Chalcogen Bonded Directly To The 2- And 5- Positions Of The Thiadiazole Ring Patents (Class 548/142)
  • Patent number: 5414090
    Abstract: An adduct of 2,5-dimercapto-1,2,4 -thiadiazole, an epoxide, a formaldehyde and 4,4'-isopropylidenediphenol represented by the formula ##STR1## where A is H or ##STR2## where R is H or a (C.sub.1 -C.sub.30) alkyl group and n=1-4.
    Type: Grant
    Filed: November 2, 1993
    Date of Patent: May 9, 1995
    Assignee: Texaco Inc.
    Inventors: Doris Love, Julian H. Dancy, Jayne M. Lucas
  • Patent number: 5409944
    Abstract: Disclosed are compounds of Formula I useful in the treatment of cyclooxygenase mediated diseases such as pain, fever and inflammation of a variety of conditions including rheumatic fever, symptoms associated with influenza or other viral infections, common cold, low back and neck pain, dysmenorrhea, headache, toothache, sprains and strains, myositis, neuralgia, synovitis, arthritis, including rheumatoid arthritis degenerative joint diseases (osteoarthritis), gout and ankylosing spondylitis, bursitis, burns, injuries.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: April 25, 1995
    Assignee: Merck Frosst Canada, Inc.
    Inventors: W. Cameron Black, Chun-Sing Li, Daniel Guay, Petpiboon Prasit, Patrick Roy
  • Patent number: 5362880
    Abstract: Disclosed is a method of preparing a photographic coupler comprised of 1-aryl-3-substituted-4-heterocyclic-5-pyrazolone development inhibitor releasing coupler for use in a photographic element, said coupler capable of reacting with oxidized color developer to release a heterocyclic coupling-off group containing an inhibitor.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: November 8, 1994
    Assignee: Eastman Kodak Company
    Inventor: William J. Begley
  • Patent number: 5334603
    Abstract: A compound is prepared which corresponds to the formula: ##STR1## This compound has been found to exhibit antimicrobial activity in industrial and commercial applications and compositions containing this compound are so employed.
    Type: Grant
    Filed: November 16, 1993
    Date of Patent: August 2, 1994
    Assignee: The Dow Chemical Company
    Inventors: Ravi B. Shankar, R. Garth Pews, Duane R. Romer
  • Patent number: 5332757
    Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;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 or a heteroaryl diradical;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 (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: February 8, 1993
    Date of Patent: July 26, 1994
    Assignees: Zeneca Limited, Zeneca PHARMA S A
    Inventors: Thomas G. C. Bird, Patrick Ple
  • Patent number: 5326776
    Abstract: Compounds are disclosed having the formula: ##STR1## wherein the substituents are defined herein. The compounds of the invention are angiotensin II receptor antagonists.
    Type: Grant
    Filed: February 24, 1993
    Date of Patent: July 5, 1994
    Assignee: Abbott Laboratories
    Inventors: Martin Winn, Biswanath De, Thomas M. Zydowsky, Daniel J. Kerkman, John F. DeBernardis, Saul H. Rosenberg, Kazumi Shiosaki, Fatima Z. Basha, Kenneth P. Spina, Thomas W. von Geldern, Steven Boyd, Diane M. Yamamoto, Anthony K. L. Fung
  • Patent number: 5294709
    Abstract: Methine compounds represented by the following general formula (Ia) or (Ib); ##STR1## wherein CYA represents atoms having a cyanine chromogen structure, MER represents atoms having a merocyanine chromogen structure, L represents a divalent linkage group composed of an atom or atoms containing at least one of a carbon atom, a nitrogen atom, a sulfur atom and an oxygen atom, Het represents a group containing a 5- to 7-membered hetero ring containing at least one nitrogen atom, l.sub.1 represents 1 or 2, l.sub.2 represents 0 or 1, and l.sub.3 represents 1, 2 or 3. Methine dyes using same are also disclosed.
    Type: Grant
    Filed: January 14, 1993
    Date of Patent: March 15, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshinao Ukai, Yoshio Inagaki
  • Patent number: 5276037
    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: April 14, 1993
    Date of Patent: January 4, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
  • Patent number: 5274102
    Abstract: Epoxy functional copolymers of a higher .alpha.-olefin, and an unsaturated dicarboxylic acid ester formed by copolymerization of olefin, acid ester and ethylenically unsaturated glycidyl compound can be used to form nitrogen, oxygen, phosphorus and/or sulfur-containing lubricant additives by reaction of the epoxy functionality in such a copolymer with glycidyl-reactive compounds containing nitrogen, oxygen, phosphorus and/or sulfur atoms. Alternatively, the copolymerization reaction can utilize the olefin, unsaturated acid ester, and an ethylenically unsaturated compound containing the nitrogen, phosphorus and/or sulfur atom, which compound is formed by reaction of ethylenically unsaturated glycidyl compound and an epoxy-reactive nitrogen, phosphorus, and/or sulfur-containing compound.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: December 28, 1993
    Assignee: Akzo nv
    Inventors: Theodore A. Marolewski, Eric W. Burkhardt, Uwe H. Wallfahrer
  • Patent number: 5236939
    Abstract: Substituted 1,3,4 -oxa- diazolinones of the formula (I) ##STR1## in which X represents O andY represents O or S,are disclosed as useful to combat endoparasites.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: August 17, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Bonse, Nikolaus Muller, Achim Harder
  • Patent number: 5223616
    Abstract: A heterocyclic compound which is useful for dyeing or printing hydrophobic fiber materials and which has the following formula (I), ##STR1##wherein A.sub.1, A.sub.2, A.sub.3 and A.sub.4 are each hydrogen, halogen, alkyl, alkoxy or alkenyl, X.sub.1 is --O-- or the like, R.sub.1 is a methylene or the like, X.sub.2 is a direct linkage or a divalent group of --O--, --S--, --SO--, --SO.sub.2 --, ##STR2## in which R.sub.3 is a hydrogen atom or a C.sub.1-4 alkyl group, ##STR3## in which R.sub.3 is as defined above, T and u are each independently hydrogen or a C.sub.1-4 alkyl, l is O or an integer of 1 to 3, Q is an unsubstituted or substituted 5-, 6- or 7-membered saturated or unsaturated heterocyclic residue, Y is hydrogen, C.sub.1-4 alkyl, a C.sub.1-4 alkoxy group or the like.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: June 29, 1993
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Jun Yamamoto, Junichi Sekihachi, Yosuke Yamamoto, Kazuhiro Machiguchi, Yutaka Kayane
  • Patent number: 5213709
    Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 and R.sub.2 respectively denote an alkyl group having 1-16 carbon atoms optionally substituted; X.sub.1 and X.sub.3 respectively denote a single bond, --O--, ##STR2## X.sub.2 denotes a single bond, ##STR3## A.sub.1 denotes a single bond ##STR4## A.sub.3 denotes ##STR5## A.sub.2 denotes 9, 10-dihydro-2,7-phenanthrenediyl, 2,7-fluorenediyl or 2,7-fluorenonediyl; n is 0 or 1; and X.sub.4 and X.sub.5 respectively denote hydrogen, F, Cl, Br, --CH.sub.3, --CN or --CF.sub.3, with proviso that X.sub.1 is a single bond when A.sub.1 is a single bond.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: May 25, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shinichi Nakamura
  • Patent number: 5200109
    Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 and R.sub.2 respectively denote a linear or branched alkyl group having 1-18 carbon atoms capable of including one or non-neighboring two or more methylene groups which can be replaced with at least one species of --O--, --S--, --CO--, --COO--, --OCO-- and --OCOO--; ##STR2## and n is 0 or 1.
