Guanosine Nucleotide Preparation Patents (Class 536/26.72)
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Patent number: 8759502Abstract: A protecting group for 1-nitrogen atom of an indole group including a sulfonylethyl carbamate group, wherein the protecting group is represented by the following General Formula (I) and capable of being removed from the 1-nitrogen atom of the indole group in an aprotic solvent: where R represents an alkyl group, a derivative of the alkyl group, a phenyl group or a derivative of the phenyl group.Type: GrantFiled: November 19, 2010Date of Patent: June 24, 2014Assignee: Apta Biosciences Ltd.Inventor: Tsuyoshi Fujihara
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Patent number: 8759318Abstract: Phosphoramidate compounds derived from guanine bases having enhanced therapeutic potency are provided, and these compounds in particular have enhanced potency with respect to treatment of viral infections, such as hepatitis C virus. Pharmaceutical compositions, methods of preparing the compounds, and methods of using the compounds and compositions to treat viral infections are also provided.Type: GrantFiled: January 11, 2010Date of Patent: June 24, 2014Assignees: Inhibitex, Inc., University College Cardiff Consultants LimitedInventors: Stanley Chamberlain, Jeff Hutchins, Karolina Madela, Christopher McGuigan, John Vernachio, Mohamed Aljarah, Arnaud Gilles
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Patent number: 8716263Abstract: A process for preparing phosphoramidate prodrugs or cyclic phosphate prodrugs of nucleoside derivatives, which is a compound, its stereoisomers, salts (acid or basic addition salts), hydrates, solvates, or crystalline forms thereof.Type: GrantFiled: December 23, 2009Date of Patent: May 6, 2014Assignee: Gilead Pharmasset LLCInventors: Byoung-Kwon Chun, Jinfa Du, Suguna Rachakonda, Bruce Ross, Michael Joseph Sofia, Ganapati Reddy Pamulapati, Wonsuk Chang, Hai-Ren Zhang, Dhanapalan Nagarathnam
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Publication number: 20140100186Abstract: A method of modifying a nucleotide or a nucleotide analogue to increase its overall effectiveness in treating an antiviral disease is provided. In some cases, a compound comprising a base, sugar, phosphonate moiety, and amino acid residue is provided, where the base-sugar may be a nucleoside, and the amino acid residue may be a tyrosine residue. In certain cases, the tyrosine residue contains a long chain alkyl group on the carboxamide group of the residue. Methods of inhibiting viral replication and methods of treating a viral infection are also provided.Type: ApplicationFiled: May 7, 2012Publication date: April 10, 2014Inventors: Charles E. McKenna, Boris A. Kashemirov, Ivan S. Krylov, Valeria M. Zakharova
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Publication number: 20130281682Abstract: A method for preparing a phosphitylated compound comprising the step of:—reacting a hydroxyl containing compound with a phosphitylating agent in the presence of an activator having the formula (I) wherein R=alkyl, cycloalkyl, aryl, aralkyl, heteroalkyl, heteroaryl R1, R2=either H or form a 5 to 6-membered ring together. X1, X2=independently either N or CH Y=H or Si(R4)3, with R4=alkyl, cycloalkyl, aryl, aralkyl, heteroalkyl, heteroaryl B=deprotonated acid. The hydroxyl containing compound is preferably a sugar moiety or a nucleoside or an oligomer derived therefrom.Type: ApplicationFiled: June 20, 2013Publication date: October 24, 2013Applicant: Girindus AGInventors: Meinholf Lange, Andreas Schönberger, Christina Kirchhoff, Olaf Grössel, Nadja Omelcenko, Andreas Hohlfeld, Fritz Link
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Patent number: 8450293Abstract: The invention provides analogs cyclic diguanosine monophosphate (c-di-GMP) having different substituents at the guanine C8 position.Type: GrantFiled: August 10, 2011Date of Patent: May 28, 2013Assignee: Rutgers, The State University of New JerseyInventors: Roger A. Jones, Elizabeth Veliath
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Publication number: 20120316328Abstract: A method for preparing a phosphitylated compound comprising the step of:—reacting a hydroxyl containing compound with a phosphitylating agent in the presence of an activator having the formula (I) wherein R=alkyl, cycloalkyl, aryl, aralkyl, heteroalkyl, heteroaryl R1, R2=either H or form a 5 to 6-membered ring together. X1, X2=independently either N or CH Y?H or Si(R4)3, with R4=alkyl, cycloalkyl, aryl, aralkyl, heteroalkyl, heteroaryl B=deprotonated acid. The hydroxyl containing compound is preferably a sugar moiety or a nucleoside or an oligomer derived therefrom.Type: ApplicationFiled: February 7, 2012Publication date: December 13, 2012Applicant: Girindus AGInventors: Meinolf Lange, Andreas Schönberger, Christina Kirchhoff, Olaf Grössel, Nadja Knaub, Andreas Hohlfeld, Fritz Link
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Patent number: 8173621Abstract: Cyclic phosphate of nucleoside derivatives for the treatment of viral infections in mammals, which is a compound, its stereoisomers, salts (acid or basic addition salts), hydrates, solvates, or crystalline forms thereof, represented by the following structure:Type: GrantFiled: June 5, 2009Date of Patent: May 8, 2012Assignee: Gilead Pharmasset LLCInventors: Jinfa Du, Dhanapalan Nagarathnam, Ganapati Reddy Pamulapati, Bruce S. Ross, Michael Joseph Sofia
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Publication number: 20110124592Abstract: Phosphoramidate derivatives of nucleoside compounds of formula I derived from bases such as adenine and guanine have enhanced therapeutic potency, in particular, enhanced potency with respect to the prophylaxis or treatment of a viral infection such as hepatitis C virus. The glycoside moiety of the nucleoside compound is suitably substituted at the ?-2? position with methyl and the phosphoramidate group, suitably comprises 1-naphthyl linked by —O— to the P atom.Type: ApplicationFiled: November 23, 2007Publication date: May 26, 2011Inventors: Christopher McGuigan, Plinio Perrone, Johan Neyts
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Patent number: 7935814Abstract: An object of the present invention is to provide a novel compound that is an agonist of guanosine-3?,5?-cyclic monophosphate and has an effect of activating protein kinase G. The present invention provides 8-guanosine-3?,5?-cyclic monophosphate compound which is represented by the following formula, and a pharmaceutical composition, especially a protein kinase G activating agent, which contains the 8-guanosine-3?,5?-cyclic monophosphate compound as an active ingredient.Type: GrantFiled: February 28, 2006Date of Patent: May 3, 2011Assignee: Kumamoto UniversityInventors: Takaaki Akaike, Teruo Akuta
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Publication number: 20100324278Abstract: The present invention relates to novel phosphoramidites, A-n-bz, C-n-bz, C-n-ac, G-n-ac and U are produced with an HPLC purity of greater than 98% and 31P NMR purity greater than 99%. A novel process of reverse 5??3? directed synthesis of RNA oligomers has been developed and disclosed. Using that method demonstrated high quality RNA synthesis with coupling efficiency approaching 99%.Type: ApplicationFiled: September 8, 2009Publication date: December 23, 2010Inventors: Suresh C. Srivastava, Divya Pandey, Satya P. Bajpai, Naveen P. Srivastava
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Patent number: 7825238Abstract: A method for treatment of HBV and HIV infections comprising administering the compound or salt of formula IgType: GrantFiled: January 18, 2006Date of Patent: November 2, 2010Assignee: Medivir ABInventors: Xiao-Xiong Zhou, Horst Wahling
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Publication number: 20100081802Abstract: A method for preparing a phosphitylated compound comprising the step of: -reacting hydroxyl containing compound with a phosphitylating agent in the presence of an activator having the formula (I) wherein R=alkyl, cycloalkyl, aryl, aralkyl, heteroalkyl, heteroaryl R1, R2=either H or form a 5 to 6-membered ring together. X1, X2=independently either N or CH Y?H or Si(R4)3, with R4=alkyl, cycloalkyl, aryl, aralkyl, heteroalkyl, heteroaryl B=deprotonated acid. The hydroxyl containing compound is preferably a sugar moiety or a nucleoside or an oligomer derived therefrom.Type: ApplicationFiled: December 15, 2005Publication date: April 1, 2010Applicant: Girindus AGInventors: Meinholf Lange, Andreas Schönberger, Christina Kirchhoff, Olaf Grössel, Nadja Omelcenko, Andreas Hohlfeld, Fritz Link
