Patent ID: 6169107
Filing Date: 2001-01-02
Classification: C07D

Abstract:
An indoloylguanidine derivative represented by formula (1): ##STR22## wherein: the guanidinocarbonyl group may be located at any open position on either the 5-membered or 6-membered rings comprising the indole nucleus, x=5 so that R.sub.1 is located at each position on the indole nucleus not occupied by the guanidinocarbonyl group, and each R.sub.1 independently represents a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group, a substituted C.sub.1 -C.sub.8 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a halogen atom, nitro, a C.sub.2 -C.sub.8 alkanoyl group, an arylalkanoyl group having carbon atoms up to 10, an aroyl group having carbon atoms up to 11, carboxyl, a C.sub.2 -C.sub.6 alkoxycarbonyl group, an aromatic group, a group shown by formula: --OR.sub.3, --NR.sub.6 R.sub.7, --SO.sub.2 NR.sub.6 R.sub.7 or --S(O).sub.n R.sub.40, and a group shown by formula: ##STR23## wherein A represents an oxygen atom or a group shown by formula: --S(O).sub.n -- or --N (R.sub.50)-- (in which R.sub.50 is a hydrogen atom or a C.sub.1 -C.sub.8 alkyl group; R' represents a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group or a substituted C.sub.1 -C.sub.8 alkyl group); and ##STR24## represents a saturated 3 to 8-membered hetero ring containing one nitrogen atom; R.sub.2 represents a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group, a substituted C.sub.1 -C.sub.8 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, hydroxy, a C.sub.1 -C.sub.6 alkoxy group, an aromatic group or a group shown by formula: --CH.sub.2 R.sub.20 ; R.sub.3 represents a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group, a substituted C.sub.1 -C.sub.8 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, an aromatic group or a group shown by formula: --CH.sub.2 R.sub.30, in which R.sub.30 represents an C.sub.2 -C.sub.8 alkenyl group or an C.sub.2 -C.sub.6 alkynyl group; each of R.sub.6 and R.sub.7 independently represents a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a substituted C.sub.1 -C.sub.8 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a C.sub.2 -C.sub.8 alkanoyl group, an arylalkanoyl group having carbon atoms up to 10, an aroyl group having carbon atoms up to 11, an aromatic group or a group shown by formula: --CH.sub.2 R.sub.60 (in which R.sub.60 represents a C.sub.2 -C.sub.6 alkenyl group or a C.sub.2 -C.sub.6 alkynyl group); or R.sub.6 and R.sub.7 are combined together to form a saturated 5- to 7-membered cyclic amino group which may contain other hetero atom(s) in the ring thereof; R.sub.40 represents a C.sub.1 -C.sub.8 alkyl group, a substituted C.sub.1 -C.sub.8 alkyl group or an aromatic group; n represents 0, 1 or 2; and, R.sub.20 represents a C.sub.2 -C.sub.6 alkenyl group or a C.sub.2 -C.sub.6 alkynyl group; in which: the substituent(s) of said substituted C.sub.1 -C.sub.8 alkyl group means a halogen atom, hydroxy, a C.sub.1 -C.sub.6 alkoxy group, cyano, a C.sub.2 -C.sub.8 alkanoyl group, an arylalkanoyl group having carbon atoms up to 10, an aroyl group having carbon atoms up to 11, an aromatic group, and --CONR.sub.4 R.sub.5 in which each of R.sub.4 and R.sub.5 independently represents a hydrogen atom or a C.sub.1 -C.sub.8 alkyl group or R.sub.4 and R.sub.5 are combined together to form a saturated 5- to 7-membered cyclic amino group which may contain other hetero atom(s) in the ring; --NR.sub.6 R.sub.7 ; or a group shown by: ##STR25## in which: E represents a nitrogen atom or a CH group and R"" represents a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group or a substituted C.sub.1 -C.sub.8 alkyl group substituted with hydroxy, a C.sub.1 -C.sub.8 alkoxy group, cyano, carboxyl, a C.sub.2 -C.sub.6 alkoxycarbonyl group, a C.sub.2 -C.sub.8 alkanoyl group, an arylalkanoyl group having carbon atoms up to 10, an aroyl group having carbon atoms up to 11, an aromatic group, a group shown by --NR.sub.6 R.sub.7, or a group shown by --CONR.sub.4 R.sub.5, in which each of R.sub.4 and R.sub.5 independently represents a hydrogen atom or a C.sub.1 -C.sub.8 alkyl group or R.sub.4 and R.sub.5 are combined together to form a saturated 5- to 7-membered cyclic amino group which may contain other hetero atom(s) therein; and the ring of ##STR26## is a 3- to 8-membered saturated aliphatic ring or saturated hetero ring containing one nitrogen atom; each of the aromatic groups being selected from the group consisting of (a) an aryl group having carbon atoms up to 10, (b) a 5- or 6-membered hetero-aryl group containing 1 to 4 nitrogen atom(s), (c) a 5- or 6-membered hetero-aryl group containing 1 to 2 nitrogen atom(s) and one oxygen atom or one sulfur atom, and (d) a furyl group; and, each of the aromatic groups may be substituted with a substituent selected from the group consisting of a C.sub.1 -C.sub.8 alkyl group, a substituted C.sub.1 -C.sub.8 alkyl group, a halogen atom, nitro, a C.sub.2 -C.sub.6 alkoxy-carbonyl group, carboxyl and a group selected from thas group shown by formulae: --OR.sub.3, --NR.sub.6 R.sub.7, --CONR.sub.6 R.sub.7, --SO.sub.2 NR.sub.6 R.sub.7 and --S(O).sub.n R.sub.40 ; provided that said indoloylguanidine derivative does not include 1-methyl-2-indoloylguanidine; or, a pharmaceutically acceptable acid addition salt thereof.