Patent ID: 6093738
Filing Date: 2000-07-25
Classification: A61P,C07D

Abstract:
Imidazo[1,2-d]-thiadiazole compounds corresponding to the general formula I: ##STR36## wherein X and Z are independently hydrogen, lower alkyl, halo, nitro, hydroxy, lower alkoxy, a group NR'R"", OC(O)R', OC(O)OR', OC(O)NR'R"", NR'(COR'), NHC(O)NR'R"", or NHC(O)OR', with R' and R"" being independently hydrogen, lower alkyl, aryl, lower arylalkyl or lower alkyl substituted with hydroxy, amino, lower alkylamino, carboxy or lower alkoxycarbonyl, or R' and R"" in NR'R"" when taken together forming a five or six membered heterocyclic ring selected from piperidinyl, pyrrolidinyl, morpholinyl and prolyl, the heterocyclic ring being optionally substituted with lower alkyl, carboxy, amino, phenyl, alkoxycarbonyl or di-lower alkylamino;or X and Z taken together represent a benzene ring fused to the imidazo ring and being optionally substituted with up to four substituents independently selected from hydrogen, lower alkyl, halo, nitro, hydroxy, lower alkoxy, piperazinyl or a group NR'R"", OC(O)R', OC(O)OR', OC(O)NR'R"", NR'(COR'), NHC(O)NR'R"", or NHC(O)OR', with R', R"" being as defined above;and Y is selected from:(1) groups of the formula: ##STR37## in which R.sup.7 represents hydrogen, hydroxy, lower alkyl, lower cycloalkyl, lower alkoxy, lower alkenyl, lower alkynyl, aryl, lower arylalkyl, heterocyclyl, -substituted N-heterocyclyl, heterocyclyloxy, heterocyclyl-lower alkylene, a group NR'R"" where R' and R"" are independently selected from hydrogen, lower alkyl, aryl, lower arylalkyl, and alkylene, and a group ANR'R"", AOR' wherein A is an amino acid residue or a peptide of 2 to 3 amino acid residues and R', R"" have the same definition as above(2) heterocyclyl, lower alkylene-heterocyclyl, lower alkylene-amino-heterocyclyl, amino-lower alkylene-heterocyclyl or amino-heterocyclyl, the heterocyclic ring being attached at any heteroatom or carbon atom which results in the creation of a stable structure, and the heterocyclic ring being optionally substituted with 1-3 substituents selected from lower alkyl; hydroxy; nitro; amino; lower alkylamino; di-lower alkylamino; lower alkoxy; cinnamyl, lower alkyl substituted with 1-3 substituents selected from hydroxy, lower alkylcarbamoyl, phenyl, halophenyl, heterocyclyl, carboxy and lower alkoxycarbonyl; lower acyl; lower alkoxycarbonyl; lower alkyl-sulfonyl; amido; allyl; benzyl; phenyl optionally substituted with amino, halo, hydroxy, lower alkoxy, lower alkyl, lower alkylamino or di-lower alkylamino; heterocyclyl optionally substituted with 1-3 substituents selected from nitro, hydroxy, lower alkoxy, lower alkyl, amino, halo, lower alkylamino, di-lower alkylamino; with the proviso that the heterocyclyl group Y is not 1-imidazolyl or substituted 1-imidazolyl;(3) NR'R"" or --CH.sub.2 --NR'R"" wherein R', R"" have the same definition as above;(4) ANR'R"", AOR' wherein A is an amino acid residue or a peptide of 2 to 3 amino acid residues and R', R"" have the same definition as above(5) lower 2-(alkoxycarbonyl)alkyl(6) halo(7) groups of formula R.sup.8 --CHOH--wherein R.sup.8 is hydrogen, lower alkyl, aryl, lower arylalkyl, lower cycloalkyl, lower alkenyl, lower alkynyl or heterocyclyl, the heterocyclic ring being attached at any heteroatom or carbon atom which results in the creation of a stable structure,(8) groups of formula R.sup.9 --CH.dbd.NOR.sup.10 wherein R.sup.10 is hydrogen, lower alkyl or lower arylalkyl, and R.sup.9 is lower alkyl, aryl, lower arylalkyl, lower cycloalkyl, lower alkenyl, lower alkynyl or heterocyclyl, the heterocyclic ring being attached at any carbon atom which results in the creation of a stable structure;(9) lower alkoxy, lower arylalkoxy, lower cycloalkoxy, lower heterocyclyl alkoxy or heterocyclyloxy;(10) lower alkylsulfonyl, lower alkylsulfinyl, arylsulfonyl, arylsulfinyl, lower alkyl-arylsulfonyl, lower alkyl-aryl sulfinyl, heterocyclyl-sulfonyl, heterocyclyl-sulfinyl; optionally substituted with 1 to 2 substituents selected from lower alkyl, halo, nitro, hydroxy, lower alkoxy, or groups of formula NR'R"", OC(O)R', OC(O)OR', OC(O)NR'R"", NR'(COR'), NHC(O)NR'R"", NHC(O)OR' where R' and R"" have the meanings given above;(11) groups of the formula --C(.dbd.NOH)COOR.sup.11 wherein R.sup.11 is lower alkyl(12) aryl, lower arylalkyl, or lower cycloalkyl, each group being optionally substituted with 1 to 3 substituents selected from lower alkyl, halo, nitro, amino, hydroxy, lower alkoxy, lower alkylamino, lower dialkylamino, NR'R"", OC(O)R', OC(O)OR', OC(O)NR'R"", NR'(COR'), NHC(O)NR'R"", NHC(O)OR', with R' and R"" having the meanings given above;(13) monosubstituted alkyl with substituent selected from halo, nitro, amino, hydroxy, lower alkoxy, lower alkylamino, lower dialkylamino. NR'R"", OC(O)R', OC(O)OR', OC(O)NR'R""NR'(COR'), NHC(O)NR'R"", NHC(O)OR', with R' and R"" being as defined above;(14) disubstituted alkyl with substituents selected from halo, nitro, amino, hydroxy, lower alkoxy, lower alkylamino, lower dialkylamino, NR'R"", OC(O)R', OC(O)OR', OC(O)NR'R"", NR'(COR'), NHC(O)NR'R"", NHC(O)OR', with R' and R"" being as defined above.