Naphthols Patents (Class 568/735)
  • Patent number: 8835697
    Abstract: 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: Grant
    Filed: March 20, 2012
    Date of Patent: September 16, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Daisuke Kori, Takeshi Kinsho, Katsuya Takemura, Tsutomu Ogihara, Takeru Watanabe, Hiroyuki Urano
  • Publication number: 20130274487
    Abstract: 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: Application
    Filed: December 19, 2011
    Publication date: October 17, 2013
    Applicant: FIRMENICH SA
    Inventors: Sylvia Joyeuse Adélaïde Ada Saudan, Michel Alfred Joseph Saudan
  • Publication number: 20100264359
    Abstract: 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: Application
    Filed: September 24, 2008
    Publication date: October 21, 2010
    Applicant: LANXESS DEUTSCHLAND GMBH
    Inventors: Udo Straetmans, Felix Straetmans
  • Publication number: 20100145060
    Abstract: 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: Application
    Filed: December 3, 2009
    Publication date: June 10, 2010
    Inventors: Yigang Zhao, Victor A. Snieckus
  • Publication number: 20090253919
    Abstract: 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: Application
    Filed: April 3, 2008
    Publication date: October 8, 2009
    Applicant: Board of Regents
    Inventors: Derun Li, John R. Falck
  • Patent number: 7449608
    Abstract: 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: Grant
    Filed: December 10, 2002
    Date of Patent: November 11, 2008
    Assignee: Ueno Fine Chemicals Industry, Ltd.
    Inventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori, Nobuhiro Yonetani
  • Publication number: 20080227978
    Abstract: 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: Application
    Filed: January 26, 2006
    Publication date: September 18, 2008
    Inventor: Simon Woodward
  • Publication number: 20080214507
    Abstract: 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: Application
    Filed: February 20, 2008
    Publication date: September 4, 2008
    Applicant: WYETH
    Inventors: Mahdi B. FAWZI, Parimal R. DESAI, Tianmin ZHU
  • Patent number: 7151070
    Abstract: 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: Grant
    Filed: February 27, 2003
    Date of Patent: December 19, 2006
    Assignee: Chengdu Institute of Organic Chemistry Chinese Academy of Sciences
    Inventors: Liuzhu Gong, Zhibin Luo, Quanzhong Liu, Aiqiao Mi, Yaozhong Jiang
  • Patent number: 7135590
    Abstract: 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: Grant
    Filed: August 17, 2004
    Date of Patent: November 14, 2006
    Assignee: Council of Scientific and Industrial Research
    Inventors: 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
  • Patent number: 6911563
    Abstract: 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: Grant
    Filed: December 27, 2001
    Date of Patent: June 28, 2005
    Assignees: National Institute of Advanced Industrial Science, NOK Corporation
    Inventors: Fujio Mizukami, Shuichi Niwa, Makoto Toba, Naotsugu Itoh, Tomonari Saito, Takemi Nanba, Hiroshi Shoji, Kazuhiko Haba
  • Patent number: 6838583
    Abstract: 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: Grant
    Filed: May 20, 2003
    Date of Patent: January 4, 2005
    Assignee: Warner-Lambert Company LLC
    Inventors: David Scott Harper, Robert A. Coburn, Andre Soshinsky, Constantine Georgiades, Marianne D. Huntley
  • Patent number: 6784228
    Abstract: 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: Grant
    Filed: July 9, 2002
    Date of Patent: August 31, 2004
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Ichiro Ogura, Yoshiyuki Takahashi, Tomoyuki Imada
  • Publication number: 20040133047
    Abstract: 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: Application
    Filed: May 20, 2003
    Publication date: July 8, 2004
    Inventors: Scott Allan May, Thomas Michael Wilson, Tony Yantao Zhang
  • Patent number: 6563008
    Abstract: Novel intermediates of Formula IV wherein the substituents are as defined in the specification and a process for preparing the same.
    Type: Grant
    Filed: June 29, 2001
    Date of Patent: May 13, 2003
    Assignee: Aventis Pharma S.A.
    Inventors: Dominique Lesuisse, Jean-Georges Teutsch
  • Publication number: 20020110530
    Abstract: 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: Application
    Filed: December 20, 2001
    Publication date: August 15, 2002
    Inventors: David Scott Harper, Robert A. Coburn, Andre Soshinsky, Constantine Georgiades, Marianne D. Huntley
  • Patent number: 6395904
    Abstract: 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: Grant
    Filed: June 6, 2000
    Date of Patent: May 28, 2002
    Assignee: Yale University
    Inventors: John P. Caradonna, Subhasish Mukerjee, Adonis Stassinopoulos
  • Publication number: 20010039365
    Abstract: 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: Application
    Filed: January 16, 2001
    Publication date: November 8, 2001
    Inventor: Terence Michael Barnhart
  • Publication number: 20010031887
    Abstract: 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): 1
    Type: Application
    Filed: March 8, 2001
    Publication date: October 18, 2001
    Inventor: Junji Inanaga
  • Patent number: 6252124
    Abstract: 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: Grant
    Filed: April 29, 1999
    Date of Patent: June 26, 2001
    Assignee: ILLA International, LLC
    Inventors: Vladimir Mikhailovitch Zakoshansky, Irina Ivanovna Vassilieva
  • Patent number: 6090969
    Abstract: 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: Grant
    Filed: September 8, 1998
    Date of Patent: July 18, 2000
    Assignee: Nagase and Co., Ltd.
    Inventors: Masakatsu Shibasaki, Hiroaki Sasai, Takayoshi Arai
  • Patent number: 5981806
    Abstract: 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: Grant
    Filed: March 2, 1998
    Date of Patent: November 9, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventor: Thomas Pelster
  • Patent number: 5962002
    Abstract: 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: Grant
    Filed: July 10, 1997
    Date of Patent: October 5, 1999
    Assignee: BTG International Limited
    Inventors: Bhupinder Pall Singh Khambay, Duncan Batty, Stuart Cameron, David Gordon Beddie
  • Patent number: 5952532
    Abstract: 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: Grant
    Filed: July 31, 1997
    Date of Patent: September 14, 1999
    Assignee: Sunoco, Inc.
    Inventors: Vincent A. Durante, Tilak P. Wijesekera, Swati Karmakar
  • Patent number: 5907069
    Abstract: 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: Grant
    Filed: January 20, 1998
    Date of Patent: May 25, 1999
    Assignee: Albemarle Corporation
    Inventors: Brian F. Becnel, Mahmood Sabahi, Kevin J. Theriot
  • Patent number: 5892038
    Abstract: 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: Grant
    Filed: December 8, 1997
    Date of Patent: April 6, 1999
    Assignee: Pharmacopeia, Inc.
    Inventors: Roland Ellwood Dolle, III, Hitesh K. Patel
  • Patent number: 5874588
    Abstract: 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: Grant
    Filed: September 19, 1997
    Date of Patent: February 23, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Bernd Lamatsch, Olof Wallquist
  • Patent number: 5872289
    Abstract: 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: Grant
    Filed: March 6, 1998
    Date of Patent: February 16, 1999
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John Bruce Appleby, Francis Joseph Waller, Stephen Charles Webb
  • Patent number: 5859067
    Abstract: 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: Grant
    Filed: November 12, 1997
    Date of Patent: January 12, 1999
    Inventors: Basil Don Roufogalis, Colin Charles Duke, Qian Li
  • Patent number: 5847233
    Abstract: 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: Grant
    Filed: November 20, 1997
    Date of Patent: December 8, 1998
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Shigeru Ito, Kenji Minami, Masaya Kitayama
  • Patent number: 5840999
    Abstract: 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: Grant
    Filed: March 26, 1997
    Date of Patent: November 24, 1998
    Assignee: The Perkin-Elmer Corporation
    Inventors: Scott C. Benson, Steven M. Menchen, Peter D. Theisen, Kevin M. Hennessey, Vergine C. Furniss, Joan Hauser
  • Patent number: 5798443
    Abstract: 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: Grant
    Filed: March 10, 1994
    Date of Patent: August 25, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marie Galvez, Marie-France Maurice
  • Patent number: 5786523
    Abstract: 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: Grant
    Filed: November 18, 1997
    Date of Patent: July 28, 1998
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Shigeru Ito, Kenji Minami, Masaya Kitayama
  • Patent number: 5716624
    Abstract: 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: Grant
    Filed: December 15, 1994
    Date of Patent: February 10, 1998
    Assignee: C.I.R.D. Galderma
    Inventor: Jean-Michel Bernardon
  • Patent number: 5684152
    Abstract: 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: Grant
    Filed: September 19, 1996
    Date of Patent: November 4, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Mitree M. Ponpipom, William K. Hagmann
  • Patent number: 5543564
    Abstract: 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: Grant
    Filed: January 11, 1995
    Date of Patent: August 6, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: J urgen Kulpe, Heinz Strutz, Hans-Martin R uffer, Siegbert Rittner
  • Patent number: 5510520
    Abstract: 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: Grant
    Filed: August 19, 1994
    Date of Patent: April 23, 1996
    Assignee: Kankyo Kagaku Center Co., Ltd.
