CA2387846A1 - 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 Download PDF

Info

Publication number
CA2387846A1
CA2387846A1 CA002387846A CA2387846A CA2387846A1 CA 2387846 A1 CA2387846 A1 CA 2387846A1 CA 002387846 A CA002387846 A CA 002387846A CA 2387846 A CA2387846 A CA 2387846A CA 2387846 A1 CA2387846 A1 CA 2387846A1
Authority
CA
Canada
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.)
Abandoned
Application number
CA002387846A
Other languages
English (en)
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
Individual
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 Individual filed Critical Individual
Publication of CA2387846A1 publication Critical patent/CA2387846A1/fr
Abandoned legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Virology (AREA)
  • Psychology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • AIDS & HIV (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Communicable Diseases (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (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.
CA002387846A 1999-10-18 2000-10-18 Retro-anandamides, ligands des recepteurs des cannabinoides presentant une affinite et une stabilite elevees Abandoned CA2387846A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US16003399P 1999-10-18 1999-10-18
US60/160,033 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 (1)

Publication Number Publication Date
CA2387846A1 true CA2387846A1 (fr) 2001-04-26

Family

ID=22575216

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002387846A Abandoned CA2387846A1 (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 (19)

* 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
US6943266B1 (en) 1999-10-18 2005-09-13 University Of Connecticut Bicyclic cannabinoid agonists for the cannabinoid receptor
US6995187B1 (en) 1999-10-18 2006-02-07 University Of Connecticut Peripheral cannabinoid receptor (CB2) selective ligands
US6900236B1 (en) 1999-10-18 2005-05-31 University Of Connecticut Cannabimimetic indole derivatives
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
US7057076B2 (en) 2001-07-13 2006-06-06 University Of Connecticut Bicyclic and tricyclic cannabinoids
AU2002319627A1 (en) 2001-07-20 2003-03-03 Merck And Co., Inc. Substituted imidazoles as cannabinoid receptor modulators
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
WO2004017922A2 (fr) 2002-08-23 2004-03-04 University Of Connecticut Ceto-cannabinoides possedant des indications therapeutiques
PA8591801A1 (es) 2002-12-31 2004-07-26 Pfizer Prod Inc Inhibidores benzamidicos del receptor p2x7.
US7071223B1 (en) 2002-12-31 2006-07-04 Pfizer, Inc. Benzamide inhibitors of the P2X7 receptor
AU2005258911A1 (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 (fr) * 2005-05-03 2007-06-29 Sanofi Aventis Sa Derives d'alkyl-, alkenyl-et alkynylcarbamates, leur preparation et leur application en therapeutique
CN101484004A (zh) * 2006-05-01 2009-07-15 东弗吉尼亚医学院 新型大麻素及使用方法
WO2012104793A1 (fr) * 2011-02-02 2012-08-09 Indian Council Of Medical Research Composé antibactérien et antiviral

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Also Published As

Publication number Publication date
MXPA02005102A (es) 2003-09-25
JP2003511478A (ja) 2003-03-25
WO2001028498A3 (fr) 2001-09-13
WO2001028498A2 (fr) 2001-04-26
AU1969201A (en) 2001-04-30
EP1226112A4 (fr) 2004-10-13
ZA200203910B (en) 2004-01-26
EP1226112A2 (fr) 2002-07-31

Similar Documents

Publication Publication Date Title
AU780572B2 (en) Pyrazole derivatives as cannabinoid receptor antagonists
EP1223929B1 (fr) Derives indoliques cannabimimetiques
CA2387846A1 (fr) Retro-anandamides, ligands des recepteurs des cannabinoides presentant une affinite et une stabilite elevees
US7119108B1 (en) Pyrazole derivatives as cannabinoid receptor antagonists
US20080090871A1 (en) Cannabimimetic indole derivatives
US7335688B2 (en) Bicyclic cannabinoid agonists for the cannabinoid receptor
EP1414775B1 (fr) Cannabinoide bicyclique
EP1223808B1 (fr) Ligands selectifs de recepteurs (cb2) de cannabinoides peripheriques
AU785033B2 (en) Novel bicyclic cannabinoid agonists for the cannabinoid receptor
US7741365B2 (en) Peripheral cannabinoid receptor (CB2) selective ligands
US7276613B1 (en) Retro-anandamides, high affinity and stability cannabinoid receptor ligands
EP1702617A1 (fr) Dérivés indoliques cannabimimetiques

Legal Events

Date Code Title Description
EEER Examination request
FZDE Dead