Oxy Bonded Directly To A Ring Patents (Class 568/33)
  • Patent number: 5750577
    Abstract: Novel medicinally-useful compounds are provided herein. These compounds include isomeric cyclic tetramers of formaldehyde and 1-naphthol, and the derivatives or analogues of such cyclic tetramers, and linear oligomers of chromotropic acid, or its derivatives or analogues with naphthalene.
    Type: Grant
    Filed: December 5, 1996
    Date of Patent: May 12, 1998
    Assignee: Seabright Corporation Limited
    Inventor: Paris Georghiou
  • Patent number: 5739374
    Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: April 14, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5739166
    Abstract: A class of terphenyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein each of R.sup.2 and R.sup.3 is independently selected from hydrido and halo; or wherein R.sup.2 and R.sup.3 together form --OCH.sub.2 O--; wherein each of R.sup.6 through R.sup.8 is independently selected from hydrido, lower alkyl, halo, lower alkoxy, lower haloalkyl, and lower dialkylamino; or wherein R.sup.6 and R.sup.7 together form --OCH.sub.2 O; and wherein R.sup.12 is selected from lower alkylsulfonyl and aminosulfonyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: November 29, 1994
    Date of Patent: April 14, 1998
    Assignee: G.D. Searle & Co.
    Inventors: David B. Reitz, Jinglin Li, Monica B. Norton
  • Patent number: 5736579
    Abstract: A class of substituted spiro compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula III: ##STR1## wherein n is a number selected from 0, 1 and 2; wherein R.sup.3 is methylsulfonyl or sulfamyl; and wherein R.sup.8 is selected from hydrido, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, isobutyl, methoxy, ethoxy, propoxy, butoxy, hydroxyl, mercapto, methylthio, ethylthio, cyano, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, difluorochloromethyl, dichlorofluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, trifluoromethoxy, hydroxymethyl, methoxymethyl and ethoxymethyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: November 18, 1994
    Date of Patent: April 7, 1998
    Assignee: G.D. Searle & Co.
    Inventors: David B. Reitz, Robert E. Manning, Horng-Chi Huang, Jinglin Li
  • Patent number: 5716624
    Abstract: Novel pharmaceutically/cosmetically-active polyaromatic propynyl compounds have the structural formula (1): ##STR1## in which X is one of the radicals: ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: February 10, 1998
    Assignee: C.I.R.D. Galderma
    Inventor: Jean-Michel Bernardon
  • Patent number: 5672627
    Abstract: A class of substituted spirodienes is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula III: ##STR1## wherein R.sup.3 is methylsulfonyl or sulfamyl; and wherein R.sup.8 is selected from hydrido, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, isobutyl, methoxy, ethoxy, propoxy, butoxy, hydroxyl, mercapto, methylthio, ethylthio, cyano, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, difluorochloromethyl, dichlorofluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, trifluoromethoxy, hydroxymethyl, methoxymethyl and ethoxymethyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: July 9, 1996
    Date of Patent: September 30, 1997
    Assignee: G.D. Searle & Co.
    Inventors: Horng-Chih Huang, David R. Reitz
  • Patent number: 5672626
    Abstract: A class of substituted spirodienes is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.4 and R.sup.5 is hydrido; wherein R.sup.3 is methylsulfonyl or sulfamyl; and wherein each of R.sup.6 through R.sup.10 is independently selected from hydrido, halo, alkyl, alkoxy, alkylthio, cyano, haloalkyl, haloalkoxy, hydroxyalkyl, alkoxyalkyl, hydroxyl, and mercapto; and wherein n is 1, 2 or 3; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: July 9, 1996
    Date of Patent: September 30, 1997
    Assignee: G. D. Searle & Co.
    Inventors: Horng-Chih Huang, David R. Reitz
  • Patent number: 5670651
    Abstract: Benzocyclobutene-terminated monomers of the formula ##STR1## wherein Ar is --SO.sub.2 --, --CO--, or ##STR2## are prepared by reacting a benzocyclobutene of the formula ##STR3## wherein R is --H or --SiMe.sub.3, with a difluorophenyl compound of the formula ##STR4## wherein Ar is as described previously, in the presence of a promoter. A mixture of the resins is obtained when potassium carbonate is employed as the promoter. The bis(benzocyclobutene)-terminated monomer is obtained when cesium fluoride is employed as the promoter.
