Halogen Attached Directly Or Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/504)
  • Patent number: 5672767
    Abstract: A process for the preparation of a perfluoropolyether having a general formula: ##STR1## as defined hereinbefore, which process includes the direct fluorination with elemental fluorine of a polyether having a general formula: ##STR2## as defined hereinbefore, wherein the fluorination is carried out in the presence of a solvent which is an ether having at least one substituent R.sub.F, wherein R.sub.F is a fluorinated hydrocarbon group. The said solvent ether is preferably a fluorinated volatile ether. The said solvent ether preferably has at least two groups R.sub.F which may be the same or different groups. Each group R.sub.F preferably has from two to four carbon atoms and at least two fluorine atoms. The said solvent ether may be an alicyclic ether having from 3 to 5 carbon atoms in its alicyclic ring.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: September 30, 1997
    Assignee: BNFL Fluorochemicals Ltd.
    Inventors: Richard Dickinson Chambers, Andrew Keith Joel
  • Patent number: 5663367
    Abstract: Compounds of Formula 1 ##STR1## wherein Z is selected from the group consisting of the radicals shown in Formula 2 and in Formula 3, ##STR2## Y is cycloalkyl or cycloalkenyl of 3 to 8 carbons optionally substituted with one or two R.sub.4 groups, or Y is selected from phenyl, pyridyl, thienyl, furyl, pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R.sub.4 groups, the divalent Y radical being substituted by the Z and --CR.sub.1 .dbd.CR.sub.1 --CR.sub.1 .dbd.CR.sub.1 groups on adjacent carbons; X is S, O, or NR.sub.5 ; n is 1 or 2; R.sub.1 and R.sub.2 independently are H, lower alkyl or fluoroalkyl; R.sub.3 is hydrogen, lower alkyl, Cl or Br; R.sub.4 is lower alkyl, fluoroalkyl or halogen; R.sub.5 is H or lower alkyl, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: September 2, 1997
    Assignee: Allergan
    Inventors: Vidyasagar Vuligonda, Roshantha A. Chandraratna
  • Patent number: 5635537
    Abstract: A compound of the formula ##STR1## Z is hydrogen or halogen, Q is COR.sup.1 or 5-or 6-membered aryl which may contain 1 or 2 heteroatoms selected from N, 0 or S and may be substituted or fused wherein R is hydrogen or C.sub.1 -methyl (cis-configuration), R.sup.1 is C.sub.1 -C.sub.6 alkyl or an aromatic ring which may contain heteroatoms selected from O and S and may be substituted or fused to an optionally substituted benzene ring, R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl and R.sup.3 may be different groups defined in claim 1, and enantiomers/salts thereof, processes for preparation of said compounds, pharmaceutical preparations containing said compounds, use of and method of treatment of disorders in CNS by using said compounds.
    Type: Grant
    Filed: March 18, 1993
    Date of Patent: June 3, 1997
    Assignee: Astra Aktiebolag
    Inventors: Nils-Erik Anden, Berit C. E. Backlund Hook, Anna L. Bjork, Uli A. Hacksell, Sven-Erik Hillver, Ye Liu, Eva C. Mellin, Eva M. Persson, Karl J. Vallg.ang.rda, Hong Yu
  • Patent number: 5618941
    Abstract: Compounds of formula (I) wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each H or C.sub.1 -C.sub.4 alkyl; R.sup.5 is (CH.sub.2).sub.m NHSO.sub.2 R.sup.6 or (CH).sub.m NHCOR.sup.6 ; R.sup.6 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted by aryl, aryl or heteroaryl; R.sup.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, CF.sub.3, OCF.sub.3, CN, CONH.sub.2, or S(O).sub.n (C.sub.1 -C.sub.4 alkyl); X is CH.sub.2, CHCH.sub.3, CH(OH), C(OH)CH.sub.3, C.dbd.CH.sub.2, CO or O; m is 0 or 1 and n is 0, 1 or 2, and their pharmaceutically acceptable salts and biolabile esters, are antagonists of thromboxane A.sub.2 of utility, particulary in combination with a thromboxane synthetase inhibitor, in the treatment of atherosclerosis and unstable angina and for prevention of reocclusion after percutaneous transluminal angioplasty.
    Type: Grant
    Filed: March 15, 1995
    Date of Patent: April 8, 1997
    Assignee: Pfizer Inc.
    Inventors: Roger P. Dickinson, Kevin N. Dack, John Steele
  • Patent number: 5594155
    Abstract: Anomeric 2,2-difluororibosyl azide and amine intermediates which are useful for the preparation of 2'-deoxynucleosides, and processes thereto, are provided. Processes for preparing 2'-deoxynucleosides also are provided.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: January 14, 1997
    Assignee: Eli Lilly and Company
    Inventors: Larry W. Hertel, Charles D. Jones, Julian S. Kroin, Thomas E. Mabry
  • Patent number: 5591869
    Abstract: Methylene compounds are preferably prepared by reducing an aluminum halide complex of the formula ##STR1## in which R.sup.1 represents a C.sub.6 -C.sub.10 -aryl radical which is optionally substituted by 1 to 4 C.sub.1 -C.sub.4 -alkyl radicals, 1 to 4 fluorine, chlorine and/or bromine atoms, one C.sub.1 -C.sub.8 -alkoxy group and/or one acetoxy group, or represents a heteroaryl radical which is optionally substituted by one C.sub.1 -C.sub.4 -alkyl radical and/or one fluorine, chlorine or bromine atom and contains 5 to 10 C atoms and one O or S atom andR.sup.2 represents a C.sub.1 -C.sub.12 -alkyl radical which is optionally substituted by 1 to 5 fluorine, chlorine and/or bromine atoms, independently of R.sup.1 represents a radical as defined for R.sup.1 and, in the case where R.sup.1 =a C.sub.6 -C.sub.
    Type: Grant
    Filed: December 6, 1995
    Date of Patent: January 7, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Fiege, Ferdinand Hagedorn
  • Patent number: 5591891
    Abstract: N-[Mercaptoacyl(amino acid or peptide)] compounds and S-lipophilic aliphatic carbonyl derivatives thereof, and pharmaceutical compositions comprising such compounds, as well as the use of these compounds as antihypertensives by the inhibition of neutral endopeptidase and/or peptidyldipeptidase A are disclosed. Methods for preparing the such compounds and derivatives are disclosed also.
    Type: Grant
    Filed: January 24, 1994
    Date of Patent: January 7, 1997
    Assignee: Institut National de la Sante et de la Recherche Medicale (INSERM)
    Inventors: Marie-Claude Fournie-Zaluski, Bernard-Pierre Roques
  • Patent number: 5541345
    Abstract: Anomeric 2,2-difluororibosyl azide and amine intermediates which are useful for the preparation of 2'-deoxynucleosides, and processes thereto, are provided. Processes for preparing 2'-deoxynucleosides also are provided.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: July 30, 1996
    Assignee: Eli Lilly and Company
    Inventors: Larry W. Hertel, Charles D. Jones, Julian S. Kroin, Thomas E. Mabry
  • Patent number: 5539059
    Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: July 23, 1996
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5514679
    Abstract: Compounds of the formula ##STR1## wherein: R.sub.1 and R.sub.2 are independently hydrogen, halo, alkyl, alkenyl, alkoxy, hydroxy, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, alkylthioalkynyl, hydroxyalkoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, amino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy or cyanomethyl, nitro, difluoromethyl, trifluoromethyl or cyano;Y is alkylene of 3 to 9 carbon atoms;R.sub.3 and R.sub.4 are independently hydrogen, alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkanoyl, alkanoyloxy, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, cyanomethyl, fluoroalkyl, cyano, phenyl, alkynyl, alkene, or halo;R.sub.5 is alkoxycarbonyl, alkyltetrazolyl, phenyl or a heterocycle;or a pharmaceutically acceptable acid addition salts thereof; N-oxides thereof, are useful as antipirconaviral agents.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: May 7, 1996
    Assignee: Sterling Winthrop Inc.
    Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Theodore J. Nitz
  • Patent number: 5461117
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: October 24, 1995
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5455265
    Abstract: Process of treatment of mammals, including humans to treat diseases or conditions of the type which are normally treated with retinoid-like compounds is disclosed, with pharmaceutical compositions containing an active compound which is a selective agonist of the RXR retinoid receptor sites in preference to the RAR retinoid receptor sites. A compound is defined to be a selective agonist of the RXR receptor site if the compound is at least approximately ten times more effective as an agonist in the RXR receptor sites than in the RAR receptor sites.
