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WO2012090177A3 - Cannabinoid receptor modulators - Google Patents

Cannabinoid receptor modulators Download PDF

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Publication number
WO2012090177A3
WO2012090177A3 PCT/IB2011/056007 IB2011056007W WO2012090177A3 WO 2012090177 A3 WO2012090177 A3 WO 2012090177A3 IB 2011056007 W IB2011056007 W IB 2011056007W WO 2012090177 A3 WO2012090177 A3 WO 2012090177A3
Authority
WO
WIPO (PCT)
Prior art keywords
receptor modulators
cannabinoid receptor
cannabinoid
syndromes
receptors
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/IB2011/056007
Other languages
French (fr)
Other versions
WO2012090177A2 (en
Inventor
Sanjeev Anant Kulkarni
Sachin MADAN
Nirmal Kumar JANA
Prashant Vitthalrao TALE
Narasimha Murthy CHEEMALA
Sachin Jaysing Mahangare
Prashant Popatrao VIDHATE
Chaitanya Prabhakar KULKARNI
Sapana Suresh PATEL
Amolsing Dattu PATIL
Rohan Mahadev SHINDE
Venkata P. Palle
Rajender Kumar Kamboj
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.)
Lupin Ltd
Original Assignee
Lupin Ltd
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 Lupin Ltd filed Critical Lupin Ltd
Priority to PCT/IB2012/053407 priority Critical patent/WO2013005168A2/en
Priority to IN226MUN2014 priority patent/IN2014MN00226A/en
Priority to US13/542,234 priority patent/US9006442B2/en
Publication of WO2012090177A2 publication Critical patent/WO2012090177A2/en
Publication of WO2012090177A3 publication Critical patent/WO2012090177A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/48—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system of the same carbon skeleton
    • 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]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
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    • 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
    • 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
    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/08—Bridged systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Rheumatology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Compounds of Formula (I) along with processes for their preparation that are useful for treating, preventing and/or managing the diseases, disorders, syndromes or conditions associated with the modulation of cannabinoid (CB) receptors. Methods of treating, preventing managing and/or lessening the diseases, disorders, syndromes or conditions associated with the modulation of cannabinoid (CB) receptors of Formula (I).
PCT/IB2011/056007 2010-12-30 2011-12-29 Cannabinoid receptor modulators Ceased WO2012090177A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PCT/IB2012/053407 WO2013005168A2 (en) 2011-07-05 2012-07-04 Cannabinoid receptor modulators
IN226MUN2014 IN2014MN00226A (en) 2011-07-05 2012-07-04
US13/542,234 US9006442B2 (en) 2011-07-05 2012-07-05 Cannabinoid receptor modulators

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
IN1477/KOL/2010 2010-12-30
IN1476/KOL/2010 2010-12-30
IN1477KO2010 2010-12-30
IN1476KO2010 2010-12-30
IN908KO2011 2011-07-05
IN907/KOL/2011 2011-07-05
IN905/KOL/2011 2011-07-05
IN907KO2011 2011-07-05
IN905KO2011 2011-07-05
IN908/KOL/2011 2011-07-05

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/542,234 Continuation-In-Part US9006442B2 (en) 2011-07-05 2012-07-05 Cannabinoid receptor modulators

Publications (2)

Publication Number Publication Date
WO2012090177A2 WO2012090177A2 (en) 2012-07-05
WO2012090177A3 true WO2012090177A3 (en) 2012-08-23

Family

ID=45531493

Family Applications (1)

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PCT/IB2011/056007 Ceased WO2012090177A2 (en) 2010-12-30 2011-12-29 Cannabinoid receptor modulators

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Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN2014MN00226A (en) * 2011-07-05 2015-09-25 Lupin Ltd
EP2958895B1 (en) * 2013-02-20 2020-08-19 Kala Pharmaceuticals, Inc. Therapeutic compounds and uses thereof
WO2022150962A1 (en) * 2021-01-12 2022-07-21 Westlake Pharmaceutical (Hangzhou) Co., Ltd. Protease inhibitors, preparation, and uses thereof

