Plural Chalcogens Bonded Directly To The Hetero Ring Patents (Class 549/417)
  • Patent number: 5844000
    Abstract: 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: Grant
    Filed: June 12, 1997
    Date of Patent: December 1, 1998
    Assignee: Sanofi
    Inventors: William Brian, Brian Folk, Juan Shi, Gerard Fabre, Claude Tronquet
  • Patent number: 5840751
    Abstract: 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: Grant
    Filed: October 12, 1994
    Date of Patent: November 24, 1998
    Assignee: Warner-Lambert Company
    Inventors: Edmund Lee Ellsworth, Elizabeth Lunney, Bradley Dean Tait
  • Patent number: 5811028
    Abstract: 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: Grant
    Filed: August 13, 1997
    Date of Patent: September 22, 1998
    Assignee: Kashima Oil Company
    Inventors: Tatsushi Ishizuka, Mitsunori Takeda, Masaaki Namekawa, Keizou Itoh
  • Patent number: 5808111
    Abstract: 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: Grant
    Filed: May 6, 1997
    Date of Patent: September 15, 1998
    Assignee: The Ohio State Research Foundation
    Inventor: Robert W. Curley, Jr.
  • Patent number: 5801257
    Abstract: 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: Grant
    Filed: October 20, 1997
    Date of Patent: September 1, 1998
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
  • Patent number: 5795981
    Abstract: 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: Grant
    Filed: December 16, 1996
    Date of Patent: August 18, 1998
    Assignee: Polaroid Corporation
    Inventors: John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
  • Patent number: 5789605
    Abstract: 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: Grant
    Filed: December 3, 1996
    Date of Patent: August 4, 1998
    Assignee: Trustees of the University of Pennsylvania
    Inventors: Amos B. Smith, III, Yuping Qiu, Michael Kaufman, Hirokaza Arimoto, David R. Jones, Kaoru Kobayashi
  • Patent number: 5777136
    Abstract: 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: Grant
    Filed: February 7, 1997
    Date of Patent: July 7, 1998
    Assignee: Indena S.p.A.
    Inventor: Ezio Bombardelli
  • Patent number: 5767100
    Abstract: 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: Grant
    Filed: March 13, 1996
    Date of Patent: June 16, 1998
    Assignee: Gilead Sciences, Inc.
    Inventors: Petr Alexander, Ernest J. Prisbe
  • Patent number: 5767094
    Abstract: 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: Grant
    Filed: November 7, 1996
    Date of Patent: June 16, 1998
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Kenji Tsujihara, Kunio Saito, Mitsuya Hongu, Mamoru Matsumoto, Kozo Oka
  • Patent number: 5750733
    Abstract: 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: Grant
    Filed: August 6, 1996
    Date of Patent: May 12, 1998
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Robert Vermeer, Bijan Harichian
  • Patent number: 5746933
    Abstract: 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: Grant
    Filed: November 3, 1995
    Date of Patent: May 5, 1998
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Noboru Ishida, Umekichi Sasaki, Katsuya Takigawa, Satoshi Suda
  • Patent number: 5733927
    Abstract: 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: Grant
    Filed: June 5, 1995
    Date of Patent: March 31, 1998
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Katsuhiro Imaki, Shinsuke Hashimoto, Hirohisa Wakatsuka
  • Patent number: 5719130
    Abstract: 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: Grant
    Filed: September 9, 1996
    Date of Patent: February 17, 1998
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
  • Patent number: 5719291
    Abstract: Compounds of the formula ##STR1## which have antifungal activity.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: February 17, 1998
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Yuhko Aoki, Hiromichi Kotaki, Kazunao Masubuchi, Toru Okuda, Nobuo Shimma, Takuo Tsukuda, Isao Umeda
  • Patent number: 5714484
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: February 3, 1998
    Assignee: Prototek, Inc.
    Inventors: Mary P. Zimmerman, Robert E. Smith, Mark Becker
  • Patent number: 5712254
    Abstract: 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: Grant
    Filed: December 23, 1994
    Date of Patent: January 27, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Haruyuki Chaki, Naoko Ando, Yasuhiro Morinaka, Ken-Ichi Saito, Tomoko Yugami, Rie Yoshida
  • Patent number: 5698137
    Abstract: 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: Grant
    Filed: April 15, 1996
    Date of Patent: December 16, 1997
    Assignee: Kashima Oil Company
    Inventors: Tatsushi Ishizuka, Mitsunori Takeda, Masaaki Namekawa, Keizou Itoh
  • Patent number: 5663377
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: September 2, 1997
    Assignee: The Ohio State Research Foundation
    Inventors: Robert W. Curley, Jr., Michael J. Panigot
  • Patent number: 5656750
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: August 12, 1997
    Assignee: Polaroid Corporation
    Inventors: Richard M. Allen, Peter K. Chu
  • Patent number: 5648379
    Abstract: 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: Grant
    Filed: October 19, 1994
    Date of Patent: July 15, 1997
    Assignee: 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
  • Patent number: 5646179
    Abstract: 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: Grant
    Filed: December 12, 1995
    Date of Patent: July 8, 1997
    Assignees: Analyticon Gesellschaft fur Chemische Analytik und Consulting GmbH, Diagen Institut fur Molekularbiologische Diagnostik GmbH
    Inventors: Lutz Muller-Kuhrt, Andreas Immelmann
  • Patent number: 5633089
    Abstract: 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: Grant
    Filed: September 22, 1995
    Date of Patent: May 27, 1997
    Assignee: Sony Corporation
    Inventor: Hirofumi Kondo
  • Patent number: 5631389
    Abstract: 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: Grant
    Filed: April 30, 1996
    Date of Patent: May 20, 1997
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Robert Vermeer, Van Au, Bijan Harichian
  • Patent number: 5627290
    Abstract: 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: Grant
    Filed: January 26, 1996
    Date of Patent: May 6, 1997
    Assignee: Daikin Industries, Ltd.
    Inventors: Takao Iida, Yutaka Ohira
  • Patent number: 5627194
    Abstract: 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: Grant
    Filed: October 14, 1994
    Date of Patent: May 6, 1997
    Assignee: Allelix Biopharmaceuticals Inc.
    Inventors: Sumanas Rakhit, Abdelmalik Slassi
  • Patent number: 5618775
    Abstract: 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: Grant
    Filed: August 11, 1994
    Date of Patent: April 8, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Wolfgang Ladner, Helmut Walter, Karl-Otto Westphalen, Uwe Kardorff, Matthias Gerber
  • Patent number: 5602262
    Abstract: 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: Grant
    Filed: February 3, 1995
    Date of Patent: February 11, 1997
    Assignee: Eli Lilly and Company
    Inventor: David D. Wirth
  • Patent number: 5599915
    Abstract: 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: Grant
    Filed: March 21, 1995
    Date of Patent: February 4, 1997
    Assignee: The Scripps Research Institute
    Inventors: Chi-Huey Wong, Tetsuya Kajimoto
  • Patent number: 5599953
    Abstract: 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: Grant
    Filed: May 26, 1995
    Date of Patent: February 4, 1997
    Assignee: The Ohio State Research Foundation
    Inventors: Robert W. Curley, Jr., Michael J. Robarge
  • Patent number: 5574000
    Abstract: 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: Grant
    Filed: November 17, 1994
    Date of Patent: November 12, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Kast, Dieter Kolassa, Norbert Meyer, Ulrich Schirmer, Albrecht Harreus, Jochen Wild, Karl-Otto Westphalen, Bruno Wuerzer
  • Patent number: 5574177
    Abstract: 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: Grant
    Filed: October 7, 1994
    Date of Patent: November 12, 1996
    Assignee: The Ohio State Research Foundation
    Inventors: Robert W. Curley, Jr., Michael J. Panigot
  • Patent number: 5563250
    Abstract: 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: Grant
    Filed: May 13, 1994
    Date of Patent: October 8, 1996
    Assignee: NeoRx Corporation
    Inventors: Mark D. Hylarides, Ananthachari Srinivasan, Jeffrey N. Fitzner, Vivekananda M. Vrudhula
  • Patent number: 5554771
    Abstract: The present invention relates to 2-deoxy-N-acetylneuraminic acid derivatives and methods for their preparation.
    Type: Grant
    Filed: August 16, 1995
    Date of Patent: September 10, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Chi-Huey Wong, William J. Hennen
  • Patent number: 5536850
    Abstract: The present invention relates to a novel substance DC114-A1 represented by the following formula (I): ##STR1##
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: July 16, 1996
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hirofumi Nakano, Noboru Fujii, Tamio Mizukami, Youichi Uosaki, Katsunori Kita, Eiji Kobayashi
  • Patent number: 5523320
    Abstract: 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: Grant
    Filed: January 3, 1995
    Date of Patent: June 4, 1996
    Assignee: Ohgen Research Laboratories, Ltd.
    Inventor: Kiyoshi Akiyama
  • Patent number: 5516792
    Abstract: 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: Grant
    Filed: September 30, 1994
    Date of Patent: May 14, 1996
    Assignee: Ohio State Research Foundation
    Inventors: Robert W. Curley, Jr., Michael J. Robarge
  • Patent number: 5496943
    Abstract: 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: Grant
    Filed: March 13, 1992
    Date of Patent: March 5, 1996
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Otohiko Tsuge, Taizo Hatta, Satoshi Urano, Noriyuki Tsuboniwa, Ryuzo Mizuguchi
  • Patent number: 5486623
    Abstract: 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: Grant
    Filed: December 8, 1993
    Date of Patent: January 23, 1996
    Assignee: Prototek, Inc.
    Inventors: Mary P. Zimmerman, Robert E. Smith
  • Patent number: 5482966
    Abstract: 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: Grant
    Filed: June 13, 1994
    Date of Patent: January 9, 1996
    Assignees: Zeneca Limited, Zeneca Pharma S.A.
    Inventors: Thomas G. C. Bird, Patrick Ple
  • Patent number: 5453439
    Abstract: 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: Grant
    Filed: February 8, 1993
    Date of Patent: September 26, 1995
    Assignees: Zeneca Limited, Zeneca-Pharma S.A.
    Inventor: Patrick Ple
  • Patent number: 5426111
    Abstract: 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: Grant
    Filed: November 23, 1994
    Date of Patent: June 20, 1995
    Assignee: Abbott Laboratories
    Inventors: Joseph F. Dellaria, James D. Ratajczyk, Clint D. W. Brooks, Anwer Basha
  • Patent number: 5414096
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: May 9, 1995
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Joseph A. Tino, Gregory S. Bisacchi, Saleem Ahmad
  • Patent number: 5414000
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is a substituted purinyl group including pharmaceutically acceptable salts are useful as antiviral agents.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: May 9, 1995
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Joseph A. Tino, Gregory S. Bisacchi, Saleem Ahmad
  • Patent number: 5412118
    Abstract: 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: Grant
    Filed: October 12, 1993
    Date of Patent: May 2, 1995
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Robert Vermeer, Bijan Harichian, Van Au
  • Patent number: 5403857
    Abstract: 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: Grant
    Filed: February 1, 1994
    Date of Patent: April 4, 1995
    Assignees: Imperial Chemical Industries PLC, ICI-Pharma
    Inventors: Philip N. Edwards, Keith Oldham, David Waterson
  • Patent number: 5393764
    Abstract: 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: Grant
    Filed: August 25, 1993
    Date of Patent: February 28, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 5376680
    Abstract: 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: Grant
    Filed: May 11, 1993
    Date of Patent: December 27, 1994
    Assignees: Zeneca Limited, Zeneca Pharma, S.A.
    Inventors: Philip N. Edwards, Michael S. Large
  • Patent number: 5374746
    Abstract: 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: Grant
    Filed: June 18, 1993
    Date of Patent: December 20, 1994
    Assignee: Dong-A Pharmaceutical Co., Ltd.
    Inventors: Kwang D. Ok, Moon S. Kim, Dong Y. Jung
  • Patent number: 5360817
    Abstract: 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: Grant
    Filed: November 10, 1992
    Date of Patent: November 1, 1994
    Assignee: Biota Scientific Management Pty Ltd
    Inventors: Laurence M. von Izstein, Wen-Yang Wu, Tho V. Phan, Basil Danylec, Betty Jin