Oxygen Bonded Directly At The 2-, 3-, 5-, Or 6- Position Patents (Class 552/307)
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Patent number: 11453633Abstract: Provided is a production method capable of efficiently producing a reduced coenzyme Q10 Form II crystal. The method for producing a reduced coenzyme Q10 Form II crystal includes: adding a reduced coenzyme Q10 Form II crystal as a seed crystal to a solution with a temperature of 32° C. to 43° C., the solution containing fa) at least one organic solvent selected from the group consisting of an alcohol, a hydrocarbon, an aliphatic acid ester and a nitrogen compound, and (b) reduced coenzyme Q10, to prepare a mixture, and precipitating the reduced coenzyme Q10 from the mixture, in the form of the reduced coenzyme Q10 Form II crystal.Type: GrantFiled: August 29, 2019Date of Patent: September 27, 2022Assignee: KANEKA CORPORATIONInventors: Takao Yamaguchi, Koichi Kinoshita
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Publication number: 20150018569Abstract: The present invention discloses a simple method for transforming cashew nut shell liquid into an active herbicidal composition.Type: ApplicationFiled: February 13, 2013Publication date: January 15, 2015Applicant: BANOR UNIVERSIITYInventors: Viacheslav Vitalievich Tverezovskiy, Radek Messias Braganca, Frank Arthur Howard, Spencer Matthew Gould, Paul Anthony Fowler, Mark Stephen Baird
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Publication number: 20140342998Abstract: The present invention relates to nitric oxide donor compounds having a quinone based structure, to processes for their preparation and to their use in the treatment of pathological conditions where a deficit of NO plays an important role in their pathogenesis.Type: ApplicationFiled: October 23, 2012Publication date: November 20, 2014Applicant: NICOX S.A.Inventors: Gael Ronsin, Laura Storoni, Francesca Benedini
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Patent number: 8716486Abstract: Methods of treating or suppressing oxidative stress disorders including mitochondrial diseases, impaired energy processing disorders, neurodegenerative diseases and diseases of aging are disclosed, as well as compounds useful in the methods of the invention, such as 2-heterocyclylaminoalkyl-(p-quinone) derivatives.Type: GrantFiled: June 23, 2009Date of Patent: May 6, 2014Assignee: Edison Pharmaceuticals, Inc.Inventors: Andrew W. Hinman, Orion D. Jankowski, Kieron E. Wesson
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Patent number: 8568779Abstract: The present invention aims to provide a production method capable of industrially and producing coenzyme Q10 particles having a high content and superior powder flowability characteristics by simple facility and convenient operations. The present invention provides a method of producing coenzyme Q10 particles, including mixing coenzyme Q10 and a poor solvent by stirring at a temperature not less than the melting point of coenzyme Q10, dispersing coenzyme Q10 into the form of oil droplets, and cooling them to a solidification temperature of coenzyme Q10 or below while stirring the dispersion to give solid particles, wherein the poor solvent is an aqueous solution comprising an organic solvent and/or a surfactant having an HLB of 6 or above. According to the production method of the present invention, coenzyme Q10 particles markedly superior in powder characteristics, and having, for example, a powder flowability index of not less than 80 can be obtained.Type: GrantFiled: January 10, 2008Date of Patent: October 29, 2013Assignee: Kaneka CorporationInventors: Kento Kanaya, Shiro Kitamura, Takahiro Ueda
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Publication number: 20130217902Abstract: Compounds of following general formula (I) and pharmaceutical compositions thereof for inhibiting mammalian tumor cell proliferation are disclosed. In formula (I), n is an integer from 0 to 9. The cell proliferation of breast tumor, ovarian tumor, skin tumor or liver tumor is inhibited by the compounds of the formula (I).Type: ApplicationFiled: March 27, 2012Publication date: August 22, 2013Applicant: CHINA MEDICAL UNIVERSITYInventors: You-Cheng HSEU, Hsin-Ling YANG
