CA2452881C - Novel bicyclic and tricyclic cannabinoids - Google Patents

Novel bicyclic and tricyclic cannabinoids Download PDF

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Publication number
CA2452881C
CA2452881C CA2452881A CA2452881A CA2452881C CA 2452881 C CA2452881 C CA 2452881C CA 2452881 A CA2452881 A CA 2452881A CA 2452881 A CA2452881 A CA 2452881A CA 2452881 C CA2452881 C CA 2452881C
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Prior art keywords
independently
integer
alkyl
compound
halogen
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Expired - Lifetime
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CA2452881A
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English (en)
French (fr)
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CA2452881A1 (en
Inventor
Alexandros Makriyannis
Spyridon P. Nikas
Atmaram D. Khanolkar
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University of Connecticut
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University of Connecticut
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/24—Antidepressants
    • 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
    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/02—Antidotes
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • 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
    • 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
    • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Immunology (AREA)
  • Endocrinology (AREA)
  • Virology (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Toxicology (AREA)
  • Diabetes (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Rheumatology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Reproductive Health (AREA)
  • Otolaryngology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA2452881A 2001-07-13 2002-07-11 Novel bicyclic and tricyclic cannabinoids Expired - Lifetime CA2452881C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US30522801P 2001-07-13 2001-07-13
US60/305,228 2001-07-13
PCT/US2002/021961 WO2003005960A2 (en) 2001-07-13 2002-07-11 Novel bicyclic and tricyclic cannabinoids

Publications (2)

Publication Number Publication Date
CA2452881A1 CA2452881A1 (en) 2003-01-23
CA2452881C true CA2452881C (en) 2012-03-06

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CA2452881A Expired - Lifetime CA2452881C (en) 2001-07-13 2002-07-11 Novel bicyclic and tricyclic cannabinoids

Country Status (6)

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US (2) US7057076B2 (cg-RX-API-DMAC7.html)
EP (1) EP1414775B1 (cg-RX-API-DMAC7.html)
JP (1) JP4312594B2 (cg-RX-API-DMAC7.html)
AU (1) AU2002320430A1 (cg-RX-API-DMAC7.html)
CA (1) CA2452881C (cg-RX-API-DMAC7.html)
WO (1) WO2003005960A2 (cg-RX-API-DMAC7.html)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1075470B1 (en) 1998-05-04 2003-08-13 The University Of Connecticut Novel analgesic and immunomodulatory cannabinoids
US7589220B2 (en) * 1998-06-09 2009-09-15 University Of Connecticut 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
US7741365B2 (en) * 1999-10-18 2010-06-22 University Of Connecticut Peripheral cannabinoid receptor (CB2) selective ligands
US6943266B1 (en) * 1999-10-18 2005-09-13 University Of Connecticut Bicyclic cannabinoid agonists for the cannabinoid receptor
US6900236B1 (en) * 1999-10-18 2005-05-31 University Of Connecticut Cannabimimetic indole derivatives
EP1223808B1 (en) 1999-10-18 2007-03-07 The University Of Connecticut Peripheral cannabinoid receptor (cb2) selective ligands
US7119108B1 (en) * 1999-10-18 2006-10-10 University Of Connecticut Pyrazole derivatives as cannabinoid receptor antagonists
US8084467B2 (en) * 1999-10-18 2011-12-27 University Of Connecticut Pyrazole derivatives as cannabinoid receptor antagonists
US7393842B2 (en) 2001-08-31 2008-07-01 University Of Connecticut Pyrazole analogs acting on cannabinoid receptors
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
DE60237431D1 (de) 2001-01-29 2010-10-07 Univ Connecticut Rezeptor-selektive cannabimimetische aminoalkylindole
CA2452881C (en) 2001-07-13 2012-03-06 University Of Connecticut Novel bicyclic and tricyclic cannabinoids
US7446229B2 (en) * 2001-07-13 2008-11-04 University Of Connecticut Bicyclic cannabinoids
WO2003035005A2 (en) * 2001-10-26 2003-05-01 University Of Connecticut Heteroindanes: a new class of potent cannabimimetic ligands
WO2003063758A2 (en) * 2002-01-31 2003-08-07 Pharmos Corporation Bicyclic cb2 cannabinoid receptor ligands
US7183313B2 (en) 2002-08-23 2007-02-27 University Of Connecticut Keto cannabinoids with therapeutic indications
MXPA06011423A (es) * 2004-04-02 2007-01-23 Osi Pharm Inc Inhibidores de proteina cinasa heterobiciclica sustituida en el anillo 6,6-biciclico.
WO2008001369A1 (en) * 2006-06-27 2008-01-03 Pharmos Corporation Use of cb2 receptor agonists for promoting neurogenesis
CA2679373A1 (en) 2007-03-02 2008-09-12 The University Of Tennessee Research Foundation Tri-aryl/heteroaromatic cannabinoids and use thereof
US8349876B2 (en) * 2008-05-19 2013-01-08 The University Of Tennesee Research Foundation Pyridine non-classical cannabinoid compounds and related methods of use
US8389534B2 (en) * 2008-05-19 2013-03-05 The University Of Tennessee Research Foundation Pyrimidine non-classical cannabinoid compounds and related methods of use
EP2299819A4 (en) 2008-05-19 2011-07-20 Univ Tennessee Res Foundation NONCLASSICAL PYRIDINE CANNABINOID COMPOUNDS AND ASSOCIATED METHODS FOR THEIR USE
US8022078B2 (en) * 2008-05-19 2011-09-20 University Of Tennessee Research Foundation Pyrimidine classical cannabinoid compounds and related methods of use
WO2009143183A1 (en) 2008-05-19 2009-11-26 University Of Tennessee Research Foundation, The Pyrimidine non-classical cannabinoid compounds and related methods of use
EP2346804B1 (en) 2008-10-06 2017-03-08 Yissum Research Development Company of the Hebrew University of Jerusalem, Ltd. Composition comprising cb receptor agonists and uses thereof
WO2011006099A1 (en) * 2009-07-10 2011-01-13 Northeastern University Angiogenic resorcinol derivatives

Family Cites Families (104)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US557636A (en) * 1896-04-07 baker
US3041343A (en) * 1959-10-14 1962-06-26 Sandoz Ltd 4-(thienyl-2'')-and 4-(pyridyl-3'')-5-aminopyrazoles
CH448068A (de) 1964-07-31 1967-12-15 Geigy Ag J R Verfahren zur Herstellung von neuen Guanidinderivaten
US3577458A (en) * 1966-11-14 1971-05-04 Allied Chem Process for the preparation of isocyanates
US3465024A (en) * 1966-11-14 1969-09-02 Allied Chem Process for the preparation of isocyanates
US3573327A (en) * 1970-03-23 1971-03-30 Searle & Co 3-(lower alkoxy)-7,8,9,10-tetrahydro-6h-dibenzo-(b,d) pyran-6,9-diones and derivatives thereof
US3656906A (en) * 1970-04-13 1972-04-18 Little Inc A Method for detecting and quantitating the presence of cannabinoids and analogs thereof in biological materials and resulting products
US3838131A (en) * 1972-04-03 1974-09-24 Pfizer Di(dialkylamino alkoxy)phenanthridines as antiviral agents
US3915996A (en) * 1972-10-16 1975-10-28 Abbott Lab Process for making benzopyrans
GB1436771A (en) * 1973-02-16 1976-05-26 Labaz Indole derivatives and process for preparing the same
DE2335136A1 (de) * 1973-07-06 1975-01-16 Schering Ag 7-hydroxy-delta hoch 8-tetrahydrocannabinole
US3886184A (en) 1973-08-03 1975-05-27 Lilly Co Eli Aminodibenzo(b,d)pyrans
US4278603A (en) * 1973-11-05 1981-07-14 Eli Lilly And Company Novel polymorphic crystalline form of dibenzopyranone
US3944673A (en) * 1973-11-05 1976-03-16 Eli Lilly And Company Hexahydro-dibenzo[b,d]pyran-9-ones as analgesic drugs
US3953603A (en) * 1973-11-05 1976-04-27 Eli Lilly And Company Hexahydro-dibenzo[b,d,]pyran-9-ones as psychotropic, particularly anti-depressant drugs
US3928598A (en) * 1973-11-05 1975-12-23 Lilly Co Eli Hexahydro-dibenzo{8 b,d{9 pyran-9-ones as an anti-anxiety drug
IL48824A (en) * 1976-01-12 1980-05-30 Yissum Res Dev Co Pharmaceutical compositions containing (3s,js) tetrahydrocanabinol derivatives and some novel compounds of this type
US4036857A (en) * 1976-02-02 1977-07-19 Sharps Associates Benzopyrans having an unsaturated side chain
US4088777A (en) * 1976-02-17 1978-05-09 Eli Lilly And Company Hexahydro-dibenzo[b,d]pyran-9-ones as anticonvulsant drugs
US4087547A (en) * 1976-02-17 1978-05-02 Eli Lilly And Company Hexahydro-dibenzo[b,d]pyran-9-ones in treatment of glaucoma
US4087546A (en) * 1976-02-17 1978-05-02 Eli Lilly And Company Hexahydro-dibenzo[b,d]pyran-9-ones as antiasthmatic drugs
US4087545A (en) * 1976-02-17 1978-05-02 Eli Lilly And Company Hexahydro-dibenzo[b,d]pyran-9-ones as antiemetic drugs
US4054582A (en) * 1976-07-06 1977-10-18 Eli Lilly And Company Process for converting cis-hexahydrodibenzo[b,d]pyran-9-ones to trans-hexahydrodibenzo[b,d]-pyran-9-ones
US4176233A (en) * 1976-11-10 1979-11-27 Eli Lilly And Company Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
US4102902A (en) * 1976-11-10 1978-07-25 Eli Lilly And Company Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
US4208351A (en) * 1976-11-10 1980-06-17 Eli Lilly And Company Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
US4188495A (en) * 1977-11-14 1980-02-12 Pfizer Inc. 1,9-Dihydroxyoctahydrophenanthrenes and intermediates therefor
US4152450A (en) 1978-02-17 1979-05-01 Eli Lilly And Company 9-Amino-dibenzopyrans
US4171315A (en) * 1978-03-31 1979-10-16 Eli Lilly And Company Preparation of cis-hexahydrodibenzopyranones
IL55274A (en) * 1978-08-02 1982-08-31 Yissum Res Dev Co 4-(2,6-dihydroxy-4-(dimethylheptyl)phenyl)substituted 2-pinen-10-ol and pinane derivatives,their preparation and pharmaceutical compositions comprising them
DE3025385A1 (de) * 1980-07-04 1982-01-28 Boehringer Mannheim Gmbh, 6800 Mannheim Neue tricyclische arylether, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
JPS5798228A (en) 1980-12-10 1982-06-18 Hisamitsu Pharmaceut Co Inc Biphenyl derivative
JPS5798228U (cg-RX-API-DMAC7.html) 1980-12-10 1982-06-16
US4550214A (en) * 1981-01-05 1985-10-29 Polaroid Corporation Blocked vinyl biphenyl compounds
US4395560A (en) * 1982-05-24 1983-07-26 Eli Lilly And Company Preparation of 6a,10a-trans-hexahydrodibenzopyranones
US4497827A (en) * 1982-08-30 1985-02-05 Syntex (U.S.A.) Inc. Arachidonic acid analogues as anti-inflammatory and anti-allergic agents
US4885295A (en) * 1984-08-06 1989-12-05 Sterling Drug Inc. Method of use of 3-arylcarbonyl- and 3-cycloalkyl-carbonyl-1-aminoalkyl-1H-indoles
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
IL80411A (en) * 1986-10-24 1991-08-16 Raphael Mechoulam Preparation of dibenzopyranol derivatives and pharmaceutical compositions containing them
US4833073A (en) 1987-01-27 1989-05-23 Hoffmann-La Roche Inc. Immunoassay for tetrahydrocannabinol metabolites
US4758597A (en) * 1987-05-15 1988-07-19 University Patents, Inc. Carenadiol and derivatives
HU206337B (en) * 1988-12-29 1992-10-28 Mitsui Petrochemical Ind Process for producing pyrimidine derivatives and pharmaceutical compositions
KR900012875A (ko) * 1989-02-08 1990-09-03 오스카 아끼히꼬 비페닐 유도체, 신경세포 변성수복 또는 보호제 및 여기에 사용되는 폐닐유도체의 제조방법
JPH02304080A (ja) 1989-05-17 1990-12-17 Toyo Pharma- Kk ６Ｈ―ジベンゾ［ｂ，ｄ］ピラン―６―オン誘導体，その製法及び用途
US5284867A (en) * 1989-11-07 1994-02-08 Yissum Research Development Company Of The Hebrew University In Jerusalem NMDA-blocking pharmaceutical compositions
US5521215A (en) * 1989-11-07 1996-05-28 Ramot University Authority For Applied Research And Industrial Development Ltd. NMDA-blocking pharmaceuticals
US5068234A (en) * 1990-02-26 1991-11-26 Sterling Drug Inc. 3-arylcarbonyl-1-(c-attached-n-heteryl)-1h-indoles
FR2665444B1 (fr) 1990-08-06 1992-11-27 Sanofi Sa Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant.
US6096740A (en) * 1990-11-06 2000-08-01 Ramot University Authority For Applied Research And Industrial Development Ltd. Dexanabinol derivatives and their use as neuroprotective pharmaceutical compositions
US5576436A (en) 1991-08-01 1996-11-19 Pharmaceutical Discovery Corporation Fluorescent ligands
US5635530A (en) * 1991-09-12 1997-06-03 Yissum Research Development Company Of The Hebrew University Of Jerusalem (3S,4S)-delta-6-tetrahydrocannabinol-7-oic acids and derivatives thereof, processors for their preparation and pharmaceutical compositions containing them
