EP1226112A2 - Retro-anandamides, ligands des recepteurs des cannabinoides presentant une affinite et une stabilite elevees - Google Patents

Retro-anandamides, ligands des recepteurs des cannabinoides presentant une affinite et une stabilite elevees

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Publication number
EP1226112A2
EP1226112A2 EP00982697A EP00982697A EP1226112A2 EP 1226112 A2 EP1226112 A2 EP 1226112A2 EP 00982697 A EP00982697 A EP 00982697A EP 00982697 A EP00982697 A EP 00982697A EP 1226112 A2 EP1226112 A2 EP 1226112A2
Authority
EP
European Patent Office
Prior art keywords
group
cannabinoid
receptor
anandamide
analogs
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.)
Withdrawn
Application number
EP00982697A
Other languages
German (de)
English (en)
Other versions
EP1226112A4 (fr
Inventor
Alexandros Makriyannis
Qian Liu
Andreas Goutopoulos
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.)
University of Connecticut
Original Assignee
University of Connecticut
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 University of Connecticut filed Critical University of Connecticut
Publication of EP1226112A2 publication Critical patent/EP1226112A2/fr
Publication of EP1226112A4 publication Critical patent/EP1226112A4/fr
Withdrawn legal-status Critical Current

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    • 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
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    • 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
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    • A61P31/12—Antivirals
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    • 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
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    • 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
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    • 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
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    • C07—ORGANIC CHEMISTRY
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    • 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
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    • 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

L'invention concerne de nouveaux rétro-anandamides qui possèdent des affinités élevées à l'égard des sites des récepteurs des cannabinoïdes CB1 et/ou CB2. De plus, la plupart des analogues présentent une stabilité métabolique supérieure à celle de l'arachidonyléthanolamide. L'affinité et la sélectivité améliorées à l'égard des récepteurs et/ou la stabilité métabolique supérieure de ces analogues les rend utiles d'un point de vue thérapeutique comme médicaments, chez l'être humain et l'animal, pour traiter les douleurs, le glaucome, l'épilepsie, les nausées associées à une chimiothérapie, ainsi que l'immunodépression, pour renforcer l'appétit et traiter certains troubles mentaux.
EP00982697A 1999-10-18 2000-10-18 Retro-anandamides, ligands des recepteurs des cannabinoides presentant une affinite et une stabilite elevees Withdrawn EP1226112A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US16003399P 1999-10-18 1999-10-18
US160033P 1999-10-18
PCT/US2000/041248 WO2001028498A2 (fr) 1999-10-18 2000-10-18 Retro-anandamides, ligands des recepteurs des cannabinoides presentant une affinite et une stabilite elevees

Publications (2)

Publication Number Publication Date
EP1226112A2 true EP1226112A2 (fr) 2002-07-31
EP1226112A4 EP1226112A4 (fr) 2004-10-13

Family

ID=22575216

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00982697A Withdrawn EP1226112A4 (fr) 1999-10-18 2000-10-18 Retro-anandamides, ligands des recepteurs des cannabinoides presentant une affinite et une stabilite elevees

Country Status (7)

