GB1280767A - Derivatives of 1,2-diphenyl-ethane - Google Patents
Derivatives of 1,2-diphenyl-ethaneInfo
- 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
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.
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 |
CA105,562A CA948215A (en) | 1970-03-16 | 1971-02-16 | 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 |
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 |
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 |
ES389282A ES389282A1 (en) | 1970-03-16 | 1971-03-16 | Derivatives of 1,2-diphenyl-ethane |
JP46014646A JPS515378B1 (en) | 1970-03-16 | 1971-03-16 | |
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5597271U (en) * | 1978-12-28 | 1980-07-05 |
-
1970
- 1970-03-16 GB GB02554/70A patent/GB1280767A/en not_active Expired
-
1971
- 1971-02-11 NO NO504/71A patent/NO132533C/no unknown
- 1971-02-15 ZA ZA710927A patent/ZA71927B/en unknown
- 1971-02-15 IE IE175/71A patent/IE35009B1/en unknown
- 1971-02-16 CA CA105,562A patent/CA948215A/en not_active Expired
- 1971-02-16 SE SE7101951A patent/SE393369B/en unknown
- 1971-02-18 IL IL36225A patent/IL36225A0/en unknown
- 1971-03-03 YU YU531/71A patent/YU35331B/en unknown
- 1971-03-05 FI FI657/71A patent/FI55170C/en active
- 1971-03-08 CH CH332071A patent/CH558315A/en not_active IP Right Cessation
- 1971-03-09 FR FR7108077A patent/FR2085710B1/fr not_active Expired
- 1971-03-10 BE BE764081A patent/BE764081A/en not_active IP Right Cessation
- 1971-03-11 NL NL717103249A patent/NL146140B/en not_active IP Right Cessation
- 1971-03-11 AT AT209771A patent/AT303711B/en not_active IP Right Cessation
- 1971-03-15 PH PH12292A patent/PH10518A/en unknown
- 1971-03-16 DK DK126571A patent/DK146015C/en not_active IP Right Cessation
- 1971-03-16 JP JP46014646A patent/JPS515378B1/ja active Pending
- 1971-03-16 ES ES389282A patent/ES389282A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE2110428B2 (en) | 1976-08-26 |
FI55170C (en) | 1979-06-11 |
NL146140B (en) | 1975-06-16 |
CH558315A (en) | 1975-01-31 |
DK146015B (en) | 1983-05-24 |
ZA71927B (en) | 1971-10-27 |
AT303711B (en) | 1972-12-11 |
NO132533C (en) | 1975-11-26 |
DK146015C (en) | 1983-10-24 |
PH10518A (en) | 1977-05-26 |
FR2085710A1 (en) | 1971-12-31 |
ES389282A1 (en) | 1973-06-16 |
FI55170B (en) | 1979-02-28 |
IL36225A0 (en) | 1971-04-28 |
NL7103249A (en) | 1971-09-20 |
SE393369B (en) | 1977-05-09 |
CA948215A (en) | 1974-05-28 |
DE2110428A1 (en) | 1971-10-07 |
YU35331B (en) | 1980-12-31 |
BE764081A (en) | 1971-08-02 |
IE35009L (en) | 1971-09-16 |
NO132533B (en) | 1975-08-18 |
JPS515378B1 (en) | 1976-02-19 |
YU53171A (en) | 1980-06-30 |
FR2085710B1 (en) | 1975-08-01 |
IE35009B1 (en) | 1975-10-15 |
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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 |