Thiol Or Thioether Containing Patents (Class 568/29)
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Patent number: 6232503Abstract: The present invention provides compounds having the formula wherein R1, R2, R3, R4, and R5 are independently hydrogen, chlorine, bromine, fluorine, iodine, substituted or unsubstituted linear or branched C1-C3 alkoxy, substituted or unsubstituted linear or branched C1-C3 thioalkoxy, substituted or unsubstituted linear or branched C1-C8, alkyl, hydroxyl, thiol, —CN, —CF3, —OCF3, —NO2, acetyl, or —NR6R7; R6 and R7 are independently hydrogen, methyl, or ethyl; and X is iodine or bromine. Another embodiment of the invention includes specific ethynyl benzene sulfone derivatives. The alkynyl aryl sulfones of the present invention are useful as biocides, including, but not limited to, bactericides, fungicides, and preservatives. Also, a method of preparing the halogenated alkynyl aryl sulfones of formula I is provided.Type: GrantFiled: September 21, 1999Date of Patent: May 15, 2001Assignee: Lonza Inc.Inventor: Peter C. Nirchio
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Patent number: 6232401Abstract: A polythioether includes a structure having the formula I —R1—[—S—(CH2)2—O—[—R2—O—]m—(CH2)2—S—R1—]n— I wherein R1 denotes a divalent C2-6 n-alkyl, C3-6 branched alkyl, C6-8 cycloalkyl or C6-10 alkylcycloalkyl group, —[(—CH2—)p—X—]q—(—CH2—)r—, or —[(—CH2—)p—X—]q—(—CH2—)r— in which at least one —CH2— unit is substituted with a methyl group, R2 denotes methylene, a divalent C2-6 n-alkyl, C2-6 branched alkyl, C6-8 cycloalkyl or C6-10 alkylcycloalkyl group, or —[(—CH2—)p—X—]q—(—CH2—)r—, X denotes one selected from the group consisting of O, S and —NR6, R6 denotes H or methyl, m is a rational number from 0 to 10, n is an integer from 1 to 60, p is an integer from 2 to 6, q is an integeType: GrantFiled: May 25, 1999Date of Patent: May 15, 2001Assignee: PRC-DeSoto International, Inc.Inventors: Jonathan Doherty Zook, Suzanna Gibson DeMoss, David Weldon Jordan, Chandra B. Rao
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Patent number: 6172179Abstract: A polythioether includes a structure having the formula I —R1—[—S—(CH2)2—O—[—R2—O—]m—(CH2)2—S—R1—]n— I wherein R1 denotes a C2-6 n-alkylene, C3-6 branched alkylene, C6-8cycloalkylene or C6-10 alkylcycloalkylene group, —[(—CH2—)p—X—]q—(—CH2—)r—, or —[(—CH2—)p—X—]q—(—CH2—)r— in which at least one —CH2— unit is substituted with a methyl group, R2 denotes a C2-6 n-alkylene, C2-6 branched alkylene, C6-8 cycloalkylene or C6-10 alkylcycloalkylene group, or —[(—CH2—)p—X—]q—(—CH2—)r—, X denotes one selected from the group consisting of O, S and —NR6, R6 denotes H or methyl, m is a rational number from 0 to 10, n is an integer from 1 to 60, p is an integer from 2 to 6, q is an integer fromType: GrantFiled: September 12, 1997Date of Patent: January 9, 2001Assignee: PRC-Desoto International, Inc.Inventors: Jonathan Doherty Zook, Suzanna DeMoss, David Weldon Jordan, Chandra B. Rao
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Patent number: 6130334Abstract: The invention encompasses a process for making compounds of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases.Type: GrantFiled: April 15, 1998Date of Patent: October 10, 2000Assignee: Merck & Co., Inc.Inventors: Philip J. Pye, Ashok Maliakal, Kai Rossen, Ralph P. Volante, Jess Sager
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Patent number: 6111143Abstract: This invention relates to a sulfonium salt, including its manufacturing method, which is effectively used as a photoacid initiator or radical photoinitiator during polymerization and a photoacid generator, leaving the protection groups of organic compounds, especially as an useful photoacid generator of the chemically amplified photoresist employed in semiconductor materials. Since the sulfonium salt of this invention, so prepared via one-step reaction between sulfoxide compound and aromatic compound in the presence of perfluoroalkanesulfonic anhydride, has the advantages in that by overcoming some shortcomings of the prior art to prepare the sulfonium salt via two steps using Grinard reagent, this invention may provide a novel sulfonium salt with higher yield which cannot be achieved in the prior art and also to prepare even any conventional sulfonium salt having better yield.Type: GrantFiled: August 27, 1998Date of Patent: August 29, 2000Assignee: Korea Kumbo Petrochemical Co., Ltd.Inventors: Joo-Hyeon Park, Dong-Chul Seo, Sun-Yi Park, Seong-Ju Kim
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Patent number: 6040274Abstract: 2- Aroylcyclohexanediones I ##STR1## where X, Y=O or S;Ar=phenyl or heteroaryl in each case having 1-4 substituents: halogen, cyano, nitro, --N.dbd.N--Ph, C.sub.1 -C.sub.4 -alkoxycarbonyl, --N(R.sup.9)--COR.sup.10, --N(R.sup.9)--SO.sub.2 --R.sup.11, --SO.sub.2 --N(R.sup.9)R.sup.10, --S(O).sub.m --R.sup.8 or opt. subst. C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -haloalkoxy;two adjacent C atoms of the phenyl or heteroaryl ring can also be bridged by means of a chain --C(R.sup.12).dbd.C(R.sup.13)--C(R.sup.14).dbd.C(R.sup.15)--, --Z.sup.1 --C(R.sup.12).dbd.N--, --Z.sup.1 --N.dbd.C(R.sup.12)--, --Z.sub.1 --C(R.sup.12).dbd.C(R.sup.13)--, --Z.sup.1 --C(R.sup.12).dbd.C(R.sup.13)--C(R.sup.14,R.sup.15)--, --Z.sup.1 --C (R.sup.12,R.sup.13)--C(R.sup.14,R.sup.15)--, --Z.sup.1 --C(R.sup.12,R.sup.13)--C(R.sup.14 R.sup.15)--Z.sup.2 --, --C(R.sup.12,R.sup.13)--Z.sup.1 --C(R.sup.14,R.sup.15)--C(R.sup.16,R.sup.17)--, --Z.sup.1 --N(R.sup.20)--Z.sup.2 --, --Z.sup.1 --Z.sup.Type: GrantFiled: March 18, 1997Date of Patent: March 21, 2000Assignee: BASF AktiengesellschaftInventors: Jurgen Kast, Marcus Vossen, Wolfgang von Deyn, Stefan Engel, Regina Luise Hill, Uwe Kardorff, Martina Otten, Peter Plath, Helmut Walter, Karl-Otto Westphalen, Ulf Misslitz
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Patent number: 6013649Abstract: This invention is directed to proteinase (protease) inhibitors, and more particularly to thiol sulfone inhibitors for matrix metalloproteinase 13(MMP-13), compositions of proteinase inhibitors, intermediates for the syntheses of proteinase inhibitors, processes for the preparation of proteinase inhibitors and processes for treating pathological conditions associated with pathological matrix metalloproteinase activity related to MMP-13.Type: GrantFiled: July 22, 1997Date of Patent: January 11, 2000Assignee: Monsanto CompanyInventors: John N. Freskos, S. Zaheer Abbas, Gary A. DeCrescenzo, Daniel P. Getman, Robert M. Heintz, Brent V. Mischke, Joseph J. McDonald
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Patent number: 5994588Abstract: Disclosed are novel compounds which are used as linkers to bind peptides to solid support. The novel compounds can be used for the purification of synthesized peptides and are represented by the following structural formula:X--NH--(CH.sub.2).sub.n --SO.sub.2 --CH.sub.2 --CH.sub.2 --O--CO--Y;n is an integer from 1-4; X is a thiol functionalized with a protecting group that is cleavable under acidic conditions; and Y is a leaving group.Type: GrantFiled: June 2, 1995Date of Patent: November 30, 1999Assignee: Setsuko FunakoshiInventors: Susumu Funakoshi, Hiroyuki Fukuda
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Patent number: 5962730Abstract: Sulfonyl compounds have the formula ##STR1## where n is 0, 1 or 2,Y is vinyl or a radical of the formula C.sub.2 H.sub.4 Q, where Q is hydroxyl or an alkali-detachable group,E is C.sub.3 -C.sub.6 -alkylene with or without interruption by 1 or 2 oxygen atoms in ether function,Ar is the radical of benzene or naphthalene, andR.sup.1, R.sup.2 and R.sup.3 are each hydrogen, unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, hydroxyl, halogen, nitro, amino, hydroxysulfonyl, carboxyl, carbamoyl, sulfamoyl, cyano or a radical of the formula (NH--).sub.m (CH.sub.2 --).sub.q SO.sub.2 --Y, where m is 0 or 1, q is 0, 2 or 3, and Y is as defined above.Type: GrantFiled: January 9, 1998Date of Patent: October 5, 1999Assignee: BASF AktiengesellschaftInventors: Claus Marschner, Manfred Patsch
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Patent number: 5912319Abstract: A polythioether includes a structure having the formula I--R.sup.1 --?--S--(CH.sub.2).sub.2 --O--?--R.sup.2 --O--!.sub.m --(CH.sub.2).sub.2 --S--R.sup.1 --!.sub.n --whereinR.sup.1 denotes a divalent C.sub.2-6 n-alkyl, C.sub.3-6 branched alkyl, C.sub.6-8 cycloalkyl or C.sub.6-10 alkylcycloalkyl group, --?(--CH.sub.2 --).sub.p --X--!.sub.q --(--CH.sub.2 --).sub.r --, or --?(--CH.sub.2 --).sub.p --X--!.sub.q --(--CH.sub.2 --).sub.r -- in which at least one --CH.sub.2 -- unit is substituted with a methyl group,R.sup.2 denotes methylene, a divalent C.sub.2-6 n-alkyl, C.sub.2-6 branched alkyl, C.sub.6-8 cycloalkyl or C.sub.6-10 alkylcycloalkyl group, --?(--CH.sub.2 --).sub.p --X--!.sub.q --(--CH.sub.2 --).sub.r --, or --?(--CH.sub.2 --).sub.p --X--!.sub.q --(--CH.sub.2 --).sub.r -- in which at least one --CH.sub.2 -- unit is substituted with a methyl group,X denotes one selected from the group consisting of O, S and --NR.sup.6,R.sup.Type: GrantFiled: February 19, 1997Date of Patent: June 15, 1999Assignee: Courtaulds Aerospace, Inc.Inventors: Jonathan Doherty Zook, Suzanna Gibson, David Weldon Jordan, Chandra B. Rao
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Patent number: 5843906Abstract: The present invention relates to a class of compounds represented by the Formula I ##STR1## or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the .alpha..sub.v .beta..sub.3 integrin.Type: GrantFiled: March 27, 1997Date of Patent: December 1, 1998Assignee: G. D. Searle & Co.Inventors: Nizal Chandrakumar, Michael Clare, Wendell Doubleday, Alan F. Gasiecki, Mark A. Russell
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Patent number: 5807814Abstract: Oil soluble compounds having the formula: ##STR1## wherein R and R.sup.1 are independently cyano, alkoxycarbonyl, aryloxycarbonyl, alkenyloxycarbonyl, alkylcarbonyl, arylcarbonyl, alkenylcarbonyl, alkylsulfonyl, arylsulfonyl, alkenylsulfonyl, substituted aminocarbonyl, alkylphosphoryl, arylphosphoryl, alkenylphosphoryl, aryl, or heterocyclics, or together form a carbocycle or heterocycle, and R.sup.2 and R.sup.3 are independently alkyl, alkenyl, hydroxyalkyl, sulfurized alkyl, alkoxycarbonylalkyl, arylalkyl, or borated hydroxyalkyl, with the proviso that R, R.sup.1, R.sup.2 and R.sup.3 together contain sufficient carbon atoms to render the compound oil soluble in an oil of lubricating viscosity. The compound are useful as wear protectants or extreme pressure agents to enhance wear protection or extreme pressure properties in lubricating oils and greases.Type: GrantFiled: July 5, 1996Date of Patent: September 15, 1998Assignee: Chevron Chemical CompanyInventor: Andrew W. Ho
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Patent number: 5739374Abstract: 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: GrantFiled: February 14, 1997Date of Patent: April 14, 1998Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5736579Abstract: 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: GrantFiled: November 18, 1994Date of Patent: April 7, 1998Assignee: G.D. Searle & Co.Inventors: David B. Reitz, Robert E. Manning, Horng-Chi Huang, Jinglin Li
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Patent number: 5672627Abstract: 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: GrantFiled: July 9, 1996Date of Patent: September 30, 1997Assignee: G.D. Searle & Co.Inventors: Horng-Chih Huang, David R. Reitz
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Patent number: 5672626Abstract: 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: GrantFiled: July 9, 1996Date of Patent: September 30, 1997Assignee: G. D. Searle & Co.Inventors: Horng-Chih Huang, David R. Reitz
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Patent number: 5618981Abstract: A process which can be used to produce an aromatic sulfide compound having the formula of (R.sub.4-n)(X.sub.n)(W)Ar--S--R' is provided. The process comprises contacting, in the presence of a surfactant, a halo-substituted aromatic compound in an aqueous solution with a salt of a mercaptan under conditions sufficient to produce the aromatic sulfide in which the halo-substituted aromatic compound and salt of mercaptan are each present in an amount effective to synthesize the aromatic sulfide wherein R is hydrogen or a hydrocarbyl radical, X is a hlogen, n is a number from 0 to 3, W is a substituent, Ar is an aromatic ring, and R' is a hydrocarbyl radical.Type: GrantFiled: May 19, 1995Date of Patent: April 8, 1997Assignee: Phillips Petroleum CompanyInventor: James E. Shaw
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Patent number: 5536703Abstract: The invention relates to novel thioether derivatives of substituted benzoyl bicycloalkane diones, their use as herbicides and agricultural compositions comprising the same.Type: GrantFiled: January 13, 1995Date of Patent: July 16, 1996Assignee: Sandoz Ltd.Inventor: Shy-Fuh Lee
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Patent number: 5525580Abstract: Compounds represented by general formula (I), herbicides or selective herbicides for paddy field containing said compounds as active ingredients, method of controlling growth of undesirable plants by applying the herbicides on places where control is desired. ##STR1## wherein A represents a --S(O)nR.sup.1 in which n is 0 or 2 and R.sup.1 represents a (substituted) lower alkyl; a cycloalkyl; a (substituted) benzyl; a (substituted) phenyl; or a --OR.sup.2 in which R.sup.2 represents a (substituted) phenyl;B represents a halogen, a nitro, a lower alkyl, or a lower alkylsulfonyl;D represents a hydrogen, a lower alkyl, a lower alkoxy, a lower alkoxymethyl, or a lower alkoxycarbonyl;E represents a halogen, a (substituted) lower alkoxy, a lower alkylthio, a (substituted) lower alkylsulfonyl, or a lower alkylsulfonyloxy.The herbicides of the present invention can prevent a wide variety of noxious weeds and further selectively prevent weeds on paddy field with considerably reduced phytotoxicities on rice plant.Type: GrantFiled: January 14, 1994Date of Patent: June 11, 1996Assignee: SDS Biotech K.K.Inventors: Kenichi Komatsubara, Tadashi Sato, Kenji Mikami, Yuji Yamada
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Patent number: 5462810Abstract: A magnetic recording medium comprises a nonmagnetic substrate and at least one ferromagnetic metal layer applied thereon and a protective layer formed on this metal layer and consisting of a compound which consists of an unfluorinated or partially fluorinated alkyl radical and a disulfide, hydroxyl or keto group.Type: GrantFiled: January 11, 1994Date of Patent: October 31, 1995Assignee: BASF Magnetics GmbHInventors: Harald Keller, Ulrich Jaeger, Helmut Steininger, Helmut Kopke, Klaus D. Schomann, Hans-Peter Schildberg
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Patent number: 5414135Abstract: 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: GrantFiled: November 16, 1993Date of Patent: May 9, 1995Assignee: Sterling Winthrop Inc.Inventors: Robert A. Snow, David L. Ladd
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Patent number: 5411973Abstract: 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: GrantFiled: May 18, 1993Date of Patent: May 2, 1995Assignee: Zeneca LimitedInventors: Keith Russell, James R. Empfield, Cyrus J. Ohnmacht, Keith H. Gibson
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Patent number: 5393790Abstract: 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: GrantFiled: February 10, 1994Date of Patent: February 28, 1995Assignee: G.D. Searle & Co.Inventors: David B. Reitz, Robert E. Manning, Horng-Chi Huang, Jinglin Li
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Patent number: 5382686Abstract: Nitrodiphenyl(thio) ethers in which the nitro group is in the ortho- or para-position with respect to the ether oxygen or ether sulphur can be prepared from halonitrobenzones in which the nitro group is in the ortho- or para-position with respect to the halogen and, alkali metal (thio)phenolates in liquid ammonia, the reaction being carried out under pressure and at a temperature from -30.degree. C. to +140.degree. C. and the ammonia being separated off after the reaction is completed.Type: GrantFiled: June 2, 1993Date of Patent: January 17, 1995Assignee: Bayer AktiengesellschaftInventors: Ferdinand Hagedorn, Helmut Fiege
