GB1099093A - Alkene derivatives - Google Patents
Alkene derivativesInfo
- Publication number
- GB1099093A GB1099093A GB3770065A GB3770065A GB1099093A GB 1099093 A GB1099093 A GB 1099093A GB 3770065 A GB3770065 A GB 3770065A GB 3770065 A GB3770065 A GB 3770065A GB 1099093 A GB1099093 A GB 1099093A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cis
- isomers
- trans isomers
- trans
- compositions
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
The invention comprises cis and trans isomers of compounds of the formula <FORM:1099093/C2/1> wherein R1 and R2 stand for alkyl radicals containing not more than 4 carbon atoms, or the -NR1R2 group stands for the morpholino radical, R3 and R4 stand for phenyl radicals, and X stands for a halogen atom, and the acid-addition salts thereof. The cis and trans isomers may be obtained by separation of the mixed isomers by known methods, for example, (1) by fractional crystallization of the mixed isomers or their acid-addition salts, from an organic solvent or mixture of solvents, or (2) by chromatography. An example, also describes the preparation of the mixed isomers of 1-(p-b -dimethylaminoethoxyphenyl) - 1,2 - diphenyl - 2-bromoethylene by reaction of 1-(p-hydroxyphenyl) -1,2-diphenyl-2-bromoethylene with b -dimethylaminoethyl chloride. Pharmaceutical and veterinary compositions comprise at least one of the cis and trans isomers of alkene derivatives of the above formula (other than a mixture of a cis isomer and its corresponding trans isomer) together with a pharmaceutically-acceptable diluent or carrier. The compositions are useful for the modification of the endocrine status in man and animals and may be used for the control of hormone-dependent tumours or for management of the sex-cycle and aberrations thereof. The trans isomers are preferred for anti-oestrogenic effects and the cis for oestrogenic effects. The compositions may be in the form of tablets, capsules, aqueous or oily solutions or suspensions, injectable aqueous or oily solutions or suspensions, dispersible powders or pre-mixes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3770065A GB1099093A (en) | 1965-09-03 | 1965-09-03 | Alkene derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3770065A GB1099093A (en) | 1965-09-03 | 1965-09-03 | Alkene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1099093A true GB1099093A (en) | 1968-01-17 |
Family
ID=10398386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3770065A Expired GB1099093A (en) | 1965-09-03 | 1965-09-03 | Alkene derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1099093A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0107208A1 (en) * | 1982-10-26 | 1984-05-02 | Klinge Pharma GmbH | 1,1,2-Triphenyl-but-1-ene derivatives, process for their preparation and their use as medicines |
| US4536516A (en) * | 1962-09-13 | 1985-08-20 | Imperial Chemical Industries Plc | Alkene derivatives |
| EP0287690A1 (en) * | 1987-04-21 | 1988-10-26 | HEUMANN PHARMA GMBH & CO | Stable solvent adducts of Z-1-(p-beta-dimethylamino-ethoxyphenyl)-1-(p-hydroxyphenyl)-2-phenylbut-1-ene |
| US4806685A (en) * | 1985-08-05 | 1989-02-21 | Gyogyszerkutato Inteezet/Pharmaceutical Research Institute | 1,1,2-triphenylpropane and -propene derivatives |
| WO1995008528A1 (en) * | 1993-09-24 | 1995-03-30 | Merrell Pharmaceuticals Inc. | Triaryl-ethylene derivatives for use in therapy |
| 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 |
| US11046638B2 (en) | 2019-11-14 | 2021-06-29 | Apotex Inc. | Processes for the preparation of zuclomiphene and intermediates thereof |
| US11440871B2 (en) | 2019-11-14 | 2022-09-13 | Apotex Inc. | Zuclomiphene salts and crystalline forms thereof |
| US11661396B2 (en) | 2020-01-22 | 2023-05-30 | Apotex Inc. | Crystalline forms of zuclomiphene citrate |
-
1965
- 1965-09-03 GB GB3770065A patent/GB1099093A/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4536516A (en) * | 1962-09-13 | 1985-08-20 | Imperial Chemical Industries Plc | Alkene derivatives |
| EP0107208A1 (en) * | 1982-10-26 | 1984-05-02 | Klinge Pharma GmbH | 1,1,2-Triphenyl-but-1-ene derivatives, process for their preparation and their use as medicines |
| US4806685A (en) * | 1985-08-05 | 1989-02-21 | Gyogyszerkutato Inteezet/Pharmaceutical Research Institute | 1,1,2-triphenylpropane and -propene derivatives |
| EP0287690A1 (en) * | 1987-04-21 | 1988-10-26 | HEUMANN PHARMA GMBH & CO | Stable solvent adducts of Z-1-(p-beta-dimethylamino-ethoxyphenyl)-1-(p-hydroxyphenyl)-2-phenylbut-1-ene |
| US4973755A (en) * | 1987-04-21 | 1990-11-27 | Heumann Pharma Gmbh & Co. | Stable solvent adducts of Z-1-(p-β-dimethylaminoethoxy-phenyl)-1-(p-hydroxyphenyl)-2-phenyl-but-1-ene |
| WO1995008528A1 (en) * | 1993-09-24 | 1995-03-30 | Merrell Pharmaceuticals Inc. | Triaryl-ethylene derivatives for use in therapy |
| 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 |
| US11046638B2 (en) | 2019-11-14 | 2021-06-29 | Apotex Inc. | Processes for the preparation of zuclomiphene and intermediates thereof |
| US11440871B2 (en) | 2019-11-14 | 2022-09-13 | Apotex Inc. | Zuclomiphene salts and crystalline forms thereof |
| US11661396B2 (en) | 2020-01-22 | 2023-05-30 | Apotex Inc. | Crystalline forms of zuclomiphene citrate |
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