RU2275354C2 - Способы получения кристаллов в-типа натеглинида - Google Patents
Способы получения кристаллов в-типа натеглинида Download PDFInfo
- Publication number
- RU2275354C2 RU2275354C2 RU2003111948/04A RU2003111948A RU2275354C2 RU 2275354 C2 RU2275354 C2 RU 2275354C2 RU 2003111948/04 A RU2003111948/04 A RU 2003111948/04A RU 2003111948 A RU2003111948 A RU 2003111948A RU 2275354 C2 RU2275354 C2 RU 2275354C2
- Authority
- RU
- Russia
- Prior art keywords
- crystals
- type
- nateglinide
- temperature
- nateglynide
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000001035 drying Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 229960000698 nateglinide Drugs 0.000 claims description 37
- 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 claims description 34
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 3
- -1 nateglinide hydrates Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 229940124597 therapeutic agent Drugs 0.000 abstract description 3
- 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 abstract description 2
- 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 abstract description 2
- 239000008280 blood Substances 0.000 abstract description 2
- 210000004369 blood Anatomy 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000008103 glucose Substances 0.000 abstract description 2
- 230000007423 decrease Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 7
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000012453 solvate Substances 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
- 238000004090 dissolution Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002360 preparation method Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000-324375 | 2000-10-24 | ||
| JP2000324375 | 2000-10-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2003111948A RU2003111948A (ru) | 2004-09-20 |
| RU2275354C2 true RU2275354C2 (ru) | 2006-04-27 |
Family
ID=18801920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003111948/04A RU2275354C2 (ru) | 2000-10-24 | 2001-10-23 | Способы получения кристаллов в-типа натеглинида |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US20030229249A1 (enExample) |
| EP (1) | EP1334964B1 (enExample) |
| JP (1) | JP4225057B2 (enExample) |
| KR (1) | KR100810930B1 (enExample) |
| CN (1) | CN100422143C (enExample) |
| AT (1) | ATE370115T1 (enExample) |
| AU (1) | AU2001296001A1 (enExample) |
| BR (1) | BR0114846A (enExample) |
| CA (1) | CA2426745C (enExample) |
| CY (1) | CY1106839T1 (enExample) |
| DE (1) | DE60130014T2 (enExample) |
| DK (1) | DK1334964T3 (enExample) |
| ES (1) | ES2288997T3 (enExample) |
| MX (1) | MXPA03003575A (enExample) |
| PT (1) | PT1334964E (enExample) |
| RU (1) | RU2275354C2 (enExample) |
| TW (1) | TWI293290B (enExample) |
| WO (1) | WO2002034713A1 (enExample) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001241168B2 (en) * | 2000-03-17 | 2005-06-16 | Ajinomoto Co., Inc. | Drugs for complications of diabetes and neuropathy and utilization thereof |
| MXPA03003484A (es) * | 2000-10-18 | 2003-07-14 | Ajinomoto Kk | Procedimiento para producir cristales de nateglinida. |
| ES2290173T3 (es) * | 2000-10-18 | 2008-02-16 | Ajinomoto Co., Inc. | Procedimiento para la preparacion de acilfenilalaninas. |
| JP4501054B2 (ja) * | 2000-10-24 | 2010-07-14 | 味の素株式会社 | ナテグリニド含有製剤 |
| RU2283104C2 (ru) * | 2000-10-24 | 2006-09-10 | Адзиномото Ко., Инк. | Гидрофильный фармацевтический препарат, содержащий натеглинид |
| JP4538842B2 (ja) * | 2002-04-15 | 2010-09-08 | 味の素株式会社 | 新規ナテグリニド結晶 |
| 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 |
| CA2492644A1 (en) * | 2002-07-18 | 2004-01-29 | 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 |
| US7420084B2 (en) | 2002-07-18 | 2008-09-02 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US7358390B2 (en) | 2002-07-18 | 2008-04-15 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| ES2279921T3 (es) * | 2003-11-26 | 2007-09-01 | A.M.S.A. Anonima Materie Sintetiche E Affini S.P.A. | Procedimiento para la preparacion de nateglinida preferentemente en forma b. |
| US20060004102A1 (en) * | 2004-05-07 | 2006-01-05 | Shlomit Wizel | Polymorphic forms of nateglinide |
| 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 |
| WO2006080524A1 (ja) * | 2005-01-31 | 2006-08-03 | Ajinomoto Co., Inc. | 血糖降下剤を含有する、耐糖能異常、境界型糖尿病、インスリン抵抗性及び高インスリン血症の改善ないし治療用医薬組成物 |
| 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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| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0196222B1 (en) * | 1985-03-27 | 1992-01-29 | Ajinomoto Co., Inc. | Hypoglycemic agent |
| RU2007407C1 (ru) * | 1987-12-04 | 1994-02-15 | Такеда Кемикал Индастриз ЛТД | СПОСОБ ПОЛУЧЕНИЯ КРИСТАЛЛОВ ГИДРОХЛОРИДА ГИДРАТА 7- β -[(Z)-2-(5-АМИНО - 1,2,4-ТИАДИАЗОЛ - 3-ИЛ)-2-МЕТОКСИИМИНОАЦЕТАМИДО] - 3 - [1-ИМИДАЗО-(1,2-B) ПИРИДАЗИН]МЕТИЛ - 3 - ЦЕФЕМ-4-КАРБОКСИЛАТА ИЛИ ЕГО СОЛЬВАТОВ |
| US5463116A (en) * | 1991-07-30 | 1995-10-31 | Ajinomoto Co., Inc. | Crystals of N- (trans-4-isopropylcyclohexlycarbonyl)-D-phenylalanine and methods for preparing them |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2100291T3 (es) | 1991-07-30 | 1997-06-16 | Ajinomoto Kk | Cristales de n-(trans-4-isopropilciclohexilcarbonil)-d-fenilalanina y metodos para prepararlos. |
| EP1586314B1 (en) * | 1996-11-15 | 2011-03-30 | Ajinomoto Co., Inc. | Nateglinide tablet composition |
| US6844006B1 (en) * | 1999-07-09 | 2005-01-18 | Pennfield Oil Company | Process and apparatus for the preparation of chlortetracycline-containing animal feed compositions |
| WO2001047557A1 (en) * | 1999-12-28 | 2001-07-05 | Ajinomoto Co., Inc. | Oral preparations for diabetes |
| AU2001241168B2 (en) * | 2000-03-17 | 2005-06-16 | Ajinomoto Co., Inc. | Drugs for complications of diabetes and neuropathy and utilization thereof |
| ES2290173T3 (es) * | 2000-10-18 | 2008-02-16 | Ajinomoto Co., Inc. | Procedimiento para la preparacion de acilfenilalaninas. |
| MXPA03003484A (es) * | 2000-10-18 | 2003-07-14 | Ajinomoto Kk | Procedimiento para producir cristales de nateglinida. |
| JP4501054B2 (ja) * | 2000-10-24 | 2010-07-14 | 味の素株式会社 | ナテグリニド含有製剤 |
| US7411089B2 (en) | 2002-04-15 | 2008-08-12 | Ajinomoto Co., Inc. | Nateglinide crystals |
-
2001
- 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
- 2001-10-23 CA CA002426745A patent/CA2426745C/en not_active Expired - Fee Related
- 2001-10-23 KR KR1020037005671A patent/KR100810930B1/ko not_active Expired - Fee Related
- 2001-10-23 EP EP01976819A patent/EP1334964B1/en not_active Expired - Lifetime
- 2001-10-23 JP JP2002537707A patent/JP4225057B2/ja not_active Expired - Fee Related
- 2001-10-23 AT AT01976819T patent/ATE370115T1/de active
- 2001-10-23 AU AU2001296001A patent/AU2001296001A1/en not_active Abandoned
- 2001-10-23 DE DE60130014T patent/DE60130014T2/de not_active Expired - Lifetime
- 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 ES ES01976819T patent/ES2288997T3/es not_active Expired - Lifetime
- 2001-10-23 BR BR0114846-0A patent/BR0114846A/pt not_active IP Right Cessation
- 2001-10-23 WO PCT/JP2001/009293 patent/WO2002034713A1/ja not_active Ceased
- 2001-10-23 PT PT01976819T patent/PT1334964E/pt unknown
- 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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0196222B1 (en) * | 1985-03-27 | 1992-01-29 | Ajinomoto Co., Inc. | Hypoglycemic agent |
| RU2007407C1 (ru) * | 1987-12-04 | 1994-02-15 | Такеда Кемикал Индастриз ЛТД | СПОСОБ ПОЛУЧЕНИЯ КРИСТАЛЛОВ ГИДРОХЛОРИДА ГИДРАТА 7- β -[(Z)-2-(5-АМИНО - 1,2,4-ТИАДИАЗОЛ - 3-ИЛ)-2-МЕТОКСИИМИНОАЦЕТАМИДО] - 3 - [1-ИМИДАЗО-(1,2-B) ПИРИДАЗИН]МЕТИЛ - 3 - ЦЕФЕМ-4-КАРБОКСИЛАТА ИЛИ ЕГО СОЛЬВАТОВ |
| US5463116A (en) * | 1991-07-30 | 1995-10-31 | Ajinomoto Co., Inc. | Crystals of N- (trans-4-isopropylcyclohexlycarbonyl)-D-phenylalanine and methods for preparing them |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0114846A (pt) | 2004-02-25 |
| DE60130014D1 (de) | 2007-09-27 |
| CA2426745C (en) | 2009-09-15 |
| KR100810930B1 (ko) | 2008-03-10 |
| US20030229249A1 (en) | 2003-12-11 |
| US7544834B2 (en) | 2009-06-09 |
| ES2288997T3 (es) | 2008-02-01 |
| KR20030059212A (ko) | 2003-07-07 |
| ATE370115T1 (de) | 2007-09-15 |
| US20070232829A1 (en) | 2007-10-04 |
| AU2001296001A1 (en) | 2002-05-06 |
| JPWO2002034713A1 (ja) | 2004-03-04 |
| DK1334964T3 (da) | 2007-09-24 |
| EP1334964A4 (en) | 2005-09-28 |
| PT1334964E (pt) | 2007-09-20 |
| CN1483018A (zh) | 2004-03-17 |
| CA2426745A1 (en) | 2003-04-23 |
| CN100422143C (zh) | 2008-10-01 |
| EP1334964A1 (en) | 2003-08-13 |
| DE60130014T2 (de) | 2008-05-08 |
| TWI293290B (enExample) | 2008-02-11 |
| JP4225057B2 (ja) | 2009-02-18 |
| EP1334964B1 (en) | 2007-08-15 |
| CY1106839T1 (el) | 2012-05-23 |
| WO2002034713A1 (en) | 2002-05-02 |
| MXPA03003575A (es) | 2003-07-14 |
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