JP2005503386A5 - - Google Patents
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- Publication number
- JP2005503386A5 JP2005503386A5 JP2003521228A JP2003521228A JP2005503386A5 JP 2005503386 A5 JP2005503386 A5 JP 2005503386A5 JP 2003521228 A JP2003521228 A JP 2003521228A JP 2003521228 A JP2003521228 A JP 2003521228A JP 2005503386 A5 JP2005503386 A5 JP 2005503386A5
- Authority
- JP
- Japan
- Prior art keywords
- crystal
- powder
- crystals
- ray diffraction
- diethylamino
- 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.)
- Granted
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- 239000013078 crystal Substances 0.000 claims 56
- 238000000034 method Methods 0.000 claims 25
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 23
- 238000000634 powder X-ray diffraction Methods 0.000 claims 20
- 229940049920 malate Drugs 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 14
- -1 5-fluoro-1,2-dihydro-2-oxo-3H-indole-3-ylidene Chemical group 0.000 claims 13
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- 235000011090 malic acid Nutrition 0.000 claims 9
- 239000011549 crystallization solution Substances 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 239000002904 solvent Substances 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 238000001816 cooling Methods 0.000 claims 6
- 229940099690 malic acid Drugs 0.000 claims 6
- 239000001630 malic acid Substances 0.000 claims 6
- 238000002844 melting Methods 0.000 claims 5
- 230000008018 melting Effects 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000002002 slurry Substances 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 229940116298 l- malic acid Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- WINHZLLDWRZWRT-UHFFFAOYSA-N N-[2-(diethylamino)ethyl]-5-[(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(C=C2C3=CC(F)=CC=C3NC2=O)=C1C WINHZLLDWRZWRT-UHFFFAOYSA-N 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- 230000001939 inductive effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- DDIIYGHHUMKDGI-UHFFFAOYSA-N 5-fluoro-1,3-dihydroindol-2-one Chemical compound FC1=CC=C2NC(=O)CC2=C1 DDIIYGHHUMKDGI-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000010899 nucleation Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31235301P | 2001-08-15 | 2001-08-15 | |
| PCT/US2002/025649 WO2003016305A1 (en) | 2001-08-15 | 2002-08-13 | Crystals including a malic acid salt of n-[2-(diethylamino) ethyl]-5-[(5-fluoro-2-oxo-3h-indole-3-ylidene) methyl]-2, 4-dimethyl-1h-pyrrole-3-carboxamide, processes for its preparation and compositions thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005503386A JP2005503386A (ja) | 2005-02-03 |
| JP2005503386A5 true JP2005503386A5 (enExample) | 2005-12-22 |
| JP4159988B2 JP4159988B2 (ja) | 2008-10-01 |
Family
ID=23211067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003521228A Expired - Lifetime JP4159988B2 (ja) | 2001-08-15 | 2002-08-13 | Ｎ−［２−（ジエチルアミノ）エチル］−５−［（５−フルオロ−１，２−ジヒドロ−２−オキソ−３ｈ−インドール−３−イリデン）メチル］−２，４−ジメチル−１ｈ−ピロール−３−カルボキシアミドのリンゴ酸塩を含む結晶、その製法およびその組成物 |
Country Status (42)
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| PY0323128A (es) * | 2002-09-10 | 2012-12-03 | Pharmacia Italia Spa | Formulacion sólida que comprende un compuesto de indolina, útil en el tratamiento de trastornos relacionados con proteina de quinasas |
| KR20060058728A (ko) * | 2003-10-02 | 2006-05-30 | 파마시아 앤드 업존 캄파니 엘엘씨 | 피롤-치환된 인돌리논 화합물의 염 및 다형체 |
| US20060009510A1 (en) * | 2004-07-09 | 2006-01-12 | Pharmacia & Upjohn Company Llc | Method of synthesizing indolinone compounds |
| MX2007000892A (es) * | 2004-07-22 | 2007-05-23 | Lilly Co Eli | Un hidrato variable cristalino de la sal de (s)-3-piridincarboxami da, 6-[4-[2-[[3-(9h-carbazol-4-iloxi)-2-hidroxipropil]amino]-2-met ilpropil]fenoxi]-hemisuccinato. |
| AU2006245421A1 (en) * | 2005-05-12 | 2006-11-16 | Pfizer Inc. | Anticancer combination therapy using sunitinib malate |
| NZ566033A (en) * | 2005-09-19 | 2011-04-29 | Pfizer Prod Inc | Solid salt forms of a pyrrole substituted 2-indolinone |
| US20090004213A1 (en) * | 2007-03-26 | 2009-01-01 | Immatics Biotechnologies Gmbh | Combination therapy using active immunotherapy |
| US20100256392A1 (en) * | 2007-11-21 | 2010-10-07 | Teva Pharmaceutical Industries Ltd. | Polymorphs of sunitinib base and processes for preparation thereof |
| EP2253629A1 (en) | 2007-11-21 | 2010-11-24 | Teva Pharmaceutical Industries Ltd. | Polymorphs of racemic sunitinib malate, compositions containing them and preparation thereof |
| CA2709083A1 (en) * | 2007-12-12 | 2009-06-18 | Medichem S.A. | Polymorphic forms of a 3-pyrrole substituted 2-indolinone |
| EP2090306A1 (en) | 2008-02-13 | 2009-08-19 | Ratiopharm GmbH | Pharmaceutical compositions comprising N-[2-(diethylamino)ethyl]-5-[(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide |
| EP2113248A1 (en) | 2008-04-29 | 2009-11-04 | Ratiopharm GmbH | Pharmaceutical composition comprising N-[2-(diethylamino)ethyl]-5-[(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2-,4-dimethyl-1H-pyrrole-3-carboxamide |
| US20110112164A1 (en) * | 2008-02-21 | 2011-05-12 | Generics (Uk) Limited | Novel polymorphs and processes for their preparation |
| EP2098521A1 (en) * | 2008-03-06 | 2009-09-09 | Ratiopharm GmbH | Crystal forms of N-[2-(diethylamino) ethyl]-5-[fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrolle-3-carboxamide and methods for their prepparation |
| EP2274303B1 (en) * | 2008-03-31 | 2012-08-29 | Teva Pharmaceutical Industries Ltd. | Processes for preparing sunitinib and salts thereof |
| US8466190B2 (en) | 2008-04-16 | 2013-06-18 | Natco Pharma Limited | Polymorphic forms of Sunitinib base |
| RU2468022C2 (ru) * | 2008-05-23 | 2012-11-27 | Шанхай Инститьют Оф Фармасьютикал Индастри | Производные дигидроиндолона |
| ES2392762T3 (es) * | 2008-06-13 | 2012-12-13 | Medichem, S.A. | Procedimiento para preparar una sal de malato de 2-indolinona sustituida con 3-pirrol |
| EP2138167A1 (en) | 2008-06-24 | 2009-12-30 | ratiopharm GmbH | Pharmaceutical composition comprising N-[2-(Diethylamino)ethyl]-5-[(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene) methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide |
| WO2009156837A2 (en) * | 2008-06-26 | 2009-12-30 | Medichem, S.A. | Amorphous form of a 3-pyrrole substituted 2-indolinone malate salt |
| AU2009269768A1 (en) * | 2008-07-10 | 2010-01-14 | Generics [Uk] Limited | Processes for the preparation of crystalline forms of sunitinib malate |
