GB1019576A - Synthesis of steroids - Google Patents
Synthesis of steroidsInfo
- Publication number
- GB1019576A GB1019576A GB29387/62A GB2938762A GB1019576A GB 1019576 A GB1019576 A GB 1019576A GB 29387/62 A GB29387/62 A GB 29387/62A GB 2938762 A GB2938762 A GB 2938762A GB 1019576 A GB1019576 A GB 1019576A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- acyloxy
- hydrogen
- keto
- steroids
- 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
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises a D 7-, D 7 9(11') or D 8-steriod of the general formula <FORM:1019576/C2/1> whereid Y represents oxo or x-or b -hydroxy or acyloxy, X represents oxo, acyloxy, hydroxy or hydrogen and Z represents hydroxy or acyloxy, X being oxo or hydrogen when Y is oxo, and when Y is hydroxy or acyloxy, X is acyloxy or hydrogen and the preparation thereof by treata steroid of the formula <FORM:1019576/C2/2> wherein X and Y have the above significance and B represents hydrogen or lower alkyl, with lithium aluminium hydride, treating the result ing corresponding D 7,20(22),23 - lanostatriene D 8,20(22)23, - lanostatriene or D 7,9(11),20(22)23, lano-statetraene with ozone, and reducing the result ing ozonide with zinc dust and glacial acetic acid and, if desired, forming an ester and/or oxi dizing a 3-hydroxy group and optionally a 16-hydroxy group to form a 3-keto or 3,16-diketo compound. Pharmaceutical compositions useful in the treatment of Addison's disease contain steroids of the first general formula above and a suitable pharmaceutical carrier. Steroids of the first general formula above, wherein X and Y have the significance indicated and Z represents hydrogen, are prepared by treating compounds of said general formula, wherein Y represents keto or acyloxy and Z represents hydroxy, with an organo-sulphonyl chloride to form the corresponding 21-organo-sulphonate ester, treating these compounds with an alkali metal iodide to form the corresponding 21-iodo compounds, and reducing these com pounds, for example with sodium bisulphite. If a product containing a 3b -hydroxy or acyloxy group is formed, it can be oxidized to the corresponding 3-keto compound after saponi fication of any 3-ester group. Steroids of the second general formula above wherein B, X and Y have the above significance, are prepared by treating the corresponding steroids having at ring D the formula <FORM:1019576/C2/3> wherein the symbols R may be the same or different and are hydrogen or alkyl and the symbols R1 may be the same or different and are hydrogen or hydroxy, such as eburicoic, poly-porenic, tumulosic, pinicolic, elemolic, elemonic, dehydroeburicoic, dehydroelemonic and de hydroelemolic acids (if necessary after acylating any 3-hydroxy group) with ozone and reducing the resulting ozonide to form the corresponding 24 - keto - 21 - carboxylic - compound, for ex ample, of the formula <FORM:1019576/C2/4> wherein R11 represents an acetyl group (which may also be obtained by treating said steroids having the ring D formula with a hydroxylating agent such as osmium tetroxide and then cleaving the glycol, for example of the formula <FORM:1019576/C2/5> wherein R11 represents an acetyl group), lactonizing the above 24-keto-21-carboxylic-lano stane compounds to form a mixture of steroid a - and b -lactones, for example of the general formulae <FORM:1019576/C2/6> wherein R11 has the previous significance, and dehydrogenating these compounds, for ex ample by treatment with palladium on charcoal. A resulting 3-ester may be saponified to 3-hydroxy and then oxidized to 3-keto.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13231061A | 1961-08-18 | 1961-08-18 | |
US183014A US3153038A (en) | 1962-03-28 | 1962-03-28 | Triterpenoid acid derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1019576A true GB1019576A (en) | 1966-02-09 |
Family
ID=26830254
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29387/62A Expired GB1019576A (en) | 1961-08-18 | 1962-07-31 | Synthesis of steroids |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR2879M (en) |
GB (1) | GB1019576A (en) |
-
1962
- 1962-07-31 GB GB29387/62A patent/GB1019576A/en not_active Expired
- 1962-11-05 FR FR914336A patent/FR2879M/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR2879M (en) | 1964-11-02 |
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