Patents by Inventor Hans Liepmann
Hans Liepmann 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).
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Patent number: 4649137Abstract: 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: GrantFiled: April 3, 1986Date of Patent: March 10, 1987Assignee: Kali-Chemie Pharma GmbHInventors: Horst Zeugner, Dietmar Romer, Hans Liepmann, Wolfgang Milkowski
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Patent number: 4594436Abstract: [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: GrantFiled: March 1, 1985Date of Patent: June 10, 1986Assignee: Kali-Chemie Pharma GmbHInventors: Hans Liepmann, Michael Ruhland, Herbert Muesch, Werner Benson, Henning Heinemann, Horst Zeugner
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Patent number: 4533662Abstract: 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: GrantFiled: December 14, 1981Date of Patent: August 6, 1985Assignee: Kali-Chemie Pharma GmbHInventors: Horst Zeugner, Dietmar Roemer, Hans Liepmann, Wolfgang Milkowski
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Patent number: 4508716Abstract: [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: GrantFiled: December 27, 1982Date of Patent: April 2, 1985Assignee: Kali-Chemie Pharma GmbHInventors: Hans Liepmann, Michael Ruhland, Herbert Muesch, Werner Benson, Henning Heinemann, Horst Zeugner
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Patent number: 4505908Abstract: 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: GrantFiled: September 23, 1982Date of Patent: March 19, 1985Assignee: Kali-Chemie Pharma GmbHInventors: Horst Zeugner, Michael Ruhland, Hans Liepmann, Wolfgang Milkowski, Herbert Muesch
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Patent number: 4497740Abstract: 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: GrantFiled: June 8, 1982Date of Patent: February 5, 1985Assignee: Kali-Chemie Pharma GmbHInventors: Horst Zeugner, Dietmar Romer, Hans Liepmann, Wolfgang Milkowski
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Patent number: 4482548Abstract: 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: GrantFiled: May 16, 1983Date of Patent: November 13, 1984Assignee: Kali-Chemie Pharma GmbHInventors: Dietmar Roemer, Michael Ruhland, Horst Zeugner, Wolfgang Milkowski, Hans Liepmann
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Patent number: 4402981Abstract: 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: GrantFiled: March 16, 1981Date of Patent: September 6, 1983Assignee: Kali-Chemie Pharma, GmbHInventors: Hans Liepmann, Rolf Hueschens, Wolfgang Milkowski, Horst Zeugner, Henning Heinemann, Klaus-Ullrich Wolf, Insa Hell, Reinhard Hempel
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Patent number: 4382030Abstract: Novel 2-acylaminomethyl-1H-2,3-dihydro-1,4-benzodiazepine derivatives are disclosed which possess the Formula I ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, lower alkenyl or cyclopropylmethyl;R.sub.2 represents hydrogen, lower alkyl or lower alkenyl;R.sub.3 represents a group of the formula a, b, c or d; ##STR2## wherein R is hydrogen or C.sub.1 -C.sub.3 -alkyl;R.sub.4 is hydrogen, lower alkyl, lower alkoxy, nitro or halogen, andR.sub.4 ' is hydrogen or C.sub.1 -C.sub.4 -alkyl and the aromatic groups A and B may be unsubstituted or substituted by 1 to 3 substituents such as halogen, lower alkylthio, lower alkoxy, lower alkyl, hydroxy, nitro, trifluoromethyl or methylenedioxy or ethylenedioxy and optical isomers and acid addition salts of the compounds. In addition to psycho pharmacological, diuretic and antiarrhythmic properties, the novel compounds of Formula I possess primarily outstanding analgesic activities and are low in toxicity.Type: GrantFiled: January 12, 1982Date of Patent: May 3, 1983Assignee: Kali-Chemie Pharma GmbHInventors: Horst Zeugner, Dietmar Roemer, Hans Liepmann
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Patent number: 4338314Abstract: Compounds of [1,2]anellated-7-phenyl-1,4-benzodiazepines having the formula I ##STR1## wherein X is oxygen, sulfur or NR;R is H,C.sub.1 -C.sub.5 alkyl,C.sub.1 -C.sub.5 alkyl, substituted with a terminal phenyl group, which is unsubstituted or substituted by one or 2 methoxy groups, a 3,4-methylene dioxy or 3,4-ethylenedioxy group,C.sub.2 -C.sub.5 alkyl, substituted with terminal halogen, hydroxy or methoxy or,C.sub.3 -C.sub.5 alkenylR.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are the same or different and are H, halogen, trifluoromethyl, nitro, alkyl, alkoxy, or alkylthio wherein alkyl is C.sub.1 -C.sub.4 alkyl or two neighboring groups represent a methylenedioxy or ethylenedioxy group and the acid addition salts thereof, ulcer treating pharmaceutical compositions containing these compounds and a method of medical treatment using same.Type: GrantFiled: August 16, 1979Date of Patent: July 6, 1982Assignee: Kali-Chemie Pharma GmbHInventors: Hans Liepmann, Rolf Hueschens, Wolfgang Milkowski, Horst Zeugner, Insa Hell, Klaus-Ullrich Wolf
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Patent number: 4325957Abstract: Novel 2-acylaminomethyl-1H-2,3-dihydro-1,4-benzodiazepine derivatives are disclosed which possess the Formula I ##STR1## wherein R.sub.1 represents hydrogen, lower akyl, lower alkenyl or cyclopropylmethyl;R.sub.2 represents hydrogen, lower alkyl or lower alkenyl;R.sub.3 represents a group of the formula a, b, c or d; ##STR2## wherein R is hydrogen or C.sub.1 -C.sub.3 - alkyl;R.sub.4 is hydrogen, lower alkyl, lower alkoxy, nitro or halogen, andR.sub.4 ' is hydrogen or C.sub.1 -C.sub.4 - alkyl and the aromatic groups A and B may be unsubstituted or substituted by 1 to 3 substituents such as halogen, lower alkylthio, lower alkoxy, lower alkyl, hydroxy, nitro, trifluoromethyl or methylenedioxy or ethylenedioxy and optical isomers and acid addition salts of the compounds. In addition to psycho pharmacological, diuretic and antiarrhythmic properties, the novel compounds of Formula I possess primarily outstanding analgesic activities and are low in toxicity.Type: GrantFiled: December 23, 1980Date of Patent: April 20, 1982Assignee: Kali-Chemie Pharma GmbH.Inventors: Horst Zeugner, Dietmar Roemer, Hans Liepmann, Wolfgang Milkowski
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Patent number: 4271193Abstract: N.sub.1 -benzoyl-N.sub.2 -phenyl-1,3-diaminopropan-2-ols are disclosed which exhibit a stabilizing effect on the gastric mucosa and enhance the stability and resistance of the gastic mucosa against harmful effects caused by, e.g., excessive alcohol consumption or drugs. The compounds are useful in the prophylaxis and treatment of gastritis.Further disclosed are pharmaceutical compositions which are effective in stabilizing the gastric mucosa and in the treatment and proplylaxis of gastritis and which comprise as a pharmacologically active ingredient N.sub.1 -benzoyl-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 -benzoyl-N.sub.2 -phenyl-1,3-diaminopropan-2-ols.Type: GrantFiled: June 22, 1979Date of Patent: June 2, 1981Assignee: Kali-Chemie Pharma GmbHInventors: Hans Liepmann, Rolf Hueschens, Wolfgang Milkowski, Horst Zeugner, Henning Heinemann, Klaus-Ulrich Wolf, Insa Hell, Reinhard Hempel
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Patent number: 4191770Abstract: 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: GrantFiled: April 28, 1978Date of Patent: March 4, 1980Assignee: Kali-Chemie Pharma GmbHInventors: Hans Liepmann, Rolf Hueschens, Wolfgang Milkowski, Horst Zeugner, Henning Heinemann, Klaus-Ullrich Wolf, Insa Hell, Reinhard Hempel
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Patent number: 4177287Abstract: Pharmaceutical compositions are disclosed, which are effective in the treatment and prophylaxis of ulcers and which comprise as a pharmacologically active ulcus-inhibiting ingredient a compound selected from the group of N.sub.1 -acyl-N.sub.2 -(4-chlorophenyl)-1,3-diaminopropan-2-ols, having the formula I ##STR1## wherein R.sub.1 represents 3,4-dimethoxyphenyl, 2-fluorophenyl, 2-trifluoromethylphenyl, or furyl, and pharmaceutically acceptable acid addition salts thereof, and a pharmaceutically acceptable diluent.Further disclosed is a new process for the preparation of the compounds of formula I.Type: GrantFiled: April 28, 1978Date of Patent: December 4, 1979Assignee: Kali-Chemie Pharma GmbHInventors: Hans Liepmann, Rolf Hueschens, Wolfgang Milkowski, Horst Zeugner, Henning Heinemann, Klaus-Ullrich Wolf, Insa Hell, Reinhard Hempel
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Patent number: 4170649Abstract: New 1,4-benzodiazepine derivatives are disclosed which are substituted in 2-position by cyanomethylene or carbamoylmethylene and have the formula ##STR1## wherein R.sub.1 represents hydrogen, halogen, or nitro, R.sub.2 represents hydrogen or lower alkyl, R.sub.3 represents phenyl which may be substituted by halogen or CF.sub.3, and R.sub.4 represents cyano or carbamoyl. The compounds exhibit tranquilizing activities. The cyanomethylene-compounds are prepared by oxidizing corresponding cyanomethyl compounds with Cr-VI-oxide in an acidic reaction medium. The cyanomethylene-group can subsequently be hydrolyzed into the carbamoylmethylene group.Type: GrantFiled: December 5, 1978Date of Patent: October 9, 1979Assignee: Kali-Chemie Pharma GmbHInventors: Hans Liepmann, Rolf Hueschens, Wolfgang Milkowski, Horst Zeugner, Renke Budden, Jacqueline Bahlsen