http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-786156-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_d202e9e866984fe229f6facc38f1d740 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D489-08 |
| filingDate | 1954-05-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1957-11-13-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-786156-A |
| titleOfInvention | Morphine derivatives and processes for producing them |
| abstract | The invention comprises: (a) D 6-desoxymorphine derivatives having a carbalkoxy or carbaralkoxy group on the oxygen atom attached to the carbon atom in the 3-position and a lower (1-5C) alkyl or an aryl radical attached to the carbon atom in the 6-position, and salts thereof, also other O3-acyl-6-aryl-D 6-desoxymorphines; (b) the manufacture of compounds of the general formula <FORM:0786156/IV (b)/1> (wherein R represents a lower alkyl or aryl radical and R1 an acyl radical, including the residue of a carboxylic acid as well as carbalkoxy and carbaralkoxy) by the action of a dehydrating agent on the corresponding O3-acyl-6-substituted-dihydromorphines, which may be prepared by the process of Specification 786,157; and (c) hydrolysis or alcoholysis of compounds of the general formula above to form the corresponding free hydroxy compounds (6-lower-alkyl-and 6-aryl-D 6-desoxymorphines). Process (b) may be effected by means of a phosphorus, sulphur or acyl halide (e.g. PBr3, PCl3, SOCl2, SOBr2, PCl5, SO2Cl2, SO2Br2 or acetyl chloride), advantageously in a solvent (e.g. pyridine (preferred), water, or organic solvents having no reactive hydrogen atoms), and process (c) by means of acid or alkaline reagents in aqueous, anhydrous organic or aqueous organic solvents, especially by alcoholysis with alcoholic caustic potash or by hydrolysis with dilute mineral acids (yielding a salt of the final product, such as the hydrochloride, hydrobromide, sulphate or phosphate). In examples: (1) O3-carbomethoxy - 6 - methyldihydromorphine is refluxed with SOCl2 in chloroform to produce O3-carbomethoxy - 6 - methyl - D 6 - desoxymor - phine, which is hydrolysed with aqueous alcoholic caustic potash to 6-methyl-D 6-desoxymorphine; (2) the first step of (1) is effected by standing with SOCl2 and pyridine, and the second with aqueous alcoholic caustic soda; (3) O3 - carbethoxy - 6 - methyldihydromorphine is treated as in (1); the final product is converted into its hydrochloride and hydrobromide; (4) O3 - carbethoxy - 6 - ethyldihydromorphine similarly yields O3 - carbethoxy - 6 - ethyl - D 6-desoxymorphine and 6-ethyl-D 6-desoxymorphine, the hydrobromide of which is described; (5) O3 - carbethoxy - 6 - phenyldihydromorphine similarly gives O3-carbethoxy-6-phenyl-D 6-desoxymorphine and 6 - phenyl - D 6 - desoxymorphine, the hydrochloride of which is described; (6) O3 - carbobenzoxy - 6 - methyldihydromorphine is treated as in (1); (7) O3-acetyl-6-methyldihydromorphine is treated as in the first part of (2) to produce O3-acetyl-6-methyl-D 6-desoxymorphine (the hydrochloride of which is described), and the product is hydrolysed as in the second part of (1); (8) O3-carbethoxy-6-butyl-dihydromorphine is treated as in the first part of (1) to form O3-carbethoxy-6-butyl-D 6-desoxymorphine, which is hydrolysed with aqueous alcoholic caustic soda (containing a trace of NaHSO3) to 6 - butyl - D 6 - desoxymorphine. Specification 738,207 also is referred to. |
| priorityDate | 1953-06-02-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 68.