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WO2003029185A1 (en) * 2001-10-04 2003-04-10 Astrazeneca Ab Novel compounds
WO2006038594A1 (en) * 2004-10-04 2006-04-13 Ono Pharmaceutical Co., Ltd. N-type calcium channel inhibitor
WO2006136924A1 (en) * 2005-06-22 2006-12-28 Pfizer Products Inc. Histamine-3 receptor antagonists
WO2007066784A2 (en) * 2005-12-05 2007-06-14 Otsuka Pharmaceutical Co., Ltd. Diarylether derivatives as antitumor agents
WO2008121570A1 (en) * 2007-03-29 2008-10-09 Irm Llc Compounds and methods for modulating g protein-coupled receptors
WO2008142454A1 (en) * 2007-05-22 2008-11-27 Prosidion Limited Bicyclic aryl and heteroaryl compounds for the treatment of metabolic disorders
WO2009012242A2 (en) * 2007-07-13 2009-01-22 Icagen, Inc. Sodium channel inhibitors

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GB0028702D0 (en) 2000-11-24 2001-01-10 Novartis Ag Organic compounds
PL1902034T3 (en) 2005-06-02 2011-09-30 Glenmark Pharmaceuticals Sa Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation
WO2007091950A1 (en) 2006-02-07 2007-08-16 Astrazeneca Ab Benzimidazoles and imidazopyridines useful in the treatment of diseases or disorders associated with cannabinoid receptor 2 (cb2) such as pain
US7700618B2 (en) 2006-03-06 2010-04-20 Pfizer Inc Sulfonyl benzimidazole derivatives
US7563797B2 (en) 2006-08-28 2009-07-21 Forest Laboratories Holding Limited Substituted imidazo(1,2-A)pyrimidines and imidazo(1,2-A) pyridines as cannabinoid receptor ligands
EP2139327A4 (en) 2007-03-21 2011-06-15 Janssen Pharmaceutica Nv Method for treating cb2 receptor mediated pain
WO2009053799A1 (en) 2007-10-24 2009-04-30 Glenmark Pharmaceuticals, S.A. Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation
WO2010084767A1 (en) 2009-01-22 2010-07-29 Raqualia Pharma Inc. N-substituted saturated heterocyclic sulfone compounds with cb2 receptor agonistic activity
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EP2261211A1 (en) 2009-05-20 2010-12-15 Université de Lille 2 Droit et Santé 1,4-dihydropyridine derivatives and their uses

Patent Citations (7)

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WO2003029185A1 (en) * 2001-10-04 2003-04-10 Astrazeneca Ab Novel compounds
WO2006038594A1 (en) * 2004-10-04 2006-04-13 Ono Pharmaceutical Co., Ltd. N-type calcium channel inhibitor
WO2006136924A1 (en) * 2005-06-22 2006-12-28 Pfizer Products Inc. Histamine-3 receptor antagonists
WO2007066784A2 (en) * 2005-12-05 2007-06-14 Otsuka Pharmaceutical Co., Ltd. Diarylether derivatives as antitumor agents
WO2008121570A1 (en) * 2007-03-29 2008-10-09 Irm Llc Compounds and methods for modulating g protein-coupled receptors
WO2008142454A1 (en) * 2007-05-22 2008-11-27 Prosidion Limited Bicyclic aryl and heteroaryl compounds for the treatment of metabolic disorders
WO2009012242A2 (en) * 2007-07-13 2009-01-22 Icagen, Inc. Sodium channel inhibitors

Non-Patent Citations (3)

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Title
PATEL K D ET AL: "Cannabinoid CB2 receptors in health and disease", CURRENT MEDICINAL CHEMISTRY 2010 BENTHAM SCIENCE PUBLISHERS B.V. NLD LNKD- DOI:10.2174/092986710790980041, vol. 17, no. 14, May 2010 (2010-05-01), pages 1394 - 1410, XP002674005, ISSN: 0929-8673 *
SAARI RAIMO ET AL: "Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline and quinazoline derivatives as CB2 receptor agonists.", BIOORGANIC & MEDICINAL CHEMISTRY 15 JAN 2011 LNKD- PUBMED:21215643, vol. 19, no. 2, 9 December 2010 (2010-12-09), pages 939 - 950, XP002674004, ISSN: 1464-3391 *
WORM K ET AL: "Simultaneous optimization of potency, selectivity and physicochemical properties for cannabinoid CB2 ligands", CURRENT PHARMACEUTICAL DESIGN 2009 BENTHAM SCIENCE PUBLISHERS B.V. NLD LNKD- DOI:10.2174/138161209789105027, vol. 15, no. 29, October 2009 (2009-10-01), pages 3345 - 3366, XP002674006, ISSN: 1381-6128 *

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