WO2001068586A3 - α4β1 AND α4β7 INTEGRIN INHIBITORS - Google Patents

α4β1 AND α4β7 INTEGRIN INHIBITORS Download PDF

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Publication number
WO2001068586A3
WO2001068586A3 PCT/EP2001/002749 EP0102749W WO0168586A3 WO 2001068586 A3 WO2001068586 A3 WO 2001068586A3 EP 0102749 W EP0102749 W EP 0102749W WO 0168586 A3 WO0168586 A3 WO 0168586A3
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WO
WIPO (PCT)
Prior art keywords
integrin inhibitors
inhibitors
integrins
inflammatory
therapeutic
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Application number
PCT/EP2001/002749
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French (fr)
Other versions
WO2001068586A2 (en
Inventor
Nigel Graham Cooke
Michael Lloyd Sabio
Original Assignee
Novartis Ag
Novartis Erfind Verwalt Gmbh
Nigel Graham Cooke
Michael Lloyd Sabio
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Publication date
Application filed by Novartis Ag, Novartis Erfind Verwalt Gmbh, Nigel Graham Cooke, Michael Lloyd Sabio filed Critical Novartis Ag
Priority to AU2001262089A priority Critical patent/AU2001262089A1/en
Publication of WO2001068586A2 publication Critical patent/WO2001068586A2/en
Publication of WO2001068586A3 publication Critical patent/WO2001068586A3/en

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    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C07D207/48—Sulfur atoms
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Diabetes (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compounds of formula (I) as defined and their pharmaceutically acceptable salts are inhibitors of α4β1 and/or α4β7 integrins, and are useful in inhibiting cell adhesion and in the therapeutic or prophylactic treatment of transplant rejection and inflammatory and autoimmune diseases.
PCT/EP2001/002749 2000-03-14 2001-03-12 α4β1 AND α4β7 INTEGRIN INHIBITORS WO2001068586A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001262089A AU2001262089A1 (en) 2000-03-14 2001-03-12 Alpha4beta1 and alpha4beta7 integrin inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US52570000A 2000-03-14 2000-03-14
US09/525,700 2000-03-14

Publications (2)

Publication Number Publication Date
WO2001068586A2 WO2001068586A2 (en) 2001-09-20
WO2001068586A3 true WO2001068586A3 (en) 2002-01-10

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2001/002749 WO2001068586A2 (en) 2000-03-14 2001-03-12 α4β1 AND α4β7 INTEGRIN INHIBITORS

Country Status (2)

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AU (1) AU2001262089A1 (en)
WO (1) WO2001068586A2 (en)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL374971A1 (en) 2002-08-09 2005-11-14 Transtech Pharma, Inc. Aryl and heteroaryl compounds and methods to modulate coagulation
US7015323B2 (en) 2003-05-20 2006-03-21 Genentech, Inc. Thiocarbamate inhibitors of alpha-4 integrins
US7208601B2 (en) 2003-08-08 2007-04-24 Mjalli Adnan M M Aryl and heteroaryl compounds, compositions, and methods of use
US7501538B2 (en) 2003-08-08 2009-03-10 Transtech Pharma, Inc. Aryl and heteroaryl compounds, compositions and methods of use
CA2531796A1 (en) 2003-08-08 2005-02-17 Transtech Pharma, Inc. Aryl and heteroaryl compounds, compositions, and methods of use
ATE549321T1 (en) 2006-11-22 2012-03-15 Ajinomoto Kk METHOD FOR THE PRODUCTION OF PHENYLALANINE DERIVATIVES WITH CHINAZOLINDIONE STANDARDS, AND INTERMEDIATE PRODUCTS FOR THE PRODUCTION
US9273093B2 (en) 2012-10-11 2016-03-01 Protagonist Therapeutics, Inc. α4β7 peptide dimer antagonists
HRP20211911T1 (en) 2013-03-15 2022-03-18 Protagonist Therapeutics, Inc. Hepcidin analogues and uses therof
US20140294902A1 (en) * 2013-04-02 2014-10-02 Protagonist Therapeutics, Inc. Novel a4b7 peptide antagonists
SI3143037T1 (en) 2014-05-16 2021-11-30 Protagonist Therapeutics, Inc. Alpha4beta7 integrin thioether peptide antagonists
CA2955460A1 (en) 2014-07-17 2016-01-21 Protagonist Therapeutics, Inc. Oral peptide inhibitors of interleukin-23 receptor and their use to treat inflammatory bowel diseases
EP3201217A4 (en) 2014-10-01 2018-07-18 Protagonist Therapeutics Inc. Novel cyclic monomer and dimer peptides having integrin antagonist activity
AU2015328002A1 (en) 2014-10-01 2017-04-27 Protagonist Therapeutics, Inc. Novel alpha4beta7 peptide monomer and dimer antagonists
US10787490B2 (en) 2015-07-15 2020-09-29 Protaganist Therapeutics, Inc. Peptide inhibitors of interleukin-23 receptor and their use to treat inflammatory diseases
CA3009834A1 (en) 2015-12-30 2017-07-06 Protagonist Therapeutics, Inc. Analogues of hepcidin mimetics with improved in vivo half lives
WO2017165676A1 (en) 2016-03-23 2017-09-28 Protagonist Therapeutics, Inc. METHODS FOR SYNTHESIZING α4β7 PEPTIDE ANTAGONISTS
WO2018106959A1 (en) 2016-12-07 2018-06-14 Progenity Inc. Gastrointestinal tract detection methods, devices and systems
EP4233902A3 (en) 2016-12-14 2024-02-28 Biora Therapeutics, Inc. Treatment of a disease of the gastrointestinal tract with an integrin inhibitor
CA3073806A1 (en) 2017-09-11 2019-03-14 Protagonist Therapeutics, Inc. Opioid agonist peptides and uses thereof
CA3089868A1 (en) 2018-02-08 2019-08-15 Protagonist Therapeutics, Inc. Conjugated hepcidin mimetics
US20230033021A1 (en) 2018-06-20 2023-02-02 Progenity, Inc. Treatment of a disease of the gastrointestinal tract with an integrin inhibitor
EP3873884A1 (en) 2018-10-30 2021-09-08 Gilead Sciences, Inc. Quinoline derivatives as alpha4beta7 integrin inhibitors
WO2020092401A1 (en) 2018-10-30 2020-05-07 Gilead Sciences, Inc. COMPOUNDS FOR INHIBITION OF ALPHA 4β7 INTEGRIN
JP7189368B2 (en) 2018-10-30 2022-12-13 ギリアード サイエンシーズ， インコーポレイテッド Compounds for inhibition of alpha4beta7 integrin
KR102641718B1 (en) 2018-10-30 2024-02-29 길리애드 사이언시즈, 인코포레이티드 Imidazopyridine derivatives as alpha4beta7 integrin inhibitors
KR20210095165A (en) 2018-11-19 2021-07-30 프로제너티, 인크. Methods and devices for treating diseases with biopharmaceuticals
CA3146390A1 (en) 2019-07-10 2021-01-14 Protagonist Therapeutics, Inc. Peptide inhibitors of interleukin-23 receptor and their use to treat inflammatory diseases
KR20220047323A (en) 2019-08-14 2022-04-15 길리애드 사이언시즈, 인코포레이티드 Compounds for Inhibiting Alpha 4 Beta 7 Integrin
EP4309722A2 (en) 2019-12-13 2024-01-24 Biora Therapeutics, Inc. Ingestible device for delivery of therapeutic agent to the gastrointestinal tract
EP4090670A1 (en) 2020-01-15 2022-11-23 Janssen Biotech, Inc. Peptide inhibitors of interleukin-23 receptor and their use to treat inflammatory diseases
CA3202226A1 (en) 2020-11-20 2022-05-27 Janssen Pharmaceutica Nv Compositions of peptide inhibitors of interleukin-23 receptor

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998053814A1 (en) * 1997-05-29 1998-12-03 Merck & Co., Inc. Heterocyclic amide compounds as cell adhesion inhibitors
WO1999006437A1 (en) * 1997-07-31 1999-02-11 Elan Pharmaceuticals Inc. Sulfonylated dipeptide compounds which inhibit leukocyte adhesion mediated by vla-4
WO1999035163A1 (en) * 1998-01-08 1999-07-15 Celltech Therapeutics Limited Phenylalanine derivatives
WO1999037618A1 (en) * 1998-01-27 1999-07-29 Celltech Therapeutics Limited Phenylalanine derivatives useful as pharmaceutical agents
WO1999043642A1 (en) * 1998-02-26 1999-09-02 Celltech Therapeutics Limited Phenylalanine derivatives as inhibitors of alpha4 integrins
WO1999067230A1 (en) * 1998-06-23 1999-12-29 Pharmacia & Upjohn Company INHIBITORS OF α4β1 MEDIATED CELL ADHESION

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998053814A1 (en) * 1997-05-29 1998-12-03 Merck & Co., Inc. Heterocyclic amide compounds as cell adhesion inhibitors
WO1999006437A1 (en) * 1997-07-31 1999-02-11 Elan Pharmaceuticals Inc. Sulfonylated dipeptide compounds which inhibit leukocyte adhesion mediated by vla-4
WO1999035163A1 (en) * 1998-01-08 1999-07-15 Celltech Therapeutics Limited Phenylalanine derivatives
WO1999037618A1 (en) * 1998-01-27 1999-07-29 Celltech Therapeutics Limited Phenylalanine derivatives useful as pharmaceutical agents
WO1999043642A1 (en) * 1998-02-26 1999-09-02 Celltech Therapeutics Limited Phenylalanine derivatives as inhibitors of alpha4 integrins
WO1999067230A1 (en) * 1998-06-23 1999-12-29 Pharmacia & Upjohn Company INHIBITORS OF α4β1 MEDIATED CELL ADHESION

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOEDERUNG DER CHEMISCHEN WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; XP002180175 *
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOEDERUNG DER CHEMISCHEN WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; XP002180176 *
PHARMAZIE, vol. 38, no. 3, 1983, pages 170 - 171 *
YAKUGAKU ZASSHI, vol. 74, 1954, pages 1287 *

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WO2001068586A2 (en) 2001-09-20

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