    Type: Grant
    Filed: February 12, 1996
    Date of Patent: September 23, 1997
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Loon-Seng Tan, Narayanan Venkatasubramanian
  • Patent number: 5654331
    Abstract: Diaromatic compounds, characterised in that they correspond to the following general formula: ##STR1## in which: R.sub.1 is --CH.sub.3, --CH.sub.2 OH, --COR.sub.8 or --CH.sub.2 OCOR.sub.9, R.sub.8 is H, OH, --OR.sub.10, --N(rr') or alkyl, R.sub.10 is alkyl, alkenyl, aryl or aralkyl, r and r' being H, alkyl, aryl, aralkyl, etc., r and r' together form a heterocycle, R.sub.9 is alkyl, alkenyl or a sugar residue, R.sub.2 and R.sub.3 are --OR.sub.11 or --OCOR.sub.11, R.sub.11 is H, alkyl, fluoroalkyl, aryl or aralkyl, R.sub.3 in addition being H, R.sub.4 is H, OH, alkyl, alkoxy, F, Cl or --CF.sub.3, R.sub.5 and R.sub.7 are H, OH, alkoxy, .alpha.-substituted alkyl or .alpha.,.alpha.'-disubstituted alkyl, etc., R.sub.6 is H, OH, alkyl, alkoxy, cycloalkyl, etc., R.sub.5 and R.sub.7 cannot simultaneously be OH or alkoxy and R.sub.4, R.sub.5, R.sub.6 and R.sub.7 cannot simultaneously be H, R.sub.5 and R.sub.6 or R.sub.6 and R.sub.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: August 5, 1997
    Assignee: Centre International De Recherches Dermatologiques Galderma (Cird Galderma)
    Inventor: Jean-Michel Bernardon
  • Patent number: 5648449
    Abstract: A copolyester consisting essentially of ethylene terephthalate units and further comprising 0.01 to 1 mole % based on the sum of the moles of total diol units and the moles of triol units of a triol unit represented by the following formula (I) and/or a triol unit represented by the following formula (II). ##STR1## wherein A is a group represented by formula --CH.sub.2 CH.sub.2 -- or formula --CH(CH.sub.3)CH.sub.2 --, B is a divalent hydrocarbon group, --CO--, --SO.sub.2 --, --0-- or a direct bond (-), and p, q, r, s, t and u are each an integer of 1 to 8. A process for producing the same and molded articles (in particular extrusion blow molded articles) therefrom. The copolyesters of the present invention are applicable to melt moldings accompanying melt extrusion, in particular extrusion blow molding, where parisons therefrom have good draw-down tendency and blow moldability.
    Type: Grant
    Filed: January 31, 1996
    Date of Patent: July 15, 1997
    Assignee: Kuraray Co., Ltd.
    Inventors: Shinji Tai, Tetsuya Hara, Akira Kageyu, Tsugunori Kashimura
  • Patent number: 5616759
    Abstract: Cyclohexylidene compounds of the structure: ##STR1## where X.sup.1 and X.sup.2, which may be the same or different, is hydrogen or a hydroxy-protecting group, and Y is --POPh.sub.2, or --PO (OAlkyl).sub.2, or --SO.sub.2 Ar, or --Si(Alkyl).sub.3. The compounds are used as intermediates in the preparation of 19-nor-vitamin D compounds.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: April 1, 1997
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
  • Patent number: 5596122
    Abstract: The present invention is directed to disulfonyl methane compounds for the control of parasites in vertebrate animals.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: January 21, 1997
    Assignee: Eli Lilly and Company
    Inventor: David I. Wickiser
  • Patent number: 5581006
    Abstract: A convergent synthesis of 19-nor-vitamin D compounds, specifically 19-nor-1.alpha.,25-dihydroxyvitamin D.sub.3, is disclosed. The synthesis can also readily be utilized for preparing other 1.alpha.-hydroxylated 19-nor-vitamin D compounds. The key step in the synthesis is a suitable application of Lythgoe's procedure i.e. a Horner-Wittig reaction of the lithium anion of a phosphine oxide with a Windaus Grundmann ketone to give, after any necessary deprotection, the desired 19-nor-vitamin D compound.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: December 3, 1996
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
  • Patent number: 5578251
    Abstract: A process for preparing polar disulfone-functionalized molecules, which process comprises performing one or more of the following reactions:(i) reacting a vinyl ether disulfone molecule with an activated aromatic molecule, an activated heterocyclic molecule, a dye base, or a dye olefin;(ii) reacting an enamine disulfone molecule with a dye base or a dye olefin; and(iii) reacting an alkenyl disulfone molecule having a vinylogous methyl or methylene group conjugatively located relative to the disulfone group with an aldehyde or an acetal derived from an aldehyde.
    Type: Grant
    Filed: August 5, 1994
    Date of Patent: November 26, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Gary T. Boyd, George V. Tiers, Cecil V. Francis, Eugene P. Janulis, Robert J. Koshar, Louis M. Leichter
  • Patent number: 5536752
    Abstract: The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: July 16, 1996
    Assignee: Merck Frosst Canada Inc.
    Inventors: Yves Ducharme, Jacques Y. Gauthier, Petpiboon Prasit, Yves Leblanc, Zhaoyin Wang, Serge Leger, Michel Therien
  • Patent number: 5480568
    Abstract: Alkyl aryl sulfones are disclosed which are useful as high temperature and magnetic recording media lubricants. Also disclosed are lubricating mixtures containing the alkyl aryl sulfones, magnetic recording media containing the alkyl aryl sulfones, and a process for lubricating the magnetic recording media with the alkyl aryl sulfones.
    Type: Grant
    Filed: July 22, 1994
    Date of Patent: January 2, 1996
    Assignee: The Dow Chemical Company
    Inventors: Chester E. Pawloski, Bassam S. Nader
  • Patent number: 5468903
    Abstract: A process for preparing a compound comprising a monocyclic aromatic ring having at least a first substituent and a substituted sulphonyl group at the position para to the first substituent, the process comprising mixing a reactant comprising the monocyclic aromatic ring with the first substituent and hydrogen in the position of the ring para to the first substituent, with a sulphonic acid halide derivative in the presence of a naturally occurring or synthetic zeolite capable of catalyzing a sulphonylation reaction between the reactant and the sulphonic acid halide, under conditions in which the reaction will occur.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: November 21, 1995
    Assignee: Zeneca Limited
    Inventors: Kenneth R. Randles, Brian G. Gott, Stephen T. A. K. Daley
  • Patent number: 5463083
    Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i,e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. Also disclosed is a method to treat disorders mediated by PAF and/or leukotrienes that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier, to a patient in need of such therapy.
    Type: Grant
    Filed: January 6, 1994
    Date of Patent: October 31, 1995
    Assignee: Cytomed, Inc.
    Inventors: Tesfaye Biftu, Xiong Cai, Sajjet Hussion, Gurmit Grewal, T. Y. Shen
  • Patent number: 5463133
    Abstract: The present invention is to provide phenethyl alcohol derivative represented by the general formula (I), which is a stabilizing agent for colored images, particularly improved in resistance to plasticizers for the use in recording materials. ##STR1## (wherein Y: formula (II) or formula (III) R.sup.1 : H, alkyl, aralkylR.sup.2, R.sup.3 and R.sup.4 : halogen, nitro, alkyl, alkoxy, alkenyl, alkenyloxy,R.sup.5, R.sup.6 and R.sup.7 : H, alkyl,Z: --SO.sub.2 --, --CO--, --C(CH.sub.3).sub.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: October 31, 1995
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Takehiro Sato, Kimiaki Kinosita, Minoru Kaeriyama, Tomoya Hidaka
  • Patent number: 5426234
    Abstract: A composition of matter having the general structure: ##STR1## (wherein X is F, Cl, or NO.sub.2, and Y is CO, SO.sub.2 or C(CF.sub.3).sub.2) is employed to terminate a nucleophilic reagent, resulting in the exclusive production of phenylethynyl terminated reactive oligomers which display unique thermal characteristics. A reactive diluent having the general structure: ##STR2## (wherein R is any aliphatic or aromatic moiety) is employed to decrease the melt viscosity of a phenylethynyl terminated reactive oligomer and to subsequently react therewith to provide a thermosetting material of enhanced density. These materials have features which make them attractive candidates for use as composite matrices and adhesives.
    Type: Grant
    Filed: May 16, 1994
    Date of Patent: June 20, 1995
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Robert G. Bryant, Brian J. Jensen, Paul M. Hergenrother
  • Patent number: 5418254
    Abstract: A class of 2,3-substituted cyclopenta-2,4-dienyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein each of R.sup.1 and R.sup.2 is independently selected from hydrido, lower alkyl, lower hydroxyalkyl, halo, lower haloalkyl, lower alkoxycarbonyl and carboxyl; and wherein each of R.sup.3 through R.sup.12 is independently selected from hydrido, halo, lower alkyl, lower alkylthio, cyano, hydroxyl, mercapto, lower haloalkyl, lower haloalkoxy, lower alkoxy, lower hydroxyalkyl, lower alkoxyalkyl, lower alkylsulfonyl, lower haloalkylsulfonyl and sulfamyl; provided R.sup.5 and R.sup.10 are not both hydrido or methoxy; or a pharmaceutically suitable salt or prodrug thereof.
    Type: Grant
    Filed: May 4, 1994
    Date of Patent: May 23, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Horng-Chih Huang, David R. Reitz
  • Patent number: 5414135
    Abstract: A new class of polyalkylene oxide vinyl sulfone reagents is described. Also described are a method by which these reagents can be prepared as well as a method for using them in hydrated media for the modification of proteins. The novel polymer-to-protein conjugates made by reacting these reagents with proteins have advantages over similar conjugates prepared with prior art reagents in that they are more stable against hydrolysis and retain the positive charge carrying capacity at amine sites at which the modifying reagents are attached.
    Type: Grant
    Filed: November 16, 1993
    Date of Patent: May 9, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: Robert A. Snow, David L. Ladd
  • Patent number: 5411973
    Abstract: Compounds of formula I ##STR1## wherein X, A, B, R.sup.1 and R.sup.2 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolysable ester thereof, processes for preparing the compounds and pharmaceutical compositions comprising them. The compounds are useful as potassium channel openers and as therapeutic agents in the treatment of urinary incontinence.
    Type: Grant
    Filed: May 18, 1993
    Date of Patent: May 2, 1995
    Assignee: Zeneca Limited
    Inventors: Keith Russell, James R. Empfield, Cyrus J. Ohnmacht, Keith H. Gibson
  • Patent number: 5399772
    Abstract: High purity 2,4'-dihydroxydiphenylsulfones useful as developers for thermal recording paper can be produced efficiently and with high selectivity by reacting one or more phenols and sulfuric acid in the presence as of at least one of phosphonic acid, phosphinic acid and salts thereof, in the absence of a solvent or in the presence of an aromatic hydrocarbon solvent having a boiling point at atmospheric pressure of 130.degree. to 200.degree. C., and then purifying the thus-produced crude 2,4'-dihydroxydiphenylsulfones using a mixed solvent containing (1) 5 to 20 weight % of at least one lower aliphatic alcohol and 95 to 80 weight % of at least one aromatic hydrocarbon which does not contain halogen, (2) 10 to 40 weight % of at least one ketone and 90 to 60 weight % of at least one aromatic hydrocarbon which does not contain halogen or (3) 10 to 40 weight % of at least one ester of acetic acid and 90 to 60 weight % of at least one aromatic hydrocarbon which does not contain halogen.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: March 21, 1995
    Assignee: Nicca Chemical Co., Ltd.
    Inventors: Masaaki Hosoda, Mikihiko Kurose, Yoshihiro Sasada, Hajime Saito, Masahiro Makino
  • Patent number: 5393790
    Abstract: A class of substituted spiro compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula III: ##STR1## wherein n is a number selected from 0, 1 and 2; wherein R.sup.3 is methylsulfonyl or sulfamyl; and wherein R.sup.8 is selected from hydrido, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, isobutyl, methoxy, ethoxy, propoxy, butoxy, hydroxyl, mercapto, methylthio, ethylthio, cyano, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, difluorochloromethyl, dichlorofluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, trifluoromethoxy, hydroxymethyl, methoxymethyl and ethoxymethyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: February 28, 1995
    Assignee: G.D. Searle & Co.
    Inventors: David B. Reitz, Robert E. Manning, Horng-Chi Huang, Jinglin Li
  • Patent number: 5393776
    Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5378674
    Abstract: A heat-sensitive recording material comprises a heat-sensitive color forming layer which is formed on a supporter and contains a colorless or light color leuco dyestuff as a color forming substance, a developer which develops color of the leuco dyestuff by reaction with it when heated and a sensitizer. The developer is 2,4'-dihydroxydiphenylsulfone having purity of 97 weight % or more and prepared by washing and drying crystal which is obtained by dissolving crude 2,4'-dihydroxydiphenylsulfone in an alcohol having 1 to 4 carbon atoms or in a mixture of an alcohol having 1 to 4 carbon atoms and water by heating and then cooling the solution or partially removing the solvent from the solution by distillation. The heat-sensitive recording material has excellent properties, such as reduced fog and excellent image preservation (weatherability).
    Type: Grant
    Filed: March 23, 1994
    Date of Patent: January 3, 1995
    Assignee: Nicca Chemical Co., Ltd.
    Inventors: Norio Kobayashi, Toshiaki Takahashi, Masahiro Makino, Masaaki Hosoda
  • Patent number: 5371284
    Abstract: Phenyl acetylenic acetals and thioacetals and their use in the treatment of allergy, asthma, inflammation, arthritis, hyperproliferative skin disease, psoriasis or contact dermatitis are disclosed. Also disclosed are intermediates useful for producing said phenyl acetylenic acetals and thioacetals.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: December 6, 1994
    Assignee: Schering Corporation
    Inventors: Richard J. Friary, Michael J. Green, Anil K. Saksena, Vera A. Seidl
  • Patent number: 5354511
    Abstract: Compounds having non-linear optical activity of the general formula ##STR1## wherein D and A are electron donor and acceptor groups, respectively, R.sup.1 and R.sup.2 are aromatic bridging groups, X and Y are preferably groups capable of partaking in polymerization reactions are suitable for use in polymer-based light modulator devices.
    Type: Grant
    Filed: November 27, 1992
    Date of Patent: October 11, 1994
    Assignee: AlliedSignal Inc.
    Inventors: Chengjiu Wu, Jianhui Shan, Ajay Nahata
  • Patent number: 5312952
    Abstract: This invention relates to a vinyl aromatic. Compounds of Structure (I): ##STR1## wherein R is C.sub.9 -C.sub.20 alkyl, Y is NO.sub.2, SO.sub.3 R' or H, R' is C.sub.1 -C.sub.20 alkyl, X is NO.sub.2 or C1-C.sub.20 alkyl, and R" is H or C.sub.1 -C.sub.20 alkyl, m is 2 or 3 and n is 0,1,2,3, with the proviso that when R is C.sub.9 and n=O, X and Y may not both be NO.sub.2.
    Type: Grant
    Filed: April 23, 1992
    Date of Patent: May 17, 1994
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Anthony V. Grossi, Paul E. Stott, John M. DeMassa, Howard S. Friedman, Gerald J. Abruscato
  • Patent number: 5288913
    Abstract: Process for the preparation of 4,4'-dihydroxydiphenyl sulfone in a high yield and high purity by reaction of phenol with a sulfonating agent in a chlorinated aromatic, in which phenol is reacted with a sulfonating agent in ortho-, meta- or para-chlorotoluene or in any desired mixture of these isomeric chlorotoluenes as the inert solvent, at temperatures of from about 100.degree. to about 200.degree. C.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: February 22, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Georg Grotsch
  • Patent number: 5288923
    Abstract: A process for the preparation of hydroxyalkyl ethers of diphenols is disclosed. Accordingly, aromatic polycarbonate resin is reacted with alkylene diol in the presence of a basic catalyst, at temperatures of 150.degree. to 250.degree. C. at a molar ratio of 514 10 moles of alkylene diol to 1 mole of aromatic carbonate structural units to produce the corresponding hydroxyalkyl ether. Additional embodiments entail optional reactions of the aromatic polycarbonate with cyclic alkylene carbonate and with open chain monomeric bis-(hydroxyalkyl)-carbonate. Aromatic polycarbonate waste may thus be advantageously recycled.
    Type: Grant
    Filed: January 29, 1993
    Date of Patent: February 22, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Fennhoff, Wolfgang Jacob, Manfred Ehlert
  • Patent number: 5284978
    Abstract: A method of producing diphenyl sulfone compounds of the formula (I) ##STR1## wherein R is an alkyl having 1 to 8 carbon atoms, a cycloalkyl having 3 to 8 carbon atoms, an alkenyl having 2 to 8 carbon atoms or an arylalkyl which may have substituent(s) on the aromatic ring, comprising reacting 4,4'-dihydroxydiphenyl sulfone with a compound of the formulaR--Xwherein R is as defined above and X is halogen, characterized by conducting the reaction in 0.3-1.5 weight parts of an aqueous solvent per weight part of 4,4'-dihydroxydiphenyl sulfone in the presence of 1.5-3 moles of an alkali per mole of 4,4'-dihydroxydiphenyl sulfone. Since the method of the invention permits production of 4-substituted hydroxy-4'-hydroxydiphenyl sulfones, specifically 4-n-propoxy-4'-hydroxydiphenyl sulfone or 4-isopropoxy-4'-hydroxydiphenyl sulfone using an inexpensive solvent, with good selectivity and economical feasibility, they are industrially advantageous.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: February 8, 1994
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Ryoichi Kinishi, Yoshihiro Ozaki
  • Patent number: 5283349
    Abstract: A 2,6,7-trisubstituted-3-methylenebicyclo-[3.3.0]octane of formula (I) or an enantiomer thereof, or a mixture of these in an arbitrary ratio. The compound is a key intermediate for preparation of isocarbacyclins which are useful as medicines for the circulatory system such as an antithrombotic agent, an antilipidemic agent, a hypotensive agent or an antiarterosclerotic agent.
    Type: Grant
    Filed: September 11, 1986
    Date of Patent: February 1, 1994
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Kiyoshi Bannai, Seizi Kurozumi
  • Patent number: 5281731
    Abstract: A convergent synthesis of 19-nor-vitamin D compounds, specifically 19-nor-1.alpha.,25-dihydroxyvitamin D.sub.3, is disclosed. The synthesis can also readily be utilized for preparing other 1.alpha.-hydroxylated 19-nor-vitamin D compounds. The key step in the synthesis is a suitable application of Lythgoe's procedure i.e. a Horner-Wittig reaction of the lithium anion of a phosphine oxide with a Windaus Grundmann ketone to give, after any necessary deprotection, the desired 19-nor-vitamin D compound.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: January 25, 1994
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
  • Patent number: 5274172
    Abstract: There is disclosed a process for preparing granular esters in one step by the reaction of an alcohol with acid chloride in an aqueous alkaline medium with moderate shear agitation and optionally in the presence of a surfactant.
    Type: Grant
    Filed: June 24, 1992
    Date of Patent: December 28, 1993
    Assignee: Monsanto Company
    Inventors: Yueting Chou, David A. Martin
  • Patent number: 5256826
    Abstract: A process for the preparation of aromatic carbonyl or sulfonyl compounds with a diaryl ether structure by reacting phenols with halogenated carbonyl- or sulfonylaromatic compounds in a dipolar aprotic solvent is carried out in the presence of catalytic amounts of alkali metal nitrite or an aromatic nitro, nitroso, azo, azoxy or hydrazo compound.
    Type: Grant
    Filed: August 31, 1992
    Date of Patent: October 26, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Erwin Hahn, Heinrich J. Eilingsfeld, Helmut Reichelt, Alexander Aumueller, Bernd Hupfeld
  • Patent number: 5248828
    Abstract: A method for preparing a sulfone represented by the following formula: ##STR1## wherein R' represents a lower alkyl group, an aryl group or an aryl group whose nucleus has at least one substituent selected from the group consisting of a halogen atom, nitro group, a lower alkyl group, phenyl group and a phenyl group substituted with a halogen atom, or an alkali metal salt thereof. A sulfonic acid ester of 4-hydroxybiphenyl is condensed at a temperature of 0.degree. to 200.degree. C. in a presence of a Lewis acid or a super-strong acid with a sulfonyl chloride represented by the formula R'SO.sub.2 Cl, wherein R' is the same as that defined above.
    Type: Grant
    Filed: June 10, 1992
    Date of Patent: September 28, 1993
    Assignee: Sanko Kaihatsu Kagaku Kenkyusho
    Inventors: Toranosuke Saito, Shigeru Oda, Hiroki Tsunomachi, Daishiro Kishimoto
  • Patent number: 5241121
    Abstract: A process for preparing 4,4'-dihydroxydiphenylsulfone, the process including heating 4,4'-dihydroxydiphenylsulfone and 2,4'-dihydroxydiphenylsulfone in the presence of an acid catalyst to isomerize the 2,4'-dihydroxydiphenylsulfone into 4,4'-dihydroxydiphenylsulfone, the process being characterized in that a suspension of 4,4'-dihydroxydiphenylsulfone and 2,4'-dihydroxydiphenylsulfone in a liquid dispersing medium is heated for isomerization while the liquid portion is distilled off or a crystal mixture of 4,4'-dihydroxydiphenylsulfone and 2,4'-dihydroxydiphenylsulfone is heated for isomerization to produce 4,4'-dihydroxydiphenylsulfone in the form of crystal powder.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: August 31, 1993
    Assignee: Konishi Chemical Ind. Co., Ltd.
    Inventors: Eiji Ogata, Nobuyuki Nate, Kazuo Hamano
  • Patent number: 5232836
    Abstract: Vitamin D derivatives corresponding to the following formula I ##STR1## in which R.sub.1 denotes a substituted alkyl group having 1 to 15 carbon atoms, in particular the side chains of vitamin D.sub.2 (C.sup.20 to C.sup.28) or D.sub.3 (C.sup.20 to C.sup.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: August 3, 1993
    Assignee: Ire-Medgenix S.A.
    Inventors: Roger Bouillon, Pierre J. De Clerco, Pierre Eliard, Maurits Vanderwalle
  • Patent number: 5225601
    Abstract: Abstract of the Disclosure: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: October 31, 1991
    Date of Patent: July 6, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5214070
    Abstract: The invention concerns a diaryl ether cycloalkane of the formula I, or a pharmaceutically-acceptable salt thereof, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl; X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is optionally substituted phenylene, or a 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; andR.sup.2 and R.sup.3 together form a (3-6C)alkylene group which defines an optionally substituted ring having 4 to 7 ring atoms.The invention also concerns processes for the manufacture of a diaryl ether cycloalkane of the formula I, or a pharmaceutically-acceptable salt thereof, and pharmaceutical compositions containing said cycloalkane. The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: August 21, 1991
    Date of Patent: May 25, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Thomas G. C. Bird, Philip N. Edwards
  • Patent number: 5214069
    Abstract: The invention concerns a compound of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;A.sup.1 is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;Ar.sup.2 is optionally substituted phenylene, or a 6 membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; wherein R.sup.2 is hydrogen, (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl; and whereinR.sup.3 is hydroxy-(1-4C)alkyl, mercapto-(1-4C)alkyl, (1-4C)alkoxy-(1-4C)alkyl, (3-4C)alkenyloxy-(1-4C)alkyl, (3-4C)alkynyloxy-(1-4C)alkyl, (1-4C)alkoxy-(2-4C)alkoxy-(1-4C)alkyl, (1-4C)alkylthio-(1-4C)alkyl, (1-4C)alkylsulphinyl-(1-4C)alkyl, (1-4C)alkylsulphonyl-(1-4C)alkyl, (1-4C)alkoxycarbonyl-(1-4C)alkyl, (2-4C)alkanoyl-(1-4C)alkyl, (2-4C)alkanoyloxy-(1-4C)alkyl or cyano-(1-4C)alkyl; or R.sup.
    Type: Grant
    Filed: January 23, 1992
    Date of Patent: May 25, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventor: Jean-Marc M. M. Girodeau
  • Patent number: 5210216
    Abstract: Calixarene and oxacalixarene derivatives of the formula IV: ##STR1## wherein m'+m"=0-8n=0-8m'.gtoreq.1/2(m'+m")3.ltoreq.m'+m"+n.ltoreq.8if n=0, m'+m".gtoreq.4R.sup.3 is H, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof and R.sup.3 may be the same or different on each aryl group;R.sup.15 is H or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof;X is selected from ##STR2## wherein R.sup.7 and R.sup.8 which may be the same or different are H or hydrocarbyl (including a cycloaliphatic ring formed by R.sup.7 and R.sup.8 together), aryl, hydrocarbylaryl or a substituted derivative thereof; R.sup.9 is --OH, --NH.sub.2, --NHC(O)NH.sub.2 or --NHAr, wherein Ar is aryl or a substituted derivative thereof,n' is 0 or 1.Use of the compounds for sequestration of metals is also described.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: May 11, 1993
    Assignee: Loctite (Ireland) Limited
    Inventors: Stephen J. Harris, John Guthrie, Maureen MacManus, Ciaran McArdle, Michael A. McKervey
  • Patent number: 5189223
    Abstract: The present invention provides a process for preparing 4,4'-dihydroxydiphenylsulfone which comprises subjecting a phenol and a sulfonating agent to dehydration reaction in the presence of mesitylene as a reaction medium while the produced 4,4'-dihydroxydiphenylsulfone is suspended in the mesitylene, and a process for preparing 4,4'-dihydroxydiphenylsulfone, characterized in that after the foregoing dehydration reaction, the 4,4'-dihydroxydiphenysulfone obtained as suspended in the mesitylene and/or retained in a liquid-free solid form is subjected to reaction for isomerization of 2,4'-dihydroxydiphenylsulfone produced as a by-product into 4,4'-dihydroxydiphenylsulfone with heating at a temperature of not lower than that for isomerization of 2,4'-dihydroxydiphenylsulfone into 4,4'-dihydroxydiphenylsulfone.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: February 23, 1993
    Assignee: Konishi Chemical Ind. Co., Ltd.
    Inventors: Eiji Ogata, Nobuyuki Nate
  • Patent number: 5166441
    Abstract: The present invention related to novel compounds useful in the manufacture of astaxanthin and to processes for their preparation. The novel intermediates have the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are C.sub.1-6 -alkyl which may be branched or phenyl, and ##STR2## wherein R' is alkyl, alkoxy, NO.sub.2, NH.sub.2 or halogen.
    Type: Grant
    Filed: December 9, 1991
    Date of Patent: November 24, 1992
    Assignee: NeuroSearch A/S
    Inventor: Peter Moldt
  • Patent number: 5152826
    Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: October 6, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Christopher G. Knudsen
  • Patent number: 5132463
    Abstract: Novel 1,3-Diaryl cyclopentanes of the following general formula were prepared. ##STR1## These compounds were found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and as such useful in the treatment or amelioration of various diseases or disorders mediated by the PAF, for example, hypotension, inflammation, nephritis, stroke and other cardiovascular disorders, asthma, allergic and skin diseases, peptic or stomach ulcer, shock, lung edema, psoriasis, adult respiratory distress syndrome, pain including dental pain, and aggregation of platelets.
    Type: Grant
    Filed: June 12, 1991
    Date of Patent: July 21, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Donald W. Graham, John C. Chabala, Tesfaye Biftu, Michael N. Chang, Yuan-Ching P. Chiang, Shu S. Yang, Kathryn L. Thompson
  • Patent number: 5132423
    Abstract: Reactions between a solid polar and a non-polar compound, especially nucleophilic aromatic substitution reactions between an alkali metal salt of a hydroxyaromatic compound or thio analog thereof and an activated halo- or nitro-substituted aromatic compound, are conducted in a non-polar organic solvent such as toluene or xylene, in the presence of a hexaalkylguanidinium or .alpha.,.omega.-bis(pentaalkylguanidinium)alkane salt, or a corresponding heterocyclic salt, as a phase transfer catalyst. The method is particularly useful for the preparation of bisimides from bisphenol A or 4,4'-biphenol salts and 4-nitro- or 4-halophthalimides.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: July 21, 1992
    Assignee: General Electric Company
    Inventors: Daniel J. Brunelle, Deborah A. Haitko, James P. Barren, Sunita Singh
  • Patent number: 5105016
    Abstract: Bis(cyclohexylphenol) compounds of the formula ##STR1## wherein R is an alkyl having 1 to 6 carbon atoms, Y is --S--, --SO-- or --SO.sub.2 -- with the proviso that when R is methyl in the ortho position to the hydroxy, Y is --SO-- or --SO.sub.2 --and their use. The above-mentioned compounds are useful as antioxidants and biocides for industrial use.
    Type: Grant
    Filed: November 20, 1990
    Date of Patent: April 14, 1992
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Kazumi Saeki, Akira Shimada