Patents Assigned to Solux Corporation
-
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
-
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
-
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
-
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
-
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
-
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