Chalcogen Or Nitrogen Attached Directly To Ring Carbon Of The Thiadiazole Ring By Nonionic Bonding Patents (Class 548/135)
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Patent number: 5512576Abstract: 2-Substituted 1,2,5-thiadiazolidin-3-one 1,1-dioxides, pharmaceutical compositions containing them and methods for the treatment of degenerative diseases utilizing them.Type: GrantFiled: December 2, 1994Date of Patent: April 30, 1996Assignee: Sterling Winthrop Inc.Inventors: Ranjit C. Desai, Dennis J. Hlasta
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Patent number: 5498593Abstract: Thiadiazole derivatives with excellent herbicidal effectiveness, wide herbicidal spectrum and excellent selectivity are disclosed. The thiadiazole derivatives are represented by one of the formula [I]-[IV].Type: GrantFiled: March 10, 1995Date of Patent: March 12, 1996Assignee: TOSOH CorporationInventors: Yasuaki Hanasaki, Kazuaki Tsukuda, Hiroyuki Watanabe, Kenji Tsuzuki, Mitsuyuki Murakami, Noritoshi Niimi
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Patent number: 5494925Abstract: 2-Heterocyclyloxymethyl and 2-heterocyclylthiomethyL-1,2,5-thiadiazolidin-3-one 1,1-dioxides, pharmaceutical compositions containing them and methods for the treatment of degenerative diseases utilizing them.Type: GrantFiled: December 2, 1994Date of Patent: February 27, 1996Assignee: Sterling Winthrop Inc.Inventors: John J. Court, Ranjit C. Desai, Dennis J. Hlasta
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Patent number: 5491155Abstract: Substituted thiadiazoles which correspond to the formula: ##STR1## wherein X and Y each independently represents --Br, --Cl, --OCH.sub.3, --SCN, --OCH.sub.2 SCN, --SCH.sub.2 SCN, --OCH.sub.2 CH.sub.2 SCN or --SCH.sub.2 CH.sub.2 SCN, provided that at least one of X or Y represents --SCN, --OCH.sub.2 SCN, --SCH.sub.2 SCN, --OCH.sub.2 CH.sub.2 SCN or --SCH.sub.2 CH.sub.2 SCN are disclosed.These compounds have been found to exhibit antimicrobial and marine antifouling activity in industrial and commercial applications and compositions containing these compounds are so employed.Type: GrantFiled: December 21, 1994Date of Patent: February 13, 1996Assignee: The Dow Chemical CompanyInventors: Ravi B. Shankar, R. Garth Pews, Duane R. Romer
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Patent number: 5488060Abstract: Substituted thiadiazoles which correspond to the formula: ##STR1## wherein R represents ##STR2## X represents --Br, --Cl, --F, --CH.sub.3, --OCH.sub.3, --COOCH.sub.3, --NO.sub.2, --SCH.sub.3, --SO.sub.2 CH.sub.3 or --CF.sub.3 and Y is --SCN or --SCH.sub.2 SCN.These compounds have been found to exhibit antimicrobial and marine antifouling activity in industrial and commercial applications and compositions containing these compounds are so employed.Type: GrantFiled: December 21, 1994Date of Patent: January 30, 1996Assignee: The Dow Chemical CompanyInventors: Ravi B. Shanker, Duane R. Romer, R. Garth Pews
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Patent number: 5482966Abstract: 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: GrantFiled: June 13, 1994Date of Patent: January 9, 1996Assignees: Zeneca Limited, Zeneca Pharma S.A.Inventors: Thomas G. C. Bird, Patrick Ple
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Patent number: 5482916Abstract: Thiadiazole derivatives with excellent herbicidal effectiveness, wide herbicidal spectrum and excellent selectivity are disclosed. The thiadiazole derivatives are represented by one of the formula [I]-[IV].Type: GrantFiled: March 5, 1993Date of Patent: January 9, 1996Assignee: Tosoh CorporationInventors: Yasuaki Hanasaki, Kazuaki Tsukuda, Hiroyuki Watanabe, Kenji Tsuzuki, Mitsuyuki Murakami, Noritoshi Niimi
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Patent number: 5478849Abstract: Disclosed is (a) 1,2,5-thiadiazole derivatives represented by the following formulae [I] or [III]: ##STR1## wherein X and Y are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, a nitro group, a trifluoromethyl group, a carboxyl group, an alkoxycarbonyl group having from 2 to 5 carbon atoms, a naphthyl group or a tetrahydronaphthyl group; and A represents an alkyl group having from 1 to 6 carbon atoms, --C(.dbd.O)OR.sup.1, --C(.dbd.O)NR.sup.2 R.sup.3, a phenyl group which may be substituted by at least one of an alkyl group having from 1 to 6 carbon atoms and an alkoxy group having from 1 to 4 carbon atoms, --CHR.sup.4 C(.dbd.O)R.sup.5 or --C(.dbd.O)R.sup.6, in which R.sup.1 represents an alkyl group having from 1 to 6 carbon atoms, R.sup.2 and R.sup.3 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms, R.sup.Type: GrantFiled: April 21, 1994Date of Patent: December 26, 1995Assignee: Tosoh CorporationInventors: Yasuaki Hanasaki, Hiroyuki Watanabe, Kimio Katsuura, Masatoshi Fujiwara, Teruhiko Ide
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Patent number: 5464809Abstract: Fungicidal new 2-methoximinocarboxylic esters of the general formula (I) ##STR1## in which Ar represents one of the radicals ##STR2## and A represents one of the radicals --CH.sub.2 --; ##STR3## where Y represents one of the radicals ##STR4## --O--CH.sub.2 --; --CH.sub.2 --O--; --S--CH.sub.2 --; ##STR5## --SO.sub.2 --CH.sub.2 --; --O--; --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,n represents the number 0 or 1,R represents alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, or represents optionally substituted cycloalkyl, or represents optionally substituted aryl or represents optionally substituted heteroaryl, and, moreover, in the event that n is 0, also represents halogen, andX.sup.1, X.sup.2, X.sup.3 and X.sup.4 independently of one another in each case represent hydrogen, halogen, hydroxyl or methoxy, but where, in the event that X.sup.2 represents bromine, X.sup.3 does not simultaneously represent hydroxyl or methoxy.Type: GrantFiled: September 12, 1994Date of Patent: November 7, 1995Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Dieter Berg, Heinz-Wilhelm Dehne, Stefan Dutzmann
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Patent number: 5457122Abstract: The phenylalkan(en)oic acids of the formula: ##STR1## as defined herein, possess an antagonistic activity on leukotriene B.sub.4.Type: GrantFiled: July 13, 1993Date of Patent: October 10, 1995Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Mitoshi Konno, Takahiko Nakae, Nobuyuki Hamanaka
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Patent number: 5453433Abstract: Compounds of the formula; ##STR1## wherein: Thi is thiadiazolyl or substituted thiadiazolyl;Y is alkylene bridge of 3-9 carbon atoms;R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinyl alkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluoromethyl, or cyano;R.sub.3 is alkoxycarbonyl, phenyl, alkyltetrazolyl, or heterocyclyl; or a pharmaceutically acceptable salt thereof are effective antipicornaviral agents.Type: GrantFiled: May 13, 1994Date of Patent: September 26, 1995Assignee: Sterling Winthrop Inc.Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Theodore J. Nitz
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Patent number: 5441969Abstract: The present invention discloses compounds of the formula ##STR1## or a pharmaceutically-acceptable addition salt thereof whereinR' and R" independently of each other are hydrogen or alkyl, or R' and R" together form a 3 to 6 membered alkylene chain;one of R.sup.1 and R.sup.2 is aryl which may be substituted one or more times with halogen, CF.sub.3, CN, OH, alkyl, cycloalkylalkyl, alkenyl, alkynyl, alkoxy, amino, nitro, sulphamoyl, tetrazolyl, CO.sub.2 H, CO.sub.2 -alkyl and the other of R.sup.1 and R.sup.2 is hydrogen, halogen, alkoxy, amino or alkyl; andR.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of each other are hydrogen, halogen, amino, nitro, CN, OH, CF.sub.3, alkyl or alkoxy; and n is 0 or 1; provided that neither of R.sup.1 and R.sup.2 is phenyl or substituted phenyl when n is 0.The compounds are useful as pharmaceuticals, for example, in the treatment of ischemia, anoxia, migraine and psychosis.Type: GrantFiled: December 22, 1993Date of Patent: August 15, 1995Assignee: NeuroSearch A/SInventors: Oskar Axelsson, Dan Peters, Elsebet O Nielsen
