GB1182257A - 03-Alkyl-21-Hydroxy-18,19-Dinorpregn-4-Ene-3,20-Diones and Derivatives Thereof - Google Patents
03-Alkyl-21-Hydroxy-18,19-Dinorpregn-4-Ene-3,20-Diones and Derivatives ThereofInfo
- Publication number
- GB1182257A GB1182257A GB2234266A GB2234266A GB1182257A GB 1182257 A GB1182257 A GB 1182257A GB 2234266 A GB2234266 A GB 2234266A GB 2234266 A GB2234266 A GB 2234266A GB 1182257 A GB1182257 A GB 1182257A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ols
- give
- prepared
- steroid
- pregna
- 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
- 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
1,182,257. 13 - Alkyl - 21 - hydroxy - 18,19- dinorpregn - 4 - ene - 3,20 - diones. H. SMITH. 16 May, 1967 [19 May, 1966], No. 22342/66 Heading C2U. Novel steroids of the formula (wherein R<SP>1</SP> is C 2-4 n-alkyl; R is H or acyl; and X is acyloxymethylene, hydroxymethylene or carbonyl), alone or in admixture with their 13α-entantiomers, are prepared (1) from the corresponding 17-acetyl or -halocarbonyl steroids by standard procedures; or (2) from corresponding steroids containing in ring A a protected 3-keto group together with appropriate double bonds by hydrolysis. Process (1) may be effected (a) by converting a 17-halo. carbonyl steroid to the 21-diazo-pregnen-20-one and hydrolysing or acylolysing this to the required 20-on-21-ol or its acylate, the halocarbonyl steroid being prepared in turn by converting by a Wittig reaction the corresponding 3 - alkoxy - gona - 1,3,5(10) - trien - 17 - one to the corresponding 17-methylene compound, hydroborating this to the 17-hydroxy-methyl compound, oxidizing this to the 17-carboxy compound, reducing in ring A by the Birch method to give the corresponding gona-2,5(10)- diene and hydrolysing this to the gon-4-en-3- one, and halogenating the 17-carboxy group; or (b) by converting a 17-acetyl steroid to the haloacetyl compound and acylolysing to give the required 21-acyloxy-pregnen-20-one; or (c) by converting the 17-acetyl steroid to the 21-ethoxalyl derivative, halogenating this and acylolysing the product to give a product as in (b). Starting materials for process (2) are desirably 3-alkoxy-pregna-2,5(10)-dienes, prepared by Birch reduction of the pregna-1,3,5(10)- triene-20,21-diols or 20-on-21-ols or mono- or di-acylates thereof, the 20,21-diols being in turn prepared by ethoxyethynylating the appropriate gona- 1,3,5(10)-trien-17-ones, either hydrogenating and acid treating the thus-produced 21- ethoxy - 17α - pregna - 1,3,5(10) - trien - 20 - ynols to give the corresponding pregna-1,3,5(10), 17(20)-tetraen-21-ones and reducing these to the 21-ols or acid treating the 21-ethoxy-20-yn-ols to give 17-carboxymethylene compounds and reducing these to the 21-ols, and then tetrahydropyranylating these and hydroborating the products. The starting materials for process (2) may also be prepared by methods similar to those detailed under (a), (b) and (c) above. 17-Hydroxy or acyloxy-acetyl products may be reduced to the 21-ols and any of these compounds may be acylated or hydrolysed as appropriate. Specification 1,115,635 is referred to. The steroids of the invention, which have mineralo-corticoid or other steroid hormone activity, may be made up into pharmaceutical compositions with suitable carriers.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2234266A GB1182257A (en) | 1966-05-19 | 1966-05-19 | 03-Alkyl-21-Hydroxy-18,19-Dinorpregn-4-Ene-3,20-Diones and Derivatives Thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2234266A GB1182257A (en) | 1966-05-19 | 1966-05-19 | 03-Alkyl-21-Hydroxy-18,19-Dinorpregn-4-Ene-3,20-Diones and Derivatives Thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1182257A true GB1182257A (en) | 1970-02-25 |
Family
ID=10177849
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2234266A Expired GB1182257A (en) | 1966-05-19 | 1966-05-19 | 03-Alkyl-21-Hydroxy-18,19-Dinorpregn-4-Ene-3,20-Diones and Derivatives Thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1182257A (en) |
-
1966
- 1966-05-19 GB GB2234266A patent/GB1182257A/en not_active Expired
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB1494097A (en) | D-homo-20-keto-pregnanes | |
GB1472922A (en) | Pregnanoic acid derivatives | |
GB1182257A (en) | 03-Alkyl-21-Hydroxy-18,19-Dinorpregn-4-Ene-3,20-Diones and Derivatives Thereof | |
GB1298974A (en) | 7beta-ALKYL-STEROIDS | |
GB1277266A (en) | 07-acetylgonanes and derivatives therefor | |
GB1383334A (en) | 15alpha,16alpha-methylene-steroids | |
GB1530615A (en) | 15,16-methylene-steroids of the pregnane series | |
GB1174358A (en) | 6-Methyl-16-Methylene-21-Fluoro-Steroids of the Pregnane Series. | |
GB1260398A (en) | NEW 18-METHYL-5alpha-H-ANDROSTANES | |
GB1206873A (en) | 7alpha-METHYL-ANDROSTENE COMPOUNDS | |
GB1097656A (en) | A process for the manufacture of steroids of the pregnane series | |
GB1185381A (en) | 05,16beta-Methylene Steroids of the 19-Nor-Androstane Series and Process for their Manufacture | |
AT275054B (en) | Process for the production of new 9β, 10α-steroids | |
GB1213118A (en) | PROCESS FOR PREPARING 9alpha-FLUORO-16-METHYLENE-PREDNISOLONE OR PREDNISONE, AND 21-ESTERS THEREOF | |
GB1196476A (en) | 21-Fluoro-Delta<4,6>-Pregnadienes and process for their manufacture | |
AT230027B (en) | Process for the preparation of 4-methyl-3-oxo-Δ <4> -steroids | |
DE1493108C (en) | Steroid compounds | |
GB980245A (en) | New-6-alkyl-steroids | |
GB1225038A (en) | 4-CHLORO-1,2alpha-METHYLENE-Delta<4>,<6>-PREGNADIEN-17alpha-OL-3,20-DIONE AND ITS 17-ESTERS | |
GB1205101A (en) | 3-oxo-a-nor-b-homo-pregnadienes and a process for their manufacture | |
GB1214507A (en) | 03-alkyl-11-oxygenated-gonenes | |
GB1004463A (en) | Process for the production of í¸-androstene and í¸-pregnene compounds | |
GB1061036A (en) | Steroidal 6-chloro-4,6-dienes and preparation thereof | |
GB1130115A (en) | 16-methyl-4-pregnen-3ªß-ol-20-ones and their preparation | |
GB1060491A (en) | Improvements in or relating to í¸ 9-ß-steroids |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PLNP | Patent lapsed through nonpayment of renewal fees |