http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1343921-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_76195fd1cd08192222699d8e7a88c231 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D413-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D281-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D267-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D267-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D281-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D281-16 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D281-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D267-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D281-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D413-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D267-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D281-16 |
| filingDate | 1971-02-23^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1974-01-16^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1343921-A |
| titleOfInvention | Tricyclic guanidine derivatives |
| abstract | 1343921 Tricyclic ganidine derivatives E R SQUIBB & SONS Inc 23 Feb 1971 5238/71 Heading C2C Novel compounds of Formula I and acid addition salts thereof, wherein the R radicals may be the same or different and represent hydrogen, lower alkyl, monocyclic arylalkyl or monocyclic aryl; R<SP>3</SP> and R<SP>4</SP> may be the same or different and represent hydrogen, halogen, lower alkyl, cyclolower alkyl, cyano, lower haloalkyl, lower alkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower haloalkoxy, lower haloalkylthio, aminsulfonyl or N,N-dilower alkylaminosulfonyl; X represents oxygen or sulfur; m is 0 or 1; n is 0, 1 or 2; p is 0, 1 or 2; the sum of m+n+p=1 to 3; r is 2 to 5; and the terms "lower alkyl" and "lower alkoxy" mean that such radicals contain up to 8 carbon atoms, are prepared (a) by reacting a compound of Formula II with cyanamide, an R<SP>1</SP>-substituted cyanamide, a 2-alkyl-2-thiopseudourea sulphate or a 1-R<SP>1</SP>- substituted-2-alkyl-2-thiopseudourea sulphate or (b) for compounds I in which R<SP>1</SP> is H, by reacting a compound II with (i) cyanogen bromide and, e.g. reacting the cyanamide intermediate with a combination of ammonium sulphate and ammonium hydroxide, or (ii) ammonium thiocyanate to give the corresponding thiourea derivative which is converted directly to the desired compound I by treatment with a combination of ammonia and a mercuric halide, or is first converted to the corresponding 2-methyl-2-thiopseudourea derivative and this compound then reacted with a combination of ammonium hydroxide and ammonium sulphate. Compounds of Formula II are prepared by (i) reduction of appropriate nitriles or amides, or (ii) reaction of appropriate haloalkylene compounds with amines of formula H 2 NR<SP>2</SP>, or (iii) reaction of appropriate phthalimido compounds with hydrazine. The nitriles are prepared by reaction of compounds of Formula III with an unsaturated nitrile, e.g. acrylonitrile. The amides are prepared by hydrolysis of the nitriles. The haloalkylene compounds are prepared by reaction of a compound III with a haloalkylene halide, or by reaction of a compound III with a haloalkanol followed by reaction of the intermediate with a halogenating agent. 10,12 - Dihydrodibenzo[c, f][1,5] - thiazocine is prepared by reacting o-nitro-α-toluene thiol with o-bromobenzyl bromide to give o-bromobenzyl o-nitrobenzyl sulphide, reducing this to give o-(o-bromobenzylthiomethyl)aniline, treating this with formic acid to give o-(o-bromobenzylthiomethyl)-formanilide, and cyclizing this to give the desired compound. 3-Chloro-10,12-dibenzo- [c,f][1,5]thiazocine is similarly prepared. 2 - Bromo - 4 - chlorobenzyl bromide is prepared via 2-bromo-4-chlorotoluene by bromination of p-chlorotoluene. Pharmaceutical compositions having antidepressant, sedative and hypotensive activity, for oral or parenteral administration, comprise a compound I or acid addition salt thereof together with a carrier. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-105315229-A |
| priorityDate | 1971-02-23^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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