GB1142485A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB1142485A GB1142485A GB39137/68A GB3913768A GB1142485A GB 1142485 A GB1142485 A GB 1142485A GB 39137/68 A GB39137/68 A GB 39137/68A GB 3913768 A GB3913768 A GB 3913768A GB 1142485 A GB1142485 A GB 1142485A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- treating
- formula
- symbol
- acetic acid
- 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
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,142,485. Steroids. UPJOHN CO. 23 March, 1966 [24 March, 1965], No. 39137/68. Divided out of 1,142,484. Heading C2U. The invention comprises novel compounds having the general formulµ wherein R, R 1 and R 2 each represent hydrogen or methyl, and W 3 is Y is hydrogen or fluorine, W 1 is in which the symbol represents an alkylenedioxy radical of the formula in which n is 1 or 2 and R 6 is hydrogen or alkyl and R 5 is aryl, and processes for their preparation (a) by treating a compound of the formula wherein R, R 1 , R 2 and W 1 and the symbol have the same meanings as previously given, with an alkoxyacetylene magnesium halide to form the corresponding 6#-ethoxy-ethynyl-5α- hydroxy compound, hydrolysing the latter to form the corresponding 3-oxo-6#-acetic acid alkyl ester, treating the latter with a secondary cyclic amine to form the corresponding 3- enamine and reducing and hydrolysing the latter, (b) by treating a compound of the formula wherein R, R 1 , R 2 , W 1 and the symbol have the same meaning as previously given, or a 17-acylate thereof with an alkoxyacetylene magnesium halide to form the corresponding 6#-ethynyl-5α-hydroxy compound, reducing and hydrolysing the latter with an organic carboxylic acid followed by lithium aluminium hydride to form the corresponding 6#-(2<SP>1</SP>-hydroxyethyl) 5α-hydroxy compound and subjecting the latter to acid hydrolysis and dehydration, (c) by treating a compound of the formula wherein R, R 1 , R 2 , W 1 and the symbol have the same meaning as previously given, in an inert organic solvent with boron trifluorideethyl ether under anhydrous conditions to form the corresponding 6-oxo compound, acylating the latter at the 17-position to form the corresponding 6-carbalkoxymethyl-6-hydroxy compound, dehydrating the latter to form an isomeric mixture of the corresponding androst-5- ene-6-acetic acid alkyl ester, 5α-androst-6- acetic acid alkyl ester and the 5α-androstane- #<SP>6</SP>'α acetic acid alkyl ester, which are reduced and hydrolysed, (d) by treating a compound of the formula wherein X is Y and R 5 and the symbol have the same meaning as previously given, with an alkoxyacetylene magnesium halide to form the corresponding 6#-alkoxy-ethynyl-5xhydroxy compound, hydrolysing the latter to form the corresponding 3-oxo-6#-acetic acid alkyl ester, reacting the latter with a secondary cyclic amine to give the corresponding 3- enamine and reducing the 3-enamine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44252565A | 1965-03-24 | 1965-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1142485A true GB1142485A (en) | 1969-02-05 |
Family
ID=23757139
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39137/68A Expired GB1142485A (en) | 1965-03-24 | 1966-03-23 | Improvements in or relating to steroids and the manufacture thereof |
| GB12857/66A Expired GB1142484A (en) | 1965-03-24 | 1966-03-23 | Improvements in or relating to steroids and the manufacture thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12857/66A Expired GB1142484A (en) | 1965-03-24 | 1966-03-23 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3600412A (en) |
| CH (1) | CH481082A (en) |
| DE (1) | DE1593610A1 (en) |
| GB (2) | GB1142485A (en) |
| IL (1) | IL25298A (en) |
| NL (1) | NL6603861A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5319115A (en) * | 1987-08-25 | 1994-06-07 | Cocensys Inc. | Method for making 3α-hydroxy, 3β-substituted-pregnanes |
-
1965
- 1965-03-24 US US442525A patent/US3600412A/en not_active Expired - Lifetime
-
1966
- 1966-03-03 IL IL25298A patent/IL25298A/en unknown
- 1966-03-11 CH CH350066A patent/CH481082A/en not_active IP Right Cessation
- 1966-03-15 DE DE19661593610 patent/DE1593610A1/en active Pending
- 1966-03-23 GB GB39137/68A patent/GB1142485A/en not_active Expired
- 1966-03-23 GB GB12857/66A patent/GB1142484A/en not_active Expired
- 1966-03-24 NL NL6603861A patent/NL6603861A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH481082A (en) | 1969-11-15 |
| US3600412A (en) | 1971-08-17 |
| GB1142484A (en) | 1969-02-05 |
| DE1593610A1 (en) | 1970-12-03 |
| IL25298A (en) | 1970-08-19 |
| NL6603861A (en) | 1966-09-26 |
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