AU2001294265A1 - Process for producing nateglinide crystal - Google Patents
Process for producing nateglinide crystalInfo
- Publication number
- AU2001294265A1 AU2001294265A1 AU2001294265A AU9426501A AU2001294265A1 AU 2001294265 A1 AU2001294265 A1 AU 2001294265A1 AU 2001294265 A AU2001294265 A AU 2001294265A AU 9426501 A AU9426501 A AU 9426501A AU 2001294265 A1 AU2001294265 A1 AU 2001294265A1
- Authority
- AU
- Australia
- Prior art keywords
- nateglinide
- producing
- reaction mixture
- ketone solvent
- crystals
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 title abstract 5
- 229960000698 nateglinide Drugs 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 4
- 239000013078 crystal Substances 0.000 title abstract 3
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- YXGDSBSUTMGHOL-UHFFFAOYSA-N 4-propan-2-ylcyclohexane-1-carbonyl chloride Chemical compound CC(C)C1CCC(C(Cl)=O)CC1 YXGDSBSUTMGHOL-UHFFFAOYSA-N 0.000 abstract 1
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 abstract 1
- 229930182832 D-phenylalanine Natural products 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 239000012046 mixed solvent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
There is provided methods for producing nateglinide crystals, which comprises the steps of adding an acid(s) to a reaction mixture containing nateglinide to make it acidic, the reaction mixture being obtained by reacting trans-4-isopropylcyclohexylcarbonyl chloride with D-phenylalanine in a mixed solvent of ketone solvent and water in the presence of an alkali; and then adjusting the temperature of the mixture to 58 DEG C to 72 DEG C and the concentration of ketone solvent to more than 8wt% and less than 22wt% to conduct precipitation of nateglinide crystals. This producing method is the industrially beneficial methods for crystallization of nateglinide.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000-317604 | 2000-10-18 | ||
| JP2000317604 | 2000-10-18 | ||
| PCT/JP2001/009069 WO2002032854A1 (en) | 2000-10-18 | 2001-10-16 | Process for producing nateglinide crystal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001294265A1 true AU2001294265A1 (en) | 2002-04-29 |
Family
ID=18796362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001294265A Abandoned AU2001294265A1 (en) | 2000-10-18 | 2001-10-16 | Process for producing nateglinide crystal |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US7208622B2 (en) |
| EP (1) | EP1334963B1 (en) |
| JP (1) | JP4114200B2 (en) |
| KR (1) | KR100819358B1 (en) |
| CN (2) | CN1232502C (en) |
| AT (1) | ATE368641T1 (en) |
| AU (1) | AU2001294265A1 (en) |
| BR (1) | BR0114729A (en) |
| CA (1) | CA2425538C (en) |
| CY (1) | CY1106837T1 (en) |
| DE (1) | DE60129728T2 (en) |
| DK (1) | DK1334963T3 (en) |
| ES (1) | ES2291356T3 (en) |
| MX (1) | MXPA03003484A (en) |
| PT (1) | PT1334963E (en) |
| RU (2) | RU2273629C2 (en) |
| TW (1) | TWI251588B (en) |
| WO (1) | WO2002032854A1 (en) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ521366A (en) * | 2000-03-17 | 2005-07-29 | Ajinomoto Kk | Drugs for complications of diabetes and neuropathy, and utilisation thereof |
| MXPA03003484A (en) | 2000-10-18 | 2003-07-14 | Ajinomoto Kk | Process for producing nateglinide crystal. |
| ES2290173T3 (en) * | 2000-10-18 | 2008-02-16 | Ajinomoto Co., Inc. | PROCEDURE FOR THE PREPARATION OF ACILFENILALANINAS. |
| AU2001296000A1 (en) * | 2000-10-24 | 2002-05-27 | Ajinomoto Co., Inc. | Nateglinide-containing hydrophilic drug preparations |
| DK1334964T3 (en) * | 2000-10-24 | 2007-09-24 | Ajinomoto Kk | Process for the preparation of B-form nateglinide crystals |
| WO2002034254A1 (en) * | 2000-10-24 | 2002-05-02 | Ajinomoto Co.,Inc. | Nateglinide-containing preparations |
| EP2264004A1 (en) * | 2002-04-15 | 2010-12-22 | Ajinomoto Co., Inc. | New nateglinide crystals |
| US7411089B2 (en) | 2002-04-15 | 2008-08-12 | Ajinomoto Co., Inc. | Nateglinide crystals |
| WO2004005240A1 (en) * | 2002-07-03 | 2004-01-15 | Teva Pharmaceutical Industries Ltd. | Process for preparing nateglinide and intermediates thereof |
| US6861553B2 (en) | 2002-07-03 | 2005-03-01 | Teva Pharmaceuticals Industries Ltd. | Process for preparing nateglinide and intermediates thereof |
| US7420084B2 (en) | 2002-07-18 | 2008-09-02 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| WO2004009532A1 (en) * | 2002-07-18 | 2004-01-29 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US7148376B2 (en) | 2002-07-18 | 2006-12-12 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US7358390B2 (en) | 2002-07-18 | 2008-04-15 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US7534913B2 (en) | 2002-07-18 | 2009-05-19 | Teva Pharmaceutica Industries Ltd. | Crystalline form of nateglinide |
| CN1318392C (en) * | 2003-01-17 | 2007-05-30 | 中国人民解放军军事医学科学院毒物药物研究所 | Improved preparation method of Nagelinei |
| EP1616886A4 (en) * | 2003-02-18 | 2006-06-14 | Konishi Co Ltd | Curing resin, method for producing same and curing resin composition |
| 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 |
| EP1535900B1 (en) * | 2003-11-26 | 2006-12-27 | A.M.S.A. ANONIMA MATERIE SINTETICHE E AFFINI S.p.A. | Process for the preparation of nateglinide, preferably in b-form |
| WO2005110972A1 (en) * | 2004-05-07 | 2005-11-24 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| GB0413084D0 (en) | 2004-06-11 | 2004-07-14 | Cipla Ltd | Process |
| US7425648B2 (en) | 2005-01-03 | 2008-09-16 | A.M.S.A. Anonima Materie Sintetiche E. Affini S.P.A. | Process for the preparation of nateglinide, preferably in B-form |
| WO2006080524A1 (en) * | 2005-01-31 | 2006-08-03 | Ajinomoto Co., Inc. | Medicinal composition for ameliorating or treating glucose intolerance, borderline diabetes, insulin resistance and hyperinsulinemia containing hypoglycemic agent |
| EP2003113A4 (en) * | 2006-03-31 | 2012-07-18 | Ajinomoto Kk | Process for production of carboxylic acid chloride compound |
| WO2007113650A2 (en) * | 2006-04-05 | 2007-10-11 | Cadila Pharmaceuticals Limited | A novel and improved process fro the preparation of nateglinide and its polymorph form-h |
| KR100837843B1 (en) * | 2006-12-26 | 2008-06-13 | 씨제이제일제당 (주) | Nateglinide crystalline form, preparation method thereof, and pharmaceutical composition comprising the same |
| KR101226024B1 (en) * | 2010-06-08 | 2013-01-24 | 삼성중공업 주식회사 | A vessel |
| AU2011266820A1 (en) | 2010-06-14 | 2013-01-24 | Cipla Limited | A process for the preparation of nateglinide |
| KR20150146007A (en) | 2014-06-20 | 2015-12-31 | 주식회사 씨트리 | A new method for producing nateglinide |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6354321A (en) * | 1985-03-27 | 1988-03-08 | Ajinomoto Co Inc | Blood sugar lowering agent |
| AU615966B2 (en) * | 1987-12-04 | 1991-10-17 | Takeda Chemical Industries Ltd. | Crystals of cephem hydrochloride |
| GB8820844D0 (en) * | 1988-09-05 | 1988-10-05 | Pfizer Ltd | Therapeutic agents |
| US5041232A (en) * | 1990-03-16 | 1991-08-20 | Lever Brothers Company, Division Of Conopco, Inc. | Sulfonimines as bleach catalysts |
| JPH0415221A (en) | 1990-05-08 | 1992-01-20 | Daicel Chem Ind Ltd | Preparation of polycarbonate |
| US5463116A (en) * | 1991-07-30 | 1995-10-31 | Ajinomoto Co., Inc. | Crystals of N- (trans-4-isopropylcyclohexlycarbonyl)-D-phenylalanine and methods for preparing them |
| DE10199058I2 (en) * | 1991-07-30 | 2006-04-27 | Alcm Co | Crystals of N- (trans-4-isopropylcyclohexylcarbonyl) -D-phenylalanine and process for their preparation |
| JPH0717899A (en) * | 1993-07-01 | 1995-01-20 | Ajinomoto Co Inc | Production of carboxylic acid chloride |
| ES2257772T3 (en) | 1996-11-15 | 2006-08-01 | Ajinomoto Co., Inc. | PREPARATION OF NATEGLINIDA IN TABLETS. |
| DE60039315D1 (en) | 1999-12-28 | 2008-08-07 | Ajinomoto Kk | Antidiabetic preparation for oral administration |
| NZ521366A (en) | 2000-03-17 | 2005-07-29 | Ajinomoto Kk | Drugs for complications of diabetes and neuropathy, and utilisation thereof |
| ES2290173T3 (en) | 2000-10-18 | 2008-02-16 | Ajinomoto Co., Inc. | PROCEDURE FOR THE PREPARATION OF ACILFENILALANINAS. |
| MXPA03003484A (en) | 2000-10-18 | 2003-07-14 | Ajinomoto Kk | Process for producing nateglinide crystal. |
| DK1334964T3 (en) | 2000-10-24 | 2007-09-24 | Ajinomoto Kk | Process for the preparation of B-form nateglinide crystals |
| WO2002034254A1 (en) | 2000-10-24 | 2002-05-02 | Ajinomoto Co.,Inc. | Nateglinide-containing preparations |
| US6842673B2 (en) | 2002-06-05 | 2005-01-11 | Visteon Global Technologies, Inc. | Engine engagement control for a hybrid electric vehicle |
-
2001
- 2001-10-16 MX MXPA03003484A patent/MXPA03003484A/en active IP Right Grant
- 2001-10-16 DE DE60129728T patent/DE60129728T2/en not_active Expired - Lifetime
- 2001-10-16 DK DK01974875T patent/DK1334963T3/en active
- 2001-10-16 CA CA2425538A patent/CA2425538C/en not_active Expired - Fee Related
- 2001-10-16 CN CNB018206581A patent/CN1232502C/en not_active Expired - Fee Related
- 2001-10-16 RU RU2003111021/04A patent/RU2273629C2/en not_active IP Right Cessation
- 2001-10-16 JP JP2002536038A patent/JP4114200B2/en not_active Expired - Lifetime
- 2001-10-16 PT PT01974875T patent/PT1334963E/en unknown
- 2001-10-16 EP EP01974875A patent/EP1334963B1/en not_active Expired - Lifetime
- 2001-10-16 AT AT01974875T patent/ATE368641T1/en active
- 2001-10-16 WO PCT/JP2001/009069 patent/WO2002032854A1/en not_active Ceased
- 2001-10-16 RU RU2005137243/04A patent/RU2318801C2/en not_active IP Right Cessation
- 2001-10-16 KR KR1020037005388A patent/KR100819358B1/en not_active Expired - Fee Related
- 2001-10-16 BR BR0114729-3A patent/BR0114729A/en not_active IP Right Cessation
- 2001-10-16 CN CNB2005101188521A patent/CN100384814C/en not_active Expired - Fee Related
- 2001-10-16 ES ES01974875T patent/ES2291356T3/en not_active Expired - Lifetime
- 2001-10-16 AU AU2001294265A patent/AU2001294265A1/en not_active Abandoned
- 2001-10-17 TW TW090125697A patent/TWI251588B/en not_active IP Right Cessation
-
2003
- 2003-04-18 US US10/418,105 patent/US7208622B2/en not_active Expired - Fee Related
-
2007
- 2007-03-14 US US11/686,073 patent/US7459582B2/en not_active Expired - Fee Related
- 2007-08-28 CY CY20071101133T patent/CY1106837T1/en unknown
-
2008
- 2008-10-31 US US12/262,634 patent/US20090076301A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20070167523A1 (en) | 2007-07-19 |
| RU2318801C2 (en) | 2008-03-10 |
| CA2425538A1 (en) | 2003-04-10 |
| TWI251588B (en) | 2006-03-21 |
| DE60129728T2 (en) | 2008-04-24 |
| DE60129728D1 (en) | 2007-09-13 |
| BR0114729A (en) | 2003-10-14 |
| KR20030059203A (en) | 2003-07-07 |
| US20090076301A1 (en) | 2009-03-19 |
| US20040030182A1 (en) | 2004-02-12 |
| EP1334963A4 (en) | 2005-08-17 |
| ATE368641T1 (en) | 2007-08-15 |
| RU2005137243A (en) | 2007-06-10 |
| JP4114200B2 (en) | 2008-07-09 |
| CN1232502C (en) | 2005-12-21 |
| ES2291356T3 (en) | 2008-03-01 |
| CN1481356A (en) | 2004-03-10 |
| US7459582B2 (en) | 2008-12-02 |
| RU2273629C2 (en) | 2006-04-10 |
| CN1769263A (en) | 2006-05-10 |
| US7208622B2 (en) | 2007-04-24 |
| DK1334963T3 (en) | 2007-09-24 |
| PT1334963E (en) | 2007-09-20 |
| CA2425538C (en) | 2010-10-12 |
| CN100384814C (en) | 2008-04-30 |
| EP1334963A1 (en) | 2003-08-13 |
| MXPA03003484A (en) | 2003-07-14 |
| WO2002032854A1 (en) | 2002-04-25 |
| EP1334963B1 (en) | 2007-08-01 |
| JPWO2002032854A1 (en) | 2004-02-26 |
| KR100819358B1 (en) | 2008-04-04 |
| CY1106837T1 (en) | 2012-05-23 |
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