GB1548259A - Process for manufacture of steroid carboxylic acid lactones - Google Patents
Process for manufacture of steroid carboxylic acid lactonesInfo
- Publication number
- GB1548259A GB1548259A GB2430576A GB2430576A GB1548259A GB 1548259 A GB1548259 A GB 1548259A GB 2430576 A GB2430576 A GB 2430576A GB 2430576 A GB2430576 A GB 2430576A GB 1548259 A GB1548259 A GB 1548259A
- Authority
- GB
- United Kingdom
- Prior art keywords
- canrenone
- beta
- alpha
- formation
- acetal
- 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
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
A process for the preparation of canrenone of the formula <IMAGE> starts from an acetal of 3 beta ,17 alpha -dihydroxy-17 alpha -pregn-5-ene-21-carbaldehyde and comprises the following sequence: a) bromination in position 5,6 b) oxidation of the 3 beta -hydroxy group to the 3-oxo group with formation of the 4-ene structure c) dehydrobromination in position 5,6 with formation of the 4,6-diene structure d) ring closure in position 17 by means of a compound of six-valent chromium, e.g. chromic acid, in acid solution or else starts from dehydroepiandrosterone and entails reaction with a chloropropionaldehyde acetal in the presence of lithium to give the abovementioned starting acetal and further processing as in stages a) to d). The further processing of the canrenone prepared in this way to give derivatives thereof is also described, namely on the one hand by addition of a thiocarboxylic acid, e.g. thioacetic acid, onto the 5,6-double bond of canrenone to give corresponding spironolactones, and on the other hand by cleavage of the spiro lactone ring using metal hydroxides with formation of the metal salt of the corresponding 17 beta -carboxyethyl-17 alpha -hydroxysteroid. The products of the process are known aldosterone antagonists. The described processes provide better yields and are simpler than known methods.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH769675A CH612953A5 (en) | 1975-06-13 | 1975-06-13 | Process for the preparation of steroid carbolactones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1548259A true GB1548259A (en) | 1979-07-11 |
Family
ID=4329149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2430576A Expired GB1548259A (en) | 1975-06-13 | 1976-06-11 | Process for manufacture of steroid carboxylic acid lactones |
Country Status (12)
| Country | Link |
|---|---|
| JP (2) | JPS52256A (en) |
| AT (1) | AT356299B (en) |
| BE (1) | BE842870A (en) |
| CA (1) | CA1065849A (en) |
| CH (2) | CH612953A5 (en) |
| DE (1) | DE2625723A1 (en) |
| DK (1) | DK142992C (en) |
| FR (1) | FR2313934A1 (en) |
| GB (1) | GB1548259A (en) |
| MX (1) | MX3537E (en) |
| NL (1) | NL7606350A (en) |
| SE (1) | SE416951B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3330084A1 (en) * | 1983-08-17 | 1985-03-07 | Schering AG, 1000 Berlin und 4709 Bergkamen | 7 alpha -Alkoxycarbonyl-3-oxo-17 alpha -pregn-4-ene-21,17-carbolactones and their 21-carboxylic acid salts, process for the preparation thereof, and pharmaceutical products containing these |
| JPS6095799A (en) * | 1983-10-31 | 1985-05-29 | Nec Corp | Programmable read-only memory |
| US8334375B2 (en) | 2009-04-10 | 2012-12-18 | Evestra, Inc. | Methods for the preparation of drospirenone |
| CN101731164B (en) * | 2009-11-12 | 2012-06-27 | 中国水产科学研究院渔业机械仪器研究所 | Closed water-flowing type aquaculture net cage |
| CN108047299B (en) * | 2017-12-29 | 2021-11-09 | 广西万德药业有限公司 | Preparation method of important intermediate of canrenone |
| CN113528607B (en) * | 2021-08-08 | 2023-07-11 | 浙江神洲药业有限公司 | Method for preparing spirolactone by chemical-enzymatic method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1250818B (en) * | 1963-10-01 | 1967-09-28 | G. D. Searle & Co., Chicago, 111. (V. St. A.) | Process for the production of 3-oxozl4.asteroids |
| US3682894A (en) * | 1970-02-24 | 1972-08-08 | Searle & Co | Process for preparing 3-oxo-delta4,6-steroids |
| DE2248834A1 (en) * | 1972-10-05 | 1974-04-11 | Hoechst Ag | METHOD FOR MANUFACTURING BETA (3-KETO-7 ALPHA-ACETYLTHIO-17BETA-HYDROXY4-ANDROSTEN-17 ALPHA-YL) -PROPIONIC ACID GAMMA -LACTONE |
| DE2251476A1 (en) * | 1972-10-20 | 1974-05-02 | Hoechst Ag | PROCESS FOR THE PRODUCTION OF BETA (3-KETO-7 ALPHA-THIOACYL-17 BETA-HYDROXY4-ANDROSTEN-17 ALPHA -YL) -PROPIONIC ACID GAMMA -LACTONES |
-
1975
- 1975-06-13 CH CH769675A patent/CH612953A5/en not_active IP Right Cessation
-
1976
- 1976-05-21 SE SE7605799A patent/SE416951B/en not_active IP Right Cessation
- 1976-06-09 DE DE19762625723 patent/DE2625723A1/en not_active Ceased
- 1976-06-11 BE BE167857A patent/BE842870A/en not_active IP Right Cessation
- 1976-06-11 AT AT425476A patent/AT356299B/en not_active IP Right Cessation
- 1976-06-11 FR FR7617760A patent/FR2313934A1/en active Granted
- 1976-06-11 CA CA254,684A patent/CA1065849A/en not_active Expired
- 1976-06-11 GB GB2430576A patent/GB1548259A/en not_active Expired
- 1976-06-11 NL NL7606350A patent/NL7606350A/en unknown
- 1976-06-11 MX MX30176U patent/MX3537E/en unknown
- 1976-06-11 DK DK264476A patent/DK142992C/en active
- 1976-06-12 JP JP6824976A patent/JPS52256A/en active Granted
-
1979
- 1979-04-05 CH CH318579A patent/CH617443A5/en not_active IP Right Cessation
-
1984
- 1984-08-10 JP JP16662584A patent/JPS6056998A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1065849A (en) | 1979-11-06 |
| SE7605799L (en) | 1976-12-14 |
| FR2313934B1 (en) | 1978-10-20 |
| SE416951B (en) | 1981-02-16 |
| FR2313934A1 (en) | 1977-01-07 |
| DK264476A (en) | 1976-12-14 |
| CH617443A5 (en) | 1980-05-30 |
| ATA425476A (en) | 1979-09-15 |
| AT356299B (en) | 1980-04-25 |
| CH612953A5 (en) | 1979-08-31 |
| JPS6357438B2 (en) | 1988-11-11 |
| DK142992C (en) | 1981-10-05 |
| NL7606350A (en) | 1976-12-15 |
| DE2625723A1 (en) | 1976-12-23 |
| BE842870A (en) | 1976-12-13 |
| MX3537E (en) | 1981-02-10 |
| DK142992B (en) | 1981-03-09 |
| JPS52256A (en) | 1977-01-05 |
| JPS6159320B2 (en) | 1986-12-16 |
| JPS6056998A (en) | 1985-04-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |