Ether Oxygen Bonded Directly To Benzene Ring Patents (Class 568/630)
  • Patent number: 6852895
    Abstract: The present invention provides a convergent method for the synthesis of ubiquinones and ubiquinone analogues. Also provided are precursors of ubiquinones and their analogues that are useful in the methods of the invention.
    Type: Grant
    Filed: September 27, 2002
    Date of Patent: February 8, 2005
    Assignee: Zymes, Inc.
    Inventors: Bruce H. Lipshutz, Paul Mollard
  • Patent number: 6835786
    Abstract: There are provided a polyfunctional (meth)acrylate compound which has the excellent properties of polyphenylene ether and is excellent in heat resistance and electric characteristics and excellent in reactivity by introducing a polyfunctional (meth)acrylate group into a bifunctional polyphenylene ether oligomer, and a cured product thereof which has a high glass transition temperature and has a low dielectric constant and a low dielectric loss tangent.
    Type: Grant
    Filed: July 25, 2003
    Date of Patent: December 28, 2004
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kenji Ishii, Yasumasa Norisue, Daisuke Ohno, Makoto Miyamoto
  • Patent number: 6822114
    Abstract: Roflumilast and new key intermediates therefor are prepared by processes involving use of carbonylation technology. Good overall yields can be achieved using available starting materials. The starting material for the process can be catechol, an o-R1-phenol, an o-R1-p-X-phenol, or a 1-X-3-R1-4-R2-benzene, where R1, is a C1-6 alkoxy, C3-7 cycloalkoxy, C3-7 cycloalkylmethoxy, or benzyloxy group, or a C1-4 alkoxy group which is completely or partially substituted by fluorine; R2 is a C1-4 alkoxy group which is completely or partially substituted by fluorine; and X is Cl, Br, or I.
    Type: Grant
    Filed: October 8, 2002
    Date of Patent: November 23, 2004
    Assignee: Albemarle Corporation
    Inventors: Eric L. Williams, Tse-Chong Wu
  • Patent number: 6809223
    Abstract: An improved method is described for making 9-deoxy-PGF1-type compounds. In contrast to the prior art, the method is stereoselective and requires fewer steps than the known methods for making these compounds. “Also described are novel intermediate compounds used in the process described for making 9-deoxy-PGF1-type compounds.
    Type: Grant
    Filed: August 27, 2003
    Date of Patent: October 26, 2004
    Assignee: United Therapeutics Corporation
    Inventors: Robert M. Moriarty, Hitesh Bhatra
  • Patent number: 6800605
    Abstract: New thyroid receptor ligands are provided which have the general formula in which: X is —O—, —S—, —CH2—, —CO—, or —NH—; Y is —(CH2)n— where n is an integer from 1 to 5, or cis- or trans-ethylene; R1 is halogen, trifluoromethyl, or alkyl of 1 to 6 carbons or cycloalkyl of 3 to 7 carbons; R2 and R3 are the same or different and are hydrogen, halogen, alkyl of 1 to 4 carbons or cycloalkyl of 3 to 6 carbons, at least one of R2 and R3 being other than hydrogen; R4 is hydrogen or lower alkyl; R5 is hydrogen or lower alkyl; R6 is carboxylic acid, or esters or prodrugs; R7 is hydrogen or an alkanoyl or an aroyl. In addition, a method is provided for preventing, inhibiting or treating a disease associated with metabolism dysfunction or which is dependent upon the expression of a T3 regulated gene, wherein a compound as described above is administered in a therapeutically effective amount.
    Type: Grant
    Filed: January 16, 2001
    Date of Patent: October 5, 2004
    Assignee: Bristol-Myers Squibb Company
    Inventors: Todd J. Friends, Denis E. Ryono, Minsheng Zhang
  • Patent number: 6770463
    Abstract: There is provided a process for the preparation of a chiral insecticidal and acaricidal compound of formula I. Also provided are intermediate compounds useful in the process of the present invention.
    Type: Grant
    Filed: August 2, 2001
    Date of Patent: August 3, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: John Francis Chiarello, Brian Lee Buckwalter, Timothy Claude Barden
  • Patent number: 6768025
    Abstract: Benzoylcyclohexanedione derivatives of the formula (I) and their use as herbicides are described. In this formula (I), R1, R3, and R4 are various radicals, L—(R2)n is haloalkyl, and n is 0 to 2.
    Type: Grant
    Filed: April 4, 2002
    Date of Patent: July 27, 2004
    Assignee: Aventis CropScience GmbH
    Inventors: Thomas Seitz, Andreas van Almsick, Lothar Willms, Thomas Auler, Hermann Bieringer, Hubert Menne
  • Patent number: 6765079
    Abstract: Novel cross linked polymer films prepared from poly4-[(4-cardanylazo]benzoic acid and poly4-[(4-acryloylcardanylazo]benzoic acid are disclosed. The invention also relates to novel monomers 4-[(4-cardanylazo] benzoic acid and 4-[(4-acryloylcardanylazo] benzoic acid and polymers thereof as well processes for the preparation thereof.
    Type: Grant
    Filed: March 24, 2003
    Date of Patent: July 20, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Muthusamy Saminathan, Chennakkattu Krishna Sadasivan Pillai
  • Patent number: 6756512
    Abstract: The invention relates to a novel process for preparing 2-alkyl-3-chlorophenols.
    Type: Grant
    Filed: October 30, 2002
    Date of Patent: June 29, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Hübsch, Reinhard Lantzsch, Thorsten Müh, Holger Weintritt
  • Patent number: 6750372
    Abstract: A method for producing an aryl ether produced by bonding an aryloxy of hydroxyaryl with an organic group of organic halogen, which comprises reacting hydroxyaryl with organic halogen in gaseous carbon dioxide or supercritical carbon dioxide in the presence of base and catalytic amount of onium salt.
    Type: Grant
    Filed: July 30, 2002
    Date of Patent: June 15, 2004
    Assignee: Japan Science and Technology Agency
    Inventor: Masaaki Yoshida
  • Patent number: 6706929
    Abstract: An accelerated process for preparing an O-methyl phenol comprising reacting a phenol with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to another aspect, the invention provides an accelerated process for preparing an N-methyl heteroaromatic compound comprising reacting an NH-containing heteroaromatic compound with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to an additional aspect, the invention provides an accelerated process for preparing a methylated aminophenol comprising reacting an aminophenol having at least one N—H with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine.
    Type: Grant
    Filed: June 12, 2003
    Date of Patent: March 16, 2004
    Assignee: Novartis AG
    Inventors: Wen-Chung Shieh, Steven Dell
  • Publication number: 20030216583
    Abstract: An accelerated process for preparing an O-methyl phenol comprising reacting a phenol with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to another aspect, the invention provides an accelerated process for preparing an N-methyl heteroaromatic compound comprising reacting an NH-containing heteroaromatic compound with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to an additional aspect, the invention provides an accelerated process for preparing a methylated aminophenol comprising reacting an aminophenol having at least one N—H with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine.
    Type: Application
    Filed: June 12, 2003
    Publication date: November 20, 2003
    Inventors: Wen-Chung Shieh, Steven Dell
  • Patent number: 6632963
    Abstract: Novel pharmaceutically/cosmetically-active bicyclic aromatic compounds have the structural formula (I): in which Ar1 is a radical having one of the structural formulae (a)-(c): Ar2 is a radical having one of the following formulae (d)-(h): and X is a radical having one of the following formulae (i)-(l): 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: March 29, 1999
    Date of Patent: October 14, 2003
    Assignee: Galderma Research & Development S.N.C.
    Inventor: Jean-Michel Bernardon
  • Patent number: 6624334
    Abstract: Aryl alkyl ethers can be produced by the reaction of hydroxyaromatics with an alcohol in the presence of a catalyst. This process achieves higher yields of aryl alkyl ethers and the formation of ring-alkylated products and dialkyl ethers is markedly reduced.
    Type: Grant
    Filed: April 8, 2002
    Date of Patent: September 23, 2003
    Assignees: Haarmann & Reimer GmbH, Bayer Aktiengesellschaft
    Inventors: Efim Biller, Edgar Fuhrmann, Detlef Hagena, Heinz Günter Janneck, Jörg Talbiersky, Lutz Walther
  • Patent number: 6608232
    Abstract: The invention concerns a method for preparing a benzylic-type ether from an aromatic compound. The inventive method for preparing a benzylic-type ether from an aromatic compound is characterised in that it consists in: in a first step, acylating an aromatic compound by reacting said aromatic compound with an acylating agent, in the presence of an efficient amount of zeolite or a Friedel-Crafts catalyst leading to a ketonic compound; in a second step, reducing the carbonyl group into carbinol leading to a benzylic alcohol; in a third step, etherifying the hydroxyl group, by reacting the benzylic alcohol with another alcohol, in the presence of an efficient amount of zeolite.
    Type: Grant
    Filed: July 3, 2001
    Date of Patent: August 19, 2003
    Inventors: Roland Jacquot, Michel Spagnol
  • Patent number: 6608212
    Abstract: The present invention provides a process for preparing a vinylaromatic compound comprising reacting an arylmetal reagent selected from arylmagnesium reagents and aryllithium reagents with a vinylphosphate in the presence of a palladium catalyst. The present invention also provides a process for preparing a vinylphosphate comprising reacting an enolizable ketone with a sterically hindered Grignard reagent and a halophosphate diester.
    Type: Grant
    Filed: June 4, 2002
    Date of Patent: August 19, 2003
    Assignees: Pfizer, Inc., DSM NV
    Inventor: Joseph Miller
  • Patent number: 6590127
    Abstract: The present invention relates to a process for the preparation of high purity and yield &agr;-asarone, trans 2,4,5-trimethoxy cinnamaldehyde, 2,4,5-trimethoxy-phenyl propionone, from &bgr;-asarone or &bgr;-asarone rich Acorus calamus oil containing &agr; and &ggr;-asarone by hydrogenating, followed by treatment with DDQ with or without solid support of silica gel or alumina in dry organic solvent and &agr;-asarone can also be obtained by treating the hydrogenated product of &bgr;-asarone or &bgr;-asarone rich Acorus calamus with DDQ in an aqueous organic solvent to obtain an intermediate 2,4,5-trimethoxy phenyl propionone, which in turn is reduced with sodiumborohydride to obtain the corresponding 2,4,5-trimethoxy-phenyl propanol and followed by final treatment with a dehydrating agent.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: July 8, 2003
    Assignee: Council of Scientific & Industrial Research
    Inventors: Arun Kumar Sinha, Bhupendra Prasad Joshi, Ruchi Acharya
  • Publication number: 20030120124
    Abstract: A palladium catalyzed cross-coupling of aryldiazonium salts with organosilanes is disclosed. New reactions that are user friendly and environmentally friendly are now possible, including some reactions that could not be achieved using prior methods. The organosilanes that may be cross-coupled with aryldiazonium salts include, for example, Ar′—Si(L)3, where Ar′=aryl, and where L=CH3, OCH3, F, Cl, R, or OR.
    Type: Application
    Filed: November 8, 2001
    Publication date: June 26, 2003
    Inventor: David A. Spivak
  • Publication number: 20030114715
    Abstract: Alkenyl ethers are prepared by reacting the corresponding alcohols or phenols with acetylenes in the liquid phase in the presence of basic alkali metal compounds and a cocatalyst comprising compounds of the formula (Ia) and/or (Ib)
    Type: Application
    Filed: October 3, 2002
    Publication date: June 19, 2003
    Inventors: Arnd Boettcher, Rolf Pinkos, Rudolf Erich Lorenz
  • Patent number: 6552213
    Abstract: The present invention relates to a new stereoselective method for the preparation of tris-O-substituted-(E)-1-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)ethene derivative of the formula (I) which is a key intermediate in the synthesis of trans-resveratrol (I, R2=R2=R3=H). The invention also provides a method for the exclusive synthesis of trans-isomer of compounds of formula (I) without any contamination of cis-isomer.
    Type: Grant
    Filed: May 24, 2002
    Date of Patent: April 22, 2003
    Assignee: Orchid Chemicals & Pharmaceuticals Limited, India
    Inventors: Pandurang Balwant Deshpande, Udayampalayam Palanisamy Senthilkumar, Gnanaprakasam Andrew
  • Publication number: 20030073848
    Abstract: An accelerated process for preparing an O-methyl phenol comprising reacting a phenol with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to another aspect, the invention provides an accelerated process for preparing an N-methyl heteroaromatic compound comprising reacting an NH-containing heteroaromatic compound with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to an additional aspect, the invention provides an accelerated process for preparing a methylated aminophenol comprising reacting an aminophenol having at least one N—H with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine.
    Type: Application
    Filed: October 17, 2001
    Publication date: April 17, 2003
    Inventors: Wen-Chung Shieh, Steven J. Dell
  • Patent number: 6509507
    Abstract: A process for preparing polymerizable biaryl derivatives comprises reacting an aromatic comprising a 6-membered ring which bears ester or benzylic OH groups in the 1,4 position with a second aromatic in a palladium-catalyzed cross-coupling reaction to give a biaryl and converting the ester or benzylic OH groups into polymerizable groups in one or more steps. The biaryls obtained are suitable for preparing polymers which are used as electroluminescence materials.
    Type: Grant
    Filed: October 16, 2001
    Date of Patent: January 21, 2003
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Jochen Krause
  • Patent number: 6498278
    Abstract: A method for the preparation of &ggr;-hydroxy ethers from cyclic organic carbonates and active-hydrogen-containing compounds in one form includes the steps of contacting an active-hydrogen-containing compound and a cyclic organic carbonate compound containing a six-membered ring, and a catalyst, running the reaction at a suitable temperature, and isolating the &ggr;-hydroxy ether as a mixture that can be purified or used directly as produced in the reaction.
    Type: Grant
    Filed: September 5, 2001
    Date of Patent: December 24, 2002
    Assignee: Huntsman Petrochemical Corporation
    Inventors: John H. Clements, Howard P. Klein, Edward T. Marquis
  • Patent number: 6462240
    Abstract: 3-Substituted benzotrifluorides are selectively deprotonated and functionalized in the 2-position. The selectivity is achieved by equilibrating the mixture of lithiobenzotrifluorides initially formed in the presence of a primary or secondary amine catalyst.
    Type: Grant
    Filed: June 14, 2001
    Date of Patent: October 8, 2002
    Assignee: Dow AgroSciences LLC
    Inventors: Michael Glenn Smith, Mark Andrew Pobanz, Gary A. Roth, Michael A. Gonzalez
  • Patent number: 6444858
    Abstract: The present invention provides a method for alkoxylating organic compounds comprising contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective to alkoxylate the organic compound. The alkylene oxide is maintained in vapor form during transport to said reaction vessel, during discharge into said reaction vessel, and during contacting of the organic compound with the alkylene oxide. The result is an alkoxylated product containing less flocculant.
    Type: Grant
    Filed: April 19, 1999
    Date of Patent: September 3, 2002
    Assignee: Baker Hughes Incorporated
    Inventor: Philip Leung
  • Publication number: 20020119106
    Abstract: A antimicrobial compound, compositions containing the same, and method of using the same for reducing the presence of microorganism on a substrate or in a fluid environment comprising an antimicrobial effective carrier and at least one antimicrobial compounds including non-halogenated phenyl substituted phenol compounds.
    Type: Application
    Filed: December 20, 2001
    Publication date: August 29, 2002
    Inventors: David Scott Harper, Robert A. Coburn, Constantine Georgiades, Andre Soshinsky, Marianne D. Huntley
  • Patent number: 6441205
    Abstract: The invention provides a novel compound 4-(p-methoxy-phenyl)-2-aminobutane exhibiting growth inhibition and antifeedant activity and represented by the structural formula. C11H17ON=4-(p-methoxy phenyl)-2-amino butane and an insecticidal composition comprising an effective amount of the novel compound and appropriate adjuvant.
    Type: Grant
    Filed: May 19, 2000
    Date of Patent: August 27, 2002
    Assignee: Council of Scientific and Industrial Research
    Inventors: Sunil Kumar Chattopadhyay, Koneni Venkata Sashidhara, Vinayak Tripathi, Arun Kumar Tripathi, Veena Prajapati, Sushil Kumar
  • Patent number: 6420130
    Abstract: The invention provides a compound, useful as an optical probe or sensor of the activity of at least one cytochrome P450 enzyme, and methods of using the compound to screen candidate drugs, and candidate drugs identified by these methods.
    Type: Grant
    Filed: April 28, 1999
    Date of Patent: July 16, 2002
    Assignee: Aurora Biosciences Corporation
    Inventors: Lewis R. Makings, Gregor Zlokarnik
  • Patent number: 6399837
    Abstract: A method of polymerizing at least one olefin comprising contacting the olefin with a catalyst composition comprising: 1) a procatalyst composition comprising a magnesium and titanium-containing component and an electron donor compound of the structure: wherein R1 is ethoxy, and R2 is an alkoxy group having from one to ten carbon atoms, and R3-R6 are each individually, hydrogen, hydrocarbyl, hydrocarboxy, nitro, a silyl group or a halogen, 2) a cocatalyst and optionally 3) a selectivity control agent.
    Type: Grant
    Filed: June 5, 2000
    Date of Patent: June 4, 2002
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stanley Edward Wilson, Robert Converse Brady, III
  • Patent number: 6399785
    Abstract: The invention is directed to multiply-substituted fullerene derivatives of novel configurations, and methods for their preparation and use. The methods involve the combinatorial synthesis of a library of fullerene derivatives and comprises the steps of forming a mixture of fullerene derivatives by reacting the Cn fullerene with two or more reactive precursor compounds, and removing the unreacted compounds to yield the fullerene derivatives having the desired activity. Methods for the identification and screening of a combinatorial library of fullerenes by 3He-nuclear magnetic resonance and electrospray mass spectrometry to define members with the optimal desired activity are also provided.
    Type: Grant
    Filed: October 30, 2000
    Date of Patent: June 4, 2002
    Assignee: C-Sixty, Inc.
    Inventors: Randall B. Murphy, Stephen R. Wilson, Quing Lu
  • Publication number: 20020058765
    Abstract: The present invention relates to a metal-free cyclopentadienide compound which, in conjunction with a metallocene, is able to form a catalyst system that can be used for the polymerization of olefins. It is thus possible to dispense with the use of methylaluminoxane (MAO) or boron-containing compounds as co-catalyst and nevertheless achieve a high degree of catalytic activity. The invention relates also to a process for the preparation of the metal-free cyclopentadienide compound and to the use thereof as a catalyst component in the preparation of polyolefins.
    Type: Application
    Filed: August 3, 2001
    Publication date: May 16, 2002
    Inventors: Sigurd Becke, Uwe Denninger, Steffen Kahlert, Werner Obrecht, Claudia Schmid, Heike Windisch
  • Patent number: 6388146
    Abstract: The polymerizable compound of this invention is represented by general formula (I): where R is H, R′, R′O, R′COO, or R′OCO, R′ is a linear or branched alkyl group or alkenyl group having 1 to about 15 carbon atoms, A1 and A2 are independently a cyclohexane ring or a benzene ring which may include a substituent represented by formula (II) below; X is H or CH3; and Y1, Y2, Y3, and Y4 are independently H, F, Cl, CH3, CH3O, CF3, or CF3O wherein at least two of Y1, Y2, Y3, and Y4 are H and, if both A1 and A2 are cyclohexane rings, at least one of Y1, Y2, Y3, and Y4 is not H: where Y5, Y6, Y7, and Y8 are independently H, F, Cl, CH3, CH3O, CF3, or CF3O, at least two of Y5, Y6, Y7, and Y8 are H.
    Type: Grant
    Filed: January 27, 1999
    Date of Patent: May 14, 2002
    Assignees: Sharp Kabushiki Kaisha, Kanto Kagaku Kabushiki Kaisha
    Inventors: Noriaki Onishi, Aya Miyazaki, Hoyo Mizobe, Masahiko Yoshida, Kenji Suzuki
  • Patent number: 6379590
    Abstract: A new method for producing unsymmetrically substituted fluorenyl compounds, one step of which is the preparation of 2,7-disubstituted fluoren-9-one derivatives via the nucleophilic substitution of a compound of the formula D wherein A′ is selected from the group consisting of —Br, —Cl, —F, —NO2, and —CN; A is selected from the group consisting of —NO2, —CN, —CO2R, —C(O)R, —SO2R, —SO2RF, —C(CN)═C(CN)2 and —CH═C(CN)2; RF is —CpF2p+1, p=from about 0 to about 10; R is an straight, branched or cyclic aliphatic alkyl group having about 1 to 10 carbon atoms, or an aromatic group such as phenyl or naphthyl; and is a carbonyl or a protected carbonyl such as a ketal or thio-ketal such as wherein R′ is —CrH2r+1; R″ is —(CH2)r—; and r is independently 2 or 3, with a nucleophilic reagent in the presence of an aprotic solvent
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: April 30, 2002
    Assignee: AlliedSignal Inc.
    Inventors: Chengjiu Wu, Jianhui Shan
  • Patent number: 6369279
    Abstract: Styrene derivatives of formula (1) are novel wherein R1 is hydrogen, C1-20 alkyl, fluoro-substituted C1-20 alkyl, chloro, or trichloromethyl, R2 is a phenol protecting group, p, q and r are integers in the range of 0≦p<5, 0≦q<5, 0<r<5, and 0<p+q<5. Polymers obtained by polymerizing the styrene derivatives are useful as the base polymer of resist compositions.
    Type: Grant
    Filed: September 7, 2000
    Date of Patent: April 9, 2002
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Mutsuo Nakashima, Jun Hatakeyama, Jun Watanabe, Yuji Harada
  • Patent number: 6355813
    Abstract: Invented is an improved process for preparing aromatic ring-fused cyclopentane derivatives. Preferred compounds prepared by this invention are indane carboxylates and cyclopentanopyridine derivatives. The most preferred compounds prepared by this invention are (+)(1S, 2R, 3S)-3-[2-(2-hydroxyeth-1-yloxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof and (+)(1S, 2R, 3S)-3-(2-carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof. Also invented are novel intermediates useful in preparing these compounds.
    Type: Grant
    Filed: June 29, 2000
    Date of Patent: March 12, 2002
    Assignee: SmithKline Beecham Corporation
    Inventors: William Morrow Clark, Ivan Lantos, Robert John Mills, Lendon Norwood Pridgen, Ann Marie Tickner
  • Publication number: 20020026084
    Abstract: A process for the production of a styrene compound is provided. The process comprises reacting a Grignard reagent prepared from a tertiary butoxyphenyl halide with a vinyl halide in the presence of a catalyst, wherein the catalyst is at least one member selected from the group consisting of manganese catalyst, iron catalyst, cobalt catalyst and rhodium catalyst. The process overcomes the problems involved in the prior art, and is economical and safe. The styrene compound by the process is free from biphenyl.
    Type: Application
    Filed: August 8, 2001
    Publication date: February 28, 2002
    Applicant: Tosoh Corporation
    Inventors: Shin-Ichi Ishikawa, Hisao Eguchi
  • Patent number: 6333436
    Abstract: Styrene derivatives of formula (1) are novel wherein R1 is H, F, C1-20 alkyl or fluorinated C1-20 alkyl, R2 in cis or trans conformation is F, C1-20 alkyl or fluorinated C1-20 alkyl, R3 is a phenol protecting group, p, q and r are integers in the range of 0≦p<5, 0≦q<5, 0<r<5, and 0≦p+q<5. Polymers obtained by polymerizing the styrene derivatives are useful as the base polymer of resist compositions.
    Type: Grant
    Filed: October 12, 2000
    Date of Patent: December 25, 2001
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Matsuo Nakashima, Jun Hatakeyama, Jun Watanabe, Yuji Harada
  • Patent number: 6323373
    Abstract: A process for preparing polymerizable biaryl derivatives comprises reacting an aromatic comprising a 6-membered ring which bears ester or benzylic OH groups in the 1,4 position with a second aromatic in a palladium-catalyzed cross-coupling reaction to give a biaryl and converting the ester or benzylic OH groups into polymerizable groups in one or more steps. The biaryls obtained are suitable for preparing polymers which are used as electroluminescence materials.
    Type: Grant
    Filed: June 9, 1999
    Date of Patent: November 27, 2001
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Jochen Krause
  • Patent number: 6316675
    Abstract: A process for the synthesis of olefins having aromatic substituents is described in which olefins are reacted with aryl halides in the presence of catalysts consisting of palladium compounds and tetraaryl phosphonium salts.
    Type: Grant
    Filed: September 23, 1999
    Date of Patent: November 13, 2001
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer
  • Patent number: 6291723
    Abstract: A catalyst composition comprising trifluoromethanesulfonic acid (also referred to as triflic acid) and a sufficient quantity of a substance (also referred to as a retarder) to decrease but not eliminate the catalytic activity of the acid is disclosed. Also disclosed, is a method and composition for condensing a hydroxyaryl with a diene by use of the catalyst composition. The method is capable of producing condensates having: a mole ratio of 1 mole of the diene to one mole of the hydroxyaryl; one mole of diene to two moles of the hydroxyaryl as well as higher molecular weight products such as resins by changes in temperature, time of reaction, type and quantity of retarder and other variables.
    Type: Grant
    Filed: September 2, 1999
    Date of Patent: September 18, 2001
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur H. Gerber
  • Patent number: 6274635
    Abstract: The present invention provides a method, compounds, and compositions for treating a disease associated with immune dysfunction. In accordance with the method, a pharmacologically-acceptable composition including at least one compound selected from the group of compounds consisting of 5-alkyl-resorcinol derivatives, cannabinol derivatives, cannabidiol derivatives, cannabigerol derivatives, and combinations thereof is administered to a patient under conditions sufficient to attenuate the dysfunction within the immune system. The invention also provides an antiviral cannabinol derivative that can be used in the inventive method. The invention also provides an alkylated resorcinol derivative and a method of using the alkylated resorcinol derivative to attenuate the growth of a neoplasm. The method and compound are useful for treating diseases of the immune system, such as HIV disease and neoplastic disorders.
    Type: Grant
    Filed: March 22, 2000
    Date of Patent: August 14, 2001
    Assignee: Immugen Pharmaceuticals Inc.
    Inventor: Craig A. Travis
  • Publication number: 20010008942
    Abstract: A method for preparing an aryl ether compound is provided in which an alcohol is reacted with an aromatic compound in the presence of a base, and a transition metal catalyst selected from the group consisting of platinum and nickel to form an aryl ether. The aromatic compound comprises an activated substituent, X, said activated substituent being a moiety such that its conjugate acid HX has a pKa of less than 5.0. The catalyst is preferably a soluble palladium complex in the presence of supporting ligands.
    Type: Application
    Filed: December 21, 2000
    Publication date: July 19, 2001
    Inventors: Stephen L. Buchwald, John P. Wolfe, Michael Palucki
  • Patent number: 6239317
    Abstract: There is described a four step process for the production of halogeno-o-hydroxydiphenyl compounds having the formula in which X is —O—or —CH2—; m is 1 to 3; and n is 1 or 2; wherein in the first step, a diphenyl compound is chlorinated; in a second step the chlorinated compound is acylated in a Friedel-Crafts reaction and optionally again chlorinated after the acylation; in a third step the acyl compound is oxidised; and in a fourth step the oxidized compound is hydrolyzed. The compounds of formula (1) are useful for the protection of organic materials against microorganisms.
    Type: Grant
    Filed: February 5, 1998
    Date of Patent: May 29, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Surendra Umesh Kulkarni, Vadiraj Subbanna Ekkundi, Pradeep Jeevaji Nadkarni, Chandrasekhar Dayal Mudaliar, Kishore Ramachandra Nivalkar
  • Patent number: 6229054
    Abstract: The present invention comprises a process for the hydroxyalkylation of cardanol with cyclic organic carbonates in the presence of organic or inorganic catalysts and a novel composition of matter produced by that process. The unique molecular structure of cardanol allows the use of a variety of organic or inorganic basic catalysts, including triethylamine, imidazol, sodium hydroxide and sodium carbonate, in the hydroxyalkylation reaction without forming quantities of undesirable side-products. According to this invention, the final product, monohydroxyalkylcardanyl ether, can be obtained with high yield and high purity. The product has a light color and its color stability is enhanced by replacing the phenol's hydroxyl group with a more stable hydroxyalkoxyl group.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: May 8, 2001
    Assignee: Cardolite Corporation
    Inventors: Zhisheng Dai, Meng J. Chen
  • Publication number: 20010000520
    Abstract: The invention relates to a novel process for the manufacture of very low molecular weight polyphenylene ether resin, typically within the intrinsic viscosity range of about 0.08 dl/g to about 0.16 dl/g as measured in chloroform at 25° C. The method preferably comprises 2,6-dimethylphenol as a monovalent phenol species.
    Type: Application
    Filed: December 13, 2000
    Publication date: April 26, 2001
    Applicant: General Electric Co.
    Inventors: Adrianus J.F.M. Braat, Hugo Ingelbrecht, Ruud Trion
  • Patent number: 6211416
    Abstract: Enol ethers of the formula I where R1 is an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical which may carry further substituents which do not react with acetylenes or allenes, and the radicals R, independently of one another, are hydrogen or aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radicals, which may be bonded to one another to form a ring, and m is 0 or 1, are prepared by reacting an acetal or ketal of the formula II with an acetylene or allene of the formula III or IV where R and R1 have the abovementioned meanings, in the gas phase at elevated temperatures in the presence of a zinc- or cadmium- and silicon- and oxygen-containing heterogeneous catalyst.
    Type: Grant
    Filed: December 6, 1999
    Date of Patent: April 3, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Joaquim Henrique Teles, Norbert Rieber, Klaus Breuer, Dirk Demuth, Hartmut Hibst, Heinz Etzrodt, Udo Rheude
  • Patent number: 6184381
    Abstract: This document describes a novel and practically excellent process for the preparation of optically active compounds, such as optically active alcohols or amines which are useful for various applications, for example, as synthetic intermediates of pharmaceuticals, liquid crystal materials, and reagents for optical resolution, wherein a hydrogen transfer type asymmetric reduction is carried out in the presence of both a transition metal complex and an optically active nitrogen compound or a transition metal complex having an optically active nitrogen compounds as an asymmetric ligand, and a hydrogen-donating organic or inorganic compound.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: February 6, 2001
    Assignees: Japan Science & Technology Corp., NKK Corp., Takeda Chemical Industries, Asahi Kasei Kogyo Kabushiki Kaisha, Takasago Intl. Corp.
    Inventors: Takao Ikariya, Shohei Hashiguchi, Jun Takehara, Nobuyuki Uematsu, Kazuhiko Matsumura, Ryoji Noyori, Akio Fujii
  • Patent number: 6180833
    Abstract: Stable, enzymatically triggered chemiluminescent 1,2-dioxetanes with improved water solubility and storage stability are provided as well as synthetic processes and intermediates used in their preparation. Dioxetanes further substituted with two or more water-solubilizing groups disposed on the dioxetane structure and an additional fluorine atom or lower alkyl group provide superior performance by eliminating the problem of reagent carryover when used in assays performed on capsule chemistry analytical systems. These dioxetanes display substantially improved stability on storage. Compositions comprising these dioxetanes, a non-polymeric cationic surfactant enhancer and optionally a fluorescer, for providing enhanced chemiluminescence are also provided.
    Type: Grant
    Filed: January 4, 2000
    Date of Patent: January 30, 2001
    Assignee: Lumigen, Inc.
    Inventor: Kumar Thakur
  • Patent number: 6172272
    Abstract: A high-yield process for converting lignin into reformulated, partially oxygenated gasoline compositions of high quality is provided. The process is a two-stage catalytic reaction process that produces a reformulated, partially oxygenated gasoline product with a controlled amount of aromatics. In the first stage of the process, a lignin feed material is subjected to a base-catalyzed depolymerization reaction, followed by a selective hydrocracking reaction which utilizes a superacid catalyst to produce a high oxygen-content depolymerized lignin product mainly composed of alkylated phenols, alkylated alkoxyphenols, and alkylbenzenes.
    Type: Grant
    Filed: August 18, 1999
    Date of Patent: January 9, 2001
    Assignee: The University of Utah
    Inventors: Joseph S. Shabtai, Wlodzimierz W. Zmierczak, Esteban Chornet
  • Patent number: 6166272
    Abstract: Disclosed is a method of fluorinating a substrate having the general formula ##STR1## where each R is independently selected from halogen, alkyl from C.sub.1 to C.sub.12, aryl from C.sub.6 to C.sub.12, alkoxide from C.sub.1 to C.sub.12, aryloxide from C.sub.6 to C.sub.12, nitro, amino, alkylamino from C.sub.1 to C.sub.12, and arylamino from C.sub.6 to C.sub.12, each X is independently selected from halogen and at least one X is chlorine or bromine, each m is independently selected from 0 to 5, n is 0 or 1, p is 0 or 1, q is 0 or 1, and n+p+q is 1. The substrate is heated to a temperature of about 40 to about 100.degree. C. and is reacted with a fluorinating agent in the presence of about 0.05 to about 2 wt % molybdenum trioxide. The composition of the substrate, the catalyst, and the fluorinating agent is also disclosed.
    Type: Grant
    Filed: August 12, 1999
    Date of Patent: December 26, 2000
    Assignee: Occidental Chemical Corporation
    Inventor: Sanjay Mandal