Derivatives of methylene diphosphonic acid, preparation of...

C - Chemistry – Metallurgy – 07 – F

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C07F 9/38 (2006.01) A61K 31/00 (2006.01) C07F 9/40 (2006.01) C07F 9/58 (2006.01) C07F 9/6506 (2006.01) C07F 9/6512 (2006.01) C07F 9/6541 (2006.01)

Patent

CA 1267650

Abstract The present invention relates to new pharmaceutically-active products of the formula Image (I) in which: - R1 is hydrogen or a straight or branched lower alkyl group having from 1 to 4 carbon atoms, - R2 is : . hydrogen, . an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted by a hydroxy group, a thiol group, one or more halogen atoms, an alkoxycarbonyl group, a phenyl group or an Image group where Z1 and Z2, considered independently of one another, are hydrogen or an alkyl group having from 1 to 4 carbon atoms, a phenyl group which is unsubstituted or substituted one or more times by halogen, a nitro group, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, trifluoromethyl, an NH2 group, a COOH group or a COO-alkyl group, .a Image group, where X is oxygen or sulfur and Z1 and Z2 are as defined above, . a heterocyclic aromatic radical with 5 or 6 rings members, containing 1 or 2 heteroatoms chosen from amongst nitrogen and sulfur, or . a heterocyclic radical with 5 ring members fused to a benzene ring having the formula : Image where X is oxygen, an NH group or sulfur and R4 is hydrogen or a halogen atom, - R3 is hydrogen or a hydroxyl group, and - n is integer between 0 and 10, with the proviso that n cannot be 0 if R3 is OH, and with the further proviso that : - R2 is different from the methyl or pyridyl group when R1 = R3 = H and n = 0 ; - R2 is different from the phenyl group when R1 is an ethyl group, R3 = H and n = 0 ; - R2 is different from the group having the formula Image wherein Q is a halogen atom, a nitro group or a trifluoromethyl group, P is methyl or ethyl group when R1 is a methyl or ethyl group, R3 = H and n = 0 ; - R2 is different from an alkyl group or a non-substituted phenyl group when R3 = OH and n = 1 ; and the salts of said derivatives with inorganic or organic bases when R1 = H. These compounds have antiinflammatory activity.

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