http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1062704-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_1bf2ba08adb8ed810fa2aafc13dea308 |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/Y02P20-55 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D459-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D459-00 |
| filingDate | 1966-02-03-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1967-03-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1062704-A |
| titleOfInvention | Diesters of 18-hydroxy-yohimbane-carboxylic acids |
| abstract | Novel compounds of the formula <FORM:1062704/C2/1> wherein R1 is a C1- 3 alkyl radical, R2 and R3, which may be the same or different, are H, alkyl (which may be joined together to form a ring) or aryl, which may be substituted by one, two or three C1- 3 alkoxy radicals, and R4 is CH3O- or H, and their salts with inorganic and organic acids, and their optically active isomers, are prepared by reacting a compound of formula <FORM:1062704/C2/2> wherein R1 and R4 are as previously defined, in a known manner with a reactive carboxylic derivative of an a -hydroxy acid of formula <FORM:1062704/C2/3> wherein R2 and R3 are as previously defined, and X is a protective group, and the protective group in the resulting reserpic acid derivative is split off, whereupon the desired product obtained is, if desired, converted into a salt with an organic or inorganic acid, and/or separated into its optically active isomers. The compounds are of use in the pharmacological field. 18 - (O - tetrahydropyranyl - DL - mandelic acid) ester of methyl reserpate, which may optionally bear up to three CH3O- groups on the mandelic acid benzene ring, and 18-(a -tetrahydropyranyloxy - cyclohexane - carboxylic acid) ester of methyl reserpate are isolated reserpic acid derivatives, as intermediates in the above process. The imidazolide of O-tetrahydropyranyl-DL-(and L)-mandelic acid and also the 3,4-dimethoxy and 3,4,5-trimethoxy DL-derivatives thereof are prepared by reacting the corresponding mandelic acid with dihydropyran in the presence of p-toluene sulphonic acid to give the corresponding tetrahydropyranyl ester of O-tetrahydropyranyl mandelic acid, which is then reacted with NaOH to give the Na-salt of the O-tetrahydropyranyl mandelic acid, followed by acidification to the free acid, with oxalic acid, which is then reacted with N,N1-carbonyldiimidazole to give the imidazolide. The imidazolide of a -tetrahydropyranyloxy-cyclohexane-carboxylic acid is prepared by reacting cyclohexanone cyanohydrin with dihydropyran to give a -tetrahydropyranyloxy-cyclohexane-carboxylic acid nitrile, which is then subjected to alkaline saponification, yielding the free acid, which is subsequently reacted with N, N1-carbonyldiimidazole. |
| priorityDate | 1965-02-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 35.