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 |
|---|---|---|---|---|
| SI1419151T1 (sl) | 2001-08-15 | 2014-04-30 | Pharmacia & Upjohn Company Llc | Kristali, ki vključujejo sol jabolčne kisline N-(2-(dietilamino)etil)-5-((5-fluoro-1,2-dihidro-2-okso-3H-indol-3- iliden)metil)-2,4-dimetil-1H-pirol-3-karboksamida, postopki za njihovo pripravo in sestavki le-teh |
| 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 |
| MXPA06003661A (es) * | 2003-10-02 | 2006-06-05 | Pharmacia & Upjohn Co Llc | Sales y polimorfos de un compuesto de indolinona sustituido con pirrol. |
| US20060009510A1 (en) * | 2004-07-09 | 2006-01-12 | Pharmacia & Upjohn Company Llc | Method of synthesizing indolinone compounds |
| PL1773811T3 (pl) * | 2004-07-22 | 2011-02-28 | Lilly Co Eli | Krystaliczny zmienny hydrat soli hemibursztynianowej (s)-6-(4-(2-((3(9h-karbazol-4-iloksy)-2-hydroksypropylo)amino)-2-metylopropylo)fenoksy)-3-pirydynokarboksy amidu |
| AU2006245421A1 (en) * | 2005-05-12 | 2006-11-16 | Pfizer Inc. | Anticancer combination therapy using sunitinib malate |
| RU2399619C2 (ru) * | 2005-09-19 | 2010-09-20 | Пфайзер Продактс Инк. | Твердые солевые формы замещенного пирролом 2-индолинона |
| 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 |
| WO2009067686A2 (en) * | 2007-11-21 | 2009-05-28 | Teva Pharmaceutical Industries Ltd. | Sunitinib hemi-l-malate, polymorphs and preparation thereof, polymorphs of racemic sunitinib malate, compositins containing sunitinib base and malic acid and preparation thereof |
| CN101939314B (zh) * | 2007-12-12 | 2014-04-02 | 麦迪凯姆股份公司 | 3-吡咯取代的2-吲哚酮的多晶型物 |
| 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 |
| EP2252607A2 (en) * | 2008-02-21 | 2010-11-24 | 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 |
| CA2720164A1 (en) * | 2008-03-31 | 2009-10-08 | Teva Pharmaceutical Industries Ltd. | Processes for preparing sunitinib and salts thereof |
| WO2009128083A1 (en) * | 2008-04-16 | 2009-10-22 | Natco Pharma Limited | Novel polymorphic forms of sunitinib base |
| CN102066362B (zh) | 2008-05-23 | 2014-07-30 | 上海医药工业研究院 | 二氢吲哚酮衍生物 |
| SI2313371T1 (sl) * | 2008-06-13 | 2013-02-28 | Medichem, S.A. | Postopek za pripravo soli 3-pirol substituirane 2-indolinonske jabolčne kisline |
| 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 |
| JP2011527330A (ja) * | 2008-07-10 | 2011-10-27 | ジェネリクス・（ユーケー）・リミテッド | スニチニブリンゴ酸塩の結晶形の調製方法 |
| CA2731605A1 (en) * | 2008-07-24 | 2010-01-28 | Teva Pharmaceutical Industries Ltd. | Sunitinib and salts thereof and their polymorphs |
| EP2342195B1 (en) * | 2008-07-24 | 2014-09-10 | Medichem, S.A. | Crystalline forms of a 3-pyrrole substituted 2-indolinone malate salt |
| CA2734965A1 (en) * | 2008-08-25 | 2010-03-04 | Generics [Uk] Limited | Novel crystalline form and processes for its preparation |
| CN102197034A (zh) * | 2008-08-25 | 2011-09-21 | 基因里克斯(英国)有限公司 | 舒尼替尼的新型多晶型物及其制备方法 |
| CN102177155A (zh) * | 2008-10-10 | 2011-09-07 | 麦迪凯姆股份公司 | 一种3-吡咯取代的2-吲哚酮苹果酸盐的制备工艺 |
| 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 |
| TW201920110A (zh) | 2009-01-16 | 2019-06-01 | 美商艾克塞里克斯公司 | 包含n-(4-{[6,7-雙(甲氧基)喹啉-4-基]氧基}苯基)-n'-(4-氟苯基)環丙烷-1,1-二甲醯胺之蘋果酸鹽之醫藥組合物及其用途 |
