Patents Assigned to Kali-Chemie Pharma GmbH
  • Patent number: 4672062
    Abstract: 3-amino-2,3-dihydro-1-benzoxepine compounds corresponding to the general Formula I ##STR1## wherein R.sub.1 and R.sub.2 may each be hydrogen, halogen, lower alkyl or lower alkoxy, or if one of R.sub.1 and R.sub.2 is hydrogen, the other may also be nitro or trifluoromethyl, R.sub.3 represents hydrogen or a lower alkyl group which optionally may be substituted by hydroxy, lower alnoxy, an optionally substituted phenyl group or an optionally substituted amino group, and R.sub.4 represents hydrogen or lower alkyl, or R.sub.3 and R.sub.4 together with the nitrogen atom form a 5 or 6 member heterocycle. The compounds exhibit pharmacological, especially antidepressive, activity.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: June 9, 1987
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Heinrich-Wilhelm Ohlendorf, Michael Ruhland, Klaus-Ullrich Wolf
  • Patent number: 4672063
    Abstract: 5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3-one compounds of the Formula ##STR1## in which R.sub.1 is a straight-chain, branched or cyclic alkyl group with up to 6 carbon atoms, Z is an alkylene chain with 2 to 4 carbon atoms, and 1-phenyl substituent is an optionally substituted phenyl ring, and R.sub.4 is a phenyl or pyridyl group which is optionally substituted and their preparation are described. The compounds have pharmacological, particularly antiallergic, properties.
    Type: Grant
    Filed: November 21, 1985
    Date of Patent: June 9, 1987
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Daniel Jasserand, Marie-Odile Christen, Dominique Biard, Dimitri Yavordios
  • Patent number: 4649137
    Abstract: New 2-acylaminomethyl-1H-2,3-dihydro-1,4-benzodiazepine compounds are described having the general formula I ##STR1## wherein R.sub.1 is a hydrogen atom or a lower alkyl or alkenyl radical or the cyclopropylmethyl radical, R.sub.2 is a hydrogen atom, n is 0, 1 or 2, R.sub.3 is an optionally substituted furyl, thienyl, pyrrolyl, pyridyl or phenyl radical, R.sub.4 is an optionally substituted furyl, thienyl or, pyrrolyl radical, R.sub.5 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxyl, lower alkylthio, nitro, trifuloromethyl, cyano, amino, lower mono- or dialkylamino, lower monoalkanoylamino, lower N-alkyl-N-alkanoylamino or lower alkanoyloxy radical, and R.sub.6 is a hydrogen atom, or a lower alkyl or lower alkoxy radical or R.sub.5 and R.sub.6 together denote a methylenedioxy or ethylenedioxy radical. The compounds have pharmacological, for example, analgesic, properties.
    Type: Grant
    Filed: April 3, 1986
    Date of Patent: March 10, 1987
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Horst Zeugner, Dietmar Romer, Hans Liepmann, Wolfgang Milkowski
  • Patent number: 4594436
    Abstract: [1,2]-fused 1,4-benzodiazepine compounds are disclosed corresponding to the general formula I ##STR1## wherein X is an oxygen or sulfur atom or an optionally substituted imino group, R.sub.1 is a hydrogen or halogen atom, lower alkyl radical, a lower alkoxy radical or a nitro group and R.sub.2 is a hydrogen or halogen atom, a lower alkyl radical, a lower alkoxy radical or a nitro group, or if R.sub.1 is a hydrogen atom, R.sub.2 may also be a lower alkylthio radical, or, if R.sub.1 is a hydrogen atom and X is a sulfur atom or an imino group, R.sub.2 may be a trifluoromethyl radical; or R.sub.1 and R.sub.2 are bonded to adjacent carbon atoms and together denote a methylenedioxy or ethylenedioxy radical; R.sub.3 is an optionally substituted furyl, thienyl, pyrrolyl or pyridyl radical and n is zero or, if R.sub.3 is furyl or thienyl, n may be 0 or 1. The compounds may be in the form of their optical isomers or acid addition salts. The compounds exhibit neuroleptic properties.
    Type: Grant
    Filed: March 1, 1985
    Date of Patent: June 10, 1986
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Hans Liepmann, Michael Ruhland, Herbert Muesch, Werner Benson, Henning Heinemann, Horst Zeugner
  • Patent number: 4558052
    Abstract: 10-bromosandwicine and 10-bromoisosandwicine and acid addition salts thereof are disclosed. There novel compounds possess valuable pharmacological properties e.g. heart rhythm regulatory properties. Furthermore they are valuable intermediates for the preparation of 10-brominated N.sub.b -quaternary sandwicine derivatives which exhibit heart rhythm regulatory and adrenolytic properties. 10-bromosandwicine is prepared by brominating sandwicine and can subsequently be isomerized into 10-bromoisosandwicine.
    Type: Grant
    Filed: June 8, 1984
    Date of Patent: December 10, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Wolfgang Kehrbach, Joachim Wegener
  • Patent number: 4554274
    Abstract: New quaternary derivatives of 10-bromoajmaline and 10-bromoisoajmaline are disclosed which exhibit antiarrhythmic and adrenolytic properties and which have the formula I ##STR1## wherein R represents a carbon-attached organic group containing 1 to 10 carbon atoms and A.sup.- represents an acid anion as well as pharmaceutical formulations thereof and processes and intermediates for their preparation.
    Type: Grant
    Filed: May 31, 1984
    Date of Patent: November 19, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Wolfgang Kehrbach, Joachim Wegener, Ulrich Kuehl, Renke Budden, Gerd Buschmann
  • Patent number: 4552877
    Abstract: New N.sub.b -quaternary 10-bromosandwicine and 10-bromoisosandwicine derivatives are disclosed which exhibit antiarrhythmic properties and adrenolytic properties and which have the formula I ##STR1## wherein R represents a carbon-attached organic group containing 1 to 10 carbon atoms and A.sup..crclbar. represents an acid anion, as well as pharmaceutical formulations thereof and processes and intermediates for their preparation.
    Type: Grant
    Filed: May 31, 1984
    Date of Patent: November 12, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Wolfgang Kehrbach, Joachim Wegener, Ulrich Kuehl, Renke Budden, Gerd Buschmann
  • Patent number: 4550112
    Abstract: Novel 3,7-diaza bicyclo-(3,3,1)-nonane compounds are described which are represented by the formula: ##STR1## wherein Z.sub.1 and Z.sub.2 each denotes hydrogen,R.sub.1 and R.sub.2 each denotes (A) a substituent which contains up to 12 carbon atoms and which is selected from the group consisting of alkyl, alkenyl, and alkinyl, or (B) a cycloalkyl group containing 3 to 6 carbon atoms which is attached to the nitrogen atom directly or by an alkylene group containing 1 to 3 carbon atoms, andR.sub.3 and R.sub.4 each denotes an alkyl group with up to 7 carbon atoms, or both together form an alkylene chain represented by the formula --(CH.sub.2).sub.n --, wherein n is an integer ranging between about 3 and 6, such that the substituents R.sub.1, R.sub.2, R.sub.3, and R.sub.4 together contain at least 5 carbon atoms. Also described are processes of producing said compounds, pharmaceutical compositions containing compounds of Formula I, and methods of preparing and using said compositions.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: October 29, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Uwe Schoen, Bernd Hachmeister, Wolfgang Kehrbach, Ulrich Kuehl, Gerd Buschmann
  • Patent number: 4537975
    Abstract: Compounds corresponding to the formula: ##STR1## wherein R.sub.1 and R.sub.3 each represent hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl; R.sub.2 and R.sub.4 each represent hydrogen, halogen, lower alkyl or lower alkoxy; Z represents an alkylene radical with 2 to 6 carbon atoms and Y" is halogen, hydroxyl, lower alkanesulphonyl, benzenesulphonyl, or lower alkyl or halogen substituted benzenesulphonyl, and acid addition salts thereof, with the proviso the Y" is other than chlorine if R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each are hydrogen and Z is ethylene or propylene. The claimed compounds are useful intermediates in the synthesis of 1-phenyl-2-[(4-substituted piperazinyl) alkyl]-1,2-dihydro-3H-indazol-3-ones which exhibit antiallergic activity.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: August 27, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Henning Heinemann, Daniel Jasserand, Wolfgang Milkowski, Dimitri Yavordios, Horst Zeugner
  • Patent number: 4533662
    Abstract: Novel 2-acyl amino methyl-5-phenyl-1H-2,3-dihydro-1,4-benzo diazepine compounds of the following Formula I ##STR1## which have valuable pharmacological properties are provided. In said Formula I the acyl group --CO--R.sub.3 represents a benzoyl group or a phenyl alkanoyl group which may be unsubstituted or mono- or di-substituted in the phenyl ring. The substituent R.sub.1 in said compounds indicates lower alkyl, lower alkenyl, or cyclopropyl methyl, and the substituent R.sub.2 indicates hydrogen, lower alkyl, or lower alkenyl, while the substituent R.sub.6 indicates hydrogen, halogen, lower alkyl, lower alkoxy, hydroxyl, lower alkylthio, nitro, trifluoro methyl, cyano, amino, mono- or di-lower alkyl amino, lower mono-alkanoyl amino, lower N-alkyl-N-alkanoyl amino, or lower alkanoyloxy, and the substituent R.sub.7 indicates hydrogen, halogen, lower alkyl, lower alkoxy, hydroxyl, or lower alkanoyloxy, whereby R.sub.6 and R.sub.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: August 6, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Horst Zeugner, Dietmar Roemer, Hans Liepmann, Wolfgang Milkowski
  • Patent number: 4515944
    Abstract: Intermediates of the isomeric formulae II or III ##STR1## wherein R.sub.1 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxyl, trifluoromethyl or lower alkanoyloxy group,R.sub.2 is a hydrogen or halogen atom, or a lower alkyl or lower alkoxy group, orR.sub.1 and R.sub.2 are bonded to adjacent carbon atoms and together denote a methylenedioxy or ethylenedioxy group,R.sub.3 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxy, trifluoromethyl or lower alkanoyloxy group,R.sub.4 is a hydrogen or halogen atom, or a lower alkyl or lower alkoxy group, orR.sub.3 and R.sub.4 are bonded to adjacent carbon atoms and together denote a methylenedioxy or ethylenedioxy group, Z is an alkylene group with 2 to 6 carbon atoms, Z' is an alkylene group with 2 to 4 carbon atoms, Y is a halogen atom, and Y' is a halogen atom, and acid addition salts thereof, are useful to prepare antiallergic 2-piperazinoalkyl-1, 5-diphenylpyrazolin-3-ones.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: May 7, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Henning Heinemann, Daniel Jasserand, Wolfgang Milkowski, Dimitri Yavordios, Horst Zeugner
  • Patent number: 4508716
    Abstract: [1,2]-fused 1,4-benzodiazepine compounds are disclosed corresponding to the general formula I ##STR1## wherein X is an oxygen or sulfur atom or an optionally substituted imino group, R.sub.1 is a hydrogen or halogen atom, lower alkyl radical, a lower alkoxy radical or a nitro group and R.sub.2 is a hydrogen or halogen atom, a lower alkyl radical, a lower alkoxy radical or a nitro group, or if R.sub.1 is a hydrogen atom, R.sub.2 may also be a lower alkylthio radical, or, if R.sub.1 is a hydrogen atom and X is a sulfur atom or an imino group, R.sub.2 may be a trifluoromethyl radical; or R.sub.1 and R.sub.2 are bonded to adjacent carbon atoms and together denote a methylenedioxy or ethylenedioxy radical; R.sub.3 is an optionally substituted furyl, thienyl, pyrrolyl or pyridyl radical and n is zero or, if R.sub.3 is furyl or thienyl, n may be 0 or 1. The compounds may be in the form of their optical isomers or acid addition salts. The compounds exhibit neuroleptic properties.
