http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1017696-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/C07F1-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F1-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61K31-33 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F1-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F1-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-33 |
| filingDate | 1962-09-14-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1966-01-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1017696-A |
| titleOfInvention | Substituted 5h-dibenzo[a, d]cycloheptenes and 10,11-dihydro-5h-dibenzo[a, d]cycloheptenes |
| abstract | The invention comprises substituted 5H-dibenzo[a,d]cycloheptene and their 10,11-dihydro derivatives which compounds have the general formulae <FORM:1017696/C2/1> wherein Z represents -CH2CH2CH2- or -CCCH2-which may be further substituted by a C1-C4 alkyl radical, each of R and R1 represents a C1-C6 alkyl radical or a cycloalkyl, phenyl or benzyl radical provided that when R and R1 are other than alkyl radicals the total number of carbon atoms in R and R1 does not exceed 9 and provided further that when Z is the radical -CH2CH2CH2-which radical may by further substituted by a C1-C4 alkyl radical and R and R1 are both alkyl radicals they are linked together through a nitrogen atom to form a 1-lower alkyl-4-piperazinyl radical, and when Z is the radical -CCH2-which radical may be further substituted with a C1-C4 alkyl radical, R and R1 may be linked together through a carbon, nitrogen or oxygen atom to form a 1-piperidyl, 4-morpholinyl, 1-pyrrolidyl or 1 - (C1- 4 alkyl) - 4 - piperazinyl ring, and each of X and X1 represents a hydrogen or a halogen atom or a C1- 4 alkoxy, C1- 4 alkylmercapto, C1- 4 alkylsulphonyl or C2- 8 dialkylsulphamoyl group and acid addition salts thereof; and a process for the preparation of compounds of the above general formulae wherein Z represents -CH2CH2CH2- or -CCCH2-which may be further substituted by a C1-C4 alkyl radical, and each of R and R1 is a C1-C6 alkyl radical or a cycloalkyl, phenyl or benzyl radical provided that when R and R1 are other than alkyl radicals the total number of carbon atoms in R and R1 does not exceed 9 and provided further that when R and R1 are both alkyl radicals, they may be linked together through carbon, nitrogen or oxygen atoms to form a 1-piperidyl, 4-morpholinyl, 1-pyrrolidyl or 1-C1- 4 alkyl-4-piperazinyl ring, by reacting the required 5-halo-substituted 5H-dibenzo[a,d]cycloheptene or 10,11-dihydro derivative thereof with the required organo-metal compound of the formula <FORM:1017696/C2/2> wherein Y represents lithium or Hal-Mg. Acid addition salts of the compound defined above are also mentioned. Pharmaceutical compositions useful as anti-depressants contain as the active ingredients the substituted 5H-dibenzo[a,d]cycloheptenes and their 10,11-dihydro derivatives defined above. The compositions may be administered in the form of powders, capsules, tablets, elixirs, solutions or aqueous suspensions. 5 - Chloro - 3 - methylmercapto - 5H - dibenzo[a,d]cycloheptene is prepared by reacting methyl mercaptan and cuprous chloride, reacting the resulting cuprous methyl mercaptide with 3-bromo - 5H - dibenzo[a,d]cyclohepten - 5 - one to form 3 - methylmercapto - 5H - dibenzo[a,d]-cyclohepten-5-one, reducing this compound with potassium borohydride to form 3-methyl-mercapto - 5H - dibenzo[a,d]cyclohepten - 5 - ol, treating this compound with hydrogen chloride to form the desired corresponding 5-chloro compound. 5 - Chloro - 3 - dimethylsulphamoyl - 5H - dibenzo[a,d]cyclohepten is prepared by reacting 3 - bromo - 10,11 - dihydro - 5H - dibenzo[a,d]-cyclohepten-5-one with fluosulphonic acid to form 3 - bromo - 7 - fluorosulphonyl - 10,11 - dihydro - 5H - dibenzo[a,d]cyclohepten - 5 - one, treating this compound with dimethylamine to form 3 - bromo - 7 - dimethylsulphamoyl - 10,11 -dihydro - 5H - dibenzo[a,d]cyclohepten - 5 - one, hydrogenating this compound in the presence of palladium on charcoal to form 3-dimethylsulphamoyl - 10,11 - dihydro - 5H - dibenzo[a,d]-cyclohepten-5-one, treating this compound with N-bromosuccinimide and benzoyl peroxide to form 3 - dimethylsulphamoyl - 5H - dibenzo[a,d]-cyclohepten-3-one, reducing this compound with potassium borohydride to form 3-dimethylsulphamoyl - 5H - dibenzo[a,d]cyclohepten - 5 - ol, and treating this compound with hydrogen chloride to form the desired 5-chloro compound. 5 - Chloro - 3 - dimethylsulphamoyl - 10,11 -dihydro - 5H - dibenzo[a,d]cycloheptene is prepared by reducing 3-dimethylsulphamoyl-10,11-dihydro - 5H - dibenzo[a,d]cyclohepten-5-one with potassium borohydride and treating the resulting 3 - dimethylsulphamoyl - 10,11 - dihydro - 5H - dibenzo[a,d]cyclohepten - 5 - ol with hydrogen chloride. Organo-metal compounds of the general formula <FORM:1017696/C2/3> wherein Y represents lithium or Hal-Mg in which Hal is a halogen, preferably chlorine or bromine, and R, R1 and Z have the significance indicated in the first paragraph above, are prepared by the usual methods from magnesium and the required organo-halides, and from phenyl-lithium and the required substituted hydrocarbon. Reference has been directed by the Comptroller to Specifications 858,188 and 975,465. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-0056616-A3 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-0056616-A2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-0056617-A3 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-0056617-A2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4513002-A |
| priorityDate | 1961-09-25-04:00^^<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: 85.