Phenethylamines Having Beta Alkyl Substituent Patents (Class 564/382)
  • Patent number: 8957067
    Abstract: A pharmaceutical composition comprising a drug substance consisting essentially of a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound wherein the amine containing pharmaceutical active compound is selected from the group consisting of racemic or single isomer ritalinic acid or phenethylamine derivatives and the drug substance has a physical form selected from amorphous and polymorphic.
    Type: Grant
    Filed: April 12, 2012
    Date of Patent: February 17, 2015
    Assignee: Pisgah Laboratories, Inc.
    Inventors: Clifford Riley King, Stephen G. D'Ambrosio, David W. Bristol
  • Patent number: 8877975
    Abstract: The invention relates to novel cyclohexylamine derivatives and their use in the treatment and/or prevention of central nervous system (CNS) disorders, such as depression, anxiety, schizophrenia and sleep disorder as well as methods for their synthesis. The invention also relates to pharmaceutical compositions containing the compounds of the invention, as well as methods of inhibiting reuptake of endogenous monoamines, such as dopamine, serotonin and norepinephrine from the synaptic cleft and methods of modulating one or more monoamine transporter.
    Type: Grant
    Filed: January 15, 2010
    Date of Patent: November 4, 2014
    Assignee: Sunovion Pharmaceuticals Inc.
    Inventors: Liming Shao, Fengjiang Wang, Scott Christopher Malcolm, Michael Charles Hewitt, Larry R. Bush, Jianguo Ma, Mark A. Varney, Una Campbell, Sharon Rae Engel, Larry Wendell Hardy, Patrick Koch, John E. Campbell
  • Patent number: 8716278
    Abstract: A pharmaceutical composition comprising a drug substance consisting essentially of a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound wherein the amine containing pharmaceutical active compound is selected from the group consisting of racemic or single isomer ritalinic acid or phenethylamine derivatives and the drug substance has a physical form selected from amorphous and polymorphic.
    Type: Grant
    Filed: April 11, 2012
    Date of Patent: May 6, 2014
    Assignee: Pisgah Laboratories, Inc.
    Inventors: Clifford Riley King, Stephen G. D'Ambrosio, David W. Bristol
  • Publication number: 20110124859
    Abstract: The present invention relates to a process for preparing betamimetics of formula 1, wherein n denotes 1 or 2; R1 denotes hydrogen, halogen, C1-4-alkyl or O—C1-4-alkyl; R2 denotes hydrogen, halogen, C1-4-alkyl or O—C1-4-alkyl; R3 denotes hydrogen, C1-4-alkyl, OH, halogen, O—C1-4-alkyl, O—C1-4-alkylene-COOH, O—C1-4-alkylene-COO—C1-4-alkyl.
    Type: Application
    Filed: February 7, 2011
    Publication date: May 26, 2011
    Applicant: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
    Inventors: Thomas KRUEGER, Uwe RIES, Juergen SCHNAUBELT, Werner RALL, Zeno A. LEUTER, Adil DURAN, Rainer SOYKA
  • Patent number: 7834062
    Abstract: The present invention relates to Mannich base antimalarial aminoalkylphenol compounds and their use against protozoa of the genus Plasmodium, particularly emerging strains of drug-resistant Plasmodia. This invention further relates to compositions containing such compounds and a process for making the compounds. This and other aspects of the invention are realized upon review of the entire specification.
    Type: Grant
    Filed: August 13, 2009
    Date of Patent: November 16, 2010
    Assignee: Merck Sharp & Dohme Corp.
    Inventors: Conrad P. Dorn, Mary Ann Powles, Thomas F. Walsh, Matthew J. Wyvratt
  • Publication number: 20100286124
    Abstract: The present invention relates to new prop-2-yn-1-amine inhibitors of monoamine oxidase type B activity, pharmaceutical compositions thereof, and methods of use thereof.
    Type: Application
    Filed: April 9, 2010
    Publication date: November 11, 2010
    Applicant: AUSPEX PHARMACEUTICALS, INC.
    Inventors: Thomas G. Gant, Sepehr Sarshar
  • Patent number: 7589127
    Abstract: The present invention relates to Mannich base antimalarial aminoalkylphenol compounds and their use against protozoa of the genus Plasmodium, particularly emerging strains of drug-resistant Plasmodia. This invention further relates to compositions containing such compounds and a process for making the compounds. This and other aspects of the invention are realized upon review of the entire specification.
    Type: Grant
    Filed: June 20, 2003
    Date of Patent: September 15, 2009
    Assignee: Merck & Co., Inc.
    Inventors: Conrad P. Dorn, Mary Ann Powles, Thomas F. Walsh, Matthew J. Wyvratt
  • Patent number: 7435267
    Abstract: The present invention relates to novel secondary para-phenylenediamines bearing an alkoxy group, to a process for preparing them, and to their use in the oxidation dyeing of hair. The invention also relates to a composition for dyeing keratin fibers, in particular human keratin fibers such as hair, containing, in a medium that is suitable for dyeing, at least one secondary para-phenylenediamine. Further, the invention relates to a process for dyeing keratin fibers using the aforementioned composition, and to a dyeing kit containing the composition.
    Type: Grant
    Filed: February 28, 2005
    Date of Patent: October 14, 2008
    Assignee: L'Oreal S.A.
    Inventors: Stéphane Sabelle, Jean-Jacques Vandenbossche
  • Patent number: 6861561
    Abstract: The invention relates to substituted aromatic polycyclic 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.
    Type: Grant
    Filed: September 26, 2002
    Date of Patent: March 1, 2005
    Assignee: G. D. Searle & Co.
    Inventors: James A. Sikorski, Richard C. Durley, Mark A. Massa, Jane L. Wang, Deborah A. Mischke, Barry L. Parnas, Melvin L. Rueppel
  • 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: 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: 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
  • Publication number: 20040049079
    Abstract: A method of inhibiting or preventing the use of anhydrous ammonia as a solvent in a dissolving metal reduction process comprises adding to anhydrous ammonia a chemical reagent which is capable of scavenging solvated electrons generated when alkali or alkaline earth metal is dissolved in the anhydrous ammonia, the chemical reagent being added to the anhydrous ammonia such that when alkali metal is dissolved in the anhydrous ammonia containing the chemical reagent and thereafter ephedrine, pseudoephedrine or combination thereof is introduced to the anhydrous ammonia to produce a reaction product, the methamphetamine yield in the reaction product is below 50%, preferably below 10%. and more preferably below 1%. Preferred chemical reagents include Fe(III)citrate, ferrocene, 2-chloro-6-(trichloromethyl)pyridine and 1,1,1,2-tetrafluoroethane.
    Type: Application
    Filed: December 9, 2002
    Publication date: March 11, 2004
    Inventors: George M. Murray, Craig A. Kelly, O. Manuel Uy, Lawrence W. Hunter, David S. Lawrence
  • 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: 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: 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: 6521667
    Abstract: The present invention features calcilytic compounds. “Calcilytic compounds” refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.
    Type: Grant
    Filed: August 11, 1998
    Date of Patent: February 18, 2003
    Assignees: NPS Pharmaceuticals, Inc., SmithKline Beecham, PLC, SmithKline Beecham, Corp.
    Inventors: Eric G. Del Mar, Robert M. Barmore, Derek Sheehan, Bradford C. Van Wagenen, James F. Callahan, Richard M. Keenan, Nikesh R. Kotecha, Maria Amparo Lago, Linda Sue Southall, Mervyn Thompson
  • Patent number: 6482859
    Abstract: The invention relates to novel pesticidally active compounds of the general formula I as well as possible isomers and mixtures of isomers thereof, wherein n is a number zero or one; and R1 is C1-C12alkyl that is unsubstituted or may be substituted by C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C3-C8cycloalkyl, cyano, C1C6alkoxycarbonyl, C3-C6alkenyloxycarbonyl or by C3-C6alkynyloxycarbonyl; C3-C8cycloalkyl; C2-C12alkenyl; C2-C12alkynyl; C1-C12haloalkyl: or a group NR11R12 wherein R11 and R12 are each independently of the other hydrogen or C1-C8alkyl, or together are tetra- or penta-methylene; R2 and R3 are each independently of the other hydrogen; C1-C8alkyl; C1-C8alkyl substituted by hydroxy, C1-C4alkoxy, mercapto or by C1-C4alkylthio; C3-C8alkenyl; C3-C8alkynyl; C3-C8cycloalkyl; C3-C8cycloalkyl-C1-C4alkyl; or the two groups R2 and R3 together with the carbon atom to which they are bonded form a three- to eight-membered ring; R4, R5, R6 and R7 are identical or different and are ea
    Type: Grant
    Filed: February 4, 2000
    Date of Patent: November 19, 2002
    Assignee: Syngenta Crop Protection, Inc.
    Inventors: Martin Zeller, André Jeanguenat
  • 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: 6410749
    Abstract: Process for preparing optically active &bgr;-amino alcohols represented by a general formula (2): Ra—C*H(OH)—C*H(Rb)—Rc wherein Ra and Rc are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, Rb is one member selected from among groups represented by the following general formulae; (3) R1CO(R2)N—, and (4) R1CO(R1′CO)N—, and C* is an asymmetric carbon atom, characterized by reacting a racemic &agr;-aminocarbonyl compound represented by the general formula (1): Ra—CO—CH(Rb)—Rc, with hydrogen in the presence of an optically active transition metal compound represented by a general formula (7): MaXY(Px)m(Nx)n wherein Ma represents a metal atom belonging to VIII-group of the periodic law, X and Y represent each independently hydrogen, halogeno, Px represents a phosphine ligand, Nx represents an amine ligand, at least one of Px and Nx is optically active, and m and n each independently represent 0 or an integer of 1 th
    Type: Grant
    Filed: July 17, 2001
    Date of Patent: June 25, 2002
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Eiji Katayama, Daisuke Sato, Hirohito Ooka, Tsutomu Inoue
  • Patent number: 6277849
    Abstract: The invention relates to novel pesticidally active compounds of the general formula I as well as possible isomers and isomeric mixtures thereof, wherein n is a number zero or one; and R1 is C1-C12alkyl that is unsubstituted or may be substituted by C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C3-C8acycloalkyl, cyano, C1-C6alkoxycarbonyl, C3-C8alkenyloxycarbonyl, C1-C5alkynyloxycarbonyl; C3-C8cycloalkyl; C2-C12alkenyl: C2-C12alknyl; C1-C12haloalkyl or a group NR11R12; wherein R11, and R12 are each independently of the other hydrogen, C1-C6alkyl or together are tetra- or penta-methylene; R2 and R3 are each independently of the other hydrogen; C1-C8alkyl; C1-C8alkyl substituted by hydroxy, C1-C4alkoxy, mercapto or by C1C4alkylthio; C3-C8alkenyl; C3-C8alkynyl; C3-C8cycloalkyl; C3-C8acycloalkyl-C1-C4alkyl or wherein the two groups R2 and R3 together with the carbon atom to which they are bonded form a three- to eight-membered ring; R4, R5, R6 and R7 are identical or different and are eac
    Type: Grant
    Filed: August 24, 1999
    Date of Patent: August 21, 2001
    Assignee: Syngenta Crop Protection, Inc.
    Inventor: Martin Zeller
  • Patent number: 6090170
    Abstract: The present invention relates to derivatives of polyalkenyl amine substituted with numerous hydroxy groups of the following formula (I) useful as a novel fuel detergent. ##STR1## wherein polyalkenyl denotes a branched alkyl derived from polyolefin which has a molecular weight of 400.about.5,000 and is prepared with olefin having 2 to 6 carbon atoms; m is an integer ranging from 2 to 10, R.sup.1, R.sup.2 and R.sup.3 may be identical or different, and represent a hydrogen atom or a linear or branched alkyl having 1 to 4 carbon atoms: R.sup.4 and R.sup.5 may be identical or different, and denote a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group, a hydroxyalkyl, a phenyl, naphthyl, an aminoalkyl of formula (II) or a polyaminoalkylene of formula (III) ##STR2## wherein R.sup.6 denotes a C.sub.2 -C.sub.10 alkylene group: R.sup.7 and R.sup.8 may be identical or different, and denote a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group, a phenyl, a naphthyl or a C.sub.1 -C.sub.
    Type: Grant
    Filed: December 31, 1998
    Date of Patent: July 18, 2000
    Assignee: Daelim Industrial Co., Ltd.
    Inventors: Hyun-ki Yun, Jung-jin Kim, Yong-hwa Yeom, Il-seung Kim, Myeong-seog Kim, Byung-keel Sohn, Kyu-shon Jung
  • Patent number: 6057371
    Abstract: The invention relates to methods for the treatment of central nervous system disorders, gastrointestinal disorders, drug abuse, angina, migraine, hypertension and depression by administering a pharmaceutical composition comprising an effective amount of certain sigma receptor ligands to a patient in need of such treatment. The invention further relates to novel sigma receptor ligands having high binding to the sigma receptor and pharmaceutical compositions thereof. Unexpectedly, certain of the sigma receptor ligands of the present invention have selectivity for the sigma receptor over the DA, PCP and 5-HT.sub.1A receptors.
    Type: Grant
    Filed: June 10, 1992
    Date of Patent: May 2, 2000
    Assignee: Virginia Commonwealth University
    Inventor: Richard A. Glennon
  • Patent number: 5874601
    Abstract: A process of protecting a 1,2- or 1,3-aminoalcohol for reductive amination coupling is provided. The alcohol is protected with trimethylsilyl chloride. Trimethylsilyl protected norepinephrine derivatives useful in the preparation of arbutamine are also provided.
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: February 23, 1999
    Assignee: Abbott Laboratories
    Inventors: William T. Monte, Aline C. Lindbeck
  • 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: 5587398
    Abstract: Novel meta substituted arylakylamine compounds are disclosed. These compounds can be administered as small molecule drugs to treat diseases or conditions associated with insufficient serotonin mediated nerve transmission (e.g. depression and obesity).
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: December 24, 1996
    Assignee: David R. Elmaleh
    Inventors: David R. Elmaleh, Alan J. Fischman
  • Patent number: 5367073
    Abstract: The present invention relates to a process for the synthesis of chiral enantiomerically pure .beta.-amino alcohols which are extraordinarily important as therapeutic agents for the treatment of a variety of human disorders and as chiral auxiliaries in organic synthesis. The hydroboration of enamines is a versatile and convenient method for the synthesis of both racemic and enantiomerically pure .beta.-amino alcohols in high yields. This methodology enables the synthesis of virtually any .beta.-amino alcohol. Hydroboration of these enamines with chiral organic borohydrides, e.g. either mono- or diisopinocampheylborane, followed by oxidation with aqueous or solid NaOH/30% H.sub.2 O.sub.2 or Me.sub.3 NO, gives the corresponding chiral .beta.-amino alcohol. Enantiomeric excesses ranged from 60% for reactions run at 25.degree. C. to greater than 99% for reactions run at -25.degree. C.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: November 22, 1994
    Assignee: The Regents of the University of California
    Inventors: Bakthan Singaram, Gary B. Fisher, Christian T. Goralski, Lawrence W. Nicholson
  • Patent number: 5318994
    Abstract: Compounds of the formula: ##STR1## in which: A represents ##STR2## R represents linear or branched lower alkyl, R.sub.1 represents hydrogen or linear or branched lower alkyl, andR.sub.2 represents aryl or lower arylalkyl or aryl or lower arylalkyl substituted by lower alkyl, lower alkoxy, trifluoromethyl, or halogen, aryl means phenyl or naphthyl, as well as optical isomers, epimers and diastereoisomers and addition salts thereof with a pharmaceutically-acceptable acid, lower alkyl and lower alkoxy having 1 to 6 carbon atoms inclusive, andmedicaments containing the same which are useful for the treatment of disorders of the melatoninergic system.
    Type: Grant
    Filed: November 3, 1992
    Date of Patent: June 7, 1994
    Assignee: Adir et Compagnie
    Inventors: Jean Andrieux, Raymond Houssin, Said Yous, Beatrice Guardiola, Daniel Lesieur
  • Patent number: 5292956
    Abstract: Tertiary amines corresponding to the formula Z.sub.2 Z'N in which Z is a 3,5-dihydrocarbyl-4-hydroxyphenalkyl group having the structure: ##STR1## wherein R is hydrogen or an alkyl group of 1-3 carbons; R' and R" are hydrocarbyl groups independently selected from alkyls and cycloalkyls of up to six carbons; n represents zero or one; and Z' is Z or an alkyl, alkenyl, or aralkyl group of up to 18 carbons are novel compounds having antioxidant activity in organic materials which are normally susceptible to oxidative deterioration. They are especially valuable as antioxidants for lubricants.
    Type: Grant
    Filed: September 1, 1992
    Date of Patent: March 8, 1994
    Assignee: Ethyl Corporation
    Inventor: Vincent J. Gatto
  • Patent number: 5274002
    Abstract: Novel trisubstituted phenyl analogs are now found to have activity as for the treatment of congestive heart failure.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: December 28, 1993
    Assignee: Warner-Lambert Company
    Inventor: Lynn D. Hawkins
  • Patent number: 5220068
    Abstract: The present invention relates to a pharmaceutical composition comprising as active ingredient a compound of the Formula I ##STR1## wherein R.sup.1 stands for straight or branched chain alkyl comprising 1 to 8 carbon atoms; phenyl alkyl having 7 to 10 carbon atoms; phenyl; or cycloalkyl comprising 3 to 8 carbon atoms;R.sup.2 stands for straight or branched chain alkyl comprising 1 to 8 carbon atoms; alkyl comprising 1 to 8 carbon atoms substituted by halogen, hydroxy, alkoxy having 1 to 4 carbon atoms or by one or two phenyl groups; phenyl; or cycloalkyl having 3 to 8 carbon atoms,with the proviso that groups R.sup.1 and R.sup.2 together contain at least three carbon atoms. The invention also relates to a process for the preparation of compounds of the Formula I by methods known per se.
    Type: Grant
    Filed: January 29, 1991
    Date of Patent: June 15, 1993
    Assignee: Chinoin Gyogyszer - es Vegyeszeti Termekek Gyara Rt.
    Inventors: Jozsef Knoll, Antal Simay, Eva Szinnyei, Eva Somfai, Zoltan Torok, Karoly Mozsolits, Janos Bergmann
  • Patent number: 5220066
    Abstract: This invention provides a process for directly preparing arylethylamines and their salts from (.alpha.-halo-.alpha.-oximino)acetophenones. The process involves hydrogenation in presence of a transition metal catalyst. The process is illustrated by conversion of 4-hydroxy-(.alpha.-chloro-.alpha.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: June 15, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed Tafesh, B. Frank Wood, Joseph A. McDonough, Graham N. Mott
  • Patent number: 5220067
    Abstract: This invention provides a process for directly preparing hydrohalide salts of arylethylamines from (.alpha.-chloro-.alpha.-oximino)acetophenones. The process involves hydrogenation in presence of a transition metal catalyst in an organic acid in substantial absence of moisture. The process is illustrated by conversion of 4-hydroxy (.alpha.-chloro-.alpha.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: June 15, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed Tafesh, B. Frank Wood, Joseph A. McDonough, Graham N. Mott
  • Patent number: 5214156
    Abstract: This invention is therapeutically useful tetralins and pharmaceutically acceptable acid addition salts thereof of the formula ##STR1## wherein YR.sub.1 is OR.sub.1 at the 8 position where R.sub.1 is --CH.sub.2 --(C.sub.3-8 cycloalkyl);R.sub.2 is hydrogen or C.sub.1-3 alkyl;R.sub.3 is --CH.sub.2 --(C.sub.3-8 cycloalkyl);R.sub.4 is hydrogen, C.sub.1-8 alkyl, --CH.sub.2 --(C.sub.3-4 cycloalkyl), --(CH.sub.2).sub.m --R.sub.5 or --CH.sub.2 --CH.sub.2 --X--(CH.sub.2).sub.n CH.sub.3 ; n is zero to 3 and m is 2 or 3; X is oxygen or sulfur;R.sub.5 is phenyl, C.sub.1-3 alkoxy, C.sub.1-3 alkyl, 2-thiophene, 3-thiophene, or phenyl substituted with one or two substituent groups selected from chlorine, bromine or fluorine; and with the proviso that when R.sub.3 contains more than four carbon atoms and R.sub.4 is alkyl, said alkyl contains from 1 to 3 carbon atoms.Alternatively, --YR.sub.1 is --S--(C.sub.1-3 alkyl) at the 5, 6, 7 or 8 position of the aromatic ring or OR.sub.1 at the 8 position where R.sub.
