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US 2004/0167113 A1Published application
Bis-aryl sulfonamides
OwnerSolomon Ugashe, Zheng Wei +4inventors
InventorsSolomon Ugashe, Zheng Wei, J.J. Wright, Andrew Pennell, Brett Premack, Thomas Schall
Life of this patent
Estimating the term…
Abstract
Compounds are provided that act as potent antagonists of chemokine receptors. The compounds are generally aryl sulfonamide derivatives and are useful in pharmaceutical compositions, methods for the treatment of chemokine receptor-mediated diseases, and as controls in assays for the identification of chemokine antagonists.
Claims67
A modulator of the formula (I) or a salt thereof:
- 91
- where
- L is —C(O)—, —S—, —S(O)— or —S(O)2—;
- X represents from 1 to 4 substituents independently selected from the group consisting of halogen, —CN, —OH, —OR1, —C(O)R1, —CO2R1, —O(CO)R1, —C(O)NR1R2, —OC(O)NR1R2, —SR1, —SOR1, —SO2R1, —SO2NR1R2, —NR1R2, —NR1C(O)R2, —NR1C(O)2R2, —NR1SO2R2, —NR1(CO)NR1R2, unsubstituted C2-8 alkyl, substituted C1-8 alkyl, unsubstituted or substituted C2-8 alkenyl, unsubstituted or substituted C2-8 alkynyl, unsubstituted or substituted C3-8 cycloalkyl, unsubstituted or substituted 6- to 10-membered aryl, unsubstituted or substituted 5- to 10-membered heteroaryl, and unsubstituted or substituted 3- to 10-membered heterocyclyl;
- R1, R2 and R3 are each independently selected from the group consisting of hydrogen, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C3-6 cycloalkyl, unsubstituted or substituted C2-6 alkenyl, unsubstituted or substituted C2-6 alkynyl, unsubstituted or substituted 6- to 10-membered aryl, unsubstituted or substituted 5- to 10-membered heteroaryl, unsubstituted or substituted aryl-C1-4 alkyl, unsubstituted or substituted aryl-C1-4 alkyl, and unsubstituted or substituted aryloxy-C1-4 alkyl;
- or
- two of R1, R2 and R3 together with the atom(s) to which they are attached, may form an unsubstituted or substituted 5-, 6- or 7-membered ring;
- Y represents from 1 to 3 substituents, each independently selected from the group consisting of halogen, —CN, —OH, —OR4, —C(O)R4, —CO2R4, —SR4, —SOR4, —SO2R4, and unsubstituted or substituted C1-4 alkyl;
- R4 is selected from the group consisting of hydrogen, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C3-6 cycloalkyl, unsubstituted or substituted C2-6 alkenyl, and unsubstituted or substituted C2-6 alkynyl;
- Z represents 0 to 5 substituents independently selected from the group consisting of halogen, unsubstituted or substituted C1-8 alkyl, unsubstituted or substituted C3-8 cycloalkyl, unsubstituted or substituted C2-8 alkenyl, unsubstituted or substituted C2-8 alkynyl, unsubstituted or substituted C18 alkoxy, ═O, —CN, —NO2, —OH, —OR7, —OC(O)R7, —CO2R7, —C(O)R7, —CONR7R8, —OC(O)NR7R8, —NR7C(O)R8, —NR7C(O)NR8R9, —NR7R8, —NR7CO2R8, —SR7, —SOR7, —SO2R7, —SO2NR7R8, —NR7SO2R8, unsubstituted or substituted 6- to 10-membered aryl, unsubstituted or substituted heteroaryl and unsubstituted or substituted heterocyclyl;
- and
- R7, R8 and R9 are each independently hydrogen, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C3-6 cycloalkyl, unsubstituted or substituted C2-6 alkenyl, unsubstituted or substituted C2-6 alkynyl, unsubstituted or substituted phenyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted aryl-C1-4 alkyl, and unsubstituted or substituted aryloxy-C1-4 alkyl;
- or where any two of R7, R8 and R9 together with the atom(s) to which they are attached, may form a 5-, 6- or 7-membered ring.
10 more elements
A modulator of one of the formulae (II) or (III) or a salt thereof:
- 92
- 93
- where X′ and X″ are each independently selected from the group consisting of hydrogen, halogen, —CN, —OH, —OR1, —C(O)R1, —CO2R1, —O(CO)R1, —C(O)NR1R2, —OC(O)NR1R2, —SR1, —SOR1, —SO2R1, —SO2NR1R2, —NR1R2, —NR1C(O)R2, —NR1C(O)2R2, —NR1SO2R2, —NR1(CO)NR2R3, unsubstituted or substituted C1-8 alkyl, unsubstituted or substituted C2-8 alkenyl, unsubstituted or substituted C2-8 alkynyl, unsubstituted or substituted C3-8 cycloalkyl, unsubstituted or substituted 6- to 10-membered aryl, unsubstituted or substituted 5- to 10-membered heteroaryl, and unsubstituted or substituted 3- to 10-membered heterocyclyl, with the proviso that if one of X′ and X″ is hydrogen than the other is not hydrogen or unsubstituted methyl;
- R1, R2 and R3 are each independently selected from the group consisting of hydrogen, C1-6 alkyl, C3-6 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, 6- to 10-membered aryl, 5- to 10-membered heteroaryl, aryl-C1-4 alkyl, aryl-1-4 alkyl, and aryloxy-C1-4 alkyl;
- or
- two of R1, R2 and R3 together with the atom(s) to which they are attached, may form a 5-, 6- or 7-membered ring;
- Y′ and Y″ are each independently selected from the group consisting of hydrogen, halogen, —CN, —OH, —OR4, —C(O)R4, —CO2R4, —SR4, —SOR4, —SO2R4, and unsubstituted or substituted C1-4 alkyl, with the proviso that Y′ and Y″ cannot both be hydrogen simultaneously;
- R4 is selected from the group consisting of hydrogen, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C3-6 cycloalkyl, unsubstituted or substituted C2-6 alkenyl, and unsubstituted or substituted C2-6 alkynyl;
- Z′ and Z″ are each independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C1-8 alkyl, unsubstituted or substituted C3-8 cycloalkyl, unsubstituted or substituted C2-8 alkenyl, unsubstituted or substituted C2-8 alkynyl, unsubstituted or substituted C1-8 alkoxy, ═O, —CN, —NO2, —OH, —OR7, —OC(O)R7, —CO2R7, —C(O)R7, —CONR7R8, —OC(O)NR7R8, —NR7C(O)R8, —NR7C(O)NR8R9, —NR7R8, —NR7CO2R8, —SR7, —SOR7, —SO2R7, —SO2NR7R8, —NR7SO2R8, unsubstituted or substituted 6- to 10-membered aryl, unsubstituted or substituted 5- or 6-membered heteroaryl and unsubstituted or substituted 3- to 7-membered heterocyclyl;
- and
- where R7, R8 and R9 are each independently hydrogen, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C3-6 cycloalkyl, unsubstituted or substituted C2-6 alkenyl, unsubstituted or substituted C2-6 alkynyl, unsubstituted or substituted phenyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted aryl-C1-4 alkyl, and unsubstituted or substituted aryloxy-C1-4 alkyl;
- or where any two of R7, R8 and R9 together with the atom(s) to which they are attached, may form a 5-, 6- or 7-membered ring.
9 more elements
Dependencies are inferred from the claim text.