Abstract: This invention relates to pharmaceutical compositions containing quinolin-2,5-diones of formula ##STR1## wherein A, B, R.sup.1 to R.sup.3 and X are defined hereinbelow, some of which are novel, which compounds have valuable pharmacological properties, particularly analgesic antipyretic and/or antiphlogistic effects, to new intermediates and processes for preparing them.
Type:
Grant
Filed:
September 27, 1989
Date of Patent:
November 26, 1991
Assignee:
Karl Thomae GmbH
Inventors:
Erich Muller, Josef Nickl, deceased, Armin Heckel, Gunther Engelhardt
Abstract: The specification describes a new process and apparatus for the controlled release of metered quantities of lubricating liquids or suspensions for applying a coating of lubricant to mechanically stressed zones of pressing tools in tablet-making machines, wherein the lubricating solution or suspension is fed into one or more liquid valves synchronously with the cadence of the tablet-making machine from a pressureless storage container by means of a pulsation-free pump, and any pressure variations occuring in the liquid supply line to the valves are compensated by changes in the times of opening of the valves.
Abstract: The invention relates to new morpholines and morpholine-N-oxides of formula ##STR1## wherein the substituents are defined hereunder, which compounds have valuable pharmacological properties, namely an effect on the metabolism, preferably the effect of lowering blood sugar and reducing body fat, and the effect of lowering the atherogenic .beta.-lipoproteins VLDL and LDL, and a performance enhancing effect in animals.
Type:
Grant
Filed:
March 23, 1989
Date of Patent:
June 25, 1991
Assignee:
Dr. Karl Thomae, GmbH
Inventors:
Manfred Reiffen, Michael Mark, Robert Sauter, Wolfgang Grell
Abstract: 5,11-Dihydro-6H-pyrido[2,3-b][1,4]-benzo-diazepinones substituted in the 11-position corresponding to general formula I ##STR1## wherein R.sup.1 and R.sup.2 represent hydrogen atoms or alkyl groups having 1 to 3 carbon atoms, A.sup.1 is a straight-chained or branched alkylene group with 1 to 5 carbon atoms, A.sup.2 is a methylene group or, if R.sup.1 is hydrogen and R.sup.2 is methyl, A.sup.2 may also be an ethylene group, and the physiologically acceptable acid addition salts thereof are suitable for treating bradycardia and bradyarrhythmia and spasm in the colon, bladder and bronchi.
Type:
Grant
Filed:
June 15, 1989
Date of Patent:
June 25, 1991
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Gerhard Mihm, Wolfgang Eberlein, Welfhard Engel, Gunter Trummlitz, Norbert Mayer, Henri Doods, Rudolf Hammer
Abstract: A method for treating abstructive respiratory passage disorders which comprises the use of 5,11-dihydro-11-[[(1-methyl-4-piperidinyl)-amino]carbonyl]-6H-dibenz[b,e]a zepin-6-one; 5,11-dihydro-11-[(1-methyl-4-piperazinyl)acetyl]-6H-dibenz[b,e]azepin-6-on e, 5,11-dihydro-11-[(4-methyl-1-piperazinyl)acetyl]-6H-dibenz[b,e]azepin-6-on e, alone or in combination.
Type:
Grant
Filed:
November 17, 1989
Date of Patent:
April 30, 1991
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Wolfgang Eberlein, Wolfhard Engel, Gerhard Mihm, Klaus Rudolf, Henri Doods, Norbert Mayer
Abstract: The invention relates to new sulphonamidoethyl compounds having valuable pharmacological properties, particularly anti-thrombotic properties, and which are also thromboxane antagonists.
Type:
Grant
Filed:
March 3, 1989
Date of Patent:
April 16, 1991
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Armin Heckel, Josef Nickl, Erich Muller, Berthold Narr, Johannes Weisenberger, Wolfgang Eisert, Thomas Muller
Abstract: Novel condensed diazepinone of general formula I are described, ##STR1## wherein B represents one of the divalent groups ##STR2## and X.sup.1, X.sup.2, A.sup.1, A.sup.2 and R.sup.1 to R.sup.10 are as defined in herein useful as vagal pacemakers for treating bradycardia and bradyarrhythmia. The novel diazepinones also have spasmolytic properties on peripheral organs, antiemetic properties and are capable of promoting cerebral blood flow.
Type:
Grant
Filed:
May 30, 1989
Date of Patent:
April 9, 1991
Assignee:
Karl Thomae GmbH
Inventors:
Wolfhard Engel, Wolfgang Eberlein, Gerhard Mihm, Gunther Trummlitz, Norbert Mayer, Adriaan De Jonge
Abstract: A method for treating shock in a patient, which comprises administering to the patient a therapeutically effective amount of a diazepinone of the general formula: ##STR1## wherein A represents a 5,11-dihydro-6H-pyrido[2,3-b] [1,4] benzodiazepin-6-one group bound in the 11-position; a 5,10-dihydro-11H-dibenzo [b,e] [1,4] diazepin-11-one group bound in the 5-position; a 5,11-dihydro-10H-pyrido [3-2b] [1-4] benzodiazepin-10-one group bound in the 5-position; a 4,9-dihydro-10H-thieno [3,4-b] [1,5] benzodiazpin-10-one group bound in the 4-position, unsubstituted or substituted at the 1- or 3-position or both in the 1- and 3-position by an alkyl group having from 1 to 4 carbon atoms, or in the 3-positionby chlorine, fluorine or bromine; a 6-11-dihydro-5H-pyrido [2,3-b] [1,5] benzodiazepin-5-one group bound in the 11-position; or a 1-methyl-1,4,9,10-tetrahydropyrrolo-[3,2-b] [1,5] benzodiazepin-10-one group bound in the 4-position, unsubstituted or substituted at the 3-position by methyl or methyl or chlorine;R.sub.
Type:
Grant
Filed:
May 17, 1989
Date of Patent:
March 19, 1991
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Wolfgang Eberlein, Volker Trach, Wolfhard Engel, Gerhard Mihm, Norbert Mayer, Henri Doods, Richard Reichl
Abstract: Disclosed are substituted bis(4-aminophenyl)-sulfones of general formula ##STR1## wherein R.sub.1 is hydrogen, alkyl or cycloalkyl; group,R.sub.2 is hydrogen or C.sub.1 -C.sub.3 alkyl,R.sub.3 is nitrile, C.sub.1 -C.sub.3 alkylaminocarbonyl, di C.sub.1 -C.sub.3 alkylaminocarbonyl, C.sub.3 -C.sub.7 N-cycloalkyl-C.sub.1 -C.sub.3 alkylaminocarbonyl C.sub.1 -C.sub.3 alkylamino, C.sub.1 -C.sub.3, di alkylaminocarbonyl alkoxy, alkylaminosulfonyl, di C.sub.1 -C.sub.3 alkylaminono, diC.sub.1 -C.sub.3 alkylaminosulfonyl, hydroxy C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkylcarbonyl, amino C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy C.sub.1 -C.sub.3 alkyl groupor, when R.sub.1 and R.sub.2 are each hydrogen, R.sub.3 can be hydroxy, hydroxycarbonyl C.sub.1 -C.sub.3 alkoxy or di C.sub.1 -C.sub.3 aminocarbonylalkoxy;or, when R.sub.1 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 cycloalkyl and R.sub.2 is hydrogen or C.sub.1 -C.sub.3 alkyl, R.sub.
Type:
Grant
Filed:
January 26, 1989
Date of Patent:
February 12, 1991
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Joachim K. Seydel, Helmut Pieper, Gerd Kruger, Klaus Noll, Johannes Keck, Uwe Lechner
Abstract: New substituted pyrido[2,3-b][1,4]benzodiazepin-6-ones suitable as vagal pacemakers for the treatment of bradycardias and bradyarrhythmias in human and veterinary medicine are described.
Type:
Grant
Filed:
July 31, 1987
Date of Patent:
November 20, 1990
Assignee:
Karl Thomae GmbH
Inventors:
Wolfhard Engel, Wolfgang Eberlein, Gunter Trummlitz, Gerhard Mihm, Norbert Mayer, Adriaan de Jonge
Abstract: The invention relates to a process for preparing enantiomerically pure S(+)-propan-1,2-diol and R(-)-propan-1,2-diol from L(-)-lactide or D(+)-lactide, respectively.
Abstract: New condensed diazepinones of general formula I are described ##STR1## wherein B represents one of the divalent groups ##STR2## and X.sup.1, X.sup.2, A, R.sup.1 to R.sup.10 and Z are defined as in the specification.
Type:
Grant
Filed:
August 9, 1988
Date of Patent:
June 5, 1990
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Wolfhard Engel, Gunter Trummlitz, Wolfgang Eberlein, Gerhard Mihm, Norbert Mayer, Adriaan De Jonge, Klaus Rudolf
Abstract: The invention relates to new benzenesulphonamidoindanyl compounds useful in the treatment and prophylaxis of thromboembolic diseases, arteriosclerosis and tumor metastasis.
Type:
Grant
Filed:
February 1, 1989
Date of Patent:
May 29, 1990
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Josef Nickl, Armin Heckel, Erich Muller, Berthold Narr, Johannes Weisenberger, Wolfgang Eisert, Thomas Muller
Abstract: The present invention relates to new heteroaromatic amine derivatives of general formula ##STR1## wherein the substituents are defined hereinbelow, which have valuable pharmacological properties, particularly a heart rate lowering activity and a positive inotropic activity.
Type:
Grant
Filed:
November 25, 1987
Date of Patent:
March 27, 1990
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Andreas Bomhard, Joachim Heider, Manfred Psiorz, Norbert Hauel, Berthold Narr, Klaus Noll, Christian Lillie, Walter Kobinger, Willi Diederen
Abstract: (.+-.)-1-[4-[Ethyl[2-(4-methoxyphenyl)-1-methylethyl]-amino]-1-oxobutyl]-N, N-dimethyl-4-piperidine carboxamide and (+)-1-[4-[ethyl[2-(4-methoxyphenyl)-1-methylethyl]-amino]-1-oxobutyl]N,N-d imethyl-4-piperidinecarboxamide, as well as the physiologically acceptable acid addition salts of these compounds are suitable for the treatment of bradycardia and bradyarrhythmia.
Type:
Grant
Filed:
January 17, 1989
Date of Patent:
February 27, 1990
Assignee:
Dr. Karl Thomae, GmbH
Inventors:
Wolfgang Eberlein, Wolfhard Engel, Gerhard Mihm, Norbert Mayer, Adriaan de Jonge
Abstract: This invention relates to new tetrahydrobenzthiazoles of general formula ##STR1## wherein R.sub.1 represents a hydrogen atom, an alkyl group, an alkenyl or alkynyl group, an alkanoyl group, a phenyl alkyl or phenyl alkanoyl group, while the above mentioned phenyl nucleic may each be substituted by 1 or 2 halogen atoms,R.sub.2 represents a hydrogen atom or an alkyl group,R.sub.3 represents a hydrogen atom, an alkyl group a cycloalkyl group, an alkenyl or alkynyl group, an alkanoyl group, a phenyl alkyl or phenyl alkanoyl group, while the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms,R.sub.4 represents a hydrogen atom, an alkyl group, an alkyl or alkenyl group, orR.sub.3 and R.sub.4 together with the nitrogen atom between them represent a pyrrolidino, piperidino, hexamethyleneimino or morpholino group, the enantiomers and the acid addition salts thereof.The compounds of general formula I above in which one of the groups R.sub.1 or R.sub.3 or both groups R.sub.1 and R.sub.
Type:
Grant
Filed:
October 12, 1988
Date of Patent:
December 12, 1989
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Gerhart Griss, deceased, Claus Schneider, Rudolf Hurnaus, Walter Kobinger, Ludwig Pichler, Rudolf Bauer, Joachim Mierau, Dieter Hinzen, Gunter Schingnitz
Abstract: There are described new condensed diazepinones of general formula ##STR1## wherein .circle.B represents one of the divalent groups ##STR2## and D represents the groups ##STR3## and X.sup.1, X.sup.2 represents a .dbd.CH-- group or, if .circle.B assumes the meaning of the divalent group S, U or W, they may also represent an N atom, A.sup.1 and A.sup.2 in general represent lower alkylene groups, Z represents a C--C bond or the groups, --O--, --S--, --CH.sub.2 --, or --(CH.sub.2).sub.2 --; R represents hydrogen or methyl, R.sup.1 and R.sup.2 generally represent alkyl groups which, together with the nitrogen atom between them, may also form a saturated monocylic, heterocyclic group, R.sub.3 represents alkyl, chlorine or hydrogen, R.sub.4 represents hydrogen or methyl, R.sup.5 and R.sup.6 represent hydrogen, halogen or alkyl, R.sub.7 represents hydrogen, chlorine or methyl, R.sup.8 represents hydrogen or lower alkyl, R.sup.9 represents hydrogen, halogen, lower alkyl and R.sup.10 represents hydrogen or methyl and R.
Type:
Grant
Filed:
December 18, 1987
Date of Patent:
October 10, 1989
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Wolfhard Engel, Wolfgang Eberlein, Gerhard Mihm, Gunter Trummlitz, Norbert Mayer, Adriaan De Jonge
Abstract: Galenic compositions containing an oral antidiabetic agent and having an improved release of active substance as well as processes for producing these compositions are provided. The pharmaceutical compositions are characterized in that the onset of the activity and the duration of activity are adapted to the particular needs of diabetics with regard to proper control of metabolism and the associated proper release of insulin. A basic or acidic excipient in a solvent is added to the anti-diabetically active substance in a quantity such that the active substance is made soluble, and then a solubilizing agent is added. The solution is applied to a water-insoluble carrier, the solvent is evaporated, and the residue is further processed to yield the various compositions.
Type:
Grant
Filed:
September 30, 1987
Date of Patent:
October 10, 1989
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Rolf Brickl, Gottfried Schepky, Eckhard Rupprecht, Andreas Greischel
Abstract: The present invention relates to new naphthyl derivatives of general formula ##STR1## wherein N represents the number 1 or 2,A represents a --CH.sub.2 --, --CO--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, ##STR2## while the atom marked with an x is linked to the phenyl nucleus, E represents a straight chained alkylene group optionally substituted by an alkyl group,G represents a straight chained alkylene group optionally substituted by an alkyl group,L represents a bond or an oxygen atom, if G represents a straight chained alkylene group with 2 to 5 carbon atoms optionally substituted by an alkyl group,R.sub.1 and R.sub.2, which may be identical or different, represent alkyl or alkoxy groups or R.sub.1 and R.sub.2 together represent an alkylenedioxy group,R.sub.3 represents a hydrogen atom, or an alkyl or an allyl group,R.sub.4, R.sub.5 and R.sub.
Type:
Grant
Filed:
September 11, 1987
Date of Patent:
October 3, 1989
Assignee:
Dr. Karl Thomae GmbH
Inventors:
Joachim Heider, Manfred Psiorz, Andreas Bomhard, Norbert Hauel, Berthold Narr, Klaus Noll, Christian Lillie, Walter Kobinger, Jurgen Dammgen