WO2000005223A3 - Heterocyclic derivatives and their use as integrin inhibitors - Google Patents

Heterocyclic derivatives and their use as integrin inhibitors Download PDF

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Publication number
WO2000005223A3
WO2000005223A3 PCT/GB1999/002330 GB9902330W WO0005223A3 WO 2000005223 A3 WO2000005223 A3 WO 2000005223A3 GB 9902330 W GB9902330 W GB 9902330W WO 0005223 A3 WO0005223 A3 WO 0005223A3
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WIPO (PCT)
Prior art keywords
group
linked
formation
amide bond
ch2ch2s
Prior art date
Application number
PCT/GB1999/002330
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French (fr)
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WO2000005223A2 (en
Inventor
David Robert Brittain
Craig Johnstone
Gareth Morse Davies
Michael Stewart Large
Original Assignee
Astrazeneca Ab
David Robert Brittain
Craig Johnstone
Gareth Morse Davies
Michael Stewart Large
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 GBGB9815970.0A external-priority patent/GB9815970D0/en
Priority claimed from GBGB9815972.6A external-priority patent/GB9815972D0/en
Priority claimed from GBGB9914441.2A external-priority patent/GB9914441D0/en
Application filed by Astrazeneca Ab, David Robert Brittain, Craig Johnstone, Gareth Morse Davies, Michael Stewart Large filed Critical Astrazeneca Ab
Priority to EP99934885A priority Critical patent/EP1133484A2/en
Priority to JP2000561179A priority patent/JP2002521375A/en
Priority to AU50521/99A priority patent/AU5052199A/en
Publication of WO2000005223A2 publication Critical patent/WO2000005223A2/en
Publication of WO2000005223A3 publication Critical patent/WO2000005223A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
    • C04B41/4572—Partial coating or impregnation of the surface of the substrate
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/80—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only ceramics
    • C04B41/81—Coating or impregnation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms
    • 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
    • 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
    • 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
    • C07D417/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/14—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 three or more hetero rings

Abstract

Compound of formula (I) wherein: A is a bicyclic heteroaryl, optionally substituted with one or more substituents; B is aryl or a mono or bicyclic heteroaryl, each of which can be optionally subsituted with one or more subsituents; Z is -X(CRaRb)aCO, -NH, -CO or the group X-(CH2)bCONH (CH2)cNH where X is oxygen, sulphur, amino, alkylamino or a direct bond, R?a and Rb¿ are independently hydrogen or C¿1-4? alkyl, a is an integer from 1 to 4, b is 1 or 2 and c is from 2 to 5, and; W is -NHCH(R?w¿)CO- or OC(Rw)CHNH where Rw is -CH¿2?CH(CH3)2-CH2CH2S(CH3) or CH2CH2S(O2)(CH3); q is 0 or 1 and when q is 0 Z is linked to the group W by the formation of an amide bond between Z and Y, and when q is 1 Z is linked to the group W by the formation of an amide bond between Z and W and W is linked to the group Y by the formation of an amide bond between W and Y; Y is a fragment derived from the C-terminus of a compound which inhibits the interaction between the integrin αIIbβ3 and its ligand fibrinogen; R?1¿ is hydrogen, C¿1-5?alkyl, C1-3 alkanoyl or C1-3 alkoxycarbonyl; or a pharmaceutically acceptable salt or in vivo hydrolysable derivative thereof.
PCT/GB1999/002330 1998-07-23 1999-07-20 Heterocyclic derivatives and their use as integrin inhibitors WO2000005223A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP99934885A EP1133484A2 (en) 1998-07-23 1999-07-20 Heterocyclic derivatives and their use as integrin inhibitors
JP2000561179A JP2002521375A (en) 1998-07-23 1999-07-20 Compound
AU50521/99A AU5052199A (en) 1998-07-23 1999-07-20 Chemical compounds

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GBGB9815970.0A GB9815970D0 (en) 1998-07-23 1998-07-23 Chemical compounds
GBGB9815972.6A GB9815972D0 (en) 1998-07-23 1998-07-23 Chemical compounds
GB9815972.6 1999-06-22
GB9914441.2 1999-06-22
GB9815970.0 1999-06-22
GBGB9914441.2A GB9914441D0 (en) 1999-06-22 1999-06-22 Chemical compounds

Publications (2)

Publication Number Publication Date
WO2000005223A2 WO2000005223A2 (en) 2000-02-03
WO2000005223A3 true WO2000005223A3 (en) 2001-07-12

Family

ID=27269410

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1999/002330 WO2000005223A2 (en) 1998-07-23 1999-07-20 Heterocyclic derivatives and their use as integrin inhibitors

Country Status (4)

Country Link
EP (1) EP1133484A2 (en)
JP (1) JP2002521375A (en)
AU (1) AU5052199A (en)
WO (1) WO2000005223A2 (en)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT1153017E (en) * 1999-02-16 2006-07-31 Aventis Pharma Ltd BICYCLIC COMPOUNDS AND THEIR USE AS INTEGRIN RECEPTOR LIGANDS
AU2018301A (en) 1999-12-28 2001-07-24 Pfizer Products Inc. Non-peptidyl inhibitors of vla-4 dependent cell binding useful in treating inflammatory, autoimmune, and respiratory diseases
GB0001348D0 (en) * 2000-01-21 2000-03-08 Astrazeneca Uk Ltd Chemical compounds
GB0001346D0 (en) * 2000-01-21 2000-03-08 Astrazeneca Uk Ltd Chemical compounds
GB0004686D0 (en) * 2000-02-28 2000-04-19 Aventis Pharma Ltd Chemical compounds
IL156064A0 (en) 2000-12-28 2003-12-23 Daiichi Seiyaku Co Vla-4 inhibitors
ZA200304059B (en) * 2000-12-28 2004-07-06 Daiichi Seiyaku Co VLA-4 inhibitors.
JP4164871B2 (en) 2001-07-26 2008-10-15 味の素株式会社 Novel phenylpropionic acid derivatives
US7351719B2 (en) 2002-10-31 2008-04-01 Boehringer Ingelheim Pharma Gmbh & Co. Kg Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds
EP1650205B1 (en) 2003-07-24 2012-04-25 Daiichi Sankyo Company, Limited Cyclohexanecarboxylic acid compound
DE10360745A1 (en) * 2003-12-23 2005-07-28 Boehringer Ingelheim Pharma Gmbh & Co. Kg New amide compounds having MCH antagonist activity and medicaments containing these compounds
US7592373B2 (en) 2003-12-23 2009-09-22 Boehringer Ingelheim International Gmbh Amide compounds with MCH antagonistic activity and medicaments comprising these compounds
US7470712B2 (en) 2004-01-21 2008-12-30 Bristol-Myers Squibb Company Amino-benzazoles as P2Y1 receptor inhibitors
US7524862B2 (en) 2004-04-14 2009-04-28 Boehringer Ingelheim International Gmbh Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds
DE102004017934A1 (en) 2004-04-14 2005-11-03 Boehringer Ingelheim Pharma Gmbh & Co. Kg New alkyne compounds having MCH antagonist activity and medicaments containing these compounds
DE102006021878A1 (en) * 2006-05-11 2007-11-15 Sanofi-Aventis Phenylamino-benzoxazole substituted carboxylic acids, process for their preparation and their use as medicaments
US8759535B2 (en) 2010-02-18 2014-06-24 High Point Pharmaceuticals, Llc Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof
WO2016089648A1 (en) 2014-12-01 2016-06-09 Vtv Therapeutics Llc Bach 1 inhibitors in combination with nrf2 activators and pharmaceutical compositions thereof
BR112021007213A2 (en) 2018-10-30 2021-08-10 Gilead Sciences, Inc. quinoline derivatives as alpha4beta7 integrin inhibitors
CA3114240C (en) 2018-10-30 2023-09-05 Gilead Sciences, Inc. Imidazopyridine derivatives as alpha4beta7 integrin inhibitors
CA3115820A1 (en) 2018-10-30 2020-05-07 Gilead Sciences, Inc. Compounds for inhibition of .alpha.4.beta.7 integrin
CN112969504B (en) 2018-10-30 2024-04-09 吉利德科学公司 Compounds for inhibiting alpha 4 beta 7 integrin
AU2020329207B2 (en) 2019-08-14 2024-02-29 Gilead Sciences, Inc. Compounds for inhibition of alpha 4 beta 7 integrin

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996022966A1 (en) * 1995-01-23 1996-08-01 Biogen, Inc. Cell adhesion inhibitors
WO1997008145A1 (en) * 1995-08-30 1997-03-06 G.D. Searle & Co. Meta-guanidine, urea, thiourea or azacyclic amino benzoic acid derivatives as integrin antagonists
WO1997036862A1 (en) * 1996-03-29 1997-10-09 G.D. Searle & Co. META-SUBSTITUTED PHENYLENE DERIVATIVES AND THEIR USE AS ALPHAvBETA3 INTEGRIN ANTAGONISTS OR INHIBITORS
WO1999024398A2 (en) * 1997-11-12 1999-05-20 Astrazeneca Uk Limited Urea derivatives and their use as integrin inhibitors

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996022966A1 (en) * 1995-01-23 1996-08-01 Biogen, Inc. Cell adhesion inhibitors
WO1997008145A1 (en) * 1995-08-30 1997-03-06 G.D. Searle & Co. Meta-guanidine, urea, thiourea or azacyclic amino benzoic acid derivatives as integrin antagonists
WO1997036862A1 (en) * 1996-03-29 1997-10-09 G.D. Searle & Co. META-SUBSTITUTED PHENYLENE DERIVATIVES AND THEIR USE AS ALPHAvBETA3 INTEGRIN ANTAGONISTS OR INHIBITORS
WO1999024398A2 (en) * 1997-11-12 1999-05-20 Astrazeneca Uk Limited Urea derivatives and their use as integrin inhibitors

Also Published As

Publication number Publication date
WO2000005223A2 (en) 2000-02-03
AU5052199A (en) 2000-02-14
EP1133484A2 (en) 2001-09-19
JP2002521375A (en) 2002-07-16

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