GB1208039A - 0-HYDROXY-7alpha-METHYL-OESTRADIOL DERIVATIVES - Google Patents
0-HYDROXY-7alpha-METHYL-OESTRADIOL DERIVATIVESInfo
- Publication number
- GB1208039A GB1208039A GB2793968A GB2793968A GB1208039A GB 1208039 A GB1208039 A GB 1208039A GB 2793968 A GB2793968 A GB 2793968A GB 2793968 A GB2793968 A GB 2793968A GB 1208039 A GB1208039 A GB 1208039A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydroxy
- estrone
- esterified
- etherified
- 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- JUAJXSMWFOFDFC-MNHDCVOLSA-N (7r,8r,9s,13s,14s)-3-hydroxy-7,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-one Chemical compound C1C[C@]2(C)C(=O)CC[C@H]2[C@@H]2[C@H](C)CC3=CC(O)=CC=C3[C@H]21 JUAJXSMWFOFDFC-MNHDCVOLSA-N 0.000 abstract 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 230000001076 estrogenic effect Effects 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000016087 ovulation Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
1,208,039. 1 - Hydroxy - 7α - methyl - estradiol derivatives. SCHERING A.G. 12 June, 1968, No. 27939/68. Heading C2U. Novel steriods of the formula (in which R 1 and R 2 is each H, C 1-6 alkyl or a saturated oxyheterocyclic group or an acyl radical; and R 3 is H or an optionally halogensubstituted C 1-6 aliphatic hydrocarbon group) and the novel 1,3 - diacetate and 1,3 - bis - tetrahydropyranyl ether of 1 - hydroxy - 7α - methyl - estrone are prepared by etherification or esterification of 1- hydroxy - 7α - methyl - estrone and formation of the group α - R 3 (#- OR 2 ) from the free, esterified or etherified 17 - ketone by known methods. In the products free hydroxy groups can be esterified or etherified and/or esterified or etherified hydroxy groups hydrolysed. 1 - Hydroxy - 7α - methyl estrone is prepared by reacting 7α -methyl - estrone (prepared by hydrolysis of the tetrahydropyranyl ether) with lead tetra-acetate in glacial acetic acid to give 7α - methyl - #<SP>1,4</SP> - estradien - 10# - ol - 3,17 - dione acetate and treating this with a little conc. H 2 SO 4 in acetic anhydride. The steriods of the above general formula have oestrogenic activity and inhibit ovulation, and they may be made up into pharmaceutical compositions for oral or parenteral administration.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2793968A GB1208039A (en) | 1968-06-12 | 1968-06-12 | 0-HYDROXY-7alpha-METHYL-OESTRADIOL DERIVATIVES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2793968A GB1208039A (en) | 1968-06-12 | 1968-06-12 | 0-HYDROXY-7alpha-METHYL-OESTRADIOL DERIVATIVES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1208039A true GB1208039A (en) | 1970-10-07 |
Family
ID=10267712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2793968A Expired GB1208039A (en) | 1968-06-12 | 1968-06-12 | 0-HYDROXY-7alpha-METHYL-OESTRADIOL DERIVATIVES |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1208039A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3951959A (en) * | 1973-07-13 | 1976-04-20 | Schering Aktiengesellschaft | 1,3-Oxygenated 8α-estratrienes |
-
1968
- 1968-06-12 GB GB2793968A patent/GB1208039A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3951959A (en) * | 1973-07-13 | 1976-04-20 | Schering Aktiengesellschaft | 1,3-Oxygenated 8α-estratrienes |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |