Patents by Inventor Walter Haarmann
Walter Haarmann 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: 4191776Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, fluorine, chlorine, bromine, methyl, methoxy, methylthio or cyano;R.sub.2 is hydrogen or fluorine;R.sub.3 is carboxyl, (alkoxy of 1 to 6 carbon atoms)-carbonyl, methoxy-(alkoxy of 1 to 6 carbon atoms)-carbonyl, (alkenyloxy of 2 to 6 carbon atoms)-carbonyl, (aralkoxy of 7 to 12 carbon atoms)-carbonyl, phenoxy-carbonyl or pyridyl-methoxy-carbonyl,A is (alkyl of 1 to 3 carbon atoms)-methylene,m is 1 or 2; andn is 0, 1, 2 or 3;and, when R.sub.3 is carboxyl, non-toxic salts thereof formed with an inorganic or organic base. The compounds as well as the salts are useful as antithrombotics, anticholesteremics and anticoagulants.Type: GrantFiled: November 18, 1977Date of Patent: March 4, 1980Assignee: Boehringer Ingelheim GmbHInventors: Josef Nickl, Erich Muller, Berthold Narr, Walter Haarmann, Wolfgang Schroter, Rudolf Kadatz
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Patent number: 4182887Abstract: 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: GrantFiled: September 19, 1977Date of Patent: January 8, 1980Assignee: Boehringer Ingelheim GmbHInventors: Josef Roch, Erich Muller, Berthold Narr, Josef Nickl, Walter Haarmann
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Patent number: 4176184Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is lower alkyl; phenyl-lower alkyl; cycloalkyl of 3 to 6 carbon atoms; phenyl; mono- or di-substituted phenyl, where the substituents, which may be identical to or different from each other, are each halogen, hydroxyl, methoxy, methylmercapto, methylsulfinyl, methylsulfonyl or benzyloxy; andA is hydrogen or ##STR2## where R.sub.2 is hydrogen or lower alkyl;R.sub.3 is lower alkyl or dimethoxyphenyl-lower alkyl; orR.sub.2 and R.sub.3, together with each other and the nitrogen atom to which they are attached, are piperidino, morpholino or N'-lower alkyl-piperazino; andn is 2 or 3;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as cardiotonics, hypotensives, antithrombotics and antiarrhythmics.Type: GrantFiled: July 17, 1978Date of Patent: November 27, 1979Assignee: Boehringer Ingelheim GmbHInventors: Volkhard Austel, Eberhard Kutter, Joachim Heider, Wolfgang Eberlein, Walter Kobinger, Christian Lillie, Willi Diederen, Walter Haarmann
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Patent number: 4137313Abstract: 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: GrantFiled: January 27, 1978Date of Patent: January 30, 1979Assignee: Boehringer Ingelheim GmbHInventors: Gunter Trummlitz, Wolfhard Engel, Ernst Seeger, Walter Haarmann, Gunther Engelhardt
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Patent number: 4105765Abstract: 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: GrantFiled: September 29, 1977Date of Patent: August 8, 1978Assignee: Boehringer Ingelheim GmbHInventors: Werner Kummer, Helmut Stahle, Herbert Koppe, Walter Haarmann, Richard Reichl
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Patent number: 4080503Abstract: 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: GrantFiled: July 16, 1973Date of Patent: March 21, 1978Assignee: Boehringer Ingelheim GmbHInventors: Werner Kummer, Herbert Koppe, Helmut Stahle, Walter Haarmann
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Patent number: 4073905Abstract: 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: GrantFiled: March 9, 1977Date of Patent: February 14, 1978Assignee: Boehringer Ingelheim GmbHInventors: Werner Kummer, Herbert Koppe, Helmut Stahle, Walter Haarmann
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Patent number: 4062973Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or halogen,R.sub.2 is hydroxyl, alkoxy of 1 to 6 carbon atoms, aralkoxy of 7 to 10 carbon atoms, amino, (alkyl of 1 to 3 carbon atoms)-amino, piperidino or morpholino, andn is 0, 1 or 2,Diastereoisomers thereof and, when R.sub.2 is hydroxyl, non-toxic, pharmacologically acceptable salts thereof formed with an inorganic or organic base; the compounds, their diastereoisomers and the salts are useful as antithrombotics, anti-hypercholesteremics and anti-hyperglyceridemics.Type: GrantFiled: October 6, 1976Date of Patent: December 13, 1977Assignee: Boehringer Ingelheim GmbHInventors: Josef Nickl, Berthold Narr, Erich Muller, Josef Roch, Walter Haarmann
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Patent number: 4058616Abstract: 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: GrantFiled: June 3, 1976Date of Patent: November 15, 1977Assignee: Boehringer Ingelheim GmbHInventors: Werner Kummer, Helmut Stahle, Herbert Koppe, Walter Haarmann, Richard Reichl
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Patent number: 3993683Abstract: Compounds of the formula ##SPC1##WhereinR.sub.1 is hydrogen, fluorine, bromine, methyl, methoxy, methylthio, nitro, cyano or, when A is other than methylene, R.sub.2 is hydrogen, R.sub.3 is carboxyl, m is 2 and n is 0, also chlorine;R.sub.2 is hydrogen or fluorine;R.sub.3 is hydrogen, methyl, hydroxymethyl, carboxyl, (alkoxy of 1 to 6 carbon atoms)-carbonyl, methoxy-(alkoxy of 1 to 6 carbon atoms)-carbonyl, (alkenyloxy of 2 to 6 carbon atoms)-carbonyl, (aralkoxy of 7 to 12 carbon atoms)-carbonyl, phenoxy-carbonyl, pyridylmethoxy-carbonyl, amino-carbonyl, (alkyl of 1 to 3 carbon atoms-amino)-carbonyl, (dialkyl of 1 to 3 carbon atoms-amino)-carbonyl, phenylamino-carbonyl, morpholino-carbonyl, piperidino-carbonyl, thiomorpholino-carbonyl, (1-oxidothiomorpholino)-carbonyl or (1,1-dioxido-thiomorpholino)-carbonyl;A is methylene, (alkyl of 1 to 3 carbon atoms)-methylene, di-(alkyl of 1 to 3 carbon atoms)-methylene, hydroxymethyl-methylene, hydroxymethylene or carbonyl;m is 1 or 2; andn is 0, 1, 2 or 3;And, when R.Type: GrantFiled: May 14, 1975Date of Patent: November 23, 1976Assignee: Boehringer Ingelheim GmbHInventors: Josef Nickl, Erich Muller, Berthold Narr, Walter Haarmann, Wolfgang Schroter, Rudolf Kadatz
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Patent number: 3992535Abstract: Compounds of the formula ##SPC1##WhereinR.sub.1 is hydrogen, methyl or ethyl, andAr is phenyl, 3-chlorophenyl, 3-bromophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 3-tolyl, 2-methoxyphenyl, 3-methoxyphenyl, 2-pyridyl, 4-methyl-2-pyridyl, 6-methyl-2-pyridyl, 3-hydroxy-2-pyridyl, 3-pyridyl, 4-pyridyl, 6-chloro-3-pyridazinyl, 2-pyrazinyl, 6-chloro-2-pyrazinyl, 6-chloro-4-pyrimidinyl, 2-thiazolyl, 4-methyl-2-thiazolyl, 4-ethyl-2-thiazolyl, 5-methyl-2-thiazolyl, 5-ethyl-2-thiazolyl, 4,5-dimethyl-2-thiazolyl, 4-ethyl-5-methyl-2-thiazolyl, 5-ethyl-4-methyl-2-thiazolyl, 2-benzothiazolyl, 4,5,6,7-tetrahydro-2-benzothiazolyl, 5,6-dihydro-7H-thiopyrano[4,3-d]thiazol-2-yl, 3-methyl-5-isothiazolyl, 1,3,4-thiadiazolyl, 5-methyl-1,3,4-thiadiazol-2-yl or 5-methyl-3-isoxazolyl,And non-toxic, pharmacologically acceptable salts thereof formed with an inorganic or organic base; the compounds as well as their salts are useful as inhibitors of platelet adhesion and aggregation.Type: GrantFiled: October 29, 1975Date of Patent: November 16, 1976Assignee: Boehringer Ingelheim GmbHInventors: Gunter Trummlitz, Helmut Teufel, Wolfhard Engel, Ernst Seeger, Walter Haarmann, Gunther Engelhardt
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Patent number: 3975384Abstract: Compounds of the formula ##SPC1##WhereinR.sub.1 is alkoxy of 1 to 3 carbon atoms, morpholino, thiomorpholino, 1-oxido-thiomorpholino, 1,1-dioxido-thiomorpholino, or ##EQU1## where A is hydrogen, alkanoyl of 1 to 4 carbon atoms, alkenoyl of 2 to 4 carbon atoms, methoxy-(alkanoyl of 1 to 4 carbon atoms), carboxyl-(alkanoyl of 1 to 4 carbon atoms), acetyl-(alkanoyl of 1 to 4 carbon atoms), methoxy-(alkenoyl of 2 to 4 carbon atoms), carboxyl-(alkenoyl of 2 to 4 carbon atoms), acetyl-(alkenoyl of 2 to 4 carbon atoms), aminocarbonyl, mono(alkyl of 1 to 4 carbon atoms)-aminocarbonyl, di-(alkyl of 1 to 4 carbon atoms)-aminocarbonyl, methoxymethylaminocarbonyl, pyridinoyl, salicyloyl, furanoyl, or (alkyl of 1 to 3 carbon atoms)-sulfonyl,R.sub.2 is morpholino, thiomorpholino, 1-oxido-thiomorpholino, 1,1-dioxido-thiomorpholino, piperazino or N'-[acetyl-(alkanoyl of 1 to 3 arbon atoms)]-piperazino,R.sub.3 is hydrogen, chlorine, bromine, nitro, cyano, formyl, acetyl or carbalkoxy of 2 to 4 carbon atoms, andR.sub.Type: GrantFiled: August 14, 1974Date of Patent: August 17, 1976Assignee: Boehringer Ingelheim GmbHInventors: Berthold Narr, Josef Roch, Erich Muller, Walter Haarmann
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Patent number: 3975524Abstract: Compounds of the formula ##SPC1##WhereinR.sub.1 is hydrogen, alkyl of 1 to 3 carbon atoms, alkanoyl of 1 to 3 carbon atoms, or alkoxycarbonyl of 2 to 4 carbon atoms,R.sub.2 is morpholino, thiomorpholino or 1-oxido-thiomorpholino, andR.sub.3 is hydrogen, fluorine, chlorine, bromine, methyl, methoxy or nitro,And non-toxic, pharmacologicaly acceptable acid addition salts thereof; the compounds as well as the salts are useful as anticoagulants.Type: GrantFiled: April 11, 1975Date of Patent: August 17, 1976Assignee: Boehringer Ingelheim GmbHInventors: Josef Nickl, Erich Muller, Wolfgang Schroter, Walter Haarmann, Josef Roch