Plural Chalcogens Bonded Directly To The Hetero Ring Patents (Class 549/417)
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Patent number: 5844000Abstract: This invention relates to novel propenone oxime ethers, methods of preparing them and pharmaceutical compositions containing them. The compounds have the formula: ##STR1## wherein R.sup.1 is H, or glucuronide;R.sup.2 and R.sup.3 are independently H or methyl;R.sup.4 is 0, or glucuronide, andn is 0 or 1, provided that when R.sup.1 is H, n is 1.Type: GrantFiled: June 12, 1997Date of Patent: December 1, 1998Assignee: SanofiInventors: William Brian, Brian Folk, Juan Shi, Gerard Fabre, Claude Tronquet
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Patent number: 5840751Abstract: The present invention relates to novel 5,6-dihydropyrone derivatives and related structures which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The 5,6-dihydropyrone derivatives are useful in the development of therapies for the treatment of bacterial and viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of multifunctionalized 5,6-dihydropyrones and of related structures.Type: GrantFiled: October 12, 1994Date of Patent: November 24, 1998Assignee: Warner-Lambert CompanyInventors: Edmund Lee Ellsworth, Elizabeth Lunney, Bradley Dean Tait
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Patent number: 5811028Abstract: A 2H-5,6-optically active dihydropyran derivative represented by the general formula (I) or (I'): ##STR1## wherein Rf represents a fluoroalkyl group having 1 or 2 carbon atoms; a liquid crystal composition and a liquid crystal device comprising the derivative; and a racemic mixture comprising at least one type of the derivative. The derivative is a novel compound which exhibits the liquid crystal property by itself or can be used as an excellent dopant providing a high speed response to a composition comprising it even when the compound does not exhibit the liquid crystal property by itself. The derivative also exhibits a large spontaneous polarization.Type: GrantFiled: August 13, 1997Date of Patent: September 22, 1998Assignee: Kashima Oil CompanyInventors: Tatsushi Ishizuka, Mitsunori Takeda, Masaaki Namekawa, Keizou Itoh
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Patent number: 5808111Abstract: Novel acitretinamide compounds which are soluble and stable in water and useful in aqueous delivery systems, particularly to treat cancer, are provided. The novel acitretinamide compounds, 1-(D-glucopyranosyl)acitretinamide, 1-(D-glucopyranuronosyl)acitretinamide and the metal salts thereof, are hereinafter collectively referred to as the "acitretinamide compounds". The invention also relates to novel methods of making the acitretinamide compounds.Type: GrantFiled: May 6, 1997Date of Patent: September 15, 1998Assignee: The Ohio State Research FoundationInventor: Robert W. Curley, Jr.
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Patent number: 5801257Abstract: Novel anthracycline derivatives have now been produced, which exhibit higher antitumor activities and lower toxicities than those of daunomycin, adriamycin etc. that have been clinically used as anticancer agents. That is, a daunomycinone or adriamycinone derivative represented by the general formula (I): ##STR1## wherein R is a hydrogen atom or a hydroxyl group, and 7-O-(2,6-dideoxy-6,6,6-trifluoro-.alpha.-L-lyxo-hexopyranosyl)adriamycinon e derivative which is an adriamycinone derivative represented by formula (II): ##STR2## have now been newly synthesized. The novel anthracycline derivatives having the general formula (I) and formula (II), respectively, show excellent anticancer or antitumor activities and are of low toxicities. These novel compounds are very useful as anticancer or antitumor agents and are expected to be useful for the therapeutic treatments of a variety of cancers and tumors, similarly to daunomycin or adriamycin.Type: GrantFiled: October 20, 1997Date of Patent: September 1, 1998Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
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Patent number: 5795981Abstract: 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: December 16, 1996Date of Patent: August 18, 1998Assignee: Polaroid CorporationInventors: John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
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Patent number: 5789605Abstract: Synthetic methods for lactone-containing compounds such as the discodermolides are provided, as are compounds which mimic the chemical and/or biological activity thereof, and methods and intermediates useful in their preparation.Type: GrantFiled: December 3, 1996Date of Patent: August 4, 1998Assignee: Trustees of the University of PennsylvaniaInventors: Amos B. Smith, III, Yuping Qiu, Michael Kaufman, Hirokaza Arimoto, David R. Jones, Kaoru Kobayashi
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Patent number: 5777136Abstract: A process for the preparation of compounds having the formula ##STR1## wherein: R is a methoxy or thiomethyl group;R.sub.1 is a .beta.-D-glycopyranosyloxy or6-deoxygalactopyranosyloxy residue; andR.sub.2 is a C.sub.1 -C.sub.7 alkyl groupwhich process comprises reacting a protected material selected from the group consisting of derivatives of 1-fluoroglucose and 1-fluorofucose with a compound having the formula ##STR2## wherein R and R.sub.2 are as defined above to form a crude reaction product containing at least one compound of formula (I).Type: GrantFiled: February 7, 1997Date of Patent: July 7, 1998Assignee: Indena S.p.A.Inventor: Ezio Bombardelli
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Patent number: 5767100Abstract: In accordance with this invention novel compounds are provided that are selected from saturated and unsaturated pyrans and furans substituted with at least a phosphonate group and a heterocyclic base. These compounds are useful as antiinfectives, flame retardants, diagnostic oligonucleotides and immunogens.Type: GrantFiled: March 13, 1996Date of Patent: June 16, 1998Assignee: Gilead Sciences, Inc.Inventors: Petr Alexander, Ernest J. Prisbe
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Patent number: 5767094Abstract: A propiophenone derivative the formula ?I!: ##STR1## wherein R' is a lower alkanoyl group and R" is a hydrogen atom, or R' is a hydrogen atom and R" is a lower alkoxycarbonyl group, or a pharmaceutically acceptable salt thereof. Said compounds have excellent hypoglycemic activity so that they are useful in the prophylaxis or treatment of diabetes.Type: GrantFiled: November 7, 1996Date of Patent: June 16, 1998Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Kenji Tsujihara, Kunio Saito, Mitsuya Hongu, Mamoru Matsumoto, Kozo Oka
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Patent number: 5750733Abstract: The present invention relates to novel hydroxy-containing alkyl glycamide surfactants and detergent composition comprising said surfactants. Since they surprisingly provide low foam, these surfactants can be used as cleansing surfactants in applications where low foaming is desirable.Type: GrantFiled: August 6, 1996Date of Patent: May 12, 1998Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Robert Vermeer, Bijan Harichian
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Patent number: 5746933Abstract: A lubricating oil for refrigerating machines comprises polyoxyalkylene compounds represented by the formula (I): ##STR1## Wherein A is a residue obtained from a compound which has both a heterocyclic ring having an ether linkage therein and hydroxyl groups by eliminating the hydroxyl groups from the compound; R.sup.1 and R.sup.2 are each an alkylene group; R.sup.3 is an alkyl group; R.sup.4 is hydrogen atom or an alkyl group; a and b are each a positive integer and l, m, and n are each an integer of 0 or more; and a.multidot.1+b.multidot.m=2 to 100 and l+m+n=2 to 20; further,the polyoxyalkylene compounds have a hydroxyl value ranging from 0 to 30.0 mgKOH/g and satisfies the following formula (1)0.5<p/(p+q)<1.0 (1)wherein p is the number of butylene groups represented by R.sup.1 and R.sup.2, and q is the number of all alkylene groups excluding the butylene groups.Type: GrantFiled: November 3, 1995Date of Patent: May 5, 1998Assignee: Nippon Oil Co., Ltd.Inventors: Noboru Ishida, Umekichi Sasaki, Katsuya Takigawa, Satoshi Suda
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Patent number: 5733927Abstract: A method for improving the solubility of a salt of a glucopyranose derivative of formula (I) ##STR1## wherein R.sup.2, R.sup.3 and Y.sup.+ are as defined herein. The compound of formula (I) possesses enhanced activity for cellular immunity, and therefore is useful as an enhancing agent for immunity. It also possesses inducing activity for TNF, IL-1, and IFN, and therefore is useful as an anti-tumor agent.Type: GrantFiled: June 5, 1995Date of Patent: March 31, 1998Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Katsuhiro Imaki, Shinsuke Hashimoto, Hirohisa Wakatsuka
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Patent number: 5719130Abstract: Novel anthracycline derivatives have now been produced, which exhibit higher antitumor activities and lower toxicities than those of daunomycin, adriamycin etc. that have been clinically used as anticancer agents. That is, a daunomycinone or adriamycinone derivative represented by the general formula (I): ##STR1## wherein R is a hydrogen atom or a hydroxyl group.Type: GrantFiled: September 9, 1996Date of Patent: February 17, 1998Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
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Patent number: 5719291Abstract: Compounds of the formula ##STR1## which have antifungal activity.Type: GrantFiled: May 3, 1995Date of Patent: February 17, 1998Assignee: Hoffmann-La Roche Inc.Inventors: Yuhko Aoki, Hiromichi Kotaki, Kazunao Masubuchi, Toru Okuda, Nobuo Shimma, Takuo Tsukuda, Isao Umeda
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Patent number: 5714484Abstract: Cysteine protease inhibitors which deactivate the protease by covalently bonding to the cysteine protease and releasing the enolate of a 1,3-dicarbonyl (or its enolic form). The cysteine protease inhibitors of the present invention accordingly comprise a first portion which targets a desired cysteine protease and positions the inhibitor near the thiolate anion portion of the active site of the protease, and a second portion which covalently bonds to the cysteine protease and irreversibly deactivates that protease by providing a carbonyl or carbonyl-equivalent which is attacked by the thiolate anion of the active site of the cysteine protease to sequentially cleave a .beta.-dicarbonyl enol ether leaving group.Type: GrantFiled: June 7, 1995Date of Patent: February 3, 1998Assignee: Prototek, Inc.Inventors: Mary P. Zimmerman, Robert E. Smith, Mark Becker
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Patent number: 5712254Abstract: Sialic acid derivatives represented by the general formula (I): ##STR1## wherein R.sup.1 is a steroidal compound residue; R.sup.2 is H or alkyl;R.sup.3 is alkyl; ##STR2## wherein each of R.sup.6 and R.sup.7 is H, alkyl or the like and I is an integer of 0 to 6; or the like;X is O or S;R.sup.4 is H or acyl; and R.sup.5 is R.sup.14 O-- (R.sup.14 is H or acyl) or R.sup.15 NH--(R.sup.15 is acyl or the like);their salts, hydrates or solvates are provided.Sialic acid derivatives of the present invention are expected to be effective medicines for the prevention and therapy of senile dementia including Alzheimer's disease and the like, because they increase ChAT activity in cholinergic neurons.Type: GrantFiled: December 23, 1994Date of Patent: January 27, 1998Assignee: Mitsubishi Chemical CorporationInventors: Haruyuki Chaki, Naoko Ando, Yasuhiro Morinaka, Ken-Ichi Saito, Tomoko Yugami, Rie Yoshida
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Patent number: 5698137Abstract: A 2H-5,6-optically active dihydropyran derivative represented by the general formula (I) or (I'): ##STR1## wherein Rf represents a fluoroalkyl group having 1 or 2 carbon atoms; a liquid crystal composition and a liquid crystal device comprising the derivative; and a racemic mixture comprising at least one type of the derivative. The derivative is a novel compound which exhibits the liquid crystal property by itself or can be used as an excellent dopant providing a high speed response to a composition comprising it even when the compound does not exhibit the liquid crystal property by itself. The derivative also exhibits a large spontaneous polarization.Type: GrantFiled: April 15, 1996Date of Patent: December 16, 1997Assignee: Kashima Oil CompanyInventors: Tatsushi Ishizuka, Mitsunori Takeda, Masaaki Namekawa, Keizou Itoh
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Patent number: 5663377Abstract: The present invention provides breast cancer chemopreventive arylamide analogues of retinoic acid, more particularly C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide that resist both .beta.-glucuronidase mediated enzymatic hydrolysis as well as acid catalyzed hydrolysis. Specifically, the drugs include 4-(retinamido)phenyl-C-glucuronide; 4-(retinamido)phenyl-C-glucoside; 4-(retinamido)benzyl-C-xyloside; 4-(retinamido)benzyl-C-glucoside; 4-(retinamido)benzyl-C-glucuronide; and 4-(retinamido)phenyl-C-xyloside.Type: GrantFiled: June 6, 1995Date of Patent: September 2, 1997Assignee: The Ohio State Research FoundationInventors: Robert W. Curley, Jr., Michael J. Panigot
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Patent number: 5656750Abstract: 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: June 6, 1995Date of Patent: August 12, 1997Assignee: Polaroid CorporationInventors: Richard M. Allen, Peter K. Chu
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Patent number: 5648379Abstract: 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: October 19, 1994Date of Patent: July 15, 1997Assignee: Biota Scientific Management Pty., Ltd.Inventors: Laurence Mark Von Itzstein, Wen-Yang Wu, Tho Van Phan, Basil Danylec, Betty Jin, Peter Malcolm Colman, Joseph Noozhumurry Varghese
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Patent number: 5646179Abstract: The invention relates to novel .gamma.-pyrones, .gamma.-pyridones and .gamma.-thiopyrones and their use as medicaments against viral diseases, preferably for the treatment of retroviral diseases, comprising compounds of the formula (I), in which R.sub.1 and R.sub.2 stand for hydrogen, a branched-chain or unbranched-chain C.sub.1 to C.sub.26, preferably C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.26 alkenyl or C.sub.1 to C.sub.26 alkinyl group or combinations thereof; R.sub.3 stands for a branched-chain or unbranched-chain C.sub.1 to C.sub.26 alkyl group; and R.sub.4 stands for a C.sub.3 to C.sub.26 cycloalkyl, branched-chain or unbranched-chain alkyl, alkenyl or alkinyl group. The hydrogen atoms of the methylenic group in R.sub.1, R.sub.2 and R.sub.4 may be substituted by O alkyl (C.sub.1 to C.sub.6), O acyl, O aryl, O aralkyl and alkyl (C.sub.1 to C.sub.6) groups, and in R.sub.4 also by halogenated groups, oxo groups and hydroxylic groups with double links.Type: GrantFiled: December 12, 1995Date of Patent: July 8, 1997Assignees: Analyticon Gesellschaft fur Chemische Analytik und Consulting GmbH, Diagen Institut fur Molekularbiologische Diagnostik GmbHInventors: Lutz Muller-Kuhrt, Andreas Immelmann
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Patent number: 5633089Abstract: There is provided a lubricant which is produced by dissolving a sorbitan ester compound in a solvent such as hexane or toluene. In the sorbitan ester compound, at least one of hydroxyl groups of 1,5-sorbitan is linked by ester linkage to a perfluoro polyether having a terminal carboxyl group and at least an other hydroxyl group is linked by ester linkage to a hydrocarbon having a terminal carboxyl group. There is also provided a thin magnetic metal film type magnetic recording medium or a coated magnetic recording medium in which the above lubricant is held on the surface of a magnetic layer. The lubricant exhibits superior lubricating effects under all conditions and is capable of maintaining the lubricating effects for prolonged time. Consequently, the magnetic recording medium which has the lubricant held on the magnetic layer exhibits superior running durability and resistance against abrasion.Type: GrantFiled: September 22, 1995Date of Patent: May 27, 1997Assignee: Sony CorporationInventor: Hirofumi Kondo
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Patent number: 5631389Abstract: The present invention relates to a new class of carbohydrate based nonionic surfactant, i.e., alkyl and alkenyl glycasuccinimide, and a process for their manufacture.Type: GrantFiled: April 30, 1996Date of Patent: May 20, 1997Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Robert Vermeer, Van Au, Bijan Harichian
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Patent number: 5627290Abstract: The invention pertains to 2,7-Deoxy-7-fluoro-2,3-didehydrosialic acid and an intermediate thereof which are useful for developing practical drugs, such as an antiviral agent, a preventing agent for viral diseases, etc. and for a clinical application. In addition, they are also useful as a carcinostatic agent and an immunomodulation agent.Type: GrantFiled: January 26, 1996Date of Patent: May 6, 1997Assignee: Daikin Industries, Ltd.Inventors: Takao Iida, Yutaka Ohira
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Patent number: 5627194Abstract: Novel guanidino-substituted compounds are described having the following general formula (I): ##STR1## in which X may be carbon, oxygen, nitrogen or sulfur; R.sub.1 may be H, OH, linear or branched lower alkyl, lower alkoxy, lower (alkyl-substituted alkoxy), lower alkyl-amine, lower alkyl-thio, hydroxy substituted lower alkoxy, lower alkoxy-alkoxy substituted lower alkoxy, hydroxy substituted lower alkyl-amine, alkoxy substituted lower alkyl-amine and terminally guanidino-substituted linear of branched lower alkyl, lower alkoxy, lower (alkyl-substituted alkoxy), lower alkyl-amine or lower alkyl-thio; and R.sub.2 and R.sub.3 are independently one of linear or branched lower alkyl, alkoxy, alkyl-substituted alkoxy and alkylamine.These compounds have been found to inhibit effectively herpesvirus replication. Particularly preferred compounds in accordance with formula (I) for this purpose are guanidino-substituted sugar derivatives.Type: GrantFiled: October 14, 1994Date of Patent: May 6, 1997Assignee: Allelix Biopharmaceuticals Inc.Inventors: Sumanas Rakhit, Abdelmalik Slassi
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Patent number: 5618775Abstract: Mixtures of optically active cyclohexenone oxime ethers having R- and S-configuration in the oxime ether moiety of the formula I ##STR1## (R.sup.1 =C.sub.1 -C.sub.6 -alkyl; ##STR2## X=C.sub.1-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl; m=0-3 or 1-4 where all X's are halogen;n=0-3 or 1-5 where all X's are halogen;R.sup.2 =C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl, substituted or unsubstituted C.sub.5 -C.sub.7 -cycloalkenyl, substituted or unsubstituted 5-membered saturated heterocyclic structure, substituted or unsubstituted 6- or 7-membered heterocyclic structure, substituted or unsubstituted 5-membered heteroaromatic structure, substituted or unsubstituted phenyl or pyridyl)and their agriculturally useful salts and esters with C.sub.1 -C.sub.10 -carboxylic acids and inorganic acids.Type: GrantFiled: August 11, 1994Date of Patent: April 8, 1997Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Wolfgang Ladner, Helmut Walter, Karl-Otto Westphalen, Uwe Kardorff, Matthias Gerber
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Patent number: 5602262Abstract: A process for producing intermediate compounds 2-deoxy 2,2-difluoro-.beta.-D-ribo-pentopyranose (III) from 3,3-difluoro-4,5,6-O-trihydroxy-5,6-O-(1-ethylpropylidene)hexene (I). The process of preparing intermediate compound (I) involves reacting D-glyceraldehyde pentanide with an organometallic complex of 3-bromo-3,3-difluoropropene. The process of preparing intermediate compound (III) involves ozonolysis and then hydrolysis. The intermediate compounds (I) and (III) are used in the preparation of 2'-deoxy-2',2'-difluorocytidine which is an antiviral agent.Type: GrantFiled: February 3, 1995Date of Patent: February 11, 1997Assignee: Eli Lilly and CompanyInventor: David D. Wirth
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Patent number: 5599915Abstract: Sialyl Lewis.sup.x mimetic compounds are disclosed that are free of sialyl groups and glycosidically-linked fucosyl groups. These compounds exhibit about the same inhibition of selectin-medicated cellular adhesion as does sialyl Lewis.sup.x itself.Type: GrantFiled: March 21, 1995Date of Patent: February 4, 1997Assignee: The Scripps Research InstituteInventors: Chi-Huey Wong, Tetsuya Kajimoto
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Patent number: 5599953Abstract: The present invention provides breast cancer chemopreventive arylamide analogues of retinoic acid, more particularly C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide and N-glycoside analogue of retinoyl .beta.-glucuronide that resist both .beta.-glucuronidase mediated enzymatic hydrolysis as well as acid catalyzed hydrolysis. Specifically, the drugs include 4-(retinamido)phenyl-C-glucuronide; 4-(retinamido)phenyl-C-glucoside; 4-(retinamido)benzyl-C-xyloside; 4-(retinamido)benzyl-C-glucoside; 4-(retinamido)benzyl-C-glucuronide; 4-(retinamido)phenyl-C-xyloside, 1-(B-D-glucopyranosyl) retinamide and 1-(D-glucopyranosyluronosly) retinamide. The invention also relates to a method for making such drugs.Type: GrantFiled: May 26, 1995Date of Patent: February 4, 1997Assignee: The Ohio State Research FoundationInventors: Robert W. Curley, Jr., Michael J. Robarge
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Patent number: 5574000Abstract: Cyclohexenone oxime ethers of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, A is substituted or unsubstituted C.sub.4 -alkylene or C.sub.4 -alkenylene,X is nitro, cyano, halogen, C.sub.1 -C.sub.4 -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 benzyloxycarbonyl and/or phenyl,n is from 0 to 3 or from 1 to 5 when X is halogen,R.sup.2 is C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -alkythio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.Type: GrantFiled: November 17, 1994Date of Patent: November 12, 1996Assignee: BASF AktiengesellschaftInventors: Juergen Kast, Dieter Kolassa, Norbert Meyer, Ulrich Schirmer, Albrecht Harreus, Jochen Wild, Karl-Otto Westphalen, Bruno Wuerzer
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Patent number: 5574177Abstract: The present invention provides breast cancer chemopreventive arylamide analogues of retinoic acid, more particularly C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide that resist both .beta.-glucuronidase mediated enzymatic hydrolysis as well as acid catalyzed hydrolysis. Specifically, the drugs include 4-(retinamido)phenyl-C-glucuronide; 4-(retinamido)phenyl-C-glucoside; 4-(retinamido)benzyl-C-xyloside; 4-(retinamido)benzyl-C-glucoside; 4-(retinamido)benzyl-C-glucuronide; and 4-(retinamido)phenyl-C-xyloside.Type: GrantFiled: October 7, 1994Date of Patent: November 12, 1996Assignee: The Ohio State Research FoundationInventors: Robert W. Curley, Jr., Michael J. Panigot
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Patent number: 5563250Abstract: The present invention provides cleavable conjugates whose linkers contain a labile bond that is cleavable under a variety of mild conditions, including weakly acidic. Since the agent may be bonded directly to the linker, cleavage can result in release of native agent. The invention also provides methods for producing cleavable conjugates. Preferred agents include drugs, toxins, biological response modifiers, radiodiagnostic compounds, radiotherapeutic compounds, and derivatives thereof. The targeting molecule employed in the invention may be an intact molecule, a fragment thereof, or a functional equivalent thereof. In a particularly preferred embodiment, the targeting molecule is a monoclonal antibody directed towards a tumor-associated antigen in man. The invention further provides methods for delivering to the cytoplasm of a target cell an agent free of its targeting molecule carrier.Type: GrantFiled: May 13, 1994Date of Patent: October 8, 1996Assignee: NeoRx CorporationInventors: Mark D. Hylarides, Ananthachari Srinivasan, Jeffrey N. Fitzner, Vivekananda M. Vrudhula
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Patent number: 5554771Abstract: The present invention relates to 2-deoxy-N-acetylneuraminic acid derivatives and methods for their preparation.Type: GrantFiled: August 16, 1995Date of Patent: September 10, 1996Assignee: G. D. Searle & Co.Inventors: Chi-Huey Wong, William J. Hennen
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Patent number: 5536850Abstract: The present invention relates to a novel substance DC114-A1 represented by the following formula (I): ##STR1##Type: GrantFiled: March 1, 1995Date of Patent: July 16, 1996Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Hirofumi Nakano, Noboru Fujii, Tamio Mizukami, Youichi Uosaki, Katsunori Kita, Eiji Kobayashi
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Patent number: 5523320Abstract: N-methyldeacetylcolchiceinamide derivatives represented by the formula ##STR1## wherein R denotes a residue obtained by removing COOH from a C.sub.3 -C.sub.7 sugar carboxylic acid, and hydroxyl groups present in the residue may properly be protected with a protecting group for a hydroxyl group.The N-methyldeacetylcolchiceinamide derivatives have less toxicity and strong effect for inhibiting proliferation of tumor cells, and are expected to be used as a carcinostatic.Type: GrantFiled: January 3, 1995Date of Patent: June 4, 1996Assignee: Ohgen Research Laboratories, Ltd.Inventor: Kiyoshi Akiyama
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Patent number: 5516792Abstract: The present invention provides breast cancer chemopreventive arylamide analogues of retinoic acid, more particularly C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide and N-glycoside analogue of retinoyl .beta.-glucuronide that resist both .beta.-glucuronidase mediated enzymatic hydrolysis as well as acid catalyzed hydrolysis. Specifically, the drugs include 4-(retinamido)phenyl-C-glucuronide; 4-(retinamido)phenyl-C-glucoside; 4-(retinamido)benzyl-C-xyloside; 4-(retinamido)benzyl-C-glucoside; 4-(retinamido)benzyl-C-glucuronide; 4-(retinamido)phenyl-C-xyloside, 1-(B-D-glucopyranosyl) retinamide and 1-(D-glucopyranosyluronosly) retinamide. The invention also relates to a method for making such drugs.Type: GrantFiled: September 30, 1994Date of Patent: May 14, 1996Assignee: Ohio State Research FoundationInventors: Robert W. Curley, Jr., Michael J. Robarge
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Patent number: 5496943Abstract: Disclosed is a novel heterocyclic compound selected from the group consisting of the compounds [IV] to [VII], [IX] and [X]. The heterocyclic compound is useful for reactive materials in chemical industry. A process for producing the heterocyclic compound is also disclosed.Type: GrantFiled: March 13, 1992Date of Patent: March 5, 1996Assignee: Nippon Paint Co., Ltd.Inventors: Otohiko Tsuge, Taizo Hatta, Satoshi Urano, Noriyuki Tsuboniwa, Ryuzo Mizuguchi
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Patent number: 5486623Abstract: A class of cysteine protease inhibitors which inactivate a cysteine protease by covalently bonding to the protease and releasing a heterocyclic leaving group is presented. The cysteine protease inhibitors of the present invention comprise a first portion which targets a desired cysteine protease and positions the inhibitor near the thiolate anion portion of the active site of the protease, and a second portion which covalently bonds to the cysteine protease and irreversibly deactivates that protease by providing a carbonyl or carbonyl-equivalent which is attacked by the thiolate anion of the active site of the cysteine protease to sequentially cleave a heterocyclic leaving group. The heterocyclic leaving group of the protease inhibitor is of the formula: --O-- Het, where Het is a heterocycle having 4-7 atoms in the ring, with at least one of the heterocycle atoms being N, O or S.Type: GrantFiled: December 8, 1993Date of Patent: January 23, 1996Assignee: Prototek, Inc.Inventors: Mary P. Zimmerman, Robert E. Smith
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Patent number: 5482966Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene or a heteroaryl diradical;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.sup.2 --A.sup.3 -- which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.Type: GrantFiled: June 13, 1994Date of Patent: January 9, 1996Assignees: Zeneca Limited, Zeneca Pharma S.A.Inventors: Thomas G. C. Bird, Patrick Ple
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Patent number: 5453439Abstract: The invention concerns hydroxylamine derivatives of the formula I ##STR1## wherein R.sup.4 is hydrogen, carbamoyl, (1-4C)alkyl, (2-5C)alkanoyl, N-(1-4C)alkylcarbamoyl, N,N-di-(1-4C)alkylcarbamoyl, benzoyl or phenylsulphonyl;R.sup.5 includes hydrogen, (1-4C)alkyl and (2-5C)alkanoyl;R.sup.6 is hydrogen, (1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl;R.sup.7 is hydrogen or (1-4C)alkyl;Ar.sup.1 is phenylene;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl, thiazolediyl, oxazolediyl, thiadiazolediyl or oxadiazolediyl;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.sup.2 --A.sup.3 -- which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is independently (1-3C)alkylene and X.sup.Type: GrantFiled: February 8, 1993Date of Patent: September 26, 1995Assignees: Zeneca Limited, Zeneca-Pharma S.A.Inventor: Patrick Ple
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Patent number: 5426111Abstract: Compounds of formula ##STR1## Ar is selected from (a) phenyl, (b) phenyl substituted with one or more groups selected from halogen, cyano, alkyl, haloalkyl, alkoxy, and alkoxycarbonyl, (c) furyl, (d) furyl substituted with one or more groups selected from halogen, alkyl, and alkoxy, (e) pyridyl, (f) pyridyl substituted with one or more groups selected from halogen, alkyl, and alkoxy, (g) thienyl, and (h) thienyl substituted with one or more groups selected from halogen, alkyl, and alkoxy; L is selected from alkylene of one to three carbon atoms, alkenylene of two to three carbon atoms, and alkynylene of two to three carbon atoms, and ##STR2## wherein p is an integer of 1 to 4, inclusive, and R.sup.4 is selected from the group consisting of hydrogen, alkyl of one to four carbon atoms, halogen, haloalkyl of one to four carbon atoms, and alkoxy of one to six carbon atoms;R.sup.1 is alkyl; R.sup.2 is hydrogen or alkyl; m is 1 or 2; Z is oxygen or CHOR.sup.Type: GrantFiled: November 23, 1994Date of Patent: June 20, 1995Assignee: Abbott LaboratoriesInventors: Joseph F. Dellaria, James D. Ratajczyk, Clint D. W. Brooks, Anwer Basha
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Patent number: 5414096Type: GrantFiled: February 22, 1994Date of Patent: May 9, 1995Assignee: Bristol-Myers Squibb Co.Inventors: Joseph A. Tino, Gregory S. Bisacchi, Saleem Ahmad
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Patent number: 5414000Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is a substituted purinyl group including pharmaceutically acceptable salts are useful as antiviral agents.Type: GrantFiled: February 22, 1994Date of Patent: May 9, 1995Assignee: Bristol-Myers Squibb Co.Inventors: Joseph A. Tino, Gregory S. Bisacchi, Saleem Ahmad
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Patent number: 5412118Abstract: The present invention relates to liquid and powdered surfactant compositions comprising alkyl (alkyl glycosid) uronamide compounds. Compositions comprising these compounds have been found to provide significant benefits such as stable, aqueous foam (in shampoo compositions) and enhanced detergency and oily soil removal (in detergent compositions).Type: GrantFiled: October 12, 1993Date of Patent: May 2, 1995Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Robert Vermeer, Bijan Harichian, Van Au
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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: 5393764Abstract: The compounds of the present invention comprise substituted phenolic thioethers represented by the formula ##STR1## wherein: R.sup.1 and R.sup.2 are the same or different and independently represent tert-alkyl or phenyl; R.sup.3 represents hydrogen or alkyl; X represents --(CH.sub.2).sub.w --B--(CH.sub.2).sub.y -- wherein B represents O, S, or CH.sub.2 and w and y can each independently be an integer from 0 to 3 with the proviso that the sum of w+y is equal to or less than 3; A represents O or S(O).sub.n wherein n is 0, 1 or 2; p is an integer from 1 to 4; and R represents alkyl; OH; OR.sup.4 wherein R.sup.4 is alkyl of 1 to 4 carbon atoms; NR.sup.5 R.sup.6 wherein R.sup.5 is hydrogen or alkyl and R.sup.6 is hydrogen, alkyl, heterocyclealkyl in which the hetercyclic ring may optionally be substituted; cycloalkyl; substituted cycloalkyl; phenyl; substituted phenyl; phenylalkyl; or substituted phenylalkyl; or NR.sup.5 R.sup.6 together form a heterocyclic ring which may optionally be substituted; or R is (CH.Type: GrantFiled: August 25, 1993Date of Patent: February 28, 1995Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 5376680Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 is hydrogen, (1-4C)alkyl, halogeno-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl; R.sup.5 is hydrogen, (1-4C)alkyl, halogeno-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, or a heteroaryl moiety selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, furyl, thienyl, oxazolyl and thiazolyl;A.sup.4 is (1-4C)alkylene;Ar.sup.1 is phenylene, pyridinediyl or pyrimidinediyl;A.sup.1 is a direct link to X.sup.1 or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl or thiazolediyl;R.sup.1 is hydrogen, (1-4C)alkyl, (3-C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is independently (1-3C)alkylene and X.sup.Type: GrantFiled: May 11, 1993Date of Patent: December 27, 1994Assignees: Zeneca Limited, Zeneca Pharma, S.A.Inventors: Philip N. Edwards, Michael S. Large
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Patent number: 5374746Abstract: The present invention relates to a L-talopyranoside derivative of the formula (I): ##STR1## wherein, A is hydrogen atom, a lower alkyl group having 1 to 5 carbon atoms, or a hydroxyl-protecting group;B.sub.1 and B.sub.2, the same or different from each other, are independently hydrogen atom or a hydroxyl-protecting group;R.sub.1 and R.sub.2 may form a alkylene group with a carbon atom of 5-position of the sugar skeleton, or one of them is hydrogen atom and the other is CH.sub.2 X wherein, X is hydrogen, or a protected or un-protected hydroxyl group.Provided that, the following compounds are excepted: ##STR2## wherein, B.sub.1 and B.sub.2 are independently hydrogen atom or acetyl. L-talopyronoside derivatives of the present invention is a very useful intermediate for the synthesis of anthracycline antibiotics having an antitumor activity.Type: GrantFiled: June 18, 1993Date of Patent: December 20, 1994Assignee: Dong-A Pharmaceutical Co., Ltd.Inventors: Kwang D. Ok, Moon S. Kim, Dong Y. Jung
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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