Six-membered Alicyclic Ring Containing Patents (Class 558/430)
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Patent number: 6359061Abstract: Amide compounds of formula (I), combinatorial libraries of amide compounds and methods of preparing the same are provided. Libraries of the invention are useful for screening in biological assays in order to identify pharmaceutically useful compounds.Type: GrantFiled: March 19, 1999Date of Patent: March 19, 2002Assignee: ISIS Pharmaceuticals, Inc.Inventors: Eric Edward Swayze, Peter William Davis
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Patent number: 6310032Abstract: Described are &agr;-oxygen-substituted cyclohexane propionitriles having the structure: wherein R20 and R21 are the same or different C1-C3 lower alkoxy; or wherein R20 is hydrogen and R21 is hydroxy, C1-C3 lower alkoxy or C1-C3 lower acyloxy; and wherein R1, R2, R3, R4, R5, R6 and R7 are the same or different hydrogen or C1-C4 lower alkyl, and uses thereof for their organoleptic properties in augmenting or enhancing or imparting aromas in or to perfume compositions, colognes, microporous polymers or perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair care compositions and the like.Type: GrantFiled: March 2, 2000Date of Patent: October 30, 2001Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Richard A. Weiss, Marie R. Hanna, Charles E. J. Beck
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Patent number: 6174922Abstract: The present invention provides novel sulphonamide derivatives which are useful for potentiating glutamate receptor function in a mammal requiring treatment, processes for their preparation, and pharmaceutical compositions containing them.Type: GrantFiled: February 23, 1999Date of Patent: January 16, 2001Assignee: Eli Lilly and CompanyInventors: Macklin Brian Arnold, Paul Leslie Ornstein, Dennis Michael Zimmerman, Ana Maria Escribano
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Patent number: 6168839Abstract: Novel liquid crystalline compounds which have a wide temperature range of liquid crystal phase, are excellent in miscibility with other liquid crystalline compounds, have a low viscosity, are low in toxicity, and are safe; liquid crystal compositions comprising the liquid crystalline compound; and liquid crystal display devices fabricated by using the composition are provided; and the compounds are cyclohexane derivatives expressed by the general formula (1) wherein R represents an alkylene chain having 2 to 10 carbon atoms in which alkylene chain ethylene group (—CH2CH2—) may be replaced by ethenylene group (—CH═CH—) or methylenoxy group (—OCH2—); and M represents COOH or CN group.Type: GrantFiled: June 21, 1999Date of Patent: January 2, 2001Assignee: Chisso CorporationInventors: Atsuko Fujita, Shuichi Matsui, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 6046353Abstract: A method of making (.+-.)-3-(aminomethyl)-5-methylhexanoic acid that comprises condensing isovaleraldehyde with ##STR1## to form primarily ##STR2## reacting the ##STR3## with a cyanide source to form ##STR4## decarboxylating the ##STR5## to form ##STR6## hydrolyzing the ##STR7## with an alkali or alkaline earth metal hydroxide to form an alkali or alkaline earth metal carboxylate salt; and hydrogenating the alkali or alkaline earth metal carboxylate salt to form (.+-.)-3-(aminomethyl)-5-methylhexanoic acid, wherein R.sub.1 and R.sub.2 are the same or different and are hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, benzyl, or C.sub.3 -C.sub.6 cycloalkyl. The present invention also provides a method of making (.+-.Type: GrantFiled: August 26, 1998Date of Patent: April 4, 2000Assignee: Warner-Lambert CompanyInventors: Todd Michel Grote, Brian Keith Huckabee, Thomas Mulhern, Denis Martin Sobieray, Robert Daniel Titus
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Patent number: 5856518Abstract: This invention is to provide a compound represented by the following formula (I) and a compound represented by the following formula (II) useful as an antibacterial agent which is obtained by the compound of folmula (I), and also to provide a novel synthetic process for the inexpensive, short-step and industrially advantageous production thereof.Type: GrantFiled: November 26, 1997Date of Patent: January 5, 1999Assignee: Daiichi Pharmaceutical Co., Ltd.Inventors: Toshifumi Akiba, Tutomu Ebata, Tatsuru Saito, Sadahiro Shimizu, Keiichi Hirai, Naoki Ohta, Toshiaki Tojo
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Patent number: 5834619Abstract: Polymeric compositions having inherent electroconductive properties and unsaturated electron-donor and electron-receptor polymerizable monomers for producing such compositions in the form of blends of homopolymers of such monomers or as copolymers of such monomers.Type: GrantFiled: July 11, 1996Date of Patent: November 10, 1998Assignee: Northrop Grumman CorporationInventor: Nicholas T. Castellucci
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Patent number: 5814612Abstract: The present invention provides a purified retinoid compound characterized by a molecular mass of about 320 daltons and an atomic composition of C.sub.20 H.sub.32 O.sub.3. The present invention also provides a purified retinoid compound having the structure: ##STR1## wherein the configuration of the C7, C9, and C11 double bond independently is Z or E and the absolute configuration at C13 and C14 is independently R or S; wherein R1 is alkyl, alkyl halide, alcohol, ester, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, acyl halide, amide, nitrile, or amine; R2 and R3 are independently hydroxyl, halide, alkoxy, ester, alkyl, alcohol, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, nitrile, amine, azide, alkyl halide, acid halide, acid azide, or amide; or wherein R2 and R3, or R1 and R2 are replaced by a 13,14-oxirane or a 14,15-oxirane group, respectively.Type: GrantFiled: May 6, 1992Date of Patent: September 29, 1998Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia in the City of New YorkInventors: Jochen Buck, Ulrich Hammerling, Fadila Derguini, Koji Nakanishi
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Patent number: 5811455Type: GrantFiled: May 24, 1995Date of Patent: September 22, 1998Assignee: SmithKline Beecham CorporationInventors: Siegfried Benjamin Christensen, IV, Paul Elliot Bender, Cornelia Jutta Forster
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Patent number: 5763483Abstract: Novel carbocyclic compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and assay methods for detecting neuraminidase activity are also described.Type: GrantFiled: December 27, 1996Date of Patent: June 9, 1998Assignee: Gilead Sciences, Inc.Inventors: Norbert W. Bischofberger, Choung U. Kim, Willard Lew, Hongtao Liu, Matthew A. Williams
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Patent number: 5750765Abstract: Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-substituted quinone methide compound.Type: GrantFiled: August 27, 1996Date of Patent: May 12, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Peter Nesvadba, Samuel Evans, Matthew E. Gande, Volker H. von Ahn, Roland A. E. Winter
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Patent number: 5650511Abstract: Derivatives of 9-deazaguanine are prepared by reacting an aldehyde or ketone with a dialkylaminomalonate to form the corresponding enamine. The enamine is then reacted with a base to form a cyclic pyrrole. The cyclic pyrrole is reacted with an urea compound to provide a protected guanidino compound. The guanidino is converted to the desired 9-deazaguanine derivative by reacting with trifluoracetic acid or with an alkoxide or hydroxide followed by neutralization with an acid.Type: GrantFiled: December 12, 1995Date of Patent: July 22, 1997Assignee: BioCryst Pharmaceuticals, Inc.Inventors: Arthur J. Elliott, David A. Walsh
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Patent number: 5631286Abstract: Novel cyclohexanes of formulas (I) and (II) are described herein. They inhibit the production of Tumor Necrosis Factor and are useful in the treatment of disease states mediated or exacerbated by TNF production: these compounds are also useful in the mediation or inhibition of enzymatic or catalytic activity of phosphodiesterase IV.Type: GrantFiled: May 24, 1995Date of Patent: May 20, 1997Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Paul E. Bender, Cornelia J. Forster
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Patent number: 5620831Abstract: Disclosed are novel cyanoguanidine derivatives which are usable as an epoxy resin curing agent and are represented by the following general formula (1). A thermosetting resin composition and a photocurable and thermosetting resin composition containing the following cyanoguanidine derivatives and other derivatives as the epoxy resin curing agent are also disclosed. ##STR1## wherein R.sup.1 represents a substituent selected from the group consisting of the following substituents (a) through (k).Type: GrantFiled: March 28, 1995Date of Patent: April 15, 1997Assignee: Taiyo Ink Manufacturing Co., Ltd.Inventor: Osamu Kawana
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Patent number: 5583247Abstract: Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-substituted quinone methide compound.Type: GrantFiled: April 14, 1995Date of Patent: December 10, 1996Assignee: Ciba-Geigy CorporationInventors: Peter Nesvadba, Samuel Evans, Matthew E. Gande, Volker H. von Ahn, Roland A. E. Winter
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Patent number: 5508444Abstract: Novel substituted cis-1,2-dihydroxy-cyclohexadiene compounds, useful as intermediates in the production of compounds for use as intermediates in the production of agrochemicals and pharmaceuticals, and a microbial process for the preparation thereof.Type: GrantFiled: November 17, 1994Date of Patent: April 16, 1996Assignee: Zeneca LimitedInventors: Andrew J. Blacker, Martin Brown, Martin C. Bowden
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Patent number: 5476960Abstract: An .alpha.-aminonitrile compound derived from the reaction, in the presence of a cyanide source of (1) a bisulfite adduct of a carbonyl compound selected from the group consisting of an aldehyde and a ketone with (2) a fatty alkyl alkylene diamine containing two reactible amino functionalities which is of the formula RNHR.sub.1 NH.sub.2, where R is fatty alkyl and R.sub.1 is lower alkylene of up to six carbon atoms.Type: GrantFiled: April 7, 1994Date of Patent: December 19, 1995Assignee: Akzo Nobel N.V.Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
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Patent number: 5468870Abstract: Dye-donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer containing a dye corresponding to the following formula ##STR1## wherein Z represents CN, COOR.sup.1 or CONR.sup.2 R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 each independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or R.sup.2 and R.sup.3 together represent the necessary atoms to close a heterocyclic nucleus or substituted heterocyclic nucleus;Y represents OR.sup.4 or NR.sup.5 R.sup.6 or CN;R.sup.4 represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, SO.sub.2 R.sup.7, COR.sup.7, CSR.sup.7, POR.sup.7 R.sup.8 ;R.sup.5 and R.sup.6 each independently has one of the significances given to R.sup.4 or represent substituted or unsubstituted amino, or R.sup.5 and R.sup.Type: GrantFiled: October 20, 1994Date of Patent: November 21, 1995Assignee: AGFA-GAVAERT, N.V.Inventor: Luc J. Vanmaele
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Patent number: 5449686Abstract: Novel cyclohexanes of Formulas (I) and (II) ##STR1## are described herein. They inhibit the production of Tumor Necrosis Factor and are useful in the treatment of disease states mediated or exacerbated by TNF production; these compounds are also useful in the mediation or inhibition of enzymatic or catalytic activity of phosphodiesterase V.Type: GrantFiled: September 29, 1994Date of Patent: September 12, 1995Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Paul E. Bender, Cornelia J. Forster
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Patent number: 5371292Abstract: A process for the preparation of 3-aminomethyl-3,5,5-trimethyl-cyclohexylamine from 3-cyano-3,5,5-trimethyl-cyclohexanone, wherein the following stages are carried out in discrete reaction chambers:a) the 3-cyano-3,5,5-trimethyl-cyclohexanone is reacted in a first reaction chamber with excess ammonia over an acidic metal oxide catalyst at a temperature of from 20.degree. to 150.degree. C. and a pressure of from 15 to 500 bar, andb) in a second reaction chamber, the reaction product from stage a) is hydrogenated with hydrogen at a temperature of from 60.degree. to 150.degree. C. and a pressure of from 50 to 300 bar in the presence of excess ammonia over a catalyst containing cobalt, nickel, ruthenium, and/or some other noble metal, which catalyst optionally contains a basic component or is supported by neutral or basic supporting material.Type: GrantFiled: July 15, 1993Date of Patent: December 6, 1994Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Wolfgang Harder
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Patent number: 5354901Abstract: Perfluoro(cycloaliphatic methyleneoxyalkylene) compositions are provided. These compositions comprise perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds having (a) a perfluorocycloaliphatic moiety which can have up to two perfluoroalkyl substituents and a perfluoroalkylene substituent, and (b) a perfluoromethyleneoxyalkylene carbonyl fluoride radical, the methylene group of the radical being bonded to a ring carbon atom or the perfluoroalkylene substituent of the moiety and the alkylene group of the perfluoromethyleneoxyalkylene carbonyl fluoride being a perfluoro(methyl)methylene group, a perfluoroisopropyleneoxy(methyl)methylene group, or a poly(perfluoroisopropyleneoxy)perfluoro(methyl)methylene group having up to about 10 perfluoroisopropyleneoxy units.Type: GrantFiled: February 1, 1993Date of Patent: October 11, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard M. Flynn, Patricia M. Savu
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Patent number: 5354777Abstract: New cyanoalkene derivatives of the formula (I) ##STR1## are described, in which R and R.sup.1 have the meaning given in the description, and a process for their preparation.The new cyanoalkene derivatives are used for combating microorganisms for the protection of industrial materials.Type: GrantFiled: February 23, 1993Date of Patent: October 11, 1994Assignee: Bayer AktiengesellschaftInventors: Peter Wachtler, Wilfried Paulus, Georg-Wilhelm Ludwig
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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: 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: 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
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Patent number: 5329023Abstract: The invention relates to a method of preparing optically active alcohols which consist substantially (at least 75% e.e.) or entirely of one enantiomer of formula 4 ##STR1## wherein R and A are as defined therein. The method comprises, which maintaining enantiomeric excess, converting an optically active cyanohydrin of formula 1 ##STR2## into optically active protected cyanohydrin of formula 2 ##STR3## converting the protected cyanohydrin of formula 2 into an optically active compound of formula 3 ##STR4## removing the protecting group B.Type: GrantFiled: June 15, 1992Date of Patent: July 12, 1994Assignee: Duphar International Research B.V.Inventors: Johannes Brussee, Arne Van Der Gen
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Patent number: 5319126Abstract: .alpha.-aminonitrile compounds derived from a fatty alkyl alkylene diamine containing two reactible amino functionalities are disclosed.Type: GrantFiled: January 29, 1993Date of Patent: June 7, 1994Assignee: Akzo n.v.Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
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Patent number: 5292902Abstract: The invention concerns a process for the manufacture of a mixture of (3a.alpha.,5a.beta.,9a.alpha.,9b.beta.)-dodecahydro-3a,6,6,9a-tetramethyln aphtho-[2,1-b]furan and (3a.alpha.,5a.beta.,9a.alpha.,9b.alpha.)-dodecahydro-3a,6,6,9a-tetramethyl naphtho[2,1-b]furan which utilizes the substituted hexenoic acids, 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-2- or -3-enoic acid. The invention also concerns nitriles and a process for manufacture of the hexonic acids from the nitriles, having the formula ##STR1## wherein one of the bonds denotes a single bond and the other denotes a double bond, and, R represents hydrogen or the ester group COOR.sup.1 in which R.sup.1 represents a lower alkyl or aryl group.Type: GrantFiled: July 24, 1992Date of Patent: March 8, 1994Assignee: Givaudan-Roure CorporationInventor: Daniel Helmlinger
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Patent number: 5241087Abstract: A method of enantiomerically enriching chiral cyanohydrins is disclosed that involves selective cleavage of the unwanted enantiomer into its cleavage products HCN and the corresponding aldehyde or ketone by use of an enantioselective dehydrocyanation catalyst, coupled with simultaneous removal of at least one of the dehydrocyanation products.Type: GrantFiled: March 9, 1992Date of Patent: August 31, 1993Assignee: Bend Research, Inc.Inventor: Paul van Eikeren
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Patent number: 5196423Abstract: Unsaturated cyclohexylacetic acid derivatives of the formula I ##STR1## where U is.dbd.NOCH.sub.3, .dbd.CHOCH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3, .dbd.CH--CH.sub.2 --CH.sub.3, .dbd.N--NH--CH.sub.3 or .dbd.CH--S--CH.sub.3,n is from 0 to 10,A is hydrogen or substituted or unsubstituted alkyl, cycloalkyl, aryl or hetaryl, andX is a single bond when n is 0, and oxygen, sulfur or a single bond when n is not 0, and the plant-compatible acid addition products and base addition products thereof, and fungicides and insecticides containing these compounds.Type: GrantFiled: June 15, 1992Date of Patent: March 23, 1993Assignee: BASF AktiengesellschaftInventors: Bernd Mueller, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5185460Abstract: Aminoacetonitrile derivatives, where the 2-position of aminoacetonitrile is optionally substituted by alkylthio groups, arylthio groups and heterocyclicthio groups. The process for making such compounds comprises reacting hydrogen cyanide with the desired corresponding R-S-H and recovering the crystallized salt thereof. The aminoacetonitrile derivatives are useful as starting materials to produce pharmaceutical and agricultural intermediates such as benzomide derivatives with fungicidal and herbicidal activities.Type: GrantFiled: April 22, 1992Date of Patent: February 9, 1993Assignee: Nippon Soda Co., Ltd.Inventors: Seiji Tazaki, Nobuhiro Umeda, Nobuo Matsui, Tomio Yagihara, Katsunori Mikuma
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Patent number: 5175170Abstract: Non-peptidyl compounds characterized generally as cycloalkyl/cycloalkylkyl-N-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest of the formula ##STR1## wherein R.sub.1 is selected from cycloalkyl and cycloakylalkyl groups, wherein said cycloalkyl group contains three to about eight carbon atoms and the acyclic alkyl portion of said cycloakylalkyl group contains one to about eight carbon atoms; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; and wherein R.sub.7 is isobutyl or ethyl; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: July 29, 1991Date of Patent: December 29, 1992Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
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Patent number: 5169973Abstract: Alpha-aminonitriles can be synthesized by the reaction, at ambient temperature without use of catalyst, of essentially stoichiometric amounts of amine, aldehyde (either monoaldehyde or dialdehyde) and trimethylsilyl cyanide.Type: GrantFiled: April 15, 1991Date of Patent: December 8, 1992Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Harry W. Gibson, Jean-Pierre LeBlanc
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Patent number: 5166373Abstract: The present invention provides novel acyclic terpenes of the formula: ##STR1## which are useful as intermediates for the industrially advantageous production of sarcophytol A.Type: GrantFiled: December 30, 1991Date of Patent: November 24, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Cyclohexenone derivatives, their preparation and their use as herbicides and plant growth regulators
Patent number: 5154753Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, Y and Z have the meanings given in the disclosure, processes for their manufacture, herbicidal and growth-regulating agents containing the novel active ingredients, and processes for combating unwanted plant growth and for regulating plant growth.Type: GrantFiled: August 14, 1991Date of Patent: October 13, 1992Assignee: BASF AktiengesellschaftInventors: Norbert Meyer, Johann Jung, Wilhelm Rademacher, Dieter Kolassa, Rainer Becker, Dieter Jahn, Michael Keil, Ulrich Schirmer, Bruno Wuerzer -
Patent number: 5126349Abstract: Substituted 3-thio-2-propynenitriles are prepared which correspond to the formula:R--S--C.tbd.C--C.tbd.Nwherein R is an alkyl, cyclic alkyl, aryl, or heterocyclo group.These compounds have been found to exhibit a high degree of antimicrobial activity in industrial and commercial applications and compositions containing these compounds are so employed.Type: GrantFiled: December 26, 1990Date of Patent: June 30, 1992Assignee: The Dow Chemical CompanyInventors: Connie I. Deford, Charles D. Gartner, Kalakota S. Reddy, John K. Swayze, David E. Wallick, Warren L. Treptow, George A. Paul, Billy R. Hardas
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Patent number: 5126374Abstract: Guanidines I ##STR1## (A=C.sub.5 -C.sub.12 -cycloalkyl which may bear up to three further substituents; benzyl substituted in the para-position; R.sup.1, R.sup.2, R.sup.3 =H, C.sub.1 -C.sub.4 -alkyl; R.sup.4 -C.sub.5 -C.sub.18 -alkyl which may be interrupted by oxygen, C.sub.5 -C.sub.18 -alkenyl, C.sub.4 -C.sub.18 -alkynyl or phenyl-C.sub.1 -C.sub.6 -alkyl, and these groups may bear up to three further substituents and the phenyl moiety of the phenylalkyl may additionally bear a phenoxy group or up to three C.sub.2 -C.sub.4 -alkenyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.6 -alkyl or haloalkyl groups, C.sub.5 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.8 -alkyl, where the ring may bear up to three further substituents; A=benzyl and R.sup.4 =C.sub.3 -C.sub.4 -alkyl which may be interrupted by oxygen, or C.sub.4 -alkenyl, both of which may bear up to three further substituents; R.sup.3 +R.sup.4 =C.sub.5 -C.sub.Type: GrantFiled: July 3, 1990Date of Patent: June 30, 1992Assignee: BASF AktiengesellschaftInventors: Matthias Zipplies, Hubert Sauter, Franz Roehl, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5106984Abstract: 2-Hydrocarbyl-3,6-dichloropyridines are prepared from dichloromethyl hydrocarbyl ketones and acrylonitrile in a two-step process involving an addition reaction under basic conditions to form intermediate 1,1-dichloro-3-cyanopropyl hydrocarbyl ketones and a subsequent cyclization reaction in the presence of hydrogen chloride. Thus, 3,6-dichloro-2-methylpyridine is prepared from 1,1-dichloro-2-propanone and acrylonitrile by the formation and further reaction of 4,4-dichloro-5-oxo-hexanenitrile. The intermediates and products are novel compounds useful in the preparation of herbicides and nitrification inhibitors.Type: GrantFiled: February 24, 1987Date of Patent: April 21, 1992Assignee: The Dow Chemical CompanyInventors: Marc E. Halpern, Jon A. Orvik, Thomas J. Dietsche
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Patent number: 5077426Abstract: A process for preparing .alpha.-formylamino nitriles of the formula Ia ##STR1## and Ib ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and each is hydrogen or unsubstituted or substituted, with substituents which are inert under the reaction conditions, aliphatic or heteroaliphatic radicals with 1 to 10, cycloaliphatic or heterocycloaliphatic radicals with 3 to 6, araliphatic radicals with 7 to 12, heteroaraliphatic radicals with 4 to 12, aromatic radicals with 6 to 10 or heteroarometic radicals with 3 to 10 carbon atoms, with the priviso that at least one of R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 is hydrogen, comprises reacting an iminodiacetonitrile of the formula II ##STR3## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meanings, with formamide of the formula III ##STR4## in the presence of formic acid or with a compound which provides formic acid, in the presence of acids.Type: GrantFiled: December 13, 1990Date of Patent: December 31, 1991Assignee: BASF AktiengesellschaftInventors: Rolf Fikentscher, Michael Kroener
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Patent number: 5077427Abstract: A process for preparing .alpha.-formylamino nitriles of the formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or unsubstituted or substituted, with substituents which are inert under the reaction conditions, aliphatic or heteroaliphatic radicals with 1 to 10, cycloaliphatic or heterocycloaliphatic radicals with 3 to 6, araliphatic radicals with 7 to 12, heteroaraliphatic radicals with 4 to 12, aromatic radicals with 6 to 10 or heteroaromatic radicals with 3 to 10 carbon atoms, by reacting cyanohydrins of the formula II ##STR2## with the formamide III ##STR3## in the presence of acids, entails adding at least one ammonium salt to the reaction mixture.Type: GrantFiled: December 13, 1990Date of Patent: December 31, 1991Assignee: BASF AktiengesellschaftInventors: Rolf Fikentscher, Michael Kroener
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Patent number: 5075031Abstract: A mesomorphic compound represented by the formula: ##STR1## wherein R.sub.1 denotes an alkyl group having 1-16 carbon atoms; R.sub.2 denotes an alkyl group having 2-10 carbon atoms; X denotes a single bond or --O--; Y denotes --OCH.sub.2 --, ##STR2## Z denotes a single bond, ##STR3## respectively and independently denote ##STR4## k, l and n are respectively 0, 1 or 2 satisfying the relation of k+l+n=2 or 3; C* denotes an asymmetric carbon atom. The mesomorphic compound, when added as a component, provides a liquid crystal composition showing an improved field respective characteristic or is effective in preventing occurrence of a reverse domain.Type: GrantFiled: December 20, 1989Date of Patent: December 24, 1991Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Takashi Kimura, Yoko Yamada, Kazushige Yamagishi
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Patent number: 5070202Abstract: A process for the production of alkylaminonitriles by reacting 2-pentenenitrile and an alkylamine in the presence of 15 to 60% by weight water.Type: GrantFiled: March 28, 1990Date of Patent: December 3, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank E. Herkes
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Patent number: 5011970Abstract: Nitriles of the formula: ##STR1## wherein R is hydrogen or an alkyl radical of 1 to 6 carbon atoms and the dashed lines represent carbon-carbon single or double bonds.These compounds are useful in a variety of perfumery applications.Type: GrantFiled: November 28, 1986Date of Patent: April 30, 1991Assignee: PFW(Nederland)B.V.Inventor: Willem Lenselink
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Patent number: 5008429Abstract: An improvement in a process for the industrial application of the Knoevenagel synthesis in an acid solution, resulting in a steady flow of waste gas.Type: GrantFiled: December 6, 1989Date of Patent: April 16, 1991Assignee: Huels AktiengesellschaftInventors: Manfred Kaufhold, Josef Metz
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Patent number: 4985582Abstract: Bicyclo-[2,2,1]-heptanes, bicyclo-[2,2,2]-octanes and bicyclo-[2,2,3]-nonanes, having 2 or 3 ring hetero atoms selected from O, S and N substituted at the 1-position by a carbocyclic group other than an alkynylphenyl group, and substituted at the 4-position and optionally substituted at the 3 and/or 5 position, are valuable pesticides, particularly insecticides and acaricides. Various cyclization processes are disclosed to form the various bicyclo ring systems.Type: GrantFiled: September 1, 1989Date of Patent: January 15, 1991Assignee: The Wellcome Foundation Ltd.Inventor: John P. Larkin
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Patent number: 4968820Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4 = in any two cases (a) hydroxy and MC--CO--O or, independently of each other, MC--CO--O and (b), independently of each other (C.sub.1 -C.sub.10)alkoxy, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group, and it being possible for Y.sup.2 and Y.sup.3, in the case of (C.sub.1 -C.sub.10)alkoxy, also to be jointly part of a dioxolane ring, or Y.sup.1 and Y.sup.4 jointly = 0 as part of a tetrahydrofuran ring, and Y.sup.2 and Y.sup.3 = hydroxy and MC--CO--O or, independently of each other, MC--CO--O. Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.Type: GrantFiled: July 11, 1988Date of Patent: November 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunter Scherowsky, Manel Gunaratne
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Patent number: 4966726Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1 =H, (C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group,Y.sup.2 =(C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, it being possible for Y.sup.1 and Y.sup.2 to jointly represent a MC--CH group, which is then part of a dioxolane ring,X=COOR.sup.1, CONH.sub.2, CONR.sup.2 R.sup.3 or C.tbd.N,R.sup.1 =(C.sub.1 -C.sub.10)alkyl or MC--CH.sub.2, andR.sup.2, R.sup.3 =H and (C.sub.1 -C.sub.4)alkyl or, independently of each other, (C.sub.1 -C.sub.4)alkyl.Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.Type: GrantFiled: July 18, 1988Date of Patent: October 30, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunter Scherowsky, Manel Gunaratne
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Patent number: 4950774Abstract: A 2,5-disubstituted-7,7,8,8-tetracyanoquinodimethane of the general formula ##STR1## wherein R.sup.1 is hydrogen or methyl, X is COOR.sup.2 (in which R.sup.2 is hydrogen or C.sub.1-10 alkyl), --CONR.sup.3 R.sup.4 (in which R.sup.3 and R.sup.4 each is hydrogen or C.sub.1-4 alkyl) or --CN, provided that when R.sup.1 is hydrogen, X is --CN or --CONR.sup.3 R.sup.4. The tetracyanoquinodimethane derivatives are starting materials for the production of polyamides, polyurethanes or organic semiconductor devices.Type: GrantFiled: October 23, 1987Date of Patent: August 21, 1990Assignee: Nippon Gohsei Kagaku Kogyo KabushikiInventor: Takeo Kawabata
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Patent number: 4943384Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-groups, and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --Z.sup.o --A-- or --A--Z.sup.o --A.sup.4 --,A is a trans-1,4-cyclohexylene or 1,4-cyclohexenylene group which is unsubstituted or is monosubstituted or polysubstituted in the 2-, 3-, 5- and/or 6-position by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group each of which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, which trans-1,4-cyclohexylene or 1,4-cyclohexenylene group can optionally also be substituted in the 1-position and/or 4-position and one or two CH.sub.Type: GrantFiled: November 21, 1986Date of Patent: July 24, 1990Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
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Patent number: RE35230Abstract: A method of enantiomerically enriching chiral cyanohydrins is disclosed that involves selective cleavage of the unwanted enantiomer into its cleavage products HCN and the corresponding aldehyde or ketone by use of an enantioselective dehydrocyanation catalyst, coupled with simultaneous removal of at least one of the dehydrocyanation products.Type: GrantFiled: February 7, 1994Date of Patent: May 7, 1996Assignee: Bend Research, Inc.Inventor: Paul van Eikeren