GB886964A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB886964A GB886964A GB25814/61A GB2581461A GB886964A GB 886964 A GB886964 A GB 886964A GB 25814/61 A GB25814/61 A GB 25814/61A GB 2581461 A GB2581461 A GB 2581461A GB 886964 A GB886964 A GB 886964A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acylate
- hydroxyprogesterone
- oxido
- dione
- alkylene
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 hydrocarbon carboxylic acid Chemical class 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- ALSXNTIVNJBNQE-ZWONNITHSA-N (8r,9r,10s,13r,14s,17s)-17-ethyl-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15,16,17-hexadecahydrocyclopenta[a]phenanthrene Chemical class C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 ALSXNTIVNJBNQE-ZWONNITHSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises a 5,6-oxido-17a -hydroxypregnane-3,20-dione 17-acylate 3-alkylene ketal wherein the acyl group is of a hydrocarbon carboxylic acid containing 1-12 carbon atoms and wherein the alkylene radical contains not more than 8 carbon atoms, and the attaching oxygen to carbon bonds are separated by a chain of at least 2 and not more than 3 carbon atoms, the corresponding 19-nonpregnane compounds, a compound of the formula <FORM:0886964/IV (b)/1> wherein R11 is hydrogen and Ac is the acyl group defined above, a compound of the formula <FORM:0886964/IV (b)/2> wherein R is the alkylene radical defined above and Ac is the acyl radical defined above and processes for the preparation thereof by treating a 17a -hydroxyprogesterone I with an anhydride or halide of an organic carboxylic acid to obtain the corresponding enol acylate of 17a -hydroxyprogesterone 17-acylate which is hydrolysed to give 17a -hydroxyprogesterone-17-acylate II, treating II with an alkane diol to obtain 17a -hydroxyprogesterone 17a -acylate 3-alkylene ketal III, and treating III with a peracid to obtain 5a ,6a -oxido-17a -hydroxy-pregnane-3,20-dione 17-acylate, 3-alkylene ketal IV. The 19-norpregnane compounds are similarly converted. Examples describe the preparations of 5a ,6a -oxido-17-hydroxypregnane-3,20-dione 17-acetate, 5a ,6a -oxido - 17a - hydroxy - 19 - norpregnane - 3, 20 - dione 17-acetate 3-ethylene ketal. Specification 848,881 also is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US886964XA | 1957-11-29 | 1957-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB886964A true GB886964A (en) | 1962-01-10 |
Family
ID=22212898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25814/61A Expired GB886964A (en) | 1957-11-29 | 1958-11-25 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB886964A (en) |
-
1958
- 1958-11-25 GB GB25814/61A patent/GB886964A/en not_active Expired
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