Patents by Inventor Olaf Loge
Olaf Loge 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: 6225347Abstract: The invention relates to 9-halogen-(Z) prostane derivatives of formula I in which Z represents the radicals Hal represents a chlorine or fluorine atom in the alpha or beta position, R1 represents the radical with R2 meaning a hydrogen atom, an alkyl, cycloalkyl, aryl or heterocyclic radical or R1 represents the radical with R3 meaning an acid radical or the radical R2 and A represents a —CH2—CH2—, a trans-CH═CH or —C≡C group, W represents a free or a functionally modified group, and the respective OH groups can be in the alpha or beta position, D and E together represent a direct bond or D represents a straight-chain alkylene group with 1-10 C atoms, a branched-chain alkylene group with 2-10 C atoms or an annular alkylene group with 3-10 C atoms, which optionally can be substituted by fluorine atoms, and E represents an oxygen or sulfur atom, a direct bond, a C≡C bond or aType: GrantFiled: September 27, 1994Date of Patent: May 1, 2001Assignee: Schering AktiengesellschaftInventors: Bernd Buchmann, Werner Skuballa, Helmut Vorbrueggen, Bernd Raduechel, Olaf Loge, Walter Elger, Claus-Steffen Stuerzebecher, Karl-Heinz Thierauch
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Patent number: 5891910Abstract: The invention relates to 9-halogen-(Z) prostane derivatives of formula I ##STR1## in which ##STR2## Z represents the radicals Hal represents a chlorine or fluorine atom,R.sub.1 represents ##STR3## A represents a --CH.sub.2 --CH.sub.2 --, a trans--CH=CH or --C.ident.C, W represents a free or a functionally modified ##STR4## group, D and E together represent a direct bond orD represents a straight-chain alkylene group with 1-10 C atoms, a branched-chain alkylene group with 2-10 C atoms or an annular alkylene group with 3-10 C atoms, which optionally can be substituted by fluorine atoms, andE represents an oxygen or sulfur atom, a direct bond, a C.ident.C bond or a --CR.sub.6 =CR.sub.7 group, and R.sub.6 and R.sub.7 are different and mean a hydrogen atom, a chlorine atom or a C.sub.1 -C.sub.4 alkyl group,R.sub.4 represents a free or functionally modified hydroxy,R.sub.5 means a hydrogen atom, an alkyl, a halogen-substituted alkyl, a cycloalkyl or an optionally substituted aryl or a heterocyclic group.Type: GrantFiled: June 6, 1995Date of Patent: April 6, 1999Assignee: Schering AktiengesellschaftInventors: Bernd Buchmann, Werner Skuballa, Helmut Vorbrueggen, Bernd Raduechel, Olaf Loge, Walter Elger, Claus-Steffen Stuerzebecher, Karl-Heinz Thierauch
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Patent number: 5204371Abstract: Compounds of the formula ##STR1## wherein the 9-chlorine atom can be in the .alpha.-or .beta.-position,A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2,--, trans--CH.dbd.CH--, or --CH.tbd.C--, W is hydroxymethylene orD and E together represent a direct bond orD is a straight-chain or branched alkylene group of 1-10 carbon atoms, optionally substituted by fluorine, andE is oxygen or sulfur or a direct bond, andR.sub.4 is hydroxy or hydroxy etherified or esterified as defined for W above;R.sub.5 is a C.sub.1-10 hydrocarbon aliphatic group; a C.sub.1-10 hydrocarbon aliphatic group substituted by aryl, a substituted aryl as defined for R.sub.2 above, or halogen; or cycloalkyl, substituted cycloalkyl, aryl, substituted aryl or aromatic heterocyclic, all as defined for R.sub.2 above;or a physiologically acceptable salt thereof with a base when R.sub.1 is OH,have valuable pharmacologoical properties.Type: GrantFiled: November 15, 1991Date of Patent: April 20, 1993Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
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Patent number: 5079259Abstract: A 9-chloroprostane of the formula ##STR1## wherein the 9-chlorine atom can be in the .alpha. or .beta.-position and R.sub.1, R.sub.4, R.sub.5, A, B, W, D and E are as described hereinafter which are useful as medical agents.Type: GrantFiled: September 8, 1987Date of Patent: January 7, 1992Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
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Patent number: 5049582Abstract: The invention relates to an agent for cytoprotection in the liver, in the pancreas and in the kidney, characterized in that it contains prostacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1-10 carbon atoms,A is a --CH.sub.2 --CH.sub.2 --, trans-CH.dbd.CH-- or --C.tbd.C--group,W is a free hydroxymethyl group or a hydroxymethyl group functionally modified at the hydroxy group, the OH-group being in the .alpha.- or .beta.-position,X is a CH.sub.2 -group or an oxygen atom,Z is hydrogen or a cyano group,D is a straight-chain or branched saturated alkylene group of 1-5 carbon atoms,E is a --C.tbd.C--bond or a direct bond,R.sub.2 is a straight- or branched-chain, saturated alkyl group of 1-7 carbon atoms,R.sub.3 is a free or functionally modified hydroxy group,and, if R.sub.1 means a hydrogen atom, the salts thereof with physiologically compatible bases,and to a process for the preparation of the aforementioned agents.Type: GrantFiled: February 27, 1989Date of Patent: September 17, 1991Assignee: Schering AktiengesellschaftInventors: Guido Adler, Rolf Schulte-Hermann, Olaf Loge
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Patent number: 5047525Abstract: The present application encompasses pharmaceutical preparations, characterized in that they contain as the active component a cyclodextrin clathrate of a prostaglandin of general Formula I ##STR1## wherein R.sub.1 is a hydrogen atom or a straight-chain or branched alkyl residue of up to 10 carbon atoms,R.sub.2 is an alkyl, cycloalkyl, or optionally substituted phenyl group,A and B jointly mean a direct bond orA means a straight- or branched-chain alkylene group of up to 10 carbon atoms andB means an oxygen atom, a direct bond, or a --C.tbd.C--bond, andX means a chlorine or fluorine atom.Type: GrantFiled: July 6, 1990Date of Patent: September 10, 1991Assignee: Schering AktiengesellschaftInventors: Bernd Raduechel, Werner Skuballa, Olaf Loge, Johann-Wilhelm Tack
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Patent number: 5010065Abstract: The invention relates to cyclodextrin clathrates of 5-cyanoprostacyclin analogs.Type: GrantFiled: November 28, 1988Date of Patent: April 23, 1991Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Helmut Dahl, Helmut Vorbrueggen, Olaf Loge, Karl-Heinz Thierauch
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Patent number: 5004752Abstract: The invention relates to 9-halo-15-cycloalkyl prostaglandin derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen or methyl,R.sub.2 is fluorine or chlorine,n is 0 or 1,and, if R.sub.1 is hydrogen, the salts thereof with physiologically compatible bases or the cyclodextrin clathrates thereof, processes for their preparation, and their pharmaceutical usage.Type: GrantFiled: May 8, 1989Date of Patent: April 2, 1991Assignee: Schering AktiengesellschaftInventors: Bernd Raduechel, Werner Skuballa, Helmut Vorbrueggen, Olaf Loge, Ekkehard Schilliner
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Patent number: 4983629Abstract: 11-Haloprostane derivatives of general Formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or a --C.tbd.C--group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.Type: GrantFiled: June 21, 1989Date of Patent: January 8, 1991Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
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Patent number: 4894391Abstract: 5-Cyanoprostacyclins of Formula I ##STR1## wherein A is a --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C-group,W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position, D and E together form a direct bond orD is the group ##STR3## a straight-chain, saturated alkylene group of 1-5 carbon atoms, a branched, saturated or a straight-chain, unsaturated alkylene group of 2-5 carbon atoms, any of which can optionally be substituted by fluorine atoms,n is the number 1, 2, or 3,E is oxygen, sulfur, a --C.tbd.C-bond, a direct bond, or a --CR.sub.4 .dbd.CR.sub.5 -group wherein R.sub.4 and R.sub.5 are different and can be a hydrogen atom or an alkyl group of 1-3 carbon atoms,R.sub.2 is an alkyl, cycloalkyl, optionally substituted aryl, or heterocyclic group,R.sub.1 is a free or functionally modified hydroxy group, andR.sub.3 is an acetal residue ##STR4## wherein R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.Type: GrantFiled: June 25, 1984Date of Patent: January 16, 1990Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Helmut Dahl, Bernd Raduchel, Helmut Vorbruggen, Olaf Loge
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Patent number: 4870104Abstract: 11-Haloprostane derivatives of general formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH-group,B is a --CH.sub.2 --CH.sub.2 -- or trans-CH.dbd.CH-- or a --C.tbd.C-group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C-bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.Type: GrantFiled: November 12, 1986Date of Patent: September 26, 1989Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
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Patent number: 4835175Abstract: Indole derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen, alkyl of 1-6 carbon atoms, or benzylR.sub.2 is hydrogen, alkyl of up to 4 carbon atoms, free or esterified hydroxyalkyl of up to 4 carbon atoms, or free, amidated or esterified carboxy or carboxyalkyl,R.sub.3 is hydrogen or alkyl containing 1-6 carbon atoms,R.sub.4 is hydrogen or alkyl containing 1-6 carbon atoms andR.sub.5 is hydrogen, or alkyl, alkenyl, or cycloalkyl, all of which per se contain up to 6 carbon atoms, and all of which are optionally substituted by a free or esterified carboxy group or by an optionally substituted phenyl group; or a polymethylene group of up to 8 carbon atoms linking the first indole residue to a second indole residue of Formula Ia ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as defined above,and the physiologically acceptable salts thereof with acids and, optionally, their alkali metal and alkaline earth metal salts,possess valuable pharmacological properties, such as stimulating .beta.Type: GrantFiled: October 10, 1986Date of Patent: May 30, 1989Assignee: Schering AktiengesellschaftInventors: Josef Heindl, Olaf Loge
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Patent number: 4789685Abstract: 9-fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.- position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.Type: GrantFiled: January 20, 1987Date of Patent: December 6, 1988Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4721729Abstract: Carbacyclins of Formula I ##STR1## wherein R.sub.1 is an alkyl, cycloalkyl, aryl, aralkyl, or heterocyclic group,Y is a keto group or a hydroxymethylene group,X is a --CH.sub.2 -- group or an oxygen atom,A is a --CH.sub.2 --CH.sub.2 --, a trans--CH.dbd.CH-- or a --C.tbd.C-- group,W is a hydroxymethylene group or a ##STR2## D is the group ##STR3## a straight-chain or branched, saturated alkylene group or unsaturated alkylene group of up to 5 carbon atoms which can optionally be substituted by 1-2 fluorine atoms,n is 1, 2 or 3,E is a direct bond, a --C.tbd.C-- group or a --CR.sub.4 .dbd.CR.sub.5 -- group wherein R.sub.4 is hydrogen or an alkyl group and R.sub.5 is hydrogen, halogen or an alkyl group,R.sub.2 is an alkyl, cycloalkyl, aryl, or heterocyclic group, andR.sub.3 is a hydroxy group,are valuable, e.g., as cytoprotective agents.Type: GrantFiled: February 8, 1985Date of Patent: January 26, 1988Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Robert Nickolson, Martin Haberey, Olaf Loge, Claus-Steffen Stuerzebecher
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Patent number: 4699920Abstract: The invention relates to 9-halo-.DELTA..sup.2 -prostane derivatives of general Formula I ##STR1## wherein Hal is a fluorine or chlorine atom in the .alpha.- or .beta.-position,R.sub.1 is the residue OR.sub.2 with R.sub.2 meaning a hydrogen atom, alkyl, cycloalkyl, aryl or a heterocyclic residue; or the residue NHR.sub.3 wherein R.sub.3 means an acid residue or the residue R.sub.2 andA is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or --C.tbd.C--group,W is a free or functionally modified hydroxymethylene or ##STR2## wherein the respective OH-groups can be in the .alpha.- or .beta.-position,D and E jointly mean a direct bond orD is a straight- or branched-chain alkylene group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 --group wherein R.sub.6 is a hydrogen atom or an alkyl group and R.sub.Type: GrantFiled: September 17, 1985Date of Patent: October 13, 1987Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge
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Patent number: 4560786Abstract: .DELTA..sup.8,9 -Prostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 ; A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH;B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR4## wherein the OH--group can be in the .alpha.-- or .beta.-- position; D and E jointly are a direct bond orD is straight chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen, sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine or alkyl;R.sub.4 is free or functionally modified hydroxy andR.sub.Type: GrantFiled: June 24, 1982Date of Patent: December 24, 1985Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4489092Abstract: Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans-CH.dbd.CH, --C.tbd.C-- or ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CH or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.Type: GrantFiled: September 1, 1982Date of Patent: December 18, 1984Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
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Patent number: 4454339Abstract: 9-Fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.-position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.Type: GrantFiled: July 6, 1982Date of Patent: June 12, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4444788Abstract: Compounds of the formula ##STR1## wherein the 9-chlorine atom can be in the .alpha.- or .beta.-position,R.sub.1 is OR.sub.2, or NHR.sub.3 wherein R.sub.3 is H or the acyl group ofa C.sub.1-15 hydrocarbon carboxylic or sulfonic acid;A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --,trans--CH.dbd.CH--, or --C.tbd.C--, ##STR2## wherein the OH-group in each case can be in the .alpha.- or .beta.-position, and can be etherified or esterified by tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, trimethylsilyl dimethyl, tert-butylsilyl, tribenzylsilyl, acetyl, propionyl, butyryl or benzoyl;D and E together represent a direct bond orD is a straight-chain or branched alkylene group of 1-10 carbon atoms, optionally substituted by fluorine, andE is oxygen or sulfur or a direct bond, andR.sub.4 is hydroxy or hydroxy etherified or esterified as defined for W above;R.sub.5 is a C.sub.1-10 hydrocarbon aliphatic group; a C.sub.Type: GrantFiled: June 10, 1982Date of Patent: April 24, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
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Patent number: 4364951Abstract: Prostane derivatives of the formula ##STR1## wherein B is straight-chain or branched alkylene of 1-10 carbon atoms,A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is hydroxymethylene or a ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position, and is optionally modified by replacement of the H atom with an ether or acyl group which is conventional for such replacements in prostaglandins and which is readily cleavable at physiological pH's;D and E together are a direct bond orD is straight-chain or branched alkylene of 1-10 carbon atoms, or, such an alkylene of 4-10 carbon atoms containing a double bond in the 2- or 3- position, all of which can optionally be substituted by fluorine, 1,2-methylene, 1,1-trimethylene, or methoxy;E is oxygen, sulfur, --C.tbd.C-- or a direct bond;R.sub.2 is C.sub.1-10, C.sub.2-10 alkenyl,each of which optionally is substituted phenyl, 1-naphthyl or 2-naphthyl, each of which is substituted as defined below; C.sub.Type: GrantFiled: November 2, 1981Date of Patent: December 21, 1982Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Helmut Vorbrueggen, Olaf Loge, Peter Vischer, Bernd Raduchel