Patent EA-004770-B1 (EA)
Title: Novel esters derived from (rr,ss)-2-hydroxybenzoate of 3-(2-dimethylaminomethyl-1-hydroxycyclohexyl)phenyl
Inventor: HUGUET CLOTET JUAN
IPC: C07B53/00
Filed: 2000-12-26
Abstract: 1. A compound of general formula (I): wherein: R1 is halogen, unsubstituted or substituted partially or totally by halogen C1-C6 alkyl, OR3, NO2 or phenyl unsubstituted or substituted partially or totally by a halogen atom, where R3 is C1-C6 alkyl, R2 is H or CH3CO-; and the salts and optical isomers thereof. 2. A compound according to claim 1, characterized in that R1 is halogen, such as F, Cl, Br, halosubstituted phenyl or hydro(C1-C6 fluoroalkyl). 3. A compound according to claim 1, characterized in that it is selected from one of the following: (RR-SS)-2-Acetoxy-4-trifluoromethyl-benzoic acid 3-(2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-phenyl ester, (RR-SS)-2-Hydroxy-4-trifluoromethyl-benzoic acid 3-(2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-phenyl ester, (RR-SS)-4-Chloro-2-hydroxy-benzoic acid 3-(2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-phenyl ester, (RR-SS)-2-Hydroxy-4-methyl-benzoic acid 3-(2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-phenyl ester, (RR-SS)-2-Hydroxy-4-methoxy-benzoic acid 3-(2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-phenyl ester, (RR-SS)-2-Hydroxy-5-nitro-benzoic acid 3-(2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-phenyl ester, (RR-SS)-2',4'-Difluoro-3-hydroxy-biphenyl-4-carboxylic acid 3-(2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-phenyl ester. 4. A process for obtaining a compound of general formula (I) as claimed in claim 1, characterized in that a compound of formula (II) is reacted with a compound of general formula (III): wherein: R1 and R2 have the same meaning as above, and L = OH, halogen, , O-R4 or -CO-R5, where R4 = C1-C6 alkyl, phenyl, optionally substituted phenyl, and R5 = Alkyl, a phenyl ring optionally substituted with one or more substituents, or a heterocyclic ring optionally substituted with one or more substituents, in an inert solvent, at temperatures ranging from -20 degree C to 120 degree C. 5. A process according to claim 4, characterized in that a condensation promoting agent is added. 6. A process according to claim 4, characterized in that said inert solvent is selected from dichloromethane, tetrahydrofuran, acetonitrile, 1,2-dichloroethane, ethyl acetate, dimethoxyethane or dioxane, preferably dichloromethane or tetrahydrofuran. 7. A process according to claim 5, characterized in that said condensation promoting agent is selected from carbonyldiimidazole, dicyclohexylcarbodiimide, triethylamine ethylchloroformate, triethylamine benzotriazoletosylate or diethylchlorophosphate, preferably carbonyldiimidazole or dicyclohexylcarbodiimide. 8. A process according to claim 4, characterized in that said temperature range is from 0 degree and 35 degree C. 9. The use of a compound of general formula (I) according to any of claims 1 to 3, for the production of a medicament for the treatment of pain. 10. A pharmaceutical composition, which comprises a compound of general formula (I) according to any of claims 1 to 3 and a pharmaceutically acceptable excipient, for the treatment of pain.