| US8618309B2 (en) * | 2008-07-24 | 2013-12-31 | Teva Pharmaceutical Industries Ltd. | Sunitinib and salts thereof and their polymorphs |
| WO2010010454A2 (en) | 2008-07-24 | 2010-01-28 | Medichem, S.A. | Crystalline forms of a 3-pyrrole substituted 2-indolinone malate salt |
| EP2315764A2 (en) * | 2008-08-25 | 2011-05-04 | Generics [UK] Limited | Crystalline form of sunitinib and processes for its preparation |
| EP2318393A1 (en) * | 2008-08-25 | 2011-05-11 | Generics [UK] Limited | Novel polymorphs of sunitinib and processes for their preparation |
| WO2010041134A1 (en) * | 2008-10-10 | 2010-04-15 | Medichem, S.A. | Process for preparing a 3-pyrrole subsituted 2-indolinone malate salt |
| EP2181991A1 (en) | 2008-10-28 | 2010-05-05 | LEK Pharmaceuticals D.D. | Novel salts of sunitinib |
| EP2186809A1 (en) * | 2008-11-13 | 2010-05-19 | LEK Pharmaceuticals D.D. | New crystal form of sunitinib malate |
| EP2896618A1 (en) | 2009-01-02 | 2015-07-22 | Hetero Research Foundation | Polymorphs of sunitinib malate |
| RS52754B2 (sr) | 2009-01-16 | 2022-08-31 | Exelixis Inc | Malat so n-(4- {[6,7-bis(metiloksi)hinolin-4-il]oksi}fenil-n'- (4-fluorofenil) ciklopropan-1,1-dikarboksamid-a, i njeni kristalni oblici za lečenje karcinoma |
| EP2255792A1 (en) | 2009-05-20 | 2010-12-01 | Ratiopharm GmbH | Pharmaceutical compositions for N-[2-(Diethylamino)ethyl]5-[(fluoro-1,2-dihydro-2-oxo-3H-indole-3-ylidene) methyl]-2,4-dimenthyl-1H-pyrrole-3-carboxamide |
| WO2011004200A1 (en) | 2009-07-10 | 2011-01-13 | Generics [Uk] Limited | Novel pyrrole derivatives |
| CA2774634A1 (en) | 2009-09-16 | 2011-03-24 | Ranbaxy Laboratories Limited | Salts of sunitinib |
| 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 |
| WO2011061613A1 (en) | 2009-11-19 | 2011-05-26 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline form ii 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 |
| WO2011100325A2 (en) | 2010-02-09 | 2011-08-18 | Sicor Inc. | Polymorphs of sunitinib salts |
| WO2011104555A2 (en) | 2010-02-25 | 2011-09-01 | Generics [Uk] Limited | Novel process |
| EP2542550A1 (en) | 2010-03-04 | 2013-01-09 | Ranbaxy Laboratories Limited | Process for the direct preparation of malic acid salt of sunitinib |
| AU2011228765A1 (en) | 2010-03-18 | 2012-10-11 | Ranbaxy Laboratories Limited | Process for the preparation of malic acid salt of sunitinib |
| WO2011128699A2 (en) | 2010-04-16 | 2011-10-20 | Generics [Uk] Limited | Novel process |
| WO2012042421A1 (en) | 2010-09-29 | 2012-04-05 | Pfizer Inc. | Method of treating abnormal cell growth |
| US20140178368A1 (en) | 2011-04-19 | 2014-06-26 | Leslie Lynne SHARP | Combinations of anti-4-1bb antibodies and adcc-inducing antibodies for the treatment of cancer |
| 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 |
| PL399027A1 (pl) | 2012-04-27 | 2013-10-28 | Instytut Farmaceutyczny | Sposób otrzymywania N-[2-(dietylamino)etylo]-5-formylo-2,4-dimetylo-1H-pirolo-3-karboksyamidu o wysokiej czystosci i jego zastosowanie do wytwarzania sunitynibu |
| CA2871711A1 (en) | 2012-05-04 | 2013-11-07 | Pfizer Inc. | Prostate-associated antigens and vaccine-based immunotherapy regimens |
| US9278955B2 (en) | 2013-10-18 | 2016-03-08 | Sun Pharmaceutical Industries Limited | Ascorbic acid salt of sunitinib |
| 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 |
| CA2928908C (en) | 2013-11-01 | 2021-01-12 | Pfizer Inc. | Vectors for expression of prostate-associated antigens |
| 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 |
| CN104744442B (zh) * | 2013-12-25 | 2019-05-28 | 江苏豪森药业集团有限公司 | 苹果酸舒尼替尼的制备方法 |
| RU2567535C1 (ru) * | 2014-10-01 | 2015-11-10 | Олег Ростиславович Михайлов | КРИСТАЛЛИЧЕСКАЯ ε-МОДИФИКАЦИЯ N-[2-(ДИЭТИЛАМИНО)ЭТИЛ]-5-[(Z)-(5-ФТОР-1,2-ДИГИДРО-2-ОКСО-3Н-ИНДОЛ-3-ИЛИДЕН)МЕТИЛ]-2,4-ДИМЕТИЛ-1Н-ПИРРОЛ-3-КАРБОКСАМИД МАЛАТА, СПОСОБ ЕЕ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ЕЕ ОСНОВЕ |
| CN105712979A (zh) * | 2014-12-05 | 2016-06-29 | 广州白云山医药集团股份有限公司白云山制药总厂 | 一种苹果酸舒尼替尼晶型ⅰ的制备方法 |
| EP3539536A1 (en) | 2018-03-15 | 2019-09-18 | MH10 Spolka z ograniczona odpowiedzialnoscia | A pharmaceutical composition of sunitinib or its salt thereof in its polymorphic form i |
| WO2020216450A1 (en) | 2019-04-25 | 2020-10-29 | Synthon B.V. | Pharmaceutical composition comprising amorphous sunitinib |
| CA3136711A1 (en) * | 2019-04-18 | 2020-10-22 | Meter Health, Inc. | Methods and compositions for treating respiratory arrhythmias |
| JP7633786B2 (ja) * | 2020-09-18 | 2025-02-20 | 日本化薬株式会社 | スニチニブリンゴ酸塩を有効成分とする医薬錠剤 |
| KR20240025990A (ko) | 2022-08-19 | 2024-02-27 | 주식회사 스카이테라퓨틱스 | 무정형 수니티닙, 그 제조방법 및 이를 포함한 의약 조성물 |
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| US20110112164A1 (en) | 2008-02-21 | 2011-05-12 | Generics (Uk) Limited | Novel polymorphs and processes for their preparation |
| WO2009156837A2 (en) | 2008-06-26 | 2009-12-30 | Medichem, S.A. | Amorphous form of a 3-pyrrole substituted 2-indolinone malate salt |
-
2002
- 2002-08-13 EP EP11156767.3A patent/EP2332934B1/en not_active Expired - Lifetime
- 2002-08-13 DK DK02759342.5T patent/DK1419151T3/da active
- 2002-08-13 CN CNB02815892XA patent/CN100439360C/zh not_active Ceased
- 2002-08-13 RS YU10304A patent/RS53251B/sr unknown
- 2002-08-13 CZ CZ2004196A patent/CZ2004196A3/cs unknown
- 2002-08-13 UA UA2004021084A patent/UA76483C2/uk unknown
- 2002-08-13 EP EP16196036.4A patent/EP3168218B1/en not_active Expired - Lifetime
- 2002-08-13 SI SI200231093T patent/SI3168218T1/sl unknown
- 2002-08-13 MX MXPA04001452A patent/MXPA04001452A/es active IP Right Grant
- 2002-08-13 CN CNB2005101286242A patent/CN100364991C/zh not_active Expired - Lifetime
- 2002-08-13 BR BR0211612-0A patent/BR0211612A/pt not_active Application Discontinuation
- 2002-08-13 PT PT2759342T patent/PT1419151E/pt unknown
- 2002-08-13 EA EA200400183A patent/EA006445B9/ru unknown
- 2002-08-13 GE GE5446A patent/GEP20063777B/en unknown
- 2002-08-13 ES ES02759342.5T patent/ES2453164T3/es not_active Expired - Lifetime
- 2002-08-13 IL IL16009702A patent/IL160097A0/xx active IP Right Grant
- 2002-08-13 US US10/218,985 patent/US20030069298A1/en not_active Abandoned
- 2002-08-13 DK DK16196036.4T patent/DK3168218T3/en active
- 2002-08-13 JP JP2003521228A patent/JP4159988B2/ja not_active Expired - Lifetime
- 2002-08-13 KR KR1020047002173A patent/KR100639281B1/ko not_active Expired - Lifetime
- 2002-08-13 PL PL368317A patent/PL216524B1/pl unknown
- 2002-08-13 HR HR20040112A patent/HRP20040112B1/xx not_active IP Right Cessation
- 2002-08-13 SI SI200231043T patent/SI1419151T1/sl unknown
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