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

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999057106A1 (fr) 1998-05-04 1999-11-11 The University Of Connecticut Nouveaux cannabinoides analgesiques et immunomodulateurs
US7589220B2 (en) 1998-06-09 2009-09-15 University Of Connecticut Inhibitors of the anandamide transporter
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 (de) 1999-10-18 2007-11-15 The University Of Connecticut, Farmington Für periphäre cannabinoid-rezeptoren selektive liganden
US6943266B1 (en) 1999-10-18 2005-09-13 University Of Connecticut Bicyclic cannabinoid agonists for the cannabinoid receptor
US7119108B1 (en) 1999-10-18 2006-10-10 University Of Connecticut Pyrazole derivatives as cannabinoid receptor antagonists
US6900236B1 (en) 1999-10-18 2005-05-31 University Of Connecticut Cannabimimetic indole derivatives
US7393842B2 (en) 2001-08-31 2008-07-01 University Of Connecticut Pyrazole analogs acting on cannabinoid receptors
ES2181601B2 (es) * 2001-07-27 2004-04-01 Univ Madrid Complutense Derivados de acido araquidonico con afinidad por el transportador de anandamida
AU2001284061A1 (en) * 2000-07-28 2002-02-18 Universidad Complutense De Madrid Novel araquidonic acid derivatives with affinity toward the anandamide transporter
JP2004532185A (ja) 2001-01-26 2004-10-21 ユニバーシティ オブ コネチカット 新規なカンナビミメティックリガンド
WO2002060447A1 (fr) 2001-01-29 2002-08-08 University Of Connecticut Aminoalkylindoles cannabimimetiques selectifs d'un recepteur
US7057076B2 (en) 2001-07-13 2006-06-06 University Of Connecticut Bicyclic and tricyclic cannabinoids
WO2003007887A2 (fr) 2001-07-20 2003-01-30 Merck & Co., Inc. Imidazoles substitues servant de modulateurs de recepteurs de cannabinoides
PA8557501A1 (es) 2001-11-12 2003-06-30 Pfizer Prod Inc Benzamida, heteroarilamida y amidas inversas
WO2003042190A1 (fr) 2001-11-12 2003-05-22 Pfizer Products Inc. Derives de n-adamantylalkyle benzamide en tant qu'antagonistes du recepteur p2x7
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 (es) 2002-12-31 2004-07-26 Pfizer Prod Inc Inhibidores benzamidicos del receptor p2x7.
WO2006003500A1 (fr) 2004-06-29 2006-01-12 Pfizer Products Inc. Procedes permettant de preparer des derives de 5-[4-(2-hydroxy-propyl)-3,5-dioxo-4,5-dihydro-3h-[1,2,4]triazin-2-yl]-benzamides par deprotection des precurseurs proteges par hydroxyle
FR2885364B1 (fr) * 2005-05-03 2007-06-29 Sanofi Aventis Sa Derives d'alkyl-, alkenyl-et alkynylcarbamates, leur preparation et leur application en therapeutique
EP2020850A4 (fr) * 2006-05-01 2010-10-13 Eastern Virginia Med School Nouveaux cannabinoïdes et procédés d'utilisation
WO2012104793A1 (fr) * 2011-02-02 2012-08-09 Indian Council Of Medical Research Composé antibactérien et antiviral

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JPS61126069A (ja) * 1984-11-21 1986-06-13 Res Dev Corp Of Japan プロスタグランジン誘導体
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

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BERGLUND B A ET AL: "STRUCTURAL REQUIREMENTS FOR ARACHIDONYLETHANOLAMIDE INTERACTION WITH CB1 AND CB2 CANNABINOID RECEPTORS: PHARMACOLOGY OF THE CARBONYL AND ETHANOLAMIDE GROUPS" PROSTAGLANDINS LEUKOTRIENES AND ESSENTIAL FATTY ACIDS, CHURCHILL LIVINGSTONE MEDICAL JOURNALS,, GB, vol. 59, no. 2, 1998, pages 111-118, XP009032879 ISSN: 0952-3278 *
See also references of WO0128498A2 *
SONYUAN L. ET AL.: "Novel analogues of Arachidonylethanolamide (Anandamide):Affinities for the CB1 and CB2 Cannabinoid Receptors and Metabolic Stability" JOURNAL OF MEDICINAL CHEMISTRY, vol. 41, no. 27, 1998, pages 5353-5361, XP002288102 *

Also Published As

Publication number Publication date
JP2003511478A (ja) 2003-03-25
WO2001028498A2 (fr) 2001-04-26
CA2387846A1 (fr) 2001-04-26
AU1969201A (en) 2001-04-30
MXPA02005102A (es) 2003-09-25
WO2001028498A3 (fr) 2001-09-13
ZA200203910B (en) 2004-01-26
EP1226112A4 (fr) 2004-10-13

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