Naphthols Patents (Class 568/735)
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Patent number: 8835697Abstract: A biphenyl derivative having formula (1) is provided wherein Ar1 and Ar2 denote a benzene or naphthalene ring, and x and z each are 0 or 1. A material comprising the biphenyl derivative or a polymer comprising recurring units of the biphenyl derivative is spin coated and heat treated to form a resist bottom layer having improved properties, optimum values of n and k, step coverage, etch resistance, heat resistance, solvent resistance, and minimized outgassing.Type: GrantFiled: March 20, 2012Date of Patent: September 16, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Daisuke Kori, Takeshi Kinsho, Katsuya Takemura, Tsutomu Ogihara, Takeru Watanabe, Hiroyuki Urano
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Publication number: 20130274487Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of specific ruthenium catalysts, or pre-catalysts, in hydrogenation processes for the reduction of ketones and/or aldehydes into the corresponding alcohol respectively. Said catalysts are ruthenium complexes comprising a tetradentate ligand (L4) coordinating the ruthenium with: two nitrogen atoms, each in the form of a primary or secondary amine (i.e. a NH2 or NH group) or N-alkyl imine functional groups (i.e. a C?N group), and two sulfur atoms, each in the form of thioether functional groups.Type: ApplicationFiled: December 19, 2011Publication date: October 17, 2013Applicant: FIRMENICH SAInventors: Sylvia Joyeuse Adélaïde Ada Saudan, Michel Alfred Joseph Saudan
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Publication number: 20100264359Abstract: The present invention relates to biocidal mixtures containing at least one biocide that is not a polyamine and at least one polyamine, and also to the use of the abovementioned biocidal mixtures in material protection. A special aspect of the invention relates in addition to a method for decolorizing and/or preventing discolorations of pyrithione-containing industrial materials by polyamines.Type: ApplicationFiled: September 24, 2008Publication date: October 21, 2010Applicant: LANXESS DEUTSCHLAND GMBHInventors: Udo Straetmans, Felix Straetmans
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Publication number: 20100145060Abstract: Embodiments of the invention provide a method of using Schwartz Reagent, Cp2Zr(H)Cl, without accumulating or isolating it. Methods provide mixtures of Cp2ZrCl2, reductants that selectively reduce Cp2ZrCl2, and substrates. After reaction of Cp2ZrCl2 and the reductant, an intermediate reduction product is formed, apparently Schwartz Reagent. The in situ Schwartz Reagent then selectively reduces certain functional groups on the substrate. Substrates include tertiary amides, tertiary benzamides, aryl O-carbamates, and heteroaryl N-carbamates, which are reduced to aldehydes, benzaldehydes, aromatic alcohols, and heteroaromatics, respectively. Compared to prior methods, reagents are inexpensive and stable, reaction times are short, and reaction temperature in certain cases is conveniently room temperature. It has been estimated that using the in situ method described herein instead of synthesized or commercially obtained Schwartz Reagent provides a 50% reduction in cost.Type: ApplicationFiled: December 3, 2009Publication date: June 10, 2010Inventors: Yigang Zhao, Victor A. Snieckus
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Publication number: 20090253919Abstract: Chiral thioureas are effective catalysts for the borane reduction of prochiral ketones to optically active alcohols. A prochiral ketone may be reduced to an optically active alcohol in the presence of a substantially sub-stoichiometric amount of chiral thiourea. The asymmetric thiourea compound of the present invention may be produced according to a production method described herein.Type: ApplicationFiled: April 3, 2008Publication date: October 8, 2009Applicant: Board of RegentsInventors: Derun Li, John R. Falck
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Patent number: 7449608Abstract: The present invention provides a novel naphthol derivative represented by the following general formula (I). The novel naphthol derivative of the present invention is useful as a positively electrifiable charge control agent. The present invention further provides an electrophotographic toner comprising a charge control agent comprising the novel naphthol derivative represented by formula (I).Type: GrantFiled: December 10, 2002Date of Patent: November 11, 2008Assignee: Ueno Fine Chemicals Industry, Ltd.Inventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori, Nobuhiro Yonetani
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Publication number: 20080227978Abstract: A process for converting a carbonyl group within a substrate to a chiral alcohol moiety comprising reacting the carbonyl containing substrate with an organoaluminium reagent in the presence of a Group 5-12 transition metal based catalyst which is complexed with a chiral ligand; novel chiral ligands and organoluminium reagents, a chiral ligand or organoaluminium reagent for use in the process.Type: ApplicationFiled: January 26, 2006Publication date: September 18, 2008Inventor: Simon Woodward
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Publication number: 20080214507Abstract: Compounds of formula II wherein each R1 and R2 is independently selected from H and —P(O)(R3)(R4), provided that at least one of R1 and R2 is —P(O)(R3)(R4); each R3 and R4 is independently selected from the group consisting of H, —OH, C1-C6 alkyl and C1-C6 alkoxy; or a pharmaceutically acceptable salt thereof. Pharmaceutical compositions comprising a compound of formula II, and methods of administering such compounds and compositions.Type: ApplicationFiled: February 20, 2008Publication date: September 4, 2008Applicant: WYETHInventors: Mahdi B. FAWZI, Parimal R. DESAI, Tianmin ZHU
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Patent number: 7151070Abstract: The compound of this invention is a useful catalyst for the oxidative coupling of naphthol. Its originality lies in that it is a novel vanadium complex of Schiff's base formed by a chiral amino acid and a formyl biphenol or its derivative. Its axis chirality is induced to form by the chiral amino acid. It has the general formula: where R represents a benzyl, an isopropyl, an isobutyl or a tertiary butyl and the configuration of the amino acid is R or S. The compound can catalyze oxidative coupling of naphthol or its derivative to form binaphthol or its derivatives with a high optical purity.Type: GrantFiled: February 27, 2003Date of Patent: December 19, 2006Assignee: Chengdu Institute of Organic Chemistry Chinese Academy of SciencesInventors: Liuzhu Gong, Zhibin Luo, Quanzhong Liu, Aiqiao Mi, Yaozhong Jiang
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Patent number: 7135590Abstract: This invention provides a plant growth regulatory activity of a new biologically active synthetic molecule methanone-(3?,4?,5?-trimethoxy) phenyl, 1-naphthyl, 2-O-4?-ethyl but-2?-enoate. More particularly, the invention relates to the potent plant growth promoting activity of a gallic acid derivative having a structure represented by Formula 1 and a molecular formulae C26H26O7. This invention also provides a novel process for preparation of said molecule from a naturally occurring compound and testing it for growth regulating activity using Bacopa test system developed at CIMAP (Khanuja et al.Type: GrantFiled: August 17, 2004Date of Patent: November 14, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Suman Preet Singh Khanuja, Mahendra Pandurang Darokar, Ankur Garg, Togarrati Padmapriya, Ajit Kumar Shasany, Arvind Singh Negi, Sunia Kumar Chattopadhyay, Kachin Srivastava, Asish Kumar Bhattacharya
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Patent number: 6911563Abstract: A method for carrying out a reaction of one substance capable of being activated by a catalyst with another substance capable of reacting with said one substance activated, characterized in that the substance capable of being activated is activated by passing the substance through a diaphragm type catalyst and the reaction is thus performed in one reaction step; a method for producing an aromatic alcohol utilizing the above method; and a reaction apparatus suitable for these reactions. In the method, one substance is activated by passing through a diaphragm type catalyst and an objective reaction is carried out by using the activated substance, and the reaction can be performed in one reaction step and with safety. Moreover, the contact of the above activated substance with a compound to be reacted therewith can be freely controlled, and therefore, over-reaction can be prevented and an objective product can be produced in high yield.Type: GrantFiled: December 27, 2001Date of Patent: June 28, 2005Assignees: National Institute of Advanced Industrial Science, NOK CorporationInventors: Fujio Mizukami, Shuichi Niwa, Makoto Toba, Naotsugu Itoh, Tomonari Saito, Takemi Nanba, Hiroshi Shoji, Kazuhiko Haba
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Patent number: 6838583Abstract: An antimicrobial compound, composition containing such compound, and method of use of the same for reducing the presence of microorganism on a substrate or in a fluid environment comprising an antimicrobial effective carrier and one or more essential antimicrobial compounds including non-halogenated naphthol compounds.Type: GrantFiled: May 20, 2003Date of Patent: January 4, 2005Assignee: Warner-Lambert Company LLCInventors: David Scott Harper, Robert A. Coburn, Andre Soshinsky, Constantine Georgiades, Marianne D. Huntley
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Patent number: 6784228Abstract: The present invention relates to an epoxy resin composition a cure article thereof, a novel epoxy resin used therein, a polyhydric phenol compound suited for used as an intermediate thereof, and a process for preparing the same. One of the objects to be achieved by the present invention is to exert the heat resistance, the moisture resistance, the dielectric performances and the flame-resistant effect required of electric or electronic materials such as semiconductor encapsulating materials and varnishes for circuit boards in the epoxy resin composition.Type: GrantFiled: July 9, 2002Date of Patent: August 31, 2004Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Ichiro Ogura, Yoshiyuki Takahashi, Tomoyuki Imada
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Publication number: 20040133047Abstract: The present invention relates to a one-pot process for preparing a compound of formula I: I; by reacting a compound of formula II with a compound of formula III: in the presence of a suitable solvent, a suitable base, a palladium catalyst and a suitable ligand.Type: ApplicationFiled: May 20, 2003Publication date: July 8, 2004Inventors: Scott Allan May, Thomas Michael Wilson, Tony Yantao Zhang
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Patent number: 6563008Abstract: Novel intermediates of Formula IV wherein the substituents are as defined in the specification and a process for preparing the same.Type: GrantFiled: June 29, 2001Date of Patent: May 13, 2003Assignee: Aventis Pharma S.A.Inventors: Dominique Lesuisse, Jean-Georges Teutsch
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Publication number: 20020110530Abstract: An antimicrobial compound, composition containing such compound, and method of use of the same for reducing the presence of microorganism on a substrate or in a fluid environment comprising an antimicrobial effective carrier and one or more essential antimicrobial compounds including non-halogenated naphthol compounds.Type: ApplicationFiled: December 20, 2001Publication date: August 15, 2002Inventors: David Scott Harper, Robert A. Coburn, Andre Soshinsky, Constantine Georgiades, Marianne D. Huntley
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Patent number: 6395904Abstract: The subject invention provides a binuclear metal complex having structure (I) wherein M1, and M2 are independently selected from the group consisting of Fe, Co, Mn and Ru; wherein m and n are independently +2 or +3; wherein R1, R2, R3, R4, R5 and R6 are independently a linear C1-C6 alkyl, C5-C6 cycloalkyl, phenyl, etc.; wherein (i) R1 and R2, (ii) R3 and R4, or (iii) R5 and R6 independently and optionally are linked covalently and together with the respective adjoining C atom comprise a spirocyclic ring; wherein i, j and k are integers such that 2≦i+j+k≦4; wherein p is 1 or 2, and q is 0, 1 or 2 such that m+n−4=p×q; wherein (i) R1 or R2 and R3 or R4, (ii) R3 or R4 and R4 or R5, or (iii) R1 or R2 and R5 or R6 independently and optionally are linked covalently and together with the respective adjoining C atoms comprise a fused ring; wherein Ar is 1,2-phenylene, 1,2- or 2,3-naphthylene, etc.Type: GrantFiled: June 6, 2000Date of Patent: May 28, 2002Assignee: Yale UniversityInventors: John P. Caradonna, Subhasish Mukerjee, Adonis Stassinopoulos
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Publication number: 20010039365Abstract: A method and composition are disclosed for the hydroxylation of aromatic substrates in the presence of oxygen, hydrogen, and a catalyst. In a preferred embodiment, benzene is oxidized to phenol in the presence of oxygen, a vanadium catalyst, and hydrogen. The method is economical, safe, and amenable to commercial scale-up.Type: ApplicationFiled: January 16, 2001Publication date: November 8, 2001Inventor: Terence Michael Barnhart
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Publication number: 20010031887Abstract: An optically active binaphthol derivative of the following formula (1) or (2), an optically active phosphate derivative of the following formula (3) or (4), processes for their production, and an asymmetry identifying agent comprising the derivative of the formula (3) or (4): 1Type: ApplicationFiled: March 8, 2001Publication date: October 18, 2001Inventor: Junji Inanaga
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Patent number: 6252124Abstract: A new phenol and acetone production process reduces the amount of necessary stages for obtaining phenol and acetone, results in higher yield of desired products and requires less complex equipment implementation and less energy than current processes of a similar type.Type: GrantFiled: April 29, 1999Date of Patent: June 26, 2001Assignee: ILLA International, LLCInventors: Vladimir Mikhailovitch Zakoshansky, Irina Ivanovna Vassilieva
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Patent number: 6090969Abstract: A process for producing an asymmetric compound using a metal complex containing no rare earth metal element is disclosed. The process affords an optically active compound having high optical purity. Optically active binaphthol having the chemical formula and lithium aluminum hydride are reacted, or the optically active binaphthol, a dialkyl aluminum hydride, and a base containing an alkali metal (or a base containing alkaline earth metal) are reacted to prepare a metal complex comprising optically active binaphthol, aluminum, and alkali metal (or alkaline earth metal). This metal complex can be used as a catalyst to perform an asymmetric Michael reaction, an asymmetric phosphonylation reaction, or the like, to obtain, in a high yield, an asymmetric compound having high optical purity.Type: GrantFiled: September 8, 1998Date of Patent: July 18, 2000Assignee: Nagase and Co., Ltd.Inventors: Masakatsu Shibasaki, Hiroaki Sasai, Takayoshi Arai
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Patent number: 5981806Abstract: The present invention relates to a process for the preparation of hydroxynaphthalenes of formula (I) ##STR1## wherein n represents a number from 1 to 6,X denotes C.sub.1 -C.sub.6 alkyl, halogen, carboxyl, carboxylic acid ester, nitro, chlorosulphonyl, arylsulphonyl, hydroxyl, alkoxy, acyloxy, or an amino or aminosulphonyl that is unsubstituted or N-substituted with alkyl or aryl, or two radicals X, together with the adjacent carbon atoms to which they are bonded, form a fused-on aromatic, cycloaliphatic, or heterocyclic ring, andm denotes a number from 0 to 6, wherein if m is greater than 1, then each X can have different or identical meanings,by reacting(1) a naphthalenesulphonic acid of formula (II) or a salt thereof ##STR2## wherein n and m have the above meanings and X.sub.1 has the same meaning as X or is SO.sub.3 H, with(2) alkali in the presence of(3) an alkylated urea derivative.Type: GrantFiled: March 2, 1998Date of Patent: November 9, 1999Assignee: Bayer AktiengesellschaftInventor: Thomas Pelster
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Patent number: 5962002Abstract: This invention relates to 1,1,1,4-substituted naphthaline compounds, compositions, processes for their preparation and processes for their use as pesticides, especially insecticides, acaricides and fungicides.Type: GrantFiled: July 10, 1997Date of Patent: October 5, 1999Assignee: BTG International LimitedInventors: Bhupinder Pall Singh Khambay, Duncan Batty, Stuart Cameron, David Gordon Beddie
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Patent number: 5952532Abstract: A process is disclosed for the catalytic hydroxylation of aromatic hydrocarbons which comprises contacting aromatic feedstock with oxidant comprising molecular oxygen, under suitable reaction conditions, in the presence of a catalyst comprising three essential components: a support; transition metal selected from the group consisting of vanadium, niobium, copper, palladium, nickel and silver, or combinations thereof, and a promoter comprising a multidentate chelating, binucleating ligand. The catalysts may further comprise additional metal ions. The process is particularly suited, for example, to the one-step conversion of benzene to phenol.Type: GrantFiled: July 31, 1997Date of Patent: September 14, 1999Assignee: Sunoco, Inc.Inventors: Vincent A. Durante, Tilak P. Wijesekera, Swati Karmakar
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Patent number: 5907069Abstract: In producing nabumetone or precursor thereof, use is made of 2-bromo-6-methoxynaphthalene formed by (a) methylating 6-bromo-2-naphthol with methyl bromide or methyl chloride, in a halogen-free liquid solvent comprising at least about 40% by weight of one or more compounds of the formula RZ where R is a hydrogen atom or an alkyl group, and Z is a hydroxyl group or a cyanide group with the proviso that if Z is a cyanide group, R is an alkyl group, and in the presence of at least one strong base; and (b) recovering and purifying 2-bromo-6-methoxynaphthalene so formed.Type: GrantFiled: January 20, 1998Date of Patent: May 25, 1999Assignee: Albemarle CorporationInventors: Brian F. Becnel, Mahmood Sabahi, Kevin J. Theriot
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Patent number: 5892038Abstract: Compounds of Formula I ##STR1## are disclosed as inhibitors of plasmepsin and cathepsin D. The compounds are therefore useful to treat diseases such as malaria. In preferred compounds of formula I, Y is the residue of an N-acylated amino acid, a substituted 4-aminoproline or a substituted piperazinealkanoic acid. Intermediates in the solid phase synthesis of compounds of formula I, in which the compounds are attached to a solid support, are also disclosed.Type: GrantFiled: December 8, 1997Date of Patent: April 6, 1999Assignee: Pharmacopeia, Inc.Inventors: Roland Ellwood Dolle, III, Hitesh K. Patel
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Patent number: 5874588Abstract: Diketopyrrolopyrroles of formula I ##STR1## are prepared by reacting a diketopyrrolopyrrole of formula II ##STR2## with a) formic acid or b) a compound of formula IIIX'--H (III)or with an alkali metal formate or alkaline earth metal formate together with carbon monoxide in the presence of a catalyst, wherein, in formulae I, II and III, A is a direct bond or a group ##STR3## wherein phenylene is bound to the pyrrolopyrrole, R.sub.1, R.sub.2 and R.sub.3 are each independently of one another hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylamino, C.sub.1 -C.sub.6 alkylmercapto, --CF.sub.3, --CN or --NO.sub.2, X is X' or OH, X' is --OR.sub.4 or --N(R.sub.5)(R.sub.6), wherein R.sub.4 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.6 cycloalkyl; phenyl or naphthyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylamino, --CN or --NO.sub.2, R.sub.5 and R.sub.Type: GrantFiled: September 19, 1997Date of Patent: February 23, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Bernd Lamatsch, Olof Wallquist
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Patent number: 5872289Abstract: A liquid-phase process for hydrolyzing a carboxylic acid alkyl ester having 2 to 18 carbon atoms to provide a product mixture comprising a carboxylic acid and an alcohol comprising contacting a feedstock comprising the carboxylic acid alkyl ester and water with an acidic carbon catalyst under reaction conditions sufficient to form the product mixture comprising the carboxylic acid and the alcohol. Suitable acidic carbon catalysts include charcoal and carbons produced from a variety of sources including coconut shells, coal, wood and peat. Carbon catalysts may be rendered acidic by treatment with nitric acid.Type: GrantFiled: March 6, 1998Date of Patent: February 16, 1999Assignee: Air Products and Chemicals, Inc.Inventors: John Bruce Appleby, Francis Joseph Waller, Stephen Charles Webb
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Patent number: 5859067Abstract: Use of a compound of formula (I), wherein Ar is an aromatic ring system comprising one or more optionally substituted phenyl rings optionally linked to or fused with one or more other optionally substituted phenyl rings or one or more 5 or 6-membered, optionally substituted heterocyclic rings wherein the heteroatom is oxygen; and wherein the ring system comprises 1-4 phenyl rings and wherein Ar can be linked to another Ar via a group X wherein the Ar is independently selected; where X is optionally substituted C.sub.1-20 alkylene, C.sub.2-20 alkenylene or C.sub.2-20 alkynylene; R is hydrogen; C.sub.1-20 alkenyl, C.sub.2-20 alkynyl, C.sub.2-20 alkanoyl, C.sub.2-20 alkynoyl, each of which can be optionally substituted; R.sub.1 is independently selected and is hydrogen; optionally substituted C.sub.1-12 alkyl, C.sub.2-12 alkenyl, C.sub.2-12 alkynyl; --COOR'--NR'R', halogen, --OR', --COR', --CONR'R', .dbd.O, --SR', --SO.sub.3 R', --SO.sub.2 NR'R', --SOR', --SO.sub.2 R', --NO.sub.Type: GrantFiled: November 12, 1997Date of Patent: January 12, 1999Inventors: Basil Don Roufogalis, Colin Charles Duke, Qian Li
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Patent number: 5847233Abstract: A naphthol derivative represented by the general formula (I) ?wherein Y and Y' indicate --(CONH).sub.n --X or --COR; X is a phenyl group, a naphthyl group, an anthraquinonyl group, a benzimidazolonyl group or a carbazolyl group; R is a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, a halogen atom, a benzyloxy group, a phenyloxy group or a phenacyloxy group; R.sub.2 is a hydrogen atom, an alkaline metal, an alkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms or a phenylalkyl group; Z is a group selected from the group consisting of a hydrogen atom, a halogen atom, a nitro group, a nitroso group and an amino group (Z may be substituted on any ring of the naphthalene ring); and n is an integer of 1 or 2; provided that R.sub.2 and Z do not simultaneously indicate a hydrogen atom when both R simultaneously indicate a hydroxyl group!, and a process for producing the same.Type: GrantFiled: November 20, 1997Date of Patent: December 8, 1998Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Shigeru Ito, Kenji Minami, Masaya Kitayama
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Patent number: 5840999Abstract: A class of asymmetric monobenzoxanthene compounds useful as fluorescent dyes are disclosed having the structure ##STR1## wherein Y.sub.1, and Y.sub.2 are individually hydroxyl, amino, imminium, or oxygen, R.sub.1 -R.sub.8 are hydrogen, fluorine, chlorine, alkyl alkene, alkyne, sulfonate, amino, amido, nitrile, alkoxy, linking group, and combinations thereof, and R.sub.9 is acetylene, alkane, alkene, cyano, substituted phenyl and combinations thereof The invention ftrther includes novel intermediate compounds useful for the synthesis of asymmetric benzoxanthene compounds having the general structure ##STR2## where substituents R.sub.3 -R.sub.7 correspond to like-referenced substituents in the structure of described above, and Y.sub.2 is hydroxyl or amine. In another aspect, the invention includes methods for synthesizing the above dye compounds and intermediates.Type: GrantFiled: March 26, 1997Date of Patent: November 24, 1998Assignee: The Perkin-Elmer CorporationInventors: Scott C. Benson, Steven M. Menchen, Peter D. Theisen, Kevin M. Hennessey, Vergine C. Furniss, Joan Hauser
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Patent number: 5798443Abstract: The present invention relates to a reaction and dissolving medium for the synthesis of peptides. This reaction and dissolving medium for peptide synthesis and/or purification comprises a diluent A chosen from a group of water-immiscible solvents and a phenol B. This peptide synthesis can be used to synthesize medicaments, vaccines, agro-foodstuff products or plant protection products.Type: GrantFiled: March 10, 1994Date of Patent: August 25, 1998Assignee: Rhone-Poulenc ChimieInventors: Marie Galvez, Marie-France Maurice
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Patent number: 5786523Abstract: A naphthol derivative represented by the general formula (I) ?wherein Y and Y' indicate --(CONH).sub.n --X or --COR; X is a phenyl group, a naphthyl group, an anthraquinonyl group, a benzimidazolonyl group or a carbazolyl group; R is a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, a halogen atom, a benzyloxy group, a phenyloxy group or a phenacyloxy group; R.sub.2 is a hydrogen atom, an alkaline metal, an alkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms or a phenylalkyl group; Z is a group selected from the group consisting of a hydrogen atom, a halogen atom, a nitro group, a nitroso group and an amino group (Z may be substituted on any ring of the naphthalene ring); and n is an integer of 1 or 2; provided that R.sub.2 and Z do not simultaneously indicate a hydrogen atom when both R simultaneously indicate a hydroxyl group!, and a process for producing the same.Type: GrantFiled: November 18, 1997Date of Patent: July 28, 1998Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Shigeru Ito, Kenji Minami, Masaya Kitayama
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Patent number: 5716624Abstract: Novel pharmaceutically/cosmetically-active polyaromatic propynyl compounds have the structural formula (1): ##STR1## in which X is one of the radicals: ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: December 15, 1994Date of Patent: February 10, 1998Assignee: C.I.R.D. GaldermaInventor: Jean-Michel Bernardon
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Patent number: 5684152Abstract: Carboxy-peptidyl compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophobic epidermolysis bullosa, coronary thrombosis associated with atherosclerotic plaque rupture, and aneurysmal aortic disease. This invention relates to a process of making the carboxy-peptidyl compounds of formula I.Type: GrantFiled: September 19, 1996Date of Patent: November 4, 1997Assignee: Merck & Co., Inc.Inventors: Mitree M. Ponpipom, William K. Hagmann
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Patent number: 5543564Abstract: This invention embodies a process for releasing acidic organic compounds in high yield and good purity from aqueous solutions of their salts which comprises converting the salts by carbon dioxide to their corresponding free acidic organic compounds and metal hydrogen carbonates, removing the acidic organic compounds from the mixture by extraction with an essentially water-insoluble organic solvent, and re-extracting the organic phase with carbon dioxide containing water. Using this process, the acidic organic compounds are completely released from their corresponding salts, i.e., the organic solution is free of salt. The acidic organic compounds released by the claimed process are organic compounds which contain acidic protons which can be replaced by metals. Some examples are carboxylic acids, sulfonic acids, phosphonic acids, phenols, naphthols, and aliphatic alcohols.Type: GrantFiled: January 11, 1995Date of Patent: August 6, 1996Assignee: Hoechst AktiengesellschaftInventors: J urgen Kulpe, Heinz Strutz, Hans-Martin R uffer, Siegbert Rittner
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Patent number: 5510520Abstract: The present invention provides three optical resolution methods. The first aspect comprises the steps of adding an optically active bifunctional resolving reagent to a bifunctional compound to form a liquid material, precipitating crystals therefrom, and treating the crystals and the liquid material separately with an acidic material, a basic material, or a basic material and an acidic material, to obtain a pair of enantiomers of an optically active bifunctional compound. The second aspect comprises an optical resolution method by which one necessary enantiomer of a pair of enantiomers in an optically active bifunctional compound is exclusively obtained. The third aspect comprises a method for racemizing one unnecessary enantiomer of a pair of enantiomers in an optically active bifunctional compound which is formed by the optical resolution method of the present invention.Type: GrantFiled: August 19, 1994Date of Patent: April 23, 1996Assignee: Kankyo Kagaku Center Co., Ltd.Inventor: Masatoshi Kawashima
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Patent number: 5426243Abstract: An improved process for the preparation of 1,6-dibromo-2 -naphthol is disclosed. The improvement is accomplished by carrying out the reaction in an organic solvent at a temperature of from about 40.degree. to about 60.degree. C. in the presence of a catalytically-effective amount of a compound of the formula: ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and are alkyl, cycloalkyl, phenyl, substituted phenyl, naphthyl, substituted naphthyl heteroaryl, substituted heteroaryl or R.sub.1 taken together with R.sub.2 and the nitrogen atom form a heteroaryl or substituted heteroaryl group in which the heteroatom is nitrogen and X is an inorganic anion.Type: GrantFiled: August 17, 1994Date of Patent: June 20, 1995Assignee: Albemarle CorporationInventor: Jean-Pierre Lecouve
