Multideoxy Or Didehydro Patents (Class 536/28.2)
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Publication number: 20100075917Abstract: The invention relates to a pharmaceutical composition containing as an active ingredient at least one compound selected from the compounds of the formula (II), in which the S atom is bonded to the nucleoside carbon at T or to the nucleoside carbon at 3?, and from the compounds of the following formula (III): formulae in which B is a nucleotide natural or modified base, x is 0, 1 or 2, and R1 and R represent a carbonated group or a molecular hydrocarbon remnant that can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si, X where X is halogen. The invention also relates to pharmaceutically acceptable carrier.Type: ApplicationFiled: October 29, 2007Publication date: March 25, 2010Applicant: UNIVERSITE JOSEPH FOURIER (GRENOBLE 1)Inventors: Jean-Luc Decout, Beatrice Gerland, Jerome Desire, Michel Lepoivre, Jan Balzarini
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Publication number: 20090318380Abstract: Embodiments of the invention are to compounds, methods, and compositions for use in the treatment of viral infections. More specifically embodiments of the invention are 2?,4?-substituted nucleoside compounds useful for the treatment of viral infections, such as HIV, HCV, and HBV infections.Type: ApplicationFiled: November 14, 2008Publication date: December 24, 2009Applicant: PHARMASSET, INC.Inventors: MICHAEL JOSEPH SOFIA, JINFA DU
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Publication number: 20090264637Abstract: Process for preparing a compound of the formula (I) R1-S(O)x—S(O)yR2 in which R1 represents a molecular hydrocarbon radical which can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si and X, where X represents a halogen; R2, independently of R1, represents a carbon-containing group or a molecular hydrocarbon radical which can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si and X, where X represents a halogen, and x and y are selected from 0 and 1 in such a way that the sum of x and y is not more than 1, characterized in that a compound of formula (II) R1-S(O)x—R3-Si(R4)(R5)(R6) in which R3 represents a hydrocarbon chain of two carbon atoms, which is optionally unsaturated and/or substituted, and R4, R5 and R6, which are identical or different, each represent, independently of one another, aType: ApplicationFiled: April 24, 2007Publication date: October 22, 2009Applicant: UNIVERSITE JOSEPH FOURIER (GRENOBLE 1)Inventors: Jean-Luc Decout, Beatrice Gerland, Jerome Desire
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Patent number: 7601702Abstract: Deoxyuridine derivatives of Formula (I?); where A is O, S or CH2; B is O, S or CHR3; R1 is H, or various substituents; R2 is H, F; R3 is H, F, OH, NH2; or R2 and R3 together form a chemical bond; D is —NHCO—, —CONH—, —O—, —C(?O)—, —CH?CH, —C?C—, —NR5—; R4 is hydrogen or various substituents; R5 is H, C1-C4 alkyl, C1-C4 alkanoyl; E is Si or C; R6, R7 and R8 are independently selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, or a stable monocyclic, bicyclic or tricyclic ring system have utility in the prophylaxis of treatment of parasitic diseases such as malaria.Type: GrantFiled: January 6, 2005Date of Patent: October 13, 2009Assignee: Medivir ABInventors: Ian Gilbert, Corinne Nguyen, Gian Filippo Ruda, Alessandro Schipani, Ganasan Kasinathan, Nils-Gunnar Johansson, Dolores Gonzalez Pacanowska
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Publication number: 20090233879Abstract: The present patent application relates to the novel nucleoside derivatives and novel intermediates, which are useful to antiviral, anti tumor and immunomodulatory activity, method of treating diseases, conditions and/or disorders modulated by viral infections with them, and processes for preparing them.Type: ApplicationFiled: March 12, 2009Publication date: September 17, 2009Applicant: HETERO DRUGS LIMITEDInventors: Bandi Parthasaradhi REDDY, Vedula Manohar SHARMA, Kura Rathnakar REDDY, Musku Madhanmohan REDDY, Jennepalli SREENU, Aryasomayajula RATNAKAR
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Publication number: 20090232833Abstract: The present invention provides polymeric delivery systems including hindered ester moieties. Methods of making the polymeric delivery systems and methods of treating mammals using the same are also disclosed.Type: ApplicationFiled: March 12, 2009Publication date: September 17, 2009Applicant: ENZON PHARMACEUTICALS, INC.Inventor: Hong ZHAO
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Patent number: 7589078Abstract: The present invention relates to compounds according to the general formula: wherein B is or and the remaining variables are defined in the specification, and compositions comprising the compounds. The compounds are useful as anti-viral agents in viral therapy.Type: GrantFiled: February 18, 2004Date of Patent: September 15, 2009Assignee: Yale UniversityInventors: Yung-chi Cheng, Hiromichi Tanaka, Masanori Baba
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Publication number: 20090176730Abstract: The present invention is directed to a method and composition of treating or preventing viral infections, in particular, human immunodeficiency virus (HIV) and hepatitis B virus (HBV) infections, in human patients or other animal hosts, comprising the administration of N.sup.4-acyl-2?,3?-dideoxy-5-fluorocytidine or N.sup.4-acyl-2?,3?-didehydro-2?,3?-dideoxy-5-fluorocytidine, and pharmaceutically acceptable salts, prodrugs, and other derivatives thereof.Type: ApplicationFiled: January 4, 2008Publication date: July 9, 2009Applicant: Pharmasset, Inc.Inventors: Michael J. Otto, Junxing Shi, Kyoichi A. Watanabe
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Publication number: 20090022664Abstract: The present invention relates to novel compounds suitable for or already radiolabelled with 18F, methods of making such compounds and use of such compounds for diagnostic imaging.Type: ApplicationFiled: September 7, 2007Publication date: January 22, 2009Inventors: Ananth Srinivasan, Thomas Brumby, Timo Stellfeld, Keith Graham, Ulrike Voigtmann, Jessica Becaud, Linjing Mu
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Publication number: 20090016958Abstract: Disclosed herein are novel radiolabeled nucleosides and methods for detecting cellular proliferation in a mammal, the method comprising administrating an effective amount of a radiolabeled nucleoside; the method comprising: a) administering to the mammal a diagnostically effective amount of the nucleoside to the mammal; b) allowing the nucleoside to distribute into the effective tissue; and c) imaging the tissue, wherein an increase in binding of the compound to tissue compared to a normal control level of binding indicates that the mammal is suffering from a disease involving cellular proliferation.Type: ApplicationFiled: March 3, 2008Publication date: January 15, 2009Inventors: Hartmuth C. Kolb, Joseph C. Walsh, Robert M. Yeh, Kai Chen, Umesh Gangadharmath, Brian Duclos, Vani P. Mocharla, Farhad Karimi, Henry C. Padgett, Qianwa Liang, Tieming Zhao
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Publication number: 20080312428Abstract: The present invention provides a method for preparing pure Stavudine having purity more than 99.5% comprises: i) Converting 3?,5?-anhydrothymidine to crude Stavudine, ii) Converting crude Stavudine to stable solvates of Stavudine, iii) Desolvation of the solvates to give pure Stavudine. The present invention also disclosed novel solvates of Stavudine and conversion of novel Stavudine solvates to Stavudine.Type: ApplicationFiled: November 17, 2006Publication date: December 18, 2008Applicant: MATRIX LABORATORIES LTDInventors: Purna Chandra Ray, Jagan Mohana Chary Tummanapalli, Seeta Ramanjaneyulu Gorantla
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Patent number: 7429572Abstract: The disclosed invention provides compositions and methods of treating a Flaviviridae infection, including hepatitis C virus, West Nile Virus, yellow fever virus, and a rhinovirus infection in a host, including animals, and especially humans, using a (2?R)-2?-deoxy-2?-fluoro-2?-C-methyl nucleosides, or a pharmaceutically acceptable salt or prodrug thereof.Type: GrantFiled: April 21, 2004Date of Patent: September 30, 2008Assignee: Pharmasset, Inc.Inventor: Jeremy Clark
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Patent number: 7192936Abstract: 2? and/or 3? prodrugs of 1?, 2?, 3? or 4?-branchednucleosides, and their pharmaceutically acceptable salts and derivatives are described. These prodrugs are useful in the prevention and treatment of Flaviviridae infections, including HCV infection, and other related conditions. Compounds and compositions of the prodrugs of the present invention are described. Methods and uses are also provided that include the administration of an effective amount of the prodrugs of the present invention, or their pharmaceutically acceptable salts or derivatives. These drugs may optionally be administered in combination or alteration with further anti-viral agents to prevent or treat Flaviviridae infections and other related conditions.Type: GrantFiled: December 6, 2004Date of Patent: March 20, 2007Assignees: Idenix Pharmaceuticals, Inc., Centre National de la Recherche Scientifique, Universita Degli Studi Di CagliariInventors: Paola LaColla, Richard Storer, Gilles Gosselin, Jean-Pierre Sommadossi
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Patent number: 7169766Abstract: A method and composition for treating a host infected with hepatitis C comprising administering an effective hepatitis C treatment amount of a described 1?, 2? or 3?-modified nucleoside or a pharmaceutically acceptable salt or prodrug thereof, is provided.Type: GrantFiled: June 20, 2003Date of Patent: January 30, 2007Assignees: Idenix Pharmaceuticals, Inc., Universita Degli Studi di CagliariInventors: Jean-Pierre Sommadossi, Paulo LaColla
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Patent number: 7163929Abstract: A method and composition for treating a host infected with flavivirus or pestivirus comprising administering an effective flavivirus or pestivirus treatment amount of a described 1?, 2? or 3?-modified nucleoside or a pharmaceutically acceptable salt or prodrug thereof, is provided.Type: GrantFiled: June 20, 2003Date of Patent: January 16, 2007Assignees: Idenix Pharmaceuticals, Inc., Universita Degli Studi Di CagliariInventors: Jean-Pierre Sommadossi, Paulo LaColla
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Patent number: 7148207Abstract: This invention relates to a quick-release tablet formulation with >99.19% pure fludara (high-purity fludara) as an active ingredient in a defined composition of residual contaminants.Type: GrantFiled: December 20, 2002Date of Patent: December 12, 2006Assignee: Schering AktiengesellschaftInventors: Wolfgang Heil, Ulf Tistam, Ralph Lipp, Johannes-Wilhelm Tack
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Patent number: 7119096Abstract: Uracil reductase inactivators, notably a 5-substituted uracil or 5,6-dihydro-5-substituted uracil, potentiate 5-flourouracil and find use particularly in the treatment of cancer. The 5-substituent is selected from bromo, ido, cyano, halo-substituted C1-4 alkyl, C2-6 alkenyl, 1-halo-C2-6 alkenyl and halo-substituted C2-6 alkynyl.Type: GrantFiled: October 1, 2001Date of Patent: October 10, 2006Assignee: SmithKlineBeecham CorporationInventors: Thomas Spector, David J. T. Porter, Saad G. Rahim
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Patent number: 7101861Abstract: A method and composition for treating a host infected with flavivirus or pestivirus comprising administering an effective flavivirus or pestivirus treatment amount of a described 1?, 2? or 3?-modified nucleoside or a pharmaceutically acceptable salt or prodrug thereof, is provided.Type: GrantFiled: June 20, 2003Date of Patent: September 5, 2006Assignees: Indenix Pharmaceuticals, Inc., Universita Degli Studi Di CagliariInventors: Jean-Pierre Sommadossi, Paulo LaColla
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Patent number: 6974802Abstract: A method of treating HBV or HIV infections comprising administering to an individual an effective amount of the compound of formula IId?: wherein R2 is the residue of an aliphatic L-amino acid, p is 0, 1, or 2-20, and q is 0, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: November 16, 2001Date of Patent: December 13, 2005Assignee: Medivir ABInventors: Xiao-Xiong Zhou, Nils Gunnar Johansson, Horst Wahling
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Patent number: 6960568Abstract: The invention provides novel nucleosides and related processes, pharmaceutical compositions, and methods. The novel nucleosides are useful in a wide variety of antiviral, antineoplastic, and antibacterial applications. Preferred embodiments of the instant invention include novel 2 halogen-substituted, 3 halogen-substituted, and 2?,3?dihalogen-substituted analogues of 3-deazaadenosine, and novel 3 halogen-substituted analogues of 3-deazaguanosine. Compounds of the instant invention, including 4-Amino-6-fluoro-1-(?-D-ribofuranosyl)imidazo[4,5-c]pyridine and 6-Amino-7-bromo-1,5-dihydro-1-?-D-ribofuranosylimidazo[4,5-c]pyridin-4-one, have exhibited potent antiviral and anticancer activity in vitro. The compounds are also useful in the concomitant treatment of bacterial infections associated with viral infections such as AIDS.Type: GrantFiled: December 17, 2002Date of Patent: November 1, 2005Assignee: Yale UniversityInventors: Alan C. Sartorelli, Yung-Chi Cheng, Mao-Chin Liu
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Patent number: 6930097Abstract: A compound of formula 1-[3,4-dihydroxy-5-(2-hydroxyethyl)tetrahydrofuran-2-yl]pryimidine-2,4(1H,3H)-dione has inhibitory effects of matrix metalloproteinase-2 (gelatinase A) enzyme and binding of TNF? to TNF?-RI.Type: GrantFiled: April 21, 2003Date of Patent: August 16, 2005Assignee: Advanced Gene Technology Corp.Inventors: Li-Wei Hsu, Su-Chen Chang, Jeng-Woei Lee, Pang-Hsi Liu, Hui-Ping Lee, Yi-Ching Chen, Chun-Tsun Chen
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Patent number: 6924271Abstract: The invention is directed to 3-?-D-ribofuranosylthiazolo[4,5-d]pyridimine nucleosides and pharmaceutical compositions containing such compounds that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds.Type: GrantFiled: November 27, 2002Date of Patent: August 2, 2005Assignee: Anadys Pharmaceuticals, Inc.Inventors: Devron R. Averett, Stephen E. Webber, Joseph R. Lennox, Erik J. Rueden
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Patent number: 6914054Abstract: A method and composition for treating a host infected with hepatitis C comprising administering an effective hepatitis C treatment amount of a described 1?, 2? or 3?-modified nucleoside or a pharmaceutically acceptable salt or prodrug thereof, is provided.Type: GrantFiled: May 23, 2001Date of Patent: July 5, 2005Assignee: Idenix Pharmaceuticals, Inc.Inventors: Jean-Pierre Sommadossi, Paulo LaColla
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Patent number: 6846918Abstract: This invention discloses a method for the preparation of 2?-modified nucleosides, using a palladium catalyst and an alkene functionalized with a heteroatom. Included in the invention are the novel pyrimidines and purines that can be prepared according to the method of the invention and oligonucleotides containing said modified pyrimidines and purines.Type: GrantFiled: January 24, 2003Date of Patent: January 25, 2005Assignee: Gilead Sciences, Inc.Inventors: Jeffrey T. Beckvermit, Chi Tu
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Patent number: 6841675Abstract: A novel nucleoside analog is disclosed which comprises a piperazine ring in the place of the ring ribose or deoxyribose sugar. Monomers utilizing a broad variety of nucleobases are disclosed, as well as oligomers comprising the monomers disclosed herein linked by a variety of linkages, including amide, phosphonamide, and sulfonamide linkages. A method of synthesizing the nucleoside analogs is also disclosed.Type: GrantFiled: June 13, 2002Date of Patent: January 11, 2005Assignee: The Regents of the University of CaliforniaInventors: Jurgen Schmidt, Louis A. Silks, Ryszard Michalczyk
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Patent number: 6822089Abstract: Methods for preparing deoxynucleosides from their corresponding ribonucleosides by forming 3-tert-butylphenoxythiocarbonylderivatives of the ribonucleosides and subsequently effecting radical deoxygenation reactions at the carbon atoms to be deoxygenated.Type: GrantFiled: March 29, 2000Date of Patent: November 23, 2004Assignee: ISIS Pharmaceuticals, Inc.Inventors: Yogesh S. Sanghvi, Zhiqiang Guo
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Patent number: 6812219Abstract: A method and composition for treating a host infected with flavivirus or pestivirus comprising administering an effective flavivirus or pestivirus treatment amount of a described 1′, 2′ or 3′-modified nucleoside or a pharmaceutically acceptable salt or prodrug thereof, is provided.Type: GrantFiled: May 23, 2001Date of Patent: November 2, 2004Assignee: Idenix Pharmaceuticals, Inc.Inventors: Paulo LaColla, Jean-Pierre Sommadossi
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Patent number: 6784161Abstract: The present invention relates to a method for the treatment or prevention of Flavivirus infections using nucleoside analogues in a host comprising administering a therapeutically effective amount of a compound having the formula I or a pharmaceutically acceptable salt thereof.Type: GrantFiled: February 20, 2001Date of Patent: August 31, 2004Assignee: BioChem Pharma, Inc.Inventors: Hicham Moulay Alaoui Ismaili, Yun-Xing Cheng, Jean-François Lavallée, Arshad Siddiqui, Richard Storer
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Publication number: 20040147479Abstract: The invention provides a method of synthesizing &bgr;-L-5-fluoro-2′,3′-dideoxy-2′,3′-didehydrocytidine (&bgr;-L-FD4C). The method allows for large-scale production of &bgr;-L-FD4C in an efficient, cost-effective, and environmentally sound manner.Type: ApplicationFiled: April 11, 2003Publication date: July 29, 2004Applicant: Achillion Pharmaceuticals, Inc.Inventors: Bo Kowalczyk, Zhao Li, Ralph M. Schure, Lisa Dunkle
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Patent number: 6680303Abstract: A method and composition for the treatment of HIV and HBV infections in humans and other host animals is disclosed that includes the administration of an effective amount of a [5-carboxamido or 5-fluoro]-2′,3′-dideoxy-2′,3′-didehydro-pyrimidine nucleoside or a [5-carboxamido or 5-fluoro]-3′-modified-pyrimidine nucleoside, or a mixture or a pharmaceutically acceptable derivative thereof, including a 5′ or N4 alkylated or acrylated derivative, or a pharmaceutically acceptable salt thereof, in a pharmaceutically acceptable carrier.Type: GrantFiled: May 15, 2002Date of Patent: January 20, 2004Assignee: Emory UniversityInventors: Raymond F. Schinazi, Dennis C. Liotta
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Patent number: 6670336Abstract: Aryl phosphate derivatives of d4T with para-bromo substitution on the aryl group show markedly increased potency as anti-HIV agents without undesirable levels of cytotoxic activity. In particular, these derivatives are potent inhibitors of HIV reverse transcriptase. In a preferred aspect of the present invention, the phosphorus of the aryl phosphate group is further substituted with an amino acid residue that may be esterified or substituted, such as a methoxy alaninyl group.Type: GrantFiled: April 13, 2000Date of Patent: December 30, 2003Assignee: Parker Hughes InstituteInventors: Fatih M. Uckun, Rakesh Vig
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Publication number: 20030216575Abstract: This invention is directed to novel pyranosyl cytosine compounds depicted graphically as structure I. This invention is further directed to a unique methodology for their preparation using solid-phase methodology. These hexopyranosyl cytosine derived natural product analogs share their parent compounds broad-spectrum antimicrobial and anti-fungal profile and represent a vast, novel compound class of 50S rRNA directed inhibitors of protein translation.Type: ApplicationFiled: February 4, 2002Publication date: November 20, 2003Inventors: Michael T. Migawa, Eric E. Swayze, Richard H. Griffey
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Patent number: 6635753Abstract: There are disclosed novel Stavudine solvates as follows: Stavudine NN-dimethyllacetamide solvates; Stavudine NN-dimethylacrylamide solvates and Stavudine NN-dimethylpropionamide solvates and processes for producing Stavudine NN-dimethylacetamide solvates, Stavudine NN dimethylacrylamide solvates and Stavudine NN dimethylpropionamide solvates which results in pure Stavudine.Type: GrantFiled: September 30, 1998Date of Patent: October 21, 2003Assignee: Brantford Chemicals Inc.Inventors: Bruno K. Radatus, K. S. Keshava Murthy
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Patent number: 6602664Abstract: It has been discovered that 3′-azido-2′,3′-dideoxyuridine (CS-87) induces a transient mutation in HIV-1 at the 70th codon (K to R, i.e., lysine to arginine) of the reverse transcriptase region of the virus. Based on this discovery, a method and composition for treating HIV is provided that includes administering CS-87 or its pharmaceutically acceptable salt or prodrug to a human in need of therapy in combination or alternation with a drug that induces a mutation in HIV-1 at a location other than the 70th codon of the reverse transcriptase region. This invention can be practiced by referring to the published mutation patterns for known anti-HIV drugs, or by determining the mutation pattern for a new drug.Type: GrantFiled: February 26, 2001Date of Patent: August 5, 2003Assignees: Emory University, Idenix Pharmaceuticals, Inc.Inventors: Raymond F. Schinazi, Martin L. Bryant, Maureen W. Myers
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Patent number: 6555676Abstract: Compounds of formula RS—P(═O)(QR)—Nu where: R is a radical —(CH2)n—W—X; X is a radical —C(═Z)(Y) or —S—U; Z is O or S; W is O or S; Q is O or S; Y and U are an alkyl, aryl or saccharide radical which is optionally substituted with, for example, an OH, SH or NH group; n is equal to 1 to 4, preferably 1 or 2; and Nu is a radical consisting of a residue of a biologically active compound or the dephosphorylated residue of a compound which is biologically active when it bears a phosphate or phosphonate group.Type: GrantFiled: September 21, 2001Date of Patent: April 29, 2003Assignee: Centre National de la Recherche ScientifiqueInventors: Gilles Gosselin, Jean-Louis Imbach, Christian Perigaud
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Publication number: 20030069414Abstract: Modified nucleosides and methods of making and using the nucleosides are disclosed. The compounds can be prepared by reacting nucleoside starting materials that contain a suitable leaving group at one or more of the carbon atoms in the purine or pyrimidine ring, with a vinylstannane, carbon monoxide, and a palladium catalyst to provide 1-ene-3-one intermediates. These intermediates are then reacted with suitably functionalized primary or secondary amines via a Michael reaction. When the intermediate is a 5-position modified pyrimidine ring, and the amine contains a second hydrogen, it can do a second Michael reaction with the ene-one or the ene-imine in the pyrimidine ring. Appropriate modification of the amine reactant can yield products with various bioactivities. The nucleosides can be used therapeutically as anti-cancer, anti-bacterial or anti-viral drugs. The nucleosides can also be used for diagnostic applications, for example, by incorporating a radiolabel or fluorescent label into the molecule.Type: ApplicationFiled: August 9, 2002Publication date: April 10, 2003Applicant: GILEAD SCIENCES, INC.Inventors: Gary P. Kirschenheuter, Bruce Eaton
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Patent number: 6528495Abstract: Aryl phosphate derivatives of d4T with para-bromo substitution on the aryl group show markedly increased potency as anti-HIV agents without undesirable levels of cytotoxic activity. In particular, these derivatives are potent inhibitors of HIV reverse transcriptase. In a preferred aspect of the present invention, the phosphorus of the aryl phosphate group is further substituted with an amino acid residue that may be esterified or substituted, such as a methoxy alaninyl group.Type: GrantFiled: April 13, 2000Date of Patent: March 4, 2003Assignee: Parker Hughes InstituteInventors: Fatih M. Uckun, Rakesh Vig
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Patent number: 6503890Abstract: Aryl phosphate nucleoside derivatives show potent activity against HIV without undesirable levels of cytotoxic activity. Examples of aryl phosphate nucleoside derivatives include aryl phosphate derivatives of d4T with para-bromo substitution on the aryl group. In particular, these derivatives are potent inhibitors of HIV reverse transcriptase. In a preferred aspect of the present invention, the phosphorus of the aryl phosphate group is further substituted with an amino acid residue that may be esterified or substituted, such as a methoxy alaninyl group.Type: GrantFiled: November 29, 1999Date of Patent: January 7, 2003Assignee: Parker Hughes InstituteInventor: Fatih M. Uckun
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Publication number: 20020198224Abstract: The present invention is an efficient synthetic route to 2′,3′-dideoxy-2′,3 ′-didehydro-nucleosides from available precursors with the option of introducing functionality as needed, such as, the 2′,3′-dideoxy and 2′- or 3′-deoxyribo-nucleoside analogs as well as additional derivatives obtained by subsequent functional group manipulations. Briefly, the present invention discloses a method for the preparation of &bgr;-D and &bgr;-L-2′,3′-dideoxy-2′,3′-didehydro-nucleosides starting from appropriately substituted ribonucleosides in two, optionally three steps: Step (1) a haloacylation, such as haloacetylation, and in particular, bromoacetylation; Step (2) a reductive elimination; and optionally, Step (3) a deprotection. The haloacylation of step (1) can form the 2′-acyl-3′-halonucleoside, the 3′-acyl-2′-halonucleoside, or a mixture thereof.Type: ApplicationFiled: March 1, 2002Publication date: December 26, 2002Inventors: Fuqiang Jin, Pasquale N. Confalone
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Patent number: 6482805Abstract: Contraceptive activity as well as anti-viral protection can be provided by contraceptive compositions containing a pyrimidine-based nucleoside or nucleotide exhibiting spermicidal or sperm-immobilizing activity. In one example, the active ingredient contains a thymine ring (e.g. AZT) that has 5-halo, 6-alkoxy substitution. Additional improvements in anti-HIV activity for certain AZT derivatives are seen by providing the pentose ring of AZT with aryl phosphate substitution.Type: GrantFiled: December 1, 2000Date of Patent: November 19, 2002Assignee: Parker Hughes InstituteInventors: Fatih M. Uckun, Osmond D'Cruz, Taracad Venkatachalam
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Patent number: 6458772Abstract: Compounds of the formula I or corresponding monohydroxynucleoside derivatives wherein: R1 is hydroxy, amino or carboxy: optionally having esterified/amide bonded thereon; a C4-C22 saturated or unsaturated, optionally substituted fatty acid or alcohol, or an aliphatic L-amino acid; R2 is the residue of an aliphatic L-amino acid; L1 is a trifunctional linker group; L2 is absent or a difunctional linker group; and pharmaceutically acceptable salts thereof have favorable pharmacological properties and are antivirally active.Type: GrantFiled: February 12, 1999Date of Patent: October 1, 2002Assignee: Medivir ABInventors: Xiao-Xiong Zhou, Nils Gunnar Johansson, Horst Wahling, Christian Sund, Hans Wallberg, Lourdes Salvador, Stefan Lindstrom, Christer Sahlberg
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Patent number: 6458773Abstract: Compounds and pharmaceutical compositions active against hepatitis B virus are provided, as is a method for the treatment of hepatitis B virus infection in humans and other host animals is provided comprising administering an effective amount of a &bgr;-L-(2′or 3′-azido)-2′,3′-dideoxy-5-fluorocytosine of the formula wherein R is H, acyl, monophosphate, diphosphate, or triphosphate, or a stabilized phosphate derivative (to form a stabilized nucleotide prodrug), and R′is H, acyl, or alkyl.Type: GrantFiled: November 5, 1999Date of Patent: October 1, 2002Assignees: Emory University, Centre National de la Recherche Scientifique, UAB Research FoundationInventors: Gilles Gosselin, Jean-Louis Imbach, Jean-Pierre Sommadossi, Raymond F. Schinazi
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Publication number: 20020120130Abstract: Method for the sterospecific preparation of 2′ or 3′ deoxy and 2′, 3′-dideoxy-&bgr;-L-pentofuranonucleoside compounds. 2′ or 3′ deoxy and 2′, 3′-dideoxy-&bgr;-L-pentofuranonucleoside compounds are also described. Finally, the invention concerns the use of these compounds, and particularly 2′, 3′ dideoxy-&bgr;-L-fluorocytidine, as drugs, and especially as anti-viral agents.Type: ApplicationFiled: September 14, 2001Publication date: August 29, 2002Inventors: Gilles Gosselin, Jean-Louis Imbach, Anne-Marie Aubertin, Jean-Pierre Sommadossi, Raymond F. Schinazi
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Patent number: 6392032Abstract: Heavily fluorinated sugar analogs of formula wherein R1 is selected from alkyl, alkenyl, aryl, —CH2—O-alkyl, —CH2—O-aryl, —CH2OPO3H, —CH2—O-carbohydrate, —CH2—NH-peptide, or —CH2—O-peptide; wherein R2 is selected from hydroxy, —O-carbohydrate, —NH-peptide, wherein R3 is selected from H, halogen, lower alkyl, lower alkenyl, lower haloalkyl, lower haloalkenyl, amino, mono- or di-lower alkylamino; wherein R4 is selected from amino, hydroxy, alkoxy, or halogen; and wherein R5 is H or amino. The compounds of formula (I) are useful as antiviral and antineoplastic agents and the compounds of formula (II) are useful as plant growth inhibitors and herbicides.Type: GrantFiled: September 2, 1999Date of Patent: May 21, 2002Assignee: Board of Regents University of Nebraska-LincolnInventor: Stephen G. Dimagno
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Patent number: 6384019Abstract: The invention provides Gemcitabine esters or amides in which the 3′- and/or 5′-OH group and/or the N4-amino group is derivatised with a C18- and/or C20-saturated or mono-unsaturated acyl group, preferably an acyl group selected from oleoyl, elaidoyl, cis-eicosenoyl and trans-eicosenoyl. The Gemcitabine esters and amides are useful as anti-cancer and anti-viral agents.Type: GrantFiled: September 15, 1999Date of Patent: May 7, 2002Assignee: Norsk Hydro ASAInventors: Finn Myhren, Bernt Børretzen, Are Dalen, Marit Liland Sandvold
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Publication number: 20020042391Abstract: The invention provides Gemcitabine esters or amides in which the 3′- and/or 5′-OH group and/or the N4-amino group is derivatised with a C18- and/or C20-saturated or mono-unsaturated acyl group, preferably an acyl group selected from oleoyl, elaidoyl, cis-eicosenioyl and trans-eicosenoyl. The Gemcitabine esters and amides are useful as anti-cancer and anti-viral agents.Type: ApplicationFiled: September 15, 1999Publication date: April 11, 2002Inventors: FINN MYHREN, BERNT BORRETZEN, ARE DALEN, MARIT LILAND SANDVOLD
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Publication number: 20020019356Abstract: A method of increasing efficiency and/or decreasing the cytotoxic effect of a human immunodeficiency virus (HIV) reproduction-suppressing drug such as Azidothimidin (AZT) involves administering the drug to an HIV-positive patient and subjecting the patient to hyperbaric oxygenation (HBO).Type: ApplicationFiled: May 3, 1999Publication date: February 14, 2002Inventors: VLADIMIR ILICH PAKHOMOV, EDUARD VLADIMIROVICH KARAMOV, ALEXANDR EVGENEVICH SOKOLOV, GALINA VLADIMIROVNA KORNILAEVA, MIKHAIL YUREVICH SHTSHELKANOV, VLADIMIR NIKOLAEVICH KOSTYUNIN
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Patent number: 6297223Abstract: Uracil reductase inactivators, notably a 5-substituted uracil or 5,6-dihydro-5-substituted uracil, potentiate 5-fluorouracil and find use particularly in the treatment of cancer. The 5-substituent is selected from bromo, iodo, cyano, halo-substituted C1-4 alkyl, C2-6 alkenyl, 1-halo-C2-6 alkenyl and halo-substituted C2-6 aklynyl.Type: GrantFiled: June 30, 2000Date of Patent: October 2, 2001Assignee: Glaxo Wellcome Inc.Inventors: Thomas Spector, David J. T. Porter, Saad G. Rahim
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Patent number: 6268374Abstract: The present invention relates to a group of 5-substituted uracil derivatives which are inactivators of uracil reductase and which are particularly useful in cancer chemotherapy, especially in combination with antimetabolite antineoplastic agents such as 5-fluorouracil.Type: GrantFiled: July 23, 1993Date of Patent: July 31, 2001Assignee: Glaxo Wellcome Inc.Inventors: Thomas Spector, David J. T. Porter, Saad G. Rahim
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Treatment of HIV by administration of &bgr;-D-2?, 3?-didehydro-2?,3?-dideoxy-5-fluorocytidine (D4FC)
Patent number: 6232300Abstract: A method and composition for the treatment of HIV and HBV infections in humans and other host animals is disclosed that includes the administration of an effective amount of a [5-carboxamido or 5-fluoro]-2′,3′-dideoxy-2′,3′-didehydro-pyrimidine nucleoside or a [5-carboxamido or 5-fluoro]-3′-modified-pyrimidine nucleoside, or a mixture or a pharmaceutically acceptable derivative thereof, including a 5′ or N4 alkylated or acylated derivative, or a pharmaceutically acceptable salt thereof, in a pharmaceutically acceptable carrier.Type: GrantFiled: May 12, 1999Date of Patent: May 15, 2001Assignee: Emory UniversityInventors: Raymond F. Schinazi, Dennis C. Liotta