US20030229249A1 - Methods for producing nateglinide B-type crystals - Google Patents
Methods for producing nateglinide B-type crystals Download PDFInfo
- Publication number
- US20030229249A1 US20030229249A1 US10/421,888 US42188803A US2003229249A1 US 20030229249 A1 US20030229249 A1 US 20030229249A1 US 42188803 A US42188803 A US 42188803A US 2003229249 A1 US2003229249 A1 US 2003229249A1
- Authority
- US
- United States
- Prior art keywords
- crystals
- nateglinide
- type crystals
- type
- crystal
- 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
- 239000013078 crystal Substances 0.000 title claims abstract description 103
- 229960000698 nateglinide Drugs 0.000 title claims abstract description 41
- 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 39
- 238000000034 method Methods 0.000 title claims abstract description 14
- 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 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010438 heat treatment 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
- 239000000463 material Substances 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
- 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
- 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
- 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
Definitions
- the present invention relates to methods for producing nateglinide (its chemical name: N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine) that is useful as a therapeutic agent for diabetes. More specifically, it relates to methods for producing nateglinide B-type crystals substantially free of H-type crystals.
- nateglinide is useful as a therapeutic agent for diabetes because it effectively lowers blood glucose by oral administration (Japanese Patent Publication No. Hei 4-15221).
- Japanese Patent Publication No. Hei 4-15221 Japanese Patent Publication No. Hei 4-15221.
- the crystallization has to be carefully conducted under precisely controlled conditions in order to separate H-type crystals and difficulty of such crystallization procedure was problematic (see Japanese Patent No. 2,508,949).
- one of crystal polymorphs of nateglinide has an advantage in that the B-type crystals can be easily prepared by conducting the crystallization under cooling.
- the B-type crystals are transferred to the H-type crystals during the production stage.
- H-type crystals were contaminated in the resulting B-type crystals.
- a contamination of crystal polymorphs be as small as possible.
- An object of the present invention is to provide methods for producing B-type crystals of nateglinide at an industrial scale without allowing other forms of the crystalline polymorphism to coexist.
- the present invention provides a method for producing B-type crystals of nateglinide substantially free of H-type crystals, which comprises drying solvated wet crystals of nateglinide at a low temperature until no solvent remains and making a crystal conversion thereof.
- the present invention provides a method for producing B-type crystals of nateglinide substantially free of H-type crystals, which comprises drying solvated materials containing nateglinide hydrates obtained by crystallizing out from a nateglinide-containing solution under cooling, at a temperature of 50° C. or lower until no solvent remains, and heating the resultant at a temperature of 60 to 110° C. to convert the crystal form of the resultant into B-type crystal.
- Examples of the solvated wet crystals of nateglinide employed in the present invention include solvates with an alcohol such as methanol, ethanol and isopropyl alcohol, an acetate such as methyl acetate and ethyl acetate, or water.
- the solvates with an alcohol or hydrate are usually used as the solvated wet crystals of nateglinide.
- nateglinide is added to 60% ethanol aqueous solution so that the concentration of nateglinide becomes 5 wt %, dissolved at a temperature of around 30° C. and cooled down to 10° C. or lower to obtain the solvates.
- the hydrates can be easily obtained by adding water to an alcohol solution, preferably ethanol solution, of nateglinide, cooling it to 10° C. or lower, thereby crystals are precipitated out, and separating the resulting crystals therefrom.
- an alcohol solution preferably ethanol solution
- nateglinide nateglinide
- Solvated wet crystals obtained are dried until no solvent remains any longer.
- the temperature employed may vary depending on the type and the amount of a solvent associated with the crystals, and may usually be 60° C. or lower, preferably 50° C. or lower. While no lower limit of the temperature is specified, a temperature of 20° C. or higher is usually employed in an economical point of view. Usually, it is preferable that the drying be conducted under the reduced pressure, and the drying can be completed in a short time of period when the pressure is as reduced as industrially possible.
- the dried crystals obtained are converted into B-type crystals by heating at 60 to 110° C., preferably 70 to 110° C.
- the crystal conversion is preferably conducted for 0.5 to 48 hours, more preferably 1 to 24 hours.
- H-type crystals contaminated in the B-type crystals can be analyzed with DSC. It is preferable that no H-type crystals be detected by analyzing B-type crystals of nateglinide with the DSC.
- the drying temperature at an early stage causes no substantial problem when wet B-type crystals of nateglinide are dried at a small scale in a laboratory since the solvent after the separation of the crystals remains only in a small amount and the drier can rapidly reach the maximum reduced pressure.
- the B-type crystals free of H-type crystals can be produced according to methods of the present invention, even in a production at an industrial scale, for example, production of 5 Kg or more of the B-type crystals per one batch, in which the solvent remains in the crystals in a large amount after the separation from the liquid where the crystallization is conducted and the time period required for reaching the maximum reduced pressure is relatively long in the drying step.
- the crystals were subjected to DSC, which revealed the presence of a peak specific to the B-type crystals (melting point: about 130° C.) without showing a peak specific to the H-type crystals (melting point: about 139° C.). Therefore, it is concluded that the resulting crystals are only B-type crystals which are substantially free of the H-type crystals.
- B-type crystals of nateglinide can be produced at an industrial scale without allowing other crystal forms to be present, and a pharmaceutical formulation containing B-type crystals of nateglinide as a single nateglinide crystal can be provided at a low cost.
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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/757,769 US7544834B2 (en) | 2000-10-24 | 2007-06-04 | Methods for producing nateglinide B-type crystals |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000324375 | 2000-10-24 | ||
| JP2000-324375 | 2000-10-24 | ||
| PCT/JP2001/009293 WO2002034713A1 (fr) | 2000-10-24 | 2001-10-23 | Procede de production de cristaux de nateglinide a forme b |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2001/009293 Continuation WO2002034713A1 (fr) | 2000-10-24 | 2001-10-23 | Procede de production de cristaux de nateglinide a forme b |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/757,769 Continuation US7544834B2 (en) | 2000-10-24 | 2007-06-04 | Methods for producing nateglinide B-type crystals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20030229249A1 true US20030229249A1 (en) | 2003-12-11 |
Family
ID=18801920
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/421,888 Abandoned US20030229249A1 (en) | 2000-10-24 | 2003-04-24 | Methods for producing nateglinide B-type crystals |
| US11/757,769 Expired - Fee Related US7544834B2 (en) | 2000-10-24 | 2007-06-04 | Methods for producing nateglinide B-type crystals |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/757,769 Expired - Fee Related US7544834B2 (en) | 2000-10-24 | 2007-06-04 | Methods for producing nateglinide B-type crystals |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US20030229249A1 (cs) |
| EP (1) | EP1334964B1 (cs) |
| JP (1) | JP4225057B2 (cs) |
| KR (1) | KR100810930B1 (cs) |
| CN (1) | CN100422143C (cs) |
| AT (1) | ATE370115T1 (cs) |
| AU (1) | AU2001296001A1 (cs) |
| BR (1) | BR0114846A (cs) |
| CA (1) | CA2426745C (cs) |
| CY (1) | CY1106839T1 (cs) |
| DE (1) | DE60130014T2 (cs) |
| DK (1) | DK1334964T3 (cs) |
| ES (1) | ES2288997T3 (cs) |
| MX (1) | MXPA03003575A (cs) |
| PT (1) | PT1334964E (cs) |
| RU (1) | RU2275354C2 (cs) |
| TW (1) | TWI293290B (cs) |
| WO (1) | WO2002034713A1 (cs) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030073729A1 (en) * | 2000-03-17 | 2003-04-17 | Ajinomoto Co. Inc | Medicaments for diabetic complication and neuropathy, and uses thereof |
| US20040014815A1 (en) * | 2000-10-24 | 2004-01-22 | Ajinomoto Co. Inc. | Nateglinide-containing preparation |
| US20040024219A1 (en) * | 2000-10-18 | 2004-02-05 | Ajinomoto Co. Inc | Methods for producing acylphenylalanine |
| US20040029968A1 (en) * | 2000-10-24 | 2004-02-12 | Ajinomoto Co. Inc | Nateglinide-containing hydrophilic pharmaceutical preparation |
| US20040030182A1 (en) * | 2000-10-18 | 2004-02-12 | Ajinomoto Co. Inc. | Methods for producing nateglinide crystals |
| WO2005110395A1 (en) * | 2004-05-19 | 2005-11-24 | University Of South Carolina | System and device for magnetic drug targeting with magnetic drug carrier particles |
| WO2007135533A1 (en) * | 2006-05-23 | 2007-11-29 | Aurobindo Pharma Limited | Process for preparing nateglinide b-type crystals |
| US20070275999A1 (en) * | 2005-01-31 | 2007-11-29 | Ajinomoto Co., Inc. | Pharmaceutical compositions containing a hypoglycemic agent(s) for improving or treating impaired glucose tolerance, borderline diabetes, insulin resistance or hyperinsulinemia |
| US7411089B2 (en) | 2002-04-15 | 2008-08-12 | Ajinomoto Co., Inc. | Nateglinide crystals |
| US20080319075A1 (en) * | 2002-07-18 | 2008-12-25 | Ronit Yahalomi | Polymorphic forms of nateglinide |
| WO2005113485A3 (en) * | 2004-05-20 | 2009-04-30 | Reddys Lab Ltd Dr | Stable nateglinide form b compositions |
| WO2011157986A1 (en) | 2010-06-14 | 2011-12-22 | Cipla Limited | A process for the preparation of nateglinide |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6861553B2 (en) | 2002-07-03 | 2005-03-01 | Teva Pharmaceuticals Industries Ltd. | Process for preparing nateglinide and intermediates thereof |
| 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 |
| US7358390B2 (en) | 2002-07-18 | 2008-04-15 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| JP2006511614A (ja) * | 2002-07-18 | 2006-04-06 | テバ ファーマシューティカル インダストリーズ リミティド | ナテグリニドの多形性形状 |
| ATE349418T1 (de) * | 2003-11-26 | 2007-01-15 | A M S A Anonima Materie Sint E | Verfahren zur herstellung von nateglinidin der b- form |
| WO2005110972A1 (en) * | 2004-05-07 | 2005-11-24 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| 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 |
| KR100837843B1 (ko) * | 2006-12-26 | 2008-06-13 | 씨제이제일제당 (주) | 나테글리나이드 결정형, 그 제조방법, 및 그를 포함하는약제학적 조성물 |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030021843A1 (en) * | 1999-12-28 | 2003-01-30 | Ajinomoto Co. Inc | Antidiabetic preparation for oral administration |
| US20030073729A1 (en) * | 2000-03-17 | 2003-04-17 | Ajinomoto Co. Inc | Medicaments for diabetic complication and neuropathy, and uses thereof |
| US20040014815A1 (en) * | 2000-10-24 | 2004-01-22 | Ajinomoto Co. Inc. | Nateglinide-containing preparation |
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| US20040030182A1 (en) * | 2000-10-18 | 2004-02-12 | Ajinomoto Co. Inc. | Methods for producing nateglinide crystals |
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| AU615966B2 (en) * | 1987-12-04 | 1991-10-17 | Takeda Chemical Industries Ltd. | Crystals of cephem hydrochloride |
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| ATE149483T1 (de) | 1991-07-30 | 1997-03-15 | Ajinomoto Kk | Kristalle von n-(trans-4- isopropylcyclohexylcarbonyl)-d-phenylalanin und verfahren zu ihrer herstellung |
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2001
- 2001-10-23 KR KR1020037005671A patent/KR100810930B1/ko not_active Expired - Fee Related
- 2001-10-23 RU RU2003111948/04A patent/RU2275354C2/ru not_active IP Right Cessation
- 2001-10-23 AT AT01976819T patent/ATE370115T1/de active
- 2001-10-23 CN CNB018212999A patent/CN100422143C/zh not_active Expired - Fee Related
- 2001-10-23 BR BR0114846-0A patent/BR0114846A/pt not_active IP Right Cessation
- 2001-10-23 AU AU2001296001A patent/AU2001296001A1/en not_active Abandoned
- 2001-10-23 ES ES01976819T patent/ES2288997T3/es not_active Expired - Lifetime
- 2001-10-23 PT PT01976819T patent/PT1334964E/pt unknown
- 2001-10-23 CA CA002426745A patent/CA2426745C/en not_active Expired - Fee Related
- 2001-10-23 MX MXPA03003575A patent/MXPA03003575A/es active IP Right Grant
- 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 DK DK01976819T patent/DK1334964T3/da active
- 2001-10-23 WO PCT/JP2001/009293 patent/WO2002034713A1/ja active IP Right Grant
- 2001-10-23 JP JP2002537707A patent/JP4225057B2/ja not_active Expired - Fee Related
- 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
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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
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6844008B2 (en) * | 1996-11-15 | 2005-01-18 | Ajinomoto Co., Inc. | Tablet composition |
| US20030021843A1 (en) * | 1999-12-28 | 2003-01-30 | Ajinomoto Co. Inc | Antidiabetic preparation for oral administration |
| US20030073729A1 (en) * | 2000-03-17 | 2003-04-17 | Ajinomoto Co. Inc | Medicaments for diabetic complication and neuropathy, and uses thereof |
| US20040024219A1 (en) * | 2000-10-18 | 2004-02-05 | Ajinomoto Co. Inc | Methods for producing acylphenylalanine |
| US20040030182A1 (en) * | 2000-10-18 | 2004-02-12 | Ajinomoto Co. Inc. | Methods for producing nateglinide crystals |
| US20040014815A1 (en) * | 2000-10-24 | 2004-01-22 | Ajinomoto Co. Inc. | Nateglinide-containing preparation |
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030073729A1 (en) * | 2000-03-17 | 2003-04-17 | Ajinomoto Co. Inc | Medicaments for diabetic complication and neuropathy, and uses thereof |
| US7459582B2 (en) | 2000-10-18 | 2008-12-02 | Ajinomoto Co., Inc. | Methods for producing nateglinide crystals |
| US20090076301A1 (en) * | 2000-10-18 | 2009-03-19 | Ajinomoto Co. Inc | Methods for producing nateglinide crystals |
| US20040030182A1 (en) * | 2000-10-18 | 2004-02-12 | Ajinomoto Co. Inc. | Methods for producing nateglinide crystals |
| US7030268B2 (en) | 2000-10-18 | 2006-04-18 | Ajinomoto Co., Inc. | Methods for producing acylphenylalanine |
| US20060155143A1 (en) * | 2000-10-18 | 2006-07-13 | Ajinomoto Co. Inc | Methods for producing acylphenylalanine |
| US7208622B2 (en) | 2000-10-18 | 2007-04-24 | Ajinomoto Co., Inc. | Methods for producing nateglinide crystals |
| US20070167523A1 (en) * | 2000-10-18 | 2007-07-19 | Ajinomoto Co. Inc | Methods for producing nateglinide crystals |
| US7659428B2 (en) | 2000-10-18 | 2010-02-09 | Ajinomoto Co., Inc. | Methods for producing acylphenylalanine |
| US20040024219A1 (en) * | 2000-10-18 | 2004-02-05 | Ajinomoto Co. Inc | Methods for producing acylphenylalanine |
| US20040029968A1 (en) * | 2000-10-24 | 2004-02-12 | Ajinomoto Co. Inc | Nateglinide-containing hydrophilic pharmaceutical preparation |
| US20040014815A1 (en) * | 2000-10-24 | 2004-01-22 | Ajinomoto Co. Inc. | Nateglinide-containing preparation |
| US7605180B2 (en) | 2000-10-24 | 2009-10-20 | Ajinomoto Co., Inc. | Nateglinide-containing preparation |
| US20090203791A1 (en) * | 2000-10-24 | 2009-08-13 | Ajinomoto Co. Inc | Nateglinide-containing preparation |
| US7977507B2 (en) | 2002-04-15 | 2011-07-12 | Ajinomoto Co., Inc. | Nateglinide crystals |
| US7888531B2 (en) | 2002-04-15 | 2011-02-15 | Ajinomoto Co., Inc. | Nateglinide crystals |
| US20080194867A1 (en) * | 2002-04-15 | 2008-08-14 | Ajinomoto Co., Inc. | Nateglinide crystals |
| US20110092733A1 (en) * | 2002-04-15 | 2011-04-21 | Ajinomoto Co., Inc. | Nateglinide crystals |
| US7411089B2 (en) | 2002-04-15 | 2008-08-12 | Ajinomoto Co., Inc. | Nateglinide crystals |
| US7586001B2 (en) | 2002-04-15 | 2009-09-08 | Ajinomoto Co., Inc. | Nateglinide crystals |
| US20090253933A1 (en) * | 2002-04-15 | 2009-10-08 | Ajinomoto Co., Inc. | Nateglinide crystals |
| US20080319075A1 (en) * | 2002-07-18 | 2008-12-25 | Ronit Yahalomi | Polymorphic forms of nateglinide |
| WO2005110395A1 (en) * | 2004-05-19 | 2005-11-24 | University Of South Carolina | System and device for magnetic drug targeting with magnetic drug carrier particles |
| WO2005113485A3 (en) * | 2004-05-20 | 2009-04-30 | Reddys Lab Ltd Dr | Stable nateglinide form b compositions |
| US20070275999A1 (en) * | 2005-01-31 | 2007-11-29 | Ajinomoto Co., Inc. | Pharmaceutical compositions containing a hypoglycemic agent(s) for improving or treating impaired glucose tolerance, borderline diabetes, insulin resistance or hyperinsulinemia |
| WO2007135533A1 (en) * | 2006-05-23 | 2007-11-29 | Aurobindo Pharma Limited | Process for preparing nateglinide b-type crystals |
| WO2011157986A1 (en) | 2010-06-14 | 2011-12-22 | Cipla Limited | A process for the preparation of nateglinide |
| US9150499B2 (en) | 2010-06-14 | 2015-10-06 | Cipla Limited | Process for the preparation of nateglinide |
Also Published As
| Publication number | Publication date |
|---|---|
| US7544834B2 (en) | 2009-06-09 |
| BR0114846A (pt) | 2004-02-25 |
| TWI293290B (cs) | 2008-02-11 |
| EP1334964A4 (en) | 2005-09-28 |
| JPWO2002034713A1 (ja) | 2004-03-04 |
| DK1334964T3 (da) | 2007-09-24 |
| ES2288997T3 (es) | 2008-02-01 |
| PT1334964E (pt) | 2007-09-20 |
| US20070232829A1 (en) | 2007-10-04 |
| EP1334964B1 (en) | 2007-08-15 |
| CA2426745A1 (en) | 2003-04-23 |
| RU2275354C2 (ru) | 2006-04-27 |
| WO2002034713A1 (fr) | 2002-05-02 |
| KR20030059212A (ko) | 2003-07-07 |
| AU2001296001A1 (en) | 2002-05-06 |
| EP1334964A1 (en) | 2003-08-13 |
| ATE370115T1 (de) | 2007-09-15 |
| JP4225057B2 (ja) | 2009-02-18 |
| MXPA03003575A (es) | 2003-07-14 |
| DE60130014D1 (de) | 2007-09-27 |
| DE60130014T2 (de) | 2008-05-08 |
| KR100810930B1 (ko) | 2008-03-10 |
| CN1483018A (zh) | 2004-03-17 |
| CN100422143C (zh) | 2008-10-01 |
| CA2426745C (en) | 2009-09-15 |
| CY1106839T1 (el) | 2012-05-23 |
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