At Least Three Carbons Bonded Directly To The Cyclohexadiene Patents (Class 552/310)
  • Patent number: 10364231
    Abstract: 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: Grant
    Filed: August 14, 2017
    Date of Patent: July 30, 2019
    Assignee: BASF SE
    Inventors: Richard Dehn, Michael Kraus, Martine Dehn, Manuel Danz, Joaquim Henrique Teles
  • Patent number: 9162957
    Abstract: 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: Grant
    Filed: July 19, 2012
    Date of Patent: October 20, 2015
    Assignee: Edison Pharmaceuticals, Inc.
    Inventor: Paul Mollard
  • Publication number: 20140342998
    Abstract: 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: Application
    Filed: October 23, 2012
    Publication date: November 20, 2014
    Applicant: NICOX S.A.
    Inventors: Gael Ronsin, Laura Storoni, Francesca Benedini
  • Publication number: 20120295985
    Abstract: 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: Application
    Filed: November 18, 2011
    Publication date: November 22, 2012
    Inventors: Guy M. Miller, William D. Shrader, Martin J. Thoolen
  • Patent number: 8106223
    Abstract: 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: Grant
    Filed: October 27, 2009
    Date of Patent: January 31, 2012
    Assignee: Edison Pharmaceuticals, Inc.
    Inventors: Kieron E. Wesson, Andrew W. Hinman, Orion D. Jankowski
  • Publication number: 20100273894
    Abstract: 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: Application
    Filed: April 27, 2010
    Publication date: October 28, 2010
    Inventor: Guy M. MILLER
  • Patent number: 7064124
    Abstract: A NF-?B inhibitor represented by the following formula (I) is provided: ?
    Type: Grant
    Filed: March 27, 2002
    Date of Patent: June 20, 2006
    Assignees: Daiichi Suntory Pharma Co., Ltd., Daiichi Suntory Biomedical Research Co., Ltd.
    Inventors: Kenji Suzuki, Yoichi Nunokawa, Naohisa Ogou
  • Patent number: 6815565
    Abstract: 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: Grant
    Filed: November 7, 2003
    Date of Patent: November 9, 2004
    Assignee: General Electric Company
    Inventors: Ryan Christopher Mills, Eric James Pressman, Timothy Leigh Chuck, John Yaw Ofori
  • Patent number: 6693221
    Abstract: 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: Grant
    Filed: April 4, 2003
    Date of Patent: February 17, 2004
    Assignee: General Electric Company
    Inventors: Ryan Christopher Mills, Timothy Leigh Chuck
  • Patent number: 6506539
    Abstract: 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: Grant
    Filed: April 6, 2001
    Date of Patent: January 14, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinichi Morishima, Takashi Usami
  • Patent number: 6500972
    Abstract: 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: Grant
    Filed: July 25, 2001
    Date of Patent: December 31, 2002
    Assignee: Chinese Petroleim Corp.
    Inventors: Soofin Cheng, Chia-Lung Tsai, Berryinne Chou, Debasish Das
  • Patent number: 6346634
    Abstract: 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: Grant
    Filed: May 1, 2000
    Date of Patent: February 12, 2002
    Assignee: Teijin Limited
    Inventors: Zhi Zhang, Declan P. Naughton, Yoshihiko Sumi, Atsushi Imaizumi
  • Patent number: 5804601
    Abstract: 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: Grant
    Filed: April 9, 1996
    Date of Patent: September 8, 1998
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kaneyoshi Kato, Shokyo Miki, Ken-ichi Naruo, Hideki Takahashi
  • Patent number: 5565586
    Abstract: 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: Grant
    Filed: March 1, 1995
    Date of Patent: October 15, 1996
    Assignee: Eisai Chemical Co., Ltd.
    Inventors: Kimio Hamamura, Chiaki Seki, Masayuki Konishi
  • Patent number: 5534548
    Abstract: 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: Grant
    Filed: May 3, 1994
    Date of Patent: July 9, 1996
    Assignee: TAP Pharmaceuticals, Inc.
    Inventor: Anthony Killian
  • Patent number: 5318993
    Abstract: 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: Grant
    Filed: April 16, 1993
    Date of Patent: June 7, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5310957
    Abstract: Processes for the preparation of tetracyano-1,4-hydroquinone and its conversion to tetracyano-1,4-benzoquinone via a disilver salt are disclosed.
    Type: Grant
    Filed: November 10, 1992
    Date of Patent: May 10, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carlos Vazquez
  • Patent number: 5304658
    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.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: Grant
    Filed: August 3, 1992
    Date of Patent: April 19, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Yoshitaka Maki
  • Patent number: 5304663
    Abstract: 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: Grant
    Filed: September 15, 1993
    Date of Patent: April 19, 1994
    Assignees: Lonza Ltd., Sankyo Company Ltd.
    Inventor: David Laffan
  • Patent number: 5288752
    Abstract: 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: Grant
    Filed: November 23, 1992
    Date of Patent: February 22, 1994
    Assignee: Suntory Limited
    Inventors: Toshio Tatsuoka, Kenji Suzuki, Fumio Satoh, Seiji Miyano, Kunihiro Sumoto
  • Patent number: 5262552
    Abstract: 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: Grant
    Filed: February 20, 1991
    Date of Patent: November 16, 1993
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5245059
    Abstract: 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: Grant
    Filed: March 3, 1989
    Date of Patent: September 14, 1993
    Assignee: Japan as represented by Director General of Agency of Industrial Science and Technology
    Inventors: Masao Shimizu, Katsuomi Takehira, Takashi Hayakawa, Hideo Orita
  • Patent number: 5210239
    Abstract: 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: Grant
    Filed: August 31, 1990
    Date of Patent: May 11, 1993
    Assignee: 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
  • Patent number: 5208391
    Abstract: Processes for the preparation of tetracyano-1,4-hydroquinone and its conversion to tetracyano-1,4-benzoquinone via a disilver salt are disclosed.
    Type: Grant
    Filed: July 18, 1991
    Date of Patent: May 4, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carlos Vazquez
  • 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: 5104996
    Abstract: 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: Grant
    Filed: May 11, 1988
    Date of Patent: April 14, 1992
    Assignee: Eisai Co., Ltd.
    Inventors: Noriyasu Hirose, Kimio Hamamura, Yuichi Inai, Kiiti Ema, Takashi Banba, Shizumasa Kijima
  • Patent number: 5104874
    Abstract: 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: Grant
    Filed: December 13, 1990
    Date of Patent: April 14, 1992
    Assignee: Pfizer Inc.
    Inventors: Takafumi Ikeda, Hiroaki Wakabayashi, Masami Nakane
  • Patent number: 5068367
    Abstract: Processes for the preparation of tetracyano-1,4-hydroquinone and its conversion to tetracyano-1,4-benzoquinone via a disilver salt are disclosed.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: November 26, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Carlos Vazquez, Joel S. Miller
  • Patent number: 5041572
    Abstract: 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: Grant
    Filed: March 13, 1990
    Date of Patent: August 20, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Hoercher, Barbara Jessel, Bernhard Bockstiegel, Paul Grafen, Harald Laas
  • Patent number: 4943645
    Abstract: 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: Grant
    Filed: August 8, 1989
    Date of Patent: July 24, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Hisayoshi Okazaki, Isuke Imada
  • Patent number: 4913851
    Abstract: 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: Grant
    Filed: May 15, 1989
    Date of Patent: April 3, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ka-kong Chan, Gabriel G. Saucy
  • Patent number: 4874752
    Abstract: 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: Grant
    Filed: November 8, 1988
    Date of Patent: October 17, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Hisayoshi Okazaki, Isuke Imada