Use of thiophene compounds for the manufacture of a medicament against tumours

Claim 2

A pharmaceutical composition containing an effective amount of a compound of formula wherein R 1 is hydrogen, p-nitrophenoxy, halogen, carboxy, CON(R 5 ,R 6 ), CONH(CHR 9 ) n -COOH, CH 2 NHR 8 , NH(CHR 9 ) n AR 10 , CH=NOH, NO 2 , CHO, OR 7 , where in turn R 5 and R 6 , the same or different, are hydrogen, a straight or branched alkyl having 1-8C atoms, a heterocyclic ring selected from the group comprising thiophene and imidazole, ascorbyl, peptidyl having up to 5 amino acids or a sugar radical; or R 5 and R 6 , together with the nitrogen atom to which they are linked, are the groups necessary for forming a 5-membered heterocyclic ring which may contain other heteroatoms selected from the group consisting of 0 and N; R 7 has the meanings indicated above for R 5 and R 6 ; R 8 is an acyl of an aliphatic carboxylic acid having 1-4C atoms; R 9 is hydrogen or methyl; R 10 is methyl or phenyl; n is 1,2,3 or 4; and A is CO or SO 2 ; R 2 is hydrogen, N0 2 , halogen, CH(COOH) 2 , OH, (CH 2 ) n COOH where in turn n is 0,1,2,3 or 4; R 3 is hydrogen, NO 2 , OH; R 4 is hydrogen, N0 2 , halogen, SO 2 CH 3 , OH, N(R 5 ,R 6 ) where in turn R 5 and R 6 have the meanings indicated above, provided however that at least two of the substituents R 1 , R 2 , R 3 and R 4 are not hydrogen or an addition salt thereof with pharmaceutically acceptable acids or bases, together with a pharmaceutically acceptable diluent.

Claim 3

A pharmaceutical composition according to claim 1, containing a compound of formula I wherein R is H, bromine, iodine, carboxy, p-nitrophenoxy, CON(R 5 ,R 6 ), CONH(CHR 9 ) n -COOH, NH(CHR 9 ) n AR 10 , CH=NOH where in turn R 5 and R 6 , the same or different, are hydrogen, a straight or branched alkyl having 1-3C atoms, or together with the nitrogen atom to which they are linked, are the groups necessary to complete a morpholine or a piperazine ring; R 9 is hydrogen or methyl; R 10 is methyl or phenyl; n is 1,2 or 3; and A is CO or S0 2 ; R is hydrogen, nitro, carboxy or CH(COOH) 2 ; R 3 is hydrogen or nitro; and R 4 is hydrogen, bromine, iodine, nitro or SO 2 CH 3 .

Claim 4

A compound of formula: wherein R 1 is hydrogen, p-nitrophenoxy, halogen, carboxy, CON(R 5 , R 6 ), CONH(CHR 9 ) n -COOH, CH 2 NHR 8 , NH(CHR 9 ) n AR 10 , CH=NOH, NO 2 , CHO, OR 7 where in turn R 5 and R 6 , the same or different, are hydrogen, straight or branched alkyl having 1-8 C atoms, a heterocyclic ring selected from the group comprising thiophene and imidazole, ascorbyl, peptidyl having up to 5 amino acids or a sugar radical, or R 5 and R 6 , together with the atom of nitrogen to which they are linked, form the groups necessary for completing a 5-membered heterocyclic nucleus which may contain other heteroatoms selected from the group consisting of 0 or N; R 7 has the meanings indicated above for R 5 and R 6 ; R 8 is an acyl of an aliphatic carboxylic acid with 1-4 C atoms; R 9 is hydrogen or methyl; R 10 is methyl or phenyl; n is 1,2,3 or 4; and A is CO or SO 2 ; R 2 is hydrogen, NO 2 , halogen, CH(COOH) 2 , OH, (CH 2 ) n COOH where in turn n is 0,1,2 3 or 4; R 3 is hydrogen, NO 2 , OH; R 4 is hydrogen, NO 2 , halogen, SO 2 CH 3 , OH, N(R 5 ,R 6 ) where in turn R 5 and R 6 have the meanings indicated above, provided however that at least two of the substituents R 1 , R 2 , R 3 and R 4 are not hydrogen and R is not H when R 2 and R 4 are NO and R 3 is H; is not I when R is NO 2 , R 3 is H, and R 4 is NO or CH 3 SO 2 ; is not p-nitrophenoxy when R is NO 2 , R 3 and R 4 are H; and is not CONH 2 or COOH when R 4 is NO 2 , R 2 and R 3 are H; and addition salts thereof with pharmaceutically acceptable acids or bases.

Claim 5

A compound of formula: wherein R 1 is hydrogen, p-nitrophenoxy, halogen, carboxy, CON(R 5 , R 6 ), CONH(CHR 9 ) n -COOH, CH 2 NHR 8 , NH(CHR 9 ) n AR 10 , CH=NOH, NO 2 , CHO, OR 7 where in turn R 5 and R 6 , the same or different, are hydrogen, straight or branched alkyl having 1-8 C atoms, a heterocyclic ring selected from the group comprising thiophene and imidazole, ascorbyl, peptidyl having up to 5 amino acids or a sugar radical, or R 5 and R 6 , together with the atom of nitrogen to which they are linked, form the groups necessary for completing a 5-membered heterocyclic nucleus which may contain other heteroatoms selected from the group consisting of 0 or N; R 7 has the meanings indicated above for R 5 and R 6 ; R 8 is an acyl of an aliphatic carboxylic acid with 1-4 C atoms; R 9 is hydrogen or methyl; R 10 is methyl or phenyl; n is 1,2,3 or 4; and A is CO or SO 2 ; R 2 is hydrogen, NO 2 , halogen, CH(COOH) 2 , OH, (CH 2 ) n COOH where in turn n is 0,1,2 3 or 4; R 3 is hydrogen, NO 2 , OH; R 4 is hydrogen, NO 2 , halogen, SO 2 CH 3 , OH, N(R 5 ,R 6 ) where in turn R 5 and R 6 have the meanings indicated above, provided however that at least two of the substituents R 1 , R 2 , R 3 and R 4 are not hydrogen and R is not H when R 2 and R 4 are NO and R 3 is H; is not I when R is NO 2 , R 3 is H, and R 4 is NO or CH 3 SO 2 ; is not p-nitrophenoxy when R is NO 2 , R 3 and R 4 are H; and is not CONH 2 or COOH when R 4 is NO 2 , R 2 and R 3 are H; and addition salts thereof with pharmaceutically acceptable acids or bases.

Claim 6

A compound according to claim 3, wherein R 1 is H, bromine, iodine, carboxy, p-nitrophenoxy, CON(R 5 ,R 6 ), CONH(CHR 9 ) n -COOH, NH(CHR 9 ) n AR 10 , CH=NOH where in turn R 5 and R 6 , the same or different, are hydrogen, a straight or branched alkyl having 1-3 C atoms, or together with the nitrogen atom to which they are linked, are the groups necessary to complete a morpholine or a piperazine ring; R 9 is hydrogen or methyl; R 10 is methyl or phenyl; n is 1, 2 or 3; and A is CO or SO 2 ; R 2 is hydrogen, nitro, carboxy or CH(COOH) 2 ; R 3 is hydrogen or nitro; and R 4 is hydrogen, bromine, iodine, nitro or SO 2 CH 3 .

Claim 7

A method of treating tumors comprising administering to a patient in need thereof a pharmaceutical composition according to claim 1 or 2 above.