Patent number: 4182887
Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is mono- or di-substituted amino, where the substituents are selected from the group consisting of alkyl of 1 to 6 carbon atoms, cyclohexyl, allyl and benzyl; unsubstituted, mono-substituted or di-substituted pyrrolidino, piperidino, hexamethyleneimino, morpholino, piperazino, thiomorpholino, 1-oxido-thiomorpholino or 1,1-dioxido-thiomorpholino, where the substituents are selected from the group consisting of methyl, hydroxymethyl, hydroxyl, phenyl and benzyl; 1,2,5,6-tetrahydropyridino; 1,2,3,4-tetrahydroisoquinolino; indolino; or 3,6-ethylene-hexamethyleneimino;R.sub.2 is hydrogen, methyl or benzyl; andR.sub.3 is hydrogen, halogen, alkyl of 1 to 3 carbon atoms or alkoxy of 1 to 3 carbon atoms;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as antiphlogistics and antithrombotics.
Type:
Grant
Filed:
September 19, 1977
Date of Patent:
January 8, 1980
Assignee:
Boehringer Ingelheim GmbH
Inventors:
Josef Roch, Erich Muller, Berthold Narr, Josef Nickl, Walter Haarmann
Patent number: 4180573
Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, halo-lower alkyl, hydroxy-lower alkyl, di(lower alkyl)amino-lower alkyl, phenyl, tolyl, methoxy-phenyl, nitro-phenyl, halo-phenyl, pyridyl, pyrimidinyl or --CO--R.sub.4, where R.sub.4 is hydrogen, alkyl or 1 to 17 carbon atoms, alkoxy of 1 to 2 carbon atoms, phenyl, tolyl, methoxy-phenyl, halo-phenyl, nitro-phenyl or pyridyl;R.sub.2 is hydrogen, fluorine, chlorine, or bromine; andR.sub.3 is chlorine, bromine or lower alkyl,and non-toxic, pharmacologically acceptable acid addition salts of certain of these compounds. The compounds as well as the salts are useful as anxiolytics, tranquilizers, sedatives or neuroleptics.
Type:
Grant
Filed:
July 13, 1978
Date of Patent:
December 25, 1979
Assignee:
Boehringer Ingelheim GmbH
Inventors:
Karl-Heinz Weber, Adolf Langbein, Claus Schneider, Erich Lehr, Karin Boke, Franz J. Kuhn
Patent number: 4154829
Abstract: Racemic and optically active compounds of the formulaQ--C.sub.n H.sub.2n --NH--Rwherein Q is ##STR1## where R.sub.1 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl or amino,R.sub.2 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or trifluoromethyl,R.sub.1 and R.sub.2, together with each other, are methylenedioxy or ethylenedioxy, andA is --O--, --CH.sub.2 --CH.sub.2 --, --O--CH.sub.2 -- where the oxygen is bonded to the benzene ring, or --NR.sub.3 -- where R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms,N is an integer from 2 to 6, inclusive, andR is hydrogen, benzyl or ##STR2## where R.sub.4 is hydrogen, methyl or ethyl,R.sub.5, r.sub.6 and R.sub.7, which may be identical to or different from each other, are each hydrogen, halogen, hydroxymethyl, trifluoromethyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro, cyano, --CONHR.sub.3, --CONHOH, --COOR.sub.3, R.sub.
Type:
Grant
Filed:
March 2, 1977
Date of Patent:
May 15, 1979
Assignee:
Boehringer Ingelheim GmbH
Inventors:
Anton Mentrup, Kurt Schromm, Ernst-Otto Renth, Richard Reichl, Werner Traunecker, Wolfgang Hoefke
Patent number: 4146638
Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is halogen, hydroxyl, amino, alkyl, alkoxy or acylamido,R.sub.2 is hydrogen, hydroxyl, alkyl, alkoxy or carboxamido,R.sub.3 is hydrogen, halogen, alkyl or alkoxy,R.sub.4 is hydrogen, methyl or ethyl, andR.sub.5 and R.sub.6 are each hydrogen, halogen, alkyl, alkoxy, benzyloxy, hydroxyl, amino, cyano, carboxyl, carbalkoxy, carboxamido, alkylenecarboxamido or acylamido,Provided, however, that, when R.sub.1 is 4-hydroxyl or 4-chloro, R.sub.2 and R.sub.3 are hydrogen, R.sub.4 is methyl and R.sub.5 is halogen or 2-halo, R.sub.6 is other than 4-hydroxyl or 4-benzyloxy; and nontoxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as cardiotonics, vasodilators, hypotensives and antiarrhythmics.
Type:
Grant
Filed:
May 15, 1978
Date of Patent:
March 27, 1979
Assignee:
Boehringer Ingelheim GmbH
Inventors:
Ernst-Otto Renth, Anton Mentrup, Kurt Schromm, Herbert Koppe, Richard Reichl