Nucleoside phosphoramidates

• US 8,735,569 B2
• Filed: 07/08/2013
• Issued: 05/27/2014
• Est. Priority Date: 05/20/2009
• Status: Active Grant

• Current Assignee: Gilead Sciences Inc.
• Original Assignee: Gilead Pharmasset LLC (Gilead Sciences Inc.)
• Inventors: Ross, Bruce S., Sofia, Michael Joseph, Pamulapati, Ganapati Reddy, Rachakonda, Suguna, Zhang, Hai-Ren, Chun, Byoung-Kwon, Wang, Peiyuan
• Primary Examiner(s): LEWIS, PATRICK T
• Application Number:
  US13/936,448
• Publication Number:
  US 20130310551A1
• Time in Patent Office: 323 Days
• Field of Search: None
• US Class Current: 536/25.33
• CPC Class Codes: A61K 31/7072 having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61K 9/20 Pills, tablets, discs, rods A61K9/0004, A61K9/0007, A61K9/0056, A61K9/0065 take precedence; for reconstitution of a drink A61K9/0095
• CPC Class Codes: A61P 31/14 for RNA viruses
• CPC Class Codes: C07B 2200/13 Crystalline forms, e.g. polymorphs
• CPC Class Codes: C07F 9/2479 Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 19/10 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 23/00 Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12 esters with inorganic acids C07H11/00; metal salts, see parent compounds

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.

Claims

1. A compound represented by the following structure:

3. The compound according to claim 1, wherein the compound is crystalline.

4. A process for preparing the compound according to claim 3, which comprises:

crystallizing a compound represented by the following structure;

6. A process for preparing a compound represented by the following structure (S_P-4):

2. A compound represented by the following structure:

5. A process for preparing a compound represented by the following structure (S_P-4):