Chalcogen Attached Directly To The Polycyclo Ring System By Nonionic Bonding Patents (Class 548/259)
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Patent number: 5521318Abstract: There is disclosed a compound represented by formula (I): ##STR1## wherein R.sup.1 represents a tert-butyl group, a phenyl group having an alkoxy group with 1 to 18 carbon atoms in the paraposition, or an indoline-1-yl group; R.sup.2 represents a group substitutable on the benzene ring; and n is an integer of 0 to 4, provided that when R.sup.1 represents a tert-butyl group, n is not 0. The compound may be used as a synthesis intermediate from which a yellow coupler can be synthesized in a simple manner. Using the compound, a yellow coupler can be readily produced on an industrial scale with the short process.Type: GrantFiled: April 21, 1995Date of Patent: May 28, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Katsuyoshi Yamakawa, Tadahisa Sato, Koichi Hanaki
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Patent number: 5516914Abstract: 2-(2-Hydroxyphenyl)-2H-benzotriazole UV-absorbers substituted at the 5-position of the benzo ring by a thioether group exhibit enhanced absorption in the near visible range (over 350 nm) allowing said compounds to be particularly effective in protecting polymer systems which are prone to degradation caused by actinic irradiation with wavelengths over 350 nm.Type: GrantFiled: November 1, 1993Date of Patent: May 14, 1996Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Volker H. von Ahn, Tyler A. Stevenson, Mark S. Holt, Ramanathan Ravichandran
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Patent number: 5516751Abstract: There are provided o-carboxy-(5-oxo-2-imidazolin-2-yl)benzoheterocyclic compounds wherein the fused heterocyclic ring system is a 5-membered ring containing one, two or three nitrogen atoms, derivatives of said benzoheterocyclic compounds and a method for the use therewith to control monocotyledenous and dicotyledenous plant species.Type: GrantFiled: May 24, 1995Date of Patent: May 14, 1996Assignee: American Cyanamid CompanyInventor: Robert F. Doehner, Jr.
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Patent number: 5504214Abstract: Substituted benzotriazoles, which contain at least 2 fluorine atoms per molecule, are excellent intermediates for preparing active compounds for pharmaceuticals and plant-protection agents; however, they themselves also exhibit a fungicidal effect.Type: GrantFiled: January 21, 1994Date of Patent: April 2, 1996Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Bernd Baasner, Gerd Hanssler
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Patent number: 5498616Abstract: The present invention is directed to irreversible inhibitors of serine and cysteine proteases which most preferably contain a 1-oxytriazole or 1-oxyimidazole functionality. Methods for the use of the protease inhibitors are also described.Type: GrantFiled: November 4, 1994Date of Patent: March 12, 1996Assignee: Cephalon, Inc.Inventors: John P. Mallamo, Ron Bihovsky, Sankar Chatterjee, Rabindranath Tripathy
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Patent number: 5488112Abstract: The invention relates to dimeric 2-(2'-hydroxyphenyl)benzotriazoles of the formula I ##STR1## in which p is 0 or 1; is C.sub.1 -C.sub.12 alkylene;R.sub.1 and R'.sub.1, independently of one another, are hydrogen, halogen, C.sub.1 -C.sub.18 aklyl, C.sub.1 -C.sub.18 alkoxy or --CN;R.sub.2 and R'.sub.2, independently of one another, are hydrogen or C.sub.1 -C.sub.18 alkyl or together are C.sub.2 -C.sub.12 alkylene or C.sub.2 -C.sub.12 hydroxyalkylene; andR.sub.3 and R'.sub.3, independently of one another, are hydrogen, halogen, C.sub.1 -C.sub.18 alkyl or C.sub.1 -C.sub.18 alkoxy.The compounds of formula I are highly suitable for the stabilization of organic material against the harmful effects of heat, oxygen and light, in particular UV radiation.Type: GrantFiled: February 22, 1995Date of Patent: January 30, 1996Assignee: Ciba-Geigy CorporationInventors: Dieter Reinehr, Jean-Pierre Bacher, Andre Schmitter
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Patent number: 5484762Abstract: There is provided an aryloxy-N-(substituted phenyl)benzotriazole compound having the structural formula I ##STR1## Further provided are a composition and a method comprising that compound for the control of undesirable plant species.Type: GrantFiled: February 10, 1995Date of Patent: January 16, 1996Assignee: American Cyanamid CompanyInventors: Michael E. Condon, Alvin D. Crews, Jr., Mark C. Manfredi
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Patent number: 5466819Abstract: Provided are ultraviolet stabilizers which are diphenylmethane compounds of the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are independently C.sub.1 to C.sub.8 alkyl, cyclopentyl, cyclohexyl or cumyl; and X is selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.12 alkyl and C.sub.1 to C.sub.12 alkoxy. The invention also pertains to a process for their preparation and stabilized polymer blends containing the stabilizers.Type: GrantFiled: July 6, 1994Date of Patent: November 14, 1995Assignee: Fairmount Chemical Company, Inc.Inventors: William E. Leistner, Semyon Moshchitsky
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Patent number: 5453517Abstract: The invention relates to fluorescent and/or reactive derivatives of 1,2-bis-(2-aminophenoxyethane)-N,N,N',N'-tetraacetic acid (BAPTA) according to the formula: ##STR1## where at least one of W and X is a functional group, with or without a spacer, that terminates in an alcohol or phenol, a thiol, a haloacetamide, an alkyl halide, an amine or aniline, a carboxylic acid, an anhydride, an isocyanate, an isothiocyanate, a maleimide, or an activated ester. The BAPTA-like molecule may be further substituted, one or more times, by additional functional groups with or without spacers or by CH.sub.3, NO.sub.2, CF.sub.3, F, Cl, Br, I, or carboxylic acid derivatives or pharmaceutically acceptable salts thereof, or by indolyl or benzofuran fluorophores. The functional groups allow for subsequent covalent attachment of one or more oxygen heterocycle fluorophores (e.g. fluorescein, coumarin, rhodamine); or polymolecular assemblies (e.g.Type: GrantFiled: February 25, 1992Date of Patent: September 26, 1995Assignee: Molecular Probes, Inc.Inventors: Michael A. Kuhn, Richard P. Haugland
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Patent number: 5438142Abstract: Compounds useful as polymer stabilizers which are polymerizable into condensation polymer systems are disclosed and claimed. A particularly preferred embodiment is 1-(3'-(benzotriazol-2"-yl)-4'-hydroxyphenyl)-1,1-bis(4-hydroxyphenyl)ethan e.Type: GrantFiled: August 10, 1993Date of Patent: August 1, 1995Assignee: Hoechst Celanese Corp.Inventors: John R. Fritsch, Olan S. Fruchey, Debasish Kuila, George Kvakovszky, Mark A. Murphy, Michael T. Sheehan, James R Sounik, Richard Vicari
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Patent number: 5436349Abstract: 2-(2-Hydroxyphenyl)-2H-benzotriazole UV-absorbers substituted at the 5-position of the benzo ring by a sulfoxide or sulfone group exhibit enhanced absorption in the near visible range (over 350 nm) allowing said compounds to be particularly effective in protecting polymer systems which are prone to degradation caused by actinic irradiation with wavelengths over 350 nm.Type: GrantFiled: November 1, 1993Date of Patent: July 25, 1995Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Volker H. von Ahn, Tyler A. Stevenson, Mark S. Holt, Ramanathan Ravichandran
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Patent number: 5429770Abstract: Low-molecular-weight and polymeric liquid-crystalline 2-substituted benzotriazoles of the formula ##STR1## are used as photoconductors or electrophotographic recording materials or as fluorescent dyes for fluorescent displays.Type: GrantFiled: May 18, 1994Date of Patent: July 4, 1995Assignee: BASF AktiengesellschaftInventors: Friedrich Closs, Karl Siemensmeyer, Dirk Funhoff
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Patent number: 5410071Abstract: A composition that, when present in a polymer matrix, reduces the deleterious effect of UV light absorption by the polymer is provided, which comprises a sulfur-containing derivative of hydroxyphenylbenzotriazole having the formula of: ##STR1## wherein each X is selected from the group consisting of hydrogen, halogens, cyano, alkyl, phenyl group, biphenyl group, arylthio, amine, ketone, aldehyde, alkoxy, hydroxy, carboxylic acid group, oligomer and combinations thereof and can have carbon atoms up to about 20; n is a whole number from 1 to 5; n' is a whole number from 0 to 4; n" is a whole number from 1 to 2 and each n" can be the same or different; q is an integer from 1 to 10; each Y is selected from the group consisting of --S(O)(O)--, --S(O)--, and --S--; each R can be selected from the group consisting of hydrogen, alkyl group, alkenyl group, aralkyl group, alkaryl group, and combinations thereof and can have 0 to about 10 carbon atoms; each OH group can be at either the 2'- or the 6'-position, or both.Type: GrantFiled: February 17, 1994Date of Patent: April 25, 1995Assignee: Phillips Petroleum CompanyInventors: Paul J. DesLauriers, Paritosh K. Das, Darryl R. Fahey
