CA2493026C - Anthranylamidopyrimidines inhibant vegfr-2 et vegfr-3 - Google Patents

Anthranylamidopyrimidines inhibant vegfr-2 et vegfr-3 Download PDF

Info

Publication number
CA2493026C
CA2493026C CA2493026A CA2493026A CA2493026C CA 2493026 C CA2493026 C CA 2493026C CA 2493026 A CA2493026 A CA 2493026A CA 2493026 A CA2493026 A CA 2493026A CA 2493026 C CA2493026 C CA 2493026C
Authority
CA
Canada
Prior art keywords
alkyl
alkoxy
halo
group
differently
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.)
Expired - Fee Related
Application number
CA2493026A
Other languages
English (en)
Other versions
CA2493026A1 (fr
Inventor
Andreas Huth
Martin Krueger
Ludwig Zorn
Stuart Ince
Karl-Heinz Thierauch
Andreas Menrad
Martin Haberey
Holger Hess-Stump
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.)
Bayer Pharma AG
Original Assignee
Bayer Schering Pharma AG
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
Priority claimed from DE10235690A external-priority patent/DE10235690A1/de
Priority claimed from DE10328036A external-priority patent/DE10328036A1/de
Application filed by Bayer Schering Pharma AG filed Critical Bayer Schering Pharma AG
Publication of CA2493026A1 publication Critical patent/CA2493026A1/fr
Application granted granted Critical
Publication of CA2493026C publication Critical patent/CA2493026C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • 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
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • 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
    • 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
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
    • C07D413/02—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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Reproductive Health (AREA)
  • Endocrinology (AREA)
  • Diabetes (AREA)
  • Ophthalmology & Optometry (AREA)
  • Hematology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Oncology (AREA)
  • Vascular Medicine (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Obesity (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pregnancy & Childbirth (AREA)
  • Emergency Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Transplantation (AREA)
  • Orthopedic Medicine & Surgery (AREA)

Abstract

L'invention concerne des anthranylamidopyridinamides inhibant VEGFR-2 et VEGFR-3, leur fabrication et leur utilisation en tant que médicament destiné au traitement de maladies déclenchées par une angiogenèse persistante, ainsi que des produits intermédiaires destinés à la fabrication de ces composés. Les composés selon l'invention peuvent servir d'immunosuppresseurs en cas de croissance de tumeurs et métastases, psoriasis, sarcome de Kaposi, resténose telle que resténose provoquée par stent, endométriose, maladie de Crohn, maladie de Hodgkin, leucémie, arthrite telle qu'arthrite rhumatoïde, hémangiome, angiofibrome, maladies des yeux telles que rétinopathie diabétique, glaucome néovasculaire, maladies des reins telles que glomérulonéphrite, néphropathie diabétique, néphrosclérose maligne, syndrome microangiopathique thrombique, rejets de greffe et glomérulopathie, maladies fibrotiques telles que cirrhose du foie, maladies membrano-prolifératives, artériosclérose, blessures des tissus nerveux et inhibition de la réocclusion de vaisseaux après traitement avec sonde à ballonnet, installation de prothèses vasculaires ou de dispositifs mécaniques servant à maintenir des vaisseaux ouverts tels que des stents, taches de vieillesse ou dermite de contact, ou servir à favoriser une cicatrisation sans traces. Les composés selon l'invention peuvent également servir d'inhibiteurs de VEGFR-3 en cas de lymphangiogenèse.
CA2493026A 2002-07-31 2003-07-22 Anthranylamidopyrimidines inhibant vegfr-2 et vegfr-3 Expired - Fee Related CA2493026C (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE10235690.4 2002-07-31
DE10235690A DE10235690A1 (de) 2002-07-31 2002-07-31 VEGFR-2 und VEGFR-3 inhibitorische Anthranylamidpyridinamide
DE10328036A DE10328036A1 (de) 2003-06-19 2003-06-19 VEGFR-2 und VEGFR-3 inhibitorische Anthranylamidpyridine
DE10328036.7 2003-06-19
PCT/EP2003/007964 WO2004013102A1 (fr) 2002-07-31 2003-07-22 Anthranylamidopyrimidines inhibant vegfr-2 et vegfr-3

Publications (2)

Publication Number Publication Date
CA2493026A1 CA2493026A1 (fr) 2004-02-12
CA2493026C true CA2493026C (fr) 2011-05-24

Family

ID=31496742

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2493026A Expired - Fee Related CA2493026C (fr) 2002-07-31 2003-07-22 Anthranylamidopyrimidines inhibant vegfr-2 et vegfr-3

Country Status (18)

Country Link
EP (1) EP1594841A1 (fr)
JP (2) JP4777648B2 (fr)
KR (1) KR20050026535A (fr)
CN (1) CN1671666A (fr)
AU (1) AU2003281855A1 (fr)
BR (1) BR0313122A (fr)
CA (1) CA2493026C (fr)
CO (1) CO5720998A2 (fr)
CR (1) CR7673A (fr)
EC (1) ECSP055631A (fr)
HR (1) HRP20050187A2 (fr)
IL (1) IL166377A0 (fr)
MX (1) MXPA04012948A (fr)
NO (1) NO20051035L (fr)
PL (1) PL374610A1 (fr)
RS (1) RS20050084A (fr)
RU (1) RU2005105683A (fr)
WO (1) WO2004013102A1 (fr)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7615565B2 (en) 2002-07-31 2009-11-10 Bayer Schering Pharma Aktiengesellschaft VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridines
GB0229022D0 (en) * 2002-12-12 2003-01-15 Novartis Ag Organic Compounds
CA2511970C (fr) 2003-01-14 2012-06-26 Cytokinetics, Inc. Derives de l'uree utiles pour traiter l'insuffisance cardiaque
DE102004009238A1 (de) * 2004-02-26 2005-09-08 Merck Patent Gmbh Arylamid-Derivate
PL1765327T3 (pl) 2004-06-17 2015-01-30 Cytokinetics Inc Związki, kompozycje i sposoby
US7176222B2 (en) 2004-07-27 2007-02-13 Cytokinetics, Inc. Syntheses of ureas
EP1657241A1 (fr) * 2004-11-03 2006-05-17 Schering Aktiengesellschaft Nouveaux urées d' anthranylamide pyridine ayant une activité inhibitrice de kinase du récepteur de VEGF
EP1655297A1 (fr) * 2004-11-03 2006-05-10 Schering Aktiengesellschaft Pyridineurées de nicotinamide commes inhibiteurs du recepteur kinase du facteur de croissance endothéliale vasculaire (VEGF)
US7906533B2 (en) 2004-11-03 2011-03-15 Bayer Schering Pharma Ag Nicotinamide pyridinureas as vascular endothelial growth factor (VEGF) receptor kinase inhibitors
EP1655295A1 (fr) * 2004-11-03 2006-05-10 Schering Aktiengesellschaft Anthranilamide pyridinurées comme inhibiteurs de kinase du récepteur VEGF
KR20060071812A (ko) * 2004-12-22 2006-06-27 주식회사 엘지생명과학 신규한 3-(2-아미노-6-피리디닐)-4-히드록시페닐 아민유도체
WO2006070878A1 (fr) * 2004-12-28 2006-07-06 Astellas Pharma Inc. Derive d'acide carboxylique ou sel de ce derive
US7538223B2 (en) 2005-08-04 2009-05-26 Cytokinetics, Inc. Compounds, compositions and methods
US7825120B2 (en) 2005-12-15 2010-11-02 Cytokinetics, Inc. Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas
ES2419007T3 (es) 2005-12-15 2013-08-19 Cytokinetics, Inc. Ciertas entidades químicas, composiciones y procedimientos
EP1959962A2 (fr) 2005-12-16 2008-08-27 Cytokinetics, Inc. Entites chimiques, compositions et methodes
WO2007078839A2 (fr) 2005-12-19 2007-07-12 Cytokinetics, Inc. Composes, compositions et methodes
EP1975166A1 (fr) * 2007-03-30 2008-10-01 Bayer Schering Pharma AG Synthèse d'anthranilamides
EP2008658A1 (fr) * 2007-06-28 2008-12-31 Bayer Schering Pharma Aktiengesellschaft Combinaison synergique de anthranilamide pyridinurées et dérivés du benzamide
WO2009156484A2 (fr) * 2008-06-27 2009-12-30 Novartis Ag Composés organiques
AU2009287152B2 (en) * 2008-08-27 2014-09-25 Leo Pharma A/S Pyridine derivatives as VEGFR-2 receptor and protein tyrosine kinase inhibitors
CN101676267B (zh) 2008-09-16 2012-12-26 江苏恒瑞医药股份有限公司 N-[4-(1-氰基环戊基)苯基]-2-(4-吡啶甲基)氨基-3-吡啶甲酰胺的盐
EP2349440B1 (fr) 2008-10-07 2019-08-21 Mc10, Inc. Ballonnet de cathéter comportant un circuit intégré étirable et un réseau de détecteurs
US8886334B2 (en) 2008-10-07 2014-11-11 Mc10, Inc. Systems, methods, and devices using stretchable or flexible electronics for medical applications
US8389862B2 (en) 2008-10-07 2013-03-05 Mc10, Inc. Extremely stretchable electronics
US8372726B2 (en) 2008-10-07 2013-02-12 Mc10, Inc. Methods and applications of non-planar imaging arrays
US8097926B2 (en) 2008-10-07 2012-01-17 Mc10, Inc. Systems, methods, and devices having stretchable integrated circuitry for sensing and delivering therapy
US9723122B2 (en) 2009-10-01 2017-08-01 Mc10, Inc. Protective cases with integrated electronics
JP2014523633A (ja) 2011-05-27 2014-09-11 エムシー１０ インコーポレイテッド 電子的、光学的、且つ／又は機械的装置及びシステム並びにこれらの装置及びシステムを製造する方法
US9171794B2 (en) 2012-10-09 2015-10-27 Mc10, Inc. Embedding thin chips in polymer
CN104086484B (zh) * 2014-07-08 2016-05-25 上海宣创生物科技有限公司 烟酰胺类衍生物的甲磺酸盐溶剂化物晶体及其制备方法和应用
CN105541708A (zh) * 2014-10-28 2016-05-04 华东理工常熟研究院有限公司 硫酸阿帕替尼的新晶型
CN105622498A (zh) * 2014-10-28 2016-06-01 华东理工常熟研究院有限公司 硫酸阿帕替尼的新晶型
CN105622499A (zh) * 2014-10-28 2016-06-01 华东理工常熟研究院有限公司 硫酸阿帕替尼的新晶型
JO3705B1 (ar) * 2014-11-26 2021-01-31 Bayer Pharma AG إندازولات مستبدلة جديدة، عمليات لتحضيرها، مستحضرات دوائية تحتوي عليها واستخدامها في إنتاج أدوية
US20200216413A1 (en) * 2016-06-01 2020-07-09 Bayer Animal Health Gmbh Substituted indazoles useful for treatment and prevention of allergic and/or inflammatory diseases in animals
CN106496107A (zh) * 2016-08-31 2017-03-15 浙江永宁药业股份有限公司 Vegfr‑2抑制剂及其制备方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9824579D0 (en) * 1998-11-10 1999-01-06 Novartis Ag Organic compounds
GB0001930D0 (en) * 2000-01-27 2000-03-22 Novartis Ag Organic compounds
DE10023486C1 (de) * 2000-05-09 2002-03-14 Schering Ag Ortho substituierte Anthranilsäureamide und deren Verwendung als Arzneimittel
DE10023485A1 (de) * 2000-05-09 2001-11-22 Schering Ag Anthranylalkyl- und -cycloalkylamide und deren Verwendung als Arzneimittel
US6995162B2 (en) * 2001-01-12 2006-02-07 Amgen Inc. Substituted alkylamine derivatives and methods of use
US20030134836A1 (en) * 2001-01-12 2003-07-17 Amgen Inc. Substituted arylamine derivatives and methods of use
US6878714B2 (en) * 2001-01-12 2005-04-12 Amgen Inc. Substituted alkylamine derivatives and methods of use
US20020147198A1 (en) * 2001-01-12 2002-10-10 Guoqing Chen Substituted arylamine derivatives and methods of use
KR20030094395A (ko) * 2001-05-08 2003-12-11 쉐링 악티엔게젤샤프트 Ｖｅｇｆｒ-2 및 ｖｅｇｆｒ-3의 억제제로서의 선택적안트라닐아미드 피리딘 아미드
AU2002350217A1 (en) * 2001-12-04 2003-06-17 Bristol-Myers Squibb Company Glycinamides as factor xa inhibitors

