Benzofuran-2-sulfonamides pyridine derivatives as chemokine receptor modulators
First Claim
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1. A method of treating a disorder associated with chemokine receptor modulation, which comprises administering to a mammal in need thereof, a pharmaceutical composition comprising a therapeutically effective amount of at least one compound of Formula I
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Abstract
The present invention relates to novel benzofuran-2-sulfonamide pyridine derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of chemokine receptors.
18 Citations
8 Claims
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1. A method of treating a disorder associated with chemokine receptor modulation, which comprises administering to a mammal in need thereof, a pharmaceutical composition comprising a therapeutically effective amount of at least one compound of Formula I
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2. The method according to claim 1 wherein:
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R1 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R2 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R3 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R4 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R5 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R6 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R7 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R8 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R9 is S, S(O), S(O)2; a is 0 or 1; R11 is hydrogen, CN, substituted or unsubstituted C1-6 alkyl, CF3, OR12, NR13R14, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted heterocycle, substituted or unsubstituted C3-8 cycloalkyl, substituted or unsubstituted C2-6 alkyne, substituted or unsubstituted C2-6 alkene or COR15; R12 is hydrogen or substituted or unsubstituted C1-6 alkyl; R13 is hydrogen or substituted or unsubstituted C1-6 alkyl or can from an optionally substituted heterocycle with R14; R14 is hydrogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted heterocycle or substituted or unsubstituted C6-10 aryl or can from an optionally substituted heterocycle with R13; R15 is hydrogen, hydroxyl, substituted or unsubstituted heterocycle, substituted or unsubstituted C6-10 aryl or substituted or unsubstituted C1-6 alkyl; and R18 is hydrogen or substituted or unsubstituted C1-6 alkyl.
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3. The method according to claim 1 wherein the compound of Formula I is selected from:
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N-[2-(benzylthio)-5-chloropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfinyl)-5-chloropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfonyl)-5-chloropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-{5-chloro-2-[(pyridin-3-ylmethyl)thio]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-{5-chloro-2-[(pyridin-3-ylmethyl)sulfinyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-{5-chloro-2-[(pyridin-3-ylmethyl)sulfonyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-(5-chloro-2-{[(1-oxidopyridin-3-yl)methyl]sulfonyl}pyridin-3-yl)-1-benzofuran-2-sulfonamide; N-[2-(benzylthio)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfinyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfonyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-{2-[(3-aminobenzyl)sulfanyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-{2-[(3-aminobenzyl)sulfinyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; tert-butyl {3-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfonyl)methyl]phenyl}carbamate; N-{2-[(3-aminobenzyl)sulfonyl]pyridin-3-yl}1-benzofuran-2-sulfonamide; N-[2-(benzylsulfanyl)-5-fluoropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfinyl)-5-fluoropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfonyl)-5-fluoropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-{2-[(3-aminobenzyl)sulfanyl]-5-chloropyridin-3-yl}-1-benzofuran-2-sulfonamide; N-{2-[(3-aminobenzyl)sulfinyl]-5-chloropyridin-3-yl}-1-benzofuran-2-sulfonamide; N-{2-[(3-aminobenzyl)sulfonyl]-5-chloropyridin-3-yl}1-benzofuran-2-sulfonamide; N-[2-(benzylsulfanyl)-5-methylpyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfinyl)-5-methylpyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfonyl)-5-methylpyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-chloro-2-(phenylsulfanyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-chloro-2-(phenylsulfonyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-chloro-2-(phenylsulfinyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfanyl)methyl]benzoate; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfanyl)methyl]benzoic acid; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfinyl)methyl]benzoate; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfonyl)methyl]benzoate; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfonyl)methyl]benzoic acid; N-[5-fluoro-2-(phenylsulfanyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-fluoro-2-(phenylsulfinyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-fluoro-2-(phenylsulfonyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfinyl)methyl]benzoic acid; N-[5-methyl-2-(phenylsulfanyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-methyl-2-(phenylsulfinyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-methyl-2-(phenylsulfonyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; 2-({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfanyl)benzoic acid; 3-({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfanyl)benzoic acid; 2-({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfinyl)benzoic acid; 2-({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfonyl)benzoic acid; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-methylpyridin-2-yl}sulfanyl)methyl]benzoic acid; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-methylpyridin-2-yl}sulfinyl)methyl]benzoic acid; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfanyl)methyl]benzoate; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfanyl)methyl]benzoic acid; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfinyl)methyl]benzoate; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfinyl)methyl]benzoic acid; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfonyl)methyl]benzoate; and 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfonyl)methyl]benzoic acid.
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4. The method of claim 1, wherein:
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R1 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R2 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R3 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R4 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R5 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R6 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R7 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R8 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R9 is O; a is 0 or 1; R11 is hydrogen, CN, substituted or unsubstituted C1-6 alkyl, CF3, OR12, NR13R14, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted heterocycle, substituted or unsubstituted C3-8 cycloalkyl, substituted or unsubstituted C2-6 alkyne, substituted or unsubstituted C2-6 alkene or COR15; R12 is hydrogen or substituted or unsubstituted C1-6 alkyl; R13 is hydrogen or substituted or unsubstituted C1-6 alkyl or can from an optionally substituted heterocycle with R14; R14 is hydrogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted heterocycle or substituted or unsubstituted C6-10 aryl or can from an optionally substituted heterocycle with R13; R15 is hydrogen, hydroxyl, substituted or unsubstituted heterocycle, substituted or unsubstituted C6-10 aryl or substituted or unsubstituted C1-6 alkyl; and R18 is hydrogen or substituted or unsubstituted C1-6 alkyl.
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5. The method according to claim 1 wherein:
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R1 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R2 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R3 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R4 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R5 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R6 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R7 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R8 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R9 is C(O); a is 0 or 1; R11 is hydrogen, CN, substituted or unsubstituted C1-6 alkyl, CF3, OR12, NR13R14, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted heterocycle, substituted or unsubstituted C3-8 cycloalkyl, substituted or unsubstituted C2-6 alkyne, substituted or unsubstituted C2-6 alkene or COR15; R12 is hydrogen or substituted or unsubstituted C1-6 alkyl; R13 is hydrogen or substituted or unsubstituted C1-6 alkyl or can from an optionally substituted heterocycle with R14; R14 is hydrogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted heterocycle or substituted or unsubstituted C6-10 aryl or can from an optionally substituted heterocycle with R13; R15 is hydrogen, hydroxyl, substituted or unsubstituted heterocycle, substituted or unsubstituted C6-10 aryl or substituted or unsubstituted C1-6 alkyl; and R18 is hydrogen or substituted or unsubstituted C1-6 alkyl.
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6. The method according to claim 1 wherein:
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R1 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R2 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R3 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R4 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R5 is hydrogen, halogen or substituted or unsubstituted C1-6 alkyl; R6 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R7 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R8 is hydrogen, halogen, CN, substituted or unsubstituted C1-6 alkyl, OR12, NR13R14, or COR15; R9 is —
C(═
NOR16)—
;a is 0 or 1; R11 is hydrogen, CN, substituted or unsubstituted C1-6 alkyl, CF3, OR12, NR13R14, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted heterocycle, substituted or unsubstituted C3-8 cycloalkyl, substituted or unsubstituted C2-6 alkyne, substituted or unsubstituted C2-6 alkene or COR15; R12 is hydrogen or substituted or unsubstituted C1-6 alkyl; R13 is hydrogen or substituted or unsubstituted C1-6 alkyl or can from an optionally substituted heterocycle with R14; R14 is hydrogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted heterocycle or substituted or unsubstituted C6-10 aryl or can from an optionally substituted heterocycle with R13; R15 is hydrogen, hydroxyl, substituted or unsubstituted heterocycle, substituted or unsubstituted C6-10 aryl or substituted or unsubstituted C1-6 alkyl; R16 is hydrogen or substituted or unsubstituted C1-6 alkyl; and R18 is hydrogen or substituted or unsubstituted C1-6 alkyl.
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7. The method according to claim 1 wherein the compound of Formula I is selected from:
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N-[2-(benzylsulfanyl)-5-chloropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfinyl)-5-chloropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfonyl)-5-chloropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-{5-chloro-2-[(pyridin-3-ylmethyl)sulfanyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-{5-chloro-2-[(pyridin-3-ylmethyl)sulfinyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-{5-chloro-2-[(pyridin-3-ylmethyl)sulfonyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-(5-chloro-2{-[(1-oxidopyridin-3-yl)methyl]sulfonyl}pyridin-3-yl)-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfanyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfinyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfonyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-{2-[(3-aminobenzyl)sulfanyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-{2-[(3-aminobenzyl)sulfinyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; tert-butyl {3-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfonyl)methyl]phenyl}carbamate; N-{2-[(3-aminobenzyl)sulfonyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfanyl)-5-fluoropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfinyl)-5-fluoropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfonyl)-5-fluoropyridin-3-yl]-1-benzofuran-2-sulfonamide; N-{2-[(3-aminobenzyl)sulfanyl]-5-chloropyridin-3-yl}-1-benzofuran-2-sulfonamide; N-{2-[(3-aminobenzyl)sulfinyl]-5-chloropyridin-3-yl}-1-benzofuran-2-sulfonamide; N-{2-[(3-aminobenzyl)sulfonyl]-5-chloropyridin-3-yl}-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfanyl)-5-methylpyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfinyl)-5-methylpyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[2-(benzylsulfonyl)-5-methylpyridin-3-yl]-1-benzofuran-2-sulfonamide; N-{5-chloro-2-[(2-methylpyridin-3-yl)oxy]pyridin-3-yl}-1-benzofuran-2-sulfonamide; 2-({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}oxy)benzoic acid; methyl 2-({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}oxy)benzoate; N-[5-chloro-2-(morpholin-4-ylcarbonyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-{5-chloro-2-[(4-oxopiperidin-1-yl)carbonyl]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-[5-chloro-2-(phenylcarbonyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-chloro-2-(phenylsulfanyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-chloro-2-(phenylsulfonyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-chloro-2-(phenylsulfinyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-{5-chloro-2-[(2-methylpyridin-3-yl)methoxy]pyridin-3-yl}-1-benzofuran-2-sulfonamide; N-[5-chloro-2-(phenylacetyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfanyl)methyl]benzoate; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfanyl)methyl]benzoic acid; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfinyl)methyl]benzoate; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfonyl)methyl]benzoate; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfonyl)methyl]benzoic acid; N-[5-fluoro-2-(phenylsulfanyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-fluoro-2-(phenylsulfinyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-fluoro-2-(phenylsulfonyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfinyl)methyl]benzoic acid; N-[5-methyl-2-(phenylsulfanyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-methyl-2-(phenylsulfinyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; N-[5-methyl-2-(phenylsulfonyl)pyridin-3-yl]-1-benzofuran-2-sulfonamide; 2-({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfanyl)benzoic acid; 3-({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfanyl)benzoic acid; 2-({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfinyl)benzoic acid; 2-({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-chloropyridin-2-yl}sulfonyl)benzoic acid; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-methylpyridin-2-yl}sulfanyl)methyl]benzoic acid; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]-5-methylpyridin-2-yl}sulfinyl)methyl]benzoic acid; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfanyl)methyl]benzoate; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfanyl)methyl]benzoic acid; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfinyl)methyl]benzoate; 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfinyl)methyl]benzoic acid; methyl 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfonyl)methyl]benzoate; and 2-[({3-[(1-benzofuran-2-ylsulfonyl)amino]pyridin-2-yl}sulfonyl)methyl]benzoic acid.
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8. The method of claim 1 wherein the mammal is a human.
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2. The method according to claim 1 wherein:
Specification
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Current AssigneeAllergan, Inc. (Canada) (Abbvie Incorporated)
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Original AssigneeAllergan, Inc. (Canada) (Abbvie Incorporated)
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InventorsYuan, Haiqing, Beard, Richard L., Garst, Michael E., Liu, Xiaoxia, Donello, John E., Viswanath, Veena
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Primary Examiner(s)TRAN, MY CHAU T
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Application NumberUS14/334,145Publication NumberTime in Patent Office761 DaysField of Search514/332, 514/333, 514/336, 514/337US Class Current1/1CPC Class CodesA61P 29/00 Non-central analgesic, anti...C07D 307/78 Benzo [b] furans; Hydrogena...C07D 307/82 with hetero atoms or with c...C07D 405/12 linked by a chain containin...C07D 405/14 containing three or more he...