US 7,582,626 B2Granted

5,6-dihydro-1H-pyridin-2-one compounds

AssigneeAnadys Pharmaceuticals, Inc.

InventorsChinh V. Tran, Frank Ruebsam, Yuefen Zhou, Peter Dragovich, Alan X. Xiang

Life of this patent

Estimating the term…

Abstract

The invention is directed to 5,6-dihydro-1H-pyridin-2-one compounds of Formula I and pharmaceutical compositions containing such compounds that are useful in treating hepatitis C virus infections: wherein Z is X is N or CR9; Y is —(CR4R5)n—; n is 2, 3, 4, or 5; and R1 through R9 are defined herein.

Claims20

Dependent claims

A compound of Formula I

wherein
Z is
X is N,
Y is —(CR4R5)n—,
n is 2, 3, 4, or 5,
R1 and R6 are independently H or C1-C6 alkyl,
R2, R3, R4, and R5 are independently H, C1-C6 alkyl, halo, or R2 and R3 or R4 and R5 combine with the atom to which they are attached to form a 3- to 6-membered spirocyclic ring,
R7 is H, C1-C6 alkyl, C3-C8 cycloalkyl, —C1-C6 alkylene(C3-C8 cycloalkyl), —C1-C6 alkylene(aryl), —C1-C6 alkylene(heterocyclyl), aryl, heterocyclyl, or —NR10R11, wherein R10 and R11 are independently H, C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C6 alkenyl
R8 is H, halo, nitro, —CHR12S(O)2R13, —C(S(O)2R13)═CHR12—, —NR13R14, —NR12S(O)2R13, or —NR12S(O)2NR13R14, wherein R12, R13, and R14 are independently H, C1-C6 alkyl C3-C8 cycloalkyl, aryl, or heterocyclyl, or R12 and R13 or R13 and R14 combine with the atom(s) to which they are attached to form a 5- or 6-membered heterocyclyl ring,
wherein the above alkyl, alkylene, aryl, cycloalkyl, or heterocyclyl moieties provided in R1, R2, R3, R4, R5, R6, R7, R10, R11, R12,R13, and R14 are each optionally and independently substituted by 1-3 substituents selected from
alkylamine,
amino,
aryl, cycloalkyl, heterocyclyl,
C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 alkylamine, C1-C6 dialkylamine, C2-C6 alkenyl, or C2-C6 alkynyl, wherein each of which may be interrupted by one or more hetero atoms,
carboxyl,
cyano,
halo,
hydroxy,
nitro,
—C(O)OH, —C(O)2—(C1-C6 alkyl), —C(O)2—(C3-C8 cycloalkyl), —C(O)2-(aryl), —C(O)2-(heterocyclyl), —C(O)2—(C1-C6 alkylene)aryl, —C(O)2—(C1-C6 alkylene)heterocyclyl, —C(O)2—(C1-C6 alkylene)cycloalkyl, —C(O)(C1-C6 alkyl), —C(O)(C3-C8 cycloalkyl), —C(O)(aryl), —C(O)(heterocyclyl), —C(O)(C1-C6 alkylene)aryl, —C(O)(C1-C6 alkylene)heterocyclyl, and —C(O)(C1-C6 alkylene)cycloalkyl,
wherein each of the above optional substituents can be further optionally substituted by 1-5 substituents selected from amino, cyano, halo, hydroxy, nitro, C1-C6 alkylamine, C1-C6 dialkylamine, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkenyl, and C1-C6 hydroxyalkyl, wherein each alkyl is optionally substituted by one or more halo substituents,
or a pharmaceutically acceptable salt, hydrate, tautomer or stereoisomer thereof.

19 more elements

A compound of Formula I

wherein
Z is
with one carbon-carbon double bond among the bonds indicated by the dotted line,
X is N,
m is 1 or 2,
R1 and R6 are independently H or C1-C6 alkyl,
R7 is H, C1-C6 alkyl, C3-C8 cycloalkyl, —C1-C6 alkylene(C3-C8 cycloalkyl), —C1-C6 alkylene(aryl), —C1-C6 alkylene(heterocyclyl), aryl, heterocyclyl, or —NR10R11, wherein R10 and R11 are independently H, C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C6-alkenyl
R8 is H, halo, nitro, —CHR12S(O)2R13, —C(S(O)2R13)═CHR12—, —NR13R14, —NR12S(O)2R13, or —NR12S(O)2NR13R14, wherein R12, R13, and R14 are independently H, C1-C6 alkyl, C3-C8 cycloalkyl, aryl, or heterocyclyl, or R12 and R13 or R13 and R14 combine with the atom(s) to which they are attached to form a 5- or 6-membered heterocyclyl ring,
wherein the above alkyl, alkylene, aryl, cycloalkyl, or heterocyclyl moieties provided in R1, R6, R7, R10, R11, R12, R13, and R14 are each optionally and independently substituted by 1-3 substituents selected from
alkylamine,
amino,
aryl, cycloalkyl, heterocyclyl,
C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 alkylamine, C1-C6 dialkylamine, C2-C6 alkenyl, or C2-C6 alkynyl, wherein each of which may be interrupted by one or more hetero atoms,
carboxyl,
cyano,
halo,
hydroxy,
nitro,
—C(O)OH, —C(O)2—(C1-C6 alkyl), —C(O)2—(C3-C8 cycloalkyl), —C(O)2-(aryl), —C(O)2-(heterocyclyl), —C(O)2—(C1-C6 alkylene)aryl, —C(O)2—(C1-C6 alkylene)heterocyclyl,
—C(O)2—(C1-C6 alkylene)cycloalkyl, —C(O)(C1-C6 alkyl), —C(O)(C3-C8 cycloalkyl),
—C(O)(aryl), —C(O)(heterocyclyl), —C(O)(C1-C6 alkylene)aryl, —C(O)(C1-C6 alkylene)heterocyclyl, and —C(O)(C1-C6 alkylene)cycloalkyl,
wherein each of the above optional substituents can be further optionally substituted by 1-5 substituents selected from amino, cyano, halo, hydroxy, nitro, C1-C6 alkylamine, C1-C6 dialkylamine, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkenyl, and C1-C6 hydroxyalkyl, wherein each alkyl is optionally substituted by one or more halo substituents,
or a pharmaceutically acceptable salt, hydrate, tautomer or stereoisomer thereof.

