CN100439360C - 包括n-[2-(二乙氨基)乙基]-5-[(5-氟-2-氧代-3h-吲哚-3-亚基)甲基]-2,4-二甲基-1h-吡咯-3-甲酰胺的苹果酸盐的晶体、其制备方法和其组合物 - Google Patents

包括n-[2-(二乙氨基)乙基]-5-[(5-氟-2-氧代-3h-吲哚-3-亚基)甲基]-2,4-二甲基-1h-吡咯-3-甲酰胺的苹果酸盐的晶体、其制备方法和其组合物 Download PDF

Info

Publication number
CN100439360C
CN100439360C CNB02815892XA CN02815892A CN100439360C CN 100439360 C CN100439360 C CN 100439360C CN B02815892X A CNB02815892X A CN B02815892XA CN 02815892 A CN02815892 A CN 02815892A CN 100439360 C CN100439360 C CN 100439360C
Authority
CN
China
Prior art keywords
crystal
methyl
pyrrole
oxo
fluoro
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.)
Ceased
Application number
CNB02815892XA
Other languages
English (en)
Chinese (zh)
Other versions
CN1543462A (zh
Inventor
M·霍利
T·J·弗莱克
S·P·普雷斯科特
M·T·马洛尼
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pharmacia and Upjohn Co LLC
Original Assignee
Pharmacia and Upjohn Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=23211067&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN100439360(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Pharmacia and Upjohn Co filed Critical Pharmacia and Upjohn Co
Publication of CN1543462A publication Critical patent/CN1543462A/zh
Application granted granted Critical
Publication of CN100439360C publication Critical patent/CN100439360C/zh
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Oncology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)
CNB02815892XA 2001-08-15 2002-08-13 包括n-[2-(二乙氨基)乙基]-5-[(5-氟-2-氧代-3h-吲哚-3-亚基)甲基]-2,4-二甲基-1h-吡咯-3-甲酰胺的苹果酸盐的晶体、其制备方法和其组合物 Ceased CN100439360C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US31235301P 2001-08-15 2001-08-15
US60/312,353 2001-08-15

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CNB2005101286242A Division CN100364991C (zh) 2001-08-15 2002-08-13 2,4-二甲基-1h-吡咯-3-甲酰胺衍生物的苹果酸盐的晶体、其制备方法和其组合物

Publications (2)

Publication Number Publication Date
CN1543462A CN1543462A (zh) 2004-11-03
CN100439360C true CN100439360C (zh) 2008-12-03

Family

ID=23211067

Family Applications (2)

Application Number Title Priority Date Filing Date
CNB02815892XA Ceased CN100439360C (zh) 2001-08-15 2002-08-13 包括n-[2-(二乙氨基)乙基]-5-[(5-氟-2-氧代-3h-吲哚-3-亚基)甲基]-2,4-二甲基-1h-吡咯-3-甲酰胺的苹果酸盐的晶体、其制备方法和其组合物
CNB2005101286242A Expired - Lifetime CN100364991C (zh) 2001-08-15 2002-08-13 2,4-二甲基-1h-吡咯-3-甲酰胺衍生物的苹果酸盐的晶体、其制备方法和其组合物

Family Applications After (1)

Application Number Title Priority Date Filing Date
CNB2005101286242A Expired - Lifetime CN100364991C (zh) 2001-08-15 2002-08-13 2,4-二甲基-1h-吡咯-3-甲酰胺衍生物的苹果酸盐的晶体、其制备方法和其组合物

Country Status (42)

Country Link
US (2) US20030069298A1 (OSRAM)
EP (3) EP2332934B1 (OSRAM)
JP (1) JP4159988B2 (OSRAM)
KR (1) KR100639281B1 (OSRAM)
CN (2) CN100439360C (OSRAM)
AP (1) AP1660A (OSRAM)
AR (1) AR036261A1 (OSRAM)
AU (1) AU2002324684B2 (OSRAM)
BG (1) BG108553A (OSRAM)
BR (1) BR0211612A (OSRAM)
CA (1) CA2455050C (OSRAM)
CO (1) CO5550431A2 (OSRAM)
CU (1) CU23713B7 (OSRAM)
CY (1) CY1121552T1 (OSRAM)
CZ (1) CZ2004196A3 (OSRAM)
DK (2) DK3168218T3 (OSRAM)
EA (1) EA006445B9 (OSRAM)
EC (1) ECSP044975A (OSRAM)
ES (3) ES2453164T3 (OSRAM)
GE (1) GEP20063777B (OSRAM)
HR (1) HRP20040112B1 (OSRAM)
HU (1) HU229206B1 (OSRAM)
IL (1) IL160097A0 (OSRAM)
IS (1) IS7147A (OSRAM)
MA (1) MA27058A1 (OSRAM)
ME (1) ME00414B (OSRAM)
MX (1) MXPA04001452A (OSRAM)
MY (1) MY139383A (OSRAM)
NO (1) NO326508B1 (OSRAM)
NZ (1) NZ531232A (OSRAM)
OA (1) OA12650A (OSRAM)
PL (1) PL216524B1 (OSRAM)
PT (2) PT1419151E (OSRAM)
RS (1) RS53251B (OSRAM)
SI (2) SI1419151T1 (OSRAM)
SK (1) SK902004A3 (OSRAM)
TN (1) TNSN04028A1 (OSRAM)
TR (1) TR201900509T4 (OSRAM)
TW (1) TWI269796B (OSRAM)
UA (1) UA76483C2 (OSRAM)
WO (1) WO2003016305A1 (OSRAM)
ZA (1) ZA200400706B (OSRAM)

