Alpha Aralkyl Benzyl Amines Patents (Class 564/373)
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Patent number: 5616804Abstract: The present process involves preparing dibenzylamine through the hydrogenation of benzaldehyde in the presence of ammonia and a catalyst containing palladium using a small amount of solvent or dispersion medium. With the present process, dibenzylamine can be prepared with high selectivity in a relatively short reaction time and with complete conversion of the benzaldehyde, at which makes it commercially attractive. In the present process, a palladium-carbon catalyst is preferably used.Type: GrantFiled: November 17, 1995Date of Patent: April 1, 1997Assignee: DSM N.V.Inventors: Anna M. C. F. Castelijns, Peter J. D. Maas
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Patent number: 5539120Abstract: There is provided a method of treatment of neurological disorders, such as epilepsy, stroke and cerebral ischaemia, which comprises the administration of a compound of Formula I: ##STR1## wherein, Ar.sub.1 and Ar.sub.2, which may be the same or different, independently represent phenyl or phenyl substituted by one or more of amino, nitro, halogen, hydroxy, C1 to 6 alkoxy, C1 to 6 alkyl or cyano;R.sub.1 represents hydrogen, C1 to 6 alkyl, C1 to 6 alkoxycarbonyl;R.sub.2 represents hydrogen or COCH.sub.2 NH.sub.2 ;R.sub.3 represents hydrogen or C1 to 6 alkyl;in addition, when R.sub.2 represents hydrogen either one or both of Ar.sub.1 and Ar.sub.2 may also represent 2-, 3- or 4-pyridinyl and R.sub.1 may also represent trihalomethyl;or a pharmaceutically acceptable salt thereof.Some of the compounds of formula I are novel, and these are also provided, together with pharmaceutical compositions containing the novel compounds.Type: GrantFiled: March 6, 1995Date of Patent: July 23, 1996Inventors: Ronald C. Griffith, James J. Napier
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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: 5516929Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallochloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.Type: GrantFiled: February 12, 1993Date of Patent: May 14, 1996Assignee: Massachusetts Institute of TechnologyInventors: K. Barry Sharpless, Matthias Beller, Brent Blackburn, Yasuhiro Kawanami, Hoi-Lun Kwong, Yasukazu Ogino, Tomoyuki Shibata, Tatsuzo Ukita, Lisa Wang
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Patent number: 5510519Abstract: Disclosed are optically active secondary amine compounds and salts thereof having the general formula (I): ##STR1## a process for the preparation of the optically active secondary amine compounds and salts thereof, and the use of such compounds. Such compounds exhibit a high resolution power and hence are useful agents for optical resolution.Type: GrantFiled: December 13, 1993Date of Patent: April 23, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Junko Kudo, Toshio Nishioka
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Patent number: 5430044Abstract: There is provided a method of treatment of neurological disorders, such as epilepsy, stroke and cerebral ischaemia, which comprises the administration of a compound of Formula I: ##STR1## wherein, Ar.sub.1 and Ar.sub.2, which may be the same or different, independently represent phenyl or phenyl substituted by one or more of amino, nitro, halogen, hydroxy, C1 to 6 alkoxy, C1 to 6 alkyl or cyano;R.sub.1 represents hydrogen, C1 to 6 alkyl, C1 to 6 alkoxycarbonyl;R.sub.2 represents hydrogen or COCH.sub.2 NH.sub.2 ;R.sub.3 represents hydrogen or C1 to 6 alkyl;in addition, when R.sub.2 represents hydrogen either one or both of Ar.sub.1 and Ar.sub.2 may also represent 2-, 3- or 4-pyridinyl and R.sub.1 may also represent trihalomethyl;or a pharmaceutically acceptable salt thereof.Some of the compounds of formula I are novel, and these are also provided, together with pharmaceutical compositions containing the novel compounds.Type: GrantFiled: July 16, 1992Date of Patent: July 4, 1995Assignee: Fisons CorporationInventors: Ronald C. Griffith, James J. Napier
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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: 5298660Abstract: Disclosed are optically active secondary amine compounds and salts thereof having the general formula (I): ##STR1## a process for the preparation of the optically active secondary amine compounds and salts thereof, and the use of such compounds. Such compounds exhibit a high resolution power and hence are useful agents for optical resolution.Type: GrantFiled: April 6, 1992Date of Patent: March 29, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Junko Kudo, Toshio Nishioka
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Patent number: 5260461Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, an aqueous solution, a base, a ferricyanide salt and an osmium-containing compound are combined. The chiral ligand is an alkaloid or alkaloid derivative linked to an organic substituent of at least 300 daltons molecular weight through a planar aromatic spacer group. The organic substituent can be another alkaloid or alkaloid derivative. With the described chiral ligands, asymmetric dihydroxylation of olefins with high yields and enantiomeric excesses are achieved.Type: GrantFiled: October 10, 1991Date of Patent: November 9, 1993Assignee: Massachusetts Institute of TechnologyInventors: Jens Hartung, K. Barry Sharpless
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Patent number: 5200561Abstract: Disclosed is a process for producing an optically active amine represented by the formula (IV) ##STR1## wherein R.sub.7 and R.sub.8 each denote an alkyl group, aryl group or aralkyl group, providing that they do not denote the same group at the same time, and * indicates an asymmetric carbon atom, which comprises reacting an asymmetric reducing agent obtained from (1) an optically active amine derivative represented by the formula (I) ##STR2## wherein R.sub.1 denotes an alkyl group, aryl group or aralkyl group; R.sub.2 denotes a hydrogen atom, alkyl group or aralkyl group; R.sub.3 denotes an aryl group or a substituent represented by the formula (II) ##STR3## wherein R.sub.4 and R.sub.5 each denote a hydrogen atom, aryl group or aralkyl group, and * is as defined above, (2) a metal borohydride and (3) sulfuric acid, with either the syn-isomer or the anti-isomer of an oxime derivative represented by the formula (III) or with a mixture rich in either one of the two isomers ##STR4## wherein R.sub.Type: GrantFiled: October 7, 1991Date of Patent: April 6, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Naoto Konya, Yukio Yoneyoshi, Yoji Sakito, Shinji Nishii, Gohfu Suzukamo, Hiroko Sakane
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Patent number: 5196601Abstract: Disclosed herein is a process for producing an alcohol or an amine by reducing a compound having a formyl, keto, nitro, oxirane, ester, nitrile, amide or halogenated carboxyl group with an alkali metal boro-hydride in the presence of a compound having a hydroxyl group and ether linkage. According to the present invention, a functional group having a great steric hindrance can be reduced, and a corresponding alcohol or amine can efficiently be produced under very mild conditions on an industrial scale.Type: GrantFiled: June 17, 1992Date of Patent: March 23, 1993Assignee: Kao CorporationInventors: Tomohito Kitsuki, Yoshiaki Fujikura
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Patent number: 5147873Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, or a pharmaceutically acceptable cation;Y is cyclopropyl, ethyl or p-fluorophenyl, and X is hydrogen or fluoro, or X and Y taken together form a group ##STR2## wherein R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; or a pharmaceutically acceptable salt thereof. Also disclosed are antibacterial pharmaceutical compositions comprising the foregoing compounds, methods of using the compounds in treating bacterial infections, and intermediates for the preparation of the compounds.Type: GrantFiled: February 15, 1991Date of Patent: September 15, 1992Assignee: Pfizer Inc.Inventor: Edward F. Kleinman
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Patent number: 5145998Abstract: A method for producing an optically active amine which is an important compound as a resolving agent for medicines, agricultural chemicals, intermediates thereof, etc is disclosed.Type: GrantFiled: October 2, 1990Date of Patent: September 8, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Yoji Sakito, Gohfu Suzukamo, Yukio Yoneyoshi
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Patent number: 5099019Abstract: Disclosed are .DELTA..sup.9(11) -steroids (VI) and amino substituted steroids (XI) which contain an amino group attached to the terminal carbon atom of the C.sub.17 -side chain, more particularly amino steroids (Ia and Ib), aromatic steroids (II), .DELTA..sup.16 -steroids (IIIa and IIIb), reduced A-ring steroids (IV), .DELTA..sup.17(20) -steroids (Va and Vb) and .DELTA..sup.9(11) -steroids (VI) which are useful as pharmaceutical agents for treating a number of conditions.Type: GrantFiled: August 8, 1988Date of Patent: March 24, 1992Assignee: Upjohn CompanyInventors: John M. McCall, Donald E. Ayer, E. Jonathan Jacobsen, Frederick J. VanDoornik, John R. Palmer, Harold A. Karnes
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Patent number: 5089639Abstract: N-Cycloalkylalkylamines of formula I: ##STR1## in which: R1 is phenyl which is optionally mono-, di- or trisubstituted by halogens or lower alkyl, haloalkyl or lower alkoxy radicals, or is an aromatic heterocyclic radical having 5 to 7 chain members, in which the hetero atom is nitrogen, oxygen or sulphur,R2 is lower alkyl,R3 is hydrogen or lower alkyl,m has the value of 1 or 2,R4 is cycloalkyl --CH(CH2)n, in which a carbon atom may carry a radical Rx, which is lower alkyl or phenyl; and in which n has the values from 2 to 5,R5 is phenyl, which can be mono-, di- or trisubstituted by halogens or by lower alkoxy radicals, andQ represents an ethylene-1,2-diyl group --CH.dbd.Type: GrantFiled: January 24, 1991Date of Patent: February 18, 1992Assignee: Jouveinal S.A.Inventors: Gilbert G. Aubard, Alain P. Calvet, Jean-Pierre Defaux, Claude J. Gouret, Agnes M. Grouhel, Henry L. Jacobelli, Jean-Louis Junien, Xavier B. Pascaud, Francois F. Roman, James P. Hudspeth, Yuan Lin
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Patent number: 5034419Abstract: N-Cycloalkylalkylamines of formula I: ##STR1## in which: R1 is phenyl which is optionally mono-, di- or trisubstituted by halogens or lower alkyl, haloalkyl or lower alkoxy radicals, or is an aromatic heterocyclic radical having 5 to 7 chain members, in which the hetero atom is nitrogen, oxygen or sulphur,R2 is lower alkyl,R3 is hydrogen or lower alkyl,m has the value of 1 or 2,R4 is cycloalkyl --CH(CH2)n, in which a carbon atom may carry a radical Rx, which is lower alkyl or phenyl; and in which n has the values from 2 to 5,R5 is phenyl, which can be mono-, di- or trisubstituted by halogens or by lower alkoxy radicals, andQ represents an ethylene-1,2-diyl group --CH.dbd.Type: GrantFiled: February 26, 1990Date of Patent: July 23, 1991Assignee: L'OrealInventors: Gilbert G. Aubard, Alain P. Calvet, Jean-Pierre DeFaux, Claude J. Gouret, Agnes M. Grouhel, Henry L. Jacobelli, Jean-Louis Junien, Xavier Pascaud, Francois F. Roman, James P. Hudspeth, Yuan Lin
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Patent number: 5011996Abstract: Reaction products of oxo compounds and amines or ammonia, in which at least one substituent is aromatic and monosubstituted to trisubstituted by halogen, can be catalytically hydrogenated to the respective amines, the halogen essentially being completely retained if an Ni-containing or Co-containing catalyst is employed and the reaction is carried out in the presence of organic sulphur compounds.Type: GrantFiled: July 5, 1989Date of Patent: April 30, 1991Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kiel, Heinz Ziemann
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Patent number: 4996235Abstract: The present invention provides 3,4-diphenylbutanamines capable of selectively inhibiting the uptake of serotonin and norepinephrine.Type: GrantFiled: November 25, 1987Date of Patent: February 26, 1991Assignee: Eli Lilly and CompanyInventors: David W. Robertson, David T. Wong
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Patent number: 4968721Abstract: Novel 4-phenyl-1,3-benzodiazepines and 2-amino-.alpha.-phenylphenethylamines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants. The 2-amino-.alpha.-phenylphenethylamines are useful as anticonvulsant and neuroprotective agents.Type: GrantFiled: January 4, 1989Date of Patent: November 6, 1990Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Manfred Worm, Charles A. Crichlow
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Patent number: 4965364Abstract: An osmium-catalyzed method of addition to an olefin. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an amine oxide an osmium-containing compound and, optionally a tetraalkyl ammonium compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, an amine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative or an amine derivative and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, N-methyl morpholine N-oxide and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.Type: GrantFiled: September 28, 1988Date of Patent: October 23, 1990Assignee: Massachusetts Institute of TechnologyInventors: Istvan E. Marko, K. Barry Sharpless
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Patent number: 4914241Abstract: Diamines of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, alkyl, aryl, alkoxy, aralkyl or cycloalkyl and X is a group of the formula(CR.sup.4 R.sup.5).sub.m (II)where R.sup.4 and R.sup.5 have the meanings given above for R.sup.1 and m is from 1 to 12, are prepared by a process in which a diamine of the formula ##STR2## where R.sup.1, R.sup.2 and X are the groups described above, is reacted with an olefin of the formula ##STR3## where R.sup.6 and R.sup.9 are each hydrogen or alkyl which is straight-chain in the .alpha.-position, in the presence of a zeolite as a catalyst.Type: GrantFiled: June 15, 1988Date of Patent: April 3, 1990Assignee: BASF AktiengesellschaftInventors: Michael Hesse, Wolfgang Hoelderich, Matthias Schwarzmann
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Patent number: 4912259Abstract: A pentadiene compound of the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is a C.sub.1 -C.sub.4 alkyl group or a substituted or unsubstituted aryl or aralkyl group, R.sub.5 is an alkyl group, and X is a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group or a halogen atom.Type: GrantFiled: August 5, 1988Date of Patent: March 27, 1990Assignee: Hodogaya Chemical Co., Ltd.Inventors: Kazuo Kaneko, Masahiko Yamaguchi, Michihiro Gonda, Kensaku Okano, Kazuyuki Wakasugi
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Patent number: 4876282Abstract: The present invention provides 1-phenyl-(naphthalenyl)alkylamines which are selective inhibitors of serotonin uptake.Type: GrantFiled: November 25, 1987Date of Patent: October 24, 1989Assignee: Eli Lilly and CompanyInventors: David W. Robertson, David T. Wong
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Patent number: 4855502Abstract: Novel 4-phenyl-1,3-benzodiazepines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants.Type: GrantFiled: August 27, 1982Date of Patent: August 8, 1989Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Lawrence L. Martin, Manfred Worm, Charles A. Crishlow
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Patent number: 4836958Abstract: The instant invention relates to fluorinated cationic compounds of the formula ##STR1## wherein R.sub.f is a perfluoroalkyl or perfluoroalkoxy-perfluoroalkyl group;R.sub.1 is alkylene optionally interrupted by --O--, --S--, --SO.sub.2 --, --SO.sub.2 NR'--, --CO.sub.2 --, --NR'--, or --CONR'-- where R' is hydrogen or lower alkyl;m is 0, 1 or 2;R.sub.2 is linear or branched alkylene;R.sub.3, R.sub.4, and R.sub.5 independently of one another represent alkyl or arylalkyl groups which are unsubstituted or substituted by hydroxyl, lower alkoxy, halogen, cyano or by polyalkyleneoxy, or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical or R.sub.3, R.sub.4 and R.sub.5 together with nitrogen atom that links them represent a substituted or unsubstituted pyridine ring; andA.sup..crclbar. represents the anion of an organic or inorganic acid; and their particular use as surfactants.Type: GrantFiled: July 31, 1986Date of Patent: June 6, 1989Assignee: Ciba-Geigy CorporationInventor: Athanasios Karydas
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Patent number: 4822914Abstract: Novel 4-phenyl-1,3-benzodiazepines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants.Type: GrantFiled: August 27, 1982Date of Patent: April 18, 1989Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Lawrence L. Martin, Manfred Worm, Charles A. Crichlow
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Patent number: 4716248Abstract: New compounds having the formula:X--(YQNH.sub.2).sub.p Iwherein p is 1 or 2 and the residues QNH.sub.2 are the same or different and each is a residue of formula: ##STR1## wherein n is an integer from 1 to 15; R.sub.1 is C.sub.1 -C.sub.8 alkyl; R.sub.2 is C.sub.1 -C.sub.4 alkyl; or R.sub.1 and R.sub.2 ; together with the carbon atom to which they are attached, from a C.sub.5 -C.sub.8 cycloalkylene residue; R.sub.3 is H or C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl or C.sub.6 -C.sub.10 aryl; and Y is a divalent residue of formula: ##STR2## wherein R.sub.4 and R.sub.5 are H or C.sub.1 -C.sub.4 alkyl or, when p is 1, the group R.sub.4, together with the group X, can form a tetramethylene chain substituted by the group QNH.sub.2, X is NH.sub.2 or QNH.sub.2 or X may be combined with R.sub.4 as hereinbefore defined; and, when p is 2, X is a direct bond or a --CH.sub.Type: GrantFiled: October 12, 1984Date of Patent: December 29, 1987Assignee: Ciba-Geigy CorporationInventors: Frederick H. Howell, Josef Pfeifer
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Patent number: 4647446Abstract: A method for detecting the blood flow in animals, particularly in the brain, is provided wherein a detectable amount of a novel radioactive compound of the formula I is administered to one animal: ##STR1## wherein R.sub.1 and R.sub.2 are independently alkyl of 1 to 6 carbon atoms or benzyl;R.sub.3 is alkyl of 1 to 6 carbon atoms, benzyl, cyclopropylalkyl of 4 to 6 carbon atoms, or cyanoalkyl of 2 to 6 carbon atoms;R.sub.4 is hydrogen, benzyl or alkyl of 1 to 6 carbon atoms;with the provisos that R.sub.4 is not isopropyl and when R.sub.4 is methyl, R.sub.3 is not benzyl;and X is a radioactive halogen.Type: GrantFiled: May 9, 1985Date of Patent: March 3, 1987Assignee: The Regents of the University of CaliforniaInventors: Thornton W. Sargent, III, Alexander T. Shulgin, Chester A. Mathis
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Patent number: 4600797Abstract: Process for the preparation of a nitroaminobenzene by nitrating an aminobenzene which is protected at the nitrogen wherein the nitration is carried out by the simultaneous combination of nitric acid and the aminobenzene to be nitrated, in the presence of inert solvents such as methylene chloride.Type: GrantFiled: February 18, 1983Date of Patent: July 15, 1986Assignee: Bayer AktiengesellschaftInventor: Willi Schossler
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Patent number: 4550206Abstract: Tetrahalobenzene compounds of the formula (I): ##STR1## in which X is independently chloro or, preferably, fluoro and Y is hydrogen or --N.sup.+ R.sub.3 A.sup.- in which each R is independently C.sub.1-4 alkyl and A is a radical capable of forming an anion A.sup.-, are prepared by(a) alkylating a compound of formula (II): ##STR2## or a salt thereof, to form a compound of formula (III): ##STR3## (b) treating the compound of formula (III) with a quaternizing agent of formula RA to form a compound of formula (IV): ##STR4## and (c) partially or completely reductively cleaving the compound of formula (IV) to replace one or both --N.sup.+ R.sub.3 A.sup.- groups by hydrogen.Compounds (I), in which Y is --N.sup.+ R.sub.3 A.sup.-, (III) and (IV) are novel. Compound (I) is useful in the synthesis of insecticides.Type: GrantFiled: January 11, 1984Date of Patent: October 29, 1985Assignee: Imperial Chemical Industries LimitedInventor: Peter J. Richardson
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Patent number: 4536599Abstract: An amine of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each hydrogen, alkyl or the like and n is 1, 2 or 3, including .alpha.-phenyl-.beta.-(p-tolyl)-ethylamine, which is useful as an optically resolving agent, an intermediate of medicines and the like, is effectively produced by a novel process comprising hydrolysis of the corresponding nitrile of the formula, ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and n are the same as above, followed by alkali-decomposition of the resulting amide of the formula, ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and n are the same as above. An amide including the above one is effectively produced by hydrolysis of the corresponding nitrile in the presence of a base and hydrogen peroxide using an organic quaternary ammonium salt and/or a tertiary amine as a catalyst.Type: GrantFiled: November 1, 1979Date of Patent: August 20, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Fujio Masuko, Tadashi Katsura
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Patent number: 4536601Abstract: Optically active N-substituted phenylalaninols of the formula (I): ##STR1## wherein R is isopropyl, 1-ethylpropyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylbenzyl, 4-methoxybenzyl, or 3,4-methylenedioxybenzyl; and acid addition salts thereof which are useful as a resolving agent, and a process for preparing D-3-acetylthio-2-methylpropionic acid which comprises reacting DL-3-acetylthio-2-methylpropionic acid with an optically active N-substituted phenylalaninol of the formula (I) to form diastereomeric salts, subjecting the formed diastereomeric salts to a fractional crystallization from a solvent to separate the D-acid salt from the L-acid salt, and then decomposing the D-acid salt with a mineral acid to give D-3-acetylthio-2-methylpropionic acid.Type: GrantFiled: September 23, 1983Date of Patent: August 20, 1985Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Masatoshi Tukamoto, Tadahiro Sawayama
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Patent number: 4463191Abstract: There is disclosed a process for the reductive alkylation of aromatic nitro-containing compounds with ketones or aldehydes wherein the improvement is characterized in that a specific polymer bound co-catalyst system is utilized. More specifically, a polymer bound anthranilic acid palladium complex is used in conjunction with a bound sulfonic acid resin as a catalyst system in a reaction to produce compounds such as N-phenyl-N'-alkyl-p-phenylenediamine.Type: GrantFiled: September 26, 1983Date of Patent: July 31, 1984Assignee: The Goodyear Tire & Rubber CompanyInventors: Richard M. D'Sidocky, Dane K. Parker
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Patent number: 4461728Abstract: The invention relates to compounds of the formula ##STR1## where Y is --OH; halogen; ##STR2## where R.sub.1 is a straight chain or branched chain alkyl group having 1 to 5 carbon atoms, or aryl; and R.sub.2 is --C(CH.sub.3).sub.3 or --O--C(CH.sub.3).sub.3. Processes for preparing the compounds are provided. The compounds are useful as intermediates in the preparation of 4-phenyl-1,3-benzodiazepins, which exhibit activity as antidepressants, analgetics and anticonvulsants.Type: GrantFiled: November 12, 1982Date of Patent: July 24, 1984Assignee: Hoechst Roussel Pharmaceuticals Inc.Inventors: Thomas B. K. Lee, George E. Lee
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Patent number: 4396517Abstract: Reaction products from certain phenol, aldehydes and amines are effective friction reducing additives in lubricants and in liquid fuels, such as gasoline and alcohol fuels.Type: GrantFiled: August 10, 1981Date of Patent: August 2, 1983Assignee: Mobil Oil CorporationInventors: Robert M. Gemmill, Jr., Andrew G. Horodysky
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Patent number: 4360511Abstract: Certain radioiodine containing amines useful as brain imaging agents are disclosed. The compounds of the invention are represented by the formula ##STR1## wherein I is a radioisotope of iodine with I-123 being preferred, R is lower alkyl or halogen, R.sub.1 and R.sub.2 are the same or different and are selected from the group consisting of hydrogen and lower alkyl, R.sub.3 and R.sub.4 are the same or different and are selected from the group consisting of hydrogen, alkyl, aryl, substituted aryl, aralkyl, substituted aralkyl and substituted carbamoyl methyl or R.sub.3 and R.sub.4 taken together with the nitrogen to which they are attached form a 5- or 6-membered ring which may be substituted with one or more lower alkyl groups, x is 0 to 4, y is 0 to 3 and z is 0 or 1 and pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: June 19, 1980Date of Patent: November 23, 1982Assignee: Medi-Physics, Inc.Inventors: Ronald M. Baldwin, Tz-Hong Lin, Harry S. Winchell
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Patent number: 4312861Abstract: Aralkylamines of the formula:R.sup.1 --CH.sub.2 --N(R.sup.3)--R.sup.2whereinR.sup.1 is a phenyl substituted by one of:(I) alkyls,(II) halo and(III) nitro;R.sup.2 is(IV) alkyl having from 4 to 10 carbon atoms, four of which are in one chain,(V) alkyl interrupted by an oxygen atom, i.e. an alkoxyalkyl or ether radical, or(VI) hydroxyalkyl wherein the alkyl is either (IV) or (V) and the hydroxy is the sole substituent;R.sup.3 is a hydrogen atom, alkyl having from 1 to 4 carbon atoms or such alkyl substituted by a dialkylphosphinyl group;a physiologically-compatible acid-addition salt thereof and a pharmaceutical composition containing such compound(s) as active ingredient(s) are valuable in view of the physiological activity, e.g. vasotonic, capillary sealing and antiarrhythmic, of the aralkylamines and their physiologically-compatible acid-addition salts.Type: GrantFiled: June 13, 1977Date of Patent: January 26, 1982Assignee: Hoechst AktiengesellschaftInventors: Istvan Boksay, Alfons Soder, Volkher Bollmann, Rolf-Ortwin Weber
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Patent number: 4309424Abstract: Novel 4-phenyl-1,3-benzodiazepines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants.Type: GrantFiled: November 5, 1979Date of Patent: January 5, 1982Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Lawrence L. Martin, Manfred Worm, Charles A. Crichlow
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Patent number: 4292242Abstract: Aminomethylation of olefins which employs a homogeneous catalyst which is a solution in a suitable solvent of mixed ruthenium and iron carbonyls. The overall reaction may be represented as follows: ##STR1## where R.sub.1 and R.sub.2 are hydrogen or essentially hydrocarbon groups. The reaction proceeds by way of an aldehyde intermediate. Accordingly, the starting material may be an aldehyde instead of an olefin.Type: GrantFiled: August 26, 1980Date of Patent: September 29, 1981Assignee: SRI InternationalInventor: Richard M. Laine
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Patent number: 4288626Abstract: A process for prolonging the activity of catalysts during the hydrogenation of unsaturated dinitriles comprising pretreating the dinitrile feed with a crystalline zeolite.Type: GrantFiled: September 5, 1980Date of Patent: September 8, 1981Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: RE35053Abstract: Disclosed are .DELTA..sup.9(11) -steroids (VI) and amino substituted steroids (XI) which contain an amino group attached to the terminal carbon atom of the C.sub.17 -side chain, more particularly amino steroids (Ia and Ib), aromatic steroids (II), .DELTA..sup.16 -steroids (IIIa and IIIb), reduced A-ring steroids (IV), .DELTA..sup.17(20) -steroids (Va and Vb) and .DELTA..sup.9(11) -steroids (VI) which are useful as pharmaceutical agents for treating a number of conditions.Type: GrantFiled: October 9, 1992Date of Patent: October 10, 1995Assignee: The Upjohn CompanyInventors: John M. McCall, E. Jon Jacobsen