Chalcogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding (e.g., Sulfato Betaines, Etc.) Patents (Class 546/339)
  • Patent number: 6093864
    Abstract: An aromatic dimethylidyne compound of the formula: ##STR1## wherein X and Y are the same or different and are each an alkyl having 1 to 4 carbons, a phenyl, a cyclohexyl, a naphthyl, or a pyridyl and Ar' is ##STR2## A process for preparing an aromatic dimethylidyne compound which comprises condensing a phosphorus compound and a ketone compound.
    Type: Grant
    Filed: July 2, 1993
    Date of Patent: July 25, 2000
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Hiroshi Tokailin, Hisahiro Higashi, Chishio Hosokawa
  • Patent number: 6080839
    Abstract: The invention relates to a novel labeling reactant, suitable for labeling of a biospecific binding reactant using solid-phase synthesis. The invention further concerns new labeling methods. The novel labeling reactant has the formula (I) ##STR1## wherein -A- is a bivalent aromatic structure capable of absorbing light or energy and transferring the excitation energy to a lanthanide ion after the product made by the said solid-phase synthesis has been released from the used solid support, deprotected and converted to a lanthanide chelate;-G- is a bridge replacing a hydrogen atom in A;R is a protected amino acid residue --CH(NHX)COOH, where X is a transient protecting group, or its active ester, where said ester is e.g. an N-hydroxysuccinimido, p-nitrophenol or pentafluorophenol ester; andR' is --COOR'" where R'" is an alkyl of 1 to 4 carbon atoms, phenyl or benzyl, which phenyl or benzyl can be substituted or unsubstituted.
    Type: Grant
    Filed: June 25, 1998
    Date of Patent: June 27, 2000
    Assignee: Wallac Oy
    Inventors: Harri Takalo, Jari Hovinen, Veli-Matti Mukkala, Paivi Liitti, Heikki Mikola
  • Patent number: 6046217
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: September 11, 1998
    Date of Patent: April 4, 2000
    Assignee: Merck Frosst Canada & Co.
    Inventors: Richard Friesen, Rejean Fortin, Daniel Dube, Denis Deschenes
  • Patent number: 6040450
    Abstract: The invention encompasses a process for making compounds of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases.
    Type: Grant
    Filed: September 15, 1998
    Date of Patent: March 21, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Ian W. Davies, Michel Journet, Linda Gerena, Robert D. Larsen, Philip J. Pye, Kai Rossen
  • Patent number: 6034090
    Abstract: The invention relates to compounds of the formula in which: Y is --CH-- or --N--; R.sub.1 is hydrogen, a halogen or a CF.sub.3, (C.sub.1 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)alkoxy group; R.sub.2 is a methyl or ethyl group; R.sub.3 and R.sub.4 are each hydrogen or a (C.sub.1 -C.sub.3)alkyl; and X is:(a) a (C.sub.1 -C.sub.6)alkyl, a (C.sub.1 -C.sub.6)alkoxy, a (C.sub.3 -C.sub.7)carboxyalkyl, a (C.sub.1 -C.sub.4)alkoxy-carbonyl(C.sub.1 -C.sub.6)alkyl, a (C.sub.3 -C.sub.7)carboxyalkoxy or a (C.sub.1 -C.sub.4)alkoxycarbonyl-(C.sub.1 -C.sub.6)alkoxy;(b) a radical selected from (C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkoxy, (C.sub.3 -C.sub.7)-cycloalkylmethyl, (C.sub.3 -C.sub.7)cycloalkylamino and cyclohexenyl, it being possible for said radical to be substituted by a halogen, hydroxyl, (C.sub.1 -C.sub.4)-alkoxy, carboxyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, amino or mono- or di-(C.sub.1 -C.sub.4)-alkylamino; or(c) a group selected from a phenyl, phenoxy, phenylamino, N-(C.sub.1 -C.sub.
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: March 7, 2000
    Assignee: Sanofi-Synthlabo
    Inventors: Marco Baroni, Rosanna Cardamone, Jacqueline Fournier, Umberto Guzzi
  • Patent number: 6022973
    Abstract: A process for preparing pyridinecarboxylic esters of the general formula: ##STR1## wherein R.sup.1 is hydrogen, a C.sub.1 -C.sub.6 -alkyl group, a C.sub.1 -C.sub.4 -alkoxycarbonyl group or a C.sub.1 -C.sub.4 -alkoxymethyl group, R.sup.2 is a C.sub.1 -C.sub.4 -alkyl group and X is chlorine or bromine. The pyridinecarboxylic esters are obtained by reacting the corresponding 2,3-dihalopyridines with carbon monoxide and a C.sub.1 -C.sub.4 -alkanol in the presence of a weak base and a complex of palladium with a bis(diphenylphosphine). Pyridinecarboxylic esters are intermediates for preparing herbicides and drugs against fibrotic diseases.
    Type: Grant
    Filed: March 30, 1999
    Date of Patent: February 8, 2000
    Assignee: Lonza Ltd.
    Inventors: Yves Bessard, Gerhard Stucky, Jean-Paul Roduit
  • Patent number: 6015821
    Abstract: Compounds, compositions, and methods of use as a pharmaceutical, where the compounds have structure (I), where B is --C(.dbd.O)-- or --CH.sub.2 --O--, C is a direct bond or is a diol residue, a hydroxy-substituted carboxylic acid residue, or a dicarboxylic acid residue, and D is a fatty acid residue or a fatty alcohol residue, where the acid residues or alcohol residues for ester linkages with the corresponding alcohols or acids.
    Type: Grant
    Filed: March 3, 1998
    Date of Patent: January 18, 2000
    Inventors: David Frederick Horrobin, Mehar Manku, Austin McMordie, Philip Knowles, Peter Redden, Andrea Pitt
  • Patent number: 6013795
    Abstract: Briefly, in one aspect, the present invention provides compositions of open-chain, .alpha.-branched fluoroalkylcarbonyl fluorides, and derivatives thereof.
    Type: Grant
    Filed: November 4, 1996
    Date of Patent: January 11, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Anthony P. Manzara, Wei-Qiang Fan, Richard M. Stern, George G. I. Moore
  • Patent number: 6013649
    Abstract: This invention is directed to proteinase (protease) inhibitors, and more particularly to thiol sulfone inhibitors for matrix metalloproteinase 13(MMP-13), compositions of proteinase inhibitors, intermediates for the syntheses of proteinase inhibitors, processes for the preparation of proteinase inhibitors and processes for treating pathological conditions associated with pathological matrix metalloproteinase activity related to MMP-13.
    Type: Grant
    Filed: July 22, 1997
    Date of Patent: January 11, 2000
    Assignee: Monsanto Company
    Inventors: John N. Freskos, S. Zaheer Abbas, Gary A. DeCrescenzo, Daniel P. Getman, Robert M. Heintz, Brent V. Mischke, Joseph J. McDonald
  • Patent number: 6010642
    Abstract: Disclosed is to provide an azine derivative as a novel liquid crystal compound, a novel process for the preparation of an asymmetrical azine in a high reaction yield with an extremely small amount of by-products such as symmetrical azines, a nematic liquid crystal composition containing the azine derivative which exhibits a broad driving temperature range and an excellent response for the desired high birefringence index, a liquid crystal display device such as TN-LCD, STN-LCD and TFT-LCD having improved electro-optical properties comprising the liquid crystal composition as a constituent material, and a light-scattering type liquid crystal display system which exhibits a suppressed memory phenomenon, a higher uniformity in turbidity for display and improved display properties and response against temperature change while maintaining and improving the required display properties such as fast switching time, lower voltage driving, higher light-control layer resistivity and higher contrast ratio even in the for
    Type: Grant
    Filed: August 21, 1997
    Date of Patent: January 4, 2000
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Haruyoshi Takatsu, Sadao Takehara, Kiyofumi Takeuchi, Makoto Negishi, Norie Osawa, Masashi Osawa, Shinji Ogawa, Hirokazu Yanagihara
  • Patent number: 6005133
    Abstract: The enantioselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the presence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulae (I) and (II). The compounds of formulae (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulae (I) and (II) may be generated in situ.
    Type: Grant
    Filed: October 10, 1995
    Date of Patent: December 21, 1999
    Assignee: Pfizer Inc.
    Inventor: George Joseph Quallich
  • Patent number: 6001843
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating COX-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. The invention also encompasses certain pharmaceutical compositions for treatment of COX-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: October 29, 1998
    Date of Patent: December 14, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Daniel Dube, Rejean Fortin, Richard Friesen, Zhaoyin Wang, Jacques Yves Gauthier
  • Patent number: 5998625
    Abstract: This invention relates to a process for the preparation of a key intermediate using an chiral additive to effect an asymmetric conjugate addition.
    Type: Grant
    Filed: January 5, 1998
    Date of Patent: December 7, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Richard D. Tillyer, David M. Tschaen, Feng Xu
  • 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: 5962483
    Abstract: Compounds of general formula (1) ##STR1## are described wherein Y is a halogen atom or a group --OR.sup.1, where R.sup.1 is an optionally substituted alkyl group; X is --O--, --S-- or --N(R.sup.7)--, where R.sup.7 is a hydrogen atom or an alkyl group; R.sup.2 is an optionally substituted cycloalkyl or cycloalkenyl group; R.sup.3 and R.sup.4, which may be the same or different, is each a hydrogen atom or an alkyl, --CO.sub.2 R.sup.8 (where R.sup.8 is a hydrogen atom or an alkyl, aryl, or aralkyl group), --CONR.sup.9 R.sup.10 (where R.sup.9 and R.sup.10 which may be the same or different is each a hydrogen atom or an alkyl, aryl or aralkyl group), --CSNR.sup.9 R.sup.10, --CN, --CH.sub.2 CN group; Z is --(CH.sub.2).sub.n -- (where n is zero or an integer 1, 2 or 3; R.sup.5 is an optionally substituted monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen, sulphur or nitrogen atoms; R.sup.
    Type: Grant
    Filed: January 16, 1998
    Date of Patent: October 5, 1999
    Assignee: Celltech Therapeutics, Limited
    Inventors: Graham John Warrellow, Valerie Anne Cole, Rikki Peter Alexander
  • Patent number: 5958838
    Abstract: Arylheterocycles having the general formula (I): ##STR1## and process for preparing them. The arylheterocycles having the general formula (I) display high herbicidal activity.
    Type: Grant
    Filed: November 23, 1998
    Date of Patent: September 28, 1999
    Assignee: Isagro Ricerca S.r.l.
    Inventors: Franco Bettarini, Piero La Porta, Giovanni Meazza, Giampaolo Zanardi, Ernesto Signorini, Domenico Portoso
  • Patent number: 5958837
    Abstract: Substituted 2-phenylpyridines I ##STR1## wherein all variables are as defined in the specification are used as herbicides and for the desiccation/defoliation of plants.
    Type: Grant
    Filed: June 18, 1997
    Date of Patent: September 28, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schaefer, Gerhard Hamprecht, Elisabeth Heistracher, Ralf Klintz, Hartmann Konig, Helmut Walter, Karl-Otto Westphalen, Ulf Misslitz
  • Patent number: 5948915
    Abstract: A cyclobutenedione derivative. It comprises substituted or non-substituted aromatic group A; conjugated chain B which may contain an aromatic bonding group; and hydrogen bonding or ion bonding cyclobutenedionyl group C having an aromatic group which is bonded to the conjugated chain B, wherein A and B and C are bonded in the form of A--B--C. Crystal of the derivative is used as a non-linear optical device.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: September 7, 1999
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Yasunari Nishikata, Lyong Sun Pu
  • Patent number: 5932586
    Abstract: This invention relates to ortho substituted phenyl compounds as inhibitors of prostaglandin synthase, to pharmaceutical compositions comprising such compounds and to methods of using such compounds as antiinflammatory and antipyretic agents.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: August 3, 1999
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Douglas Guy Batt, Donald Joseph Phillip Pinto, Michael James Orwat, Joseph James Petraitis, William John Pitts
  • 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: 5922880
    Abstract: The dihalopropene compounds of the general formula ?I! have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: July 13, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriyasu Sakamoto, Sanshiro Matsuo, Masaya Suzuki, Taro Hirose, Kazunori Tsushima, Kimitoshi Umeda
  • Patent number: 5922742
