GB912036A - 11-methylene-5ª--steroids - Google Patents
11-methylene-5ª--steroidsInfo
- Publication number
- GB912036A GB912036A GB2206760A GB2206760A GB912036A GB 912036 A GB912036 A GB 912036A GB 2206760 A GB2206760 A GB 2206760A GB 2206760 A GB2206760 A GB 2206760A GB 912036 A GB912036 A GB 912036A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylene
- steroids
- hydroxy
- spirostan
- acetate
- 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
- 150000003431 steroids Chemical class 0.000 abstract 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000012445 acidic reagent Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J11/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises (1) a process for preparing steroids having, apart from substituents at the 16- and 17-positions, the formula <FORM:0912036/IV (b)/1> (wherein R is CHOH, CHO Acyl or CO) which comprises dehydrating and isomerizing with an acidic reagent the corresponding 11b -hydroxy-11a -methyl-5a -steroids; and (2) as new steroids, 17b - hydroxy-11-methylene-5a -androstan-3-one and the 17-acetate and -propionate thereof, 3b ,20b -dihydroxy - 11 - methylene-5a -pregnane and the diacetate thereof, 11-methylene - 5a ,25D - spirostan-3-one and 3b -hydroxy - 11 - methylene-5a ,25D-spirostan and the 3-acetate thereof. The process may be performed in one operation using formic, perchloric, sulphuric or toluene-p-sulphonic acid which may be dissolved in a lower fatty acid or anhydride or mixture thereof, or in two stages using thionyl chloride in pyridine at -20 to 40 DEG C. to effect dehydration to an 11-methyl-D 9(11)-5a -steroid which is then treated with formic acid in an inert solvent or one of the other acids referred to above in a lower fatty acid. If the starting material is a 3b ,11b -dihydroxy steroid it may be wholly or partially transformed by the acidic treatment into a 3-acyl derivative of the 11-methylene product, which may then be saponified to the free hydroxy compound or fully acylated. Examples are given. Specification 912,035 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2206760A GB912036A (en) | 1960-06-23 | 1960-06-23 | 11-methylene-5ª--steroids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2206760A GB912036A (en) | 1960-06-23 | 1960-06-23 | 11-methylene-5ª--steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB912036A true GB912036A (en) | 1962-12-05 |
Family
ID=10173366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2206760A Expired GB912036A (en) | 1960-06-23 | 1960-06-23 | 11-methylene-5ª--steroids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB912036A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2361120A1 (en) * | 1972-12-09 | 1974-06-12 | Akzo Nv | 11,11-ALKYLIDAL STEROIDS AND METHOD FOR MANUFACTURING THEREOF |
| EP1042352A4 (en) * | 1997-11-26 | 2004-12-22 | Res Triangle Inst | ANDROGENIC STEROID COMPOUNDS AND METHOD OF MANUFACTURE AND USE THEREOF |
| WO2015075693A1 (en) | 2013-11-25 | 2015-05-28 | Richter Gedeon Nyrt. | Process for the synthesis of (11 beta.17alpha)-17-acetoxy-1 1 -methyl-19-norpregn-4-en-3.20-dione |
-
1960
- 1960-06-23 GB GB2206760A patent/GB912036A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2361120A1 (en) * | 1972-12-09 | 1974-06-12 | Akzo Nv | 11,11-ALKYLIDAL STEROIDS AND METHOD FOR MANUFACTURING THEREOF |
| EP1042352A4 (en) * | 1997-11-26 | 2004-12-22 | Res Triangle Inst | ANDROGENIC STEROID COMPOUNDS AND METHOD OF MANUFACTURE AND USE THEREOF |
| WO2015075693A1 (en) | 2013-11-25 | 2015-05-28 | Richter Gedeon Nyrt. | Process for the synthesis of (11 beta.17alpha)-17-acetoxy-1 1 -methyl-19-norpregn-4-en-3.20-dione |
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