CA2774868C - Novel arylated camphenes, processes for their preparation and uses thereof - Google Patents

Novel arylated camphenes, processes for their preparation and uses thereof Download PDF

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Publication number
CA2774868C
CA2774868C CA2774868A CA2774868A CA2774868C CA 2774868 C CA2774868 C CA 2774868C CA 2774868 A CA2774868 A CA 2774868A CA 2774868 A CA2774868 A CA 2774868A CA 2774868 C CA2774868 C CA 2774868C
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Prior art keywords
dimethoxy
branched
straight
compound according
hept
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Expired - Fee Related
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CA2774868A
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English (en)
French (fr)
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CA2774868A1 (en
Inventor
Raphael Mechoulam
Lital Magid
Esther Shohami
Itai Bab
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Yissum Research Development Co of Hebrew University of Jerusalem
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Yissum Research Development Co of Hebrew University of Jerusalem
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    • 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
    • C07D311/94—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 condensed with rings other than six-membered or with ring systems containing such rings
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • 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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A—HUMAN NECESSITIES
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    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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    • 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
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    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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    • 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
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • 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
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

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  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Diabetes (AREA)
  • Rheumatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Epidemiology (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Obesity (AREA)
  • Immunology (AREA)
  • Otolaryngology (AREA)
  • Nutrition Science (AREA)
  • Pulmonology (AREA)
  • Psychiatry (AREA)
  • Ophthalmology & Optometry (AREA)
  • Reproductive Health (AREA)
  • Emergency Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
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CA2774868A 2009-11-19 2010-11-18 Novel arylated camphenes, processes for their preparation and uses thereof Expired - Fee Related CA2774868C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US26267709P 2009-11-19 2009-11-19
US61/262,677 2009-11-19
PCT/IL2010/000970 WO2011061744A2 (en) 2009-11-19 2010-11-18 Novel arylated camphenes, processes for their preparation and uses thereof

Publications (2)

Publication Number Publication Date
CA2774868A1 CA2774868A1 (en) 2011-05-26
CA2774868C true CA2774868C (en) 2018-09-04

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ID=43875675

Family Applications (1)

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CA2774868A Expired - Fee Related CA2774868C (en) 2009-11-19 2010-11-18 Novel arylated camphenes, processes for their preparation and uses thereof

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US (2) US8722938B2 (enExample)
EP (1) EP2501669B1 (enExample)
JP (1) JP5960058B2 (enExample)
KR (1) KR20120091196A (enExample)
CN (1) CN102648174B (enExample)
AU (1) AU2010320467B2 (enExample)
BR (1) BR112012010518A2 (enExample)
CA (1) CA2774868C (enExample)
CL (1) CL2012001290A1 (enExample)
CO (1) CO6481008A2 (enExample)
CR (1) CR20120247A (enExample)
EC (1) ECSP12011864A (enExample)
ES (1) ES2665519T3 (enExample)
IL (1) IL218216A (enExample)
MA (1) MA33753B1 (enExample)
MX (2) MX355972B (enExample)
MY (1) MY184647A (enExample)
NZ (1) NZ599106A (enExample)
PE (1) PE20121187A1 (enExample)
PH (1) PH12012500897A1 (enExample)
RU (1) RU2578715C2 (enExample)
SG (2) SG10201407706VA (enExample)
UA (1) UA109414C2 (enExample)
WO (1) WO2011061744A2 (enExample)
ZA (1) ZA201200752B (enExample)

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RU2578715C2 (ru) * 2009-11-19 2016-03-27 Йиссум Рисерч Дивелопмент Компани Оф Дзе Хебрю Юниверсити Оф Иерусалим, Лтд. Новые арилированные камфены, способы их получения и их применения
KR20170072876A (ko) 2014-10-27 2017-06-27 에프. 호프만-라 로슈 아게 방사성 표지된 카나비노이드 수용체 2 리간드
US9585867B2 (en) 2015-08-06 2017-03-07 Charles Everett Ankner Cannabinod formulation for the sedation of a human or animal
US20170038184A1 (en) 2015-08-06 2017-02-09 Charles E. Ankner Formulation delivery system
MX2018004632A (es) * 2015-10-16 2018-11-09 Scythian Biosciences Inc Metodos y composiciones para el tratamiento de una lesion cerebral traumatica.
EP3538507A1 (en) 2016-11-13 2019-09-18 Yissum Research and Development Company of the Hebrew University of Jerusalem Ltd. Process for the preparation of hu-910 and crystalline structure thereof
RU2651754C1 (ru) * 2016-11-25 2018-04-23 Федеральное государственное бюджетное учреждение науки Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) ПРИМЕНЕНИЕ АЛИФАТИЧЕСКИХ ИМИНОПРОИЗВОДНЫХ КАМФОРЫ В КАЧЕСТВЕ ЭФФЕКТИВНЫХ ИНГИБИТОРОВ РЕПРОДУКЦИИ ВИРУСА ГРИППА штамм A/California/07/09 (H1N1) pdm09 и A/Puerto Rico/8/34 (H1N1)
KR102063962B1 (ko) * 2017-10-25 2020-01-08 대구대학교 산학협력단 캄펜을 유효성분으로 함유하는 골다공증의 예방 또는 치료용 약학적 조성물
EP3840854A4 (en) * 2018-08-20 2022-06-29 Bessor Pharma, LLC Novel cannabinoids and cannabinoid acids and their derivatives
US20250002435A1 (en) * 2021-10-10 2025-01-02 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Arylated fenchone derivatives, compositions comprising them, processes for their preparation and uses thereof

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CN102648174A (zh) 2012-08-22
US20120245366A1 (en) 2012-09-27
KR20120091196A (ko) 2012-08-17
IL218216A (en) 2015-05-31
UA109414C2 (uk) 2015-08-25
SG179203A1 (en) 2012-04-27
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EP2501669B1 (en) 2018-01-24
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RU2578715C2 (ru) 2016-03-27
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