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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: 5387691Abstract: 2-(Benzotriazol-2-yl)-4-alkyl-6-(2-hydroxy-3-benzoyl-6-alkoxybenzyl)phenols am prepared by reacting a Mannich base of a 2-(2-hydroxy-5-alkylphenyl)-2H-benzotriazole with a 2-hydroxy-4-alkoxybenzophenone. The hybrid products exhibit outstanding efficacy in protecting organic substrates from light-induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.Type: GrantFiled: March 5, 1993Date of Patent: February 7, 1995Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, John J. Luzzi, Gregory R. Coughlin
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Patent number: 5362881Abstract: Provided are ultraviolet stabilizers which are diphenylmethane compounds of the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are independently C.sub.1 to C.sub.8 alkyl, cyclopentyl, cyclohexyl or cumyl; and X is selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.12 alkyl and C.sub.1 to C.sub.12 alkoxy. The invention also pertains to a process for their preparation and stabilized polymer blends containing the stabilizers.Type: GrantFiled: May 27, 1993Date of Patent: November 8, 1994Assignee: Fairmount Chemical Company, Inc.Inventors: William E. Leistner, Semyon Moshchitsky
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Patent number: 5324711Abstract: This invention is directed to certain substituted aryloxy benzotriazole compounds which are herbicidal agents. The structures of these compounds are represented by formulas I and II shown below: ##STR1## wherein M is C--X, N or N.sup.+ --O.sup.- ;W, X, Y and Z each independently represent hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 haloalkoxy;n is 0, 1 or 2;R is hydrogen, C.sub.1 -C.sub.4 alkyl, aryl or when taken together with R.sub.1, R and R.sub.1 may form a ring in which RR.sub.1 are represented by the structure --(CH.sub.2).sub.m -- where m is an integer of 2, 3, 4 or 5;R.sub.1 and R.sub.2 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl or when taken together R.sub.1 and R.sub.2 may form a ring in which R.sub.1 R.sub.2 are represented by the structure --(CH.sub.2).sub.m -- where m is an integer of 2, 3, 4 or 5;R.sub.3 is cyano, ##STR2## CH.sub.2 OR.sub.8 or CH(OR.sub.9).sub.2 ; Q is OH, OR.sub.4 or NR.sub.5 R.sub.6 ;A is O, NOR.sub.5, NCOR.sub.5, NNR.sub.5 R.Type: GrantFiled: October 5, 1989Date of Patent: June 28, 1994Assignee: American Cyanamid CompanyInventors: Donald R. Nielsen, Thomas A. Lies
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Patent number: 5322853Abstract: Novel benzotriazolesulfonic acid derivatives of formula ##STR1## wherein: R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy having at least two identical or different halogen atoms, CF.sub.3, nitro or the group N(R')R", wherein R' and R" are each independently of the other C.sub.1 -C.sub.4 alkyl;R.sub.2 is phenoxy or phenylthio each of which is unsubstituted or mono- to tri-substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy having at least two identical or different halogen atoms, cyano, nitro, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, phenyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by C.sub.1 -C.sub.4 alkoxy; or R.sub.2 is the radical O--CH.sub.2 --O;R.sub.3 is alkyl, aryl or aralkyl having a maximum of 14 carbon atoms, these radicals can be substituted by halogen, C.sub.1 -C.sub.Type: GrantFiled: April 23, 1993Date of Patent: June 21, 1994Assignee: Ciba-Geigy CorporationInventors: Peter Ackermann, Max Schellenbaum
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Patent number: 5319091Abstract: A composition that, when present in a polymer matrix, reduces the deleterious effect of UV light absorption by the polymer is provided, which comprises a sulfur-containing derivative of hydroxyphenylbenzotriazole having the formula of: ##STR1## wherein each X is selected from the group consisting of hydrogen, halogens, cyano, alkyl, phenyl group, biphenyl group, arylthio, amine, ketone, aldehyde, alkoxy, hydroxy, carboxylic acid group, oligomer and combinations thereof and can have carbon atoms up to about 20; n is a whole number from 1 to 5; n' is a whole number from 0 to 4; n" is a whole number from 1 to 2 and each n" can be the same or different; q is an integer from 1 to 10; each Y is selected from the group consisting of --S(O) (O)--, --S(O)--, and --S--; each R can be selected from the group consisting of hydrogen, alkyl group, alkenyl group, aralkyl group, alkaryl group, and combinations thereof and can have 0 to about 10 carbon atoms; each OH group can be at either the 2'- or the 6'-position, or both.Type: GrantFiled: November 24, 1992Date of Patent: June 7, 1994Assignee: Phillips Petroleum CompanyInventors: Paul J. DesLauriers, Paritsoh K. Das, Darryl R. Fahey, Frederick J. Cornforth
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Patent number: 5319090Abstract: Hydrazide functionalized benzotrialzole and oxanilide ultraviolet absorbers (Formulas I and II) useful for stabilizing coreactive or inert polymeric compositions and novel intermediates (Formula III used to make certain types of compounds of Formula I) are disclosed and have the general formulas: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, X, Y, all substituents thereof, and n are set forth in the Summary of the Invention.Type: GrantFiled: May 18, 1993Date of Patent: June 7, 1994Assignee: Elf Atochem North America, Inc.Inventors: Ronald E. MacLeay, Terry N. Myers
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Patent number: 5292890Abstract: Provided are asymmetrical, ultraviolet stabilizers which are hydroxyphenyl benzotriazolylphenol compounds of the formula: ##STR1## wherein: R.sub.1 is C.sub.1 to C.sub.18 alkyl, C.sub.6 to C.sub.10 aryl, C.sub.7 to C.sub.16 arylalkyl, C.sub.1 to C.sub.12 alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.7 to C.sub.16 arylalkoxy, cyclopentyl, cyclohexyl or cumyl;R.sub.2 is C.sub.1 to C.sub.18 alkyl, C.sub.6 to C.sub.10 aryl, C.sub.7 to C.sub.16 arylalkyl, C.sub.1 to C.sub.12 alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.7 to C.sub.16 arylalkoxy, cyclopentyl, cyclohexyl or cumyl;R.sub.1 is different from R.sub.2 ; andX is selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.12 alkyl, and C.sub.1 to C.sub.12 alkoxy. The invention also pertains to a process for their preparation and stabilized polymer blends containing the stabilizers.Type: GrantFiled: May 5, 1993Date of Patent: March 8, 1994Assignee: Fairmount Chemical Company, Inc.Inventors: Semyon Moshchitsky, William E. Leistner
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Patent number: 5280124Abstract: 2-(2-Hydroxyphenyl)-2H-benzotriazole UV-absorbers substituted at the 5-position of the benzo ring by a sulfoxide or sulfone group exhibit enhanced absorption in the near visible range (over 350 nm) allowing said compounds to be particularly effective in protecting polymer systems which are prone to degradation caused by actinic irradiation with wavelengths over 350 nm.Type: GrantFiled: February 5, 1992Date of Patent: January 18, 1994Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Volker H. von Ahn, Tyler A. Stevenson, Mark S. Holt, Ramanathan Ravichandran
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Patent number: 5278314Abstract: 2-(2-Hydroxyphenyl)-2H-benzotriazole UV-absorbers substituted at the 5-position of the benzo ring by a thioether group exhibit enhanced absorption in the near visible range (over 350 nm) allowing said compounds to be particularly effective in protecting polymer systems which are prone to degradation caused by actinic irradiation with wavelengths over 350 nm.Type: GrantFiled: February 5, 1992Date of Patent: January 11, 1994Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Volker H. von Ahn, Tyler A. Stevenson, Mark S. Holt, Ramanathan Ravichandran
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Patent number: 5276161Abstract: 2-(2-Hydroxyphenyl)-2H-benzotriazoles of the formula ##STR1## in which R is hydrogen, C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.1 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl or phenyl-C.sub.1 -C.sub.4 alkyl and R.sub.2 is C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, phenyl-C.sub.1 -C.sub.4 alkyl or a group --C.sub.n H.sub.2n --COOR.sub.3, in which n is 0 to 4 and R.sub.3 is hydrogen or C.sub.1 -C.sub.12 alkyl, can be prepared particularly advantageously by catalytic hydrogenation of a suitable o-nitroazo compound in the presence of a Pt, Pd, Pt/Pd or Rh hydrogenation catalyst and an alkylenediamine or an acyclic or cyclic polyalkylene polyamine in a halogenated or nonhalogenated aromatic hydrocarbon as solvent.Type: GrantFiled: September 13, 1990Date of Patent: January 4, 1994Assignee: Ciba-Geigy CorporationInventors: Helmut Prestel, Rudolf Maul
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Patent number: 5262541Abstract: A process for producing 2-aryl-2H-benzotriazole by reducing an o-nitroazobenzene with a saccharide having an aldehyde group as a reducing agent in the presence of fluorenol as a catalyst and a base in solution. The reaction is conducted at a temperature of from about 60.degree. C. to about 80.degree. C. The reaction time and amount of catalyst is significantly reduced compared to the use of an aromatic ketone catalyst. The invention also provides a method for producing 2-aryl-2H-benzotriazole by reducing a 2-aryl-2H-benzotriazole-N-oxide intermediate with a saccharide having an aldehyde group as a reducing agent, in the presence of fluorenol under similar conditions.Type: GrantFiled: December 15, 1992Date of Patent: November 16, 1993Assignee: Fairmont Chemical Company, Inc.Inventors: Semyon Moshchitsky, William E. Leistner, Howard R. Leistner
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Patent number: 5250698Abstract: 2-(2-Hydroxy-3-perfluoroalkylthiomethyl-5-alkylphenyl)-2H-benzotriazoles are prepared by reacting the Mannich base hydrohalide or quaternary salt of a 2-(2-hydroxy-5-alkylphenyl)-2H-benzotriazole with a perfluoroalkyl mercaptan. The products exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.Type: GrantFiled: August 5, 1992Date of Patent: October 5, 1993Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Gregory R. Coughlin
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Patent number: 5232936Abstract: The present invention relates to novel hydantoin derivatives, processes for producing said hydantoin derivatives, pharmaceutical compositions containing at least one of said hydantoin derivatives as aldose reductase inhibitors and novel intermediate compounds in the synthesis of said hydantoin derivatives.The present invention is based on the selection of a hydantoin which is bonded by a sulfonyl group to various substituents at the 1-position of the hydantoin skeleton.The compounds of the present invention have a strong inhibitory activity against aldose reductase. These compounds are extremely useful for the treatment and/or prevention of various forms of diabetic complications based on the accumulation of polyol metabolites.Type: GrantFiled: January 23, 1991Date of Patent: August 3, 1993Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Ei Mochida, Kimihiro Murakami, Kazuo Kato, Katsuaki Kato, Jun Okuda, Ichitomo Miwa
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Patent number: 5229521Abstract: Compounds of formula ##STR1## wherein R.sub.1 is hydrogen alkyl, alkoxy, phenyl, phenylaklyl or halogen, and R.sub.2 is alkyl phenyl, phenylaklyl or cycloalkyl, are prepared by reacting a compound of formula ##STR2## with a compound of formula ##STR3## wherein R.sub.3 and R.sub.4 are alkyl, and formaldehyde, in a one-pot process in the absence of a solvent.Type: GrantFiled: October 23, 1992Date of Patent: July 20, 1993Assignee: Ciba-Geigy CorporationInventors: Reto Luisoli, Werner Stegmann
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Patent number: 5217983Abstract: (Indol-1'-ylmethyl)-, (Indazol-1'-ylmethyl)-, (Benzimidazol-1'-ylmethyl)-, and (Benzotriazol-1'-ylmethyl)- phenylacetaldehydes as Topical Antiinflammatories.Type: GrantFiled: March 27, 1992Date of Patent: June 8, 1993Assignee: Du Pont Merck Pharmaceutical CompanyInventor: Joseph J. Petraitis
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Patent number: 5206378Abstract: Ultraviolet light stabilizers are chemically bound to anhydride containing polymers or copolymers. Polymeric stabilizers are prepared by the reaction of primary amino or hydrazido-substituted UV absorbers with some or all of the anhydride groups of the polymer or copolymer to form pendant stabilizer substituted imide or amic acid groups. The polymer bound stabilizers are not lost from the polymer system by volatilization, migration, or extraction, even at high temperature. The polymer stabilizers of this invention may be used as they are or as concentrates to stabilize other polymer systems.Type: GrantFiled: November 14, 1991Date of Patent: April 27, 1993Assignee: Elf Atochem North America, Inc.Inventors: Ronald E. MacLeay, Terry N. Myers
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Patent number: 5190574Abstract: A herbicidal compound of formula (I): ##STR1## in which the dotted line indicates the presence of two double bonds arranged so as to form a fused hetero-aromatic ring system;Py is an optionally substituted pyrazole ring;W is O or NR.sup.1 ; where R.sup.1 is hydrogen or lower alkyl;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.5)CH.sub.2, COCH.sub.2 ;where n is 0, 1 or 2;R.sup.2 and R.sup.3 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.6 R.sup.7, or R.sup.2 and R.sup.3 together with the carbon to which they are attached form an optionally substituted alkenyl or cycloalkyl group;R.sup.4 is CO.sub.2 R.sup.8, CN, COR.sup.8, CH.sub.2 OR.sup.8, CH(OH)R.sup.8, CH(OR.sup.8)R.sup.9, CSNH.sub.2, COSR.sup.8, CSOR.sup.8, CONHSO.sub.2 R.sup.8, CONR.sup.10 R.sup.11, CONHNR.sup.10 R.sup.11, CONHN.sup.+ R.sup.10 R.sup.11 R.sup.12 R.sup.14-, CO.sub.2.sup.- R.sup.15+ or COON.dbd.CR.sup.10 R.sup.11 ;R.sup.15+ is an agriculturally acceptable cation and R.sup.Type: GrantFiled: February 7, 1991Date of Patent: March 2, 1993Assignee: Imperial Chemical Industries plcInventors: David P. J. Pearson, John E. D. Barton, Christopher J. Mathews, David Cartwright, Susan P. Barnett
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Patent number: 5187289Abstract: A method of preparing 2-phenylbenzotriazoles expressed by Formula I: ##STR1## (wherein R.sub.1 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a carboxyl group or a sulfonic acid group; R.sub.2 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxyl group having 1 to 4 carbon atoms; R.sub.3 denotes a hydrogen or chlorine atom, an alkyl group having 1 to 12 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a phenyl group, a phenyl group substituted by an alkyl group having 1 to 8 carbon atoms, a phenoxy group or a phenylalkyl group with an alkyl part having 1 to 4 carbon atoms; R.sub.4 denotes a hydrogen or chlorine atom, a hydroxyl group or an alkoxyl group having 1 to 4 carbon atoms; and R.sub.Type: GrantFiled: July 31, 1991Date of Patent: February 16, 1993Assignee: Chemipro Kasei Kaisha, Ltd.Inventors: Naohiko Fukuoka, Kazunobu Kubota, Kunitoshi Iguchi
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Patent number: 5157046Abstract: A method for treating skin disorders in warm-blooded animals, said method comprising administering to said warm-blooded animals an effective amount of an appropriately substituted benzimidazole or benzotriazole which suppresses the metabolism of retinoids. Compositions comprising said compounds and an effective amount of a retinoid.Type: GrantFiled: November 13, 1989Date of Patent: October 20, 1992Assignee: Janssen Pharmaceutica N.V.Inventors: Jean P. F. Van Wauwe, Alfons H. M. Raeymaekers
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Patent number: 5147902Abstract: An ultraviolet light absorbing occular lens comprising a vinyl type copolymer containing from 0.01 to 0.5% by weight of a benzotriazole type ultraviolet light absorbing monomer as chemically bonded therewith, the ultravioleet light absorbing monomer having the formula: ##STR1## (wherein R.sub.1 is H or CH.sub.3 and n is 2 or 3).Type: GrantFiled: November 26, 1991Date of Patent: September 15, 1992Assignee: Menicon Co., Ltd.Inventors: Makoto Ichikawa, Kazuharu Niwa, Kazuhiko Nakada
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Patent number: 5104992Abstract: A method of preparing 2-phenylbenzotriazoles expressed by Formula I: ##STR1## (wherein R.sub.1 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a carboxyl group or a sulfonic acid group; R.sub.2 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxyl group having 1 to 4 carbon atoms; R.sub.3 denotes a hydrogen or chlorine atom, an alkyl group having 1 to 12 carbon atoms, a lower alkoxy group having 1 to 4 carbon atoms, a phenyl group, a phenyl group substituted by an alkyl group having 1 to 8 carbon atoms, a phenoxy group or a phenylalkyl group with an alkyl part having 1 to 4 carbon atoms; R.sub.4 denotes a hydrogen or chlorine atom, a hydroxyl group or an alkoxyl group having 1 to 4 carbon atoms; and R.sub.Type: GrantFiled: April 2, 1990Date of Patent: April 14, 1992Assignee: Chemipro Kasei Kaisha, Ltd.Inventors: Naohiko Fukuoka, Kazunobu Kubota, Kunitoshi Iguchi
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Patent number: 5101059Abstract: This invention relates to compounds of the formula a compound of the formula ##STR1## wherein X is O, CR.sub.7 R.sub.8, S or NR.sub.9 wherein R.sub.7 and R.sub.8 are independently hydrogen, or lower alkyl, and R.sub.9 is lower alkyl;n is 0 or 1;R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, monoorganosilyl, diorganosilyl, triorganosilyl, halogen, aryl, or nitro;R.sub.3 is hydrogen, lower alkyl, monoorganosilyl, diorganosilyl, triorganosilyl, halogen, 9-fluorenylalkyl, cycloalkyl, aryl or aralkyl;R.sub.4 and R.sub.5 are independently hydrogen, lower alkyl, or aryl or one of R.sub.4 and R.sub.5 is 9-fluorenyl;R.sub.6 is H or COZ wherein Z is an amino acid, a peptide residue or a leaving group; andwith the provisos that when n is 0 and R.sub.3 is hydrogen, R.sub.1 and R.sub.2 are not hydrogen, halogen or nitro; that when n is 0 and R.sub.3 is lower alkyl, R.sub.1 and R.sub.2 are not hydrogen; and that when X is O or CR.sub.7 R.sub.8 wherein R.sub.7 and R.sub.8 are H, that R.sub.1, R.sub.2, R.sub.Type: GrantFiled: December 5, 1989Date of Patent: March 31, 1992Assignee: Research Corporation Technologies, Inc.Inventors: Louis A. Carpino, An-Chuu Wu
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Patent number: 5099027Abstract: Polymerizable ethylenically unsaturated monomers comprising the reaction product of a 1,2-epoxy group-containing polymerizable ethylenically unsaturated monomer and a 2(2-hydroxyphenyl)2H-benzotriazole compound of the structure: ##STR1## where X is=to H, OR and NR.sub.2 where R=alkyl; Z'=H and C.sub.2 H.sub.4 OH; Z and Y=H when Z'=C.sub.2 H.sub.4 OH; when Z'=H, Y and Z=OH or Y=H and Z.times.OH are disclosed. The monomers are useful in preparing free radical initiated addition polymers. Polymers can also be prepared by first preparing a free radical initiated addition polymer derived from a 1,2-epoxy group-containing polymerizable ethylenically unsaturated monomer and subsequently reacting the polymer with the benzotriazole compound. Both types of polymer contain permanent polymer-bound ultraviolet light stabilizers and are useful as binders for exterior coatings, as resins for the manufacture of optical lenses, and as components for sunscreens and suntanning lotions.Type: GrantFiled: September 15, 1988Date of Patent: March 24, 1992Assignee: PPG Industries, Inc.Inventors: Otto Vogl, Chongli Zhang
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Patent number: 5097040Type: GrantFiled: November 20, 1990Date of Patent: March 17, 1992Assignee: Shionogi & Co., Ltd.Inventors: Shigeru Narita, Takayasu Kitagawa
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Patent number: 5097041Abstract: There is disclosed a process in which a melt of a 2-aryl-2H-benzotriazole containing colored contaminants, or a solution thereof in an organic nonpolar solvent, is purified by treatment with a strongly acidic synthetic cationic exchange resin.Type: GrantFiled: October 11, 1990Date of Patent: March 17, 1992Assignee: Ciba-Geigy CorporationInventors: Ariane Higel, Sebastian Staubli, Daniel Thibaut, Hans Horisberger
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Patent number: 5086097Abstract: A thermoplastic molding composition comprising a polycarbonate resin and a benzotriazole ortho carbonate having an improved level of resistance to deterioration caused by exposure to ultraviolet radiation is disclosed. The ultraviolet stabilizer of the invention conforms to ##STR1## wherein R.sub.1 denotes a hydrogen or a halogen atom or a C.sub.1-4 alkyl or alkoxy group,R.sub.2 and R.sub.3 independently represent a hydrogen atom, a C.sub.1-12 alkyl, a C.sub.1-4 alkoxy group, a phenyl or a phenoxy radical, andR.sub.4 denotes a C.sub.1-12 alkylene or a C.sub.6-30 arylene group. The composition is suitable for the preparation of molded articles having an improved level of resistance to ultraviolet radiation.Type: GrantFiled: January 7, 1991Date of Patent: February 4, 1992Assignee: Mobay CorporationInventors: Steven A. Jorissen, Sivaram Krishnan
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Patent number: 5071995Abstract: Provided are 2-hydroxyphenylbenzotriazol compounds with excellent ultraviolet absorbability and high thermal stability. They can be used as ultraviolet absorber for any polymer.Type: GrantFiled: September 29, 1989Date of Patent: December 10, 1991Assignee: Kuraray Co., Ltd.Inventors: Tsugunori Kashimura, Tsutomu Miura, Keiji Matsumura
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Patent number: 5066656Abstract: (6,7-dihydro-5H-pyrrolo[1,2-c]imidazolyl-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridinyl-5-yl) substituted 1H-benzotriazole derivatives, compositions containing the same and methods of treating estrogen dependent disorders.Type: GrantFiled: September 10, 1990Date of Patent: November 19, 1991Assignee: Janssen Pharmaceutica N.V.Inventors: Michael N. Greco, Marcel A. C. Janssen
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Patent number: 5047554Abstract: This invention relates to novel 3-substituted-2-oxindole derivatives which are inhibitors of prostaglandin H.sub.2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H.sub.2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases. This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H.sub.2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.Type: GrantFiled: January 31, 1990Date of Patent: September 10, 1991Assignee: Pfizer Inc.Inventors: Frederick J. Ehrgott, Carl J. Goddard, Gary R. Schulte