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Patent number: 5409944Abstract: 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: GrantFiled: March 12, 1993Date of Patent: April 25, 1995Assignee: Merck Frosst Canada, Inc.Inventors: W. Cameron Black, Chun-Sing Li, Daniel Guay, Petpiboon Prasit, Patrick Roy
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Patent number: 5403930Abstract: A compound of the formula Het--NR--SO.sub.2 --Ph.sup.2 --A--Ph.sup.1 (COOH)(OH) and tautomic form, salts, solvates, C.sub.1-6 alkyl esters and pharmaceutical compositions of the compound. Ph.sup.1 and Ph.sup.2 are benzene rings with the proviso that carboxy and hydroxy are ortho to one another. Het includes an optionally substituted heterocyclic ring which includes conjugated double bonds and binds to nitrogen in NR. The compound is characterized in that A is a bridge which is stable against reduction because it is not azo, and in that R is hydrogen or lower alkyl.The invention also includes the preparation of the compound and its use as a drug, particularly for treating autoimmune diseases.Type: GrantFiled: October 7, 1993Date of Patent: April 4, 1995Assignee: Pharmacia ABInventors: Hubert Agback, Leif Ahrgren, Thomas Berglindh, Martin Haraldsson, Goran Smedeg.ang.rd, Lars-Inge Olsson
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Patent number: 5391720Abstract: Disclosed is an imidazole azo dye of formula (I), which is useful for image formation and as a filter dye, which has a sharp absorption wave and which is fast to light, heat, air, moisture and chemicals. Also disclosed is a thermal transfer dye-donating material containing imidazole azo dye(s) of formula (I) preferably along with aminopyrazole azo dye(s) of formula (II). The material gives a high-density image with good color reproduction, and the image formed has improved storage stability. ##STR1## In (I), B and C independently represent a hydrogen atom or a substituent capable of being substituted in the imidazole ring; A represents an aryl or heterocyclic group; provided that when B is a hydrogen atom, C is not a hydrogen atom nor an alkyl group having from 1 to 3 carbon atoms; provided that when C is a hydrogen atom, B is not a substituted nor unsubstituted alkyl group; provided that C is not a mercapto group or an alkylthio group; and provided that B is not a carboxyl group.Type: GrantFiled: December 3, 1992Date of Patent: February 21, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Hisashi Mikoshiba, Tomomi Tateishi
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Patent number: 5369107Abstract: Compounds of the formula: ##STR1## wherein A is S, SO, or SO.sub.2, R.sup.1 is H or acyl, R.sup.2 is H, alkyl, hydroxyalkyl, halogen or carboxy, and R.sup.3 is pyridyl are claimed. The compounds are useful as therapeutic agents for the treatment of e.g. rheumatism, nephritis and thrombocytopenia.Type: GrantFiled: July 13, 1993Date of Patent: November 29, 1994Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Masaaki Matsuo, Takashi Ogino, Norihiro Igari, Hachiro Seno, Kyoichi Shimomura
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Patent number: 5336420Abstract: An aromatic functional fluid, specifically a monoalkylated tetradecyl diphenyl oxide synthetic lubricant, contains a polymer-supported reaction product of an organic quaternary ammonium salt, derived from a mercapto-heterocycle and a quaternary ammonium salt. To produce the polymer-supported organic quaternary ammonium salt, the salt is reacted with a dicarboxylic acid or anhydride, specifically 2-dodecen-1-ylsuccinic anhydride. An arylamine antioxidant, such as alkylated phenyl naphthylamine, can be added to the polymer supported organic quaternary ammonium salt-treated functional fluid to impart extra antioxidant and stability properties.Type: GrantFiled: December 14, 1992Date of Patent: August 9, 1994Assignee: Mobil Oil CorporationInventors: Andrew G. Horodysky, Shih-Ying Hsu, Andrew Jeng, Leslie R. Rudnick
