GB1128379A

GB1128379A – Novel alkene derivatives, process for the preparation thereof and compositions containing the same
– Google Patents

GB1128379A – Novel alkene derivatives, process for the preparation thereof and compositions containing the same
– Google Patents
Novel alkene derivatives, process for the preparation thereof and compositions containing the same

Info

Publication number
GB1128379A

GB1128379A
GB27483/66A
GB2748366A
GB1128379A
GB 1128379 A
GB1128379 A
GB 1128379A
GB 27483/66 A
GB27483/66 A
GB 27483/66A
GB 2748366 A
GB2748366 A
GB 2748366A
GB 1128379 A
GB1128379 A
GB 1128379A
Authority
GB
United Kingdom
Prior art keywords
prepared
alkene
reaction
ethyl
phenyl
Prior art date
1966-06-20
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
GB27483/66A
Inventor
Dora Nellie Richardson
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.)

Imperial Chemical Industries Ltd

Original Assignee
Imperial Chemical Industries 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.)
1966-06-20
Filing date
1966-06-20
Publication date
1968-09-25

1966-06-20
Application filed by Imperial Chemical Industries Ltd
filed
Critical
Imperial Chemical Industries Ltd

1966-06-20
Priority to GB27483/66A
priority
Critical
patent/GB1128379A/en

1967-05-22
Priority to US640365A
priority
patent/US3493606A/en

1967-06-07
Priority to DE19671618565
priority
patent/DE1618565C3/en

1967-06-19
Priority to FR110993A
priority
patent/FR1535567A/en

1967-06-19
Priority to CS4484A
priority
patent/CS150543B2/cs

1967-06-19
Priority to SE08634/67A
priority
patent/SE339465B/xx

1967-06-19
Priority to CH865067A
priority
patent/CH507905A/en

1967-06-19
Priority to NL6708487A
priority
patent/NL6708487A/xx

1967-06-19
Priority to BE700166D
priority
patent/BE700166A/xx

1967-06-20
Priority to DK318667AA
priority
patent/DK119457B/en

1967-06-20
Priority to JP42039549A
priority
patent/JPS5026530B1/ja

1967-09-18
Priority to FR7070D
priority
patent/FR7070M/fr

1968-09-25
Publication of GB1128379A
publication
Critical
patent/GB1128379A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

A—HUMAN NECESSITIES

A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE

A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES

A61K31/00—Medicinal preparations containing organic active ingredients

A61K31/13—Amines

A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C43/00—Ethers; Compounds having groups, groups or groups