US5538993A (en) * 1991-09-12 1996-07-23 Yissum Research Development Company Certain tetrahydrocannabinol-7-oic acid derivatives
FR2692575B1 (fr) 1992-06-23 1995-06-30 Sanofi Elf Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant.
US5489580A (en) * 1992-11-05 1996-02-06 University Of Connecticut Phospholipid compounds and use therefor
IL103932A (en) 1992-11-30 1997-02-18 Yissum Res & Dev Fatty acid and pharmaceutical compositions containing them
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
US5440052A (en) * 1993-08-06 1995-08-08 University Of Connecticut Compositions useful as a cannabinoid receptor probe
FR2714057B1 (fr) * 1993-12-17 1996-03-08 Sanofi Elf Nouveaux dérivés du 3-pyrazolecarboxamide, procédé pour leur préparation et compositions pharmaceutiques les contenant.
US5434295A (en) * 1994-02-07 1995-07-18 Yissum Research Development Company Neuroprotective pharmaceutical compositions of 4-phenylpinene derivatives and certain novel 4-phenylpinene compounds
US5631297A (en) * 1994-07-11 1997-05-20 Pate; David W. Anandamides useful for the treatment of intraocular hypertension, ophthalmic compositions containing the same and methods of use of the same
US5596106A (en) * 1994-07-15 1997-01-21 Eli Lilly And Company Cannabinoid receptor antagonists
US5532237A (en) * 1995-02-15 1996-07-02 Merck Frosst Canada, Inc. Indole derivatives with affinity for the cannabinoid receptor
US5605906A (en) * 1995-03-24 1997-02-25 Merck Frosst Canada, Inc. Cannabinoid receptor agonists
US5804601A (en) * 1995-04-10 1998-09-08 Takeda Chemical Industries, Ltd. Aromatic hydroxamic acid compounds, their production and use
FR2735774B1 (fr) 1995-06-21 1997-09-12 Sanofi Sa Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant
IL115245A (en) * 1995-09-11 2002-12-01 Yissum Res Dev Co Tumor necrosis factor inhibiting pharmaceuticals
FR2741621B1 (fr) * 1995-11-23 1998-02-13 Sanofi Sa Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant
FR2742148B1 (fr) * 1995-12-08 1999-10-22 Sanofi Sa Nouveaux derives du pyrazole-3-carboxamide, procede pour leur preparation et compositions pharmaceutiques les contenant
US5688825A (en) * 1996-05-31 1997-11-18 University Of Connecticut Anandamide amidase inhibitors as analgesic agents
US5760225A (en) * 1996-11-15 1998-06-02 Neurogen Corporation Certain pyrazole derivatives as corticotropin-releasing factor receptor CRF1 specific ligands
DE19706903A1 (de) * 1997-02-21 1998-08-27 Bayer Ag Verwendung von bekannten Agonisten des zentralen Cannabinoid-Rezeptors CB 1
JP2001516361A (ja) * 1997-03-18 2001-09-25 スミスクライン・ビーチャム・コーポレイション 新規カンナビノイド受容体作動薬
US5925628A (en) * 1997-03-31 1999-07-20 Genzyme Corporation Cationic amphiphiles for intracellular delivery of therapeutic molecules
US5939429A (en) * 1997-09-30 1999-08-17 Virginia Commonwealth University Cardiovascular uses of cannabinoid compounds
CA2340444A1 (en) 1998-05-04 1999-11-11 The University Of Connecticut Cannabinoids selective for the cb2 receptor