| 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 |
| WO2011033472A1 (en) | 2009-09-16 | 2011-03-24 | Ranbaxy Laboratories Limited | Salts of sunitinib |
| EP2499133A2 (en) | 2009-11-12 | 2012-09-19 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline form i of l-malic acid salt of sunitinib |
| US8916716B2 (en) | 2009-11-19 | 2014-12-23 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline form II of L-malic acid salt of sunitinib |
| WO2011092664A1 (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 |
| WO2011107919A1 (en) | 2010-03-04 | 2011-09-09 | Ranbaxy Laboratories Limited | Process for the direct preparation of malic acid salt of sunitinib |
| CA2793359A1 (en) | 2010-03-18 | 2011-09-22 | 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 |
| CN104114550A (zh) | 2012-03-23 | 2014-10-22 | 劳拉斯实验室私人有限公司 | 制备舒尼替尼及其酸加成盐的改进的方法 |
| 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 |
| PL2844282T3 (pl) | 2012-05-04 | 2019-11-29 | Pfizer | Antygeny związane z gruczołem krokowym i schematy immunoterapii oparte na szczepionce |
| 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 |
| US9278955B2 (en) | 2013-10-18 | 2016-03-08 | Sun Pharmaceutical Industries Limited | Ascorbic acid salt of sunitinib |
| EP3524262A1 (en) | 2013-11-01 | 2019-08-14 | 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 |
| US20220192989A1 (en) * | 2019-04-18 | 2022-06-23 | Meter Health, Inc. | Methods and compositions for treating respiratory arrhythmias |
| EP3958845A1 (en) | 2019-04-25 | 2022-03-02 | Synthon B.V. | Pharmaceutical composition comprising amorphous sunitinib |
| 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 |
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-
2002
- 2002-08-13 SI SI200231043T patent/SI1419151T1/sl unknown
- 2002-08-13 KR KR1020047002173A patent/KR100639281B1/ko not_active Expired - Lifetime
- 2002-08-13 EP EP16196036.4A patent/EP3168218B1/en not_active Expired - Lifetime
- 2002-08-13 US US10/218,985 patent/US20030069298A1/en not_active Abandoned
- 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 JP JP2003521228A patent/JP4159988B2/ja not_active Expired - Lifetime
- 2002-08-13 RS YU10304A patent/RS53251B/sr unknown
- 2002-08-13 SK SK90-2004A patent/SK902004A3/sk unknown
- 2002-08-13 DK DK02759342.5T patent/DK1419151T3/da active
- 2002-08-13 SI SI200231093T patent/SI3168218T1/sl unknown
- 2002-08-13 AP APAP/P/2004/002976A patent/AP1660A/en active
- 2002-08-13 HR HR20040112A patent/HRP20040112B1/xx not_active IP Right Cessation
- 2002-08-13 AU AU2002324684A patent/AU2002324684B2/en not_active Expired
- 2002-08-13 PL PL368317A patent/PL216524B1/pl unknown
- 2002-08-13 EP EP02759342.5A patent/EP1419151B1/en not_active Expired - Lifetime
- 2002-08-13 IL IL16009702A patent/IL160097A0/xx active IP Right Grant
- 2002-08-13 WO PCT/US2002/025649 patent/WO2003016305A1/en not_active Ceased
- 2002-08-13 PT PT2759342T patent/PT1419151E/pt unknown
- 2002-08-13 CA CA002455050A patent/CA2455050C/en not_active Expired - Lifetime
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