Patents by Inventor Victor Matvienko
Victor Matvienko has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20190382432Abstract: The present invention relates to a stable crystalline monohydrate of epirubicin hydrochloride having water content in the range between 2.7% and 3.5% (w/w) and being devoid of residual solvents as well as to a corresponding method for its production. The method comprises: (a) adding at least a first solvent and at least a second solvent to epirubicin hydrochloride, wherein the first solvent is a linear or branched C4 to C5 alcohol, and the second solvent is a linear or branched C2 to C3 alcohol; (b) adjusting in the solution obtained the water content to an amount in the range between 7% and 12% (w/w); and (c) heating the mixture to a temperature of 70° C. to 90° C. in order to allow crystallization.Type: ApplicationFiled: July 24, 2019Publication date: December 19, 2019Inventors: Alexander Zabudkin, Victor Matvienko, Alexey Matvyeyev
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Patent number: 10030043Abstract: The present invention relates to a method for the high yield production of the anticancer nucleoside clofarabine, the method comprising the preparation of 2-chloroadenosine by enzymatic transglycosylation between 2-chloroadenine and nucleosides, benzoylation, isomerization, sulfonate ester formation, fluorination, and deprotection.Type: GrantFiled: April 22, 2015Date of Patent: July 24, 2018Assignee: Synbias Pharma AGInventors: Alexander Zabudkin, Victor Matvienko, Iaroslav Matviienko, Volodymyr Sypchenko
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Publication number: 20170044204Abstract: The present invention relates to a method for the high yield production of the anticancer nucleoside clofarabine, the method comprising the preparation of 2-chloroadenosine by enzymatic transglycosylation between 2-chloroadenine and nucleosides, benzoylation, isomerization, sulfonate ester formation, fluorination, and deprotection.Type: ApplicationFiled: April 22, 2015Publication date: February 16, 2017Inventors: Alexander ZABUDKIN, Victor MATVIENKO, Iaroslav MATVIIENKO, Volodymyr SYPCHENKO
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Patent number: 9035032Abstract: A method of preparing the anthracyclin carminomycin using a starting material comprising daunorubicin. The method comprises reacting daunorubicin or N-protected daunorubicin with soft Lewis acids for the demethylation of the 4-methoxy group, resulting in a reaction mass. The reaction mass is treated with an aqueous solution of a strong organic acid or a mineral acid. After decomposition of the resulting carminomycin and Lewis acids reactive complex, the reaction mass is extracted using a water insoluble organic solvent. As a result, carminomycin is extracted as a base.Type: GrantFiled: December 13, 2006Date of Patent: May 19, 2015Assignee: SOLUX CORPORATIONInventors: Alexander F. Zabudkin, Victor Matvienko, Alexey Matveev, Aleksandr M. Itkin
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Patent number: 8846882Abstract: The present invention relates to a method for the synthesis of 4-demethoxydaunorubicin (idarubicin) having the chemical structure of formula (I), which involves the demethylation of 3?-Prot-daunorubicin in the presence of a soft Lewis acid. The method of the present invention does not comprise cleavage of the glycosidic linkage at carbon C7, thus resulting in a faster synthesis cycle and an improved yield of the final product.Type: GrantFiled: April 29, 2011Date of Patent: September 30, 2014Assignee: Synbias Pharma AGInventors: Alexander Zabudkin, Victor Matvienko, Alexey Matvyeyev
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Publication number: 20140271874Abstract: The present invention relates to a stable crystalline monohydrate of epirubicin hydrochloride having water content in the range between 2.7% and 3.5% (w/w) and being devoid of residual solvents as well as to a corresponding method for its production. The method comprises: (a) adding at least a first solvent and at least a second solvent to epirubicin hydrochloride, wherein the first solvent is a linear or branched C4 to C5 alcohol, and the second solvent is a linear or branched C2 to C3 alcohol; (b) adjusting in the solution obtained the water content to an amount in the range between 7% and 12% (w/w); and (c) heating the mixture to a temperature of 70° C. to 90° C. in order to allow crystallization.Type: ApplicationFiled: March 13, 2014Publication date: September 18, 2014Applicant: Synbias Pharma Ltd.Inventors: Alexander Zabudkin, Victor Matvienko, Alexey Matvyeyev
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Patent number: 8802830Abstract: A method of preparing an anthracyclin such as epirubicin from a starting material comprising 13-dihydrodaunorubicine (13-daunorubicinol). The method comprises producing N-Trifluoroacetyl-13-daunorubicinol from 13-daunorubicinol by acylation. The N-Trifluoroacetyl-13-daunorubicinol is reacted with an aprotic solvent and an acylating agent to produce an intermediate sulfoxy salt which is treated with a strong base to produce 4?-keto-N-Trifluoroacetyldaunorubicin. The 4?-keto-N-Trifluoroacetyldaunorubicin is reacted with a reducing agent, such as borohydride of an alkaline metal, to produce N-Trifluoroacetyl-4?-epi-daunorubicin. The N-Trifluoroacetyl-4?-epi-daunorubicin is hydrolyzed in a basic solution to produce an intermediate compound. The intermediate compound is reacted with a halogenizing agent to produce a 14-Hal-derivative. The 14-Hal derivative is hydrolized in the presence of a formate of an alkaline metal to produce the desired final compound.Type: GrantFiled: December 18, 2006Date of Patent: August 12, 2014Assignee: Solux CorporationInventors: Alexander F. Zabudkin, Victor Matvienko, Aleksandr M. Itkin, Alexey Matveev
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Patent number: 8357785Abstract: A method for the aralkylation of anthracyclins by utilizing an aralkylating agent R3—CH2X (for example, BnBr) in accordance with the reaction pathway describe by the scheme shown in FIG. 1. The present invention recognizes that 4-R1, 3?-N3-Daunomycines are suitable substrates for selective 4?-O-benzylation, yielding 4-R1, 3?-N3-4?-O-Aralkyl-Daunorubicines (in particular, 4?-O-Bn-Daunomycines). Thus, the present invention provides a pathway for a simple production of 4?-O-aralkylated derivatives of anthracyclines which can be effectively used to produce anthracyclines.Type: GrantFiled: May 23, 2008Date of Patent: January 22, 2013Assignee: Solux CorporationInventors: Alexander F. Zabudkin, Victor Matvienko, Alexey Matveev, Aleksandr M. Itkin
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Publication number: 20120277415Abstract: The present invention relates to a method for the synthesis of 4-demethoxydaunorubicin (idarubicin) having the chemical structure of formula (I), which involves the demethylation of 3?-Prot-daunorubicin in the presence of a soft Lewis acid. The method of the present invention does not comprise cleavage of the glycosidic linkage at carbon C7, thus resulting in a faster synthesis cycle and an improved yield of the final product.Type: ApplicationFiled: April 29, 2011Publication date: November 1, 2012Inventors: Alexander Zabudkin, Victor Matvienko, Alexey Matvyeyev
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Publication number: 20090176974Abstract: A method for the aralkylation of anthracyclins by utilizing an aralkylating agent R3-CH2X (for example, BnBr) in accordance with the reaction pathway describe by the scheme shown in FIG. 1. The present invention recognizes that 4-R1, 3?-N3-Daunomycines are suitable substrates for selective 4?-O-benzylation, yielding 4-R1, 3?-N3-4?-O-Aralkyl-Daunorubicines (in particular, 4?-O-Bn-Daunomycines). Thus, the present invention provides a pathway for a simple production of 4?-O-aralkylated derivatives of anthracyclines which can be effectively used to produce anthracyclines.Type: ApplicationFiled: May 23, 2008Publication date: July 9, 2009Inventors: Alexander F. Zabudkin, Victor Matvienko, Alexey Matveev, Aleksandr M. Itkin
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Publication number: 20090099346Abstract: A crystalline form of epirubicin hydrochloride, named herein as “type II” crystalline epirubicin hydrochloride, has excellent thermal stability. Type II crystalline epirubicin hydrochloride has a powder X-ray diffraction pattern having average values of diffraction angle (2?) and relative intensity P(%) as presented in the following table: Diffraction Angle Relative Intensity 2? P % 5.2 100 9.2 24.5 10.3 14.3 13.7 32.8 14.6 10.9 15.5 49.3 18 19.1 19.2 21.1 19.4 11.3 20.7 19.9 21.1 29.7 21.4 18 22 23.1 22.5 69.6 23.6 20.5 24.1 72.1 25.8 67 26.1 15.9 27.7 47.9 29.8 38 31.9 14.1 32.1 16.7 36.4 16.6 37.7 18.8 41.1 14.Type: ApplicationFiled: October 5, 2008Publication date: April 16, 2009Inventors: Victor Matvienko, Alexey Matvyeyev, Aleksandr M. Itkin, Alexander F. Zabudkin
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Patent number: 7485707Abstract: A crystalline form of epirubicin hydrochloride, named herein as “type II” crystalline epirubicin hydrochloride, has excellent thermal stability. Type II crystalline epirubicin hydrochloride has a powder X-ray diffraction pattern having average values of diffraction angle (2?) and relative intensity P(%) as presented in the following table: Diffraction Angle Relative Intensity 2? P (%) 5.236 9.8 9.212 12.5 13.732 15.5 16.446 4.8 18.234 5 21.114 9.7 22.529 25.5 24.071 29.9 25.879 18.4 27.762 16.5 29.757 10.1 34.392 4.4 38.157 13.1 44.293 5.9 64.699 7.7 77.815 100.Type: GrantFiled: June 25, 2004Date of Patent: February 3, 2009Assignee: Solux CorporationInventors: Victor Matvienko, Alexey Matvyeyev, Alexander F. Zabudkin, Aleksandr M. Itkin
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Patent number: 7388083Abstract: A method of synthesizing R1, R2-substituted-4? (ax. or eq.)-OH anthracyclines and their corresponding salts of Formula (1) from daunorubicin or N-Trifluoroacetyl-4-R1-derivatives of daunorubicin, wherein R1 is defined as H, OH, and 4?-HO is defined as ax[ial]. The method includes producing N-Trifluoroacetyl daunorubicin and treating the N-Trifluoroacetyldaunorubicin or N-Trifluoroacetyl-4-R1-derivatives of daunorubicin, wherein R1 is defined as H, OH, with dimethylsulfoxide activated by different acylating agents. The attained intermediate product is then treated with a strong base (ex. tertiary amines) resulting in the 4?-keto-N-Trifluoroacetyl-4-R1 daunorubicin wherein R1 is defined as H, OH, OMe. The 4?-keto-N-Trifluoroacetyl-4-R1-daunorubicin is reacted with a reducing agent, a derivative of a borohydride of an alkaline metal MHBL3 , to produce N-Trifluoroacetyl-4?-epi-4-R1-daunorubicin.Type: GrantFiled: March 4, 2006Date of Patent: June 17, 2008Assignee: Solux CorporationInventors: Victor Matvienko, Alexey Matvyeyev, Alexander F. Zabudkin, Aleksandr M. Itkin
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Publication number: 20070142309Abstract: A method of preparing an anthracyclin such as epirubicin from a starting material comprising 13-dihydrodaunorubicine (13-daunorubicinol). The method comprises producing N-Trifluoroacetyl-13-daunorubicinol from 13-daunorubicinol by acylation. The N-Trifluoroacetyl-13-daunorubicinol is reacted with an aprotic solvent and an acylating agent to produce an intermediate sulfoxy salt which is treated with a strong base to produce 4?-keto-N-Trifluoroacetyldaunorubicin. The 4?-keto-N-Trifluoroacetyldaunorubicin is reacted with a reducing agent, such as borohydride of an alkaline metal, to produce N-Trifluoroacetyl-4?-epi-daunorubicin. The N-Trifluoroacetyl-4?-epi-daunorubicin is hydrolyzed in a basic solution to produce an intermediate compound. The intermediate compound is reacted with a halogenizing agent to produce a 14-Hal-derivative. The 14-Hal derivative is hydrolized in the presence of a formate of an alkaline metal to produce the desired final compound.Type: ApplicationFiled: December 18, 2006Publication date: June 21, 2007Inventors: Alexander Zabudkin, Victor Matvienko, Aleksandr Itkin, Alexey Matveev
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Publication number: 20070135624Abstract: A method of preparing the anthracyclin carminomycin using a starting material comprising daunorubicin. The method comprises reacting daunorubicin or N-protected daunorubicin with soft Lewis acids for the demethylation of the 4-methoxy group, resulting in a reaction mass. The reaction mass is treated with an aqueous solution of a strong organic acid or a mineral acid. After decomposition of the resulting carminomycin and Lewis acids reactive complex, the reaction mass is extracted using a water insoluble organic solvent. As a result, carminomycin is extracted as a base.Type: ApplicationFiled: December 13, 2006Publication date: June 14, 2007Inventors: Alexander Zabudkin, Victor Matvienko, Alexey Matveev, Aleksandr Itkin
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Publication number: 20060223766Abstract: A method of synthesizing R1, R2-substituted-4? (ax. or eq.)-OH anthracyclines and their corresponding salts of Formula (1) from daunorubicin or N-Trifluoroacetyl-4-R1-derivatives of daunorubicin, wherein R1 is defined as H, OH, and 4?-HO is defined as ax[ial]. The method includes producing N-Trifluoroacetyl daunorubicin and treating the N-Trifluoroacetyldaunorubicin or N-Trifluoroacetyl-4-R1-derivatives of daunorubicin, wherein R1 is defined as H, OH, with dimethylsulfoxide activated by different acylating agents. The attained intermediate product is then treated with a strong base (ex. tertiary amines) resulting in the 4?-keto-N-Trifluoroacetyl-4-R1 daunorubicin wherein R1 is defined as H, OH, OMe. The 4?-keto-N-Trifluoroacetyl-4-R1-daunorubicin is reacted with a reducing agent, a derivative of a borohydride of an alkaline metal MHBL3 , to produce N-Trifluoroacetyl-4?-epi-4-R1-daunorubicin.Type: ApplicationFiled: March 4, 2006Publication date: October 5, 2006Inventors: Victor Matvienko, Alexey Matvyeyev, Alexander Zabudkin, Aleksandr Itkin
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Publication number: 20060205684Abstract: A method of synthesizing 4-R-substituted anthracyclines and their corresponding salts from 4-demethyldaunorubicin includes the steps of treating 4-demethyldaunorubicin with a sulfonylating agent to form 4-demethyl-4-sulfonyl-R3-daunorubicin. 4-Demethyl-4-R3-sulfonyl-daunorubicin is then subject to a reducing agent in the presence of a transition metal catalyst in a temperature range of about 30° C. to about 100° C. in a polar aprotic solvent in an inert atmosphere. Protected 4-demethoxy-4-R-daunomycin then undergoes hydrolysis in a basic solution to form the 4-R-substituted anthracyclines. The novel method lacks the step of forming a stereospecific glycoside bond between aglycone and aminoglycoside. The method also increases the yield of the final product up to 30 to 40%.Type: ApplicationFiled: May 29, 2006Publication date: September 14, 2006Inventors: Alexander Zabudkin, Victor Matvienko, Alexey Matvyeyev, Aleksandr Itkin
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Patent number: 7053191Abstract: A method of synthesizing 4-R-substituted anthracyclines and their corresponding salts from 4-demethyldaunorubicin includes the steps of treating 4-demethyldaunorubicin with a sulfonylating agent to form 4-demethyl-4-sulfonyl-R3-daunorubicin. 4-Demethyl-4-R3-sulfonyl-daunorubicin is then subject to a reducing agent in the presence of a transition metal catalyst in a temperature range of about 30° C. to about 100° C. in a polar aprotic solvent in an inert atmosphere. Protected 4-demethoxy-4-R-daunomycin then undergoes hydrolysis in a basic solution to form the 4-R-substituted anthracyclines. The novel method lacks the step of forming a stereospecific glycoside bond between aglycone and aminoglycoside. The method also increases the yield of the final product up to 30 to 40%.Type: GrantFiled: April 23, 2004Date of Patent: May 30, 2006Assignee: Solux CorporationInventors: Alexander F. Zabudkin, Victor Matvienko, Alexey Matvyeyev, Aleksandr M. Itkin
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Publication number: 20060063726Abstract: A crystalline form of epirubicin hydrochloride, named herein as “type II” crystalline epirubicin hydrochloride, has excellent thermal stability. Type II crystalline epirubicin hydrochloride has a powder X-ray diffraction pattern having average values of diffraction angle (2?) and relative intensity P(%) as presented in the following table: Diffraction Angle Relative Intensity 2? P(%) 5.236 9.8 9.212 12.5 13.732 15.5 16.446 4.8 18.234 5 21.114 9.7 22.529 25.5 24.071 29.9 25.879 18.4 27.762 16.5 29.757 10.1 34.392 4.4 38.157 13.1 44.293 5.9 64.699 7.7 77.Type: ApplicationFiled: June 25, 2004Publication date: March 23, 2006Inventors: Victor Matvienko, Alexey Matvyeyev, Alexander Zabudkin, Aleksandr Itkin
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Publication number: 20040236086Abstract: A method of synthesizing 4-R-substituted anthracyclines and their corresponding salts from 4-demethyldaunorubicin includes the steps of treating 4-demethyldaunorubicin with a sulfonylating agent to form 4-demethyl-4-sulfonyl-R3-daunorubicin. 4-Demethyl-4-R3-sulfonyl-daunorubicin is then subject to a reducing agent in the presence of a transition metal catalyst in a temperature range of about 30° C. to about 100° C. in a polar aprotic solvent in an inert atmosphere. Protected 4-demethoxy-4-R-daunomycin then undergoes hydrolysis in a basic solution to form the 4-R-substituted anthracyclines. The novel method lacks the step of forming a stereospecific glycoside bond between aglycone and aminoglycoside. The method also increases the yield of the final product up to 30 to 40%.Type: ApplicationFiled: April 23, 2004Publication date: November 25, 2004Inventors: Alexander F. Zabudkin, Victor Matvienko, Alexey Matvyeyev, Aleksandr M. Itkin