CA2323111A1 - New substituted indolinones, the preparation thereof and their use as pharmaceutical compositions - Google Patents

New substituted indolinones, the preparation thereof and their use as pharmaceutical compositions Download PDF

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Publication number
CA2323111A1
CA2323111A1 CA002323111A CA2323111A CA2323111A1 CA 2323111 A1 CA2323111 A1 CA 2323111A1 CA 002323111 A CA002323111 A CA 002323111A CA 2323111 A CA2323111 A CA 2323111A CA 2323111 A1 CA2323111 A1 CA 2323111A1
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CA
Canada
Prior art keywords
pharmaceutical compositions
preparation
substituted indolinones
new substituted
indolinones
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
Application number
CA002323111A
Other languages
French (fr)
Other versions
CA2323111C (en
Inventor
Armin Heckel
Rainer Walter
Wolfgang Grell
Jacobus C. A. Van Meel
Norbert Redemann
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Individual
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
Application filed by Individual filed Critical Individual
Publication of CA2323111A1 publication Critical patent/CA2323111A1/en
Application granted granted Critical
Publication of CA2323111C publication Critical patent/CA2323111C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/34—Oxygen atoms in position 2
    • 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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Neurology (AREA)
  • Virology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Molecular Biology (AREA)
  • Hospice & Palliative Care (AREA)
  • AIDS & HIV (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

The present invention relates to substituted indolinones of general formula (see formula I) wherein R1 to R5 and X are defined as in claim 1, the isomers thereof and the salts thereof, particularly the physiologically acceptable salts thereof which have valuable pharmacological properties, particularly an inhibitory effect on various kinases and cycline/CDK
complexes and on the proliferation of various tumour cells, pharmaceutical compositions containing these compounds, their use and processes for preparing them.
CA002323111A 1998-04-15 1999-04-10 New substituted indolinones, the preparation thereof and their use as pharmaceutical compositions Expired - Fee Related CA2323111C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19816624A DE19816624A1 (en) 1998-04-15 1998-04-15 Novel substituted indolinones, their preparation and their use as pharmaceuticals
DE19816624.9 1998-04-15
PCT/EP1999/002436 WO1999052869A1 (en) 1998-04-15 1999-04-10 Substituted indolinones having an inhibiting effect on kinases and cycline/cdk complexes

Publications (2)

Publication Number Publication Date
CA2323111A1 true CA2323111A1 (en) 1999-10-21
CA2323111C CA2323111C (en) 2009-09-15

Family

ID=7864562

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002323111A Expired - Fee Related CA2323111C (en) 1998-04-15 1999-04-10 New substituted indolinones, the preparation thereof and their use as pharmaceutical compositions

Country Status (31)

Country Link
EP (1) EP1071665B1 (en)
JP (1) JP4015365B2 (en)
KR (1) KR100588250B1 (en)
CN (1) CN100338036C (en)
AR (1) AR015763A1 (en)
AT (1) ATE251138T1 (en)
AU (1) AU749829B2 (en)
BG (1) BG64443B1 (en)
BR (1) BR9909688A (en)
CA (1) CA2323111C (en)
CO (1) CO5011040A1 (en)
DE (2) DE19816624A1 (en)
DK (1) DK1071665T3 (en)
EA (1) EA003532B1 (en)
EE (1) EE04432B1 (en)
ES (1) ES2207209T3 (en)
HU (1) HUP0101568A3 (en)
ID (1) ID26420A (en)
IL (1) IL138036A0 (en)
MY (1) MY122357A (en)
NO (1) NO317298B1 (en)
NZ (1) NZ507967A (en)
PL (1) PL343314A1 (en)
PT (1) PT1071665E (en)
SK (1) SK283824B6 (en)
TR (1) TR200002980T2 (en)
TW (1) TW510897B (en)
UA (1) UA63009C2 (en)
WO (1) WO1999052869A1 (en)
YU (1) YU59800A (en)
ZA (1) ZA200004623B (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7741361B2 (en) 2004-12-27 2010-06-22 Boehringer Ingelheim Pharmaceuticals, Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof
US7795272B2 (en) 2004-03-13 2010-09-14 Boehringer Ingelheim Pharmaceutical, Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof
US7858616B2 (en) 2002-07-23 2010-12-28 Boehringer Ingelheim Pharma Gmbh & Co. Kg Indolinone derivatives substituted in the 6 position, their preparation and their use as medicaments
US7932392B2 (en) 2002-03-26 2011-04-26 Boehringer Ingelheim Pharmaceuticals, Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof
US8268859B2 (en) 2008-06-06 2012-09-18 Boehringer Ingelheim International Gmbh Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof
US8658637B2 (en) 2006-12-06 2014-02-25 Boehringer Ingelheim International Gmbh Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof
US8741897B2 (en) 2003-09-24 2014-06-03 Boehringer Ingelheim Pharmaceuticals Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof
US20160022638A1 (en) * 2013-03-15 2016-01-28 Ligand Pharmaceuticals Incorporated Methods of treatment associated with the granulocyte colony-stimulating factor receptor
US10154990B2 (en) 2004-12-24 2018-12-18 Boehringer Ingelheim International Gmbh Medicaments for the treatment or prevention of fibrotic diseases

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6569868B2 (en) 1998-04-16 2003-05-27 Sugen, Inc. 2-indolinone derivatives as modulators of protein kinase activity
GB9904933D0 (en) 1999-03-04 1999-04-28 Glaxo Group Ltd Compounds
US6624171B1 (en) 1999-03-04 2003-09-23 Smithkline Beecham Corporation Substituted aza-oxindole derivatives
GB9904932D0 (en) * 1999-03-04 1999-04-28 Glaxo Group Ltd Composition and method for preventing/reducing the severity of side effects of chemotherapy and/or radiation therapy
GB9904995D0 (en) * 1999-03-04 1999-04-28 Glaxo Group Ltd Substituted aza-oxindole derivatives
DE19924401A1 (en) * 1999-05-27 2000-11-30 Boehringer Ingelheim Pharma Novel substituted indolinones, their preparation and their use as pharmaceuticals
MXPA02002097A (en) * 1999-08-27 2002-11-07 Boehringer Ingelheim Pharma Substituted indolinones as tyrosine kinase inhibitors.
US6762180B1 (en) 1999-10-13 2004-07-13 Boehringer Ingelheim Pharma Kg Substituted indolines which inhibit receptor tyrosine kinases
UA75054C2 (en) * 1999-10-13 2006-03-15 Бьорінгер Інгельхайм Фарма Гмбх & Ко. Кг Substituted in position 6 indolinones, producing and use thereof as medicament
US6620818B1 (en) 2000-03-01 2003-09-16 Smithkline Beecham Corporation Method for reducing the severity of side effects of chemotherapy and/or radiation therapy
MY128450A (en) 2000-05-24 2007-02-28 Upjohn Co 1-(pyrrolidin-1-ylmethyl)-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
CA2410509A1 (en) 2000-06-02 2001-12-13 Sugen, Inc. Indolinone derivatives as protein kinase/phosphatase inhibitors
JP2004517840A (en) * 2000-11-27 2004-06-17 フアルマシア・イタリア・エツセ・ピー・アー Phenylacetamide-pyrazole derivatives and their use as antitumor agents
DE10117204A1 (en) 2001-04-06 2002-10-10 Boehringer Ingelheim Pharma Indolinones substituted in the 6-position, their preparation and their use as medicaments
US6599902B2 (en) 2001-05-30 2003-07-29 Sugen, Inc. 5-aralkysufonyl-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives as kinase inhibitors
DE10233500A1 (en) * 2002-07-24 2004-02-19 Boehringer Ingelheim Pharma Gmbh & Co. Kg 3-Z- [1- (4- (N - ((4-methyl-piperazin-1-yl) -methylcarbonyl) -N-methyl-amino) -anilino) -1-phenyl-methylene] -6-methoxycarbonyl- 2-indolinone monoethanesulfonate and its use as a medicament
DE10237423A1 (en) * 2002-08-16 2004-02-19 Boehringer Ingelheim Pharma Gmbh & Co. Kg Treating immunological (or related) diseases, e.g. inflammatory bowel disease, rheumatoid arthritis or psoriasis, comprises administration of 3-methylene-2-indolinone derivative or quinazoline compound
JP4879492B2 (en) * 2002-11-27 2012-02-22 アラーガン、インコーポレイテッド Kinase inhibitors for the treatment of diseases
US20050043233A1 (en) 2003-04-29 2005-02-24 Boehringer Ingelheim International Gmbh Combinations for the treatment of diseases involving cell proliferation, migration or apoptosis of myeloma cells or angiogenesis
ATE414701T1 (en) * 2003-10-03 2008-12-15 Boehringer Ingelheim Pharma FLUORESCENCE PROBE FOR USE IN A PROTEIN KINASE INHIBITOR BINDING ASSAY
DE102004012070A1 (en) * 2004-03-12 2005-09-29 Boehringer Ingelheim Pharma Gmbh & Co. Kg New cycloalkyl-containing 5-acylindolinones, their preparation and their use as medicaments
US7781475B2 (en) 2005-06-10 2010-08-24 Merck Patent Gmbh Oxindoles as kinase inhibitors
WO2007057399A2 (en) * 2005-11-15 2007-05-24 Boehringer Ingelheim International Gmbh Treatment of cancer with indole derivatives
US20170065529A1 (en) 2015-09-09 2017-03-09 Boehringer Ingelheim International Gmbh Pharmaceutical dosage form for immediate release of an indolinone derivative
WO2011032320A1 (en) * 2009-09-21 2011-03-24 F. Hoffmann-La Roche Ag Novel alkene oxindole derivatives
CN109293551A (en) * 2011-11-14 2019-02-01 利亘制药公司 Method and composition relevant to granulocyte colony stimulating factor receptor
CN107033064B (en) * 2017-04-28 2019-07-09 西安医学院 A kind of 3- (morpholine replaces fragrant imido grpup) Benzazole compounds and its preparation method and application
CN111285872B (en) * 2018-12-06 2022-05-17 北京志健金瑞生物医药科技有限公司 Indole-2-ketone derivative and preparation method and application thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9501567D0 (en) * 1995-01-26 1995-03-15 Pharmacia Spa Hydrosoluble 3-arylidene-2-oxindole derivatives as tyrosine kinase inhibitors
US5880141A (en) * 1995-06-07 1999-03-09 Sugen, Inc. Benzylidene-Z-indoline compounds for the treatment of disease
GB9718913D0 (en) * 1997-09-05 1997-11-12 Glaxo Group Ltd Substituted oxindole derivatives
DE19824922A1 (en) * 1998-06-04 1999-12-09 Boehringer Ingelheim Pharma Novel substituted indolinones, their preparation and their use as pharmaceuticals
UA75054C2 (en) * 1999-10-13 2006-03-15 Бьорінгер Інгельхайм Фарма Гмбх & Ко. Кг Substituted in position 6 indolinones, producing and use thereof as medicament

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7932392B2 (en) 2002-03-26 2011-04-26 Boehringer Ingelheim Pharmaceuticals, Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof
US8212040B2 (en) 2002-03-26 2012-07-03 Boehringer Ingelheim Pharmaceuticals, Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and thereof
US7858616B2 (en) 2002-07-23 2010-12-28 Boehringer Ingelheim Pharma Gmbh & Co. Kg Indolinone derivatives substituted in the 6 position, their preparation and their use as medicaments
US8741897B2 (en) 2003-09-24 2014-06-03 Boehringer Ingelheim Pharmaceuticals Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof
US7795272B2 (en) 2004-03-13 2010-09-14 Boehringer Ingelheim Pharmaceutical, Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof
US10154990B2 (en) 2004-12-24 2018-12-18 Boehringer Ingelheim International Gmbh Medicaments for the treatment or prevention of fibrotic diseases
US7741361B2 (en) 2004-12-27 2010-06-22 Boehringer Ingelheim Pharmaceuticals, Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof
US8658637B2 (en) 2006-12-06 2014-02-25 Boehringer Ingelheim International Gmbh Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof
US8268859B2 (en) 2008-06-06 2012-09-18 Boehringer Ingelheim International Gmbh Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof
US20160022638A1 (en) * 2013-03-15 2016-01-28 Ligand Pharmaceuticals Incorporated Methods of treatment associated with the granulocyte colony-stimulating factor receptor
US9962370B2 (en) * 2013-03-15 2018-05-08 Ligand Pharmaceuticals Incorporated Methods of treatment associated with the granulocyte colony-stimulating factor receptor
US10420748B2 (en) * 2013-03-15 2019-09-24 Ligand Pharmaceuticals Incorporated Methods of treatment associated with the granulocyte colony-stimulating factor receptor

Also Published As

Publication number Publication date
AU3814999A (en) 1999-11-01
DE59907199D1 (en) 2003-11-06
CO5011040A1 (en) 2001-02-28
BR9909688A (en) 2000-12-19
HUP0101568A2 (en) 2001-09-28
IL138036A0 (en) 2001-10-31
SK15132000A3 (en) 2001-03-12
YU59800A (en) 2003-04-30
CN1297438A (en) 2001-05-30
SK283824B6 (en) 2004-02-03
DK1071665T3 (en) 2004-01-05
TR200002980T2 (en) 2001-02-21
JP4015365B2 (en) 2007-11-28
CN100338036C (en) 2007-09-19
EE200000598A (en) 2002-04-15
ATE251138T1 (en) 2003-10-15
EP1071665A1 (en) 2001-01-31
NO20005151D0 (en) 2000-10-13
HUP0101568A3 (en) 2002-12-28
BG64443B1 (en) 2005-02-28
DE19816624A1 (en) 1999-10-21
TW510897B (en) 2002-11-21
MY122357A (en) 2006-04-29
UA63009C2 (en) 2004-01-15
NZ507967A (en) 2003-04-29
KR20010042731A (en) 2001-05-25
PL343314A1 (en) 2001-08-13
AU749829B2 (en) 2002-07-04
WO1999052869A1 (en) 1999-10-21
ES2207209T3 (en) 2004-05-16
ID26420A (en) 2000-12-21
EE04432B1 (en) 2005-02-15
EA003532B1 (en) 2003-06-26
ZA200004623B (en) 2001-05-30
NO20005151L (en) 2000-10-13
NO317298B1 (en) 2004-10-04
EA200001021A1 (en) 2001-06-25
KR100588250B1 (en) 2006-06-13
AR015763A1 (en) 2001-05-16
PT1071665E (en) 2004-02-27
JP2002511449A (en) 2002-04-16
BG104813A (en) 2001-08-31
EP1071665B1 (en) 2003-10-01
CA2323111C (en) 2009-09-15

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