FR2370742A1 - Preparation stereoselective d'hexahydro-dibenzopyranones et intermediaires appropries - Google Patents

Preparation stereoselective d'hexahydro-dibenzopyranones et intermediaires appropries

Info

Publication number
FR2370742A1
FR2370742A1 FR7720645A FR7720645A FR2370742A1 FR 2370742 A1 FR2370742 A1 FR 2370742A1 FR 7720645 A FR7720645 A FR 7720645A FR 7720645 A FR7720645 A FR 7720645A FR 2370742 A1 FR2370742 A1 FR 2370742A1
Authority
FR
France
Prior art keywords
dimethyl
hexahydro
substituted
optically active
dibenzopyranones
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.)
Granted
Application number
FR7720645A
Other languages
English (en)
Other versions
FR2370742B1 (fr
Inventor
Robert Allen Archer
William Allen Day
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of FR2370742A1 publication Critical patent/FR2370742A1/fr
Application granted granted Critical
Publication of FR2370742B1 publication Critical patent/FR2370742B1/fr
Granted legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrane Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Saccharide Compounds (AREA)

Abstract

L'invention concerne la préparation stéréosélective d'hexahydrodibenzopyranones, et les intermédiaires appropriés. On fait réagir une 4-(2,6-dihydroxyphényl 4-substitué)-6,6-diméthyl-2-norpinanone optiquement active avec un acide protonique pour former un isomère optique d'une cis-1-hydroxy-6,6-diméthyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzoØb,dõpyran-9-one substituée en position 3. La réaction de ladite norpinanone avec un acide de Lewis donne un isomère optique de la trans-1-hydroxy-6,6-diméthyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzoØb.dõpyran-9-one substituée en position 3. On prépare les norpinanones de départ par réaction résorcinol substitué en position 5 avec un 6,6-diméthyl-2,4-diacétoxy-2-norpinène ou un 6,6-diméthyl-2,2-diacétoxy-2-norpinène optiquement actifs que l'on obtient à partir de beta -pinènes optiquement actifs. Les produits finals obtenus sont actifs sur le plan pharmacologique.
FR7720645A 1976-11-10 1977-07-05 Preparation stereoselective d'hexahydro-dibenzopyranones et intermediaires appropries Granted FR2370742A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/740,502 US4102902A (en) 1976-11-10 1976-11-10 Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor

Publications (2)

Publication Number Publication Date
FR2370742A1 true FR2370742A1 (fr) 1978-06-09
FR2370742B1 FR2370742B1 (fr) 1980-12-26

Family

ID=24976773

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7720645A Granted FR2370742A1 (fr) 1976-11-10 1977-07-05 Preparation stereoselective d'hexahydro-dibenzopyranones et intermediaires appropries

Country Status (30)

Country Link
US (1) US4102902A (fr)
JP (2) JPS5925792B2 (fr)
AT (1) AT356103B (fr)
AU (1) AU509355B2 (fr)
BE (1) BE856413A (fr)
BG (2) BG28411A4 (fr)
CA (1) CA1101875A (fr)
CH (2) CH632506A5 (fr)
CS (1) CS196376B2 (fr)
DD (2) DD140455A5 (fr)
DE (3) DE2729859C2 (fr)
DK (1) DK301477A (fr)
ES (3) ES460387A1 (fr)
FR (1) FR2370742A1 (fr)
GB (2) GB1584181A (fr)
GR (1) GR66417B (fr)
HU (2) HU177308B (fr)
IE (1) IE45247B1 (fr)
IL (3) IL52427A (fr)
MX (1) MX5172E (fr)
NL (1) NL7707467A (fr)
NZ (1) NZ184526A (fr)
PH (3) PH13827A (fr)
PL (2) PL104356B1 (fr)
PT (1) PT66746B (fr)
RO (1) RO78780A (fr)
SE (3) SE428020B (fr)
SU (2) SU786898A3 (fr)
YU (1) YU163677A (fr)
ZA (1) ZA773960B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2432498A1 (fr) * 1978-08-02 1980-02-29 Yissum Res Dev Co Nouveaux derives du pinene et leur preparation

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63501288A (ja) * 1985-09-20 1988-05-19 ジ・アップジョン・カンパニ− １，４−ナフタレンジオ−ルおよび１，４−ヒドロキノン誘導体
US4939169A (en) * 1985-09-20 1990-07-03 The Upjohn Company 1,4-naphthalenediol and 1,4-hydroquinone derivatives
IL80411A (en) * 1986-10-24 1991-08-16 Raphael Mechoulam Preparation of dibenzopyranol derivatives and pharmaceutical compositions containing them
JPH0315035A (ja) * 1989-03-03 1991-01-23 Konica Corp カメラ
JP2577671B2 (ja) * 1990-06-11 1997-02-05 高砂熱学工業株式会社 気化式精密加湿装置
CA2340445A1 (fr) * 1998-05-04 1999-11-11 The University Of Connecticut Nouveaux cannabinoides analgesiques et immunomodulateurs
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
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
US8084467B2 (en) * 1999-10-18 2011-12-27 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
EP1224155B1 (fr) * 1999-10-18 2007-02-21 The University Of Connecticut Nouveaux agonistes de cannabinoides bicycliques destines au recepteur de cannabinoides
US6943266B1 (en) * 1999-10-18 2005-09-13 University Of Connecticut Bicyclic cannabinoid agonists for the cannabinoid receptor
DE60033834T2 (de) 1999-10-18 2007-11-15 The University Of Connecticut, Farmington Für periphäre cannabinoid-rezeptoren selektive liganden
US7393842B2 (en) * 2001-08-31 2008-07-01 University Of Connecticut Pyrazole analogs acting on cannabinoid receptors
CA2435409A1 (fr) * 2001-01-26 2002-08-01 University Of Connecticut Nouveaux ligands cannabimimetiques
EP1363632B1 (fr) 2001-01-29 2010-08-25 The University of Connecticut Aminoalkylindoles cannabimimetiques selectifs d'un recepteur
JP4312594B2 (ja) * 2001-07-13 2009-08-12 ユニバーシティ オブ コネチカット 新規な二環式及び三環式カンナビノイド
WO2003035005A2 (fr) * 2001-10-26 2003-05-01 University Of Connecticut Heteroindanes: nouvelle classe de ligands cannabimimetiques efficaces
WO2003091189A1 (fr) * 2002-04-25 2003-11-06 Virginia Commonwealth University Cannabinoides
EP1545502A4 (fr) 2002-08-23 2008-12-24 Univ Connecticut Ceto-cannabinoides possedant des indications therapeutiques
ZA200802767B (en) * 2005-09-29 2009-09-30 Amr Technology Inc Process for production of delta-9-tetrahydrocannabinol
US9763894B2 (en) * 2006-12-05 2017-09-19 Virginia Commonwealth University Inflammation therapy
PL222532B1 (pl) 2012-04-05 2016-08-31 Akademia Morska W Szczecinie Sposób i układ do diagnozowania układu wtryskowego silników o zapłonie samoczynnym, zwłaszcza silników okrętowych
US12029718B2 (en) 2021-11-09 2024-07-09 Cct Sciences, Llc Process for production of essentially pure delta-9-tetrahydrocannabinol

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3856820A (en) * 1973-07-18 1974-12-24 Smithkline Corp 2-AMINOMETHYL DIBENZO (b,d) PYRANS
US3856821A (en) * 1973-07-18 1974-12-24 Smithkline Corp ALKOXY DIBENZO (b,d) PYRANS
US3856822A (en) * 1973-07-18 1974-12-24 Smithkline Corp 3-alkenyl dibenzo (b,d)pyrans
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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2432498A1 (fr) * 1978-08-02 1980-02-29 Yissum Res Dev Co Nouveaux derives du pinene et leur preparation

Also Published As

Publication number Publication date
IL52427A0 (en) 1977-08-31
DE2729859C2 (de) 1984-08-23
RO78780A (fr) 1982-04-12
ES460388A1 (es) 1978-04-01
PH14708A (en) 1981-11-13
PL199362A1 (pl) 1978-05-22
IL60590A0 (en) 1980-09-16
NZ184526A (en) 1979-03-16
PT66746A (en) 1977-07-01
DE2729859A1 (de) 1978-05-11
IL52427A (en) 1981-10-30
CH632506A5 (de) 1982-10-15
GB1584181A (en) 1981-02-11
HU177308B (en) 1981-09-28
SE8005316L (sv) 1980-07-22
IE45247L (en) 1978-05-10
CA1101875A (fr) 1981-05-26
PL104356B1 (pl) 1979-08-31
BG28411A4 (en) 1980-04-15
ZA773960B (en) 1979-02-28
SE428020B (sv) 1983-05-30
US4102902A (en) 1978-07-25
ES460387A1 (es) 1978-04-01
DK301477A (da) 1978-05-11
IL60589A0 (en) 1980-09-16
JPS5912654B2 (ja) 1984-03-24
PL104432B1 (pl) 1979-08-31
BE856413A (fr) 1978-01-04
PH13890A (en) 1980-10-27
JPS5925792B2 (ja) 1984-06-21
SU786898A3 (ru) 1980-12-07
JPS5359670A (en) 1978-05-29
IE45247B1 (en) 1982-07-14
SU1128829A3 (ru) 1984-12-07
PT66746B (en) 1978-11-27
ES460389A1 (es) 1978-04-16
JPS5865244A (ja) 1983-04-18
DD140455A5 (de) 1980-03-05
CS196376B2 (en) 1980-03-31
PH13827A (en) 1980-10-07
YU163677A (en) 1982-10-31
SE7707633L (sv) 1978-05-11
MX5172E (es) 1983-04-18
GR66417B (fr) 1981-03-20
AT356103B (de) 1980-04-10
SE8005314L (sv) 1980-07-22
HU183286B (en) 1984-04-28
DE2760005C2 (de) 1984-04-26
ATA483677A (de) 1979-09-15
BG28061A3 (en) 1980-02-25
GB1584182A (en) 1981-02-11
DD134350A5 (de) 1979-02-21
AU509355B2 (en) 1980-05-08
AU2668477A (en) 1979-01-04
CH632481A5 (de) 1982-10-15
NL7707467A (nl) 1978-05-12
FR2370742B1 (fr) 1980-12-26
SE434510B (sv) 1984-07-30
DE2760006C2 (de) 1985-07-04

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