At Least Three Carbons Bonded Directly To The Cyclohexadiene Patents (Class 552/310)
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Patent number: 10364231Abstract: The invention relates to a method for producing 2,3,5-trimethyl benzoquinone or a compound containing 2,3,5-trimethyl benzoquinone, the method comprising the following steps: Oxidation of 2,3,6-trimethylphenol with oxygen or an oxygen-containing gas in a two-or multi-phase reaction medium in the presence of a catalyst or catalyst system containing at least one copper (II)-halide to a mixture containing 2,3,5-trimethyl benzoquinone, characterized in that the reaction medium contains water and at least one secondary aliphatic acyclic alcohol having 6 or more, preferably 7 or more, carbon atoms.Type: GrantFiled: August 14, 2017Date of Patent: July 30, 2019Assignee: BASF SEInventors: Richard Dehn, Michael Kraus, Martine Dehn, Manuel Danz, Joaquim Henrique Teles
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Patent number: 9162957Abstract: A method of producing alpha-tocotrienol quinone or a stereoisomer thereof, the method comprising selective opening of alpha-tocotrienol chroman to alpha-tocotrienol quinone in the presence of non-alpha tocotrienol chromans by oxidizing alpha-tocotrienol with a metal salt oxidizing agent, wherein the stoichiometric ratio of metal salt oxidizing agent/alpha-tocotrienol is at least 4:1 and wherein said metal oxidizing agent is added in sequential additions, in order to reduce oxidation of any amounts of non-alpha tocotrienol chromans that might have been present in the starting alpha-tocotrienol chroman material. This process uses conditions favoring oxidation rates of the alpha tocotrienol chroman vs. the non-alpha tocotrienol chromans.Type: GrantFiled: July 19, 2012Date of Patent: October 20, 2015Assignee: Edison Pharmaceuticals, Inc.Inventor: Paul Mollard
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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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Publication number: 20120295985Abstract: The present invention is concerned with a method for improving blood glucose control or for preventing or treating a condition requiring increasing insulin sensitivity or reducing insulin resistance in a subject in need of such control which comprises administering to the subject a composition comprising a therapeutically effective amount of one or more quinones of Formula I.Type: ApplicationFiled: November 18, 2011Publication date: November 22, 2012Inventors: Guy M. Miller, William D. Shrader, Martin J. Thoolen
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Patent number: 8106223Abstract: The invention discloses novel processes for production, enrichment and/or isolation of alpha-tocotrienol from source material comprising at least one non-alpha-tocotrienol, such as natural extracts comprising mixed tocotrienols.Type: GrantFiled: October 27, 2009Date of Patent: January 31, 2012Assignee: Edison Pharmaceuticals, Inc.Inventors: Kieron E. Wesson, Andrew W. Hinman, Orion D. Jankowski
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Publication number: 20100273894Abstract: The present invention relates to methods of treating Leber's hereditary optic neuropathy and dominant optic atrophy with tocotrienol quinones, including alpha-tocotrienol quinone, in order to alleviate symptoms of the disease.Type: ApplicationFiled: April 27, 2010Publication date: October 28, 2010Inventor: Guy M. MILLER
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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: 6815565Abstract: A method is described for the simultaneous preparation of p-bromophenols and p-benzoquinones, intermediates useful in the preparation of hydroquinones and 4,4′-dihydroxybiphenyls, respectively. Hydroquinones and 4,4′-dihydroxybiphenyls are useful monomers for the preparation of a variety of polymers. The method also comprises reducing the p-benzoquinone to its corresponding hydroquinone in the presence of the p-bromophenol. Limiting the amount of HBr present in the reaction mixture was shown to control the amount of benzoquinone produced. The method also allows for the recycling of many of the reagents used, thereby reducing the cost of producing each monomer.Type: GrantFiled: November 7, 2003Date of Patent: November 9, 2004Assignee: General Electric CompanyInventors: Ryan Christopher Mills, Eric James Pressman, Timothy Leigh Chuck, John Yaw Ofori
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Patent number: 6693221Abstract: A method is described for the simultaneous preparation of 4-bromophenols and p-benzoquinones, intermediates useful in the preparation of hydroquinones and 4,4′-dihydroxybiphenyls respectively. Hydroquinones and 4,4′-dihydroxybiphenyls are useful monomers for the preparation of a variety of polymers. In one example phenol is reacted with in the presence of HBr, a catalytic amount of cupric bromide and a stoichiometric excess of oxygen under relatively mild conditions to provide a mixture of the phenol, 4-bromophenol, and 1,4-benzoquinone. Phenol conversion was 54 percent and selectivities for bromophenol and benzoquinone were 23% and 37% respectively. Limiting the amount of HBr present in the reaction mixture was shown to control the amount of benzoquinone produced.Type: GrantFiled: April 4, 2003Date of Patent: February 17, 2004Assignee: General Electric CompanyInventors: Ryan Christopher Mills, Timothy Leigh Chuck
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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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Patent number: 6500972Abstract: A method of oxidizing trimethylphenol (TMP) to trimethylbenzoquinone (TMBQ) by various molecular sieves containing various transition metals. In this method, TMP, a molecular sieve containing a transition metal in its framework, an oxidant and a solvent are mixed together to form a reaction system. The reaction system reacting at a temperature of about room temperature to 150° C. to obtain TMBQ, and the concentration of TMP is about 5-60% wt.Type: GrantFiled: July 25, 2001Date of Patent: December 31, 2002Assignee: Chinese Petroleim Corp.Inventors: Soofin Cheng, Chia-Lung Tsai, Berryinne Chou, Debasish Das
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Patent number: 6346634Abstract: Compounds for use in the treatment of heart disease include a superoxide scavenger and an organic nitrate or nitrite moiety. The compounds can be represented by the formula (A)n(B)m, in which A is a superoxide scavenger, B is an organic nitrate or organic nitrite moiety, and n and m are values between 1 and 8. These compounds do not suffer from the problem of patient tolerance that is associated with the use of conventional agents such as organic nitrates.Type: GrantFiled: May 1, 2000Date of Patent: February 12, 2002Assignee: Teijin LimitedInventors: Zhi Zhang, Declan P. Naughton, Yoshihiko Sumi, Atsushi Imaizumi
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Patent number: 5804601Abstract: The present invention relates to a compound of the formula: ##STR1## wherein Ar represents an optionally substituted aromatic group; Q represents a divalent aliphatic hydrocarbon group; R.sub.1 represents hydrogen, cyano, an optionally substituted hydrocarbon group, a group of the formula: ##STR2## wherein R.sup.3 and R.sub.4 independently represent hydrogen, acyl or an optionally substituted hydrocarbon group, or R.sup.3 and R.sup.4 jointly form a ring, or acyl; R.sup.2 represents acyl; ......... represents a single bond or a double bond; m represents 1 or 2 or a salt, a process of producing thereof and an anti-neurodegenerative composition.Type: GrantFiled: April 9, 1996Date of Patent: September 8, 1998Assignee: Takeda Chemical Industries, Ltd.Inventors: Kaneyoshi Kato, Shokyo Miki, Ken-ichi Naruo, Hideki Takahashi
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Patent number: 5565586Abstract: A process for the industrial preparation of the quinone derivative represented by the following general formula: ##STR1## which is an intermediate for chroman derivatives useful as a blood sugar lowering agent, and novel intermediates, encompasses the following:(1) Oxidation of the corresponding hydroquinone derivative, and(2) Hydrolysis of the corresponding acyl hydroquinone derivative with a Claisen alkali, followed by the oxidation of resulting hydrolyzate.Type: GrantFiled: March 1, 1995Date of Patent: October 15, 1996Assignee: Eisai Chemical Co., Ltd.Inventors: Kimio Hamamura, Chiaki Seki, Masayuki Konishi
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Patent number: 5534548Abstract: Straight-chain alkanoic acids, substituted at the .OMEGA.-carbon atom by a substituted phenyl, naphthyl, furyl, or thienyl group and by a substituted 1,4-benzoquinon-2-yl group are effective in the therapy or prophylaxis of conditions associated with lipid peroxide injury to vascular endothelium particularly preeclampsia and eclampsia in pregnant females.Type: GrantFiled: May 3, 1994Date of Patent: July 9, 1996Assignee: TAP Pharmaceuticals, Inc.Inventor: Anthony Killian
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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: 5310957Abstract: Processes for the preparation of tetracyano-1,4-hydroquinone and its conversion to tetracyano-1,4-benzoquinone via a disilver salt are disclosed.Type: GrantFiled: November 10, 1992Date of Patent: May 10, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carlos Vazquez
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Patent number: 5304658Abstract: 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.tbd.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 polyunsaturate fatty acids, particularly production inhibitory activity of lipid peroxides (antioxidant activity), thromboxane A.sub.Type: GrantFiled: August 3, 1992Date of Patent: April 19, 1994Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Yoshitaka Maki
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Patent number: 5304663Abstract: A novel process for the preparation of pentaalkylchromenes of the general formula: ##STR1## wherein R denotes a lower alkyl group having 1 to 4 C atoms and R.sub.1 denotes a phenyl group which is unsubstituted or substituted by a lower alkyl group having 1 to 4 C atoms, by halogen or by a nitro group, or an alkanoyl group having 1 to 4 C atoms. In the process, a trialkylhydroquinone is reacted with a halogenated butenol to give a substituted tetraalkyhydroquinone, which is oxidized. Then the halogen atom is substituted with a suitable nucleophile and the compound is finally cyclized to give the final product. The pentaalkylchromenes are suitable intermediates for the preparation of hypolipidaemic pharmaceuticals.Type: GrantFiled: September 15, 1993Date of Patent: April 19, 1994Assignees: Lonza Ltd., Sankyo Company Ltd.Inventor: David Laffan
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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: 5262552Abstract: An optically active (S)- or (R)-pentane compound of the general formula (11): ##STR1## wherein R.sub.11, R.sub.12 and R.sub.13 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R.sub.14 represents a hydroxy, protected hydroxy or oxo group, if R.sub.14 is an oxo group, the ring denoting benzene in the above formula (11) is benzoquinone, R.sub.15 represents a hydrogen atom, hydroxy or acyloxy group, R.sub.16 represents a hydroxy or acyloxy group, and the chiral central carbon marked with a symbol * in said formula (11) alternatively has one of an R-configuration and an S-configuration, is disclosed. Further, intermediate products of the compound of the formula (11) are also disclosed. Still further, a process for manufacturing the above compounds is disclosed. The compound of the formula (11) is easily synthesized from an easily available optically active starting material.Type: GrantFiled: February 20, 1991Date of Patent: November 16, 1993Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5245059Abstract: 2,3,5-Trimethyl-p-benzoquinone is prepared advantageously by the catalytic oxidation of 2,3,5- or 2,3,6-trimethylphenol with hydrogen peroxide in an organic solvent, which is preferably acetic acid, in the presence of a catalyst which is a heteropolyacid of silicon or phosphorus as the center atom selected from phosphomolybdic acid, silicomolybdic acid, phosphotungstic acid and silicotungstic acid. The reaction proceeds rapidly even at room temperature to give the product in a high yield so that the method is industrially advantageous in addition to the advantages in respect of the inexpensiveness of the reactants and catalyst and absence of any noxious byproducts which may cause environmental pollution.Type: GrantFiled: March 3, 1989Date of Patent: September 14, 1993Assignee: Japan as represented by Director General of Agency of Industrial Science and TechnologyInventors: Masao Shimizu, Katsuomi Takehira, Takashi Hayakawa, Hideo Orita
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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: 5208391Abstract: Processes for the preparation of tetracyano-1,4-hydroquinone and its conversion to tetracyano-1,4-benzoquinone via a disilver salt are disclosed.Type: GrantFiled: July 18, 1991Date of Patent: May 4, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carlos Vazquez
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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: 5104996Abstract: 2,3,5-trimethyl-benzoquinone is produced by oxidizing 2,3,6-trimethyl-phenol in the presence of a catalyst of cupric chloride and lithium chloride in a solvent mixture of an aromatic hydrocarbon and a lower aliphatic alcohol having 1 to 4 carbon atoms.Type: GrantFiled: May 11, 1988Date of Patent: April 14, 1992Assignee: Eisai Co., Ltd.Inventors: Noriyasu Hirose, Kimio Hamamura, Yuichi Inai, Kiiti Ema, Takashi Banba, Shizumasa Kijima
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Patent number: 5104874Abstract: A series of 2-amino-5,6-dimethyl-1,4-benzoquinone derivatives, inhibitors of cyclooxygenase and lipoxygenase and useful as antiallergic and antiinflammatory agents.Type: GrantFiled: December 13, 1990Date of Patent: April 14, 1992Assignee: Pfizer Inc.Inventors: Takafumi Ikeda, Hiroaki Wakabayashi, Masami Nakane
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Patent number: 5068367Abstract: Processes for the preparation of tetracyano-1,4-hydroquinone and its conversion to tetracyano-1,4-benzoquinone via a disilver salt are disclosed.Type: GrantFiled: January 31, 1990Date of Patent: November 26, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Carlos Vazquez, Joel S. Miller
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Patent number: 5041572Abstract: 2,3,5-Trimethyl-p-benzoquinone is prepared by oxidation of trimethylphenol with oxygen or an oxygen-containing gas in the presence of a catalyst containing a copper(II) halide in a two-phase reaction medium consisting of water and an aliphatic alcohol at elevated temperatures by a process in which the reaction is carried out in a mixture of water and a saturated aliphatic alcohol of 12 to 18 carbon atoms, having a flashpoint greater than 120.degree. C., such as 1-dodecanol, 1-tetradecanol, 1-hexadecanol or 1-octadecanol, in particular 1-dodecanol, and at from 60.degree. to 100.degree. C.Particularly good yields of TMQ are obtained if the reaction is carried out in the presence of a copper(II) halide, such as CuCl.sub.2 or CuBr.sub.2, and of an alkaline earth metal halide, in particular CaCl.sub.2 or MgCl.sub.2, or of an alkali metal halide, in particular LiCl or NaCl, as the catalyst system.Type: GrantFiled: March 13, 1990Date of Patent: August 20, 1991Assignee: BASF AktiengesellschaftInventors: Ulrich Hoercher, Barbara Jessel, Bernhard Bockstiegel, Paul Grafen, Harald Laas
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Patent number: 4943645Abstract: 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: ##STR5## (wherein l is an integer of 1 to 4 and R.sub.Type: GrantFiled: August 8, 1989Date of Patent: July 24, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Hisayoshi Okazaki, Isuke Imada
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Patent number: 4913851Abstract: An asymmetric synthesis for Vitamin E in an optically active pure form for 4-(2,5-diloweralkanoyloxy)-3,4,6-trimethylphenyl-butan-2-one and intermediates therein.Type: GrantFiled: May 15, 1989Date of Patent: April 3, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Ka-kong Chan, Gabriel G. Saucy
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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