FR2370742A1 - Preparation stereoselective d'hexahydro-dibenzopyranones et intermediaires appropries - Google Patents
Preparation stereoselective d'hexahydro-dibenzopyranones et intermediaires appropriesInfo
- 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
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.
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)
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)
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)
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 |
-
1976
- 1976-11-10 US US05/740,502 patent/US4102902A/en not_active Expired - Lifetime
-
1977
- 1977-06-29 GB GB27138/77A patent/GB1584181A/en not_active Expired
- 1977-06-29 GB GB1144/80A patent/GB1584182A/en not_active Expired
- 1977-06-30 NZ NZ184526A patent/NZ184526A/xx unknown
- 1977-06-30 CA CA281,784A patent/CA1101875A/fr not_active Expired
- 1977-06-30 PH PH19935A patent/PH13827A/en unknown
- 1977-06-30 IL IL52427A patent/IL52427A/xx unknown
- 1977-06-30 SE SE7707633A patent/SE428020B/xx not_active IP Right Cessation
- 1977-06-30 ZA ZA00773960A patent/ZA773960B/xx unknown
- 1977-06-30 PT PT66746A patent/PT66746B/pt unknown
- 1977-07-01 YU YU01636/77A patent/YU163677A/xx unknown
- 1977-07-01 BG BG7737819A patent/BG28411A4/xx unknown
- 1977-07-01 BG BG7736778A patent/BG28061A3/xx unknown
- 1977-07-01 DE DE2729859A patent/DE2729859C2/de not_active Expired
- 1977-07-01 DE DE2760005A patent/DE2760005C2/de not_active Expired
- 1977-07-01 AU AU26684/77A patent/AU509355B2/en not_active Expired
- 1977-07-01 DE DE2760006A patent/DE2760006C2/de not_active Expired
- 1977-07-04 SU SU772497362A patent/SU786898A3/ru active
- 1977-07-04 PL PL1977199362A patent/PL104356B1/pl unknown
- 1977-07-04 ES ES460387A patent/ES460387A1/es not_active Expired
- 1977-07-04 PL PL1977206420A patent/PL104432B1/pl unknown
- 1977-07-04 MX MX775872U patent/MX5172E/es unknown
- 1977-07-04 CH CH819477A patent/CH632506A5/de not_active IP Right Cessation
- 1977-07-04 JP JP52081489A patent/JPS5925792B2/ja not_active Expired
- 1977-07-04 ES ES460388A patent/ES460388A1/es not_active Expired
- 1977-07-04 BE BE1008247A patent/BE856413A/fr not_active IP Right Cessation
- 1977-07-04 ES ES460389A patent/ES460389A1/es not_active Expired
- 1977-07-05 HU HU77EI755A patent/HU177308B/hu unknown
- 1977-07-05 NL NL7707467A patent/NL7707467A/xx not_active Application Discontinuation
- 1977-07-05 DD DD77208796A patent/DD140455A5/de unknown
- 1977-07-05 GR GR53879A patent/GR66417B/el unknown
- 1977-07-05 IE IE1389/77A patent/IE45247B1/en unknown
- 1977-07-05 DK DK301477A patent/DK301477A/da not_active Application Discontinuation
- 1977-07-05 FR FR7720645A patent/FR2370742A1/fr active Granted
- 1977-07-05 DD DD77199899A patent/DD134350A5/xx unknown
- 1977-07-05 HU HU81113A patent/HU183286B/hu unknown
- 1977-07-05 RO RO7798966A patent/RO78780A/fr unknown
- 1977-07-06 AT AT483677A patent/AT356103B/de not_active IP Right Cessation
- 1977-07-06 CS CS774518A patent/CS196376B2/cs unknown
- 1977-10-28 PH PH20381A patent/PH13890A/en unknown
- 1977-10-28 PH PH20382A patent/PH14708A/en unknown
-
1978
- 1978-07-06 SU SU782633652A patent/SU1128829A3/ru active
-
1980
- 1980-07-15 IL IL60590A patent/IL60590A0/xx unknown
- 1980-07-15 IL IL60589A patent/IL60589A0/xx unknown
- 1980-07-22 SE SE8005314A patent/SE8005314L/sv not_active Application Discontinuation
- 1980-07-22 SE SE8005316A patent/SE434510B/sv unknown
-
1982
- 1982-02-05 CH CH71882A patent/CH632481A5/de not_active IP Right Cessation
- 1982-04-16 JP JP57064621A patent/JPS5912654B2/ja not_active Expired
Cited By (1)
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 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |