WO2001028498A3 - Retro-anandamides, high affinity and stability cannabinoid receptor ligands - Google Patents

Retro-anandamides, high affinity and stability cannabinoid receptor ligands Download PDF

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Publication number
WO2001028498A3
WO2001028498A3 PCT/US2000/041248 US0041248W WO0128498A3 WO 2001028498 A3 WO2001028498 A3 WO 2001028498A3 US 0041248 W US0041248 W US 0041248W WO 0128498 A3 WO0128498 A3 WO 0128498A3
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WO
WIPO (PCT)
Prior art keywords
anandamides
retro
stability
high affinity
receptor ligands
Prior art date
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Ceased
Application number
PCT/US2000/041248
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French (fr)
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WO2001028498A2 (en
Inventor
Alexandros Makriyannis
Qian Liu
Andreas Goutopoulos
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University of Connecticut
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University of Connecticut
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Publication date
Application filed by University of Connecticut filed Critical University of Connecticut
Priority to AU19692/01A priority Critical patent/AU1969201A/en
Priority to JP2001531094A priority patent/JP2003511478A/en
Priority to US10/110,862 priority patent/US7276613B1/en
Priority to EP00982697A priority patent/EP1226112A4/en
Priority to MXPA02005102A priority patent/MXPA02005102A/en
Priority to CA002387846A priority patent/CA2387846A1/en
Publication of WO2001028498A2 publication Critical patent/WO2001028498A2/en
Publication of WO2001028498A3 publication Critical patent/WO2001028498A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C07D295/20—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 carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • 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
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
    • 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
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Psychology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Virology (AREA)
  • Cardiology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Molecular Biology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • AIDS & HIV (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Novel retro-anandamides are presented which have high affinities for the cannabinoid CB1 and/or CB2 receptor sites. Further, most of the analogs exhibit greater metabolic stability than arachidonylethanolamide. The improved receptor affinity and selectivity and/or greater metabolic stability make these analogs therapeutically useful as medications in individuals and animals for treatment of pain, glaucoma, epilepsy, nausea associated with chemotherapy, as well as suppression of the immune system, enhancement of appetite and in treatment of certain mental disorders.
PCT/US2000/041248 1998-11-24 2000-10-18 Retro-anandamides, high affinity and stability cannabinoid receptor ligands Ceased WO2001028498A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU19692/01A AU1969201A (en) 1999-10-18 2000-10-18 Retro-anandamides, high affinity and stability cannabinoid receptor ligands
JP2001531094A JP2003511478A (en) 1999-10-18 2000-10-18 Retro-anandamide, a high affinity and stable cannabinoid receptor ligand
US10/110,862 US7276613B1 (en) 1998-11-24 2000-10-18 Retro-anandamides, high affinity and stability cannabinoid receptor ligands
EP00982697A EP1226112A4 (en) 1999-10-18 2000-10-18 RETRO ANANDAMID, CANNABINOID RECEPTOR LIGANDS WITH HIGH AFFINITY AND STABILITY
MXPA02005102A MXPA02005102A (en) 1999-10-18 2000-10-18 Retro anandamides, high affinity and stability cannabinoid receptor ligands.
CA002387846A CA2387846A1 (en) 1999-10-18 2000-10-18 Retro-anandamides, high affinity and stability cannabinoid receptor ligands

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16003399P 1999-10-18 1999-10-18
US60/160,033 1999-10-18

Publications (2)

Publication Number Publication Date
WO2001028498A2 WO2001028498A2 (en) 2001-04-26
WO2001028498A3 true WO2001028498A3 (en) 2001-09-13

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ID=22575216

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PCT/US2000/041248 Ceased WO2001028498A2 (en) 1998-11-24 2000-10-18 Retro-anandamides, high affinity and stability cannabinoid receptor ligands

Country Status (7)

Country Link
EP (1) EP1226112A4 (en)
JP (1) JP2003511478A (en)
AU (1) AU1969201A (en)
CA (1) CA2387846A1 (en)
MX (1) MXPA02005102A (en)
WO (1) WO2001028498A2 (en)
ZA (1) ZA200203910B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7119108B1 (en) 1999-10-18 2006-10-10 University Of Connecticut Pyrazole derivatives as cannabinoid receptor antagonists
US7173027B2 (en) 2001-01-29 2007-02-06 University Of Connecticut Receptor selective cannabimimetic aminoalkylindoles
US7241799B2 (en) 1999-10-18 2007-07-10 University Of Connecticut Cannabimimetic indole derivatives
US7285683B2 (en) 2001-07-13 2007-10-23 University Of Connecticut Bicyclic and tricyclic cannabinoids
US7335688B2 (en) 1999-10-18 2008-02-26 University Of Connecticut Bicyclic cannabinoid agonists for the cannabinoid receptor
US7393842B2 (en) 2001-08-31 2008-07-01 University Of Connecticut Pyrazole analogs acting on cannabinoid receptors
US7589220B2 (en) 1998-06-09 2009-09-15 University Of Connecticut Inhibitors of the anandamide transporter

