Chalcogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding (e.g., Sulfato Betaines, Etc.) Patents (Class 546/339)
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Patent number: 6093864Abstract: 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: GrantFiled: July 2, 1993Date of Patent: July 25, 2000Assignee: Idemitsu Kosan Co., Ltd.Inventors: Hiroshi Tokailin, Hisahiro Higashi, Chishio Hosokawa
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Patent number: 6080839Abstract: 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: GrantFiled: June 25, 1998Date of Patent: June 27, 2000Assignee: Wallac OyInventors: Harri Takalo, Jari Hovinen, Veli-Matti Mukkala, Paivi Liitti, Heikki Mikola
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Patent number: 6046217Abstract: 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: GrantFiled: September 11, 1998Date of Patent: April 4, 2000Assignee: Merck Frosst Canada & Co.Inventors: Richard Friesen, Rejean Fortin, Daniel Dube, Denis Deschenes
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Patent number: 6040450Abstract: The invention encompasses a process for making compounds of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases.Type: GrantFiled: September 15, 1998Date of Patent: March 21, 2000Assignee: Merck & Co., Inc.Inventors: Ian W. Davies, Michel Journet, Linda Gerena, Robert D. Larsen, Philip J. Pye, Kai Rossen
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Patent number: 6034090Abstract: 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: GrantFiled: July 27, 1999Date of Patent: March 7, 2000Assignee: Sanofi-SynthlaboInventors: Marco Baroni, Rosanna Cardamone, Jacqueline Fournier, Umberto Guzzi
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Patent number: 6022973Abstract: 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: GrantFiled: March 30, 1999Date of Patent: February 8, 2000Assignee: Lonza Ltd.Inventors: Yves Bessard, Gerhard Stucky, Jean-Paul Roduit
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Patent number: 6015821Abstract: 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: GrantFiled: March 3, 1998Date of Patent: January 18, 2000Inventors: David Frederick Horrobin, Mehar Manku, Austin McMordie, Philip Knowles, Peter Redden, Andrea Pitt
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Patent number: 6013795Abstract: Briefly, in one aspect, the present invention provides compositions of open-chain, .alpha.-branched fluoroalkylcarbonyl fluorides, and derivatives thereof.Type: GrantFiled: November 4, 1996Date of Patent: January 11, 2000Assignee: 3M Innovative Properties CompanyInventors: Anthony P. Manzara, Wei-Qiang Fan, Richard M. Stern, George G. I. Moore
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Patent number: 6013649Abstract: 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: GrantFiled: July 22, 1997Date of Patent: January 11, 2000Assignee: Monsanto CompanyInventors: John N. Freskos, S. Zaheer Abbas, Gary A. DeCrescenzo, Daniel P. Getman, Robert M. Heintz, Brent V. Mischke, Joseph J. McDonald
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Patent number: 6010642Abstract: 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 forType: GrantFiled: August 21, 1997Date of Patent: January 4, 2000Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Haruyoshi Takatsu, Sadao Takehara, Kiyofumi Takeuchi, Makoto Negishi, Norie Osawa, Masashi Osawa, Shinji Ogawa, Hirokazu Yanagihara
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Patent number: 6005133Abstract: 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: GrantFiled: October 10, 1995Date of Patent: December 21, 1999Assignee: Pfizer Inc.Inventor: George Joseph Quallich
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Patent number: 6001843Abstract: 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: GrantFiled: October 29, 1998Date of Patent: December 14, 1999Assignee: Merck & Co., Inc.Inventors: Daniel Dube, Rejean Fortin, Richard Friesen, Zhaoyin Wang, Jacques Yves Gauthier
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Patent number: 5998625Abstract: This invention relates to a process for the preparation of a key intermediate using an chiral additive to effect an asymmetric conjugate addition.Type: GrantFiled: January 5, 1998Date of Patent: December 7, 1999Assignee: Merck & Co., Inc.Inventors: Richard D. Tillyer, David M. Tschaen, Feng Xu
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Patent number: 5990314Abstract: 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: GrantFiled: June 7, 1996Date of Patent: November 23, 1999Assignee: SmithKline Beecham CorporationInventor: Robert A. Daines
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Patent number: 5962483Abstract: 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: GrantFiled: January 16, 1998Date of Patent: October 5, 1999Assignee: Celltech Therapeutics, LimitedInventors: Graham John Warrellow, Valerie Anne Cole, Rikki Peter Alexander
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Patent number: 5958838Abstract: Arylheterocycles having the general formula (I): ##STR1## and process for preparing them. The arylheterocycles having the general formula (I) display high herbicidal activity.Type: GrantFiled: November 23, 1998Date of Patent: September 28, 1999Assignee: Isagro Ricerca S.r.l.Inventors: Franco Bettarini, Piero La Porta, Giovanni Meazza, Giampaolo Zanardi, Ernesto Signorini, Domenico Portoso
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Patent number: 5958837Abstract: 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: GrantFiled: June 18, 1997Date of Patent: September 28, 1999Assignee: BASF AktiengesellschaftInventors: Peter Schaefer, Gerhard Hamprecht, Elisabeth Heistracher, Ralf Klintz, Hartmann Konig, Helmut Walter, Karl-Otto Westphalen, Ulf Misslitz
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Patent number: 5948915Abstract: 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: GrantFiled: September 29, 1997Date of Patent: September 7, 1999Assignee: Fuji Xerox Co., Ltd.Inventors: Yasunari Nishikata, Lyong Sun Pu
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Patent number: 5932586Abstract: 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: GrantFiled: November 19, 1996Date of Patent: August 3, 1999Assignee: DuPont Pharmaceuticals CompanyInventors: Douglas Guy Batt, Donald Joseph Phillip Pinto, Michael James Orwat, Joseph James Petraitis, William John Pitts
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Patent number: 5925645Abstract: 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: GrantFiled: March 13, 1997Date of Patent: July 20, 1999Assignee: Bayer AktiengesellschaftInventors: Gunter Schmidt, Rolf Angerbauer, Arndt Brandes, Michael Logers, Matthias Muller-Gliemann, Hilmar Bischoff, Delf Schmidt, Stefan Wohlfeil
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Patent number: 5922880Abstract: 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: GrantFiled: May 20, 1997Date of Patent: July 13, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Noriyasu Sakamoto, Sanshiro Matsuo, Masaya Suzuki, Taro Hirose, Kazunori Tsushima, Kimitoshi Umeda
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Patent number: 5922742Abstract: 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: GrantFiled: April 2, 1997Date of Patent: July 13, 1999Assignee: Merck Frosst CanadaInventors: Cameron Black, Zhaoyin Wang, Greg Hughes
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Patent number: 5919937Abstract: 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: GrantFiled: October 7, 1998Date of Patent: July 6, 1999Assignee: Merck & Co., Inc.Inventors: Joseph E. Lynch, Kenneth M. Wells, Yao-Jun Shi
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Patent number: 5919792Abstract: 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: GrantFiled: October 28, 1997Date of Patent: July 6, 1999Assignee: Merck & Co., Inc.Inventors: Mark E. Duggan, George D. Hartman, William F. Hoffman, Nathan C. Ihle
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Patent number: 5919930Abstract: 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: GrantFiled: July 26, 1995Date of Patent: July 6, 1999Assignee: Hoechst AktiengesellschaftInventors: Steffen Haber, Javier Manero
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Patent number: 5912350Abstract: 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: GrantFiled: October 8, 1997Date of Patent: June 15, 1999Assignee: Neurogen CorporationInventors: Jun Yuan, Andrew Thurkauf
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Patent number: 5906989Abstract: 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: GrantFiled: May 26, 1998Date of Patent: May 25, 1999Assignee: Allergan Sales, Inc.Inventor: Robert M. Burk
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Patent number: 5900417Abstract: 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: GrantFiled: February 27, 1996Date of Patent: May 4, 1999Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
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Patent number: 5891896Abstract: 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: GrantFiled: December 20, 1996Date of Patent: April 6, 1999Assignee: Celltech Therapeutics Ltd.Inventors: Graham John Warrellow, Julien Alistair Brown
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Patent number: 5876628Abstract: 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: GrantFiled: October 18, 1995Date of Patent: March 2, 1999Assignee: Hoechst AktiengesellschaftInventors: Gerhard Illian, Hubert Schlosser, Ingrid Muller, Thoshiaki Nonaka, Kazuya Nagao, Ayako Takeichi, Hidenori Fujiwara, Rainer Wingen
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Patent number: 5872117Abstract: 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: GrantFiled: November 4, 1997Date of Patent: February 16, 1999Assignee: Toyama Chemical Co., Ltd.Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
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Patent number: 5869506Abstract: 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: GrantFiled: January 30, 1997Date of Patent: February 9, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Izumi, Hiroshi Ikegami, Masaya Suzuki, Noriyasu Sakamoto, Hirotaka Takano
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Patent number: 5869677Abstract: 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: GrantFiled: February 27, 1996Date of Patent: February 9, 1999Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
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Patent number: 5866593Abstract: 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: GrantFiled: November 4, 1997Date of Patent: February 2, 1999Assignee: Celltech Therapeutics Ltd.Inventors: Graham John Warrellow, Ewan Campbell Boyd, Rikki Peter Alexander
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Patent number: 5863926Abstract: 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: GrantFiled: October 6, 1997Date of Patent: January 26, 1999Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
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Patent number: 5861419Abstract: 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: GrantFiled: July 11, 1997Date of Patent: January 19, 1999Assignee: Merck Frosst Canad, Inc.Inventors: Daniel Dube, Richard Friesen, Rejean Fortin, Zhaoyin Wang, Jacques Yves Gauthier
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Patent number: 5856498Abstract: 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: GrantFiled: September 16, 1997Date of Patent: January 5, 1999Assignee: Merck & Co., Inc.Inventors: Ilias K. Dorziotis, Ioannis N. Houpis, Jaemoon Lee, Ralph P. Volante
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Patent number: 5851427Abstract: 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: GrantFiled: February 23, 1996Date of Patent: December 22, 1998Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5851424Abstract: 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: GrantFiled: July 25, 1996Date of Patent: December 22, 1998Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5849749Abstract: 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: GrantFiled: June 27, 1997Date of Patent: December 15, 1998Assignee: Bayer AktiengesellschaftInventors: Peter Fey, Rolf Angerbauer, Delf Schmidt, Hilmar Bischoff, Wolfgang Kanhai, Martin Radtke, Wolfgang Karl
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Patent number: 5840724Abstract: 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: GrantFiled: June 24, 1997Date of Patent: November 24, 1998Assignee: Rhone-Poulenc Rorer LimitedInventors: Garry Fenton, Andrew David Morley, Malcolm Norman Palfreyman, Andrew James Ratcliffe, Brian William Sharp, Keith Alfred James Stuttle, Sukanthini Thurairatnam, Bernard Yvon Jack Vacher
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Patent number: 5820785Abstract: 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: GrantFiled: November 18, 1996Date of Patent: October 13, 1998Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Hubert Schlosser, Dietmar Jungbauer
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Patent number: 5817836Abstract: 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: GrantFiled: May 12, 1997Date of Patent: October 6, 1998Assignee: AllerganInventors: Vidyasagar Vuligonda, Roshantha A. Chandraratna
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Patent number: 5808082Abstract: 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: GrantFiled: April 22, 1997Date of Patent: September 15, 1998Assignee: Merck & Co., Inc.Inventors: Woo-Baeg Choi, Hywyn R. D. Churchill, Joseph E. Lynch, Paul J. Reider, Ralph P. Volante
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Patent number: 5808124Abstract: 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: GrantFiled: June 21, 1996Date of Patent: September 15, 1998Assignee: AllerganInventors: Richard L. Beard, Min Teng, Alan T. Johnson, Vidyasagar Vuligonda, Roshantha A. Chandraratna
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Patent number: 5800733Abstract: 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: GrantFiled: July 25, 1996Date of Patent: September 1, 1998Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5798373Abstract: 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: GrantFiled: December 20, 1996Date of Patent: August 25, 1998Assignee: Celltech Therapeutics, LimitedInventor: Graham John Warrellow
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Patent number: 5786354Abstract: 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: GrantFiled: June 20, 1995Date of Patent: July 28, 1998Assignee: Celltech Therapeutics, LimitedInventors: Graham John Warrellow, Rikki Peter Alexander
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Patent number: 5783522Abstract: 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: GrantFiled: January 11, 1996Date of Patent: July 21, 1998Assignee: BASF AktiengesellschaftInventors: Peter Schaefer, Gerhard Hamprecht, Elisabeth Heistracher, Hartmann Koenig, Ralf Klintz, Peter Muenster, Harald Rang, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
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Patent number: 5780477Abstract: 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: GrantFiled: June 21, 1995Date of Patent: July 14, 1998Assignee: Celltech Therapeutics, LimitedInventors: John Clifford Head, Graham John Warrellow, Rikki Peter Alexander