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Patent number: 5332757Abstract: 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: GrantFiled: February 8, 1993Date of Patent: July 26, 1994Assignees: Zeneca Limited, Zeneca PHARMA S AInventors: Thomas G. C. Bird, Patrick Ple
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Patent number: 5326776Abstract: Compounds are disclosed having the formula: ##STR1## wherein the substituents are defined herein. The compounds of the invention are angiotensin II receptor antagonists.Type: GrantFiled: February 24, 1993Date of Patent: July 5, 1994Assignee: Abbott LaboratoriesInventors: 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
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Patent number: 5324837Abstract: 3,4-Diaryl-4,5-dihydro-1H-pyrazole compounds having a selected 5- or 6-membered aromatic heterocyclic moiety in the 4-position and an optionally substituted phenyl moiety in the 3-position, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2-pyridinyl)-1H-pyrazo le were prepared as intermediates in the preparation of insecticidal 3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds. The 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds can be prepared from appropriate 1,2-diarylethanone compounds by successive treatments with N,N,N',N'-tetramethyldiaminomethane in dichloromethane in the presence of acetic anhydride (to form a Mannich adduct) and hydrazine in the presence of a catalytic amount of trifluoroacetic acid.Type: GrantFiled: August 17, 1992Date of Patent: June 28, 1994Assignee: DowElancoInventors: James M. Renga, Kevin L. McLaren, James T. Pechacek, Michael J. Ricks, Yulan C. Tong
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Patent number: 5302718Abstract: A compound of the formula Het--NR--SO.sub.2 --Ph.sup.2 --A--Ph.sup.1 (COOH)(OH) and tautomeric form, salts, solvates, C.sub.1-6 alkyl esters and pharmaceutical compositions of the compound. Ph.sup.1 and Ph.sup.2 are benzene rings with the proviso that carboxy and hydroxy are ortho to one another. Het includes an optionally substituted heterocyclic ring which includes conjugated double bonds and binds to nitrogen in NR. The compound is characterized in that A is a bridge which is stable against reduction because it is not azo, and in that R is hydrogen or lower alkyl.The invention also includes the preparation of the compound and its use as a drug, particularly for treating autoimmune diseases.Type: GrantFiled: November 9, 1992Date of Patent: April 12, 1994Assignee: Kabi Pharmacia ABInventors: Hubert Agback, Leif Ahrgren, Thomas Berglindh, Martin Haraldsson, Goran Smedegard, Lars-Inge Olsson
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Patent number: 5298515Abstract: Abstract of the Disclosure: N-Hetaryl-2-nitroanilines Ia and Ib ##STR1## (R.sup.1 =H, halogen, C.sub.1 -C.sub.4 -alkoxy; R.sup.2 =NO.sub.2, CN, halogen, C.sub.1 -C.sub.4 -haloalkyl; R.sup.3 =NO.sub.2, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -haloalkyl; R.sup.4 =CO--R.sup.5,CO--OR.sup.5, SO.sub.2 R.sup.5 with R.sup.5 =C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl or naphthyl; Q=H, alkali metal or alkaline earth metal ion, substituted or unsubstituted ammonium ion, phosphonium, sulfonium or sulfoxonium ion, one equivalent of a transition metal cation; Het=thienyl, thiazolyl, isothiazolyl or thiadiazolyl, each of which is linked via a ring carbon to the basic element, which can be fused to a non-aromatic C.sub.5 -C.sub.8 -ring and/or can additionally carry on each other carbon one of the following: CN, SCN, NO.sub.2, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, substituted or unsubstituted phenyl, naphthyl, benzyl or thienyl, CO--R.sup.5, CO--OR.sup.5, NR.sup.6 R.sup.7 ; R.Type: GrantFiled: October 6, 1992Date of Patent: March 29, 1994Assignee: BASF AktiengesellschaftInventors: Juergen Schubert, Reiner Kober, Gerhard Hamprecht, Hubert Sauter, Uwe Kardorff, Christoph Kuenast
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Patent number: 5281614Abstract: Novel substituted triazolinone, triazolinethione, and triazolinimine compounds of the formula I are useful as angiotensin II antagonists.Type: GrantFiled: November 2, 1992Date of Patent: January 25, 1994Assignee: Merck & Co., Inc.Inventors: Wallace T. Ashton, Prasun K. Chakravarty, Linda L. Chang, William J. Greenlee, Dooseop Kim, Nathan B. Mantlo, Arthur A. Patchett
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Patent number: 5276037Abstract: 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: GrantFiled: April 14, 1993Date of Patent: January 4, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
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Patent number: 5223616Abstract: 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: GrantFiled: November 4, 1991Date of Patent: June 29, 1993Assignee: Sumitomo Chemical Company, Ltd.Inventors: Jun Yamamoto, Junichi Sekihachi, Yosuke Yamamoto, Kazuhiro Machiguchi, Yutaka Kayane
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Patent number: 5206252Abstract: The compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.2-6 alkoxycarbonyl, nitro, cyano, halogeno, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.2-6 alkanoylamino, C.sub.2-6 perfluoroalkanoylamino, C.sub.1-12 mono- or di-alkylamino, C.sub.1-6 alkylsulfonyl, C.sub.6-12 arylsulfonyl, carboxyl, C.sub.2-12 mono- or di-alkylcarbamoyl, or hydrogen; a and b together form an --O-- linkage or a direct bond; R.sub.3 and R.sub.4, independent from each other, are C.sub.1-6 alkyl when a and b form an --O-- linkage or, H or C.sub.1-6 alkyl when a and b form a direct bond; either R.sub.5 is hydrogen, hydroxyl, C.sub.2-6 alkanoyloxy, C.sub.7-12 aroyloxy, carbamoyloxy, formyloxy, C.sub.2-6 alkoxycarbonyloxy, mono or di C.sub.2-12 alkylcarbamoyloxy, and R.sub.6 is hydrogen, or R.sub.5 and R.sub.6 together are a bond; R.Type: GrantFiled: May 8, 1992Date of Patent: April 27, 1993Assignee: American Home Products CorporationInventors: John A. Butera, Jehan F. Bagli
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Patent number: 5194167Abstract: Quaternary ammonium salts of mercaptothiadiazoles and related heterocyclic derivatives have been found to be effective antioxidant and antiwear additives for lubricants and fuels.Type: GrantFiled: May 8, 1991Date of Patent: March 16, 1993Assignee: Mobil Oil CorporationInventors: Shih-Ying Hsu, Andrew G. Horodysky
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Patent number: 5194446Abstract: 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: GrantFiled: July 24, 1991Date of Patent: March 16, 1993Assignee: A. H. Robins Company, IncorporatedInventors: Young S. Lo, Joseph C. Nolan, William J. Welstead, Jr., David A. Walsh, Dwight A. Shamblee, Ibrahim M. Uwaydah
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Patent number: 5186850Abstract: 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: GrantFiled: July 9, 1992Date of Patent: February 16, 1993Assignee: Mobil Oil CorporationInventors: Abraham O. M. Okorodudu, Angeline B. Cardis, Ross A. Kremer
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Patent number: 5171861Abstract: Dimercaptothiadiazole reacted with arylsulfonic acids preformed or formed in situ in lubricants provide multifunctional antioxidant, antiwear, and corrosion inhibiting properties thereto.Type: GrantFiled: October 29, 1990Date of Patent: December 15, 1992Assignee: Mobil Oil CorporationInventors: Robert E. Ernhoffer, Arjun K. Goyal, Andrew G. Horodysky, Derek A. Law, Shi-Ming Wu
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Patent number: 5102568Abstract: 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: GrantFiled: February 5, 1988Date of Patent: April 7, 1992Assignee: ATOCHEM North America, Inc.Inventors: James P. King, Billy L. Hill
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Patent number: 5051420Abstract: Invention compounds of the formula: ##STR1## wherein Z is ##STR2## are novel. Compounds of the above formula have shown antiarrhythmic activity in an electrophysiological assay.Type: GrantFiled: March 4, 1991Date of Patent: September 24, 1991Assignee: A. H. Robins Company, IncorporatedInventors: Mark R. Hellberg, James R. Shanklin, Jr.
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Patent number: 4990668Abstract: Described is a process for preparing a racemic or chiral aryloxypropanolamine (1) or arylethanolamine (2) of the formula ##STR1## wherein Ar is aryl, substituted aryl, heteroaryl, or aralkyl and R is alkyl, substituted alkyl, aralkyl, or WB wherein W is a straight or branched chain alkylene of from 1 to about 6 carbon atoms and wherein B is --NR.sub.2 COR.sub.3, --NR.sub.2 CONR.sub.3 R.sub.4, --NR.sub.2 SO.sub.2 R.sub.3, --NR.sub.2 SO.sub.2 NR.sub.3 R.sub.4, or --NR.sub.2 COOR.sub.5, where R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.3 and R.sub.5 are not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.3 or --NR.sub.3 COOR.sub.5, or R.sub.3 and R.sub.4 may together with N form a 5- to 7-membered heterocyclic group.The process can be used to prepare beta-blocking agents, useful in the treatment of cardiac conditions.Type: GrantFiled: December 4, 1985Date of Patent: February 5, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Khuong H. X. Mai, Ghanshyam Patil, William L. Matier
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Patent number: 4920231Abstract: 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: GrantFiled: March 30, 1989Date of Patent: April 24, 1990Assignee: Roussel UclafInventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
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Patent number: 4914206Abstract: The present invention provides lankacidin derivatives of the formula ##STR1## and procedures for the production thereof. The lankacidin derivatives [1] show excellent antimicrobial activities and thus can be used for prophylaxis and treatment of infectious disease in animals.Type: GrantFiled: December 15, 1988Date of Patent: April 3, 1990Assignee: Takeda Chemical Industries, LTD.Inventors: Isao Minamida, Naoto Hashimoto
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Patent number: 4912224Abstract: An antibacterial 7beta-(carboxyalkenoyl)amino-3-cephem-4-carboxylic acid represented by the following formula: ##STR1## (wherein R is aryl or a heterocyclic group;R.sup.1 is hydrogen or halogen;R.sup.2 is a single bond, alkylene, or thiaalkylene;R.sup.3 is a hydrogen atom or carboxy modifying group;R.sup.4 is hydrogen or methoxy;R.sup.5 is hydrogen or a 3-substituent of cephalosporins;R.sup.6 is a hydrogen atom or carboxy modifying group; andX is oxygen, sulfur, or sulfinyl)a pharmaceutical composition containing the same, and a method for treating a bacterial infection with the same.Type: GrantFiled: December 9, 1987Date of Patent: March 27, 1990Assignee: Shionogi & Co., Ltd.Inventor: Yoshio Hamashima
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Patent number: 4906393Abstract: Mixed phenol/dimercaptothiadiazole-derived hydroxythioether borates have been found to be effective antiwear/antioxidant multifunctional additives for lubricants.Type: GrantFiled: December 30, 1988Date of Patent: March 6, 1990Assignee: Mobil Oil CorporationInventors: Liehpao O. Farng, Andrew G. Horodysky, William F. Olszewski
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Patent number: 4904660Abstract: Novel compounds of the following formula (I) and their salts: A compound of the formula (I) ##STR1## These compounds are expected to be useful for renin inhibitors. Thus, the compounds are useful medical agents, in particular, anti-hypertensive agents.Type: GrantFiled: February 25, 1988Date of Patent: February 27, 1990Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Kohji Nakano, Takashi Fujikura, Ryuichiro Hara, Masato Ichihara, Yukiko Fukunaga, Masayuki Shibasaki
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Patent number: 4902804Abstract: 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: GrantFiled: September 6, 1988Date of Patent: February 20, 1990Assignee: Pennwalt CorporationInventors: James P. King, Sameeh S. Toukan
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Patent number: 4889553Abstract: Herbicidal triazole sulphonamides of the formula: ##STR1## and salts thereof, where: R.sup.1 represents hydrogen or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, acyl, alkoxycarbonyl, aminocarbonyl, sulphonyl or heterocyclic group;R.sup.2 represents hydrogen, halo, cyano, hydroxy, mercapto, a substituted or unsubstituted alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, acyl, alkoxycarbonyl, aminocarbonyl, aryl or amino group, or a heterocyclic group;R.sup.3 represents a substituted or unsubstituted heterocyclic, benzheterocyclic, aryl or aralkyl group; andR.sup.4 represents hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, acyl, aroyl, alkylsulphonyl, alkoxycarbonyl, aminocarbonyl, aralkyl, or a group of the formula: ##STR2## where R.sup.1 and R.sup.2 are as defined hereinbefore, processes for their preparation and compositions containing them.Type: GrantFiled: May 15, 1987Date of Patent: December 26, 1989Assignee: Schering AgrochemicalsInventors: Graham P. Rowson, John C. Head, Jurgen Westermann, Martin Kruger, Friedrich Arndt, Richard Rees
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Patent number: 4882342Abstract: The present invention concerns new 5-alkylbenzimidazoles of the formula: ##STR1## wherein R.sub.1 is a phenyl ring of the formula: ##STR2## or R.sub.1 is naphthyl, heterocycle or a bicyclic heterocycle and R.sub.1 -R.sub.7 are described in claim 1.These compounds are useful for prophylaxis or treatment of heart and circulatory disease especially to increase contractility of the heart, lower blood pressure and/or influence the thrombocyte function and improve the microcirculation.Type: GrantFiled: October 6, 1987Date of Patent: November 21, 1989Assignee: Boehringer Mannheim GmbHInventors: Wolfgang von der Saal, Jens-Peter Holck, Alfred Mertens, Bernd Muller-Beckmann, Lothar Kling
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Patent number: 4876351Abstract: A process for the separation of a mixture of syn and anti oxime isomers one from the other which comprises adsorbing said mixed oxime isomers onto a non-functional macroreticular adsorption resin, and eluting said resin to yield at least one eluate fraction containing one of said isomers while being substantially free of the other of said isomers.The application of this process to the separation of syn and anti isomers of cephalosporin compounds possessing an oxime grouping in a side-chain in the 7.beta.-position, and of acids corresponding to this 7.beta.-side chain, is described.Type: GrantFiled: October 30, 1987Date of Patent: October 24, 1989Assignee: Glaxo Group LimitedInventors: Colin Robinson, David T. Eastlick, Audrey J. Bownass
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Patent number: 4871719Abstract: 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: GrantFiled: March 16, 1988Date of Patent: October 3, 1989Assignee: Ciba-Geigy CorporationInventor: Peter Maienfisch
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Patent number: 4863945Abstract: Pyrrolobenzimidazoles of the formula: ##STR1## are useful for treatment of heart and circulatory diseases. R.sub.1 is substituted phenyl; or optionally substituted naphthyl or a five- or six-membered heterocyclic group which can be condensed with a phenyl ring to form a bicyclic radical. R.sub.2 is hydrogen, alkyl, alkenyl or cycloalkenyl; R.sub.3 is alkyl, alkenyl or hydroxyalkyl or with R.sub.2 together forms cycloakylene; or R.sub.2 and R.sub.3 together form alkylidene or cycloalkylidene. R.sub.4 is hydrogen or lower alkanoyl. X is a valency bond, alkylene, vinylene, imino or carbonylamino. T stands for two hydrogen atoms. When X is a valency bond, R.sub.1 can also be hydrogen, hydrocarbyl which may also contain oxygen, amino, sulfur, carbonyl and sulfonyl groups. When X is imino or carbonylamino or when R.sub.1 is a bicyclic radical, T can also be oxygen. The compounds also include the tautomers and physiologically acceptable salts with inorganic and organic acids.Type: GrantFiled: December 10, 1987Date of Patent: September 5, 1989Assignee: Boehringer Mannheim GmbHInventors: Walter-Gunar Friebe, Alfred Mertens, Klaus Strein, Erwin Boehm
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Patent number: 4855310Abstract: 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: GrantFiled: March 25, 1988Date of Patent: August 8, 1989Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Kiyoshi Murase, Toshiyasu Mase, Hiromu Hara, Kenichi Tomioka
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Patent number: 4851410Abstract: 1,4-disubstituted pyrazole derivatives of the formula I ##STR1## where R.sup.1 and R.sup.2 independently of one another are each hydrogen, lower alkyl or benzyl, or R.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, may be a pyrrolidino, piperidino or morpholino radical, n is an integer from 2 to 5 and Z is a radical of the formula ##STR2## or QNR.sup.1 R.sup.2 where R.sup.1 and R.sup.2 have the same meanings as above, Q is ##STR3## A is CHR.sup.3 or NR.sup.3 in which R.sup.3 is CN, NO.sub.2, SO.sub.2 -aryl or SO.sub.2 -lower alkyl and m may be 0 or 1, and their pharmaceutically tolerated salts, processes for their preparation, pharmaceutical compositions containing the compounds of formula I, the use of such compositions and an intermediate of the formula III ##STR4## where R.sup.1, R.sup.2 and n have the same meanings as above, in the preparation of the compounds of the formula I.The compounds are useful to block histamine H.sub.2.sup.- receptors.Type: GrantFiled: November 15, 1988Date of Patent: July 25, 1989Assignee: BASF AktiengesellschaftInventors: Bernd Ostersehlt, Norbert Rieber, Josef Gries
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Patent number: 4851406Abstract: The present invention provides indole derivatives of the general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, carboxyl, cyano, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or aryl radical, R.sub.2 is a hydrogen atom or an alkyl, trihalogenomethyl, hydroxyl, cycloalkyl, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl radical; R.sub.2 is a heterocyclic five-membered ring containing 1 to 4 heteroatoms or a heterocyclic six-membered ring containing 1 to 5 heteroatoms, the heteroatoms of the five- and six-membered rings being the same or different and being nitrogen, oxygen or sulphur and one or more of the nitrogen atoms optionally carrying an oxygen atom, the said five- and six-membered rings optionally being substituted by one or more alkyl, alkoxy, alkylthio, oxo, hydroxyl, nitro, amino, halogen or cyano groups; or R.sub.Type: GrantFiled: September 4, 1986Date of Patent: July 25, 1989Assignee: Boehringer Mannheim GmbHInventors: Alfred Mertens, Wolfgang von der Saal, Walter-Gunar Friebe, Bernd Muller-Beckmann, Gisbert Sponer
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Patent number: 4835280Abstract: The present invention provides Indolines of the formula: ##STR1## ps useful to provide pharmaceutically active pyrrolobenzimidazoles or tautomers thereof, of the formula: These compounds are useful for treating heart or circulatory diseases, especially those which respond to a change of blood pressure, an increase in cardiac output and/or a change in micro-circulation.Type: GrantFiled: July 14, 1987Date of Patent: May 30, 1989Assignee: Boehringer Mannheim GmbHInventors: Alfred Martens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckman, Klaus Strein, Egon Roesch
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Patent number: 4831032Abstract: The present invention provides benzimidazoles of the general formula: ##STR1## wherein R.sub.1, X, A, and R.sub.2 are as defined in the specification. The present invention also provides processes for the preparation of these new benzimidazoles and pharmaceutical compositions containing them, as well as intermediates for the preparation thereof.The new benzimidazoles are useful to treat heart or circulatory diseases which respond to a lowering of blood pressure, a positive inotropic action and/or an improvement in microcirculation.Type: GrantFiled: July 3, 1986Date of Patent: May 16, 1989Assignee: Boehringer Mannheim GmbHInventors: Wolfgang von der Saal, Alfred Mertens, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein
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Patent number: 4810282Abstract: This invention relates to ortho-(isoxazolyl, isothiazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, and triazolyl)benzenesulfonamides and their use as herbicides.Type: GrantFiled: June 10, 1987Date of Patent: March 7, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Morris P. Rorer