GB943952A - A new steroid compound and its formation - Google Patents
A new steroid compound and its formationInfo
- Publication number
- GB943952A GB943952A GB4418360A GB4418360A GB943952A GB 943952 A GB943952 A GB 943952A GB 4418360 A GB4418360 A GB 4418360A GB 4418360 A GB4418360 A GB 4418360A GB 943952 A GB943952 A GB 943952A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- dione
- hydroxy
- trione
- compound
- 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
- 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
- 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
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- 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 18-nor-pregn-16-ene-3, 11, 20-trione and processes for the production thereof which comprise the steps of first reacting a 3a -acyloxy-17-hydroxy-17-methyl-18-nor -D-homoetiocholan-11-one with a Grignard reagent to yield a 3a -acyloxy-17-hydroxy-17-methyl-18-nor-D-homoetiocholan-11 -one, saponifying this latter and then oxidising the product and reacting same with a hydrogen halide to form the corresponding 17 - halogeno - 17 - methyl-18-nor-D-homoetiocholane-3, 11-dione thereafter eliminating the hydrogen halide from this compound to give a mixture of the D 16 and D 17 isomers of 17 - methyl - 18 - nor - D - homoetiocholene-3, 11-dione, resolving the mixture so as to separate the 17-methyl-18-nor-D-homoetiochol-16-en-3, 11-dione therefrom and then subjecting this compound to the action of ozone so as to form the 16, 17-ozonide of 17-methyl-18-nor-D-homoetiocholane-3, 11-dione reducing this product to give either 1b - formylmethylene - 2a -acetonyl-4bb -methyl-8ab -perhydrophenanthrene-4, 7-dione or the isomeric compound 16#x-hydroxy-18-nor-pregnane-3, 11, 20-trione and finally dehydrating either product of the reduction reaction to yield the desired 18-norpregn-16-ene-3, 11, 20-trione. Oxidation of the 3a -hydroxy group may be effected with N-bromosuccimide in t-butanol, elimination of hydrogen halide with a lithium-halidelithium carbonate couple and reduction of the ozonide with zinc and acetic acid. Specifications 832,244, 922,315, 943,951, 943,956, 943,957 and 943,958 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR814116A FR1280589A (en) | 1959-12-24 | 1959-12-24 | New 18-nor pregnanic derivative and method of preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
GB943952A true GB943952A (en) | 1963-12-11 |
Family
ID=8723042
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4519062A Expired GB943956A (en) | 1959-12-24 | 1960-12-22 | Novel steroid compounds and processes for their preparation |
GB4519162A Expired GB943957A (en) | 1959-12-24 | 1960-12-22 | New steroid compounds and processes for the production thereof |
GB4519262A Expired GB943958A (en) | 1959-12-24 | 1960-12-22 | Novel steroid compounds and processes for their preparation |
GB4418360A Expired GB943952A (en) | 1959-12-24 | 1960-12-22 | A new steroid compound and its formation |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4519062A Expired GB943956A (en) | 1959-12-24 | 1960-12-22 | Novel steroid compounds and processes for their preparation |
GB4519162A Expired GB943957A (en) | 1959-12-24 | 1960-12-22 | New steroid compounds and processes for the production thereof |
GB4519262A Expired GB943958A (en) | 1959-12-24 | 1960-12-22 | Novel steroid compounds and processes for their preparation |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH394189A (en) |
FR (1) | FR1280589A (en) |
GB (4) | GB943956A (en) |
-
1959
- 1959-12-24 FR FR814116A patent/FR1280589A/en not_active Expired
-
1960
- 1960-12-22 CH CH1440560A patent/CH394189A/en unknown
- 1960-12-22 GB GB4519062A patent/GB943956A/en not_active Expired
- 1960-12-22 GB GB4519162A patent/GB943957A/en not_active Expired
- 1960-12-22 GB GB4519262A patent/GB943958A/en not_active Expired
- 1960-12-22 GB GB4418360A patent/GB943952A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH394189A (en) | 1965-06-30 |
GB943956A (en) | 1963-12-11 |
GB943958A (en) | 1963-12-11 |
GB943957A (en) | 1963-12-11 |
FR1280589A (en) | 1962-01-08 |
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