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Patent number: 6713623Abstract: Disclosed are novel bicyclic tris(anhydride)s useful as intermediates in the synthesis of biologically active compounds, and the compounds which may be synthesized from such intermediates.Type: GrantFiled: November 13, 2001Date of Patent: March 30, 2004Assignee: Pharmasset, Ltd.Inventors: Krzysztof W. Pankiewicz, Krystyna Lesiak, Kyoichi A. Watanabe
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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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Patent number: 6531589Abstract: The invention provides new methods for synthesizing oligonucleotides that allow for deprotection of the oligonucleotides under more mild conditions than existing methods. The invention further provides a nucleoside base protecting group that is stable under oligonucleotide synthesis conditions, but which can be removed under more mild conditions than existing protecting groups, as well as nucleoside synthons having such base protecting groups.Type: GrantFiled: February 8, 1996Date of Patent: March 11, 2003Assignee: Hybridon, Inc.Inventors: Radhakrishnan P. Iyer, Theresa Devlin, Ivan Habus, Dong Yu, Sudhir Agrawal, Nan-Hui Ho
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Patent number: 6399589Abstract: 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: December 10, 1998Date of Patent: June 4, 2002Assignee: ISIS Pharmaceuticals, Inc.Inventors: Gilles Gosselin, Jean-Louis Imbach, Christian Perigaud
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Patent number: 6329519Abstract: A compound of formula (I) wherein B1 is a radical of a nucleoside base, R1 is hydrogen or a hydroxy-protecting group, R2 is hydrogen, hydroxy or a 2′-nucleoside-modifying atom or group, R3 is an unsubstituted or substituted C1 to C10 alkyl, C2 to C10 alkenyl, C4 to C10 cycloalkylalkyl, C6 to C10 aryl or C7 to C13 aralkyl group, and Z is halogen or a group of formula (II) where R4 and R5 are each independently an unsubstituted or substituted C1 to C10 alkyl, C2 to C10 alkenyl, C4 to C10 cycloalkylalkyl, C6 to C10 aryl or C7 to C13 aralkyl group, or R4 is said group and R5 is hydrogen or R4 and R5 together with the nitrogen atom to which they are attached denote a five- to thirteen-membered heterocyclic ring, or Z is a group of formula (III): Nuc-O—, where Nuc is the residue of a natural or synthetic nucleoside or oligonucleotide after removal of a 5′-hydroxyl group therefrom attached through a 5′-methylene thereof to the indicated oxygen atom.Type: GrantFiled: March 15, 1999Date of Patent: December 11, 2001Assignee: ISIS Pharmaceuticals, Inc.Inventors: Stephen Paul Collingwood, Heinz Ernst Moser, Karl-Heinz Altmann, Mark Edward Douglas
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Patent number: 6326490Abstract: Disclosed are novel bicyclic tris(anhydride)s useful as intermediates in the synthesis of biolologically active compounds, and the compounds which may be synthesized from such intermediates.Type: GrantFiled: October 10, 1997Date of Patent: December 4, 2001Assignee: Pharmasset, Ltd.Inventors: Krzysztof W. Pankiewicz, Krystyna Lesiak, Kyoichi A. Watanabe
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Patent number: 6232465Abstract: A method for the stepwise creation of phosphodiester bonds between desired nucleosides resulting in the synthesis of polynucleotides having a predetermined nucleotide sequence by preparing an initiation substrate containing a free and unmodified 3′-hydroxyl group; attaching a mononucleotide selected according to the order of the predetermined nucleotide sequence to the 3′-hydroxyl of the initiating substrate in a solution containing a catalytic amount of an enzyme capable of catalyzing the 5′ to 3′ phosphodiester linkage of the 5′-phosphate of the mononucleotide to the 3′-hydroxyl of the initiating substrate, wherein the mononucleotide contains a protected 3′-hydroxyl group, whereby the protected mononucleotide is covalently linked to the initiating substrate and further additions are hindered by the 3′-hydroxyl protecting group. Methods in which a mononucleotide immobilized on a solid support is added to a free polynucleotide chain are also disclosed.Type: GrantFiled: June 7, 1995Date of Patent: May 15, 2001Inventors: Andrew C. Hiatt, Floyd Rose