20 more elements

A compound selected from

cis-N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,8,9,9a-octahydro-1H-cyclohepta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,9,10,10a-decahydro-cycloocta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
cis-N-[3-(4-Hydroxy-2-oxo-1-pyridin-2-ylmethyl-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
cis-N-{3-[1-(5-Fluoro-pyridin-2-ylmethyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
cis-N-{3-[1-(2-Dimethylamino-ethyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
cis-N-[3-(1-Benzyl-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
cis-N-{3-[1-(3-Fluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
cis-N-[3-(4-Hydroxy-2-oxo-1-phenethyl-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
cis-N-[3-(1-Cyclopentyl-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
(4aR,7aS)-N-{3-[1-(3-Chloro-4-fluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
(4aR,7aS)-N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
(4aR,8aS)-N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,8a-octahydro-quinolin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
(4aR,7aS)-N-{3-[4-Hydroxy-2-oxo-1-(4-trifluoromethyl-benzyl)-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
(4aR,7aS)-N-{3-[4-Hydroxy-2-oxo-1-(3-trifluoromethyl-benzyl)-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-1,2,4a,5,6,8a-hexahydro-quinolin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
cis-N-{3-[2-(3-Methylbutyl)-5-hydroxy-3-oxo-2-aza-bicyclo[4.3.0]non-4-en-4-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
cis-N-{3-[2-(3,3-Dimethylbutyl)-5-hydroxy-3-oxo-2-aza-bicyclo[4.3.0]non-4-en-4-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
cis-N-{3-[2-Cyclopropylethyl-5-hydroxy-3-oxo-2-aza-bicyclo[4.3.0]non-4-en-4-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-{3-[2-(3-Methylbutyl)-5-hydroxy-3-oxo-2-aza-bicyclo[4.4.0]dec-4-en-4-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-{3-[2-(3,3-Dimethylbutyl)-5-hydroxy-3-oxo-2-aza-bicyclo[4.4.0] dec-4-en-4-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
(4aR,7aS)-N-{3-[1-(4-Fluoro-3-methyl-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
(4aR,7aS)-N-{3-[4-Hydroxy-1-(3-methyl-benzyl)-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
cis-2-Amino-ethanesulfonic acid {3-[1-(4-fluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-amide,
(4aS,7aR)-N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
(4aR,7aS)-N-{3-[1-(3,4-Difluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
(4aR,7aS)-N-{3-[4-Hydroxy-1-(3-methyl-butyl)-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
(4aR,7aS)-N-{3-[1-(3,3-Dimethyl-butyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
(4aR,7aS)-N-[3-(1-Cyclopropylmethyl-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
(4aS,8aR)-N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,8a-octahydro-quinolin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-{3-[1-(3,3-Dimethyl-butyl)-4-hydroxy-2-oxo-2,4a,5,6,7,8,9,9a-octahydro-1H-cyclohepta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-{3-[4-Hydroxy-1-(3-methyl-butyl)-2-oxo-2,4a,5,6,7,8,9,9a-octahydro-1H-cyclohepta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-{3-[4-Hydroxy-1-(3-methyl-butyl)-2-oxo-2,4a,5,6,7,8,9,9a-octahydro-1H-cyclohepta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-N-methyl-methanesulfonamide,
N-{3-[1-(3,3-Dimethyl-butyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,9,10,10a-decahydro-cycloocta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-{3-[1-(3,3-Dimethyl-butyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,9,10,10a-decahydro-cycloocta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-N-methyl-methanesulfonamide,
cis-N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-1,2,4a,5,8,8a-hexahydro-quinolin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
cis-N-[3-(1-Dimethylamino-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide hydrochloride,
(4aR,7aS)-1-(4-Fluoro-benzyl)-4-hydroxy-3-(7-iodo-1,1-dioxo-1,4-dihydro-1λ6 benzo[1,2,4]thiadiazin-3-yl)-1,4a,5,6,7,7a-hexahydro-[1]pyrindin-2-one,
(4aR,7aS)-N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-benzenesulfonamide,
cis-N-[3-(1-Cyclobutylamino-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide trifluoroacetic acid salt,
(4aR,7aS)-3-(1,1-Dioxo-7-piperidin-1-yl-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-1-(4-fluoro-benzyl)-4-hydroxy-1,4a,5,6,7,7a-hexahydro-[1]pyrindin-2-one,
cis-N-[3-(1-Cyclohexyl-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
(4aR,7aS)-3-[7-(1,1-Dioxo-4,5-dihydro-1H-1λ6-thiophen-2-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl]-1-(4-fluoro-benzyl)-4-hydroxy-1,4a,5,6,7,7a-hexahydro-[1]pyrindin-2-one,
(4aR,7aS)-3-[7-(1,1-Dioxo-tetrahydro-1λ6-thiophen-2-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl]-1-(4-fluoro-benzyl)-4-hydroxy-1,4a,5,6,7,7a-hexahydro-[1]pyrindin-2-one,
1-(4-Fluoro-benzyl)-4-hydroxy-3-(7-iodo-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-1,4a,5,6,7,8,9,9a-octahydro-cyclohepta[b]pyridin-2-one,
cis-N-[3-(1-Cyclobutylmethyl-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
cis-N-[3-(4-Hydroxy-2-oxo-1-phenyl-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
N-[3-(1-Cyclohexyl-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,8a-octahydro-quinolin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
1-(4-Fluoro-benzyl)-4-hydroxy-3-(7-iodo-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-4a,5,6,7,8,8a-hexahydro-1H-quinolin-2-one,
3-(1,1-Dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-1-(4-fluoro-benzyl)-4-hydroxy-1,4a,5,6,7,7a-hexahydro-[1]pyrindin-2-one,
(4aR,7aS)-N-{3-[1-(4-Fluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-C-phenyl-methanesulfonamide,
cis-N-[3-(4-Hydroxy-1-methyl-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
cis-N-[3-(1-Ethyl-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
cis-N-[3-(4-Hydroxy-1-isopropyl-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide,
cis-N-{3-[1-(4-Chloro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-{3-[1-(2-Cyclopropyl-ethyl)-4-hydroxy-2-oxo-2,4a,5,6,7,8,9,9a-octahydro-1H-cyclohepta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide,
N-[3-(4-Hydroxy-2-oxo-2,4a,5,6,7,8,9,9a-octahydro-1H-cyclohepta[b]pyridin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide, and
N-[3-(1-Cyclobutylamino-4-hydroxy-2-oxo-2,4a,5,6,7,8,9,9a-octahydro-1H-cyclohepta[b]pyridin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide trifluoroacetic acid salt.

55 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/955,144Filed 12 Dec 2007 · us provisional application
Priority: 12 Dec 2006
Published: US 2009/0111798 A130 Apr 2009
Granted: 1 Sep 2009
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 417/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…
A61P 31/12
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antivirals
A61P 31/14
Antivirals: for RNA viruses

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Application60/874,253Us provisional application · filed 12 Dec 2006
Application60/907,479Us provisional application · filed 3 Apr 2007
US 2009/0111798 A1Pre-grant publication · published 30 Apr 2009
US 7,582,626 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of Formula I

wherein
Z is
X is N,
Y is —(CR4R5)n—,
n is 2, 3, 4, or 5,
R1 and R6 are independently H or C1-C6 alkyl,
R2, R3, R4, and R5 are independently H, C1-C6 alkyl, halo, or R2 and R3 or R4 and R5 combine with the atom to which they are attached to form a 3- to 6-membered spirocyclic ring,
R7 is H, C1-C6 alkyl, C3-C8 cycloalkyl, —C1-C6 alkylene(C3-C8 cycloalkyl), —C1-C6 alkylene(aryl), —C1-C6 alkylene(heterocyclyl), aryl, heterocyclyl, or —NR10R11, wherein R10 and R11 are independently H, C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C6 alkenyl
R8 is H, halo, nitro, —CHR12S(O)2R13, —C(S(O)2R13)═CHR12—, —NR13R14, —NR12S(O)2R13, or —NR12S(O)2NR13R14, wherein R12, R13, and R14 are independently H, C1-C6 alkyl C3-C8 cycloalkyl, aryl, or heterocyclyl, or R12 and R13 or R13 and R14 combine with the atom(s) to which they are attached to form a 5- or 6-membered heterocyclyl ring,
wherein the above alkyl, alkylene, aryl, cycloalkyl, or heterocyclyl moieties provided in R1, R2, R3, R4, R5, R6, R7, R10, R11, R12,R13, and R14 are each optionally and independently substituted by 1-3 substituents selected from
alkylamine,
amino,
aryl, cycloalkyl, heterocyclyl,
C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 alkylamine, C1-C6 dialkylamine, C2-C6 alkenyl, or C2-C6 alkynyl, wherein each of which may be interrupted by one or more hetero atoms,
carboxyl,
cyano,
halo,
hydroxy,
nitro,
—C(O)OH, —C(O)2—(C1-C6 alkyl), —C(O)2—(C3-C8 cycloalkyl), —C(O)2-(aryl), —C(O)2-(heterocyclyl), —C(O)2—(C1-C6 alkylene)aryl, —C(O)2—(C1-C6 alkylene)heterocyclyl, —C(O)2—(C1-C6 alkylene)cycloalkyl, —C(O)(C1-C6 alkyl), —C(O)(C3-C8 cycloalkyl), —C(O)(aryl), —C(O)(heterocyclyl), —C(O)(C1-C6 alkylene)aryl, —C(O)(C1-C6 alkylene)heterocyclyl, and —C(O)(C1-C6 alkylene)cycloalkyl,
wherein each of the above optional substituents can be further optionally substituted by 1-5 substituents selected from amino, cyano, halo, hydroxy, nitro, C1-C6 alkylamine, C1-C6 dialkylamine, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkenyl, and C1-C6 hydroxyalkyl, wherein each alkyl is optionally substituted by one or more halo substituents,
or a pharmaceutically acceptable salt, hydrate, tautomer or stereoisomer thereof.

19 more elements

Facts

Application

11/955,144Filed 12 Dec 2007 · us provisional application

Priority

12 Dec 2006

Published

US 2009/0111798 A130 Apr 2009

Granted

1 Sep 2009

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 417/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…
A61P 31/12
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antivirals
A61P 31/14
Antivirals: for RNA viruses