FIELD: chemistry.
SUBSTANCE: invention relates to a novel form of [[(S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]mono[3-(hexadecyloxy)propyl]ester of phosphonic acid, characterised by an X-ray diffraction pattern which includes peaks at angles 2θ of about 5.5, 19.3, 20.8 and 21.3 degrees and a purity of more than 91%, which can be used in the pharmaceutical industry, as well as to a method for production thereof. The disclosed method includes reacting cytosine with (S)-trityl glycidyl ether in the presence of a metal carbonate to form (S)-N1-[(2-hydroxy-3-triphenylmethoxy)propyl]cytosine; reacting (S)-N1-[(2-hydroxy-3-triphenylmethoxy)propyl]cytosine with a sodium salt of mono[3-(hexadecyloxy)propyl]ether of p-[[[(4-methylphenyl)sulphonyl]oxy]methyl]phosphonic acid in the presence of magnesium di-tert-butoxide to form [[(S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)-2-(triphenylmethoxy)ethyl]methyl]mono[3-(hexadecyloxy)propyl]ester of phosphonic acid; removing the protective group to obtain [[(S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]mono[3-(hexadecyloxy)propyl]ester of phosphonic acid and re-crystallisation thereof from methanol, ethanol, isopropanol, methanol:acetone:water, methanol:acetone or methanol:water systems.
EFFECT: disclosed is a novel form of a biologically active compound, which is convenient for producing prodrugs, and a novel efficient method for production thereof.
17 cl, 9 dwg, 14 ex, 22 tbl
| Title | Year | Author | Number |
|---|---|---|---|
| METHODS OF PRODUCING OPTICALLY ACTIVE CIS-2-HYDROXYMETHYL-4-(CYTOSIN-1'-YL)-1,3-OXATHIOLANE OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF | 2005 |
|
RU2430919C2 |
| PHOSPHONATE DERIVATIVES | 2000 |
|
RU2258707C2 |
| METHOD OF PRODUCING CONDENSED IMIDAZOLE DERIVATIVES | 2016 |
|
RU2734818C2 |
| 1,6-DIAZABICYCLO[3,2,1]OCTAN-7-ONА DERIVATIVES AND USING THEM IN TREATING BACTERIAL INFECTIONS | 2012 |
|
RU2570423C2 |
| ABT-263 CRYSTALLINE FORMS AND SOLVATES FOR TREATMENT OF BCL-2 PROTEIN RELATED DISEASES | 2010 |
|
RU2551376C2 |
| HIGH PENETRATION COMPOSITIONS OR PRODRUGS OF ANTIMICROBIALS AND ANTIMICROBIAL-RELATED COMPOUNDS | 2010 |
|
RU2586287C2 |
| METHOD OF SYNTHESIS OF ANALOGUES OF HORMONES OF THE THYROID GLAND AND THEIR POLYMORPHS | 2013 |
|
RU2668960C2 |
| PHARMACEUTICAL COMPOSITIONS INCLUDING NEP (NEUTRAL ENDOPEPTIDASE) INHIBITORS, INHIBITORS OF ENDOGENOUS ENDOTHELIN-PRODUCING SYSTEM AND HMG (HYDROXYMETHYLGLUTARYL) CoA REDUCTASE INHIBITORS | 2005 |
|
RU2410118C2 |
| METHOD FOR SYNTHESIS OF THYROID HORMONE ANALOGUES AND THEIR POLYMORPHS | 2021 |
|
RU2802282C2 |
| 4'-SUBSTITUTED NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS AND PRODUCTION THEREOF | 2016 |
|
RU2720811C2 |
