JP5193863B2 - 2−(3−シアノ−4−イソブチルオキシフェニル)−4−メチル−5−チアゾールカルボン酸の結晶多形体の製造方法 - Google Patents
2−(3−シアノ−4−イソブチルオキシフェニル)−4−メチル−5−チアゾールカルボン酸の結晶多形体の製造方法 Download PDFInfo
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- JP5193863B2 JP5193863B2 JP2008522538A JP2008522538A JP5193863B2 JP 5193863 B2 JP5193863 B2 JP 5193863B2 JP 2008522538 A JP2008522538 A JP 2008522538A JP 2008522538 A JP2008522538 A JP 2008522538A JP 5193863 B2 JP5193863 B2 JP 5193863B2
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- methanol
- isobutyloxyphenyl
- cyano
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- BQSJTQLCZDPROO-UHFFFAOYSA-N febuxostat Chemical compound C1=C(C#N)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)S1 BQSJTQLCZDPROO-UHFFFAOYSA-N 0.000 title claims description 13
- 238000000034 method Methods 0.000 title description 5
- 239000013078 crystal Substances 0.000 claims description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 239000012046 mixed solvent Substances 0.000 claims description 5
- 238000010899 nucleation Methods 0.000 claims 2
- -1 (Cyano-4-isobutyloxyphenyl) -4-methyl-5-thiazolecarboxylic acid Chemical compound 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GGILVSGZJAFNSH-UHFFFAOYSA-N CC1=C(SCN1C2=C(C=C(C=C2)OCC(C)C)C#N)C(=O)O Chemical compound CC1=C(SCN1C2=C(C=C(C=C2)OCC(C)C)C#N)C(=O)O GGILVSGZJAFNSH-UHFFFAOYSA-N 0.000 description 1
- 201000001431 Hyperuricemia Diseases 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Description
左上:0.25+(r−0.007)/(0.01175−0.007)×(0.41−0.25)(mg/mL),50+(r−0.007)/(0.01175−0.007)×(30−50)(分)
左下:0.25+(r−0.007)/(0.01175−0.007)×(0.41−0.25)(mg/mL),40+(r−0.007)/(0.01175−0.007)×(25−40)(分)
右上:1.25(mg/mL),50+(r−0.007)/(0.01175−0.007)×(30−50)(分)
右下:1.25(mg/mL),40+(r−0.007)/(0.01175−0.007)×(25−40)(分)
また、上記は水添加速度の数値に基づいて内挿したものであるが、本発明の目的が達成される範囲において、r<0.007、r>0.01175(単位はmL/分/mL)に外挿してもよい。この場合も同様に、適宜定めた前提条件の水添加速度に基づいて他の具体的条件を容易に計算できるから、その外挿範囲が本発明の目的を達するものであるかどうかは、当業者であれば試行により容易に判断することができる。
[実施例1]
0.024mol/Lの2−(3−シアノ−4−イソブチルオキシフェニル)−4−メチル−5−チアゾールカルボン酸のメタノール/水(95/5)溶液を調製し、その40mLに、内温を40℃に保ちながら0.28mL/分の速度で水を14.2mL添加した。水の添加中、40分経過した時点で種晶(A晶)を10mg添加した。析出した結晶をろ取したのちに乾燥した。得られた結晶の粉末X線回折を行ったところ、A晶であった。また、種晶の添加量を20mgから40mgに変化させても同様にA晶が得られた。
Claims (1)
- 2−(3−シアノ−4−イソブチルオキシフェニル)−4−メチル−5−チアゾールカルボン酸をメタノールまたはメタノール/水混合溶媒(ただしメタノール/水の容量比は90/10以上)に溶解し、次に水をメタノール/水の比率が7/3になるまで40℃以下の状態を保ちながら添加し、さらにかかる水添加中の特定の時期に特定量の種晶を加えることにより2−(3−シアノ−4−イソブチルオキシフェニル)−4−メチル−5−チアゾールカルボン酸のA晶を製造する方法であって、初期濃度が0.024±0.008mol/L、水添加速度が0.007mL/分/mLのとき、種晶添加量および種晶添加時間を図1の領域Iで示される条件とすることを特徴とする方法。
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JP2008522538A JP5193863B2 (ja) | 2006-06-23 | 2007-06-22 | 2−(3−シアノ−4−イソブチルオキシフェニル)−4−メチル−5−チアゾールカルボン酸の結晶多形体の製造方法 |
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JP2006173774 | 2006-06-23 | ||
JP2006173774 | 2006-06-23 | ||
JP2008522538A JP5193863B2 (ja) | 2006-06-23 | 2007-06-22 | 2−(3−シアノ−4−イソブチルオキシフェニル)−4−メチル−5−チアゾールカルボン酸の結晶多形体の製造方法 |
PCT/JP2007/062593 WO2007148787A1 (ja) | 2006-06-23 | 2007-06-22 | 2-(3-シアノ-4-イソブチルオキシフェニル)-4-メチル-5-チアゾールカルボン酸の結晶多形体の製造方法 |
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JPWO2007148787A1 JPWO2007148787A1 (ja) | 2009-11-19 |
JP5193863B2 true JP5193863B2 (ja) | 2013-05-08 |
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US (1) | US8148542B2 (ja) |
EP (1) | EP2039691B1 (ja) |
JP (1) | JP5193863B2 (ja) |
CA (1) | CA2656264C (ja) |
WO (1) | WO2007148787A1 (ja) |
Families Citing this family (8)
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CN101781270B (zh) * | 2009-01-20 | 2013-03-27 | 重庆医药工业研究院有限责任公司 | 一种高纯度的非布司他及其制备方法 |
EP2532654A1 (en) * | 2009-06-10 | 2012-12-12 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of febuxostat |
WO2011080651A2 (en) | 2009-12-31 | 2011-07-07 | Ranbaxy Laboratories Limited | Polymorphic forms of febuxostat |
CA2792036A1 (en) | 2010-03-04 | 2011-09-09 | Ranbaxy Laboratories Limited | Polymorph of 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid |
WO2012098501A1 (en) | 2011-01-21 | 2012-07-26 | Ranbaxy Laboratories Limited | Febuxostat co-crystals |
EP2502920A1 (en) | 2011-03-25 | 2012-09-26 | Sandoz Ag | Crystallization process of Febuxostat from A |
US20150031732A1 (en) | 2011-04-15 | 2015-01-29 | Ranbaxy Laboratories Limited | Febuxostat solid dispersion |
CA2948792A1 (en) * | 2014-05-13 | 2015-11-19 | Teijin Pharma Limited | Novel crystalline polymorphs of pyridine derivative and method for producing the same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1999065885A1 (en) * | 1998-06-19 | 1999-12-23 | Teijin Limited | Polymorphic modifications of 2-(3-cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazole-carboxylic acid and processes for the preparation thereof |
JP2003261548A (ja) * | 2002-03-07 | 2003-09-19 | Teijin Ltd | 2−(3−シアノ−4−イソブチルオキシフェニル)−4−メチル−5−チアゾールカルボン酸の結晶多形体の製造方法 |
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- 2007-06-22 WO PCT/JP2007/062593 patent/WO2007148787A1/ja active Application Filing
- 2007-06-22 EP EP07767403.4A patent/EP2039691B1/en active Active
- 2007-06-22 CA CA2656264A patent/CA2656264C/en active Active
- 2007-06-22 US US12/306,170 patent/US8148542B2/en active Active
- 2007-06-22 JP JP2008522538A patent/JP5193863B2/ja active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999065885A1 (en) * | 1998-06-19 | 1999-12-23 | Teijin Limited | Polymorphic modifications of 2-(3-cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazole-carboxylic acid and processes for the preparation thereof |
JP2003261548A (ja) * | 2002-03-07 | 2003-09-19 | Teijin Ltd | 2−(3−シアノ−4−イソブチルオキシフェニル)−4−メチル−5−チアゾールカルボン酸の結晶多形体の製造方法 |
Non-Patent Citations (4)
Title |
---|
JPN6012005950; KITAMURA, M.: 'Effect of Temperature on Antisolvent Crystallization and Transformation Behaviors of Thiazole-Deriva' Crystal Growth & Design 6(5), 2006, p. 1214-1218 * |
JPN6012005952; KITAMURA, K.: 'Controlling Factors and Mechanism of Polymorphic Crystallization' Crystal Growth & Design 4(6), 2004, p. 1153-1159 * |
JPN6012005953; 北村光孝: '分離プロセス開発の展望 結晶多形の選択的析出技術の開発' ケミカルエンジニヤリング 48(5), 2003, p. 357-365 * |
JPN6012005955; 林善治: 'チアゾール誘導体結晶多形の溶解と析出挙動' 化学工学会秋季大会研究発表講演要旨集 36, 2003, p. 936 * |
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Publication number | Publication date |
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EP2039691B1 (en) | 2013-09-18 |
JPWO2007148787A1 (ja) | 2009-11-19 |
EP2039691A4 (en) | 2010-11-24 |
CA2656264C (en) | 2014-07-08 |
EP2039691A1 (en) | 2009-03-25 |
CA2656264A1 (en) | 2007-12-27 |
WO2007148787A1 (ja) | 2007-12-27 |
US20090203919A1 (en) | 2009-08-13 |
US8148542B2 (en) | 2012-04-03 |
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