Chalcogen Or Nitrogen Attached Directly To The Hetero Ring By Nonionic Bonding Patents (Class 549/28)
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Patent number: 5523312Abstract: Disclosed herein are compounds and pharmaceutical compositions useful for combating picornaviruses and preventing or treating picornaviral infections. The compounds have the formula: ##STR1## wherein Het.sub.1 is chosen from the group consisting of oxazolyl, isoxazolyl, oxadiazolyl;Y is an alkylene bridge of 3 to 9 carbon atoms;Het.sub.2 is benzofuranyl or indolyl;R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, acetyl, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinyl alkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluromethyl, or cyano; andR.sub.3 is oxazolyl, oxadiazolyl, isoxazolyl or any of these substituted with alkyl, halo, alkoxyalkyl, cycloalkyl, haloalkyl, hydroxyalkyl, alkoxy, hydroxy, furyl, thienyl, or fluoroalkyl;the N-oxide thereof or a pharmaceutically acceptable acid addition salt thereof.Type: GrantFiled: September 27, 1994Date of Patent: June 4, 1996Assignee: Sterling Winthrop Inc.Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Gee-Hong Kuo, Theodore J. Nitz, Michael Reuman
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Patent number: 5506262Abstract: Disclosed herein are compounds of structural formula (I) ##STR1## which are useful as cholesterol lowering agents. These compounds are also useful as inhibitors of squalene synthetase, inhibitors of fungal growth, inhibitors of farnesyl-protein transferase and farnesylation of the oncogene protein Ras. These compounds are also useful in the treatment of cancer.Type: GrantFiled: November 10, 1993Date of Patent: April 9, 1996Assignee: Merck & Co., Inc.Inventors: Robert M. Burk, William H. Parsons, John J. Acton, III, Gregory D. Berger, Tesfaye Biftu, Robert L. Bugianesi, Yuan-Ching P. Chiang, Claude Dufresne, Narindar N. Girotra, Robert W. Marquis, Jr., Chan-Hwa Kuo, Sandra P. Plevyak, Mitree M. Ponpipom, Lori L. Whiting, James D. Bergstrom, Conrad Santini
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Patent number: 5504056Abstract: A heterocyclic cyclohexanedione derivative represented by the general formula I!: ##STR1## wherein R.sup.1 is optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclic ring; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 may be the same or different from one another and each independently represents hydrogen or lower alkyl; R.sup.6 is hydrogen; R.sup.7 is OR.sup.8 wherein R.sup.8 is hydrogen, lower alkyl, aralkyl, lower acyl, alkylsulfonyl or arylsulfonyl; or R.sup.6 and R.sup.7 are combined together to represent a single bond; X is oxygen, sulfur or N--R.sup.9 wherein R.sup.9 is hydrogen, lower alkyl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclic ring, a salts thereof, a process for producing the same, and a herbicides comprising the same.Type: GrantFiled: July 20, 1994Date of Patent: April 2, 1996Assignee: Nippon Soda Co., Ltd.Inventors: Hiroyuki Adachi, Toshio Aihara, Katsunori Tanaka, Takashi Kawana, Shigeo Yamada, Hideo Hosaka
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Patent number: 5491152Abstract: The present invention provides compounds of Formula I, ##STR1## or a pharmaceutically acceptable salt forms thereof, which are inhibitors of acyl-Coenzyme A: cholesterol O-acyltransferase (ACAT), pharmaceutical compositions containing such compounds, processes for the preparation of such compounds, and the use of such compounds as antihypercholesterolemic and/or antiatherosclerotic agents.Type: GrantFiled: March 23, 1994Date of Patent: February 13, 1996Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Richard G. Wilde, Soo S. Ko, Jeffrey T. Billheimer
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Patent number: 5484805Abstract: The invention concerns a heterocyclene derivative of the formula I ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a 9- or 10-membered bicyclic heterocyclic moiety;A.sup.1 is a direct link to X.sup.1 or (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar.sup.2 is optionally substituted 5-membered heterocyclene moiety;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sub.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 5 to 7 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: July 8, 1994Date of Patent: January 16, 1996Assignees: Imperial Chemical Industries PLC, ICI PharmaInventor: Thomas G. C. Bird
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Patent number: 5480893Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.Type: GrantFiled: May 13, 1994Date of Patent: January 2, 1996Assignee: Merck & Co., Inc.Inventors: Samuel L. Graham, S. Jane deSolms
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Patent number: 5480858Abstract: Cyclohexanedione derivatives of the formula (I), ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group, R.sup.2 is a C.sub.1 -C.sub.4 alkyl group, each of R.sup.3, R.sup.4 and R.sup.5 is independently hydrogen or a C.sub.1 -C.sub.4 alkyl group, and n is an integer of 0 to 2, or salts thereof exhibit high selectivity for corn, wheat and barley, and can control gramineous weeds and broad-leaved weeds at low dosages.Type: GrantFiled: January 13, 1995Date of Patent: January 2, 1996Assignee: Idemitsu Kosan Co., Ltd.Inventors: Masashi Sakamoto, Mitsuru Shibata, Ichiro Nasuno, Kazuyoshi Koike
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Patent number: 5478928Abstract: 2',3'-dideoxy-4'-thioribonucleosides useful as antiviral agents in the treatment and prevention of AIDS are disclosed. In accordance with one aspect of the invention there are provided compounds of the formula ##STR1## where X.dbd.H, N.sub.3 or F, and B is a member selected from the group consisting of pyrimidine, 5-azapyrimidine, 6-azapyrimidine, 3-deazapyrimidine, purine, 3-deazapurine, 7-deazapurine, 8-azapurine, and 2-azapurine bases. The intermediate 1-O-acetyl-5-O-t-butyldiphenylsilyl-4-thio-2,3-dideoxyribofuranose is useful in the production of certain of the 2',3'-dideoxy-4'-thioribonucleosides. Other intermediates include the 4-thio-2,3-dideoxyribofuranose having different hydroxyl protecting groups and leaving groups.Type: GrantFiled: October 29, 1993Date of Patent: December 26, 1995Assignee: Southern Research InstituteInventors: John A. Montgomery, John A. Secrist, III
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Patent number: 5470974Abstract: A composition of polymer molecules effective to bind, with substantially uniform binding affinity, to a single-stranded polynucleotide containing a target sequence of bases. The polymer molecules are composed of a sequence of base-pairing moieties effective to hydrogen bond to corresponding, complementary bases in the target sequence, under selected binding conditions, and a predominantly uncharged, achiral backbone supporting the base-pairing moieties at positions and in orientations which allow hydrogen bonding between the pairing moieties of the polymer and the corresponding complementary bases in the target sequence. The composition has diagnostic uses, in a solid-support assay system, and therapeutic uses involving inhibition or inactivation of target polynucleotides.Type: GrantFiled: February 25, 1994Date of Patent: November 28, 1995Assignee: Neu-Gene Development GroupInventors: James Summerton, Dwight Weller, Eugene Stirchak
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Patent number: 5468878Abstract: Cyclohexanedione derivatives of the general formula (I), ##STR1## wherein: R is a C.sub.1 -C.sub.4 alkyl group,each of R.sup.1 to R.sup.6 is independently hydrogen or a C.sub.1 -C.sub.4 alkyl group,X.sup.1 is a C.sub.1 -C.sub.4 alkyl group,X.sup.2 is hydrogen or a C.sub.1 -C.sub.4 alkyl group, andn is an integer of 0 to 2.or salta thereof exhibit high selectivity for corn, wheat and barley, can control gramineous weeds and broad-leaved weeds at a low dosage, and can be desirably used as an active ingredient of a herbicide.Type: GrantFiled: February 2, 1995Date of Patent: November 21, 1995Assignee: Idemitsu Kosan Co., Ltd.Inventors: Ichiro Nasuno, Mitsuru Shibata, Masashi Sakamoto, Kazuyoshi Koike
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Patent number: 5428061Abstract: New organic nitrate compounds, formed by condensing a nitrato alkanoic acid with a sulfur-containing amino acid or peptide, which prevent nitrate tolerance or overcome existing tolerance and which are useful for the treatment of cardiac diseases including circulatory diseases, high blood pressure, cardiac insufficiency and for dilating the peripheral vessels.Type: GrantFiled: September 7, 1993Date of Patent: June 27, 1995Assignee: Schwarz Pharma AGInventors: Klaus Sandrock, Joachim Hutter, Eike Noack
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Patent number: 5405976Abstract: Dyes comprising an inner salt of a compound of the formula:Q.sup.1 =Z-Q.sup.2wherein:Q.sup.1 is a 4-(benz[b]-4H-pyrylium)methylidene, 4-(benz[b]-4H-thiopyrylium)methylidene or 4-(benz[b]-4H-selenopyrylium)methylidene grouping;Z is a 1,3-(2-hydroxy-4-oxo-2-cyclobutylidene) hydroxide or 1,3-(2-hydroxy-4,5-dioxo-2-cyclopentylidene) hydroxide ring; andQ.sup.2 is a 4-(benz[b]-4H-pyran-4-ylidene)methyl, 4-(benz[b]-4H-thiopyran-4-ylidene)methyl or 4-(benz[b]-4H-selenopyran-4-ylidene)methyl grouping;wherein at least one of the groupings Q.sup.1 and Q.sup.Type: GrantFiled: September 24, 1993Date of Patent: April 11, 1995Assignee: Polaroid CorporationInventors: Stephen J. Telfer, Robert P. Short, Stephen G. Stroud, Anthony J. Puttick, Socorro Ramos, Michael J. Zuraw
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Patent number: 5403857Abstract: The invention concerns benzenesulphonamide derivatives of the formula I ##STR1## wherein R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; R.sup.2 and R.sup.3 together form -A.sup.2 -X.sup.2 -A.sup.3 - which defines a ring having 5 or 6 ring atoms, wherein A.sup.2 and A.sup.3 each is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl; A.sup.1 is a direct link to X.sup.1 or is (1-3C) alkylene; X.sup.1 is oxy, thio or imino; Ar is optionally substituted phenylene; R.sup.4 is (1-4C)alkyl, fluoro-(2-4C)alkyl or optionally substituted phenyl or a heterocyclic moiety; R.sup.5 is hydrogen or (1-4C)alkyl; and R.sup.6 is hydrogen, halogeno, trifluoromethyl, (1-4C)alkyl or (1-4C)alkoxy; or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.Type: GrantFiled: February 1, 1994Date of Patent: April 4, 1995Assignees: Imperial Chemical Industries PLC, ICI-PharmaInventors: Philip N. Edwards, Keith Oldham, David Waterson
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Patent number: 5399589Abstract: Oxalyl hydrazide-hydroxamic acid derivatives of the formula I ##STR1## where the substituents have the following meanings: R, R.sup.1, R.sup.2 and R.sup.3 independently of one another arehydrogen, substituted or unsubstituted alkyl, alkenyl or alkynyl orsubstituted or unsubstituted cycloalkyl or cycloalkylmethyl,substituted or unsubstituted cycloalkenyl or cycloalkenylmethyl,substituted or unsubstituted phenyl, phenylalkyl, phenylalkenyl, hetaryl- or hetarylalkyl radicals, where R.sup.2 and R.sup.3 may also. together with the nitrogen atom whose substituents they are, form a 5- or 6-membered ring, orR.sup.2 together with R.sup.3 is the group ##STR2## where R.sup.4 and R.sup.5 are one of the radicals R, R.sup.1, R.sup.2 or R.sup.3, or R.sup.4 together with R.sup.5 and the carbon atom whose substituents they are, are monocyclic or polycyclic cycloalkyl, orR.sup.4 together with R.sup.5 and the carbon atom whose substituents they are, form a 5- or 6-membered, saturated heterocycle containing O, S or --N(R.sup.Type: GrantFiled: November 29, 1993Date of Patent: March 21, 1995Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Albrecht Harreus, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5395946Abstract: The invention related to a method of preparing a protein or a proteinaceous material labelled with a metalradionuclide and intended for diagnostic or therapeutic application, by reacting a protein or a proteinaceous material with an agent for coupling the radionuclide to the protein or the proteinaceous material, a protein conjugate being formed, and by then complexing the radionuclide with the conjugate thus formed to a radionuclide complex.Type: GrantFiled: August 7, 1990Date of Patent: March 7, 1995Inventors: Wilhelmus T. Goedemans, Karel J. Panek
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Patent number: 5360815Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.Type: GrantFiled: June 23, 1993Date of Patent: November 1, 1994Assignee: Merck Frosst Canada, Inc.Inventors: Rejean Fortin, Yves Girard, Erich Grimm, John Hutchinson, John Scheigetz
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Patent number: 5360817Abstract: Derivatives and analogues of 2-deoxy-2,3-didehydro-N-acetyl neuraminic acid, pharmaceutical formulations thereof, methods for their preparation .and their use in the treatment of viral infections, in particular influenza, are described.Type: GrantFiled: November 10, 1992Date of Patent: November 1, 1994Assignee: Biota Scientific Management Pty LtdInventors: Laurence M. von Izstein, Wen-Yang Wu, Tho V. Phan, Basil Danylec, Betty Jin
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Patent number: 5354873Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an aromatic unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an acyl, aliphatic, cycloaliphatic, aromatic or heterocyclic group, subject to the proviso that one of R.sup.3 and R.sup.4 may be an amino or substituted amino group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a nitrogenous heterocyclic ring) are useful as near infra-red absorbers.Type: GrantFiled: November 20, 1992Date of Patent: October 11, 1994Assignee: Polaroid CorporationInventors: Richard M. Allen, Peter K. Chu, John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
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Patent number: 5352802Abstract: Certain chemical compounds, which are aromatic heterocyclic-substituted derivatives of 4H-thiopyran-1,1-dioxide, are electron-transport agents. These compounds exhibit good speed and toe voltage properties in electrophotographic elements.Type: GrantFiled: September 7, 1993Date of Patent: October 4, 1994Assignee: Eastman Kodak CompanyInventors: Michael R. Detty, John A. Sinicropi, J. Robin Cowdery, Ralph H. Young
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Patent number: 5338735Abstract: Compounds of the formula: ##STR1## in which each R.sup.1 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or nitro, and n is 0, 1, 2 or 3, R.sup.2 is hydrogen, C.sub.1-4 alkyl or C.sub.2-4 alkenyl, R.sup.3 and R.sup.4 are each hydrogen, C.sub.1-4 alkyl, optionally substituted phenyl or C.sub.6-9 cycloalkyl optionally substituted by 1 to 4 C.sub.1-4 alkyl groups, R.sup.5 is optionally substituted phenyl, tetrahydronaphthyl, phthalimido, saccharinyl, glutaramido, C.sub.6-10 cycloalkyl optionally substituted with 1 to 4 C.sub.1-4 alkyl groups or a phenyl group, or C.sub.4-9 heterosubstituted cycloalkyl optionally substituted with 1 to 4 alkyl groups, x is 1, 2 or 3, y is 0 or 1 and z is 0, 1, 2 or 3; and salts thereof.The compounds are indicated for use in the treatment of disorders of the central nervous system.Type: GrantFiled: August 12, 1993Date of Patent: August 16, 1994Assignee: Lilly Industries LimitedInventors: John Fairhurst, David E. Tupper
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Patent number: 5326783Abstract: This invention is directed to compounds of formula (I) which are novel C3- or C5-acyl sulfonamide, carboxamic acid or tetrazolyl analogs of the Zaragozic acids. These compounds inhibit the enzyme squalene synthase and are useful as cholesterol lowering agents.Type: GrantFiled: January 19, 1993Date of Patent: July 5, 1994Assignee: Merck & Co., Inc.Inventors: Tesfaye Biftu, Chan-Hwa Kuo, Conrad Santini
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Patent number: 5319102Abstract: Heterocyclic-alkylene quinoxalinyloxyphenoxypropanoate compounds exhibit unexpectedly desirable selective herbicidal activity. Also disclosed are compositions comprising such compounds as well as a method of controlling the growth of undesirable plants employing such compounds.Type: GrantFiled: April 30, 1992Date of Patent: June 7, 1994Assignee: Uniroyal Chemical Company, Inc.Inventors: Robert G. Davis, Allyn R. Bell, John A. Minatelli
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Patent number: 5314891Abstract: The invention concerns benzenesulphonamide derivatives of the formula I ##STR1## wherein R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl;R.sup.2 and R.sup.3 together form --A.sup.2 --X.sup.2 --A.sup.3 -- which defines a ring having 5 or 6 ring atoms, wherein A.sup.2 and A.sup.3 each is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio or imino;Ar is optionally substituted phenylene;R.sup.4 is (1-4C)alkyl, fluoro-(2-4C)alkyl or optionally substituted phenyl or a heterocyclic moiety;R.sup.5 is hydrogen or (1-4C)alkyl; andR.sup.6 is hydrogen, halogeno, trifluoromethyl, (1-4C)alkyl or (1-4C)alkoxy;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.Type: GrantFiled: September 10, 1992Date of Patent: May 24, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Philip N. Edwards, Keith Oldham, David Waterson
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Patent number: 5288903Abstract: Preparation of 3-pentenoic acid by the reaction of 3-pentenoylchloride, water and butadiene. 3-chloro-1-butene and 1-chloro-2-butene are also formed. Preferably the 3-pentenoylchloride is formed by the reaction of chlorobutene with carbon monoxide using a palladium catalyst.Type: GrantFiled: July 26, 1993Date of Patent: February 22, 1994Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio E. Bunel, Chen-Chou Chiang, Michael B. D'Amore, Erik J. Schaumann, Leon S. Scott
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Patent number: 5281720Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.Type: GrantFiled: October 26, 1992Date of Patent: January 25, 1994Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Yves Girard, John W. Gillard, Laird A. Trimble, John Scheigetz, James A. Yergey, Yves Ducharme, Deborah A. Nicoll-Griffith, John H. Hutchinson
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Patent number: 5258401Abstract: Disclosed herein are compounds of structural formula (I) ##STR1## which are useful as cholesterol lowering agents. These compounds are also useful as inhibitors of squalene synthase, inhibitors of fungal growth, inhibitors of farnesyl-protein transferase and farnesylation of the oncogene protein Ras. These compounds are also useful in the treatment of cancer.Type: GrantFiled: September 10, 1992Date of Patent: November 2, 1993Assignee: Merck & Co., Inc.Inventors: Gregory D. Berger, Robert W. Marquis, Jr., Albert J. Robichaud, Edward M. Scolnick
