Acyclic Hydrocarbyl Group Bonded Directly To The Methylene Carbon Patents (Class 564/392)
  • Publication number: 20150105559
    Abstract: Disclosed is a method for producing a compound having an amino group and/or a hydroxyl group from a substrate compound having an atomic group containing CO or CS by eliminating such atomic group. The substrate compound, having an atomic group containing CO or CS (for example, an amide, a carbamate, or the like), is allowed to react with a compound expressed by formula (I) below, at a temperature of 120° C. or lower, preferably in the presence of an ammonium salt, to eliminate such atomic group containing CO or CS. In formula (I) A may not be present, and in a case where A is present, A represents an alkyl group having 1 to 6 carbon atoms. H2N-A—NH2 (I) - - -.
    Type: Application
    Filed: March 4, 2013
    Publication date: April 16, 2015
    Applicant: Kyushu University, National University Corporation
    Inventors: Takashi Ohshima, Hiroyuki Morimoto, Yuhei Shimizu
  • Patent number: 8846125
    Abstract: The present invention relates to enaminocarbonyl compounds with the formula I. The present invention also relates to the use of compounds with the formula I for the modification of the taste of a product and/or preparation for oral administration.
    Type: Grant
    Filed: February 2, 2010
    Date of Patent: September 30, 2014
    Assignee: Instytut Chemii Organicznej, Polska Akademia Nauk
    Inventors: Piotr Krajewski, Agnieszka Woźniak
  • Publication number: 20140142304
    Abstract: There is provided a process for producing an aminopropyne or an enaminone comprising the step of reacting a metal acetylide, an amine and a carbonyl-containing compound in the presence of a transition metal catalyst. There is also provided a process for producing an aminopropyne comprising the step of reacting a metal acetylide, an amine and a halide-containing compound in the presence of a transition metal catalyst at a reaction temperature of 50° C. to 150° C. There are also provided processes to further synthesize the aminopropyne produced to obtain a butyneamine, another aminopropyne or a triazol.
    Type: Application
    Filed: July 6, 2012
    Publication date: May 22, 2014
    Applicant: Agency for Science, Technology and Research
    Inventors: Yugen Zhang, Dingyi Yu, Zhewang Lin
  • Publication number: 20140046095
    Abstract: A method of preparing (S)-2-amino-5-methoxytetralin hydrochloride[(S)-2-amino-5-methoxyl-1,2,3,4-tetrahydronaphthalene hydrochloride], comprising the steps of: (1) producing a compound (I) by addition-elimination reaction of 5-methoxy-2-tetralone and R-(+)-a-phenylethylamine; (2) producing a compound (II) by reduction reaction of the compound (I) with a reducing agent; and (3) producing a compound (II) hydrochloride by reacting the compound (II) with a salt-forming agent, then carrying out reduction reaction with a palladium-carbon catalyst to produce (S)-2-amino-5-methoxytetralin hydrochloride. The method can significantly increase the yield of (S)-2-amino-5-methoxytetralin hydrochloride with short synthetic path, low preparation cost and less pollution, which is environmentally friendly and is suitable for medical industrialized production. The structural formulae of the compound (I) and the compound (II) are: resepectively.
    Type: Application
    Filed: August 8, 2012
    Publication date: February 13, 2014
    Applicant: ANHUI KELONG INSTITUTE OF PHARMACEUTICAL
    Inventors: Qingyun HUANG, Qingguo HUANG, Meixian LOU
  • Publication number: 20140039181
    Abstract: The invention relates to a method for producing a N-substituted amine compound by catalyzed alkylation. The method uses amine and alcohol or two kinds of amines as the reaction materials, employs composite metal oxides catalyst at a reaction temperature of 80-180° C. to catalyze the reaction for 6-36 hours, so as to produce the N-substituted amine compound. The reaction condition of the method of the invention is relatively moderate, using a catalyst made of cheap non-noble metals, which is non-caustic and easy to be separated and reused. The reaction does not need any medium and has relatively high conversion rate and selectivity.
    Type: Application
    Filed: December 28, 2012
    Publication date: February 6, 2014
    Applicant: Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences
    Inventor: Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences
  • Publication number: 20110274803
    Abstract: The present invention relates to enaminocarbonyl compounds with the formula I, in which X denotes O or CH2, Y denotes N and each of R1 and R2 denotes hydrogen, or Y denotes a CH and either R1 or R2 denotes a C1-4 alkyl, and the remaining R1 or R2 denotes hydrogen, selected (for Y denoting CH and R1 or R2 denoting a C1-4 alkyl) from a group encompassing a mixture of R and S enantiomers enriched in either enantiomer R or enantiomer S, enantiomer R and enantiomer S. The present invention also relates to the use of compounds with the formula I, in which X denotes O or CH2, Y denotes a CH and either R1 or R2 is selected from a group encompassing hydrogen and a C1-4 alkyl, and the remaining R1 or R2 denotes hydrogen, for the modification of the taste of a product and/or preparation for oral administration.
    Type: Application
    Filed: February 2, 2010
    Publication date: November 10, 2011
    Inventors: Piotr Krajewski, Agnieszka Wozniak
  • Publication number: 20110213146
    Abstract: One aspect of the invention relates to a method of animation or amidation, comprising the step of combining a substrate, comprising a reactive C—H bond, and an amine or amide, comprising a reactive N—H bond, in the presence of an oxidizing agent and a metal-containing catalyst, thereby forming a product with a covalent bond between the carbon of the reactive C—H bond and the nitrogen of the reactive N—H bond.
    Type: Application
    Filed: September 3, 2009
    Publication date: September 1, 2011
    Applicant: Georgetown University
    Inventor: Timothy H. Warren
  • Patent number: 7393979
    Abstract: The present invention relates to a process for producing an optically active 1-alkyl-substituted 2,2,2-trifluoroethylamine, which is an important intermediate of medicines and agricultural chemicals, and which is represented by the formula [3] [in the formula R represents a lower alkyl group of a carbon and * represents an asymmetric carbon], or its salt by subjecting an optically active imine represented by the formula [1] to an asymmetric reduction under hydrogen atmosphere using a metal catalyst of Group VIII to convert it into an optically active secondary amine represented by the formula [2] and then by subjecting the secondary amine or its salt to hydrogenolysis. [Chem.
    Type: Grant
    Filed: June 8, 2004
    Date of Patent: July 1, 2008
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Yokusu Kuriyama, Manabu Yasumoto, Masatomi Kanai, Kenjin Inomiya, Takashi Ootsuka, Koji Ueda
  • Patent number: 7081551
    Abstract: Optically active (R)-1-(4-trifluoromethylphenyl)ethylamine is a novel compound as an important intermediate for medicines and agricultural chemicals. This compound can be obtained with high optical purity and high yield by a process including the steps of (a) a dehydrocondensation of 4?-(trifluoromethyl)acetophenone and an optically active (R)-1-phenylethylamine to obtain an optically active imine; (b) asymmetrically reducing the imine into an optically active secondary amine; (c) reacting the amine with an organic acid (phthalic acid or benzenesulfonic acid), thereby obtaining a product that is a phthalate of or benzenesulfonate of the amine; (d) subjecting the product of the step (c) to a hydrogenolysis, thereby obtaining a product that is a phthalate of or benzenesuilfonate of optically active (R)-1-(4-trifluoromethylphenyl)ethylamine; and (e) neutralizing the product of the step (d) into the optically active (R)-1-(4-trifluoromethylphenyl)ethylamine.
    Type: Grant
    Filed: May 21, 2003
    Date of Patent: July 25, 2006
    Assignee: Central Glass Co., Ltd.
    Inventors: Akihiro Ishii, Manabu Yasumoto, Yokusu Kuriyama, Masatomi Kanai, Kanjin Inomiya
  • Publication number: 20040235961
    Abstract: An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula 4 is produced by a process including (a) reacting an optically active secondary amine, represented by the formula 1, with an alkylation agent R2—X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula 3; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative, 1
    Type: Application
    Filed: November 4, 2003
    Publication date: November 25, 2004
    Inventors: Akihiro Ishii, Masatomi Kanai, Yokusu Kuriyama, Manabu Yasumoto, Kenjin Inomiya, Takashi Ootsuka, Koji Ueda
  • Patent number: 6765023
    Abstract: The invention relates to substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-disubstituted reverse aminoalcohols.
    Type: Grant
    Filed: May 23, 2002
    Date of Patent: July 20, 2004
    Assignee: Pfizer, Inc.
    Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6723753
    Abstract: The invention relates to substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N-benzyl-N-phenyl aminoalcohols.
    Type: Grant
    Filed: February 7, 2002
    Date of Patent: April 20, 2004
    Assignee: Pharmacia Corporation
    Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6723752
    Abstract: The invention relates to substituted aryl and heteroaryl (R)-Chiral Halogenated 1-Substitutedamino-(n+1 )-Alkanol compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Novel high yield, stereoselective processes for the preparation of the chiral substituted alkanol compounds from chiral and achiral intermediates are described. Preferred (R)-Chiral 1-Substitutedamino-(n+1)-Alkanol compounds are substituted (R)-Chiral N-benzyl-N-phenyl aminoalcohols.
    Type: Grant
    Filed: December 12, 2001
    Date of Patent: April 20, 2004
    Assignee: Pharmacia Corporation
    Inventors: James A. Sikorski, Richard C. Durley, Margaret L. Grapperhaus, Mark A. Massa, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Brian S. Hickory, Monica B. Norton, William F. Vernier, Deborah A. Mischke, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6683099
    Abstract: The invention relates to substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-disubstituted cycloalkyl aminoalcohols.
    Type: Grant
    Filed: May 23, 2002
    Date of Patent: January 27, 2004
    Assignee: Pharmacia Corporation
    Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6683113
    Abstract: The invention relates to substituted aryl and heteroaryl (R)-Chiral Halogenated 1-Substitutedamino-(n+1)-Alkanol compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Novel high yield, stereoselective processes for the preparation of the chiral substituted alkanol compounds from chiral and achiral intermediates are described. Preferred (R)-Chiral 1-Substitutedamino-(n+1)-Alkanol compounds are substituted (R)-Chiral N,N-bis-benzyl aminoalcohols.
    Type: Grant
    Filed: December 12, 2001
    Date of Patent: January 27, 2004
    Assignee: Pharmacia Corporation
    Inventors: James A. Sikorski, Richard C. Durley, Margaret L. Grapperhaus, Mark A. Massa, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Brian S. Hickory, Monica B. Norton, William F. Vernier, Deborah A. Mischke, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6677375
    Abstract: The invention relates to substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-bis-benzyl aminoalcohols.
    Type: Grant
    Filed: May 23, 2002
    Date of Patent: January 13, 2004
    Assignee: Pharmacia Corporation
    Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6677380
    Abstract: The invention relates to substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-disubstituted mercapto amines.
    Type: Grant
    Filed: May 23, 2002
    Date of Patent: January 13, 2004
    Assignee: Pharmacia Corporation
    Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6476075
    Abstract: The invention relates to substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-bis-benzyl aminoalcohols.
    Type: Grant
    Filed: November 14, 2001
    Date of Patent: November 5, 2002
    Assignee: G.D. Searle & Co.
    Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6476057
    Abstract: The invention relates to use of substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-disubstituted cycloalkyl aminoalcohols.
    Type: Grant
    Filed: November 14, 2001
    Date of Patent: November 5, 2002
    Assignee: G.D. Searle & Co.
    Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6462092
    Abstract: The invention relates to use of substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-disubstituted reverse aminoalcohols.
    Type: Grant
    Filed: November 14, 2001
    Date of Patent: October 8, 2002
    Assignee: G.D. Searle & Co.
    Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6458849
    Abstract: The invention relates to use of substituted polycyclic aryl and heteroaryl tertiary-heteroalkyamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-disubstituted mercapto amines.
    Type: Grant
    Filed: November 14, 2001
    Date of Patent: October 1, 2002
    Assignee: G.D. Searle & Co.
    Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6362373
    Abstract: The disclosed invention comprises a compound having the formula: in which R1 and R2 independently represent a hydrogen or an alkyl group of 4 carbon atoms or greater. Further disclosed is a process for the preparation of the disclosed chiral amino alcohols from a starting amine compound and a limonene oxide.
    Type: Grant
    Filed: September 13, 2000
    Date of Patent: March 26, 2002
    Assignees: The Dow Chemical Company
    Inventors: Christian T. Goralski, Bakthan Singaram, William Chrisman
  • Patent number: 6291713
    Abstract: 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: Grant
    Filed: September 23, 1999
    Date of Patent: September 18, 2001
    Assignee: Metallgesellschaft Aktiengesellschaft
    Inventors: Philip Jones, Paul Knochel
  • Patent number: 6037498
    Abstract: This invention relates to novel compounds of general formula (I) ##STR1## wherein R.sup.1 represents an organic group, R.sup.2 represents a hydrogen atom or an organic group, and the asterisk denotes that the group R.sup.1 is predominantly in the R- or S-configuration such that the compound is in substantially enantiomerically pure form. The compounds are a useful source of chiral nucleophiles, e.g. undergoing stereoselective Michael addition to .alpha.,.beta.-unsaturated carboxylic acid derivatives.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: March 14, 2000
    Assignee: Oxford Asymmetry International PLC
    Inventors: Stephen Graham Davies, Mario Eugenio Cosamino Polywka, David Roy Fenwick, Frank Reed
  • Patent number: 6001884
    Abstract: The present invention features molecules which can modulate one or activities of an inorganic ion receptor. Preferably, the molecule can mimic or block the effect of extracellular Ca.sup.2+ on a calcium receptor. The preferred use of such molecules is to treat diseases or disorders by altering inorganic ion receptor activity, preferably calcium receptor activity.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: December 14, 1999
    Assignee: NPS Pharmaceuticals, Inc.
    Inventors: Edward F. Nemeth, Bradford C. Van Wagenen, Manuel F. Balandrin, Eric G. Delmar, Scott T. Moe
  • Patent number: 5981599
    Abstract: The present invention features compounds able to modulate one or more activities of an inorganic ion receptor and methods for treating diseases or disorders using such compounds. Preferred compounds can mimic or block the effect of extracellular calcium on a cell surface calcium receptor.
    Type: Grant
    Filed: April 30, 1997
    Date of Patent: November 9, 1999
    Assignee: NPS Pharmaceuticals, Inc.
    Inventors: Scott T. Moe, Bradford C. Van Wagenen, Eric G. DelMar, Richard Trovato, Manuel F. Balandrin
  • Patent number: 5932726
    Abstract: The present invention provides novel methods for the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1- benzoxazin-2-one of formula (VI-i) ##STR1## which is useful as a human immunodeficiency virus (HIV) reverse transcriptase inhibitor.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: August 3, 1999
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Michael Ernest Pierce, Anusuya Choudhury, Rodney Lawrence Parsons, Jr., Lilian Alicia Radesca
  • Patent number: 5872299
    Abstract: 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: Grant
    Filed: May 8, 1997
    Date of Patent: February 16, 1999
    Assignee: 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
  • Patent number: 5773617
    Abstract: 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: Grant
    Filed: February 22, 1996
    Date of Patent: June 30, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Marie Bernard, Errol Blart, Jean-Pierre Genet, Sandrine Lemaire-Audoire, Monique Savignac
  • Patent number: 5739405
    Abstract: 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: Grant
    Filed: December 4, 1996
    Date of Patent: April 14, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Karsten Eller, Rudolf Kummer, Peter Stops
  • Patent number: 5726308
    Abstract: 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: Grant
    Filed: March 22, 1996
    Date of Patent: March 10, 1998
    Assignee: FMC Corporation
    Inventors: Randy W. Hall, Robert S. Wedinger, Terry L. Rathman, James A. Schwindeman
  • Patent number: 5686616
    Abstract: A novel process for preparing an optically active amine by asymmetric hydrogenation of an imine compound, such as an imine compound prepared by condensing benzylamine and acetophenone, in the presence of a catalytic amount of an iridium-optically active phosphine complex and benzylamine or a benzylamine derivative. The present invention provides an optically active amine of high optical purity.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: November 11, 1997
    Assignee: Takasago International Corporation
    Inventors: Kazuhide Tani, Tsuneaki Yamagata, Yasutaka Kataoka, Hidenori Kumobayashi
  • Patent number: 5665756
    Abstract: Novel aminoalkyloximes of the formula ##STR1## wherein: a. X is hydrogen, loweralkyl, loweralkoxy, halogen, trifluoromethyl, or a group of the formula ##STR2## wherein Y is hydrogen or loweralkyl, and p is 1 or 2; b. A is a group of the formula ##STR3## c. R.sup.1 and R.sup.2 are independently hydrogen or lowerakyl; and d. m is 2 to 6 and n is 0, or 2 to 6, inclusive, serotonin reuptake inhibitors, useful for treating depression and obsessive compulsive disorders are described. Also described are precursors of and processes for the preparation of such aminoakyloximes.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: September 9, 1997
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
  • Patent number: 5292893
    Abstract: A process is provided for catalytically reducing imines, oximes, hydrazones and related compounds. Moreover, there is provided a process for the catalytic asymmetric reduction of imines, oximes, hydrazones, and the like, using enantiomerically enriched catalysts, to provide chiral amine reaction products which are enriched in one enantiomer. Catalytic asymmetric reduction can also be carried out using an achiral precatalyst in combination with aThe U.S. Government has rights in this invention pursuant to NIH Grant Number GM 34917.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: March 8, 1994
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Christopher A. Willoughby
  • Patent number: 5117061
    Abstract: Novel anilines of the 2,6-dialkyl-4-dialkylaminomethylaniline type are prepared by reacting a secondary amine and an aldehyde with a primary aniline reactant having a free para position and substituents in both ortho positions in the presence of an acid catalyst, the amounts of amine and acid employed being at least equimolar with respect to the amount of aldehyde, and the reaction being conducted by adding the primary aniline reactant to a preformed mixture of the secondary amine, aldehyde, and acid.
    Type: Grant
    Filed: May 12, 1986
    Date of Patent: May 26, 1992
    Assignee: Ethyl Corporation
    Inventor: Kju H. Shin
  • Patent number: 5017723
    Abstract: Substituted ethylamines of the formula ##STR1## wherein R.sub.1 is phenyl optionally mono-, di- or trisubstituted by halogen, lower alkyl, lower haloalkyl or lower alkoxy, or is an aromatic heterocycle having 5 to 7 chains wherein the heteroatom is nitrogen, oxygen or sulfur,R.sub.2 is lower alkyl,R.sub.3 and R.sub.4, each independently, represent hydrogen, lower alkyl or lower alkenyl,R.sub.5 is phenyl optionally mono-, di- or trisubstituted by halogen or lower alkoxy or is an aromatic heterocycle having 5 to 7 chains wherein the heteroatom is nitrogen, oxygen or sulfur andQ represents a --CH.dbd.CH-- ethylene group or a 1,2-diyl ##STR2## propane group, their acid addition salts and their optically active forms. These substituted ethylamines have psycotropic properties and are useful as medicines.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: May 21, 1991
    Assignee: Jouveinal S.A.
    Inventors: Gilbert G. Aubard, Alain P. Calvet, Claude J. Gouret, Agnes M. Grouhel, Henry L. Jacobelli, Jean-Louis Junien, Xavier B. Pascaud, Francois J. Roman, Claude D. Soulard, James P. Hudspeth, Yuan Lin
  • Patent number: 4990669
    Abstract: The invention relates to new optically active .alpha.-amino aldehydes of the formulae ##STR1## in which R.sub.1 represents an optionally substituted alkyl, alkenyl, aralkyl or aryl radical, andR.sub.2 and R.sub.3, independently of one another, denote an optionally substituted alkyl, alkenyl, cycloalkyl or aralkyl group, together form an optionally substituted phenylene-(1,2)-bis-methylene radical, or R.sub.2 is an optionally substituted, alkyl, cycloalkyl or aralkyl radical, and R.sub.3 forms together with R.sub.1 a 1,3-propylene radical.a process for the preparation thereof, and the use thereof for the stereoselective preparation of optically active .beta.-amino alcohols.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred T. Reetz, Mark W. Drewes
  • Patent number: 4962234
    Abstract: An antioxidant for lubricating oils comprising an amine compound selected from substituted benzylamines or a substituted 1-amino-1,2,3,4-tetrahydro-naphthalene. The preferred anti-oxidants are N-(alpha -methyl -p -octylbenzyl) aniline, N-(alpha-methylbenzyl)- p -nonylaniline or 1-( p -dodecylanilino)-1,2,3,4-tetrahydronaphthalene.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: October 9, 1990
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Baldev K. Bandlish, Frederick C. Loveless, Walter Nudenberg
  • Patent number: 4921980
    Abstract: A process for the preparation of N-alkylanilines is described, the most essential feature of which comprises reacting corresponding anilines at 150.degree. to 300.degree.C. with corresponding alcohols in the presence of a catalyst consisting of silica gel as carrier, of 0.2 to 10% of platinum and of 0.05 to 3% of a compound of a metal of the groups Ia and/or IIa of the Periodic Table, with the catalyst additionally containing at least one compound of an element of the groups Ib, IVa, IVb, Vb, VIIb and VIII in such an amount that the atomic ratio of platinum to the sum of these elements is 1 to 6.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: May 1, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Milos Rusek
  • Patent number: 4898986
    Abstract: Disclosed is a novel inosose compound represented by the general formula: ##STR1## wherein X.sup.1 and X.sup.2 are both halogen; X.sup.1 is hydrogen and X.sup.2 is halogen; or X.sup.1 is --SQ.sup.1 and X.sup.2 is --SQ.sup.2 (each of Q.sup.1 and Q.sup.2 is lower alkyl or Q.sup.1 and Q.sup.2 may form lower alkylene), R.sup.1 is a protective group for hydroxyl and Y is .dbd.O, .dbd.N--Z (Z is hydroxyl which may be protected) or ##STR2## (A is hydrogen or an amine residue), particularly to the compound wherein the symbol Y is oxygen.The inosose compound is useful as intermediates for production of valiolamine and the N-substituted derivatives thereof, which have potent .alpha.-glucosidase inhibiting activities and are useful as preventives or therapeutics for symptoms of hyperglycemia and various diseases derived therefrom in human and animals, such as diabetes, obesity and hyperlipemia.
    Type: Grant
    Filed: August 31, 1987
    Date of Patent: February 6, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Satoshi Horii, Hiroshi Fukase
  • Patent number: 4891424
    Abstract: 4-Aralkyl-2-nitro-2'-hydroxy-3',5'-dialkyl (or cumyl)-azobenzenes are made by coupling the corresponding diazotized 4-aralkyl-o-nitroaniline with the corresponding phenol. These azobenzene intermediates are used to prepare the corresponding 2H-benzotriazole UV absorber stabilizers substituted on the 5-position of the benzo ring by an aralkyl group, preferably alpha,alpha-dimethylbenzyl.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: January 2, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Roland A. E. Winter
  • Patent number: 4795757
    Abstract: Compounds of the formula: ##STR1## and pharmaceutically acceptable salts thereof, wherein: Ar is phenyl, naphthyl, heteroaryl, indole, or fused arylcycloalkyl optionally substituted with hydroxy, halo, CF.sub.3, NO.sub.2, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or aryloxy;A and A' are each hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy or aryloxy;X is cyano, nitro, COOR, SR, SOR or SOOR;R is H, C.sub.1-6 alkyl or aryl;n n' and n" are each 0 to 4; andm, m' and m" are each 1 to 4, have calcium channel blocking activity.
    Type: Grant
    Filed: November 20, 1986
    Date of Patent: January 3, 1989
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: John R. Regan, Jeffrey N. Barton, John T. Suh, Jerry W. Skiles
  • Patent number: 4777294
    Abstract: A compound of the formula: ##STR1## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group, or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, B is hydrogen or hydroxyl, and their production and use.These compounds exhibit excellent inhibitory activity against .alpha.-glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: October 11, 1988
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase
  • Patent number: 4701559
    Abstract: A compound of the formula: ##STR1## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group, or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, B is hydrogen or hydroxyl, and their production and use.These compounds exhibit excellent inhibitory activity against .alpha.-glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.
    Type: Grant
    Filed: December 28, 1981
    Date of Patent: October 20, 1987
    Assignee: Takeda Chemical Industries, Inc.
    Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase
  • Patent number: 4486602
    Abstract: A compound of the formula: ##STR1## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group; or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, and their production and use.These compounds exhibit excellent inhibitory activity against glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.
    Type: Grant
    Filed: September 29, 1981
    Date of Patent: December 4, 1984
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase
  • Patent number: 4484004
    Abstract: There are described novel substituted 1,11-diaminoundecanes, particularly those of the formula ##STR1## [R.sub.1 is alkyl having 1-12 C atoms, R.sub.2 is hydrogen or alkyl having 1-12 C atoms, R.sub.3 is alkyl having 1-12 C atoms, cycloalkyl having 4-12 C atoms, aralkyl having 7 or 8 C atoms, unsubstituted or substituted aryl, pyridyl, furyl or thienyl, R.sub.4 is hydrogen, alkyl having 1-12 C atoms, cycloalkyl having 4-12 C atoms, or unsubstituted or substituted aryl, or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together are alkylene having 3-11 C atoms], and processes for producing them. The compound of the formula I can be used for example for producing polycondensation products, particularly polyamides. They can be used also as curing agents for epoxide resins.
    Type: Grant
    Filed: September 22, 1982
    Date of Patent: November 20, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Reinehr, Josef Pfeifer
  • Patent number: 4463191
    Abstract: 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: Grant
    Filed: September 26, 1983
    Date of Patent: July 31, 1984
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Richard M. D'Sidocky, Dane K. Parker
  • Patent number: 4388206
    Abstract: An aqueous composition for inhibiting the corrosion of metals placed therein is described. The composition comprises a non-oxidizing acid, and, as a corrosion inhibitor, an effective amount of a 3-di(higher)alkylamino-3-phenylprop-1-yne.
    Type: Grant
    Filed: December 1, 1981
    Date of Patent: June 14, 1983
    Assignee: GAF Corporation
    Inventors: Eugene V. Hort, Lowell R. Anderson, Dru W. Alwani
  • Patent number: 4372956
    Abstract: A 5,10-dihydroimidazo[2,1-b]quinazoline in which at least one ring carbon atom, other than the carbon atom in the 2-position, bears a substituent, or a pharmaceutically acceptable acid addition salt thereof is a useful cardiotonic agent and vasodilator in heart insufficiency and a blood platelet aggregation inhibitor.
    Type: Grant
    Filed: November 18, 1980
    Date of Patent: February 8, 1983
    Assignee: Sandoz Ltd.
    Inventor: Hans Ott
  • Patent number: 4332807
    Abstract: Novel substituted-benzyl derivatives of 11-endo-amino-5,6,7,8,9,10-hexahydro-2-hydroxy (or methoxy)-6,9-methanobenzocyclooctene (or nonene) of the formula: ##STR1## are centrally-acting analgesics effective in the relief of pain.
    Type: Grant
    Filed: January 26, 1981
    Date of Patent: June 1, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Patrice C. Belanger, Robert N. Young