Patents Examined by Joseph Paul Brust
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Patent number: 5349103Abstract: A process for the preparation of a nitrile of formula ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl, by reaction of an aldehyde of formula ##STR2## wherein R is as defined above, with hydroxylamine sulfate and subsequent dehydration, which process comprises carrying out the reaction in propionic acid in the presence of a salt of propionic acid by heating to an external temperature in the range from 140.degree. to 165.degree. C., preferably from 150.degree. to 160.degree. C., for 2 to 6 hours, preferably for 3 to 5 hours, under atmospheric pressure, and simultaneously distilling the mixture of propionic acid and water from the system until a solution forms, and thereafter removing the mixture of propionic acid and water at 100.degree.-130.degree. C., preferably 110.degree.-120.degree. C., by vacuum distillation, and then isolating the resultant nitrile by standard procedures.Type: GrantFiled: January 21, 1994Date of Patent: September 20, 1994Assignee: Ciba-Geigy CorporationInventor: Bilge Gulec
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Patent number: 5347032Abstract: A process for the preparation of C.sub.4 -C.sub.10 alkyl cyanoacetates by the reaction of cyanoacetic acid with C.sub.4 -C.sub.10 alkanols at a temperature of from 35.degree. to 150.degree. C. and under a pressure of from 70 to 1013 mbar, in the presence of catalytic amounts of acid, while a C.sub.4 -C.sub.10 alkanol/water azeotrope is separated during the reaction.Type: GrantFiled: August 2, 1993Date of Patent: September 13, 1994Assignee: BASF AktiengesellschaftInventors: Helmut Reichelt, Clemens Grund
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Patent number: 5347033Abstract: A process for preparing 5-cyanovaleramide by reacting adiponitrile with water at from 50.degree. to 200.degree. C. in the presence of a supported unionized-copper catalyst comprises employing from 1 to 15 mol of water per mole of adiponitrile and a residence time of from 5 to 60 minutes.Type: GrantFiled: June 28, 1993Date of Patent: September 13, 1994Assignee: BASF AktiengesellschaftInventors: Tom Witzel, Eberhard Fuchs, Franz Merger
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Patent number: 5344842Abstract: The invention relates to novel thiosemicarbazones of formula I ##STR1## wherein R.sub.1 is lower alkyl, lower alk-2-en-1-yl or lower alk-2-yn-1-yl,R.sub.2 and R.sub.3 independently of one another are hydrogen or lower alkyl, or R.sub.2 and R.sub.3 together are lower alkylidene,R.sub.4 is hydrogen, lower alkyl, lower alkoxy, aryl or aryl-lower alkyl, or the group --C(.dbd.O)--R.sub.6 wherein R.sub.6 is lower alkyl, aryl, heteroaryl, aryloxy, aryl-lower alkoxy or lower alk-2-en-1-yloxy,R.sub.5 is aryl, aryl-lower alkyl, unsaturated or saturated heterocyclyl-lower alkyl, lower alkoxycarbonyl-lower alkyl or the group --C(.dbd.O)--R.sub.7 wherein R.sub.7 is lower alkyl, aryl, aryl-lower alkyl, aryl-lower alkenyl, heteroaryl, aryloxy, aryl-lower alkoxy or lower alk-2-en-1-yloxy, or, when R.sub.4 is other than hydrogen, R.sub.Type: GrantFiled: May 24, 1993Date of Patent: September 6, 1994Assignee: Ciba-Geigy CorporationInventor: Martin Missbach
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Patent number: 5344955Abstract: 1-Amino-1-cyanamido-2,2-dicyanoethylene, sodium salt is prepared by a process which comprises reacting malononitrile with sodium dicyanamide at an elevated temperature and in the presence of an aprotic, dipolar solvent. The subject compound is useful as an intermediate to prepare substituted pyrimidines.Type: GrantFiled: July 26, 1993Date of Patent: September 6, 1994Assignee: Ciba-Geigy CorporationInventor: Ward H. Oliver
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Patent number: 5342961Abstract: A process is disclosed for producing fluid imidazolinium tensides by reaction of 1-hydroxyethyl-2-alkylimidazolines with neutralized quaternary agents and hydrolysis of the quaternary products thus obtained with aqueous bases. The 1-hydroxyethyl -2-alkylimidazolines are added at a high temperature to an aqueous solution of the neutralized quaternary agents at a molar proportion between imidazoline derivates and the quaternary agents from 1:1.5 to 1:3. The reaction mixture thus obtained is maintained at a temperature in a range of 70.degree. to 85.degree. C. for 30 to 120 minutes, 0.85 to 1.0 mol alkali metal hydroxides, referred to the amount of quaternary agents added during step (a), are added thereto within the 30 to 120 minutes at a temperature in the range of 75.degree. to 85.degree. C., and the reaction mixture thus obtained is maintained at a temperature in the range of 75.degree. to 90.degree. C. for 140 to 220 minutes.Type: GrantFiled: August 6, 1993Date of Patent: August 30, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Guenter Uphues, Sven Jaensch, Uwe Ploog, Udo Steinberner
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Patent number: 5340831Abstract: Muscarinic receptor antagonists of formula (I), and their pharmaceutically acceptable salts, wherein Y is --CH.sub.2 --, --(CH.sub.2).sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.2 O-- or --CH.sub.2 S--; R is --CH or --CONH.sub.2 ; and R.sup.1 is a group of formula (a), where R.sup.2 and R.sup.3 are each independently H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --(CH.sub.2).sub.n OH, halo, trifluoromethyl, cyano, --(CH.sub.2).sub.n NR.sup.4 R.sup.5, --CO(C.sub.1 -C.sub.4 alkyl), --OCO(C.sub.1 -C.sub.4 alkyl), --CH(OH)(C.sub.1 -C.sub.4 alkyl), --C(OH)(C.sub.1 -C.sub.4 alkyl.sub.2, --SO.sub.2 NH.sub.2, --(CH.sub.2).sub.n CONR.sup.6 R.sup.7 or --(CH.sub.2).sub.n COO(C.sub.1 -C.sub.4 alkyl); R.sup.4 is H or C.sub.1 -C.sub.4 alkyl; R.sup.5 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkysulphonyl; R.sup.6 and R.sup.7 are each independently H or C.sub.1 -C.sub.4 alkyl; and n is 0, 1 or 2. The compounds are particularly useful in treating irritable bowel syndrome.Type: GrantFiled: June 12, 1990Date of Patent: August 23, 1994Assignee: Pfizer Inc.Inventors: Peter E. Cross, Alexander R. MacKenzie
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Patent number: 5340824Type: GrantFiled: December 2, 1992Date of Patent: August 23, 1994Assignee: Rhone-Poulenc Rorer S.A.Inventors: Claude Gueremy, Patrick Jimonet, Serge Mignani
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Patent number: 5338747Abstract: The invention relates to pharmaceutical and cosmetic compositions comprising at least one benzisothiazolinone-1-dioxide derivative with the formula: ##STR1## where R.sup.1 can be hydrogen, and R.sup.2 can be certain generally hydrophobic C.sub.8 -C.sub.20 aliphatic groups or the group: ##STR2## where R.sup.5 is aliphatic or else R.sup.2 is a saturated or unsaturated C.sub.2 -C.sub.6 group ending in an aromatic nucleus.These compositions can be used to inhibit elastases such as human leucocytic elastase. They may be applied topically as a cosmetic.Many of the benzisothiazolinone-1-dioxide derivative specified as active ingredient in such compositions are novel compounds.Type: GrantFiled: March 7, 1991Date of Patent: August 16, 1994Assignee: Chesebrough-Pond's USA Co., Division of Conopco, Inc.Inventors: Ladislas Robert, Elemer Moczar, William G. Hornebeck, Christiane M. P. Kerneur
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Patent number: 5336670Abstract: Compounds of the formula ##STR1## wherein X is hydrogen, halogen or an optionally substituted alkyl, Y is selected from the group consisting of hydrogen, halogen optionally substituted alkyl, an optionally substituted aryl or arylalkyl, --(CH.sub.2).sub.m Si (Alk.sub.1).sub.3, --(CH.sub.2).sub.n OAlk.sub.2 or --(CH.sub.2).sub.p SAlk.sub.3, m, n and p are an integer from 0 to 6, Alk.sub.1, Alk.sub.2 and Alk.sub.3 are alkyl and R is alkyl of 1 to 18 carbon atoms or the remainder of an alcohol used in the pyrethrinoid series having pesticide properties.Type: GrantFiled: December 17, 1992Date of Patent: August 9, 1994Assignee: Roussel-UclafInventors: Marc Benoit, Jean-Pierre Demoute, Jean-Marc Girodeau
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Patent number: 5336779Abstract: In producing formylimidazoles by catalytically oxidizing the corresponding 4- or 5-hydroxymethylimidazoles, the catalytic oxidation is carried out in the presence of a noble metal catalyst while oxygen or air is blown into the reaction system. In this case, it is particularly desirable that the catalytic oxidation in the presence of a noble metal catalyst be carried out in a solvent comprising an aqueous alkali or in a mixed solvent composed of an aqueous alkali and an organic solvent immiscible with water.Type: GrantFiled: September 23, 1993Date of Patent: August 9, 1994Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki KaishaInventors: Toshio Yamamoto, Kazumasa Hirata, Shigenori Wakabayashi, Akio Katsuura
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Patent number: 5336804Abstract: The alkanes, e.g., propane, are ammoxidized into admixtures containing .alpha.,.beta.-unsaturated nitriles, e.g., admixture of acrylonitrile and propylene, by reacting such alkane with ammonia and oxygen, in vapor phase, in the presence of a catalytically effective amount of a solid catalyst, at least one active catalytic phase of which having the empirical formula (I):VSb.sub.a Bi.sub.b O.sub.x (I)optionally also containing iron and/or gallium and/or indium, in which a is a whole or fractional number equal to or greater than 1, b is a whole or fractional number equal to or greater than 0.01, and x is a whole or fractional number provided by the oxidation number of the other elements of the at least one active catalytic phase.Type: GrantFiled: February 8, 1993Date of Patent: August 9, 1994Assignee: Rhone-Poulenc ChimieInventors: Gilbert Blanchard, Gilbert Ferre
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Patent number: 5334743Abstract: The alkanes, e.g., propane, are selectively converted (ammoxidized) into admixtures comprising .alpha.,.beta.-unsaturated nitriles, e.g., acrylonitrile, by reacting same with ammonia and oxygen, in vapor phase, and in the presence of a catalytically effective amount of a solid catalyst, the catalytically active phase of which comprising (1) molybdenum, vanadium and oxygen and (2) at least one of the elements, manganese, zinc, cobalt, copper, lithium, sodium, potassium and silver.Type: GrantFiled: December 16, 1992Date of Patent: August 2, 1994Assignee: Rhone-Poulenc ChimieInventors: Gilbert Blanchard, Elisabeth Bordes, Gilbert Ferre
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Patent number: 5334721Abstract: The invention relates to a process for the preparation of high yields of 5-oxohexane nitriles with minimum formation of 1 undesired isomer. Such nitriles may be utilized as starting materials for the preparation of pharmaceutical and agrochemical intermediates and as well as final products. The process comprises reacting a methyl ketone and an .alpha.,.beta.-unsaturated nitrile in the presence of a catalytically effective amount of a strong base. One of the products which may be created by the process is 2,4-dimethyl-5-oxohexane nitrile.Type: GrantFiled: July 29, 1993Date of Patent: August 2, 1994Assignee: Stamicarbon B.V.Inventors: Anna M. C. F. Castelijns, Henricus J. Arts, Richard Green
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Patent number: 5334745Abstract: 3-Aminopropionitriles of the general formula I ##STR1## where R.sup.1,R.sup.2,R.sup.3,R.sup.4 and R.sup.5 independently of one another are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.8 -aminoalkyl, C.sub.1 -C.sub.8 -cyanoalkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.7 -C.sub.20 -aralkyl or aryl,are prepared by a process in which an amine of the general formula II ##STR2## is reacted with an acrylonitrile of the general formula III ##STR3## where the substituents have the abovementioned meanings, in a molar ratio of from 0.9:1 to 100:1 over a heterogeneous catalyst at from 40.degree. to 200.degree. C. and from 1 to 350 bar.Type: GrantFiled: May 28, 1993Date of Patent: August 2, 1994Assignee: BASF AktiengesellschaftInventors: Martin Brudermueller, Tom Witzel, Franz Merger
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Patent number: 5334744Abstract: A process for obtaining an isomer of a compound of general formulaR--CH(CN)--R' (I)wherein each of R and R' may be any organic radical linked directly or through a heteroatom to the carbon atom bearing the cyano group provided that at least one of R and R' comprises at least one resolved chiral center which is stable under the conditions of the process, or a racemic modification comprising the isomer and its enantiomer, which comprises the step of treating the epimer of the isomer, or the racemate comprising the epimer and the enantiomer of the epimer, in solution in a polar organic solvent, or in slurry in a polar organic liquid diluent in which the epimer or the racemate is partially soluble, with a source of cyanide ions, in the absence of a base, the isomer, or the racemic modification comprising the isomer and its enantiomer, being less soluble in the solvent or diluent than the epimer of the isomer, or the racemate comprising the epimer of the isomer and the enantiomer of the epimer, respectively.Type: GrantFiled: December 23, 1992Date of Patent: August 2, 1994Assignee: Zeneca Ltd.Inventors: Ernest S. Cleugh, David J. Milner
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Patent number: 5334611Abstract: Novel mitomycin derivatives represented by the formula (I) are obtained by introducing a substituent at the 6-position. The mitomycin derivatives of the present invention have an antitumor activity.Type: GrantFiled: August 3, 1993Date of Patent: August 2, 1994Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Hitoshi Arai, Yutaka Kanda, Motomichi Kono, Masaji Kasai, Tadashi Ashizawa, Katsushige Gomi
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Patent number: 5332825Abstract: This invention relates to two processes for preparing aminoacetonitriles in one vessel under anhydrous conditions. Process I involves the steps of: (A) reacting trimethylsilyl cyanide and an aldehyde in a water miscible amide solvent to obtain a silyl blocked cyanohydrin solution; (B) adding a catalytic amount of water to the silyl blocked cyanohydrin solution from Step (A); and (C) passing ammonia through the solution to obtain an aminoacetonitrile. Process II involves the steps of: (A') reacting trimethylsilyl cyanide with an aldehyde in the absence of solvent to form a silyl blocked cyanohydrin; (B') adding a water miscible amide solvent to the silyl blocked cyanohydrin from Step (A') to obtain a solution; and (C') passing ammonia through the solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.Type: GrantFiled: October 13, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventor: Paul R. Buckland
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Patent number: 5332844Abstract: Straight-chain acrylonitrile dimers including 1,4-dicyanobutene, 1,4-dicyanobutadiene and adiponitrile are produced at a high selectivity rate and yield by dimerizing acrylonitrile in the presence of a catalyst comprising at least one ruthenium compound, for example dichloro-tetrakis (dimethylsulfoxide) ruthenium, and in the presence of at least one organic acid, for example, propionic acid, and optionally in the further presence of a basic compound, a reducing compound and/or a sulfoxide compound.Type: GrantFiled: March 4, 1993Date of Patent: July 26, 1994Assignee: Ube Industries, Ltd.Inventors: Ryoji Sugise, Kouichi Kashiwagi, Masashi Shirai, Toshihiro Shimakawa
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Patent number: 5332826Abstract: This invention relates to a process for preparing aminoacetonitriles in one vessel. The process involves the steps of: (A) reacting an alkali metal cyanide with an aldehyde in water to form a cyanohydrin; (B) extracting the cyanohydrin formed in Step (A) into a water immiscible solvent to form a two phase system comprising a water immiscible phase containing the cyanohydrin and an aqueous phase; (C) removing at least 50 weight percent, based on the weight of the water immiscible phase, of the water immiscible solvent from the water immiscible phase thereby concentrating the cyanohydrin; (D) adding a water miscible amide solvent to the concentrated cyanohydrin to form a cyanohydrin solution; and (E) passing ammonia through the cyanohydrin solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.Type: GrantFiled: October 13, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventor: Paul R. Buckland