CA2484395A1 - Heterocycles bicycliques, medicaments contenant ces composes, leur utilisation et leur procede de production - Google Patents

Heterocycles bicycliques, medicaments contenant ces composes, leur utilisation et leur procede de production Download PDF

Info

Publication number
CA2484395A1
CA2484395A1 CA002484395A CA2484395A CA2484395A1 CA 2484395 A1 CA2484395 A1 CA 2484395A1 CA 002484395 A CA002484395 A CA 002484395A CA 2484395 A CA2484395 A CA 2484395A CA 2484395 A1 CA2484395 A1 CA 2484395A1
Authority
CA
Canada
Prior art keywords
group
denotes
carbon atoms
atoms
atom
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
CA002484395A
Other languages
English (en)
Other versions
CA2484395C (fr
Inventor
Frank Himmelsbach
Birgit Jung
Flavio Solca
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 CA2484395A1 publication Critical patent/CA2484395A1/fr
Application granted granted Critical
Publication of CA2484395C publication Critical patent/CA2484395C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • 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
    • A61P11/08—Bronchodilators
    • 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
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems

Landscapes

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

Abstract

La présente invention concerne des hétérocycles bicycliques de la formule générale (I), où R?a¿, R?b¿, R?c¿, A, B, C, D, E et X ont la définition donnée dans la revendication 1, leurs tautomères, leurs stéréo-isomères, leurs mélanges et leurs sels, notamment leurs sels physiologiquement compatibles avec des acides inorganiques ou organiques ayant de précieuses caractéristiques pharmacologiques, notamment une action inhibitrice sur la transduction de signaux transmise par la tyrosine-kinase. L'invention concerne également leur utilisation pour le traitement de maladies, notamment de maladies tumorales et de l'hypertrophie de la prostate (BPH), de maladies des poumons et des voies respiratoires, ainsi que leur production.
CA2484395A 2002-04-19 2003-04-14 Heterocycles bicycliques, medicaments contenant ces composes, leur utilisation et leur procede de production Expired - Fee Related CA2484395C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10217689.2 2002-04-19
DE10217689A DE10217689A1 (de) 2002-04-19 2002-04-19 Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, ihre Verwendung und Verfahren zu ihrer Herstellung
PCT/EP2003/003828 WO2003089439A1 (fr) 2002-04-19 2003-04-14 Heterocycles bicycliques, medicaments contenant ces composes, leur utilisation et leur procede de production

Publications (2)

Publication Number Publication Date
CA2484395A1 true CA2484395A1 (fr) 2003-10-30
CA2484395C CA2484395C (fr) 2011-11-22

Family

ID=29224623

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2484395A Expired - Fee Related CA2484395C (fr) 2002-04-19 2003-04-14 Heterocycles bicycliques, medicaments contenant ces composes, leur utilisation et leur procede de production

Country Status (10)

Country Link
EP (1) EP1499619A1 (fr)
JP (1) JP4527406B2 (fr)
AR (1) AR039571A1 (fr)
AU (1) AU2003226806A1 (fr)
CA (1) CA2484395C (fr)
DE (1) DE10217689A1 (fr)
PE (1) PE20040171A1 (fr)
TW (1) TW200408643A (fr)
UY (1) UY27767A1 (fr)
WO (1) WO2003089439A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7863281B2 (en) 2002-04-19 2011-01-04 Boehringer Ingelheim Pharma Gmbh & Co. Kg Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUP0201900A3 (en) 1999-06-21 2003-02-28 Boehringer Ingelheim Pharma Bicyclic heterocycles, pharmaceutical compositions containing them, 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
CA2491191C (fr) 2002-07-15 2014-02-04 Exelixis, Inc. Modulateurs de kinase de type recepteur et procedes d'utilisation
US8309562B2 (en) 2003-07-03 2012-11-13 Myrexis, Inc. Compounds and therapeutical use thereof
ES2925655T3 (es) 2003-09-26 2022-10-19 Exelixis Inc Moduladores c-Met y métodos de uso
PT1746999E (pt) * 2004-05-06 2012-01-11 Warner Lambert Co 4-fenilamino-quinazolin-6-il-amidas
US8258145B2 (en) 2005-01-03 2012-09-04 Myrexis, Inc. Method of treating brain cancer
CA2592900A1 (fr) 2005-01-03 2006-07-13 Myriad Genetics Inc. Composes et utilisation therapeutique associee
KR100832594B1 (ko) * 2005-11-08 2008-05-27 한미약품 주식회사 다중저해제로서의 퀴나졸린 유도체 및 이의 제조방법
CA2833706C (fr) 2005-11-11 2014-10-21 Boehringer Ingelheim International Gmbh Derives de quinazoline pour le traitement des affections cancereuses
AU2007299080B2 (en) 2006-09-18 2013-04-18 Boehringer Ingelheim International Gmbh Method for treating cancer harboring EGFR mutations
TWI447108B (zh) 2009-01-16 2014-08-01 Exelixis Inc 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及其結晶型
AU2010266725A1 (en) 2009-07-02 2012-02-23 Newgen Therapeutics, Inc. Phosphorus containing quinazoline compounds and methods of use
DK2451445T3 (da) 2009-07-06 2019-06-24 Boehringer Ingelheim Int Fremgangsmåde til at tørre bibw2992, dets salte og faste farmaceutiske formuleringer omfattende denne aktive ingrediens
UA108618C2 (uk) 2009-08-07 2015-05-25 Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку
CN102020639A (zh) 2009-09-14 2011-04-20 上海恒瑞医药有限公司 6-氨基喹唑啉或3-氰基喹啉类衍生物、其制备方法及其在医药上的应用
HUE033575T2 (hu) 2011-05-26 2017-12-28 Xuanzhu Pharma Co Ltd Tirozin-kináz inhibitor kinazolin származék, elõállítási eljárása és alkalmazása
JP2014532063A (ja) * 2011-10-12 2014-12-04 テリジェン リミテッドＴｅｌｉｇｅｎｅ Ｌｔｄ キナーゼ阻害剤としてのキナゾリン誘導体およびその使用方法
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
AU2019346550A1 (en) 2018-09-25 2021-04-22 Black Diamond Therapeutics, Inc. Quinazoline derivatives as tyrosine kinase inhibitor, compositions, methods of making them and their use

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2249446C (fr) * 1996-04-12 2008-06-17 Warner-Lambert Company Inhibiteurs irreversibles de tyrosine kinases
TW436485B (en) * 1997-08-01 2001-05-28 American Cyanamid Co Substituted quinazoline derivatives
AU6159499A (en) * 1998-09-29 2000-04-17 Wyeth Holdings Corporation Substituted 3-cyanoquinolines as protein tyrosine kinases inhibitors
DE19908567A1 (de) * 1999-02-27 2000-08-31 Boehringer Ingelheim Pharma Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung
AU3281600A (en) * 1999-02-27 2000-09-21 Boehringer Ingelheim Pharma Gmbh & Co. Kg 4-amino-quinazoline and quinoline derivatives having an inhibitory effect on signal transsduction mediated by tyrosine kinases
HUP0201900A3 (en) * 1999-06-21 2003-02-28 Boehringer Ingelheim Pharma Bicyclic heterocycles, pharmaceutical compositions containing them, their use and methods for the production thereof
ES2280375T3 (es) * 2000-04-08 2007-09-16 BOEHRINGER INGELHEIM PHARMA GMBH &amp; CO.KG Heterociclos biciclicos, medicamentos que contienen estos compuestos, su uso y procedimiento para su preparacion.
DE10017539A1 (de) * 2000-04-08 2001-10-11 Boehringer Ingelheim Pharma Bicyclische Heterocyclen, diese Verbingungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung
DE10042061A1 (de) * 2000-08-26 2002-03-07 Boehringer Ingelheim Pharma Bicyclische Heterocyclen,diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung
DE10042062A1 (de) * 2000-08-26 2002-03-07 Boehringer Ingelheim Pharma Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Hertellung

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7863281B2 (en) 2002-04-19 2011-01-04 Boehringer Ingelheim Pharma Gmbh & Co. Kg Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof

Also Published As

Publication number Publication date
UY27767A1 (es) 2003-11-28
AR039571A1 (es) 2005-02-23
EP1499619A1 (fr) 2005-01-26
DE10217689A1 (de) 2003-11-13
JP2005526837A (ja) 2005-09-08
PE20040171A1 (es) 2004-06-02
CA2484395C (fr) 2011-11-22
JP4527406B2 (ja) 2010-08-18
AU2003226806A1 (en) 2003-11-03
WO2003089439A1 (fr) 2003-10-30
TW200408643A (en) 2004-06-01

Similar Documents

Publication Publication Date Title
CA2484395A1 (fr) Heterocycles bicycliques, medicaments contenant ces composes, leur utilisation et leur procede de production
US7863281B2 (en) Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof
US7049438B2 (en) Quinazoline derivatives for treatment of tumours
EP2215085B1 (fr) Dérivés de pyridine et de pyrazine utiles pour le traitement de troubles de la prolifération cellulaire
US20070213367A1 (en) Substituted 3-cyanoquinolines as MEK inhibitors
CA2491191A1 (fr) Modulateurs de kinase de type recepteur et procedes d&#39;utilisation
TW200302221A (en) Quinazoline derivatives
SK282236B6 (sk) Chinazolínové deriváty, spôsob ich prípravy, farmaceutický prostriedok, ktorý ich obsahuje a ich použitie
JP2003530395A (ja) 二環式複素環化合物、これらの化合物を含む医薬組成物、それらの使用及びそれらの調製方法
EP1326859A1 (fr) Derives quinazoline a activite anti-tumorale
JP2008515961A (ja) 癌に対する使用のためのキナゾリン誘導体
US20070191346A1 (en) 3-Cyano-quinoline derivatives
JP2009528335A (ja) キナゾリン誘導体
IL168013A (en) Quinazoline derivatives, processes for preparation thereof, pharmaceutical compositions comprising the same and uses thereof
CA2516426A1 (fr) Heterocycles bicycliques, medicaments les contenant, leur utilisation et leurs procedes de production
WO2003048159A1 (fr) Derives de la quinoleine
US7504408B2 (en) Quinzoline derivatives for use in the treatment of cancer
WO2003053960A2 (fr) Composes chimiques
WO2003047583A1 (fr) Compositions pharmaceutiques comprenant des derives de 3-cyanoquinoline a substitution benzofuranyle et leur utilisation dans le traitement de tumeurs solides
CA2540501A1 (fr) Derives de quinoleine et de quinazoline, medicaments contenant ces composes, utilisation et procede de production de ceux-ci
WO2003047585A1 (fr) Compositions pharmaceutiques contenant des derives de 3-cyanoquinoline a substitution benzofuranyle et leur utilisation dans le traitement de tumeurs solides
WO2003047582A1 (fr) Derives de la quinoleine, utilises en tant qu&#39;agents antitumoraux
WO2004056812A1 (fr) Derives de 4-(pyridin-4-ylamino)-quinazoline utilises comme agents anticancereux
WO2004081000A1 (fr) Dérivés quinazoliniques
CN102627632A (zh) 一种胺基喹唑啉衍生物及其制备方法和用途

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20130415