http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-978531-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_4acae202b6a15394281949545e70d2f6 |
| filingDate | 1962-03-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1964-12-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-978531-A |
| titleOfInvention | Yohimbane derivatives |
| abstract | The invention comprises 6,6-dimethyl -16b -methoxycarbonyl -17a - methoxy -18b - hydroxy-3a , 20a -yohimbane, 6,6-dimethyl -16b - methoxycarbonyl -17a - methoxy -18b - hydroxy-3b , 20a -yohimbane, 6,6-dimethyl -16b - methoxycarbonyl-17a - methoxy -18b - acetoxy-3a , 20a -yohimbane, laevorotatory (pyridine) 6,6-dimethyl -16b -methoxycarbonyl -17a - methoxy -18b - acetoxy-3b , 20a -yohimbane, dextrorotatory (pyridine) 6,6-dimethyl -16b - methoxycarbonyl -17a -methoxy -18b - acetoxy-D 3(14) 20a -yohimbane and laevorotatory (pyridine) 6,6-dimethyl -16b -methoxycarbonyl -17a - methoxy -18b - (31, 41, 51-trimethoxybenzoyloxy)-3b , 20a -yohimbane and its salts with acids having physiologically compatible anions: it comprises also the process for the preparation of the above compounds by condensing 1b -carboxymethyl-2b -methoxycarbonyl -3a - methoxy -4b - acetoxy -6b - formylcyclohexane or an ester thereof with b , b -dimethyltryptamine and converting the resulting Schiffs base e.g. 6,6-dimethyl -16b - methoxycarbonyl -17a - methoxy -18b - acetoxy 2,3-3,4-diseco D 4(21) 20a -yohimbane -3- oic acid to the desired product by reduction of the 4,21-double bond e.g. with alkali-metal borohydride to the corresponding yohimbane -3- oic acid, lactam formation between the 3- and 4-positions, e.g. by heating, to give the 6,6-dimethyl -16b - methoxycarbonyl -17a - methoxy -18b - acetoxy-2, 3-seco -3- oxo -20a - yohimbane, cyclisation between the 2- and 3-positions e.g. by treatment with POCl3, to give dextrorotatory (pyridine) 6,6-dimethyl -16b - methoxycarbonyl -17a - methoxy -18b - acetoxy- D 3(14)-20a -yohimbane, reduction to form laevorotatory (pyridine] 6,6-dimethyl-16b -methoxycarbonyl -17a - methoxy -18b -acetoxy-3b , 20a -yohimbane and the corresponding 3a , 20a -yohimbane together with some of the hydrolysis product 6,6-dimethyl -16b - methoxycarbonyl -17a - methoxy -18b - hydroxy-3a , 20a -yohimbane, hydrolysis of the -18b - acetoxy-3b isomer suitably by an alkali-metal borohydride to the corresponding 18b -hydroxy compound and acylation of this with 3,4,5-trimethoxybenzoyl chloride to 6,6-dimethyl -16b - methoxycarbonyl -17a - methoxy -18b - (31, 41, 51-trimethoxybenzoyloxy)-3b , 20a -yohimbane (laevorotator in pyridine). Pharmaceutical preparations having a depressive activity on the central nervous system comprise the above laevorotatory 6,6-dimethyl-16b -methoxycarbonyl -17a -methoxy -18b - (31, 41, 51-trimethoxybenzoyloxy) -3b , 20a -yohimbane or a non-toxic salt thereof together with a carrier or excipient, suitably in the dosage units containing 1-10 mg. of active compound. The preparations may, for example, take the form of solutions, suspensions, tablets, capsules, pills or suppositories. Specifications 868,485 and 969,266 are referred to. |
| priorityDate | 1961-03-21-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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