Patents by Inventor Klaus Annen
Klaus Annen 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: 4432976Abstract: Corticoids of Formula I ##STR1## wherein is a single bond or a double bond,X is hydrogen, fluorine, or chlorine,Y represents two hydrogen atoms or an oxygen atom, andZ is hydrogen or acyloxy of 2-6 carbon atoms, are pharmacologically active compounds, e.g., as anti-inflammatories.Type: GrantFiled: August 23, 1982Date of Patent: February 21, 1984Assignee: Schering AktiengesellschaftInventors: Klaus Annen, Henry Laurent, Helmut Hofmeister
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Patent number: 4404141Abstract: .DELTA..sup.16 - and .DELTA..sup.17 -21-chloro-20-keto steroids of the formula ##STR1## wherein n is 1 or 2,C.sub.1 C.sub.2 and C.sub.9 C.sub.11 represent a CC-single or CC-double bond,R.sub.1 is H or OH,R.sub.2 is H or CH.sub.3,R.sub.3 is H or F wherein, when R.sub.3 =F, C.sub.9 C.sub.11 is a CC-single bond, andR.sub.4 is H, CH.sub.3, or F,are valuable intermediates for preparation of highly effective, known steroids.A process for preparing these compounds involves heating the corresponding 11.beta.- and/or 17.alpha.- or 17a.alpha.-nitrooxy-21-mesyloxy-20-keto steroids with lithium chloride in a dipolar aprotic solvent at temperatures above room temperature.Type: GrantFiled: March 9, 1982Date of Patent: September 13, 1983Assignee: Schering AktiengesellschaftInventors: Klaus Annen, Henry Laurent, Helmut Hofmeister
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Patent number: 4390530Abstract: 3-Deoxy-.DELTA..sup.15 -steroids of the formula ##STR1## wherein R.sup.1 is hydrogen or an acyl group of a C.sub.1-15 hydrocarbon carboxylic acid, andR.sup.2 is ethynyl, chloroethynyl or propynyl are valuable progestationally effective compounds having low attendant androgenic side effects.Type: GrantFiled: February 11, 1981Date of Patent: June 28, 1983Assignee: Schering, A.G.Inventors: Helmut Hofmeister, Rudolf Wiechert, Klaus Annen, Henry Laurent, Sybille Beier
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Patent number: 4371529Abstract: 11-Methylene-.DELTA..sup.15 -steroids of Formula I ##STR1## wherein R.sup.1 is hydrogen or acyl andR.sup.2 is ethynyl, chloroethynyl or propynyl,are distinguished by a strong progestational activity and exhibit only a very low androgenic side effect.Type: GrantFiled: November 6, 1981Date of Patent: February 1, 1983Assignee: Schering, AktiengesellschaftInventors: Helmut Hofmeister, Karl Petzoldt, Klaus Annen, Henry Laurent, Rudolf Wiechert, Hermann Steinbeck
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Patent number: 4353985Abstract: A process for preparing an 11.beta.-hydroxy steroid of the formula ##STR1## wherein represents a single bond or a double bond;X is hydrogen, fluorine, chlorine or methyl; andV is methylene, ethylene, ethylidene or vinylidene;comprises fermenting an 11-deoxy steroid of the formula ##STR2## wherein , X and V are as defined above,R.sub.1 is hydrogen or C.sub.1-6 -alkyl; andR.sub.2 is C.sub.1-6 -alkyl;with a fungal culture of a genus Curvularia.Type: GrantFiled: July 14, 1980Date of Patent: October 12, 1982Assignee: Schering AktiengesellschaftInventors: Karl Petzoldt, Klaus Annen, Henry Laurent, Rudolf Wiechert
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Patent number: 4330541Abstract: Novel corticoid 17-thioacetals of the formula: ##STR1## wherein X is hydrogen, fluorine or methyl,R.sub.1 is hydrogen or C.sub.1 -C.sub.6 alkyl, andR.sub.2 is hydrogen or the acyl group of a C.sub.1-16 - hydrocarbon carboxylic acid,have valuable medicinal properties, e.g., as antiinflammatories.Type: GrantFiled: January 21, 1981Date of Patent: May 18, 1982Assignee: Schering AktiengesellschaftInventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Karl Petzoldt, Rudolf Wiechert
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Patent number: 4322349Abstract: A process for preparing a 6-methylene-.DELTA..sup.4 -3-keto steroid of the formula ##STR1## wherein R is hydrogen, alkoxy of up to 6 carbon atoms or acyloxy of up to 6 carbon atoms wherein the acyl group is that of a carboxylic acid, andR' is the CD-ring system of a steroid of the androstane or pregnane series,comprising reacting the corresponding .DELTA..sup.4 -3-keto steroid of the formula ##STR2## with a formaldehyde derivative of the formulaX(CH.sub.2 O).sub.n Ywhereinn is 1, 3 or an integer on the order of 100-1000, andX is C.sub.1-5 alkoxy and Y is C.sub.1-5 alkyl when n is 1,X and Y represent a single bond between the terminal C atom and the terminal O atom when n is 3, andX is hydroxy and Y is hydrogen when n is an integer on the order of 100-1000,in an inert solvent in the presence of a condensation agent which is a strong acida strongly acidic cation exchanger or a phosphoric acid derivative.Type: GrantFiled: February 17, 1981Date of Patent: March 30, 1982Assignee: Schering AktiengesellschaftInventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert
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Patent number: 4277468Abstract: 11-Methylene steroids of Formula I ##STR1## wherein R is hydrogen or acyl, andX is oxygen or two hydrogen atomshave valuable pharmacological properties.Type: GrantFiled: March 28, 1980Date of Patent: July 7, 1981Assignee: Schering AktiengesellschaftInventors: Helmut Hofmeister, Rudolf Wiechert, Klaus Annen, Henry Laurent, Hermann Steinbeck
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Patent number: 4243664Abstract: Novel corticoids of formula I ##STR1## wherein X is .beta.-hydroxymethylene, .beta.-fluoromethylene or carbonyl; Y is fluorine, chlorine, hydroxy, or acyloxy of 1-10 carbon atoms; and R.sub.1 is acyloxy of 1-10 carbon atoms, possess strong anti-inflammatory activity when administered topically and display only minor systemic side effects.Type: GrantFiled: March 13, 1979Date of Patent: January 6, 1981Assignee: Schering AktiengesellschaftInventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert, Hans Wendt, Joachim F. Kapp
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Patent number: 4207316Abstract: Corticoids of the formula ##STR1## wherein represents a single bond or a double bond;X is hydrogen, fluorine, chlorine or methyl;Y is hydrogen and Z is hydrogen, fluorine or chlorine, orY and Z together are a carbon-to-carbon bond;V is .beta.-hydroxymethylene, .beta.-chloromethylene or carbonyl;W is methylene, ethylidene or vinylidene;Q is oxygen or sulfur;R.sub.1 is alkyl of 1-8 carbon atoms, alkyl of 2-8 carbon atoms with an oxygen atom between two of the carbon atoms or benzyl, and R.sub.2 is hydrogen or alkyl of 1-4 carbon atoms, orR.sub.1 and R.sub.2 collectively are trimethylene or tetramethylene; andR.sub.3 is hydrogen, fluorine, chlorine, hydroxy, or hydroxy esterified by a C.sub.1-16 hydrocarbon carboxylic acid have valuable pharmacological properties, e.g., anti-inflammatory activity.Type: GrantFiled: January 25, 1979Date of Patent: June 10, 1980Assignee: Schering AktiengesellschaftInventors: Ernst Schottle, Alfred Weber, Mario Kennecke, Helmut Dahl, Joachim-Friedrich Kapp, Hans Wendt, Klaus Annen, Henry Laurent, Rudolf Wiechert
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Patent number: 4176126Abstract: Novel corticoids of formula I ##STR1## wherein X is .beta.-hydroxymethylene, .beta.-fluoromethylene or carbonyl; Y is fluorine, chlorine, hydroxy, or acyloxy of 1-10 carbon atoms; and R.sub.1 is acyloxy of 1-10 carbon atoms, possess strong anti-inflammatory activity when administered topically and display only minor systemic side effects.Type: GrantFiled: October 4, 1977Date of Patent: November 27, 1979Assignee: Schering AktiengesellschaftInventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert, Hans Wendt, Joachim-Friedrich Kapp
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Patent number: 4102908Abstract: A process for the preparation of pregnane derivatives of the formula ##STR1## wherein R.sub.1 is methyl or ethyl and R.sub.2 is methyl, ethyl, formyl, or acetyl, comprises reacting a nitrate ester of the formula ##STR2## wherein R.sub.1 is as above, in the presence of a catalytic amount of a mercury salt of a lower carboxylic acid with formic acid or acetic acid in a dipolar aprotic or basic solvent or with methanol or ethanol in an aprotonic, especially water-miscible, solvent in the presence of a mineral acid.Type: GrantFiled: June 1, 1977Date of Patent: July 25, 1978Assignee: Schering AktiengesellschaftInventors: Helmut Hofmeister, Klaus Annen, Henry Laurent, Rudolf Wiechert
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Patent number: 4081537Abstract: .DELTA..sup.15 -Steroids of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, trialkylsilyl or acyl; R.sub.2 is ethynyl, chloroethynyl or propinyl; and X is an oxygen atom, ##STR2## or NOR.sub.4 wherein R.sub.3 is a hydrogen atom or acyl and R.sub.4 is a hydrogen atom, acyl, alkyl or tetrahydropyranyl, possess progestational and ovulation and nidation inhibiting activities.Type: GrantFiled: October 4, 1976Date of Patent: March 28, 1978Assignee: Schering AktiengesellschaftInventors: Helmut Hofmeister, Rudolf Wiechert, Klaus Annen, Henry Laurent, Hermann Steinbeck
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Patent number: 4073900Abstract: 11.beta.-Fluoropregnenes of the formula ##STR1## wherein 6 7 IS A SINGLE OR DOUBLE BOND,R.sub.1 and R.sub.2 each are H or collectively CH.sub.2 or a single bond;R.sub.3 is H or, when 6 7 is a double bond, H, F or Cl,X or O or HOR.sub.4 andR.sub.4 is H or acyl, strong progestational activity and only weak antiandrogenic activity.Type: GrantFiled: October 19, 1976Date of Patent: February 14, 1978Assignee: Schering AktiengesellschaftInventors: Helmut Hofmeister, Henry Laurent, Rudolf Wiechert, Klaus Annen, Hermann Steinbeck
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Patent number: 4049804Abstract: Pregnanoic acid derivatives of general formula ##STR1## wherein is a single bond or a double bond; X is hydrogen, fluorine or methyl; Y is hydrogen, fluorine or chlorine; Z is .beta.-hydroxymethylene, .beta.-acyloxymethylene, .beta.-fluoromethylene, .beta.-chloromethylene, carbonyl or methylene; R.sub.1 is hydrogen, methyl in the .alpha.- or .beta.-position or methylene and R.sub.2 is hydrogen, hydroxy or acyloxy, or R.sub.1 and R.sub.2 collectively are alkylidendioxy and U.sub.1 is halogen, halogenated alkyl of 1-5 carbon atoms or halogenated phenyl, are topically effective anti-inflammatory agents.Type: GrantFiled: March 19, 1976Date of Patent: September 20, 1977Assignee: Schering AktiengesellschaftInventors: Henry Laurent, Klaus Annen, Rudolf Wiechert, Helmut Hofmeister
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Patent number: 4016269Abstract: Novel estrogenic 17.alpha.-hydroxy-1,3,5(10),15-estratetraenes of the formula ##STR1## wherein R.sub.1 is H, lower alkyl or lower acyl, R.sub.2 is lower alkyl and R.sub.3 is H, lower alkyl, lower acyl or tetrahydropyranyloxy, are produced by (a) reacting a 16.alpha.,17.alpha.-epoxy-estratriene with lithium halide or HCl in glacial acetic acid; converting the resulting halohydrin into a 16-halo-17-tetrahydropyranyl ether; and splitting off hydrogen halide from therefrom; or (b) reacting the 16.alpha.,17.alpha.-epoxy-estratriene with diphenylselenide and alkali metal borohydride; oxidizing the thus-produced 17.alpha.-hydroxy-16.beta.-phenylselenide to the corresponding phenylselenide oxide; and forming the .DELTA..sup.15 double bond by heating with removal of phenyl--Se--OH.Type: GrantFiled: August 11, 1975Date of Patent: April 5, 1977Assignee: Schering AktiengesellschaftInventors: Helmut Hofmeister, Klaus Annen, Rudolf Wiechert, Henry Laurent
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Patent number: 4008312Abstract: Pregnane-21-oic acid derivatives of the formula ##STR1## wherein THE LINKAGE REPRESENTS A SINGLE BOND OR A DOUBLE BOND;X is hydrogen, fluorine or chlorine;Y is methylene, hydroxymethylene, alkanoyloxymethylene, carbonyl, fluoromethylene or chloromethylene;R.sub.1 is hydrogen, alkyl of 1-6 carbon atoms, phenyl or naphthyl substituted with 0-3 lower alkyl, lower alkoxy or chlorine; andR.sub.2 represents a hydrogen atom, the cation of a physiologically compatible base or the residue of a physiologically acceptable alcohol of 1-18 carbon atoms.These compounds exhibit useful antiinflammatory activity when topically applied to inflamed skin.Type: GrantFiled: October 29, 1975Date of Patent: February 15, 1977Assignee: Schering AktiengesellschaftInventors: Klaus Annen, Helmut Hofmeister, Henry Laurent, Klaus Kieslich, Hans Wendt, Peter Klaus Mengel
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Patent number: 3966713Abstract: 11.beta.-Fluoroandrostenes of the formula ##SPC1##Wherein R.sub.1 and R.sub.2 are hydrogen atoms, methylene or another C--C bond; R.sub.3 is H or Cl, R.sub.4 is H, F or Cl; and X is carbonyl, .beta.-hydroxymethylene, or an ester or ether thereof or .alpha.-alkyl-.beta.-hydroxymethylene or an ester thereof, possess androgenic activity and can be prepared by the dehalogenation of a corresponding 9.alpha.-halo-11.beta.-F steroid.Type: GrantFiled: February 25, 1975Date of Patent: June 29, 1976Assignee: Schering AktiengesellschaftInventors: Helmut Hofmeister, Henry Laurent, Rudolf Wiechert, Klaus Annen, Hermann Steinbeck