EP1075470B1 (en) 1998-05-04 2003-08-13 The University Of Connecticut Novel analgesic and immunomodulatory cannabinoids
US7897598B2 (en) * 1998-06-09 2011-03-01 Alexandros Makriyannis Inhibitors of the anandamide transporter
JP2002517479A (ja) 1998-06-09 2002-06-18 ザ・ユニバ−シティ・オブ・コネチカット 鎮痛薬としてのアナンダミド輸送体阻害剤
US7589220B2 (en) * 1998-06-09 2009-09-15 University Of Connecticut Inhibitors of the anandamide transporter
WO2001028498A2 (en) 1999-10-18 2001-04-26 University Of Connecticut Retro-anandamides, high affinity and stability cannabinoid receptor ligands
WO2000032200A1 (en) 1998-11-24 2000-06-08 Alexandros Makriyannis Cannabimimetic lipid amides as useful medications
US6900236B1 (en) * 1999-10-18 2005-05-31 University Of Connecticut Cannabimimetic indole derivatives
JP2003512357A (ja) 1999-10-18 2003-04-02 ユニバーシティ オブ コネチカット カンナビノイドレセプタ拮抗物質としてのピラゾール誘導体
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
MXPA02005104A (es) * 1999-10-18 2003-09-25 Alexipharma Inc Agonistas novedosos de canabinoide biciclico para el receptor canabinoide.
US7393842B2 (en) * 2001-08-31 2008-07-01 University Of Connecticut Pyrazole analogs acting on cannabinoid receptors
EP1223808B1 (en) 1999-10-18 2007-03-07 The University Of Connecticut Peripheral cannabinoid receptor (cb2) selective ligands
WO2001028557A1 (en) 1999-10-18 2001-04-26 University Of Connecticut Cannabimimetic indole derivatives
US8084467B2 (en) * 1999-10-18 2011-12-27 University Of Connecticut Pyrazole derivatives as cannabinoid receptor antagonists
IL132661A (en) 1999-10-31 2008-11-26 Raphael Mechoulam Agonists specific for peripheral cannabinoid receptors
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
AU783522B2 (en) * 2000-06-22 2005-11-03 Pharmos Corporation Novel non-psychotropic cannabinoids
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
DE60237431D1 (de) 2001-01-29 2010-10-07 Univ Connecticut Rezeptor-selektive cannabimimetische aminoalkylindole
WO2002088056A1 (en) * 2001-05-02 2002-11-07 Exxonmobil Chemical Patents Inc. Xylene isomerization
CA2452881C (en) * 2001-07-13 2012-03-06 University Of Connecticut Novel bicyclic and tricyclic cannabinoids
JP2005507875A (ja) 2001-08-31 2005-03-24 ユニバーシティ オブ コネチカット カンナビノイド受容体に作用する新規なピラゾール類似体
WO2003035005A2 (en) 2001-10-26 2003-05-01 University Of Connecticut Heteroindanes: a new class of potent cannabimimetic ligands
WO2003063758A2 (en) 2002-01-31 2003-08-07 Pharmos Corporation Bicyclic cb2 cannabinoid receptor ligands
IL147941A0 (en) 2002-01-31 2002-08-14 Pharmos Corp Bicyclic cb2 cannabinoid receptor ligands
EP1542948A4 (en) 2002-08-23 2008-12-17 Univ Connecticut NEW BIPHENYL AND BIPHENYLENE CANNABINOIDS
US7183313B2 (en) * 2002-08-23 2007-02-27 University Of Connecticut Keto cannabinoids with therapeutic indications

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AU2002320430A1 (en) 2003-01-29
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US20040236116A1 (en) 2004-11-25
EP1414775A2 (en) 2004-05-06
US7057076B2 (en) 2006-06-06
JP2005504736A (ja) 2005-02-17
JP4312594B2 (ja) 2009-08-12
WO2003005960A2 (en) 2003-01-23

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