Process for the synthesis of trans-alkenoic acids, use thereof
AssigneeCouncil of Scientific and Industrial Research
InventorsVishwa Nath Gupta, Vikram Bhardwaj, Bhupinder Singh, Bal Krishan Chandan, Krishan Avtar Suri, Naresh Kumar Satti, Om Parkash Suri, Sukhdev Swami Handa
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Abstract
The present invention relates to a process for the preparation of trans-alkenoic acids of general formula CH3—(CH2)n—CH—(CH2)m CO2H where n=4 to 9 m−8 to 16. More particularly, the present invention relates to a process for he preparation of trans-tetracos-15-enoic acid, which is a bioactive constituent possessing dose-related hepatoprotective activity. The present invention also relates to the use thereof for hepatoprotection.
Claims21
Process for preparation of a trans-alkenoic acid of the formula CH3—(CH2)n—CH—CH—(CH2)mCOOH wherein n is 4 to 9, m is 8 to 16, said process comprising (i) reducing a bis noralkenoic acid to the corresponding alkenol in he presence of metal hydride (ii) reacting the alkenol obtained above with a brominating agent at a temperature in the range of 10 to 25° C. for 1 to 4 hours and recovering the bromoalkene so formed, (iii) condensing the bromoalkene obtained above with dialkyl malonate, ethyl acetoacetate or ethyl cyanoacetate in the presence of an alkali metal alkoxide to give dicarbalkoxyalkene followed by hydrolysis to give corresponding dicarboxylic acid, (iv) decarboxylating the dicarboxylic acid obtained above partially to trans-alkenoic acid.
Use of trans-alkenoic acids of general formula CH3-(CH2)n—CH—(CH2)mCO2H where n =4 to 9 m=8 to 16 for dose related hepatoprotection.
A method for hepatroprotection comprising administering to a patient a trans-alkenoic acid of general formula CH3—(CH2)n—CH═(CH2)mCO2H where n=4 to 9 m=8 to 16 in an amount of 12.5 to 100 mg per kg body weight of the patient.
A process for preparing a pharmaceutical composition for hepatoprotection comprising mixing a trans-alkenoic acid of general formula CH3—(CH2)n—CH—(CH2)m CO2H where n=4 to 9 m=8 to 16 in a pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.