JPH09511493A - デキサナビノール誘導体及び同誘導体の神経保護薬剤組成物としての利用 - Google Patents

デキサナビノール誘導体及び同誘導体の神経保護薬剤組成物としての利用

Info

Publication number: JPH09511493A
Authority: JP; Japan
Prior art keywords: alkyl; compound; dexanabinol; group; compound according
Prior art date: 1994-02-07
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.): Pending

Application number

JP7520787A

Other languages

English (en)

Japanese (ja)

Inventor

メコウラム、ラファエル

ポップ、エミール

ソコロブスキー、モーデカイ

クルッグ、ヨエル

ビゴン、アネイト

Original Assignee

レイモットユニバーシティーオーソリティーフォーアプライドリサーチアンドインダストリアルディベロップメントリミテッド

イッサムリサーチディベロップメントカンパニーオブザヘブルユニバーシティーインエルサレム

ファーモスコーポレイション

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.)

1994-02-07

Filing date

1995-02-06

Publication date

1997-11-18

1995-02-06 Application filed by レイモットユニバーシティーオーソリティーフォーアプライドリサーチアンドインダストリアルディベロップメントリミテッド, イッサムリサーチディベロップメントカンパニーオブザヘブルユニバーシティーインエルサレム, ファーモスコーポレイション filed Critical レイモットユニバーシティーオーソリティーフォーアプライドリサーチアンドインダストリアルディベロップメントリミテッド

1997-11-18 Publication of JPH09511493A publication Critical patent/JPH09511493A/ja

Status Pending legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title abstract description 60
SSQJFGMEZBFMNV-PMACEKPBSA-N dexanabinol Chemical class C1C(CO)=CC[C@@H]2C(C)(C)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@H]21 SSQJFGMEZBFMNV-PMACEKPBSA-N 0.000 title description 201
239000003814 drug Substances 0.000 title description 35
229940079593 drug Drugs 0.000 title description 31
230000000324 neuroprotective effect Effects 0.000 title description 20
150000001875 compounds Chemical class 0.000 claims abstract description 187
230000006378 damage Effects 0.000 claims abstract description 77
208000014674 injury Diseases 0.000 claims abstract description 50
208000027418 Wounds and injury Diseases 0.000 claims abstract description 37
210000003169 central nervous system Anatomy 0.000 claims abstract description 26
206010029350 Neurotoxicity Diseases 0.000 claims abstract description 16
206010044221 Toxic encephalopathy Diseases 0.000 claims abstract description 16
231100000228 neurotoxicity Toxicity 0.000 claims abstract description 16
230000007135 neurotoxicity Effects 0.000 claims abstract description 16
208000010496 Heart Arrest Diseases 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
-1 heterocyclyl radicals Chemical class 0.000 claims description 99
239000000243 solution Substances 0.000 claims description 99
238000000034 method Methods 0.000 claims description 61
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
229910001868 water Inorganic materials 0.000 claims description 45
210000005036 nerve Anatomy 0.000 claims description 41
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
206010030113 Oedema Diseases 0.000 claims description 27
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 24
206010019196 Head injury Diseases 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 18
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 17
206010028851 Necrosis Diseases 0.000 claims description 16
230000017074 necrotic cell death Effects 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 15
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239000001257 hydrogen Substances 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
208000006011 Stroke Diseases 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 13
125000001453 quaternary ammonium group Chemical group 0.000 claims description 13
208000024891 symptom Diseases 0.000 claims description 13
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 12
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239000007864 aqueous solution Substances 0.000 claims description 11
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 9
206010008120 Cerebral ischaemia Diseases 0.000 claims description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000006184 cosolvent Substances 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
230000001404 mediated effect Effects 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
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125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
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125000004122 cyclic group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
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150000002431 hydrogen Chemical group 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
229940024606 amino acid Drugs 0.000 claims description 3
150000001413 amino acids Chemical class 0.000 claims description 3
NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
208000020431 spinal cord injury Diseases 0.000 claims description 3
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
239000002563 ionic surfactant Substances 0.000 claims description 2
239000000787 lecithin Substances 0.000 claims description 2
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235000010445 lecithin Nutrition 0.000 claims description 2
239000002736 nonionic surfactant Substances 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims 2
150000001449 anionic compounds Chemical class 0.000 claims 2
125000003710 aryl alkyl group Chemical group 0.000 claims 2
125000003118 aryl group Chemical group 0.000 claims 2
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IOGYHRRCLCUDCC-UHFFFAOYSA-L disodium hydroxy-dioxido-sulfanylidene-lambda5-phosphane Chemical compound P(=S)([O-])([O-])O.[Na+].[Na+] IOGYHRRCLCUDCC-UHFFFAOYSA-L 0.000 claims 1
239000003995 emulsifying agent Substances 0.000 claims 1
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239000004480 active ingredient Substances 0.000 abstract description 15
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 5
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HCAWPGARWVBULJ-IAGOWNOFSA-N delta8-THC Chemical compound C1C(C)=CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 HCAWPGARWVBULJ-IAGOWNOFSA-N 0.000 abstract 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Pyrane Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP7520787A 1994-02-07 1995-02-06 デキサナビノール誘導体及び同誘導体の神経保護薬剤組成物としての利用 Pending JPH09511493A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/192,886 US5521215A (en)	1989-11-07	1994-02-07	NMDA-blocking pharmaceuticals
US192,886		1994-02-07
PCT/US1995/001470 WO1995020958A1 (en)	1994-02-07	1995-02-06	Dexanabinol derivatives and their use as neuroprotective pharmaceutical compositions

Publications (1)

Publication Number	Publication Date
JPH09511493A true JPH09511493A (ja)	1997-11-18

Family

ID=22711431

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7520787A Pending JPH09511493A (ja)	1994-02-07	1995-02-06	デキサナビノール誘導体及び同誘導体の神経保護薬剤組成物としての利用

Country Status (10)

Country	Link
US (1)	US5521215A (2)
EP (1)	EP0765160B1 (2)
JP (1)	JPH09511493A (2)
AT (1)	ATE237324T1 (2)
AU (1)	AU690221B2 (2)
CA (1)	CA2183466A1 (2)
DE (1)	DE69530389T2 (2)
IL (1)	IL112572A0 (2)
SG (1)	SG49625A1 (2)
WO (1)	WO1995020958A1 (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2004532215A (ja) *	2001-04-06	2004-10-21	ザボードオブトラスティーズオブザユニバーシティオブイリノイ	睡眠時の自律的安定性に関するカンナビノイドの機能的役割

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5455279A (en) *	1991-04-19	1995-10-03	The Children's Medical Center Corporation	Regimen method of mediating neuronal damage using nitroglycerine
US5904144A (en) *	1996-03-22	1999-05-18	Cytotherapeutics, Inc.	Method for treating ophthalmic diseases
US6299895B1 (en)	1997-03-24	2001-10-09	Neurotech S.A.	Device and method for treating ophthalmic diseases
US5824662A (en) *	1996-09-27	1998-10-20	Guilford Pharmaceuticals Inc.	Treatment of global and focal ischemia using naaladase inhibitors
US6017903A (en)	1996-09-27	2000-01-25	Guilford Pharmaceuticals Inc.	Pharmaceutical compositions and methods of treating a glutamate abnormality and effecting a neuronal activity in an animal using NAALADase inhibitors
PL332413A1 (en)	1996-09-27	1999-09-13	Guilford Pharm Inc	Compositions containing inhibitors of naaladase as well as methods of treating glutamatic anomaly and influencing neuronic functions among animals
DE19706903A1 (de) *	1997-02-21	1998-08-27	Bayer Ag	Verwendung von bekannten Agonisten des zentralen Cannabinoid-Rezeptors CB 1
EP1019041A4 (en) *	1997-05-07	2002-04-17	Unimed Pharmaceutical Inc	METHODS TO IMPROVE BEHAVIORAL BEHAVIOR AND RAISE MIND IN PEOPLE
EP0994709A4 (en) *	1997-06-30	2006-02-01	Allergan Inc	CALCIUM BLOCKER FOR THE TREATMENT OF PROLIFERATIVE VITREORETINOPATHY
US20050009884A1 (en) *	1997-06-30	2005-01-13	Dreyer Evan B.	Calcium blockers to treat proliferative retinal diseases
US6110139A (en) *	1997-10-21	2000-08-29	Loubser; Paul Gerhard	Retrograde perfusion monitoring and control system
WO1999025350A1 (en) *	1997-11-14	1999-05-27	Alcon Laboratories, Inc.	Treatment of diabetic retinopathy
GB9807639D0 (en)	1998-04-14	1998-06-10	Kennedy Rheumatology Inst	Anti-inflammatory agents
AU766988B2 (en) *	1998-04-21	2003-10-30	Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The	Cannabinoids as antioxidants and neuroprotectants
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
US7589220B2 (en) *	1998-06-09	2009-09-15	University Of Connecticut	Inhibitors of the anandamide transporter
US7161016B1 (en)	1998-11-24	2007-01-09	University Of Connecticut	Cannabimimetic lipid amides as useful medications
US7276613B1 (en)	1998-11-24	2007-10-02	University Of Connecticut	Retro-anandamides, high affinity and stability cannabinoid receptor ligands
US6943266B1 (en) *	1999-10-18	2005-09-13	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
US6900236B1 (en)	1999-10-18	2005-05-31	University Of Connecticut	Cannabimimetic indole derivatives
DE60033834T2 (de)	1999-10-18	2007-11-15	The University Of Connecticut, Farmington	Für periphäre cannabinoid-rezeptoren selektive liganden
