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WO2004058755A3 - Compound libraries of imidazo[1,5-a]pyridin-3-yl derivatives and related heterobicycles for targetting compounds capable of binding to g-protein coupled receptors - Google Patents

Compound libraries of imidazo[1,5-a]pyridin-3-yl derivatives and related heterobicycles for targetting compounds capable of binding to g-protein coupled receptors Download PDF

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Publication number
WO2004058755A3
WO2004058755A3 PCT/GB2003/005652 GB0305652W WO2004058755A3 WO 2004058755 A3 WO2004058755 A3 WO 2004058755A3 GB 0305652 W GB0305652 W GB 0305652W WO 2004058755 A3 WO2004058755 A3 WO 2004058755A3
Authority
WO
WIPO (PCT)
Prior art keywords
protein coupled
coupled receptors
heterobicycles
targetting
imidazo
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.)
Ceased
Application number
PCT/GB2003/005652
Other languages
French (fr)
Other versions
WO2004058755A2 (en
Inventor
Terence Ward
Roger Crossley
Jacqueline Anne Macritchie
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.)
BIOFOCUS PLC
Original Assignee
BIOFOCUS PLC
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 GB0230195A external-priority patent/GB0230195D0/en
Application filed by BIOFOCUS PLC filed Critical BIOFOCUS PLC
Priority to AU2003290333A priority Critical patent/AU2003290333A1/en
Priority to PCT/GB2003/005652 priority patent/WO2004058755A2/en
Publication of WO2004058755A2 publication Critical patent/WO2004058755A2/en
Publication of WO2004058755A3 publication Critical patent/WO2004058755A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4747—Quinolines; Isoquinolines spiro-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D241/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07D405/10—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 carbon chain containing aromatic rings
    • 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
    • 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
    • C07D471/04—Ortho-condensed systems
    • 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
    • C07D471/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C40—COMBINATORIAL TECHNOLOGY
    • C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
    • C40B40/00—Libraries per se, e.g. arrays, mixtures
    • C40B40/04—Libraries containing only organic compounds
    • C—CHEMISTRY; METALLURGY
    • C40—COMBINATORIAL TECHNOLOGY
    • C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
    • C40B50/00—Methods of creating libraries, e.g. combinatorial synthesis
    • C40B50/08—Liquid phase synthesis, i.e. wherein all library building blocks are in liquid phase or in solution during library creation; Particular methods of cleavage from the liquid support

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Structural Engineering (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention provides a library designed to take advantage of a common recognition feature of G-protein coupled receptors, namely the ‘benzhydryl’ or ‘rabbit ears’ arrangement of aromatic rings. In addition the library utilises several themes common in GPCRs selecting for subsets which recognise basic and ‘acidic’ ligands. The library comprises or consists of a set of structurally related compounds of general formulae (A)or (B). The present invention also provides intermediates (formula (3)).
PCT/GB2003/005652 2002-12-24 2003-12-24 Compound libraries of imidazo[1,5-a]pyridin-3-yl derivatives and related heterobicycles for targetting compounds capable of binding to g-protein coupled receptors Ceased WO2004058755A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003290333A AU2003290333A1 (en) 2002-12-24 2003-12-24 Compound libraries of imidazo(1,5-a)pyridin-3-yl derivatives and related heterobicycles for targetting compounds capable of binding to g-protein coupled receptors
PCT/GB2003/005652 WO2004058755A2 (en) 2002-12-24 2003-12-24 Compound libraries of imidazo[1,5-a]pyridin-3-yl derivatives and related heterobicycles for targetting compounds capable of binding to g-protein coupled receptors

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0230195A GB0230195D0 (en) 2002-12-24 2002-12-24 Compound Libraries
GB0230195.0 2002-12-24
PCT/GB2003/005652 WO2004058755A2 (en) 2002-12-24 2003-12-24 Compound libraries of imidazo[1,5-a]pyridin-3-yl derivatives and related heterobicycles for targetting compounds capable of binding to g-protein coupled receptors

Publications (2)

Publication Number Publication Date
WO2004058755A2 WO2004058755A2 (en) 2004-07-15
WO2004058755A3 true WO2004058755A3 (en) 2004-08-19

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PCT/GB2003/005652 Ceased WO2004058755A2 (en) 2002-12-24 2003-12-24 Compound libraries of imidazo[1,5-a]pyridin-3-yl derivatives and related heterobicycles for targetting compounds capable of binding to g-protein coupled receptors

Country Status (2)

Country Link
AU (1) AU2003290333A1 (en)
WO (1) WO2004058755A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0320983D0 (en) * 2003-09-08 2003-10-08 Biofocus Plc Compound libraries
WO2008022060A2 (en) * 2006-08-14 2008-02-21 Novartis Ag Imidazo-pyridine derivatives for modulating protein kinase activity
WO2009038012A1 (en) * 2007-09-18 2009-03-26 Taisho Pharmaceutical Co., Ltd. Heterocyclic compound
MX2013015058A (en) 2011-06-24 2014-01-20 Amgen Inc Trpm8 antagonists and their use in treatments.
EP2723717A2 (en) 2011-06-24 2014-04-30 Amgen Inc. Trpm8 antagonists and their use in treatments
US8952009B2 (en) 2012-08-06 2015-02-10 Amgen Inc. Chroman derivatives as TRPM8 inhibitors
WO2018175512A1 (en) * 2017-03-22 2018-09-27 Suzhou Baijibugong Pharmaceutical Technology Co. Ltd. Bruton's tyrosine kinase inhibitors

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0114572A1 (en) * 1982-12-21 1984-08-01 Ciba-Geigy Ag Substituted imidazo(1,5-a)pyridines
WO2001027119A2 (en) * 1999-10-08 2001-04-19 Grünenthal GmbH Substance library containing bicyclic imidazo-5-yl-amines and/or bicyclic imidazo-3-yl-amines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0114572A1 (en) * 1982-12-21 1984-08-01 Ciba-Geigy Ag Substituted imidazo(1,5-a)pyridines
WO2001027119A2 (en) * 1999-10-08 2001-04-19 Grünenthal GmbH Substance library containing bicyclic imidazo-5-yl-amines and/or bicyclic imidazo-3-yl-amines

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
CURTIN M L ET AL: "Discovery an Evaluation of a Series of 3-Acylindole Imidazopyridine Platelet-Activating Factor Antagonists", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 41, no. 1, 1998, pages 74 - 95, XP002109994, ISSN: 0022-2623 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 22 July 1993 (1993-07-22), XP002280235, Database accession no. 5943812 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 22 July 1993 (1993-07-22), XP002280236, Database accession no. 5943235 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 22 July 1993 (1993-07-22), XP002280239, Database accession no. 645164 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 27 June 1988 (1988-06-27), XP002280231, Database accession no. BRN134243 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 28 April 1997 (1997-04-28), XP002280238, Database accession no. 645058 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 28 November 1988 (1988-11-28), XP002280232, Database accession no. 475308 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 28 November 1988 (1988-11-28), XP002280233, Database accession no. 475309 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 28 November 1988 (1988-11-28), XP002280234, Database accession no. 477795 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 28 November 1988 (1988-11-28), XP002280237, Database accession no. 514116 *

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Publication number Publication date
AU2003290333A1 (en) 2004-07-22
AU2003290333A8 (en) 2004-07-22
WO2004058755A2 (en) 2004-07-15

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