The Chalcogen Is In An -oh Or -om Group (m Is Group Ia Or Group Iia Light Metal) Patents (Class 546/344)
  • Publication number: 20090326235
    Abstract: The present invention relates to anhydrous solutions of MX3-Z LiA in a solvent, wherein M is a lanthanide including lanthanum, or yttrium or indium; z>0; and X and A are independently or both monovalent anions, preferably Cl, Br or I. The solution is readily prepared by dissolving or suspending MX3 or its hydrate and z equiv LiA in water or hydrophilic solvents, or mixtures thereof, removing the solvent under vacuum and dissolving the resulting powder in another solvent. The solution of MX3-Z LiA can advantageously be used e.g. in addition reactions of Grignard reagents to ketones and imines. Even the catalytic use of MX3-Z LiA is possible.
    Type: Application
    Filed: September 1, 2006
    Publication date: December 31, 2009
    Inventors: Paul Knochel, Arkady Krasovskiy, Felix Kopp
  • Patent number: 7586015
    Abstract: A process is used for the preparation of 1,3,2-oxazaborolidine compounds. This process prepares compounds of formula (I) or (IA): in which: R1 is an alkyl or an aryl; and R2, R3, R4 and R5 are especially a hydrogen atom or an alkyl, wherein the following are reacted in two steps: a) a boric precursor compound with an acetal compound to give a boronate compound; and b) the boronate compound with an amino alcohol compound. This process avoids by-products and exhibits a very good stereospecificity.
    Type: Grant
    Filed: January 25, 2007
    Date of Patent: September 8, 2009
    Assignee: Zach System
    Inventors: Alain Burgos, Stëphane Frein
  • Publication number: 20080262011
    Abstract: The present invention relates to a compound of formula I, or a pharmaceutically acceptable salt thereof. Formula (I), wherein R1 and R2 are each independently H or alkyl; Y is an alkyl group. CONR3R4, COOR5SO2NR16R17, NHSO2R18 or CN; X is an aryl or heteroaryl group, each of which may be optionally substituted with one or more substituents selected from (CH2)mZ where Z is halogen, OH, CN, alkyl, alkoxy, NO2, CF3, CONR6R7, CN, NR8R9, COOR10 or NHCOR11 and m is 0 to 3; R3 to R11 are each independently H, alkyl or aryl, wherein said alkyl and aryl groups are optionally substituted by one or more substituents selected from halogen, OH, CN, alkyl, alkoxy, NO2, CF3, CONR12R13, CN, NH2, COOR14, NHCOR15, and CN; R12 to R18 are each independently H or alkyl, more preferably H or Me; n is 1 to 6; wherein the compound is other than 3?,5?-dimethyl-4-(1,1-dimethylheptyl)-1,1?-biphenyl-2-ol.
    Type: Application
    Filed: December 21, 2005
    Publication date: October 23, 2008
    Inventors: David Selwood, Cristina Visintin, David Baker, Gareth Pryce, Masahiro Okuyama
  • Publication number: 20080249308
    Abstract: The invention relates to a new class of ruthenium (II) complexes containing as ligands 2-(aminomethyl)pyridines and phosphines, proven to be extremely active catalysts in the reduction of ketones to alcohols via hydrogen transfer. By using 2-propanol as the hydrogen source with the ruthenium complexes, high yields of the corresponding alcohol can be rapidly obtained starting from linear and cyclic alkyl aryl, dialkyl and diaryl ketones. The conversion of ketones to alcohols can reach 100% if operating in a gaseous hydrogen atmosphere (2-3 atm). Where the phosphines used are optically active, starting from prochiral ketone compounds various types of optically active alcohols can be produced, being important intermediates in the pharmaceutical industry, in the agrochemical industry and for fine chemicals generally.
    Type: Application
    Filed: May 2, 2005
    Publication date: October 9, 2008
    Inventors: Walter Baratta, Katia Siega, Micaela Toniutti, Pierluigi Rigo
  • Publication number: 20080177020
    Abstract: A non-metallocene organometallic complex comprising a tridentate ligand and a metal bonded to a tridentate ligand, wherein two substituted aryl groups in the tridentate ligand are connected to a cyclic group at the ortho position via semi-rigid ring-ring linkages, and selected so to provide the resulting non-metallocene organometallic complex with a CS geometry, a C1 geometry, a C2 geometry or a C2v geometry.
