GB791771A - Steroid compounds - Google Patents
Steroid compoundsInfo
- Publication number
- GB791771A GB791771A GB20460/55A GB2046055A GB791771A GB 791771 A GB791771 A GB 791771A GB 20460/55 A GB20460/55 A GB 20460/55A GB 2046055 A GB2046055 A GB 2046055A GB 791771 A GB791771 A GB 791771A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dione
- pregnene
- acetate
- triol
- diol
- 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
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Abstract
D 9(11) - Anhydro - cyclopentanophenanthrene compounds are prepared by reacting an 11b -hydroxycyclopentanophenanthrene compound having a hydrogen atom attached to the 11-carbon atom with an alkyl sulphonyl chloride, e.g. a sulphonyl chloride containing 1 to 8, preferably 1 to 4, carbon atoms. It is preferable to use the sulphonyl chloride in amounts from 1 to 10 mols. per mol. of cyclopentanophenanthrene reactant. A solvent such as a hydrocarbon or chlorinated hydrocarbon may be used in the process. The reaction may be carried out in the presence of a tertiary amine and/or an amide of a secondary amine, suitable tertiary amines being pyridine, N-methyl- and N-ethyl-morpholine, a ,g -lutidine, collidine, nicotine, trimethyl-, triethyl- and tripropyl-amine, dimethyl- and diethyl-aniline, and N-heptyl-, N-amyl-, N-butyl-, N-propyl-, N-ethyl- and N-methyl-piperidine, and suitable amides being dimethylformamide and dimethylacetamide. The amine and/or amide may be solvents or a solvent for the 11b -hydroxy-cyclopentanophenanthrene reactant e.g. from 1 to 10 mols. of said amine or said amide or a mixture thereof per mol. of 11b -hydroxy-cyclopentanophenanthrene reactant may be used. The reaction may be carried out in an organic solvent which does not consist wholly of the tertiary amine and/or amide, e.g. the solvent may comprise a hydrocarbon or chlorinated hydrocarbon such as a mixture of benzene and pyridine, or a mixture of methylene chloride and pyridine. Other solvents which may be used are chloroform, acetone, propylene glycol and methyl ethyl ketone and mixtures thereof. Cyclopentanophenanthrene reactants which may be used in the above process are pregnanes and pregnenes, particularly the D 4-pregnenes. Substituents other than the 11b -hydroxy group which may be present in the steroid reactants are 3,20-keto groups and 3,17a -hydroxy groups. It is desirable to convert a 21-hydroxy group into an ester thereof before reaction with the sulphonyl chloride. Reactants specifically mentioned are the 21-esters of D 4-pregnene-11b ,17a ,21-triol-3,20-dione-particularly the acetate, propionate, formate, butyrate, benzoate, t-butyl-acetate, hemisuccinate and phenylacetate esters, D 4 - pregnene - 11b ,17a - diol - 3,20 - dione, D 4-pregnene - 11b - ol - 3,20 - dione, D 4 - pregnene-11b ,21 - diol - 3,20 - dione - 121 - acetate, acetate esters of D 4 - pregnene - 11b ,17a ,20,21 - tetrol3,20 - dione, D 4 - androstene - 11b - ol - 3,17-dione, D 4 - pregnene - 11b ,17a ,21 - triol - 3,20-dione, pregnane - 11b - ol - 3,20 - dione, pregnane - 11b ,21 - diol, 3,20 - dione - 21 - acetate, pregnane - 11b ,17a ,21 - triol - 3,20 - dione, allopregnane - 11b ,17a ,21 - triol - 3,20 - dione, D 5-pregnene - 3b ,11b - diol - 20 - one, and D 5-pregnene - 11b ,17a ,21 - triol - 3,20 - dione - 21-acetate - 3,20 - bis - ethylene ketal. In the examples, D 4,9(11) - pregnadiene - 17a ,21 - diol-3,20 - dione - 21 - acetate is prepared. Specification 750,866 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US791771XA | 1954-07-29 | 1954-07-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB791771A true GB791771A (en) | 1958-03-12 |
Family
ID=22148909
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB20460/55A Expired GB791771A (en) | 1954-07-29 | 1955-07-14 | Steroid compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB791771A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10159682B2 (en) | 2007-08-03 | 2018-12-25 | Cassiopea S.P.A. | Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives |
US10603327B2 (en) | 2015-06-22 | 2020-03-31 | Cassiopea S.P.A. | High concentration formulation |
-
1955
- 1955-07-14 GB GB20460/55A patent/GB791771A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10159682B2 (en) | 2007-08-03 | 2018-12-25 | Cassiopea S.P.A. | Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives |
US10166245B2 (en) | 2007-08-03 | 2019-01-01 | Cassiopea S.P.A. | Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives |
US10716796B2 (en) | 2007-08-03 | 2020-07-21 | Cassiopea S.P.A. | Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives |
US11207332B2 (en) | 2007-08-03 | 2021-12-28 | Cassiopea S.P.A. | Enzymatic process for obtaining 17 α-monoesters of cortexolone and/or its 9,11-dehydroderivatives |
US11938141B2 (en) | 2007-08-03 | 2024-03-26 | Cassiopea S.P.A. | Enzymatic process for obtaining 17 alpha-monoesters of cortexolone and/or its 9,11-dehydroderivatives |
US10603327B2 (en) | 2015-06-22 | 2020-03-31 | Cassiopea S.P.A. | High concentration formulation |
US10980819B2 (en) | 2015-06-22 | 2021-04-20 | Cassiopea S.P.A. | High concentration formulation |
US11213531B2 (en) | 2015-06-22 | 2022-01-04 | Cassiopea S.P.A. | High concentration formulation |
US11883415B2 (en) | 2015-06-22 | 2024-01-30 | Cassiopea S.P.A. | High concentration formulation |
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