Patents Assigned to Biochemistry of the Academy of Sciences of the Czech Republic
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Publication number: 20190040036Abstract: Described herein are hypervalent iodine reagents.Type: ApplicationFiled: August 6, 2018Publication date: February 7, 2019Applicants: ETH Zurich, INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY ACADEMY OF SCIENCES OF THE CZECH REPUBLIC, V.V.IInventors: Vaclav MATOUSEK, Petr BEIER, Antonio TOGNI
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Patent number: 10040812Abstract: A hypervalent iodine of formula (I) or formula (II) wherein R is a nucleophile and a method for their production is described. Such compounds can be used for fluoroethylation of compounds carrying a reactive group. A preferred compound carrying a reactive group is cystein in any environment such as peptide targets.Type: GrantFiled: August 3, 2015Date of Patent: August 7, 2018Assignees: ETH ZURICH, INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY ACADEMY OF SCIENCES OF THE CZECH REPUBLIC, V.V.IInventors: Vaclav Matousek, Petr Beier, Antonio Togni
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Publication number: 20170233420Abstract: A hypervalent iodine of formula (I) or formula (II) wherein R is a nucleophile and a method for their production is described. Such compounds can be used for fluoroethylation of compounds carrying a reactive group. A preferred compound carrying a reactive group is cystein in any environment such as peptide targets.Type: ApplicationFiled: August 3, 2015Publication date: August 17, 2017Applicants: ETH Zurich, INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY ACADEMY OF SCIENCES OF THE CZECH REPUBLIC, V.V.IInventors: Vaclav MATOUSEK, Petr BEIER, Antonio TOGNI
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Patent number: 8153787Abstract: The present invention provides 5-azacytosine derivatives with antiviral activity, specifically having viral replication inhibiting properties, more particularly in DNA viruses such as pox-, papilloma- and herpes viruses in humans. The invention also provides pharmaceutical compositions comprising such 5-azacytosine derivatives as active ingredients in combination with pharmaceutically acceptable carriers, which are useful for the treatment of subjects suffering from viral infections.Type: GrantFiled: December 8, 2006Date of Patent: April 10, 2012Assignees: K.U. Leuven Research & Development, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech RepublicInventors: Antonin Holy, Marcela Krecmerova, Alois Piskala, Graciela Andrei, Robert Snoeck, Erik De Clercq, Johan Neyts, Lieve Naesens
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Publication number: 20090005346Abstract: The present invention provides 5-azacytosine derivatives with antiviral activity, specifically having viral replication inhibiting properties, more particularly in DNA viruses such as pox-, papilloma- and herpes viruses in humans. The invention also provides pharmaceutical compositions comprising such 5-azacytosine derivatives as active ingredients in combination with pharmaceutically acceptable carriers, which are useful for the treatment of subjects suffering from viral infections.Type: ApplicationFiled: December 8, 2006Publication date: January 1, 2009Applicants: K.U.Leuven Research & Development, Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech RepublicInventors: Antonin Holy, Marcela Krecmerova, Alois Piskala, Graciela Andrei, Erik De Clercq, Robert Snoeck, Johan Neyts, Lieve Naesens
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Patent number: 7115592Abstract: Novel compounds are provided having formula (I) where R1, R2, R3, R4, Z, X and * are defined herein. Also provided are antiviral methods for use and processes for synthesis of the compounds of formula (I).Type: GrantFiled: June 16, 2004Date of Patent: October 3, 2006Assignees: Institute of Organic Chemistry, Biochemistry of the Academy of Sciences of the Czech RepublicInventors: Jan M. R. Balzarini, Erik D. A. De Clercq, Antonin Holy, Dana Hockova
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Patent number: 6818633Abstract: Novel compounds are provided having formula (I) where R1, R2, R3, R4, Z, X and * are defined herein. Also provided are antiviral methods for use and processes for synthesis of the compounds of formula (I).Type: GrantFiled: June 28, 2002Date of Patent: November 16, 2004Assignees: Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Jan M. R. Balzarini, Erik D. A. De Clercq, Antonin Holy
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Patent number: 6653296Abstract: Resolved enantiomers of the formula (IA) and (IB) wherein B is a purine or pyrimidine base or aza and/or deaza analogs thereof are useful in antiviral pharmaceutical compositions to treat retroviral infections.Type: GrantFiled: February 2, 1995Date of Patent: November 25, 2003Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Antonin Holy, Hana Dvorakova, Erik Desire Alice De Clercq, Jan Marie Rene Balzarini
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Patent number: 6479673Abstract: Resolved enantiomers of the formula wherein B is a purine or pyrimidine base or aza and/or deaza analogs thereof are useful in antiviral pharmaceutical compositions to treat retroviral infections.Type: GrantFiled: February 8, 2000Date of Patent: November 12, 2002Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting, V.Z.W.Inventors: Antonin Holý, Hana Dvo{haeck over (r)}áková, Erik Desire Alice DeClercq, Jan Marie Rene Balzarini
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Patent number: 6057305Abstract: Resolved enantiomers of the formula ##STR1## wherein B is a purine or pyrimidine base or aza and/or deaza analogs thereof are useful in antiviral pharmaceutical compositions to treat retroviral infections.Type: GrantFiled: August 5, 1992Date of Patent: May 2, 2000Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting, v.z.w.Inventors: Antonin Holy, Hana Dvorakova, Erik Desire Alice DeClercq, Jan Marie Rene Balzarini
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Patent number: 5977061Abstract: Novel PMP, PME and HPMP and related compounds containing N-6 substituted 2,6-diaminopurine and adenine bases are provided. These compounds are useful in a variety of utilities, including as intermediates in the preparation of flame retardants, diagnostic reagents and therapeutics, including antivirals. Of particular note are compounds otherwise not known to possess anti-DNA viral activity that become potent inhibitors of DNA viruses upon substitution of the N-6 site, thereby providing a novel and unexpected and surprising use for such compounds.Type: GrantFiled: April 21, 1995Date of Patent: November 2, 1999Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting, v.z.w.Inventors: Antonin Holy, Erik Desire Alice De Clercq
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Patent number: 5869467Abstract: This invention relates to new nucleotide analogues and solves the technical problem of their use as biologically active compounds. The subject of this invention are N-(2-phosphonylmethoxyethyl) and N-(3-hydroxy-2-phosphonylmethoxypropyl) derivatives of pyrimidine and purine bases, easily accessible from heterocyolic bases and their N-(2-hydroxyethyl) or N-(2,3-dihydroxypropyl) derivatives. Some of the compounds, according to this invention, exhibit a marked antiviral activity or can be converted into such active compounds by chemical transformations.Type: GrantFiled: March 28, 1995Date of Patent: February 9, 1999Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Antonin Holy, Ivan Rosenberg, Erik D. A. De Clercq
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Patent number: 5854228Abstract: A series of compounds of Formula I which have anti-tumor activity, and are useful in treating viral infections, their compositions and use. ##STR1## In Formula I B is a purine or pyrimidine base; alk.sub.1 alk.sub.2 and alk.sub.3 are chemical bonds or alkylene groups; Q is hydrogen or hydroxyl; and R.sub.1 -R.sub.4 are hydrogen or alkyl.Type: GrantFiled: June 7, 1995Date of Patent: December 29, 1998Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Robert W. Webb, II, Joanne J. Bronson, John C. Martin
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Patent number: 5837871Abstract: Provided are compounds of the following formulae:A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula ##STR1## wherein X and X' are the same or different and are hydrogen or alkyl. R and R' are the same or different and are hydrogen, alkyl, hydroyalkyl or alkanoyl andB is a purine or pyrimidine base.Type: GrantFiled: June 7, 1995Date of Patent: November 17, 1998Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting, v.z.w.Inventors: Choung Un Kim, John C. Martin, Bing Uh Luh, Peter F. Misco
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Patent number: 5792756Abstract: There are disclosed novel oral prodrugs of phosphonate nucleotide analogs which are hydrolyzable under physiological conditions to yield compounds which are useful as antiviral agents, especially as agents effective against RNA and DNA viruses. They may also find use as antitumor agents.Type: GrantFiled: June 7, 1995Date of Patent: August 11, 1998Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: John E. Starrett, Jr., Muzammil M. Mansuri, John C. Martin, David R. Tortolani, Joanne J. Bronson
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Patent number: 5744600Abstract: A compound of the Formula I or Formula II ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, hydroxy, chlorine, fluorine, bromine, or an organic substituent having 1 to 5 carbon atoms and selected from acyloxy having a hydrocarbon stem of 1 to 4 carbon atoms, alkoxy, alkylthio, amino, alkylamino and dialkylamino;R.sup.3 and R.sup.4 are independently hydrogen, or organic phosphonic ester substituents having 1 to 12 carbon atoms and selected from alkyl, alkenyl, aryl, and aralkyl; andB is a heterocyclic group selected from the group consisting of pyrimidine, purine, triazine, deazapurine, and triazole, attached through a ring nitrogen atom thereof optionally substituted with 1 to 3 substituents selected from the group consisting of hydroxy, mercapto, amino, hydrazino, fluoro, chloro, bromo, iodo, C.sub.1 to C.sub.3 alkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C1-C3 alkoxy, and C1-C3 alkylthio;and the pharmaceutically acceptable acid addition, metal, and amine salts thereof.Type: GrantFiled: December 16, 1994Date of Patent: April 28, 1998Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Muzammil M. Mansuri, John C. Martin, Thomas W. Hudyma, Joanne J. Bronson, Louis M. Ferrara
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Patent number: 5733896Abstract: N-(3-Fluoro-2-phosphonylmethoxypropyl) derivatives of purine and pyrimidine heterocyclic bases, method of producing them and their use as active principles of drugs.The invention relates to suppression of multiplication of viruses, particularly retroviruses, by application of the new compounds, N-(3-fluoro-2-phosphonylmethoxypropyl) derivatives of purine and pyrimidine heterocyclic bases. These compounds are obtained by the reaction of the N-(3-fluoro-2-hydroxypropyl) derivatives of purine and pyrimidine heterocyclic bases with diesters of p-toluenesulfonyloxymethylphosphonic acid in the presence of sodium hydride.Type: GrantFiled: March 18, 1994Date of Patent: March 31, 1998Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Antonin Holy, Jindrich Jindrich, Erik De Clercq, Jan Balzarini
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Patent number: 5726174Abstract: Provided are compounds of the following formulae:A phosphonomethoxymethyoxymethyl purine/pyridimidine derivative of the formula ##STR1## wherein X and X' are the same or different and are hydrogen or alkyl. R and R' are the same or different and are hydrogen, alkyl, hydroxyalkyl or alkanoyl andB is a purine or pyrimidine base.A compound of formula (II) or (VIII) ##STR2## wherein the broken line is an optional bond; X, R and X' are the same or different and are H or alkyl with 1 to 6 carbon atoms;wherein in the compound of formula (II), Y and Z are the same or different and are H; OH; alkyl having 1 to 6 carbon atoms; alkyl having 1 to 6 carbon atoms which is substituted with halogen, hydroxy, amino or azido; or Y and Z are taken together to form an oxygen atom or a methylene group; or Y is taken together with X' to complete a cyclic phosphonate having the structure of formula (III) ##STR3## wherein R.sup.Type: GrantFiled: June 7, 1995Date of Patent: March 10, 1998Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Choung Un Kim, John C. Martin, Bing Uh Luh, Peter F. Misco
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Patent number: 5696263Abstract: Compounds are provided that generally have the structure BCH.sub.2 CH(R)OCH.sub.2 P(O)(OH).sub.2, wherein B is a purinyl or pyrimidinyl base and R is C.sub.1-2 alkyl substituted with azido or amino, straight or branched alkenyl of 2-6 carbon atoms or alkynyl of 2-6 carbon atoms, together with the monester and diesters of such compounds with a C.sub.1-5 alkanol, and the corresponding salts, hydrates, solvates, the (R) or (S) isomers and the racemic (RS) mixtures thereof. The compounds have desirable antiviral activity.Type: GrantFiled: December 6, 1994Date of Patent: December 9, 1997Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Kuo-Long Yu, Joanne J. Bronson, John C. Martin
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Patent number: 5696265Abstract: Provided are compounds of the following formulae:A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula ##STR1## wherein X and X' are the same or different and are hydrogen or alkyl. R and R' are the same or different and are hydrogen, alkyl, hydroxyalkyl or alkanoyl andB is a purine or pyrimidine base.A 4'-phosphonomethoxytetrahydrofuranyl-1'-purine-pyrimidine of the formula ##STR2## wherein X and X' are the same or different and are hydrogen or alkyl, Y and Z are the same or different and are hydrogen, hydroxyl or alkyl or Y+Z is an alkenyl, an epoxide or cyclopropyl, andB is a purine or pyrimidine base.Type: GrantFiled: June 7, 1995Date of Patent: December 9, 1997Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Choung Un Kim, John C. Martin, Bing Uh Luh, Peter F. Misco