Benzyl Amines Wherein The Benzene Ring Has No Other Substituents Patents (Class 564/391)
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Patent number: 6429335Abstract: The present invention relates to a process for preparing amines of formula (I) R1—CH2—NH2 (I), wherein R1 represents optionally branched C1-C12-alkyl, C3-C8-cycloalkyl, C6-C12-aryl or C6-C12-aryl substituted with halogen-and/or C1-C12-alkyl, C7-C10-aralkyl or C7-C10-aralkyl substituted on the aryl radical by halogen and/or C1-C12-alkyl, or an aldose residue of the formula CiH2i+1Oi in which i is 2 to 5 and wherein one hydrogen of the aldose residue is optionally replaced by a saccharide residue, by catalytically hydrogenating aldehydes of formula (II) R1—CHO (II), wherein R1 has the meaning indicated for formula (I), in the presence of ammonia, a hydrogenation catalyst, and disodium tetraborate.Type: GrantFiled: December 12, 2001Date of Patent: August 6, 2002Assignee: Bayer AktiengesellschaftInventor: Wolfgang Kiel
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Patent number: 6380432Abstract: The present invention provides novel aromatic diamines useful in preparing polyimides for optical alignment layers in liquid crystal displays. The novel compositions comprise side-chains general formula I —L1—D—L2—Cf wherein D comprises 1 to 4 carbon-carbon double bonds, Cf is a monovalent C4 to C20 fluorocarbon radical and L1 and L2 are linking groups.Type: GrantFiled: December 20, 2000Date of Patent: April 30, 2002Assignee: Elsicon Inc.Inventors: Wayne M. Gibbons, Patricia A. Rose, Paul J. Shannon, Hanxing Zheng
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Patent number: 6362372Abstract: The invention relates to a process for producing a trifluoromethylbenzylamine represented by the following general formula (1), where each R independently represents a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, an alkyl group having a carbon atom number of 1-4, an alkoxy group having a carbon atom number of 1-4, an amino group, a hydroxyl group or a trifluoromethyl group, and n represents an integer from 0 to 4. The process includes hydrogenating a trifluoromethylbenzonitrile by hydrogen in an organic solvent in the presence of ammonia and a catalyst containing a platinum group element. This trifluoromethylbenzonitrile is represented by the following general formula (2), where R and n are defined as above. With this process, it is possible to obtain the trifluoromethylbenzylamine at an extremely high yield.Type: GrantFiled: April 12, 2001Date of Patent: March 26, 2002Assignee: Central Glass Company, LimitedInventors: Satoru Narizuka, Takashi Kume
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Patent number: 6291713Abstract: There is described a process of transferring &agr;,&bgr;-unsaturated alkyl groups to an electrophile (aldehyde, ketone, nitrile, imine, alkyne) by means of a masked zinc alkyl in an aprotic solvent.Type: GrantFiled: September 23, 1999Date of Patent: September 18, 2001Assignee: Metallgesellschaft AktiengesellschaftInventors: Philip Jones, Paul Knochel
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Patent number: 6288278Abstract: 3-amino-3-arylpropan-1-ol compounds corresponding to the formula I in which R1 to R5, A and X have the meanings according to claim 1, and their preparation and use as medicaments.Type: GrantFiled: April 7, 2000Date of Patent: September 11, 2001Assignee: Gruenenthal GmbHInventors: Bernd Sundermann, Hagen-Heinrich Hennies, Babette-Yvonne Koegel, Helmut Buschmann
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Patent number: 6235871Abstract: The transition metal-catalyzed amination of aryl halides, in conjunction with an orthogonal protective group scheme, forms the basis of two routes to oligoaniline precursors. The oligoaniline precursors are soluble in a variety of common organic solvents, and are easily converted to the deprotected oligoanilines. The method allows the preparation of oligoanilines of even or odd chain lengths, and the incorporation of a variety of functional groups into the oligomers. Polyanilines of low polydispersity can also be prepared by this method.Type: GrantFiled: December 2, 1998Date of Patent: May 22, 2001Assignee: Massachusetts Institute of TechnologyInventors: Robert A. Singer, Joseph P. Sadighi, Stephen L. Buchwald, Thomas Mackewitz
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Patent number: 6235936Abstract: A method is provided for the transition metal-catalyzed arylation, or vinylation, of hydrazines, hydrazones, and the like. Additionally, the invention provides a conceptually novel strategy, the cornerstone of which is the transition metal-catalyzed arylation or vinylation method, for the synthesis of indoles, carbazoles, and the like. The methods and strategies of the invention may be utilized in standard, parallel, and combinatorial synthetic protocols.Type: GrantFiled: February 26, 1998Date of Patent: May 22, 2001Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Seble Wagaw, Oliver Fabian Geis
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Patent number: 6232467Abstract: Amines and amino acids are prepared by reacting an amine, a carbonyl derivative, and an organoboron compound under mild conditions.Type: GrantFiled: June 27, 1997Date of Patent: May 15, 2001Assignee: University of Southern CaliforniaInventors: Nicos A. Petasis, Ilia A. Zavialov
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Patent number: 6175041Abstract: The invention relates to a process for producing a trifluoromethylbenzylamine represented by the following general formula (1). This process includes hydrogenating a trifliuoromethylbenzonitrile represented by the following general formula (2) by hydrogen in an organic solvent in the presence of ammonia, using a Raney catalyst, where each R independently represents a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, an alkyl group having a carbon atom number of 1-4, an alkoxy group having a carbon atom number of 1-4, an amino group, a hydroxyl group or a trifluoromethyl group, and n represents an integer from 0 to 4, where R and n are defined as above. With this process, it is possible to obtain the trifluoromethylbenzylamine easily and inexpensively at an extremely high yield.Type: GrantFiled: March 7, 2000Date of Patent: January 16, 2001Assignee: Central Glass Company, LimitedInventors: Seiji Takasaki, Takahiro Koizumi, Takashi Kume, Michio Ishida, Satoru Narizuka, Eri Tsukada
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Patent number: 6169200Abstract: The present invention provides a simple and inexpensive method for producing &agr;-hydroxy-&bgr;-aminocarboxylic acids and their esters. An ester of an N-protected &agr;-amino acid ester is converted into a &bgr;-ketosulfoxide, which is then processed with an acid to give an &agr;-ketohemimercaptal. Next, this is acylated and then processed with a base to obtain an N-protected &agr;-acyloxy-&bgr;-amino-thioester, which is then saponified to obtain an intended compound. According to the method of the present invention, it is possible to produce &agr;-hydroxy-&bgr;-aminocarboxylic acid derivatives, which are intermediates in producing various HIV protease inhibitors, renin inhibitors and carcinostatics, from a-amino acids. The method comprises reduced reaction steps, the selectivity in the method to give the intended product is high, and the yield of the product obtained is high.Type: GrantFiled: November 5, 1998Date of Patent: January 2, 2001Assignee: Ajinomoto Co., Inc.Inventors: Takayuki Suzuki, Yutaka Honda, Kunisuke Izawa
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Patent number: 6169116Abstract: Compounds of formula I wherein R1, R2, R3, R4 and R5 are as defined in the description, are useful as pharmaceuticals.Type: GrantFiled: June 28, 1999Date of Patent: January 2, 2001Assignee: Novartis AGInventor: Robert Swoboda
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Patent number: 6127550Abstract: This invention is directed to methods for stereospecifically preparing [(1-optionally substituted aryl)- or (1-optionally substituted heteroaryl)]-2-substituted ethyl-2-amines, having chirality at the 2-position, and to intermediates to the substituted ethyl-2-amines.Type: GrantFiled: March 11, 1999Date of Patent: October 3, 2000Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Luc Grondard, Jean-Paul Casimir, Patrick Leon, Michael K. O'Brien, Matthew R. Powers, Daniel Robin
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Patent number: 6072085Abstract: The method of the present invention provides a simple general route to a wide range of secondary amines.Type: GrantFiled: September 30, 1997Date of Patent: June 6, 2000Assignee: Massachusetts Institute of TechnologyInventors: Xavier Verdaguer, Udo E. W. Lange, Stephen L. Buchwald
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Patent number: 6057358Abstract: Novel amine derivatives of the following general formula (I): ##STR1## (wherein) A may denote --(CH.sub.2)--O--, --(CH.sub.2).sub.2 --O--, or --(CH.sub.2).sub.2 --NH--;B may denote --(CH.sub.2).sub.2 --;R.sub.1 may denote a hydrogen atom, a halogen atom, a nitro group, a 1-pyrrolyl group, an acetamido group, an amino group or a dimethylamino group;R.sub.2 may denote a hydrogen atom or a nitro group;R.sub.3 and R.sub.4 may denote a hydrogen atom;R.sub.8a and R.sub.8b which are the same may denote a chlorine atom or a methoxy group;R.sub.9 may denote a hydrogen atom or an amino group;R may denote a methyl group; andX may denote a methanesulfonamido group, a 1-imidazolyl group or a nitro group or a salts thereof are useful as antiarrhythmic drugs.Type: GrantFiled: May 27, 1997Date of Patent: May 2, 2000Assignee: C&C Research Labs.Inventors: You Sup Chung, Hak Yeop Kim, Kyung Yun Jung, Jae Ki Min, Shigeru Tanabe
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Patent number: 5929281Abstract: A heterocyclic aromatic halide or an aryl halide is reacted with an amine compound in the presence of a base to give a heterocyclic aromatic amine or an arylamine, respectively. In this reaction, a catalyst comprising a palladium compound and a tertiary phosphine is used for the preparation of a heterocyclic aromatic amine, and a catalyst comprising a palladium compound and a trialkylphosphine is used for the preparation of an arylamine.Type: GrantFiled: April 15, 1997Date of Patent: July 27, 1999Assignee: Tosoh CorporationInventors: Masakazu Nishiyama, Yasuyuki Koie
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Patent number: 5883284Abstract: The present invention provides a simple and inexpensive method for producing .alpha.-hydroxy-.beta.-aminocarboxylic acids and their esters.An ester of an N-protected .alpha.-amino acid ester is converted into a .beta.-ketosulfoxide, which is then processed with an acid to give an .alpha.-ketohemimercaptal. Next, this is acylated and then processed with a base to obtain an N-protected .alpha.-acyloxy-.beta.-amino-thioester, which is then saponified to obtain an intended compound. According to the method of the present invention, it is possible to produce .alpha.-hydroxy-.beta.-aminocarboxylic acid derivatives, which are intermediates in producing various HIV protease inhibitors, renin inhibitors and carcinostatics, from a-amino acids. The method comprises reduced reaction steps, the selectivity in the method to give the intended product is high, and the yield of the product obtained is high.Type: GrantFiled: June 17, 1998Date of Patent: March 16, 1999Assignee: Ajinomoto Co., Inc.Inventors: Takayuki Suzuki, Yutaka Honda, Kunisuke Izawa
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Patent number: 5872298Abstract: A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide or cyanohydrin from a chiral alpha amino aldehyde.Type: GrantFiled: April 9, 1997Date of Patent: February 16, 1999Assignee: G. D. Searle & Co.Inventors: John S Ng, Claire A Przybyla, Richard A Mueller, Michael L Vazquez, Daniel P Getman, John J Freskos, Gary A DeCrescenzo, Deborah E Bertenshaw, Robert M Heintz, Suhong Zhang, Chin Liu, Scott A Laneman
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Patent number: 5773617Abstract: The present invention relates to a reagent and to a process which are useful, when carrying out an organic synthesis, for cleaving an allylic group from a function which is protected with the latter.This reagent is defined in that it contains:a) a solvent system;b) a catalyst containing at least one element from column VIII of the Periodic Table of the Elements, the said element from column VIII of the Periodic Table being coordinated with at least one coordination agent which is soluble in the said solvent system;c) a compound which is at least partially soluble in the said solvent system and which contains at least one nucleophilic function.Application to organic synthesis.Type: GrantFiled: February 22, 1996Date of Patent: June 30, 1998Assignee: Rhone-Poulenc ChimieInventors: Jean-Marie Bernard, Errol Blart, Jean-Pierre Genet, Sandrine Lemaire-Audoire, Monique Savignac
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Patent number: 5739405Abstract: A process for the preparation of amines of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 denote hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.3 -C.sub.20 cycloalkyl, C.sub.4 -C.sub.20 alkylcycloalkyl, C.sub.4 -C.sub.20 cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 alkylaryl, or C.sub.7 -C.sub.20 aralkyl,R.sup.1 and R.sup.2 together denote a saturated or unsaturated C.sub.3 -C.sub.9 alkylene dichain andR.sup.3 or R.sup.5 denotes C.sub.21 -C.sub.200 alkyl, C.sub.21 -C.sub.200 alkenyl or they together form a C.sub.2 -C.sub.12 alkylene dichain,by the reaction of olefins of the general formula II ##STR2## in which R.sup.3, R.sup.4, R.sup.5, and R.sup.6 have the above meanings, with ammonia or primary or secondary amines of the general formula III ##STR3## in which R.sup.1 and R.sup.2 have the above meanings, at temperatures ranging from 200.degree. to 350.degree. C.Type: GrantFiled: December 4, 1996Date of Patent: April 14, 1998Assignee: BASF AktiengesellschaftInventors: Karsten Eller, Rudolf Kummer, Peter Stops
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Patent number: 5726308Abstract: A process for preparing high purity solutions of highly substituted lithium amide bases by direct reaction of lithium metal with highly substituted amine bases alone or in an ether solvent, a hydrocarbon solvent or in a mixed ether/hydrocarbon solvent mixture, optionally in the presence of a catalyst selected from tin salts and transition metal salts of Groups 4B, 5B, 6B, 7B, and 8 of the Periodic Table.Type: GrantFiled: March 22, 1996Date of Patent: March 10, 1998Assignee: FMC CorporationInventors: Randy W. Hall, Robert S. Wedinger, Terry L. Rathman, James A. Schwindeman
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Patent number: 5719298Abstract: A method of producing a pantothenic acid derivative of formula (I): ##STR1## wherein each of R.sup.1 and R.sup.2 is different, and is a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, or a phenyl group; or a straight chain aliphatic hydrocarbon group having 5 to 10 carbon atoms, is provided, including methods of producing the starting materials for producing the same and novel amine derivative that can be used for the production of the pantothenic acid derivative.Type: GrantFiled: May 22, 1995Date of Patent: February 17, 1998Assignee: Fujirebio Inc.Inventors: Hiroshi Ikawa, Hajime Matsumoto
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Patent number: 5710099Abstract: Novel bioactive compounds which when applied to plants in bioregulatory amounts, enhance plant development responses, resulting in enhanced plant properties such as increased total biomass, increased yield, and increased plant quality. Some of the compounds increase the content of taxol and related taxanes in yew plants. One compound, 2-?diethylaminoethyl!-2-methylpropylether causes plants treated with the compound to have resistance to chewing insects. The compound 2-?diethylaminoethyl!-2-methyl-2-phenylpropylether causes plants treated with the compound to have resistance to sucking insects.Type: GrantFiled: February 27, 1996Date of Patent: January 20, 1998Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Henry Yokoyama, Harold W. Gausman
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Patent number: 5698741Abstract: An improved synthesis of a highly potent HIV reverse transcription inhibitor is disclosed, involving an acetylide and a trifluoromethyl ketone which produces a chiral product in the presence of a chiral amino alcohol.Type: GrantFiled: July 15, 1996Date of Patent: December 16, 1997Assignee: Merck & Co. Inc.Inventors: Andrew S. Thompson, Edward G. Corley, Edward J. J. Grabowski, Nobuyoshi Yasuda
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Patent number: 5659069Abstract: This invention discloses an improved method for the [2+2+2] cyclotrimerization reaction in aqueous solutions using a water soluble transition metal catalyst.Type: GrantFiled: March 20, 1996Date of Patent: August 19, 1997Assignee: NeXstar Pharmaceuticals, Inc.Inventors: Bruce Eaton, Matthew S. Sigman
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Patent number: 5652271Abstract: Compounds of formula I ##STR1## and pharmaceutically acceptable salts thereof in which m is 0, 1 or 2; n is 2, 3, 4 or 5; X is carbonyl or a group of formula II ##STR2## in which R.sub.5 is H or alkyl; Y is an alkylene chain optionally substituted by one or more alkyl groups; Z is an alkylene chain containing 2 to 5 carbon atoms optionally substituted by one or more alkyl groups; R is phenyl optionally substituted by one or more halo substituents or R is naphthyl; and R.sub.1 and R.sub.2, which are the same or different, are H, alkyl, or arylalkyl, provided that when R.sub.1 is benzyl, R.sub.2 is H or methyl;have utility in the treatment of depression, anxiety, Parkinson's disease, obesity, cognitive disorders, seizures, neurological disorders such as epilepsy, and as neuroprotective agents to protect against conditions such as stroke.Type: GrantFiled: December 22, 1995Date of Patent: July 29, 1997Assignee: Knoll AktiengesellschaftInventors: Paul John Harris, David John Heal
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Patent number: 5633405Abstract: An improved synthesis of a highly potent HIV reverse transcription inhibitor is disclosed, involving an acetylide and a trifluoromethyl ketone which produces a chiral product in the presence of a chiral amino alcohol.Type: GrantFiled: May 25, 1995Date of Patent: May 27, 1997Assignee: Merck & Co., Inc.Inventors: Andrew S. Thompson, Edward G. Corley, Edward J.J. Grabowski, Nobuyoshi Yasuda
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Patent number: 5576460Abstract: A method of preparing an arylamine compound includes reacting a metal amide comprising a metal selected from the group consisting of tin, boron, zinc, magnesium, indium and silicon, with an aromatic compound comprising an activated substituent in the presence of a transition metal catalyst to form an arylamine. The method is useful in preparing mixtures of arylamines for use in screening for pharmaceutical and biological activity and in preparing poly(anilines).Type: GrantFiled: July 27, 1994Date of Patent: November 19, 1996Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Anil Guram
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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: 5536878Abstract: Disclosed are (1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and (2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added. In a further aspect, a method is provided for the preparation of aminodiphenylamine by reacting phenylenediamine and cyclohexanone in the presence of a hydrogen transfer catalyst in a sulfur-free polar solvent while using nitroaniline as a hydrogen acceptor.Type: GrantFiled: December 2, 1994Date of Patent: July 16, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou, Masae Uchida
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Patent number: 5536877Abstract: A process for the preparation of arylbenzylamines by the reaction of arylamines with a benzyl chloride, wherein the reaction is carried out in the presence of both a phase-transfer catalyst and a base selected from the group consisting of the inorganic bases and salts of weak organic acids.Type: GrantFiled: March 23, 1995Date of Patent: July 16, 1996Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Hammer, Gerd Husslein
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Patent number: 5521309Abstract: An anionic polymerization initiator includes the C-lithio reaction product of an organolithium compound and a tertiary-amino allyllithium or a tertiary-amino xylyllithium. When used in an anionic polymerization, a functional group from the initiator is incorporated onto the head of the growing polymer and a lithium atom is incorporated at the "living" end of the polymer chain prior to quenching. The initiator may be used to polymerize a monomer(s) including diolefin monomers, monovinyl aromatic monomers and trienes, and the living ends of the polymers are effectively maintained even at temperatures of up to 300.degree. F. and higher. Such polymers exhibit an increased efficiency in coupling termination reactions, and products prepared from such polymers exhibit improved hysteresis characteristics. Products such as tires and the like can be prepared from such polymers and from vulcanizable elastomer compositions employing the polymers.Type: GrantFiled: December 23, 1994Date of Patent: May 28, 1996Assignee: Bridgestone CorporationInventors: Thomas A. Antkowiak, James E. Hall, David F. Lawson, John R. Schreffler, Mark L. Stayer, Jr.
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Patent number: 5508280Abstract: This invention relates to novel derivatives of 5H-dibenzo (a,d)cycloheptenes, to the processes for their preparation, to their muscarinic receptor antagonist properties and to their end-use application for treating Parkinson's Disease, tardive dyskinesia, and motion sickness.Type: GrantFiled: January 30, 1995Date of Patent: April 16, 1996Assignee: Merrell Pharmaceuticals, Inc.Inventors: Marcel Hibert, Luc Van Hijfte, Mary Richards, Paul Moser
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Patent number: 5470977Abstract: The present invention provides novel ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes, 3-aminochromanes, and 3-aminothiochromanes, including their corresponding sulfoxides and sulfones, which ring-substituted compounds exhibit agonist activity at the serotonin 1A receptor.Type: GrantFiled: March 14, 1995Date of Patent: November 28, 1995Assignee: Eli Lilly and CompanyInventors: John M. Schaus, Craig S. Hoechstetter, Diane Huser, Charles J. Paget, Robert D. Titus
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Patent number: 5468775Abstract: The present invention concerns enaminones having the formula: ##STR1## wherein R is from the group consisting of COOCH.sub.3 and COOC.sub.2 H.sub.5 ; R.sup.1 is from the group consisting of H and CH.sub.3 ; R.sup.2 is from the group consisting of H when R.sup.1 is CH.sub.3 and CH.sub.3 when R.sup.1 is H; and R.sup.3 is from the group of first radicals consisting of benzyl, phenethyl, disubstituted phenyl and trisubstituted phenyl. The substituted species are second radicals having positive lipophilicity selected from the group consisting of F, Cl, Br, and I.Type: GrantFiled: March 2, 1993Date of Patent: November 21, 1995Assignee: Howard UniversityInventors: Kenneth R. Scott, Jesse M. Nicholson, Ivan O. Edafiogho
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Patent number: 5442119Abstract: A catalytic asymmetric reduction process, which, by hydrogenating trisubstituted olefins, yields a corresponding organic compound having a high level of enantiomeric purity is disclosed. The reduction process utilizes a chiral metal catalyst that includes a metal or metal complex that is selected from groups 3, 4, 5, or 6, lanthanides and actinides. Moreover, the process uses hydrogen as the stoichiometric reducing agent and may be carried out at pressures ranging from about 1 to 200 atmospheres.Type: GrantFiled: July 12, 1993Date of Patent: August 15, 1995Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Richard D. Broene
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Patent number: 5430187Abstract: The method for manufacturing dibenzylamine by reacting benzaldehyde and ammonia in the presence of hydrogen and a hydrogenation catalyst in an inert organic solvent is characterized by the fact that the reaction is conducted with an ammonia ratio of >0.5 mol per mol benzaldehyde and with a hydrogenation catalyst containing a platinum metal and/or a ferrous metal on a carrier. The method is performed at low temperatures, preferably 40.degree.-90.degree. C. In particular, a high selectivity for dibenzylamine of more than 90% is achieved with practically complete benzaldehyde conversion.Type: GrantFiled: May 17, 1994Date of Patent: July 4, 1995Assignee: Akzo N.V.Inventors: Burkhard Weuste, Manfred Bergfeld
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Ring-substituted 2-amino-1,2,3,4-tetra-hydronaphthalenes, 3-aminochromanes, and 3-aminothiochromanes
Patent number: 5426229Abstract: The present invention provides novel ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes, 3-aminochromanes, and 3-aminothiochromanes, including their corresponding sulfoxides and sulfones, which ring-substituted compounds exhibit agonist activity at the serotonin 1A receptor.Type: GrantFiled: December 16, 1993Date of Patent: June 20, 1995Assignee: Eli Lilly and CompanyInventors: John M. Schaus, Craig S. Hoechstetter, Diane Huser, Charles J. Paget, Robert D. Titus -
Patent number: 5410081Abstract: Compounds of the formula (I) ##STR1## are prepared by reacting 2-mercaptoethanol with compounds of the general formula (II) ##STR2## the substituents having the definition given in the description.Type: GrantFiled: June 24, 1994Date of Patent: April 25, 1995Assignee: Bayer AktiengesellschaftInventors: Klaus Kunde, Karl-Josef Herd
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Patent number: 5334628Abstract: Amine derivatives having the general formula (I): ##STR1## wherein X is selected from the group consisting of ##STR2## wherein Q is oxygen, sulfur or nitrogen atom, and ##STR3## wherein Q is as above; Y is selected from the group consisting of ##STR4## R.sup.1 is hydrogen atom or an alkyl group; R.sup.2 is hydrogen atom or an alkyl group; R.sup.3 is hydrogen atom, a halogen atom or an alkyl group; R.sup.4 hydrogen atom, an alkyl group, a cycloalkyl group, a halogenated alkyl group or a halogen atom; R.sup.5 is hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, nitro group or hydroxy group; R.sup.5 is attached to an arbitrary position of X, and R.sup.3 or R.sup.4 is attached to an arbitrary position of Y.The amine derivatives (I) are useful as fungicides.Type: GrantFiled: December 31, 1992Date of Patent: August 2, 1994Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Tetsuya Maeda, Toshiyuki Yamamoto, Mituo Takase, Kazuya Sasaki, Tadashi Arika, Mamoru Yokoo, Rieko Hashimoto, Kouji Amemiya, Sakae Koshikawa
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Patent number: 5329054Abstract: Activated carboxylic acids and esters such as pentafluorobenzoic acid are rapidly decarboxylated in high yields by reacting the acid or ester with an alkanolamine reagent which catalyzes the reaction.Type: GrantFiled: July 19, 1993Date of Patent: July 12, 1994Assignee: Albemarle CorporationInventors: Kevin J. Theriot, Niomi L. Krzystowczyk, Yueh-Dong Chen, Edward A. Burt, Lawrence H. Shepherd, Jr.
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Patent number: 5322963Abstract: Intermediate compounds (formula [III]and [IV]) useful as starting materials for the synthesis of amino acid derivatives which have renin inhibitory activity and which are useful as remedies for hypertension are prepared stereoselectively in high yield, without requiring complicated process steps. In this method, by reaction of .alpha.-amino aldehyde derivative [I] and compound [II] in the presence of BF.sub.3.OEt.sub.2, as shown in the following reaction formula, .alpha.-amino-.beta.-hydroxy-.delta.-ketone derivative [III] is prepared, and furthermore, by reducing it as required, compound [IV] is obtained: ##STR1## (where R.sup.1 is a protective group on the amino group, R.sup.2 is a lower alkyl group which may be branched, and R.sup.4 is a cyclohexyl group or phenyl group).Type: GrantFiled: October 5, 1992Date of Patent: June 21, 1994Assignee: Japan Tobacco, Inc.Inventors: Saizo Shibata, Eiji Shirakawa, Yasuki Yamada, Koji Ando, Itsuo Uchida
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Patent number: 5294638Abstract: Pharmacologically active compounds corresponding to the general formula I: ##STR1## wherein m represents 1-4,n represents 2-5,R.sup.1 is hydrogen or lower alkyl,R.sup.2 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, andR.sup.3 is hydrogen, lower alkyl, lower alkoxy or halogen, orR.sup.2 and R.sup.3 are linked to adjacent carbon atoms and together form an alkylenedioxy group with 1-2 carbon atoms,R.sup.4 represents a saturated monocyclic or bicyclic hydrocarbon radical derived from terpenes and having 10 or 11 hydrocarbon atoms, andZ represents oxygen, an N--R.sup.5 group, wherein R.sup.5 is lower alkyl, or if R.sup.4 is a dihydronopyl radical, Z may also be sulfur,and their acid addition salts.Type: GrantFiled: January 19, 1993Date of Patent: March 15, 1994Assignee: Kali-Chemie Pharma GmbHInventors: Insa Hell, Ulf Preuschoff, Hermann Kraehling, Samuel David, Ivan Ban, Marie-Odile Christen
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Patent number: 5252750Abstract: Polyolefin derivatives, which are useful not only as the photoconductive materials for electrophotography, but also as a charge transporting material employed in a function-separating type photoconductor which uses an organic or inorganic pigment as a charge generating material, and an electrophotographic photoconductor containing at least one of the above polyolefin derivatives in a photoconductive layer thereof, are disclosed.Type: GrantFiled: June 3, 1991Date of Patent: October 12, 1993Assignees: Ricoh Company, Ltd., Hodogaya Chemical Company, Ltd.Inventors: Mitsuru Hashimoto, Tomoyuki Shimada, Nobuo Suzuki, Takayuki Sakai, Susumu Suzuka, Masaomi Sasaki
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Patent number: 5248826Abstract: An electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed thereon comprising as an effective component at least one polyether compound represented by formula (I): ##STR1## wherein Ar represents a phenylene group or a biphenylene group; R.sup.1 and R.sup.2 each represent an alkyl group which may have a substituent, or an aryl group which may have a substituent; and n is an integer of 1 to 4. Furthermore, charge transporting material comprising the above polyether compound, polyether compounds having formula (II) for use in the electrophotographic photoconductor and a method of preparing the same are disclosed, ##STR2## wherein m is an integer of 1 or 2.Type: GrantFiled: July 29, 1992Date of Patent: September 28, 1993Assignee: Ricoh Company, Ltd.Inventors: Masaomi Sasaki, Tamotsu Aruga, Tomoyuki Shimada
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Patent number: 5237100Abstract: Substituted benzylcycloalkenylurea derivatives of the formula (I) ##STR1## wherein X represents a halogen atom or a lower alkyl group, Y represents an oxygen atom or a sulfur atom,R.sup.1 represents a cycloalkenyl group andR.sup.2 represents a lower alkyl group, a cycloalkyl group, a benzyl group or a phenyl group optionally substituted by 1 to 5 substituents selected from the group consisting of a hydroxyl group or a lower alkoxy groupand their use as fungicides. They can be synthesized, for example, by reacting of a substituted benzyl-cycloalkenylamine with an isocyanate or by reacting of a carbamoyl halide with an amine. The starting material, the substituted benzyl-cycloalkenyl amines, are also new.Type: GrantFiled: April 23, 1992Date of Patent: August 17, 1993Assignee: Nihon Bayer Agrochem K.K.Inventors: Yasuo Yamada, Junichi Saito, Tatsuo Tamura, Shinji Sakawa
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Patent number: 5196454Abstract: The invention relates to novel 2,5-diaminotetralines of the formula: ##STR1## wherein R1, R2, R3 and R4 are defined herein, processes for preparing them and their use in pharmaceutical compositions. The novel 2,5-diaminotetralines are useful in treating diseases caused by disorders of the dopaminergic systems.Type: GrantFiled: June 15, 1990Date of Patent: March 23, 1993Assignee: Boehringer Ingelheim KGInventors: Matthias Grauert, Herbert Merz, Joachim Mierau, Gunter Schingnitz, Claus Schneider
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Patent number: 5166438Abstract: A charge transporting material comprising a 1,3-pentadiene derivative having formula (I):A--CH.dbd.CH--CH.dbd.CH--CH.sub.2 --A (I)wherein A represents a 9-anthryl group which may have a substituent, a N-substituted carbazolyl group which may have a substituent, a N-substituted phenothiazinyl group which may have a substituent or ##STR1## in which Ar represents an arylene group which may have a substituent, R.sup.1 and R.sup.2 each represent an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent; an electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed thereon, which comprises as an effective component at least one of the 1,3-pentadiene derivatives of the above formula (I); and novel 1,3-pentadiene derivatives of the formula (I), provided that in the formula (I), R.sup.1 and R.sup.2 cannot be a methyl group at the same time, are disclosed.Type: GrantFiled: August 23, 1991Date of Patent: November 24, 1992Assignees: Ricoh Company, Ltd., Hodogaya Chemical Co., Ltd.Inventors: Mitsuru Hashimoto, Masaomi Sasaki, Tomoyuki Shimada, Nobuo Suzuki, Takayuki Sakai, Susumu Suzuka
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Patent number: 5153235Abstract: The present invention relates to a process for the production of elastic, compact or cellular moldings based on elastomers containing N-benzylurea groups in bound form, by reactinga) one or more organic and/or modified organic polyisocyanates withb) N-benzylpolyoxyalkylene-polyamines or mixtures of N-benzylpolyoxyalkylene-polyamines and polyoxyalkylene-polyamines containing from 2 to 4 primary amino groups andc) one or more alkyl-substituted aromatic polyamines having a molecular weight of up to 500,in the presence or absence ofd) catalystsand, if desired,e) blowing agents,f) auxiliaries and/org) additives,and to the N-benzylpolyoxyalkylene-polyamines and mixtures of N-benzylpolyoxyalkylene-polyamines and polyoxyalkylene-polyamines containing from 2 to 4 primary amino groups which can be used for this purpose, and to the elastomers prepared.Type: GrantFiled: January 24, 1992Date of Patent: October 6, 1992Assignee: BASF AktiengesellschaftInventors: Johannes Becker, Guenther Matzke, Hans U. Schmidt, Willibald Schoenleben
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Patent number: 5082938Abstract: Enhanced branched chain hydroxyl compounds are provided of formulaY--(Z).sub.1-6wherein Y is the residue of a nucleophile devoid of conjugated divalent linking moieties, and each Z is a poly(oxyalkylene) moiety having a molecular weight of from about 200-10,000 and containing at least one glycidol residue, wherein at least one of the primary oxy sites of said glycidol residue is linked preferably directly to a first epoxide residue of three or more carbons, and wherein said first epoxide residue is linked through a secondary oxy site preferably directly to a second epoxide reside having a primary terminal hydroxyl.Type: GrantFiled: March 1, 1990Date of Patent: January 21, 1992Assignee: Milliken Research CorporationInventors: Edward W. Kluger, David J. Moody
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Patent number: 5051409Abstract: 2-Aminodecalin derivatives of the formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are H or methyl,A is H, OH, O-alkylcarbonyl, O-benzoyl or O-CH.sub.3,R.sup.4 is H, cyclopropyl, alkyl, alkenyl, or alkynyl,R.sup.5 is alkyl, alkenyl or alkynyl which is substituted or unsubstituted,cycloalkyl or cycloalkenyl whic is substituted or unsubstituted, substituted phenylalkyl, substituted cycloalkyl-alkyl, substituted 5-membered heterocyclic ring, bicycloalkyl-alkyl orR.sup.4 and R.sup.5, together with the nitrogen atom, are a substituted or unsubstituted, saturated or unsaturated piperidine radical,their plant-tolerated salts and N-oxides, and fungicides containing these compounds.Type: GrantFiled: November 1, 1989Date of Patent: September 24, 1991Assignee: BASF AktiengesellschaftInventors: Matthias Zipplies, Bernhard Zipperer, Hubert Sauter, Norbert Goetz, Franz Roehl, Eberhard Ammermann, Gisela Lorenz