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999057106A1 (en) 1998-05-04 1999-11-11 The University Of Connecticut Novel analgesic and immunomodulatory cannabinoids
US7897598B2 (en) 1998-06-09 2011-03-01 Alexandros Makriyannis Inhibitors of the anandamide transporter
US7276613B1 (en) 1998-11-24 2007-10-02 University Of Connecticut Retro-anandamides, high affinity and stability cannabinoid receptor ligands
US7161016B1 (en) 1998-11-24 2007-01-09 University Of Connecticut Cannabimimetic lipid amides as useful medications
DE60033834T2 (en) 1999-10-18 2007-11-15 The University Of Connecticut, Farmington FOR PERIPHERAL CANNABINOID RECEPTORS SELECTIVE LIGANDS
ES2181601B2 (en) * 2001-07-27 2004-04-01 Univ Madrid Complutense ARAQUIDONIC ACID DERIVATIVES AFFINED BY THE ANANDAMIDE CARRIER
AU2001284061A1 (en) * 2000-07-28 2002-02-18 Universidad Complutense De Madrid Novel araquidonic acid derivatives with affinity toward the anandamide transporter
JP2004532185A (en) 2001-01-26 2004-10-21 ユニバーシティ オブ コネチカット New cannabimetic ligands
WO2003007887A2 (en) 2001-07-20 2003-01-30 Merck & Co., Inc. Substituted imidazoles as cannabinoid receptor modulators
PA8557501A1 (en) 2001-11-12 2003-06-30 Pfizer Prod Inc BENZAMIDA, HETEROARILAMIDA AND INVESTED AMIDAS
WO2003042190A1 (en) 2001-11-12 2003-05-22 Pfizer Products Inc. N-alkyl-adamantyl derivatives as p2x7-receptor antagonists
AU2003217961B2 (en) 2002-03-08 2008-02-28 Signal Pharmaceuticals, Llc Combination therapy for treating, preventing or managing proliferative disorders and cancers
US7183313B2 (en) 2002-08-23 2007-02-27 University Of Connecticut Keto cannabinoids with therapeutic indications
US7071223B1 (en) 2002-12-31 2006-07-04 Pfizer, Inc. Benzamide inhibitors of the P2X7 receptor
PA8591801A1 (en) 2002-12-31 2004-07-26 Pfizer Prod Inc BENZAMID INHIBITORS OF THE P2X7 RECEIVER.
WO2006003500A1 (en) 2004-06-29 2006-01-12 Pfizer Products Inc. Method for preparing 5-`4-(2-hydroxy-propyl)-3,5-dioxo-4,5-dihydro-3h`1,2,4!triazin-2-yl!-benzamide derivatives by deprotecting the hydroxyl-protected precursers
FR2885364B1 (en) * 2005-05-03 2007-06-29 Sanofi Aventis Sa ALKYL-, ALKENYL- AND ALKYNYLCARBAMATES DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
EP2020850A4 (en) * 2006-05-01 2010-10-13 Eastern Virginia Med School NEW CANNABINOIDS AND METHODS OF USE
WO2012104793A1 (en) * 2011-02-02 2012-08-09 Indian Council Of Medical Research An antibacterial and antiviral compound

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4812457A (en) * 1984-11-21 1989-03-14 Research Development Corporation Prostaglandin derivatives
US5618955A (en) * 1992-11-30 1997-04-08 Yissum Research Development Company Of The Hebrew University Of Jerusalem Fatty acid derivatives and pharmaceutical compositions containing same
US5688825A (en) * 1996-05-31 1997-11-18 University Of Connecticut Anandamide amidase inhibitors as analgesic agents
US5925628A (en) * 1997-03-31 1999-07-20 Genzyme Corporation Cationic amphiphiles for intracellular delivery of therapeutic molecules

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4812457A (en) * 1984-11-21 1989-03-14 Research Development Corporation Prostaglandin derivatives
US5618955A (en) * 1992-11-30 1997-04-08 Yissum Research Development Company Of The Hebrew University Of Jerusalem Fatty acid derivatives and pharmaceutical compositions containing same
US5688825A (en) * 1996-05-31 1997-11-18 University Of Connecticut Anandamide amidase inhibitors as analgesic agents
US5874459A (en) * 1996-05-31 1999-02-23 University Of Connecticut Anandamide amidase inhibitors as analgesic agents
US5925628A (en) * 1997-03-31 1999-07-20 Genzyme Corporation Cationic amphiphiles for intracellular delivery of therapeutic molecules

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1226112A4 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7589220B2 (en) 1998-06-09 2009-09-15 University Of Connecticut Inhibitors of the anandamide transporter
US7119108B1 (en) 1999-10-18 2006-10-10 University Of Connecticut Pyrazole derivatives as cannabinoid receptor antagonists
US7241799B2 (en) 1999-10-18 2007-07-10 University Of Connecticut Cannabimimetic indole derivatives
US7335688B2 (en) 1999-10-18 2008-02-26 University Of Connecticut Bicyclic cannabinoid agonists for the cannabinoid receptor
US7173027B2 (en) 2001-01-29 2007-02-06 University Of Connecticut Receptor selective cannabimimetic aminoalkylindoles
US7285683B2 (en) 2001-07-13 2007-10-23 University Of Connecticut Bicyclic and tricyclic cannabinoids
US7393842B2 (en) 2001-08-31 2008-07-01 University Of Connecticut Pyrazole analogs acting on cannabinoid receptors

Also Published As

Publication number Publication date
EP1226112A2 (en) 2002-07-31
JP2003511478A (en) 2003-03-25
WO2001028498A2 (en) 2001-04-26
CA2387846A1 (en) 2001-04-26
AU1969201A (en) 2001-04-30
MXPA02005102A (en) 2003-09-25
ZA200203910B (en) 2004-01-26
EP1226112A4 (en) 2004-10-13

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