Patent NZ-507525-A (NZ)
Title: Polycyclic azaindole compounds
Inventor: GUILLAUMET GERALD
IPC: A61K31/4355
Filed: 2000-10-13
Abstract: Compounds of formula (1) wherein: R1 represents a halogen atom or a group -R, -OR, -S(O)nR, -NRR', -NR-C(=Z)-R', -NR-C(=Z)-OR', -NR-C(=Z)-NR'R", R-N-SO2R', -C(=Z)-NRR', or -SO2NRR'; n is 0, 1 or 2; Z represents a sulphur or oxygen atom; R, R' and R", which may be identical or different, represent a hydrogen atom or an unsubstituted or substituted linear or branched alkyl group, an unsubstituted or substituted linear or branched alkenyl group, an unsubstituted or substituted linear or branched alkynyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted cycloalkyl-alkyl group in which the alkyl moiety is linear or branched, an aryl group, an aryl-alkyl group in which the alkyl moiety is linear or branched, a heteroaryl group or a heteroaryl-alkyl group in which the alkyl moiety is linear or branched, it also being possible for (R and R') and (R' and R") to form together with the nitrogen atom carrying them a morpholinyl, piperidinyl, piperazinyl or pyrrolidinyl group, those groups being unsubstituted or substituted; G1 represents an alkylene chain having from 1 to 4 carbon atoms, optionally substituted by a group R, OR, COR or COOR or G1 represents an alkylene chain having from 1 to 4 carbon atoms in which one of CH2 group can be replaced by a cycloalkylene group; A represents a group -C(=Z)-NRR', -NR-C(=Z)R' OR -NR-C(=Z)NR'R"; B forms with the nitrogen atom and the carbon atom to which it is attached a ring having from 5 to 8 ring members, which may contain one or more unsaturated bonds and may contain, in addition to the nitrogen atom, an additional hetero atom selected from oxygen, sulphur and nitrogen; R2 and R3, which may be identical or different, represent a hydrogen atom or a linear or branched alkyl group, a linear or branched alkoxy group or a hydroxy group, or R 2 and R 3 together form an oxo group; R4 and R5 represent a hydrogen atom or form together with two adjacent atoms of the B ring carrying them a group selected from aryl and heteroaryl; the symbol --- means that the bond may be single or double, with the proviso that the valence of the atoms is respected; it being understood that: the term "substituted" applied to the terms "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "morpholinyl", "piperidinyl", "piperazinyl" and "pyrrolidinyl" means that those groups may be substituted by one or more groups selected from hydroxy, oxo, alkoxy, alkyl, polyhaloalkyl, and halogen atoms; the term "substituted" applied to the term "cycloalkylalkyl" means that the cyclic moiety of the group is substituted by one or more groups selected from hydroxy, oxo, alkoxy, alkyl, polyhaloalkyl, and halogen atoms; the term "aryl" is understood to mean a phenyl, naphthyl or biphenyl group, those groups being unsubstituted or substituted by one or more identical or different groups selected from hydroxy, alkoxy, alkyl, amino, alkylamino, dialkylamino, nitro, cyano, polyhaloalkyl, formyl, carboxy, alkoxycarbonyl, amido, and halogen atoms; the term "heteroaryl" is understood to mean a furyl, pyrrolyl, imidazolyl, pyridyl, thienyl, pyrazinyl, benzothienyl, benzofuranyl, indolyl, benzimidazolyl, quinolyl or quinazolinyl group, those groups being unsubstituted or substituted by one or more identical or different groups selected from hydroxy, alkoxy, alkyl, amino, alkylamino, dialkylamino, nitro, cyano, polyhaloalkyl, formyl, carboxy, amido, and halogen atoms; their enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base. These compounds are useful in the treatment of disorders of the melatoninergic system.