Patents Assigned to Siegfried Aktiengesellschaft
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Patent number: 4689233Abstract: The present invention relates to a coronary therapeutic agent in the form of soft gelatin capsules, which contain the active substance nifedipine in an organic solvent. In the prior art, there where problems regarding the capsule size and with respect to the low nifedipine active substance concentration. These problems are obviated by the invention, in that nifedipine with PVP, optionally as a coprecipitate and without glycerin, is dissolved in THFP and consequently permits a capsule weight of in all only e.g. 162 mg.Type: GrantFiled: January 6, 1986Date of Patent: August 25, 1987Assignee: Siegfried AktiengesellschaftInventors: Stephan Dvorsky, Franz Radivojevich, Hans Joss
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Patent number: 4668786Abstract: New derivatives of theophylline having the formula ##STR1## wherein R is hydrogen or a hydroxy group, and n is an integer of 0.ltoreq.n.ltoreq.3 and/or the pharmaceutically acceptable, acid addition salts thereof, exhibit in addition to other properties, histamine-serotinine- bradykynine- antagonistic, anti-anaphylactic and .beta.-adrenergic stimulating effects.Type: GrantFiled: December 26, 1985Date of Patent: May 26, 1987Assignee: Siegfried AktiengesellschaftInventors: Kurt Thiele, Felix Geissmann, Ludwig Zirngibl, Ulrich Jahn
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Patent number: 4652659Abstract: 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid carboxymethyl ester as known per se is obtainable by a novel and more simple method comprising mild acid hydrolysis of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxyacetic tetrahydropyran-2-yl ester. The final product is a valuable drug having antiinflammatory activity.Type: GrantFiled: October 16, 1984Date of Patent: March 24, 1987Assignee: Siegfried AktiengesellschaftInventors: Rene Gnehm, Rolf Weber
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Patent number: 4603204Abstract: New derivatives of theophylline having the formula ##STR1## in which R denotes hydrogen or OH, n the numbers 0 or 1, X either >CH-- or >N--, Y either --O-- or --CO-- and R a five membered or six membered aryl ring or hetero-aryl ring, that is substituted in given cases with halogen, short chain alkyl groups, alkoxy groups or halogen-alkyl, and exhibit in addition to other properties, histamine-, serotinine- bradykynine- antagonistic, anti-anaphylactic and -adrenergic stimulating effects.Type: GrantFiled: March 11, 1983Date of Patent: July 29, 1986Assignee: Siegfried AktiengesellschaftInventors: Kurt Thiele, Felix Geissmann, Ludwig Zirngibl, Ulrich Jahn
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Patent number: 4554356Abstract: A process for the manufacture of imidazolylvinyl ethers of the formula ##STR1## wherein Im represents the substituted or unsubstituted 1-H-imidazol-1-yl group and An, R and Y are defined hereinbelow by condensation of a corresponding ketone of the formulaAr--CO--CHR--Im (II)with the splitting-off of a Z group, with a condensable substance of the formulaZ--Y (III)in the aqueous solution of a strong inorganic base, preferably in concentrated aqueous soda lye. The reaction may also be carried out in the presence of a second liquid organic phase, preferably benzene or toluene, especially in the presence of a phase transfer catalyst in this case. Through careful crystallization of the product manufactured according to this method, it is possible to manufacture approximately pure E-isomers of the imidazolylvinyl ether of formula (I), without the requirement of chromatographic separation.Type: GrantFiled: January 16, 1985Date of Patent: November 19, 1985Assignee: Siegfried AktiengesellschaftInventors: Ludwig Zirngibl, Kurt Thiele
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Patent number: 4550175Abstract: For preparing substantially pure (Z)-1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)-0-(2,4-dichlorobenzyl)-ethano ne oxime ether having the formula ##STR1## i.e. the cis-isomer of said oxime ether in a stereospecifically pure form, the pure (Z)-stereoisomer of the corresponding ethanone oxime is first converted into an alkali salt in a polar solvent, such as acetone or dimethylformamide, using an alkali in an amount somewhat less than the equimolar amount with respect to the said ethanone oxime, and is then converted to the desired ether by reacting it at a temperature not higher than 40.degree. C. with a halogen compound capable of forming the desired ether. Isolation of the ether product is obtained as the free base or by precipitating it as an acid addition salt upon addition of a suitable organic or mineral acid, preferably nitric acid.Type: GrantFiled: March 15, 1984Date of Patent: October 29, 1985Assignee: Siegfried AktiengesellschaftInventors: Georg Mixich, Kurt Thiele
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Patent number: 4531965Abstract: A method of selectively controlling weeds in crop areas, notably vineyards or fruit plantations, by applying a composition that includes different active herbicidal ingredients; the composition comprises a synergistic combination of about 1 part, by weight, of methyl-5-(2,4-dichlorophenoxy)-2-nitrobenzoate as a first active ingredient, and about 1 to 5 parts, by weight, of 3-tert.butyl-5-chloro-6-methyl-uracil as a second active ingredient.The novel composition comprises said synergistic combination and may further contain a mineral oil and adjuvants such as an emulsifier.Type: GrantFiled: November 22, 1982Date of Patent: July 30, 1985Assignee: Siegfried AktiengesellschaftInventors: Jacques Meyer, Walter Scharen
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Patent number: 4503237Abstract: 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-3-indole acetic acid as known per se is obtainable by means of a novel and more simple method. This method comprises hydrolizing 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indole acetic acid tetrahydropyranyl ester, which ester is a novel compound. The final product obtained is a valuable drug having antiinflammatory activity.Type: GrantFiled: December 16, 1982Date of Patent: March 5, 1985Assignee: Siegfried AktiengesellschaftInventors: Ren/e/ Gnehm, Rolf Weber
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Patent number: 4483999Abstract: Novel compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, halogen, or alkyl or alkoxy containing from 1 to 4 carbon atoms,R.sup.2 is hydrogen, halogen, hydroxy or alkyl of alkoxy containing from 1 to 4 carbon atoms,n and m are integers such that the sum (n+m) lies in the range from 3 to 10 inclusive and n differs from m, andx is alkyl containing from 1 to 4 carbon atoms, hydrogen or a cation which is a metal cation of main Groups 1, 2 and 3 of the Periodic System of the Elements, an organic base cation or an ammonium ion. These compounds have pharmaceutical utility by virtue of their considerable ability to reduce the level of fatty substances in the blood.Type: GrantFiled: March 1, 1977Date of Patent: November 20, 1984Assignee: Siegfried AktiengesellschaftInventors: Kurt Thiele, Quazi Ahmed, Rudolf Adrian, Ulrich Jahn
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Patent number: 4474956Abstract: In the preparation of 4-hydroxy-2-methyl-N-2-pyridyl-2H-benzothiazine-3-carboxamide 1,1-dioxide by reacting the corresponding 3-methoxycarbonyl compound with 2-aminopyridine, a dramatic increase in the yield is obtained if the reaction is carried out in the presence of 0.1 to 1.5 mole equivalent (based on the 3-methoxycarbonyl compound) of an alkyl- or arylsulfonic acid.Type: GrantFiled: June 29, 1983Date of Patent: October 2, 1984Assignee: Siegfried AktiengesellschaftInventors: Ludwig Zirngibl, Rene Gnehm
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Patent number: 4463195Abstract: Ortho-nitrobenzaldehyde, a well known compound suitable as an indicator and as an intermediate for many organic syntheses including production of pharmaceuticals, is obtained by contacting a C.sub.1 -C.sub.4 lower alkyl ester of o-nitrophenyl pyruvic acid in the form of its enolate, i.e. the enol salt or enol ester, with hydrogen peroxide; the enol salt can be the enolate of an alkali metal, an alkaline earth metal or of aluminum, and the enol ester can be the ester formed by the enolic hydroxyl and formic, acetic, propionic or butyric acid.Type: GrantFiled: April 14, 1983Date of Patent: July 31, 1984Assignee: Siegfried AktiengesellschaftInventors: Hans-Rudolf Marti, Rene Gnehm
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Patent number: 4443612Abstract: 1-Aryl-2-(1H-imidazol-1-yl)-ethanone oxime ethers are known to exist as a mixture of isomers corresponding to the formulae: ##STR1## To prepare such an isomer in a stereospecifically pure form, the pure stereoisomer of the corresponding ethanone oxime is first converted into an alkali salt in a polar solvent, such as acetone or dimethylformamide, using an alkali in an amount somewhat less than the equimolar amount with respect to the said ethanone oxime, and is then converted to the desired ether by reacting it at a temperature not higher than 40.degree. C. with a halogen compound capable of forming the desired ether. Isolation of the ether product is obtained as the free base or by precipitating it as an acid addition salt upon addition of a suitable organic or mineral acid, preferably nitric acid.Type: GrantFiled: August 30, 1982Date of Patent: April 17, 1984Assignee: Siegfried AktiengesellschaftInventors: Georg Mixich, Kurt Thiele
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Patent number: 4440561Abstract: Compositions containing Bifenox and Linuron in combination with a mineral oil, such as white oil, show a remarkable synergism of the constituents and are of use as pre-harvest defoliants for crop plants, e.g. for desiccation of potato plants.Type: GrantFiled: February 3, 1982Date of Patent: April 3, 1984Assignee: Siegfried AktiengesellschaftInventors: Jacques Meyer, Walter E. Scharen
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Patent number: 4436913Abstract: 1H- and 2H- indazole derivatives and pharmaceuticals containing these blood-pressure lowering 1H- and 2H- indazole derivatives of the formula ##STR1## and their acid addition salts, wherein R1 may be in position 1 or position 2 on the nitrogen atoms in formula I. The groups R1, R2 and R3 represent hydrogen or the usual lower molecular groups. The R group is a 2-imidazolinylamino group or a 3,4,5,6-tetryhydropyrimidinylamino group, wherein these groups may also be present in their tautomeric forms. These groups may also be in an aryl group in the R1 group, in which case the R group may also be a halogen atom. R may only represent one of the heterocyclic secondary or tertiary amino groups in the 4 or 7 position for the 1H- indazole derivatives when the R1 group is simultaneously an aryl or an aralkyl group.Type: GrantFiled: April 28, 1982Date of Patent: March 13, 1984Assignee: Siegfried AktiengesellschaftInventors: Istvan Molnar, Kurt Thiele, Felix Geissmann, Ulrich Jahn
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Patent number: 4352931Abstract: Novel benzologs or pyrazolo-quinazoline derivatives of the formula (I) ##STR1## wherein X and Y are independently selected from oxygen, sulphur and imino and wherein ring (C) is a pyrazole ring fused to ring (B) via one of the three ortho positions or sides of ring (B); the fused pyrazole ring (C) is either in the 4,3- or the 3,4-arrangement; and tautomers of formula (I) compounds; when X is not oxygen, i.e. stands for sulphur or imino, Y may stand for a covalent bond that links the hydrogen directly to the carbon atom in position 2.Two methods for producing the novel formula (I) compounds are disclosed. The first or indazole method starts from a precursor having a benzene moiety (ring B) and a pyrazolo moiety (ring C) fused therewith, i.e. the indazole structure; ring (B) carries two vicinal substituents for forming the pyrimidine moiety or ring (A) by cyclization. The second or quinazoline method starts from a precursor having the pyrimidine moiety (A) and the benzene moiety (B) fused therewith, i.e.Type: GrantFiled: May 22, 1980Date of Patent: October 5, 1982Assignee: Siegfried AktiengesellschaftInventors: Eckehard K. T. Cuny, Frieder W. Lichtenthaler, Alfred R. Moser
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Patent number: 4330545Abstract: Aryl-imidazol-1-yl vinyl ethers and their acid addition salts are disclosed, wherein the imidazolyl vinyl ether has the formula: ##STR1## Ar in the formula represents a substituted or unsubstituted aryl or heterocyclic radical; R represents hydrogen or a C.sub.1 -C.sub.12 alkyl or cycloalkyl (saturated or unsaturated) or Ar as above; Im represents a 1-H-imidazol-1-yl group (unsubstituted or substituted); and Y represents a saturated or unsaturated C.sub.1 -C.sub.12 alkyl or a group --Z--Ar in which Ar has the above meaning and --Z-- is a saturated or unsaturated C.sub.1 -C.sub.12 alkylene wherein each of the alkyl and the alkylene may have a carbon chain once or twice interrupted by or, in the case of the alkylene, terminated on its Ar-end by oxy, thio, sulfinyl or sulfonyl bridges, always with the proviso that at least one of Ar and Y is a heterocyclic radical. These compounds are wide-spectrum fungicides and bactericides, and the preferred compounds among them are hydrophilic.Type: GrantFiled: May 19, 1980Date of Patent: May 18, 1982Assignee: Siegfried AktiengesellschaftInventors: Ludwig Zirngibl, Johanna Fischer, Kurt Thiele
