Bicyclic heteroaromatic compounds
View Patent ↗A bicyclic heteroaromatic compound according to general formula I, or a pharmaceutically acceptable salt thereof, wherein R1 is (3-8C)cycloalkyl, (2-7C)heterocycloalkyl, (6-14C)aryl or (4-13C)heteroaryl; all optionally substituted with one or more substituents; R2 is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (6-14C)aryl or (4-13C)heteroaryl; R3 is (1-8C)alkyl, (3-8C)cycloalkyl, (2-7C)heterocycloalkyl, (6-14C)aryl or (4-13C)heteroaryl; Y is CH or N; Z is NH2 or OH; A is S, N(H), N(R), O or a bond and B is N(H), O or a bond; X1-X2 is C═C, C(O)—NH, NH—C(O), C(O)—O, O—C(O), C═N, N═C or S or O. The compounds of the invention can be used in fertility regulation therapies.
1. A bicyclic heteroaromatic compound according to general formula I, or a pharmaceutically acceptable salt thereof,
wherein
R 1 is (3-8C)cycloalkyl, (2-7C)heterocycloalkyl, (6-14C)aryl or (4-13C)heteroaryl; all optionally substituted with one or more substituents selected from N(R 4 )R 5 , NHR 5 , R 5 , OR 5 and/or SR 5 ;
R 2 is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (6-14C)aryl or (4-13C)heteroaryl;
R 3 is (1-8C)alkyl, (3-8C)cycloalkyl, (2-7C)heterocycloalkyl, (6-14C)aryl or (4-13C)heteroaryl;
R 4 can be selected from the same groups as described for R 2 ,
R 5 is (2-7C)heterocycloalkylcarbonyl, (2-8C)alkenylsulfonyl, (2-8C)alkenoxycarbonyl, (6-14C)arylsulfonyl, (6-14C)arylaminocarbonyl, (6-14C)aryloxycarbonyl, (6-14C)arylaminosulfonyl, (6-14C)aryloxysulfonyl, or
(1-8C)alkylsulfonyl, (1-8C)(di)alkylaminocarbonyl, (1-8C)alkoxycarbonyl, (1-8C)(di)alkylaminosulfonyl, or (1-8C)alkoxysulfonyl,
the alkyl group of which may be optionally substituted with one or more substituents selected from hydroxyl, (1-8C)alkoxy, (2-7C)heterocycloalkyl(1-8C)alkoxy, (3-8C)cycloalkyl(1-8C)alkoxy, (6-14C)aryl(1-8C)alkoxy, (4-13C)heteroaryl(1-8C)alkoxy, (2-7C)heterocycloalkyl, (3-8C)cycloalkyl, (6-14C)aryl, (4-13C)heteroaryl, (1-8C)alkoxycarbonyl, (6-14C)aryloxycarbonyl, (1-8C)alkylcarbonyloxy, (6-14C)arylcarbonyloxy, (1-8C)alkylcarbonyl, (6-14C)arylcarbonyl, amine, (1-8C)alkylaminocarbonyl, (6-14C)arylaminocarbonyl, (1-8C)alkylcarbonylamino, (6-14C)arylcarbonylamino, (6-14C)(di)arylamino, (di)[(1-3C)alkoxy(1-3C)alkyl]amino and/or (1-8C)(di)alkylamino;
Y is N;
Z is NH 2 or OH;
A is S, N(H), N(R 4 ), O or a bond;
B is N(H) or a bond; and
X1-X2 is S or O.
2. The compound according to claim 1 , wherein Z is NH 2 .
3. The compound according to claim 1 , wherein R 1 is (6-14C)aryl or (4-13C)heteroaryl, optionally substituted with one or more substituents selected from N(R 4 )R 5 , NHR 5 , R 5 , OR 5 or SR 5 .
4. The compound according to claim 3 , wherein R 5 is (2-7C)heterocycloalkylcarbonyl, or (1-8C)(di)alkylaminocarbonyl, the alkyl group of which may be optionally substituted with (2-7C)heterocycloalkyl, (4-13C)heteroaryl, (1-8C)alkoxycarbonyl, (1-8C)alkylaminocarbonyl, (1-8C)alkylcarbonylamino, (6-14C)arylcarbonylamino, amine and/or (1-8C)(di)alkylamino.
5. The compound according to claim 3 , wherein R 1 is phenyl, optionally substituted with one or more substituents.
6. The compound according to claim 5 , wherein R 1 is substituted at the meta position.
7. The compound according to claim 1 , wherein B is N(H), or B is a bond and R 3 is (2-7C)heterocycloalkyl.
8. The compound according to claim 1 , wherein X1-X2 is S.
9. A pharmaceutical composition comprising a bicyclic heteroaromatic compound according to claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable auxiliary.
10. A method of treating infertility in a patient in need thereof comprising:
administering to the patient an effective amount of the compound according to claim 1 or a pharmaceutically acceptable salt thereof.