Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Piperidine Ring Patents (Class 546/245)
  • Patent number: 5827858
    Abstract: HIV protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain these compounds and optionally other anti-viral agents as active ingredients, are suitable for treating patients or hosts infected with the HIV virus, which is known to cause AIDS.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 27, 1998
    Assignee: Agouron Pharmaceuticals, Inc.
    Inventors: Vincent J. Kalish, Siegfried Heinz Reich, John H. Tatlock, Michael J. Rodriguez
  • Patent number: 5811434
    Abstract: The present invention relates to methods and pharmaceutical compositions for stimulating the growth of neurites in nerve cells. The compositions comprise a neurotrophic amount of a compound and a neurotrophic factor, such as nerve growth factor (NGF). The methods comprise treating nerve cells with the above compositions or compositions comprising the compound without a neurotropic factor. The methods of this invention can be used to promote repair of neuronal damage caused by disease or physical trauma.
    Type: Grant
    Filed: November 13, 1996
    Date of Patent: September 22, 1998
    Assignee: Vertex Pharmacueticals Incorporated
    Inventors: Robert E. Zelle, Michael Su
  • Patent number: 5792787
    Abstract: Dithiocarboxylates, and in particular, dithiocarbamates, block the induced expression of the endothelial cell surface adhesion molecule VCAM-1, and are therefor useful in the treatment of cardiovascular disease, including atherosclerosis, post-angioplasty restenosis, coronary artery diseases, and angina, as well as noncardiovascular inflammatory diseases that are mediated by VCAM-1.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: August 11, 1998
    Assignee: Emory University
    Inventors: Russell M. Medford, R. Wayne Alexander, Margaret K. Offermann
  • Patent number: 5789404
    Abstract: 3-Substituted 1-arylindole compounds are provided having general formula (I) ##STR1## wherein Ar is an optionally substituted aryl group; X represents a divalent hydrocarbon group, methyleneoxy or -thioxo; R.sup.1 -R.sup.4 are hydrogen or other substituents; R.sup.5 is hydrogen, alkyl, alkenyl, etc.; R.sup.6 and R.sup.7 are independently hydrogen, alkyl, alkenyl, etc.; R.sup.8 is alkyl, alkenyl or R.sup.8 represents a group of formula 1a or 1b; wherein n is an integer from 2-8; W is O or S; U is N or CH; Z is (CH.sub.2).sub.m, m being 2 or 3, 1,2-phenylene optionally substituted with halogen or trifluoromethyl, CH.dbd.CH, COCH.sub.2 or CSCH.sub.2 ; V is O, S, CH.sub.2 or NR.sup.10, wherein R.sup.10 is hydrogen, alkyl, alkenyl, cycloalkyl, etc.; U.sup.1 is O, S, CH.sub.2 or a group NR.sup.11, wherein R.sup.11 is hydrogen, alkyl, alkenyl, etc.; and V.sup.1 is NR.sup.12 R.sup.13, OR.sup.14, SR.sup.15 or CR.sup.16 R.sup.17 R.sup.18, where R.sup.12 -R.sup.18 are as the R.sup.10 substituents; R.sup.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: August 4, 1998
    Assignee: H. Lundbeck A/S
    Inventors: Kim Andersen, Jens Kristian Perregaard
  • Patent number: 5783697
    Abstract: Vinyl carbamate compounds are prepared by reacting appropriate secondary amines with carbon dioxide and acetylenically unsaturated compounds in the presence of a compound of a metal from the platinum group, in particular a ruthenium compound, with either one of the two process steps (a) and (b) or, preferably, both being carried out:(a) the acetylene compound is reinjected during the reaction;(b) the reaction is carried out in the presence of a tertiary amine.
    Type: Grant
    Filed: January 21, 1997
    Date of Patent: July 21, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Marc Heider, Jochem Henkelmann, Michael Karcher, Thomas Ruhl
  • Patent number: 5776927
    Abstract: This invention relates to compounds which inhibit thrombin or factor Xa. The compounds contain an aldehyde functionality and a methionine sulfone or S-substituted cysteine sulfone residue. The compounds and their pharmaceutical compositions are useful for preventing thrombosis in mammals which are suspected of having a condition characterized by abnormal thrombosis.
    Type: Grant
    Filed: April 18, 1994
    Date of Patent: July 7, 1998
    Assignee: Corvas International, Inc.
    Inventors: Matthew M. Abelman, Robert J. Ardecky
  • Patent number: 5776971
    Abstract: Selected heterocyclecarbonyl amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 7, 1998
    Assignee: G.D. Searle & Co.
    Inventors: Daniel P. Getman, Gary A. DeCrescenzo, John N. Freskos, Michael L. Vazquez, James A. Sikorski, Balekudru Devadas, Srinivasan Nagarajan, David L. Brown, Joseph J. McDonald
  • 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: 5744485
    Abstract: The present invention relates to compounds that can maintain, increase, or restore sensitivity of cells to therapeutic or prophylactic agents. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well-suited for treatment of multi-drug resistant cells, for prevention of the development of multi-drug resistance, and for use in multi-drug resistant cancer therapy.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: April 28, 1998
    Assignee: Vertex Pharmaceuticals Incorporated
    Inventors: Robert Edward Zelle, Matthew W. Harding
  • Patent number: 5741792
    Abstract: Heterocyclic thrombin inhibitors are provided which have the structure ##STR1## wherein n, R, R.sup.1, R.sup.2, R.sup.3, G, G.sub.x, R.sup.6 ', Ra, Xa, R.sup.6, Rb, R.sub.3, p, Q, A and R.sup.4 are as defined herein.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: April 21, 1998
    Assignee: Bristol-Myers Squibb Company
    Inventors: Spencer D. Kimball, Jagabandhu Das, Wan Fang Lau, Steven E. Hall, Wen-Ching Han
  • Patent number: 5741799
    Abstract: Heterocyclic thrombin inhibitors are provided which have the structure ##STR1## wherein n, R, R.sup.1, R.sup.2, R.sup.3, G, G.sub.x, R.sup.6', Ra, Xa, R.sup.6, Rb, R.sub.3, p, Q, A and R.sup.4 are as defined herein.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: April 21, 1998
    Assignee: Bristol-Myers Squibb Company
    Inventors: Spencer D. Kimball, Jagabandhu Das, Wan Fang Lau, Steven E. Hall, Wen-Ching Han
  • Patent number: 5723470
    Abstract: Novel 3,4,4-trifluorobutenoic acid derivatives of the formula ##STR1## wherein Q is --(C.dbd.W)--R.sub.2 wherein W is O or S, and R.sub.2 is an aliphatic or aromatic group when W.dbd.O; --OR.sub.50 ; --SR.sub.50 ; or --NR.sub.50 R.sub.60 wherein R.sub.60 is hydrogen or R.sub.50 ; NR.sub.7 R.sub.8 ; a heterocyclic group; phenyl substituted by alkyl; or any agronomically acceptable salt thereof having usefulness as nematocides, insecticides and acaricides.
    Type: Grant
    Filed: February 12, 1996
    Date of Patent: March 3, 1998
    Assignee: Monsanto Company
    Inventors: Dennis Paul Phillion, Peter Gerrard Ruminski, Gopichand Yalamanchili
  • Patent number: 5719141
    Abstract: Compounds of the formula I ##STR1## in which R.sub.1 is arylamino, N-aryl-N-(lower alkoxy-lower alkyl)-amino, N-aryl-N-aryl-lower alkyl-amino or heterocyclyl bonded via a ring carbon atom, X is a carbonyl or methylene group, R.sub.2 and R.sub.3 independently of one another are hydrogen or lower alkyl or, together with the carbon atom with which they are bonded, are a cycloalkylidene radical, R.sub.4 is hydrogen, lower alkyl, lower alkanoyl or lower alkoxycarbonyl, R.sub.5 is hydroxyl, lower alkanoyloxy or lower alkoxycarbonyloxy, R.sub.6 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, cycloalkyl-lower alkyl, aryl-lower alkyl or heteroaryl-lower alkyl having 5 to 7 ring atoms in the heteroaryl ring and R.sub.7 is hydrogen or lower alkyl, or R.sub.6 and R.sub.7, together with the carbon atom with which they are bonded, are a cydoalkylidene radical and R.sub.
    Type: Grant
    Filed: September 8, 1995
    Date of Patent: February 17, 1998
    Assignee: Novartis Corporation
    Inventors: Vittorio Rasetti, Heinrich Rueger, Jurgen Klaus Maibaum, Robert Mah, Markus Grutter, Nissim Claude Cohen
  • Patent number: 5693807
    Abstract: The invention relates to substituted hydroquinone derivatives of the general formula I ##STR1## wherein R.sub.4 is lower alkyl and either R.sub.1 is hydroxy, halogen, a group of the formula --P(=O)(R.sub.5)R.sub.6 (Ia), a group of the formula --P.sup.+ (R.sub.7)(R.sub.8)R.sub.9 X.sup.- (Ib) or a group of the formula --Si(R.sub.7)(R.sub.8)R.sub.9 (Ic), M is methylene, R.sub.2 is hydrogen or a group of the formula ##STR2## and R.sub.3 is hydrogen or halogen, or .sub.1 is hydroxy or lower alkoxy, M is carbonyl, R.sub.2 is hydrogen and R.sub.3 is halogen, each of R.sub.5 and R.sub.6, independently of the other, is lower alkyl, lower alkoxy Or N,N-di-lower alkylamino, or is benzyl, benzyloxy, phenyl or phenoxy, each of which is unsubstituted or mono- or di-substituted at the phenyl ring, to a process for the preparation of those compounds and to the use of those compounds, and to a process in which those compounds are used.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 2, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Gottfried Sedelmeier, Gerhard Fischer
  • Patent number: 5686469
    Abstract: Compounds which suppress human T-lymphocyte proliferation are disclosed.
    Type: Grant
    Filed: December 12, 1995
    Date of Patent: November 11, 1997
    Assignee: Miles Inc.
    Inventors: Richard D. Connell, David G. Osterman, Michael E. Katz, Robert D. Dally
  • Patent number: 5686424
    Abstract: A class of compounds that suppress human T-lymphocyte proliferation is disclosed.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: November 11, 1997
    Assignee: Miles Inc.
    Inventors: Richard D. Connell, David G. Osterman, Michael E. Katz
  • Patent number: 5679679
    Abstract: Certain aralkyl diazabicyloalkyl compounds are described for treatment of CNS disorders such as cerebral ischemia, psychoses and convulsions. Compounds of particular interest are of the formula: ##STR1## wherein: each of R.sup.1, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 is independently selected from the group consisting of hydrido, loweralkyl, benzyl and haloloweralkyl;each of R.sup.2, R.sup.3, and R.sup.8 through R.sup.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: October 21, 1997
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Wayne Bowen, Brian R. de Costa, Celia Dominguez, Xiao-Shu He, Kenner C. Rice
  • Patent number: 5672583
    Abstract: Novel Carboxy-peptidyl compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophobic epidermolysis bullosa, coronary thrombosis associated with atherosclerotic plaque rupture, and aneurysmal aortic disease. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also have utility as a means for birth control by preventing ovulation or implantation.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: September 30, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Kevin Chapman, William Hagmann, Philippe Durette, Craig Esser, Ihor Kopka, Charles Caldwell
  • Patent number: 5650508
    Abstract: A novel class of peptide .alpha.-ketoamides useful for selectively inhibiting serine proteases, selectively inhibiting cysteine proteases, generally inhibiting all serine proteases, and generally inhibiting all cysteine proteases, having the formula M.sub.1 --AA--NH--CHR.sub.2 --CO--CO--NR.sub.3 R.sub.4, M.sub.1 --AA.sub.2 --AA.sub.1 --CO--NR.sub.3 R.sub.4, M.sub.1 --AA--AA--AA--CO--NR.sub.3 R.sub.4, M.sub.1 --AA--AA--AA--AA--CO--NR.sub.3 R.sub.4, or M.sub.1 --AA--CO--NR.sub.3 R.sub.4.
    Type: Grant
    Filed: October 6, 1995
    Date of Patent: July 22, 1997
    Assignee: Georgia Tech Research Corporation
    Inventor: James C. Powers
  • Patent number: 5650540
    Abstract: Provided is a method of producing a highly pure amide compound in a high yield, wherein a silazane compound and/or a silane compound having at least one silicone-nitrogen bond are added to a reaction mixture obtained by reacting an acylfluoride group-containing compound with an amino compound, wherein the amide compound is present together with hydrogen fluroide and/or the amine hydrofluoride, thereby removing the hydrogen fluoride and/or the amine hydrofluoride from the reaction mixture.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: July 22, 1997
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takashi Matsuda, Shinichi Sato, Noriyuki Koike
  • Patent number: 5646165
    Abstract: This invention relates to compounds which inhibit thrombin or factor Xa. The compounds contain an aldehyde functionality and a methionine sulfone or S-substituted cysteine sulfone residue. The compounds and their pharmaceutical compositions are useful for preventing thrombosis in mammals which are suspected of having a condition characterized by abnormal thrombosis.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: July 8, 1997
    Assignee: Corvas International, Inc.
    Inventors: Matthew M. Abelman, Robert J. Ardecky, Ruth F. Nutt
  • Patent number: 5631376
    Abstract: A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: May 20, 1997
    Assignee: Abbott Laboratories
    Inventors: Daniel W. Norbeck, Hing L. Sham, Dale J. Kempf, Chen Zhao
  • Patent number: 5624936
    Abstract: The present invention comprises analogs of the CA.sup.1 A.sup.2 X motif of the protein Ras that is modified by farnesylation in vivo. These CA.sup.1 A.sup.2 X analogs inhibit the farnesyl-protein transferase and the farnesylation of certain proteins. Furthermore, these CA.sup.1 A.sup.2 X analogs differ from those previously described as inhibitors of farnesyl-protein transferase in that they do not have a thiol moiety. The lack of the thiol offers unique advantages in terms of improved pharmacokinetic behavior in animals, prevention of thiol-dependent chemical reactions, such as rapid autoxidation and disulfide formation with endogenous thiols, and reduced systemic toxicity. The compounds of the instant invention also incorporate a cyclic amine moiety in the A.sup.2 position of the motif. Further contained in this invention are chemotherapeutic compositions containing these farnesyl transferase inhibitors and methods for their production.
    Type: Grant
    Filed: February 13, 1996
    Date of Patent: April 29, 1997
    Assignee: Merck & Co., Inc.
    Inventor: S. Jane deSolms
  • Patent number: 5622971
    Abstract: A compound of the formula (I): ##STR1## or a pharmaceutically acceptable salt thereof is disclosed, as well as processes for and intermediates in the preparation thereof, and a method of antagonizing endothelin.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: April 22, 1997
    Assignee: Abbott Laboratories
    Inventors: Martin Winn, Steven A. Boyd, Charles W. Hutchins, Hwan-Soo Jae, Andrew S. Tasker, Thomas W. von Geldern, Jeffrey A. Kester, Bryan K. Sorensen
  • Patent number: 5610144
    Abstract: This invention relates to compositions of formula: ##STR1## and their salts, their preparation and the medicaments containing them.
    Type: Grant
    Filed: June 27, 1994
    Date of Patent: March 11, 1997
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Marc Capet, Claude Cotrel, Claude Guyon, Michel Joannic, Franco Manfre, G erard Roussel, Marie-Christine Dubroeuco, Michel Cheve, Gilles Dutruc-Rosset
  • Patent number: 5608109
    Abstract: The present invention relates to a hydrazine derivative represented by the formula (I): ##STR1## (wherein each of Ar.sup.1 and Ar.sup.2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted heteroaryl group, or the like, R.sup.1 is an alkyl group or the like, and A is a divalent radical having --C.dbd.N--N-- or --CH--NH--N-- as a fundamental skeleton), which is a useful compound as an agricultural and horticultural insecticide.
    Type: Grant
    Filed: December 7, 1994
    Date of Patent: March 4, 1997
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Kazuhiro Takagi, Tetsuji Ohshima, Nobuyoshi Hasegawa, Chiaki Katoh, Atsushi Kanaoka, Hideo Kanno
  • Patent number: 5597917
    Abstract: A process for the dissolution of chemical compounds by use of ureas in which at least one of the urea's two nitrogen atoms is part of a non-aromatic ring which can be broken by an oxygen or sulphur atom as a chemical solvent, and a method of producing tri- or tetraalkylated ureas or bis ureas wherein at least one of the urea's nitrogen atoms is part of a non-aromatic ring which can be broken by an oxygen or sulphur atom by means of dialkylating the --NH.sub.2 group of a urea with an alkene or alkene arylene alkene dihalogenide, disulphonate or dihydrogen sulphonate in the presence of a solid base and a phase-transfer catalyst.
    Type: Grant
    Filed: January 30, 1995
    Date of Patent: January 28, 1997
    Assignee: DSM Chemie Linz GmbH
    Inventors: Kurt A. Hackl, Markus R ossler, Martin M ullner, Gerhard Stern
  • Patent number: 5554633
    Abstract: Compounds of formula (I), and salts and prodrugs thereof, wherein Q is optionally substituted phenyl or benzhydryl; X and Y are each H or together form a group=O; Z is O, S or NR.sup.9, where R.sup.9 is H or C.sub.1-6 alkyl; R.sup.1 represents H or C.sub.1-6 alkyl; R.sup.2 represents C.sub.1-6 alkyl substituted by CONR.sup.7 (CH.sub.2).sub.p R.sup.8 (where R.sup.7 is H or C.sub.1-6 alkyl, R.sup.8 is optionally substituted heteroaryl and p is 0, 1, 2, 3, 4, 5 or 6); R.sup.3 represents H, C.sub.1-6 alkyl or C.sub.2-6 alkynyl; R.sup.4 represents H, C.sub.1-6 alkyl or optionally substitute phenyl; R.sup.5 represents optionally substituted phenyl; R.sup.6 is H or C.sub.1-6 alkyl; and q is 0, 1, 2 or 3; are tachykinin antagonists useful in therapy.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: September 10, 1996
    Assignee: Merck, Sharp & Dohme, Ltd.
    Inventor: Martin R. Teall
  • Patent number: 5554756
    Abstract: Compositions containing compounds ##STR1## and their pharmaceutically acceptable acid addition salts inhibit proteases of viral origin and can be used as medicaments for the treatment or prophylaxis of viral infections. They can be manufactured according to generally known procedures.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: September 10, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Balraj K. Handa, Peter J. Machin, Joseph A. Martin, Sally Redshaw, Gareth J. Thomas
  • Patent number: 5552543
    Abstract: Novel six-membered hetero "N" compounds having antibiotic activity, represented by the formula: ##STR1## where X.dbd.S, O, CH.sub.2, or SeY.dbd.OH, NH.sub.2, NHCOR.sub.9, or SHR.sub.1,R.sub.2,R.sub.3,R.sub.4,R.sub.5,R.sub.6,R.sub.7 (which may be identical or different).dbd.H, alkyl, or arylR.sub.9 .dbd.a .beta.-lactam active side chain;computer models for evaluating such compounds and processes for preparing them.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: September 3, 1996
    Assignee: Simon Fraser University
    Inventors: Saul Wolfe, Stephen Bruder
  • Patent number: 5538998
    Abstract: There are provided with a novel N-substituted-3-halopropiolamide compound, a method of producing the compound, and a composition for controlling noxious organisms containing the compound. The present compound exhibits superior antimicrobial and antifungal effects. Pest control agents containing the compound can advantageously be used for wide applications.
    Type: Grant
    Filed: October 21, 1994
    Date of Patent: July 23, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshihiro Sugihara, Toshiro Yamashita, Sachio Shibata, Koichi Matsumura, Yosei Kuwazuru
  • Patent number: 5532259
    Abstract: Isoxazole-4-carboxamides and hydroxyalkylidenecyanoacetamides, pharmaceuticals containing these compounds and their useIsoxazole-4-carboxamide derivatives and hydroxyalkylidene-cyanoacetamide derivatives are suitable for the treatment of carcinoses. These compounds can be prepared by known processes. Some of the compounds are novel and are additionally suitable for the treatment of rheumatic disorders.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 2, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Robert R. Bartlett, Friedrich-Johannes Kammerer
  • Patent number: 5510349
    Abstract: Urea-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 23, 1996
    Assignee: G.D. Searle & Co.