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Publication number: 20130158126Abstract: Cannabinoid quinone derivatives. The present invention refers to cannabinoid quinone derivatives to be used as medicaments, particularly as PPAR gamma (PPARg) agonists for treating diseases which etiology is based on an impaired PPARg function as transcription factor i.e. PPARg-related diseases.Type: ApplicationFiled: March 26, 2010Publication date: June 20, 2013Applicant: VIVACELL BIOTECHNOLOGY ESPAÑA, S.L.Inventors: Eduardo Muñoz Blanco, Giovanni Appendino, María Luz Bellido Cabello De Alba
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Publication number: 20120201802Abstract: The present invention aims to provide a component having not only an ability to reduce oxidized coenzyme Q10 and an ability to stabilize reduced coenzyme Q10, but also nutrient, flavor, broad utility and the like, and a utilization method thereof. The present invention relates to a safe and convenient method of producing reduced coenzyme Q10, including reducing oxidized coenzyme Q10 by using, as a component derived from a naturally-occurring substance, which is safe for the body, any one or more components selected from the group consisting of an acerola extract, a tea extract, a rosemary extract, a pine bark extract and a Vaccinium vitis-idaea extract. In addition, the present invention also relates to a method of stabilizing reduced coenzyme Q10 in the co-presence of a component derived from a naturally-occurring substance, and a stabilized composition.Type: ApplicationFiled: October 14, 2010Publication date: August 9, 2012Applicant: Keneka CorporationInventors: Takao Yamaguchi, Takaaki Jikihara, Shiro Kitamura, Yasuyoshi Ueda
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Publication number: 20120130098Abstract: The present invention relates to novel carboxylic acid-substituted idebenone derivatives, skin treatment compositions containing these carboxylic acid-substituted idebenone derivatives, methods of treating skin changes by topical application of these carboxylic acid-substituted idebenone derivatives, and their methods of synthesis. The carboxylic acid-substituted idebenone derivatives of the present invention are unexpectedly effective in treating skin, particularly with respect to skin tolerance. When included in a topical composition, the carboxylic acid-substituted idebenone derivatives of the present invention have an antioxidant effect that is useful in treating a skin change.Type: ApplicationFiled: January 13, 2012Publication date: May 24, 2012Applicant: ELIZABETH ARDEN, INC.Inventors: Falko Diedrich, Joseph A. Lewis, II, Joseph C. DiNardo, Birgit Neudecker, Eberhard Weiland
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Patent number: 7829555Abstract: The invention provides a method of targeting a drug to areas of hypoxic and/or ischemic tissue within the body in which the desired drug species is linked to a non-cytotoxic bioreductive carrier. Also provided by the invention are novel bioreductive conjugates comprising a non-cytotoxic bioreductive moiety with linked-thereto at least one therapeutic agent. The compounds of the invention are particularly suitable for the treatment of rheumatoid arthritis and other arthritic conditions, diabetes, atherosclerosis, stroke, sepsis, Alzheimer's disease and other neurological disorders, cancer, kidney disease, digestive diseases, liver disease, chronic periodontitis or ischemia following tissue transplantation.Type: GrantFiled: February 13, 1998Date of Patent: November 9, 2010Assignee: The University of ManchesterInventors: David Blake, Declan Naughton, Ged Adams, Margaret Adams, legal representative, Ian Stratford, Christopher Morris, Mohammed Jaffar, Matthew Naylor
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Publication number: 20100004473Abstract: The present invention aims to provide a production method capable of industrially and producing coenzyme Q10 particles having a high content and superior powder flowability characteristics by simple facility and convenient operations. The present invention provides a method of producing coenzyme Q10 particles, including mixing coenzyme Q10 and a poor solvent by stirring at a temperature not less than the melting point of coenzyme Q10, dispersing coenzyme Q10 into the form of oil droplets, and cooling them to a solidification temperature of coenzyme Q10 or below while stirring the dispersion to give solid particles, wherein the poor solvent is an aqueous solution comprising an organic solvent and/or a surfactant having an HLB of 6 or above. According to the production method of the present invention, coenzyme Q10 particles markedly superior in powder characteristics, and having, for example, a powder flowability index of not less than 80 can be obtained.Type: ApplicationFiled: January 10, 2008Publication date: January 7, 2010Applicant: KANEKA CORPORATIONInventors: Kento Kanaya, Shiro Kitamura, Takahiro Ueda
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Publication number: 20090036693Abstract: According to the present invention, a method of purifying ubiquinone-10, which includes separating and removing a substance structurally similar to ubiquinone-10 contained in a starting material solution containing ubiquinone-10 by the use of a porous crosslinked acrylic polymer, more preferably, a method of purifying ubiquinone-10 by separating and removing a substance structurally similar to ubiquinone-10 contained in a starting material solution, which includes feeding a starting material solution containing ubiquinone-10 in a simulated moving bed chromatography apparatus wherein a solution can circulate in one direction in a packed-bed wherein a porous crosslinked acrylic polymer is packed, and flowing an eluent in the packed-bed in one direction, is provided.Type: ApplicationFiled: June 9, 2006Publication date: February 5, 2009Applicants: Kyowa Hakko Kogyo Co., Ltd., Nippon Rensui Co.Inventors: Hiroshi Nagano, Hiroto Yamanashi, Hideki Murata
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Patent number: 7122543Abstract: A substituted benzoic acid derivative which is represented by the following formula (I) and has an NF-?B inhibiting action (in the formula, R3, R4 and R5 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon(s) or an alkoxy group having 1 to 6 carbon(s); R9 and R10 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon(s) or an acyl group having 2 to 11 carbons); R2 represents an optionally-substituted aromatic hydrocarbon group or an optionally-substituted heterocyclic group; and X represents a carboxyl group which may be esterified or amidated)Type: GrantFiled: September 11, 2002Date of Patent: October 17, 2006Assignee: Daiichi Suntory Pharma Co., Ltd.Inventors: Kenji Suzuki, Yoichi Nunokawa
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Patent number: 7064124Abstract: A NF-?B inhibitor represented by the following formula (I) is provided: ?Type: GrantFiled: March 27, 2002Date of Patent: June 20, 2006Assignees: Daiichi Suntory Pharma Co., Ltd., Daiichi Suntory Biomedical Research Co., Ltd.Inventors: Kenji Suzuki, Yoichi Nunokawa, Naohisa Ogou
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Patent number: 6828450Abstract: This invention provides analogs of triptycene which are useful as anticancer drugs, as well as for other uses. The potency of these compounds is in a similar magnitude as daunomycin, a currently used anticancer drug. Each compound of the invention produces one or more desired effects (blocking nucleoside transport, inhibiting nucleic acid or protein syntheses, decreasing the proliferation and viability of cancer cells, inducing DNA fragmentation or retaining their effectiveness against multidrug-resistant tumor cells).Type: GrantFiled: October 9, 2001Date of Patent: December 7, 2004Assignee: Kansas State University Research FoundationInventors: Duy Hua, Jean-Pierre Perchellet
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Publication number: 20040151711Abstract: Processes for the stereospecific synthesis of coenzyme Q10, ubiquinone, are disclosed; a semi synthetic procedure using solanesol derived from tobacco waste as the starting material. The process of the invention results in high yields of isometrically useful compositions containing the optically pure isomers.Type: ApplicationFiled: November 5, 2003Publication date: August 5, 2004Inventor: Daniel David West
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Patent number: 6686485Abstract: Processes for the stereospecific synthesis of coenzyme Q10, ubiquinone, are disclosed; a semi synthetic procedure using solanesol derived from tobacco waste as the starting material. The process of the invention results in high yields of isometrically useful compositions containing the optically pure isomers.Type: GrantFiled: April 19, 2001Date of Patent: February 3, 2004Inventor: Daniel David West
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Patent number: 6506539Abstract: A complex of a dye cation and an anionic TCNQ derivative of the formula (I): in which [Dye]+ is a dye cation, L1 is a linking group, R1 is a substituent group, p is an integer of 1-4, and r is an integer of 0-3 under the condition of 1<p+r<4, is favorably employable as a dye compound for preparing a recording layer of CD-R or DVD-R.Type: GrantFiled: April 6, 2001Date of Patent: January 14, 2003Assignee: Fuji Photo Film Co., Ltd.Inventors: Shinichi Morishima, Takashi Usami
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Publication number: 20020156302Abstract: Processes for the stereospecific synthesis of coenzyme Q10, ubiquinone, are disclosed; a semi synthetic procedure using solanesol derived from tobacco waste as the starting material. The process of the invention results in high yields of isometrically useful compositions containing the optically pure isomers.Type: ApplicationFiled: April 19, 2001Publication date: October 24, 2002Inventor: Daniel David West
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Patent number: 5864048Abstract: The present description relates to new anthraquinone-derivatives endowed with inhibitory activity of the serine proteinase enzymes, useful for the treatment of rheumatoid arthritis, acute respiratory syndrome of adult, and pulmonary emphysema, and to new processes for the preparation of rhein derivatives.Type: GrantFiled: July 31, 1997Date of Patent: January 26, 1999Assignee: Laboratoire Medidom S.A.Inventor: Guido Di Napoli
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Patent number: 5847171Abstract: The invention is drawn to organic compounds of the general formulae L--A--Z or L--A'--L' as defined in the specification. The compounds are readily crystallizable and can be used for their ferromagnetic properties.Type: GrantFiled: September 16, 1997Date of Patent: December 8, 1998Assignee: Alcatel Alsthom Compagnie Generale D'ElectriciteInventors: Stanislas Galaj, Alain Le Mehaute
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Patent number: 5714622Abstract: The invention is drawn to organic compounds of the general formulae L--A--Z or L--A'--L' as defined in the specification. The compounds are readily crystallizable and can be used for their ferromagnetic properties.Type: GrantFiled: April 12, 1996Date of Patent: February 3, 1998Assignee: Alcatel Alsthom Compagnie Generale D'ElectriciteInventors: Stanislas Galaj, Alain Le Mehaute
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Patent number: 5616734Abstract: The invention relates to the use of compounds of the formula IR.sup.1.sub.a Re.sub.b O.sub.c (I),where a is from 1 to 6, b is from 1 to 4 and c is from 1 to 14 and the sum of a, b and c is in accordance with the valence of from 5 to 7 of the rhenium, with the proviso that c is not greater than 3.multidot.b, and where R.sup.1 is identical or different and is an aliphatic hydrocarbon radical having from 1 to 10 carbon atoms, an aromatic hydrocarbon radical having from 6 to 10 carbon atoms or an arylalkyl radical having from 7 to 9 carbon atoms, with the radicals R.sup.1 being able, if desired, to be identically or differently substituted independently of one another and, in the case of .sigma.-bonded radicals, at least one hydrogen atom still being bonded to the carbon atom in the .alpha. position, as catalysts for the oxidation of electron-rich aromatic compounds and their derivatives and to a process for the oxidation of electron-rich aromatic compounds which comprises oxidizing electron-rich C.sub.6 -C.sub.Type: GrantFiled: January 25, 1995Date of Patent: April 1, 1997Assignee: Hoechst AktiengesellschaftInventors: Wolfgang A. Herrmann, Joao D. G. Correia, Richard Fischer, Waldemar Adam, Jianhua Lin, Chantu R. Saha-Moller, Masao Shimizu
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Patent number: 5328819Abstract: An azomethine dye represented by the following general formula (I) ##STR1## wherein A represents a dye residue formed by removing one hydrogen atom from an indophenol or indoaniline dye; L represents a divalent bonding group; and Z represents a non-metallic atomic group required for forming a three-membered to eight-membered heterocyclic ring together with N, provided that a carbonyl group is not directly bonded to N in the heterocyclic ring. Also disclosed is a silver halide photographic material having an emulsion layer with a covering power of at least 60, and wherein the silver halide photographic material contains at least one member of the dyes of general formula (I) in such an amount that an increase in transmission density in unexposed areas caused by the incorporation of the dye therein after development is not more than 0.06.Type: GrantFiled: August 12, 1992Date of Patent: July 12, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Shigeru Ohno, Yukio Miyaki, Shigeru Yamazaki
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Patent number: 5318993Abstract: The present invention relates to novel benzoquinones which are useful as antihyperlipidemic agents. The present invention also provides a process for their preparation, pharmaceutical compositions, and a method for treating birds and mammals in need thereof which comprises administering to said host an effective amount of a benzoquinone of the present invention.Type: GrantFiled: April 16, 1993Date of Patent: June 7, 1994Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5288752Abstract: A compound having the formula (I): ##STR1## wherein A is --CH.sub.2 --, R.sup.1 is CH.sub.3 or OCH.sub.3 ; R.sup.2 is hydroxy or carboxy, carboxylic acid or carboxylic acid ester group; R.sup.3 is H or a lower alkyl; and n is 0 or an integer of 1 to 6 or a pharmaceutically acceptable salt thereof.Type: GrantFiled: November 23, 1992Date of Patent: February 22, 1994Assignee: Suntory LimitedInventors: Toshio Tatsuoka, Kenji Suzuki, Fumio Satoh, Seiji Miyano, Kunihiro Sumoto
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Patent number: 5283355Abstract: Compounds of the Formula (5) and processes for their preparation and use, particularly in the manufacture of unsymmetrical triphenodioxazine dyes: ##STR1## wherein: Y is H, alkyl, substituted alkyl, alkoxy, Cl or Br;R is a group of Formula (3) ##STR2## R.sup.1 and R.sup.2 are each independently alkyl, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form an optionally substituted 4, 5 or 6 membered alicyclic or heterocyclic ring;R.sup.3 is H;Z is Cl, Br or A--NH; andA is H or the residue of a primary amine.Type: GrantFiled: October 22, 1991Date of Patent: February 1, 1994Assignee: Imperial Chemical Industries PLCInventor: William J. E. Norris
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Patent number: 5220042Abstract: 1,4-Benzoquinone derivatives and benzene derivatives having cerebral- and cardiac-blood flow improving activities and preventive activities of cerebral ischema with low toxicities, and thus are useful as activators for cardiac and cebral metabolisms, curing agents for heart failure, cardiac and cerebral blood flow improving agents, as well as anti-allergic agents for slow reacting allergy (IV-type allergy).Type: GrantFiled: November 21, 1989Date of Patent: June 15, 1993Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Hideyuki Iwaki, Yoshiyasu Fukuyama, Kuniaki Matsui
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Patent number: 5210239Abstract: A quinone derivative useful in the treatment of hepatic diseases defined by the general formula: ##STR1## where R1 is selected from the group consisting of alkyl, alkenly, alkynyl or heterocycle, R2 is a substituted nitrogen containing radical wherein the substituents on said nitrogen are selected from the group consisting of hydrogen, substituted or unsubstituted lower alkyl or heterocycles, and where said nitrogen may be a ring heteroatom, and R3, R4 and R5, may be the same or different and each are hydrogen, lower alkyl or lower alkoxy groups.Type: GrantFiled: August 31, 1990Date of Patent: May 11, 1993Assignee: Eisai Co., Ltd.Inventors: Shinya Abe, Yasushi Okamoto, Katsuya Tagami, Shigeki Hibi, Junichi Nagakawa, Kazuo Hirota, Ieharu Hishinuma, Kaname Miyamoto, Takashi Yamanaka, Hiromitsu Yokohama, Tsutomu Yoshimura, Tohru Horie, Yasunori Akita, Koichi Katayama, Isao Yamatsu
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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: 5175318Abstract: Phenols are oxidated to quinones with hydrogen peroxide in the presence of catalytic amounts of bromine, iodine, hydrogen bromide and hydrogen iodide.Type: GrantFiled: April 7, 1992Date of Patent: December 29, 1992Assignees: Consiglio Nazionale Della Ricerche, Enicham Synthesis, Brichima, S.p.A.Inventors: Francesco Minisci, Attilio Citterio, Elena Vismara, Silvia De Bernardinis, Carlo Neri, Luciano Pallini, Mariano Correale
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Patent number: 5091545Abstract: The present invention relates to a process for the catalytic oxidation of hydroxy containing aromatic compounds to form the respective quinone compounds comprising contacting a hydroxy containing aromatic compound of the formula: ##STR1## with a molecular oxygen containing gas in the presence of: (a) a catalytic amount of a cobalt (II) compound,(b) a primary aliphatic amine having the nitrogen atom attached to a tertiary carbon, and(c) an alcohol selected from the group consisting of methyl alcohol, ethyl alcohol, isopropyl alcohol, butyl alcohol, 2,2,2-trifluoroethanol and benzyl alcohol,wherein X is of the formula ##STR2## wherein R is individually selected from the group of radicals consisting of hydrogen, an alkyl having from about 1 to about 18 carbon atoms, an alkoxy having from about 1 to 8 carbon atoms, a phenyl and an aralkyl having 7 to 12 carbon atoms.Type: GrantFiled: March 2, 1990Date of Patent: February 25, 1992Assignee: The Goodyear Tire & Rubber CompanyInventor: Dane K. Parker
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Patent number: 5057514Abstract: 1. A compound having the formula (I): ##STR1## wherein A is --CH.sub.2 --, --O--, or --S--; R.sup.1 is CH.sub.3 or OCH.sub.3 ; R.sup.2 is hydroxy of carboxy which may be optionally esterized or amidated; R.sup.3 is H or a lower alkyl; and n is 0 or an integer of 1 to 6 or a pharmaceutically acceptable sale thereof.Type: GrantFiled: December 20, 1988Date of Patent: October 15, 1991Assignee: Suntory LimitedInventors: Toshio Tatsuoka, Kenji Suzuki, Fumio Satoh, Seiji Miyano, Kunihiro Sumoto
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Patent number: 4992469Abstract: A quinone derivative of the formula (I): ##STR1## in which A is a group of the formula (IV): ##STR2## or a group of the formula (V): ##STR3## in which X and Y are either the same as or different from each other and each are hydroxy, methoxy or hydrogen; and n is an integer of 1 to 5,is disclosed. The compound is useful as a medicament.Type: GrantFiled: May 29, 1985Date of Patent: February 12, 1991Assignees: Eisai Co., Ltd., Nagoya UniversityInventors: Takayuki Ozawa, Morimitsu Nishikimi, Hiroshi Suzuki, Yoshiharu Shimomura, Isao Yamatsu, Shinya Abe, Kouji Yamada, Tohru Fujimori, Takanobu Takamura
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Patent number: 4952712Abstract: 2,3-Dimethoxy-5-methylbenzoquinone is prepared by oxidizing 3,4,5-trimethoxytoluene by reaction with hydrogen peroxide in the presence of a catalyst which is a heteropolyacid selected from phosphomolybdic acids, phosphotungstic acids, silicomolybdic acids and silicotungstic acids or a salt thereof.Type: GrantFiled: March 13, 1989Date of Patent: August 28, 1990Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Hideo Orita, Masao Shimizu, Takashi Hayakawa, Katsuomi Takehira
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Patent number: 4933489Abstract: An improved process for the manufacture of the antipsoriatic agent, 6-chloro-1,4-diacetoxy-2,3-dimethoxynaphthalene, is herein described which involves in situ Diels-Alder coupling of 2,3-dimethoxybenzo-1,4-quinone with a 3-chloro-1-alkoxy-1,3-butadiene; 1,4-elimination of the alcohol with aromatization of the chlorine-bearing ring, and acetylation.Type: GrantFiled: October 24, 1985Date of Patent: June 12, 1990Assignee: Warner-Lambert CompanyInventor: Daniel L. Flynn
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Patent number: 4874752Abstract: A novel benzoquinone derivative of the general formula: ##STR1## [wherein R.sub.1 and R.sub.2 are the same or different and each is methyl or methoxy; n is an integer of 0 to 21; m is 0 or 1, Z is a group of the formula: ##STR2## (wherein R.sub.3 and R.sub.4 are the same or different and each is hydrogen or an alkyl group which may optionally be substituted or, R.sub.3 and R.sub.4 together with the adjacent nitrogen atom form a morpholino group), a group of the formula: --COR.sub.5 (wherein R.sub.5 is an .alpha.-amino acid residue or a substituted or unsubstituted glucosamine residue), a group of the formula: ##STR3## (wherein R.sub.6 is a divalent hydrocarbon group of 1 to 3 carbon atoms), a group of the formula: ##STR4## (wherein R.sub.6 has the same meaning as defined above) or a group of the formula: --CH.dbd.CH).sub.l COR.sub.7 (wherein l is an integer of 1 to 4 and R.sub.Type: GrantFiled: November 8, 1988Date of Patent: October 17, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Hisayoshi Okazaki, Isuke Imada