http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-693754-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_6ed3169cb6d93e11328ffbf655f7f0d0 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D489-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D489-08 |
| filingDate | 1950-04-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1953-07-08-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-693754-A |
| titleOfInvention | New therapeutic compounds |
| abstract | The invention comprises amines of the formula <FORM:0693754/IV (b)/1> where R1 and R2 are methyl or ethyl (same or different), R3 and R4 are methyl or one may be hydrogen, and R5 and R6 are phenyl. These are made from the corresponding amino-alcohols R1R2N-CHR3-CHR4-CR R6OH by conversion into the chlorides with thionyl chloride at 30-80 DEG C. and then splitting off hydrogen chloride. This may happen spontaneously, or if not, the chloride is treated with a tertiary amine, preferably a further mol. of the amino-alcohol. The chlorides and the alkenes may be isolated in the form of salts. The products were originally believed to be the ethers of the amino-alcohols. In the examples: (1) b - dimethylaminobutyronitrile is made from allyl cyanide and dimethylamine and converted into the ethyl ester of the corresponding acid, e.g. by ethanolic hydrogen chloride; the ester is treated with 2 mols. of phenylmagnesium bromide to give 1 : 1-diphenyl-3-dimethylaminobutanol (isolated as hydrochloride); treatment of the latter with thionyl chloride gives 1 : 1-diphenyl-3-dimethylaminobutene-1 directly, purified as hydrochloride; (2) a -methyl-b -dimethylaminopropiophenone is made (as hydrochloride) from propiophenone, dimethylamine hydrochloride and paraformaldehyde, and treated with phenylmagnesium bromide to give 1 : 1-diphenyl-2-methyl-3-dimethylaminopropanol; the hydrochloride of the latter with thionyl chloride forms the salt of 1 : 1 - diphenyl - 2 - methyl - 3 - dimethylaminopropyl chloride; treatment of the latter with a further mol. of the amino-alcohol yields the hydrochloride of 1 : 1-diphenyl-2-methyl-3-dimethylaminopropene-1; (3) as in (2) using pyridine instead of the amino-alcohol in the final step. The invention does not include compounds when made by the process of Specification 624,117.ALSO:Analgetic compositions comprise a compound of the formula <FORM:0693754/VI/1> where R1 and R2 are methyl or ethyl (same or different), R3 and R4 are methyl or one may be hydrogen, and R5 and R6 are phenyl, together with morphine or a derivative thereof or a synthetic analgetic of the morphine type. Examples of the latter are amidone i.e. dl-6-dimethylamine-4,4-diphenyl-3-heptanone, pethidine i.e. N - methyl-4-phenyl-4-carbethoxy-pi-peridine and ketobemidone i.e. 4-(m-hydroxyphenyl)-1-methyl-4-piperidyl ethyl ketone. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-2894033-A |
| priorityDate | 1949-04-07-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 47.