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Patent number: 5422038Abstract: Optically active naphthalene derivatives including optically active naphthylcarboxylic acid derivative, hydroxynaphthalene derivative, alkoxynaphthylalkanol derivative and alkylnaphthylalkanol derivative have the following structural formula: ##STR1## wherein R.sup.1 denotes an alkyl group of 3-20 carbon atoms, R.sup.2 denotes an alkyl group of 1-20 carbon atoms optionally substituted with halogen atom(s) or an alkoxyalkyl group of 2-20 carbon atoms optionally substituted with halogen atom(s), X denotes --COO-- or --OCO--, k, l and m denotes 0 or 1 respectively, n denotes an integer of 0-6, p denotes 0 or 1, and the asterisk indicates an asymmetric carbon atom, with the proviso that when k is 0, l and m are not 1 at the same time, and when k is 1, m is 1, and when n is 0 and m is 1, X is --COO--.Type: GrantFiled: December 14, 1993Date of Patent: June 6, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Shoji Toda, Takayuki Higashii, Isao Kurimoto, Masayoshi Minai, Chizu Sekine, Takeshi Tani, Koichi Fujisawa
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Patent number: 5420362Abstract: 4-Halo-1-naphthol is reacted with a secondary amine and formaldehyde to produce a reaction mixture containing a Mannich base which is hydrogenated to produce 2-methyl-1-naphthol. Advantageously, the procedure can be carried out in one pot.Type: GrantFiled: October 8, 1993Date of Patent: May 30, 1995Assignee: Clairol, Inc.Inventors: Mu-Ill Lim, Linas Stasaitis, Yuo-Guo Pan, Alexander Chan
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Patent number: 5395962Abstract: The present invention provides three optical resolution methods. The first aspect comprises the steps of adding an optically active bifunctional resolving reagent to a bifunctional compound to form a liquid material, precipitating crystals therefrom, and treating the crystals and the liquid material separately with an acidic material, a basic material, or a basic material and an acidic material, to obtain a pair of enantiomers of an optically active bifunctional compound. The second aspect comprises an optical resolution method by which one necessary enantiomer of a pair of enantiomers in an optically active bifunctional compound is exclusively obtained. The third aspect comprises a method for racemizing one unnecessary enantiomer of a pair of enantiomers in an optically active bifunctional compound which is formed by the optical resolution method of the present invention.Type: GrantFiled: November 16, 1992Date of Patent: March 7, 1995Assignee: Kankyo Kagaku Center Co., Ltd.Inventor: Masatoshi Kawashima
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Patent number: 5256829Abstract: Dibrominated naphthol compounds, e.g., 1,6-dibromo-2-hydroxynaphthalene, are regioselectively catalytically hydromonodebrominated, e.g., into 6-bromo-2-hydroxynaphthalene, by reacting such dibromonaphthols with molecular hydrogen, or a precursor compound that generates nascent hydrogen in the medium of reaction, in an acidic organic solvent and in the presence of a catalytically effective amount of a tungsten carbide-based catalyst.Type: GrantFiled: October 2, 1992Date of Patent: October 26, 1993Assignee: Potasse et Produits ChimiquesInventor: Roland Jacquot
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Patent number: 5233097Abstract: Certain crystalline titanoaluminosilicate molecular sieve compositions having titanium, aluminum, and silicon present as framework tetrahedral oxide units are particularly effective in hydroxylating the aromatic nucleus of aromatic compounds using hydrogen peroxide, even where the hydrogen peroxide is used at concentrations of 10 weight percent or less. The variant where the exchangeable hydrogens of the titanoaluminosilicate are replaced by an alkali or alkaline earth metal cation is particularly favored because of the concomitant increase in selectivity. Excellent utilization of hydrogen peroxide often is observed, even when the hydroxylation is effected at temperatures under about 60.degree. C.Type: GrantFiled: October 15, 1992Date of Patent: August 3, 1993Assignee: UOPInventors: Laszlo T. Nemeth, Eric M. Hyatt, Thomas P. Malloy
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Patent number: 5180742Abstract: Quinone derivatives of the general formula: ##STR1## (wherein R.sup.1 and R.sup.2 are the same or different, and independently are a hydrogen atom or a methyl or methoxy group, or R.sup.1 and R.sup.2 combine with each other to represent --CH.dbd.CH--CH.dbd.CH--R.sup.3 is a hydrogen atom or a methyl group; R.sup.4 is an aliphatic, aromatic or heterocyclic group which may be substituted; R.sup.5 is a methyl or methoxy group, a hydroxymethyl group which may be substituted or a carboxyl group which may be esterified or amidated; Z is a group represented by --C.dbd.C--, --CH.dbd.CH--, ##STR2## n is an integer of 0 to 10; m is an integer of 0 to 3; k is an integer of 0 to 5, provided, however, that in the case of m being 2 or 3, Z and k can vary arbitrarily within the bracketed repeating units) are novel compounds, possess metabolism ameliorating action for polyunsaturated fatty acids, particularly production inhibitory activity of lipid peroxides (antioxidant activity), thromboxane A.sub.Type: GrantFiled: January 9, 1987Date of Patent: January 19, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Yoshitaka Maki
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Patent number: 5087769Abstract: A method of forming 6-substituted-2-vinyl naphthalene from a 2-substituted naphthalene compound wherein the substituent in the 2-position is an ortho-para directing electron-donating group not reactive with hydrogen fluoride, comprises contacting the naphthalene compound and an acylating agent with substantially anhydrous hydrogen fluoride to acylate the naphthalene compound to a 6-substituted-2-acylnaphthalene compound, hydrogenating the 6-substituted-2-acylnaphthalene compound to convert the 2-acyl substituent to an alcohol substituent, dehydrating the product of hydrogenation in the presence of a free radical inhibitor to convert the alcohol substituent to an olefinic substituent, and isolating the formed 6-substituted-2-vinylnaphthalene subsequent to the dehydration.Type: GrantFiled: September 26, 1990Date of Patent: February 11, 1992Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Henry C. Linstid, III., Kenneth G. Davenport
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Patent number: 5043483Abstract: Process for the alkylation of phenols comprising reacting a phenol with a vinyl-aromatic hydrocarbon in the presence of an acidic catalyst and of a solvent.Type: GrantFiled: November 28, 1988Date of Patent: August 27, 1991Assignee: Montedison S.p.A.Inventors: Loris Sogli, Raffaele Ungarelli, L. Lawrence Chapoy
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Patent number: 5041639Abstract: New polysubstituted derivatives of naphthalene. These derivatives correspond to the following formula: ##STR1## in which: R.sub.1 to R.sub.4 is H or CH.sub.3R.sub.5 is ##STR2## or (iv) the radical: 2-oxazolinyl m is 0 or 1R.sub.8.sbsb.r is H, alkyl, OR.sub.11, R.sub.11 being H, alkyl or ##STR3## R.sub.13 being alkyl or aryl or R.sub.8 is ##STR4## when m=1, r' and r" representing H, alkyl mono or polyhydroxyalkyl, aryl or a heterocycle when they are taken together, R.sub.9 is H or alkyl, R.sub.10 is H, alkyl and the acetals of the said compounds ##STR5## --OR.sub.14, R.sub.14 being H, alkyl, mono or polyhydroxyalkyl, aryl or aralkyl a rest of a sugar or represents ##STR6## being 0, 1, 2 or 3 R.sub.6 represents a hydrogen atom or a lower alkyl radical,R.sub.7 represents H, alkyl, halogen, hydroxyl, sulfydryl, alkoxy, alkylthio, acyloxy, acylthio, acylamino or primary, secondari or tertiary amino and the salts of the said compounds.These compounds find an application in the cosmetic and pharmaceutical fields.Type: GrantFiled: September 15, 1989Date of Patent: August 20, 1991Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
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Patent number: 4962241Abstract: The process of the present invention for producing dihydroxynaphthalenes comprises hydrolyzing a diacyloxynaphthalene in a water-containing solvent in the presence of an acid catalyst. The use of an acid as a hydrolyzing catalyst enables dihydroxynaphthalenes to be obtained with high purity and in high yield.Type: GrantFiled: February 3, 1989Date of Patent: October 9, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Masaaki Yasuda, Hisaya Miki
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Patent number: 4879421Abstract: A method is provided for the production of optically active (S)-(-)- and (R)-(+)-binaphthol and catalyzed asymmetric hydrolysis of corresponding racemic (R,S)-(.+-.)-binaphthol an (R,S)(.+-.)-spirobiindanol diesters.Type: GrantFiled: August 15, 1988Date of Patent: November 7, 1989Assignee: General Electric CompanyInventor: Romas J. Kazlauskas
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Patent number: 4861920Abstract: Process for the preparation of 2,6-dihydroxynaphthalene from 2,6-dialkylnaphthalenes, which are dissolved in an inert solvent and are oxidized at temperatures from 50.degree. to 150.degree. C. by means of oxygen or oxygen donors, in the presence of an alkali metal salt or alkaline earth metal salt of an organic carboxylic acid having 5 to 14 carbon atoms, to give the corresponding 2,6-dialkylnaphthalene dihydroperoxides, and the latter are subsequently hydrolysed.The process results in pure, easily isolatable products in a good yield. The process products according to the invention are valuable intermediates for, inter alia, dyes, plastics, synthetic fibres, polymeric liquid crystals or pharmaceuticals.Type: GrantFiled: March 14, 1988Date of Patent: August 29, 1989Assignee: Ciba-Geigy CorporationInventors: Martin Clausen, Paul Rys