JP2011527330A5 - - Google Patents
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- Publication number
- JP2011527330A5 JP2011527330A5 JP2011517242A JP2011517242A JP2011527330A5 JP 2011527330 A5 JP2011527330 A5 JP 2011527330A5 JP 2011517242 A JP2011517242 A JP 2011517242A JP 2011517242 A JP2011517242 A JP 2011517242A JP 2011527330 A5 JP2011527330 A5 JP 2011527330A5
- Authority
- JP
- Japan
- Prior art keywords
- malic acid
- sunitinib
- iii
- mixture
- methanol
- 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.)
- Pending
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 45
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 38
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 38
- 235000011090 malic acid Nutrition 0.000 claims 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 33
- 229940099690 malic acid Drugs 0.000 claims 30
- 239000001630 malic acid Substances 0.000 claims 30
- 239000002904 solvent Substances 0.000 claims 27
- 239000002147 L01XE04 - Sunitinib Substances 0.000 claims 25
- 229960001796 sunitinib Drugs 0.000 claims 25
- WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims 25
- 239000000203 mixture Substances 0.000 claims 22
- 239000007787 solid Substances 0.000 claims 21
- 238000000034 method Methods 0.000 claims 16
- LBWFXVZLPYTWQI-IPOVEDGCSA-N n-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide;(2s)-2-hydroxybutanedioic acid Chemical group OC(=O)[C@@H](O)CC(O)=O.CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C LBWFXVZLPYTWQI-IPOVEDGCSA-N 0.000 claims 15
- 239000002002 slurry Substances 0.000 claims 12
- 238000003756 stirring Methods 0.000 claims 11
- 238000002955 isolation Methods 0.000 claims 7
- 238000001035 drying Methods 0.000 claims 6
- 238000010992 reflux Methods 0.000 claims 5
- BJEPYKJPYRNKOW-UWTATZPHSA-N (R)-malic acid Chemical compound OC(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 238000010438 heat treatment Methods 0.000 claims 4
- 229940116298 l- malic acid Drugs 0.000 claims 4
- 230000001394 metastastic effect Effects 0.000 claims 4
- 206010061289 metastatic neoplasm Diseases 0.000 claims 4
- 238000001914 filtration Methods 0.000 claims 3
- 238000005406 washing Methods 0.000 claims 3
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 208000011645 metastatic carcinoma Diseases 0.000 claims 2
- 238000002156 mixing Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229960002812 sunitinib malate Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1193/KOL/2008 | 2008-07-10 | ||
| IN1193KO2008 | 2008-07-10 | ||
| PCT/GB2009/050818 WO2010004339A1 (en) | 2008-07-10 | 2009-07-09 | Processes for the preparation of crystalline forms of sunitinib malate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011527330A JP2011527330A (ja) | 2011-10-27 |
| JP2011527330A5 true JP2011527330A5 (enExample) | 2012-08-23 |
Family
ID=41100787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011517242A Pending JP2011527330A (ja) | 2008-07-10 | 2009-07-09 | スニチニブリンゴ酸塩の結晶形の調製方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20110257237A1 (enExample) |
| EP (1) | EP2297138A1 (enExample) |
| JP (1) | JP2011527330A (enExample) |
| CN (1) | CN102203085A (enExample) |
| AU (1) | AU2009269768A1 (enExample) |
| CA (1) | CA2730079A1 (enExample) |
| WO (1) | WO2010004339A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2315764A2 (en) * | 2008-08-25 | 2011-05-04 | Generics [UK] Limited | Crystalline form of sunitinib and processes for its preparation |
| US20120271056A1 (en) * | 2009-11-12 | 2012-10-25 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline form i of l-malic acid salt of sunitinib |
| CA2788709A1 (en) | 2010-01-29 | 2011-08-04 | Ranbaxy Laboratories Limited | Crystalline forms of l-malic acid salt of sunitinib |
| ES2709110T3 (es) | 2012-03-23 | 2019-04-15 | Laurus Labs Ltd | Un proceso mejorado para la preparación de sunitinib y sus sales de adición de ácido |
| US9604968B2 (en) | 2013-10-18 | 2017-03-28 | Sun Pharmaceutical Industries Limited | Pure crystalline Form II of L-malic acid salt of sunitinib and processes for its preparation |
| CN104693187A (zh) * | 2013-12-10 | 2015-06-10 | 安杰世纪生物科技（北京）有限公司 | 一种舒尼替尼L-苹果酸盐晶型λ及其制备方法 |
| CN105085490A (zh) * | 2014-05-09 | 2015-11-25 | 上海科胜药物研发有限公司 | 新的舒尼替尼苹果酸盐晶型及其制备方法 |
| CN115057814A (zh) * | 2021-12-07 | 2022-09-16 | 山东新时代药业有限公司 | 一种米力农苹果酸盐晶体 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE122008000002I1 (de) * | 2000-02-15 | 2008-04-17 | Sugen Inc | Pyrrol substituierte indolin-2-on protein kinase inhibitoren |
| EP2332934B1 (en) * | 2001-08-15 | 2017-03-01 | Pharmacia & Upjohn Company LLC | Processes for the preparation of crystals including a malic acid salt of n-[2-(diethylamino)ethyl]-5-[(5-fluoro-1,2-dihydro-2-oxo-3h-indole-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide. |
| CN1758914A (zh) * | 2003-02-24 | 2006-04-12 | 苏根公司 | 用吲哚啉酮化合物治疗过度骨质溶解 |
| US20040209937A1 (en) * | 2003-02-24 | 2004-10-21 | Sugen, Inc. | Treatment of excessive osteolysis with indolinone compounds |
| EP2253629A1 (en) * | 2007-11-21 | 2010-11-24 | Teva Pharmaceutical Industries Ltd. | Polymorphs of racemic sunitinib malate, compositions containing them and preparation thereof |
-
2009
- 2009-07-09 AU AU2009269768A patent/AU2009269768A1/en not_active Abandoned
- 2009-07-09 JP JP2011517242A patent/JP2011527330A/ja active Pending
- 2009-07-09 CN CN2009801339602A patent/CN102203085A/zh active Pending
- 2009-07-09 EP EP09785297A patent/EP2297138A1/en not_active Withdrawn
- 2009-07-09 US US13/002,917 patent/US20110257237A1/en not_active Abandoned
- 2009-07-09 WO PCT/GB2009/050818 patent/WO2010004339A1/en not_active Ceased
- 2009-07-09 CA CA2730079A patent/CA2730079A1/en not_active Abandoned
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