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Patent number: 5354511Abstract: 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: GrantFiled: November 27, 1992Date of Patent: October 11, 1994Assignee: AlliedSignal Inc.Inventors: Chengjiu Wu, Jianhui Shan, Ajay Nahata
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Patent number: 5350878Abstract: This invention provides 1) novel reactive fluorinated compounds derived from a specified class of telomers or cotelomers of fluoroolefins; and 2) stable products and stable polymers thereof obtained by reaction or polycondensation of the novel reactive fluorinated compounds with specified classes of hydrogenated aliphatic, alicyclic, aromatic reactive compounds, telechelic oligomers and block polymers wherein said stable products and polymers contain hetero atoms such as oxygen, sulfur or nitrogen and are characterized by high thermal and chemical resistance.Type: GrantFiled: February 10, 1993Date of Patent: September 27, 1994Assignee: Dow Corning CorporationInventor: Gerardo Caporiccio
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Patent number: 5302757Abstract: A composition of matter including an onium salt and a method of forming images. The onium salt has a chromophore which absorbs ultraviolet radiation, an S, Se, As, N or P atom which is free of substituents exhibiting a higher energy occupied molecular orbital than the chromophore; an insulating group which links the chromophore to the S, Se, As, N or P atom of the salt and substantially prevents .pi. resonance from the chromophore through the S, Se, As, N or P atom; and an anion. The onium salt is capable of forming a Bronsted acid upon exposure to ultraviolet radiation in the presence of a proton source. In the method of forming images, the onium salt is exposed to ultraviolet radiation in the presence of a proton source, to convert said onium salt to a Bronsted acid.Type: GrantFiled: September 14, 1992Date of Patent: April 12, 1994Assignee: Eastman Kodak CompanyInventor: Franklin D. Saeva
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Patent number: 5225601Abstract: 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: GrantFiled: October 31, 1991Date of Patent: July 6, 1993Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5221750Abstract: 2-aryl-4-isoxazolin-3-1-derivatives of formula (I), useful as intermediates for positive working compounds in silver halide photographic materials ##STR1## wherein R.sup.1 represents a substituted or unsubstituted alkyl having from 1 to 6 carbon atoms or a substituted or unsubstituted aryl having from 6 to 24 carbon atoms; and R.sup.2, R.sup.3, and R.sup.4, are the same or different, each having up to 20 carbon atoms and each represents hydrogen, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted acyl, a substituted or unsubstituted alkoxycarbonyl, a substituted or unsubstituted aryloxycarbonyl, halogen, nitro, a substituted or unsubstituted carbamoyl, a substituted or unsubstituted sulfamoyl, a substituted or unsubstituted sulfonyl, cyano, or trifluoromethyl, with the proviso that at least one of said R.sup.2 and R.sup.3 is cyano, a substituted or unsubstituted sulfonyl, trifluoromethyl, or nitro.Type: GrantFiled: January 13, 1992Date of Patent: June 22, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Koki Nakamura, Shigeru Nakamura
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Patent number: 5214070Abstract: 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: GrantFiled: August 21, 1991Date of Patent: May 25, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Thomas G. C. Bird, Philip N. Edwards
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Patent number: 5210187Abstract: Double attachment reactive dyes have the formula ##STR1## where U.sup.1 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR2## where Q.sup.1 and Q.sup.2 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.3 is a group which is detachable under alkaline reaction conditions,Z is the radical ##STR3## where each Q.sup.4 is independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl which may be substituted by cyano, U.sup.2 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR4## where Q.sup.5 and Q.sup.6 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.7 is a group which is detachable under alkaline reaction conditions, and w is 0, 1 or 2,t is 0, 1 or 2,v is 1 or 2 and X and L are each as defined in the description, with the proviso that at least one of the two radicals U.sup.1 and U.sup.2 is not C.sub.1 -C.sub.Type: GrantFiled: April 9, 1992Date of Patent: May 11, 1993Assignee: BASF AktiengesellschaftInventors: Manfred Patsch, Uwe Nahr, Friedrich Wirsing, Joerg L. Jessen, Klaus Pandl, Claus Marschner, Matthias Dust
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Patent number: 5153227Abstract: The invention concerns novel pharmaceutical compositions for use in the treatment of certain complications of diabetes and galactosemia and which contain a nitromethane derivative (or its non-toxic salt) as active ingredient. The nitromethane derivatives are inhibitors of the enzyme aldose reductase. Many of the inhibitors are novel and are provided, together with processes for their manufacture and use, as further features of the invention.Type: GrantFiled: February 6, 1989Date of Patent: October 6, 1992Assignee: Imperial Chemical Industries PLCInventors: Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey J. Morris, John Preston
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Patent number: 5152826Abstract: 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: GrantFiled: October 16, 1991Date of Patent: October 6, 1992Assignee: Imperial Chemical Industries PLCInventor: Christopher G. Knudsen
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Patent number: 5149857Abstract: A process for producing sulfonium compounds represented by the general formula (III) which comprises reacting alkylthiophenol derivatives represented by the general formula (I) and dialkyl sulfate represented by the general formula (II).General Formula (I): ##STR1## General Formula (II): (R.sup.2).sub.2 SO.sub.Type: GrantFiled: May 29, 1990Date of Patent: September 22, 1992Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Mutsuhiko Takeda, Isao Hagiwara, Fumiya Zaima, Shuzabu Sakaguchi
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Patent number: 5145996Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl mercapto-alcohols of the formulas I and IIHS--[CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 ]--OH (I)HS--[CH.sub.2 C(CH.sub.2 X.sub.1 --R.sub.f).sub.2 CH.sub.2 ]--OH (II)are prepared from the corresponding perfluorinated neopentyl oxetans where R.sub.f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is a linking group, and X and X.sub.1 are heteroatom moieties.The reaction products of these fluorinated mercapto-alcohols with electrophiles are disclosed as are certain functional derivatives. Compositions containing such materials provide improved thermal stability and useful low surface energy oil and water repellent coatings for textiles, glass, paper, leather, and other materials.Type: GrantFiled: February 25, 1991Date of Patent: September 8, 1992Assignee: Ciba-Geigy CorporationInventors: Michael Jacobson, Kirtland P. Clark
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Patent number: 5132462Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- to 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.Type: GrantFiled: March 7, 1991Date of Patent: July 21, 1992Assignee: Ciba-Geigy CorporationInventor: Hans Tobler
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Patent number: 5132463Abstract: 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: GrantFiled: June 12, 1991Date of Patent: July 21, 1992Assignee: 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
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Patent number: 5132423Abstract: 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: GrantFiled: March 13, 1991Date of Patent: July 21, 1992Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Deborah A. Haitko, James P. Barren, Sunita Singh