    Type: Grant
    Filed: December 27, 1982
    Date of Patent: April 2, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Hans Liepmann, Michael Ruhland, Herbert Muesch, Werner Benson, Henning Heinemann, Horst Zeugner
  • Patent number: 4505908
    Abstract: Disclosed are 7-bromo-5-(2-halophenyl)-1H-2,3-dihydro-1,4-benzodiazepines of the formula I ##STR1## in which R.sub.1 is a hydrogen atom or a lower alkoxy or alkanoyloxy radical and R.sub.2 is a halogen atom. The compounds possess psychopharmacological, and especially anti-aggressive properties. To manufacture compounds of formula I, corresponding 2-halomethyl-7-bromo-5-(2-halophenyl)-1H-2,3-dihydro-1,4-benzodiazepines are cyclized to corresponding 7-bromo-1,2-methylene-5-(2-halophenyl)-1H-2,3-dihydro-1,4-benzodiazepines and in these the aziridine ring is opened through treatment with a lower alcohol or a lower carboxylic acid in the presence of a Lewis acid.
    Type: Grant
    Filed: September 23, 1982
    Date of Patent: March 19, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Horst Zeugner, Michael Ruhland, Hans Liepmann, Wolfgang Milkowski, Herbert Muesch
  • Patent number: 4497740
    Abstract: New 2-acylaminomethyl-1H-2,3-dihydro-1,4-benzodiazepine compounds are described having the general formula I ##STR1## wherein R.sub.1 is a hydrogen atom or a lower alkyl or alkenyl radical or the cyclopropylmethyl radical, R.sub.2 is a hydrogen atom, or a lower alkyl or alkenyl radical, n is 0, 1 or 2, R.sub.3 is an optionally substituted furyl, thienyl, pyrrolyl, pyridyl or phenyl radical, R.sub.4 is an optionally substituted furyl, thienyl, pyrrolyl or pyridyl radical, R.sub.5 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxyl, lower alkylthio, nitro, trifluoromethyl, cyano, amino, lower mono- or dialkylamino, lower monoalkanoylamino, lower N-alkyl-N-alkanoylamino or lower alkanoyloxy radical, and R.sub.6 is a hydrogen atom, or a lower alkyl or lower alkoxy radical or R.sub.5 and R.sub.6 together denote a methylenedioxy or ethylenedioxy radical. The compounds have pharmacological, for example, analgesic, properties.
    Type: Grant
    Filed: June 8, 1982
    Date of Patent: February 5, 1985
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Horst Zeugner, Dietmar Romer, Hans Liepmann, Wolfgang Milkowski
  • Patent number: 4482548
    Abstract: Highly effective analgesic pharmaceutical compositions and methods of using same are described. Said compositions contain, as analgesic agent, a 5-phenyl-1H-2,3-dihydro-1,4-benzodiazepine compound of the formula ##STR1## wherein R.sub.1 indicates a substituent selected from the group consisting of hydrogen and lower alkyl,R.sub.2 indicates a substituent selected from the group consisting of hydrogen, lower alkyl, and lower alkanoyl,R.sub.3 indicates a substituent selected from the group consisting of hydrogen and halogen, andR.sub.4 indicates halogen,or a physiologically compatible acid addition salt thereof.
    Type: Grant
    Filed: May 16, 1983
    Date of Patent: November 13, 1984
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Dietmar Roemer, Michael Ruhland, Horst Zeugner, Wolfgang Milkowski, Hans Liepmann
  • Patent number: 4451468
    Abstract: Acidiferous salts of 17-.beta.-n-pentyl sparteine are crystallized out of a solution of 17-.beta.-n-pentyl sparteine and a dicarboxylic acid selected from the group consisting of tartaric acid, fumaric acid or mixtures thereof. The novel acidiferous pentyl sparteine salts are employed in pharmaceutical compositions for the treatment of cardiac disorders and in venous therapeutical applications, and process improved stability and pharmacological properties.
    Type: Grant
    Filed: September 30, 1981
    Date of Patent: May 29, 1984
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Bernd Hachmeister, Wolfgang Milkowski, Ulrich Kuhl, Gerd Buschmann, Renke Budden
  • Patent number: 4448777
    Abstract: New 1-phenylindazol-3-one compounds are described which have the formula I ##STR1## where R.sub.1 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy or trifluoromethyl radical, R.sub.2 is a hydrogen or halogen atom, or a lower alkyl or lower alkoxy radical, R.sub.3 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy or trifluoromethyl radical, R.sub.4 is a hydrogen or halogen, atom, or a lower alkyl or lower alkoxy radical, Z is an alkylene radical with 2 to 6 carbon atoms and R.sub.5 is an unsubstituted or substituted pyridyl radical, a thienyl radical or an unsubstituted or substituted phenyl radical. The compounds have pharmacological actions, for example antiallergic actions. Methods of preparing these compounds are described as well as intermediates useful in these methods. Pharmaceutical compositions containing the compounds are also described.
    Type: Grant
    Filed: August 19, 1982
    Date of Patent: May 15, 1984
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Henning Heinemann, Daniel Jasserand, Wolfgang Milkowski, Dimitri Yavordios, Horst Zeugner
  • Patent number: 4442102
    Abstract: New 1,5-diphenylpyrazolin-3-one compounds and a method of preparing them are described. The compounds have the general formula I ##STR1## where R.sub.1 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxy, trifluoromethyl or lower alkanoyloxy radical, R.sub.2 is a hydrogen or halogen atom, or a lower alkyl, or lower alkoxy radical, or R.sub.1 and R.sub.2 are bonded to adjacent carbon atoms and together denote a methylenedioxy or ethylenedioxy radical, R.sub.3 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxy, trifluoromethyl or lower alkanoyloxy radical, R.sub.4 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy radical, or R.sub.3 and R.sub.4 are bonded to adjacent carbon atoms and together denote a methylenedioxy or ethylenedioxy radical, Z is an alkylene radical with 2 to 6 carbon atoms and R.sub.5 is an optionally substituted pyridyl radical, a thienyl radical or an optionally substituted phenyl radical.
    Type: Grant
    Filed: August 19, 1982
    Date of Patent: April 10, 1984
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Henning Heinemann, Daniel Jasserand, Wolfgang Milkowski, Dimitri Yavordios, Horst Zeugner
  • Patent number: 4415577
    Abstract: Disclosed are a novel dimeric sparteine derivative, the 17S,17'S-bissparteine, and its physiologically compatible acid addition salts. Said compounds are produced by dimerization of 17-hydroxy sparteine or 17-dehydrosparteine salts by means of activated magnesium or an alkali metal. Pharmaceutical compositions containing said novel dimeric sparteine derivatives and their preparation are also described.
    Type: Grant
    Filed: August 19, 1981
    Date of Patent: November 15, 1983
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Bernd Hachmeister, Wolfgang Kehrbach, Ulrich Kuehl, Gerd Buschmann
  • Patent number: 4402981
    Abstract: N.sub.1 -acyl-N.sub.2 -phenyl-1,3-diaminopropan-2-ols are disclosed which possess ulcer-inhibiting activities.Further disclosed are pharmaceutical compositions which are effective in the treatment and prophylaxis of ulcers and which comprise as a pharmacologically active ulcus-inhibiting ingredient N.sub.1 -acyl-N.sub.2 -phenyl-1,3-diaminopropan-2-ols, or a pharmaceutically acceptable acid addition salt thereof, and a pharmaceutically acceptable diluent.Further disclosed are processes for the preparation of the N.sub.1 -acyl-N.sub.2 -phenyl-1,3-diaminopropan-2-ols.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: September 6, 1983
    Assignee: Kali-Chemie Pharma, GmbH
    Inventors: Hans Liepmann, Rolf Hueschens, Wolfgang Milkowski, Horst Zeugner, Henning Heinemann, Klaus-Ullrich Wolf, Insa Hell, Reinhard Hempel