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ531232A (en) 2001-08-15 2004-11-26 Pharmacia & Upjohn Inc 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
TW200418836A (en) * 2002-09-10 2004-10-01 Pharmacia Italia Spa Formulations comprising an indolinone compound
PT1670785E (pt) * 2003-10-02 2010-09-16 Pharmacia & Upjohn Co Llc Sais e polimorfos de um composto de indolinona substituída com pirrole
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
WO2007034272A1 (en) 2005-09-19 2007-03-29 Pfizer Products 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
CA2699306A1 (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
WO2009074862A1 (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
JP2011512396A (ja) * 2008-02-21 2011-04-21 ジェネリクス・（ユーケー）・リミテッド 新規な多形およびその調製方法
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
ES2391501T3 (es) * 2008-03-31 2012-11-27 Teva Pharmaceutical Industries Ltd. Procedimientos para preparar sunitinib y sales del mismo
CA2720943A1 (en) * 2008-04-16 2009-10-22 Natco Pharma Limited Novel polymorphic forms of sunitinib base
KR101375156B1 (ko) 2008-05-23 2014-03-18 쟝수 치아타이 티안큉 파마수티컬 주식회사 디하이드로인돌리논 유도체들
EP2313371B1 (en) * 2008-06-13 2012-08-15 Medichem, S.A. Process for preparing a 3-pyrrole substituted 2-indolinone malate salt
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
CA2730079A1 (en) * 2008-07-10 2010-01-14 Generics [Uk] Limited Processes for the preparation of crystalline forms of sunitinib malate
EP2342195B1 (en) 2008-07-24 2014-09-10 Medichem, S.A. Crystalline forms of a 3-pyrrole substituted 2-indolinone malate salt
WO2010011834A2 (en) * 2008-07-24 2010-01-28 Teva Pharmaceutical Industries Ltd. Sunitinib and salts thereof and their polymorphs
WO2010023473A2 (en) * 2008-08-25 2010-03-04 Generics [Uk] Limited Novel crystalline form and processes for its preparation
JP2012500838A (ja) * 2008-08-25 2012-01-12 ジェネリクス・（ユーケー）・リミテッド スニチニブの新規な多形およびその調製方法
AR073807A1 (es) * 2008-10-10 2010-12-01 Medichem Sa Proceso para preparar el malato de sunitinib, sal de un acido mas debil que el malato como compuesto intermediario, y proceso para preparar dicha sal intermediaria.
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
US8329740B2 (en) 2009-01-02 2012-12-11 Hetero Research Foundation Polymorphs of sunitinib malate
DK2387563T4 (da) 2009-01-16 2022-07-18 Exelixis Inc Malatsalt af n-(4-{ [ 6, 7-bis(methyloxy)quinolin-4-yl]oxy}phenyl-n'-(4-fluorphenyl)cyclopropan-1,1-dicarboxamid, og krystallinske former deraf til behandling af cancer
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
AU2010296849A1 (en) 2009-09-16 2012-05-03 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
EP2528913A1 (en) 2010-01-29 2012-12-05 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
CA2792039A1 (en) 2010-03-04 2011-09-09 Ranbaxy Laboratories Limited Process for the direct preparation of malic acid salt of sunitinib
EP2547674A1 (en) 2010-03-18 2013-01-23 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
CA2830972C (en) 2011-04-19 2018-11-20 Pfizer Inc. Combinations of anti-4-1bb antibodies and adcc-inducing antibodies for the treatment of cancer
US9206163B2 (en) 2012-03-23 2015-12-08 Laurus Labs Private Ltd. Process for the preparation of sunitinib and its acid addition salts thereof
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
NZ701324A (en) 2012-05-04 2016-09-30 Pfizer 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
MY182168A (en) 2013-11-01 2021-01-18 Pfizer 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
AU2020257415A1 (en) * 2019-04-18 2021-11-11 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

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001037820A2 (en) * 1999-11-24 2001-05-31 Sugen, Inc. Ionizable indolinone derivatives and their use as ptk ligands
WO2001060814A2 (en) * 2000-02-15 2001-08-23 Sugen, Inc. Pyrrole substituted 2-indolinone protein kinase inhibitors

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL168919B1 (pl) 1990-10-15 1996-05-31 Pfizer Sposób wytwarzania nowych pochodnych indolu PL PL PL PL
IL100091A (en) 1990-12-12 1998-08-16 Zeneca Ltd Pharmaceutical compositions containing a physical form of n-[4-[5-(cyclopentyloxycarbonyl)amino-1-methyl indol-3-yl-methyl]-2-methylbenzenesulpho-namide and process for their preparation
ES2116411T3 (es) 1992-06-05 1998-07-16 Merck Sharp & Dohme La sal sulfato de un triazol sustituido, composiciones farmaceuticas de la misma y su uso en terapia
ES2157254T3 (es) * 1993-03-12 2001-08-16 Upjohn Co Ceftiofur (acido libre) cristalino.
US6288057B1 (en) 1994-08-31 2001-09-11 Eli Lilly And Company Physical form of dihydro-2,3-benzodiazepine derivative
DE19503966C2 (de) 1995-02-07 1998-07-02 Mack Chem Pharm Kristallmodifikation von 2,4-Diamino-6-hydroxymethylpteridin-Hydrobromid, Verfahren zu dessen Herstellung und dessen Verwendung
US5597663A (en) * 1995-05-30 1997-01-28 Motorola, Inc. Low temperature molten lithium salt electrolytes for electrochemical cells
US5880141A (en) * 1995-06-07 1999-03-09 Sugen, Inc. Benzylidene-Z-indoline compounds for the treatment of disease
US5673451A (en) * 1995-07-06 1997-10-07 Moore; James R. Instructional toothbrush
US20020045746A1 (en) 1995-12-11 2002-04-18 Barton Kathleen P. Eplerenone crystalline form
US20020038021A1 (en) 1995-12-11 2002-03-28 Barton Kathleen P. Eplerenone crystalline form exhibiting enhanced dissolution rate
US6066647A (en) 1996-07-29 2000-05-23 Pfizer Inc. Zwitterionic forms of trovafloxacin
CA2264104A1 (en) * 1996-08-14 1998-02-19 G.D. Searle & Co. Crystalline form of 4-[5-methyl-3-phenylisoxazol-4-yl]benzenesulfonamide
EP0949203A4 (en) 1996-12-25 2006-01-18 Nippon Kayaku Kk FINE CISPLATIN POWDER AND PROCESS FOR PRODUCING THE SAME
US5777185A (en) * 1997-09-09 1998-07-07 Laroche Industries Inc. Production of organic fluorine compounds
US6133305A (en) * 1997-09-26 2000-10-17 Sugen, Inc. 3-(substituted)-2-indolinones compounds and use thereof as inhibitors of protein kinase activity
US6012678A (en) * 1998-01-26 2000-01-11 The Boeing Company Galley vacuum waste disposal system
CZ298170B6 (cs) 1998-06-19 2007-07-11 Teijin Limited Polymorfní a amorfní modifikace 2-(3-kyan-4-isobutoxyfenyl)-4-methyl-5-thiazolkarboxylové kyseliny a zpusob jejich prípravy
WO2000035908A1 (en) * 1998-12-17 2000-06-22 F. Hoffmann-La Roche Ag 4-alkenyl (and alkynyl) oxindoles as inhibitors of cyclin-dependent kinases, in particular cdk2
US6239141B1 (en) * 1999-06-04 2001-05-29 Pfizer Inc. Trovafloxacin oral suspensions
US6316672B1 (en) 2001-01-31 2001-11-13 Grayson Walker Stowell Form a of fluoxetine hydrochloride
NZ531232A (en) 2001-08-15 2004-11-26 Pharmacia & Upjohn Inc 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
JP2011512396A (ja) 2008-02-21 2011-04-21 ジェネリクス・（ユーケー）・リミテッド 新規な多形およびその調製方法
WO2009156837A2 (en) 2008-06-26 2009-12-30 Medichem, S.A. Amorphous form of a 3-pyrrole substituted 2-indolinone malate salt

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001037820A2 (en) * 1999-11-24 2001-05-31 Sugen, Inc. Ionizable indolinone derivatives and their use as ptk ligands
WO2001060814A2 (en) * 2000-02-15 2001-08-23 Sugen, Inc. Pyrrole substituted 2-indolinone protein kinase inhibitors

Also Published As

Publication number Publication date
MXPA04001452A (es) 2004-05-20
DK3168218T3 (en) 2019-01-14
NO326508B1 (no) 2008-12-15
DK1419151T3 (da) 2014-03-31
EP2332934B1 (en) 2017-03-01
JP4159988B2 (ja) 2008-10-01
ECSP044975A (es) 2004-03-23
ES2623094T3 (es) 2017-07-10
GEP20063777B (en) 2006-03-27
PL368317A1 (en) 2005-03-21
EP1419151A1 (en) 2004-05-19
KR20040030074A (ko) 2004-04-08
AP1660A (en) 2006-09-09
PT3168218T (pt) 2019-01-11
US7435832B2 (en) 2008-10-14
ZA200400706B (en) 2005-05-25
MY139383A (en) 2009-09-30
SK902004A3 (sk) 2005-03-04
HK1088008A1 (zh) 2006-10-27
IS7147A (is) 2004-02-10
EA006445B1 (ru) 2005-12-29
CA2455050C (en) 2007-02-20
BR0211612A (pt) 2004-08-24
HK1066542A1 (en) 2005-03-24
OA12650A (en) 2006-06-19
EP3168218B1 (en) 2018-11-14
RS53251B (sr) 2014-08-29
EP1419151B1 (en) 2014-02-26
CU20040029A7 (es) 2008-03-14
TWI269796B (en) 2007-01-01
AP2004002976A0 (en) 2004-03-31
HRP20040112B1 (en) 2012-03-31
EP2332934A1 (en) 2011-06-15
CY1121552T1 (el) 2020-05-29
SI3168218T1 (sl) 2019-05-31
HRP20040112A2 (en) 2004-06-30
RS10304A (sr) 2007-02-05
EA200400183A1 (ru) 2004-08-26
CA2455050A1 (en) 2003-02-27
AU2002324684B2 (en) 2006-10-05
SI1419151T1 (sl) 2014-04-30
KR100639281B1 (ko) 2006-10-31
PL216524B1 (pl) 2014-04-30
CU23713B7 (es) 2011-10-05
HUP0700036A2 (en) 2008-10-28
US20070191458A1 (en) 2007-08-16
CN1543462A (zh) 2004-11-03
CN100364991C (zh) 2008-01-30
NZ531232A (en) 2004-11-26
US20030069298A1 (en) 2003-04-10
CN1789264A (zh) 2006-06-21
ME00414B (me) 2011-10-10
TNSN04028A1 (fr) 2006-06-01
UA76483C2 (en) 2006-08-15
ES2705063T3 (es) 2019-03-21
CO5550431A2 (es) 2005-08-31
IL160097A0 (en) 2004-06-20
NO20041054L (no) 2004-03-12
JP2005503386A (ja) 2005-02-03
TR201900509T4 (tr) 2019-02-21
WO2003016305A1 (en) 2003-02-27
AR036261A1 (es) 2004-08-25
PT1419151E (pt) 2014-03-27
HU229206B1 (en) 2013-09-30
BG108553A (bg) 2005-04-30
ES2453164T3 (es) 2014-04-04
MA27058A1 (fr) 2004-12-20
EA006445B9 (ru) 2017-02-28
EP3168218A1 (en) 2017-05-17
CZ2004196A3 (cs) 2005-01-12

Similar Documents

Publication Publication Date Title
CN100439360C (zh) 包括n-[2-(二乙氨基)乙基]-5-[(5-氟-2-氧代-3h-吲哚-3-亚基)甲基]-2,4-二甲基-1h-吡咯-3-甲酰胺的苹果酸盐的晶体、其制备方法和其组合物
AU2002324684A1 (en) 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
CA3233057A1 (en) Egfr inhibitor polymorph forms
EP4438613A1 (en) Mono-p-toluenesulfonate of axl kinase inhibitor and crystal form thereof
CN103298784A (zh) 一种酪氨酸激酶抑制剂的盐形式
HK1066542B (en) 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
WO2024260348A1 (zh) 二氢蝶啶酮类化合物的结晶及其制备方法
HK1088008B (en) 2, 4-dimethyl-1h-pyrrole-3-carboxamide, processes for its preparation and compositions thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
REG Reference to a national code

Ref country code: HK

Ref legal event code: DE

Ref document number: 1066542

Country of ref document: HK

C14 Grant of patent or utility model
GR01 Patent grant
REG Reference to a national code

Ref country code: HK

Ref legal event code: GR

Ref document number: 1066542

Country of ref document: HK

CP01 Change in the name or title of a patent holder
CP01 Change in the name or title of a patent holder

Address after: Michigan

Patentee after: PHARMACIA & UPJOHN CO.,LLC

Address before: Michigan

Patentee before: PHARMACIA & UPJOHN Co.

CX01 Expiry of patent term
CX01 Expiry of patent term

Granted publication date: 20081203

IW01 Full invalidation of patent right

Decision date of declaring invalidation: 20210408

Decision number of declaring invalidation: 49117

Granted publication date: 20081203