GB968255A - New unsaturated 16-methylene-3-keto-steroids and process for their manufacture - Google Patents
New unsaturated 16-methylene-3-keto-steroids and process for their manufactureInfo
- Publication number
- GB968255A GB968255A GB43424/62A GB4342462A GB968255A GB 968255 A GB968255 A GB 968255A GB 43424/62 A GB43424/62 A GB 43424/62A GB 4342462 A GB4342462 A GB 4342462A GB 968255 A GB968255 A GB 968255A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- steroids
- hydroxylating
- dehydro derivatives
- dehydrogenating
- 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
- 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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises steroids of the general formula: <FORM:0968255/C1/1> and the corresponding 1-dehydro derivatives, wherein X represents hydrogen or fluorine, Y represents a free or esterified hydroxy group, and R represents H(b OH) or O, and the preparation thereof by treating steroids of the general formula: <FORM:0968255/C1/2> wherein X and Y have the above significance, R1 represents H,H;H, a - or b -OH; or O, and A-B represents: <FORM:0968255/C1/3> with chloranil and, when R1 represents H,H, 11-hydroxylating the product microbiologically and, for the production of the 1-dehydro derivatives, dehydrogenating the product with 1,2-dichloro-5,6-dicyano-p-benzoquinone or with dehydrogenating micro-organisms such as those of the genus Alternaria, Didymella, Calonectria, Colletotrichum, Cylindrocarpon, Fusarium, Ophiobolus, Septomyxa, Vermicularia, Acetobacter, Aerobacter, Alcaligenes, Bacillus, Corynebacterium, Crysipelothrix, Listeria, Micromonospora, Mycobacterium, Nocardia, Protaminobacter, Pseudomonas, and Streptomyces. A steroid of the first general formula above containing an 11a -hydroxy group may be oxidized to form an 11-keto compound, or containing a 21-ester group may be saponified to a 21-hydroxy which may then be re-esterified as required. The 11-hydroxylation may be carried out with an 11b -hydroxylating micro-organism such as fungi of the genus Curvularia, Stachylidium and Streptomyces, or with an 11a -hydroxylating microorganism such as Absidia, Cunninghammella, Fusarium, Mucor, Penicillium and Rhizopus. Therapeutic compositions suitable for parenteral, enteral or local application and having corticoid properties contain as the active ingredients steroids of the first general formula above and the corresponding 1-dehydro derivatives.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEM50922A DE1212528B (en) | 1961-11-18 | 1961-11-18 | Process for the preparation of delta 1,4,6-16-methylene-3, 20-diketo-steroids |
DEM50923A DE1215706B (en) | 1961-11-18 | 1961-11-18 | Process for the preparation of delta 4,6-16-methylene-3, 20-diketo-steroids |
DEM50991A DE1204223B (en) | 1961-11-25 | 1961-11-25 | Process for the production of unsaturated 16-methylene-3-keto-steroids |
Publications (1)
Publication Number | Publication Date |
---|---|
GB968255A true GB968255A (en) | 1964-09-02 |
Family
ID=27211586
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB43424/62A Expired GB968255A (en) | 1961-11-18 | 1962-11-16 | New unsaturated 16-methylene-3-keto-steroids and process for their manufacture |
Country Status (4)
Country | Link |
---|---|
CH (1) | CH420137A (en) |
FR (1) | FR2491M (en) |
GB (1) | GB968255A (en) |
SE (1) | SE314064B (en) |
-
1962
- 1962-10-09 CH CH1185062A patent/CH420137A/en unknown
- 1962-11-12 SE SE12104/62A patent/SE314064B/xx unknown
- 1962-11-16 FR FR915630A patent/FR2491M/en active Active
- 1962-11-16 GB GB43424/62A patent/GB968255A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH420137A (en) | 1966-09-15 |
SE314064B (en) | 1969-09-01 |
FR2491M (en) | 1964-04-27 |
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