GB1280767A - Derivatives of 1,2-diphenyl-ethane - Google Patents

Derivatives of 1,2-diphenyl-ethane

Info

Publication number
GB1280767A
GB1280767A GB02554/70A GB1255470A GB1280767A GB 1280767 A GB1280767 A GB 1280767A GB 02554/70 A GB02554/70 A GB 02554/70A GB 1255470 A GB1255470 A GB 1255470A GB 1280767 A GB1280767 A GB 1280767A
Authority
GB
United Kingdom
Prior art keywords
general formula
alkyl group
hydrogen atom
reaction
formula above
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
GB02554/70A
Inventor
John Cameron Turner
Rosalind Po Kuen Chan
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.)
BIOREK LAB Ltd
Original Assignee
BIOREK LAB Ltd
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 BIOREK LAB Ltd filed Critical BIOREK LAB Ltd
Priority to GB02554/70A priority Critical patent/GB1280767A/en
Priority to NO504/71A priority patent/NO132533C/no
Priority to IE175/71A priority patent/IE35009B1/en
Priority to ZA710927A priority patent/ZA71927B/en
Priority to SE7101951A priority patent/SE393369B/en
Priority to CA105,562A priority patent/CA948215A/en
Priority to IL36225A priority patent/IL36225A0/en
Priority to YU531/71A priority patent/YU35331B/en
Priority to DE19712110428 priority patent/DE2110428C3/en
Priority to FI657/71A priority patent/FI55170C/en
Priority to CH332071A priority patent/CH558315A/en
Priority to FR7108077A priority patent/FR2085710B1/fr
Priority to BE764081A priority patent/BE764081A/en
Priority to NL717103249A priority patent/NL146140B/en
Priority to AT209771A priority patent/AT303711B/en
Priority to PH12292A priority patent/PH10518A/en
Priority to JP46014646A priority patent/JPS515378B1/ja
Priority to ES389282A priority patent/ES389282A1/en
Priority to DK126571A priority patent/DK146015C/en
Publication of GB1280767A publication Critical patent/GB1280767A/en
Priority to US05/563,119 priority patent/US4051263A/en
Expired 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
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • 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
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07C39/24—Halogenated derivatives
    • C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
    • 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
    • C07C45/46—Friedel-Crafts reactions

Landscapes

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

Abstract

1280767 3,3<SP>1</SP> - Dihalo - 4,4<SP>1</SP> - dihydroxydibenzyls BIOREX LABORATORIES Ltd 19 April 1971 [16 March 1970] 12554/70 Heading C2C Novel 3,31 - dihalo - 4,4<SP>1</SP> - dihydroxydibenzyls of the general formula wherein R is a hydrogen atom or a C 1-6 alkyl or benzyl group, R 1 and R 2 are each a C 1-6 alkyl group, with the proviso that they are not both a methyl or ethyl group, and X is a halogen atom, are prepared (a) when R is a C 1-6 alkyl group, by hydrogenation of a diphenylethylene of the general formula wherein R<SP>11</SP> is a C 1-6 alkyl group; (b) when R is a hydrogen atom, by dealkylation of the corresponding compound in which R is an alkyl group; (c) when R is a C 1-6 alkyl group, by reaction of an ether of the general formula with a haloethanol of the general formula Hal-CH(R 1 )-CH(OH)R 2 , wherein Hal is a halogen atom; (d) when X is a chlorine or bromine atom and R is a hydrogen or C 1-6 alkyl group, by treatment of the corresponding compound in which X is a hydrogen atom with bromine, chlorine or sulphuryl chloride, as appropriate; (e) when R is a C 1-6 alkyl group, by reaction of a Grignard reagent and a benzyl halide of the resepctive general formulµ wherein R 3 is a C 3-6 alkyl group; (f) when R is a C 1-6 alkyl or benzyl group, by reaction of the corresponding compound in which R is a hydrogen atom with a C 1-6 alkyl or benzyl halide in the presence of an alkali metal hydroxide and an inert solvent; and (g) when R is a hydrogen atom, by hydrogenolysis of the corresponding compound in which R is a benzyl group. Diphenyl ethylenes of the second general formula above are prepared by reaction of an ether of the third general formula above with a ketone of the general formula 4,4<SP>1</SP>-Dihydroxydibenzyls of the first general formula above wherein X is a hydrogen atom and R is a hydrogen atom or C 1-6 alkyl group are prepared by reaction of an ether of the general formula with a ketone of the seventh general formula above, hydrogenation of the resulting diphenylethylene of the second general formula above wherein X is a hydrogen atom and optional dealkylation of the resulting desired product in which R is a C 1-6 alkyl group. Benzyl halides of the sixth general formula above are prepared by reaction of an ether of the third general formula above with an acid halide of the general formula R 3 COHal, reduction of the resulting ketone of the general formula and halogenation of the resulting alcohol of the general formula Pharmaceutical compositions having oestrogenic activity comprise, as active ingredient, at least one 3, 3<SP>1</SP>-dihalo-4,4<SP>1</SP>-dihydroxydibenzyl of the first general formula above, together with a solid or liquid pharmaceutical diluent or carrier, and may be administered orally.
GB02554/70A 1970-03-16 1970-03-16 Derivatives of 1,2-diphenyl-ethane Expired GB1280767A (en)

Priority Applications (20)

Application Number Priority Date Filing Date Title
GB02554/70A GB1280767A (en) 1970-03-16 1970-03-16 Derivatives of 1,2-diphenyl-ethane
NO504/71A NO132533C (en) 1970-03-16 1971-02-11
IE175/71A IE35009B1 (en) 1970-03-16 1971-02-15 Derivatives of 1,2-diphenyl-ethane
ZA710927A ZA71927B (en) 1970-03-16 1971-02-15 Derivatives of 1,2-diphenyl-ethane
SE7101951A SE393369B (en) 1970-03-16 1971-02-16 PROCEDURE FOR PREPARING CERTAIN STATED 1,2-DIPHENYLOXI DERIVATIVES WITH OSTROGENIC PROPERTIES
CA105,562A CA948215A (en) 1970-03-16 1971-02-16 Derivatives of 1,2-diphenyl-ethane
IL36225A IL36225A0 (en) 1970-03-16 1971-02-18 Derivatives of 1,2-diphenyl-ethane and processes for their preparation
YU531/71A YU35331B (en) 1970-03-16 1971-03-03 Process for obtaining 1,2-diphenylethane derivatives
DE19712110428 DE2110428C3 (en) 1970-03-16 1971-03-04 1,2-Diphenyläthanderivate, process for their preparation and medicaments containing these compounds
FI657/71A FI55170C (en) 1970-03-16 1971-03-05 FOERFARANDE FOER FRAMSTAELLNING AV NYA GONADOTROPIN INHIBERANDE 3 3'-DIFLUOR-4 4'-DIHYDROXIDIBENSYLDERIVAT
CH332071A CH558315A (en) 1970-03-16 1971-03-08 PROCESS FOR PRODUCING NEW 1,2-DIPHENYLAETHANE DERIVATIVES.
FR7108077A FR2085710B1 (en) 1970-03-16 1971-03-09
BE764081A BE764081A (en) 1970-03-16 1971-03-10 1,2-DIPHENYL-ETHANE DERIVATIVES
NL717103249A NL146140B (en) 1970-03-16 1971-03-11 PROCESS OF PREPARING A PHARMACEUTICAL PREPARATION WITH OESTROGEN ACTION, PREPARATION THEREFORE OBTAINED AND PROCESS FOR PREPARING SUITABLE COMPOUNDS.
AT209771A AT303711B (en) 1970-03-16 1971-03-11 Process for the preparation of new 1,2-diphenylethane derivatives
PH12292A PH10518A (en) 1970-03-16 1971-03-15 Derivatives of 1,2-diphenyl ethane
JP46014646A JPS515378B1 (en) 1970-03-16 1971-03-16
ES389282A ES389282A1 (en) 1970-03-16 1971-03-16 Derivatives of 1,2-diphenyl-ethane
DK126571A DK146015C (en) 1970-03-16 1971-03-16 ANALOGY PROCEDURE FOR THE PREPARATION OF ERYTHRO OR MESO FORMS OF 3,3'-DIFLUOR-4,4'-DIHYDROXYDIBENZYL DERIVATIVES
US05/563,119 US4051263A (en) 1970-03-16 1975-03-27 Derivatives of 1,2-diphenyl-ethane

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB02554/70A GB1280767A (en) 1970-03-16 1970-03-16 Derivatives of 1,2-diphenyl-ethane

Publications (1)

Publication Number Publication Date
GB1280767A true GB1280767A (en) 1972-07-05

Family

ID=10006781

Family Applications (1)

Application Number Title Priority Date Filing Date
GB02554/70A Expired GB1280767A (en) 1970-03-16 1970-03-16 Derivatives of 1,2-diphenyl-ethane

Country Status (18)

Country Link
JP (1) JPS515378B1 (en)
AT (1) AT303711B (en)
BE (1) BE764081A (en)
CA (1) CA948215A (en)
CH (1) CH558315A (en)
DK (1) DK146015C (en)
ES (1) ES389282A1 (en)
FI (1) FI55170C (en)
FR (1) FR2085710B1 (en)
GB (1) GB1280767A (en)
IE (1) IE35009B1 (en)
IL (1) IL36225A0 (en)
NL (1) NL146140B (en)
NO (1) NO132533C (en)
PH (1) PH10518A (en)
SE (1) SE393369B (en)
YU (1) YU35331B (en)
ZA (1) ZA71927B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5597271U (en) * 1978-12-28 1980-07-05

Also Published As

Publication number Publication date
FI55170C (en) 1979-06-11
FI55170B (en) 1979-02-28
SE393369B (en) 1977-05-09
CH558315A (en) 1975-01-31
JPS515378B1 (en) 1976-02-19
NO132533B (en) 1975-08-18
AT303711B (en) 1972-12-11
FR2085710A1 (en) 1971-12-31
YU53171A (en) 1980-06-30
NL7103249A (en) 1971-09-20
NO132533C (en) 1975-11-26
DK146015C (en) 1983-10-24
BE764081A (en) 1971-08-02
DE2110428B2 (en) 1976-08-26
IL36225A0 (en) 1971-04-28
YU35331B (en) 1980-12-31
IE35009B1 (en) 1975-10-15
CA948215A (en) 1974-05-28
ES389282A1 (en) 1973-06-16
DE2110428A1 (en) 1971-10-07
NL146140B (en) 1975-06-16
IE35009L (en) 1971-09-16
FR2085710B1 (en) 1975-08-01
PH10518A (en) 1977-05-26
ZA71927B (en) 1971-10-27
DK146015B (en) 1983-05-24

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee