CA2426745C - Methods for producing nateglinide b-type crystals - Google Patents
Methods for producing nateglinide b-type crystals Download PDFInfo
- Publication number
- CA2426745C CA2426745C CA002426745A CA2426745A CA2426745C CA 2426745 C CA2426745 C CA 2426745C CA 002426745 A CA002426745 A CA 002426745A CA 2426745 A CA2426745 A CA 2426745A CA 2426745 C CA2426745 C CA 2426745C
- Authority
- CA
- Canada
- Prior art keywords
- crystals
- nateglinide
- type crystals
- type
- drying
- 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.)
- Expired - Fee Related
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 100
- 229960000698 nateglinide Drugs 0.000 title claims abstract description 42
- 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 claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000001035 drying Methods 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- -1 nateglinide hydrates Chemical class 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- OELFLUMRDSZNSF-OFLPRAFFSA-N (2R)-2-[[oxo-(4-propan-2-ylcyclohexyl)methyl]amino]-3-phenylpropanoic acid Chemical compound C1CC(C(C)C)CCC1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-OFLPRAFFSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000324375 | 2000-10-24 | ||
| JP2000-324375 | 2000-10-24 | ||
| PCT/JP2001/009293 WO2002034713A1 (en) | 2000-10-24 | 2001-10-23 | Process for producing b-form nateglinide crystal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2426745A1 CA2426745A1 (en) | 2003-04-23 |
| CA2426745C true CA2426745C (en) | 2009-09-15 |
Family
ID=18801920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002426745A Expired - Fee Related CA2426745C (en) | 2000-10-24 | 2001-10-23 | Methods for producing nateglinide b-type crystals |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US20030229249A1 (OSRAM) |
| EP (1) | EP1334964B1 (OSRAM) |
| JP (1) | JP4225057B2 (OSRAM) |
| KR (1) | KR100810930B1 (OSRAM) |
| CN (1) | CN100422143C (OSRAM) |
| AT (1) | ATE370115T1 (OSRAM) |
| AU (1) | AU2001296001A1 (OSRAM) |
| BR (1) | BR0114846A (OSRAM) |
| CA (1) | CA2426745C (OSRAM) |
| CY (1) | CY1106839T1 (OSRAM) |
| DE (1) | DE60130014T2 (OSRAM) |
| DK (1) | DK1334964T3 (OSRAM) |
| ES (1) | ES2288997T3 (OSRAM) |
| MX (1) | MXPA03003575A (OSRAM) |
| PT (1) | PT1334964E (OSRAM) |
| RU (1) | RU2275354C2 (OSRAM) |
| TW (1) | TWI293290B (OSRAM) |
| WO (1) | WO2002034713A1 (OSRAM) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK14922002A3 (sk) * | 2000-03-17 | 2003-04-01 | Ajinomoto Co., Inc. | Farmaceutický prostriedok na prevenciu, zlepšenie a/alebo liečenie diabetickej komplikácie a použitie postprandiálnej látky na zníženie hladiny krvného cukru |
| PT1334962E (pt) * | 2000-10-18 | 2007-10-09 | Ajinomoto Kk | ''processo de preparação de acilfenilalaninas'' |
| BR0114729A (pt) * | 2000-10-18 | 2003-10-14 | Ajinomoto Kk | Métodos para produzir cristais de nateglinida, e cristais do tipo h, cristais de nateglinida, e, cristais do tipo h de nateglinida |
| BR0114897A (pt) * | 2000-10-24 | 2003-08-12 | Ajinomoto Kk | Preparação farmacêutica hidrofìlica contendo nateglinida, e, método para a preparação da mesma |
| DE60135674D1 (de) * | 2000-10-24 | 2008-10-16 | Ajinomoto Kk | Nateglinid enthaltende präparate |
| EP2261202A1 (en) * | 2002-04-15 | 2010-12-15 | Ajinomoto Co., Inc. | New nateglinide crystals |
| US7411089B2 (en) | 2002-04-15 | 2008-08-12 | Ajinomoto Co., Inc. | Nateglinide crystals |
| US6861553B2 (en) | 2002-07-03 | 2005-03-01 | Teva Pharmaceuticals Industries Ltd. | Process for preparing nateglinide and intermediates thereof |
| US7358390B2 (en) | 2002-07-18 | 2008-04-15 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| EP1467964A1 (en) * | 2002-07-18 | 2004-10-20 | Teva Pharmaceutical Industries Limited | Polymorphic forms of nateglinide |
| US7420084B2 (en) * | 2002-07-18 | 2008-09-02 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US7534913B2 (en) | 2002-07-18 | 2009-05-19 | Teva Pharmaceutica Industries Ltd. | Crystalline form of nateglinide |
| US7148376B2 (en) | 2002-07-18 | 2006-12-12 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| 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 |
| KR20070009726A (ko) * | 2004-05-07 | 2007-01-18 | 테바 파마슈티컬 인더스트리즈 리미티드 | 나테글리나이드의 다형태 |
| US20070231393A1 (en) * | 2004-05-19 | 2007-10-04 | University Of South Carolina | System and Device for Magnetic Drug Targeting with Magnetic Drug Carrier Particles |
| WO2005113485A2 (en) * | 2004-05-20 | 2005-12-01 | Dr. Reddy's Laboratories Ltd. | Stable nateglinide form b compositions |
| 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 |
| EP1891971A4 (en) * | 2005-01-31 | 2010-02-03 | Ajinomoto Kk | MEDICAL COMPOSITION USING HYPERGLY CRAB MEDICAMENT TO TREAT OR TREAT GLUCOSE-INTOLERANCE, BORDERLINE DIABETES, INSULIN RESISTANCE AND HYPERINSULINEMIA |
| WO2007135533A1 (en) * | 2006-05-23 | 2007-11-29 | Aurobindo Pharma Limited | Process for preparing nateglinide b-type crystals |
| KR100837843B1 (ko) * | 2006-12-26 | 2008-06-13 | 씨제이제일제당 (주) | 나테글리나이드 결정형, 그 제조방법, 및 그를 포함하는약제학적 조성물 |
| KR20130087485A (ko) | 2010-06-14 | 2013-08-06 | 씨아이피엘에이 엘티디. | 나테글리니드의 제조 방법 |
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| US9108942B1 (en) | 2014-11-05 | 2015-08-18 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| WO2014020480A2 (en) | 2012-08-03 | 2014-02-06 | Mahesh Kandula | Compositions and methods for the treatment migraine and neurologic diseases |
| WO2014037833A2 (en) | 2012-09-06 | 2014-03-13 | Mahesh Kandula | Compositions and methods for the treatment inflammation and lipid disorders |
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| US9333187B1 (en) | 2013-05-15 | 2016-05-10 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory bowel disease |
| AU2014276346A1 (en) | 2013-06-04 | 2015-12-24 | Cellixbio Private Limited | Compositions and methods for the treatment of diabetes and pre-diabetes |
| US9096537B1 (en) | 2014-12-31 | 2015-08-04 | Mahesh Kandula | Compositions and methods for the treatment of mucositis |
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| US9175008B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Prodrugs of anti-platelet agents |
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| CN104402756B (zh) * | 2014-11-27 | 2016-08-31 | 天方药业有限公司 | 一种高纯度那格列奈的制备方法 |
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| CN109369443A (zh) * | 2018-11-05 | 2019-02-22 | 扬子江药业集团江苏海慈生物药业有限公司 | 一种新的那格列奈h晶型的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6354321A (ja) * | 1985-03-27 | 1988-03-08 | Ajinomoto Co Inc | 血糖降下剤 |
| AU615966B2 (en) * | 1987-12-04 | 1991-10-17 | Takeda Chemical Industries Ltd. | Crystals of cephem hydrochloride |
| US5463116A (en) * | 1991-07-30 | 1995-10-31 | Ajinomoto Co., Inc. | Crystals of N- (trans-4-isopropylcyclohexlycarbonyl)-D-phenylalanine and methods for preparing them |
| ES2100291T3 (es) | 1991-07-30 | 1997-06-16 | Ajinomoto Kk | Cristales de n-(trans-4-isopropilciclohexilcarbonil)-d-fenilalanina y metodos para prepararlos. |
| EP0965339B1 (en) * | 1996-11-15 | 2006-04-05 | Ajinomoto Co., Inc. | Tabletted nateglinide preparation |
| US6844006B1 (en) * | 1999-07-09 | 2005-01-18 | Pennfield Oil Company | Process and apparatus for the preparation of chlortetracycline-containing animal feed compositions |
| KR20020063282A (ko) * | 1999-12-28 | 2002-08-01 | 아지노모토 가부시키가이샤 | 경구 투여용 당뇨병 치료제 |
| SK14922002A3 (sk) * | 2000-03-17 | 2003-04-01 | Ajinomoto Co., Inc. | Farmaceutický prostriedok na prevenciu, zlepšenie a/alebo liečenie diabetickej komplikácie a použitie postprandiálnej látky na zníženie hladiny krvného cukru |
| BR0114729A (pt) * | 2000-10-18 | 2003-10-14 | Ajinomoto Kk | Métodos para produzir cristais de nateglinida, e cristais do tipo h, cristais de nateglinida, e, cristais do tipo h de nateglinida |
| PT1334962E (pt) * | 2000-10-18 | 2007-10-09 | Ajinomoto Kk | ''processo de preparação de acilfenilalaninas'' |
| DE60135674D1 (de) * | 2000-10-24 | 2008-10-16 | Ajinomoto Kk | Nateglinid enthaltende präparate |
| US7411089B2 (en) | 2002-04-15 | 2008-08-12 | Ajinomoto Co., Inc. | Nateglinide crystals |
-
2001
- 2001-10-23 ES ES01976819T patent/ES2288997T3/es not_active Expired - Lifetime
- 2001-10-23 CA CA002426745A patent/CA2426745C/en not_active Expired - Fee Related
- 2001-10-23 BR BR0114846-0A patent/BR0114846A/pt not_active IP Right Cessation
- 2001-10-23 KR KR1020037005671A patent/KR100810930B1/ko not_active Expired - Fee Related
- 2001-10-23 AT AT01976819T patent/ATE370115T1/de active
- 2001-10-23 EP EP01976819A patent/EP1334964B1/en not_active Expired - Lifetime
- 2001-10-23 DE DE60130014T patent/DE60130014T2/de not_active Expired - Lifetime
- 2001-10-23 AU AU2001296001A patent/AU2001296001A1/en not_active Abandoned
- 2001-10-23 PT PT01976819T patent/PT1334964E/pt unknown
- 2001-10-23 JP JP2002537707A patent/JP4225057B2/ja not_active Expired - Fee Related
- 2001-10-23 WO PCT/JP2001/009293 patent/WO2002034713A1/ja not_active Ceased
- 2001-10-23 DK DK01976819T patent/DK1334964T3/da active
- 2001-10-23 CN CNB018212999A patent/CN100422143C/zh not_active Expired - Fee Related
- 2001-10-23 RU RU2003111948/04A patent/RU2275354C2/ru not_active IP Right Cessation
- 2001-10-23 MX MXPA03003575A patent/MXPA03003575A/es active IP Right Grant
- 2001-10-24 TW TW090126305A patent/TWI293290B/zh not_active IP Right Cessation
-
2003
- 2003-04-24 US US10/421,888 patent/US20030229249A1/en not_active Abandoned
-
2007
- 2007-06-04 US US11/757,769 patent/US7544834B2/en not_active Expired - Fee Related
- 2007-08-28 CY CY20071101136T patent/CY1106839T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT1334964E (pt) | 2007-09-20 |
| US20070232829A1 (en) | 2007-10-04 |
| EP1334964A4 (en) | 2005-09-28 |
| BR0114846A (pt) | 2004-02-25 |
| AU2001296001A1 (en) | 2002-05-06 |
| KR100810930B1 (ko) | 2008-03-10 |
| EP1334964A1 (en) | 2003-08-13 |
| KR20030059212A (ko) | 2003-07-07 |
| DE60130014D1 (de) | 2007-09-27 |
| CY1106839T1 (el) | 2012-05-23 |
| MXPA03003575A (es) | 2003-07-14 |
| JP4225057B2 (ja) | 2009-02-18 |
| WO2002034713A1 (en) | 2002-05-02 |
| CA2426745A1 (en) | 2003-04-23 |
| JPWO2002034713A1 (ja) | 2004-03-04 |
| ATE370115T1 (de) | 2007-09-15 |
| US20030229249A1 (en) | 2003-12-11 |
| CN1483018A (zh) | 2004-03-17 |
| TWI293290B (OSRAM) | 2008-02-11 |
| DE60130014T2 (de) | 2008-05-08 |
| US7544834B2 (en) | 2009-06-09 |
| RU2275354C2 (ru) | 2006-04-27 |
| DK1334964T3 (da) | 2007-09-24 |
| CN100422143C (zh) | 2008-10-01 |
| ES2288997T3 (es) | 2008-02-01 |
| EP1334964B1 (en) | 2007-08-15 |
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