CA2426745C - Methods for producing nateglinide b-type crystals - Google Patents

Methods for producing nateglinide b-type crystals Download PDF

Info

Publication number: CA2426745C
Authority: CA; Canada
Prior art keywords: crystals; nateglinide; type crystals; type; drying
Prior art date: 2000-10-24
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

Application number

CA002426745A

Other languages

English (en)

French (fr)

Other versions

CA2426745A1 (en

Inventor

Michito Sumikawa

Makoto Maruo

Kazuo Miyazaki

Shigehiro Nishina

Yukiko Matsuzawa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ajinomoto Co Inc

Original Assignee

Ajinomoto Co Inc

Priority date (The priority date 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 date listed.)

2000-10-24

Filing date

2001-10-23

Publication date

2009-09-15

2001-10-23 Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc

2003-04-23 Publication of CA2426745A1 publication Critical patent/CA2426745A1/en

2009-09-15 Application granted granted Critical

2009-09-15 Publication of CA2426745C publication Critical patent/CA2426745C/en

2021-10-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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)

CA002426745A 2000-10-24 2001-10-23 Methods for producing nateglinide b-type crystals Expired - Fee Related CA2426745C (en)

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

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KR20070104953A (ko) *	2000-03-17	2007-10-29	아지노모토 가부시키가이샤	신경 장애용 약제
PT1334962E (pt) *	2000-10-18	2007-10-09	Ajinomoto Kk	''processo de preparação de acilfenilalaninas''
CA2425538C (en) *	2000-10-18	2010-10-12	Ajinomoto Co., Inc.	Methods for producing nateglinide crystals
RU2271805C2 (ru) *	2000-10-24	2006-03-20	Адзиномото Ко., Инк.	Препарат, содержащий натеглинид
ATE429217T1 (de) *	2000-10-24	2009-05-15	Ajinomoto Kk	Nateglinid enthaltende hydrophile arzneimittelpräparate
US7411089B2 (en)	2002-04-15	2008-08-12	Ajinomoto Co., Inc.	Nateglinide crystals
EP2264004A1 (en) *	2002-04-15	2010-12-22	Ajinomoto Co., Inc.	New nateglinide crystals
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
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
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
DE60310734T2 (de) *	2003-11-26	2007-10-11	A.M.S.A. Anonima Matèrie Sintètiche e Affini S.p.A.	Verfahren zur Herstellung von Nateglinid in der 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
AU2011266820A1 (en)	2010-06-14	2013-01-24	Cipla Limited	A process for the preparation of nateglinide
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PT1334962E (pt) *	2000-10-18	2007-10-09	Ajinomoto Kk	''processo de preparação de acilfenilalaninas''
RU2271805C2 (ru) *	2000-10-24	2006-03-20	Адзиномото Ко., Инк.	Препарат, содержащий натеглинид
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2001
- 2001-10-23 CA CA002426745A patent/CA2426745C/en not_active Expired - Fee Related
- 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 RU RU2003111948/04A patent/RU2275354C2/ru not_active IP Right Cessation
- 2001-10-23 AT AT01976819T patent/ATE370115T1/de active
- 2001-10-23 WO PCT/JP2001/009293 patent/WO2002034713A1/ja not_active Ceased
- 2001-10-23 MX MXPA03003575A patent/MXPA03003575A/es active IP Right Grant
- 2001-10-23 CN CNB018212999A patent/CN100422143C/zh not_active Expired - Fee Related
- 2001-10-23 DK DK01976819T patent/DK1334964T3/da active
- 2001-10-23 AU AU2001296001A patent/AU2001296001A1/en not_active Abandoned
- 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 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 DE DE60130014T patent/DE60130014T2/de not_active Expired - Lifetime
- 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
RU2275354C2 (ru)	2006-04-27
DK1334964T3 (da)	2007-09-24
CY1106839T1 (el)	2012-05-23
EP1334964A1 (en)	2003-08-13
KR20030059212A (ko)	2003-07-07
ATE370115T1 (de)	2007-09-15
EP1334964B1 (en)	2007-08-15
PT1334964E (pt)	2007-09-20
WO2002034713A1 (en)	2002-05-02
BR0114846A (pt)	2004-02-25
MXPA03003575A (es)	2003-07-14
US20070232829A1 (en)	2007-10-04
TWI293290B (2)	2008-02-11
JPWO2002034713A1 (ja)	2004-03-04
DE60130014D1 (de)	2007-09-27
US20030229249A1 (en)	2003-12-11
CN100422143C (zh)	2008-10-01
ES2288997T3 (es)	2008-02-01
KR100810930B1 (ko)	2008-03-10
CA2426745A1 (en)	2003-04-23
JP4225057B2 (ja)	2009-02-18
EP1334964A4 (en)	2005-09-28
CN1483018A (zh)	2004-03-17
AU2001296001A1 (en)	2002-05-06
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