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US 2004/0110786 A1Published application
4-Oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamides as antiviral agents
AssigneePharmacia & Upjohn Company
InventorsMark E. Schnute, Fred L. Ciske, Michael J. Genin, Joseph Walter Strohbach, Suvit Thaisrivongs
Life of this patent
Estimating the term…
Abstract
The present invention provides a compound of formula as described herein, which are useful as antiviral agents, in particular, as agents against viruses of the herpes family.
Claims55
A compound of a compound of formula I:
- 37
- its enantiomeric, diastereomeric, or tautomeric isomer thereof, or a pharmaceutically acceptable salt thereof wherein,
- G is phenyl substituted with from one (1) to five (5) R1 substituents;
- each R1 is independently
- (a) Cl,
- (b) Br,
- (c) F,
- (d) CN,
- (e) C1-7alkyl, or
- (f) NO2;
- R2 is
- (a) H,
- (b) R5,
- (c) NR7R8,
- (d) SO2R10, or
- (e) OR9;
- A is C1-7alkyl;
- W is a five- (5) or six- (6) membered heterocyclic ring having one (1), two (2) or three (3) heteroatoms selected from the group consisting of O, S(O)k, and N wherein W is optionally substituted with one or more OH, oxo (═O), or C1-7alkyl;
- B is
- (a) C1-7alkyl optionally substituted by OH or NR7R8,
- (b) O, or
- (c) NR11;
- R3 is
- (a) phenyl, optionally fused to a benzene or pyridine ring, and optionally substituted by R12, wherein optionally any two adjacent R12 substituents taken together constitute a group of the formula —O(CH2)O—, —(NH)C(═O)(CH2)jO—, or —CH2)i—, or
- (b) a five- (5) or six- (6) membered heteroaryl bonded via a carbon atom having one (1), two (2), or three (3) heteroatoms selected from the group consisting of O, S, and N—Z, wherein R3 is optionally fused to a benzene or pyridine ring, and optionally substituted with one or more R12, wherein Z is absence, H, or C1-4alkyl;
- R4 is
- (a) H,
- (b) halo, or
- (c) C1-4alkyl optionally substituted by halo;
- R5 is
- (a) (CH2)mOCH2CH2OR11,
- (b) het, wherein said het is bound via a carbon atom,
- (c) aryl,
- (d) C1-7alkyl which may be partially unsaturated and is optionally substituted by one or more R6 substituents, or
- (e) C3-8cycloalkyl which may be partially unsaturated and optionally substituted by one or more R6 or C1-7alkyl optionally substituted by R6;
- R6 is
- (a) OR9,
- (b) SR9,
- (c) NR7R8,
- (d) halo,
- (e) CONR7R8,
- (f) CO2R9,
- (g) het,
- (h) phenyl, optionally substituted by R12,
- (i) CN,
- (j) oxo,
- (k) SO2NR9R11,
- (l) SOmR10, or
- (m) P(═O)(OR11)(R11);
- R7 and R8 are independently
- (a) H,
- (b) aryl,
- (c) C1-7alkyl which may be partially unsaturated and is optionally substituted by one or more NR11R11, OR11, SR11, SOmR10, CONR11R11, CO2R11, het, aryl, cyano, or halo,
- (d) C3-8cycloalkyl,
- (e) (C═O)R10, or
- (f) R7 and R8 together with the nitrogen to which they are attached form a het;
- R9 is
- (a) H,
- (b) aryl,
- (c) het, wherein the het is bound through a carbon atom,
- (d) C1-4alkyl which is optionally partially unsaturated and is optionally substituted by one or more aryl, het, OR11, SR11, NR11R11, halo, or C3-8cycloalkyl substituents and which C3-8cycloalkyl is optionally substituted by OR11, or
- (e) C3-8cycloalkyl which is optionally partially unsaturated and is optionally substituted by one or more halo, OR11, SR11, or NR11R11substituents;
- R10 is
- (a) aryl,
- (b) het,
- (c) C1-7alkyl which is optionally partially unsaturated and is optionally substituted by one or more aryl, het, OR11, SR11, NR11R11, halo, or C3-8cycloalkyl substituents and which C3-8cycloalkyl is optionally substituted by OR11, or
- (d) C3-8cycloalkyl which is optionally partially unsaturated and is optionally substituted by one or more halo, OR11, SR11, or NR11R11 substituents;
- R11 is
- (a) H, or
- (b) C1-7alkyl;
- R12 is
- (a) halo,
- (b) OR14,
- (c) SR11,
- (d) NR7R8,
- (e) phenyl, optionally substituted by halo, C1-7alkyl, or C1-7alkoxy,
- (f) C1-7alkyl which is optionally partially unsaturated and optionally substituted by R13,
- (g) cyano,
- (h) nitro,
- (i) CONR7R8,
- (j) SO2NR7R8,
- (k) CO2R11, or
- (l) NHC(═O)R11;
- R13 is
- (a) phenyl, optionally substituted by halo, C1-7alkyl, or C1-7alkoxy,
- (b) OR11,
- (c) O(CH2CH2O)nR11,
- (d) NR7R8or
- (e) halo;
- R14 is
- (a) H
- (b) alkyl, optionally substituted by halo,
- (c) phenyl, optionally substituted by halo, C1-7alkyl, or C1-7alkoxy, or
- (d) —(CH2CH2O)nOR11;
- wherein any aryl is optionally substituted with one or more substituents selected from the group consisting of halo, OR11, NR11R11, cyano, CO2R11, or C1-7alkyl in which said C1-7alkyl is optionally substituted by one to three halo, OR11, or NR11R11;
- wherein any het is optionally substituted with one or more substituents selected from the group consisting of halo, OR11, NR11R11, cyano, CO2R11, oxo (═O), or C1-7alkyl in which said C1-7alkyl is optionally substituted by one to three halo, OR11, or NR11R11;
- i is 3 or 4;
- j is 0 or 1;
- k is 0, 1, or 2;
- each n is independently 1, 2, 3, 4 or 5;
- and
- each m is independently 1 or 2;
99 more elements
Dependencies are inferred from the claim text.