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Patent number: 5116869Abstract: 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: GrantFiled: September 3, 1991Date of Patent: May 26, 1992Assignee: Teijin LimitedInventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
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Patent number: 5110343Abstract: The invention relates to a herbicidal composition having an inert carrier and an effective amount of a compound having the formula ##STR1## wherein X is the same or different substituent selected from the group consisting of halogen, nitro, C.sub.1-6 alkyl, halo C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio and C.sub.1-6 alkylsulfonyl;n is 1, 2, 3 or 4;R.sup.1 is C.sub.1-6 alkyl which is substituted by cyano, halogen, hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulfonyl or tetrahydropyranyloxy; C.sub.1-6 alkylthio, phenylthio, pyridyl or tetrahydropyranyl;R.sup.2 is C.sub.1-6 alkyl;l is 0, 1 or 2.Type: GrantFiled: May 24, 1990Date of Patent: May 5, 1992Assignee: Nippon Soda Co., Ltd.Inventors: Akiyoshi Ueda, Haruhito Ohishi, Toshio Aihara, Hisao Ishikawa, Kazuyuki Tomida, Hideo Hosaka
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Patent number: 5100460Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.Type: GrantFiled: July 13, 1989Date of Patent: March 31, 1992Assignee: Rhone-Poulenc AgrochimieInventors: Philippe Desbordes, Michel Euvrard
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Patent number: 5097068Abstract: Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexandediones. The intermediate benzoic acids of this invention have the following structural formula ##STR1## wherein R.sup.6 is chlorine, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or hydroxy; n is the integer 0 or 2; and R.sup.7 is C.sub.1 -C.sub.4 alkyl.Type: GrantFiled: December 7, 1989Date of Patent: March 17, 1992Assignee: ICI Americas, Inc.Inventor: David L. Lee
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Patent number: 5084478Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl;wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent or each is hydrogen or alkyl, alkoxy or dialkylamino, provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkylwherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --;and wherein R.sup.9 is alkyl of up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.Type: GrantFiled: April 14, 1989Date of Patent: January 28, 1992Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, Howard Tucker
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Patent number: 5047420Abstract: 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 mediate 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: GrantFiled: August 21, 1989Date of Patent: September 10, 1991Assignee: Merck & Co., Inc.Inventors: Donald W. Graham, Tesfaye Biftu, John C. Chabala, Michael N. Chang, Yuan-Ching P. Chiang, Kathryn L. Thompson, Shu S. Yang
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Patent number: 5041600Abstract: Arylcyclobutenealkyl diethers of oligomers containing a plurality of aromatic rings at least two of which are joined by a sulfone moiety, are self-curing at temperatures above about 150.degree. C. The cured products exhibit good properties of strength and toughness.Type: GrantFiled: January 29, 1990Date of Patent: August 20, 1991Assignee: Shell Oil CompanyInventor: Pui K. Wong
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Patent number: 5015775Abstract: Alkyl aryl sulfones of the formula R--SO.sub.2 --AR--Y.sub.n, wherein Ar is an aryl compound, Y is a substituent on the aryl compound and R is alkyl or cycloalkyl, and liquid mixtures of positional isomers of the same are prepared by reacting an aryl compound of the formula Ar--Y.sub.n, with an alkyl sulfonic acid of the formula R--SO.sub.3 H and a phosphorus reagent, preferably under heat. Particularly good yields and pure products are obtained using phosphorus pentoxide. Alkyl aryl sulfones produced by this method are a liquid mixture preferably containing at least two positional isomers, wherein no isomer is present in an amount of more than about 50% of the isomer mixture.Type: GrantFiled: March 31, 1988Date of Patent: May 14, 1991Assignee: Atochem North America, Inc.Inventors: James L. Reilly, Gordon R. Leader
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Patent number: 5011931Abstract: A process to prepare compounds of formula I ##STR1## in which n=0, 1 or 2 comprising the cyclisation of compounds of formula II ##STR2## in which n=0, 1 or 2. The cyclisation may be effected in the presence of an organic or inorganic base or thermally at a temperature in the range 40.degree.-160.degree. C.Compounds of formula II and certain analogues thereof are disclosed as cardiovascular agents.Type: GrantFiled: June 23, 1989Date of Patent: April 30, 1991Assignee: The Boots Company PLCInventors: Lachlan MacLean, David L. Roberts, Kenneth Barron, Kenneth J. Nichol, Albert E. Harrison
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Patent number: 5004841Abstract: Aromatic compounds, such as benzene or biphenyl, are alkylated with an alkylating agent having from one to eight carbons atoms, such as propylene, in the presence of an acidic mordenite zeolite catalyst under conditions sufficient to produce a mixture of substituted aromatic compounds enriched in the linear alkylated isomers, such as p-diisopropylbenzene or p,p'-di(isopropyl)biphenyl, respectively. The novel acidic mordenite catalyst is characterized by its silica/alumina molar ratio, its porosity, and a Symmetry Index. The p,p'-disubstituted isomers of aromatic compounds are useful as monomers in the preparation of thermotropic, liquid crystal polymers.Type: GrantFiled: March 14, 1989Date of Patent: April 2, 1991Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Joseph J. Maj, Stephen C. Rocke
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Patent number: 4990677Abstract: Fungicidal and plant growth-regulating azolylmethylcyclopropyl derivatives of the formula ##STR1## in which R represents halogen, alkyl or optionally substituted phenyhl, or represents the groupings --Y--R.sup.2,whereinY represents oxygen, sulphur, SO or SO.sub.2 andR.sup.2 represents optionally substituted phenyl,R.sup.1 represents hydrogen, alkyl or acyl,X represents nitrogen or a CH group,Z represents halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 or 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy with 1 or 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio with 1 or 2 carbon atoms and 1 to 5 halogen atoms or phenyl which is optionally substituted by alkyl with 1 or 2 carbon atoms and/or halogen, or represents phenoxy which is optionally substituted by alkyl with 1 or 2 carbon atoms and/or halogen andm represents the number 0, 1, 2 or 3, and addition products thereof with acids and metal salts.Type: GrantFiled: February 12, 1990Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Klaus Stroech, Wilhelm Brandes, Stefan Dutzmann
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Patent number: 4980510Abstract: Thiophenols of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of each other each stand for hydrogen, halogen, nitro, alkyl, alkoxy, alkylthio, alkoxyalkyl, alkylthioalkyl, haloalkyl, haloalkoxy or alkylcarboxyl, optionally substituted aryl or optionally substituted hetaryl,R.sup.5 stands for alkyl, alkoxyalkyl, alkylthioalkyl, haloalkyl, alkenyl, haloalkenyl, optionally substituted aryl or optionally substituted hetaryl, andX stands for carbonyl, sulphinyl or sulphonyl can be obtained by reacting halobenzenes of the formula ##STR2## in which Hal stands for halogen, first with sodium hydrogen sulphide or sodium sulphide in the presence of a diluent to form compounds of the formula ##STR3## and then adding an acid to form the thiophenol, some of the thiophenols are novel and all can be used to form aryethioaminopyridides which are employed as herbicides.Type: GrantFiled: July 14, 1988Date of Patent: December 25, 1990Assignee: Bayer AktiengesellschaftInventors: Hermann Hagemann, Klaus Sasse, Reiner Fischer