http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-836973-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/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J5-00 |
classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J5-00 |
filingDate | 1957-02-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationDate | 1960-06-09-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationNumber | GB-836973-A |
titleOfInvention | Improvements in or relating to steroids and the manufacture thereof |
abstract | The invention comprises a compound having the general formula <FORM:0836973/IV (b)/1> wherein R is hydrogen or an acyl radical of a hydrocarbon carboxylic acid containing from 1-8 carbon atoms inclusive, R1 is a lower alkyl radical containing from 1-8 carbon atoms inclusive and X1 is bromine, chlorine, fluorine or iodine and a process for the production thereof, which comprises dehydrating a compound having the formula <FORM:0836973/IV (b)/2> wherein R1 is as defined above and Ac is the acyl radical of a hydrocarbon carboxylic acid containing from 1-8 carbon atoms inclusive, with a hypohalous acid and anhydrous SO2 to produce a compound having the formula <FORM:0836973/IV (b)/3> wherein R1 and Ac are as above defined, treating the latter compound with hypohalous acid in which the halogen is Cl, Br or I to form a compound having the formula <FORM:0836973/IV (b)/4> wherein R1 and Ac are as above defined and X is bromine, chlorine or iodine, treating this compound with a base to yield a compound having the formula <FORM:0836973/IV (b)/5> wherein R1 and Ac are as above defined and then treating the thus produced epoxy compound with a hydrogen halide wherein the halogen is chlorine, bromine, fluorine or iodine in the presence of a strong mineral acid to produce a 2-lower-alkyl-9a -halo-11b ,17a -dihydroxy - 21 - acyloxy - 4,6 - pregnadiene - 3,20 - dione and then if desired hydrolysing the latter compound to form the corresponding 2-lower alkyl - 9a - halo - 11b ,17a ,21 - trihydroxy - 4,6 - pregnadiene-3,20-dione. The first dehydration step may be effected with POCl3, HCl, H2SO4 in acetic acid, or with an N-haloamide or N-haloimide by treating the intermediate hypohalite with dry SO2 in an organic base. The 9-halo compound is obtained from the 9(11)-dehydro compound by adding hypochlorous or hypobromous acids. The 9-fluoro compound is obtained therefrom by cyclization with potassium acetate, sodium bicarbonate, or sodium acetate to form a 9(11)-epoxy compound followed by reaction with HF in the presence of a strong acid. Examples describe the preparation of 2 - ethyl - 9a - chloro - 11b ,17a ,21 - trihydroxy - 4,6 - pregnadiene - 3,20 - dione - 21 - acetate, 2 - methyl - 9a - bromo - 11b ,17a ,21 - trihydroxy-4,6 - pregnadiene - 3,20 - dione - 21 - acetate and the corresponding 2-propyl-, 2-benzyl-, 2-butyl-, 2-hexyl- and 2-octyl compounds. Additionally, 9a -fluoro and 9a -iodo compounds and other 21-esters are illustrated.ALSO:Compounds having the formula <FORM:0836973/VI/1> wherein R is hydrogen or an acyl radical of a hydrocarbon carboxylic acid containing 1-8 carbon atoms inclusive, R1 is a lower alkyl radical containing 1-8 carbon atoms inclusive and X1 is bromine, chlorine, fluorine or iodine, are employed topically in dermatological and ophthalmic ointments and therapeutic dentifrices. A suitable dermatological and ophthalmic ointment comprises wool fat, mineral oil, 2 - methyl - 9a - fluoro - 11b ,17a - dihydroxy - 21 - acetoxy K 4,6 - pregnadiene - 3,20 - dione and white petrolatum. An antibiotic such as neomycin sulphate, bacitracin, circulin, polymyxin B sulphate, gramicidin, streptomycin sulphate, dihydrostreptomycin sulphate, oxytetracycline, chlortetracycline, tetracycline, and chloramphenicol or sulphonamides may also be present. A therapeutic dentifrice comprises precipitated calcium carbonate, titanium oxide, distilled water, methylcellulose, sodium lauryl sulphate, glycerine, methyl-p-hydroxybenzoate, 2 - methyl - 9a - fluoro - 11b ,17a - dihydroxy - 21 - acetoxy - 41,6 - pregnadiene - 3 - one, cinnamon oil, peppermint oil and spearmint oil. Saccharine may be used for sweetening and the titanium oxide may be substituted by calcium carbonate or dicalcium phosphate. Antibiotics may also be present. A dental ointment comprises white petrolatum, white wax, 2-methyl-9a - fluoro - 11b ,17a - dihydroxy - 21 - acetoxy - 4,6 - pregnadiene - 3,20 - dione and flavouring oil. Antibiotics and/or sulphonamides may be added. |
priorityDate | 1956-03-29-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 80.