    Type: Grant
    Filed: April 10, 1992
    Date of Patent: May 25, 1993
    Assignee: The Upjohn Company
    Inventors: Bengt R. Andersson, Per Arvid E. Carlsson, Kjell A. I. Svensson, Hakan V. Wikstrom
  • Patent number: 5200561
    Abstract: 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: Grant
    Filed: October 7, 1991
    Date of Patent: April 6, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Naoto Konya, Yukio Yoneyoshi, Yoji Sakito, Shinji Nishii, Gohfu Suzukamo, Hiroko Sakane
  • Patent number: 5198587
    Abstract: Phenethylamine derivatives shown by the general formula ##STR1## wherein Ro represents a lower alkyl group; R.sub.1 represents a lower alkyl group or a lower alkoxy group; R.sub.2 represents hydrogen atom or a hydroxyl group; R.sub.3 and R.sub.4 each represents hydrogen atom or a lower alkyl group; R.sub.5 represents hydrogen atom or a lower alkoxy group; X represents oxygen atom or a methylene group; m is an integer of 1-3; and n is an integer of 0-2 and the acid addition salts thereof.These compounds exhibit a strong .alpha.-adrenergic blocking action and are useful as an antihypertensive agent.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: March 30, 1993
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kazuo Imai, Kunihiro Niigata, Takashi Fujikura, Shinichi Hashimoto, Toichi Takenaka, Kazuo Honda
  • Patent number: 5175368
    Abstract: Arylalkylamines (as the hydrochloride salt), e.g. tyramine hydrochloride, are prepared by hydrogenating substituted or unsubstituted aryl-.alpha.-oximinoalkyl ketones, e.g. p-hydroxyisonitroacetophenone, in either in an aqueous reaction medium comprising hydrochloric acid, essentially without the presence of a lower alkyl alcohol in said reaction medium, or in an aqueous reaction medium comprising water, hydrochloric acid, and a lower alkyl alcohol, wherein the alcohol comprises less than about 90% by volume of the reaction medium. A substituent on the aryl portion of the aryl-.alpha.-oximinoalkyl ketone must be on a position which activates the aromatic ring.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: December 29, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed M. Tafesh, Joseph A. McDonough, Graham N. Mott
  • Patent number: 4996316
    Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.
    Type: Grant
    Filed: December 24, 1988
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
  • Patent number: 4913891
    Abstract: This invention involves a new strategy for imaging and mapping enzyme activity in the living human and animal body using positron emitter-labeled suicide enzyme inactivators or inhibitors which become covalently bound to the enzyme as a result of enzymatic catalysis. Two such suicide inactivators for monoamine oxidase have been labeled with carbon-11 and used to map the enzyme subtypes in the living human and animal body using PET. By using positron emission tomography to image the distribution of radioactivity produced by the body penetrating radiation emitted by carbon-11, a map of functionally active monoamine oxidase activity is obtained. Clorgyline and L-deprenyl are suicide enzyme inhibitors and irreversibly inhibit monoamine oxidase. When these inhibitors are labeled with carbon-11 they provide selective probes for monoamine oxidase localization and reactivity in vivo using positron emission tomography.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: April 3, 1990
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Joanna S. Fowler, Robert R. MacGregor, Alfred P. Wolf, Bengt Langstrom
  • Patent number: 4898889
    Abstract: Acetylene compounds of the formula (I): ##STR1## wherein Y, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as described herein, m is 0-3, n is 0-2 and Ar is phenyl or an aromatic heterocycle are disclosed. The compounds possess antihypertensive and anti-anginal properties and may be used in the treatment of humans. Methods for the preparation and use of such acetylene compounds are also disclosed.
    Type: Grant
    Filed: March 27, 1989
    Date of Patent: February 6, 1990
    Assignee: McNeilab, Inc.
    Inventor: John R. Carson
  • 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: 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: 4725602
    Abstract: Acetylenes of the following formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2, R.sup.3, n and R.sup.4 are defined herein and R.sup.5 is hydrogen, alkyl, cycloalkyl or substituted alkyl are useful vasodilators and antihypertensives.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: February 16, 1988
    Assignee: McNeilab, Inc.
    Inventor: John R. Carson
  • 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: 4622218
    Abstract: Testicularly acting drug species are site-specifically/sustainedly delivered to the testes by administering to a male in need of such treatment a pharmacologically effective amount of the target drug species [D] tethered to a reduced, blood-testis barrier penetrating lipoidal form [D--DHC] of a dihydropyridine.revreaction.pyridinium salt type redox carrier, e.g. 1,4-dihydrotrigonelline. Oxidation of the dihydropyridine carrier moiety in vivo to the ionic pyridinium salt type drug/carrier entity [D--QC].sup.+ prevents elimination thereof from the testes, while elimination from the general circulation is accelerated, resulting in significant and prolongedly sustained testicular-specific drug activity, whether ascribable to the cleavage of the [D--QC].sup.+ entity and sustained release of the drug [D] in the testes and/or to [D--QC].sup.+ itself.
    Type: Grant
    Filed: March 15, 1983
    Date of Patent: November 11, 1986
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • Patent number: 4616082
    Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and Q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification,The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: October 7, 1986
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4549015
    Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification.The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: October 22, 1985
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • 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