http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-874374-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_c902faf6ae746c51fc8010672fc22894 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J5-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J5-00 |
| filingDate | 1958-11-25-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1961-08-02-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-874374-A |
| titleOfInvention | Improvements in or relating to steroids and the manufacture thereof |
| abstract | The invention comprises compounds having the formulae <FORM:0874374/IV (b)/1> <FORM:0874374/IV (b)/2> <FORM:0874374/IV (b)/3> wherein the 1,2-carbon atom linkage is a single or a double bond linkage, Z is a halogen, and X is the carbonyl radical or the hydroxymethylene radical a process which comprises treating 6-fluoro-11-hydroxy-4-pregnene-3,20-dione with a dehydration agent to obtain 6-fluoro-4,9(11)-pregnadiene-3,20-dione, which on treatment with hypohalous acid in which the halogen is bromine chlorine or iodine gives 6-fluoro-9a -halo-11b -hydroxy-4-pregnene-3,20-dione; said 9a -halo compound is treated with a mild base to give 6-fluoro-9,11b -oxido-4-pregnene-3,20-dione which on treatment with hydrogen halide, e.g. HF, HCl, HBr gives the corresponding 6-fluoro-9a -halo-11b -hydroxy-4-pregnene-3,20-dione which can be oxidised to produce 6-fluoro-9a -halo-4-pregnene-3,11,20-trione. The 6-fluoro-9a -halo-11-oxygenated-4-pregnene-3,20-dione may then be dehydrogenated using microorganisms, e.g. Septomyxa, Corynebacterium, Didymella, Calonectria, Alternaria, etc. to obtain 6-fluoro-11b -hydroxy-1,4-pregnadiene-3,20-dione and 6-fluoro-1,4-pregnadiene-3,11,20-trione. The dehydrogenation may also be effected chemically by means of selenium dioxide. Alternatively the D 1,4-pregnadienes are obtained by a similar series of reactions starting with 6-fluoro-11b -hydroxy-1,4-pregnadiene-3,20-dione which is obtained by dehydrogenating 6-fluoro-11b -hydroxy-4-pregnene-3,20-dione. The process of the invention is applicable to both 6a and 6b -fluoro compounds. The 6b compounds are converted into 6a compounds by treatment with hydrogen halide, e.g. gaseous HCl. Alternatively epimerisation of the 6b ,9a -di-fluoro compounds may be effected with alkali. Specific compounds claimed are 6,9a -difluoro-11b -hydroxy-4-pregnene-3,20-dione, 6,9a - di-fluoro-4-pregnene-3,11,20-trione, 6,9a -difluoro-11b -hydroxy-1,4-pregnadiene-3,20-dione, 6,9a -difluoro - 1,4 - pregnadiene - 3,11,20-trione, 6-fluoro-9a -bromo - 11b - hydroxy - 4 - pregnene-3,20-dione, 6-fluoro-9a -bromo-11b -hydroxy-1,4-pregnadiene-3,20-dione, 6-fluoro-9,11b oxido-4-pregnene-3,20-dione, 6-fluoro-9,11b -oxido-1,4-pregnadiene-3,20-dione, 6-fluoro-4,9(11)-pregnadiene-3,20-dione and 6-fluoro-1,4,9(11)-pregnatriene-3,20-dione. Specifications 724,094 and 874,375 are referred to.ALSO:Pharmaceutical compositions incorporating compounds having the formula <FORM:0874374/VI/1> wherein the 1,2-carbon atom linkage is a single bond or a double bond linkage, X is the carbonyl radical or the hydroxymethylene radical and Y is fluorine, chlorine, or bromine, are administered orally as pills, tablets, capsules, solutions, syrups or elixirs, in liquid forms as injectable products, or topically as ointments, creams or lotions, with or without coacting antibiotics and germicides. Specifications 724,094 and 874,375 are referred to. |
| priorityDate | 1957-11-29-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 51.