http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1062713-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_6b6fc801b5bfe5304ffa40d938db6e09 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-74 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-70 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-44 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D211-48 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-74 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-70 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-48 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D211-44 |
| filingDate | 1964-08-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1967-03-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1062713-A |
| titleOfInvention | 4'-hydroxy-4'-piperidyl-ketones |
| abstract | The invention comprises compounds of the general formula <FORM:1062713/C2/1> and acid addition salts thereof wherein R1 is hydrogen or alkyl containing up to 12 carbon atoms or alkenyl containing 3-5 carbon atoms or cyclopropylmethyl or phenylalkyl containing 7-9 carbon atoms, R2 is hydrogen or methyl or is linked with R3 to give an optionally methyl substituted polymethylene chain containing 3-6 carbon atoms, R3 is alkyl containing up to 4 carbon atoms, phenyl, phenylalkyl containing from 7-9 carbon atoms or styryl, or is linked to R2 as described above, and R4 is hydrogen or methyl, and acid addition salts thereof, and the preparation thereof by one of the following methods:-(a) reaction of a compound of the general formula <FORM:1062713/C2/2> with a ketone of the formula R3-CO-CH2-R2, (b) hydrolysis of an imine of the general formula <FORM:1062713/C2/3> wherein R5 is a hydrocarbon radical, preferably cyclohexyl, and M is an alkali metal atom, (c) reaction of a compound of the general formula <FORM:1062713/C2/4> wherein R111 is a radical corresponding to R1 or is the benzyloxycarbonyl radical and R31 is R3 minus CH2, with an aqueous mineral acid containing mercury II ions and by splitting off any benzyloxycarbonyl radical R111 by means of hydrogenolysis, or (d) reaction of a compound of the first general formula above wherein R1 is hydrogen and R2, R3 and R4 have the meanings given above with a reactive ester of a compound of the general formula R11-OH, wherein R11 has any meaning given for R other than hydrogen, and if desired converting any compound obtained into a salt with an inorganic or organic acid. Imines of the third general formula above may be prepared by converting a ketimine of the formula <FORM:1062713/C2/5> into its alkali metal compound, particularly the lithium compound, and reacting the latter with a compound of the general formula <FORM:1062713/C2/6> wherein R11 has any meaning given for R1 other than hydrogen. Ketimines of the above formula are prepared by reaction of the corresponding ketone with a primary amine in an inert solvent. The compounds of the fourth general formula above wherein R111, R31, R2 and R4 have the above meanings are prepared by reaction of a1-benzyloxycarbonyl-4-piperidone of the last formula above with a suitable propargyl halide. Therapeutic compositions in conventional forms for oral or parenteral administration, having analgetic and antitussive activity, comprise a compound of the first general formula above, or a pharmaceutically acceptable acid addition salt thereof, and at least one pharmaceutically acceptable carrier. |
| priorityDate | 1963-07-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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Total number of triples: 25.