GB1205719A - Pharmaceutically active derivatives of 4-phenylbicyclo[2.2.2]octane and oct-2-enecarbinols and carboxaldehydes - Google Patents

Pharmaceutically active derivatives of 4-phenylbicyclo[2.2.2]octane and oct-2-enecarbinols and carboxaldehydes

Info

Publication number
GB1205719A
GB1205719A GB58118/68A GB5811868A GB1205719A GB 1205719 A GB1205719 A GB 1205719A GB 58118/68 A GB58118/68 A GB 58118/68A GB 5811868 A GB5811868 A GB 5811868A GB 1205719 A GB1205719 A GB 1205719A
Authority
GB
United Kingdom
Prior art keywords
oct
group
octane
ene
phenyl
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
GB58118/68A
Inventor
Paul Edward Aldrich
Edward Charles Hermann
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours 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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1205719A publication Critical patent/GB1205719A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
    • C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/34—Monohydroxylic alcohols containing six-membered aromatic rings and other 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
    • C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
    • 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
    • C07C45/71—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 being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/46—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/47—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/44—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing eight carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,205,719. 4 - Phenyl - bicyclo [2.2.2] octane and oct-2-ene-1-carbinol and -carboxaldehyde derivatives. E.I. DU PONT DE NEMOURS & CO. 6 Dec., 1968 [8 Dec., 1967], No. 58118/68. Heading C2C. Novel 4 - phenyl - bicyclo [2.2.2] octane and oct-2-ene-1-carbinol and -carboxaldehyde derivatives of the general formula wherein A is a single or double bond; R 1 is a hydrogen atom or a hydroxyl, methoxy, ethoxy, propoxy or butoxy group or a group of the formula RCOO-, in which R is a C 1-12 alkyl group; and R 2 is a -CHO or -CH 2 OR 3 group, in which R 3 is a hydrogen atom or a monoacyl group derived from a pharmaceutically acceptable mono- or di-basic carboxylic acid, are prepared (a) when R 2 is a -CH 2 OH group, by reduction of a 4-phenyl-bicyclo [2.2.2] octane or oct-2-ene-1-carboxylic acid derivative of the general formula above, wherein R 2 is a -COOH or -COO alkyl group; or (b) when R 2 is a - CHO group, by treatment of a 4-phenylbicyclo [2.2.2] octane or oct-2-ene-1-carboxylic acid of the general formula above, wherein R 2 is a -COOH group with either (i) lithium metal in methylamine, followed by slowly adding ethyl alcohol and evaporating the liquid, dissolving the residue in water, and followed by acidification to precipitate out the desired carboxaldehyde, or (ii) phosphorus pentachloride, phosphoryl chloride or thionyl chloride and converting the acid chloride so obtained to the corresponding carboxaldehyde by either hydrogenating it with a catalyst, such as palladiumon-barium sulphate, in the presence of a regulator, such as quinoline-sulphur, or treating it with a mercaptan in pyridine to give a thiol ester and reducing the thiol ester in the presence of deactivated Raney nickel. 4 - Phenylbicyclo [2.2.2] oct-2-ene-1-carboxylic acid ethyl ester is prepared by reaction of acetophenone with diethylethoxymethylene malonate in ethanol in the presence of sodium ethoxide under a nitrogen atmosphere, followed by reaction of the resulting intermediate with anhydrous hydrogen fluoride and reaction of the obtained 3-carbethoxy-6-phenyl-2H-pyran-2- one with ethylene under pressure and with heating. Pharmaceutical compositions effective for preventing pregnancy in animals comprise, as active ingredient, a 4-phenyl-bicyclo [2.2.2] octane or oct-2-ene-1-carbinol of the general formula above, together with a pharmaceutically acceptable diluent or carrier, and may be administered orally, rectally or parenterally.
GB58118/68A 1967-12-08 1968-12-06 Pharmaceutically active derivatives of 4-phenylbicyclo[2.2.2]octane and oct-2-enecarbinols and carboxaldehydes Expired GB1205719A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US68898967A 1967-12-08 1967-12-08

Publications (1)

Publication Number Publication Date
GB1205719A true GB1205719A (en) 1970-09-16

Family

ID=24766619

Family Applications (1)

Application Number Title Priority Date Filing Date
GB58118/68A Expired GB1205719A (en) 1967-12-08 1968-12-06 Pharmaceutically active derivatives of 4-phenylbicyclo[2.2.2]octane and oct-2-enecarbinols and carboxaldehydes

Country Status (7)

Country Link
US (1) US3564060A (en)
BE (1) BE725074A (en)
DE (1) DE1812906A1 (en)
FR (1) FR1597754A (en)
GB (1) GB1205719A (en)
IL (1) IL31091A0 (en)
NL (1) NL6817514A (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2658881B1 (en) * 1990-02-27 1992-04-30 Valeo SUPPORT ASSEMBLY OF A CLUTCH MECHANISM, PARTICULARLY FOR A MOTOR VEHICLE.
DE19510349C2 (en) * 1995-03-22 1997-03-20 Gloeckler Dichtsysteme Guenter Fastener
DE19534034A1 (en) * 1995-09-14 1997-03-20 Mann & Hummel Filter Fastener device for components in motor industry
DE19546072C2 (en) * 1995-12-09 1998-04-09 Gloeckler Dichtsysteme Guenter Fastener
US6044536A (en) * 1995-12-23 2000-04-04 Richard Bergner Gmbh & Co. Method for making an assembly unit
DE19924502C2 (en) * 1999-05-28 2003-08-07 Elringklinger Ag Screw with sleeve
DE10215883B4 (en) 2002-04-11 2005-09-08 Kamax-Werke Rudolf Kellermann Gmbh & Co. Kg Connecting element with a screw and a captive arranged support element
EP3071541B1 (en) * 2013-11-21 2023-06-07 Marquette University Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform
WO2018183800A1 (en) * 2017-03-30 2018-10-04 Marquette University Substituted (4'-hydroxyphenyl)cycloalkane and (4'-hydroxyphenyl)cycloalkene compounds and uses thereof as selective agonists of the estrogen receptor beta isoform for enhanced memory consolidation

Also Published As

Publication number Publication date
IL31091A0 (en) 1969-01-29
US3564060A (en) 1971-02-16
DE1812906A1 (en) 1969-07-03
BE725074A (en) 1969-06-06
FR1597754A (en) 1970-06-29
NL6817514A (en) 1969-06-10

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees