Of Acyclic Carboxylic Acid Anhydride Patents (Class 564/144)
  • Patent number: 9006488
    Abstract: A solvent-free mechanical process of reacting amine compounds with acetylating agents resulting in amides such as acetaminophen is described.
    Type: Grant
    Filed: March 20, 2014
    Date of Patent: April 14, 2015
    Inventors: Muhammad Amin, Muhammad S. Iqbal
  • Patent number: 8946476
    Abstract: The present patent application relates to an alternative process for the preparation of amino derivatives. In particular, the present application relates to an improved process for the manufacture of Lacosamide (LCM), (R)-2-acetamido-N-benzyl-3-methoxypropion-amide, which is useful as an anticonvulsive drug. In a particular aspect, the present invention relates to a process of manufacture of optically enriched (R)-2-acetamido-N-benzyl-3-methoxypropion-amide (I) comprising resolution of 2-acetamido-N-benzyl-3-methoxypropion-amide (II).
    Type: Grant
    Filed: November 6, 2009
    Date of Patent: February 3, 2015
    Assignee: UCB Pharma GmbH
    Inventors: Didier Bouvy, Alain Merschaert, Véronique Pinilla, Joerg Hamann, Ralf Kanzler, Antoine Thomas
  • Patent number: 8907132
    Abstract: Processes for preparing and purifying (R)-2-acetamido-N-benzyl-3-methoxy-propionamide of formula-1 and intermediates thereof are provided.
    Type: Grant
    Filed: February 9, 2011
    Date of Patent: December 9, 2014
    Assignee: MSN Laboratories Private Limited
    Inventors: Manne Satyanarayana Reddy, Sajja Eswaraiah, Aluru Srinivas, Revu Satyanarayana
  • Publication number: 20140288330
    Abstract: The invention relates to a process for preparing N-alkyl(meth)acrylamides by reacting (meth)acrylic anhydride with corresponding alkylamines.
    Type: Application
    Filed: November 20, 2012
    Publication date: September 25, 2014
    Applicant: Evonik Roehm GmbH
    Inventors: Dirk Broell, Benedikt Laux, Christian Maul, Patrick Peter, Claus Zimmer
  • Patent number: 8722931
    Abstract: The invention is directed to a compound represented by the Formula (1) as defined herein, and a method for preparing a compound represented by the Formula (1) which includes: reacting a diamine compound represented by the Formula (2) as defined herein with a methacrylic anhydride or an acrylic anhydride under a condition where an organic acid having a pKa of 2.0 or more is present in an amount of 0.5 to 5.0 moles based on 1 mole of the diamine compound to obtain a reaction mixture; adding phosphoric acid to the reaction mixture; and purifying the reaction mixture by extraction with an organic solvent.
    Type: Grant
    Filed: December 21, 2011
    Date of Patent: May 13, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Yu Iwai, Takafumi Nakayama, Junya Abe, Ichiro Koyama
  • Patent number: 8445723
    Abstract: Methods of producing the N-alkyl(alkyl)acrylamides. In a general embodiment, the present disclosure provides a method of producing an N-alkyl (alkyl)acrylamide comprising providing an aqueous solution comprising an N-alkyl amine and adding to the aqueous solution a base and an (alkyl)acrylic anhydride to form a precipitated N-alkyl(alkyl)acrylamide.
    Type: Grant
    Filed: August 19, 2008
    Date of Patent: May 21, 2013
    Assignee: Nalco Company
    Inventor: John D. Morris
  • Patent number: 8436206
    Abstract: Process for the industrial synthesis of the compound of formula (I) Application of such process in the synthesis of agomelatine.
    Type: Grant
    Filed: July 30, 2012
    Date of Patent: May 7, 2013
    Assignee: Les Laboratoires Servier
    Inventors: Thierry DuBuffet, Jean-Pierre Lecouve, Jean-Paul Hermet
  • Publication number: 20130041180
    Abstract: Processes for preparing and purifying (R)-2-acetamido-N-benzyl-3-methoxy-propionamide of formula-1 and intermediates thereof are provided.
    Type: Application
    Filed: February 9, 2011
    Publication date: February 14, 2013
    Inventors: Manne Satyanarayana Reddy, Sajja Eswaraiah, Aluru Srinivas, Revu Satyanarayana
  • Publication number: 20120330062
    Abstract: Process for the industrial synthesis of the compound of formula (I) Application of such process in the synthesis of agomelatine.
    Type: Application
    Filed: July 30, 2012
    Publication date: December 27, 2012
    Applicant: LES LABORATOIRES SERVIER
    Inventors: Thierry Dubuffet, Jean-Pierre Lecouve, Jean-Paul Hermet
  • Publication number: 20120165572
    Abstract: The invention is directed to a compound represented by the Formula (1) as defined herein, and a method for preparing a compound represented by the Formula (1) which includes: reacting a diamine compound represented by the Formula (2) as defined herein with a methacrylic anhydride or an acrylic anhydride under a condition where an organic acid having a pKa of 2.0 or more is present in an amount of 0.5 to 5.0 moles based on 1 mole of the diamine compound to obtain a reaction mixture; adding phosphoric acid to the reaction mixture; and purifying the reaction mixture by extraction with an organic solvent.
    Type: Application
    Filed: December 21, 2011
    Publication date: June 28, 2012
    Applicant: FUJIFILM CORPORATION
    Inventors: Yu IWAI, Takafumi NAKAYAMA, Junya ABE, Ichiro KOYAMA
  • Publication number: 20110218312
    Abstract: A novel process is described which allows N-isopropyl(meth)acrylamide to be obtained in high purity and yield in a simple manner, by reacting methacrylic anhydride with isopropylamine, optionally in a solvent.
    Type: Application
    Filed: November 19, 2009
    Publication date: September 8, 2011
    Applicant: EVONIK ROEHM GmbH
    Inventors: Joachim Knebel, Wilhelm Karnbrock, Volker Kerscher
  • Patent number: 7985820
    Abstract: A non-water soluble polymeric surfactant is prepared by reacting a polymerized/bodied unsaturated oil with maleic anhydride followed by a further partial or complete reaction with an amine to form an amide; or an alcohol to form an ester.
    Type: Grant
    Filed: October 15, 2007
    Date of Patent: July 26, 2011
    Assignee: Sun Chemical Corporation
    Inventors: Ramasamy Krishnan, Kenneth Smith, Neil Young, Inessa Gurevich
  • Publication number: 20100048951
    Abstract: Methods of producing the N-alkyl(alkyl)acrylamides. In a general embodiment, the present disclosure provides a method of producing an N-alkyl (alkyl)acrylamide comprising providing an aqueous solution comprising an N-alkyl amine and adding to the aqueous solution a base and an (alkyl)acrylic anhydride to form a precipitated N-alkyl(alkyl)acrylamide.
    Type: Application
    Filed: August 19, 2008
    Publication date: February 25, 2010
    Inventor: John D. Morris
  • Patent number: 7329780
    Abstract: Provided is a method of preparing an optically pure compound having formula 1 or its salts. The method includes: reacting (R)-2-(4-methoxy-3-aminosulfonyl-phenyl)-1 -methylethylamine or its salts with a compound selected from the group consisting of chloroacetic acid, bromoacetic acid, fluoroacetic acid, iodoacetic acid, ?-halogenoacetic acid anhydride, and ?-halogenoacetyl halide in the presence of a base or an acylating agent.
    Type: Grant
    Filed: December 9, 2004
    Date of Patent: February 12, 2008
    Assignee: CJ Corporation
    Inventors: Seong Hwan Cho, Dong Kwon Lim, Kwang Hyeg Lee, Yong Sik Youn, Choong Sil Park
  • Patent number: 6927290
    Abstract: There is disclosed an advantageous mixed acid anhydride production method of formula (1): R1C(O)OY(O)n(R2)p??(1) wherein R1, R2 and Y denote the same as defined below, n and p denote an integer of 1 or 2, which is characterized by adding a carboxylic acid of formula (2); R1COOH??(2) wherein R1 denotes a hydrogen atom, an optionally substituted alkyl group or the like, an organic base to a solution of a carboxylic acid activating agent of formula (3); (R2)pY(O)nX??(3) wherein R2 denotes an optionally substituted aliphatic hydrocarbyl group or the like, Y denotes a carbon atom, a phosphorus atom, or a sulfur atom, and X denotes a chlorine atom or the like.
    Type: Grant
    Filed: May 10, 2004
    Date of Patent: August 9, 2005
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Miki, Hideki Ushio, Isao Kurimoto
  • Patent number: 6350909
    Abstract: The invention relates to new imides, to a plurality of processes for their preparation and to their use as fungicides.
    Type: Grant
    Filed: January 2, 2001
    Date of Patent: February 26, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich Heinemann, Herbert Gayer, Peter Gerdes, Martin Vaupel, Astrid Mauler-Machnik, Gerd Hänssler, Klaus Stenzel, Martin Kugler, Thomas Jaetsch, Peter Wachtler
  • Patent number: 6166243
    Abstract: Disclosed herein is a method for making compounds having the structural formulae (I) or (II): ##STR1## wherein: X is a) phenyl; lower phenylalkoxy; phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from C.sub.1 -C.sub.4 alkoxy; hydroxyl; halogen; lower alkyl; and lower alkylthio; or c) along with the phenyl to which it is attached, forms a multiple fused ring heterocycle such as dibenzofuranyl; Y is H, C.sub.1 -C.sub.4 alkanoyl, C.sub.1 -C.sub.4 haloalkanoyl dialkoxyphosphoryl, alkylaminocarbonyl, haloalkylsulfonyl, or C.sub.1 -C.sub.4 alkoxy carbonyl; and R is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 cycloalkoxy, haloalkyl, alkoxyalkyl, arylalkoxy, alkenyl, alkylthio, alkoxycarbonyl, alkylamino, heteroaryl, arylalkyl, haloalkoxy, aryloxy, or C.sub.3 -C.sub.
    Type: Grant
    Filed: November 1, 1999
    Date of Patent: December 26, 2000
    Assignee: CK Witco Corporation
    Inventors: Haihong Jin, Joseph A. Feiccabrino
  • Patent number: 6121326
    Abstract: Compounds which are useful as a tachykinin antagonist are substituted alkyltetraamine derivatives which are represented by the following formula (I) or a pharmaceutically acceptable salt, a complex compound or a solvate thereof. ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and each is a phenyl group which may be substituted with one or more hydroxyl, lower alkoxy and/or acyloxy group(s). The compounds are useful as an anti-inflammatory agent, anti-allergic agent, analgesic, antiemetic, agent for irritable colon syndrome, agent for dermal disease, agent for vasospastic disease, agent for cerebral ischemic disease, antidepressant, antianxiety agent, agent for autoimmune disease, antispasmodic, and as a muscle relaxant, etc.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: September 19, 2000
    Assignee: Nippon Zoki Pharmaceutical Co., Ltd.
    Inventors: Atsushi Yamamoto, Ko Nakamura, Masanori Otsuka
  • Patent number: 6001881
    Abstract: Benzoylguanidines of the formula I ##STR1## in which: R(1) to R(4) have the meanings given in the claims, are antiarrhythmic pharmaceuticals, having a cardioprotective component, which are also valuable for the prevention of ischemically induced damage, in particular in association with the triggering of ischemically induced cardiac arrhythmias. As a consequence of inhibiting the cellular Na.sup.+ /H.sup.+ exchange mechanism, they are used for treating acute or chronic damage triggered by ischemia. In addition to this, they are notable for their strong inhibitory effect on the proliferation of cells. They are suitable for preventing the genesis of high blood pressure.
    Type: Grant
    Filed: June 4, 1997
    Date of Patent: December 14, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Weichert, Joachim Brendel, Heinz-Werner Kleemann, Hans Jochen Lang, Jan-Robert Schwark, Udo Albus, Wolfgang Scholz
  • Patent number: 5929281
    Abstract: A heterocyclic aromatic halide or an aryl halide is reacted with an amine compound in the presence of a base to give a heterocyclic aromatic amine or an arylamine, respectively. In this reaction, a catalyst comprising a palladium compound and a tertiary phosphine is used for the preparation of a heterocyclic aromatic amine, and a catalyst comprising a palladium compound and a trialkylphosphine is used for the preparation of an arylamine.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: July 27, 1999
    Assignee: Tosoh Corporation
    Inventors: Masakazu Nishiyama, Yasuyuki Koie
  • Patent number: 5892112
    Abstract: Synthetic mammalian matrix metalloprotease inhibitors are disclosed that are useful for treating or preventing diseases wherein said diseases are caused by unwanted mammalian matrix metalloprotease activity and include skin disorders, keratoconus, restenosis, rheumatoid arthritis, wounds, cancer, angiogenesis and shock.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: April 6, 1999
    Assignees: Glycomed Incorporated, The University of Florida
    Inventors: Daniel E. Levy, Damian Grobelny, Cho Tang, Kevin R. Holme, Richard E. Galardy, Gregory S. Schultz, Asaad Nematalia, John H. Musser
  • Patent number: 5783735
    Abstract: A process for preparing polymeric amides is disclosed. The process comprises sequentially reacting a hydrocarbon polymer functionalized (e.g., via the Koch reaction) to contain acid, ester, thioacid and/or thioester groups with a heavy polyamine to form a partially derivatized product in which at least about 85% of the functional groups are converted to heavy (thio)amide groups, and then reacting the partially derivatized product with an excess of light amine to complete the derivatization by converting substantially all of the remaining functional groups to light (thio)amide groups. Products of the foregoing process are also disclosed, which products are useful as additives in fuels and in lubricants.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: July 21, 1998
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jacob I. Emert, Joseph V. Cusumano, David C. Dankworth, William D. Diana, William B. Eckstrom, Keith R. Gorda, Antonio Gutierrez, Jon E. Stanat, Warren A. Thaler, Stephen Zushma
  • Patent number: 5700839
    Abstract: Benzoylguanidines of the formula I ##STR1## wherein R.sup.1 and R.sup.2 have the meanings indicated herein, and their physiologically acceptable salts, show anti-arrhythmic properties and act as inhibitors of the cellular NA.sup.+ /H.sup.+ antiporter.
    Type: Grant
    Filed: October 20, 1995
    Date of Patent: December 23, 1997
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Rolf Gericke, Dieter Dorsch, Manfred Baumgarth, Klaus-Otto Minck, Norbert Beier
  • Patent number: 5648535
    Abstract: A process for the production of N-acylaminophenols by the concurrent hydrogenation of a nitrophenol to an aminophenol and the acylation of the aminophenol with acyl anhydride takes place on a continuous basis in a stirred tank reactor in which liquid product is continuously withdrawn from the reactor. Of particular interest is the manufacture of acetaminophen, N-acetyl-p-aminophenol by continuous reaction of p-ntirophenol, hydrogen and acetic anhydride.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: July 15, 1997
    Assignee: Hoechst Celanese Corp.
    Inventors: James A. Foster, Werner H. Mueller, Debra A. Ryan, Hartmut Wiezer
  • Patent number: 5606098
    Abstract: Amides and esters of perfluoropolyoxaalkylene-sulfo- or perfluoropolyoxaalkylene-carboxylic acids of the general following formula:R.sub.F R.sub.F.sup.I ZQ, whereR.sub.F =CF.sub.3 O--, C.sub.2 F.sub.5 O--, C.sub.3 F.sub.7 O--, C.sub.8 F.sub.17 O--,R.sub.F.sup.I= ##STR1## --(CF.sub.2 CF.sub.2 O--).sub.n CF.sub.2 --, --(CF.sub.2 CF.sub.2 CF.sub.2 O).sub.n CF.sub.2 CF.sub.2 --,where n=8-55;Z=--CO--, --SO.sub.2 --,Q=--N(C.sub.m H.sub.2m OH).sub.2, where m=2, 3, 4, 6, 8, 10--N[(C.sub.2 H.sub.4 O).sub.4 C.sub.3 H.sub.6 OH].sub.2,--NH--C.sub.2 H.sub.4 OR.sub..eta., where R.eta.=CH.sub.3 --, C.sub.2 H.sub.5 --, C.sub.3 H.sub.7 --,--NH(C.sub.2 H.sub.4 O).sub.5 H,--OC.sub.1 H.sub.21 N(C.sub.1 H.sub.21 OH).sub.2, where .eta.=1, 2, 4C.sub.k H.sub.2k+1 O--, where k=6, 8, 10.
    Type: Grant
    Filed: October 3, 1995
    Date of Patent: February 25, 1997
    Assignee: AO "Avtokoninvest"
    Inventors: Nikolai A. Ryabinin, Aleksandr N. Ryabinin
  • Patent number: 5492545
    Abstract: Additives which improve the low-temperature properties of distillate fuels are the reaction products of (1) diols, and (2) the product of pyromellitic dianhydride and combinations of two or more different aminoalcohols with long-chain hydrocarbyl groups attached.
    Type: Grant
    Filed: August 15, 1994
    Date of Patent: February 20, 1996
    Assignee: Mobil Oil Corporation
    Inventors: David J. Baillargeon, Angeline B. Cardis, Dale B. Heck
  • Patent number: 5399760
    Abstract: A method is provided for purifying crude N-acetyl-para-aminophenol (APAP) containing color bodies or their precursors, the method comprising: a) forming a solution of the crude APAP; and b) subsequently contacting the solution with substoichiometric quantifies of an acetylating agent for a sufficient period of time to convert said color bodies or their precursors to substantially non-color bodies/stable, colorless substances; said quantities of acetylating agent provided is such that substantially none of the APAP is converted to other compounds.
    Type: Grant
    Filed: August 11, 1993
    Date of Patent: March 21, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Edward G. Zey, Olan S. Fruchey, Thomas H. Shockley, Joe S. Trevino, B. Frank Wood, Daniel D. Lindley
  • Patent number: 5344979
    Abstract: A method is provided for purifying a crude N-acetyl-para-aminophenol (APAP) containing color bodies or their precursors, the method comprising: a) forming a wet crude APAP; and b) subsequently drying said crude APAP in the presence of a sufficient amount of an acetylating agent for a sufficient period of time to convert said color bodies or their precursors to substantially non-color bodies.
    Type: Grant
    Filed: April 29, 1993
    Date of Patent: September 6, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Edward G. Zey, George A. Blay
  • Patent number: 5288906
    Abstract: Optionally substituted p-aminophenol compounds, easily converted into the N-acylated derivatives thereof, are prepared by hydrogenating the corresponding nitrobenzene, in solution in a saturated aliphatic monocarboxylic acid, notably acetic acid, in the presence of an effective amount of a protonic acid.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: February 22, 1994
    Assignee: Rhone-Poulence Chimie
    Inventors: Michel Gubelmann, Christian Maliverney
  • Patent number: 5239048
    Abstract: Block polyamido polyamine condensation products of an aromatic polycarboxylic acid component with a polyoxyalkylene polyamine component prepared by reacting the polycarboxylic acid component with an amount of the polyoxyalkylene polyamine component sufficient to react each carboxyl group with 1 mole of the polyoxyalkylene polyamine component.The polyoxyalkylene polyamine being selected from the group consisting of polyoxypropylene diamines, polyoxyethylene diamines, polyoxyethylene/oxypropylene diamines and polyoxypropylene triamines, and the aromatic polycarboxylic acid component being selected from the group consisting of C.sub.8 to C.sub.28 benzene dicarboxylic acids, benzene tricarboxylic acids, naphthalene carboxylates, hemimellitic acid, 1,1,3-trimethyl-3-phenylindan-4',5-dicarboxylic acid, trimellitic acid, and anhydrides and C.sub.1 to C.sub.4 alkyl esters thereof.
    Type: Grant
    Filed: May 4, 1990
    Date of Patent: August 24, 1993
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5220063
    Abstract: Acylamides or amine acylate salts of arylalkanolamines are prepared by reacting an arylisonitrosoalkanone with hydrogen and a carboxylic acid, carboxylic acid anhydride or carboxylic acid ester or mixture thereof in the presence of a transition metal catalyst; optionally the product is converted to the corresponding arylalkanolamine hydrochloride salt by reaction of the acylamide or amine acylate salt of the arylalkanolamine with hydrogen chloride in a C.sub.1 -C.sub.3 alkyl alcohol.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: June 15, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
  • Patent number: 5206436
    Abstract: Process for purifying, by crystallization, TAED having a titer.gtoreq.99.5% from a mixture containing crude TAED obtained by acetylation of DAED, wherein the purification process is performed in two different stages (1, 2), characterized in that the temperatures at which the stages are performed differ from one another (delta t) by values comprised between 55.degree. and 110.degree..
    Type: Grant
    Filed: July 22, 1991
    Date of Patent: April 27, 1993
    Assignee: Caffaro S.p.A.
    Inventors: Enrico Pontoglio, Giordano Donelli, Sandro Parodi
  • Patent number: 5155269
    Abstract: A process for removing impurities from an aqueous feed mixture comprising a reaction solution produced by catalytic hydrogenation of nitrobenzene in an acid aqueous medium. An aqueous feed mixture comprising the reaction solution is contacted with an extractant comprising aniline for extraction from the feed mixture of 4,4'-diaminodiphenylether, thereby providing a primary raffinate that contains p-aminophenol and is contaminated with aniline. The primary raffinate is contacted at a pH of between about 5.5 and about 8.0 with a purifying solvent, the purifying solvent comprising an organic solvent effective for extraction of aniline from the primary raffinate, thereby producing a purified raffinate comprising p-aminophenol.Also described is a unified process for the preparation of N-acetyl-p-aminophenol in which p-aminophenol contained in the aforesaid purified raffinate is acetylated without prior separation of solid p-aminophenol from the raffinate.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: October 13, 1992
    Assignee: Mallinckrodt
    Inventors: Thomas J. Dunn, Vojko B. Jovanovic
  • Patent number: 5128441
    Abstract: A block polyamido primary amine condensation product prepared by reacting a defined polyoxyalkylene polyamine having terminal primary amine groups with an amount of a defined dicarboxylic acid or an anhydride or a C.sub.1 to C.sub.4 alkyl ester thereof, sufficient to react one mole of the dicarboxylic acid reactant with each primary amine group of the polyoxyalkylene polyamine to thereby prepare an intermediate condensation reaction product containing terminal carboxyl groups, and reacting one mole of a defined organic di-primary amine with each terminal carboxyl group of the said intermediate condensation reaction product to thereby provide, as the principal product of the reaction a block polyamido primary amine condensation product.
    Type: Grant
    Filed: May 4, 1990
    Date of Patent: July 7, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5105009
    Abstract: Intermediates of Formula ##STR1## where R is a methylthio, methylsulfoxy, methylsulfonyl or a nitro group; andX1 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl, phenyl or phenylalkyl(1-6C), where the phenyl ring may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX1 together with X2 is an oxygen atom or an alkylene having from two to five Carbon atoms; orX1 together with X2 and R4 is a chain of formula ##STR2## where p is 3 or 4 and q is 1 or 2; and X2 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl or phenyl which may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX2 together with R4 is ##STR3## where n is 1 or 2; m is 0 or 1; X is hydrogen, halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; andX3 is hydrogen or --CO--R4 where R4 is hydrogen, 1-6 alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl, phenylalkyl(1-6C) or phenyl where the phenyl ring may be substituted by one or two halogen, 1-3 alkyl, 1-3 alkoxy or nitro; andX4 is --OH, fluorine,
    Type: Grant
    Filed: February 29, 1988
    Date of Patent: April 14, 1992
    Assignee: Zambon S.p.A.
    Inventors: Giancarlo Jommi, Dario Chiarino
  • Patent number: 5101012
    Abstract: This invention relates to a composition prepared by reacting(a) at least one reaction product of a hydrocarbyl substituted carboxylic acid or anhydride having a hydrocarbyl group containing from about 8 to about 150 carbon atoms and at least one polyamine wherein the reaction product has at least one NH group capable of addition to a double bond; with(b) at least one sulfo compound represented by the following formula: ##STR1## wherein each R.sub.1 is independently hydrogen or a hydrocarbyl group;a is zero or one;Q is a hydrocarbylene group or --C(X)N(R.sub.2)Q'--;R.sub.2 is hydrogen or a hydrocarbyl group;X is sulfur or oxygen;each Q' is a hydrocarbylene group; andZ is --S(O)OH, or --S(O).sub.2 OH or an ester, a metal salt or an ammonium salt of the sulfo compound.The invention also relates to polymer fabrics treated with the compositions of the present invention. The treated polymer fabrics have improved wicking/wetting characteristics.
    Type: Grant
    Filed: August 6, 1991
    Date of Patent: March 31, 1992
    Assignee: The Lubrizol Corporation
    Inventor: Kasturi Lal
  • Patent number: 5091572
    Abstract: Liquid amine terminated polyamide addition products having an average molecular weight of about 3,000 to about 10,000 are prepared by the non-catalytic reaction of a dicarboxylic acid having a molecular weight within the range of about 130 to about 700 with a higher molecular weight polyoxypropylene diamine having an average molecular weight within the range of about 1,500 to about 6,000 and with a lower molecular weight polyoxypropylene diamine having an average molecular weight within the range of about 200 to about 700, the reaction conditions including a temperature within the range of about 150.degree. to about 280.degree. C., a pressure of about 0.1 to 20 atmospheres and a reaction time of about 2 to about 5 hours.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: February 25, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Wei-Yang Su
  • Patent number: 5047586
    Abstract: A process for the preparation of 4-acylamino-2-aminoalkoxybenzenes of the general formula (1) ##STR1## in which R denotes an alkyl-C.sub.1 -C.sub.6 - or alkoxy-C.sub.1 -C.sub.4 -alkylene-C.sub.1 -C.sub.4 group and R' denotes a methyl or ethyl group, by pumping a solution or suspension of a 2,4-dinitroalkoxybenzene of the general formula (2) ##STR2## in which R has the abovementioned meaning, in a butyl acetate into a stirred suspension of a nickel catalyst on a kieselguhr carrier in butyl acetate, which has been initially introduced into an autoclave, at a hydrogen pressure of about 5 to about 50 bar, and a temperature of about 60.degree. to about 120.degree. C., at a rate which corresponds to the rate of hydrogenation of 2,4-dinitroalkoxybenzene to 2,4-diaminoalkoxybenzene, dehydrating the reduction solution by azeotropic distillation, after the hydrogenation, and acylating the resulting 2,4-diaminoalkoxybenzene with about 0.90 to 0.
    Type: Grant
    Filed: August 22, 1990
    Date of Patent: September 10, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Heise, Manfred Hintzmann
  • Patent number: 5039306
    Abstract: Additives which improve the low-temperature properties of distillate fuels are the reaction products of (1) diols, and (2) the product of pyromellitic dianhydride and aminoalcohols and/or amines with long-chain hydrocarbyl groups attached.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: August 13, 1991
    Assignee: Mobil Oil Corp.
    Inventors: David J. Baillargeon, Angeline B. Cardis, Dale B. Heck
  • Patent number: 5039309
    Abstract: Additives comprising the reaction products of aminodiols and the product of pyromellitic dianhydride and aminoalcohols and/or amines with long-chain hydrocarbyl groups improve the low-temperature properties of distillate fuels.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: August 13, 1991
    Assignee: Mobil Oil Corporation
    Inventors: David J. Baillargeon, Angeline B. Cardis, Dale B. Heck
  • Patent number: 5002588
    Abstract: Additive reaction products of (1) hydrocarbyl diols, and (2) the product of benzophenone tetracarboxylic dianhydride and hydrocarbyl aminoalcohols and/or amines improve the low-temperature properties of distillate fuels when added thereto.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: March 26, 1991
    Assignee: Mobil Oil Corporation
    Inventors: David J. Baillargeon, Angeline B. Cardis, Dale B. Heck
  • Patent number: 5002589
    Abstract: Additives which improve the low-temperature properties of distillate fuels are the reaction products of (1) diaminodiols, and (2) the product of pyromellitic dianhydride and aminoalcohols and/or amines with long-chain hydrocarbyl groups attached.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: March 26, 1991
    Assignee: Mobil Oil Corp.
    Inventors: David J. Baillargeon, Angeline B. Cardis, Dale B. Heck
  • Patent number: 5000758
    Abstract: Additives comprising the reaction products of aminodiols and the products of benzophenone tetracarboxylic dianhydride and aminoalcohols and/or amines with long-chain hydrocarbyl groups attached improve the low-temperature properties of distillate fuels.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: March 19, 1991
    Assignee: Mobil Oil Corp.
    Inventors: David J. Baillargeon, Angeline B. Cardis, Dale B. Heck
  • Patent number: 4990671
    Abstract: N-acylated dialkylaminophenols are produced at greater yields under mild reaction conditions by a novel in situ process which begins with catalytic hydrogenation of dialkylnitrosophenols in an aprotic organic reaction medium.
    Type: Grant
    Filed: December 7, 1989
    Date of Patent: February 5, 1991
    Assignee: Mallinckrodt, Inc.
    Inventors: Neil Dunski, Henry J. Buehler
  • Patent number: 4898977
    Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4780542
    Abstract: The invention relates to the preparation of an ester or an amide from an anhydride with an alcohol or an amine, wherein the anhydride is first prepared by reacting an acid and an alkyl chloroformate in a 100% aqueous medium, that is, 100% water.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: October 25, 1988
    Assignee: Montefiore Medical Center
    Inventor: Iraj Lalezari
  • Patent number: 4744798
    Abstract: Benzophenone derivatives, e.g., benzophenone tetracarboxylic dianhydride, and esters or mixtures thereof when reacted with various hydrocarbyl amines provide additives that are highly useful as fuel detergents, intake valve and exhaust gas valve deposit reducers.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: May 17, 1988
    Assignee: Mobil Oil Corporation
    Inventor: Harry J. Andress
  • Patent number: 4670589
    Abstract: Production of N-acetyl-p-aminophenol by hydrogenation of p-nitrophenol to p-aminophenol and concurrently acetylating the p-aminophenol with acetic anhydride with the acetylation controlled so that substantially no excess acetic anhydride is present in the system until the hydrogenation reaction has reached substantial completion.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: June 2, 1987
    Assignee: Monsanto Company
    Inventors: John H. Van Ness, J. Bruce Warner
  • Patent number: 4658054
    Abstract: A process for the preparation of 5,6-dialkoxyanthranilic acids is described. The 5,6-dialkoxyanthranilic acids are useful in the preparation of substituted quinazolinediones which are active cardiotonic agents.
    Type: Grant
    Filed: July 29, 1985
    Date of Patent: April 14, 1987
    Assignee: Ortho Pharmaceutical Corporation
    Inventor: Richard A. Conley
  • Patent number: 4499283
    Abstract: This disclosure describes a novel process for the preparation of 2-(n-propyl)-4-methyl-5-(lower alkanoyl)imidazoles which are useful as intermediates for the preparation of anti-asthmatic agents.
    Type: Grant
    Filed: June 28, 1982
    Date of Patent: February 12, 1985
    Assignee: American Cyanamid Company
    Inventors: Sivaraman Raghu, Steven L. Peake