Cyclobutyl In Acid Moiety Patents (Class 560/123)
  • Patent number: 6417389
    Abstract: This invention relates to a novel advantageous process for the stereoselective preparation of 2-hydroxy-4-phenylbutyrates (HPB esters) and of their precursors. This is done by starting from readily accessible &agr;-unsaturated &agr;-hydroxy-&ggr;-keto esters which can be prepared by Claisen condensation.
    Type: Grant
    Filed: September 25, 2000
    Date of Patent: July 9, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Martin Studer, Peter Herold, Adriano Indolese, Stefan Burckhardt
  • Patent number: 6383454
    Abstract: A process for fluorinating a hydrocarbon substrate is by mixing it with an inert diluent and mixing the diluted substrate with a gaseous fluorinating reagent to form a foam reaction mixture. The fluorinating reagent reacts with the substrate in the form to foam product. The foam is separated into a liquid component which contains product and a gas component. Product is withdrawn from the liquid component which is then returned to the diluting step. Fluorinating reagent is fed into the gas component which is then recirculated to the mixing step. An installation for fluorinating a hydrocarbon substrate includes, in sequence as a circuit, a dilution stage, a mixing stage, a reaction stage and a separation stage. Liquid returning means feeds liquid from the separation stage to the dilution stage, and gas recirculation means feeds gas from the separation stage to the mixing stage.
    Type: Grant
    Filed: July 13, 2001
    Date of Patent: May 7, 2002
    Assignee: South Africa Nuclear Energy Corporation Ltd.
    Inventors: Driekus Van Der Westhuizen, Petrus Johannes Venter
  • Patent number: 6376699
    Abstract: Hydroazinecarboxylic acid ester of the formula In which R1 is an optionally substituted alkyl group, an aryl group, an arylalkyl group or a cycloalkyl group, and R3 is an optionally substituted alkyl group.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: April 23, 2002
    Assignee: Lonza AG
    Inventor: Ulrich Veith
  • Patent number: 6369194
    Abstract: The invention relates to compounds of formula where R is a structural diversity element selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, peptidyl, heteroatom-substituted alkyl, cycloalkyl, and amines; and Nu is a structural diversity element derived from a nucleophile, NuH, selected from the group consisting of amines, amino acids, peptide, water, hydrogen sulfide, alcohols, and thiols. The invention also relates to arrays and combinatorial libraries of such compounds, and to a method of preparing such compounds.
    Type: Grant
    Filed: November 9, 1998
    Date of Patent: April 9, 2002
    Assignee: Yale University
    Inventor: Harry H. Wasserman
  • Patent number: 6329429
    Abstract: GABA analogs such as gabapentin and pregabalin are useful to prevent and treat inflammatory diseases.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: December 11, 2001
    Assignee: Warner-Lambert Company
    Inventors: Denis Schrier, Charles Price Taylor, Jr., Karin Nanette Westlund High
  • Patent number: 6258975
    Abstract: Provided is an industrially useful process for producing an optically active 2-hydroxy-4-arylbutyric acid or its ester. An optically active acyloxysuccinic anhydride is reacted with an aromatic compound in the presence of a Lewis acid to produce an optically active 2-acyloxy-4-oxo-4-arylbutyric acid. The 2-acyloxy-4-oxo-4-arylbutyric acid is converted to an optically active 2-acyloxy-4-arylbutyric acid through catalytic reduction. The 2-acyloxy-4-arylbutyric acid is hydrolyzed in the presence of an acid or an alkali to produce an optically active 2-hydroxy-4-arylbutyric acid. The 2-hydroxy-4-arylbutyric acid is reacted with an alcohol in the presence of an acid to produce an optically active 2-hydroxy-4-arylbutyric acid ester.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: July 10, 2001
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masahiko Kurauchi, Yoshimasa Hagiwara, Hiroyuki Matsueda, Takashi Nakano, Kunisuke Izawa
  • Patent number: 6245922
    Abstract: A photoactive compound that is the reaction product of an alkenyl azlactone compound and a nucleophilic aromatic ketone is described. Mer units derived from this compound can be used, for example, to crosslink via a hydrogen abstracting mechanism acrylic polymers in which they are incorporated.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: June 12, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Steven M. Heilmann, Gaddam N. Babu, Larry R. Krepski, Howell K. Smith, II, Daniel E. Mickus
  • Patent number: 6156896
    Abstract: The present invention provides several methods of synthesis and separation in which organic/fluorous phase separation techniques are used to effect separations. The present invention also provides novel compositions of matter comprising fluorous Si, Sn and Ge compounds.
    Type: Grant
    Filed: May 15, 1998
    Date of Patent: December 5, 2000
    Assignee: University of Pittsburgh
    Inventors: Dennis P. Curran, Sabine Hadida Ruah, Masahide Hoshino, Armido Studer, Peter Wipf, Patrick Jeger, Sun-Young Kim, Rafael Ferritto
  • Patent number: 6153650
    Abstract: Novel gamma aminobutyric acids of formula (I) are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, inflammation, and gastrointestinal damage. Processes for the preparation and intermediates useful in the preparation are also disclosed.
    Type: Grant
    Filed: March 1, 1999
    Date of Patent: November 28, 2000
    Assignee: Warner-Lambert Company
    Inventors: Justin Stephen Bryans, David Christopher Horwell, Clare Octavia Kneen, Andrew John Thorpe, David Juergen Wustrow
  • Patent number: 6118019
    Abstract: A 3-alkoxypropionic ester derivative, an olefin polymerization solid catalyst component using the same, an olefin polymerization catalyst using the same, and a process for the preparation of a polyolefin using the same. The 3-alkoxypropionic ester derivative is represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrocarbon group having from 1 to 10 carbon atoms; R.sup.2 represents a hydrocarbon group having from 1 to 20 carbon atoms; R.sup.3 represents a hydrocarbon group having from 1 to 20 carbon atoms; and R.sup.4 represents a branched hydrocarbon group having 3 or more carbon atoms.
    Type: Grant
    Filed: December 29, 1998
    Date of Patent: September 12, 2000
    Assignee: Showa Denko K.K.
    Inventors: Masaki Fushimi, Shintaro Inazawa
  • Patent number: 6111130
    Abstract: The present invention relates to a process for the preparation of trifluoromethylated derivatives of the formula CF.sub.3 CCl.dbd.CHCH.sub.2 OC(.dbd.O)R, wherein R is unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl, unsubstituted or substituted C.sub.3 to C.sub.7 cycloalkyl, unsubstituted or substituted C.sub.2 to C.sub.12 alkenyl, a benzyl group unsubstituted or substituted with R', a phenyl group unsubstituted or substituted with R'; R' is an unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl; and wherein where R and/or R' are substituted each is substituted with R', by reaction of HCFC-353 with carboxylic acid salts. The trifluoromethylated derivatives, particularly CF.sub.3 CCl.dbd.CHCH.sub.2 OC(.dbd.O)CH.sub.3, are versatile intermediates for the synthesis of a wide variety of trifluoromethylated organic compounds, which find utility as pharmaceuticals, agricultural chemicals, and materials such as liquid crystals.
    Type: Grant
    Filed: May 10, 1999
    Date of Patent: August 29, 2000
    Assignee: AlliedSignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 6100424
    Abstract: Aminoacetic acid esters of formula I in which R.sup.1, R.sup.2 and R.sup.3 are identical or different hydrocarbon radicals, or any two of these radicals form a carbon ring with the carbon atom to which they are attached and R.sup.4 is hydrogen or an alkyl radical having 1-4 carbon atoms, are prepared by reacting an .alpha.-substituted malonic acid monoamide ester of formula II ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meanings above, by the Hofmann degradation reaction, with a hypohalite in an amount of up to 1.5 equivalents in an aqueous-basic medium containing base in an amount of 0.8-1.5 equivalents per mol. of starting malonic acid monoamide ester II.
    Type: Grant
    Filed: July 9, 1999
    Date of Patent: August 8, 2000
    Assignee: Degussa-Huels Aktiengesellschaft
    Inventor: Wolfgang Kleemiss
  • Patent number: 6025519
    Abstract: Cyclobutane-1,2-dicarboxylic esters of the formula: ##STR1## in which R.sup.1 is a C.sub.1-8 -alkyl group, an optionally substituted mono- or bicyclic cycloaliphatic group having 3 to 10 ring carbon atoms, an optionally substituted aryl or arylalkyl group or an optionally substituted saturated heterocyclic group and R.sup.2 is either C.sub.1-4 -alkyl or both radicals R.sup.2 together form a group of the formula --(CH.sub.2).sub.n --(n is 2 to 4), are prepared from the corresponding maleic or fumaric esters and ketene acetals in the presence of a Lewis acid and a sterically hindered base. The reaction is stereoselective when optically active maleic or fumaric esters are employed. The cyclobutane-1,2-dicarboxylic esters (I), in particular those having trans configuration, are intermediates in the synthesis of pharmaceutically active compounds.
    Type: Grant
    Filed: July 20, 1998
    Date of Patent: February 15, 2000
    Assignee: Lonza, Ltd.
    Inventor: Andreas Brunner
  • Patent number: 5986095
    Abstract: A process is described for preparing a compound of the formula or the S-enantiomer thereof,wherein:R is alkyl, aryl, cycloalkyl, aralkyl, or cycloalkylalkyl,R.sup.1 is halogen;R.sup.2 is halogen, alkyl, cycloalkyl, aryl or ##STR1## wherein the process comprises treating the associated racemic alcohol with an acylatingagent ##STR2## (wherein L is a leaving group) and an enzyme or microorganism capable of enantioselective acylation. This process may also be used to isolate the unreacted R- or S-alcohol. The acylated product may be enantioselectively hydrolyzed with a lipase or lipase-supplying microorganism to the S- or R-alcohol. Compounds prepared by this invention are useful antipsychotic agents or useful intermediates therefor.
    Type: Grant
    Filed: January 6, 1992
    Date of Patent: November 16, 1999
    Assignee: E.R. Squibb & Sons, Inc.
    Inventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
  • Patent number: 5952521
    Abstract: Surfactants useful as dispersing aids in the preparation of compositions comprising a hydrophilic colloid having hydrophobic particles dispersed therein have the structure ##STR1## wherein M is a cation; X represents a group having the structure ##STR2## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represents hydrogen or alkyl; or R.sup.1 and R.sup.2 taken together represent cycloalkyl; or R.sup.3 and R.sup.4 taken together represent cycloalkyl; and, n represents 0 or 1; provided that the total number of carbon atoms in each X group is 3 or 4, and when R.sup.1 is hydrogen R.sup.2 is other than methyl. Such surfactants offer coating and photographic property advantages when incorporated in multilayer photographic materials comprising a support bearing a plurality of hydrophilic colloid layers.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: September 14, 1999
    Assignee: Eastman Kodak Company
    Inventors: Alan Robert Pitt, Trevor John Wear, Danuta Gibson
  • Patent number: 5939554
    Abstract: A method for preparing a diarylalanine compound is provided. The method includes reacting a diarylaminopropanediol with a reducing agent to form a diarylaminopropanol compound and/or contacting a serine ester derivative with an aryl metal reagent to form diarylaminopropanediol. A diarylmethyloxazolidinone compound is also provided.
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: August 17, 1999
    Assignee: NDSU Research Foundation
    Inventors: Mukund P. Sibi, Prasad K. Despande, Anthony J. LaLoggia
  • Patent number: 5863931
    Abstract: Amidino derivatives of formula (I) and salts, and pharmaceutically acceptable esters and amides thereof, in which: R.sup.1 is a C.sub.1-6 straight or branched chain alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.3-6 cycloalkyl group or a C.sub.3-6 cycloalkylC.sub.1-6 alkyl group; Q is an alkylene, alkenylene or alkynylene group having 3 to 6 carbon atoms and which may optionally be substituted by one or more C.sub.1-3 alkyl groups; a group of formula --(CH.sub.2).sub.p X(CH.sub.2).sub.q -- where p is 2 or 3, q is 1 or 2 and X is S(O).sub.x where x is 0, 1 or 2, O or NR.sup.2 where R.sup.2 is H or C.sub.1-6 alkyl; or a group of formula --(CH.sub.2).sub.r A(CH.sub.2).sub.s -- where r is 0, 1 or 2, s is 0, 1 or 2 and A is a 3 to 6 membered carbocyclic or heterocyclic ring which may optionally be substituted by one or more suitable substituents such as C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy, halo, nitro, cyano, trifluoro C.sub.1-6 alkyl, amino, C.sub.1-6 alkylamino or diC.sub.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: January 26, 1999
    Assignee: Glaxo Wellcome Inc.
    Inventors: Richard Mansfield Beams, Harold Francis Hodson, Richard Michael John Palmer
  • Patent number: 5859283
    Abstract: 4-Substituted isoxazole derivatives of formula I: ##STR1## wherein R, R.sup.1, R.sup.2, Q and n have the meanings defined in the description, which possess valuable herbicidal properties and intermediates useful in their preparation.
    Type: Grant
    Filed: February 11, 1998
    Date of Patent: January 12, 1999
    Assignee: Rhone-Poulenc Agriculture Limited
    Inventor: Susan Mary Cramp
  • Patent number: 5783593
    Abstract: The present invention provides a compound of the formula ##STR1## which inhibit squalene synthetase and cholesterol biosynthesis and are useful in the treatment of e.g., hyperlipidaemia, atherosclerosis, or fungal infections, processes for the preparation of the compounds of the invention, intermediates useful in these processes, and pharmaceutical compositions containing the compounds.
    Type: Grant
    Filed: April 29, 1996
    Date of Patent: July 21, 1998
    Assignee: Abbott Laboratories
    Inventors: William R. Baker, Saul H. Rosenberg, Anthony K. L. Fung, Todd W. Rockway, Stephen A. Fakhoury, David S. Garvey, B. Gregory Donner, Stephen J. O'Connor, Rajnandan N. Prasad, Wang Shen, David M. Stout, Gerard M. Sullivan
  • Patent number: 5773614
    Abstract: (1R,trans) Diprotected 3-methylene-1,2-cyclopropanedimethanol is oxidized to an optically active diol ##STR1## which is then cyclized to an orthoester ##STR2## This orthoester is then treated with a Lewis acid catalyst to give the cyclobutanone ##STR3## which is useful as an intermediate in the preparation of the antiviral agent ?1R-(1.alpha.,2.beta.,3.alpha.)!-2-amino-9-?2,3-bis(hydroxymethyl)cyclobut yl!-1,9-dihydro-6H-purin-6-one.
    Type: Grant
    Filed: September 13, 1996
    Date of Patent: June 30, 1998
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Jollie D. Godfrey, Jr., Richard H. Mueller
  • Patent number: 5631401
    Abstract: The present invention provides a compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof, which are useful in inhibiting protein farnesyltransferase and the farnesylation of the oncogene protein Ras or inhibiting de novo squalene production resulting in the inhibition of cholesterol biosynthesis, processes for the preparation of the compounds of the invention in addition to intermediates useful in these processes, a pharmaceutical composition, and to methods of using such compounds.
    Type: Grant
    Filed: January 24, 1995
    Date of Patent: May 20, 1997
    Assignee: Abbott Laboratories
    Inventors: Herman H. Stein, William R. Baker, Anthony K. L. Fung, Saul H. Rosenberg, Todd W. Rockway, Stephen A. Fakhoury, David S. Garvey, B. Gregory Donner, William J. McClellan, Stephen J. O'Connor, Rajnandan Prasad, Wang Shen, Gerard M. Sullivan
  • Patent number: 5623087
    Abstract: A method for preparing a diarylalanine compound is provided. The method includes reacting a diarylaminopropanediol with a reducing agent to form a diarylaminopropanol compound and/or contacting a serine ester derivative with an aryl metal reagent to form diarylaminopropanediol. A diarylmethyloxazolidinone compound is also provided.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: April 22, 1997
    Assignee: NDSU-Research Foundation
    Inventors: Mukund P. Sibi, Prasad K. Despande, Anthony J. LaLoggia
  • Patent number: 5610188
    Abstract: Compounds of the formula ##STR1## wherein the variables are defined in the specification. The compounds and their salts are soft anticholinergic/antisecretory agents especially useful as mydriatics and as antiperspirants.
    Type: Grant
    Filed: December 30, 1994
    Date of Patent: March 11, 1997
    Assignee: University of Florida
    Inventors: Richard H. Hammer, Nicholas S. Bodor
  • Patent number: 5565490
    Abstract: p-Hydroxyaniline derivatives of the formula I ##STR1## where the substituents have the following meanings: R.sup.1 is hydrogen, or unsubstituted or substituted alkyl;R.sup.2 and R.sup.3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;R.sup.4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl,OR.sup.5 or NR.sup.6 R.sup.7, whereR.sup.5, R.sup.6 are unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, andR.sup.7 is hydrogen or alkyl,and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests, and also compounds of the formula VI ##STR2## and their salts, processes for their preparation, compositions containing them and their use as intermediates and for controlling pests are described.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: October 15, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Oliver Wagner, Karl Eicken, Norbert G otz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5556864
    Abstract: Compounds of formula (I): ##STR1## [wherein: R.sup.1 is aryl; R.sup.2 is hydrogen, alkyl, alkoxy, halogen or cyano; R.sup.3 is a group of formula --B--NR.sup.4 R.sup.5, where R.sup.4 and R.sup.5 are independently hydrogen, alkyl or substituted alkyl or R.sup.4 and R.sup.5, together with the nitrogen to which they are attached, form a heterocycle, and B is alkylene or a group of formula --CH.sub.2 CH(OR.sup.6)CH.sub.2 --, where R.sup.6 is hydrogen, alkanoyl, substituted alkanoyl or arylcarbonyl, or a group of formula --D--R.sup.7, where D is a single bond or alkylene and R.sup.7 is a heterocycle; and A is alkylene; and pharmaceutically acceptable salts and esters thereof] are useful for the treatment and prevention of circulatory diseases and psychosis.
    Type: Grant
    Filed: January 5, 1995
    Date of Patent: September 17, 1996
    Assignee: Sankyo Company, Limited
    Inventors: Koichi Fujimoto, Naoki Tanaka, Fumitoshi Asai, Tomiyoshi Ito, Hiroyuki Koike
  • Patent number: 5545747
    Abstract: An optically inactive cyclobutanecarboxylic acid derivative of the general formula ##STR1## wherein R.sup.1 is a hydrogen atom or a straight or branched chain alkyl group having 1-14 carbon atoms, R.sup.2 is a straight or branched chain alkyl group having 1-14 carbon atoms, X.sup.1 and X.sup.2 independently represent hydrogen or fluorine atoms, as well as a liquid crystalline composition containing at least one such derivative.
    Type: Grant
    Filed: August 1, 1994
    Date of Patent: August 13, 1996
    Assignee: Kanto Kagaku Kabushiki Kaisha
    Inventors: Megumi Kawaguchi, Hiromi Inoue, Atsushi Sugiura, Kenji Suzuki, Tsunenori Fujii
  • Patent number: 5534188
    Abstract: An acetylene derivative represented by general formula (I): ##STR1## wherein R.sup.1 is saturated or unsaturated alkyl group having 3-20 carbon atoms, R.sup.2 is saturated or unsaturated alkyl group having 1-20 carbon atoms which may optionally be substituted by halogen atom or alkoxyalkyl group having 2-20 carbon atoms, A and B represent phenylene group or the like or taken as --A--B-- represent naphthalene group or the like, m and s are each 0 or 1, n is integer of 1-6, and * means asymmetric carbon atom; a process for producing said acetylene derivative, a liquid crystal composition using the same as active ingredient, and a liquid crystal element using said composition.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: July 9, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Takayuki Higashii, Shoji Toda, Naoyuki Takano, Kayoko Ueda, Koichi Fujisawa
  • Patent number: 5453464
    Abstract: This invention provides the use and preparation of certain 2,2'-diacetyl-bisacetoacetates and bis(beta-ketoesters). These compounds are useful in coating formulations as crosslinkers in conjunction with polyester, acrylic and/or other hydroxylated resins to provide coatings that cure at about 100.degree. and 175.degree. C. Certain combinations of these crosslinkers and resins cure at unusually low temperatures and provide films with good combinations of flexibility, hardness and adhesion.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: September 26, 1995
    Assignee: Eastman Chemical Company
    Inventors: J. Stewart Witzeman, Allen L. Crain
  • Patent number: 5445764
    Abstract: The invention relates to methylenecyclobutane benzene derivatives of the formula I ##STR1## in which R.sup.1, A.sup.1, Z.sup.1, L.sup.1, L.sup.2, m, V, W, Y and n have the meaning given in claim 1, and to their use as components of liquid-crystalline media for electrooptical displays.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: August 29, 1995
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Eike Poetsch, Werner Binder, Volker Meyer, Ulrich Finkenzeller, Bernhard Rieger
  • Patent number: 5434267
    Abstract: Process for the preparation of compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and n have the meaning given in the description, by reacting acetates with carbon monoxide in the presence of a basic auxiliary, followed by alkylation. The products are intermediates for fungicidal acrylates.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: July 18, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
  • Patent number: 5391571
    Abstract: The compounds of the formula: ##STR1## in which R.sup.1 is alkyl of 4 or more carbon atoms, cycloalkyl, 1-adamantyl, 2-adamantyl, 3-noradamantyl, 3-methyl-1-adamantyl, 1-fluorenyl, 9-fluorenyl, cycloalkylalkyl, phenyl, substituted phenyl, alkyl, alkoxy, halo, nitro, cyano or trifluoromethyl, phenylalkyl or substituted phenylalkyl, where the substituent on the benzene ring is alkyl, alkoxy, halo, nitro, cyano, trifluoromethyl or phenyl; R.sup.2 is hydrogen, alkyl or R.sup.1 taken with R.sup.2 and the nitrogen atom to which they are attached form a heterocyclic moiety of the formula: ##STR2## wherein ##STR3## in which R.sup.7 is hydrogen, alkyl, hydroxy, alkanoyloxy, hydroxyalkyl, hydroxycarbonyl, alkoxycarbonyl, phenyl or substituted phenyl, in which the substituent is alkyl, alkoxy, halo, nitro, cyano, haloalkyl, perhaloalkyl or dialkylaminoalkyl; R.sup.8 is hydrogen or alkyl or R.sup.7 and R.sup.8 taken together are polymethylene; R.sup.
    Type: Grant
    Filed: May 13, 1993
    Date of Patent: February 21, 1995
    Assignee: American Home Products Corporation
    Inventors: Richard E. Mewshaw, Thomas J. Commons, Donald P. Strike
  • Patent number: 5384072
    Abstract: The invention relates to methylenecyclobutane derivatives of the formula I ##STR1## in which R.sup.1, A.sup.1, A.sup.2, Z.sup.1, Z.sup.2, L.sup.1, L.sup.2, X, Y and m are as defined in claim 1, and to the use thereof as a component of liquid-crystalline media for electrooptical displays.
    Type: Grant
    Filed: September 15, 1993
    Date of Patent: January 24, 1995
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Eike Poetsch, Werner Binder, Thomas Geelhaar
  • Patent number: 5344962
    Abstract: Cyclobutane intermediates wherein the absolute stereochemistry is (1S,2R) of the formula ##STR1## are disclosed. These intermediates are useful in the preparation of compounds having anti-viral activity.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: September 6, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Saleem Ahmad
  • Patent number: 5312963
    Abstract: The present invention relates to a process for the preparation of substituted cyclobutanes and their use as intermediates for the preparation of anti-viral nucleoside analogs.
    Type: Grant
    Filed: June 14, 1993
    Date of Patent: May 17, 1994
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Richard J. Pariza, Steven M. Hannick, Thomas J. Sowin, Elizabeth M. Doherty
  • Patent number: 5292924
    Abstract: .alpha.-Fluoro-substituted N-acryloylamino acid derivatives of the formula ##STR1## are used to make polymers optionally for chromatographic resolution of racemates into their enantiomers. The fluorine atom improves performance in many instances.
    Type: Grant
    Filed: November 13, 1992
    Date of Patent: March 8, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Grosser, Walter Lange, Bruno Bomer, Dieter Arlt, Dietmar Bielefeldt
  • Patent number: 5286746
    Abstract: Antihypercholesterolemic activity is exhibited by compounds of the formula ##STR1## wherein: X is hydrogen, alkali metal or ammonium;Y is hydrogen, alkyl, cycloalkyl, aryl, or aralkyl; ##STR2## R is hydrogen, alkyl, ammonium, alkylammonium, or alkali metal (such as Na, Li, or K); andn is 1 or 2.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: February 15, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Kathleen M. Poss
  • Patent number: 5278338
    Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: January 11, 1994
    Assignee: Ethyl Corporation
    Inventor: Rhonda L. Trace
  • Patent number: 5264152
    Abstract: An optically active compound represented by the formula (I): ##STR1## wherein R is a straight or branched chain alkyl or alkoxy group having 1 to 15 carbon atoms, ##STR2## is a 1,4-cyclohexylene or 1,4-phenylene group, ##STR3## is a 1,4-phenylene or 3-fluoro-1,4-phenylene group, X is a mono-, di- or tri-fluoromethyl group, W is a straight or branched chain or cyclic alkylene group having 1 to 16 carbon atoms or a straight or branched chain alkenylene group having 2 to 16 carbon atoms, Y is a bond or --COO--, and Z is a straight or branched chain alkyl group having 1 to 8 carbon atoms, a phenyl group or a hydrogen atom, which is useful as a component of ferroelectric liquid crystal compositions or as a device utilizing said composition.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: November 23, 1993
    Assignee: Sharp Kabushiki Kaisha
    Inventors: Makoto Shiomi, Mitsuhiro Koden, Tomoaki Kuratate, Fumiaki Funada
  • Patent number: 5256806
    Abstract: Novel intermediates useful in the preparation of the optically active antiviral compound [1R-(1.alpha.,2.beta.,3.alpha.)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobut yl]-1,9-dihydro-6H-purin-6-one are described.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: October 26, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Gregory S. Bisacchi, Toomas Mitt
  • Patent number: 5247125
    Abstract: Novel thiol-terminated hydroxyamides, and processes for their preparation and use are provided. These hydroxyamide compounds may be prepared by the reaction of a mercapto-functional alkyl ester, such as methylmercaptopropionate, with a molar excess of an alcohol-substituted amine, such as a b-hydroxyalkyl amine. The thiol-terminated hydroxyamides are useful as polymerization chain transfer agents, particularly when it is desirable to form polymers or oligomers containing functional hydroxyamide end groups. By chain terminating such polymers or oligomers with reactive hydroxyamide end groups the polymers or oligomers can be further reacted with acid-containing monomers or polymers to form block or graft copolymers.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: September 21, 1993
    Assignee: Rohm and Haas Company
    Inventors: Andrew W. Gross, William D. Emmons
  • Patent number: 5221765
    Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.2 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 75.degree. C. to about 200.degree. C.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: June 22, 1993
    Assignee: Ethyl Corporation
    Inventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
  • Patent number: 5206389
    Abstract: These acrylates are those of formulae: ##STR1## where R=C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, aryl, arylalkyl or alkylaryl; Y=C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.12 aryl, heterocyclic radical whose ring contains from 5 to 10 members and whose heteroatom is chosen from N, O and S, an alkylaryl in which the alkyl part contains from 1 to 4 carbon atoms, Y not being able to denote 1,4-phenylene when R denotes methyl; and Z=hydrocarbon radical containing at least 2 C forming with O and the 2 adjacent Cs a ring containing from 4 to 8 members.To prepare them, an acrylate of formula CH.sub.2 .dbd.CH--COOR is reacted with a dialdehyde OHC--Y--CHO in the presence of an effective quantity of at least one functionalisation catalyst.The invention also relates to the preparation of new polymers and copolymers from the said acrylates.
    Type: Grant
    Filed: June 27, 1991
    Date of Patent: April 27, 1993
    Assignee: Atochem
    Inventors: Marie-Christine Berthe, Paul Caubere, Yves Fort
  • Patent number: 5202459
    Abstract: The present invention relates to a process for producing cyclobutane derivatives represented by general formula (28): ##STR1## (wherein R represents a substituent; R.sub.2 represents an electron attracting group and Nu represents a substituent corresponding to nucleophilic reagent), by reacting a compound represented by general formula (27): ##STR2## (wherein R has the same significance as defined above and R.sub.1 represents an electron attracting group) with nucleophilic reagents Nu.sup..crclbar. in a solvent.The compounds of formula (28) are useful as intermediates for synthesis of, for example, 9-[2,3-bis(hydroxymethyl)cyclobutan-1-yl]guanine which is expected to be useful as an antiviral agent.
    Type: Grant
    Filed: October 16, 1990
    Date of Patent: April 13, 1993
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Chikara Kaneko, Nobuya Katagiri
  • Patent number: 5196541
    Abstract: There is described a new process for the preparation of substituted 3-aminoacrylic esters of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and n have the meaning given in the description.The 3-aminoacrylic esters of the formula (I) are obtained by reacting acetic esters of the formula (II)R.sup.1 --(X).sub.n --CH.sub.2 --COOR.sup.
    Type: Grant
    Filed: August 2, 1991
    Date of Patent: March 23, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Gayer, Alexander Klausener, Peter C. Knuppel, Fritz Maurer
  • Patent number: 5183932
    Abstract: Herbicidal substituted 4-amino-5-alkylthio-1,2,4-triazol-3-ones of the formula ##STR1## in which R.sup.1 represents in each case straight-chain or branched alkyl, alkenyl or alkinyl, each of which has up to 4 carbon atoms, andR.sup.2 represents sec-butyl, tert.-butyl or optionally substituted C.sub.5 -C.sub.10 -alkyl, alkenyl or alkinyl, or piperidyl- or morpholinyl-alkyl, optionally substituted C.sub.3, C.sub.4, C.sub.5 and C.sub.7 -cycloalkyl, substituted cyclohexyl, or optionally substituted benzyl, phenethyl, naphthylmethyl or naphthylethyl.
    Type: Grant
    Filed: February 12, 1991
    Date of Patent: February 2, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus-Helmut Muller, Joachim Kluth, Klaus Konig, Karl-Rudolf Gassen, Kurt Findeisen, Markus Lindig, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt
  • Patent number: 5177109
    Abstract: Compounds, compositions and methods are described for treating a CNS disorder such as a cognitive disorder, epilepsy, depression, Parkinson's disease, Alzheimer's disease, a neurodegenerative disease or neurotoxic injury. Compound of interest are 2-amino-4,5-methyleneadipic acid compounds and derivatives defined by the formula I: ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, ##STR2## with each of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein each of X and Y is independently selected from hydroxyl, alkoxy, alkylthio, amino and ##STR3## with each of R.sup.6 and R.sup.7 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein any of R.sup.1 through R.sup.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: January 5, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Roberto Pellicciari, Benedetto Natalini, Maura Marinozzi, Alexis A. Cordi, Joseph B. Monahan, Thomas H. Lanthorn
  • Patent number: 5164526
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each represent hydrogen, alkyl, alkenyl, cycloalkyl, aryl or aralkyl are produced by a new environmentally acceptable process.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: November 17, 1992
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventor: Ingolf Macher
  • Patent number: 5153352
    Abstract: A compound of the formula: ##STR1## wherein A is a purin-9-yl group, a heterocyclic isostere of a purin-9-yl group, a pyrimidin-1-yl group or a heterocyclic isostere of a pyrimidin-1-yl group; E is hydrogen, --CH.sub.2 OH or --OH; and G and D are independently selected from hydrogen, C.sub.1 to C.sub.10 alkyl, --OH, --CH.sub.2 OH, --CH.sub.2 OR.sub.20 wherein R.sub.20 is C.sub.1 to C.sub.6 alkyl, --CH.sub.2 OC(O)R.sub.21 wherein R.sub.21 is C.sub.1 to C.sub.10 alkyl, --CH.sub.2 OC(O)CH(R.sub.22)(NHR.sub.23) wherein R.sub.22 is the side chain of any of the naturally occuring amino acids and R.sub.23 is hydrogen or --C(O)CH(R.sub.24)(NH.sub.2) wherein R.sub.24 is the side chain of any of the naturally occuring amino acids, --CH.sub.1 SH, --Ch.sub.2 Cl, --Ch.sub.2 F, --CH.sub.2 Br, --CH.sub.2 I, --C(O)H, --CH.sub.2 CN, --CH.sub.2 N.sub.3, --CH.sub.2 NR.sub.1 R.sub.2, --CO.sub.2 R.sub.1, --CH.sub.2 CH.sub.2 OH, --CH.sub.2 CH.sub.2 OR.sub.20 wherein R.sub.20 is as defined above, --CH.sub.2 CH.sub.2 OC(O)R.sub.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: October 6, 1992
    Assignee: Bristol-Myers Squibb Company
    Inventors: Daniel W. Norbeck, Richard J. Pariza, Steven M. Hannick, Thomas J. Sowin
  • Patent number: 5130462
    Abstract: Cyclobutane derivatives of the formulas ##STR1## wherein P is a hydroxy protecting group and X is a leaving group are useful intermediates in the preparation of antiviral compounds.
    Type: Grant
    Filed: February 19, 1991
    Date of Patent: July 14, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: William A. Slusarchyk, Robert Zahler
  • Patent number: RE34652
    Abstract: Novel fluorinated, acrylamide monomers are prepared from 2-alkenyl azlactones reacted with fluorinated alcohols. The novel monomers have the formula ##STR1## wherein R.sup.1 and R.sup.6 are independently hydrogen or methyl;R.sup.2 and R.sup.3 independently can be an alkyl, cycloalkyl, or aryl group, or R.sup.2 and R.sup.3 taken together with the carbon to which they are joined can form a carbocyclic ring containing 4 to 12 ring atoms;R.sup.4 and R.sup.5 are independently hydrogen or lower alkyl;a is 0 or 1;b is 1 or 2;X is a single bond, CH.sub.2, CH.sub.2 OCH.sub.2, and CH.sub.2 CH.sub.2 OCH.sub.2 ; andR.sub.F is a substantially perfluorinated alkyl, cycloalkyl, or aryl group when b is 1 and perfluorinated alkylene when b is 2.Novel polymers and copolymers can be prepared from the monomers of the invention.
    Type: Grant
    Filed: June 3, 1992
    Date of Patent: June 28, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Steven M. Heilmann, Larry R. Krepski, Dean M. Moren, Jerald K. Rasmussen, Howell K. Smith, II