Patents Assigned to Boehringer Ingelheim GmbH
  • Patent number: 4137313
    Abstract: Compounds of the formula ##STR1## WHEREIN R.sub.1 is hydrogen, methyl or ethyl;R.sub.2 is methyl or ethyl;Y is hydrogen, fluorine, chlorine, bromine, methoxy, methyl, ethyl or trifluoromethyl; andAr is 2-thiazolyl which may have one or two methyl or ethyl substituents attached thereto; 5,6-dihydro-4H-cyclopentathiazol-2-yl; 4,5,6,7-tetrahydro-2-benzothiazolyl; 2-benzothiazolyl; 3-isothiazolyl which may have a methyl substituent attached thereto; 2-pyridyl which may have a methyl or hydroxyl substituent attached thereto; 3-pyridyl; 4-pyridyl; 4-pyrimidinyl; pyrazinyl; 2-benzimidazolyl; 2-oxazolyl which may have a methyl substituent attached thereto; 2-benzoxazolyl; or phenyl which may have a fluoro, chloro, bromo, methyl, ethyl, trifluoromethyl or methoxy substituent attached thereto; and non-toxic, pharmacologically acceptable salts thereof formed with inorganic or organic bases. The compounds as well as their salts are useful as antiphlogistics and blood platelet aggregation inhibitors.
    Type: Grant
    Filed: January 27, 1978
    Date of Patent: January 30, 1979
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Gunter Trummlitz, Wolfhard Engel, Ernst Seeger, Walter Haarmann, Gunther Engelhardt
  • Patent number: 4136185
    Abstract: Compounds of the formula ##STR1## wherein R is phenyl; phenyl having one or two substituents attached thereto, said substituents being selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, chlorine and trifluoromethyl; naphthyl; tetrahydronaphthyl; indanyl; pyridyl; isoquinolyl; or thiazolyl;R.sub.3 is hydrogen, alkyl of 1 to 4 carbon atoms;R.sub.4 and R.sub.5 are each hydrogen or alkyl of 1 to 4 carbon atoms;Q is oxygen or two hydrogens;R.sub.2 is hydrogen, alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms or halogen;A is a single carbon-to-carbon bond or --OCH.sub.2 --;R.sub.6 is hydrogen, hydroxyl, alkoxy of 1 to 4 carbon atoms or alkanolyloxy of 1 to 4 carbon atoms, andM is 0, 1, 2, 3, 4 or 5, but other than O when R.sub.
    Type: Grant
    Filed: March 15, 1978
    Date of Patent: January 23, 1979
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Ernst-Otto Renth, Anton Mentrup, Kurt Schromm, Peter Danneberg
  • Patent number: 4134980
    Abstract: Compounds of the formula ##STR1## wherein A is ##STR2## where R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms; R.sub.2 is alkoxy of 1 to 3 carbon atoms;R.sub.3 is alkoxy of 1 to 3 carbon atoms or, together with R.sub.2, methylenedioxy or ethylenedioxy;R.sub.4 is hydrogen, alkyl of 1 to 3 carbon atoms or benzyl;R.sub.5 is hydrogen or alkyl of 1 to 3 carbon atoms;R.sub.6 is hydrogen or alkoxy of 1 to 3 carbon atoms;R.sub.7 is alkoxy of 1 to 3 carbon atoms or, together with R.sub.6, methylenedioxy or ethylenedioxy; andN is 2 or 3;And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as heart rate reducers and mild antihypertensives.This invention relates to novel N-(phenylalkylaminoalkyl)-substituted quinazolinones and phthalazinones and nontoxic acid addition salts thereof, as well as to various methods of preparing these compounds.
    Type: Grant
    Filed: August 24, 1977
    Date of Patent: January 16, 1979
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Wolfgang Eberlein, Volkhard Austel, Joachim Heider, Jurgen Dammgen, Rudolf Kadatz, Christian Lillie, Walter Kobinger
  • Patent number: 4133888
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is methyl, ethyl or propyl; and R.sub.2 is hydrogen, methyl or ethyl; and non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as analgesics and morphine antagonists.
