Patents by Inventor Helmut Vorbruggen

Helmut Vorbruggen 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).

  • Patent number: 4692464
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is (a) hydrogen, (b) C.sub.1-10 alkyl, (c) C.sub.1-10 alkyl substituted by halogen; C.sub.1-4 alkoxy; C.sub.6-10 aryl; C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group; di-C.sub.1-4 -alkylamino; or tri-C.sub.1-4 -alkylammonium, (d) C.sub.4-10 cycloalkyl, (e) C.sub.4-10 cycloalkyl substituted by C.sub.1-4 alkyl, (f) C.sub.6-10 aryl, (g) C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group, or (h) an aromatic heterocycle of 5 or 6 ring atoms one of which is O, N or S;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--;W is hydroxymethylene, RO-methylene, CH.sub.3 or CH.sub.3, ##STR2## wherein OH or OR is in the .alpha.- or .beta.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: September 8, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Gerda Mannesmann, Wolfgang Losert, Jorge Casals
  • Patent number: 4631276
    Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is a prostaglandin or prostacyclin residue;Y is oxygen, sulfur, imino, or N-(C.sub.1 -C.sub.4 -alkyl) imino;Q is (CR.sub.6 R.sub.7).sub.p wherein p is an integer of 0 to 3;R.sub.2 is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; C.sub.1 -C.sub.4 -alkoxycarbonyl; benzyloxycarbonyl; cyano; or di-C.sub.1 -C.sub.4 -alkylamino-carbonyl;R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 each independently is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; or aryl; andR.sub.3 and R.sub.4 together form a trimethylene, tetramethylene, or 1,3-butadienylene group when R.sub.2 and R.sub.5 together represent a direct bond;have valuable pharmacological properties, e.g., as blood-pressure-lowering or abortive agents.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: December 23, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Walter Elger, Michael-Harold Town, Ekkehard Schillinger
  • Patent number: 4489092
    Abstract: 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: Grant
    Filed: September 1, 1982
    Date of Patent: December 18, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
  • Patent number: 4466969
    Abstract: Prostacyclin, although having a useful dilating effect on blood vessels, is not sufficiently stable to ensure successful use as a hypotensive agent.A 7-oxo prostacyclin derivative of the general formula ##STR1## in which R.sub.1 represents the radical OR.sub.3 whereinR.sub.3 represents hydrogen, a straight-chain or branched optionally substituted, (C.sub.1 -C.sub.10)alkyl, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted heterocyclic,orR.sub.1 represents the radical NHR.sub.4 whereinR.sub.4 represents hydrogen, or a group derived from an unsaturated or saturated, unsubstituted or substituted, (C.sub.1 -C.sub.15)organic carboxylic or sulphonic acid,A represents --CH.sub.2 --CH.sub.2 --, cis--CH.dbd.CH-- or trans--CH.dbd.CH--,W represents ##STR2## either having a free or functionally modified hydroxy group which may be in the .alpha.- or .beta.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: August 21, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Robert C. Nikolson, Helmut Vorbruggen, Jorge Casals-Stenzel, Gerda Mannesmann
  • Patent number: 4423067
    Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, a heterocyclic residue, or NHR.sub.3, wherein R.sub.3 is an acid residue or hydrogen;X is oxygen;A is --CH.sub.2 --CH.sub.2 --, 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 is a straight-chain or branched, saturated or unsaturated aliphatic group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms, 1,2-methylene, 1,1-trimethylene;E is --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 are hydrogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group;R.sub.5 is free or functionally modified hydroxy and,when R.sub.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: December 27, 1983
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
  • Patent number: 4391814
    Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is the residue of an antiphlogistically effective carboxylic acid of the formula R.sub.1 COOH,n is an integer 1, 2, or 3, andX is oxygen, sulfur, or optionally alkylated nitrogenhave valuable antiinflammatory activity.
    Type: Grant
    Filed: December 23, 1981
    Date of Patent: July 5, 1983
    Assignee: Schering Aktiengesellschaft
    Inventor: Helmut Vorbruggen
  • Patent number: 4379927
    Abstract: A process for preparing imidazoleacetic acid derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen, alkyl, cycloalkyl, aralkyl, aryl, a heterocyclic group, amino, or amino substituted by alkyl, cycloalkyl, aralkyl, or aryl,R.sub.2 is hydrogen, alkyl, cycloalkyl, aralkyl, aryl, or a heterocyclic group,R.sub.1 and R.sub.2 together form a ring, andR.sub.3 is alkoxy, aralkoxy, amino, mono- or dialkylamino, pyrrolidino, piperidino, morpholino, or arylamino or heteroarylamino, each optionally substituted in the aryl portion,comprises reacting the corresponding amidine or guanidine of Formula II ##STR2## wherein R.sub.1 and R.sub.2 are as defined above and(HY) represents an optional inorganic mineral acid or an organic acid,with the corresponding acetoacetic acid derivative of Formula III ##STR3## wherein R.sub.3 is as defined above,X is a halogen, andR.sub.4 is trialkyl- or triaralkylsilyl, alkyl, or aralkyl.
    Type: Grant
    Filed: February 16, 1982
    Date of Patent: April 12, 1983
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz
  • Patent number: 4364950
    Abstract: 5-cyano-prostacyclins of the formula ##STR1## wherein R.sub.1 is OR.sub.2 or NHR.sub.3 ; R.sub.2 and R.sub.3 each independently is (a) H, (b) C.sub.1-10 -alkyl, (c) C.sub.1-10 -alkyl substituted by halo, C.sub.1-4 -alkoxy or phenyl, 1-naphthyl or 2-naphthyl, each optionally substituted as defined below, (d) C.sub.4-10 -cycloalkyl, (e) C.sub.4-10 -cycloalkyl substituted by C.sub.1-4 -alkyl, (f) phenyl, 1-naphthyl or 2-naphthyl, (g) phenyl, 1-naphthyl or 2-naphthyl substituted by 1-3 halogen atoms, phenyl, 1-3 alkyl groups of 1-4 C atoms each, or a chloromethyl-, fluoromethyl-, trifluoromethyl-, carboxyl-, hydroxy- or alkoxy-group of 1-4 C atoms, or (h) an aromatic, 5- or 6-membered heterocyclic ring containing one hetero atom which is O, N or S, the remaining atoms being carbon; R.sub.3 also possibly being an acyl group of a C.sub.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: December 21, 1982
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Helmut Vorbruggen, Bernd Raduchel, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
  • Patent number: 4359467
    Abstract: 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: Grant
    Filed: April 22, 1981
    Date of Patent: November 16, 1982
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
  • Patent number: 4284646
    Abstract: 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: Grant
    Filed: August 24, 1979
    Date of Patent: August 18, 1981
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
  • Patent number: 4256745
    Abstract: 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: Grant
    Filed: March 2, 1978
    Date of Patent: March 17, 1981
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
  • Patent number: 4247635
    Abstract: A process for the preparation of a 15 .alpha.-hydroxyprostaglandin intermediate of the formula ##STR1## wherein R.sub.1 is phenoxymethyl, phenoxymethyl substituted on the phenyl moiety by halogen or trifluoromethyl, or alkyl of 1-5 carbon atoms, andR.sub.2 is hydrogen, acetyl, benzoyl or p-phenylbenzoyl,which comprises stereospecifically microbiologically reducing a corresponding 15-ketone of the formula ##STR2## with a strain of the microorganism Kloeckera, Saccharomyces or Hansenula.
    Type: Grant
    Filed: December 5, 1979
    Date of Patent: January 27, 1981
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Kieslich, Bernd Raduchel, Werner Skubalia, Helmut Vorbruggen, Helmut Dahl
  • Patent number: 4235930
    Abstract: 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: Grant
    Filed: June 29, 1978
    Date of Patent: November 25, 1980
    Assignee: Schering, A.G.
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
  • Patent number: 4219479
    Abstract: 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: Grant
    Filed: November 24, 1978
    Date of Patent: August 26, 1980
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Werner Skuballa, Bernd Raduchel, Wolfgang Losert, Olaf Loge, Bernd Muller, Gerda Mannesmann
  • Patent number: 4209613
    Abstract: In a process for preparing a nucleoside by silylating the corresponding nucleoside base and reacting the silylated base with a 1-O-acyl, 1-O-alkyl, or 1-halogen derivative of a blocked monosaccharide or oligosaccharide in the presence of a catalyst, an improvement comprises silylating the base and reacting the sugar derivative in a single step.
    Type: Grant
    Filed: December 20, 1978
    Date of Patent: June 24, 1980
    Assignee: Schering Aktiengesellschaft
    Inventor: Helmut Vorbruggen
  • Patent number: 4203914
    Abstract: A process for the preparation of a perfluoroalkanesulphonic acid ester of the formulaC.sub.n F.sub.2n+1 SO.sub.3 Si R.sup.1 R.sup.2 R.sup.3comprising reacting a silane of the formulaR.sup.1 R.sup.2 R.sup.3 R.sup.4 Siwith a perfluoroalkanesulphonic acid of the formulaC.sub.n F.sub.2n+1 SO.sub.3 HwhereinR.sup.1, R.sup.2 and R.sup.3 each independently is alkyl with 1 to 6 carbon atoms,R.sup.4 is methyl, andn is from 1 to 12.Compounds wherein the total number of carbon atoms in Cn, R.sup.1, R.sup.2 and R.sup.3 is at least 6 are new and especially useful as silylating agents in organic cyntheses.
    Type: Grant
    Filed: January 8, 1979
    Date of Patent: May 20, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich Finke, Hans-Heinrich Moretto, Hans Niederprum, Helmut Vorbruggen
  • Patent number: 4191694
    Abstract: 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: Grant
    Filed: July 26, 1978
    Date of Patent: March 4, 1980
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Bernd Muller, Gerda Mannesmann, Olaf Loge, Ekkehardt Schillinger, Jorge Casals-Stenzel
  • Patent number: 4159343
    Abstract: 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: Grant
    Filed: March 3, 1978
    Date of Patent: June 26, 1979
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
  • Patent number: 4154953
    Abstract: 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: Grant
    Filed: August 19, 1977
    Date of Patent: May 15, 1979
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Wolfgang Losert
  • Patent number: 4109078
    Abstract: Nucleosides of the formula ##STR1## wherein Z is a free or blocked polysaccharide residue;X is O or S;m is 0 or 1;M.sub.1 is 0 or 1;R.sub.1 and R.sub.2 collectively are a saturated or unsaturated, optionally substituted bivalent organic radical containing up to two nitrogen atoms; andR.sub.3 and R.sub.4 independently are hydrogen, alkyl, alkoxycarbonyl, alkylaminocarbonyl, carboxyl, or nitrile group, or collectively are one of the bivalent radicals ##STR2## and substituted or hydrogenated analogs thereof, are sorbents useful for the separation of nucleoside mixtures.
    Type: Grant
    Filed: March 26, 1976
    Date of Patent: August 22, 1978
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Ulrich Niedballa