Disclosed herein are nucleotide analogs, methods of synthesizing nucleotide analogs and methods of treating diseases and/or conditions such as a HCV infection with one or more nucleotide analogs.

Substituted nucleosides, nucleotides and analogs thereof

Disclosed herein are aza-pyridone compounds, pharmaceutical compositions that include one or more aza-pyridone compounds, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a disease and/or a condition, including an orthomyxovirus infection, with an aza-pyridone compounds. Examples of an orthomyxovirus viral infection include an influenza infection.

Aza-pyridone compounds and uses thereof

Disclosed herein are pharmaceutical compositions that can include a thionucleotide analog for use in combination therapy with other agents, Also disclosed herein are methods of treating diseases and/or conditions with a pharmaceutical composition that can include a thionucleotide analog in combination therapy with other agents.

Pharmaceutical combinations comprising a thionucleotide analog

Disclosed herein are methods of preparing a phosphorothioate nucleotide analog, which are useful in treating diseases and/or conditions such as viral infections.

Methods of preparing substituted nucleotide analogs

Described herein is a composition that includes a thionucleotide analogue and daclatasvir, or a pharmaceutically acceptable salt of the foregoing, for ameliorating and/or treating a hepatitis C viral infection.

Hepatitis C viral infection treatment using a combination of compounds

The present application relates to solid state forms, for example, crystalline forms of 2′-C-methyluridine-5′-(O-phenyl-N—(S)-1-(isopropoxycarbonyl)ethyl)thiophosphoramidate, pharmaceutical compositions that can include one or more solid forms of 2′-C-methyluridine-5′-(O-phenyl-N—(S)-1-(isopropoxycarbonyl)ethyl)thiophosphoramidate, and methods of treating or ameliorating diseases and/or conditions with one or more solid forms of 2′-C-methyluridine-5′-(O-phenyl-N—(S)-1-(isopropoxycarbonyl)ethyl)thiophosphoramidate. Also disclosed herein are methods of treating diseases and/or conditions with one or more solid forms of 2′-C-methyluridine-5′-(O-phenyl-N—(S)-1-(isopropoxycarbonyl)ethyl)thiophosphoramidate in combination with one or more other agents.

Solid Forms of a Thiophosphoramidate Nucleotide Prodrug

A method of preparing Compound (1): or a pharmaceutically acceptable salt thereof includes: a) reacting Compound (A) with 3,3- dimetylbut-l-yne in the presence of one or more palladium catalysts selected from the group consisting of Pd(PPh3)4 and Pd(PPh3)2Cl2, and one or more copper catalysts selected from the group consisting of Cul, CuBr, and CuCl, to generate Compound (B); b) treating Compound (B) with an acid to generate Compound (C): c) reducing the cyclohexanone of Compound (C) to cyclohexanol to generate Compound (D); and d) reacting Compound (D) with a base to generate Compound (1), wherein Compounds (A), (B), (C), and (D) are each as depicted herein.

Methods for preparation of thiophene compounds

La presente invention concerne les formes polymorphes M, H, P, X et ZA du compose (1) represente par la formule developpee suivante : . Un procede de preparation de la forme polymorphe M du compose (1) comprend une etape consistant a agiter un melange associant le compose (1) et un systeme de solvant contenant de l'isopropanol, de l'acetate d'ethyle, de l'acetate de n-butyle, de l'acetate de methyle, de l'acetone, de la 2-butanone (methylethylcetone (MEK)) ou de l'heptane, ou une combinaison de ceux-ci, a une temperature se situant dans un intervalle de 10 a 47 °C, en vue de l'obtention de la forme M du compose (1). Un procede de preparation de la forme polymorphe H du compose (1) comprend une etape consistant a agiter une solution du compose (1) a une temperature se situant dans un intervalle de 48 a 70 °C, en vue de l'obtention de la forme H du compose (1). Un procede de preparation de la forme polymorphe P du compose (1) comprend une etape consistant a agiter un melange associant le compose (1) et un systeme de solvant contenant un solvant choisi dans le groupe constitue du dichloromethane et du tetrahydrofurane (THF), ou une combinaison de ceux-ci, a temperature ambiante, en vue de l'obtention de la forme P du compose (1).
Un procede de preparation de la forme polymorphe X du compose (1) comprend une etape consistant a eliminer l'acetate d'ethyle du solvate d'acetate d'ethyle constituant la forme polymorphe G du compose (1). Un procede de preparation de la forme polymorphe ZA du compose (1) comprend une etape consistant a eliminer l'acetate de n-butyle du solvate d'acetate de n-butyle constituant la forme polymorphe A du compose (1).

Composés de type thiophène

L'invention concerne un procede de preparation du compose (1) : ou d'un sel de qualite pharmaceutique de celui-ci. Ce procede consiste : a) a faire reagir le compose (A) avec du 3,3-dimethylbut-1-yne en presence d'un ou de plusieurs catalyseurs a base de palladium choisis dans le groupe constitue par Pd(PPh 3 ) 4 et Pd(PPh 3 ) 2 Cl 2 , et d'un ou de plusieurs catalyseurs a base de cuivre choisis dans le groupe constitue par CuI, CuBr et CuCl, pour generer le compose (B); b) a traiter le compose (B) par un acide pour generer le compose (C) : c) a reduire la cyclohexanone du compose (C) en cyclohexanol pour generer le compose (D); d) a faire reagir le compose (D) avec une base pour generer le compose (1), les composes (A), (B), (C) et (D) etant chacun tels que representes par les presentes.

Procédés de préparation de composés du thiophène

La presente invention concerne un procede de preparation d'un solvate du compose (1), le procede comprenant l'agitation d'un melange contenant le compose (1) et un solvant souhaite. Le compose (1) est represente par la formule structurelle (I) suivante. Le solvate du compose (1) est choisi dans le groupe comprenant : le compose 1-H 2 O; le compose 1-ethanol, isopropanol; le compose 1-acetone; le compose 1-acetate d'ethyle; le compose 1-acetate d'isopropyle; le compose 1-acetate d'ethyle-2-methyl THF; le compose 1-ethanol; le compose 1-acetate de n-butyle; le compose 1-heptane; le compose 1-2-butanone; et le compose 1-acetate de methyle. Le rapport molaire compose 1/H 2 O va de 1/0,5 a 1/3.

Composés de thiophène

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