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US 2016/0096842 A1Published application
Anti-influenza compositions and methods
AssigneeBioCryst Pharmaceuticals, Inc.
InventorsWilliam P. Sheridan, Shanta Bantia, Pravin L. Kotian, Yarlagadda S. Babu
Life of this patent
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Abstract
Disclosed are novel compounds comprising an imino-ribose derivative covalently linked to a carbocycle or heterocycle. Pharmaceutical compositions comprising the compounds of the invention are also described. Methods of inhibition, treatment and/or suppression of viral infections with the compounds of the invention are also described. The compositions or methods may optionally comprise one or more additional anti-viral agents.
Claims37
A compound of formula I:
- wherein
- R1 is selected from
- R2 is a bond, O, or S;
- R3 is a bond, C(═O), C(═S), C(═NR10), OC(═O), OC(═S), OC(═NR10), N(R11)C(═O), N(R11)C(═S), or N(R11)C(═NR10);
- R4 is OH or N(R15)2;
- R5 is H or N(R15)2;
- R6 is R11, C(═O)—R11, or SO2—R11;
- R7 is H or R12, wherein R12 is optionally substituted with one or more groups selected from lower alkyl, OR11, O—C(═O)—R11, O—C(═O)O—R11, O—C(═O)N(R11)2, O—C(═S)—R11, O—C(═S)O—R11, and O—C(═S)N(R11)2;
- R8 is OR11, O—C(═O)—R11, O—C(═O)O—R11, O—C(═O)N(R11)2, O—C(═S)—R11, O—C(═S)O—R11, O—C(═S)N(R11)2, N(R11)2, N(R11)C(═O)—R11, N(R11)C(═O)O(R11)2, N(R11)C(═O)N(R11)2, N(R11)C(═S)—R11, N(R11)C(═S)O—R11, N(R11)C(═S)N(R11)2, or N(R11)C(═NR10)N(R11)2;
- R9 is H, OH, O—C(═O)O—R11, O—C(═O)N(R11)2, O—C(═S)—R11, O—C(═S)O—R11, O—C(═S)N(R11)2;
- B is a bond, R12, R12—R13, R12—R13—R14, R12—O—R13, R12—S—R13, R12—N(R11)2—R13, R12—C(═O)—R13, R12—C(═S)—R13, R12—C(═NR10)—R13, R12—OC(═O)—R13, R12—C(═S)—R13, R12—OC(═NR10)—R13, R12—SC(═O)—R13, R12—SC(═S)—R13, R12—SC(═NR10)—R13, R12—N(R11)C(═O)—R13, R12—N(R11)C(═S)—R13, R12—N(R11)C(═NR10)—R13, R12—OC(═O)—OR13, R12—OC(═S)—OR13, R12—OC(═NR10)—OR13, R12—OC(═O)—N(R11)R13, R12—OC(═S)—N(R11)R13, R12—OC(═NR10)—N(R11)OR13, R12—OC(═O)—SR13, R12—OC(═S)—SR13, R12—OC(═NR10)—SR13, R12—N(R11)C(═O)—OR13, R12—N(R11)C(═S)—OR13, R12—N(R11)C(═NR10)—OR13, R12—N(R11)C(═O)—N(R11)R13, R12—N(R11)C(═S)—N(R11)R13, R12—N(R11)C(═NR10)—N(R11)R13, R12—N(R11)C(═O)—SR13, R12—N(R11)C(═S)—SR13, R12—N(R11)C(═NR10)—SR13, R12—SC(═O)—OR13, R12—SC(═S)—OR13, R12—SC(═NR10)—OR13, R12—SC(═O)—SR13, R12—SC(═S)—SR13, R12—SC(═NR10)—SR13, R12—SC(═O)—N(R11)R13, R12—SC(═S)—N(R11)R13, or R12—SC(═NR10)—N(R11)R13;
- wherein each R12, R13, and R14 are optionally substituted with one or more R15;
- R10 is independently H, lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, aryl, heteroaryl, OR11, or N(R11)2;
- R11 is independently H, lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, aryl, or heteroaryl;
- R12 is independently lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, aryl, or heteroaryl;
- R13 is independently lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, aryl, or heteroaryl;
- R14 is independently lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, aryl, or heteroaryl;
- and
- R15 is independently halogen, R10, OC(═O)R11, OC(═S)R11, OC(═NR10)R11, OC(═O)OR11, OC(═S)OR11, OC(═NR10)OR11, OC(═O)N(R11)2, OC(═S)N(R11)2, OC(═NR10)N(R11)2, N(R11)C(═O)R11, N(R11)C(═S)R11, N(R11)C(═NR10)R11, N(R11)C(═O)OR11, N(R11)C(═S)OR11, N(R11)C(═NR10)OR11, N(R11)C(═O)N(R11)2, N(R11)C(═S)N(R11)2, or N(R11)C(═NR10)N(R11)2;
- or a pharmaceutically acceptable salt thereof.
17 more elements
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5-7. (canceled)
9-11. (canceled)
13-15. (canceled)
(canceled)
A method for inhibiting, treating or suppressing a viral infection, comprising administering to a subject in need thereof an effective amount of a compound of formula I:
- wherein
- R1 is selected from
- R2 is a bond, O, or S;
- R3 is a bond, C(═O), C(═S), C(═NR10), OC(═O), OC(═S), OC(═NR10), N(R11)C(═O), N(R11)C(═S), or N(R11)C(═NR10);
- R4 is OH or N(R15)2;
- R5 is H or N(R15)2;
- R6 is R11, C(═O)—R11, or SO2—R11;
- R7 is H or R12, wherein R12 is optionally substituted with one or more groups selected from lower alkyl, OR11, O—C(═O)O—R11, O—C(═O)N(R11)2, O—C(═S)—R11, O—C(═S)O—R11, and O—C(═S)N(R11)2;
- R8 is OR11, O—C(═O)—R11, O—C(═O)O—R11, O—C(═O)N(R11)2, O—C(═S)—R11, O—C(═S)O—R11, O—C(═S)N(R11)2, N(R11)2, N(R11)C(═O)—R11, N(R11)C(═O)O(R11)2, N(R11)C(═O)N(R11)2, N(R11)C(═S)—R11, N(R11)C(═S)O—R11, N(R11)C(═S)N(R11)2, or N(R11)C(═NR10)N(R11)2;
- R9 is H, OH, O—C(═O)O—R11, O—C(═O)N(R11)2, O—C(═S)—R11, O—C(═S)O—R11, O—C(═S)N(R11)2;
- B is a bond, R12, R12—R13, R12—R13—R14, R12—O—R13, R12—S—R13, R12—N(R11)2—R13, R12—C(═O)—R13, R12—C(═S)—R13, R12—C(═NR10)—R13, R12—OC(═O)—R13, R12—C(═S)—R13, R12—OC(═NR10)—R13, R12—SC(═O)—R13, R12—SC(═S)—R13, R12—SC(═NR10)—R13, R12—N(R11)C(═O)—R13, R12—N(R11)C(═S)—R13, R12—N(R11)C(═NR10)—R13, R12—OC(═O)—OR13, R12—OC(═S)—OR13, R12—OC(═NR10)—OR13, R12—OC(═O)—N(R11)R13, R12—OC(═S)—N(R11)R13, R12—OC(═NR10)—N(R11)OR13, R12—OC(═O)—SR13, R12—OC(═S)—SR13, R12—OC(═NR10)—SR13, R12—N(R11)C(═O)—OR13, R12—N(R11)C(═S)—OR13, R12—N(R11)C(═NR10)—OR13, R12—N(R11)C(═O)—N(R11)R13, R12—N(R11)C(═S)—N(R11)R13, R12—N(R11)C(═NR10)—N(R11)R13, R12—N(R11)C(═O)—SR13, R12—N(R11)C(═S)—SR13, R12—N(R11)C(═NR10)—SR13, R12—SC(═O)—OR13, R12—SC(═S)—OR13, R12—SC(═NR10)—OR13, R12—SC(═O)—SR13, R12—SC(═S)—SR13, R12—SC(═NR10)—SR13, R12—SC(═O)—N(R11)R13, R12—SC(═S)—N(R11)R13, or R12—SC(═NR10)—N(R11)R13;
- wherein each R12, R13, and R14 are optionally substituted with one or more R15;
- R10 is independently H, lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, aryl, heteroaryl, OR11, or N(R11)2;
- R11 is independently H, lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, aryl, or heteroaryl;
- R12 is independently lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, aryl, or heteroaryl;
- R13 is independently lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, aryl, or heteroaryl;
- R14 is independently lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, aryl, or heteroaryl;
- and
- R15 is independently halogen, R10, OC(═O)R11, OC(═S)R11, OC(═NR10)R11, OC(═O)OR11, OC(═S)OR11, OC(═NR10)OR11, OC(═O)N(R11)2, OC(═S)N(R11)2, OC(═NR10)N(R11)2, N(R11)C(═O)R11, N(R11)C(═S)R11, N(R11)C(═NR10)R11, N(R11)C(═O)OR11, N(R11)C(═S)OR11, N(R11)C(═NR10)OR11, N(R11)C(═O)N(R11)2, N(R11)C(═S)N(R11)2, or N(R11)C(═NR10)N(R11)2;
- or a pharmaceutically acceptable salt thereof.
17 more elements
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(canceled)
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31-37. (canceled)
Dependencies are inferred from the claim text.