Hydroxy Or Halogen Attached Directly Or Indirectly To The Hetero Ring By Acyclic Nonionic Bonding (h Of -oh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 549/423)
  • Patent number: 5808111
    Abstract: Novel acitretinamide compounds which are soluble and stable in water and useful in aqueous delivery systems, particularly to treat cancer, are provided. The novel acitretinamide compounds, 1-(D-glucopyranosyl)acitretinamide, 1-(D-glucopyranuronosyl)acitretinamide and the metal salts thereof, are hereinafter collectively referred to as the "acitretinamide compounds". The invention also relates to novel methods of making the acitretinamide compounds.
    Type: Grant
    Filed: May 6, 1997
    Date of Patent: September 15, 1998
    Assignee: The Ohio State Research Foundation
    Inventor: Robert W. Curley, Jr.
  • Patent number: 5648379
    Abstract: Derivatives and analogues of 2-deoxy-2,3-didehydro-N-acetyl neuraminic acid, pharmaceutical formulations thereof, methods for their preparation and their use in the treatment of viral infections, in particular influenza, are described.
    Type: Grant
    Filed: October 19, 1994
    Date of Patent: July 15, 1997
    Assignee: Biota Scientific Management Pty., Ltd.
    Inventors: Laurence Mark Von Itzstein, Wen-Yang Wu, Tho Van Phan, Basil Danylec, Betty Jin, Peter Malcolm Colman, Joseph Noozhumurry Varghese
  • Patent number: 5602262
    Abstract: A process for producing intermediate compounds 2-deoxy 2,2-difluoro-.beta.-D-ribo-pentopyranose (III) from 3,3-difluoro-4,5,6-O-trihydroxy-5,6-O-(1-ethylpropylidene)hexene (I). The process of preparing intermediate compound (I) involves reacting D-glyceraldehyde pentanide with an organometallic complex of 3-bromo-3,3-difluoropropene. The process of preparing intermediate compound (III) involves ozonolysis and then hydrolysis. The intermediate compounds (I) and (III) are used in the preparation of 2'-deoxy-2',2'-difluorocytidine which is an antiviral agent.
    Type: Grant
    Filed: February 3, 1995
    Date of Patent: February 11, 1997
    Assignee: Eli Lilly and Company
    Inventor: David D. Wirth
  • Patent number: 5453439
    Abstract: The invention concerns hydroxylamine derivatives of the formula I ##STR1## wherein R.sup.4 is hydrogen, carbamoyl, (1-4C)alkyl, (2-5C)alkanoyl, N-(1-4C)alkylcarbamoyl, N,N-di-(1-4C)alkylcarbamoyl, benzoyl or phenylsulphonyl;R.sup.5 includes hydrogen, (1-4C)alkyl and (2-5C)alkanoyl;R.sup.6 is hydrogen, (1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl;R.sup.7 is hydrogen or (1-4C)alkyl;Ar.sup.1 is phenylene;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl, thiazolediyl, oxazolediyl, thiadiazolediyl or oxadiazolediyl;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is independently (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: February 8, 1993
    Date of Patent: September 26, 1995
    Assignees: Zeneca Limited, Zeneca-Pharma S.A.
    Inventor: Patrick Ple
  • Patent number: 5403857
    Abstract: The invention concerns benzenesulphonamide derivatives of the formula I ##STR1## wherein R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; R.sup.2 and R.sup.3 together form -A.sup.2 -X.sup.2 -A.sup.3 - which defines a ring having 5 or 6 ring atoms, wherein A.sup.2 and A.sup.3 each is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl; A.sup.1 is a direct link to X.sup.1 or is (1-3C) alkylene; X.sup.1 is oxy, thio or imino; Ar is optionally substituted phenylene; R.sup.4 is (1-4C)alkyl, fluoro-(2-4C)alkyl or optionally substituted phenyl or a heterocyclic moiety; R.sup.5 is hydrogen or (1-4C)alkyl; and R.sup.6 is hydrogen, halogeno, trifluoromethyl, (1-4C)alkyl or (1-4C)alkoxy; or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: February 1, 1994
    Date of Patent: April 4, 1995
    Assignees: Imperial Chemical Industries PLC, ICI-Pharma
    Inventors: Philip N. Edwards, Keith Oldham, David Waterson
  • Patent number: 5387701
    Abstract: A process for preparing 4-hydroxymethyltetrahydropyran comprises reacting tetrahydrofurans of the general formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 - to C.sub.6 -alkyl or --CO--R.sup.2, andR.sup.2 is hydrogen or C.sub.1 - to C.sub.6 -alkyl,at from 0.degree. to 400.degree. C. and from 0.001 to 400 bar in the presence of acidic catalysts.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: February 7, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Weyer, Rolf Fischer, Werner Schnurr, Norbert Goetz, Thomas Kuekenhoehner
  • Patent number: 5376680
    Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 is hydrogen, (1-4C)alkyl, halogeno-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl; R.sup.5 is hydrogen, (1-4C)alkyl, halogeno-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, or a heteroaryl moiety selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, furyl, thienyl, oxazolyl and thiazolyl;A.sup.4 is (1-4C)alkylene;Ar.sup.1 is phenylene, pyridinediyl or pyrimidinediyl;A.sup.1 is a direct link to X.sup.1 or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl or thiazolediyl;R.sup.1 is hydrogen, (1-4C)alkyl, (3-C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is independently (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: December 27, 1994
    Assignees: Zeneca Limited, Zeneca Pharma, S.A.
    Inventors: Philip N. Edwards, Michael S. Large
  • Patent number: 5360815
    Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.
    Type: Grant
    Filed: June 23, 1993
    Date of Patent: November 1, 1994
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Rejean Fortin, Yves Girard, Erich Grimm, John Hutchinson, John Scheigetz
  • Patent number: 5360817
    Abstract: Derivatives and analogues of 2-deoxy-2,3-didehydro-N-acetyl neuraminic acid, pharmaceutical formulations thereof, methods for their preparation .and their use in the treatment of viral infections, in particular influenza, are described.
    Type: Grant
    Filed: November 10, 1992
    Date of Patent: November 1, 1994
    Assignee: Biota Scientific Management Pty Ltd
    Inventors: Laurence M. von Izstein, Wen-Yang Wu, Tho V. Phan, Basil Danylec, Betty Jin
  • Patent number: 5350765
    Abstract: Compounds of the structure ##STR1## where Ar is optionally substituted carbocyclic aryl, 5- or 6-membered heterocyclic aryl, 10-membered bicyclic heterocyclic aryl containing one or two nitrogen atoms, 9- or 10-membered heterocyclic containing one or two nitrogen atoms and optionally containing a further nitrogen or oxygen atom and one oxo or thioxo substituent, benzo[b]furyl, or benzo[b]thienyl, A.sub.1 is propynyl, methylene, or a direct link to X, X is oxy, thio, sulfonyl, or NR.sub.4, A.sub.2 is selected from ##STR2## where Y is hydrogen, halogen, or nitrile; Z is hydrogen, R.sub.1 is alkyl, and R.sub.2 is hydrogen or alkyl are potent inhibitors of lipoxygenase enzymes and thus inhibit the biosynthesis of leukotrienes. These compounds are useful in the treatment or amelioration of allergic and inflammatory disease states.
