Imidazopyridine derivatives and their use

Claim 2

A compound of the formula (I'"): ##STR68## wherein X is S, S(O) S(O) 2 , O or NR 3 (wherein R 3 is a hydrogen or an optionally substituted hydrocarbon group); A is a hydrocarbon group selected from the group consisting of (1) a group represented by the formula ##STR69## wherein l, m and n are integers of 0 to 5; R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are hydrogen, an optionally substituted lower alkyl, aralkyl or aryl group; and wherein R 4 and R 5 , R 6 and R 7 or R 8 and R 9 may bind together to form a ring, or R 4 or R 6 may bind together with R 8 or R 9 to form a ring; (2) a group represented by the formula --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; and (3) a group represented by the formula ##STR70## wherein o and p are integers of 0 to 5; R 1 and R 2 are the same or different and are a hydrogen, an optionally substituted hydrocarbon group, a halogen, a nitro group, a nitroso group, an optionally protected amino group, a lower alkoxycarbonyl group or a lower alkyl carbamoyl group; and B 3 is a hydroxyl group acylated by an acyl group derived from a carboxylic acid or a N-hydrocarbon substituted carbamic acid, or its salt or solvate.

Claim 3

A compound according to claim 1, wherein each optionally substituted hydrocarbon group of R 1 and R 2 is independently C 1-6 alkyl, phenyl-C 1-6 alkyl, naphthyl-C 1-6 alkyl or C 4-24 aryl, which may have 1 to 4 substituents; the optionally substituted hydrocarbon group of R 3 is C 1-6 alkyl, phenyl-C 1-6 alkyl or naphthyl-C 1-6 alkyl, which may have 1 to 4 substituents; B 3 is --O--CO--NR 15 R 16 or --O--CO--R 19 , wherein R 15 is (1) a hydrogen, or (2) a C 1-30 straight or branched alkyl, a C 3-8 cycloalkyl, a saturated bi- or tricyclic hydrocarbon group formed by fusing 5 to 8 membered rings, a C 2-30 alkenyl, a phenyl-C 1-6 alkyl, a naphthyl-C 1-6 alkyl or a C 4-24 aryl, which may have 1 to 4 substituents; R 16 and R 19 are independently a C 1-30 straight or a branched alkyl, a C 3-8 cycloalkyl, a saturated bi- or tricyclic hydrocarbon group formed by fusing 5 to 8 membered rings, a C 2-30 alkenyl, a phenyl-C 1-6 alkyl, a naphthyl-C 1-6 alkyl or a C 4-24 aryl; said substituent of C 1-6 alkyl is halogen, nitro, amino, N-mono C 1-6 alkylamino, N,N-di C 1-6 alkylamino, 4 to 7 membered cyclic amino, C 1-6 alkoxy, C 6-10 aryloxy, carbamoyl, cyano, hydroxy, carboxy, C 1-6 alkoxycarbonyl or C 1-6 alkylcarbonyl; said substituent of phenyl-C 1-6 alkyl or naphthyl-C 1-6 alkyl is halogen, C 1-6 alkyl, C 1-6 alkoxy, nitro, cyano, hydroxy, C 1-6 alkoxycarbonyl, carbamoyl or C 1-6 alkylcarbamoyl; said substituent of C 4-24 aryl is halogen, C 1-6 alkyl, C 1-6 alkoxy, nitro, cyano, oxo, hydroxy, amino, C 1-6 alkoxycarbonyl, carbamoyl or C 1-6 alkylcarbamoyl; the optionally protected amino group of R 1 and R 2 is amino, acylamino or tritylamino, and wherein the acyl group is --CO--R 16 , --CO--OR 16 , --SO 2 R 17 , --CO--NR 14 R 15 or --CS--NR 14 R 15 , R 15 and R 16 are as defined above, R 14 is the same as that of R 15 , and R 17 is the same as that of R 16 ; and the lower alkoxycarbonyl and lower alkylcarbamoyl of R 1 and R 2 are C 1-6 alkoxycarbonyl and C 1-6 alkylcarbamoyl respectively.

Claim 4

A compound according to claim 1, wherein X is S or O and B 3 is --O--CONHR 16 (wherein R 16 is a C 1-30 straight or a branched alkyl, a C 3-8 cycloalkyl, a saturated bi- or tricyclic hydrocarbon group formed by fusing 5 to 8 membered rings, a C 2-30 alkenyl, a phenyl-C 1-6 alkyl, a naphthyl-C 1-6 alkyl or a C 4-24 aryl).

Claim 5

A compound according to claim 1 which is 5-[2-(methylcarbamoyloxy)ethylthio]imidazo[1,2-a]pyridine, or 5-[2-[3-(hydroxy)propylcarbamoyloxy]ethylthio]imidazo[1,2-a]pyridine.

Claim 6

A calmodulin inhibitory composition comprising a compound of the formula (I'") as defined in claim 1, or a pharmaceutically acceptable salt or solvate thereof, and a pharmaceutically acceptable carrier, diluent or excipient.

Claim 7

A method for inhibiting calmodulin comprising administering an effective amount of a compound of the formula (I'") as defined in claim 1, or a pharmaceutically acceptable salt or solvate thereof optionally together with a pharmaceutically acceptable carrier, diluent or excipient to a patient requiring such inhibition.