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Patent number: 4305942Abstract: Therapeutic xanthine oxidase inhibitor composition containing as an active ingredient 3-dimethylamino-7-methyl-1,2-(n-propylmalonyl)-1,2-dihydro-1,2,4-benzotria zine dihydrate of the formula ##STR1## Uratic diathesis in warm-blooded animals is therapeutically treated by administering the aforementioned xanthine oxidase inhibitor to such animals, e.g., human, either orally or by means of an injection, thereby inhibiting their xanthine oxidase activity.Type: GrantFiled: October 28, 1980Date of Patent: December 15, 1981Assignee: Siegfried AktiengesellschaftInventors: Kurt Thiele, James S. G. Cox, Johanna Fischer, Ulrich Jahn
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Patent number: 4229367Abstract: Trans-4-alkyl-cyanoarylcyclohexanes are prepared in a stereoselective manner from arylcarboxylic acids of the formula Ar-[Ar].sub.n -Ar-4-COOH, Ar being aryl and n being 0 to 2, by first converting such a carboxylic acid to a mixture of the cis and trans isomers of the corresponding cyclohexa-2,5-diene-4-carboxylic acid, esterifying the resulting isomer mixture with a lower alkanol and further hydrogenating the resulting esters/isomers to produce the cis and trans isomers of the corresponding cyclohexane-4-carboxylic acid esters, isomerizing the cis isomers in the mixture to the trans isomer thereby producing a mixture containing the trans isomer substantially free from cis isomer, stereospecifically saponifying the trans isomer, growing a carbon chain of desired length on the carboxyl group of the resulting carboxylic acid, reducing the carbonyl group thereof, and introducing a cyano group into the terminal aryl group. The resulting product is useful as a nematic liquid crystal.Type: GrantFiled: May 15, 1979Date of Patent: October 21, 1980Assignee: Siegfried AktiengesellschaftInventors: Bernhard Granwehr, Rene Gnehm
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Patent number: 4223143Abstract: Novel quinazoline derivatives of the formula (1) ##STR1## wherein ring C is a pyrazole ring fused to ring B in two vicinal positions thereof that are not fused with ring A. The novel formula (1) compounds or pyrazolo-quinazoline-ones are structurally related to allopurinol, a well known drug useful in the treatment of gout and are expected to replace or complement allopurinol in the therapeutic use thereof. The generic name Benzoallopurinol is suggested for the novel formula (1) compounds; formula (1) includes angular and linear structures of the interfused rings A, B and C.Two methods for producing the novel formula (1) compounds are disclosed. The first method starts from the indazole structure that includes the interfused rings B and C, and ring A is formed on the indazole moiety. The second method starts from the quinazoline structure that includes interfused rings A and B, and the pyrazole ring C is formed on the benzo moiety (ring B) of the quinazoline structure.Type: GrantFiled: December 11, 1978Date of Patent: September 16, 1980Assignee: Siegfried AktiengesellschaftInventors: Eckehard K. T. Cuny, Frieder W. Lichtenthaler
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Patent number: 4214095Abstract: Novel compounds of the formula (1) ##STR1## wherein R.sup.1 and R.sup.2 are different lower alkyls and R.sup.3 is a lower alkyl or a methyl pyridine group, and the acid addition salts of formula (1) compounds when R.sup.3 is methyl pyridine. The novel compounds have an asymmetric C-atom and may be in the form of the D,L racemates or the D or L stereoisomers.These compounds are useful in the treatment of hypercholesterolemia and hyperlipidemia because of their high effectiveness in reducing the level of cholesterol and lipids in the blood combined with very low general toxicities and substantially reduced hepatomegalitic effects.Type: GrantFiled: January 25, 1979Date of Patent: July 22, 1980Assignee: Siegfried AktiengesellschaftInventors: Kurt Thiele, Quazi Ahmed, Rudolf Adrian, Ulrich Jahn