    Type: Grant
    Filed: August 30, 1993
    Date of Patent: September 27, 1994
    Assignee: Abbott Laboratories
    Inventors: Joseph F. Dellaria, Jimmie L. Moore, Dee W. Brooks
  • Patent number: 5349071
    Abstract: Processes for synthesizing tertiary alkynols by reacting carbonyl-group-containing compounds with alkynes in the presence of a basic catalyst are disclosed. Preferred products are 6,10,14-trimethyl-4-pentadecyn-6-ol compounds having the structure: ##STR1## A preferred, novel compound, 6,10,14-trimethyl-4-pentadecyne-2,6-diol, can be used in the synthesis of Vitamin E or Vitamin K.sub.1.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: September 20, 1994
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • Patent number: 5308852
    Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: May 3, 1994
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Yves Girard, Daniel Delorme, Rejean Fortin, Daniel Dube, Pierre Hamel, Carol Lepine, Yves Ducharme
  • Patent number: 5260442
    Abstract: The invention concerns quinolinium salt intermediates of the formula I ##STR1## and processes for their manufacture; and their use in the manufacture of aryloxymethyl-substituted 1-alkyl-2-quinolone derivatives which are 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: December 5, 1991
    Date of Patent: November 9, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Jonathan Hutton, David Waterson
  • Patent number: 5254581
    Abstract: The invention concerns a cyclic ether derivative of the formula I ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a 9- or 10-membered bicyclic heterocyclic moiety;A.sup.1 is a direct link to X.sup.1 or (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar.sup.2 is optionally substituted phenylene or pyridylene;R.sup.1 includes hydrogen, (1-4C)alkyl, (1-4C)alkcxycarbonyl and (1-4C)alkylthio; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 5 to 7 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: February 2, 1993
    Date of Patent: October 19, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Pierre A. R. Bruneau, Robert I. Dowell, David Waterson
  • Patent number: 5250715
    Abstract: The present invention provides an optically active 2-methylenepentane derivative represented by the general formula ##STR1## (wherein R.sup.1 is a protective group for hydroxyl, R.sup.3 is a protective group for hydroxyl, X is a halogen atom or R.sup.4 SO.sub.3 group (wherein R.sup.4 is an alkyl or an aryl), and the symbol * represents an asymmetric carbon atom).
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: October 5, 1993
    Assignee: Daiso Co., Ltd.
    Inventors: Takashi Takahashi, Yoshikazu Takehira
  • Patent number: 5250710
    Abstract: The present invention relates to dihydropyran derivatives, processes for preparing, and processes of using the derivatives. The derivatives are prepared by condensation of lithium dienolate of prenal with an aldehyde or a ketone.The pyran derivative prepared from .beta.-ionylideneacetaldehyde when treated in the presence of a catalyst directly forms retinal.
    Type: Grant
    Filed: May 7, 1992
    Date of Patent: October 5, 1993
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre F. Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5225438
    Abstract: The invention concerns an aryl derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X.sup.1 is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X.sup.1 is a group of the formula--X.sup.4 --CR.sub.2 -- or --CR.sub.2 --X.sup.4 --whereinX.sup.4 is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl;each of Ar.sup.2 and Ar.sup.3 is optionally substituted phenylene;X.sup.2 is oxy, thio, sulphinyl or sulphonyl;R.sup.1 is (1-4C)alkyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X.sup.3 --A.sup.2 -- which together with the carbon atom to which A.sup.1 and A.sup.2 are attached define a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: July 6, 1993
    Assignees: Imperial Chemical Industries PLC, I.C.I.-Pharma
    Inventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
  • Patent number: 5157133
    Abstract: The present invention relates to dihydropyran derivatives, processes for preparing, and processes of using the derivatives. The derivatives are prepared by condensation of lithium dienolate of prenal with an aldehyde or a ketone.The pyran derivative prepared from .beta.-ionylideneacetaldehyde when treated in the presence of a catalyst directly forms retinal.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: October 20, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre F. Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5149843
    Abstract: Conjugated diene compounds of the general formula: ##STR1## which are industrially advantageous intermediates for preparing sarcophytol A useful as an anticarcinogenic promotor or antitumor agent are provided.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5141952
    Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein the dotted lines represent a possible endo or exo double bond, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms and ##STR2## R'.sub.2 is alkyl of 1 to 8 carbon atoms or aryl of 6 to 14 carbon atoms, X is --O-- or --NR--, R is selected from the group consisting of --OH, hydrogen, ##STR3## and --COOR', R' is hydrogen or alkyl of 1 to 8 carbon atoms, Y is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and alkenyl and alkynyl of 2 to 8 carbon atoms, all optionally substituted with at least one halogen or --OH, with the proviso that if Y is --OH, X is not --NH-- and their non-toxic, pharmaceutically acceptable addition salts of acids or bases having antibacterial and immunological properties.
    Type: Grant
    Filed: June 18, 1991
    Date of Patent: August 25, 1992
    Assignee: Roussel Uclaf
    Inventors: Constantin Agouridas, Patrick Fauveau
  • Patent number: 5134148
    Abstract: The invention concerns a heterocycle of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 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;and R.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 4 to 7 ring atoms, wherein A.sup.2 and A.sup.3, which may be the same or different, each is (1-4C)alkylene and X.sup.
    Type: Grant
    Filed: September 5, 1991
    Date of Patent: July 28, 1992
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Graham C. Crawley, Philip N. Edwards, Jean-Marc M. M. Girodeau
  • Patent number: 5128489
    Abstract: A process for production of an optically active isomer of 2-(tetrahydropyran-2-yloxy)-1-propanol represented by formula (I): ##STR1## is disclosed, which comprises reacting an optically active isomer of a 1-acyloxy-2-propanol represented by formula (II): ##STR2## wherein R is a substituted or unsubstituted aryl group, with 3,4-dihydro-2H-pyran to obtain an optically active isomer of a 1-acyloxy-2-(tetrahydropyran-2-yloxy)propane represented by formula (III): ##STR3## wherein R is as defined above, and hydrolyzing the compound (III) to eliminate the acyl group. The optically active isomer of 2-(tetrahydropyran-2-yloxy)-1-propanol represented by formula (I) is an intermediate for synthesis of pyridobenzoxazine derivatives useful as a synthetic antibacterial agent, particularly an optically active isomer of ofloxacin.
    Type: Grant
    Filed: October 4, 1990
    Date of Patent: July 7, 1992
    Assignees: Takasago International Corporation, Daiichi Pharmaceutical Co., Ltd.
    Inventors: Hidenori Kumobayashi, Akio Tachikawa, Yoshiki Okeda, Toshihiro Fujiwara
  • Patent number: 5116869
    Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: May 26, 1992
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
  • Patent number: 5110949
    Abstract: An improved method for synthesizing leukotriene B.sub.4 and derivatives thereof is disclosed, as are novel intermediates used in the process. Unlike prior art processes, the method of this invention involves a step in which 2(R)-[[(1,1-dimethylethyl)diphenylsilyl]oxy]dec-4 (Z)-ene-1-ol or a related compound is coupled with methyl-[5(S)-[[1,1dimethylethyl)-diphenylsilyl]oxy]-dec-8 (E)-10-(dimethylphosphono)-6-ynoate.
    Type: Grant
    Filed: September 13, 1989
    Date of Patent: May 5, 1992
    Assignee: University of Pennsylvania
    Inventors: Yoshihiro Abe, Kyriacos C. Nicolaou
  • Patent number: 5098930
    Abstract: The invention concerns a heterocyclic derivative 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; andR.sup.2 and R.sup.3 together form a group of the formula -A.sup.2 -X-A.sup.3 - wherein each of A.sup.2 and A.sup.3 is (1-4C)alkylene and X is oxy, thio, sulphinyl, sulphonyl or imino;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: March 24, 1992
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Philip N. Edwards, Jean-Marc M. M. Girodeau
  • Patent number: 5055592
    Abstract: This invention relates to the novel processes for the preparation of a 16-methoxy-16-methyl prostaglandin E.sub.1 derivative and to the novel intermediates useful therefor.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: October 8, 1991
    Assignee: Merrell Dow Pharmaceuticals
    Inventors: Michael Kolb, Luc Van Hijfte
  • Patent number: 5053507
    Abstract: Optical active compounds of the formula (1), (2), (3) and (4): ##STR1## The compounds (1), (2) and (3) are useful as raw materials of chiral dopants to be added for forming liquid crystal compositions, medicines or agricultural chemicals, and the compound (4) is useful as chiral dopants to be added for forming liquid crystal compositions.
    Type: Grant
    Filed: March 21, 1990
    Date of Patent: October 1, 1991
    Assignee: Arakawa Kagaku Kogyo Kabushiki Kaisha
    Inventors: Fumio Moriuchi, Hiroshi Yano, Kazushige Kajita
  • Patent number: 5049681
    Abstract: A novel optically active allyl alcohol derivative represented by the following general formulae (I), (II), (III) and (IV): ##STR1## The novel optically active allyl alcohol can be used effectively for producing leucotrienes B.sub.4 by the process of reacting an optically active halogen substituted allyl alcohol and a novel optically active acetylene-substituted allyl alcohol.
    Type: Grant
    Filed: July 8, 1988
    Date of Patent: September 17, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 5017583
    Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are leukotriene antagonists. These compounds inhibit SRS-A and leukotriene synthesis and are antagonists of SRS-A and are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.
    Type: Grant
    Filed: February 23, 1988
    Date of Patent: May 21, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
  • Patent number: 4996375
    Abstract: Novel methyl carbinol derivatives of Vitamin E and a method for their manufacture.
    Type: Grant
    Filed: April 24, 1989
    Date of Patent: February 26, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Josef Hubscher
  • Patent number: 4983747
    Abstract: Disclosed is a process for the preparation of a perfluoroorganic compound, which comprises fluorinating a partially fluorinated or unfluorinated organic compound having carbon-to-fluorine bonds under mild conditions and then, contacting the resulting reaction mixture with a fluorine gas at a temperature of 110.degree. to 180.degree. C.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: January 8, 1991
    Assignee: Tokuyama Soda Kabushiki Kaisha
    Inventors: Masakatsu Nishimura, Naoya Okada, Yasuo Murata, Yasuhiko Hirai
  • Patent number: 4965376
    Abstract: 3,9-Dihydroxynonyne and its derivatives protected at the 9-OH function, of the general formula I ##STR1## where R is hydrogen or a conventional alcohol protective group, and processes for the preparation of the compounds I.
    Type: Grant
    Filed: April 18, 1989
    Date of Patent: October 23, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Huellmann, Rainer Becker, Gerald Lauterbach, Ernst Buschmann, Heinz Eckhardt, Walter Himmele, Christiane Brueckner
  • Patent number: 4933510
    Abstract: Propanol derivatives of formula (I) wherein X is a leaving group; R.sub.1 is H or a protecting group; and R.sub.2 is H, and R.sub.3 is a group--CH.sub.2 Y wherein Y is a leaving group; or R.sub.2 and R.sub.3 together form .dbd.CH.sub.2. The propanol derivatives of the formula (I) are useful as multifunctional alkylating agents.
    Type: Grant
    Filed: March 13, 1989
    Date of Patent: June 12, 1990
    Assignee: Symbicom Aktiebolag
    Inventors: Hans G. Magnusson, Torbjorn Frejd
  • Patent number: 4889939
    Abstract: Compounds suitable for being used as lubricants, having general formula:(I) RO--(C.sub.3 F.sub.6 O).sub.m --(CFXO).sub.n --CFX--L, or(II) R"CFXO--(C.sub.3 F.sub.6 O).sub.x (CFXO).sub.y --(C.sub.2 F.sub.4 O).sub.z --CFX--L, whereR=--CF.sub.3, --C.sub.2 F.sub.5, --C.sub.3 F.sub.7X=F, --CF.sub.3R"=F, --CF.sub.3, --C.sub.2 F.sub.5m=an integer from 3 to 100n=a finite integer, or =zero, wherefore m+n ranges from 3 to 100, provided that, if n is finite, m/n ranges from 5 to 20 and R is preferably =CF.sub.3, if n=zero, R is preferably --C.sub.2 F.sub.5 or --C.sub.3 F.sub.7x=a finite integer, or =zeroy, z=finite integers, such that x+y+z ranges from 5 to 200, while (x+z)/y ranges from 5 to 0.5, provided that when x=zero, z/y ranges from 1 to 0.5 and y+z ranges from 5 to 200 n while X is preferably F, and R"=LL=group Y-Z, where:Y=--CH.sub.2 O--, --CH.sub.2 --OCH.sub.2, --CF.sub.2, --CF.sub.
    Type: Grant
    Filed: April 11, 1988
    Date of Patent: December 26, 1989
    Assignee: Montedison S.p.A.
    Inventors: Gerardo Caporiccio, Ezio Strepparola, Mario A. Scarati
  • Patent number: 4861922
    Abstract: There is disclosed a method of hydroformylating 3-methyl-3-buten-1-ol and analogs thereof with carbon monoxide and hydrogen in the presence of a rhodium compound free from modification by a ligand containing an element belonging to the group V of the periodic table as well as a method of producing 3-methylpentane-1,5-diol and .beta.-methyl-.delta.-valerolactone using such hydroformylation product.
    Type: Grant
    Filed: February 11, 1987
    Date of Patent: August 29, 1989
    Assignee: Kuraray Company, Ltd.
    Inventors: Yasuo Tokitoh, Noriaki Yoshimura
  • Patent number: 4837345
    Abstract: A process for producing a tetrahydropyran-3-one derivative of the formula: ##STR1## wherein R is a hydrogen atom; a straight chained or branched C.sub.1 -C.sub.10 alkyl group which is unsubstituted or substituted by a halogen atom, a hydroxyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylcarbonyloxy group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 mono- or dialkylamino group, a C.sub.3 -C.sub.6 cycloaklyl group, a C.sub.1 -C.sub.6 alkylaminocarbonyl group, a C.sub.1 -C.sub.6 alkylcarbonylamino group, a C.sub.1 -C.sub.6 alkylcarbonyl group or a phenyl or benzoyl group which is unsubstituted or substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkythio group or a C.sub.1 -C.sub.6 alkoxycarbonyl group; a C.sub.3 -C.sub.6 cycloalkyl group; or a phenyl or biphenyl group which is unsubstituted or substituted by a halogen atom, a C.sub.1 -C.sub.6 alkoxy group or C.sub.1 -C.sub.
    Type: Grant
    Filed: December 31, 1987
    Date of Patent: June 6, 1989
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Tatsuo Numata, Masataka Hatanaka, Junichi Watanabe
  • Patent number: 4835292
    Abstract: (2R,3S,4R)-(+)- and (2S,3R,4S)-(-)-2,4-dimethyl-3-tetrahydropyranyloxy-1-heptanols which are important intermediates for synthesis of invictolide, one component of a queen recognition peromone of red imported fire ant.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: May 30, 1989
    Assignee: Nitto Electric Industrial
    Inventors: Shuji Senda, Yutaka Nakazono, Kenji Mori
  • Patent number: 4825006
    Abstract: A process for producing vitamin A represented by the formula ##STR1## which comprises treating a compound represented by the formula ##STR2## wherein R.sup.1 represents an aryl group which may be substituted, R.sup.21 and R.sup.22 each represents a hydrogen atom or a lower alkanoyl group, R.sup.3 represents an acetal-type protective group for a hydroxyl group, and X represents a halogen atom, with a base; and novel intermediate compounds useful for the above process.
    Type: Grant
    Filed: December 3, 1985
    Date of Patent: April 25, 1989
    Assignee: Kuraray Co., Ltd.
    Inventors: Junzo Otera, Tadakatsu Mandai, Mikio Kawada
  • Patent number: 4818431
    Abstract: New tetrahydropyran derivatives of the formula I ##STR1## in which G is H.sub.2 or .dbd.O, R.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, it also being possible for one or two CH.sub.2 groups to be replaced by O atoms, or are F, Cl, Br or CN, R.sup.2 is also H, A.sup.1 and A.sup.2 are each 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl groups which are unsubstituted or substituted by 1-4 F atoms, Z.sup.1 and Z.sup.2 are each --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, or a single bond, m and n are each 0, 1, 2 or 3, but (m+n) is at least 1 and at most 3, it being possible, when m is 2 or 3, for the group A.sup.1 and, when n is 2 or 3, for the groups A.sup.2 each to be identical or different from one another, and the acid addition salts of those among these compounds which are basic, are suitable for use as components in liquid-crystal dielectrics.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: April 4, 1989
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Joachim Krause, Peter Fuss
  • Patent number: 4808737
    Abstract: The hydroformylation of 3-methyl-3-buten-1-ol with hydrogen and carbon monoxide, when carried out under relatively mild conditions, gives 2-hydroxy-4-methyltetrahydropyran (MHP) in high rate of reaction and in high selectivity even in a very low rhodium catalyst concentration. MHP is useful as a starting material for the production of 3-methyl-1,5-pentanediol and .beta.-methyl-.delta.-valerolactone which are in turn usable as raw materials for producing polyesters and polyurethanes. The process according to the invention can give such MHP advantageously from the industrial viewpoint and has very great industrial utility.
    Type: Grant
    Filed: October 22, 1986
    Date of Patent: February 28, 1989
    Assignee: Kuraray Co., Ltd.
    Inventors: Noriaki Yoshimura, Yasuo Tokitoh
  • Patent number: 4782168
    Abstract: A 2,3-dihydro-2,3,5-trimethyl-4H-pyran-4-one derivative represented by general formula: ##STR1## where R is ##STR2## --CH(OCH.sub.3).sub.2, --CH(OC.sub.2 H.sub.5).sub.2, --CHO, --CH.sub.2 OH, --CH.dbd.CH.sub.2, .dbd.CHCH.sub.2 CH.sub.3, --CH.dbd.CHCH.sub.3 or ##STR3## The derivative is useful as a sex attractant for drugstore beetles.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: November 1, 1988
    Assignees: Japan Tobacco, Inc., Fuji Flavor Co., Ltd.
    Inventors: Hisashi Kodama, Keiko Mochizuki, Masahiro Kohno, Akio Ohnishi, Mikio Ono
  • Patent number: 4719227
    Abstract: Iodopropargyl ethers of the formula ##STR1## wherein A represents oxygen or a methylene group,R.sup.1 denotes hydrogen or lower alkyl,R.sup.2 and R.sup.3 are identical or different and represent hydrogen, lower alkyl, alkenyl or unsubstituted or halogen-substituted phenyl, or R.sup.2 and R.sup.3 together form a carbocyclic ring with 4 to 7 C atoms,L and m represent 0, 1 or 2,k denotes 0 or 1 andn denotes an integer from 0 to 4, with the proviso that if 1 is 0, n represents 1, 2, 3 or 4,can be prepared by reaction of the corresponding propargyl ethers with iodinating agents. The iodopropargyl ethers are active compounds in microbicidal agents.
    Type: Grant
    Filed: February 27, 1986
    Date of Patent: January 12, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerold Schade, Wilfried Paulus, Hans-Georg Schmitt
  • Patent number: 4709059
    Abstract: Epoxy compounds for use as epoxy resins are prepared from relatively inexpensive and renewable resources via a selective halogenation process. Primary pendant hydroxyl groups on straight carbon chain compounds with oxygen atoms pendant to each carbon are selectively halogenated with, for example, carbon tetrachloride. A scavenger agent, triphenylphosphine and pyridine, is used to complex the residual portion of reacted halogenating agent. One additional step with the halogenated intermediate yields epoxy compounds which, when cured, yield epoxy resins.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: November 24, 1987
    Assignee: The Dow Chemical Company
    Inventors: Stoil K. Dirlikov, Connie J. Schneider
  • Patent number: 4680307
    Abstract: A compound of the formula: ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group, Y.sup.1 is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or C.sub.1 -C.sub.4 alkyl group), ##STR4## (R.sup.6 is as defined above), ##STR5## R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a shingle linkage to from a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: July 14, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Muraoka, Toshio Nakamura, Akihiko Sugie, Keiichi Ono, Michihiro Yamamoto
  • Patent number: 4665092
    Abstract: Alkenes of the formula (I) and epoxides (II) used to make them are useful as anti-inflammatory and antiallergic pharmaceuticals: ##STR1## wherein R.sup.1 =H or CH.sub.3 ; R.sup.2 =phenyl, substituted phenyl, benzyl or a cysteinyl moiety; R.sup.4 and R.sup.5 =alkyl; n=O or 1; and R.sup.3 is as described.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: May 12, 1987
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Michael P. Ferro, Michael P. Wachter
  • Patent number: 4663468
    Abstract: There is disclosed a method of hydroformylating 3-methyl-3-buten-1-ol and analogs thereof with carbon monoxide and hydrogen in the presence of a rhodium compound free from modification by a ligand containing an element belonging to the group V of the periodic table as well as a method of producing 3-methylpentane-1,5-diol and .beta.-methyl-.delta.-valerolactone using such hydroformylation product.
    Type: Grant
    Filed: March 12, 1985
    Date of Patent: May 5, 1987
    Assignee: Kuraray Company, Ltd.
    Inventors: Yasuo Tokitoh, Noriaki Yoshimura
  • Patent number: 4632997
    Abstract: A method for preparing a cis-bicyclo[3.3.0]octylidene derivative represented by the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or an alkyl group; R.sup.2 is a hydrogen atom or a protective group for hydroxyl group; and Y is ##STR2## where R.sup.3 is a hydrogen atom or a protective group for hydroxyl group; R.sup.4 is a hydrogen atom or a straight, branched or cyclic alkyl group, alkenyl group or alkynyl group; and X is a group represented by CH.dbd.CH or C.tbd.C,comprises carrying out the catalytic hydrogenation reaction of a (1-alkenyl)-cis-bicyclo[3.3.0]octene derivative represented by the formula: ##STR3## wherein R.sup.1, R.sup.2 and Y have the same meanings as defined above, in the presence of a metal carbonyl compound or its complex represented by the formula:Mw(CO)x(H)y(R)zwherein M is a metal element of the group VIB; R is a .pi. ligand or a phosphine ligand; w is 1 or 2; x is an integer of 3 to 6; y is 0 or 1; and z is 0 or an integer of 1 to 3.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: December 30, 1986
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa
  • Patent number: 4454330
    Abstract: A process for the preparation of a two-functional-group-containing terpenoid having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.
    Type: Grant
    Filed: March 22, 1982
    Date of Patent: June 12, 1984
    Assignees: Eisai Co., Ltd., General Director of the Agency of Industrial Science and Technology
    Inventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada
  • Patent number: 4405640
    Abstract: Insecticides of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each selected from methyl, halomethyl, and halo; X is oxygen, sulphur, sulphonyl or a group NR.sup.4 where R.sup.4 represents hydrogen, lower alkyl or lower carboxylic acyl; R.sup.3 is lower alkyl, lower alkenyl or benzyl; m has the value zero or one, and n has a value from one to four.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: September 20, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventor: Nazim Punja
  • Patent number: 4338251
    Abstract: A process for the preparation of a two-functional-group-containing terpenoid having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: July 6, 1982
    Assignees: Eisai Co., Ltd., Agency of Industrial Science and Technology
    Inventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada