| Title of Invention | A PROCESS FOR THE PREPARATION OF A COMPOUND OF FORMULA III AND A PROCESS OF EPIMERIZING A CARBOXYLIC ACID COMPOUND OF FORMULA IV |
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| Abstract | The process for the preparation of a compound of formula III and a process of epimerizing a carboxvlic acid compound of formula IV The present invention provides an efficient synthetic process for making benazepril and analogues thereof by having an intermediate compound undergo epimerization and kinetic resolution. |
| Full Text | Kinetic Resolution of a Intermediate Useful in the Production of Benazepril and Analogues Thereof group I to the 3-position carbon with a good leaving group forms crystals, its concentration in the solution becomes r idesired S,S form. Scheme 2 illustrates the conversion of (1'S,33)-3- diastereomers (hereinafter "S,S/R,S") effects- of: (1) , deactivating epimerization at the wrong also be used to conduct the epimerization and chiral 'only and do not limit the scope of the invention. The mixture was stirred and heated to 110°C for 6 hours- Subsequently, 3N aqueous NaOH (2.4L) was added to IBS-l-143°C and maintained at this temperature for 3 hours. slurry was heated to 138°C and stirred at this additional 2L of water and dried at reduced pressure to give 520g of crude solid. This solid was dissolved in a incorporated by reference in their entirety. We Claim: 1 . A process for the preparation of a compound of the formula (III) 22 is a halogen; hydroxide, carbonate and amine. solvent is dimethylacetamide. wherein R1 is hydrogen, or a lower alkyl group having 1 to 4 carbon atoms, to increase the amount of the SS diastereomer of the compound of formula II by refluxing the carboxylic acid compound of fomiula II in a solution comprising an organic solvent. 25. . The process of claim 24 wherein the SS diastereomer of the compound of formula II is converted by esterification to the ester compound of formula i 26. The process of claim 25 wherein the SS diastereomer of the compound of formula II is converted to the ester compound of formula i by reacting the compound of formula II with an alkyl halide and potassium carbonate or potassium bicarbonate. 27. The process of claim 25 wherein the alkyl halide is ethyl bromide. 28. The process of claim 24 wherein the organic solvent is selected from the group consisting of p-xylene, xylenes, ethylene glycol, propionic acid and acetic acid. 29. The process of claim 28 wherein the process of epimerizing the carboxylic acid compound of formula II in p-xylene or xylenes further comprises the esterification of the compound of formula II by reacting the compound of formula II with n.n-dimethyiacetylamide, bromoethane and potassium carbonate in said p-xyiene or xylenes solution. 30. The process of claim 25 wherein the ester compound of formula I is benazepril. 31. A process for the preparation of a compound of the formula (III), substantially as hereinabove described and exemplified. |
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1815-chenp-2003-assignement.pdf
1815-chenp-2003-claims duplicate.pdf
1815-chenp-2003-claims original.pdf
1815-chenp-2003-correspondnece-others.pdf
1815-chenp-2003-correspondnece-po.pdf
1815-chenp-2003-description(complete) duplicate.pdf
1815-chenp-2003-description(complete) original.pdf
| Patent Number | 201905 | ||||||||||||||||||
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| Indian Patent Application Number | 1815/CHENP/2003 | ||||||||||||||||||
| PG Journal Number | 05/2007 | ||||||||||||||||||
| Publication Date | 02-Feb-2007 | ||||||||||||||||||
| Grant Date | 31-Aug-2006 | ||||||||||||||||||
| Date of Filing | 18-Nov-2003 | ||||||||||||||||||
| Name of Patentee | SCINOPHARM TAIWAN LTD | ||||||||||||||||||
| Applicant Address | 1 NAN-KE 8TH ROAD, TAINAN SCIENCE-BASED INDUSTRIAL PARK, TAINAN COUNTY 741, CHINA R.O.C | ||||||||||||||||||
Inventors:
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| PCT International Classification Number | A61K | ||||||||||||||||||
| PCT International Application Number | PCT/IB02/03060 | ||||||||||||||||||
| PCT International Filing date | 2002-05-20 | ||||||||||||||||||
PCT Conventions:
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