C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/313.3
C07D 249/08 (2006.01) C07D 243/20 (2006.01) C07D 487/04 (2006.01)
Patent
CA 1157871
5207 ABSTRACT OF THE DISCLOSURE Compounds of the formula I: Image I wherein R1 is hydroxymethyl, or -CH2NR6R7, in which R8, is -CH2-C?CH, -CH2-CH=CH2, Image , or alkyl of 1 to 3 carbon atoms, inclusive; R7 is hydrogen or alkyl of 1 to 3 carbon atoms, or together Image is pyrrolidino, piperidino or morpholino; wherein R2 is hydrogen, chlorine or fluorine; wherein R3 is hydrogen, or fluorine if R2 is fluorine; wherein R4 is hydrogen, fluorine, chlorine, bormine, nitro, or trifluoromethyl; and wherein R5 is hydrogen, methyl or ethyl. These compounds, except those in which R7 is hydrogen, are produced by heating a compound of formula II: Image II - 1 - wherein R2, R3, R4, and R5 are defined as herein above, and wherein R'1 is the same as R1 except that in defining R'1, R7 may not be hydrogen, with aqueous formaldehyde in formic acid solution at reflux temperature (about 100° C.). Compounds in which R7 are hydrogen require steps further shown in the specification. The compounds of formula I and their pharmacologically acceptable acid addition salts thereof have tranquilizing, anti-anxiety and anti-convulsant activity useful for the treatment of animals and man. -1a-
252213
Macrae & Co.
Upjohn Company (the)
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