    Inventors: John J. Talley, Daniel P. Getman, Gary A. DeCrescenzo, Ko-Chung Lin, Michael L. Vazquez, Richard A. Mueller, Kathryn L. Reed, Robert M. Heintz, Michael Clare, John N. Freskos, Eric T. Sun
  • Patent number: 5510477
    Abstract: High quality acyl lactam imides are prepared by reacting an acyl lactam of the formula ##STR1## where 5 carbon atoms and an acylating acid of the formula R'CO.sub.2 H or by reacting a lactam, an anhydride of the formula (RCO).sub.2 O where R is 1 to 5 carbon atoms and an acylating acid, preferably in the presence of a base catalyst. The process affords acyl lactam imides in high yield and at lower reaction temperatures by providing for the removal of volatile carboxylic acid by-products under vacuum or by the use of a stripping gas. The acyl lactam imides are particularly suited for use as bleach activators in detergent compositions.
    Type: Grant
    Filed: March 1, 1994
    Date of Patent: April 23, 1996
    Assignee: The Procter & Gamble Company
    Inventors: Alan D. Willey, Larry E. Miller
  • Patent number: 5489690
    Abstract: An improved process for the preparation of trans-6-[2-(substituted-pyrrole-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where .alpha.-metalated N,N-disubstituted acetamide is converted in seven operations to the desired products, and specifically, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahy dro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide, as well as other valuable intermediates used in the processes and prodrugs which are bioconverted to hypolipidemic and hypocholesterolemic agents and pharmaceutical compositions of the same.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: February 6, 1996
    Assignee: Warner-Lambert Company
    Inventors: Donald E. Butler, Tung V. Le, Thomas N. Nanninga
  • Patent number: 5481035
    Abstract: Process for the preparation of asymmetrically substituted ureas, carbamates, thiocarbamates or substituted isocyanates by reaction of an adduct of isocyanic acid and a tertiary amine with a primary and secondary amine, an alcohol, a thiol or a compound having one or two non-cumulated olefinic double bonds, and a process for the preparation of N-mono- or N,N-disubstituted ureas by reaction of ammonium isocyanates with a primary or secondary amine in a diluent.
    Type: Grant
    Filed: July 6, 1993
    Date of Patent: January 2, 1996
    Assignee: Chemie Linz Gesellschaft m.b.H.
    Inventors: Martin Mullner, Gerhard Stern, Markus Rossler
  • Patent number: 5455348
    Abstract: The invention relates to cyclic imino derivatives of general formulaB--X.sub.5 --X.sub.4 --X.sub.3 --X.sub.2 --X.sub.1 --A--Y--E(I)whereinA, B, E, X.sub.2 to X.sub.5 and Y are defined as in claim 1, the stereoisomers, tautomers, mixtures and salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable pharmacological properties, preferably aggregation-inhibiting effects, pharmaceutical compositions which contain these compounds and processes for preparing them.
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: October 3, 1995
    Assignee: Karl Thomae
    Inventors: Volkhard Austel, Wolfgang Eisert, Frank Himmelsbach, Guenter Linz, Thomas Mueller, Helmut Pieper, Johannes Weisenberger
  • Patent number: 5446158
    Abstract: A process is described for the total synthesis of the macrolide immunosuppressant, FK-506, and important tricarbonyl process intermediates thereof. The tricarbonyl intermediates can be produced by the mild oxidation of 2,3-dihydroxy carboxylate compounds containing olefin moieties.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: August 29, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Todd K. Jones, Sander G. Mills, David Askin, Robert A. Reamer, Richard Desmond, David M. Tschaen, Ralph P. Volante, Ichiro Shinkai
  • Patent number: 5439918
    Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and treatment of cancer.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: August 8, 1995
    Assignee: Merck & Co., Inc.
    Inventors: S. Jane deSolms, Samuel L. Graham
  • Patent number: 5436359
    Abstract: There are disclosed novel hydroquinone derivatives of the formulas: ##STR1## The derivatives of the formula (I) have various pharmacological activities such as antioxidation in living bodies and are useful as medicaments, and the derivatives of the formula (II) are intermediates for the production thereof.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: July 25, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirotomo Masuya, Masayoshi Yamaoka
  • Patent number: 5423998
    Abstract: Amino-derivative (poly)peroxycarboxylic acids which have the formula: ##STR1## wherein the symbols have the following meanings: R, R.sub.1, and R.sub.2, which may be equal to or different from one another, represent hydrogen atoms, alkyl groups or groups selected from R, R.sub.1 and R.sub.2, which taken together with the nitrogen atom to which they are linked, give rise to an aliphatic heterocyclic group, all of them being optionally substituted;A represents a (cyclo)alkylene group, an arylene group which may also be condensed with cycloaliphatic groups, a cycloalkylene-alkylene or an alkylene-cycloalkylene group, an arylene-alkylene or an alkylene-arylene group, which may be condensed with cyclo-aliphatic groups, wherein said alkylene group may also be interrupted by --CONR.sub.3 groups, wherein R.sub.3 represents a hydrogen atom or an alkyl or aryl group;X.sup.- represents HSO.sub.4.sup.- or CH.sub.3 SO.sub.3.sup.- ; a process for their preparation; and their use as bleaching agents.
    Type: Grant
    Filed: April 13, 1993
    Date of Patent: June 13, 1995
    Assignee: Ausimont S.r.l.
    Inventors: Carlo Venturello, Claudio Cavallotti
  • Patent number: 5414083
    Abstract: A process for the dissolution of chemical compounds by use of ureas in which at least one of the urea's two nitrogen atoms is part of a non-aromatic ring which can be broken by an oxygen or sulphur atom as a chemical solvent, and a method of producing tri- or tetraalkylated ureas or bis ureas wherein at least one of the urea's nitrogen atoms is part of a non-aromatic ring which can be broken by an oxygen or sulphur atom by means of dialkylating the --NH.sub.2 group of a urea with an alkene or alkene arylene alkene dihalogenide, disulphonate or dihydrogen sulphonate in the presence of a solid base and a phase-transfer catalyst.
    Type: Grant
    Filed: January 24, 1994
    Date of Patent: May 9, 1995
    Assignee: Chemie Linz Gesellschaft m.b.H.
    Inventors: Kurt A. Hackl, Markus Rossler, Martin Mullner, Gerhard Stern
  • Patent number: 5393764
    Abstract: The compounds of the present invention comprise substituted phenolic thioethers represented by the formula ##STR1## wherein: R.sup.1 and R.sup.2 are the same or different and independently represent tert-alkyl or phenyl; R.sup.3 represents hydrogen or alkyl; X represents --(CH.sub.2).sub.w --B--(CH.sub.2).sub.y -- wherein B represents O, S, or CH.sub.2 and w and y can each independently be an integer from 0 to 3 with the proviso that the sum of w+y is equal to or less than 3; A represents O or S(O).sub.n wherein n is 0, 1 or 2; p is an integer from 1 to 4; and R represents alkyl; OH; OR.sup.4 wherein R.sup.4 is alkyl of 1 to 4 carbon atoms; NR.sup.5 R.sup.6 wherein R.sup.5 is hydrogen or alkyl and R.sup.6 is hydrogen, alkyl, heterocyclealkyl in which the hetercyclic ring may optionally be substituted; cycloalkyl; substituted cycloalkyl; phenyl; substituted phenyl; phenylalkyl; or substituted phenylalkyl; or NR.sup.5 R.sup.6 together form a heterocyclic ring which may optionally be substituted; or R is (CH.
    Type: Grant
    Filed: August 25, 1993
    Date of Patent: February 28, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 5389680
    Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.
    Type: Grant
    Filed: October 18, 1993
    Date of Patent: February 14, 1995
    Assignee: Monsanto Company
    Inventor: Peter G. Ruminski
  • Patent number: 5385918
    Abstract: Compounds which suppress human T-lymphocyte proliferation are disclosed. The active compounds essentially contain at least the following structure: ##STR1## wherein A, R.sup.1, R.sup.2, R.sup.3, n, X.sup.1 and Z are defined in the specification.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: January 31, 1995
    Assignee: Miles Inc.
