# US 4,393,004 A · 3-[(.alpha.-Substituted-benzyl]-2,3,dihydr othiazolo[3,2-a][1,3]diazacyclan-3-ol derivatives > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,393,004 A - Document ID: US4393004A - Status: Granted - Kind: A - Application number: 06/344,118 - Filed: 1982-01-29 - Granted: 1983-07-12 - Earliest claimed: 1980-11-14 - Assignees: American Cyanamid Company - Inventors: Andrew S. Tomcufcik; William B. Wright, Jr.; Joseph W. Marsico, Jr. - Web page: https://patentgrep.com/patent/US4393004A ## CPC - C07D 513/04: Ortho-condensed systems - C07C 45/63: by introduction of halogen; by substitution of halogen atoms by other halogen atoms - C07C 45/68: by increase in the number of carbon atoms - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract This disclosure describes certain novel 3-(.alpha.-substituted-benzyl)-2,3-dihydrothiazolo[3,2-a][1,3]diazacyclan- 3-ols which are useful as diuretic agents. ## Claims ### Claim 1 A compound selected from those of the formula: ##STR28## wherein R.sub.1 is hydrogen, fluoro, chloro, bromo, alkyl having from 1 to 3 carbon atoms or alkoxy having from 1 to 3 carbon atoms; R.sub.2 is hydrogen or ##STR29## wherein R.sub.1 is as hereinbefore defined; R.sub.3 is hydrogen, alkyl having from 1 to 3 carbon atoms, or a moiety selected from the group consisting of those of the formulae: ##STR30## wherein R.sub.1 and R.sub.2 are as hereinbefore defined, and Q is a divalent moiety selected from the group consisting of those of the formulae: --(CH.sub.2).sub.2 -- and --CH.dbd.CH-- as well as the pharmaceutically acceptable salts thereof. ### Claim 2 (depends on 1, 3) The compound according to claim 1, 3-diphenylmethyl-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol hydrobromide. ### Claim 3 (depends on 1, 3) The compound according to claim 1, 3-(p-fluoro-.alpha.-phenylbenzyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3 ]diazepin-3-ol hydrobromide. ### Claim 4 (depends on 1, 3) The compound according to claim 1, 3-[o-chloro-.alpha.-(p-fluorophenyl)benzyl]-2,3,5,6,7,8-hexahydrothiazolo[ 3,2-a][1,3]diazepin-3-ol hydrobromide. ### Claim 5 (depends on 1, 3) The compound according to claim 1, 3-[o-fluoro-.alpha.-(p-fluorophenyl)benzyl]-2,3,5,6,7,8-hexahydrothiazolo[ 3,2-a][1,3]diazepin-3-ol hydrobromide. ### Claim 6 (depends on 1, 3) The compound according to claim 1, 3-[bis-(p-fluorophenyl)methyl]-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]di azepin-3-ol hydrobromide. ### Claim 7 (depends on 1, 3) The compound according to claim 1, 3-(p-chloro-.alpha.-phenylbenzyl)-2,3,5,6,7,8-hexahydro-2-methylthiazolo[3 ,2-a][1,3]diazepin-3-ol hydrobromide. ### Claim 8 (depends on 1, 3) The compound according to claim 1, 3-(p-fluoro-.alpha.-phenylbenzyl)-2,3,5,6,7,8-hexahydro-2-methylthiazolo[3 ,2-a][1,3]diazepin-3-ol hydrobromide. ### Claim 9 (depends on 1, 3) The compound according to claim 1, 3-(.alpha.-phenyl-p-tolyl)benzyl-2,3,5,6,7,8-hexahydro-5H-thiazolo[3,2-a][ 1,3]diazepin-3-ol hydrobromide. ### Claim 10 (depends on 1, 3) A compound according to claim 1, 3-(p-chloro-.alpha.-phenyl)benzyl-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3 ]diazepin-3-ol hydrobromide. ### Claim 11 (depends on 1, 3) A compound according to claim 1, 3-(p-fluorobenzyl)-2-(p-fluorophenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a] [1,3]diazepin-3-ol hydrobromide. ### Claim 12 (depends on 1, 2, 3, 5, 6, 7, 8) A compound according to claim 1, 2,3,5,6,7,8-hexahydro-3-(m-methylbenzyl)-2-p-tolylthiazolo[3,2-a][1,3]diaz epin-3-ol hydrobromide. ### Claim 13 (depends on 1, 3) A compound according to claim 1, 3[m-fluoro-.alpha.-(p-fluorophenyl)benzyl]-2,3,5,6,7,8-hexahydrothiazolo[3 ,2-a][1,3]diazepin-3-ol hydrobromide. ### Claim 14 (depends on 1, 3) A compound according to claim 1, 3-(p-bromo-.alpha.-phenyl)benzyl-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1.3] diazepin-3-ol hydrobromide. ### Claim 15 (depends on 1, 3) A compound according to claim 1, 3-[p-fluoro-.alpha.-(p-tolyl)benzyl-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1 ,3]diazepin-3-ol hydrobromide. ### Claim 16 (depends on 1, 3) The compound according to claim 1, 3-[o-fluoro-.alpha.-(p-fluorophenyl)benzyl]-2,3,5,8-tetrahydrothiazolo[3,2 ][1,3]diazepin-3-ol hydrobromide. ### Claim 17 (depends on 1, 3) The compound according to claim 1, 3-[m-fluoro-.alpha.-(p-fluorophenyl)benzyl]-2,3,5,8-tetrahydrothiazolo[3,2 -a][1,3]diazepin-3-ol hydrobromide. ### Claim 18 (depends on 1, 3) A compound according to claim 1, 3-[p-chloro-.alpha.-(p-fluorophenyl)benzyl]-2,3,5,8,-tetrahydrothiazolo[3, 2-a][1,3]diazepin-3-ol hydrobromide. ### Claim 19 (depends on 1, 3) A compound according to claim 1, 3-[bis(p-fluorophenyl)methyl]-2,3,5,8-tetrahydrothiazolo[3,2-a][1,3]diazep in-3-ol hydrobromide. ### Claim 20 A compound selected from those of the formula: ##STR31## wherein R.sub.1 is hydrogen, fluoro, chloro, bromo, alkyl having from 1 to 3 carbon atoms or alkoxy having from 1 to 3 carbon atoms; R.sub.2 is hydrogen or ##STR32## wherein R.sub.1 is as hereinbefore defined; R.sub.3 is hydrogen, alkyl having from 1 to 3 carbon atoms, or a moiety selected from the group consisting of those of the formulae: ##STR33## wherein R.sub.1 and R.sub.2 are as hereinbefore defined, and Q is --(CH.sub.2).sub.3 --, as well as the pharmaceutically acceptable salts thereof. ### Claim 21 (depends on 3, 20) A compound according to claim 20, 3-diphenylmethyl-2,3,6,7,8,9-hexahydro-5H-thiazolo[3,2-a][1,3]diazocin-3-o l hydrobromide. ### Claim 22 (depends on 3, 20) A compound according to claim 20, 3-benzyl-2,3,6,7,8,9-hexahydro-2-phenyl-5H-thiazolo[3,2-a][1,3]diazocin-3- ol hydrobromide. ### Claim 23 (depends on 3, 20) A compound according to claim 20, 3-(p-fluorobenzyl)-2-(p-fluorophenyl)-2,3,6,7,8,9-hexahydro-5H-thiazolo[3, 2-a][1,3]diazocin-3-ol hydrobromide. ### Claim 24 (depends on 3, 20) A compound according to claim 20, 3-(m-fluorobenzyl)-2-(m-fluorophenyl)-2,3,6,7,8,9-hexahydro-5H-thiazolo[3, 2-a][1,3]diazocin-3-ol hydrobromide. ### Claim 25 (depends on 3, 20) A compound according to claim 20, 3-(p-chlorobenzyl)-2-p-chlorophenyl-2,3,6,7,8,9-hexahydro-5H-thiazolo[3,2- a][1,3]diazocin-3-ol hydrobromide. ### Claim 26 (depends on 3, 20) A compound according to claim 20, 3-(p-methylbenzyl)-2-(p-tolyl)-2,3,6,7,8,9-hexahydro-5H-thiazolo[3,2-a][1, 3]diazocin-3-ol hydrobromide.