Also Published As

Publication number Publication date
HRP20050187A2 (hr) 2005-10-31
MXPA04012948A (es) 2005-09-12
NO20051035L (no) 2005-04-29
JP2011026344A (ja) 2011-02-10
EP1594841A1 (fr) 2005-11-16
JP2005538112A (ja) 2005-12-15
IL166377A0 (en) 2006-01-16
RU2005105683A (ru) 2006-01-20
JP4777648B2 (ja) 2011-09-21
CR7673A (es) 2006-05-29
AU2003281855A1 (en) 2004-02-23
ECSP055631A (es) 2005-04-18
CO5720998A2 (es) 2007-01-31
BR0313122A (pt) 2005-07-05
KR20050026535A (ko) 2005-03-15
PL374610A1 (en) 2005-10-31
WO2004013102A1 (fr) 2004-02-12
RS20050084A (en) 2007-09-21
CN1671666A (zh) 2005-09-21
CA2493026A1 (fr) 2004-02-12

Similar Documents

Publication Publication Date Title
CA2493026C (fr) Anthranylamidopyrimidines inhibant vegfr-2 et vegfr-3
JP4988584B2 (ja) Ｖｅｇｆ受容体キナーゼインヒビターとしてのアントラニルアミドピリジンウレア
US7615565B2 (en) VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridines
US20040254185A1 (en) Selective anthranilamide pyridine amides as inhibitors of vegfr-2 and vegfr-3
US7906533B2 (en) Nicotinamide pyridinureas as vascular endothelial growth factor (VEGF) receptor kinase inhibitors
US7517894B2 (en) VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridines
JP5069119B2 (ja) 血管内皮成長因子（ｖｅｇｆ）受容体キナーゼインヒビターとしてのニコチンアミドピリジンウレア
US7429592B2 (en) Cyanoanthranilamide derivatives and the use thereof as medicaments
US20040147535A1 (en) VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridines
US7202260B2 (en) VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridones
ZA200600291B (en) Anthranylamide pyridones that inhibit VEGFR-2 and VEGFR-3
NZ537291A (en) VEGFR-2 and VEGFR-3 inhibitory anthranylamidopyridines for the treatment of diseases caused by persistent angiogenesis
DE10328036A1 (de) VEGFR-2 und VEGFR-3 inhibitorische Anthranylamidpyridine
DE10164590A1 (de) Anthranylamidpyridinamide als VEGFR-2 und VEGFR-3 Inhibitoren

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20140722