US20030229249A1 - Methods for producing nateglinide B-type crystals - Google Patents

Methods for producing nateglinide B-type crystals Download PDF

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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
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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
Application number
US10/421,888
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English (en)
Inventor
Michito Sumikawa
Makoto Maruo
Kazuo Miyazaki
Shigehiro Nishina
Yukiko Matsuzawa
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Ajinomoto Co Inc
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Ajinomoto Co Inc
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Publication date
Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Assigned to AJINOMOTO CO., INC. reassignment AJINOMOTO CO., INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MARUO, MAKOTO, MATSUZAWA, YUKIKO, MIYAZAKI, KAZUO, NISHINA, SHIGEHIRO, SUMIKAWA, MICHITO
Publication of US20030229249A1 publication Critical patent/US20030229249A1/en
Priority to US11/757,769 priority Critical patent/US7544834B2/en
Abandoned legal-status Critical Current

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    • 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)
US10/421,888 2000-10-24 2003-04-24 Methods for producing nateglinide B-type crystals Abandoned US20030229249A1 (en)

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
JP2000-324375 2000-10-24
JP2000324375 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

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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

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Country Status (18)

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US (2) US20030229249A1 (zh)
EP (1) EP1334964B1 (zh)
JP (1) JP4225057B2 (zh)
KR (1) KR100810930B1 (zh)
CN (1) CN100422143C (zh)
AT (1) ATE370115T1 (zh)
AU (1) AU2001296001A1 (zh)
BR (1) BR0114846A (zh)
CA (1) CA2426745C (zh)
CY (1) CY1106839T1 (zh)
DE (1) DE60130014T2 (zh)
DK (1) DK1334964T3 (zh)
ES (1) ES2288997T3 (zh)
MX (1) MXPA03003575A (zh)
PT (1) PT1334964E (zh)
RU (1) RU2275354C2 (zh)
TW (1) TWI293290B (zh)
WO (1) WO2002034713A1 (zh)

Cited By (12)

* Cited by examiner, † Cited by third party
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
US20040030182A1 (en) * 2000-10-18 2004-02-12 Ajinomoto Co. Inc. Methods for producing nateglinide crystals
US20040029968A1 (en) * 2000-10-24 2004-02-12 Ajinomoto Co. Inc Nateglinide-containing hydrophilic pharmaceutical preparation
WO2005110395A1 (en) * 2004-05-19 2005-11-24 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
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
WO2011157986A1 (en) 2010-06-14 2011-12-22 Cipla Limited A process for the preparation of nateglinide

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* Cited by examiner, † Cited by third party
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AU2003236243A1 (en) * 2002-04-15 2003-10-27 Ajinomoto Co., Inc. Novel nateglinide crystal
US6861553B2 (en) 2002-07-03 2005-03-01 Teva Pharmaceuticals Industries Ltd. Process for preparing nateglinide and intermediates thereof
AU2003253971A1 (en) * 2002-07-18 2004-02-09 Teva Pharmaceutical Industries Ltd. Polymorphic forms of nateglinide
US7534913B2 (en) 2002-07-18 2009-05-19 Teva Pharmaceutica Industries Ltd. Crystalline form of nateglinide
US7358390B2 (en) 2002-07-18 2008-04-15 Teva Pharmaceutical Industries Ltd. Polymorphic forms of nateglinide
US7148376B2 (en) 2002-07-18 2006-12-12 Teva Pharmaceutical Industries Ltd. Polymorphic forms of nateglinide
ATE349418T1 (de) * 2003-11-26 2007-01-15 A M S A Anonima Materie Sint E Verfahren zur herstellung von nateglinidin der b- form
EP1656339A1 (en) * 2004-05-07 2006-05-17 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)

* Cited by examiner, † Cited by third party
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
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
US6844008B2 (en) * 1996-11-15 2005-01-18 Ajinomoto Co., Inc. Tablet composition

