 -C 25 ) heterocyclyl, (C 2 -C 20 ) alkenyl, (C 4 -C 20 ) cycloalkenyl, (C 2 -C 20 ) alkynyl, (C 6 -C 20 ) cycloalkynyl, (C 5 -C 25 ) aryl, perhalo (C 1 -C 20 ) alkyl, salt thereof, and a combination thereof.
47 . The method of claim 46 , wherein when R 3 , R 10 , and R 11 are hydrogen, and R 9 is —CH 3 , then R 5 is not —CN.
48 . The method of claim 46 , further comprising administering at least one inhibitor selected from the group consisting of Nucleoside analog Reverse Transcriptase inhibitor (NRTi), —Non-Nucleoside analog Reverse Transcriptase inhibitor (NNRTi), Protease inhibitor (Pi), Cell Entry inhibitor (Ci), and a combination thereof.
49 . The method of claim 46 , wherein the inhibitor is a Nucleoside analog Reverse Transcriptase inhibitor (NRTi) selected from the group consisting of AZT, 3TC, FTC, ABC, ddC, ZDV, TDF, ddI, DFC, DAPD, alovidine, elvucitabine, and a combination thereof.
50 . The method of claim 46 , wherein the inhibitor is a Non-Nucleoside analog Reverse Transcriptase inhibitor (NNRTi).
51 . The method of claim 46 , wherein the inhibitor is a Non-Nucleoside analog Reverse Transcriptase inhibitor (NNRTi) selected from the group consisting of DLV, EFV, NVP, calanolide A, etravirine, TMC-278, BMS-561390, capravirine, and a combination thereof.
52 . The method of claim 46 , wherein the inhibitor is a Protease inhibitor (Pi).
53 . The method of claim 46 , wherein the inhibitor is a Protease inhibitor (Pi) selected from the group consisting of APV, TPV, IDV, SQV, LPV, FPV, RTV, ATZ, NFV, brecanavir, darunavir, and a combination thereof.
54 . The method of claim 46 , wherein the inhibitor is a Cell Entry inhibitor (Ci).
55 . The method of claim 46 , wherein the inhibitor is a Cell Entry inhibitor (Ci) selected from the group consisting of Fuzeon, ENF, aplaviroc, maraviroc, vicriviroc, T-1249, PRO-542, TNX-355, SCH-C, and a combination thereof.
56 . The method of claim 46 , wherein the animal is a human.