GB909201A - New steroid products and process of preparing them - Google Patents
New steroid products and process of preparing themInfo
- Publication number
- GB909201A GB909201A GB13767/61A GB1376761A GB909201A GB 909201 A GB909201 A GB 909201A GB 13767/61 A GB13767/61 A GB 13767/61A GB 1376761 A GB1376761 A GB 1376761A GB 909201 A GB909201 A GB 909201A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- hydrogen
- acid
- androsten
- double bond
- 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
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
-
- 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
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- 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
- 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 steroid lactones of the general formula <FORM:0909201/IV (b)/1> wherein Y represents hydrogen or methyl (there either is or is not a 2:3 double bond in the lactone ring), X represents keto, b -hydroxy and a -hydrogen, or b -acyloxy and a -hydrogen where the acyl radical is derived from an aliphatic acid containing from 1 to 9 carbon atoms, and wherein when X represents keto there is either a 4:5 double bond or a 5a -hydrogen atom, and when X is b -hydroxy (or acyloxy) and a -hydrogen there is either a 5:6-double bond or a 5a -hydrogen atom but not 2:3-double bond in the lactone ring, the salts produced by treating the above lactones with alkali, and the corresponding hydroxy-acids derived from the salts; and processes for the preparation of (a) the lactone of 4-hydroxy4 - (3b -hydroxy-5-androsten-17b -yl)-2-pentenoic acid or the corresponding butenoic acid by hydrogenating the corresponding 2-pentinoic or butinoic acid with one mol of hydrogen in the presence of Lindlar palladium in tetrahydrofuran or alcohol solution, (b) the lactone of 4-hydroxy-4-(3b -hydroxy-5-androsten-17b -yl) pentanoic acid or of 4-hydroxy-4-(3b -hydroxy-5a -androstane-17b -yl) pentanoic acid or of either of the corresponding butanoic acids by hydrogenating 4-hydroxy-4-(3b -hydroxy-5-androsten-17b -yl) pentinoic acid or the corresponding butanoic acid in the presence of 10% palladium over carbon in tetrahydrofuran or alcohol solution until the requisite amount of hydrogen is absorbed, (c) the 3-acyloxy compounds defined by the general formula above by acylating the corresponding 3-hydroxy compounds, e.g. to form 3-acetates, propionates, valerates, b -phenylpropionates, b -cyclopentylpropionates and hemisuccinates and (d) the 3-keto compounds defined by the general formula above by oxidising the corresponding 3b -hydroxy compound having the double bond, if at all, in the 5:6 position. Therapeutic compositions useful as nutriuretics contain a steroid lactone of the above general formula and a solid and/or liquid pharmaceutically acceptable carrier. p 4-Hydroxy - 4 - (3b -hydroxy-5-androsten-17b -yl)-T-pentionic and -butinoic acids are prepared by reacting ethynyl magnesium bromide with pregn-5-en-3b -ol-20-one and 17b -formyl-5-androsten-3b -ol-3-acetate to form 20-ethynyl-21-nov-5-pregnene-3b ,20-diol respectively, and reacting the 20-ethynyl compounds with a Grignard reagent and then carboxylating with carbon dioxide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT694760 | 1960-04-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB909201A true GB909201A (en) | 1962-10-31 |
Family
ID=11122612
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB13767/61A Expired GB909201A (en) | 1960-04-20 | 1961-04-17 | New steroid products and process of preparing them |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR1078M (en) |
GB (1) | GB909201A (en) |
-
1961
- 1961-04-17 GB GB13767/61A patent/GB909201A/en not_active Expired
- 1961-04-18 FR FR859056A patent/FR1078M/en active Active
Also Published As
Publication number | Publication date |
---|---|
FR1078M (en) | 1962-01-22 |
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