Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1973-09-04
1978-04-04
Rollins, Alton D.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260239BD, 2602393D, 424244, 424269, C07D48704
Patent
active
040827615
ABSTRACT:
This invention relates to novel benzodiazepinium compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, lower alkyl of 1 through 3 carbon atoms, hydroxy, mercapto, amino, monoalkylamino of 1 through 3 carbon atoms, arylamino wherein the aryl moiety is selected from the group consisting of unsubstituted and monosubstituted phenyl and naphthyl, alkanoylamino of 1 through 4 carbon atoms, aroylamino wherein the aroyl moiety is selected from the group consisting of unsubstituted and monosubstituted benzoyl and naphthoyl, alkanesulfonamido of 1 through 3 carbon atoms, and arylsulfonamido wherein the aryl moiety is selected from the group consisting of unsubstituted and monosubstituted phenyl and naphthyl; R.sub.1 is lower alkyl of 1 through 3 carbon atoms; R.sub.2 is selected from the group consisting of hydrogen and lower alkyl of 1 through 3 carbon atoms; R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are selected from the group consisting of hydrogen, lower alkyl of 1 through 3 carbon atoms, halogen, nitro, trifluoromethyl, cyano, lower alkoxy of 1 through 3 carbon atoms and lower alkylthio of 1 through 3 carbon atoms; X.sup..crclbar. is an anion derived from a pharmacologically acceptable acid addition salt; .sup..sym. is the cation of the compound. The new compounds of Formulae VI, VII, VIII, IX, X and XI, set forth below, are included within generic Formula XIII, above. The invention also relates to inner salt compounds of the formula ##STR2## wherein Y is selected from the group consisting of hydroxy, mercapto and monosubstituted amino having an electronegative substituent selected from the group consisting of arylamino, alkanoylamino, aroylamino, alkanesulfonamide and arylsulfonamide, said terms, as well as R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and .sup..sym., having the same meaning as above, and .sup..crclbar. appearing above Y indicates that the compound is an inner salt. The invention also includes novel intermediates (III) for the production of the novel compounds of Formulae IV through XI having the formula ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 have the same meaning as above. It further relates to novel compounds (XII) prepared from those of Formula VII (wherein R' is hydrogen) and having the formula ##STR4## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 have the same meaning as above. It also relates to processes for the preparation of the novel compounds of Formulae II through XII. The systemic administration to humans and animals of the new products of Formulae IV through XII depresses their central nervous systems.
REFERENCES:
patent: 3696094 (1972-10-01), Tachikawa et al.
patent: 3751426 (1973-08-01), Hester
Hodes William A.
Reynolds John T.
Rollins Alton D.
The Upjohn Company
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