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Patent number: 5047410Abstract: New pharmacologically active amidino and guanidino derivatives which are 5-HT.sub.3 receptor antagonists useful as antiemetic, gastric prokinetic and antimigrainic agents of the following general formula (I) ##STR1## , wherein the substituents are defined hereinbelow, which compounds are 5-HT.sub.3 receptor antagonists useful as antiemetic gastric prokinetic and antimigraine agents, inter alia.Type: GrantFiled: July 12, 1989Date of Patent: September 10, 1991Assignee: Istituto de Angeli S.p.A.Inventors: Arturo Donetti, Marco Turconi, Massimo Nicola, Rosamaria Micheletti
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Patent number: 5032657Abstract: Benzotriazole compounds having the formula: ##STR1## wherein R.sub.1 is H, Cl, or OCH.sub.3 ; R.sub.2 is a hydroxynaphthyl group; and R.sub.3 is a vinyl unsaturated polymerizable group. Homopolymers or copolymers thereof are effective as UV light stabilizers and absorbers.Type: GrantFiled: May 21, 1990Date of Patent: July 16, 1991Assignee: The United States of America as represented by the United States Department of EnergyInventors: Peter M. Gomez, Hermann H. Neidlinger
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Patent number: 5032498Abstract: The novel UV-absorbers are compounds of the formula ##STR1## in which R.sup.1 is, for example, hydrogen, n is one of the numbers 1 or 2 and R.sup.2 is an appropriate monovalent or divalent radical, for example --OH or --O-CH.sub.2 CH.sub.2 --O--. The UV-absorbers are used in particular for stabilising and improving lacquers and photographic material.Type: GrantFiled: August 21, 1990Date of Patent: July 16, 1991Assignee: Ciba-Geigy CorporationInventors: Jean Rody, Mario Slongo
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Patent number: 5026848Abstract: A heteroaryloxyalkylheterocyclic derivative of the Formula I:R--(CH.sub.2).sub.n --O--R.sup.1 Iis provided wherein:R is a non-fused azole moiety;n is 5, 6, 7 or 8; andR.sup.1 is a non-fused or fused substituted azole, azine, furyl or polycyclic hydrocarbon.Type: GrantFiled: March 27, 1989Date of Patent: June 25, 1991Assignee: Synphar Laboratories IncorporatedInventors: Mohsen Daneshtalab, Dai Q. Nguyen, Chan M. Ha, Hiep T. Luu, Laurence M. Tempest, Ronald G. Micetich
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Patent number: 5006660Abstract: The present invention relates to a process for producing an alkoxybenzene compound or an aryloxybenzene compound by reacting a halogenobenzene compound with an alcohol or a phenol compound in the presence of copper or a copper compound, an amine, and a base. According to the disclosure, an alkoxybenzene compound and an aryloxybenzene compound can be produced under moderate conditions in good yield with high selectivity.Type: GrantFiled: June 28, 1989Date of Patent: April 9, 1991Assignee: Fuji Photo Film Co., Ltd.Inventor: Katsuyoshi Yamakawa
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Patent number: 5003076Abstract: Novel fluorescent chiral derivatization reagent containing a compound of the formula: ##STR1## being useful for the determination of carboxylic acid enantiomers with high sensitivity, which are easily and well separated in a form of their consequent diastereomeric amides.Type: GrantFiled: September 26, 1989Date of Patent: March 26, 1991Assignee: Shionogi & Co., Ltd.Inventors: Shigeru Narita, Takayasu Kitagawa
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Patent number: 4958026Abstract: The disclosure relates to novel dopamine derivatives of general Formula I ##STR1## wherein A is a substituted phenyl residue of the structure ##STR2## wherein R.sup.1 and R.sup.2, being identical or different, mean hydrogen, C.sub.1-15 -alkyl and allyl,D is ##STR3## R.sub.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, CF.sub.3, NH.sub.2 E is ##STR4## X is OH, NH.sub.2, ##STR5## and NH--SO.sub.2 --CF.sub.3, if Y=OH, Y is OH, NH.sub.2, ##STR6## NH--SO.sub.2 --CF.sub.3 and NH--SO.sub.2 --CH.sub.3, if X=OH, but wherein X and Y do not simultaneously mean OH, with R.sup.3 being C.sub.1-4 -alkyl, andZ is H or OH, and, if Z means the hydroxy group, the residue A can also be present in the tautomeric basic form,and their acid addition salts, their preparation, and use as medicinal agents having antihypertensive activity.Type: GrantFiled: May 30, 1986Date of Patent: September 18, 1990Assignee: Schering AktiengesllschaftInventors: Klaus Schoellkopf, Rudolf Albrecht, Manfred Lehmann, Gertrud Schroeder