    Inventor: Masatoshi Kawashima
  • Patent number: 5426243
    Abstract: 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: Grant
    Filed: August 17, 1994
    Date of Patent: June 20, 1995
    Assignee: Albemarle Corporation
    Inventor: Jean-Pierre Lecouve
  • Patent number: 5422038
    Abstract: 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: Grant
    Filed: December 14, 1993
    Date of Patent: June 6, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shoji Toda, Takayuki Higashii, Isao Kurimoto, Masayoshi Minai, Chizu Sekine, Takeshi Tani, Koichi Fujisawa
  • Patent number: 5420362
    Abstract: 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: Grant
    Filed: October 8, 1993
    Date of Patent: May 30, 1995
    Assignee: Clairol, Inc.
    Inventors: Mu-Ill Lim, Linas Stasaitis, Yuo-Guo Pan, Alexander Chan
  • Patent number: 5395962
    Abstract: 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: Grant
    Filed: November 16, 1992
    Date of Patent: March 7, 1995
    Assignee: Kankyo Kagaku Center Co., Ltd.
    Inventor: Masatoshi Kawashima
  • Patent number: 5256829
    Abstract: 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: Grant
    Filed: October 2, 1992
    Date of Patent: October 26, 1993
    Assignee: Potasse et Produits Chimiques
    Inventor: Roland Jacquot
  • Patent number: 5233097
    Abstract: 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: Grant
    Filed: October 15, 1992
    Date of Patent: August 3, 1993
    Assignee: UOP
    Inventors: Laszlo T. Nemeth, Eric M. Hyatt, Thomas P. Malloy
  • Patent number: 5180742
    Abstract: 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: Grant
    Filed: January 9, 1987
    Date of Patent: January 19, 1993
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Yoshitaka Maki
  • Patent number: 5087769
    Abstract: 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: Grant
    Filed: September 26, 1990
    Date of Patent: February 11, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Henry C. Linstid, III., Kenneth G. Davenport
  • Patent number: 5043483
    Abstract: 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: Grant
    Filed: November 28, 1988
    Date of Patent: August 27, 1991
    Assignee: Montedison S.p.A.
    Inventors: Loris Sogli, Raffaele Ungarelli, L. Lawrence Chapoy
  • Patent number: 5041639
    Abstract: 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: Grant
    Filed: September 15, 1989
    Date of Patent: August 20, 1991
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
  • Patent number: 4962241
    Abstract: 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: Grant
    Filed: February 3, 1989
    Date of Patent: October 9, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Masaaki Yasuda, Hisaya Miki
  • Patent number: 4879421
    Abstract: 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: Grant
    Filed: August 15, 1988
    Date of Patent: November 7, 1989
    Assignee: General Electric Company
    Inventor: Romas J. Kazlauskas
  • Patent number: 4861920
    Abstract: 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: Grant
    Filed: March 14, 1988
    Date of Patent: August 29, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Clausen, Paul Rys