    Type: Grant
    Filed: February 11, 1993
    Date of Patent: October 3, 1995
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5384415
    Abstract: A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.
    Type: Grant
    Filed: May 28, 1993
    Date of Patent: January 24, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Manuel Mas, Pascal Metivier
  • Patent number: 5332790
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: July 26, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5322904
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: June 21, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5322903
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: June 21, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5241086
    Abstract: A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: August 31, 1993
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Manuel Mas, Pascal Metivier
  • Patent number: 5216180
    Abstract: A herbicidal hydroxyethyl-cyclopropyl-azolyl derivative of the formula ##STR1## in which R.sup.1 represents halogen, phenyl or the grouping --Z-R.sup.3, whereinZ represents oxygen, sulphur, SO or SO.sub.2 andR.sup.3 represents alkyl, phenyl or benzyl,R.sup.2 represents alkenyl, optionally substituted furyl, optionally substituted thienyl or the radical of the formula ##STR2## wherein R.sup.4 represents difluoromethoxy, 1,1,2,2-tetrafluoroethoxy, 1,1,2-trifluoro-2-chloro-ethoxy, cyano, formyl, alkoximinoalkyl, carbalkoxy, dialkoxyalkyl, phenoxyalkyl which is optionally substituted in the phenyl moiety by halogen, or benzyloxy which is optionally substituted in the phenyl moiety by halogen andR.sup.5 represents hydrogen or halogen, orR.sup.4 and R.sup.5 are linked in the ortho-position and together represent --O--CH.sub.2 --O--, orR.sup.2 represents the radical of the formula ##STR3## in which R.sup.6 represents difluoromethoxy, 1,1,2,2-tetrafluoroethoxy or 1,1,2-trifluoro-2-chloro-ethoxy, orR.sup.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: June 1, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Scherkenbeck, Monika Frie, Klaus Stroech, Thomas Himmler, Georg-W. Ludwig, Wilhelm Brandes, Stefan Dutzmann
  • Patent number: 5194619
    Abstract: The compounds of the formula I or Ia ##STR1## in which R.sup.1 is alkyl, aryl, alkoxy, alkenyl, arylalkyl, alkylaryl, aryloxy, fluoroalkyl, halogenoaryl, alkynyl, trialkylsilyl or a heteroaromatic radical,R.sup.2, R.sup.3 and R.sup.4, in addition to hydrogen, have the meanings given under R.sup.1 andR.sup.5 is hydrogen, alkyl, fluoroalkyl or alkenyl, can be obtained in a one-stage process by reaction of a compound II ##STR2## with (substituted) cyclopentadiene in the presence of a base. The compounds I and Ia are suitable as ligands for metallocene complexes which are used as catalysts in olefin polymerization.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: March 16, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dieter Reuschling, Jurgen Rohrmann, Gerhard Erker, Reiner Nolte, Michael Aulbach, Astrid Weiss
  • Patent number: 5179123
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxgen, sulfur, --CH.dbd.CH--or --CH.dbd.N--; wherein R.sub.1 is alkyl, alkenyl or alkynyl of about 1 to 20 carbon atoms; wherein R is --CO.sub.2 R.sup.2, tetrazole, methylsulfonamide or benzenesulfonamide, wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation and R.sup.3 is hydroxyl or halogen, having utility as LTB.sub.4 synthesis inhibitors.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: January 12, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • Patent number: 5126461
    Abstract: Process for ring opening compounds of the formula ##STR1## in which R.sup.1 is heteroaryl or aryl, R.sup.2 is a leaving group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R.sup.3 to R.sup.6 is other than hydrogen, by breaking the bond joining the carbon atom attached to R.sup.3 and the carbon atom attached to R.sup.6 in organic solution using silica, giving useful diene or allyl derivatives, certain of which are novel.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: June 30, 1992
    Assignee: Shell Research Limited
    Inventors: Mark S. Baird, Ian Bruce
  • Patent number: 5112977
    Abstract: Substituted naphthacenediones of the formula I ##STR1## in which R.sup.1 to R.sup.8 are H and at least one of R.sup.1 to R.sup.8, for example R.sup.2 and R.sup.3 or R.sup.2 and R.sup.6, are, for example, C.sub.1 -C.sub.20 alkoxy, C.sub.1 -C.sub.20 alkenoxy, C.sub.1 -C.sub.20 -alkylsulfinyl, --CN, --CF.sub.3, --NO.sub.2, --Si(CH.sub.3).sub.3 or --COO(C.sub.1 -C.sub.12 alkyl), are suitable, when incorporated into polymers having hydroxyalkyl groups, for currentless deposition of metals onto the polymer surface. They are in some cases suitable as photoinitiators.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: May 12, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Fischer, Marcus Baumann, Jurgen Finter, Vratislav Kvita, Carl W. Mayer, Wolfgang Wernet
  • Patent number: 5099033
    Abstract: The present invention is directed to a process of making tetrahydrofuran of the formula (D) ##STR1## resulting in 2,5-diaryltetrahydrofuran PAF antagonists of pharmaceutically acceptable purity.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: March 24, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Ichiro Shinkai, Andrew S. Thompson, Thomas R. Verhoeven
  • Patent number: 5093432
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: March 3, 1992
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5034537
    Abstract: This invention relates to (R)-.alpha.-methyl-4-halobenzenemethanamine salts of epimers of acids of the formula ##STR1## and the use of these salts to separate these epimers. These acids are leukotriene antagonists.
    Type: Grant
    Filed: February 8, 1990
    Date of Patent: July 23, 1991
    Assignee: SmithKline Beecham Corporation
    Inventor: James S. Frazee
  • Patent number: 4973716
    Abstract: A process for fluorinating hydrogenated ethereal compounds by direct reaction with elemental F.sub.2 diluted with an inert gas, wherein the starting compound is in the liquid phase, said fluorination being carried out in the presence of a per fluoropolyetheral compound and of an alkaline metal fluoride.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: November 27, 1990
    Assignee: Ausimont S.p.A.
    Inventors: Pierangelo Calini, Silvana Modena
  • Patent number: 4918207
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a pheynl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 17, 1990
    Assignee: Aldrich Chemical Co., Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4868318
    Abstract: The present invention relates to novel perfluoro chemicals (PFC), particularly perfluorocyclic ethers and polyfluorinated compounds containing a few chlorine atoms and to a method for the preparation thereof.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: September 19, 1989
    Assignee: The Green Cross Corporation
    Inventors: Kirby V. Scherer, Jr., Taizo Ono, Kouichi Yamanouchi, Kazumasa Yokoyama
  • Patent number: 4859747
    Abstract: The direct fluorination of ethers in the presence of hydrogen fluoride (HF) scavengers such as sodium fluoride and potassium fluoride is disclosed. Ethers (liquid or solid) are either mixed with the HF scavenger, coated onto the HF scavenger or placed separately with the HF scavenger into a fluorination reactor and fluorinated by exposure to elemental fluorine. The HF scavenger permits use of more severe fluorination conditions than would be possible in the absence of the scavenger, i.e. higher initial fluorine, less gradual increases in fluorine gas concentrations and greater fluorine gas flow rates.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: August 22, 1989
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Richard J. Lagow
  • Patent number: 4827002
    Abstract: There are prepared compounds of general formula: ##STR1## wherein: R.sub.1 =H, or alkyl or acyl containing from 1 to 10 carbon atoms, R.sub.2, R.sub.3, like or unlike each other, may be H, or an alkyl containing from 1 to 10 carbon atoms and where R.sub.1 and R.sub.2 may form, together, an alkylene group containing from 2 to 10 carbon atoms, and optionally including up to 2 oxygen atoms in the chain, by means of addition reaction induced by radicalic starters of 1,2-dichlorodifluoroethylene to alcohols, ethers or esters of general formula: ##STR2## wherein: R.sub.1, R.sub.2, R.sub.3 are defined as above.
    Type: Grant
    Filed: May 31, 1985
    Date of Patent: May 2, 1989
    Assignee: Montefluos S.P.A.
    Inventors: Alberto Fontana, Silvana Modena, Giovanni Moggi
  • Patent number: 4804787
    Abstract: This invention relates to a process for making an enantiomer or racemic mixture of a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta.; novel intermediates useful for preparing these compounds; and processes for making the intermediates.
    Type: Grant
    Filed: October 9, 1985
    Date of Patent: February 14, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, Douglas L. Wren, Albert R. Van Horn, Tsung-Tee Li, Colin C. Beard
  • Patent number: 4798899
    Abstract: Azolyl-tetrahydrofuran-2-ylidene-methanes of the formula ##STR1## in which A represents a nitrogen atom or the CH group,R represents alkyl, alkenyl, alkinyl, alkoxyalkyl, alkylthioalkyl, halogenoalkyl, halogenalkoxyalkyl, halogenoalkylthioalkyl, halogenoalkenyl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted arylthioalkyl, optionally substituted cycloalkyl or optionally substituted cycloalkylalkyl,R.sup.1 to R.sup.6 are identical or different and represent hydrogen, alkyl, halogenoalkyl or halogen, up to at most 3 of the substituents representing halogen or halogenoalkyl, orR.sup.1 and R.sup.2, together with the carbon atom to which they are bonded, represent optionally substituted cycloalkyl, orR.sup.2 and R.sup.3, together with the carbon atoms to which they are bonded, represent optionally substituted cycloalkyl,or addition products thereof with acids or metal salts. Some new intermediates are also shown.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: January 17, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Ludwig Elbe, Manfred Jautelat, Karl H. Buchel, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
  • Patent number: 4755567
    Abstract: The direct fluorination of ethers in the presence of hydrogen fluoride (HF) scavengers such as sodium fluoride and potassium fluoride is disclosed. Ethers (liquid or solid) are either mixed with the HF scavenger, coated onto the HF scavenger or placed separately with the HF scavenger into a fluorination reactor and fluorinated by exposure to gradually increasing concentrations of fluorine gas. The HF scavenger permits use of more severe fluorination conditions i.e. higher initial fluorine, less gradual increases in fluorine gas concentrations and greater fluorine gas flow rates.
    Type: Grant
    Filed: October 27, 1986
    Date of Patent: July 5, 1988
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Richard J. Lagow
  • Patent number: 4748249
    Abstract: Azolyl-tetrahydrofuran-2-ylidene-methanes of the formula ##STR1## in which A represents a nitrogen atom or the CH group,R represents alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, halogenoalkyl, halogenoalkoxyalkyl, halogenoalkylthioalkyl, halogenoalkenyl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted arylthioalkyl, optionally substituted cycloalkyl or optionally substituted cycloalkylalkyl,R.sup.1 to R.sup.6 are identical or different and represent hydrogen, alkyl, halogenoalkyl or halogen, up to at most 3 of the substituents representing halogen or halogenoalkyl, orR.sup.1 and R.sup.2, together with the carbon atom to which they are bonded, represent optionally substituted cycloalkyl, orR.sup.2 and R.sup.3, together with the carbon atoms to which they are bonded, represent optionally substituted cycloalkyl,or addition products thereof with acids or metal salts. Some new intermediates are also shown.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: May 31, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Ludwig Elbe, Manfred Jautelat, Karl H. Buchel, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
  • Patent number: 4743595
    Abstract: A process for efficiently preparing 2-amino-5-nitrophenol derivatives in which benzoxazole derivatives are subjected to nucleophilic substitution reaction at the 5 position thereof to obtain corresponding benzoxazole derivatives, and the oxazole ring of the benzoxazole derivatives is then subjected to ring-opening to obtain 2-amino-5-nitrophenol derivatives. The 2-amino-5-nitrophenol derivatives are useful as industrial starting materials, reducing agents or antioxidants and intermediates for cyan-image-forming couplers.
    Type: Grant
    Filed: June 12, 1985
    Date of Patent: May 10, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Isamu Itoh, Mitsunori Ono, Hidetoshi Kobayashi, Kazuyoshi Yamakawa
  • Patent number: 4739057
    Abstract: A process for converting organic hydroxyl-containing compounds to halides which comprises reacting the hydroxyl-containing compound with a phosphorushalide reagent of formula: R.sub.n PX.sub.5-n wherein n is selected from 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of straight and branched chain alkyl, alkoxy, and haloalkyl, halogen, sulfonate and mixtures thereof; and X is a halogen. It is preferred to carry out the reaction in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphoshorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture. Maintaining a reaction temperature of from about 0.degree. C.
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: April 19, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
  • Patent number: 4736045
    Abstract: Fluorinated ether, process for their preparation, and use of the fluorinated ethers as inert fluids.
    Type: Grant
    Filed: September 11, 1984
    Date of Patent: April 5, 1988
    Inventors: Frederick G. Drakesmith, Richard L. Powell, Richard D. Chambers, Brian Grievson
  • Patent number: 4658045
    Abstract: 2,5-disubstituted furans are prepared by the cyclization of a 1,4-diketone in the presence of an intermediate or large pore sized acidic zeolite catalyst, preferably at elevated temperatures.
    Type: Grant
    Filed: November 22, 1985
    Date of Patent: April 14, 1987
    Assignee: Mobil Oil Corporation
    Inventor: Ralph M. Dessau
  • Patent number: 4619940
    Abstract: Azolyl-tetrahydrofuran-2-ylidene-methanes of the formula ##STR1## in which A represents a nitrogen atom or the CH group,R represents alkyl, alkenyl, alkinyl, alkoxyalkyl, alkylthioalkyl, halogenoalkyl, halogenoalkoxyalkyl, halogenoalkylthioalkyl, halogenoalkenyl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted arylthioalkyl, optionally substituted cycloalkyl or optionally substituted cycloalkylalkyl,R.sup.1 to R.sup.6 are identical or different and represent hydrogen, alkyl, halogenoalkyl or halogen, up to at most 3 of the substituents representing halogen or halogenoalkyl, orR.sup.1 and R.sup.2, together with the carbon atom to which they are bonded, represent optionally substituted cycloalkyl, orR.sup.2 and R.sup.3, together with the carbon atoms to which they are bonded, represent optionally substituted cycloalkyl,or addition products thereof with acids or metal salts. Some new intermediates are also shown.
    Type: Grant
    Filed: October 9, 1984
    Date of Patent: October 28, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Ludwig Elbe, Manfred Jautelat, Karl H. Buchel, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
  • Patent number: 4595693
    Abstract: Analogs of 2,5-Diaryl tetrahydrofurans which were substituted or unsubstituted at 3,4-positions were prepared.These compounds are found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and thereby useful in the treatment of various diseases or disorders mediated by the PAF, for example, inflammation, cardiovascular disorder, asthma, lung edema, adult respiratory distress syndrome, pain, and aggregation of platelets.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: June 17, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Tesfaye Biftu, Thomas W. Doebber, San-Bao Hwang, Thomas R. Beattie, Tsung-Ying Shen, Robert Stevenson
  • Patent number: 4565569
    Abstract: A diphenyl sulfone compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, same or different, each a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a phenoxy group, a lower alkylthio group, a lower alkylsulfonyl group or a lower alkoxycarbonyl(lower)alkoxy group, R.sub.
    Type: Grant
    Filed: May 13, 1983
    Date of Patent: January 21, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroyuki Konishi, Naganori Hino, Hiroshi Matsumoto, Ryo Yoshida
  • Patent number: 4545812
    Abstract: A diphenyl sulfone compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group or a lower alkoxycarbonyl(lower)alkoxy group, R.sub.2 is a hydroxyl group, a lower alkenyloxy group, a lower alkynyloxy group, a halo(lower)alkoxy group, a lower alkoxy(lower)alkoxy group, a cyano(lower)alkoxy group, a lower alkoxycyano(lower)alkoxy group, a hydroxy(lower)alkoxy group, a lower alkylcarbonyloxy group, a lower alkoxycarbonyl group, a lower alkylthio(lower)alkoxy group, a lower alkenyloxy(lower)alkoxy group, a di(lower)alkylamino(lower)alkoxy group, a hydroxyimino(lower)alkoxy group, a lower alkoxyimino(lower)alkoxy group, a lower alkylsulfonyloxy group, a lower alkoxycarbonyloxy group, a di(lower)alkoxyphosphinyloxy group, an oxotetrahydrofuranyloxy group or a group of the formula: --O--A--COR.sub.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: October 8, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroyuki Konishi, Naganori Hino, Hiroshi Matsumoto, Ryo Yoshida
  • Patent number: 4539332
    Abstract: Analogs of 2,5-Diaryl tetrahydrofurans which were substituted or unsubstituted at 3,4-positions were prepared.These compounds are found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and thereby useful in the treatment of various diseases or disorders mediated by the PAF, for example, inflammation, cardiovascular disorder, asthma, lung edema, adult respiratory distress syndrome, pain, and aggregation of platelets.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: September 3, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Tesfaye Biftu, San-Bao Hwang, Thomas W. Doebber, Thomas R. Beattie, Tsung-Ying Shen
  • Patent number: 4518415
    Abstract: Compounds useful as plant growth regulators and fungicides and having the formula ##STR1## and stereoisomers thereof, wherein W is --CH.dbd. or .dbd.N--; Q is optionally substituted aryl, especially optionally substituted phenyl, or optionally substituted aralkyl or alkyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, are H, optionally substituted alkyl, cycloalkyl, aralkyl or phenyl; R.sup.7 and R.sup.8 are H, alkyl or optionally substituted phenyl; and acid addition salts and metal complexes thereof, and processes and intermediates for their preparation.
    Type: Grant
    Filed: January 21, 1983
    Date of Patent: May 21, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony F. Marchington, Timothy Lewis, John M. Clough, Paul A. Worthington, John Dalziel
  • Patent number: 4487953
    Abstract: Compounds of Formula (I) ##STR1## wherein the 9-bromine atom can be in the .alpha.- or .beta.-position,R.sub.1 is CH.sub.2 OH or C(O)OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is C(O)NHR.sub.3 wherein R.sub.3 is an acid residue or R.sub.2 ; andA is --CH.sub.2 --CH.sub.2 -- or cis --CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH--, or --C.tbd.C--;W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D and E together are a direct bond; orD is straight-chain, branched, or cyclic alkylene of 1-10 carbon atoms, optionally substituted by fluorine atoms; andE is oxygen, sulfur, a direct bond --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 are different from each other and each is hydrogen, chlorine, or C.sub.1 -C.sub.4 -alkyl;R.sub.4 is a free or functionally modified hydroxy group;R.sub.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: December 11, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger
  • Patent number: 4487776
    Abstract: The invention relates to azolyl-phenoxy-tetrahydrofuran-2-ylidene-methanes defined herein under formula (I). Also included in the invention are compositions containing said compounds of formula (I) and methods for the use of such compounds and compositions as antimycotic agents. The invention further includes methods for the manufacture of the compounds of formula (I).
    Type: Grant
    Filed: January 27, 1983
    Date of Patent: December 11, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Ludwig Elbe, Manfred Jautelat, Karl H. Buchel, Klaus Schaller, Manfred Plempel
  • Patent number: 4454339
    Abstract: 9-Fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.-position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: June 12, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
  • Patent number: 4450217
    Abstract: Novel chalcogenopentalene compounds having a tellurium atom in the 6a position, and methods of making chalcogenopentalenes having a tellurium or a selenium atom in the 6a position are disclosed. The chalcogenopentalene compounds are useful as sensitizers in electrophotographic compositions and elements containing an electron donor and as charge emitters in multilayer photoconductive elements.
    Type: Grant
    Filed: March 15, 1983
    Date of Patent: May 22, 1984
    Assignee: Eastman Kodak Company
    Inventors: Michael R. Detty, Jerome H. Perlstein
  • Patent number: 4423234
    Abstract: Improved yields of biaromatic compounds, e.g., unsymmetrical biphenyl compounds, result by incorporating metallic copper in a non-aqueous diazonium-type coupling reaction.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: December 27, 1983
    Assignee: FMC Corporation
    Inventors: Ernest L. Plummer, David E. Seelye
  • Patent number: 4414216
    Abstract: There are disclosed tetrahydrofuran compounds and analogs thereof of the formula: ##STR1## and pharmaceutically acceptable acid addition salts thereof, wherein X is oxygen or sulfur, R.sup.1 and R.sup.2 are each hydrogen, halogen, lower alkyl or lower alkoxy, and Am is a group of the formula: ##STR2## wherein Z is oxygen or sulfur, R.sup.3 is hydrogen or halogen, R.sup.4 is hydrogen, lower alkyl or phenyl which may be substituted by 1 to 3 substituents at any position(s) on the phenyl nucleus, each substituent being independently selected from halogen, lower alkyl and lower alkoxy, and R.sup.5 is hydrogen or lower alkyl. Such compounds are useful as neuroleptics.
    Type: Grant
    Filed: June 21, 1982
    Date of Patent: November 8, 1983
    Assignee: Yoshitomi Phamaceutical Industries, Ltd.
    Inventors: Takeshi Kawakita, Yasuaki Chihara, Takemi Fukuda, Michihide Setoguchi, Tetsuya Tahara