    Type: Grant
    Filed: January 15, 1992
    Date of Patent: April 6, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takashi Iwaki, Takao Takiguchi, Shinichi Nakamura, Yoko Yamada, Takeshi Togano, Shosei Mori
  • Patent number: 5194446
    Abstract: Methods of treating chronic arthritis and osteoporosis which utilize both known and novel compounds which would fall under the general formula:(HO)p--A--[--OS(O).sub.2 NR.sup.1 R.sup.2 ].sub.zwherein A encompasses a wide range of values including but not limited to aryl, loweralkyl, cycloalkyl, and carbohydrates including sucrose and fructose; p is equal to the number of unreacted hydroxy groups contained on the molecule and may be zero; z is the number of --OS(O).sub.2 NR.sup.1 R.sup.2 groups and is always at least one; R.sup.1 and R.sup.2 are selected from hydrogen, loweralkyl, carboxy and the like; a novel process for preparing the compounds is provided wherein an appropriate sulfamic acid aryl ester is reacted with a hydroxy substituted A radical which may or may not contain thereon protected carboxyl, amino or hydroxy substituents, in an aprotic solvent containing a tertiary amine base. Pharmaceutical compositions for the treatment of chronic arthritis and osteoporosis are also provided.
    Type: Grant
    Filed: July 24, 1991
    Date of Patent: March 16, 1993
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Young S. Lo, Joseph C. Nolan, William J. Welstead, Jr., David A. Walsh, Dwight A. Shamblee, Ibrahim M. Uwaydah
  • Patent number: 5194621
    Abstract: Disclosed are novel compounds prepared by reacting mono- or disulfide dimers of 2,5-dimercapto-1,3,4-thiadiazole with an aliphatic or aromatic alcohol and aldehyde. The compounds are effective antiwear agents and antioxidants when incorporated into lubricating compositions.
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: March 16, 1993
    Assignee: R. T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Robert J. Luo
  • Patent number: 5188746
    Abstract: The invention relates to zinc and phosphorus free additives for lubricating compositions which are produced by a free radical reaction between a dimercaptothiadiazole and monomer oligomer or homologue of acrylates or methacrylate, which in minor amounts impart antiwear/extreme pressure and antioxidation properties to the lubricant.
    Type: Grant
    Filed: November 1, 1990
    Date of Patent: February 23, 1993
    Assignee: Mobil Oil Corporation
    Inventor: Robert H. Davis
  • Patent number: 5186850
    Abstract: The incorporation of the heterocyclic dimercaptothiadiazole functionality into the alkenylsuccinimide dispersant structures via the Mannich alkylaminomethylkation procedure provides a class of ashless non-phosphorus dispersants with multifunctional antiwear, antioxidant and corrosion inhibitor properties in lubricant compositions.
    Type: Grant
    Filed: July 9, 1992
    Date of Patent: February 16, 1993
    Assignee: Mobil Oil Corporation
    Inventors: Abraham O. M. Okorodudu, Angeline B. Cardis, Ross A. Kremer
  • Patent number: 5177212
    Abstract: Disclosed are novel compounds prepared by reacting 2,5-dimercapto-1,3,4-thiadiazole, aliphatic or aromatic aldehyde and alkylated phenol in the molar ratio of 1:1:1 to 2:2:1. The 2,5-dimercapto-1,3,4-thiadiazole may be substituted in the 2-position by terpene, polymeric and succinate residues. The compounds are effective antiwear agents and antioxidants when incorporated into lubricating compositions.
    Type: Grant
    Filed: July 26, 1991
    Date of Patent: January 5, 1993
    Assignee: R.T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Steven G. Donnelly
  • Patent number: 5177213
    Abstract: Disclosed are novel succinic acid derivatives of 2(and 5)-2-hydroxyethylthio)-1,3,4-thiadiazole. These compounds are shown to be effective multifunctional additives for improving the anticorrosion and performance characteristics of lubricants and alcohol-based fuels.
    Type: Grant
    Filed: July 20, 1989
    Date of Patent: January 5, 1993
    Assignee: R. T. Vanderbilt Company, Inc.
    Inventor: Thomas J. Karol
  • Patent number: 5171861
    Abstract: Dimercaptothiadiazole reacted with arylsulfonic acids preformed or formed in situ in lubricants provide multifunctional antioxidant, antiwear, and corrosion inhibiting properties thereto.
    Type: Grant
    Filed: October 29, 1990
    Date of Patent: December 15, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Robert E. Ernhoffer, Arjun K. Goyal, Andrew G. Horodysky, Derek A. Law, Shi-Ming Wu
  • Patent number: 5152909
    Abstract: A railway diesel crankcase lubricant composition comprising a major portion of a diesel lubricating oil and a minor amount of, as an oxidation and corrosion inhibiting additive, a condensate product prepared by the process comprising:(a) reacting a dibasic acid anhydride with an oligomeric isobutylene to form a succinic anhydride;(b) reacting the succinic anhydride with an N-alkyl alkylene diamine to produce a succinimide-amine;(c) reacting the succinimide-amine with a polyaromatic diisocyanate to produce a phenylurea isocyanophenylmethane;(d) reacting the isocyanophenylmethane with a heterocyclic compound containing a thiadiazole nucleus to a condensation product of a mercaptothiadiazole-phenylmethane; and(e) recovering the condensation product.
    Type: Grant
    Filed: April 22, 1991
    Date of Patent: October 6, 1992
    Assignee: Texaco Inc.
    Inventors: Thomas F. DeRosa, Rodney L. Sung, Benjamin J. Kaufman
  • Patent number: 5137649
    Abstract: Mixed alcohol/dimercaptothiadiazole-derived hydroxy borates have been found to be effective antiwear/antioxidant multifunctional additives for lubricants.
    Type: Grant
    Filed: March 6, 1990
    Date of Patent: August 11, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Liehpao O. Farng, Andrew G. Horodysky, William F. Olszewski
  • Patent number: 5138065
    Abstract: Disclosed are novel compounds prepared by reacting molar equivalents of polyether glycol with maleic anhydride and then reacting the intermediate with 2,5-dimercapto-1,3,4-thiadiazole. The compounds are dispersants or detergents, antiwear agents and antioxidants when incorporated into lubricating compositions.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: August 11, 1992
    Assignee: R. T. Vanderbilt Company, Inc.
    Inventor: Thomas J. Karol
  • Patent number: 5126397
    Abstract: Quaternary ammonium salt derived thiadiazoles provide multifunctional antioxidant/antiwear characteristics to lubricants when incorporated therein.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: June 30, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Andrew G. Horodysky, Shih-Ying Hsu
  • Patent number: 5116853
    Abstract: Novel phenylene derivatives shown by the general formula ##STR1## wherein A represents a hydrogen atom, a phenyl group or a phenoxy group, n represents an integer of 3 to 10, R.sub.1 represents a hydrogen atom or a lower alkoxy group, X.sub.1 represents --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CONH--, B represents ##STR2## (wherein R.sub.2 represents a hydrogen atom, a halogen, atom, a nitro group, etc.), ##STR3## (wherein R.sub.3 represents a hydrogen atom, a hydroxyl group or a lower alkoxy group), X.sub.2 represents --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, etc. and D represents a carboxy group, a lower alkoxycarbonyl group or ##STR4## which are useful as drugs, particularly SRS-A (slow reacting substance of anaphylaxis) antagonist, i.e. they are useful as prophylaxis and treatment for various allergic diseases (e.g. bronchial asthma, allergic rhinitis, urticaria) or, ischemic heart diseases, inflammation, etc. induced by SRS-A.
    Type: Grant
    Filed: September 27, 1989
    Date of Patent: May 26, 1992
    Inventors: Toshiyasu Mase, Kiyoshi Murase, Hiromu Hara, Kenichi Tomioka
  • Patent number: 5110491
    Abstract: A railway diesel crankcase lubricant composition comprising a major portion of a diesel lubricating oil and a minor amount of, as an oxidation and corrosion inhibiting agent, a condensate product prepared by the process comprising:(a) reacting a dibasic acid anhydride, separately, with:(i) a oligomeric isobutylene, and(ii) 2,5-dimercapto-1,3,4,-thiadiazole, to produce, respectively, oligomeric(isobutylene-g-succinic anhydride) and 2-thio-(5-mercapto-1,3,4-thiadiazole) succinic anhydride;(b) reacting both of the succinic anhydrides with pentamethylenediamine to produce the [2-thio-(5-mercapto-1,3,4-thiadiazole)]-[oligomeric(isobutylene-g-succinic )]-pentamethylenetetraamine-bis succinimide product; and(c) recovering the bis-succinimide product.
    Type: Grant
    Filed: April 22, 1991
    Date of Patent: May 5, 1992
    Assignee: Texaco Inc.
    Inventors: Thomas F. Derosa, Rodney L. Sung, Benjamin J. Kaufman, Ronald L. O'Rourke
  • Patent number: 5102568
    Abstract: Novel thiadiazole compounds of the formula[Z--S--Q--S].sub.x Mwhere: Q is a bivalent thiadiazole ring; Z is a succinate group; M is hydrogen, a metal ion selected from the Periodic Table Groups IA, IIA, IIIA, IB, IIB, IIIB, IVB, VB, and VIB, a (MoO.sub.2).sup.+2 radical, or an amine salt; and X is a whole number equal to the valence of M are used as lubricant additives for providing antiwear and antioxidant properties to lubricant compositions.
    Type: Grant
    Filed: February 5, 1988
    Date of Patent: April 7, 1992
    Assignee: ATOCHEM North America, Inc.
    Inventors: James P. King, Billy L. Hill
  • Patent number: 5102897
    Abstract: The novel 3,5-ditertiarybutyl-4-hydroxyphenylthio-1,3,4-thiadiazoles and oxadiazoles and 3,5-ditertiarybutyl-4-hydroxyphenylmethanone-1,3,4-thiadiazoles and oxadiazoles and related compounds of the present invention are antiinflammatory agents having activity as inhibitors of 5-lipoxygenase, cyclooxygenase or both.
    Type: Grant
    Filed: January 24, 1991
    Date of Patent: April 7, 1992
    Assignee: Warner-Lambert Company
    Inventors: Diane H. Boschelli, David T. Connor, Catherine R. Kostlan, James B. Kramer, Michael D. Mullican, Jagadish C. Sircar
  • Patent number: 5103007
    Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5095024
    Abstract: Substituted 1,3,4-thiadiazolinones of the formula (I), ##STR1## in which X represents O or S,R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, halogenoalkyl, halogenoalkoxy or halogenoalkylthio,R.sup.2 represents one or more identical or different radicals from the series comprising hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy and arylthio, each of which can, in turn, be substituted as well, andR.sup.3 represents alkyl, alkenyl or alkynyl, each of which can optionally be substituted,with the exception of the compound 5-methylmercapto-3-phenyl-1,3,4-thiadiazol-2-(3H)-one, are disclosed as being useful to combat endoparasites. Compositions containing these compounds, process for preparing them, and novel intermediates are also disclosed.
    Type: Grant
    Filed: September 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Nikolaus Muller, Gerhard Bonse, Werner Lindner, Achim Harder
  • Patent number: 5093343
    Abstract: Substituted 1,3,4-oxa- and thiadiazolinones of the formula (I) ##STR1## in which R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, halogenoalkyl, halogenoalkoxy or halogenoalkylthio,R.sup.2 represents one or more identical or different radicals from among hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be sutstituted,R.sup.3 represents one or more identical or different radicals from among hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.
    Type: Grant
    Filed: September 5, 1990
    Date of Patent: March 3, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Bonse, Nikolaus Muller, Achim Harder
  • Patent number: 5081245
    Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5076961
    Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sup.1 and R.sup.2 respectively denote a linear or branched alkyl group having 1-18 carbon atoms capable of including one or two or more non-neighboring methylene groups which can be replaced with at least one species of --Z--, ##STR2## --CH.dbd.CH-- and --C.tbd.C--, wherein Z denotes --O-- or --S-- and R.sup.3 denotes hydrogen or an alkyl group having 1-5 carbon atoms; A.sup.1 denotes ##STR3## and A.sup.2 denotes any one of ##STR4## The mesomorphic compound is effective for providing a ferroelectric liquid crystal composition showing an improved low-temperature operation characteristic and a decreased temperature-dependence of response speed.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: December 31, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventors: Shinichi Nakamura, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shosei Mori
  • Patent number: 5062863
    Abstract: A diesel fuel composition comprising a major portion of middle distillates and a minor wear improving amount of a 1,3,4-thiadiazole derived from 2,5-dimercapto-1,3,4-thiadiazole and one or two moles of polyolefin having 50 to 400 carbon atoms. Furthermore, the 5-position of the 2-mercapto-1,3,4-thiadiazole may be substituted by alkylthio, 2-hydroxyalkylthio, amino or hydroxy group. The 1,3,4-thiadiazole compounds are also effective dispersants when incorporated into fuel compositions.
    Type: Grant
    Filed: May 17, 1990
    Date of Patent: November 5, 1991
    Assignee: R. T. Vanderbilt Company, Inc.
    Inventor: Thomas J. Karol
  • Patent number: 5055584
    Abstract: Disclosed are reaction products of a maleic compound and 2,5-dimercapto-1,3,4-thiadiazole. The reaction products are useful as antiwear agents and antioxidants in lubricating compositions.
    Type: Grant
    Filed: May 4, 1987
    Date of Patent: October 8, 1991
    Inventor: Thomas J. Karol
  • Patent number: 5026865
    Abstract: Disclosed are novel reaction products of 2,5-dimercapto-1,3,4-thiadiazole and epoxy compounds. These compounds are shown to be effective antiwear agents and antioxidants in lubricating compositions.
    Type: Grant
    Filed: June 3, 1987
    Date of Patent: June 25, 1991
    Assignee: R. T. Vanderbilt Company, Inc.
    Inventor: Thomas J. Karol
  • Patent number: 4992456
    Abstract: Fungicidal 2,5-disubstituted 1,3,4-thiadiazoles of the formula ##STR1## in which R.sup.1 represents alkyl or unsubstituted or substituted aralkyl andR.sup.2 represents in each case unsubstituted or substituted aryl or aralkyl, or represents an unsubstituted or substituted and optionally benzo-fused heterocyclic radical,excluding the compound 2,5-bis[(phenylmethyl)-sulphonyl]-1,3,4-thiadiazole.
    Type: Grant
    Filed: November 1, 1989
    Date of Patent: February 12, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Diehr, Albrecht Marhold, Wilhelm Brandes, Gerd Hanssler
  • Patent number: 4990273
    Abstract: An extreme pressure, anti-wear additive for lubricating compositions which is the reaction product of a 2,5-dimercapto-1,3,4-thiadiazole, an aldehyde and a primary or secondary, aliphatic or alicyclic amine.
    Type: Grant
    Filed: November 20, 1987
    Date of Patent: February 5, 1991
    Assignee: Union Oil Company of California
    Inventor: Michael C. Croudace
  • Patent number: 4952580
    Abstract: Polyhaloalkene compounds of the formula: ##STR1## wherein X is sulfur, oxygen, or nitrogen, Y.sup.1 and Y.sup.2 are fluorine, Z is hydrogen or the same as Y.sup.1 and Y.sup.2, and n is 1-4; provided that:(A) when X is sulfur, Z is fluorine and R is thienyl or substituted thienyl, thianaphthyl or substituted thianaphthyl, thiazolinyl or substituted thiazolinyl, oxadiazolyl or substituted oxadiazolyl, 3,4,4-trifluoro-3-butenyloxycarbonylmethyl, thiadiazolyl substituted by halogen or R.sup.2 S, wherein R.sup.2 is 3,4,4-trifluoro-3-butenyl or R.sup.2 is phenylmethyl or phenylthiomethyl each optionally substituted by halogen or nitro; or R is thiadiazolyl substituted by R.sup.3, wherein R.sup.3 is substituted aryl, arylalkyl, aryloxyalkyl, alkylthio, haloalkylthio, haloarylthio, cyanoalkylthio, arylalkylthio, aryloxyalkylthio, arylthioalkylthio, heterocycloalkylthio, alkenylthio, haloalkenylthio, halocycloalkylalkenylthio, wherein said aryl or heterocyclic groups of R.sup.
    Type: Grant
    Filed: November 9, 1988
    Date of Patent: August 28, 1990
    Assignee: FMC Corporation
    Inventors: Anthony J. Martinez, Thomas G. Cullen
  • Patent number: 4935157
    Abstract: This invention concerns novel 2-hydroxy-5-alkylthio-1,3,4-thiadiazoles wherein the alkyl group may be substituted by hydroxy and phenoxy groups. The compounds are effective antiwear agents and antioxidants when incorporated into lubricating compositions.
    Type: Grant
    Filed: June 5, 1989
    Date of Patent: June 19, 1990
    Assignee: R. T. Vanderbilt Company, Inc.
    Inventor: Thomas J. Karol
  • Patent number: 4925580
    Abstract: A lubricant composition or hydraulic oil composition containing at least one lubricant or one hydraulic oil and at least one 2,5-dimercapto-1,3,4-thiadiazole of general formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4, which are identical or different, are alkyl having 1 to 24 C atoms, alkenyl having 3 to 12 C atoms or phenyl-(C.sub.1 -C.sub.4)-alkyl which is unsubstituted or substituted in the phenyl radical by C.sub.1 -C.sub.4 -alkyl, or R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, with the N atom to which they are bonded, are a morpholine, piperidine, pyrrolidine, piperazine, methylpiperazine or perhydroazepine radical which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, and X and X.sup.1, which are identical or different, are H, alkyl having 1 to 23 C atoms, phenyl, phenyl-(C.sub.1 -C.sub.4)-alkyl or phenyl substituted by C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.12 -alkoxy, hydroxyl, di(C.sub.1 -C.sub.4 -alkyl)amino, halogen and/or nitro.
    Type: Grant
    Filed: December 15, 1988
    Date of Patent: May 15, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Hugo Camenzind
  • Patent number: 4920231
    Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible streoisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stereo-specific compound and all possible stereo-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: April 24, 1990
    Assignee: Roussel Uclaf
    Inventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 4910210
    Abstract: Novel compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl that is unsubstituted or substituted by halogen, phenyl, C.sub.1 -C.sub.3 alkoxy or by hydroxy, C.sub.1 -C.sub.3 alkyl that is substituted by carbonyl, O-alkylcarboxy, amino or by a heterocycle, unsubstituted or halo-substituted C.sub.3 -C.sub.7 cycloalkyl or unsubstituted cyclopropylmethyl, unsubstituted or halo-substituted C.sub.3 -C.sub.7 alkenyl, unsubstituted or halo-substituted C.sub.3 -C.sub.7 alkynyl, benzyl that is unsubstituted or mono-, di-or tri-substituted in the nucleus by C.sub.1 -C.sub.4 alkyl, halogen, nitro, cyano or by trifluoromethyl, or is the radical R.sub.2 --(O--CH.sub.2 --CH.sub.2 --)n wherein R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl and n is a number from 1 to 3, as active ingredients for controlling nematodes that parasitise plants and for preventing damage to cultivated plants caused by nematode attack.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: March 20, 1990
    Assignee: Ciba-Geigy Corp.
    Inventors: Ernst Beriger, Wolfgang Eckhardt
  • Patent number: 4908144
    Abstract: Reaction products of Dimercaptothiadiazole-derived alcohols and alkenyl succinic anhydrides and their subsequent amine reaction products have been found to be effective antiwear/antioxidant multifunctional additives for lubricants.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: March 13, 1990
    Assignee: Mobil Oil Corporation
    Inventors: Robert H. Davis, Liehpao O. Farng, Andrew G. Horodysky
  • Patent number: 4906393
    Abstract: Mixed phenol/dimercaptothiadiazole-derived hydroxythioether borates have been found to be effective antiwear/antioxidant multifunctional additives for lubricants.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: March 6, 1990
    Assignee: Mobil Oil Corporation
    Inventors: Liehpao O. Farng, Andrew G. Horodysky, William F. Olszewski
  • Patent number: 4904403
    Abstract: Disclosed are novel compounds derived from 2,5-dimercapto-1,3,4-thiadiazole and one or two moles of polyolefin having 5 to 400 carbon atoms. Furthermore, the 5-position of the 2-mercapto-1,3,4-thiadiazole may be substituted by alkylthio, 2-hydroxyalkylthio, amino or hydroxy group. The compounds are effective dispersants, antiwear agents and antioxidants when incorporated into lubricating compositions.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: February 27, 1990
    Assignee: R. T. Vanderbilt Company, Inc.
    Inventor: Thomas J. Karol
  • Patent number: 4902804
    Abstract: The reaction products of the alpha-halogenated half esters or amides of succinic acid and thiadiazole dimercaptides as new compositions of matter and their use as lubricant additives possessing multifunctional properties such as extreme pressure, antiwear, antioxidant and anticorrosion.
    Type: Grant
    Filed: September 6, 1988
    Date of Patent: February 20, 1990
    Assignee: Pennwalt Corporation
    Inventors: James P. King, Sameeh S. Toukan
  • Patent number: 4871719
    Abstract: Novel 13-spiro-2'-[tetrahydrofuran]-milbemycins of the formula I ##STR1## in which X represents one of the groups --CH(OR.sub.1)--, --C(.dbd.O)-- or --C(.dbd.N--OH)--;R.sub.1 represents hydrogen or a OH-protecting group;R.sub.2 represents methyl, ethyl, isopropyl or sec.-butyl or the group --C(CH.sub.3).dbd.CH--A in which A represents methyl, ethyl or isopropyl; andR.sub.3 represents hydrogen; C.sub.1 -C.sub.10 -alkyl; C.sub.1 -C.sub.10 -alkyl substituted by at least one substituent selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy C.sub.3 -C.sub.9 -alkoxyalkoxyalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.3 -alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, hydroxy, benzyloxy, C.sub.1 -C.sub.6 -acyl and C.sub.1 -C.sub.6 -acyloxy, it being possible for each of the above-mentioned radicals representing or containing an alkoxy group to be terminally substituted at a terminal alkoxy group by hydroxy, halogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: March 16, 1988
    Date of Patent: October 3, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Maienfisch
  • Patent number: 4855310
    Abstract: Novel heterocyclic compounds shown by the general formula ##STR1## or the pharmaceutically acceptable salts thereof useful as medicament in particular as antagonist of slow reacting substance of anaphylaxis (SRS-A).
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: August 8, 1989
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kiyoshi Murase, Toshiyasu Mase, Hiromu Hara, Kenichi Tomioka
  • Patent number: RE33778
    Abstract: Substituted 1,3-dithietane-2-carboxylic acid derivatives useful as intermediates for the preparation of highly effective penicillin and cephalosporin derivatives and the preparation thereof.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: December 24, 1991
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Masaru Iwanami, Tetsuya Maeda, Yoshinobu Nagano, Masaharu Fujimoto, Noriaki Nagano, Atsuki Yamazaki, Kasaharu Tamazawa, Kiyoshi Murase, Tadao Shibanuma