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6354321A (ja) * 1985-03-27 1988-03-08 Ajinomoto Co Inc 血糖降下剤
DE10199058I2 (de) 1991-07-30 2006-04-27 Alcm Co Kristalle von N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanin und Verfahren zu ihrer Herstellung
US5463116A (en) * 1991-07-30 1995-10-31 Ajinomoto Co., Inc. Crystals of N- (trans-4-isopropylcyclohexlycarbonyl)-D-phenylalanine and methods for preparing them
US6844006B1 (en) * 1999-07-09 2005-01-18 Pennfield Oil Company Process and apparatus for the preparation of chlortetracycline-containing animal feed compositions
US7411089B2 (en) 2002-04-15 2008-08-12 Ajinomoto Co., Inc. Nateglinide crystals

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (29)

* Cited by examiner, † Cited by third party
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
US7208622B2 (en) 2000-10-18 2007-04-24 Ajinomoto Co., Inc. Methods for producing nateglinide crystals
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
US7659428B2 (en) 2000-10-18 2010-02-09 Ajinomoto Co., Inc. Methods for producing acylphenylalanine
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
US20070167523A1 (en) * 2000-10-18 2007-07-19 Ajinomoto Co. Inc Methods for producing nateglinide crystals
US20090076301A1 (en) * 2000-10-18 2009-03-19 Ajinomoto Co. Inc Methods for producing nateglinide crystals
US7459582B2 (en) 2000-10-18 2008-12-02 Ajinomoto Co., Inc. Methods for producing nateglinide crystals
US20040029968A1 (en) * 2000-10-24 2004-02-12 Ajinomoto Co. Inc Nateglinide-containing hydrophilic pharmaceutical preparation
US7605180B2 (en) 2000-10-24 2009-10-20 Ajinomoto Co., Inc. Nateglinide-containing preparation
US20040014815A1 (en) * 2000-10-24 2004-01-22 Ajinomoto Co. Inc. Nateglinide-containing preparation
US20090203791A1 (en) * 2000-10-24 2009-08-13 Ajinomoto Co. Inc Nateglinide-containing preparation
US20080194867A1 (en) * 2002-04-15 2008-08-14 Ajinomoto Co., Inc. Nateglinide crystals
US7888531B2 (en) 2002-04-15 2011-02-15 Ajinomoto Co., Inc. Nateglinide crystals
US7977507B2 (en) 2002-04-15 2011-07-12 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
US20090253933A1 (en) * 2002-04-15 2009-10-08 Ajinomoto Co., Inc. Nateglinide crystals
US7586001B2 (en) 2002-04-15 2009-09-08 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
WO2005113485A2 (en) * 2004-05-20 2005-12-01 Dr. Reddy's Laboratories Ltd. Stable nateglinide form b compositions
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

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WO2002034713A1 (fr) 2002-05-02
EP1334964B1 (en) 2007-08-15
CN100422143C (zh) 2008-10-01
CA2426745C (en) 2009-09-15
EP1334964A1 (en) 2003-08-13
TWI293290B (zh) 2008-02-11
US7544834B2 (en) 2009-06-09
ES2288997T3 (es) 2008-02-01
US20070232829A1 (en) 2007-10-04
JPWO2002034713A1 (ja) 2004-03-04
BR0114846A (pt) 2004-02-25
JP4225057B2 (ja) 2009-02-18
PT1334964E (pt) 2007-09-20
DE60130014T2 (de) 2008-05-08
KR100810930B1 (ko) 2008-03-10
ATE370115T1 (de) 2007-09-15
CN1483018A (zh) 2004-03-17
CY1106839T1 (el) 2012-05-23
EP1334964A4 (en) 2005-09-28
MXPA03003575A (es) 2003-07-14
CA2426745A1 (en) 2003-04-23
KR20030059212A (ko) 2003-07-07
RU2275354C2 (ru) 2006-04-27
AU2001296001A1 (en) 2002-05-06
DK1334964T3 (da) 2007-09-24

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