CA2417050A1 - Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for preparing them - Google Patents

Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for preparing them Download PDF

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Publication number
CA2417050A1
CA2417050A1 CA002417050A CA2417050A CA2417050A1 CA 2417050 A1 CA2417050 A1 CA 2417050A1 CA 002417050 A CA002417050 A CA 002417050A CA 2417050 A CA2417050 A CA 2417050A CA 2417050 A1 CA2417050 A1 CA 2417050A1
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Prior art keywords
bicyclic heterocycles
preparing
compounds
processes
diseases
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Granted
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CA002417050A
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French (fr)
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CA2417050C (en
Inventor
Frank Himmelsbach
Elke Langkopf
Birgit Jung
Stefan Blech
Flavio Solca
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Boehringer Ingelheim Pharma GmbH and Co KG
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Individual
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/14—Antitussive agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/94—Nitrogen atoms
    • 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
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Urology & Nephrology (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Oncology (AREA)
  • Otolaryngology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The present invention relates to bicyclic heterocycles of general formula (see formula I) wherein R a, R b, R c and n are defined as in claim 1, the tautomers, stereoisomers and salts thereof, particularly the physiologi-cally acceptable salts thereof with inorganic or organic acids or bases which have valuable pharmacological properties, in particular an inhibitory effect on signal transduction mediated by tyrosine kinases, their use in the treatment of diseases, especially tumoral diseases and diseases of the lungs and airways, and the preparation thereof.
CA002417050A 2000-08-26 2001-08-18 Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for preparing them Expired - Fee Related CA2417050C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10042060A DE10042060A1 (en) 2000-08-26 2000-08-26 Bicyclic heterocycles, medicaments containing these compounds, their use and processes for their preparation
DE10042060.5 2000-08-26
PCT/EP2001/009537 WO2002018373A1 (en) 2000-08-26 2001-08-18 Quinazoline derivatives, medicaments containing these compounds, their use, and methods for the production thereof

Publications (2)

Publication Number Publication Date
CA2417050A1 true CA2417050A1 (en) 2002-03-07
CA2417050C CA2417050C (en) 2009-04-14

Family

ID=7653947

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002417050A Expired - Fee Related CA2417050C (en) 2000-08-26 2001-08-18 Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for preparing them

Country Status (7)

Country Link
EP (1) EP1315717A1 (en)
JP (1) JP2004517048A (en)
AU (1) AU2001284021A1 (en)
CA (1) CA2417050C (en)
DE (1) DE10042060A1 (en)
MX (1) MXPA03000873A (en)
WO (1) WO2002018373A1 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8088782B2 (en) 2008-05-13 2012-01-03 Astrazeneca Ab Crystalline 4-(3-chloro-2-fluoroanilino)-7 methoxy-6-{[1-(N-methylcarbamoylmethyl)piperidin-4-yl]oxy}quinazoline difumarate form A
US8318752B2 (en) 2003-09-19 2012-11-27 Astrazeneca Ab 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[1-(N-methylcarbamoyl-methyl)piperidin-4-yl]oxy}quinazoline, its pharmaceutically acceptable salts, and pharmaceutical compositions comprising the same
US8399667B2 (en) 2002-03-28 2013-03-19 Astrazeneca Ab 4-anilino quinazoline derivatives as antiproliferative agents
US8735410B2 (en) 2005-02-26 2014-05-27 Astrazeneca Ab Quinazoline derivatives as tyrosine kinase inhibitors

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MXPA01012899A (en) 1999-06-21 2002-07-30 Boehringer Ingelheim Pharma Bicyclic heterocycles, medicaments containing these compounds, their use and methods for the production thereof.
US7019012B2 (en) 2000-12-20 2006-03-28 Boehringer Ingelheim International Pharma Gmbh & Co. Kg Quinazoline derivatives and pharmaceutical compositions containing them
US6924285B2 (en) 2002-03-30 2005-08-02 Boehringer Ingelheim Pharma Gmbh & Co. Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them
DE10221018A1 (en) * 2002-05-11 2003-11-27 Boehringer Ingelheim Pharma Use of inhibitors of EGFR-mediated signal transduction for the treatment of benign prostatic hyperplasia (BPH) / prostatic hypertrophy
US7223749B2 (en) 2003-02-20 2007-05-29 Boehringer Ingelheim International Gmbh Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for preparing them
DE10307165A1 (en) * 2003-02-20 2004-09-02 Boehringer Ingelheim Pharma Gmbh & Co. Kg Bicyclic heterocycles, medicaments containing these compounds, their use and processes for their preparation
GB0317665D0 (en) 2003-07-29 2003-09-03 Astrazeneca Ab Qinazoline derivatives
CA2557433C (en) 2004-02-19 2013-05-14 Rexahn Corporation Quinazoline derivatives and therapeutic use thereof
US20060035893A1 (en) 2004-08-07 2006-02-16 Boehringer Ingelheim International Gmbh Pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders
PE20060777A1 (en) 2004-12-24 2006-10-06 Boehringer Ingelheim Int INDOLINONE DERIVATIVES FOR THE TREATMENT OR PREVENTION OF FIBROTIC DISEASES
KR100832594B1 (en) * 2005-11-08 2008-05-27 한미약품 주식회사 Quinazoline derivatives as an multiplex inhibitor and method for the preparation thereof
WO2007055513A1 (en) * 2005-11-08 2007-05-18 Hanmi Pharm. Co., Ltd. Quinazoline derivatives as a signal transduction inhibitor and method for the preparation thereof
EP1948179A1 (en) 2005-11-11 2008-07-30 Boehringer Ingelheim International GmbH Quinazoline derivatives for the treatment of cancer diseases
RU2492864C2 (en) 2006-09-18 2013-09-20 Бёрингер Ингельхайм Интернациональ Гмбх Method of treating cancer carrying egfr mutations
EP1921070A1 (en) 2006-11-10 2008-05-14 Boehringer Ingelheim Pharma GmbH & Co. KG Bicyclic heterocycles, medicaments comprising them, their use and process for their preparation
JP5377332B2 (en) 2007-02-06 2013-12-25 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Bicyclic heterocycles, drugs containing these compounds, their use and their preparation
CA2711582A1 (en) 2008-02-07 2009-08-13 Boehringer Ingelheim International Gmbh Spirocyclic heterocycles, formulations containing said compounds, use thereof and processes for the preparation thereof
JP5539351B2 (en) 2008-08-08 2014-07-02 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Cyclohexyloxy-substituted heterocycles, medicaments containing these compounds, and methods for producing them
WO2010054285A2 (en) 2008-11-10 2010-05-14 National Health Research Institutes Fused bicyclic and tricyclic pyrimidine compounds as tyrosine kinase inhibitors
WO2011003853A2 (en) 2009-07-06 2011-01-13 Boehringer Ingelheim International Gmbh Process for drying of bibw2992, of its salts and of solid pharmaceutical formulations comprising this active ingredient
PH12012500097A1 (en) * 2009-07-21 2011-01-27 Shanghai Inst Organic Chem Potent small molecule inhibitors of autophagy, and methods of use thereof
CN102382106A (en) * 2010-08-30 2012-03-21 黄振华 Aniline substituted quinazoline derivative
WO2013135176A1 (en) * 2012-03-16 2013-09-19 苏州迈泰生物技术有限公司 Aminoquinazoline derivative and use thereof in preparing anti-malignant tumor medicament
US9242965B2 (en) 2013-12-31 2016-01-26 Boehringer Ingelheim International Gmbh Process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form and use thereof for synthesis of EGFR tyrosine kinase inhibitors
CN108148071B (en) * 2016-11-25 2019-10-15 广东东阳光药业有限公司 Salt of amido quinazoline derivatives and application thereof
CN115894455B (en) * 2021-09-30 2024-04-19 北京赛特明强医药科技有限公司 Quinazoline compound, composition and application thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW436485B (en) * 1997-08-01 2001-05-28 American Cyanamid Co Substituted quinazoline derivatives
HUP0301132A3 (en) * 1999-02-27 2004-03-29 Boehringer Ingelheim Pharma 4-amino-quinazoline and quinoline derivatives having an inhibitory effect on signal transduction mediated by tyrosine kinases, process for their preparation their use and pharmaceutical compositions containing them
DE19911509A1 (en) * 1999-03-15 2000-09-21 Boehringer Ingelheim Pharma Bicyclic heterocycles, medicaments containing these compounds, their use and processes for their preparation
MXPA01012899A (en) * 1999-06-21 2002-07-30 Boehringer Ingelheim Pharma Bicyclic heterocycles, medicaments containing these compounds, their use and methods for the production thereof.
DE19928281A1 (en) * 1999-06-21 2000-12-28 Boehringer Ingelheim Pharma Arylamino and aralkylamino substituted quinoline and quinazoline derivatives, useful for the treatment of e.g. tumors, pulmonary, respiratory and gastrointestinal disorders and psoriasis
DE10017539A1 (en) * 2000-04-08 2001-10-11 Boehringer Ingelheim Pharma New 6-acylamino-4-amino-quinazoline or quinoline derivatives, are tyrosine kinase-mediated signal transduction inhibitors useful e.g. for treating tumors or respiratory or gastrointestinal diseases

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8399667B2 (en) 2002-03-28 2013-03-19 Astrazeneca Ab 4-anilino quinazoline derivatives as antiproliferative agents
US8318752B2 (en) 2003-09-19 2012-11-27 Astrazeneca Ab 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[1-(N-methylcarbamoyl-methyl)piperidin-4-yl]oxy}quinazoline, its pharmaceutically acceptable salts, and pharmaceutical compositions comprising the same
US8735410B2 (en) 2005-02-26 2014-05-27 Astrazeneca Ab Quinazoline derivatives as tyrosine kinase inhibitors
US8088782B2 (en) 2008-05-13 2012-01-03 Astrazeneca Ab Crystalline 4-(3-chloro-2-fluoroanilino)-7 methoxy-6-{[1-(N-methylcarbamoylmethyl)piperidin-4-yl]oxy}quinazoline difumarate form A
US8404839B2 (en) 2008-05-13 2013-03-26 Astrazeneca Ab Crystalline 4-(3-chloro-2-fluoroanilino)-7 methoxy-6-{[1-(N-methylcarbamoylmethyl)piperidin-4-yl]oxy} quinazoline difumarate Form A

Also Published As

Publication number Publication date
AU2001284021A1 (en) 2002-03-13
MXPA03000873A (en) 2003-06-06
EP1315717A1 (en) 2003-06-04
WO2002018373A1 (en) 2002-03-07
CA2417050C (en) 2009-04-14
JP2004517048A (en) 2004-06-10
DE10042060A1 (en) 2002-03-07

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