    Inventors: Richard D. Connell, David G. Osterman, Michael E. Katz, Rudolf Hanko, Stephan Schneider
  • Patent number: 5385902
    Abstract: Antimicrobial compounds of the formula ##STR1## wherein A is selected from the group consisting of alkyl; phenyl; alkoxy; phenoxy; benzyloxy; monoalkylamino; dialkylamino; cyclic amino, anilino; heterocyclic; amino substituted with heterocyclic ring, methods of making and using said compounds, and compositions comprising said compounds are disclosed.
    Type: Grant
    Filed: September 1, 1993
    Date of Patent: January 31, 1995
    Assignee: Rohm and Haas Company
    Inventor: Adam C. Hsu
  • Patent number: 5380855
    Abstract: A process for preparing N,N-substituted carbamoyl halides comprising (a) contacting carbon dioxide and a secondary amine in the presence of an aprotic organic solvent and a base selected from the group consisting of a phosphazene compound, an organic, nitrogenous base, mixtures of pyridine and a phosphazene compound or an organic, nitrogenous base, and mixtures thereof, to produce the corresponding ammonium carbamate salt, and (b) reacting the ammonium carbamate salt with a halide-containing electrophilic compound to produce the corresponding N,N-substituted carbamoyl halides. A second embodiment comprises recovering the ammonium carbamate salt of step (a) prior to reacting the ammonium carbamate salt with an halide-containing electrophilic compound in the presence of an aprotic organic solvent and a base selected from the group consisting of a phosphazene compound, an organic, nitrogenous base, mixtures of pyridine and a phosphazene compound or an organic, nitrogenous base, and mixtures thereof.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: January 10, 1995
    Assignee: Monsanto Company
    Inventors: William D. McGhee, John J. Talley
  • Patent number: 5380650
    Abstract: In an assay in which a ligand is labelled by conjugation to a dihydrophthalazinedione (DPD), e.g. luminol or isoluminol, and the conjugated DPD is reacted with an oxidant, e.g. hydrogen peroxide, and an active heme group catalyst, e.g. microperoxidase, the light intensity is enhanced by certain sterically hindered amines defined as saturated bicyclic compounds having a nitrogen atom at one or both bridgehead positions or a piperidine ring compound having four C.sub.1-4 alkyl groups at the 2- and 6- positions. 1,4-Diazabicyclo[2.2.2]-octane, known as "DABCO" is preferred.
    Type: Grant
    Filed: March 23, 1989
    Date of Patent: January 10, 1995
    Assignee: British Technology Group Ltd.
    Inventors: Geoffrey J. R. Barnard, Dean Goodwin, Robert S. Davidson
  • Patent number: 5344934
    Abstract: The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and a hydrocarbyl halide. The amine or alcohol is reacted with carbon dioxide in a suitable solvent system and in the presence of an amidine or guanidine base, to form the ammonium carbamate or carbonate salt which is then reacted in a polar aprotic solvent with a hydrocarbyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.
    Type: Grant
    Filed: November 16, 1992
    Date of Patent: September 6, 1994
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Dennis P. Riley, John J. Talley, Barry L. Parnas
  • Patent number: 5342838
    Abstract: The present invention relates to phenolic thioetheramides of the formula ##STR1## wherein R.sup.1 and R.sup.2 are tert-alkyl or phenyl, Alk.sup.1 and Alk.sup.2 are alkylene; X is sulfur or oxygen, m is 0, 1, or 2; and R is ##STR2## wherein R.sup.3 and R.sup.4 are hydrogen or alkyl and Alk.sup.3 is alkylene; or ##STR3## wherein Y is CH, N, O, or S; R.sup.6 is hydrogen, alkyl, phenyl, substituted phenyl, benzyl, substituted benzyl or a heterocyclic amine; and R.sup.7 is hydrogen or alkyl. The compounds inhibit 5-lipoxygenase and are useful in the treatment of inflammation and allergic conditions.
    Type: Grant
    Filed: December 9, 1993
    Date of Patent: August 30, 1994
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis