Nucleoside phosphoramidates

Patent metadata

Field	Value
Publication number	US-9284342-B2
Application number	US-201313925078-A
Country	US
Kind code	B2
Filing date	Jun 24, 2013
Priority date	May 20, 2009
Publication date	Mar 15, 2016
Grant date	Mar 15, 2016

Abstract

Disclosed herein are nucleoside phosphoramidates and their use as agents for treating viral diseases. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful as inhibitors of HCV NS5B polymerase, as inhibitors of HCV replication and for treatment of hepatitis C infection in mammals.

First claim

The invention claimed is:

1. A crystalline compound represented by the formula (S P -4):

having XRPD 2θ-reflections (°) at about: 6.1 and 12.7.

2. A pharmaceutical composition comprising the crystalline compound according to claim 1 and a pharmaceutically acceptable medium.

3. A method of treating a hepatitis C virus infection in a human comprising administering to the human an effective amount of the crystalline compound according to claim 1 .

4. The method according to claim 3 further comprising administering to the human another antiviral agent.

5. A process for preparing the crystalline compound according to claim 1 comprising:
exposing a second crystalline compound represented by the formula (S P -4):

having an XRPD diffraction pattern substantially as shown in FIG. 3 or FIG. 4 to atmospheric humidity to provide a first composition.

6. The process according to claim 5 further comprising:
grinding the first composition into a powder; and
allowing the powder to stand in an open vessel.

7. A process for preparing the crystalline compound according to claim 1 comprising:
suspending a second crystalline compound represented by the formula (S P -4):

having an XRPD diffraction pattern substantially as shown in FIG. 3 or FIG. 4 in water to provide a suspension.

8. The process according to claim 7 further comprising heating the suspension.

9. The process according to claim 8 further comprising cooling the suspension.

Assignees

• Gilead Pharmasset Llc

Inventors

• Ross Bruce S
• Sofia Michael Joseph
• Pamulapati Ganapati Reddy
• Rachakonda Suguna
• Zhang Hai-Ren
• Chun Byoung-Kwon
• Wang Peiyuan

Classifications

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title

• C07H23/00

  Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12 (esters with inorganic acids C07H11/00) · CPC title

• C07H19/10 Primary

  with the saccharide radical esterified by phosphoric or polyphosphoric acids · CPC title

• A61P31/14

  for RNA viruses · CPC title

• A61K31/7072 Primary

  having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine · CPC title