Patent EP-1838674-A4 (EP)
Title: Heteroaryl sulfonamides and ccr2
Inventor: UNGASHE SOLOMON
IPC: C07D213/02
Filed: 2006-01-13
Abstract: A compound of the formula (I), or a salt thereof:   
where 
Ar is selected from the group consisting of substituted or unsubstituted C 6-10  aryl and substituted or unsubstituted 5- to 10-membered heteroaryl; 
R 1  is selected from the group consisting of hydrogen, unsubstituted C 1  alkyl, substituted or unsubstituted C 3-8  alkyl, substituted or unsubstituted C 2-6  alkenyl, substituted or unsubstituted C 2-6  alkynyl, and substituted or unsubstituted 3- to 10-membered heterocyclyl; 
Y 1  is selected from the group consisting of -CR 2a -, -N-, and -N + (O) - -; 
Y 2  is selected from the group consisting of -CR 2b -, -N-, and -N + (O) - -; 
Y 3  is selected from the group consisting of -CR 2c -, -N-, and -N + (O) - -; 
R 2a , R 2b , and R 2c  are each independently selected from the group consisting of hydrogen, halogen, -CN, -C(O)R 3 , -CO 2 R 3 , -C(O)NR 3 R 4 , -OR 3 , - OC(O)R 3 , -OC(O)NR 3 R 4 , -SR 3 , -S(O)R 3 , -S(O) 2 R 3 , -S(O) 2 NR 3 R 4 , -NO 2 , -NR 3 R 4 , -NR 3 C(O)R 4 , -NR 3 C(O)OR 4 , -NR 3 S(O) 2 R 4 , -NR 3 C(O)NR 4 R 5 , substituted or unsubstituted C 1-8  alkyl, substituted or unsubstituted C 2-8  alkenyl, substituted or unsubstituted C 2-8  alkynyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10  aryl, and substituted or unsubstituted 5- to 10-membered heteroaryl; 
R 3 , R 4 , and R 5  are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8  alkyl, substituted or unsubstituted C 2-8  alkenyl, substituted or unsubstituted C 2-8  alkynyl, substituted or unsubstituted C 6-10  aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, and substituted or unsubstituted 3- to 10-membered heterocyclyl; 
R 3  and R 4 , R 4  and R 5  or R 3  and R 5  may, together with the atoms to which they are attached, form a substituted or unsubstituted 5-, 6-, or 7-membered ring; 
Y 4  is selected from the group consisting of -N- and -N + (O) - -; 
L is selected from the group consisting of a bond, -O-, -S-, -S(O)-, S(O) 2 -, - CR 6 R 7 -, -NR 8 -, -C(O)- and -NR 8 C(O)-; 
R 6  and R 7  are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1-8  alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 2-6  alkenyl, substituted or unsubstituted C 2-6  alkynyl, -CN, -OR 9 , -NR 10 R 11 , -S(O)R 9 , and -S(O) 2 R 9 ; 
R 6  and R 7  may, together with the carbon atom to which they are attached, form substituted or unsubstituted C 3-8  cycloalkyl or substituted or unsubstituted 3-to 10-membered heterocyclic ring; 
R 9  is selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8  alkyl, substituted or unsubstituted C 2-8  alkenyl, substituted or unsubstituted C 2-8  alkynyl, substituted or unsubstituted C 6-10  aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, and substituted or unsubstituted 3- to 10-membered heterocyclyl; 
R 10  and R 11  are each independently selected from the group consisting of substituted or unsubstituted C 1-8  alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10  aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted C 2-8  alkenyl, and substituted or unsubstituted C 2-8  alkynyl; 
R 10  and R 11  of -NR 10 R 11  may, together with the nitrogen, form a substituted or unsubstituted C 3-8  cycloalkyl or substituted or unsubstituted 3- to 10-membered heterocyclyl; 
R 8  is selected from the group consisting of hydrogen, C(O)R 12 , S(O) 2 R 12 , CO 2 R 12 , substituted or unsubstituted C 1-8  alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 2-6  alkenyl, and substituted or unsubstituted C 2-6  alkynyl; 
R 12  is selected from the group consisting of substituted or unsubstituted C 1-8  alkyl, substituted or unsubstituted C 2-6  alkenyl, substituted or unsubstituted C 2-6  alkynyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10  aryl, and substituted or unsubstituted 5- to 10-membered heteroaryl; 
Z 1  is selected from the group consisting of substituted or unsubstituted C 6-10  aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted 3- to 10-membered heterocyclyl, and -NR 13 R 14 ; 
R 13  and R 14  are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8  alkyl, substituted or unsubstituted C 2-8  alkenyl, substituted or unsubstituted C 2-8  alkynyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10  aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted (C 1-4  alkyl)-(C 6-10  aryl), and substituted or unsubstituted (C 1-4  alkyl)-(5- to 10-membered heteroaryl); 
R 13  and R 14  may, together with the nitrogen, form a substituted or unsubstituted 4-, 5-, 6-, or 7-membered heterocyclyl 
with the proviso that compounds of formula CC are excluded:   
where 
X 14  is selected from the group consisting of -Cl, -NO 2 , -OCH 3 , -CH 3 , - NHC(O)CH 3 , and -CH 2 CH 2 -(phenyl); 
R 65  is selected from the group consisting of hydrogen, substituted or unsubstituted C 1-4  alkyl, and substituted or unsubstituted -SO 2 (phenyl); and 
R 60  is selected from the group consisting of -NR 61 CH 2 CH 2 OR 62 , - NR 61 CH 2 CH 2 NR 63 R 64 , -NR 61 CH 2 CH 2 SR 62 ,   
where R 61  is selected from the group consisting of hydrogen and substituted or unsubstituted phenyl; 
R 62  is selected from the group consisting of substituted or unsubstituted phenyl, and substituted or unsubstituted C 1-4  alkyl; and 
R 63  and R 64  are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8  alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted -SO 2 (phenyl), - C(O)CH 3 , -C(O)C(O)OH, and -C(O) 2 C(CH 3 ) 3 .