    Type: Application
    Filed: September 21, 2007
    Publication date: July 24, 2008
    Inventors: Theodor Agapie, Suzanne Rose Golisz, Daniel Tofan, John E. Bercaw
  • Publication number: 20080139599
    Abstract: Compounds of the formula (1) in which R1, R2,X, Y and Z are as defined in the description, the processes for the preparation of these compounds, the uses thereof for the treatment of dyslipidaemia, atherosclerosis and diabetes, and the pharmaceutical compositions comprising them.
    Type: Application
    Filed: December 22, 2005
    Publication date: June 12, 2008
    Inventors: Michel Brunet, Nathalie Adje, Valerie Guyard-Dangremont, Francis Contard
  • Patent number: 7355048
    Abstract: A four-step process for preparing 1-(6-methylpyridin-3-yl)-2-[4-(methylsulfonyl)phenyl]ethanone of the formula: starting from 2-methyl-5-ethylpyridine. 1-(6-Methylpyridin-3yl)-2-[4-(methylsulfonyl)phenyl]ethanone is an intermediate for preparing inhibitors.
    Type: Grant
    Filed: January 6, 2005
    Date of Patent: April 8, 2008
    Assignees: Lonza Ltd., Merck & Co. Inc.
    Inventors: David Kuo, James E. Leresche, Ralf Proplesch, Jean-Paul Roduit, Yves Bessard, Erich Armbruster
  • Patent number: 7253192
    Abstract: This invention is concerned with compounds of the formula I: wherein one of R5, R6 and R7 is and X1, X2, R1 to R12, m, n and o are as defined in the description, and pharmaceutically acceptable salts and/or esters thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are modulated by PPAR? and/or PPAR? agonists.
    Type: Grant
    Filed: June 30, 2005
    Date of Patent: August 7, 2007
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Jean Ackermann, Johannes Aebi, Alfred Binggeli, Uwe Grether, Bernd Kuhn, Hans-Peter Maerki, Markus Meyer
  • Patent number: 7151107
    Abstract: The invention relates to the use of compounds of formula for the preparation of medicines designed for the treatment of neuronal and cerebral disorders. The invention also relates to the compounds of formula: a process for their preparation and the pharmaceutical compositions containing them.
    Type: Grant
    Filed: May 24, 2005
    Date of Patent: December 19, 2006
    Assignee: Sanofi-aventis
    Inventors: Marco Baroni, Rosanna Cardamone, Jacqueline Fournier, Umberto Guzzi, Alessandra Ielmini
  • Patent number: 7145015
    Abstract: Benzocycloheptenes of formula (I), in which R1, R2 and Y have the meanings that indicated herein, exhibit selective estrogenic activity on bones and are suitable for the production of pharmaceutical agents, especially for prophylaxis and therapy of osteoporosis:
    Type: Grant
    Filed: April 11, 2005
    Date of Patent: December 5, 2006
    Assignee: Schering AG
    Inventors: Rolf Bohlmann, Jorg Kroll, Hermann Kuenzer, Christa Hegele-Hartung, Monika Lessl, Rosemarie Lichtner, Yukishige Nishino
  • Patent number: 7144893
    Abstract: The present invention pertains to compounds of the formula (1) which are, inter alia, antiproliferative agents, anticancer agents, antimycobacterial agents, antituberculosis agents, and/or thioredoxin/thioredoxin reductase inhibitor: wherein: Q is ?O or ?N—S(?O)2—RQ;RQ is —II or optionally substituted C1-7alkyl, C3-20heterocyclyl, or C5-20aryl; Ar is optionally substituted C5-20aryl; RO is an oxy substituent; the bond marked ? is a single bond or a double bond; the bond marked ? is a single bond or a double bond; R3 and R5 are each independently ring substituents; R2 and R6 are each independently ring substituents; and pharmaceutically acceptable salts, esters, amides, solvates, hydrates, and protected forms thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for example, in the treatment of proliferative conditions, (e.g., cancer), mycobacterial infections (e.g.
    Type: Grant
    Filed: July 5, 2002
    Date of Patent: December 5, 2006
    Assignee: Cancer Research Technology Limited
    Inventors: Malcolm Francis Graham Stevens, Geoffrey Wells, Andrew David Westwell, Tracey Dawn Poole
  • Patent number: 7141673
    Abstract: A starting product for the preparation of COX-2 inhibitors, notably the compound 1-(6-methylpyridine-3-yl)-2-[(4-(methylsulfonyl)phenyl]ethanone of the formula (I): A method for making the compound.
    Type: Grant
    Filed: January 13, 2000
    Date of Patent: November 28, 2006
    Assignee: Lonza AG
    Inventors: Erich Armbruster, Yves Bessard, David Kuo, James E. Leresche, Ralf Proplesch, Jean-Paul Roduit
  • Patent number: 6949656
    Abstract: A composition for use as an antiobestic agent and preventive or therapeutic agent for diabetes, containing a compound of the formula (I): wherein, A is substituted aryl or substituted heteroaryl with one or more group(s); (here, one of following groups is at least contained as the substituent: —RA—RB (RA is S, SO, SO2, NRC, NRCSO2 (RC is hydrogen or lower alkyl) or lower alkylene); RB is optionally substituted aryl); X is O, S, NR wherein R is hydrogen or lower alkyl, or single bond; m is an integer of 0 to 4; n is an integer of 1 to 6 p is an integer of 1 to 3, pharmaceutically acceptable salt, prodrug or hydrate thereof.
    Type: Grant
    Filed: August 2, 2001
    Date of Patent: September 27, 2005
    Assignee: Shionogi & Co., Ltd.
    Inventors: Toshisada Yano, Isako Sakaguchi, Goro Katsuura, Naoki Yoshikawa
  • Patent number: 6831106
    Abstract: The present invention relates to novel triaromatic compounds having the general formula (I): as well as to a method for preparing them and to their use in pharmaceutical compositions intended for use in human or veterinary medicine (in dermatology, in carcinology and in the field of autoimmune diseases and that of organ or tissue transplants in particular), or alternatively in cosmetic compositions.
    Type: Grant
    Filed: September 5, 2002
    Date of Patent: December 14, 2004
    Assignee: Galderma Research & Development, S.N.C.
    Inventors: Jean-Michel Bernardon, Thibaud Biadatti
  • Patent number: 6790853
    Abstract: Competitive progesterone antagonists, including two novel steroids, viz., 11&bgr;,19-[4-(cyanophenyl)-o-phenylene]-17&bgr;-hydroxy-17&agr;-(3-hydroxyprop-1(Z)-enyl)-4-androsten-3-one and 11&bgr;,19-[4-(3-pyridinyl)-o-phenylene]-17&bgr;-hydroxy-17&agr;-(3-hydroxyprop-1(Z)-enyl)-4-androsten-3-one, inhibit formation of endometrial glands at below their ovulation inhibiting dose and the abortive dose, and thus achieve oral contraception in females without adversely affecting the menstrual cycle and without risk of aborting a previous implanted fertilized egg or a fetus.
    Type: Grant
    Filed: March 31, 2003
    Date of Patent: September 14, 2004
    Assignee: Schering AG
    Inventors: Krzystof Chwalisz, Walter Elger, Karin Schmidt-Gollwitzer, Eckhard Ottow
  • Patent number: 6749988
    Abstract: Novel amine compounds having a nitrogen-containing cyclic structure and a hydrating group such as a hydroxy, ether, ester, carbonyl, carbonate group or lactone ring are useful for use in resist compositions for preventing a resist film from thinning and also for enhancing the resolution and focus margin of resist.
    Type: Grant
    Filed: November 28, 2001
    Date of Patent: June 15, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Tomohiro Kobayashi, Takeru Watanabe, Takeshi Nagata
  • Patent number: 6747048
    Abstract: Novel pyridine-based thyroid receptor ligands are provided which have the general formula I wherein: X is oxygen (—O—), sulfur (—S—), sulfoxide (—S(O)—), sulfonyl (—SO2—), CR8R8 or NR8; Y is —NR8, oxygen (—O—), —CH2— or sulfur (—S—); Z is a bond or substituted or unsubstituted C1-4 alkyl; and wherein the substituents are as described herein. In addition, a method is provided for preventing, inhibiting or treating diseases or disorders associated with metabolism dysfunction or which are 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: May 7, 2003
    Date of Patent: June 8, 2004
    Assignee: Bristol-Myers Squibb Company
    Inventors: Minsheng Zhang, Jon Hangeland, Yolanda Caringal, Todd Friends
  • Patent number: 6649623
    Abstract: A composition for use as an antiobestic agent and preventive or therapeutic agent for diabetes, containing a compound of the formula (I): wherein, A is optionally substituted aryl or optionally substituted heteroaryl; X is O, S, NR wherein R is hydrogen or lower alkyl, or single bond; m is an integer of 0 to 4; n is an integer of 1 to 5; p is an integer of 1 to 3, pharmaceutically acceptable salt, prodrug or hydrate thereof.
    Type: Grant
    Filed: July 20, 2001
    Date of Patent: November 18, 2003
    Assignee: Shionogi & Co., Ltd.
    Inventors: Toshisada Yano, Isako Sakaguchi, Goro Katsuura
  • Patent number: 6608074
    Abstract: Competitive progesterone antagonists, including two novel steroids, viz., 11&bgr;,19-[4-(cyanophenyl)-o-phenylene]-17&bgr;-hydroxy-17&agr;-(3-hydroxyprop-1(Z)-enyl)-4-androsten-3-one and 11&bgr;,19-[4-(3-pyridinyl)-o-phenylene]-17&bgr;-hydroxy-17&agr;-(3-hydroxyprop-1(Z)-enyl)-4-androsten-3-one, inhibit formation of endometrial glands at below their ovulation inhibiting dose and the abortive dose, and thus achieve oral contraception in females without adversely affecting the menstrual cycle and without risk of aborting a previous implanted fertilized egg or a fetus.
    Type: Grant
    Filed: November 28, 2001
    Date of Patent: August 19, 2003
    Assignee: Schering AG
    Inventors: Krzystof Chwalisz, Walter Elger, Karin Schmidt-Gollwitzer, Eckhard Ottow
  • Patent number: 6600078
    Abstract: A heterogeneous liquid-phase process for the hydrogenation of aldehydes of Formula (I) and (III) to the corresponding alcohols of Formula (II) and (IV) which process comprises contacting alcoholic or aqueous-alcoholic solution of aldehydes and hydrogen gas with a catalyst comprising a reduced mixture of CuO and ZnO in presence of a metal of group IIIA of the Periodic Table, such as aluminium, as a promoter at a temperature of between about 110° and 180° C. and a pressure of between about 20 and 500 psig.
    Type: Grant
    Filed: August 12, 2002
    Date of Patent: July 29, 2003
    Assignee: Saudi Basic Industries Corporation
    Inventors: Meftahuddin Mahmud, Ahmad Kamal Faizi, Vidyasagar Anchoori, Abdullah Al-Qahtani
  • Patent number: 6579881
    Abstract: A 1,4-substituted cyclic amine derivative represented by the following formula or a pharmacologically acceptable salt thereof: wherein A, B, C, D, T, Y, and Z each represent a methine or a nitrogen linkage; R1, R2, R3, R4, and R5 each represent a substituent; n represents 0 or an integer of 1 to 3; m represents 0 or an integer of 1 to 6; and p represents an integer of 1 to 3. The compounds have serotonin antagonism. They are therefore clinically useful as medicaments, in particular, for treating, ameliorating, and preventing spastic paralysis. They are also useful as central muscle relaxants for ameliorating myotonia.
    Type: Grant
    Filed: May 18, 2001
    Date of Patent: June 17, 2003
    Assignee: Eisai Co., Ltd.
    Inventors: Noritaka Kitazawa, Kohshi Ueno, Keiko Takahashi, Teiji Kimura, Atsushi Sasaki, Koki Kawano, Tadashi Okabe, Makoto Komatsu, Manabu Matsunaga, Atsuhiko Kubota
  • Patent number: 6503917
    Abstract: The present invention relates to novel substituted pyridine compounds of Formula (I) wherein the moiety Z, R1, R2 and R3 are as herein defined, having estrogenic activity, to processes for their preparation, to a combinatorial library and solid phase methods for preparing libraries of the compounds, to utilizing libraries of the compounds for drug discovery, to methods of treatment and to pharmaceutical compositions thereof.
    Type: Grant
    Filed: November 1, 2000
    Date of Patent: January 7, 2003
    Assignee: Wyeth, Five Giralda Farms
    Inventors: Chingfan Chiu, Zhilian Tang, John W. Ellingboe
  • Patent number: 6486327
    Abstract: The invention relates to a method for producing hydroxymethylpyridines from the corresponding vinylpyridines by means of ozonisation in an alcohol as solvent and by means of hydrogenation of the peroxide-containing solution produced thereby, in the presence of a hydrogenation catalyst The hydrogenation solution is adjusted to a pH value of 10 to 14 by adding a base and the alcohol is distilled off and the desired hydroxymethylpyridine is isolated in high purity by extracting with an organic solvent and by means of subsequent distillative purification.
    Type: Grant
    Filed: May 2, 2002
    Date of Patent: November 26, 2002
    Assignee: DSM Fine Chemicals Austria NFG GmbH & Co KG
    Inventors: Karlheinz Giselbrecht, Rudolf Hermanseder
  • Patent number: 6420565
    Abstract: 2-lithio-5-halopyridine is formed as a predominant component of a reaction mixture by reacting BuLi with 2,5-dihalopyridine in a non-coordinating solvent.
    Type: Grant
    Filed: February 27, 2001
    Date of Patent: July 16, 2002
    Assignees: Merck & Co., Inc., Merck Frosst Canada & Co
    Inventors: Paul O'Shea, Xin Wang, Richard Tillyer
  • Patent number: 6388086
    Abstract: A process for producing a 3-(3-pyridyl)-1-propanol derivative of use as a pharmaceutical intermediate expediently with an inexpensive material is provided.
    Type: Grant
    Filed: August 2, 2000
    Date of Patent: May 14, 2002
    Assignee: Kaneka Corporation
    Inventors: Akira Nishiyama, Kazumi Okuro, Kenji Inoue
  • Patent number: 6358965
    Abstract: The invention relates to the use of compounds of formula for the preparation of medicines designed for the treatment of neuronal and cerebral disorders. The invention also relates to the compounds of formula: a process for their preparation and the pharmaceutical compositions containing them.
    Type: Grant
    Filed: August 5, 1999
    Date of Patent: March 19, 2002
    Assignee: Sanofi-Synthelabo
    Inventors: Marco Baroni, Rosanna Cardamone, Jacqueline Fournier, Umberto Guzzi, Alessandra Ielmini
  • Patent number: 6340688
    Abstract: Competitive progesterone antagonists, including two novel steroids, viz., 11&bgr;,19-[4-(cyanophenyl)-o-phenylene]-17&bgr;-hydroxy-17&agr;-(3-hydroxyprop-1(Z)-enyl)-4-androsten-3-one and 11&bgr;,19-[4-(3-pyridinyl)-o-phenylene]-17&bgr;-hydroxy-17&agr;-(3-hydroxyprop-1(Z)-enyl)-4-androsten-3-one, inhibit formation of endometrial glands at below their ovulation inhibiting dose and the abortive dose, and thus achieve oral contraception in females without adversely affecting the menstrual cycle and without risk of aborting a previous implanted fertilized egg or a fetus.
    Type: Grant
    Filed: September 17, 1998
    Date of Patent: January 22, 2002
    Assignee: Schering Aktiengesellschaft
    Inventors: Krzystof Chwalisz, Walter Elger, Karin Schmidt-Gollwitzer, Eckhard Ottow
  • Patent number: 6337305
    Abstract: Substituted 2-benz(o)ylpyridines I and salts thereof where n=0, 1; X=CO, CH2, CH(C1-C4-alkyl), CH—OH, CH—CN, CH-halogen, C(halogen)2, CH—CONH2, CH—CO—O(C1-C4-alkyl), CH—O(C1-C4-alkyl), C(CN)(C1-C4-alkyl); R1=halogen, C1-C4-haloalkyl, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl; R2=H, halogen; R3=H, NO2, OH, halogen, C1-C4-alkoxy; R4=H, NO2, OH, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy; R5=H, NO2, CN, halogen, C1-C8-alkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C8-cycloalkyl, C1-C8-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkinyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C4-alkenyloxy-C1-C4-alkyl, C2-C4-alkynyloxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, cyano-C1-C8-alkyl, cyano-C2-C8-alkenyl, cyano-C3-C8-alkynyl, unsubstituted or substituted OH, SH, SO—H, —SO2—H, COOH or NH—COOH, —SO2Cl, —N(R9,
    Type: Grant
    Filed: September 15, 1999
    Date of Patent: January 8, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schäfer, Gerhard Hamprecht, Markus Menges, Olaf Menke, Michael Rack, Cyrill Zagar, Karl-Otto Westphalen, Ulf Misslitz, Helmut Walter
  • Patent number: 6281231
    Abstract: The object is to provide a novel compound, with which there is little possibility of phytotoxicity for crop plants, and which is greatly effective in controlling various plant diseases caused by viruses pathogenic to plants, by bacteria, and by molds, and to provide agricultural chemicals, particularly agents for controlling plant diseases, containing this compound, 2,6-dichloro-4-pyridinemethanol, and/or a benzoic acid ester thereof as an active ingredient.
    Type: Grant
    Filed: March 9, 2000
    Date of Patent: August 28, 2001
    Assignee: Dainippon Ink and Chemical, Inc.
    Inventors: Toru Asada, Mika Iiyama, Hiroyuki Tsuboi, Takashi Gotou
  • Patent number: 6201158
    Abstract: The present invention relates to a process for making propargylic alcohols by zinc-mediated catalytic, asymmetric addition of acetylenes to aldehydes.
    Type: Grant
    Filed: May 27, 1999
    Date of Patent: March 13, 2001
    Assignee: Merck & Co., Inc.
    Inventors: Zhen Li, Ann Decamp, Veena Upadhyay
  • Patent number: 6147082
    Abstract: The invention relates to a novel class of compounds that have structures related to certain naturally occurring or synthetic chalcones. The invention also relates to pharmaceutical compositions comprising the compounds and methods for treating certain disorders using the pharmaceutical compositions. The invention further relates to process for synthesizing the novel class of compounds.
    Type: Grant
    Filed: December 8, 1999
    Date of Patent: November 14, 2000
    Inventors: Ezio Bombardelli, Piero Valenti
  • Patent number: 6103911
    Abstract: The present invention relates to a process for the reduction of an azetidinone-carboxylic acid to an azetidine-alcohol.
    Type: Grant
    Filed: June 15, 1999
    Date of Patent: August 15, 2000
    Assignee: Abbott Laboratories
    Inventors: James E. Resek, Shyamal I. Parekh, Pulla R. Singam, Hemant H. Patel, Michael H. Cain, Bikshandarkoil A. Narayanan
  • Patent number: 6037505
    Abstract: The anantoselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the precence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulas (I) and (II). The compounds of formulas (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulas (I) and (II) may be generated in situ.
    Type: Grant
    Filed: April 26, 1999
    Date of Patent: March 14, 2000
    Assignee: Pfizer Inc.
    Inventor: George Joseph Quallich
  • Patent number: 6022974
    Abstract: A process for the production of 2-chloro-5-chloromethylpyridine of the formula: ##STR1## starting from 6-hydroxynicotinic acid of the formula: ##STR2## In this way 6-hydroxynicotinic acid is reacted with an acid chloride to 6-hydroxynicotinoyl chloride of the formula: ##STR3## The latter is then catalytically hydrogenated with hydrogen to 6-hydroxy-5-hydroxymethylpyridine of the formula: ##STR4## The latter is then catalytically hydrogenated with hydrogen to 2-hydroxy-5-hydroxymethylpyridine of the formula: ##STR5## which is then chlorinated to the end product according to formula I.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: February 8, 2000
    Assignee: Lonza Ltd.
    Inventors: Oleg Werbitzky, Philipp Studer
  • Patent number: 5990119
    Abstract: Novel compounds of formula I are described herein. These compounds inhibit the production of Tumor Necrosis Factor and are useful in the treatment of disease states mediated or exacerbated by TNF production; these compounds are also useful in the mediation or inhibition of enzymatic or catalytic activity of phosphodiesterase IV.
    Type: Grant
    Filed: June 23, 1997
    Date of Patent: November 23, 1999
    Assignee: SmithKline Beecham Corporation
    Inventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
  • Patent number: 5990314
    Abstract: This invention relates to a compound of formula I ##STR1## These compounds are leukotriene antagonists and as such can be used in treating various diseases associated with leukotrienes.
    Type: Grant
    Filed: June 7, 1996
    Date of Patent: November 23, 1999
    Assignee: SmithKline Beecham Corporation
    Inventor: Robert A. Daines
  • Patent number: 5977105
    Abstract: A compound of formula I, ##STR1## wherein--X represents (CH.sub.2).sub.n O, (CH.sub.2).sub.n S or C.sub.2 alkylene;n represents 1 or 2;Ar.sup.1 represents indanyl, tetrahydronaphthyl, naphthyl or phenyl, which latter two groups may be substituted by one or more substituents selected from chloro, fluoro, OR.sup.1, O(CH.sub.2).sub.m CONR.sup.20 R.sup.21, C(O)R.sup.2, C.sub.1-6 alkyl (optionally substituted by one or more fluorine atoms), pyridyl, thiazinyl, phenyl or C.sub.7-9 alkylphenyl which latter two groups are optionally substituted by one or more substituent selected from halo, nitro, OR.sup.3, C.sub.1-6 alkyl (optionally substituted by one or more fluorine atoms), C(O)R.sup.4, C(O)OR.sup.5, C(O)N(R.sup.6)R.sup.7, CN, CH.sub.2 OR.sup.14, CH.sub.2 NR.sup.15 R.sup.16, N(R.sup.8)R.sup.9, N(R.sup.10)SO.sub.2 R.sup.11, N(R.sup.12)C(O)R.sup.13, OC(O)R.sup.19 and SO.sub.2 NR.sup.17 R.sup.18 ;m represents an integer 1 to 3;R.sup.1, R.sup.2 and R.sup.3 independently represent H, C.sub.
    Type: Grant
    Filed: March 3, 1997
    Date of Patent: November 2, 1999
    Assignee: Astra Pharmaeuticals Ltd.
    Inventors: David Cheshire, David Cladingboel, David Hardern, Michael Stocks
  • Patent number: 5925645
    Abstract: The 2-aryl-substituted pyridines are prepared by reacting pyridylaldehydes with organometallic compounds and then selectively reducing the products. The 2-aryl-substituted pyridines are suitable as active compounds in medicaments, in particular in medicaments for the treatment of arteriosclerosis.
    Type: Grant
    Filed: March 13, 1997
    Date of Patent: July 20, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Schmidt, Rolf Angerbauer, Arndt Brandes, Michael Logers, Matthias Muller-Gliemann, Hilmar Bischoff, Delf Schmidt, Stefan Wohlfeil
  • Patent number: 5919937
    Abstract: The invention encompasses a novel process for the formation of enantiomerically enriched mixtures of compounds of Formula I, which are useful precursors in the synthesis of phosphodiestersae IV inhibitors.
    Type: Grant
    Filed: October 7, 1998
    Date of Patent: July 6, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Joseph E. Lynch, Kenneth M. Wells, Yao-Jun Shi
  • Patent number: 5891883
    Abstract: The present invention relates to 4,4(disubstituted)cyclohexan-1-ol monomers and related compounds, pharmaceutical compositions containing these compounds, and their use in treating allergic and inflammatory diseases and for inhibiting the production of Tumor Necrosis Factor (TNF).
    Type: Grant
    Filed: September 11, 1997
    Date of Patent: April 6, 1999
    Assignee: SmithKline Beecham Corporation
    Inventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
  • Patent number: 5872117
    Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: February 16, 1999
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
  • Patent number: 5859295
    Abstract: This invention relates to canvanine analogs, their pharmaceutical compositions, and a method for treatment of cancer, particularly pancreatic cancer.
    Type: Grant
    Filed: June 18, 1996
    Date of Patent: January 12, 1999
    Assignee: University of Kentucky Research Foundation
    Inventors: Peter A. Crooks, Gerald A. Rosenthal
  • Patent number: 5808124
    Abstract: Compounds of the formula ##STR1## where the symbols have the meaning described in the application, have retinoid-like or retinoid antagonist-like biological activity.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: September 15, 1998
    Assignee: Allergan
    Inventors: Richard L. Beard, Min Teng, Alan T. Johnson, Vidyasagar Vuligonda, Roshantha A. Chandraratna
  • Patent number: 5783522
    Abstract: Substituted 2-phenylpyridines I ##STR1## R.sup.1,R.sup.3 =H, halogen, alkyl, haloalkyl, alkoxyalkyl, alkoxy, alkoxyalkoxy, OH, haloalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, SH, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, CHO, CN, CO.sub.2 H, alkoxycarbonyl, alkoxyalkoxycarbonyl, haloalkoxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxyalkylcarbonyl, CONH.sub.2, alkyl-aminocarbonyl, dialkylaminocarbonyl, pyrrolidinyl-carbonyl piperidylcarbonyl, morpholinylcarbonyl, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, pyrrolidinyl, piperidinyl, morpholinyl, alkylcarbonylamino, haloalkylcarbonylamino, alkylsulfonylamino;R.sup.2 =halogen, CN, NO.sub.2, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio; orR.sup.1 +R.sup.2 or R.sup.2 +R.sup.3 =trimethylene or tetramethylene chain;R.sup.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: July 21, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schaefer, Gerhard Hamprecht, Elisabeth Heistracher, Hartmann Koenig, Ralf Klintz, Peter Muenster, Harald Rang, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
  • Patent number: 5756497
    Abstract: This invention relates to certain novel benzoxazinone compounds and derivatives thereof, their synthesis, and their use as oxytocin receptor antagonists. One application of these compounds is in the treatment of preterm labor in mammals, especially humans. The ability of the compounds to relax uterine contractions in mammals also makes them useful for treating dysmenorrhea and stopping labor prior to cesarean delivery.
    Type: Grant
    Filed: February 27, 1997
    Date of Patent: May 26, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Ian M. Bell, Roger M. Freidinger, Peter D. Williams
  • Patent number: 5750708
    Abstract: The present invention is directed to compounds of Formula I: ##STR1## wherein: n is 2 or 3;R is dimethylamino, diethylamino, 1-piperidinyl, 1-pyrrolidinyl, 4-morpholinyl, or 1-hexamethyleneimino;R.sup.1 is hydrogen, loweralkyl of C.sub.1 -C.sub.4, phenyl, or mono or di-substituted phenyl wherein each substituent is independently halo, methyl, hydroxy, C.sub.1 -C.sub.6 -alkoxy, benzyloxy, C.sub.1 -C.sub.6 -alkanoyloxy, benzoyloxy, substituted benzoyloxy bearing 1 to 3 substituents each of which is independently halo, C.sub.1 -C.sub.4 -loweralkyl, or C.sub.1 -C.sub.4 -loweralkoxy, C.sub.1 -C.sub.5 -alkoxycarbonyloxy, or C.sub.4 -C.sub.6 -alkylsulfonyloxy;R.sup.2 is hydrogen, hydroxy, C.sub.1 -C.sub.6 -alkoxy, benzyloxy, C.sub.1 -C.sub.6 -alkanoyloxy, benzoyloxy, substituted benzoyloxy bearing 1 to 3 substituents each of which is independently halo, C.sub.1 -C.sub.4 -loweralkyl, or C.sub.1 -C.sub.4 -loweralkoxy, C.sub.1 -C.sub.5 -alkoxycarbonyloxy, or C.sub.4 -C.sub.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: May 12, 1998
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, Don Richard Finley, Ken Matsumoto
  • Patent number: 5652252
    Abstract: The subject of the invention is compounds of general formula: ##STR1## in which: X represents O or CHR,R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which are identical or different, represent a hydrogen atom or a C.sub.1 -C.sub.7 alkyl group, it being possible for R.sub.1 to additionally form a bond with R;R.sub.5 represents a hydrogen atom, a hydroxyl group or R.sub.5, taken together with R.sub.7, forms a bond or a>O; group;R.sub.6 represents a group of formula: ##STR2## in which R.sub.10 and R.sub.11, taken together with the carbon atom to which they are attached, form a nitrogenous heterocyclic group,and their N-oxides and pharmaceutically acceptable salts.These compounds are powerful activators of potassium channels.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: July 29, 1997
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Jean Jacques Berthelon, Michel Brunet, Marc Noblet, Philippe Durbin, Daniel Guerrier, Trong Nghia Luong
  • Patent number: 5643914
    Abstract: This invention relates to a compound of formula 1 ##STR1## or an N-oxide, or a pharmaceutically acceptable salt, where A is CH.sub.2 and Z is S(O).sub.q where q is 0, 1 or 2, CH.sub.2, CHOH, CO, NR.sub.x, or O, orA is C.dbd.O and Z is NR.sub.x ;m is 0-5;R.sub.x is hydrogen or lower alkyl;R is C.sub.1 to C.sub.20 -aliphatic, unsubstituted or substituted five-membered heteroaryl-C.sub.1 to C.sub.10 -aliphatic-O--, unsubstituted or substituted phenyl-C.sub.1 to C.sub.10 -aliphatic where substituted p from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo, or R is C.sub.1 to C.sub.20 -aliphatic-O--, or R is unsubstituted or substituted phenyl-C.sub.1 to C.sub.10 -aliphatic-O-- where substituted phenyl has one or more radicals selected from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo;R.sub.1 is R.sub.4, --(C.sub.1 to C.sub.5 aliphatic)R.sub.4, --(C.sub.1 to C.sub.5 aliphatic)CHO, --(C.sub.1 to C.sub.5 aliphatic)CH.sub.2 OR.sub.5;R.sub.2 and R.sub.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: July 1, 1997
    Assignee: SmithKline Beecham Corporation
    Inventor: Robert A. Daines
  • Patent number: 5637719
    Abstract: The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: June 10, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Michael Philbin
  • Patent number: 5618829
    Abstract: A pharmaceutical composition which comprises a pharmaceutically effective amount of a compound of the formula ##STR1## wherein R.sup.1 represents a hydrogen atom,R.sup.2 represents --(CH.sub.2).sub.m -Awherein m is an integer of 0 to 3, andA represents pyridyl which is unsubstituted or is substituted by C.sub.1 -C.sub.3 alkyl said alkyl being unsubstituted or substituted by phenyl, and R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each independently represent a hydrogen atom, a halogen atom, C.sub.1 -C.sub.5 alkyl which is unsubstituted or is substituted with a halogen atom or --OR.sup.13 wherein R.sup.13 represents a hydrogen atom or C.sub.1 -C.sub.5 alkyl which is unsubstituted or is substituted with a halogen atom or phenyl, or when their adjacent substituents are taken together, they represent C.sub.1 -C.sub.3 oxyalkylene having one or two oxygen atoms;or a pharmaceutically acceptable salt thereof, anda pharmaceutically acceptable carrier therefor.
    Type: Grant
    Filed: January 25, 1994
    Date of Patent: April 8, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Tamaki Yano, Hiroe Umeki, Hiroto Hara