Cyclohexyl Ring Containing Patents (Class 564/462)
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Patent number: 5693864Abstract: Disclosed herein is a process for preparing an amine terminated polyether comprising reacting a polyether containing a leaving group with a primary amine or ammonia at a temperature of about 70 to 250 degrees Centigrade.Type: GrantFiled: October 7, 1992Date of Patent: December 2, 1997Assignee: Bayer CorporationInventors: William E. Slack, Rick L. Adkins, Hans Georg Schmelzer
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Patent number: 5665877Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.Type: GrantFiled: May 17, 1996Date of Patent: September 9, 1997Assignee: Eli Lilly and CompanyInventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski, II
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Patent number: 5627215Abstract: The invention relates to compounds of formula (I), R.sub.1 and R.sub.2, each independently of the other, are selected from lower alkyl that is unsubstituted or substituted by one or more fluorine atoms which are not linked to the carbon atom of R.sub.1 or R.sub.2 bonding the nitrogen; from lower alkenyl wherein the double bond does not originate from the carbon atom that is bonded to a nitrogen bonding R.sub.1 or R.sub.2 ; from lower alkynyl wherein the triple bond does not originate from the carbon atom that is bonded to a nitrogen bonding R.sub.1 or R.sub.2 ; from cycloalkyl; and from cycloalkyl-lower alkyl; with the proviso that not more than one of the two radicals R.sub.1 and R.sub.2 is methyl; or salts thereof. The mentioned compounds are pharmacologically active against disorders that are responsive to a recuction in intracellular polyamines, such as tumours or protozoal diseases.Type: GrantFiled: August 18, 1995Date of Patent: May 6, 1997Assignee: Ciba-Geigy CorporationInventors: Jorg Frei, Jaroslav Stanek
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Patent number: 5622916Abstract: A method of combating pests which comprises applying to such pests or to a pest habitat a pesticidally effective amount of a substituted 2-cyclohexen-1-yl-amine derivative of the formula ##STR1## and addition products thereof with acids and metal salts. Most of the compounds are new.Type: GrantFiled: September 15, 1993Date of Patent: April 22, 1997Assignee: Bayer AktiengesellschaftInventors: Franz Kunisch, Peter Babczinski, Dieter Arlt, Hans-Joachim Santel, Robert R. Schmidt, Wilhelm Brandes, Harry Strang
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Patent number: 5597940Abstract: Disclosed is a process for producing .beta.-nitroenamine represented by the formula I: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and independently indicate a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group which may be optionally substituted with at least one group selected from the group consisting of a halogen atom, a lower alkoxy group, an aryloxy group, a hydroxyl group or an aryl group, or an aryl group which may be optionally substituted with a halogen atom, a lower alkyl group, a lower alkoxy group, an aryl group, an aryloxy group, a nitro group, a cyano group, an acylamino group, a di-lower alkylamino group, an arylamino group, a hydroxyl group, an arylsulfonyl group, a mercapto group, a lower alkylthio group or an arylthio group, R.sub.1 and R.sub.2 may bond together to form a cycloalkyl or bicycloalkyl and R.sub.3 is a hydrogen atom, a lower alkyl group, a cycloalkyl group or an aralkyl group; and an intermediate for producing the .beta.-nitroenamine.Type: GrantFiled: March 9, 1995Date of Patent: January 28, 1997Assignee: Sumitomo Chemical Company, LimitedInventor: Shinzo Seko
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Patent number: 5571796Abstract: The present invention is directed to methods of reducing the degree of inflammation arising from a secondary immune response in a mammal due to antigen exposure (challenge) by the administration of valienamine-related disaccharide compounds and the pharmaceutical compositions employed in the method.Type: GrantFiled: June 6, 1995Date of Patent: November 5, 1996Assignee: Alberta Research CouncilInventors: Om P. Srivastava, Roman Szweda, Richard H. Smith, Robert M. Ippolito, Ulrike Spohr
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Patent number: 5554656Abstract: The invention relates to a disinfectant concentrate which contains amine and alcohol wherein the alcohol component includes at least one glycol ether of limited miscibility with water and the amine component includes at least one secondary and/or tertiary alkyl amine free from hydroxyl groups. It also relates to a disinfectant producabile from the disinfectant concentrate, the use of the disinfectant concentrate and of the disinfectant as bactericide, in particular mycobactericide, fungicide or virucide.Type: GrantFiled: February 25, 1994Date of Patent: September 10, 1996Assignee: Reckitt & Colman Inc.Inventors: Bernd L ower, Heinz Eggensperger, Peter Goroncy-Bermes, Michael Mohr, Andreas Dettmann
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Patent number: 5541347Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.Type: GrantFiled: October 3, 1994Date of Patent: July 30, 1996Assignee: Eli Lilly and CompanyInventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski II
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Patent number: 5508411Abstract: The present invention relates to a novel enantiospecific process for preparing (S)-1-[2(S)-(1,3-dihydro-1,3-dioxo-isoindo-2-yl)-1-oxo-3-phenylpropyl ]-1,2,3,4-tetrahydro-2-pyridine-carboxylic acid methyl ester which is a useful intermediate in the preparation of [4S-[4.alpha., 7.alpha.(R*), 12b.beta.]]-7-[(1-oxo-2(S)-thio-3-phenylpropyl) amino]-1,2,3,4,6,7,8,12b-octahydro-6-oxo-pyrido[2,1-a][2]benzazepine-4-car boxylic acid and [4S-[4.alpha., 7.alpha.(R*), 12b.beta.]]-7-[(1-oxo-2(S)-acetylthio-3-phenylpropyl)amino]-1,2,3,4,6,7,8, 12b-octahydro-6-oxo-pyrido[2,1-a][2]benzazepine-4-carboxylic acid and pharmaceutically acceptable salts thereof which is useful as an inhibitor of enkephali nase and angiotensin converting enzyme and to novel intermediates thereof.Type: GrantFiled: March 30, 1996Date of Patent: April 16, 1996Assignee: Merrell Pharmaceuticals Inc.Inventor: Gary A. Flynn
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Patent number: 5502253Abstract: The present invention relates to a novel enantiospecific process for preparing (S)-1- 2(S)-(1,3-dihydro-1,3-dioxo-isoindo-2-yl)-1-oxo-3-phenylpropyl!-1,2 ,3,4-tetrahydro-2-pyridine-carboxylic acid methyl ester which is a useful intermediate in the preparation of 4S- 4.alpha., 7.alpha.(R*), 12b.beta.!!-7- (1-oxo-2(S)-thio-3-phenylpropyl)amino!-1,2,3,4,6,7,8,12b-oc tahydro-6-oxo-pyrido 2,1-a! 2!benzazepine-4-carboxylic acid and 4S- 4.alpha., 7.alpha.(R*), 12b.beta.!!-7- (1-oxo-2(S)-acetylthio-3-phenylpropyl)amino!-1,2,3,4,6,7,8, 12b-octahydro-6-oxo-pyrido 2,1-a! 2!benzazepine-4-carboxylic acid and pharmaceutically acceptable salts thereof which is useful as an inhibitor of enkephalinase and angiotensin converting enzyme and to novel intermediates thereof.Type: GrantFiled: March 30, 1995Date of Patent: March 26, 1996Assignee: Merrell Pharmaceuticals Inc.Inventor: Gary A. Flynn
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Patent number: 5491261Abstract: Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.Type: GrantFiled: July 1, 1994Date of Patent: February 13, 1996Assignee: Ciba-Geigy CorporationInventors: Marlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
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Patent number: 5481037Abstract: A process for the purification of tertiary amines in a crude mixture contaminated with undesirable primary and secondary amines which may have only a slight variance in boiling point with respect to the tertiary amine, wherein the crude mixture of the tertiary amine is treated at temperatures which may range from 0.degree. to 200.degree. C. but preferably from 20 to 150.degree. C. and at pressures of from 1 to 200 bar but most preferably under atmospheric pressure with a carboxylate of the formula ##STR1## in which R.sup.4 and R.sup.5 are selected from the group consisting of C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, and aryl or C.sub.7 -C.sub.20 -aralkyl, both optionally mono- to penta- substituted by C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, or C.sub.4 -C.sub.12 -cycloalkylalkyl, and R.sup.Type: GrantFiled: August 31, 1994Date of Patent: January 2, 1996Assignee: BASF AktiengesellschaftInventors: Eberhard Fuchs, Tom Witzel, Klaus P. Stadler
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Patent number: 5399763Abstract: A process for preparing an optically active 2-aminopropanal through oxidative cleavage of the corresponding optically active 3-amino-1,2-butanediol of the following formula (2): ##STR1## wherein R1 is a hydrocarbon group having 3 to 6 carbon atoms; R2 and R3 are each a hydrogen atom, or separately or together represent an N-protecting group; and the configuration at the *1 position is S or R. An optically active 2-aminopropanal of high purity can be obtained in a high yield by the process.Type: GrantFiled: January 14, 1994Date of Patent: March 21, 1995Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hisao Satoh, Taichi Koshigoe
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Patent number: 5399673Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.Type: GrantFiled: February 9, 1993Date of Patent: March 21, 1995Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 5393721Abstract: The present invention is directed toward artionic polymerization employing lithio amines mixed with an organic alkali metal compound and optionally, a chelating reagent. The lithio amines have the general formula (A)Li(SOL)y, where SOL is a solubilizing component, A is an alkyl, dialkyl, cycloalkyl or dicycloalkyl amine radical or a cyclic amine, and y is 0 or is from about 0.5 to about 3. The invention is also directed toward polymers and other products made using the initiator, and methods therefor. Further, the invention contemplates a polymer, a polymer composition and products therefrom, which include a functional group from the reaction product of an amine and an organolithium compound. The resulting polymers may be terminated with a terminating, coupling or linking agent, which may provide the polymer with a multifunctionality.Type: GrantFiled: October 16, 1992Date of Patent: February 28, 1995Assignee: Bridgestone CorporationInventors: Takashi Kitamura, David F. Lawson, Koichi Morita, Yoichi Ozawa
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Patent number: 5386060Abstract: A Pd catalyst in which an .alpha.- or .gamma.-Al.sub.2 O.sub.3 as support is first treated with at least one compound of the rare earth metals and with at least one compound of manganese and then with at least one palladium compound is suitable for the preparation of a mixture of optionally substituted cyclohexylamine and optionally substituted dicyclohexylamine by hydrogenation of a correspondingly substituted aniline.Type: GrantFiled: October 23, 1992Date of Patent: January 31, 1995Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Gerhard Darsow, Helmut Waldmann, Gerd-Michael Petruck
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Patent number: 5380900Abstract: Disclosed herein is an .alpha.-methylene-cyclopentanone derivative represented by the formula [I] below which is useful as an intermediate for pharmaceuticals and insecticides, especially prostaglandins. Also disclosed herein is a process for producing the derivative advantageously on an industrial scale. ##STR1## where X denotes (.alpha.-OZ, .beta.-H) or (.alpha.-H, .beta.-OZ), with Z representing a protecting group for the hydroxyl group; U denotes (.alpha.-H, .beta.-R.sup.1) or (.beta.-R.sup.1, .alpha.-H); R.sup.1 denotes ##STR2## where R.sup.2 denotes a protected hydroxyl group, a substituted or unsubstituted C.sub.1-15 alkyl group, a substituted or unsubstituted C.sub.2-15 alkenyl group, a substituted or unsubstituted C.sub.2-15 alkynyl group, or a substituted or unsubstituted C.sub.6-15 aryl group; Z' denotes a protecting group for the hydroxyl group; and k is 0 or 1).Type: GrantFiled: February 12, 1992Date of Patent: January 10, 1995Assignee: Nissan Chemical Industries, LimitedInventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5371294Abstract: Cyclohexylamine and dicyclohexylamine can be prepared as a mixture with one another by reaction of phenol with aniline, ammonia or a mixture of aniline and ammonia in the presence of hydrogen over a catalyst, the reaction being carried out according to the invention over a palladium catalyst which has a support of niobic acid or tantalic acid or a mixture of niobic acid and tantalic acid or a support containing such acids. The reaction is carried out at 100.degree.-220.degree. C. under an H.sub.2 partial pressure of 0.5-500 bar.Type: GrantFiled: October 2, 1992Date of Patent: December 6, 1994Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Josef Buysch, Gerhard Darsow
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Patent number: 5334729Abstract: The present invention relates to new rigid chelating structures, to methods for preparing these materials, and to their use in preparing radiometal labeled immunoconjugates. These new chelates include cyclohexyl EDTA monohydride, the trans forms of cyclohexyl DTPA and TTHA, and derivatives of these cyclohexyl polyaminocarboxylate materials.Type: GrantFiled: November 4, 1991Date of Patent: August 2, 1994Assignee: Associated Universities, Inc.Inventors: Ronnie C. Mease, Suresh C. Srivastava, Jean-Francois Gestin
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Patent number: 5332810Abstract: The present invention is directed toward anionic polymerization initiators which are soluble in acyclic alkane solvents. The initiators include a solubilized lithio amine having the general formula (A)Li(SOL).sub.y. SOL is a solubilizing component and A is an alkyl, dialkyl or cycloalkyl amine radical or a cyclic amine and y is from about 1 to 4. The invention is also directed toward polymers and other products made using the initiator, and methods therefore. Further, the invention contemplates a polymer, a polymer composition and products therefrom, which include a functional group from the reaction product of an amine and an organolithium compound. The resulting polymers may be terminated with a terminating, coupling or linking agent, which may provide the polymer with a multifunctionality.Type: GrantFiled: October 2, 1992Date of Patent: July 26, 1994Assignee: Bridgestone CorporationInventors: David F. Lawson, Mark L. Stayer, Jr., H. James Harwood
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Patent number: 5326911Abstract: Ortho-amides of the formula ##STR1## can be prepared by reacting salts of the formula ##STR2## with alcoholates of the formulaM.sup.1 OR.sup.1 (III)where the radicals R.sup.1 to R.sup.4, M.sup.1 and X.sup..crclbar. have the meaning given in the description. The alcoholates are employed in highly active form with an effective content of 98-100% M.sup.1 OR.sup.1.Type: GrantFiled: July 20, 1992Date of Patent: July 5, 1994Assignee: Bayer AktiengesellschaftInventors: Heinz-Ulrich Blank, Helmut Kraus, Gerhard Marzolph, Nikolaus Muller
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Patent number: 5322965Abstract: Optionally substituted cyclohexylamine and optionally substituted dicyclohexylamine can be obtained by catalytic hydrogenation of optionally substituted aniline, a catalyst being employed which contains ruthenium, palladium or a mixture of both metals, which are applied to a support of niobic acid or tantalic acid or a mixture of both. The catalyst contains the noble metal(s) in a total amount from 0.05 to 5% by weight, relative to the total weight of the catalyst. In the case of the use of both noble metals, their weight ratio to one another is 1:9-9:1.Type: GrantFiled: August 27, 1993Date of Patent: June 21, 1994Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Gerhard Darsow, Helmut Waldmann, Gerd-Michael Petruck
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Patent number: 5306316Abstract: Poly(alkylene ether) amines having the formula: ##STR1## wherein A is an amine moiety having at least one basic nitrogen atom; R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the poly(vinyl ether) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range; R.sub.2 is an alkylene group having 2 to about 8 carbon atoms; R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each independently hydrogen or a lower alkyl group having 1 to about 4 carbon atoms; R.sub.9 is an alkyl group having 1 to about 10 carbon atoms; m is 0 or 1; n is an integer from 5 to 99; and W is a hydroxy(oxypropylene) group having the formula: ##STR2## or mixtures thereof. The poly(vinyl ether) amines of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: April 1, 1993Date of Patent: April 26, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5306315Abstract: Poly(alkylene ether) amines having the formula: ##STR1## wherein A is an amine moiety having at least one basic nitrogen atom; R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the poly(vinyl ether) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range; R.sub.2 is an alkylene group having 2 to about 8 carbon atoms; R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each independently hydrogen or a lower alkyl group having 1 to about 4 carbon atoms; R.sub.9 is an alkyl group having 1 to about 10 carbon atoms; m is 0 or 1; and n is an integer from 5 to 99. The poly(vinyl ether) amines of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: April 1, 1993Date of Patent: April 26, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5288910Abstract: 4-amino-2-buten-1-ol is formed by the regioselective addition of primary amines or ammonia to 3,4-epoxy-1-butene. A quantity of a the primary amine or ammonia is reacted with 3,4-epoxy-1-butene in a reaction medium in the presence of a catalyst. The reaction medium is a liquid which has an E.sub.T (30) no less than about 32. The catalyst is a complex of palladium and phosphine ligands.Type: GrantFiled: September 4, 1992Date of Patent: February 22, 1994Assignee: Eastman Kodak CompanyInventor: Yann Hung
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Patent number: 5284976Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group. attached to boron, B is boron and Me is methyl.Type: GrantFiled: July 19, 1993Date of Patent: February 8, 1994Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5276195Abstract: A process for preparing a dimethylorganoborane represented by the formula R*BMe.sub.2 wherein R* is a chiral organyl group attached to the boron, B is boron and Me is methyl comprising treating a chiral boronic ester R*B(OR').sub.2 with a methyl magnesium salt or trimethylaluminum wherein R* is the same chiral organyl group and R' is alkyl.Type: GrantFiled: July 14, 1993Date of Patent: January 4, 1994Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5270340Abstract: A method of combating pests which comprises applying to such pests or to a pest habitat a pesticidally effective amouht of a substituted 2-cyclohexen-1-yl-amine derivative of the formula ##STR1## and addition products thereof with acids and metal salts. Most of the compounds are new.Type: GrantFiled: September 20, 1991Date of Patent: December 14, 1993Assignee: Bayer AktiengesellschaftInventors: Franz Kunisch, Peter Babczinski, Dieter Arlt, Hans-Joachim Santel, Robert R. Schmidt, Wilhelm Brandes, Harry Strang
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Patent number: 5254708Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.Type: GrantFiled: December 14, 1990Date of Patent: October 19, 1993Assignee: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5243080Abstract: The present invention provides a novel compound represented as ##STR1## The present novel compound is prepared by reacting fluorine with pyridine-boron trifluoride and is useful as a fluorinating agent in the fluorination of organic compounds.Type: GrantFiled: July 8, 1992Date of Patent: September 7, 1993Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, David Nalewajek, George A. Shia, William J. Wagner
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Patent number: 5231208Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.Type: GrantFiled: December 14, 1990Date of Patent: July 27, 1993Assignee: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5214209Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group,attached to boron, B is boron and Me is methyl.Type: GrantFiled: March 26, 1990Date of Patent: May 25, 1993Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5214212Abstract: A process for increasing the rate of catalytic hydrogenation of aromatic amines by reacting aromatic amines with hydrogen in the presence of a noble metal catalyst, an organic solvent or a mixture of solvents, and at least one salt of a transition or lanthanide metal as a promoter, in an effective amount to increase the rate of the hydrogenation reaction, decrease the induction period, and decrease the amount of higher boiler by-products.Type: GrantFiled: February 27, 1992Date of Patent: May 25, 1993Assignee: Olin CorporationInventor: Peter J. Whitman
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Patent number: 5212173Abstract: Pharmacologically active compounds corresponding to the formula I ##STR1## in which n represents 2-5,m represents 2-6,R.sup.1 denotes hydrogen or lower alkyl,R.sup.2 represents an OR.sup.4 group in which R.sup.4 denotes lower alkyl or a phenyl or phenyl-lower alkyl group which is optionally substituted in the phenyl ring, orR.sup.2 represents a ##STR2## group in which R.sup.5 and R.sup.6 independently of one another each denote hydrogen, lower alkyl or a phenyl or phenyl-lower alkyl group which is optionally substituted in the phenyl ring, orR.sup.5 and R.sup.6, together with the nitrogen atom to which they are bonded, represent a saturated 5- or 6-membered heterocycle,R.sup.3 represents a saturated monocyclic or bicyclic hydrocarbon group which is derived from terpenes and has 10 or 11 carbon atoms, andZ represents oxygen or, if R.sup.3 is a dihydronopyl group, Z may also represent sulfur,and salts thereof.Type: GrantFiled: December 19, 1991Date of Patent: May 18, 1993Assignee: Kali-Chemie Pharma GmbHInventors: Herman Kraehling, Samuel David, Insa Hell, Ulf Preuschoff, Ivan Ban, Marie-Odile Christen
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Patent number: 5210310Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group, attached to boron, B is boron and Me is methyl.Type: GrantFiled: March 26, 1990Date of Patent: May 11, 1993Assignee: Aldrich Chemical Co., Inc.Inventor: Herbert C. Brown
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Patent number: 5166444Abstract: The invention relates to bis(3-cyano-3,5,5-trimethylcyclohexylidene)-azine (=IPN-azine), a method of its preparation by reacting 1,3,3-trimethyl-5-oxocyclohexane carbonitrile (=IPN) with a source for hydrazine in a molar ratio of essentially 2 to 1 in the presence of a solvent and to a method for the further processing of the IPN-azine to 3-(aminomethyl)-3,5,5-trimethylcyclohexyl amine (isophorone diamine=IPDA) by means of a hydrogenating azine splitting with hydrogen in the presence of an organic solvent, ammonia and of a catalytic system from the series (a) of a cobalt- or nickel-containing Raney catalyst and of a cocatalyst from the series of salts of the elements aluminum, cobalt, nickel, yttrium, lanthanum, cerium, Ru, Rh, Pd, Ir and Pt or of carrier-supported noble metals from the series Ru, Rh, Pd, Ir, Pt or b) of a carrier-supported Ru-, Pd- or Pt catalyst at a pressure of 3 to 30 MPa and a temperature of 50.degree. to 150.degree. C.Type: GrantFiled: March 9, 1992Date of Patent: November 24, 1992Assignee: Degussa AGInventors: Klaus Hutchmacher, Hermann Schmitt
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Patent number: 5152826Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: October 16, 1991Date of Patent: October 6, 1992Assignee: Imperial Chemical Industries PLCInventor: Christopher G. Knudsen
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Patent number: 5149874Abstract: A method of manufacturing 3-amino-2-cyclohexene-1-one by hydrogenating m-phenylenediamene to produce a novel intermediate salt of 3-amino-2-cyclohexene-1-imine followed by hydrolysis to produce 3-amino-2-cyclohexene-1-one. The novel intermediate 3-amino-2-cyclohexene-1-imine has also be isolated.Type: GrantFiled: April 15, 1991Date of Patent: September 22, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Stephen E. Jacobson
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Patent number: 5128471Abstract: The present invention relates to a process for the production of primary amines containing aliphatically or cycloaliphatically bound amino groups, characterized in that the isocyanate groups of organic isocyanates containing aliphatically and/or cycloaliphatically bound isocyanate groups are formylated with formic acid in a first reaction step and the N-formyl groups are subsequently converted into amino groups.The present invention also relates to polyamine mixtures obtained by this process and containinga) about 40 to 90% by weight, based on the total weight of components a) and b), of N,N',N"-tris-(6-aminohexyl)-isocyanurate andb) about 10 to 60% by weight, based on the total weight of components a) and b), of higher homologs of this triamine containing more than one isocyanurate ring.Finally, the present invention relates to the use of these polyamine mixtures as hardeners for polymer precursors containing epoxide or isocyanate groups.Type: GrantFiled: April 10, 1990Date of Patent: July 7, 1992Assignee: Bayer AktiengesellschaftInventor: Hans J. Scholl
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Patent number: 5126426Abstract: Herein disclosed are an .alpha.-(aminocyclohexyl)alkylamine represented by the following general formula (II): ##STR1## wherein R represents hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms, provided that the amino group bonded to the cyclohexyl group may be in either of the 2-, 3- and 4-positions and a method for preparing it; an .alpha.-(isocyanatocyclohexyl)alkylisocyanate of Formula (II) wherein the amino groups are replaced with isocyanato groups and a method for preparing it; polyisocyanato-isocyanurate represented by the following general formula (IV): ##STR2## wherein R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: April 19, 1990Date of Patent: June 30, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuji Haseyama, Masatoshi Takagi, Kouzou Hayashi, Katsuyoshi Sasagawa, Kazuyuki Kuroda, Taisaku Kano, Kiyoshi Shikai
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Patent number: 5117055Abstract: A perfluoroalkyl halogenide represented by the formula: ##STR1## wherein X stands for one element selected from the group consisting of iodine and bromine, R.sub.f for a perfluorohydrocarbon group, n for an integer in the range of 1 to 3, and m for an integer in the range of 1 to 3, provided that n and m satisfy the relationship, n.gtoreq.m, is produced by a method which consists essentially in subjecting a perfluorocarboxylic acid fluoride represented by the formula, ##STR2## wherein R.sub.f and n have the same meanings as defined above, to a thermal reaction with a lithium halogenide represented by XI, wherein X has the same meaning as defined above.Type: GrantFiled: February 22, 1990Date of Patent: May 26, 1992Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & IndustryInventors: Takashi Abe, Eiji Hayashi, Haruhiko Fukaya
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Patent number: 5109020Abstract: The present invention relates to new fluorinated cyclohexane derivatives of the formula ##STR1## in which the symbols used have the meaning indicated in the description, a process for their preparation, intermediates of the formula ##STR2## in which the symbols have the meaning indicated in the description, and the use of the new fluorinated cyclohexane derivatives as fungicides and intermediates.Type: GrantFiled: July 9, 1990Date of Patent: April 28, 1992Assignee: Bayer AktiengesellschaftInventors: Michael Negele, Bernd Baasner
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Patent number: 5101032Abstract: Cycloalkylidene dyes have the formula ##STR1## where m is 0 or 1,L is a chemical bond or C.sub.1 -C.sub.2 -alkylene, which may be substituted,R.sup.1 is hydrogen, C.sub.1 -C.sub.20 -alkyl, which may be phenyl-substituted, substituted or unsubstituted phenyl, naphthyl or C.sub.3 -C.sub.7 -cycloalkyl,Y is oxygen or two hydrogens,X.sup.1 is oxygen andX.sup.2 is C.sub.1 -C.sub.8 -alkanoyloxy, substituted or unsubstituted benzoyloxy, C.sub.1 -C.sub.6 -trialkylsilyloxy or a radical of the formula OR.sup.1 or NR.sup.2 R.sup.3, where R.sup.1 is as defined above and R.sup.2 and R.sup.3 are identical or different and each is independently of the other C.sub.1 -C.sub.20 -alkyl, which may be phenyl-substituted, substituted or unsubstituted phenyl, naphthyl, or C.sub.3 -C.sub.7 -cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom joining them are saturated heterocyclyl, or else one of R.sup.2 and R.sup.3 is hydrogen, or X.sup.1 and X.sup.Type: GrantFiled: October 22, 1990Date of Patent: March 31, 1992Assignee: BASF AktiengesellschaftInventors: Hans-Dieter Martin, Bernhard Albert, Knut Kessel
