Benzofuran-2-sulfonamides derivatives as chemokine receptor modulators

• US 9,550,746 B2
• Filed: 01/05/2015
• Issued: 01/24/2017
• 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.
• Primary Examiner(s): Rao, Savitha
• Assistant Examiner(s): BROWN-PETTIGREW, ANGELA C
• Application Number:
  US14/589,681
• Publication Number:
  US 20150218119A1
• Time in Patent Office: 750 Days
• US Class Current: 1/1
• 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 derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of chemokine receptors.

Claims

1. A compound represented by Formula I, its individual enantiomers, individual diastereoisomers, individual tautomers or a pharmaceutically acceptable salt thereof:

2. A compound according to claim 1 selected from the group consisting of:

N-(5-chloro-2-methylphenyl)-1-benzofuran-2-sulfonamide;

methyl 2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorobenzoate;

N-(5-chloro-2-ethynylphenyl)-1-benzofuran-2-sulfonamide;

N-{5-chloro-2-[(4-oxopiperidin-1-yl)carbonyl]phenyl}-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(morpholin-4-ylcarbonyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(phenylsulfanyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(phenylsulfonyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(phenylsulfinyl)phenyl]-1-benzofuran-2-sulfonamide;

2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chloro-N-phenylbenzamide;

N-(5-chloro-2-cyanophenyl)-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(phenylacetyl)phenyl]-1-benzofuran-2-sulfonamide;

N-{5-chloro-2-[(1Z)-N-methoxy-2-phenylethanimidoyl]phenyl}-1-benzofuran-2-sulfonamide;

N-{5-chloro-2-[(1Z)-N-hydroxy-2-phenylethanimidoyl]phenyl}-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(phenylethynyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(2-phenylethyl)phenyl]-1-benzofuran-2-sulfonamide;

N-{5-chloro-2-[(Z)-2-phenylethenyl]phenyl}-1-benzofuran-2-sulfonamide;

N-[5-methyl-2-(phenylsulfanyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-methyl-2-(phenylsulfinyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-methyl-2-(phenylsulfonyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-fluoro-2-(phenylsulfanyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-fluoro-2-(phenylsulfinyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-fluoro-2-(phenylsulfonyl)phenyl]-1-benzofuran-2-sulfonamide;

2-({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}sulfanyl)benzoic acid;

3-({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}sulfanyl)benzoic acid; and

4-({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}sulfanyl)benzoic acid.

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

4. A pharmaceutical composition according to claim 3 wherein the compound is selected from:

N-(5-chloro-2-methylphenyl)-1-benzofuran-2-sulfonamide;

methyl 2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorobenzoate;

N-(5-chloro-2-ethynylphenyl)-1-benzofuran-2-sulfonamide;

N-{5-chloro-2-[(4-oxopiperidin-1-yl)carbonyl]phenyl}-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(morpholin-4-ylcarbonyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(phenylsulfanyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(phenylsulfonyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(phenylsulfinyl)phenyl]-1-benzofuran-2-sulfonamide;

2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chloro-N-phenylbenzamide;

N-(5-chloro-2-cyanophenyl)-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(phenylacetyl)phenyl]-1-benzofuran-2-sulfonamide;

N-{5-chloro-2-[(1Z)-N-methoxy-2-phenylethanimidoyl]phenyl}-1-benzofuran-2-sulfonamide;

N-{5-chloro-2-[(1Z)-N-hydroxy-2-phenylethanimidoyl]phenyl}-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(phenylethynyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-chloro-2-(2-phenylethyl)phenyl]-1-benzofuran-2-sulfonamide;

N-{5-chloro-2-[(Z)-2-phenylethenyl]phenyl}-1-benzofuran-2-sulfonamide;

N-[5-methyl-2-(phenylsulfanyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-methyl-2-(phenylsulfinyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-methyl-2-(phenylsulfonyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-fluoro-2-(phenylsulfanyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-fluoro-2-(phenylsulfinyl)phenyl]-1-benzofuran-2-sulfonamide;

N-[5-fluoro-2-(phenylsulfonyl)phenyl]-1-benzofuran-2-sulfonamide;

2-({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}sulfanyl)benzoic acid;

3-({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}sulfanyl)benzoic acid; and

4-({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}sulfanyl)benzoic acid.