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Patent number: 5246961Abstract: The present invention relates, by way of novel industrial products, to the .beta.-D-phenylthioxyloside compounds of the formula ##STR1## in which: X represents a sulfur atom or an oxygen atom;R.sub.1, R.sub.2 and R.sub.3, which are identical or different, each represent a hydrogen atom, a nitro group, a cyano group, a group --CO--R (in which R represents a C.sub.1 -C.sub.4 alkyl group or a trifluoromethyl group), an amino group, an acetamido group (NHCOCH.sub.3), a C.sub.1 -C.sub.4 alkoxy group, a trifluoromethyl group or a phenyl group substituted by one or more cyano, nitro or trifluoromethyl groups, it being possible for R.sub.1 and R.sub.2, taken together, to form, with the phenyl group to which they are bonded, a .beta.-naphthalenyl group which is unsubstituted or substituted by one or more cyano, nitro or trifluoromethyl groups; andY represents the hydrogen atom or an aliphatic acyl group.Type: GrantFiled: November 18, 1991Date of Patent: September 21, 1993Assignee: Fournier Industrie et SanteInventors: Soth Samreth, Jean Millet, Francois Bellamy
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Patent number: 5231190Abstract: Squarylium compounds of the formula: ##STR1## wherein Q.sup.1 and Q.sup.2 are each independently a pyrylium, thiopyrylium, selenopyrylium, benzpyrylium, benzthiopyrylium or benzselenopyrylium nucleus, and R.sup.1 and R.sup.2 are each independently an aliphatic or cycloaliphatic group, can be prepared by reacting a squaric acid derivative of the formula: ##STR2## with a compound of the formula Q.sup.2 CH.sub.2 R.sup.2 in the presence of a base. The derivatives of Formula II may be prepared by condensing a 2,3,4,4-tetrahalocyclobut-2-en-1-one with a compound of the formula Q.sup.1 CH.sub.2 R.sup.1 in the presence of a base to produce a compound of the formula: ##STR3## wherein Q.sup.1 and R.sup.1 are as defined above, and X represents chlorine or bromine, and hydrolyzing the compound of Formula III. Alternatively, the derivatives of Formula II may be prepared by reacting a diester, monoacid chloride monoester or diacid chloride of squaric acid with a compound of the formula Q.sup.1 CH.sub.2 R.sup.Type: GrantFiled: May 6, 1991Date of Patent: July 27, 1993Assignee: Polaroid CorporationInventors: Donald A. McGowan, Paulina P. Garcia, John W. Lee, Thomas K. Spencer, Stephen J. Telfer, Michael J. Zuraw
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Patent number: 5227499Abstract: Squarylium compounds of the formula: ##STR1## in which: Q.sup.1 and Q.sup.2 are each a Chromophoric group having an unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens;R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group; andR.sup.3, R.sup.4 and R.sup.5 are each independently a hydrogen atom, or an aliphatic, cycloaliphatic, aromatic or heterocyclic group, or an electron-withdrawing group able to lower the electron density at the carbon atom to which it is attached, subject to the provisoes that:two of R.sup.3, R.sup.4 and R.sup.5 may form a divalent group of which a single atom is double bonded to the carbon atom to which the two groups are attached, or all three of R.sup.3, R.sup.4 and R.sup.Type: GrantFiled: November 20, 1991Date of Patent: July 13, 1993Assignee: Polaroid CorporationInventors: Donald A. McGowan, Mark R. Mischke, Stephen J. Telfer
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Patent number: 5227498Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an aliphatic, cycloaliphatic, aromatic or heterocyclic group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a cycloaliphatic or aromatic ring) are useful as near infra-red absorbers.Type: GrantFiled: November 20, 1991Date of Patent: July 13, 1993Assignee: Polaroid CorporationInventors: John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
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Patent number: 5227399Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.Type: GrantFiled: October 26, 1992Date of Patent: July 13, 1993Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Yves Girard, John W. Gillard, Laird A. Trimble, John Scheigetz, James A. Yergey, Yves Ducharme, Deborah A. Nicoll-Griffith, John H. Hutchinson
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Patent number: 5206387Abstract: There are disclosed compounds having the formula ##STR1## wherein n is 1-4; R is hydrogen, loweralkyl or loweralkylcarbonyl; R.sub.1 is hydrogen, loweralkyl, loweralkylcarbonyl, aryl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, oxygen-bridged arylloweralkyl, or oxygen-bridged diaryllowerallyl; A is a direct bond of (CHR.sub.3).sub.m, m being 1-3; X is hydrogen, loweralkyl, cycloalkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkylcarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR.sub.4 or --NR.sub.5 R.sub.6, R.sub.4 being hydrogen or loweralkyl, and R.sub.5 and R.sub.6 being independently hydrogen, loweralkyl or cycloalkyl; Y is O, S or NR.sub.7 ; and each R.sub.2, each R.sub.3 and R.sub.Type: GrantFiled: October 19, 1992Date of Patent: April 27, 1993Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Gregory M. Shutske, Richard C. Effland
