Poly-4-aminopyrrole-2-carboxamido derivatives and their use as antiuiral or antitumor agents

Claim 2

A compound of formula (I) ##STR46## wherein n is zero or an integer of 1 to 3; R is (a) --NHR 3 , wherein R 3 is (a') --CON(NO)R 4 , in which R 4 is C 1 -C 4 alkyl either unsubstituted or substituted by halogen; or (b') --CO(CH 2 ) m --R 5 , in which R 5 is halogen, oxiranyl, methyloxiranyl, aziridinyl, a group ##STR47## or a group ##STR48## and m is zero or an integer of 1 to 4; or (b) ##STR49## wherein either R 6 and R 7 are the same and are each oxiranemethyl, aziridinemethyl, or C 2 -C 4 alkyl 2-substituted by halogen or by a group --OSO 2 R 8 wherein R 8 is C 1-C 4 alkyl or phenyl, or one of R 6 and R 7 is hydrogen and the other is as defined above; each group R 1 is, independently, hydrogen or C 1 -C 4 alkyl; R 2 is a C 1 -C 6 alkyl group terminating with (i) a basic moiety chosen from an amino group, a mono- or di-C 1 -C 6 alkylamino group, an amidino group, a group ##STR50## imidazolyl, imidazolinyl, tetrahydropyrimidinyl and oxazolidinyl; or (ii) a carboxy group; or (iii) a free hydroxy group --OH or a glycosilated hydroxy group --OD wherein D is a glucose, mannose or ribose sugar moiety or the daunosamine aminosugar moiety with the proviso that n is different from one when R 2 is ##STR51## and the pharmaceutically acceptable salts thereof.

Claim 3

A compound of formula (I), according to claim 1 wherein, subject to the proviso of claim 1, n is zero, 1 or 2; R is --NHR 3 wherein R 3 is (a') --CON(NO)R 4 wherein R 4 is C 1 -C 4 alkyl substituted by halogen or (b') --CO(CH 2 ) m --R 5 wherein R 5 is halogen, oxyranyl, 1-aziridinyl, a group ##STR52## or a group ##STR53## and m is zero, 1 or 2; each group R 1 is, independently, C 1 -C 4 alkyl; R 2 is a C 1 -C 6 alkyl group terminating with a basic moiety chosen from an amino group, a mono- or di-C 1 -C 6 alkyl-amino group; an amidino group, a group ##STR54## or a nitrogen containing heteromonocyclic ring selected from the group consisting of imidazolyl, imidazolinyl, tetrahydropyrimidinyl and oxazolidinyl, and the salts thereof with pharmaceutically acceptable acids.

Claim 4

A compound of formula (I), according to claim 1 wherein, subject to the proviso of claim 1, n is zero, 1 or 2; R is ##STR55## wherein R 6 and R 7 are the same and are each oxiranemethyl, 1-aziridinemethyl, or a C 2 -C 4 alkyl group 2-substituted by halogen or by a group --OSO 2 R 8 wherein R 8 is C 1 -C 4 alkyl; each group R 1 is, independently, C 1 -C 4 alkyl; R 2 is a C 1 -C 6 alkyl group terminating with a basic moiety chosen from an amino group, a mono- or a di-C 1 -C 6 alkylamino group, an amidino group, a group ##STR56## or a nitrogen containing heteromonocyclic ring selected from the group consisting of imidazolyl, imidazolinyl, tetrahydropyrimidinyl and oxazolidinyl, and the salts thereof with pharmaceutically acceptable acids.

Claim 5

A compound of formula (I) as defined in claim 1 selected from the group consisting of: β-[N-methyl-4-[N-methyl-4-(3-methyl-3-nitrosoureido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine; β-[N-methyl-4-[N-methyl-4-[3-(2-chloroethyl)-3-nitrosoureido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine; 3-[N-methyl-4-[N-methyl-4-[3-methyl-3-nitrosoureido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; 3-[N-methyl-4-[N-methyl-3-[3-(2-chloroethyl)-3-nitrosoureido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-(3-methyl-3-nitrosoureido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-[3-(2-chloroethyl)-3-nitrosoureido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; N-deformyl-N-[N-methyl-4-(3-methyl-3-nitrosoureido)pyrrole-2-carboxamido]Distamycin A; N-deformyl-N-[N-methyl-4-[3-(2-chloroethyl)-3-nitrosoureido]pyrrole-2-carboxamido]Distamycin A; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-[N-methyl-4(3-methyl-3-nitrosoureido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-[N-methyl-4[3-(2-chloroethyl)-3-nitrosoureido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; β-[N-methyl-4-[N-methyl-4-(oxiranecarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine; 3-[N-methyl-4-[N-methyl-4-(oxiranecarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-(oxiranecarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; N-deformyl-N-[N-methyl-4-(oxiranecarboxamido)pyrrole-2-carboxamido]Distamycin A; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-[N-methyl-4-(oxiranecarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; β-[N-methyl-4-[N-methyl-4-(3-methyloxiranecarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine; 3-[N-methyl-4-[N-methyl-4-(3-methyloxiranecarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-(3-methyloxiranecarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; N-deformyl-N-[N-methyl-4-(3-methyloxiranecarboxamido)pyrrole-2-carboxamido]Distamycin A; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-[N-methyl-4-(3-methyloxiranecarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; β-[N-methyl-4-[N-methyl-4-(2-chloroethylcarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine; 3-[N-methyl-4-[N-methyl-4-(2-chloroethylcarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-(2-chloroethylcarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; N-deformyl-N-[N-methyl-4-(2-chloroethylcarboxamido)pyrrole-2-carboxamido]Distamycin A; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-[N-methyl-4-(2-chloroethylcarboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; β-[N-methyl-4-[N-methyl-4-[1-(aziridine)carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine; 3-[N-methyl-4-[N-methyl-4-[1-(aziridine)carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-[1-(aziridine)carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; N-deformyl-N-[N-methyl-4-[1-(aziridine)carboxamido]pyrrole-2-carboxamido]Distamycin A; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-[N-methyl-4-[1-(aziridine)carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; β-[N-methyl-4-[N-methyl-4-[N,N-bis(2-chloroethylamino)]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine; 3-[N-methyl-4-[N-methyl-4-[N,N-bis(2-chloroethylamino)]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-[N,N-bis(chloroethylamino)]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine; N-deformyl-N-[N-methyl-4-[N,N-bis(2-chloroethylamino)]pyrrole-2-carboxamido]Distamycin A; 3-[N-methyl-4-[N-methyl-4-[N-methyl-4-[N-methyl-4-[N,N-bis(2-chloroethylamino)]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propyl-dimethylamine.

Claim 6

A hydrochloric acid salt of a compound of formula (I) as claimed in claim 4.

Claim 7

An antiviral or antitumor pharmaceutical composition containing a suitable carrier and/or diluent and, as an active principle an effective amount of a compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof.