Multideoxy Or Didehydro Patents (Class 536/27.14)
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Patent number: 6525033Abstract: A method for treating HBV infections via administration of 2′, 3′ dideoxynucleoside compounds.Type: GrantFiled: November 22, 1999Date of Patent: February 25, 2003Assignees: Emory University, University of Alabama Research Foundation, Inc.Inventors: Raymond F. Schinazi, Jean-Pierre Sommadossi, Gilles Gosselin, Jean-Louis Imbach
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Publication number: 20030004330Abstract: Novel intermediates of nucleoside derivatives, of which the 6-position of the nucleic acid base moiety is substituted with a halogen atom, are produced. Using those novel intermediates, even substrates, of which the 3′-position of the saccharide moiety is deoxylated, can be substituted at the 2′-position at an extremely high yield. Specifically, by subjecting a 3′-deoxy derivative of inosine to 6-halogenation to give a 6-halide of the derivative, and then subjecting it to 2′-deoxylation/substitution with a fluorine atom or the like, followed by further subjecting it to substitution with an amino group, a hydroxyl group or any other intended substituent at the 6-positioned halogen atom, nucleoside derivatives are produced at a high yield.Type: ApplicationFiled: August 2, 2002Publication date: January 2, 2003Applicant: AJINOMOTO CO. INCInventors: Satoshi Takamatsu, Satoshi Katayama, Naoko Hirose, Kunisuke Izawa, Tokumi Maruyama
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Patent number: 6500946Abstract: Novel intermediates of nucleoside derivatives, of which the 6-position of the nucleic acid base moiety is substituted with a halogen atom, are produced. Using those novel intermediates, even substrates, of which the 3′-position of the saccharide moiety is deoxylated, can be substituted at the 2′-position at an extremely high yield. Specifically, by subjecting a 3′-deoxy derivative of inosine to 6-halogenation to give a 6-halide of the derivative, and then subjecting it to 2′-deoxylation/substitution with a fluorine atom or the like, followed by further subjecting it to substitution with an amino group, a hydroxyl group or any other intended substituent at the 6-positioned halogen atom, nucleoside derivatives are produced at a high yield.Type: GrantFiled: May 10, 2000Date of Patent: December 31, 2002Assignee: Ajinomoto Co., Inc.Inventors: Satoshi Takamatsu, Satoshi Katayama, Naoko Hirose, Kunisuke Izawa, Tokumi Maruyama
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Patent number: 6479463Abstract: Novel purine L-nucleoside compounds are disclosed, in which both the purine rings and the sugar are either modified, functionalized or both. The novel compounds or pharmaceutically acceptable esters or salts thereof may be used in pharmaceutical compositions, and such compositions may be used to treat an infection, an infestation, a neoplasm, or an autoimmune disease. The novel compounds may also be used to modulate aspects of the immune system, including modulation of Th1 and Th2.Type: GrantFiled: June 16, 2000Date of Patent: November 12, 2002Assignee: ICN Pharmaceuticals, Inc.Inventors: Guangyi Wang, Robert Tam, Devron Averett
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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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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: 6407077Abstract: Compounds and pharmaceutical compositions active against HIV are provided, as is a method for the treatment of HIV 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: June 18, 2002Assignees: Emory University, Centre National de la Recherche Scientifique, The UAB Research FoundationInventors: Gilles Gosselin, Jean-Louis Imbach, 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: 6376472Abstract: A compound of the formula wherein K is N; Q is CH2 or O; R6 is hydrogen, alkyl, allyl, 2-methylallyl, 2-butenyl, or cycloalkyl where the nitrogen of the ring of X is substituted by Y; E is O or S; Y is hydrogen, alkyl, aralkyl, substituted aralkyl, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, heterocyclylalkyl, or substituted heterocyclylalkyl; and n and p are independently 0, 1, 2, or 3, provided that n+p is at least 1; T is hydrogen, alkyl, alkylcarbonyl, alkylthiocarbonyl, halo, carboxyl, A and B are independently hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, or OR′; or a pharmaceutically acceptable salt thereof, a pharmaceutic-ally acceptable prodrug thereof, an N-oxide thereof, a hydrate thereof or a solvate thereof.Type: GrantFiled: October 16, 1998Date of Patent: April 23, 2002Assignee: Aventis Pharmaceuticals, Inc.Inventors: Michael R. Myers, Martin P. Maguire, Alfred P. Spada, William R. Ewing, Henry W. Pauls, Yong Mi Choi-Sledeski
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Patent number: 6271212Abstract: Pharmaceutical prodrug compositions are provided comprising azide derivatives of drugs which are capable of being converted to the drug in vivo. Azide derivatives of drugs having amine, ketone and hydroxy substituents are converted in vivo to the corresponding drugs, increasing the half-life of the drugs. In addition azide prodrugs are often better able to penetrate the blood-brain barrier than the corresponding drugs. Especially useful are azide derivatives of cordycepin, 2′-F-ara-ddI, AraA, acyclovir, penciclovir and related drugs. Useful azide prodrugs are azide derivatives of therapeutic alicyclic amines, ketones, and hydroxy-substituted compounds, including aralkyl, heterocyclic aralkyl, and cyclic aliphatic compounds, where the amine or oxygen moiety is on the ring, or where the amine or oxygen moiety is on an aliphatic side chain, as well as therapeutic purines and pyrimidines, nucleoside analogs and phosphorylated nucleoside analogs.Type: GrantFiled: March 3, 1998Date of Patent: August 7, 2001Assignees: University of Georgia Research Foundation Inc., Emory UniversityInventors: Chung K. Chu, Lakshimi Kotra, Kostantine K. Manouilov, Jinfa Du, Raymond Schinazi
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Patent number: 6252061Abstract: A novel process for preparing 2-halo-6-aminopurine derivatives and their analogs is disclosed. The method comprises halogenation of 2,6-diaminopurine derivatives at the C-2 position in a specific combination of aprotic polar and nonpolar organic solvents to give the corresponding halogenated derivatives.Type: GrantFiled: March 23, 1999Date of Patent: June 26, 2001Assignee: Reliable Biopharmaceutical, Inc.Inventors: UmaShanker Sampath, Lawrence Bartlett
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Patent number: 6252060Abstract: Compounds for treating hepatitis B infections. The compounds consist of nucleoside analogues having anti-hepatitis B activity which are linked, commonly through a 5′ phosphate of the pentose residue, to one of a selected group of lipids. The lipophilic nature of these compounds provides an advantage over the use of the nucleoside analogue alone, making it possible to incorporate them into the lamellar structure of liposomes, either alone or in combination with similar lipid molecules. In the form of appropriately sized liposomes, these anti-hepatitis B agents are preferentially taken up by the liver cells which have been found to harbor the target virus.Type: GrantFiled: April 4, 1994Date of Patent: June 26, 2001Assignee: NeXstar Pharmaceuticals, Inc.Inventor: Karl Y. Hostetler
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Patent number: 6245749Abstract: A method for the treatment of a host, and in particular, a human, infected with hepatitis B virus (HBV) is provided that includes administering an effective amount of a nucleotide prodrug of &bgr;- L-2′, 3′-dideoxyadenosine, wherein the prodrug component of the nucleotide provides controlled delivery of the active species.Type: GrantFiled: July 9, 1998Date of Patent: June 12, 2001Assignee: Emory UniversityInventors: Raymond F. Schinazi, Jean-Pierre Sommadossi, Gilles Gosselin, Jean-Louis Imbach
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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 -
Patent number: 6225460Abstract: Nucleotide analogs characterized by the presence of an amidate linked amino acid or an ester linked group which is bonded to the phosphorus atom of phosphonate nucleotide analogs are disclosed. The analogs comprise a phosphoamidate or ester bond that is hydrolyzed in vivo to yield a corresponding phosphonate nucleotide analog. Methods and intermediates for their synthesis and use are described.Type: GrantFiled: February 10, 1999Date of Patent: May 1, 2001Assignee: Gilead Sciences, Inc.Inventors: Norbert W. Bischofberger, Robert J. Jones, Murty N. Arimilli, Kuei-Ying Lin, Michael S. Louie, Lawrence R. McGee, Ernest J. Prisbe, William A. Lee, Kenneth C. Cundy
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Patent number: 6207650Abstract: Provided are very highly water soluble, stable, crystalline salts of 2′,3′-dideoxy-2′,3′-didehydrothymidine (“d4T”), 2′,3′-dideoxyinosine (“ddI”), and 2′,3′-dideoxy-2′-fluoroinosine (“F-ddI”). Such salts are useful as intermediates or as antiviral agents.Type: GrantFiled: December 6, 1991Date of Patent: March 27, 2001Assignee: Bristol-Myers Squibb CompanyInventors: Joseph B. Bogardus, Murray A. Kaplan, Robert K. Perrone
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Patent number: 6194390Abstract: A method for inhibiting replication of reverse transcriptase dependent virus in plant or animal cells, comprising the step of administering to said cells a compound that depletes the intracellular pool of deoxyribonucleoside phosphate in an amount effective to inhibit replication of said virus. Hydroxyurea is one such suitable compound. Also disclosed is a method for producing incomplete reverse-transcriptase dependent viral DNA, by administering a deoxyribonucleoside phosphate-depleting drug to cells infected with such a virus.Type: GrantFiled: February 3, 2000Date of Patent: February 27, 2001Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Franco Lori, Andrea Cara, Wen-Yi Gao, Robert C. Gallo