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Patent number: 5198462Abstract: A novel heterocyclic amine derivative of the general formula: ##STR1## wherein a ring A and a ring B stand independently for an optionally substituted benzene ring, Z.degree. stands for O or S or ##STR2## stands for --CH.sub.2 --, X stands for O, S or NR.sup.1 wherein R.sup.1 stands for hydrogen atom or an alkyl group, Y stands for NH, O or (CH.sub.2).sub.n wherein n denotes 0 to 2, and R.sup.2 stands for an optionally substituted hydrocarbon group, or their salts.Type: GrantFiled: October 16, 1991Date of Patent: March 30, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Hideaki Natsugari, Hiroyuki Tawada, Hitoshi Ikeda
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Patent number: 5190573Abstract: Cyclohexenone oxime ethers ##STR1## where R.sup.1 is alkyl;A is substituted or unsubstituted alkylene or alkenylene, where methylene is replaced by an oxygen atom, a sulfur atom, a sulfoxyl group, a sulfonyl group or --NR.sup.a --,Z is phenyl or a 5- or 6-membered heteroaromatic structure;X is substituted or unsubstituted amino, nitro, cyano, halogen, alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbony or phenyl;n is 0 to 3, or 1 to 5 where X is halogen;R.sup.Type: GrantFiled: May 8, 1991Date of Patent: March 2, 1993Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Norbert Goetz, Albrecht Harreus, Bruno Wuerzer, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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Patent number: 5183904Abstract: Novel compounds and methods for the formation of disulfide linkages are presented. The novel compounds employed are substituted 2-iminothiolane hydrohalide linking agents of the following formula (I): ##STR1## wherein, X is halogen;R.sub.1 is COOR.sub.5 ; halogen; nitro; unsubstituted or halogenated C.sub.1-8 alkyl; unsubstituted or halogenated C.sub.1-8 alkoxy; unsubstituted or halogenated C.sub.2-8 alkenyl; unsubstituted or halogenated C.sub.2-8 alkynyl; unsubstituted C.sub.3-8 cycloalkyl; unsubstituted aryl; aryl substituted with 1 to 3 substituents selected from halogen, amino, unsubstituted or halogenated C.sub.1-8 alkyl, or unsubstituted or halogenated C.sub.1-8 alkoxy; unsubstituted heterocycle; or heterocycle substituted with 1 to 3 substituents selected from amino, halogen, unsubstituted or halogenated C.sub.1-8 alkyl, or unsubstituted or halogenated C.sub.1-8 alkoxy;each of R.sub.2, R.sub.3 and R.sub.4 is independently hydrogen or selected from the values of R.sub.1 ; orR.sub.1 and R.sub.Type: GrantFiled: November 20, 1991Date of Patent: February 2, 1993Assignee: Xoma CorporationInventors: Stephen F. Carroll, Dane A. Goff
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Patent number: 5149828Abstract: Tetrahydrothiopyran compound of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X and n are as defined in claim 1, are effective stabilizers for dyes and dye couplers in photographic layers. In particular, they provide protection from damage by light. They are preferably used in combination with a phenolic antioxidant.Type: GrantFiled: March 21, 1990Date of Patent: September 22, 1992Assignee: Ciba-Geigy AGInventors: Jean Rody, David G. Leppard
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Patent number: 5142054Abstract: Disclosed are new 1,3-dioxenones having the formulae ##STR1## in an optically pure state, a process for preparing same and the use thereof.Type: GrantFiled: February 12, 1991Date of Patent: August 25, 1992Assignee: Studiengesellschaft Kohle mbHInventors: Kurt Schaffner, Martin Demuth
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Patent number: 5132434Abstract: A substituted benzoyl derivative of the formula: ##STR1## wherein R is a lower alkyl group, or a phenyl group unsubstituted or substituted by a lower alkyl group, halogen atom or a lower alkoxy group;n is an integer of 2 or 3;m is an integer of from 0 to 6, and when m is an integer of from 2 to 6, the plurality of R may be the same or different from one another;l is an integer of 0, 1 or 2;X is a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower alkoxy group, or a lower haloalkyl group;Y is a hydrogen atom, a halogen atom, a nitro group, a lower alkyl group unsubstituted or substituted by a halogen atom or a lower alkoxy group, a lower alkoxy group, or a lower alkoxy carbonyl group; andZ is a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a lower alkoxy group, a lower alkylthio group, a lower haloalkylthio group, a lower alkylsulfinyl group, a lower haloalkylsulfinyl group, a lower alkylsulfonyl group, or a lower haloalkylsulfonyl group.Type: GrantFiled: January 3, 1990Date of Patent: July 21, 1992Assignee: Nissan Chemical Industries Ltd.Inventors: Junichi Watanabe, Yasuo Kondo, Masataka Hatanaka, Takashi Ikai, Koichi Suzuki, Tsutomu Nawamaki, Shigeomi Watanabe