US8084467B2 (en) *	1999-10-18	2011-12-27	University Of Connecticut	Pyrazole derivatives as cannabinoid receptor antagonists
US7119108B1 (en)	1999-10-18	2006-10-10	University Of Connecticut	Pyrazole derivatives as cannabinoid receptor antagonists
US7741365B2 (en) *	1999-10-18	2010-06-22	University Of Connecticut	Peripheral cannabinoid receptor (CB2) selective ligands
EP1299374B1 (en) *	2000-06-22	2006-12-27	Pharmos Corporation	Novel non-psychotropic cannabinoids
US7235584B2 (en) *	2000-06-22	2007-06-26	Pharmos Corporation	Non-psychotropic cannabinoids
EP1785417A3 (en) *	2000-06-22	2007-08-01	Pharmos Corporation	Novel non-psychotropic cannabinoids
US8449908B2 (en) *	2000-12-22	2013-05-28	Alltranz, Llc	Transdermal delivery of cannabidiol
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 (en)	2001-01-29	2002-08-08	University Of Connecticut	Receptor selective cannabimimetic aminoalkylindoles
US7057076B2 (en) *	2001-07-13	2006-06-06	University Of Connecticut	Bicyclic and tricyclic cannabinoids
CA2464333C (en) *	2001-10-26	2011-07-26	University Of Connecticut	Heteroindanes: a new class of potent cannabimimetic ligands
US7029918B2 (en) *	2002-01-25	2006-04-18	Roche Diagnostics Operations, Inc.	Water-soluble derivatives of lipophilic drugs
US7183313B2 (en)	2002-08-23	2007-02-27	University Of Connecticut	Keto cannabinoids with therapeutic indications
US20050192341A1 (en) *	2002-09-05	2005-09-01	Seth Kindler	Non-psychotropic cannabinoids for prevention of cognitive impairment
JP2006502159A (ja) *	2002-09-05	2006-01-19	ファーモスコーポレイション	認知障害を予防するための向精神性のないカンナビノイド
JP2006509038A (ja) *	2002-12-04	2006-03-16	ファーモスコーポレイション	医薬組成物用の高エナンチオマー純度を有するデキサナビノール
US8338648B2 (en) *	2004-06-12	2012-12-25	Signum Biosciences, Inc.	Topical compositions and methods for epithelial-related conditions
CN102766128A (zh) *	2005-09-29	2012-11-07	阿尔巴尼分子研究公司	δ-9-四氢大麻酚的生成方法
DK2176208T3 (en) *	2007-07-30	2015-04-27	Zynerba Pharmaceuticals Inc	Prodrugs of cannabidiol, compositions containing prodrugs of cannabidiol and methods of use thereof
US20090247619A1 (en) *	2008-03-06	2009-10-01	University Of Kentucky	Cannabinoid-Containing Compositions and Methods for Their Use
MA40498A (fr)	2014-09-02	2021-05-19	Texas A & M Univ Sys	Méthode de traitement de l'intoxication par organophosphates
US9585867B2 (en)	2015-08-06	2017-03-07	Charles Everett Ankner	Cannabinod formulation for the sedation of a human or animal
WO2019016814A1 (en)	2017-07-20	2019-01-24	Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd.	PHARMACEUTICAL FILM COMPOSITIONS FOR THE ADMINISTRATION OF LIPOPHILIC COMPOUNDS IN AND / OR THROUGH THE SKIN
WO2019049145A1 (en)	2017-09-11	2019-03-14	Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd.	COMPOSITIONS AND METHODS FOR NASAL BRAIN MEDICATION ADMINISTRATION FOR SYSTEMIC EFFECT
CA3116187A1 (en)	2017-11-29	2019-06-06	Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd.	Cannabinoids compositions and methods
US20220008354A1 (en)	2018-11-04	2022-01-13	Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd.	Orally administrable cannabinoids-containing compositions and methods
US12029718B2 (en)	2021-11-09	2024-07-09	Cct Sciences, Llc	Process for production of essentially pure delta-9-tetrahydrocannabinol

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1464695A (en) *	1974-06-24	1977-02-16	Smithkline Corp	Dibenzo-b,c-pyrans and pharmaceutical compositions thereof
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
US4133819A (en) *	1977-06-17	1979-01-09	Pfizer Inc.	Hexahydro-1-hydroxy-9-hydroxymethyl-3-substituted-6H-dibenzo[b,d]pyrans as analgesic agents
US4209520A (en) *	1977-06-17	1980-06-24	Pfizer Inc.	Hexahydro-1-hydroxy-9-hydroxymethyl-3-substituted-6H-dibenzo[b,d]pyrans as analgesic agents
IL80411A (en) *	1986-10-24	1991-08-16	Raphael Mechoulam	Preparation of dibenzopyranol derivatives and pharmaceutical compositions containing them

1994
- 1994-02-07 US US08/192,886 patent/US5521215A/en not_active Expired - Lifetime
1995
- 1995-02-06 SG SG1996001470A patent/SG49625A1/en unknown
- 1995-02-06 DE DE69530389T patent/DE69530389T2/de not_active Expired - Fee Related
- 1995-02-06 AT AT95909482T patent/ATE237324T1/de not_active IP Right Cessation
- 1995-02-06 AU AU17433/95A patent/AU690221B2/en not_active Ceased
- 1995-02-06 JP JP7520787A patent/JPH09511493A/ja active Pending
- 1995-02-06 EP EP95909482A patent/EP0765160B1/en not_active Expired - Lifetime
- 1995-02-06 CA CA002183466A patent/CA2183466A1/en not_active Abandoned
- 1995-02-06 WO PCT/US1995/001470 patent/WO1995020958A1/en not_active Ceased
- 1995-02-07 IL IL11257295A patent/IL112572A0/xx active IP Right Grant

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2004532215A (ja) *	2001-04-06	2004-10-21	ザボードオブトラスティーズオブザユニバーシティオブイリノイ	睡眠時の自律的安定性に関するカンナビノイドの機能的役割

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Publication number	Publication date
EP0765160A1 (en)	1997-04-02
US5521215A (en)	1996-05-28
IL112572A0 (en)	1995-05-26
DE69530389D1 (de)	2003-05-22
EP0765160B1 (en)	2003-04-16
AU1743395A (en)	1995-08-21
EP0765160A4 (2)	1997-04-09
CA2183466A1 (en)	1995-08-10
WO1995020958A1 (en)	1995-08-10
SG49625A1 (en)	1998-06-15
AU690221B2 (en)	1998-04-23
DE69530389T2 (de)	2004-03-25
ATE237324T1 (de)	2003-05-15

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JPH09511493A - デキサナビノール誘導体及び同誘導体の神経保護薬剤組成物としての利用 - Google Patents

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