Abstract: The invention relates to pyrimidine-thioalkyl pyridine derivatives corresponding to the following general formula ##STR1## in which R.sub.1 to R.sub.4, independently of one another, represent hydrogen, lower alkyl, halogen, amino or hydroxy groups, R.sub.5 represents a free electron pair or a lower alkyl group, a halogen atom, m has the value 0 or 1, the pyrimidine-thioalkyl group being bonded in the 2-, 3- or 4-position of the pyridine ring, and to therapeutically compatible acid addition salts thereof. The invention also relates to a process for producing the new pyrimidine-thioalkyl pyridine derivatives and to medicaments containing these compounds.
Type:
Grant
Filed:
September 26, 1988
Date of Patent:
June 18, 1991
Assignee:
Ludwig Heumann & Co. GmbH
Inventors:
Kurt H. Ahrens, Helmut Schickaneder, Heidrun Engler, Istvan Szeleny
Abstract: Thiomethylpyridine derivatives having bronchosecretolytic and mucolytic activity according to the formula: ##STR1## wherein R is a group attached in the 2-, 3- or 4-position of the pyridine ring which corresponds to the following general formula:Q--S--CH.sub.2 -- (II)wherein Q is a substituted or unsubstituted aryl group or a 5- or 6-membered heterocyclic group which may optionally contain one or more substituents and/or which may be condensed with an optionally substituted phenyl group or with an optionally substituted heterocycle; R' is a lower alkyl group, a halogen atom or an aminoalkyl group; and n is 0 or an integer of from 1 to 4; and the therapeutically-acceptable acid addition salts thereof.The new compounds are distinguished by surprising activity compared with known compounds, such as "Ambroxol".
Type:
Grant
Filed:
February 17, 1987
Date of Patent:
September 12, 1989
Assignee:
Ludwig Heumann & Co. GmbH
Inventors:
Helmut Schickaneder, Heidrun Engler, Istvan Szelenyi
Abstract: Thiomethylpyridine derivatives having bronchosecretolytic and mucolytic activity according to the formula: ##STR1## wherein R is a group attached in the 2-, 3- or 4-position of the pyridine ring which corresponds to the following general formula:Q--S--CH.sub.2 -- (II)wherein Q is a substituted or unsubstituted aryl group or a 5- or 6-membered heterocyclic group which may optionally contain one or more substituents and/or which may be condensed with an optionally substituted phenyl group or with an optionally substituted heterocycle;R' is a lower alkyl group, a halogen atom or an aminoalkyl group; andn is 0 or an integer of from 1 to 4;and the therapeutically-acceptable acid addition salts thereof.The new compounds are distinguished by surprising activity compared with known compounds, such as "Ambroxol".
Type:
Grant
Filed:
March 16, 1987
Date of Patent:
March 7, 1989
Assignee:
Ludwig Heumann & Co. GmbH
Inventors:
Helmut Schickaneder, Heidrun Engler, Istvan Szelenyi
Abstract: 1,3,4-Thiadiazole derivatives corresponding to the general formula I ##STR1## which constitute highly effective inhibitors for histamine-H.sub.2 receptors are described. These compounds in addition have a cytoprotective action.
Type:
Grant
Filed:
November 19, 1985
Date of Patent:
April 19, 1988
Assignee:
Ludwig Heumann & Co. GmbH
Inventors:
Helmut Schickaneder, Rolf Herter, Kurt Wegner, Walter Schunack, Istvan Szelenyi, Stefan Postius, Kurt H. Ahrens
Abstract: Benzothiazole derivatives corresponding to the general formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 represent, independently of one another, a hydrogen atom, a halogen atom, a linear C.sub.1 -C.sub.3 -alkyl group or a linear C.sub.1 -C.sub.3 -alkoxy group, R.sup.5 represents a hydrogen atom or a linear C.sub.1 -C.sub.3 -alkyl group, R.sup.6 represents a hydrogen atom, and R.sup.7 represents a formyl group, a carbalkoxy group of the formula ##STR2## wherein R.sup.8 denotes a linear or branch chained C.sub.1 -C.sub.4 -alkyl group, or it represents an acyl group of the formula ##STR3## wherein R.sup.9 denotes a linear C.sub.1 -C.sub.3 -alkyl group, or R.sup.6 and R.sup.7 together represent the group ##STR4## wherein R.sup.10 and R.sup.11 represent, independently of one another, a hydrogen atom or a linear C.sub.1 -C.sub.6 -alkyl group or R.sup.6 and R.sup.7 represent the group ##STR5## wherein R.sup.12 and R.sup.13 represent, independently of one another, a linear C.sub.1 -C.sub.
Type:
Grant
Filed:
May 12, 1987
Date of Patent:
March 22, 1988
Assignee:
Ludwig Heumann & Co. GmbH
Inventors:
Kay Brune, Heidrun Engler, Istvan Szelenyi, Peter Morsdorf, Helmut Schickaneder, Kurt H. Ahrens
Abstract: 3,4-Diazole derivatives corresponding to the general formula I ##STR1## which exert a highly selective action on histamine-H.sub.2 receptors are described. Processes for the preparation of these compounds and pharmaceutical preparations containing these compounds are also described.
Type:
Grant
Filed:
November 7, 1985
Date of Patent:
February 23, 1988
Assignee:
Ludwig Heumann & Co. GmbH
Inventors:
Kurt Wegner, Irene Kramer, Helmut Schickaneder, Walter Schunack, Istvan Szelenyi, Kurt H. Ahrens
Abstract: A simplified process for the preparation of basically substituted phenylacetonitriles, in particular of verapamil, is described. This process is carried out with fewer stages and higher yields than the known processes according to the state of the art.
Type:
Grant
Filed:
June 3, 1985
Date of Patent:
September 29, 1987
Assignee:
Ludwig Heumann & Co., GmbH
Inventors:
Lothar Kisielowski, Ingomar Grafe, Walter Liebenow, Kurt H. Ahrens
Abstract: The invention relates to the production of granulates by using a tabletting machine comprising at least one top punch and one bottom punch which co-operate with a die formed with a bore, the top punch being displaceable into the bore from outside to compress powder accommodated in the bore and the bottom punch displaceable in the bore being displaced within the bore for ejecting the powder compressed into a tablet, the tabletting machine additionally comprising a powder feed unit which introduces the powder into the bore when the top punch is in its raised position. According to the invention, a perforated plug in the bore of the die in conjunction with a granulate stripping, transporting and collecting system arranged beneath the lower end face of the perforated plug is used instead of the displaceable bottom punch for producing granulates.
Abstract: Special pyrazole derivatives corresponding to the general formula I which have a highly selective action on histamine-H.sub.2 receptors are described. Compared with other drugs known to be effective in their action on histamine-H.sub.2 receptors, these compounds have improved pharmacological properties. A method of preparation of these compounds is also described.
Type:
Grant
Filed:
October 15, 1985
Date of Patent:
May 19, 1987
Assignee:
Ludwig Heumann & Co. GmbH
Inventors:
Rolf Herter, Helmut Schickaneder, Peter Morsdorf, Stefan Postius, Istvan Szelenyi, Kurt H. Ahrens
Abstract: Alkanol derivatives corresponding to the general formula IR.sup.1 R.sup.2 N--(CH.sub.2).sub.m --Q--CH.sub.2 X--CH.sub.2 --Y--(CH.sub.2).sub.n --NHR.sup.3 (I)which have a highly selective action on histamine-H.sub.2 receptors are described. Due to this action, these compounds may advantageously be used for treatment of diseases caused by raised gastric secretion.
Type:
Grant
Filed:
January 22, 1985
Date of Patent:
April 21, 1987
Assignee:
Ludwig Heumann & Co. GmbH
Inventors:
Helmut Schickaneder, Stefan Postius, Istvan Szelenyi, Peter Morsdorf, Rolf Herter, Kurt H. Ahrens
Abstract: Diamine derivatives corresponding to the general formula IR.sup.1 R.sup.2 N--(CH.sub.2).sub.m --Q--A--NH--R--NH--B--Q'--(CH.sub.2).sub.n NR.sup.3 R.sup.4 (I)which have a highly selective action on histamine-H.sub.2 receptors and are therefore suitable for use as anti-ulcerative agents are described. Processes for the preparation of these compounds and pharmaceutical preparations containing these compounds are also described.
Type:
Grant
Filed:
March 5, 1985
Date of Patent:
April 7, 1987
Assignee:
Ludwig Heumann & Co., GmbH
Inventors:
Stefan Postius, Rolf Herter, Peter Morsdorf, Helmut Schickaneder, Istvan Szelenyi, Kurt H. Ahrens
Abstract: The invention relates to a new multistage process for the production of 4-amino-6,7-dimethoxy-2-[4-(furo-2-yl)-piperazin-1-yl]-quinazoline corresponding to the following formula ##STR1## and physiologically compatible salts thereof, which gives better yields and uses less expensive and more reactive materials than known processes. The intermediate product formed in this process, N"-cyano-N'-(3,4-dimethoxyphenyl)-O-phenylisourea, shows antihypertensive activity on its own.
Abstract: 1,3-Dioxolanyl derivatives corresponding to the general formula I ##STR1## are described. These compounds have an antimicrobial activity and may therefore advantageously be used in chemotherapy.
Type:
Grant
Filed:
December 28, 1984
Date of Patent:
January 6, 1987
Assignee:
Ludwig Heumann & Co., GmbH
Inventors:
Helmut Schickaneder, Klaus Hoxer, Kurt H. Ahrens
Abstract: Pharmaceutical preparations having an antiphlogistic action are described. The preparations contain, as active ingredient, a benzazole derivative corresponding to the general tautomeric formulae I ##STR1## wherein X represents a sulphur or oxygen atom and R.sup.1 represents a hydrogen atom and R.sup.2 a hydroxymethyl, formyl, lower carbalkoxy or lower acyl group or R.sup.1 and R.sup.2 together represent the group ##STR2## wherein R.sup.3 and R.sup.4 denote, independently of one another, a hydrogen atom or a C.sub.1 -C.sub.6 -alkyl group, or they contain a physiologically acceptable salt thereof. These pharmaceutical preparations are suitable in particular for the treatment of inflammatory conditions and for inhibiting the lipoxygenase and/or cyclooxygenase route of arachidonic acid metabolism.
Type:
Grant
Filed:
March 27, 1985
Date of Patent:
July 15, 1986
Assignee:
Ludwig Heumann & Co., GmbH
Inventors:
Peter Morsdorf, Helmut Schickaneder, Heidrun Engler, Istvan Szelenyi, Kurt H. Ahrens, Kay Brune
Abstract: The invention relates to new propan-2-ol derivatives corresponding to the following general formula ##STR1## in which R represents ##STR2## and to salts thereof with pharmacologically acceptable acids. These compounds have a selective effect on histamine-H.sub.2 -receptors.
Type:
Grant
Filed:
July 16, 1984
Date of Patent:
July 8, 1986
Assignee:
Ludwig Heumann & Co., GmbH
Inventors:
Helmut Schickaneder, Stefan Postius, Rolf Herter, Peter Morsdorf, Istvan Szelenyi, Kurt H. Ahrens
Abstract: The invention relates to special heterocyclic compounds corresponding to general tautomeric formula I which are distinguished by improved antagonistic activity on histamine-H.sub.2 -receptors. The invention also relates to a process for producing these compounds and to medicaments containing them.
Type:
Grant
Filed:
October 18, 1983
Date of Patent:
June 24, 1986
Assignee:
Ludwig Heumann & Co., GmbH
Inventors:
Istvan Szelenyi, Stefan Postius, Helmut Schickaneder, Herbert Hansen
Abstract: The invention relates to quinazoline derivatives corresponding to the following general formula ##STR1## in which R is a mono- to trisubstituted 5-ring heterocycle from the group comprising triazoles, oxadiazoles, thiazoles and imidazoles, the heterocycle being attached to the piperazine or homopiperazine ring by a carbon atom, and n has a value of 2 or 3, or R represents an N-cyanophenyl imidocarbonate group, and to physiologically compatible salts thereof, to processes for their production and to medicaments containing these compounds.
Type:
Grant
Filed:
September 10, 1984
Date of Patent:
March 25, 1986
Assignee:
Ludwig Heumann & Co. GmbH
Inventors:
Helmut Schickaneder, Istvan Szeleny, Peter Morsdorf, Kurt H. Ahrens
Abstract: The invention relates to new pyridine-pyrimidinone derivatives corresponding to the following general formula ##STR1## wherein R.sup.1 represents linear C.sub.1-6 alkyl or cycloalkyl and R.sup.2 represents linear C.sub.1-6 alkyl or R.sup.1 and R.sup.2 together with the nitrogen atom form a pyrrolidine or piperidine ring;Alk represents a linear alkylene chain C.sub.1-6 ;Q represents a benzene ring, furan ring, thiophene ring or thiazole ring;X represents oxygen, Y is a single bond and m is 2, 3 or 4 when Q represents benzene;X represents methylene, Y represents sulfur and m is 2 or 3 when Q is furan, thiophene or thiazole; andR.sup.3 represents a hydrogen atom or a lower alkyl group.These compounds show improved H.sub.2 -antagonistic activity.
Type:
Grant
Filed:
January 26, 1984
Date of Patent:
December 17, 1985
Assignee:
Ludwig Heumann & Co. GmbH
Inventors:
Helmut Schickaneder, Peter Morsdorf, Stefan Postius, Istvan Szelenyi, Rolf Herter, Herbert Hansen, Kurt H. Ahrens
Abstract: Quaternary 1,1-diphenyl-4-pyrrolidinium-2-butyne salts corresponding to the following general formula ##STR1## in which R represents methyl or ethyl and X is a chlorine or bromine atom, are described. These compounds are distinguished by improved spasmolytic and broncholytic activity.
Abstract: A compound selected from a 2,4-diamino-5-thiobenzylpyrimidine of the formula: ##STR1## in which R is selected from hydrogen, alkyl, lower alkoxy, and halogen and R' is alkyl; and pharmacologically acceptable acid addition salts thereof. These compounds have an anti-bacterial action and are sulphonamide potentiators.
Type:
Grant
Filed:
March 29, 1978
Date of Patent:
December 25, 1979
Assignee:
Ludwig Heumann, & Co. GmbH
Inventors:
Edgar Fritschi, Walter Liebenow, Jaroslav Prikryl