GB823955A - Improvements in steroid compounds and method for manufacture of same - Google Patents
Improvements in steroid compounds and method for manufacture of sameInfo
- Publication number
- GB823955A GB823955A GB11714/56A GB1171456A GB823955A GB 823955 A GB823955 A GB 823955A GB 11714/56 A GB11714/56 A GB 11714/56A GB 1171456 A GB1171456 A GB 1171456A GB 823955 A GB823955 A GB 823955A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diol
- androstan
- hydroxy
- estradiol
- ethers
- 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
- 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
Abstract
The invention comprises 16a -hydroxy steroids (and their ethers and esters) of the androstan, D 4-androsten, etiocholan, estratrien, estratetraen, and estrapentaen series having the structural formula <FORM:0823955/IV (b)/1> wherein X represents a hydrogen atom or a methyl, ethyl, propyl, butyl, amyl, isoamyl, vinyl, cyclopentylpropyl, acetyl, propionyl, butyryl, cyclopentylpropionyl, palmitoyl, benzyl, benzoyl, tolyl or naphthyl radical and Y, when present, represents a methyl radical, and a process for their preparation and of their esters and ethers by reacting the corresponding 16b -hydroxy stereoisomer with an aryl sulphonyl halide to form the corresponding 16b -aryl sulphonic ester, reacting this ester with an alkali metal salt of a lower aliphatic acid of one to four carbon atoms in a medium comprising said aliphatic acid to form the corresponding 16a -aliphatic acid ester, and if necessary hydrolysing to form the 16a -hydroxy steroid and subsequently if desired re-esterifying or etherifying the 16a -hydroxy group. In examples: (1) 1,3,5(10)-estratrien-3,16b -diol in pyridine is treated with p-toluene sulphonyl chloride and the resulting di-tosylate heated with acetic anhydride and sodium acetate and saponified to estradiol-3,16a which is purified by reacetylation and saponification; 1,3,5(10),6,8-estrapentaen-3,16a -diol and 1,3,5(10),7-estratetraen - 3,16a - diol; and (2) their diacetates and dipropionates are similarly prepared; (3) estradiol-3,16a is benzoylated in aqueous NaOH giving the 3-benzoate; and (4) in pyridine, yielding the 3,16-dibenzoate; (5) 3-methoxyestra - 1,3,5(10) - trien - 16b - ol as in (1) yields estradiol-3-methyl ether 16a -acetate; (6) androstan-3b ,16a -diol is prepared from 3b -benzoyloxy-androstan-16b -ol and subsequently (7) acetylated to the diacetate. Other specified products are 5-isoandrostan-3b ,16a -diol, estra1,3,5(10),6,8-pentaen-3,16a -diol and their ethers and esters. 3b - Benzoyloxy - androstan - 16b - ol is prepared from androstan-3b -ol-16-one benzoate by reduction with sodium borohydride; equilenin16-one is similarly reduced or hydrogenated using Adams catalyst to yield the corresponding 3,16b -diol. Specification 778,940 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US823955XA | 1955-09-01 | 1955-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB823955A true GB823955A (en) | 1959-11-18 |
Family
ID=22170926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11714/56A Expired GB823955A (en) | 1955-09-01 | 1956-04-17 | Improvements in steroid compounds and method for manufacture of same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB823955A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000047603A2 (en) * | 1999-02-09 | 2000-08-17 | Schering Aktiengesellschaft | 16-hydroxyestratrienes as selective estrogens |
| US7109360B1 (en) | 1999-02-09 | 2006-09-19 | Schering Ag | 16-hydroxyestratrienes as selectively active estrogens |
-
1956
- 1956-04-17 GB GB11714/56A patent/GB823955A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000047603A2 (en) * | 1999-02-09 | 2000-08-17 | Schering Aktiengesellschaft | 16-hydroxyestratrienes as selective estrogens |
| WO2000047603A3 (en) * | 1999-02-09 | 2001-08-02 | Schering Ag | 16-hydroxyestratrienes as selective estrogens |
| JP2002536455A (en) * | 1999-02-09 | 2002-10-29 | シエーリング アクチエンゲゼルシヤフト | 16-Hydroxyestraditriene as a selective estrogen |
| US7109360B1 (en) | 1999-02-09 | 2006-09-19 | Schering Ag | 16-hydroxyestratrienes as selectively active estrogens |
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