C07C43/02—Ethers

C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms

C07C43/14—Unsaturated ethers

Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE

Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

Y02P20/00—Technologies relating to chemical industry

Y02P20/50—Improvements relating to the production of bulk chemicals

Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

1,128,379. Aminoalkoxyphenyl alkenes. IMPERIAL CHEMICAL INDUSTRIES Ltd. 17 May, 1967 [20 June, 1966], No. 27483/66. Heading C2C. Novel cis- and trans-isomers of aminoalkoxyphenyl alkenes of the general formula wherein R1 is an alkyl radical of not more than 6 carbon atoms, A is an alkylene radical, R2 and R3, which may be the same or different, are phenyl radicals optionally bearing one or more substituents selected from halogen atoms and alkyl and alkoxy radicals, and X is a halogen atom, and acid addition salts thereof are prepared by replacement by hydrogen of a protecting group (P) in an alkene derivative of the general formula wherein P is an alkoxycarbonyl or arylsulphonyl radical, with optional formation of an acid addition salt of the product, followed by separation, if necessary, of the product so that a substantially pure cis- or trans-isomer is obtained. Pharmaceutical compositions, which modify the reproductive endocrine status in mammalian species, comprise at least one cis- or transisomer of an aminoalkoxyphenyl alkene of the first general formula above or an acid addition salt thereof and a non-toxic, pharmaceutically acceptable, inert diluent or carrier therefor. Alkene derivatives of the second general formula above may be prepared either by halogenation of an alkene derivative of the formula or, when P is an alkoxycarbonyl radical, by reaction of a dialkylaminoalkoxyphenyl alkene of the formula wherein R4 is an alkyl radical of not more than 6 carbon atoms, with a halogeno compound of the formula P-X. Alkene derivatives of the third formula above may be prepared by dehydration of the corresponding ethanol derivative. Dialkylaminoalkoxyphenyl alkenes of the fourth formula above may be prepared by reaction of the corresponding hydroxy-phenyl alkene with a dialkylaminoalkyl halide in the presence of sodium. 1-p-(3-Dimethylaminopropoxy)phenyl – 1 – p – tolyl – 2 – p – chlorophenylethanol is prepared by reaction of 4-hydroxy-41– methyl.benzophenone with 3-dimethylaminopropyl chloride in the presence of sodium, followed by treatment of the resulting 4-(3-dimethylaminopropoxy) – 41– methyl – benzophenone with a Grignard reagent prepared from p-chlorobenzyl chloride and magnesium. 1-p-[2-(NEthyl – N – p – toluenesulphonylamino)ethoxy]- phenyl-1 ,2-diphenylethanol is prepared by reaction of p-toluene sulphonyl chloride with 2- ethylaminoethanol, bromination of the resulting N – ethyl – N – (2 – hydroxy – ethyl) – p – toluenesulphonamide to give N-ethyl-N-(2-bromoethyl)- p-toluenesulphonamide, reaction of the latter compound with the sodium salt of 4-hydroxydesoxybenzoin to give 4-[2-(N-ethyl-N-p-toluenesulphonylamino)ethoxy]- desoxybenzoin, followed by treatment with a Grignard reagent prepared from bromobenzene and magnesium.

GB27483/66A
1966-06-20
1966-06-20
Novel alkene derivatives, process for the preparation thereof and compositions containing the same

Expired

GB1128379A
(en)

Priority Applications (12)

Application Number
Priority Date
Filing Date
Title

GB27483/66A

GB1128379A
(en)

1966-06-20
1966-06-20
Novel alkene derivatives, process for the preparation thereof and compositions containing the same

US640365A

US3493606A
(en)

1966-06-20
1967-05-22
Trans-isomers of 1-(loweralkylamino-alkoxy) – phenyl – 1,2 – diphenyl-2-haloethylenes and the salts thereof

DE19671618565

DE1618565C3
(en)

1966-06-20
1967-06-07

Trans isomers of alkene derivatives and processes for their preparation

FR110993A

FR1535567A
(en)

1966-06-20
1967-06-19

Alkenic derivatives and process for their manufacture

CS4484A

CS150543B2
(en)

1966-06-20
1967-06-19

SE08634/67A

SE339465B
(en)

1966-06-20
1967-06-19

CH865067A

CH507905A
(en)

1966-06-20
1967-06-19
Oestrogenic and anti-oestrogenic alkene derivs

NL6708487A

NL6708487A
(en)

1966-06-20
1967-06-19

BE700166D

BE700166A
(en)

1966-06-20
1967-06-19

DK318667AA

DK119457B
(en)

1966-06-20
1967-06-20

Analogous process for the preparation of substantially pure transisomers of p-aminoalkoxyphenylalkenes.

JP42039549A

JPS5026530B1
(en)

1966-06-20
1967-06-20

FR7070D

FR7070M
(en)

1966-06-20
1967-09-18

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

GB27483/66A

GB1128379A
(en)

1966-06-20
1966-06-20
Novel alkene derivatives, process for the preparation thereof and compositions containing the same

GB2748367

1967-05-17

Publications (1)

Publication Number
Publication Date

GB1128379A
true

GB1128379A
(en)

1968-09-25

Family
ID=26258849
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB27483/66A
Expired

GB1128379A
(en)

1966-06-20
1966-06-20
Novel alkene derivatives, process for the preparation thereof and compositions containing the same

Country Status (10)

Country
Link

US
(1)

US3493606A
(en)

JP
(1)

JPS5026530B1
(en)

BE
(1)

BE700166A
(en)

CH
(1)

CH507905A
(en)

CS
(1)

CS150543B2
(en)

DK
(1)

DK119457B
(en)

FR
(1)

FR7070M
(en)

GB
(1)

GB1128379A
(en)

NL
(1)

NL6708487A
(en)

SE
(1)

SE339465B
(en)

Cited By (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US5525633A
(en)

*

1993-09-24
1996-06-11
Merrell Dow Pharmaceuticals Inc.
Triaryl-ethylene derivatives

US5691384A
(en)

*

1994-11-29
1997-11-25
Hoechst Marion Roussel, Inc.
Method of using triaryl-ethylene derivatives in the treatment and prevention of osteoporosis

US5693674A
(en)

*

1994-11-29
1997-12-02
Hoechst Marion Roussel, Inc.
Method of using triaryl-ethylene derivatives in the treatment and prevention of osteoporosis

Families Citing this family (7)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

EP0002097B1
(en)

1977-08-22
1981-08-05
Imperial Chemical Industries Plc
Triphenylalkene derivatives, process for their preparation and pharmaceutical compositions containing them

US4206234A
(en)

*

1977-08-22
1980-06-03
Imperial Chemical Industries Limited
Triphenylbut-1-ene derivatives and pharmaceutical compositions and uses thereof

US5204337A
(en)

*

1988-10-31
1993-04-20
Endorecherche Inc.
Estrogen nucleus derivatives for use in inhibition of sex steroid activity

US5219548A
(en)

*

1990-10-01
1993-06-15
Board Of Regents, The University Of Texas System
High affinity halogenated-tamoxifen derivatives and uses thereof

ZA924811B
(en)

*

1991-06-28
1993-12-29
Endorecherche Inc
Controlled release systems and low dose androgens

US5681835A
(en)

*

1994-04-25
1997-10-28
Glaxo Wellcome Inc.
Non-steroidal ligands for the estrogen receptor

HU0002852A3
(en)

1997-08-15
2001-11-28
Univ Durham
A method of preventing or treating estrogen-dependent diseases and disorders using triphenil-ethylene derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

NL100243C
(en)

*

DE1155436B
(en)

*

1956-11-06
1963-10-10
Richardson Merrell Inc

Process for the preparation of 1- [p- (ª ‰ -Diaethylaminoaethoxy) -phenyl] -1, 2-diphenyl-2-chloroethylene

1966

1966-06-20
GB
GB27483/66A
patent/GB1128379A/en
not_active
Expired

1967

1967-05-22
US
US640365A
patent/US3493606A/en
not_active
Expired – Lifetime

1967-06-19
CS
CS4484A
patent/CS150543B2/cs
unknown

1967-06-19
NL
NL6708487A
patent/NL6708487A/xx
unknown

1967-06-19
CH
CH865067A
patent/CH507905A/en
not_active
IP Right Cessation

1967-06-19
SE
SE08634/67A
patent/SE339465B/xx
unknown

1967-06-19
BE
BE700166D
patent/BE700166A/xx
unknown

1967-06-20
DK
DK318667AA
patent/DK119457B/en
unknown

1967-06-20
JP
JP42039549A
patent/JPS5026530B1/ja
active
Pending

1967-09-18
FR
FR7070D
patent/FR7070M/fr
not_active
Expired

Cited By (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US5525633A
(en)

*

1993-09-24
1996-06-11
Merrell Dow Pharmaceuticals Inc.
Triaryl-ethylene derivatives

US5691384A
(en)

*

1994-11-29
1997-11-25
Hoechst Marion Roussel, Inc.
Method of using triaryl-ethylene derivatives in the treatment and prevention of osteoporosis

US5693674A
(en)

*

1994-11-29
1997-12-02
Hoechst Marion Roussel, Inc.
Method of using triaryl-ethylene derivatives in the treatment and prevention of osteoporosis

Also Published As

Publication number
Publication date

JPS5026530B1
(en)

1975-09-01

US3493606A
(en)

1970-02-03

CH507905A
(en)

1971-05-31

DE1618565B2
(en)

1975-12-04

DK119457B
(en)

1971-01-11

FR7070M
(en)

1969-06-30

SE339465B
(en)

1971-10-11

DE1618565A1
(en)

1970-10-29

BE700166A
(en)

1967-12-19

NL6708487A
(en)

1967-12-21

CS150543B2
(en)

1973-09-04

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