TW200514556A - Synthesis and purification of nateglinide - Google Patents
Synthesis and purification of nateglinideInfo
- Publication number
- TW200514556A TW200514556A TW092129454A TW92129454A TW200514556A TW 200514556 A TW200514556 A TW 200514556A TW 092129454 A TW092129454 A TW 092129454A TW 92129454 A TW92129454 A TW 92129454A TW 200514556 A TW200514556 A TW 200514556A
- Authority
- TW
- Taiwan
- Prior art keywords
- formula
- phenylalanine
- trans
- nateglinide
- synthesis
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
Disclosed is a method for the synthesis of [(trans-4-isopropyl cyclohexyl)-carbonyl]-D-phenylalanine (nateglinide) (formula I), including the steps of: (i) reacting trans-4-isopropyl cyclohexyl carboxylic acid (formula (5)), with an alkyl chloroformate (formula (13)), where R represents an alkyl group, in a ketonic solvent in the presence of a base at a temperature in the range of -20 DEG to 30 DEG C to form the mixed anhydride of formula (14); and, (ii) reacting said mixed anhydride with an aqueous alkali salt solution of D-phenylalanine to yield a reaction mixture including [(trans-4-isopropyl cyclohexyl)-carbonyl]-D-phenylalanine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN773MU2002 | 2002-08-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
TW200514556A true TW200514556A (en) | 2005-05-01 |
Family
ID=34259967
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW092129454A TW200514556A (en) | 2002-08-26 | 2003-10-23 | Synthesis and purification of nateglinide |
Country Status (3)
Country | Link |
---|---|
AR (1) | AR041057A1 (en) |
TW (1) | TW200514556A (en) |
WO (1) | WO2004018408A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU227073B1 (en) | 2003-07-10 | 2010-06-28 | Richter Gedeon Nyrt | Process for the preparation of chirally pure n-(trans-4-isopropyl-cyclohexylcarbonyl)-d-phenyl-alanine (nateglinide) and it's crystalline forms and the cristalline form g |
GB0413084D0 (en) | 2004-06-11 | 2004-07-14 | Cipla Ltd | Process |
WO2007135533A1 (en) * | 2006-05-23 | 2007-11-29 | Aurobindo Pharma Limited | Process for preparing nateglinide b-type crystals |
KR20150146007A (en) | 2014-06-20 | 2015-12-31 | 주식회사 씨트리 | A new method for producing nateglinide |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0717899A (en) * | 1993-07-01 | 1995-01-20 | Ajinomoto Co Inc | Production of carboxylic acid chloride |
-
2003
- 2003-08-12 WO PCT/IB2003/003270 patent/WO2004018408A1/en not_active Application Discontinuation
- 2003-08-26 AR ARP030103084A patent/AR041057A1/en unknown
- 2003-10-23 TW TW092129454A patent/TW200514556A/en unknown
Also Published As
Publication number | Publication date |
---|---|
AR041057A1 (en) | 2005-04-27 |
WO2004018408A8 (en) | 2005-03-10 |
WO2004018408A1 (en) | 2004-03-04 |
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