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Patent number: 5087756Abstract: 3-Hydroxy-2-cyclobuten-1-one salts of the general formula: ##STR1## wherein R is an ammonium group of the general formula: ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different in meaning and each is a hydrogen atom, a lower alkyl group or a cycloalkyl group or R is an alkali metal atom. The salts according for formula I are obtained by the reaction of pure 3-acetoxy-2-cyclobuten-1-one, or 1,3-cyclobutanedione or a distillation residue of the diketene production containing 3-acetoxy-2-cyclobuten-1-one, with a base. The base can be an amine of the general formula: ##STR3## wherein R.sub.1, R.sub.2 , and R.sub.3 have the above-mentioned meaning, or an alkali metal alcoholate or an alkali metal hydroxide. The salts according to formula I are suitable for the production of squaric acid, by their being halogenated in a first step and then being hydrolyzed to squaric acid in a second step.Type: GrantFiled: February 21, 1991Date of Patent: February 11, 1992Assignee: Lonza Ltd.Inventors: Barry Jackson, Thomas Scholl
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Patent number: 5023226Abstract: Substituted or unsubstituted cyclohexylamine and substituted or unsubstituted dicyclohexylamine can be produced by catalytic hydrogenation of substituted or unsubstituted aniline by using a ruthenium catalyst which in addition to ruthenium also contains palladium, platinum or palladium and platinum on a support from the group consisting of Al.sub.2 O.sub.3 and aluminum spinel treated with chromium and manganese and containing the noble metals in a total amount of 0.05-5% by weight and a weight ratio of Ru:Pd, Ru:Pt, or Ru:Pd/Pt of 1:9-9:1. All percentages are based on the total weight of the catalyst.Type: GrantFiled: January 9, 1989Date of Patent: June 11, 1991Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz, Reinhard Thiel
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Patent number: 5017725Abstract: Addition salts of cysteamine with acids are prepared by reacting aziridine with an organic sulfur compound of oxidation state -2 and with a ketone and then subjecting the thiazolidine formed as an intermediate to acid hydrolysis, by a process in which aziridine and the ketone are reacted with ammonium hydrogen sulfide or with a metal hydrogen sulfide with the addition of a moderately strong or strong acid at from -10.degree. to +100.degree. C. and a pH which is greater than or equal to 8.5 is maintained.Type: GrantFiled: January 30, 1990Date of Patent: May 21, 1991Assignee: BASF AktiengesellschaftInventors: Andreas Hohmann, Wolfgang Reuther, Rolf Fikentscher, Theo Proll
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Patent number: 4996316Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.Type: GrantFiled: December 24, 1988Date of Patent: February 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
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Patent number: 4994619Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.Type: GrantFiled: June 16, 1988Date of Patent: February 19, 1991Assignee: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 4990633Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.Type: GrantFiled: May 4, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
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Patent number: 4988682Abstract: The present invention relates to a method for inhibiting the phosphatidylinositol cycle in a cell by contacting the cell with certain myo-inositol analogs. Such myo-inositol analogs can also be utilized to treat phosphatidylinositol cycle-dependent conditions. The present invention also provides novel myo-inositol analogs.Type: GrantFiled: February 3, 1989Date of Patent: January 29, 1991Assignee: University of PittsburghInventor: Alan P. Kozikowski