Patents by Inventor Helmut Stahle

Helmut Stahle has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 4250186
    Abstract: Compounds of the formula ##STR1## wherein R is 2-bromo-4,5-dihydroxy-phenyl; 3-chloro-4-hydroxy-phenyl; 4-bromo-2,5-dihydroxy-phenyl; 3,5-dihydroxy-phenyl; 5-chloro-2,4-dihydroxy-phenyl; 3-hydroxy-4-methyl-phenyl; 2,6-dibromo-4-hydroxymethyl-phenyl; 3,5-dibromo-4-amino-phenyl; 3-methylmercapto-phenyl; 3,4,5-trihydroxy-phenyl; or 3-bromo-4-fluoro-phenyl;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as bradycardiacs.
    Type: Grant
    Filed: February 16, 1979
    Date of Patent: February 10, 1981
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Wolfgang Hoefke, Wolfram Gaida, Ludwig Pichler
  • Patent number: 4239764
    Abstract: Compounds of the formula ##STR1## where Ar represents a radical selected from the group consisting of 2,6-dichlorophenyl, 2,5-dichlorophenyl, 2-chloro-6-methylphenyl, 2-chloro-4-methylphenyl, 2,6-dichloro-4-bromophenyl, 4-cyanophenyl, 2,5-dimethoxyphenyl, and 2-methyl-5-fluorophenyl, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as bradycardiacs.
    Type: Grant
    Filed: July 16, 1979
    Date of Patent: December 16, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Wolfgang Hoefke
  • Patent number: 4220659
    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, 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--, --CH2-- or --CH.sub.2 --NH--, and R.sub.7 and R.sub.8, taken together with the nitrogen, are pyrrolidino, piperidino or morpholino; cyano-phenyl; carboxyl-phenyl; 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).sub.n -- where n is an integer from 3 to 5;R.sub.
    Type: Grant
    Filed: July 14, 1978
    Date of Patent: September 2, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Herbert Koppe, Werner Kummer, Helmut Stahle, Gojko Muacevic
  • Patent number: 4215133
    Abstract: 2-[N-(Cyclopropyl-methyl)-N-(2'-chloro-4'-methyl-thienyl-3')-amino]-2-imida zoline and non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds are useful as bradycardiacs.
    Type: Grant
    Filed: July 5, 1979
    Date of Patent: July 29, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Walter Kobinger, Christian Lillie, Ludwig Pichler
  • Patent number: 4213995
    Abstract: Compounds of the formula ##STR1## wherein R is 2,6-dichloro-4-hydroxymethyl-phenyl; 2-chloro-4-methyl-5-amino-phenyl; 2,5-dichloro-4-methyl-phenyl; 2-chloro-4-methyl-5-nitro-phenyl; 2,3-dichloro-4-methyl-phenyl; 2-chloro-4-methyl-6-nitro-phenyl; 2-chloro-4-methyl-6-amino-phenyl; 2,4,6-trifluorophenyl; tetrafluoro-phenyl; or 3-bromo-4-fluoro-phenyl; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as hypotensives.
    Type: Grant
    Filed: February 12, 1979
    Date of Patent: July 22, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Wolfgang Hoefke, Ludwig Pichler
  • Patent number: 4210659
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3, which may be identical to or different from each other, are each hydrogen, fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl, provided that one of them is other than hydrogen; andR.sub.4 and R.sub.5, which may be identical to or different from each other, are each hydrogen or methyl;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as bradycardiacs.
    Type: Grant
    Filed: June 27, 1979
    Date of Patent: July 1, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Walter Kobinger, Christian Lillie, Ludwig Pichler
  • Patent number: 4166859
    Abstract: The compound of the formula ##STR1## and non-toxic, pharmacologically acceptable acid addition salts thereof; the compound as well as the salts are useful as antihypertensives.
    Type: Grant
    Filed: June 20, 1977
    Date of Patent: September 4, 1979
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Wolfgang Hoefke
  • 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: 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: 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: 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: 4084002
    Abstract: Pharmaceutical dosage unit compositions containing as an active ingredient a 1-aryloxy-2-hydroxy-3-alkynylamino-propane selected from the group consisting of racemic or optically active compounds of the formula ##STR1## wherein R.sub.1 is a member selected from the group consisting of hydrogen; halogen; nitro; alkyl having from 1 to 5 carbon atoms; alkoxy having from 1 to 4 carbon atoms; alkenyl having from 2 to 5 carbon atoms; alkynyl having from 2 to 5 carbon atoms; alkylamino having from 1 to 5 carbon atoms; dialkylamino having from 1 to 5 carbon atoms in each alkyl; alkoxyalkyl having from 2 to 6 carbon atoms; alkylaminoalkyl having from 2 to 6 carbon atoms; dialkylaminoalkyl having from 3 to 12 carbon atoms; --(CH.sub.2).sub.x -NH.sub.2 or --(CH.sub.2).sub.x -OH, where x is an integer from 0 to 3; alkynyloxy having from 3 to 6 carbon atoms; alkenyloxy having from 3 to 6 carbon atoms; --CO-R.sub.9, where R.sub.
    Type: Grant
    Filed: November 17, 1976
    Date of Patent: April 11, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Herbert Koppe, Werner Kummer, Helmut Stahle, Gojko Muacevic
  • Patent number: 4080503
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2, which may be identical to or different from each other, are each hydrogen, chlorine, bromine or alkyl of 1 to 3 carbon atoms,R.sub.3 is hydrogen, furfuryl, hydroxyethyl, .beta.-hydroxy-phenethyl, monochlorophenyl-ethyl, dichlorophenyl-ethyl, N-ethyl-piperidyl or --A--NR.sub.6 R.sub.7,whereA is alkylene of 1 to 5 carbon atoms, andR.sub.6 and R.sub.7 are alkyl of 1 to 2 carbon atoms or, together with each other and the nitrogen atom to which they are attached, form a heterocycle selected from the group consisting of pyrrolidino, morpholino, piperazino or N'-dimethylphenyl-piperazino,R.sub.4 is hydrogen or, together with R.sub.3 and the nitrogen to which they are attached, forms a heterocycle selected from the group consisting of piperidino, morpholino, dimethyl-morpholino or N'-methyl-piperazino,R.sub.5 is hydrogen, alkyl of 1 to 3 carbon atoms, hydroxy-ethyl, diethylamino-ethyl or furfuryl,Provided, however, that R.sub.1 and R.sub.
    Type: Grant
    Filed: July 16, 1973
    Date of Patent: March 21, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Werner Kummer, Herbert Koppe, Helmut Stahle, Walter Haarmann
  • Patent number: 4073905
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2, which may be identical to or different from each other, are each hydrogen, chlorine, bromine or alkyl of 1 to 3 carbon atoms,A is alkylene of 1 to 5 carbon atoms, andR.sub.6 and R.sub.7, together with each other and the nitrogen atom to which they are attached, form a heterocycle selected from the group consisting of morpholino, piperazino or N'-dimethylphenyl-piperazino, andR.sub.5 is hydrogen, alkyl of 1 to 3 carbon atoms, hydroxyethyl, diethylamino-ethyl or furfuryl,Provided, however, that R.sub.1 and R.sub.2 are other than both hydrogen or both alkyl at the same time, and non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as the salts are useful as hypotensives, platelet aggregation inhibitors and antiarrhythmics.
    Type: Grant
    Filed: March 9, 1977
    Date of Patent: February 14, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Werner Kummer, Herbert Koppe, Helmut Stahle, Walter Haarmann
  • Patent number: 4058616
    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, which may be identical to or different from each other, are each methyl, ethyl or alkoxy-alkyl of 2 to 4 carbon atoms or, together with each other and the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocycle which may contain an additional heteroatom, such as pyrrolidino, piperidino, morpholino, piperazino or hexamethyleneimino;And non-toxic, pharmaceutically acceptable acid addition salts thereof; the compounds as well as the salts are useful as antithrombotics.
    Type: Grant
    Filed: June 3, 1976
    Date of Patent: November 15, 1977
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Werner Kummer, Helmut Stahle, Herbert Koppe, Walter Haarmann, Richard Reichl
  • Patent number: 4036972
    Abstract: Compounds of the formula ##STR1## wherein R, R.sub.1 and R.sub.2 are each hydrogen, fluorine, chlorine, bromine, methoxy or trifluoromethyl, but other than all hydrogen at the same time, andR.sub.3 is hydrogen, methyl or ethyl,And non-toxic, pharmaceutically acceptable acid addition salts thereof; the compounds as well as their salts are useful as analgesics and hypotensives.
    Type: Grant
    Filed: August 25, 1975
    Date of Patent: July 19, 1977
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Klaus Stockhaus
  • Patent number: 4031244
    Abstract: Pharmaceutical compositions containing as an active ingredient a compound of the formula ##STR1## wherein R is hydrogen or alkyl of 1 to 3 carbon atoms, and R.sub.1 is hydrogen or methyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof; and a method of using the same as anticonvulsives and antiarrhythmics.
    Type: Grant
    Filed: January 29, 1976
    Date of Patent: June 21, 1977
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Herbert Koppe, Karl Zeile, Werner Kummer, Helmut Stahle, Peter Danneberg
  • Patent number: 4025646
    Abstract: Pharmaceutical compositions containing as an active ingredient a racemic or optically active compound of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, andR.sub.2 is straight or branched hydroxyalkyl of 3 to 6 carbon atoms,Or a non-toxic, pharmacologically acceptable acid addition salt thereof; and a method of using the same as .beta.-adrenergic receptor blocking agents and hypotensives.
    Type: Grant
    Filed: January 26, 1976
    Date of Patent: May 24, 1977
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Herbert Koppe, Helmut Stahle, Werner Kummer, Werner Traunecker
  • Patent number: 4025607
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3, which may be identical to or different from each other, are each hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy or trifluoromethyl, andR.sub.4 and R.sub.5 are each hydrogen or propargyl, but other than both hydrogen or both propargyl at the same time,And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as the salts are useful as analgesics and hypotensives.
    Type: Grant
    Filed: May 17, 1976
    Date of Patent: May 24, 1977
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Klaus Stockhaus, Wolfgang Hoefke, Franz Josef Kuhn