GB1183899A - Ethers of the Pregnane Series - Google Patents
Ethers of the Pregnane SeriesInfo
- Publication number
- GB1183899A GB1183899A GB53886/68A GB5388668A GB1183899A GB 1183899 A GB1183899 A GB 1183899A GB 53886/68 A GB53886/68 A GB 53886/68A GB 5388668 A GB5388668 A GB 5388668A GB 1183899 A GB1183899 A GB 1183899A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- ols
- prepared
- hydroxy
- mixture
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
1,183,899. Steroid 3-ethers of the pregnane series. E. MERCK A.G. 13 Nov., 1968 [13 Dec., 1967], No. 53886/68. Heading C2U. Novel steroids of the formula (wherein R<SP>1</SP> is C 1-10 alkyl or C 3-7 cycloalkyl; and R<SP>2</SP> is a free or esterified OH group) and the ester salts of the acidic and basic 21-esters are prepared (1) by etherification of the corresponding 3-ols or reactive derivatives thereof with appropriate alcohols R<SP>1</SP>OH or reactive derivatives thereof or (2) by removal, by reaction with zinc in aqueous acetic acid, of the 17α-OH group from corresponding steroids containing this group; or (3) by solvolysis or hydrogenolysis of corresponding steroids in which the 20-keto group and/or the 21-R<SP>2</SP> group is or are functionally changed. Free 21-ols may be esterified. Starting materials of the formula are prepared by reduction of the 3-keto group of desoxycorticosterone possibly after esterification or etherification of the 21-hydroxy group and/or conversion of the 20-keto group to a functional derivative, to give a mixture of 3α- and 3#-ols which may be separated and protective groups if present then split off. The mixture of the individual epimers can be converted to reactive derivatives of the 3-ols, e.g. 3-halo compounds or 3-sulphonates, by standard procedures. Starting materials of the formula are prepared by reducing the bis-methylenedioxy derivative of cortexolone (prepared conventionally) to give a mixture of the epimeric 3-ols, splitting off the protecting group and etherifying, if necessary via a 3-ester or similar derivative, the epimers being separated at any appropriate stage. The novel 3-ethers of 3-hydroxy-21-(hydroxy or acyloxy) - 4 - pregnen - 20 - one are stated to possess a sodium-retaining and diuresisinhibiting action of the same order as that of 9α-fluoro-hydrocortisone and therefore to be useful for combatting Adison's disease and hypotonia. They may be made up into pharmaceutical compositions with suitable carriers.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671668444 DE1668444A1 (en) | 1967-12-13 | 1967-12-13 | AEther of the Pregnan Series and Process for Their Production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1183899A true GB1183899A (en) | 1970-03-11 |
Family
ID=5686107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB53886/68A Expired GB1183899A (en) | 1967-12-13 | 1968-11-13 | Ethers of the Pregnane Series |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3597453A (en) |
| AT (1) | AT292209B (en) |
| BE (1) | BE725269A (en) |
| BR (1) | BR6804629D0 (en) |
| ES (1) | ES361360A1 (en) |
| FR (1) | FR8163M (en) |
| GB (1) | GB1183899A (en) |
-
1968
- 1968-10-28 AT AT1050868A patent/AT292209B/en not_active IP Right Cessation
- 1968-11-13 GB GB53886/68A patent/GB1183899A/en not_active Expired
- 1968-11-21 FR FR174646A patent/FR8163M/fr not_active Expired
- 1968-12-04 US US781269A patent/US3597453A/en not_active Expired - Lifetime
- 1968-12-05 BR BR204629/68A patent/BR6804629D0/en unknown
- 1968-12-11 BE BE725269D patent/BE725269A/xx unknown
- 1968-12-12 ES ES361360A patent/ES361360A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR8163M (en) | 1970-08-24 |
| BR6804629D0 (en) | 1973-01-11 |
| ES361360A1 (en) | 1970-08-16 |
| US3597453A (en) | 1971-08-03 |
| BE725269A (en) | 1969-06-11 |
| AT292209B (en) | 1971-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1190403A (en) | 4-Hydroxy-2-Butenoic Acid Lactones | |
| Sarett | Stereoisomeric Substituted 11-Keto-20-hydroxypregnanes. I | |
| GB1495531A (en) | 11beta-alkyl steroids of the estrane series | |
| GB1183899A (en) | Ethers of the Pregnane Series | |
| GB1376892A (en) | 2beta-substituted-3alpha-hydroxysteroids and their esters | |
| US3290297A (en) | Tetrahydrofuranyl ethers of delta1, 3, 5(10)-estratriene | |
| US3032552A (en) | 1-methyl steroids of the androstane series | |
| US3061606A (en) | Delta-4-pregnenolones and method | |
| US3062846A (en) | (lower alkoxy) methyl ether derivatives of steroids and process therefor | |
| US3143557A (en) | Substituted 19-norandrosta-5(10), 9(11)-dienes and method of preparing same | |
| US3242169A (en) | 6alpha-dimethylaminomethyl-3-oxo-delta4-steroids and method for producing same | |
| US3214447A (en) | 2alpha-methyl-11-oxygenated androstanes and intermediates therefor | |
| US3228933A (en) | 3-enol ethers of 6-methyl-3-oxo-deta4-steroids and process for preparing same | |
| US2861085A (en) | 19-nordesoxycorticosterone and process therefor | |
| US3565778A (en) | Process for the manufacture of beta-hydroxy-steroid-ketones | |
| US3118919A (en) | Dienic steroids and method of preparing the same | |
| US2673863A (en) | Esters of 20, 21-ketols of the pregnane series with acids of the type of trimethyl acetic acid | |
| GB1185381A (en) | 05,16beta-Methylene Steroids of the 19-Nor-Androstane Series and Process for their Manufacture | |
| ES361690A1 (en) | 18-methylene-steroids of the pregnane series | |
| US3092626A (en) | Process for the manufacture of 16-alkyl-20:21-ketols of the pregnane series | |
| US3053858A (en) | 10-fluoro-19-nor steroids | |
| US2989552A (en) | 4-organothiomethyl-3-oxo-delta4 steroids and methods for preparing same | |
| GB1022953A (en) | New homosteroids and process for their manufacture | |
| US3000912A (en) | 2alpha-substituted methyl androstanes | |
| US3377343A (en) | 2', 2'-bistrifluoromethyloxetano(3', 4'; 16alpha, 17alpha)derivatives of the pregnane series |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLE | Entries relating assignments, transmissions, licences in the register of patents | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |