Pharmaceutical compositions containing thiophene compounds, and new thiophene compounds

Claim 1

A method for radiosensitizing cells which comprises administering to a patient in need thereof a radiosensitizing effective amount of a composition containing as an active ingredient a compound of the formula ##STR3## 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 , and wherein R 5 and R 6 are the same or different, and represent 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 groups necessary for forming a 5-membered heterocyclic ring which may contain other heteroatoms selected from the group consisting of O and N; R 7 has the meaning indicated for R 5 and R 6 above; 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, NO 2 , halogen, CH(COOH) 2 , OH, (CH 2 ) n COOH wheren 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 ) wherein R 5 and R 6 have the meaning 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 2

A method for radiosensitizing cells which comprises administering to a patient in need thereof a radiosensitizing effective amount of a composition containing as an active ingredient a compound of the formula ##STR3## 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 , and wherein R 5 and R 6 are the same or different, and represent 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 groups necessary for forming a 5-membered heterocyclic ring which may contain other heteroatoms selected from the group consisting of O and N; R 7 has the meaning indicated for R 5 and R 6 above; 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, NO 2 , halogen, CH(COOH) 2 , OH, (CH 2 ) n COOH wheren 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 ) wherein R 5 and R 6 have the meaning 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 4

A method for blocking the reaction of oxygen radicals in cells which comprises administering to a patient in need thereof an oxygen blocking effective amount of a composition containing as the active ingredient thereof a compound of the formula ##STR4## 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 , wherein R 5 and R 6 are the same or different, and respresent 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 O and N; R 7 has the meanings indicated for R 5 and R 6 above; 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, NO 2 , halogen, CH(COOH) 2 , OH, (CH 2 ) n COOH wherein 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 ) wherein R 5 and R 6 have the meaning 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 5

A method for blocking the reaction of oxygen radicals in cells which comprises administering to a patient in need thereof an oxygen blocking effective amount of a composition containing as the active ingredient thereof a compound of the formula ##STR4## 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 , wherein R 5 and R 6 are the same or different, and respresent 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 O and N; R 7 has the meanings indicated for R 5 and R 6 above; 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, NO 2 , halogen, CH(COOH) 2 , OH, (CH 2 ) n COOH wherein 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 ) wherein R 5 and R 6 have the meaning 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.