GB1464695A - Dibenzo-b,c-pyrans and pharmaceutical compositions thereof - Google Patents

Dibenzo-b,c-pyrans and pharmaceutical compositions thereof

Info

Publication number
GB1464695A
GB1464695A GB2606775A GB2606775A GB1464695A GB 1464695 A GB1464695 A GB 1464695A GB 2606775 A GB2606775 A GB 2606775A GB 2606775 A GB2606775 A GB 2606775A GB 1464695 A GB1464695 A GB 1464695A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
methyl
ring
alkyl
ethyl
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.)
Expired
Application number
GB2606775A
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.)
GlaxoSmithKline LLC
Original Assignee
SmithKline Corp
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 SmithKline Corp filed Critical SmithKline Corp
Publication of GB1464695A publication Critical patent/GB1464695A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
    • C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1464695 Dibenzo[b,d]pyrans and pharmaceutical compositions thereof SMITHKLINE CORP 19 June 1975 [24 June 1974] 26067/75 Heading C2C Novel compounds of the Formula I wherein ring A is a benzene ring, a cyclohexane ring or a cyclohexene ring with the double bond at position 6a-10a; R 1 is hydrogen, methyl or ethyl; R 2 is hydrogen or C 2-5 alkanoyl; R 3 is hydrogen, methyl or ethyl and R 4 and R 5 are hydrogen or methyl, at least one of R 3 , R 4 and R 5 being other than hydrogen; R 6 is C 4-3 alkyl and R 7 is hydrogen, methyl or ethyl, may be prepared (1) when A is a cyclohexene ring R 2 is hydrogen and R 7 is methyl or ethyl, by acid condensation of 2-acetyl or propionylcyclohexanone with a 5-alkyl resorcinol followed by reduction and acetylation to yield a compound I in which R 2 is acetyl optionally followed by hydrolysis to H at R 2 , (2) when A is a cyclohexene, R 2 is hydrogen and R 7 is hydrogen, by reduction of the corresponding pyrone and cyclizing the resulting 3<SP>1</SP>,4<SP>1</SP>,5<SP>1</SP>,6<SP>1</SP>-tetrahydro-2,6- dihydroxy - 2<SP>1 </SP>- hydroxymethyl - biphenyl; (3) when A is a benzene ring and R 2 is hydrogen by dehydrogenation of the corresponding cyclohexene ring; (4) when A is a benzene ring R 2 is hydrogen and R 7 is methyl or ethyl, heating the condensation product of 2-acetyl or propionyl cyclohexanone with a 5-alkyl resorcinol; (5) when A is cyclohexane and R 2 is hydrogen, reduction of the corresponding compound where A is cyclohexene; (6) when R 2 is alkanoyl esterifying the corresponding compound where R 2 is hydrogen. Various 5-alkyl resorcinols are prepared by reacting a 3,5-dimethoxyphenylketone or 3,5- dimethoxybenzaldehyde with an alkyl magnesium halide dehydrating the carbinol formed to yield a 5-alkenyl resorcinol dimethyl ether or a mixture of two such compounds, saturating the double bond to yield a 5-alkyl resorcinol dimethyl ether and demethylating the ether groups. 3 - (1,2 - Dimethyl - decyl) - 1 - hydroxy- 7,8,9,10 - tetrahydro - 9 - methyl - 6H - dibenzo- [b,d]pyrone is prepared by reacting 5-(1,2- dimethyldecyl) resorcinol and 5-methyl-2-carbethoxycyclohexanone in the presence of phosphorus oxychloride. 2 - Acetyl - 5 - ethylcyclohexanone is prepared by reacting 3-ethylcyclohexanone and acetylchloride in the presence of base. Pharmaceutical compositions of the compounds I with the usual excipients show depressant, sedative and tranquilizing activity and also analgesic, gastric acid secretion inhibitory and anti-inflammatory activity when administered internally.
GB2606775A 1974-06-24 1975-06-19 Dibenzo-b,c-pyrans and pharmaceutical compositions thereof Expired GB1464695A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US48253174A 1974-06-24 1974-06-24

Publications (1)

Publication Number Publication Date
GB1464695A true GB1464695A (en) 1977-02-16

Family

ID=23916449

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2606775A Expired GB1464695A (en) 1974-06-24 1975-06-19 Dibenzo-b,c-pyrans and pharmaceutical compositions thereof

Country Status (1)

Country Link
GB (1) GB1464695A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0048572A2 (en) * 1980-09-19 1982-03-31 Pfizer Inc. Substituted 2-hydroxyphenyl cycloalkanes and pharmaceutical compositions thereof
DE3141387A1 (en) * 1980-10-20 1982-08-12 Farmitalia Carlo Erba S.p.A., 20159 Milano 6-SUBSTITUTED 6H-DIBENZO (B, D) PYRANE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THE SAME
EP0765160A1 (en) * 1994-02-07 1997-04-02 RAMOT UNIVERSITY, AUTHORITY FOR APPLIED RESEARCH &amp; INDUSTRIAL DEVELOPMENT LTD. Dexanabinol derivatives and their use as neuroprotective pharmaceutical compositions

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0048572A2 (en) * 1980-09-19 1982-03-31 Pfizer Inc. Substituted 2-hydroxyphenyl cycloalkanes and pharmaceutical compositions thereof
EP0048572A3 (en) * 1980-09-19 1982-12-08 Pfizer Inc. Substituted 2-hydroxyphenyl cycloalkanes and pharmaceutical compositions thereof
DE3141387A1 (en) * 1980-10-20 1982-08-12 Farmitalia Carlo Erba S.p.A., 20159 Milano 6-SUBSTITUTED 6H-DIBENZO (B, D) PYRANE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THE SAME
EP0765160A1 (en) * 1994-02-07 1997-04-02 RAMOT UNIVERSITY, AUTHORITY FOR APPLIED RESEARCH &amp; INDUSTRIAL DEVELOPMENT LTD. Dexanabinol derivatives and their use as neuroprotective pharmaceutical compositions
EP0765160A4 (en) * 1994-02-07 1997-04-09

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee