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: 4359467Abstract: 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- ##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, CN 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: April 22, 1981Date of Patent: November 16, 1982Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
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Patent number: 4346228Abstract: 11-Oxoprostaglandin derivatives of the formula ##STR1## wherein R.sub.2 is a hydrogen atom or alkyl of 1-5 carbon atoms,R.sub.3 is alkyl of 1-5 carbon atoms, alkylaryl, cycloalkyl of 5-6 ring carbon atoms and a total of 5-10 carbon atoms; benzodioxol-2-yl, phenyl, naphthyl or phenyl or naphthyl substituted by phenyl, halogen, alkyl of 1-4 carbon atoms, chloromethyl, fluoromethyl, carboxyl or hydroxy;A is --CH.sub.2 --CH.sub.2 --, cis--CH.dbd.CH--, or trans--CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH--,D and E collectively are a direct bond or D is alkylene of 1-5 carbon atoms and E is an oxygen or sulfur atom; esters thereof; readily cleavable 9,15 and 9,15 ethers thereof; methanesulfonylamides thereof, and physiologically acceptable salts thereof with bases; possess the activity of the corresponding natural prostaglandins with a surprisingly longer duration of effectiveness, greater selectivity, and better effects, and can be produced, e.g.Type: GrantFiled: April 15, 1976Date of Patent: August 24, 1982Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4284646Abstract: 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, CN 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: August 24, 1979Date of Patent: August 18, 1981Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
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Patent number: 4256745Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.Type: GrantFiled: March 2, 1978Date of Patent: March 17, 1981Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4235930Abstract: Prostane derivatives of the formula ##STR1## wherein R.sub.1 is the residue OR.sub.2 and R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or is NHR.sub.3 wherein R.sub.3 is an acyl group derived from a hydrocarbon carboxylic or sulfonic acid of up to 15 carbon atoms;A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--Z is carbonyl or ##STR2## wherein the OR.sub.4 group can be in the .alpha.- or .beta.-position and R.sub.4 is H or a hydroxy-protective groupX Y is ##STR3## wherein R.sub.4 is as defined above, --CH.sub.2 -- CH.sub.2 -- or --CH.sub.2 --CH-- wherein R.sub.5 is alkyl or 1-5 carbon atoms, if Z is R.sub.5 carbonyl or ##STR4## X Y represents --CH.dbd.CH-- if Z is carbonyl: R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 each independently is hydrogen or an alkyl group of 1-5 carbon atoms; andR.sub.11 is alkyl of 1-5 carbon atoms;and if R.sub.Type: GrantFiled: June 29, 1978Date of Patent: November 25, 1980Assignee: Schering, A.G.Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
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Patent number: 4219479Abstract: Stabilized prostacyclins having a wide range of pharmacological activity and long duration of such activity, have the formula ##STR1## wherein R.sub.1 is (a) OR.sub.3, wherein R.sub.3 is hydrogen, alkyl, cycloalkyl, aryl or a heterocyclic residue; or (b) NHR.sub.4 wherein R.sub.4 is an acid residue;B is straight-chain or branched alkylene of 2-10 carbon atoms;A is --CH.sub.2 --CH.sub.2 --, cis--CH.dbd.CH--, trans--CH.dbd.CH-- or --C.tbd.C--,W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D and E together are a direct bond; orD is straight-chain or branched alkylene of 1-5 carbon atoms; andE is oxygen or sulfur or a direct bond,R.sub.2 is alkyl, cycloalkyl, optionally substituted aryl or a heterocyclic group; andR.sub.5 is free or functionally modified hydroxy; and when R.sub.3 is hydrogen, the salts thereof with physiologically compatible bases.Type: GrantFiled: November 24, 1978Date of Patent: August 26, 1980Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Werner Skuballa, Bernd Raduchel, Wolfgang Losert, Olaf Loge, Bernd Muller, Gerda Mannesmann
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Patent number: 4217360Abstract: 1,3-Benzodioxaneprostanoic acid compound of the formula ##STR1## wherein R.sub.1 is hydroxy, alkoxy of 1-10 carbon atoms, methylsulfamido, substituted or unsubstituted aryloxy, or O--CH.sub.2 --U--V wherein U is a direct bond, carbonyl, or carbonyloxy, and V is phenyl or phenyl substituted, e.g. by one or more of phenyl, phenoxy, alkoxy of 1-2 carbon atoms, and halogen; A is --CH.sub.2 --CH.sub.2 -- or trans --CH.dbd.CH--; B is --CH.sub.2 --CH.sub.2 -- or cis- or trans--CH.dbd.CH--; Z is hydroxymethylene or carbonyl; X Y, if Z is hydroxymethylene, is ##STR2## or, if Z is carbonyl, is ##STR3## or --CH.dbd.CH--; R.sub.2 is hydrogen or alkyl of 1-5 carbon atoms; R.sub.3 and R.sub.4 each are H, F, Cl, Br, I or CF.sub.3, CH.sub.3 or alkoxy of 1-2 carbon atoms or R.sub.3 and R.sub.4 in 6-,7-position is methylendioxy; and if R.sub.Type: GrantFiled: January 10, 1979Date of Patent: August 12, 1980Assignee: Schering AktiengesellschaftInventors: Helmut Vorbrueggen, Norbert Schwarz, Olaf Loge, Walter Elger
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Patent number: 4191694Abstract: Prostane derivatives of the formula ##STR1## wherein R.sub.1 is OR.sub.2 or NHR.sub.3 ;R.sub.2 is hydrogen, C.sub.1-10 alkyl, C.sub.4-10 cycloalkyl, C.sub.6-10 aryl, or a 5 or 6 membered heterocyclic ring having 1-3 hetero atoms selected from O, N and S;R.sub.3 is the residue of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms;W is (a) an OH-substituted methylene group, (b) a ##STR2## wherein the OH-groups in (a) or (b) can be in the .alpha.- or .beta.-position, or (c) such a group wherein the H atom of the OH group is replaced by the residue of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms or by a conventional etherifying OH-blocking group;R.sub.4 is OH or hydroxy whose H atom is replaced as defined for W; andR.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 each independently is hydrogen or alkyl of 1-5 carbon atoms; or R.sub.9 and R.sub.10 together represent a direct bond; and, when R.sub.11 is alkyl, R.sub.Type: GrantFiled: July 26, 1978Date of Patent: March 4, 1980Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Bernd Muller, Gerda Mannesmann, Olaf Loge, Ekkehardt Schillinger, Jorge Casals-Stenzel
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Patent number: 4159343Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.Type: GrantFiled: March 3, 1978Date of Patent: June 26, 1979Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4154953Abstract: Prostanoic acid esters of the formulaPG-- CH.sub.2 -- X-- Ywherein PG is the prostanoyloxy radical of a prostaglandin, X is a carbon-carbon single bond, carbonyl or carbonyloxy, and Y is substituted phenyl are easily crystallized compounds at least as active as the unesterified prostanoic acid and useful for the purification of the parent prostaglandin are prepared by reacting, in the presence of an agent which splits off hydrogen halide, the unesterified prostaglandin with a halide of the formula Hal--CH.sub.2 --X--Y, wherein Hal is a halogen atom and X and Y have the values given above.Type: GrantFiled: August 19, 1977Date of Patent: May 15, 1979Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Wolfgang Losert
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Patent number: 4105792Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.Type: GrantFiled: May 25, 1976Date of Patent: August 8, 1978Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4088775Abstract: Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, alkyl of 1-10 carbon atoms, aryl or --CH.sub.2 --U--V wherein U is a direct bond, carbonyl, or carbonyloxy and V is phenyl or substituted phenyl, e.g. substituted by at least one of phenyl, alkoxy of 1-2 carbon atoms or a halogen atom; one of R.sub.2 and R.sub.3 is hydroxy and the other is a hydrogen atom or R.sub.2 and R.sub.3 collectively are an oxygen atom; A is --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH; B is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH; D and E collectively are a direct bond, or D is alkylene or 1-5 carbon atoms and E is an oxygen or sulfur atom; R.sub.4 is alkyl of 1-10 carbon atoms, alkyl of 1-5 carbon atoms substituted by unsubstituted or substituted aryl, unsubstituted or substituted aryl, or benzodioxol-2-yl-; X--Y is ##STR2## when one of R.sub.2 and R.sub.3 is a hydroxy group and the other is a hydrogen atom or X--Y is ##STR3## or --CH.dbd.CH-- when R.sub.2 and R.sub.Type: GrantFiled: July 11, 1975Date of Patent: May 9, 1978Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Wolfgang Losert, Olaf Loge
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Patent number: 4073934Abstract: Optically active and racemic prostaglandin derivatives of the formula ##STR1## wherein R.sub.1 is --OR.sub.5 ; --NHSO.sub.2 CH.sub.3 ; or --O--CH.sub.2 --U--V; R.sub.5 is hydrogen, alkyl, aryl, or a heterocyclic group; U is a direct bond, carbonyl or carbonyloxy; and V is phenyl substituted by 1-3 phenyl, alkoxy of 1-2 carbon atoms, or halogen, preferably bromine;R.sub.2 is hydrogen or alkyl of 1-5 carbon atoms;R.sub.3 is alkyl, substituted or unsubstituted cycloalkyl, straight-chain or branched alkyl of 1-5 carbon atoms substituted by aryl or substituted aryl, when R.sub.1 is as above; or R.sub.3 is aryl or substituted aryl group when R.sub.1 is --OR.sub.5 ', --NHSO.sub.2 CH.sub.3, or --O--CH.sub.2 --U--V and R.sub.5 ' is aryl or a heterocyclic group and U and V are as above;R.sub.4 is hydrogen or an ether or acyl residue;A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH--;D is a direct bond, oxygen, or sulfur;Z is carbonyl or >CH OR.sub.4 wherein OR.sub.Type: GrantFiled: April 16, 1976Date of Patent: February 14, 1978Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4058619Abstract: Thiophene derivatives of the formula ##STR1## WHEREIN R.sub.x is --S-CHR.sub.5 -COOH or --S-CH.sub.2 -CH.sub.2 -OH, R.sub.y is 1-2 of halogen alkoxy of 1-6 carbon atoms, aralkyl of 7-10 carbon atoms, phenyl, halophenyl or alkylcarbonyl of 1-6 carbon atoms in the alkyl group, and R.sub.5 is a hydrogen atom, when R.sub.y is a halogen atom, when R.sub.5 is alkyl, their enantiomers, and their pharmacologically acceptable salts thereof with bases, possess antilipolytic activity.Type: GrantFiled: September 14, 1976Date of Patent: November 15, 1977Assignee: Schering AktiengesellschaftInventors: Hanns Ahrens, Helmut Biere, Clemens Rufer, Ralph Schmiechen, Eberhard Schroeder, Olaf Loge, Wolfgang Losert, Ekkehard Schillinger
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Patent number: 4031236Abstract: Thiophene derivatives of the formula ##STR1## IN WHICH R.sub.x is --S--CHR.sub.5 --CONHOH or --S--CHR.sub.5 -5-tetrazolyl in which R.sub.5 is H or alkyl of 1-6 carbon atoms and R.sub.y is 0-2 of alkyl or alkoxy of 1-6 carbon atoms or halogen, and their pharmacologically acceptable salts with bases, possess antilipolytic activity.Type: GrantFiled: May 20, 1975Date of Patent: June 21, 1977Assignee: Schering AktiengesellschaftInventors: Hanns Ahrens, Helmut Biere, Clemens Rufer, Ralph Schmiechen, Eberhard Schroeder, Olaf Loge, Wolfgang Losert, Ekkehard Schillinger
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Patent number: 4021450Abstract: Thiophene derivatives of the formula ##STR1## WHEREIN R.sub.x is --S-CHR.sub.5 -COOH or -S-CH.sub.2 -CH.sub.2 -OH, R.sub.y is 1-2 of halogen alkoxy of 1-6 carbon atoms, aralkyl of 7-10 carbon atoms, phenyl, halophenyl or alkylcarbonyl of 1-6 carbon atoms in the alkyl group, and R.sub.5 is a hydrogen atom, when R.sub.y is a halogen atom, when R.sub.5 is alkyl, their enantiomers, and their pharmacologically acceptable salts thereof with bases, possess antilipolytic activity.Type: GrantFiled: May 20, 1975Date of Patent: May 3, 1977Assignee: Schering AktiengesellschaftInventors: Hanns Ahrens, Helmut Biere, Clemens Rufer, Ralph Schmiechen, Eberhard Schroeder, Olaf Loge, Wolfgang Losert, Ekkehard Schillinger
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Patent number: 4004020Abstract: Prostaglandins of the formula ##STR1## wherein R.sub.1 is hydroxymethyl, carboxy, aryloxycarbonyl, alkoxycarbonyl of 1-8 carbon atoms in the alkoxy group, or the group -COO-CH.sub.2 -U-V wherein U is a direct C-C bond, carbonyl or carbonyloxy and V is phenyl substituted by phenyl, alkoxy of 1-2 carbon atoms or halogen; R.sub.2 is hydroxy and R.sub.3 is a hydrogen atom or R.sub.2 and R.sub.3 collectively are an oxygen atom; A is -CH.sub.2 -CH.sub.2 or trans-CH=CH; B is -CH.sub.2 -CH.sub.2 or CH=CH; one of R.sub.4 and R.sub.5 is hydroxy and the other is a hydrogen atom; R.sub.6 and R.sub.7 each are alkyl of 1-10 carbon atoms or collectively are alkylene of up to 7 carbon atoms and with 2-3 carbon atoms in the chain, phenylene or naphthylene; R.sub.8 is a hydrogen atom or alkyl of 1-5 carbon atoms; ##STR2## when R.sub.2 is hydroxy and R.sub.3 is a hydrogen atom or is ##STR3## or -CH=CH- when R.sub.2 and R.sub.3 collectively are an oxygen atom; or, when R.sub.Type: GrantFiled: December 19, 1974Date of Patent: January 18, 1977Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Wolfgang Losert, Olaf Loge
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Patent number: 3984454Abstract: Prostanoic acid esters of the formulaPG -- CH.sub.2 -- X -- Ywherein PG is the prostanoyloxy radical of a prostaglandin, X is a carbon-carbon single bond, carbonyl or carbonyloxy, and Y is substituted phenyl are easily crystallized compounds at least as active as the unesterified prostanoic acid and useful for the purification of the parent prostaglandin are prepared by reacting, in the presence of an agent which splits off hydrogen halide, the unesterified prostaglandin with a halide of the formula Hal--CH.sub.2 --X--Y, wherein Hal is a halogen atom and X and Y have the values given above.Type: GrantFiled: May 2, 1974Date of Patent: October 5, 1976Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Wolfgang Losert
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Patent number: 3962218Abstract: Prostaglandins of the formula ##SPC1##Wherein R.sub.1 is HOCH.sub.2, --COOH, a salt thereof or an ester thereof; R.sub.2 is OH; and R.sub.3 is H or R.sub.2 and R.sub.3 collectively are = O. A is --CH.sub. 2 --CH.sub.2 -- or --(trans)--CH=CH--, B is --CH.sub. 2 CH.sub.2 --or --(cis)--CH=CH-- and R.sub.4 --O--O--R.sub.5 is a ketal group, are superior in physiological activity to the corresponding 15-.alpha.-hydroxy-prostaglandins.Type: GrantFiled: May 23, 1974Date of Patent: June 8, 1976Assignee: Schering AktiengesellschaftInventors: Bernd Raduchel, Werner Skuballa, Helmut Vorbruggen, Walter Elger, Wolfgang Losert, Olaf Loge
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Patent number: 3960949Abstract: 1,2-Substituted biguanides of the formula ##EQU1## wherein R.sub.1 is saturated or unsaturated, straight-chain or branched hydrocarbon of 1-12 carbon atoms which is unsubstituted or substituted by one or more fluorine atoms; a cycloalkyl group of 3-6 carbon atoms; or an aryl or aralkyl group of the formula ##SPC1##With n being the integer 0, 1 or 2 and X being hydrogen or halogen; and R'.sub.1 is a hydrogen atom or a saturated or unsaturated, straight-chain or branched hydrocarbon group of 1-12 carbon atoms; or R.sub.1 and R'.sub.1 collectively with the nitrogen atom to which they are attached are a heterocyclic ring containing one or more hetero atoms; and R.sub.Type: GrantFiled: July 9, 1974Date of Patent: June 1, 1976Assignee: Schering AktiengesellschaftInventors: Hanns Ahrens, Clemens Rufer, Helmut Biere, Eberhard Schroder, Wolfgang Losert, Olaf Loge, Ekkehard Schillinger