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating COX-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of COX-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: April 2, 1997
    Date of Patent: July 13, 1999
    Assignee: Merck Frosst Canada
    Inventors: Cameron Black, Zhaoyin Wang, Greg Hughes
  • 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: 5919792
    Abstract: This invention relates to certain novel compounds and derivatives thereof, their synthesis, and their use as vitronectin receptor antagonists. The vitronectin receptor antagonist compounds of the present invention are .alpha.v.beta.3 antagonists, .alpha.v.beta.5 antagonists or dual .alpha.v.beta.3/.alpha.v.beta.5 antagonists useful for inhibiting bone resorption, treating and preventing osteoporosis, and inhibiting restenosis, diabetic retinopathy, macular degeneration, angiogenesis, atherosclerosis, inflammation and tumor growth.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: July 6, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Mark E. Duggan, George D. Hartman, William F. Hoffman, Nathan C. Ihle
  • Patent number: 5919930
    Abstract: Process for cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates.In a process for preparing polycyclic aromatic compounds by cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates under palladium catalysis in the presence of at least one water-soluble complex ligand, the reaction medium comprises an aqueous and an organic phase and the palladium is added in the form of a palladium compound soluble in the organic phase.Polycyclic aromatic compounds can thus be prepared economically and in very good yields and simultaneously very high purity, in particular without contamination by the complexing ligands.
    Type: Grant
    Filed: July 26, 1995
    Date of Patent: July 6, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Steffen Haber, Javier Manero
  • Patent number: 5912350
    Abstract: Disclosed are compounds of the formula: ##STR1## where S and V are various organic or inorganic substituents;G and K are the same or different and represent N or CR' where R' is an organic or inorganic substituent;R is hydrogen or an alkyl group;R.sub.1, X, Y, Z and T are organic or inorganic substituents; andR.sub.2 and R.sub.3 represent hydrogen or organic substituents; orNR.sub.2 R.sub.3 together represents a heterocyclic ring system;and the pharmaceutically acceptable salts thereof; which are highly selective partial agonists or antagonists at brain dopamine receptor subtypes and, thus, are useful in the diagnosis and treatment of affective disorders such as schizophrenia and depression as well as certain movement disorders such as Parkinsonism.
    Type: Grant
    Filed: October 8, 1997
    Date of Patent: June 15, 1999
    Assignee: Neurogen Corporation
    Inventors: Jun Yuan, Andrew Thurkauf
  • Patent number: 5906989
    Abstract: The invention relates to 7-?5-hydroxy-2-(hydroxyhydrocarbyl or heteroatom-substituted hydroxy hydrocarbyl)-3-hydroxy-cyclopentyl(enyl)! heptanoic or heptenoic acids and derivatives of said acids, wherein one or more of said hydroxy groups are replaced by an ether group. The compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma.
    Type: Grant
    Filed: May 26, 1998
    Date of Patent: May 25, 1999
    Assignee: Allergan Sales, Inc.
    Inventor: Robert M. Burk
  • Patent number: 5900417
    Abstract: This invention relates to certain 1,3,34-(trisubstituted)cyciohexane monomers and related compound which are useful in treating allergic and inflammatory diseases and for inhibiting the production of Tumor Necrosis Factor (TNF).
    Type: Grant
    Filed: February 27, 1996
    Date of Patent: May 4, 1999
    Assignee: SmithKline Beecham Corporation
    Inventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
  • Patent number: 5891896
    Abstract: Tri-substituted phenyl derivatives and pharmaceutical compositions containing them. In a preferred embodiment, the compounds have the general formula (2): ##STR1## wherein L is preferably --OR.sup.1 ; R.sup.a is preferably optionally substituted alkyl; R.sup.1 is preferably optionally substituted indanyl; R.sup.3 is preferably hydrogen, fluorine, hydroxy or an optionally substituted straight or branched chain alkyl group; R.sup.4 and R.sup.5 are preferably independently --(CH.sub.2).sub.t Ar, where t is zero or an integer 1, 2 or 3 wherein Ar is preferably optionally substituted monocyclic or bicyclic aryl or optionally substituted monocyclic or bicyclic heteroaryl; and R.sup.6 and R.sup.7 are preferably independently hydrogen, fluorine or optionally substituted alkyl.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: April 6, 1999
    Assignee: Celltech Therapeutics Ltd.
    Inventors: Graham John Warrellow, Julien Alistair Brown
  • Patent number: 5876628
    Abstract: Ferroelectric liquid crystal mixtures containing compounds of the formula (I): ##STR1## wherein R.sup.1 is, for example, a straight-chain or branched alkyl radical having 1 to 22 carbon atoms, in which one --CH.sub.2 -- group may be replaced by --O-- or --CO--O--.
    Type: Grant
    Filed: October 18, 1995
    Date of Patent: March 2, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Illian, Hubert Schlosser, Ingrid Muller, Thoshiaki Nonaka, Kazuya Nagao, Ayako Takeichi, Hidenori Fujiwara, Rainer Wingen
  • 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: 5869506
    Abstract: The present invention provides a fluoropropene compound represented by Formula I: ##STR1## wherein R.sup.1 represents a C.sub.1 -C.sub.10 alkyl group or other groups, Z represents an oxygen atom or other groups, R.sup.2, R.sup.3, and R.sup.4 each independently represent a C.sub.1 -C.sub.3 alkyl group or other groups, r represents an integer of 0 to 2, and X represents a halogen atom or other groups.
    Type: Grant
    Filed: January 30, 1997
    Date of Patent: February 9, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Izumi, Hiroshi Ikegami, Masaya Suzuki, Noriyasu Sakamoto, Hirotaka Takano
  • Patent number: 5869677
    Abstract: The present invention relates to novel 3,3-(disubstituted)cyclohexan-1-carboxylate 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: February 27, 1996
    Date of Patent: February 9, 1999
    Assignee: SmithKline Beecham Corporation
    Inventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
  • Patent number: 5866593
    Abstract: Compounds of the general formula (1) ##STR1## are described wherein Y is halogen or --OR.sup.1, where R.sup.1 is optionally substituted alkyl; X is --O--, --S-- or --N(R.sup.8)-, where R.sup.8 is hydrogen or alkyl; R.sup.2 is optionally substituted alkyl, alkenyl, cycloalkyl or cycloalkenyl; R.sup.3 is hydrogen, halogen or --OR.sup.9, where R.sup.9 is hydrogen or optionally substituted alkyl, alkenyl, alkoxyalkyl, or alkanoyl, or formyl, carboxamido or thiocarboxamido; R.sup.4 is --(CH.sub.2).sub.n Ar, where Ar is monocyclic or bicyclic aryl optionally containing one or more heteroatoms selected from oxygen, sulfur and nitrogen atoms, wherein Ar is substituted by an optionally substituted C.sub.3-9 cycloaliphatic group optionally containing one or more heteroatoms selected from oxygen, sulphur or --N(R.sup.8)-, and n is zero or an integer 1, 2 or 3; R.sup.5 is --(CH.sub.2).sub.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: February 2, 1999
    Assignee: Celltech Therapeutics Ltd.
    Inventors: Graham John Warrellow, Ewan Campbell Boyd, Rikki Peter Alexander
  • Patent number: 5863926
    Abstract: The present invention relates to novel 4,4-(disubstituted)cyclohexan-1-carboxylate 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: October 6, 1997
    Date of Patent: January 26, 1999
    Assignee: SmithKline Beecham Corporation
    Inventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
  • Patent number: 5861419
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating COX-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of COX-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: July 11, 1997
    Date of Patent: January 19, 1999
    Assignee: Merck Frosst Canad, Inc.
    Inventors: Daniel Dube, Richard Friesen, Rejean Fortin, Zhaoyin Wang, Jacques Yves Gauthier
  • Patent number: 5856498
    Abstract: This invention is concerned with a novel process for the preparation of a compound of structural formula I ##STR1## wherein R.sup.1 and R.sup.2 independently are aryl, C.sub.2-15 alkenyl or C.sub.1-15 alkyl, either unsubstituted or substituted with one or three substituents, which can be the same or different, selected from the group consisting of R.sup.a, wherein R.sup.a belongs to a group consisting of C.sub.1-6 alkyl, aryl, halo, --N(R.sup.3).sub.2, --NO.sub.2, --CN, --OR.sup.3, --C.sub.3-6 cycloalkoxy, --CO(R.sup.3), --COOR.sup.3, SO.sub.2 R.sup.3 and --SR.sup.3 ; wherein R3 is selected from the group consisting of hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl and aryl, said alkyl, alkenyl or aryl optionally substituted with 1 to 3 groups of R.sup.a, which is an important antiasthmatic agent.
    Type: Grant
    Filed: September 16, 1997
    Date of Patent: January 5, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Ilias K. Dorziotis, Ioannis N. Houpis, Jaemoon Lee, Ralph P. Volante
  • Patent number: 5851427
    Abstract: Photocross-linkable naphthyl derivatives include compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 each independently signify a cross-linkable group;S.sup.1 and S.sup.2 signify --(CY.sub.2).sub.m -, --O(CY.sub.2).sub.m -, --(CY.sub.2).sub.m O--, --(CY.sub.2).sub.m COO--, --(CY.sub.2).sub.m OOC--, --(Si?(CH.sub.3).sub.2 !O).sub.m -, --OCH.sub.2 (Si?(CH.sub.3).sub.2 !O).sub.m Si?(CH.sub.3).sub.2 !CH.sub.2 O-- or --NHCH.sub.2 (Si?(CH.sub.3).sub.2 !O).sub.m Si?(CH.sub.3).sub.2 !CH.sub.2 NH--;Y signifies hydrogen, fluorine or methyl;a signifies 0 or 1;b signifies 1 or 2, with the proviso that a+b=2;m signifies a whole number of 1 to 16;A.sup.1 and A.sup.2 each independently signify 1,4-phenylene, which is optionally mono- or multiply-substituted with halogen, cyano, methyl, methoxy and/or acetyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl; andZ.sup.1 and Z.sup.2 each independently signify a single bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: December 22, 1998
    Assignee: Rolic AG
    Inventor: Stephen Kelly
  • Patent number: 5851424
    Abstract: The present invention is concerned with photo cross-linkable liquid crystalline compounds of the general formula ##STR1## wherein A.sup.1 and A.sup.2 each represent a cross-linkable, mesogenic residue,liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.
    Type: Grant
    Filed: July 25, 1996
    Date of Patent: December 22, 1998
    Assignee: Rolic AG
    Inventor: Stephen Kelly
  • Patent number: 5849749
    Abstract: The 6-(hydroxymethyl-ethyl)pyridines are prepared by a process in which the 3-hydroxymethylpyridines which are hydroxyl-protected in the 6-position are oxidized to the 3-aldehyde, this is then converted into the corresponding oxoheptenoic acid derivative using a Wittig-Homer reaction, after this the oxo group is reduced to the hydroxyl group and then the isomers are separated by chromatography. The 6-(hydroxymethyl-ethyl)pyridines are suitable as active compounds in medicaments, in particular in medicaments having antiarteriosclerotic activity.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: December 15, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Fey, Rolf Angerbauer, Delf Schmidt, Hilmar Bischoff, Wolfgang Kanhai, Martin Radtke, Wolfgang Karl
  • Patent number: 5840724
    Abstract: This invention is directed to the pharmaceutical use of phenyl compounds, which are linked to an aryl moiety by various linkages, for inhibiting tumor necrosis factor. The invention is also directed to the compounds, their preparation and pharmaceutical compositions containing these compounds. Furthermore, this invention is directed to the pharmaceutical use of the compounds for inhibiting cyclic AMP phosphodiesterase.
    Type: Grant
    Filed: June 24, 1997
    Date of Patent: November 24, 1998
    Assignee: Rhone-Poulenc Rorer Limited
    Inventors: Garry Fenton, Andrew David Morley, Malcolm Norman Palfreyman, Andrew James Ratcliffe, Brian William Sharp, Keith Alfred James Stuttle, Sukanthini Thurairatnam, Bernard Yvon Jack Vacher
  • Patent number: 5820785
    Abstract: Disclosed are derivatives of fluoroalkylethynyl- and difluoroalkylethynylbenzenes of the formula (I) herein. These compounds exhibit useful properties as liquid crystal compounds and are useful in nematic liquid crystal mixtures.
    Type: Grant
    Filed: November 18, 1996
    Date of Patent: October 13, 1998
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Hubert Schlosser, Dietmar Jungbauer
  • Patent number: 5817836
    Abstract: Compounds of Formula 1 ##STR1## wherein Z is selected from the group consisting of the radicals shown in Formula 2 and in Formula 3, ##STR2## Y is cycloalkyl or cycloalkenyl of 3 to 8 carbons optionally substituted with one or two R.sub.4 groups, or Y is selected from phenyl, pyridyl, thienyl, furyl, pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R.sub.4 groups, the divalent Y radical being substituted by the Z and --CR.sub.1 .dbd.CR.sub.1 --CR.sub.1 .dbd.CR.sub.1 groups on adjacent carbons; X is S, O, or NR.sub.5 ; n is 1 or 2; R.sub.1 and R.sub.2 independently are H, lower alkyl or fluoroalkyl; R.sub.3 is hydrogen, lower alkyl, Cl or Br; R.sub.4 is lower alkyl, fluoroalkyl or halogen; R.sub.5 is H or lower alkyl, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.
    Type: Grant
    Filed: May 12, 1997
    Date of Patent: October 6, 1998
    Assignee: Allergan
    Inventors: Vidyasagar Vuligonda, Roshantha A. Chandraratna
  • Patent number: 5808082
    Abstract: A process for the preparation of Phosphodiesterase IV inhibitors is described. The process consists of eight chemical steps involving five isolations to prepare the title compound from readily available isovanillin in 35% overall yield (Scheme 1). The process is highlighted by: a) a highly diastereoselective Michael addition of phenyllithium using (1R, 2S) cis-aminoindanol as a chiral auxiliary, b) highly crystalline intermediates providing for efficient purifications, c) crystallization of the final compound as its CSA salt for excellent enantiomeric purity.
    Type: Grant
    Filed: April 22, 1997
    Date of Patent: September 15, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Woo-Baeg Choi, Hywyn R. D. Churchill, Joseph E. Lynch, Paul J. Reider, Ralph P. Volante
  • 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: 5800733
    Abstract: The present invention is concerned with photo cross-linkable liquid crystalline compounds in the formula ##STR1## wherein for example: A,B,C,D,E,F independently is pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diylZ.sup.1, Z.sup.2, Z.sup.7 independently is --(CH.sub.2).sub.s O--, --COO--, --(CH.sub.2).sub.s COO--Z.sup.3, Z.sup.4, Z.sup.8 independently is a single bond, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--Z.sup.5, Z.sup.6 independently is --(CH.sub.2).sub.s --m, n, q and r independently is 0, 1 or 2;s is a whole number of 1 to 16;R.sup.1, R.sup.2 independently is CH.sub.2 .dbd.CH--COO--, CH.sub.2 .dbd.C(CH.sub.3)--COO--R.sup.3 is H, CH, COOC.sub.n H.sub.2n+1, CnH.sub.2n+1 ; n=1 . . . 10X.sup.1, X.sup.2 and X.sup.3 independently is hydrogen, halogen, cyano or lower alkyl.The invention is also related to liquid crystalline mixtures and their use for electro-optical purpose.
    Type: Grant
    Filed: July 25, 1996
    Date of Patent: September 1, 1998
    Assignee: Rolic AG
    Inventor: Stephen Kelly
  • Patent number: 5798373
    Abstract: Tri-substituted phenyl derivatives and pharmaceutical compositions containing them. In a preferred embodiment, the compounds have the general formula (2): ##STR1## wherein L is preferably --OR; R.sup.a is preferably an optionally substituted alkyl group; R is preferably an optionally substituted cycloalkyl group; R.sup.3 is preferably hydrogen; R.sup.4 is preferably hydrogen, --(CH.sub.2).sub.t --Ar or --(CH.sub.2).sub.t --Ar--(L.sup.1).sub.n --Ar'; R.sup.5 is preferably --(CH.sub.2).sub.t --Ar or --(CH.sub.2).sub.t ---Ar--(L.sup.1).sub.n --Ar'; R.sup.6 and R.sup.7 are preferably hydrogen, L.sup.1 is preferably a divalent linking group; Ar is preferably a monocyclic or bicyclic aryl or heteroaryl group; and Ar' is preferably Ar or an Ar containing group. Compounds of the invention are potent and selective phosphodiesterase type IV inhibitors and are useful in the prophylaxis and treatment of various diseases, such as asthma, which are associated with an unwanted inflammatory response or muscular spasm.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: August 25, 1998
    Assignee: Celltech Therapeutics, Limited
    Inventor: Graham John Warrellow
  • Patent number: 5786354
    Abstract: Tri-substituted phenyl derivatives and processes for their preparation. In a preferred embodiment, the compounds have the general formula (2) ##STR1## wherein L is preferably --OR; Z is preferably --C(R.sup.3)(R.sup.4)--C(R.sup.5)(R.sup.6)(R.sup.7); R is preferably an optionally substituted cycloalkyl group: R.sup.3 is preferably hydrogen; R.sup.4 is hydrogen, --(CH.sub.2).sub.t Ar or --(CH.sub.2).sub.t --Ar--(L.sup.1).sub.n --Ar'; R.sup.5 is --(CH.sub.2).sub.t Ar or --(CH.sub.2).sub.t --Ar--(L.sup.1).sub.n --Ar'; R.sup.6 and R.sup.7 are preferably hydrogen or methyl; Ar is a monocyclic or bicyclic aryl or heteroaryl group; L.sup.1 is a divalent linking group; and Ar' is Ar or an Ar containing group. Compounds of the invention are potent and selective phosphodiesterase type IV inhibitors and are useful in the prophylaxis and treatment of various diseases, such as asthma, which are associated with an unwanted inflammatory response or muscular spasm.
    Type: Grant
    Filed: June 20, 1995
    Date of Patent: July 28, 1998
    Assignee: Celltech Therapeutics, Limited
    Inventors: Graham John Warrellow, Rikki Peter Alexander
  • 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: 5780477
    Abstract: Compounds of general formula (1) ##STR1## are described wherein .dbd.W-- is (1) .dbd.C(Y)-- where Y is a halogen atom, or an alkyl, (2) .dbd.N--; L is a --XR, ?where R is an optionally substituted alkyl, alkenyl, cycloalkyl or cyloalkenyl group!, Z is (1) a group --C(R.sup.3)(R.sup.4)C(R.sup.5)(R.sup.6)(R.sup.7) or --C(R.sup.4).dbd.C(R.sup.5)(R.sup.6) where R.sup.3 is a hydrogen or a fluorine atom or an optionally substituted straight or branched alkyl group; R.sup.4 is a group selected from --X.sup.a L.sup.1 R.sup.12 ?where X.sup.a is as defined above for X, L.sup.1 is a linker group and R.sup.12 is a hydrogen atom or a cycloaliphatic, bicyclic aryl group --Alk.sup.1 R.sup.12 ?where Alk.sup.1 is an optionally substituted straight or branched alkenyl or alkynyl chain or Z is (2) a group --C(R.sup.4)C(R.sup.5)(R.sup.6)(R.sup.7) where R.sup.4 is a group .dbd.CH.sub.2, or .dbd.CH(L.sup.1).sub.n --R.sup.12 ; and the salts, solvates, hydrates, prodrugs and N-oxides thereof.
    Type: Grant
    Filed: June 21, 1995
    Date of Patent: July 14, 1998
    Assignee: Celltech Therapeutics, Limited
    Inventors: John Clifford Head, Graham John Warrellow, Rikki Peter Alexander