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Patent number: 5114461Abstract: A 2-benzoylcyclic-1,3-dione derivative of the formula: ##STR1## wherein X represents methylene, oxygen, sulphur or --NR.sup.4 --, Y represents --C(R.sup.5) (R.sup.6)-- or oxygen, R.sup.1 represents hydrogen or alkyl optionally substituted by halogen or represents cycloalkyl, R.sup.2 represents hydrogen or R.sup.7 or R.sup.1 and R.sup.2 together represent alkylene, R.sup.3 represents halogen, hydroxy, carboxy, nitro, cyano or amino or carbamoyl (which may be substituted by one or two alkyl groups), alkoxycarbonyl, alkanoyl, or alkanoylamino, R, RO, RS, RSO or RSO.sub.2 in which R represents alkyl optionally substituted by halogen, R.sup.4 represents hydrogen or alkyl or alkoxycarbonyl, R.sup.5 represents hydrogen or alkyl or alkoxycarbonyl, R.sup.6 represents hydrogen or alkyl, R.sup.7 represents alkyl which may be substituted by halogen or alkylthio or by a group (R.sup.8).sub.n -phenyl-S-, or represents cycloalkyl or tetrahydrothiapyran-3-yl or represents a group (R.sup.8).sub.n -phenyl- in which R.sup.Type: GrantFiled: November 22, 1989Date of Patent: May 19, 1992Assignee: May & Baker LimitedInventors: Neil J. Geach, James Gilmour, Leslie R. Hatton, Philip H. G. Smith
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Patent number: 5101048Abstract: The present invention relates, by way of novel industrial products, to the .beta.-D-phenylthioxyloside compounds of the formula ##STR1## in which: X represents a sulfur atom or an oxygen atom;R.sub.1, R.sub.2 and R.sub.3, which are identical or different, each represent a hydrogen atom, a nitro group, a cyano group, a group --CO--R (in which R represents a C.sub.1 -C.sub.4 alkyl group or a trifluoromethyl group), an amino group, an acetamido group (NHCOCH.sub.3), a C.sub.1 -C.sub.4 alkoxy group, a trifluoromethyl group or a phenyl group substituted by one or more cyano, nitro or trifluoromethyl groups, it being possible for R.sub.1 and R.sub.2, taken together, to form, with the phenyl group to which they are bonded, a .beta.-naphthalenyl group which is unsubstituted or substituted by one or more cyano, nitro or trifluoromethyl groups; andY represents the hydrogen atom or an aliphatic acyl group.These compounds are useful as therapeutic agents, especially as venous antithrombotics.Type: GrantFiled: October 18, 1989Date of Patent: March 31, 1992Assignee: Fournier Industrie et SanteInventors: Jerzy Bajgrowicz, Patrice Renaut, Veronique Barberousse, Soth Samreth, Jean Millet, Francois Bellamy
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Patent number: 5100913Abstract: The present invention relates, by way of novel industrial products, to the sulfonylphenyl-.beta.-D-thioxyloside compounds of the formula ##STR1## in which: X is a sulfur atom or an oxygen atom;R is a C.sub.1 -C.sub.4 alkyl group, a substituted amino group NR.sub.1 R.sub.2 (where R.sub.1 and R.sub.2, which are identical or different, are each a C.sub.1 -C.sub.4 alkyl group, it being possible for R.sub.1 and R.sub.2, taken together, to form a piperidinyl or morpholinyl group with the nitrogen atom to which they are bonded) or a phenyl group which is unsubstituted or substituted in the para position by a cyano group or by a halogen atom; andY is the hydrogen atom or an aliphatic acyl group.These compounds are useful in therapeutics, especially as venous antithrombotics.Type: GrantFiled: March 25, 1991Date of Patent: March 31, 1992Assignee: Fournier Industrie et SanteInventors: Soth Samreth, Patrice Renaut, Jerzy Bajgrowicz, Jean Millet
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Patent number: 5091533Abstract: Compounds of the formula: ##STR1## where R.sup.2 contains certain aryls or heteroaryls are effective leukotriene inhibitors.Type: GrantFiled: March 12, 1990Date of Patent: February 25, 1992Assignee: Merck Frosst Canada, Inc.Inventors: Patrice C. Belanger, Claude Dufresne, Brian Fitzsimmons, deceased, Maryann Fitzsimmons, Heir, Yvan Guindon, Cheuk K. Lau, Joshua Rokach, John Schiegetz, Michel Therien, Robert N. Young
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Patent number: 5087288Abstract: A method of controlling plant growth is provided comprising applying to the plants or to a habitat thereof a herbicidally effective amount of a compound having the structure: ##STR1## wherein R.sup.1 is selected from the group consisting of carboxy, cyano, ester ##STR2## or amido ##STR3## wherein R.sup.2 is selected from the group consisting of a straight-chained alkyl group or a branched-chain alkyl group, of about 1 to 8 carbon atoms,R.sup.3 and R.sup.4 are selected from the group consisting of hydrogen, alkyl of about 1 to 8 carbon atoms, cycloalkyl of about 5 to 6 carbon atoms, and heterocyclyl of about 5 to 6 carbon and hetero atoms, or,R.sup.3 and R.sup.4 taken together with the nitrogen atoms to which they are attached form a heterocyclyl group having 5 to 6 carbon and hetero atoms. Also, novel compounds having the above structure are provided.Type: GrantFiled: September 17, 1990Date of Patent: February 11, 1992Assignee: Eastman Kodak CompanyInventor: Thomas R. Welter
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Patent number: 5074903Abstract: Cyclohexenone derivative of the formula ##STR1## where A is oxygen or NOR.sup.8, where R.sup.8 is alkyl, alkenyl, alkynyl, haloalkyl or haloalkenyl, chlorothienyl or alkoxyalkylB is O, S, SO or SO.sub.2,X is hydrogen or methoxycarbonyl,R.sup.1 is hydrogen, carbonylalkyl, benzoyl or a cation,R.sup.2 is alkyl,R.sup.3 and R.sup.4 are hydroxyl, chlorine, bromine, thioalkylcarboxyl, thiocarbonylalkyl, alkylcarbonyloxy, alkoxy, or alkylthio, or R.sup.3 and R.sup.4 together epoxy,R.sup.5 and R.sup.6 are hydrogen or methyl or R.sup.5 and R.sup.6 are together methyleneoxyethylene, andR.sup.7 is hydrogen or methyl,and herbicides containing these compounds.Type: GrantFiled: August 13, 1990Date of Patent: December 24, 1991Assignee: BASF AktiengesellschaftInventors: Dieter Jahn, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Bruno Wuerzer, Norbert Meyer, Johann Jung, Wilhelm Rademacher
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Patent number: 5071871Abstract: New benz[b]pyranes and pyranopyridines of formula I, ##STR1## wherein the significances of substituents V, T, W, R.sub.3 to R.sub.5, R.sub.9, R.sub.10, m, X, Y and Z are given in claim 1 and their N-oxides and their salts and their use in the treatment of raised blood pressure in the treatment of vascular disorders and other disorders in which a reduction in tension of the smooth muscles is therapeutically useful, as well as in the treatment of hair loss and baldness. Further the compounds are useful in the treatment of asthma and obstructive disorders of the respiratory system as well as in the prophylactic treatment of obstructive or inflammatory airways disease, for example asthma, as well as novel pharmaceutical compositions comprising said K.sup.+ channel activators suitable for such use.Type: GrantFiled: July 10, 1990Date of Patent: December 10, 1991Assignee: Sandoz Ltd.Inventors: Stefan Blarer, John Morley, Ian D. Chapman
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Patent number: 5049673Abstract: The present invention discloses a new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths. The new fluorescent indicator dyes combine at least one tricyclic chromophore with a tetracarboxylate parent CA.sup.2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium.sup.2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium.sup.2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA.sup.2+ ] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.Type: GrantFiled: October 30, 1987Date of Patent: September 17, 1991Assignee: The Regents of the University of CaliforniaInventors: Roger Y. Tsien, Akwasi Minta
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Patent number: 5041565Abstract: Novel hydrazinocarbonyloxylabdanes, intermediates and processes for the preparation thereof, and a method for treating cardiac failure utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: August 30, 1989Date of Patent: August 20, 1991Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Raymond W. Kosley, Jr., Gerard J. O'Malley
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Patent number: 5032312Abstract: Compounds of the formula ##STR1## wherein R.sup.1 denotes a group R.sup.3 or R.sup.3 --A.sup.4 --Z.sup.3 -- and R.sup.2 denotes a group R.sup.4 or --Z.sup.4 --A.sup.5 --R.sup.4 ; m and n each individually stand for the number 0 or 1; A.sup.1, A.sup.2, A.sup.3, A.sup.4 and A.sup.5 each independently represent unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen, trans-1,4-cyclohexylene in which optionally 2 non-adjacent methylene groups are replaced by oxygen and/or sulphur, 1-cyano-trans-1,4-cyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6-diyl; Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4 each independently signify a single covalent bond, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2, --C.tbd.C--, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 -- or the trans form of --CH.dbd.CH--CH.sub.2 O-- or --OCH.sub.2 --CH.dbd.CH--; R.sup.3 and R.sup.Type: GrantFiled: March 2, 1990Date of Patent: July 16, 1991Assignee: Hoffmann-La Roche Inc.Inventor: Stephen Kelly
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Patent number: 5026877Abstract: Disclosed are new 1,3-dioxenones having the formulae ##STR1## in an optically pure state, a process for preparing same and the use thereof.Type: GrantFiled: May 10, 1989Date of Patent: June 25, 1991Assignee: Studiengesellschaft Kohle mbHInventors: Kurt Schaffner, Martin Demuth
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Patent number: 5013849Abstract: Certain new chemical compounds are derivatives of 4H-thiopyran-1,1-dioxides, and are useful as electron-transport agents in electrophotographic elements.Type: GrantFiled: December 22, 1989Date of Patent: May 7, 1991Assignee: Eastman Kodak CompanyInventors: Norman G. Rule, Teh-Ming Kung