EP2 antagonist compounds
Described herein are compounds of Formula (II): that are EP2 antagonists, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of diseases or conditions associated with EP2 activity.
1 . A compound having the structure of Formula (II):
or a pharmaceutically acceptable salt thereof, wherein:
R 1 and R 2 are each independently hydrogen, deuterium, halogen, or C 1-4 alkyl;
R 3 and R 4 are each independently hydrogen, deuterium, halogen, or C 1-4 alkyl;
R 5 and R 6 are each independently hydrogen, deuterium, halogen, or C 1-4 alkyl; or R 5 and R 6 are taken together with the carbon atom to which they are attached to form an oxetane;
R 7 and R 8 are each independently hydrogen, deuterium, halogen, —CN, —C 1-4 alkyl, —C 1-4 haloalkyl, —OH, —O(C 1-4 alkyl), —O(C 1-4 haloalkyl), —NH 2 , —NH(C 1-4 alkyl), —N(C 1-4 alkyl) 2 , —(C 1-4 alkyl)O(C 1-4 alkyl), —C(O)OH, —C(O)O(C 1-4 alkyl), —C(O)NH 2 , —C(O)NH(C 1-4 alkyl), —C(O)N(C 1-4 alkyl) 2 , substituted or unsubstituted C 3-6 cycloalkyl, or substituted or unsubstituted 3- to 6-membered heterocycloalkyl; or R 7 and R 8 are taken together with the carbon atom to which they are attached to form a cyclopropane or an oxetane;
R 9 and R 10 are each independently hydrogen, deuterium, halogen, or C 1-4 alkyl; or R 9 and R 10 are taken together with the carbon atom to which they are attached to form an oxetane;
R A1 is halogen, C 1-4 alkyl, or cyclopropyl; and
R A2 is hydrogen, deuterium, halogen, or optionally deuterated or halogenated methyl;
each R B is independently selected from the group consisting of halogen, —CN, —C 1-4 alkyl, —C 1-4 haloalkyl, —C 1-4 aminoalkyl, —C 1-4 hydroxyalkyl, —C 1-4 methoxyalkyl, —(C 1-4 alkyl)O(C 1-4 alkyl), —C(O)(C 1-4 alkyl), —C(O)OH, —C(O)O(C 1-4 alkyl), —C(O)NH 2 , —C(O)NH(C 1-4 alkyl), —C(O)N(C 1-4 alkyl) 2 , —NH 2 , —NH(C 1-4 alkyl), —NH(C 3-6 cycloalkyl), —NH(C 3-6 heterocycloalkyl), —N(C 1-4 alkyl) 2 , —NHC(O)C 1-4 alkyl, —NHC(O)O(C 1-4 alkyl), —NHS(O) 2 C 1-4 alkyl, —OH, —O(C 1-4 alkyl), —O(C 1-4 haloalkyl), —SH, —S(C 1-4 alkyl), —S(O)(C 1-4 alkyl), —S(O)(NH)(C 1-4 alkyl), —S(O) 2 (C 1-4 alkyl), —S(O) 2 NH 2 , —S(O 2 )NHCH 3 , substituted or unsubstituted C 3-6 cycloalkyl, or substituted or unsubstituted 3- to 6-membered heterocyclyl;
Ring C is bicyclic heterocycle having one or more nitrogen atoms; or Ring C is Ring C′;
each R C is independently selected from the group consisting of halogen, —CN, —C 1-4 alkyl, —C 1-4 haloalkyl, —(C 1-4 alkyl)O(C 1-4 alkyl), —C(O)OH, —C(O)O(C 1-4 alkyl), —C(O)NH 2 , —C(O)NH(C 1-4 alkyl), —C(O)N(C 1-4 alkyl) 2 , —NH 2 , —NH(C 1-4 alkyl), —N(C 1-4 alkyl) 2 , —OH, —O(C 1-4 alkyl), —O(C 1-4 haloalkyl), —S(C 1-4 alkyl), —SO 2 C 1-4 alkyl, —SO 2 NHC 1-4 alkyl, substituted or unsubstituted C 3-6 cycloalkyl, or substituted or unsubstituted 3- to 6-membered heterocyclyl; or two R C taken together form a carbonyl;
m is 0 to 3;
n is 1, 2 or 3; and
Ring C′ is selected from the group consisting of:
2 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R A1 is halogen.
3 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R A1 is —Cl.
4 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein
is selected from the group consisting of:
5 . The compound of claim 1 , having the structure:
or a pharmaceutically acceptable salt thereof.
6 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, having the structure:
or a pharmaceutically acceptable salt thereof, wherein:
Ring C is bicyclic heterocycle having one or more nitrogen atoms; or Ring C is Ring C′;
each R C is independently selected from the group consisting of halogen, —CN, —C 1-4 alkyl, —C 1-4 haloalkyl, —(C 1-4 alkyl)O(C 1-4 alkyl), —C(O)OH, —C(O)O(C 1-4 alkyl), —C(O)NH 2 , —C(O)NH(C 1-4 alkyl), —C(O)N(C 1-4 alkyl) 2 , —NH 2 , —NH(C 1-4 alkyl), —N(C 1-4 alkyl) 2 , —OH, —O(C 1-4 alkyl), —O(C 1-4 haloalkyl), —S(C 1-4 alkyl), —SO 2 C 1-4 alkyl, —SO 2 NHC 1-4 alkyl, substituted or unsubstituted C 3-6 cycloalkyl, or substituted or unsubstituted 3- to 6-membered heterocyclyl; or two R C taken together form a carbonyl;
m is 0 to 3;
n is 1, 2 or 3; and
Ring C′ is selected from the group consisting of:
7 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring C is bicyclic heteroaryl having one, two or three nitrogen atoms.
8 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring C is bicyclic heteroaryl consisting of a pyrrole ring or pyrazole ring fused to a phenyl ring, a pyridine ring, or a pyrimidine ring.
9 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring C is a substituted or unsubstituted indole, or a substituted or unsubstituted azaindole.
10 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring C is a substituted or unsubstituted indole.
11 . The compound of claim 1 , wherein Ring C is a bicyclic heterocycle having one or more nitrogens, selected from the group consisting of:
12 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R C is halogen, and m is 0, 1, or 2.
13 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ring C is indole; Re is halogen, and m is 1.
14 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R B is independently halogen, C 1-4 alkyl, C 1-4 haloalkyl, —C(O)OH, —C(O)O(C 1-4 alkyl), —C(O)NH 2 , —C(O)NH(C 1-4 alkyl), or —C(O)N(C 1-4 alkyl) 2 .
15 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R B is independently selected from the group consisting of —F, —Cl, —CN, —CH 3 , —CH 2 F, —CHF 2 , —CF 3 , —OH, and —OCH 3 .
16 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein
each R B is independently selected from the group consisting of —F, —Cl, —CN, —CH 3 , —CH 2 F, —CHF 2 , —CF 3 , CH 2 NH 2 , —CH 2 NHBoc, —CH 2 OH, —CH 2 OCH 3 , —C(O)NH 2 , —C(O)NHCH 3 , —C(O)N(CH 3 ) 2 , —C(O)OH, —C(O)OCH 3 , —NH 2 , —NHCH 3 , —N(CH 3 ) 2 , —NH(oxetanyl), —NHC(O)CH 3 , —NHS(O) 2 CH 3 , —OH, —OCH 3 , —OCH 2 CF 3 , —S(O)(NH)CH 3 , methylpyrazolyl, and pyrazolyl.
17 . The compound of claim 1 , having the structure:
or a pharmaceutically acceptable salt thereof.
18 . The compound of claim 1 , having the structure:
or a pharmaceutically acceptable salt thereof, or a tautomer thereof, wherein:
each R B is independently selected from the group consisting of halogen, —CN, —C 1-4 alkyl, —C 1-4 haloalkyl, —C 1-4 aminoalkyl, —C 1-4 hydroxyalkyl, —C 1-4 methoxyalkyl, —(C 1-4 alkyl)((C 1-4 alkyl), —C(O)(C 1-4 alkyl), —C(O)OH, —C(O)O(C 1-4 alkyl), —C(O)NH 2 , —C(O)NH(C 1-4 alkyl), —C(O)N(C 1-4 alkyl) 2 , —NH 2 , —NH(C 1-4 alkyl), —NH(C 3-6 cycloalkyl), —NH(C 3-6 heterocycloalkyl), —N(C 1-4 alkyl) 2 , —NHC(O)C 1-4 alkyl, —NHC(O)O(C 1-4 alkyl), —NHS(O) 2 C 1-4 alkyl, —OH, —O(C 1-4 alkyl), —O(C 1-4 haloalkyl), —SH, —S(C 1-4 alkyl), —SO(C 1-4 alkyl), —S(O) 2 (C 1-4 alkyl), —S(O) 2 NH 2 , —S(O 2 )NHCH 3 , substituted or unsubstituted C 3-6 cycloalkyl, or substituted or unsubstituted 3- to 6-membered heterocyclyl; and
each R C is independently selected from the group consisting of halogen, —CN, —C 1-4 alkyl, —C 1-4 haloalkyl, —(C 1-4 alkyl)O(C 1-4 alkyl), —C(O)OH, —C(O)O(C 1-4 alkyl), —C(O)NH 2 , —C(O)NH(C 1-4 alkyl), —C(O)N(C 1-4 alkyl) 2 , —NH 2 , —NH(C 1-4 alkyl), —N(C 1-4 alkyl) 2 , —OH, —O(C 1-4 alkyl), —O(C 1-4 haloalkyl), —S(C 1-4 alkyl), —SO 2 C 1-4 alkyl, —SO 2 NHC 1-4 alkyl, substituted or unsubstituted C 3-6 cycloalkyl, or substituted or unsubstituted 3- to 6-membered heterocyclyl; or two R C taken together form a carbonyl.
19 . The compound of claim 1 , wherein n is 1.
20 . The compound of claim 1 , wherein n is 2.
21 . The compound of claim 1 , wherein n is 3.
22 . A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt, or solvate thereof, and at least one pharmaceutically acceptable excipient.
23 . A method of modulating the activity of the prostaglandin E2 receptor 2 (EP2) in a mammal comprising administering to the mammal a compound of claim 1 , or a pharmaceutically acceptable salt, or solvate thereof.
24 . A method of treating a disease or condition that would benefit from the modulation of prostaglandin E2 receptor 2 (EP2) activity comprising administering to the mammal a compound of claim 1 , or a pharmaceutically acceptable salt, or solvate thereof.