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RU2401268C2 - CRYSTALLINE FORM OF (R)-6-CYCLOPENTYL-6-(2-(2,6-DIETHYLPYRIDIN-4-YL)ETHYL)-3-((5,7-DIMETHYL-[1,2,4]TRIAZOLO[1,5-a]PYRIMIDIN-2-YL)METHYL)-4-HYDROXY-5,6-DIHYDROPYRAN-2-ONE, USE THEREOF AND PHARMACEUTICAL COMPOSITION CONTAINING SAID COMPOUND - Google Patents

CRYSTALLINE FORM OF (R)-6-CYCLOPENTYL-6-(2-(2,6-DIETHYLPYRIDIN-4-YL)ETHYL)-3-((5,7-DIMETHYL-[1,2,4]TRIAZOLO[1,5-a]PYRIMIDIN-2-YL)METHYL)-4-HYDROXY-5,6-DIHYDROPYRAN-2-ONE, USE THEREOF AND PHARMACEUTICAL COMPOSITION CONTAINING SAID COMPOUND Download PDF

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RU2401268C2
RU2401268C2 RU2008105976/04A RU2008105976A RU2401268C2 RU 2401268 C2 RU2401268 C2 RU 2401268C2 RU 2008105976/04 A RU2008105976/04 A RU 2008105976/04A RU 2008105976 A RU2008105976 A RU 2008105976A RU 2401268 C2 RU2401268 C2 RU 2401268C2
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Russia
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approximately
pharmaceutical composition
crystalline form
diethylpyridin
dihydropyran
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RU2008105976/04A
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RU2008105976A (en
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Кристофер Фредерик МЭТТЬЮЗ (US)
Кристофер Фредерик МЭТТЬЮЗ
Роберт Уилльям СКОТТ (US)
Роберт Уилльям СКОТТ
Джон Ллойд ТАКЕР (US)
Джон Ллойд ТАКЕР
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Пфайзер Инк.
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Abstract

FIELD: chemistry.
SUBSTANCE: invention relates to a crystalline form of (R)-6-cyclopentyl-6-(2-(2,6-diethylpyridin-4-yl)ethyl)-3-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl)-4-hydroxy-5,6-dihydropyran-2-one, which exhibits characteristic peaks on an X-ray powder diffraction pattern expressed in two-theta degrees, selected from approximately 7.1, approximately 12.1 and approximately 16.1; or approximately 7.1, approximately 12.1 and approximately 17.5; or approximately 7.1, approximately 12.1 and approximately 23.5; or approximately 12.1, approximately 16.1 and approximately 17.5; or approximately 12.1, approximately 16.1 and approximately 23.5; or approximately 16.1, approximately 17.5 and approximately 23.5; or approximately 7.1, approximately 17.5 and approximately 23.5; or approximately 7.1, approximately 12.1 and approximately 23.5; or approximately 7.1, approximately 16.1 and approximately 23.5, and to a pharmaceutical composition based on said compound, which can be used in medicine to prepare a medicinal agent which acts on the hepatitis C virus (HCV) in HCV-infected mammals.
EFFECT: improved properties of derivatives.
12 cl, 1 tbl, 3 dwg, 11 ex

Description

Текст описания приведен в факсимильном виде.

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The text of the description is given in facsimile form.
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Claims (12)

1. Кристаллическая форма (R)-6-циклопентил-6-(2-(2,6-диэтилпиридин-4-ил)этил)-3-((5,7-диметил-[1,2,4]триазоло[1,5-а]пиримидин-2-ил)метил)-4-гидрокси-5,6-дигидропиран-2-она, показывающая характеристические пики в картине дифракции рентгеновских лучей на порошке, выраженные в градусах два-тета, выбранные из примерно 7,1, примерно 12,1 и примерно 16,1; или примерно 7,1, примерно 12,1 и примерно 17,5; или примерно 7,1, примерно 12,1 и примерно 23,5; или примерно 12,1, примерно 16,1 и примерно 17,5; или примерно 12,1, примерно 16,1 и примерно 23,5; или примерно 16,1, примерно 17,5 и примерно 23,5; или примерно 7,1, примерно 17,5 и примерно 23,5; или примерно 7,1, примерно 12,1 и примерно 23,5; или примерно 7,1, примерно 16,1 и примерно 23,5.1. The crystalline form of (R) -6-cyclopentyl-6- (2- (2,6-diethylpyridin-4-yl) ethyl) -3 - ((5,7-dimethyl- [1,2,4] triazolo [ 1,5-a] pyrimidin-2-yl) methyl) -4-hydroxy-5,6-dihydropyran-2-one, showing the characteristic peaks in the X-ray powder diffraction pattern, expressed in two-theta degrees, selected from approximately 7.1, about 12.1 and about 16.1; or about 7.1, about 12.1, and about 17.5; or about 7.1, about 12.1, and about 23.5; or about 12.1, about 16.1 and about 17.5; or about 12.1, about 16.1 and about 23.5; or about 16.1, about 17.5, and about 23.5; or about 7.1, about 17.5, and about 23.5; or about 7.1, about 12.1, and about 23.5; or about 7.1, about 16.1 and about 23.5. 2. Кристаллическая форма по п.1, показывающая характеристические пики в картине дифракции рентгеновских лучей на порошке, выраженные в градусах два-тета, примерно 7,1, примерно 12,1, примерно 16,1, примерно 17,5 и примерно 23,5.2. The crystalline form according to claim 1, showing the characteristic peaks in the X-ray powder diffraction pattern, expressed in two-theta degrees, about 7.1, about 12.1, about 16.1, about 17.5 and about 23, 5. 3. Кристаллическая форма по п.1, показывающая характеристические пики в спектре ЯМР в твердом состоянии, выраженные в млн-1, при примерно 154,6, примерно 153,0, примерно 151,2, примерно 146,4, примерно 146,0, примерно 121,6, примерно 120,4, примерно 119,7, примерно 118,8, примерно 110,2, примерно 100,7 и примерно 100,3.3. The crystalline form of claim 1, showing characteristic peaks in the NMR spectrum in the solid state, expressed in ppm-1, at about 154.6, about 153.0, about 151.2, about 146.4, about 146.0 , about 121.6, about 120.4, about 119.7, about 118.8, about 110.2, about 100.7, and about 100.3. 4. Кристаллическая форма по п.1, показывающая температуру плавления в интервале от примерно 162°С до примерно 165°С.4. The crystalline form according to claim 1, showing a melting point in the range from about 162 ° C to about 165 ° C. 5. Кристаллическая форма (R)-6-циклопентил-6-(2-(2,6-диэтилпиридин-4-ил)этил)-3-((5,7-диметил-[1,2,4]триазоло[1,5-а]пиримидин-2-ил)метил)-4-гидрокси-5,6-дигидропиран-2-она, показывающая характеристический пик в картине дифракции рентгеновских лучей на порошке, выраженный в градусах два-тета, при примерно 7,1, пик в спектре ЯМР в твердом состоянии, выраженный в млн-1, при примерно 154,6, и температуру плавления в интервале от примерно 162°С до примерно 165°С.5. The crystalline form of (R) -6-cyclopentyl-6- (2- (2,6-diethylpyridin-4-yl) ethyl) -3 - ((5,7-dimethyl- [1,2,4] triazolo [ 1,5-a] pyrimidin-2-yl) methyl) -4-hydroxy-5,6-dihydropyran-2-one, showing the characteristic peak in the X-ray powder diffraction pattern, expressed in two-theta degrees, at about 7 1, the peak in the NMR spectrum in the solid state, expressed in ppm-1, at about 154.6, and a melting point in the range from about 162 ° C to about 165 ° C. 6. Фармацевтическая композиция, содержащая кристаллическую форму (R)-6-циклопентил-6-(2-(2,6-диэтилпиридин-4-ил)этил)-3-((5,7-диметил-[1,2,4]триазоло[1,5-а]пиримидин-2-ил)метил)-4-гидрокси-5,6-дигидропиран-2-она по любому из пп.1-5 и фармацевтически приемлемый носитель.6. A pharmaceutical composition containing a crystalline form of (R) -6-cyclopentyl-6- (2- (2,6-diethylpyridin-4-yl) ethyl) -3 - ((5,7-dimethyl- [1,2, 4] triazolo [1,5-a] pyrimidin-2-yl) methyl) -4-hydroxy-5,6-dihydropyran-2-one according to any one of claims 1 to 5 and a pharmaceutically acceptable carrier. 7. Фармацевтическая композиция по п.6, содержащая одно или более чем одно другое антивирусное вещество.7. The pharmaceutical composition according to claim 6, containing one or more than one other antiviral substance. 8. Фармацевтическая композиция по п.7, где указанные одно или более чем одно другое антивирусное вещество представляют собой ингибиторы HCV.8. The pharmaceutical composition according to claim 7, where the specified one or more than one other antiviral substance are HCV inhibitors. 9. Фармацевтическая композиция по п.8, где указанные ингибиторы HCV выбраны из группы, состоящей из интерферона альфакон-1, природного интерферона, интерферона бета-1a, интерферона омега, интерферона гамма-1b, пегилированных форм IFN-α, интерлейкина-10, BILN 2061, амантадина, тимозина альфа-1, рибавирина и вирамидина.9. The pharmaceutical composition of claim 8, wherein said HCV inhibitors are selected from the group consisting of interferon alfacon-1, natural interferon, interferon beta-1a, interferon omega, interferon gamma-1b, pegylated forms of IFN-α, interleukin-10, BILN 2061, amantadine, thymosin alpha-1, ribavirin and viramidine. 10. Фармацевтическая композиция по п.9, где указанные ингибиторы HCV представляют собой пегилированные формы IFN-α и рибавирин.10. The pharmaceutical composition according to claim 9, where these HCV inhibitors are pegylated forms of IFN-α and ribavirin. 11. Фармацевтическая композиция по любому из пп.7-10 для одновременного, последовательного или раздельного введения.11. The pharmaceutical composition according to any one of claims 7 to 10 for simultaneous, sequential or separate administration. 12. Применение кристаллической формы (R)-6-циклопентил-6-(2-(2,6-диэтилпиридин-4-ил)этил)-3-((5,7-диметил-[1,2,4]триазоло[1,5-а]пиримидин-2-ил)метил)-4-гидрокси-5,6-дигидропиран-2-она по любому из пп.1-5 или фармацевтической композиции по любому из пп.6-10 для изготовления лекарственного средства для воздействия на вирус гепатита С (HCV) у HCV-инфицированного млекопитающего. 12. The use of the crystalline form of (R) -6-cyclopentyl-6- (2- (2,6-diethylpyridin-4-yl) ethyl) -3 - ((5,7-dimethyl- [1,2,4] triazolo [1,5-a] pyrimidin-2-yl) methyl) -4-hydroxy-5,6-dihydropyran-2-one according to any one of claims 1-5 or the pharmaceutical composition according to any one of claims 6-10 for the manufacture a drug for treating hepatitis C virus (HCV) in an HCV-infected mammal.
RU2008105976/04A 2005-08-24 2006-08-16 CRYSTALLINE FORM OF (R)-6-CYCLOPENTYL-6-(2-(2,6-DIETHYLPYRIDIN-4-YL)ETHYL)-3-((5,7-DIMETHYL-[1,2,4]TRIAZOLO[1,5-a]PYRIMIDIN-2-YL)METHYL)-4-HYDROXY-5,6-DIHYDROPYRAN-2-ONE, USE THEREOF AND PHARMACEUTICAL COMPOSITION CONTAINING SAID COMPOUND RU2401268C2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US71104205P 2005-08-24 2005-08-24
US60/711,042 2005-08-24
US74427306P 2006-04-04 2006-04-04
US60/744,273 2006-04-04
US60/804,644 2006-06-13

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1468423A3 (en) * 1984-04-17 1989-03-23 Феб Дойчес Хюдрирверк Родлебен (Фирма) Method of producing 5-pipyridine-7-[n- (n-pentyl)-n-(beta-oxyethyl)-amino]-s-triazolo (1,5-alpha)) pyrimidine
WO2003095441A1 (en) * 2002-05-10 2003-11-20 Pfizer Inc. Inhibitors of hepatitis c virus rna-dependent rna polymerase, and compositions and treatments using the same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1468423A3 (en) * 1984-04-17 1989-03-23 Феб Дойчес Хюдрирверк Родлебен (Фирма) Method of producing 5-pipyridine-7-[n- (n-pentyl)-n-(beta-oxyethyl)-amino]-s-triazolo (1,5-alpha)) pyrimidine
WO2003095441A1 (en) * 2002-05-10 2003-11-20 Pfizer Inc. Inhibitors of hepatitis c virus rna-dependent rna polymerase, and compositions and treatments using the same

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Effective date: 20130817