Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1975-09-03
1977-04-05
Torrence, Dolph H.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260253, 26050119, 260570R, 2605707, C07C 9306
Patent
active
040162028
ABSTRACT:
Racemic and optically active compounds of the formula ##STR1## wherein R.sub.1 is hydrogen; halogen; nitro; alkyl of 1 to 5 carbon atoms; alkoxy of 1 to 4 carbon atoms; alkenyl of 2 to 5 carbon atoms; alkynyl of 2 to 5 carbon atoms; alkylamino of 1 to 5 carbon atoms; dialkylamino of 1 to 5 carbon atoms in each alkyl; alkoxyalkyl of 2 to 6 carbon atoms; alkylamino-alkyl of 2 to 6 carbon atoms; dialkylaminoalkyl of 3 to 12 carbon atoms; --(CH.sub.2).sub.x --NH.sub.2, --(CH.sub.2).sub.x -- OH, all where x is an integer from 0 to 3; --COOH; --COOR.sub.6, where R.sub.6 is alkyl of 1 to 4 carbon atoms; alkynyloxy of 3 to 6 carbon atoms; alkenyloxy of 3 to 6 carbon atoms; --CO--R.sub.9, --OCO--R.sub.9, --NH--CO--R.sub.9, all where R.sub.9 is alkyl of 1 to 6 carbon atoms, phenylalkyl of 7 to 10 carbon atoms or phenyl; cycloalkyl of 3 to 7 carbon atoms; --Q--CO--NR.sub.7 R.sub.8, where Q is a single bond, oxygen, --NH--, -- CH.sub.2 -- or --CH.sub.2 --NH--, and R.sub.7 and R.sub.8 are hydrogen, lower alkyl or, taken together with the nitrogen, pyrrolidino, piperidino or morpholino; phenyl; phenyl substituted with a substituent selected from the group consisting of halogen, lower alkyl, lower alkoxy, nitro, cyano and carboxyl; phenoxy; or phenoxy substituted with a substituent selected from the group consisting of halogen, lower alkyl, lower alkoxy, nitro, cyano and carboxyl;
R.sub.2 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkanoyl of 2 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, amino, nitro or, together with R.sub.1, 3,4-methylenedioxy;
R.sub.3 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or, together with R.sub.2 in the ortho-position, --CH=CH--CH=CH-- or --(CH.sub.2)n--, where n is an integer from 3 to 5;
R.sub.4 is hyddrogen or alkyl of 1 to 3 carbon atoms; and
R.sub.5 is alkyl of 1 to 3 carbon atoms or, together with R.sub.4, --(CH.sub.2).sub.p -- where p is an integer from 4 to 6; and physiologically compatible acid addition salts thereof. The compounds as well as their salts are useful as adrenolytics and hypotensives.
REFERENCES:
patent: 3459782 (1969-08-01), Koppe et al.
patent: 3541130 (1970-11-01), Koppe et al.
patent: 3712927 (1973-01-01), Howe et al.
Koppe Herbert
Kummer Werner
Muacevic Gojko
Stahle Helmut
Boehringer Ingelheim GmbH
Torrence Dolph H.
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