Ring In Alcohol Moiety Patents (Class 560/106)
  • Patent number: 7429673
    Abstract: The compounds of the general formula (I) in which X is represents two hydrogen atoms, a ?-bond, oxygen or methylene: R2 is a C6-C12 aryl, or arylalkyl residue: R3 is hydrogen, 2-hydroxyethyl or 2-aminoethyl are useful for the treatment of pathologies mediated by vanilloid receptors type I.
    Type: Grant
    Filed: July 6, 2005
    Date of Patent: September 30, 2008
    Assignee: Indena S.p.A.
    Inventors: Paolo Morazzoni, Antonella Riva, Gabriele Fontana, Giovanni Appendino, Vincenzo Di Marzo
  • Patent number: 7393970
    Abstract: The compound boron carbide, B4C, is an effective catalyst for the synthesis of aromatic esters by reacting benzoyl halides with phenols in the presence of powdered B4C.
    Type: Grant
    Filed: August 31, 2007
    Date of Patent: July 1, 2008
    Assignee: The College of N.J
    Inventor: Philip Edward Dumas
  • Patent number: 7230003
    Abstract: Prodrugs of propofol, methods of making prodrugs of propofol, pharmaceutical compositions of prodrugs of propofol and methods of using prodrugs of propofol and pharmaceutical compositions thereof to treat or prevent diseases or disorders such as migraine headache pain and post-chemotherapy or post-operative surgery nausea and vomiting are disclosed herein.
    Type: Grant
    Filed: September 9, 2004
    Date of Patent: June 12, 2007
    Assignee: XenoPort, Inc.
    Inventors: Mark A. Gallop, Feng Xu
  • Patent number: 6989462
    Abstract: A process is described for preparing compounds of formula (I) where R is H, optionally halogen-substituted alkyl, cycloalkyl, aryl, alkyl-aryl or heteroaryl, and, in alkyl and cycloalkyl, one or more CH2 groups may be replaced by —O—. The compounds of the formula (I) are valuable intermediates in the synthesis of PPAR agonists.
    Type: Grant
    Filed: March 18, 2004
    Date of Patent: January 24, 2006
    Assignee: Sanofi-Aventis Deutschland GmbH
    Inventors: Claus-Jürgen Maier, Tobias Metzenthin, Joachim Graeser, Richard Bicker, Javier Manero
  • Patent number: 6949585
    Abstract: The present invention provides a compound which has cytokine production inhibitory activity and is useful for the treatment of diseases which is associated with cytokine. The compound is represented by the following general formula (I) [wherein A represents a cyclic group which may be substituted; the partial structure -DE- represents a group represented by —CH2CH2— or —CH?CH—; W represents a group represented by —CH2—, —CH2CH2—, —CH?CH— or —CH?; the partial structure >XY— represents a group represented by >CH—(CH2)n—, >C?CH—, >CH—CH2—CH(OH)—, >CH—CH2—C(?O)—, >CH—O— or >CH—O—CO—, provided that when W is —CH?, then XY— represents C—(CH2)p—; Z represents a divalent aliphatic hydrocarbon group; R1 and R2, which may be the same or different, each represents a hydrogen atom, or a hydroxyl, alkoxy or alkoxyalkoxy group; m is an integer of 0 or 1].
    Type: Grant
    Filed: April 1, 2002
    Date of Patent: September 27, 2005
    Assignee: Eisai Co., Ltd.
    Inventors: Yoshihito Eguchi, Ken-ichi Chiba, Masaki Goto, Hiroshi Obaishi, Yoshikazu Kuboi
  • Patent number: 6903221
    Abstract: The invention relates to a method for producing ?-ketoenol esters of the general formula (Ia) or (Ib), wherein Ar, Ra and Rb are defined as in claim 1.
    Type: Grant
    Filed: August 21, 2001
    Date of Patent: June 7, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Steffen Kudis, Ulf Misslitz, Ernst Baumann, Wolfgang von Deyn, Klaus Langemann
  • Patent number: 6894076
    Abstract: New esters derived from (RR, SS)-3-(2-dimethylaminomethyl-1-hydroxycyclohexyl)phenyl 2-hydroxybenzoate, analog to Tramadol, a process for obtaining them and the use of these compounds for the production of a medicament with analgesic properties. These new products of general formula (I) exhibit an analgesic activity higher than that of tramadol.
    Type: Grant
    Filed: December 26, 2000
    Date of Patent: May 17, 2005
    Assignee: Vita-Invest, S.A.
    Inventors: Marisabel Mourelle Mancini, Elisabet De Ramon Amat, Juan Huguet Clotet
  • Patent number: 6884906
    Abstract: Described is a genus of menthyl half acid ester derivatives having the structure: and processes for producing same, wherein n is an integer of from 1 to 5; wherein X is either —OR? or —NRR?; wherein R? is hydrogen, C1-C5 lower alkyl or C3-C6 lower alkenyl; wherein R is hydrogen, C1-C5 lower alkyl, 2-hydroxyethyl or cyclopropyl and wherein R? is hydrogen, methyl or ethyl; with the proviso that when X is —OR?, n is an integer of from 3 to 5, having utility for augmenting, enhancing or imparting a taste or cooling effect or refreshing effect in or to an ingestible or topical composition.
    Type: Grant
    Filed: July 1, 2003
    Date of Patent: April 26, 2005
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark L. Dewis, Michelle E. Huber, Michael V. Cossette
  • Patent number: 6849771
    Abstract: The invention relates to a process for converting 1-phenylethanol into styrene, which process involves: (1) contacting a feed containing 1-phenylethanol, organic acid and 2-phenylethanol with a catalyst to obtain a product containing styrene, and (2) removing ester compounds based on 2-phenylethanol and organic acid from the product of step (1), in which process the feed of step (1) has a molar ratio of organic acid to 2-phenylethanol of at least 1:10.
    Type: Grant
    Filed: August 6, 2003
    Date of Patent: February 1, 2005
    Assignee: Shell Oil Company
    Inventors: Timothy Michael Nisbet, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
  • Patent number: 6846890
    Abstract: A novel norbornene derivative represented by a general formula (1m) shown below is provided. By conducting a ring opening polymerization of this norbornene derivative, or by performing a subsequent hydrogenation following the ring opening polymerization, a ring opening polymer or a hydrogenated product thereof with an excellent low birefringence can be obtained. [wherein, at least one of R1 to R4 is a group selected from the group consisting of groups represented by a general formula (1-1) shown below and groups represented by a general formula (1-2) shown below] [wherein, at least one of RA, RB and Z is a group represented by the formula —C(O)O—].
    Type: Grant
    Filed: October 8, 2002
    Date of Patent: January 25, 2005
    Assignee: JSR Corporation
    Inventors: Nobuyuki Miyaki, Yoshikazu Miyamoto, Seiji Fukuhara, Toshihiro Ootsuki
  • Patent number: 6838574
    Abstract: A medicament comprising as an active ingredient a compound or a physiologically acceptable salt thereof represented by general formula (I): wherein R1 represents a dicarba-closo-dodecaboran-yl which may be substituted with a lower alkyl group, a lower alkenyl group, carboxyl group or the like; R2 represents carboxyl group, a lower alkoxycarbonyl group, or hydroxyl group; and X represents a single bond or a linking group such as —CO—Y1— wherein Y1 represents oxygen or —N(R3)— wherein R3 represents hydrogen or a lower alkyl.
    Type: Grant
    Filed: January 21, 2000
    Date of Patent: January 4, 2005
    Assignee: Institute of Medicinal Molecular Design, Inc.
    Inventor: Yasuyuki Endo
  • Patent number: 6770775
    Abstract: A method of synthesizing highly optically enriched &agr;-halo-esters comprises reacting acid halides with a cinchona alkaloid catalyst and a base to form intermediate ketenes. The ketenes are reacted with electrophilic halogenating reagents to produce &agr;-halo-esters with high enantiomeric excess. The base can be an inorganic salt. The thus-formed &agr;-halo-esters have utility in synthesizing other optically-pure materials.
    Type: Grant
    Filed: May 18, 2001
    Date of Patent: August 3, 2004
    Inventor: Harald Wack
  • Patent number: 6753443
    Abstract: The present invention relates to a process for preparing a chiral ester according to the formula (100): by reacting (i) a racemic alcohol, (ii) a selected ruthenium complex to activate racemization of the racemic alcohol, (iii) a lipase to selectively acylate one enantiomer of the racemic alcohol, and (iv) an acyl donor compound to supply an acyl group to the lipase.
    Type: Grant
    Filed: March 2, 2001
    Date of Patent: June 22, 2004
    Assignees: Samsung Fine Chemicals Co., Ltd., Pohang University of Science and Technology
    Inventors: Jai Wook Park, Mahn-Joo Kim, Jeong Hwan Koh, Hyun Min Jung
  • Patent number: 6686483
    Abstract: The present invention provides a variety of methods that are based on stereoselective epoxidation of an olefin by an epoxidizing agent derived from a reaction between an oxidizing agent and a chiral ketone. For example, present invention provides methods for producing an epoxide from an olefin, for increasing a relative concentration of at least one stereoisomer of an olefin, and for stereoselectively producing an &agr;-acyloxy carbonyl compound. Preferably, the chiral ketone is of the formula: or a derivative thereof which is capable of converting to the chiral ketone of Formula I under the reaction conditions, where a, b, n, X, R1, R2, R3, R4, R5 and R6 are those defined herein.
    Type: Grant
    Filed: January 7, 2002
    Date of Patent: February 3, 2004
    Assignee: Colorado State University Research Foundation
    Inventor: Yian Shi
  • Patent number: 6677462
    Abstract: This invention relates to preparation of enantio-enriched compounds, and more particularly to enantio-enriched kavalactone compounds and derivatives thereof. The methods provide compounds that are useful as reagents, or building blocks, in the construction of other enantio-enriched compounds.
    Type: Grant
    Filed: August 6, 2001
    Date of Patent: January 13, 2004
    Assignee: Kava Pharmaceuticals, Inc.
    Inventors: Shoujun Chen, Lijun Sun, Joel McCleary
  • Publication number: 20030191318
    Abstract: The invention relates to a method for producing &bgr; ketoenol esters of the general formula (Ia) or (Ib), wherein Ar, Ra and Rb are defined as in claim 1. The inventive method is characterized by reacting an arylhalogenide of the general formula (II) with a 1,3-diketone of the general formula (III) or the tautomers thereof in a carbon monoxide atmosphere in the presence of an alkali and a catalyst that contains at least one transition metal of group VIII of the periodic system.
    Type: Application
    Filed: February 20, 2003
    Publication date: October 9, 2003
    Inventors: Steffen Kudis, Ulf Misslitz, Ernst Baumann, Wolfgang von Deyn, Klaus Langemann
  • Patent number: 6586609
    Abstract: Process for the esterification of organic acids with alcohols in a reactor of the chromatographic type in which the heterogeneous solid phase is capable of acting both as an esterification catalyst and as a means exhibiting preferential adsorption towards one of the reaction products (typically water). The process to which the present invention relates is particularly improved compared with conventional technology owing to the use, as the means for regenerating the catalyst, of a desorbent to which has been added a second compound, generally the anhydride of the acid used in the esterification reaction, which, by chemical reaction, completes the removal of the adsorbed water.
    Type: Grant
    Filed: November 30, 2001
    Date of Patent: July 1, 2003
    Assignee: La Chemical SpA
    Inventors: Roberto Ruggieri, Giovanni Ranghino, Gianni Carvoli, Agostino Tricella, Davino Gelosa, Massimo Morbidelli
  • Patent number: 6555703
    Abstract: The invention relates to a process for forming a carboxylic benzyl ester comprising reacting a dibenzyl ether with a carboxylic acid in the presence of a heteropolyacid and forming a carboxylic acid benzyl ester.
    Type: Grant
    Filed: August 31, 2001
    Date of Patent: April 29, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Bernd-Ulrich Schenke
  • Publication number: 20030069433
    Abstract: The invention relates to a process for the preparation of compounds having at least one —CF2O— bridge in the molecule, which comprises initially reacting a bis(alkylthio)carbenium salt with a compound containing at least one hydroxyl group in the presence of a base followed by oxidative fluorination, preferably in situ, with a fluorinating agent and an oxidizing agent to form the compound having at least one —CF2O— bridge in the molecule.
    Type: Application
    Filed: September 3, 2002
    Publication date: April 10, 2003
    Inventors: Peer Kirsch, Andreas Taugerbeck, Detlef Pauluth, Matthias Bremer
  • Patent number: 6491795
    Abstract: High-purity benzyl benzoate is recovered by distilling the residue remaining after removal of unreacted toluene and benzoic acid from a reaction mixture produced by the oxidation of toluene by molecular oxygen in the presence of a metal catalyst thereby separating a fraction of benzyl benzoate containing 80 wt % or more benzyl benzoate, 10 wt % or less benzoic acid and 10 wt % or less fluorenone, and purifying the fraction of benzyl benzoate by crystallization such as recrystallization. According to this process, it is possible to recover high-purity benzyl benzoate by a simple operation at low cost from the by-product formed in the manufacture of benzoic acid.
    Type: Grant
    Filed: February 8, 2001
    Date of Patent: December 10, 2002
    Assignee: Nippon Steel Chemical Co., Ltd.
    Inventors: Noboru Daitou, Shingo Ueda, Ryouji Akamine, Kazuyoshi Horibe, Katsuhiko Sakura
  • Patent number: 6479693
    Abstract: The present invention relates to a process for the preparation of a carboxylic acid ester of the general formula II, wherein R is alkyl or aryl, R1 is aryl, substituted aryl, naphthyl or substituted naphthyl or alkyl, R2, R3, R4 and R5 are independently hydrogen or alkyl by reacting an olefin of the general formula I wherein, R1 is aryl, substituted aryl, naphthyl or substituted naphthyl or alkyl, R2, R3, and R4 are independently hydrogen or alkyl, in the presence of an alcohol and an organic solvent and a supported aqueous phase palladium complex catalyst, in presence or absence of a protonic acid and an alkali metal halide, under carbon monoxide atmosphere, cooling the reaction mixture to ambient temperature, depressurising the reactor, flushing the reaction vessel with inert gas, separating the catalyst by filtration and removing the solvent and isolating the compound of formula II.
    Type: Grant
    Filed: March 20, 2001
    Date of Patent: November 12, 2002
    Assignee: Council of Scientific and Industial Research
    Inventors: Jayasree Seayad, Abdul Majeed Seayad, Bibhas Ranjan Sarkar, Raghunath Vitthal Chaudhari
  • Publication number: 20020111382
    Abstract: Disclosed is method for treating viral infections and compounds for use in such treatments. The method involves administering a pharmaceutical formulation including 3,5-dicaffeoylquinic acid or its analogs or derivatives to a patient.
    Type: Application
    Filed: September 6, 2001
    Publication date: August 15, 2002
    Inventors: Xiangmin Cui, Qiang Xu, Long-Ze Lin, Lianyun Zhao, Shunxiang Zhang, Lydia Wu, Yuefeng Lu
  • Patent number: 6399828
    Abstract: A process for making compound of formula I from a phenylpropanolamine salt of formula II wherein: R1 is hydrogen or a lower alkyl group; each R2 is independently a hydrogen, halogen, lower alkyl group, lower alkoxy groups, lower alkyl group substituted with 1 to 5 halogens, lower alkoxy groups substituted with 1 to 5 halogens, or both R2 together when on adjacent carbons constitute a —O(CH2)xO— where x is 1 to 4, thereby forming a ring structure fused with the phenyl group; R3 is a C1-C8-alkyl group, a C1-C12-aralkyl group, C1-C12-alkaryl group, or a phenyl group, each optionally substituted by 1 to 5 substituents selected from halogen, hydroxy, or C1-C6-alkyl; and HX is an equivalent of an organic or inorganic acid, the process comprising: (a) acylating the phenylpropanolamine salt of formula II with an acylating agent in a solvent at elevated temperature to make a reaction mixture containing an O-acylated phenylpropanolamine salt of formula III which can
    Type: Grant
    Filed: October 29, 2001
    Date of Patent: June 4, 2002
    Assignee: Boehringer Ingelheim Chemicals, Inc.
    Inventors: Robert Frederick Boswell, Young Sek Lo
  • Patent number: 6395922
    Abstract: A method for preparing novel dibenzoylresorcinol-based compounds is disclosed, wherein the dibenzoylresorcinol is bonded to a substituted or unsubstituted aryl group which does not include a pendent hydroxyl group. The groups attached to the dibenzoylresorcinol may contain a wide variety of functional sites which permit further reaction, e.g., copolymerization. The described compounds are very useful as UV light absorbers and may be used to form improved coating compositions which usually include a transparent, polymeric matrix material. The coating compositions may be applied to various substrates, e.g., thermoplastics, to afford a selection of enhanced properties, such as UV light resistance and abrasion resistance.
    Type: Grant
    Filed: June 16, 2000
    Date of Patent: May 28, 2002
    Assignee: General Electric Company
    Inventor: James Edward Pickett
  • Patent number: 6384265
    Abstract: The present invention provides a method for producing an &agr;-acyloxy carbonyl compound from an enol ester epoxide stereoselectively using an acid catalyst which is capable of affecting rearrangement of the enol ester epoxide with inversion of stereochemistry. The present invention also provides a method for kinetic resolution of a stereoisomeric mixture of enol ester epoxides using a chiral catalyst. The kinetic resolution generally involves stereoselectively producing one particular enantiomer of &agr;-acyloxy carbonyl compounds from the stereoisomeric mixture of enol ester epoxides.
    Type: Grant
    Filed: March 23, 2000
    Date of Patent: May 7, 2002
    Assignee: Colorado State University Research Foundation
    Inventor: Yian Shi
  • Patent number: 6348615
    Abstract: A process for producing (2R, 3S)-3-amino-4-phenylbutane-1,2-epoxide compounds which comprises treating a (2S, 3S)-3-amino-1-halo-2-hydroxy-4-phenylbutane compound or a (2S, 3S)-3-amino-4-phenylbutane-1,2-epoxide with a carboxylic acid quaternary ammonium salt or a carboxylic acid metal salt a quaternary ammonium salt and a quaternary ammonium salt, to give a (2S, 3S)-1-acyloxy-3-amino-2-hydroxy-4-phenylbutane compound, further treating the same with a sulfonic acid halide in the presence of an organic base to give a (2S, 3S)-1-acyloxy-3-amino-2-sulfonyloxy-4-phenylbutane compound, furthermore treating said compound with an inorganic base. An intermediate for the production of an HIV protease inhibitor can be produced from L-phenylalanine.
    Type: Grant
    Filed: May 11, 2001
    Date of Patent: February 19, 2002
    Assignee: Kaneka Corporation
    Inventors: Kazumi Okuro, Kenji Inoue
  • Patent number: 6307091
    Abstract: The present invention is to provided a trifluoro-substituted benzoic acid, an ester thereof, particularly 2,3,4-trifluoro-5-iodobenzonic acid, 2,3,4-trifluoro-5-trifluoromethylbenzonic acid, esters thereof, which are useful as a starting material for synthesizeing a quinolonecarboxylic acid compound useful as a medicine, an anti-bacterial agent or an antiviral agent, and processes for preparing these compounds and 2,4,5-trifluoro-3-iodobenzonic acid, 2,4,5-trifluoro-3-trifluoromethylbenzoic acid and esters thereof.
    Type: Grant
    Filed: October 3, 2000
    Date of Patent: October 23, 2001
    Assignee: Ube Industries, Ltd.
    Inventors: Yasuhito Yamamoto, Yasuhiro Yoneda, Kikuo Ataka, Naoyuki Yokota
  • Publication number: 20010020579
    Abstract: High-purity benzyl benzoate is recovered by distilling the residue remaining after removal of unreacted toluene and benzoic acid from a reaction mixture produced by the oxidation of toluene by molecular oxygen in the presence of a metal catalyst thereby separating a fraction of benzyl benzoate containing 80 wt % or more benzyl benzoate, 10 wt % or less benzoic acid and 10 wt % or less fluorenone, and purifying the fraction of benzyl benzoate by crystallization such as recrystallization. According to this process, it is possible to recover high-purity benzyl benzoate by a simple operation at low cost from the by-product formed in the manufacture of benzoic acid.
    Type: Application
    Filed: February 8, 2001
    Publication date: September 13, 2001
    Inventors: Noboru Daitou, Shingo Ueda, Ryouji Akamine, Kazuyoshi Horibe, Katsuhiko Sakura
  • Patent number: 6281382
    Abstract: The method of oxidizing the alkyl groups of alkylbenzenes using palladium phenanthroline acetate or a palladium acetate with modified phenanthroline ligand catalyst. The palladium acetate catalyst with modified phenanthroline has the following formula: wherein R1 is selected from the group consisting of alkyl groups of from 1 to 3 carbon atoms, OH, and NO2 groups and halogen and hydrogen atoms with at least six of the R1 groups being hydrogen atoms in the ligand.
    Type: Grant
    Filed: June 1, 2000
    Date of Patent: August 28, 2001
    Assignee: Georgia Tech Research Corp.
    Inventors: Mark G. White, Alexei V. Iretski
  • Patent number: 6258975
    Abstract: Provided is an industrially useful process for producing an optically active 2-hydroxy-4-arylbutyric acid or its ester. An optically active acyloxysuccinic anhydride is reacted with an aromatic compound in the presence of a Lewis acid to produce an optically active 2-acyloxy-4-oxo-4-arylbutyric acid. The 2-acyloxy-4-oxo-4-arylbutyric acid is converted to an optically active 2-acyloxy-4-arylbutyric acid through catalytic reduction. The 2-acyloxy-4-arylbutyric acid is hydrolyzed in the presence of an acid or an alkali to produce an optically active 2-hydroxy-4-arylbutyric acid. The 2-hydroxy-4-arylbutyric acid is reacted with an alcohol in the presence of an acid to produce an optically active 2-hydroxy-4-arylbutyric acid ester.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: July 10, 2001
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masahiko Kurauchi, Yoshimasa Hagiwara, Hiroyuki Matsueda, Takashi Nakano, Kunisuke Izawa
  • Patent number: 6255517
    Abstract: The present invention relates to a thymol derivative represented by following Chemical Formula 1, pharmaceutically acceptable salts or esters thereof, and anti-cancer agents comprising the same as an active ingredient.
    Type: Grant
    Filed: October 14, 1999
    Date of Patent: July 3, 2001
    Inventors: Ok Pyo Zee, Young Hoon Jung, Kang Ro Lee, Hyung In Moon, Hyung Geun Baek, Min Jung Lee, Dae Keun Kim
  • Patent number: 6242637
    Abstract: The invention relates to compounds of the formula in which: A is a divalent radical selected from: A1) —O—CO— A2) —CH2—O—CO— A3) —O—CH2—CO— A4) —O—CH2—CH2— A5) —N(R1)—CO— A6) —N(R1)—CO—CO— A7) —N(R1)—CH2—CH2— A8) —O—CH2— in which: R1 is a hydrogen or a (C1-C4)-alkyl; and Am is a nitrogen-containing heterocycle.
    Type: Grant
    Filed: October 20, 1998
    Date of Patent: June 5, 2001
    Assignee: Sanofi-Synthelabo
    Inventors: Xavier Emonds-Alt, Isabelle Grossriether, Patrick Gueule, Vincenzo Proietto, Didier Van Broeck
  • Patent number: 6218568
    Abstract: Process for preparing intermediates of formula (III) wherein Y1 is acyloxy, wherein acyl is of the formula R—C(O)—, wherein R is alkyl of 1-6 carbon atoms, Y2 is aralkyloxy, and Z is benzoyloxy or acyloxy, wherein acyl is as defined above. Intermediates of formula (III) are useful in a novel process for preparing the mono-L-valine ester of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol (ganciclovir). The mono-L-valine ester of ganciclovir and its pharmaceutically acceptable salts are of value as antiviral agents with improved absorption.
    Type: Grant
    Filed: February 3, 2000
    Date of Patent: April 17, 2001
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Charles A. Dvorak, Douglas L. Wren, Lawrence E. Fisher, Steven D. Axt, Eric R. Humphreys, Humberto B. Arzeno, Colin C. Beard, Sam Linh Nguyen, Yeun-Kwei Han, Christopher R. Roberts, Jan P. Lund, Paul R. Fatheree
  • Patent number: 6215017
    Abstract: Intermediates of Formula (III) wherein Y1 is acyloxy, wherein acyl is of the formula R—C(O)—, wherein R is alkyl of 1-6 carbon atoms, Y2 is aralkyloxy, and Z is benzoyloxy or acyloxy, wherein acyl is as defined above. Intermediates of formula (III) are useful in a novel process for preparing the mono-L-valine ester of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol (ganciclovir). The mono-L-valine ester of ganciclovir and its pharmaceutically acceptable salts are of value as antiviral agents with improved absorption.
    Type: Grant
    Filed: February 3, 2000
    Date of Patent: April 10, 2001
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Charles A. Dvorak, Douglas L. Wren, Lawrence E. Fisher, Steven D. Axt, Eric R. Humphreys, Humberto B. Arzeno, Colin C. Beard, Sam Linh Nguyen, Yeun-Kwei Han, Christopher R. Roberts, Jan P. Lund, Paul R. Fatheree
  • Patent number: 6187955
    Abstract: A guanidine derivative represented by formula (1), (2), (3) or its acid addition salt and a production process thereof wherein each of A and B is a C2-C8 alkylene, D is a single bond, —CO— or a C1-C6 alkylene, E is H, a lower alkyl or the like, m is 1 to 6, n is 0 to 6 and R1 is H, a lower alkyl or the like, 1 is 1 to 10 and G is H, —OH or the like and a skin cosmetic containing the same. It can exert excellent keratin layer softening effect continuously for a long period of time.
    Type: Grant
    Filed: November 6, 1997
    Date of Patent: February 13, 2001
    Assignee: Kao Corporation
    Inventors: Minoru Nagai, Hiromitsu Kawada, Mayumi Tsuchiya, Seiji Yamasaki, Akira Yamamuro, Toshiya Ono
  • Patent number: 6133471
    Abstract: A process for producing chromans, comprising reacting a phenol, a formaldehyde and an alcohol in the presence of a secondary amine and an acid, to generate an alkoxymethylphenol compound with the ortho position to the phenolic hydroxyl group substituted with an alkoxymethyl group, and reacting the alkoxymethylphenol compound with an unsaturated compound having a carbon-carbon double bond.
    Type: Grant
    Filed: October 26, 1999
    Date of Patent: October 17, 2000
    Assignee: KURARAY Co., Ltd.
    Inventors: Hiroyuki Monoe, Junko Sato, Koichi Kanehira, Yoshin Tamai
  • Patent number: 6040446
    Abstract: Process and novel intermediates for preparing the L-mono-valine ester of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol and its pharmaceutically acceptable salts. The present process and intermediates provide for reduced impurities in the mono-valine ester end-product and lower overall production costs. The process involves the condensation of a silylated guanine compound with a substituted glycerol derivative and esterification of this product with an L-valine derivative. These mono-valine products are of value as antiviral agents with improved absorption.
    Type: Grant
    Filed: July 31, 1998
    Date of Patent: March 21, 2000
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Charles A. Dvorak, Douglas L. Wren, Lawrence E. Fisher, Steven D. Axt, Eric R. Humphreys, Humberto B. Arzeno, Colin C. Beard, Sam Linh Nguyen, Yeun-Kwei Han, Christopher R. Roberts, Jan P. Lund, Paul R. Fatheree
  • Patent number: 6011063
    Abstract: Ortho-substituted benzoylguanidines of the formula I ##STR1## in which R(1) to R(5) have the meanings given in the claims, are suitable as antiarrhythmic pharmaceuticals having a cardioprotective component for infarct prophylaxis and for infarct treatment and also for the treatment of angina pectoris. They also inhibit in a preventive manner the pathophysiological processes in the formation of ischemically induced damage, in particular in the illicitation of ischemically induced cardiac arrhythmias.
    Type: Grant
    Filed: June 3, 1997
    Date of Patent: January 4, 2000
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Weichert, Joachim Brendel, Heinz-Werner Kleemann, Hans Jochen Lang, Jan-Robert Schwark, Udo Albus, Wolfgang Scholz
  • Patent number: 5986095
    Abstract: A process is described for preparing a compound of the formula or the S-enantiomer thereof,wherein:R is alkyl, aryl, cycloalkyl, aralkyl, or cycloalkylalkyl,R.sup.1 is halogen;R.sup.2 is halogen, alkyl, cycloalkyl, aryl or ##STR1## wherein the process comprises treating the associated racemic alcohol with an acylatingagent ##STR2## (wherein L is a leaving group) and an enzyme or microorganism capable of enantioselective acylation. This process may also be used to isolate the unreacted R- or S-alcohol. The acylated product may be enantioselectively hydrolyzed with a lipase or lipase-supplying microorganism to the S- or R-alcohol. Compounds prepared by this invention are useful antipsychotic agents or useful intermediates therefor.
    Type: Grant
    Filed: January 6, 1992
    Date of Patent: November 16, 1999
    Assignee: E.R. Squibb & Sons, Inc.
    Inventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
  • Patent number: 5981792
    Abstract: The process for preparing 1-functional allyl alcohol carboxylic esters comprises reacting a 3-functional allyl alcohol with the anhydride of the carboxylic acid at temperatures above 100.degree. C. in the presence of metal compounds of transition groups V to VII, namely at temperatures of 100-200.degree. C., preferably 130-150.degree. C. As metal compounds, it is possible to use oxidic metal compounds in the highest or at least second highest oxidation state of the transition metals, for example tungstic acid or its salts and/or tungsten(VI) oxide and/or molybdenum(V) oxide and/or molybdenum(VI) oxide and/or rhenium(VII) oxide. The 3-functional allyl alcohol and the carboxylic anhydride are advantageously used in equimolar amounts, if desired with a slight excess of anhydride, and an alkali metal salt of a weak acid, for example sodium carbonate or sodium acetate, can be added to the reaction mixture in an amount sufficient to trap free protons.
    Type: Grant
    Filed: February 26, 1998
    Date of Patent: November 9, 1999
    Assignee: Dragoco Gerberding & Co. AG
    Inventor: Jurgen Vollhardt
  • Patent number: 5952386
    Abstract: The present invention provides dihalopropene compounds of the general formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl or the like; L is C(.dbd.O)NH or the like; R.sub.2, R.sub.3 and R.sub.4 are independently halogen or the like; R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen or the like; m is an integer of 0 to 4; n is an integer of 0 to 2; X is chlorine or the like; Y is oxygen or the like; and Z is oxygen or the like, which have excellent insecticidal activity so that they are satisfactorily effective for the control of noxious insects.
    Type: Grant
    Filed: September 24, 1997
    Date of Patent: September 14, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Sanshiro Matsuo, Taro Hirose, Keiichi Izumi, Masaya Suzuki, Noriyasu Sakamoto, Kazunori Tsushima, Shigeru Saito, Hirotaka Takano
  • Patent number: 5905166
    Abstract: A new type of yellow dyes with general formula Q-CO--CO--X is disclosed. They can be used in photographic materials as antihalation dyes, acutance dyes or filter dyes. Preferably they are incorporated in UV sensitive contact materials for pre-press applications.
    Type: Grant
    Filed: August 12, 1997
    Date of Patent: May 18, 1999
    Assignee: Agfa-Gevaert, N.V.
    Inventor: Eric Kiekens
  • Patent number: 5858653
    Abstract: Method and reagent composition for covalent attachment of target molecules, such as nucleic acids, onto the surface of a substrate. The reagent composition includes groups capable of attracting the target molecule as well as groups capable of covalently binding to the target molecule, once attracted. Optionally, the composition can contain photoreactive groups for use in attaching the reagent composition to the surface.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: January 12, 1999
    Assignee: SurModics, Inc.
    Inventors: Lise W. Duran, Melvin J. Swanson, Richard A. Amos, Sheau-Ping J. Hu, Patrick E. Guire
  • Patent number: 5859054
    Abstract: Pharmacologically active leukotriene-B.sub.4 derivatives of general formula I, ##STR1## are described, in whichR.sub.1 represents CH.sub.2 OH, CH.sub.3, CF.sub.3, COOR.sub.4, CONR.sub.5 R.sub.6, orR.sub.2 represents H or an organic acid radical with 1-15 C atoms,R.sub.3 symbolizes H; C.sub.1 -C.sub.14 alkyl, C.sub.3 -C.sub.10 cycloalkyl optionally substituted singly or multiply; C.sub.6 -C.sub.10 aryl radicals, independently of one another, optionally substituted singly or multiply by halogen, phenyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluoromethyl, chloromethyl, trifluoromethyl, carbonyl, carboxyl or hydroxy; or a 5- to 6-membered aromatic heterocyclic ring with at least 1 heteroatom,R.sub.4 means hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 cycloalkyl; C.sub.6 -C.sub.10 aryl radicals optionally substituted by 1-3 halogen, phenyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluoromethyl, chloromethyl, trifluoromethyl, carboxyl or hydroxy; CH.sub.2 --CO--(C.sub.6 -C.sub.
    Type: Grant
    Filed: November 8, 1996
    Date of Patent: January 12, 1999
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
  • Patent number: 5798383
    Abstract: The prevent invention provides a compound of formula (I): ##STR1## wherein Ar is (a) phenyl, naphthyl and biphenyl, each optionally substituted with C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 hydroxyalkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C.sub.2-4 alkoxyalkoxy, C.sub.1-4 alkylthio, hydroxy, halo, cyano, amino, C.sub.1-4 alkylamino, di (C.sub.2-8) alkylamino, C.sub.2-6 alkanoylamino, carboxy, C.sub.2-6 alkoxycarbonyl, or optionally substituted phenyl, phenoxy, phenylthio or phenylsulfinyl or (b) furyl, benzo?b!furyl, thienyl, benzo?b!thienyl, pyridyl or quinolyl, each optionally substituted with C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, halo, C.sub.1-4 alkoxy, optionally-substituted phneyl, phenoxy or phenylthio, X is C.sub.1 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkenylene, --(CHR.sup.1).sub.m --Q.sup.1 --(CHR.sup.2).sub.n --, --O--(CHR.sup.1).sub.j --Q.sup.2 -- and --(CHR.sup.1)--O--N.dbd. in which the N.dbd. moiety is attached to the cycloalkene ring; and in which Q.sup.1 is O, S, SO, SO.sub.2, NR.
    Type: Grant
    Filed: May 8, 1997
    Date of Patent: August 25, 1998
    Assignee: Pfizer Inc.
    Inventors: Akiyoshi Kawai, Makoto Kawai, Rodney W. Stevens
  • Patent number: 5773614
    Abstract: (1R,trans) Diprotected 3-methylene-1,2-cyclopropanedimethanol is oxidized to an optically active diol ##STR1## which is then cyclized to an orthoester ##STR2## This orthoester is then treated with a Lewis acid catalyst to give the cyclobutanone ##STR3## which is useful as an intermediate in the preparation of the antiviral agent ?1R-(1.alpha.,2.beta.,3.alpha.)!-2-amino-9-?2,3-bis(hydroxymethyl)cyclobut yl!-1,9-dihydro-6H-purin-6-one.
    Type: Grant
    Filed: September 13, 1996
    Date of Patent: June 30, 1998
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Jollie D. Godfrey, Jr., Richard H. Mueller
  • Patent number: 5750765
    Abstract: Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-substituted quinone methide compound.
    Type: Grant
    Filed: August 27, 1996
    Date of Patent: May 12, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Peter Nesvadba, Samuel Evans, Matthew E. Gande, Volker H. von Ahn, Roland A. E. Winter
  • Patent number: 5741814
    Abstract: Cyclooctadiene derivative of the following formula (1): ##STR1## wherein A.sup.1, A.sup.2, A.sup.3 and A.sup.4 each independently represent COOR.sup.5 (where R.sup.5 represents a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group, a phenyl group, a C.sub.7 -C.sub.12 aralkyl group or CONR.sup.6 R.sup.7 (where R.sup.6 and R.sup.7 each independently represent a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group or a phenyl group), or A.sup.1 and A.sup.2, and/or A.sup.3 and A.sup.4 may be combined together to represent group(s) of: ##STR2## in which X represents an oxygen atom or NR.sup.8 {where R.sup.8 represents a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group or a phenyl group),R.sup.0, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group and an C.sub.1 -C.sub.10 alkyl group,the symbol ------ represents a single or double bond, and when it is a double bond, then R.sup.1 and R.sup.
    Type: Grant
    Filed: September 3, 1996
    Date of Patent: April 21, 1998
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Yasuyuki Nakajima, Hisayuki Watanabe, Michiaki Adachi, Michito Tagawa, Mitsugu Futagawa, Takashi Furusato, Hiroshi Ohya, Masanori Nishioka
  • Patent number: 5705680
    Abstract: The present invention relates to a process for the preparation of O-acylglycolanilides of the formula (1) ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen, halogen, a nitro group, a cyano group, a straight-chain or branched alkyl, alkenyl, alkynyl or alkoxy group having from 1 to 12 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, a cycloalkyl group having from 6 to 12 carbon atoms or an aryl group having from 6 to 12 carbon atoms,. R.sup.3 is hydrogen or a straight-chain or branched alkyl group having from 1 to 12 carbon atoms, and R.sup.4 is an alkyl group having from 1 to 6 carbon atoms or is a substituted or unsubstituted phenyl radical, in which an aniline of the formula (2) ##STR2## in which R.sup.1, R.sup.2 and R.sup.3 have the same meaning as in formula (1), and an O-acylglycolic acid of the general formula (3) ##STR3## in which R.sup.
    Type: Grant
    Filed: August 3, 1995
    Date of Patent: January 6, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Dierdorf, Theodor Papenfuhs
  • Patent number: RE37947
    Abstract: Novel pharmaceutically/cosmetically-active aromatic polyenic compounds have the structural formula (I): and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: December 31, 2002
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Phillippe Nedoncelle