    Type: Grant
    Filed: April 12, 1978
    Date of Patent: January 9, 1979
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Herbert Merz, Klaus Stockhaus
  • Patent number: 4130650
    Abstract: Pharmaceutical compositions containing as an active ingredient a compound of the formula ##STR1## wherein R.sub.1 is hydrogen or methyl,Ar is phenyl, 2-pyridyl, 6-methyl-2-pyridyl, 2-quinolyl, 1-methyl-benzimidazol-2-yl, 2-pyrazinyl or 3-methyl-isoxazol-5-yl, andR.sub.2 is dimethylamino, monomethylamino or morpholino,Or a non-toxic, pharmaceutically acceptable acid addition salt thereof; and a method of using the same as antiarrhythmics.
    Type: Grant
    Filed: May 25, 1977
    Date of Patent: December 19, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Erich Muller, Willi Diederen, Robin G. Shanks
  • Patent number: 4130558
    Abstract: A process for the preparation of an alkali metal salt of ampicillin, especially the sodium salt, which comprises adding to an aqueous suspension of ampicillin, at a temperature not exceeding about 4.degree. C, an aqueous solution of an equimolar or somewhat lesser amount of an alkali metal base, filtering the resulting solution until sterile, freezing the filtrate, and lyophilizing the frozen filtrate.
    Type: Grant
    Filed: May 18, 1977
    Date of Patent: December 19, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Otto Roos, Dieter Essig
  • Patent number: 4125620
    Abstract: Compounds of the formula ##STR1## wherein Z is 2-ETHYL-6-METHYL-PHENYL,2,6-di-trifluoromethyl-phenyl,2-chloro-6-trifluoromethyl-phenyl or2-fluoro-6-trifluoromethyl-phenyl,And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as the salts are useful as hypotensives.
    Type: Grant
    Filed: November 11, 1977
    Date of Patent: November 14, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Wolfgang Hoefke
  • Patent number: 4119710
    Abstract: Racemic and optically active compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, fluorine, chlorine, bromine, iodine or cyano,R.sub.2 is fluorine, trifluoromethyl, nitro or cyano, andR.sub.3 is alkyl of 3 to 5 carbon atoms, hydroxy(alkyl of 3 to 5 carbon atoms), cycloalkyl of 3 to 5 carbon atoms, 1-(3,4-methylenedioxy-phenyl)-2-propyl or 1-(p-hydroxy-phenyl)-2-propyl,And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as analgesics, uterospasmolytics, bronchospasmolytics and antispastics for the skeletal musculature, and especially as .beta..sub.2 -receptor mimetics and .beta..sub.1 -receptor blockers.
    Type: Grant
    Filed: December 28, 1976
    Date of Patent: October 10, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Gunther Engelhardt, Johannes Keck, Gerd Kruger, Klaus-Reinhold Noll, Helmut Pieper
  • Patent number: 4119728
    Abstract: Racemic and optically active compounds of the formula ##STR1## wherein R.sub.1 is --COOR.sub.6, where R.sub.6 is hydrogen or alkyl of 1 to 4 carbon atoms; --OCO--R.sub.9 or --NH--CO--R.sub.9, where R.sub.9 is alkyl of 1 to 6 carbon atoms, phenyl (alkyl of 1 to 4 carbon atoms) or phenyl; --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; cyano-phenyl; carboxylphenyl; cyano-phenoxy; or carboxyl-phenoxy;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.dbd.CH--CH.dbd.CH-- or --(CH.sub.2)n-- where n is an integer from 3 to 5;R.sub.
    Type: Grant
    Filed: November 18, 1976
    Date of Patent: October 10, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Herbert Koppe, Werner Kummer, Helmut Stahle, Gojko Muacevic
  • Patent number: 4113777
    Abstract: Compounds of the formula ##STR1## wherein X and R.sub.1 are each chlorine or bromine;R.sub.2 is isopropyl; tert.butyl; tert.pentyl; mono-, di- or tri-hydroxy-substituted branched alkyl of 3 to 5 carbon atoms; cyclohexyl; or hydroxycyclohexyl; andR.sub.3 is alkyl of 1 to 4 carbon atoms or, when R.sub.2 is other than cyclohexyl, also hydrogen;And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as secretolytics, antitussives, anti-ulcerogenics and stimulants for the production of the surfactant or antiatelectasis factor of the alveoli.
