GB911429A - New steroid compounds - Google Patents
New steroid compoundsInfo
- Publication number
- GB911429A GB911429A GB16052/61A GB1605261A GB911429A GB 911429 A GB911429 A GB 911429A GB 16052/61 A GB16052/61 A GB 16052/61A GB 1605261 A GB1605261 A GB 1605261A GB 911429 A GB911429 A GB 911429A
- Authority
- GB
- United Kingdom
- Prior art keywords
- progesterone
- methyl
- treating
- hydroxy
- hydrogen
- 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
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- 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
The invention comprises steroids of the general formula <FORM:0911429/IV (b)/1> wherein R represents hydrogen or a halogen of a free or a carboxylic esterified hydroxy group, R1 represents an aliphatic, cycloaliphatic or arylaliphatic hydrocarbon group containing from 4 to 7 carbon atoms, X represents hydrogen, fluorine or chlorine or the methyl group, Y is hydrogen or the methyl group, and Z represents hydrogen or the methyl or a free or a carboxylic esterified hydroxy group with the limitation that X, Y and Z do not all represent hydrogen except when R represents a halogen, but when one of these symbols is other than hydrogen the other two symbols represent hydrogen, and the preparation thereof by reacting a corresponding D 4-3-keto-steroid with an alcohol of the formula R1OH wherein R1 has the above significance, in the presence of an acid catalyst and a lower alkyl orthoformate in solution in an organic solvent. A preferred method of preparation comprises reacting the D 4-3-keto-steroid with a lower alkyl orthoformate in the presence of an acid catalyst and then reacting the lower alkyl enol ether of the D 4-3-keto-steroid with the alcohol R1OH. Pharmaceutical compositions having a progestational effect comprise one or more steroids of the above general formula and a non-toxic liquid or solid pharmaceutical carrier. Preferred carriers are oils such as olive, sesame, linseed, wheat germ, sunflower seed, egg yolk or pine oil. 6b -Chloro(and fluoro)-progesterone are prepared by treating progesterone ethyl enol ether with N-chlorosuccinimide and glacial acetic acid and with perchloryl fluoride respectively. 2a -Methyl-17a -acetoxy-progesterone is prepared by treating 17a -hydroxy-pregnenolone with ethyl glycol in the presence of p-toluenesulphonic acid, treating the resulting 20-ethylene ketal of 17a -hydroxy-pregnenolone with cyclohexanone and aluminium isopropylate, treating the resulting 20-ethylene ketal of progesterone with sodium hydride and diethyl oxalate to form the sodium salt of the 20-ethylene ketal of 2-ethoxyoxalyl-progesterone, reacting this compound with monopotassium phosphate, then with methyl iodide and finally with sodium methylate to form 2a -methyl-17a -hydroxy-progesterone, and acetylating this compound. 16a -Acetoxy - 17a - hydroxy - progesterone is prepared by treating pregna-4,16-dien-3,20-dione with osmium tetroxide or potassium permanganate, and acetylating the resulting 16a ,17a -dihydroxy-progesterone. 16a -Methyl-progesterone is prepared by treating pregna - 4,16-dien - 3,20 - dione with methyl magnesium bromide in the presence of cuprous chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26712A US3240671A (en) | 1960-02-06 | 1960-05-04 | Therapeutic composition containing the 3-cyclopentyl enol ether of 17alpha-acetoxy progesterone and method of using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB911429A true GB911429A (en) | 1962-11-28 |
Family
ID=21833389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16052/61A Expired GB911429A (en) | 1960-05-04 | 1961-05-03 | New steroid compounds |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH413830A (en) |
| ES (1) | ES267348A1 (en) |
| FR (1) | FR1094M (en) |
| GB (1) | GB911429A (en) |
-
1961
- 1961-05-02 FR FR860509A patent/FR1094M/en active Active
- 1961-05-03 GB GB16052/61A patent/GB911429A/en not_active Expired
- 1961-05-03 ES ES0267348A patent/ES267348A1/en not_active Expired
- 1961-05-03 CH CH517961A patent/CH413830A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES267348A1 (en) | 1961-09-01 |
| FR1094M (en) | 1962-01-29 |
| CH413830A (en) | 1966-05-31 |
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