Patents by Inventor Helmut Biere
Helmut Biere 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: 5700808Abstract: 5- or 6-substituted .beta.-carboline-3-carboxylic acid esters of Formula I ##STR1## wherein R.sup.1 is hydrogen, nitrilo, halogen, lower alkyl or lower alkoxy, andR.sup.3 is a branched C.sub.3-6 alkyl group which is optionally substituted by halogen, or a C.sub.3-6 cycloalkyl group which is optionally methyl-substituted, are valuable pharmaceuticals.Type: GrantFiled: May 18, 1994Date of Patent: December 23, 1997Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, Wolfgang Kehr, Herbert Hans Schneider, Mogens Engelstoft, Bondo John Hansen, Frank Waetjen, Tage Honore
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Patent number: 5414002Abstract: 5- or 6-substituted .beta.-carboline-3-carboxylic acid esters of Formula I ##STR1## wherein R.sup.1 is hydrogen, nitrilo, halogen, lower alkyl or lower alkoxy, andR.sup.3 is a branched C.sub.3-6 alkyl group which is optionally substituted by halogen, or a C.sub.3-6 cycloalkyl group which is optionally methyl-substituted, are valuable pharmaceuticals.Type: GrantFiled: October 3, 1989Date of Patent: May 9, 1995Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, Wolfgang Kehr, Herbert H. Schneider, Mogens Engelstoft, Bondo J. Hansen, Frank Waetjen, Tage Honore
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Patent number: 5179111Abstract: Imidazole derivatives of general Formula I ##STR1## wherein R.sup.1 means hydrogen, an optionally substituted C.sub.1-10 hydrocarbon or hetaryl residue, or a cyclic ether residue,R.sup.2 means hydrogen, halogen, an optionally substituted amino, nitro, azide, thiocyanate or cyano group, a linear or branched C.sub.1-10 -alkyl residue optionally substituted with halogen, or -OR.sup.1 wherein R.sup.1 has the above-mentioned meanings, andR.sup.1 and R.sup.2 jointly with the oxygen atom form a saturated or unsaturated 5- to 7-membered ring which can contain still another hetero atom,R.sup.3 means hydrogen, a linear or branched C.sub.1-6 -alkyl group, or a C.sub.1-6 -alkoxyalkyl group,R.sup.4 means -COOR.sup.5, -CONR.sup.6 R.sup.7, -CN, ##STR2## and their use as medicinal agents are disclosed.Type: GrantFiled: December 14, 1988Date of Patent: January 12, 1993Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Ralph Rohde, Herbert H. Schneider, Lechoslaw Turski
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Patent number: 4987146Abstract: N-hetaryl imidazole derivatives of general Formula I ##STR1##are disclosed in whichHet represents an optionally substituted monocyclic or bicyclic heteroaromate,R.sup.3 represents hydrogen, a straight or branched C.sub.1-6 -alkyl group, or a C.sub.1-6 -alkoxy-alkyl group, andR.sup.4 represents --COOR.sup.5 --CONR.sup.6 R.sup.7 --CN, ##STR2##with R.sup.5 meaning hydrogen, a straight or branched C.sub.1-6 -alkyl group, R.sup.6 and R.sup.7 are the same of different and represent hydrogen or a straight, branched, or cyclic alkyl group with up to 7 carbon atoms or, together with the nitrogen atom, form a saturated five or six ring optionally containing another heteroatom and R.sup.8 means hydrogen or a straight, branched or cyclic alkyl group with up to 7 carbon atoms.Type: GrantFiled: July 14, 1989Date of Patent: January 22, 1991Assignee: Schering AktiengesellschaftInventors: Ralph Rohde, Helmut Biere, Ralph Schmiechen, John S. Andrews, David N. Stephens
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Patent number: 4968801Abstract: Ergoline derivatives of general Formula I ##STR1## wherein C.sub.8 C.sub.9 and C.sub.9 C.sub.10 are both CC-single bonds or one is a C.dbd.C-double bond,R.sup.6 is C.sub.1-4 alkyl,R.sup.8 is methyl, hydroxymethyl, carbonylmethoxy, ureido or N,N-diethylureido, each in the .alpha.- or .beta.-position, andR is hydrogen or nitro,are prepared by dehydrogenation of corresponding 2,3-dihydroergoline derivatives using an electrophilic reagent in an apolar solvent and a base.Type: GrantFiled: May 25, 1989Date of Patent: November 6, 1990Assignee: Schering AktiengesellschaftInventors: Gerhard Sauer, Helmut Biere, Gregor Haffer, Andreas Huth
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Patent number: 4960777Abstract: Heteroaryloxy-.beta.-carboline derivatives of general Formula I ##STR1## wherein R.sup.1 is an optionally substituted heteroaryl residue,R.sup.2 is hydrogen, lower alkyl or lower alkoxyalkyl,X is a COOR.sup.3 -group wherein R.sup.3 means H or lower alkyl, or represents a CONR.sup.4 R.sup.5 -group wherein R.sup.4 and R.sup.5 mean respectively hydrogen or lower alkyl, R.sup.4 and R.sup.5 being capable of forming, together with the nitrogen atom, a 5- to 6-membered heterocycle, or means an oxadiazolyl residue of the formula ##STR2## wherein R.sup.6 means hydrogen, lower alkyl or cycloalkyl, are valuable pharmaceuticals.Type: GrantFiled: September 20, 1989Date of Patent: October 2, 1990Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, David Stephens, Mogens Engelstoft, John B. Hansen
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Patent number: 4952698Abstract: Imidazole derivatives of general formula I ##STR1## wherein R.sup.1 represents hydrogen or halogen in the o-, m- or p-position, and the halogen can occur once or repeatedly in the phenyl radical,R.sup.4 represents ##STR2## with R.sup.6 and R.sup.9 representing hydrogen or a straight or branched alkyl group with 1 to 6 carbon atoms, R.sup.7 and R.sup.8 are the same or different and represent hydrogen or a straight or branched alkyl group with 1 to 6 carbon atoms or R.sup.7 and R.sup.8 together with the nitrogen atom represent a saturated heterocyclic five-membered or six-membered ring optionally containing another heteroatom, andR.sup.5 represents hydrogen, an alkyl group with 1 to 6 carbon atoms or an alkoxyalkyl group with 1 to 6 carbon atoms, which are suitable as psychopharmaceuticals, are described.Type: GrantFiled: April 11, 1988Date of Patent: August 28, 1990Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, Herbert H. Schneider, David N. Stephens
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Patent number: 4877792Abstract: Heteroaryloxy-.beta.-carboline derivatives of general Formula I ##STR1## wherein R.sup.1 is an optionally substituted heteroaryl residue,R.sup.2 is hydrogen, lower alkyl or lower alkoxyalkyl,X is a COOR.sup.3 -group wherein R.sup.3 means H or lower alkyl, or represents a CONR.sup.4 R.sup.5 -group wherein R.sup.4 and R.sup.5 mean respectively hydrogen or lower alkyl, R.sup.4 and R.sup.5 being capable of forming, together with the nitrogen atom, a 5- to 6-membered heterocycle, or means an oxadiazolyl residue of the formula ##STR2## wherein R.sup.6 means hydrogen, lower alkyl or cycloalkyl, are valuable pharmaceuticals.Type: GrantFiled: March 9, 1987Date of Patent: October 31, 1989Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, David N. Stephens, Mogens Engelstoft, John B. Hansen
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Patent number: 4855295Abstract: 5,6,7,8-tetrahydro-beta-carbolines derivatives of formula I ##STR1## wherein R.sup.1 is an oxadiazolyl radical of the formula ##STR2## COOR.sup.3 or CONR.sup.4 R.sup.5, R.sup.2 is H, lower alkyl or cycloalkyl,R.sup.3 is H or lower alkyl,R.sup.4 and R.sup.5 are H or lower alkyl, whereby R.sup.4 and R.sup.5 cannot be hydrogen at the same time, or R.sup.4 and R.sup.5 together with the adjacent nitrogen atom form a 5- or 6-member ring, which additionally can contain a heteroatom, andR.sup.A is hydrogen, .dbd.O, cycloalkyl, --COOR.sup.3 with R.sup.3 having the above-mentioned meanings, or lower alkyl, which optionally can be substituted by OH, halogen, lower alkoxy, phenyl, phenyloxy, --NR.sup.4 R.sup.5, whereby R.sup.4 and R.sup.5 have the above-mentioned meanings, and R.sup.B can be hydrogen, lower alkyl or lower alkoxyalkyl,have valuable pharmacological properties.Type: GrantFiled: October 6, 1986Date of Patent: August 8, 1989Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Mogens Engelstoft, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, David N. Stephens
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Patent number: 4801714Abstract: Ergolinylthioureas derivatives of the general Formula I ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or acyl,R.sup.2 is hydrogen, halogen or a lower alkylthio groupR.sup.3 is lower alkyl,R.sup.4, R.sup.5 and R.sup.6, is hydrogen or lower alkyl, and each is identical or different,n=0, 1 or 2 and C.sub.9 --C.sub.10 is a single or a double bond; are produced by reacting in an ergolin-8-ylurea compound otherwise corresponding to Formula I with a --CO--NR.sup.5 R.sup.6 group in place of the --CS--Nr.sup.5 R.sup.6 group is reacted with a chlorinating agent and a thiolating agent.Type: GrantFiled: August 6, 1986Date of Patent: January 31, 1989Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Gregor Haffer
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Patent number: 4772610Abstract: Novel 1-alkyl ergolinylthiourea derivatives of the general formula ##STR1## wherein R.sup.1 is C.sub.1-6 alkyl,R.sup.2 and R.sup.3 are C.sub.1-4 alkyl,R.sup.4 is hydrogen or C.sub.1-4 alkyl andC.sub.9---- C.sub.10 is a single bond or a double bond,and the acid addition salts thereof, with the provision that when R.sup.3 and R.sup.4 are both ethyl, R.sup.1 and R.sup.2 are not methyl and acid addition salts thereof are provided; as well as a process for the preparation of these compounds. The compounds are useful as medicinal agents, e.g., for the treatment of mental depression.Type: GrantFiled: August 6, 1986Date of Patent: September 20, 1988Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Gerhard Sauer, Helmut Wachtel
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Patent number: 4757070Abstract: Compounds of formula I ##STR1## wherein n is 0 or 1,R.sup.1 is hydrogen or lower alkyl,R.sup.2 and R.sup.3 each independently is hydrogen, optionally substituted lower alkyl, acyl or aryl, or together with the nitrogen atom form a 5-6-member heterocycle,R.sup.4 is hydrogen, lower alkyl or lower alkoxyalkyl andX is COOR.sup.6, CO--NR.sup.7 R.sup.8, or an oxadiazolyl radical of the formula ##STR2## wherein R.sup.5 is H, lower alkyl or cycloalkyl,R.sup.6 is H or lower alkyl,R.sup.7 and R.sup.8 each independently is hydrogen, optionally substituted lower alkyl, acyl or aryl, orR.sup.7 and R.sup.8 together with the nitrogen atom can form a 5-6-member heterocycle,are valuable drugs, e.g., have psychotropic activity.Type: GrantFiled: December 8, 1987Date of Patent: July 12, 1988Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, David N. Stephens
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Patent number: 4731365Abstract: Compounds of formula I ##STR1## wherein n is 0 or 1,R.sup.1 is hydrogen or lower alkyl,R.sup.2 and R.sup.3 each independently is hydrogen, optionally substituted lower alkyl, acyl or aryl, or together with the nitrogen atom form a 5-6-member heterocycle,R.sup.4 is hydrogen, lower alkyl or lower alkoxyalkyl andX is COOR.sup.6, CO--NR.sup.7 R.sup.8, or an oxadiazolyl radical of the formula ##STR2## wherein R.sup.5 is H, lower alkyl or cycloalkyl,R.sup.6 is H or lower alkyl,R.sup.7 and R.sup.8 each independently is hydrogen, optionally substituted lower alkyl, acyl or aryl, orR.sup.7 and R.sup.8 together with the nitrogen atom can form a 5-6-member heterocycle,are valuable drugs, e.g., have psychotropic activity.Type: GrantFiled: December 22, 1986Date of Patent: March 15, 1988Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, David N. Stephens
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Patent number: 4731358Abstract: New substituted .beta.-carbolines of formula I ##STR1## wherein R.sup.3 is hydrogen or a non-carboxyl based substituent, and R.sup.4-9 have various meanings,are valuable pharmaceutical products with long lasting action on the central nervous system.Type: GrantFiled: September 2, 1986Date of Patent: March 15, 1988Assignee: Schering AktiengesellschaftInventors: Andreas Huth, Dieter Rahtz, Dieter Seidelmann, Helmut Schmiechen, Helmut Biere, Claus T. Braestrup
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Patent number: 4705857Abstract: Indole derivatives of formula I ##STR1## R is hydrogen, one or two halogen atoms or one or two organic radicals in the 4-, 5-, 6- or 7-position(s),R.sup.1 and R.sup.4 are the same or different and each is hydrogen, alkyl of 1 to 3 carbon atoms or alkoxyalkyl of 1 to 3 carbon atoms in each of the alkoxy and alkyl portions,R.sup.3 is phenyl, --COOalkyl, --PO.sub.3 (alkyl).sub.2, --SO.sub.2 aryl, --SO.sub.2 alkyl, ##STR2## each of 1 to 3 carbon atoms in each alkyl group, and A and B each independently is alkyl of 1 to 3 carbon atoms or together with the connecting N-atom form a pyrrolidono, piperidino, morpholino or piperazino group,are valuable intermediates for preparing valuable tryptophans and .beta.-carbolines.Type: GrantFiled: October 28, 1983Date of Patent: November 10, 1987Assignee: Schering AktiengesellschaftInventor: Helmut Biere
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Patent number: 4705856Abstract: .beta.-carbolines of formula I ##STR1## can be prepared by reacting an indole of formula II: ##STR2## with an azabutadiene of formula III ##STR3## in the presence of an acid at 50.degree.-200.degree. C.Type: GrantFiled: October 28, 1983Date of Patent: November 10, 1987Assignee: Schering AktiengesellschaftInventor: Helmut Biere
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Patent number: 4645762Abstract: Diphosphonic acid derivatives of the formula ##STR1## wherein X is cyano, 2-cyanoethyl, or 3- aminopropyl and Y is H, or X and Y together represent dimethylaminomethylene ((CH.sub.3).sub.2 NCH.dbd.), andR is hydrogen, alkyl of 1-4 carbon atoms, or a cation derived from a base, especially an alkali metal atom,excluding the cyanomethanebis (phosphonic acid diethyl ester),are pharmacologically active compounds.Type: GrantFiled: July 5, 1983Date of Patent: February 24, 1987Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Clemens Rufer, Irmgard Boettcher
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Patent number: 4503049Abstract: Diphosphonic acid derivatives of Formula I ##STR1## wherein R is hydrogen, an alkali metal atom, an alkaline earth metal atom, or an alkyl group of 1-4 carbon atoms andA is derived from a carboxylic acid having anti-inflammatory and antiphlogistic activity and containing an aromatic or heteroaromatic group, of Formula IIACOOH (II),are pharmacologically efficacious compounds.Type: GrantFiled: January 27, 1983Date of Patent: March 5, 1985Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Clemens Rufer, Irmgard Boettcher
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Patent number: 4473560Abstract: Compounds of the formula ##STR1## wherein n is 0, 1, or 2;R.sup.1 is hydrogen or alkyl of 1-4 carbon atoms;R.sup.2 is hydrogen, an alkali metal atom, an alkaline earth metal atom, or alkyl of 1-4 carbon atoms; andAr is phenyl; phenyl substituted by fluorine, chlorine, alkyl of 1-4 carbon atoms, or alkoxy of 1-4 carbon atoms; naphthyl; biphenyl; or thienyl;or when R.sup.2 is H, a physiologically acceptable salt thereof with an organic basehave valuable antiinflammatory properties.Type: GrantFiled: January 27, 1983Date of Patent: September 25, 1984Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Clemens Rufer, Irmgard Boettcher
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Patent number: 4457927Abstract: Pyrido[2,1-b]quinazolinones of the formula ##STR1## wherein X is cyano, hydroxyamidocarbonyl, carbamoyl, 5-tetrazolyl, carboxy, carboxy in the form of a salt thereof with a physiologically compatible base, carboxy esterified with a physiologically acceptable alcohol or carboxy amidated with a physiologically acceptable amine;R.sub.1 is hydrogen or methyl; andR.sub.2 through R.sub.5 are independently each hydrogen, halogen, alkyl of 1-4 carbon atoms, trifluoromethyl, carboxy, thiocyano, methylthio, methylsulfinyl, methylsulfonyl, methylsulfonimidoyl or methylsulfonamido with the proviso that two or three of the groups R.sub.2 through R.sub.5 are hydrogen; or a salt thereof with a physiologically acceptable acid or base;possess valuable pharmacological properties.Type: GrantFiled: December 22, 1982Date of Patent: July 3, 1984Assignee: Schering, AktiengesellschaftInventors: Helmut Biere, Joachim-Friedrich Kapp, Irmgard Bottcher