JP4615866B2 - N−(トランス−4−イソプロピルシクロヘキシルカルボニル)−d−フェニルアラニンの結晶形 - Google Patents
N−(トランス−4−イソプロピルシクロヘキシルカルボニル)−d−フェニルアラニンの結晶形 Download PDFInfo
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- JP4615866B2 JP4615866B2 JP2003583994A JP2003583994A JP4615866B2 JP 4615866 B2 JP4615866 B2 JP 4615866B2 JP 2003583994 A JP2003583994 A JP 2003583994A JP 2003583994 A JP2003583994 A JP 2003583994A JP 4615866 B2 JP4615866 B2 JP 4615866B2
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- nateglinide
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- OELFLUMRDSZNSF-BRWVUGGUSA-N CC(C)[C@H](CC1)CC[C@@H]1C(N[C@H](Cc1ccccc1)C(O)=O)=O Chemical compound CC(C)[C@H](CC1)CC[C@@H]1C(N[C@H](Cc1ccccc1)C(O)=O)=O OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- 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
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- 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
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
図2は、N−(トランス−4−イソプロピル−シクロヘキシルカルボニル)−D−フェニルアラニンのB−型結晶の赤外吸収スペクトルを示す。
B−型のナテグリニド結晶形の融点(mp)は、128〜131℃の範囲にあることがDSC法により測定された。
R’−型のナテグリニド結晶は、以下のように製造され得る:
H−型のナテグリニド結晶を、エタノールおよびトルエン(50%(容積)のエタノールおよび50%(容積)のトルエン;160mg/mLのナテグリニド)の混合物中で室温にて撹拌しながら溶かす。すべての固体が溶けた後に、1%ヒドロキシプロピルメチルセルロースを含有する水を添加して、沈澱を生じさせる(使用されたエタノール−トルエンの容積の約7倍)。さらに2時間撹拌した後、沈澱した固体を真空濾過により集め、洗浄し、そして減圧下で50℃にて一夜乾燥するとR’−型の結晶を得る:融点108℃。
Claims (6)
- ナテグリニドの結晶形の製造方法であって;
(a)ナテグリニドが周囲温度で容易に溶ける第1の溶媒に任意の形態のナテグリニドを溶かして溶液を形成させること;
(b)該溶液を、第1の溶媒と混和可能であり、かつ、ナテグリニドが僅かにしか溶けない第2の溶媒で処理し、ナテグリニドの結晶の沈澱を生じさせること;ならびに
(c)沈澱したナテグリニドの結晶形を単離および乾燥すること
を含み、
ここで、第1の溶媒がエタノールおよびトルエンの混合物であり、第2の溶媒が0.5〜3重量%のヒドロキシプロピルメチルセルロースを含有する水である方法。 - ナテグリニドの結晶形の沈澱を、撹拌、冷却またはナテグリニドの種晶の添加により生じさせる、請求項1に記載の方法。
- 周囲温度が、室温から溶媒の沸点までの範囲である、請求項1または2に記載の方法。
- ナテグリニドの結晶形を、大気圧または減圧下で、室温から70℃までの範囲の温度にて乾燥する、請求項1ないし3のいずれかに記載の方法。
- 第1の溶媒が50%(容積)のエタノールを含有し;第2の溶媒が1%のヒドロキシプロピルメチルセルロースを含有し;そして第1の溶媒と第2の溶媒の容積比が1:7である、請求項1ないし4のいずれかに記載の方法。
- 周囲温度が室温であり;そしてナテグリニドの結晶形を、減圧下で室温から50℃の範囲の温度にて乾燥する、請求項1ないし5のいずれかに記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US37262502P | 2002-04-15 | 2002-04-15 | |
PCT/EP2003/003864 WO2003087038A1 (en) | 2002-04-15 | 2003-04-14 | Crystal forms of n-(trans-4-isopropylcyclohexylcarbonyl)-d-phenylalanine |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010156749A Division JP2010265295A (ja) | 2002-04-15 | 2010-07-09 | N−(トランス−4−イソプロピルシクロヘキシルカルボニル)−d−フェニルアラニンの結晶形 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2005522503A JP2005522503A (ja) | 2005-07-28 |
JP2005522503A5 JP2005522503A5 (ja) | 2006-06-01 |
JP4615866B2 true JP4615866B2 (ja) | 2011-01-19 |
Family
ID=29250881
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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JP2003583994A Expired - Fee Related JP4615866B2 (ja) | 2002-04-15 | 2003-04-14 | N−(トランス−4−イソプロピルシクロヘキシルカルボニル)−d−フェニルアラニンの結晶形 |
JP2010156749A Pending JP2010265295A (ja) | 2002-04-15 | 2010-07-09 | N−(トランス−4−イソプロピルシクロヘキシルカルボニル)−d−フェニルアラニンの結晶形 |
Family Applications After (1)
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JP2010156749A Pending JP2010265295A (ja) | 2002-04-15 | 2010-07-09 | N−(トランス−4−イソプロピルシクロヘキシルカルボニル)−d−フェニルアラニンの結晶形 |
Country Status (8)
Country | Link |
---|---|
US (3) | US7247746B2 (ja) |
EP (1) | EP1497258A1 (ja) |
JP (2) | JP4615866B2 (ja) |
CN (1) | CN1304366C (ja) |
AU (1) | AU2003242520A1 (ja) |
BR (1) | BR0309210A (ja) |
CA (1) | CA2482669A1 (ja) |
WO (1) | WO2003087038A1 (ja) |
Families Citing this family (58)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
US7534913B2 (en) | 2002-07-18 | 2009-05-19 | Teva Pharmaceutica Industries Ltd. | Crystalline form 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 |
US20040077725A1 (en) * | 2002-08-28 | 2004-04-22 | Dr. Reddy's Laboratories Limited | Crystalline form of N-(trans-4-isopropylcyclohexane carbonyl)-D-phenylalanine and process for preparation thereof |
JPWO2004074330A1 (ja) * | 2003-02-18 | 2006-06-01 | コニシ株式会社 | 硬化性樹脂、その製造方法及び硬化性樹脂組成物 |
HU227073B1 (hu) * | 2003-07-10 | 2010-06-28 | Richter Gedeon Nyrt | Eljárás királisan tiszta N-(transz-4-izopropil-ciklohexilkarbonil)-D-fenil-alanin (nateglinid) és kristálymódosulatainak elõállítására, valamint a G-kristálymódosulata |
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US9290486B1 (en) | 2014-11-05 | 2016-03-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy |
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US9321716B1 (en) | 2014-11-05 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
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JPS6354321A (ja) * | 1985-03-27 | 1988-03-08 | Ajinomoto Co Inc | 血糖降下剤 |
ATE149483T1 (de) * | 1991-07-30 | 1997-03-15 | Ajinomoto Kk | 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 |
WO2003022251A1 (en) * | 2001-09-12 | 2003-03-20 | Alembic Limited | Novel stable crystal form of n-trans-4-isopropylcyclohexyl carbonyl)-d-phenylalanine and process of preparation |
WO2003087039A1 (fr) * | 2002-04-15 | 2003-10-23 | Ajinomoto Co., Inc. | Nouveau cristal de nateglinide |
-
2003
- 2003-04-14 JP JP2003583994A patent/JP4615866B2/ja not_active Expired - Fee Related
- 2003-04-14 EP EP03746296A patent/EP1497258A1/en not_active Withdrawn
- 2003-04-14 BR BR0309210-0A patent/BR0309210A/pt not_active IP Right Cessation
- 2003-04-14 CA CA002482669A patent/CA2482669A1/en not_active Abandoned
- 2003-04-14 US US10/510,927 patent/US7247746B2/en not_active Expired - Fee Related
- 2003-04-14 CN CNB038084368A patent/CN1304366C/zh not_active Expired - Lifetime
- 2003-04-14 WO PCT/EP2003/003864 patent/WO2003087038A1/en active Application Filing
- 2003-04-14 AU AU2003242520A patent/AU2003242520A1/en not_active Abandoned
-
2007
- 2007-06-20 US US11/765,818 patent/US20080081927A1/en not_active Abandoned
-
2008
- 2008-07-21 US US12/220,061 patent/US20080319222A1/en not_active Abandoned
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2010
- 2010-07-09 JP JP2010156749A patent/JP2010265295A/ja active Pending
Also Published As
Publication number | Publication date |
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CN1304366C (zh) | 2007-03-14 |
CN1646481A (zh) | 2005-07-27 |
JP2005522503A (ja) | 2005-07-28 |
US7247746B2 (en) | 2007-07-24 |
JP2010265295A (ja) | 2010-11-25 |
WO2003087038A1 (en) | 2003-10-23 |
BR0309210A (pt) | 2005-02-09 |
AU2003242520A1 (en) | 2003-10-27 |
US20050256336A1 (en) | 2005-11-17 |
CA2482669A1 (en) | 2003-10-23 |
US20080081927A1 (en) | 2008-04-03 |
EP1497258A1 (en) | 2005-01-19 |
US20080319222A1 (en) | 2008-12-25 |
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