    Type: Grant
    Filed: July 1, 1977
    Date of Patent: September 12, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Johannes Keck, Sigfrid Puschmann, Gerd Kruger, Klaus-Reinhold Noll, Matyas Leitold, Helmut Pieper
  • Patent number: 4105765
    Abstract: A compound of the formula ##STR1## wherein R.sub.1 is chlorine, bromine, fluorine or methyl;R.sub.2 and R.sub.3, which may be identical to or different from each other, are each hydrogen, chlorine or methyl;R.sub.4 is hydrogen, methyl or ethyl; andR.sub.5 and R.sub.6, together with each other and the nitrogen atom to which they are attached, are morpholino, piperazino or N-methylpiperazino;And non-toxic, pharmaceutically acceptable acid addition salts thereof; the compounds as well as the salts are useful as antithrombotics.
    Type: Grant
    Filed: September 29, 1977
    Date of Patent: August 8, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Werner Kummer, Helmut Stahle, Herbert Koppe, Walter Haarmann, Richard Reichl
  • Patent number: 4105796
    Abstract: Pharmaceutical dosage unit compositions containing as an active ingredient racemic or optically active 1-(2',6'-dimethyl-phenoxy)-2-methylamino-propane of the formula ##STR1## or a non-toxic, pharmaceutically acceptable acid addition salt thereof; and a method of using the same as anticonvulsives and antiarrhythmics.
    Type: Grant
    Filed: May 19, 1976
    Date of Patent: August 8, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Herbert Koppe, Werner Kummer, Helmut Stahle, Richard Reichl, Rolf Giesemann
  • Patent number: 4101671
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or aliphatic or aromatic carboxylic acyl,R.sub.2 is hydrogen, chlorine or bromine,R.sub.3 is fluorine, alkyl of 1 to 4 carbon atoms, trifluoromethyl, cyano, carbamoyl, carboxyl, carbalkoxy, alkoxy, acetyl, 1-hydroxyethyl or ##STR2## where R.sub.6 and R.sub.7 are each alkyl, cycloalkyl, hydroxy-cycloalkyl or, together with each other and the nitrogen atom to which they are attached, pyrrolidino, piperidino or morpholino, andR.sub.4 and R.sub.5 are each hydrogen, alkyl of 1 to 5 carbon atoms, mono- or di-hydroxy (alkyl of 1 to 5 carbon atoms), alkenyl of 2 to 4 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, mono- or di-hydroxy (cycloalkyl of 5 to 7 carbon atoms), benzyl, morpholinocarbonylmethyl or, together with each other and the nitrogen atom to which they are attached, pyrrolidino, piperidino, hexamethyleneimino, morpholino, N-methyl-piperazino or camphidino,Provided, however, that when R.sub.3 is carboxyl or carbalkoxy, R.sub.4 and R.sub.
    Type: Grant
    Filed: March 24, 1977
    Date of Patent: July 18, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Johannes Keck, Klaus-Reinhold Noll, Helmut Pieper, Gerd Kruger, Sigfrid Puschmann
  • Patent number: 4100282
    Abstract: Compounds of the formula ##STR1## wherein R is phenyl; phenyl having one or two substituents attached thereto, said substituents being selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, chlorine and trifluoromethyl; naphthyl; tetrahydronaphthyl; indanyl; pyridyl; isoquinolyl; or thiazolyl;R.sub.1 is ##STR2## where R.sub.3 is hydrogen, alkyl of 1 to 4 carbon atoms,R.sub.4 and R.sub.5 are each hydrogen or alkyl of 1 to 4 carbon atoms, andQ is oxygen or two hydrogens,R.sub.2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen,A is a single carbon-to-carbon bond or --OCH.sub.2 --,R.sub.6 is hydrogen, hydroxyl, alkoxy of 1 to 4 carbon atoms or alkanoyloxy of 1 to 4 carbon atoms, andm is 0, 1, 2, 3, 4 or 5, but other than 0 when R.sub.
    Type: Grant
    Filed: May 4, 1977
    Date of Patent: July 11, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Ernst-Otto Renth, Anton Mentrup, Kurt Schromm, Peter Danneberg
  • Patent number: 4100288
    Abstract: Diastereoisomers of the compound of the formula ##STR1## and non-toxic, pharmacologically acceptable acid addition salts thereof; the isomers as well as their salts are useful as analgesics and morphine-antagonists.
    Type: Grant
    Filed: August 13, 1976
    Date of Patent: July 11, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Herbert Merz, Gerhard Walther, Adolf Langbein, Klaus Stockhaus, Helmut Wick
  • Patent number: 4100292
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3, which may be identical or different from each other, are each hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy, hydroxyl, trifluoromethyl or cyano; andR.sub.4 is (cycloalkyl of 3 to 6 carbon atoms)-methyl; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as analgesics.
    Type: Grant
    Filed: August 12, 1977
    Date of Patent: July 11, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Klaus Stockhaus, Wolfgang Hoefke, Franz Josef Kohn
  • Patent number: 4094980
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are chlorine, orR.sub.1 is methyl and R.sub.2 is methoxy,And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as anti-hyperlipidemics and anti-hypercholesteremics with practically negligible CNS-depressing side effects.
    Type: Grant
    Filed: December 10, 1976
    Date of Patent: June 13, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Ernst-Otto Renth, Anton Mentrup, Kurt Schromm, Wilhelm Frolke
  • Patent number: 4094984
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, fluorine, chlorine, bromine, nitro or trifluoromethyl; andR.sub.2 is hydrogen, alkyl of 1 to 4 carbon atoms or hydroxyalkyl of 1 to 4 carbon atoms; and non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as tranquilizers, muscle-relaxants and anticonvulsants.
    Type: Grant
    Filed: October 6, 1977
    Date of Patent: June 13, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Karl-Heinz Weber, Adolf Bauer, Peter Danneberg, Franz Josef Kuhn
  • Patent number: 4093734
    Abstract: Compounds of the formula ##STR1## wherein (A) WHEN THE AMINO-SUBSTITUENT IS IN THE P-POSITION WITH RESPECT TO THE CARBONYL GROUP,R.sub.1 is chlorine in the o-position with respect to the carbonyl group,R.sub.2 is hydrogen, andR.sub.3 is ethylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, N-methyl-cyclohexylamino, benzylamino or 1-ethyl-pyrrolidyl-(2)-aminomethyl, or(b) when the amino-substituent is in the o--, m-- or p-position with respect to the carbonyl group,R.sub.1 is hydrogen, chlorine or bromine,R.sub.2 is trifluoromethyl, nitro or, when R.sub.4 is 1-(alkyl of 1 to 3 carbon atoms)-pyrrolidyl or 1-(alkyl of 1 to 3 carbon atoms)-piperidyl, also fluorine, chlorine, bromine or methyl,R.sub.3 is (alkyl of 1 to 5 carbon atoms)-amino, (cycloalkyl of 3 to 7 carbon atoms)-amino, benzylamino, quinuclidinyl-amino or --NH--(CH.sub.2).sub.n --R.sub.4where R.sub.
    Type: Grant
    Filed: October 22, 1976
    Date of Patent: June 6, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Gerd Kruger, Johannes Keck, Klaus Reinhold Noll, Helmut Pieper, Harald Ziegler, Helmut Ballhause, Joachim Kahling
  • Patent number: RE29628
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or aliphatic or aromatic carboxylic acyl,R.sub.2 is hydrogen, chlorine or bromine,R.sub.3 is fluorine, alkyl of 1 to 4 carbon atoms, trifluoromethyl, cyano, carbamoyl, carboxyl, carbalkoxy, alkoxy, acetyl, 1-hydroxyethyl or ##STR2## where R.sub.6 and R.sub.7 are each alkyl, cycloalkyl, hydroxy-cycloalkyl or, together with each other and the nitrogen atom to which they are attached, pyrrolidino, piperidino or morpholino, andR.sub.4 and R.sub.
    Type: Grant
    Filed: December 2, 1976
    Date of Patent: May 9, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Johannes Keck, Klaus-Reinhold Noll, Helmut Pieper, Gerd Kruger, Sigfrid Puschmann