Substituted aliphanes, cyclophanes, heteraphanes, heterophanes, hetero-heteraphanes and metallocenes useful for treating HCV infections

Patent metadata

Field	Value
Publication number	US-9468629-B2
Application number	US-201514972827-A
Country	US
Kind code	B2
Filing date	Dec 17, 2015
Priority date	May 27, 2011
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

The present disclosure provides substituted aliphanes, cyclophanes, heteraphanes, heterophanes, hetero-heteraphanes and metallocenes, of Formula I

D-M-D  (Formula I)

useful as antiviral agents. In certain embodiments disclosed herein M is a group —P-A-P— where A is

Certain substituted aliphanes, cyclophanes, heteraphanes, heterophanes, hetero-heteraphanes and metallocenes disclosed herein are potent and/or selective inhibitors of viral replication, particularly Hepatitis C virus replication. Pharmaceutical compositions/and combinations containing one or more substituted aliphanes, cyclophanes, heteraphanes, heterophanes, hetero-heteraphanes and metallocenes and a pharmaceutically acceptable carrier are also provided by this disclosure. Methods for treating viral infections, including Hepatitis C viral infections are provided by the disclosure.

First claim

What is claimed is:

1. A compound represented by the structure:

wherein R 1 is a protecting group selected from the group consisting of acetyl, benzoyl, tert-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), p-methoxybenzylcarbonyl (Moz), 9-fluorenylmethyloxycarbonyl (FMOC), benzyl, p-methoxybenzyl, 3,4-dimethoxybenzyl, and p-methoxyphenyl; and
LG 1 is halo.

2. The compound of claim 1 , wherein LG 1 is bromide.

3. The compound of claim 1 , wherein LG 1 is iodide.

4. The compound of claim 1 , having the structure:

5. A compound represented by the structure:

wherein R 1 is a protecting group selected from the group consisting of acetyl, benzoyl, tert-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), p-methoxybenzylcarbonyl (Moz), 9-fluorenylmethyloxycarbonyl (FMOC), benzyl, p-methoxybenzyl, 3,4-dimethoxybenzyl, and p-methoxyphenyl; and
LG 1 is halo.

6. The compound of claim 5 , wherein LG 1 is bromide.

7. The compound of claim 5 , wherein LG 1 is iodide.

8. The compound of claim 5 , having the structure:

9. A compound represented by the structure:

wherein R 1 is a protecting group selected from the group consisting of acetyl, benzoyl, tert-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), p-methoxybenzylcarbonyl (Moz), 9-fluorenylmethyloxycarbonyl (FMOC), benzyl, p-methoxybenzyl, 3,4-dimethoxybenzyl, and p-methoxyphenyl; and
LG 2 is a 4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl group.

10. The compound of claim 9 , having the structure:

11. A compound represented by the structure:

wherein R 1 is hydrogen or a protecting group selected from the group consisting of acetyl, benzoyl, tert-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), p-methoxybenzylcarbonyl (Moz), 9-fluorenylmethyloxycarbonyl (FMOC), benzyl, p-methoxybenzyl, 3,4-dimethoxybenzyl, and p-methoxyphenyl.

12. The compound of claim 11 , having the structure:

13. The compound of claim 11 , having the structure:

Assignees

• Achillion Pharmaceuticals Inc
• Achillion Pharmaceuticals Inc

Inventors

• Wiles Jason Allan
• Wang Qiuping
• Hashimoto Akihiro
• Pais Godwin
• Wang Xiangzhu
• Gadhachanda Venkat
• Phadke Avinash
• Deshpande Milind
• Chen Dawei

Classifications

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title

• C07F17/02

  of metals of Groups 8, 9 or 10 of the Periodic Table · CPC title

• A61K31/439

  the ring forming part of a bridged ring system, e.g. quinuclidine (8-azabicyclo [3.2.1] octanes A61K31/46) · CPC title

• C07D453/06

  containing isoquinuclidine ring systems · CPC title