BENZOFURAN-2-SULFONAMIDES PYRIDINE DERIVATIVES AS CHEMOKINE RECEPTOR MODULATORS

• US 20130231339A1
• Filed: 03/01/2013
• Published: 09/05/2013
• Est. Priority Date: 03/01/2012
• Status: Active Grant

• Current Assignee: Allergan, Inc. (Canada) (Abbvie Incorporated)
• Original Assignee: Allergan, Inc. (Canada) (Abbvie Incorporated)
• Inventors: YUAN, HAIQING, BEARD, RICHARD L., LIU, XIAOXIA, DONELLO, JOHN E., VISWANATH, VEENA, GARST, MICHAEL E.
• Granted Patent: US 8,815,915 B2
• Time in Patent Office: Days
• US Class Current: 514/233.5
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: C07D 307/78 Benzo [b] furans; Hydrogenated benzo [b] furans
• CPC Class Codes: C07D 307/82 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/14 containing three or more hetero rings

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.

Claims

1. A compound having Formula I, its enantiomers, diastereoisomers, hydrates, solvates, crystal forms and individual isomers, tautomers or a pharmaceutically acceptable salt thereof:

2. A compound according to claim 1 wherein:

R¹ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R² is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R³ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁴ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁵ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁶ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁷ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁸ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 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 C_1-6 alkyl, CF₃, OR¹², NR¹³R¹⁴, substituted or unsubstituted C_6-10 aryl, substituted or unsubstituted heterocycle, substituted or unsubstituted C_3-8 cycloalkyl, substituted or unsubstituted C_2-6 alkyne, substituted or unsubstituted C_2-6 alkene or COR¹⁵;

R¹² is hydrogen or substituted or unsubstituted C_1-6 alkyl;

R¹³ is hydrogen or substituted or unsubstituted C_1-6 alkyl or can from an optionally substituted heterocycle with R¹⁴;

R¹⁴ is hydrogen, substituted or unsubstituted C_1-6 alkyl, substituted or unsubstituted heterocycle or substituted or unsubstituted C_6-10 aryl or can from an optionally substituted heterocycle with R¹³;

R¹⁵ is hydrogen, hydroxyl, substituted or unsubstituted heterocycle, substituted or unsubstituted C_6-10 aryl or substituted or unsubstituted C_1-6 alkyl; and

R¹⁸ is hydrogen or substituted or unsubstituted C_1-6 alkyl.

3. A compound according to claim 2 selected from:

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.

4. A compound according to claim 1 wherein:

R¹ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R² is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R³ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁴ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁵ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁶ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁷ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁸ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁹ is O;

a is 0 or 1;

R¹¹ is hydrogen, CN, substituted or unsubstituted C_1-6 alkyl, CF₃, OR¹², NR¹³R¹⁴, substituted or unsubstituted C_6-10 aryl, substituted or unsubstituted heterocycle, substituted or unsubstituted C_3-8 cycloalkyl, substituted or unsubstituted C_2-6 alkyne, substituted or unsubstituted C_2-6 alkene or COR¹⁵;

R¹² is hydrogen or substituted or unsubstituted C_1-6 alkyl;

R¹³ is hydrogen or substituted or unsubstituted C_1-6 alkyl or can from an optionally substituted heterocycle with R¹⁴;

R¹⁴ is hydrogen, substituted or unsubstituted C_1-6 alkyl, substituted or unsubstituted heterocycle or substituted or unsubstituted C_6-10 aryl or can from an optionally substituted heterocycle with R¹³;

R¹⁵ is hydrogen, hydroxyl, substituted or unsubstituted heterocycle, substituted or unsubstituted C_6-10 aryl or substituted or unsubstituted C_1-6 alkyl; and

R¹⁸ is hydrogen or substituted or unsubstituted C_1-6 alkyl.

5. A compound according to claim 1 wherein:

R¹ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R² is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R³ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁴ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁵ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁶ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁷ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁸ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁹ is C(O);

a is 0 or 1;

R¹¹ is hydrogen, CN, substituted or unsubstituted C_1-6 alkyl, CF₃, OR¹², NR¹³R¹⁴, substituted or unsubstituted C_6-10 aryl, substituted or unsubstituted heterocycle, substituted or unsubstituted C_3-8 cycloalkyl, substituted or unsubstituted C_2-6 alkyne, substituted or unsubstituted C_2-6 alkene or COR¹⁵;

R¹² is hydrogen or substituted or unsubstituted C_1-6 alkyl;

R¹³ is hydrogen or substituted or unsubstituted C_1-6 alkyl or can from an optionally substituted heterocycle with R¹⁴;

R¹⁴ is hydrogen, substituted or unsubstituted C_1-6 alkyl, substituted or unsubstituted heterocycle or substituted or unsubstituted C_6-10 aryl or can from an optionally substituted heterocycle with R¹³;

R¹⁵ is hydrogen, hydroxyl, substituted or unsubstituted heterocycle, substituted or unsubstituted C_6-10 aryl or substituted or unsubstituted C_1-6 alkyl; and

R¹⁸ is hydrogen or substituted or unsubstituted C_1-6 alkyl.

6. A compound according to claim 1 wherein:

R¹ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R² is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R³ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁴ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁵ is hydrogen, halogen or substituted or unsubstituted C_1-6 alkyl;

R⁶ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁷ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁸ is hydrogen, halogen, CN, substituted or unsubstituted C_1-6 alkyl, OR¹², NR¹³R¹⁴, or COR¹⁵;

R⁹ is —

C(═

NOR¹⁶)—

;

a is 0 or 1;

R¹¹ is hydrogen, CN, substituted or unsubstituted C_1-6 alkyl, CF₃, OR¹², NR¹³R¹⁴, substituted or unsubstituted C_6-10 aryl, substituted or unsubstituted heterocycle, substituted or unsubstituted C_3-8 cycloalkyl, substituted or unsubstituted C_2-6 alkyne, substituted or unsubstituted C_2-6 alkene or COR¹⁵;

R¹² is hydrogen or substituted or unsubstituted C_1-6 alkyl;

R¹³ is hydrogen or substituted or unsubstituted C_1-6 alkyl or can from an optionally substituted heterocycle with R¹⁴;

R¹⁴ is hydrogen, substituted or unsubstituted C_1-6 alkyl, substituted or unsubstituted heterocycle or substituted or unsubstituted C_6-10 aryl or can from an optionally substituted heterocycle with R¹³;

R¹⁵ is hydrogen, hydroxyl, substituted or unsubstituted heterocycle, substituted or unsubstituted C_6-10 aryl or substituted or unsubstituted C_1-6 alkyl;

R¹⁶ is hydrogen or substituted or unsubstituted C_1-6 alkyl; and

R¹⁸ is hydrogen or substituted or unsubstituted C_1-6 alkyl.

7. A compound according to claim 1 selected from:

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.

8. A pharmaceutical composition comprising as active ingredient a therapeutically effective amount of a compound according to claim 1 and a pharmaceutically acceptable adjuvant, diluents or carrier.

9. A pharmaceutical composition according to claim 8 wherein the compound is selected from:

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.

10. 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

11. A method of claim 10, wherein the pharmaceutical composition is administered to the mammal to treat ocular inflammatory diseases and skin inflammatory diseases and conditions.

12. The method of claim 10 wherein the mammal is a human.