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US 12,611,404 B2Granted
Aza-aryl 1H-pyrazol-1-yl benzene sulfonamides
AssigneeChemoCentryx, Inc.
InventorsXi Chen, Junfa Fan, Pingchen Fan, Antoni Krasinski, Lianfa Li, Rebecca M. Lui, Jeffrey P. McMahon, Jay P. Powers, Yibin Zeng, Penglie Zhang
Life of this patent
Estimating the term…
Abstract
Compounds are provided that act as potent antagonists of the CCR(9) receptor. Animal testing demonstrates that these compounds are useful for treating inflammation, a hallmark disease for CCR(9). The compounds are generally aryl sulfonamide derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR(9)-mediated diseases, and as controls in assays for the identification of CCR(9) antagonists.
Claims10
A compound or salt of formula (II):
- wherein:
- R1 is selected from the group consisting of substituted or unsubstituted C2-8 alkyl, substituted or unsubstituted C1-8 alkoxy, and substituted or unsubstituted C3-10 heterocyclyl, and;
- R2 is H, F, or Cl;
- or
- R1 and R2 together with the carbon atoms to which they are attached form a non-aromatic carbocyclic ring or a heterocyclic ring;
- R3 is H, substituted or unsubstituted C1-2 alkyl, substituted or unsubstituted C1-2 alkoxy, or halo;
- R4 is H or F;
- R5 is H or F;
- R6 is H, —CN, —CONH2, or substituted or unsubstituted C1-8 alkyl;
- where R5 and R6 may together form a carbocyclic ring;
- L is a bond, —CH2—, or —CH(CH3)—;
- Z is selected from the group consisting of
- wherein the Z group is unsubstituted or substituted with 1 to 3 independently selected R8 substituents;
- R8 is each independently selected from the group consisting of H, halo, —CN, —OH, oxo, substituted or unsubstituted C1-8 alkyl, substituted or unsubstituted C1-8 alkoxy, and —NR20R21, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heterocyclyl;
- and
- R20 and R21 are each independently H, or substituted or unsubstituted C1-8 alkyl,
- wherein substituents for substituted alkyl including the alkyl portions of aminoalkyl, alkylamino, and alkoxy are independently selected from:
- halogen, —CN, —CO2R′, —C(O) R′, —C(O) NR′R″, oxo (═O or —O), OR′, —OC (O) R′, —OC (O) NR′R″, —NO2, —NR′C (O) R″, —NR′″C (O) NR′R″, —NR′R″, —NR′CO2R″, —NR'S (O) R″, —NR'S (O)2R″ “, —NR”'S (O) NR′R″, —NR″'S (O)2NR′R″, —SR′, —S(O) R′, —S(O)2R′, —S(O)2NR′R″, —NR′—C(NHR″)═NR″, —SiR′R″R′″, —OSiR′R″R′″, —N3, unsubstituted C6-10 aryl, unsubstituted 5- to 10-membered heteroaryl, and unsubstituted 3- to 10-membered heterocyclyl;
- wherein the number of substituents is from zero to (2m′+1), where m′ is the total number of carbon atoms in the alkyl, alkenyl, and alkynyl group;
- wherein substituents for substituted aryl, heterocyclyl, and heteroaryl are independently selected from halogen, —CN, —CO2R′, —C(O) R′, —C(O) NR′R″, oxo (═O or —O-), —OR′, —OSiR′R″R′″, —OC (O) R′, —OC (O) NR′R″, —NO2, —NR′C (O) R″, —NR′″C (O) NR′R″, —NR′R″, —NR′CO2R″, —NR'S (O) R″, —NR'S (O)2R″, —NR″'S (O) NR′R″, —NR″'S (O)2NR′R″, —SR′, —S(O) R′, —S (O)2R′, —S(O)2NR′R″, —NR′—C(NHR″)═NR′″, —SiR′R″R′″, —N3, unsubstituted C1-8 alkyl, unsubstituted C2-8 alkenyl, unsubstituted C2-8 alkynyl, unsubstituted C6-10 aryl, unsubstituted 5-to 10-membered heteroaryl, and unsubstituted 3- to 10-membered heterocyclyl;
- wherein the number of possible substituents to substituted aryl, heterocyclyl, and heteroaryl is from 0 to the total number of open valences on the ring system;
- and
- wherein R′, R″ and R′″ are each independently hydrogen, unsubstituted C1-8 alkyl, unsubstituted C2-8 alkenyl, or unsubstituted C2-8 alkynyl.
20 more elements
A composition comprising a pharmaceutically acceptable carrier and a compound or salt of formula (II):
- wherein:
- R1 is selected from the group consisting of substituted or unsubstituted C2-8 alkyl, substituted or unsubstituted C1-8 alkoxy, and substituted or unsubstituted C3-10 heterocyclyl;
- and
- R2 is H, F, or Cl;
- or
- R1 and R2 together with the carbon atoms to which they are attached form a non-aromatic carbocyclic ring or a heterocyclic ring;
- R3 is H, substituted or unsubstituted C1-2 alkyl, substituted or unsubstituted C1-2 alkoxy, or halo;
- R4 is H or F;
- R5 is H or F;
- and
- R6 is H, —CN, —CONH2, or substituted or unsubstituted C1-8 alkyl;
- or
- R5 and R6 together with the carbon atoms to which they are attached form a carbocyclic ring;
- L is a bond, —CH2—, or —CH(CH3)—;
- Z is selected from the group consisting of
- wherein the Z group is unsubstituted or substituted with 1 to 3 independently selected R& substituents;
- R8 is each independently selected from the group consisting of H, halo, —CN, —OH, oxo, substituted or unsubstituted C1-8 alkyl, substituted or unsubstituted C1-8 alkoxy, —NR20R21, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heterocyclyl;
- R20 and R21 are each independently H or substituted or unsubstituted C1-8 alkyl,
- wherein substituents for substituted alkyl including the alkyl portions of aminoalkyl, alkylamino, and alkoxy are independently selected from:
- halogen, —CN, —CO2R′, —C(O) R′, —C (O) NR′R″, oxo (═O or —O″), —OR′, —OC (O) R′, —OC (O) NR′R″, —NO2, —NR′C (O) R″, NR′″C (O) NR′R″, —NR′R″, —NR′CO2R″, —NR'S (O) R″, —NR'S (O)2R″ “, —NR”'S (O) NR′R″, —NR″'S (O)2NR′R″, —SR′, —S(O) R′, —S(O)2R′, —S(O)2NR′R″, —NR′—C(NHR″)═NR′″, —SiR′R″R′″, —OSiR′R″R′″, —N3, unsubstituted C6-10 aryl, unsubstituted 5- to 10-membered heteroaryl, and unsubstituted 3- to 10-membered heterocyclyl;
- wherein the number of substituents is from zero to (2m′+1), where m′ is the total number of carbon atoms in the alkyl, alkenyl, and alkynyl group;
- wherein substituents for substituted aryl, heterocyclyl, and heteroaryl are independently selected from halogen, —CN, —CO2R′, —C(O) R′, —C(O) NR′R″, oxo (═O or —O″), —OR′, —OSiR′R″R′″, —OC (O) R′, —OC (O) NR′R″, —NO2, —NR′C (O) R″, —NR′″C (O) NR′R″, —NR′R″, —NR′CO2R″, —NR'S (O) R″, —NR'S (O)2R″, —NR″'S (O) NR′R″, —NR″'S (O)2NR′R″, —SR′, —S (O) R′, —S(O)2R′, —S(O)2NR′R″, —NR′—C(NHR″)═NR′″, —SiR′R″R′″, —N3, unsubstituted C1-8 alkyl, unsubstituted C2-8 alkenyl, unsubstituted C2-8 alkynyl, unsubstituted C6-10 aryl, unsubstituted 5- to 10-membered heteroaryl, and unsubstituted 3- to 10-membered heterocyclyl;
- wherein the number of possible substituents to substituted aryl, heterocyclyl, and heteroaryl is from 0 to the total number of open valences on the ring system;
- and
- wherein R′, R″ and R′″ are each independently hydrogen, unsubstituted C1-8 alkyl, unsubstituted C2-8 alkenyl, or unsubstituted C2-8 alkynyl.
22 more elements
Dependencies are inferred from the claim text.