WO2007017264A3 - Pyrrolopyridinederivatives as modulators of the cannabinoid receptor for the treatment of immune and inflammatory disorders - Google Patents

Pyrrolopyridinederivatives as modulators of the cannabinoid receptor for the treatment of immune and inflammatory disorders Download PDF

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Publication number
WO2007017264A3
WO2007017264A3 PCT/EP2006/007875 EP2006007875W WO2007017264A3 WO 2007017264 A3 WO2007017264 A3 WO 2007017264A3 EP 2006007875 W EP2006007875 W EP 2006007875W WO 2007017264 A3 WO2007017264 A3 WO 2007017264A3
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WO
WIPO (PCT)
Prior art keywords
alkyl
group
hydrogen
substituted
cycloalkyl
Prior art date
Application number
PCT/EP2006/007875
Other languages
French (fr)
Other versions
WO2007017264A2 (en
Inventor
Andrew John Eatherton
Gerard Martin Paul Giblin
Karamjit Singh Jandu
Matthew Russell Johnson
William Leonard Mitchell
Alan Naylor
Jennifer Anne Sweeting
Original Assignee
Glaxo Group Ltd
Andrew John Eatherton
Gerard Martin Paul Giblin
Karamjit Singh Jandu
Matthew Russell Johnson
William Leonard Mitchell
Alan Naylor
Jennifer Anne Sweeting
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 Glaxo Group Ltd, Andrew John Eatherton, Gerard Martin Paul Giblin, Karamjit Singh Jandu, Matthew Russell Johnson, William Leonard Mitchell, Alan Naylor, Jennifer Anne Sweeting filed Critical Glaxo Group Ltd
Publication of WO2007017264A2 publication Critical patent/WO2007017264A2/en
Publication of WO2007017264A3 publication Critical patent/WO2007017264A3/en

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Classifications

    • 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
    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Immunology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to novel pyrrolopyridine derivatives of formula (I), pharmaceutical compositions containing these compounds and their use in the treatment of diseases, particularly pain, which diseases are caused directly or indirectly by an increase or decrease-in activity of the cannabinoid receptor, wherein: X1 is NH and X2 and X3 together form a -CR13=CR11-group or X3 is NR12 and X2 and X1 together form a -CR13=CR11- group; X4 is O, SO2, S, or a bond, or X4 is -NHCO or -NHCH2 such that R6X4 is R6CONH or R6CH2NH; R1 is selected from hydrogen, C1-6 alkyl, C3-6 cycloalkyl and halosubstituted C1-6 alkyl; R2 is hydrogen or (CH2)mR3 where m is 0 or 1; or R1 and R2 together with N to which they are attached form an optionally substituted 4- to 8- membered non-aromatic heterocyclyl ring; R3 is a 4- to8- membered non-aromatic heterocyclyl group, a C3-8 cycloalkyl group, a straight or branched C1-10 alkyl, a C2-10 alkenyl, a C3-8 cycloalkenyl, a C2-10 alkynyl, a C3-8 cycloalkynyl or phenyl group, any of which can be unsubstituted or substituted, or R5; wherein p is 0, 1 or 2, and X is CH2. O, S, or SO2; R6 is phenyl, C3-6 cycloalkyl, a straight or branched C1-6 alkyl group, -CH2-C3-6 cycloalkyl, -CH2-phenyl, 4- to 8- membered non-aromatic heterocyclyl group, or a bicyclic group any of which can be unsubstituted or substituted, however when X4 is a bond R6 is substituted phenyl; R7 is OH, C1-6 alkoxy, NR8aR8b, NHCOR9, NHSO2R9 or SOqR9; R8a is H or C1-6 alkyl; R8b is Hor C1-6 alkyl; R9 is C1-6 alkyl; R10 is hydrogen, substituted or unsubstituted (C1-6)alkyl or chloro; R11 is hydrogen or C1-6 alkyl; R12 is hydrogen or C1-6 alkyl; R13 is hydrogen or C1-6 alkyl; q is 0, 1 or 2.
PCT/EP2006/007875 2005-08-09 2006-08-07 Pyrrolopyridinederivatives as modulators of the cannabinoid receptor for the treatment of immune and inflammatory disorders WO2007017264A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0516379.5 2005-08-09
GBGB0516379.5A GB0516379D0 (en) 2005-08-09 2005-08-09 Compounds

Publications (2)

Publication Number Publication Date
WO2007017264A2 WO2007017264A2 (en) 2007-02-15
WO2007017264A3 true WO2007017264A3 (en) 2007-04-12

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/007875 WO2007017264A2 (en) 2005-08-09 2006-08-07 Pyrrolopyridinederivatives as modulators of the cannabinoid receptor for the treatment of immune and inflammatory disorders

Country Status (2)

Country Link
GB (1) GB0516379D0 (en)
WO (1) WO2007017264A2 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2010002712A (en) 2007-09-10 2010-06-09 Calcimedica Inc Compounds that modulate intracellular calcium.
ES2716407T3 (en) 2007-11-30 2019-06-12 Zynerba Pharmaceuticals Inc Prodrugs of tetrahydrocannabinol, compositions comprising prodrugs of tetrahydrocannabinol and methods for their use
US8389567B2 (en) 2007-12-12 2013-03-05 Calcimedica, Inc. Compounds that modulate intracellular calcium
BRPI0917719A2 (en) 2008-08-27 2019-11-19 Calcimedica Inc intracellular calcium modulating compounds
US8524763B2 (en) 2008-09-22 2013-09-03 Calcimedica, Inc. Inhibitors of store operated calcium release
CA2757188A1 (en) 2009-03-30 2010-10-07 Astellas Pharma Inc. Pyrimidine compound
EP2477982A4 (en) 2009-09-16 2013-04-03 Calcimedica Inc Compounds that modulate intracellular calcium
PL2599774T3 (en) 2010-07-29 2017-01-31 Astellas Pharma Inc. Condensed pyridine compounds as cb2 cannabinoid receptor ligands
CA2893115A1 (en) * 2012-11-30 2014-06-05 Kyowa Hakko Kirin Co., Ltd. Nitrogen-containing heterocyclic compound
CN110627846B (en) * 2019-10-30 2022-11-29 河南师范大学 Galactoside-tetrastyrene compound, preparation method thereof and application thereof as drug carrier

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001058869A2 (en) * 2000-02-11 2001-08-16 Bristol-Myers Squibb Company Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators in treating respiratory and non-respiratory diseases
US20020022624A1 (en) * 2000-07-13 2002-02-21 Kevin Dinnell Azaindole derivatives and their use as therapeutic agents
WO2005066126A1 (en) * 2003-12-23 2005-07-21 Eli Lilly And Company Cb1 modulator compounds
WO2005121140A1 (en) * 2004-06-09 2005-12-22 Glaxo Group Limited Pyrrolopyridine derivatives

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001058869A2 (en) * 2000-02-11 2001-08-16 Bristol-Myers Squibb Company Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators in treating respiratory and non-respiratory diseases
US20020022624A1 (en) * 2000-07-13 2002-02-21 Kevin Dinnell Azaindole derivatives and their use as therapeutic agents
WO2005066126A1 (en) * 2003-12-23 2005-07-21 Eli Lilly And Company Cb1 modulator compounds
WO2005121140A1 (en) * 2004-06-09 2005-12-22 Glaxo Group Limited Pyrrolopyridine derivatives

Also Published As

Publication number Publication date
GB0516379D0 (en) 2005-09-14
WO2007017264A2 (en) 2007-02-15

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