US2010324093A1PendingUtilityA1
Ccr9 inhibitors and methods of use thereof
Est. expiryMay 24, 2022(expired)· nominal 20-yr term from priority
A61P 43/00A61P 9/00A61P 9/10A61P 3/10A61P 37/00A61P 5/14A61P 7/00A61P 37/06A61P 37/08A61P 25/28A61P 29/00A61P 25/00C07C 323/49C07C 311/46C07D 409/04C07D 213/50C07C 311/44C07D 513/04C07D 401/06A61P 21/04A61P 19/02A61P 1/16C07D 409/06C07D 413/14A61P 1/04A61P 11/02A61P 17/06C07D 213/70C07C 311/21C07D 213/46C07D 213/89C07D 213/75C07D 213/80A61P 13/12C07D 405/06A61P 15/14C07C 317/34A61P 11/00C07D 413/04A61P 17/04C07C 311/29A61P 17/00C07D 213/65C07D 239/42C07D 333/34C07D 239/26C07D 213/76C07D 333/62A61P 1/00A61P 1/18C07D 213/71A61P 15/00A61P 21/00A61P 11/06C07D 237/08
57
PatentIndex Score
0
Cited by
0
References
0
Claims
Abstract
The invention relates to compounds represented by Structural Formula I, which can bind to CCR9 receptors and block the binding of a ligand (e.g., TECK) to the receptors. The invention also relates to a method of inhibiting a function of CCR9, and to the use compounds represented by Structural Formula I in research, therapeutic, prophylactic and diagnostic methods.
Claims
exact text as granted — not AI-modified1 . A compound represented by the following structural formula:
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein:
Y is C(O), O, S, S(O), or S(O) 2 ;
X 1 , X 2 , and X 3 are each, independently, N or CR, provided that at least one of
X 1 , X 2 , or X 3 is CR;
R for each occurrence and R 1 are each, independently, H or a substituent;
R 6 is H, an aliphatic carbonyl group, or an aliphatic ester;
ring A is substituted or unsubstituted; and
Ar 1 and Ar 2 are each, independently, a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl.
2 . The compound of claim 1 , wherein Ar 2 is phenyl, naphthyl, thienyl, or thianaphthenyl, each group being substituted or unsubstituted.
3 . The compound of claim 1 , wherein Ar 1 is phenyl, pyridyl, pyrimidinyl, or pyrazinyl, each group being substituted or unsubstituted.
4 . The compound of claim 1 , which is represented by the following structural formula:
or a pharmaceutically acceptable salts, solvates, or hydrates thereof,
wherein: Y is S, O, S(O), or S(O) 2 ;
R 19 and R 20 are each, independently, H or a substituent.
5 . The compound of claim 1 , which is represented by the following structural formula:
or pharmaceutically acceptable salts, solvates, or hydrates thereof,
wherein: R 1 , R 2 , R 3 , R 4 , R 5 , and each R are, independently, H, an aliphatic group, haloalkyl, halo, COOH, NO 2 , alkoxy, or haloalkoxy; and
X 4 is CR, N or N + —O − .
6 . The compound of claim 1 which is represented by the following structural formula:
or pharmaceutically acceptable salts, solvates, or hydrates thereof,
wherein:
X 4 is CR, N or N + —O − ;
R 8 is H or an electron withdrawing group;
m and n are each, independently, 0 or an integer from 1 to 3;
each R 9 is, independently, aliphatic group, haloalkyl, aryl, arylalkyl, alkoxy, cycloalkoxy, haloalkoxy, aryloxy, arylalkoxy, alkylthio, halo, nitro, cyano, hydroxy, NR 11 CO 2 R 12 , C(O)N(R 11 ) 2 , C(O)R 12 , CO 2 R 12 , OC(O)N(R 11 ) 2 , OC(O)R 12 , N(R 11 ) 2 , or NR 11 C(O)R 12 ; or two adjacent R 9 groups taken together with the atoms to which they are attached form a fused, saturated, unsaturated or partially unsaturated 5 to 7 membered ring having 0, 1 or 2 heteroatoms selected from the group consisting of N, O, and S;
each R 10 is, independently, halo, an aliphatic group, alkoxy, or haloalkyl; or two adjacent R 10 groups taken together with the atoms to which they are attached form a fused, saturated, unsaturated or partially unsaturated 5 to 7 membered ring having 0, 1 or 2 heteroatoms selected from the group consisting of N, O, and S;
each R 11 is, independently, H or an aliphatic group; and
R 12 is an aliphatic group.
7 . The compound of claim 1 wherein the compound is represented by the following structural formula:
or pharmaceutically acceptable salts, solvates, or hydrates thereof,
wherein:
ring B is substituted or unsubstituted;
p is 0 or an integer from 1-3; and
each R 13 is, independently, a halo or a substituted or unsubstituted heteroaryl.
8 . A compound selected from the group consisting of:
N-[4-Chloro-2-(2-chloro-benzoyl)-phenyl]-4-nitro-benzenesulfonamide
Thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-(2-Benzoyl-4-chloro-phenyl)-4-iodo-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-chloro-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-tert-butyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-propyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-ethyl-benzenesulfonamide
N-(2-Benzoyl-4-nitro-phenyl)-4-ethyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-isopropyl-benzenesulfonamide
N-(2-Benzoyl-4-bromo-phenyl)-4-ethyl-benzenesulfonamide
N-(2-Benzoyl-4-bromo-phenyl)-4-methoxy-benzenesulfonamide
N-(2-Benzoyl-4-bromo-phenyl)-4-isopropyl-benzenesulfonamide
4-Ethyl-N-[4-nitro-2-(3-trifluoromethyl-benzoyl)-phenyl]-benzenesulfonamide
N-[4-Chloro-2-(3-methyl-benzoyl)-phenyl]-4-ethyl-benzenesulfonamide
N-(2-Benzoyl-4-bromo-phenyl)-4-chloro-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-ethoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-propoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-isopropoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-butoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-benzyloxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-phenoxy-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridine-4-carbonyl)-phenyl]-4-ethoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridine-4-carbonyl)-phenyl]-4-isopropyl-benzenesulfonamide
N-[4-Chloro-2-(pyridine-4-carbonyl)-phenyl]-4-isobutyl-benzenesulfonamide
N-[5-Chloro-3-(pyridine-4-carbonyl)-pyridin-2-yl]-4-ethoxy-benzenesulfonamide
N-[5-Chloro-3-(pyridine-4-carbonyl)-pyridin-2-yl]-4-isopropoxy-benzenesulfonamide
N-(3-Benzoyl-5-trifluoromethyl-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-(2-Benzoyl-4-nitro-phenyl)-4-chloro-benzenesulfonamide
5-Benzoyl-6-(4-isopropoxy-benzenesulfonylamino)-nicotinic acid
N-(2-Benzoyl-4-chloro-phenyl)-2-nitro-benzenesulfonamide
N-(3-Benzoyl-5-nitro-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-(5-Benzoyl-pyrimidin-4-yl)-4-isopropoxy-benzenesulfonamide
N-(3-Benzoyl-5-trifluoromethoxy-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-(5-Benzoyl-2-trifluoromethyl-pyrimidin-4-yl)-4-isopropoxy-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-cyclopropoxy-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-cyclobutyl-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-tert-butoxy-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-cyclopentyl-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-isopropylsulfanyl-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-isopropylamino-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-cyclopropyl-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-cyclohexyl-benzenesulfonamide
N-(3-Benzenesulfinyl-5-chloro-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-(3-Benzenesulfonyl-5-chloro-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyrimidine-5-carbonyl)-phenyl]-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridazine-4-carbonyl)-phenyl]-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(2-trifluoromethyl-pyrimidine-5-carbonyl)-phenyl]-4-isopropoxy-
benzenesulfonamide
N-[4-Chloro-2-(6-trifluoromethyl-pyridazine-4-carbonyl)-phenyl]-4-isopropoxy-
benzenesulfonamide
N-[4-Chloro-2-(2-trifluoromethyl-pyrimidine-5-carbonyl)-phenyl]-4-isopropoxy-
benzenesulfonamide
N-[4-Chloro-2-(6-trifluoromethyl-pyridazine-4-carbonyl)-phenyl]-4-isopropoxy-
benzenesulfonamide
N-(2-Benzoyl-4-nitro-phenyl)-4-isopropyl-benzenesulfonamide
N-(2-Benzoyl-4-nitro-phenyl)-4-isopropoxy-benzenesulfonamide
N-(2-Benzoyl-4-nitro-phenyl)-4-methoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-trifluoromethoxy-benzenesulfonamide
5-Oxazol-5-yl-thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-[4-Chloro-2-(3-chloro-benzoyl)-phenyl]-4-methoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-methoxy-benzenesulfonamide
N-[4-Chloro-2-(3-chloro-benzoyl)-phenyl]-4-ethyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-ethylamino-benzenesulfonamide
5-(1-Methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-thiophene-2-sulfonic acid (2-benzoyl-4-
chloro-phenyl)-amide
N-(2-Benzoyl-4-iodo-phenyl)-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(3-fluoro-benzoyl)-phenyl]-4-methyl-benzenesulfonamide
N-[4-Chloro-2-(3-chloro-benzoyl)-phenyl]-4-isopropyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-nitro-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-diethylamino-benzenesulfonamide
N-(2-Benzoyl-4-fluoro-phenyl)-4-methoxy-benzenesulfonamide
4-Chloro-N-[4-chloro-2-(pyridine-3-carbonyl)-phenyl]-benzenesulfonamide
N-(2-Benzoyl-4-bromo-phenyl)-4-methyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-bromo-benzenesulfonamide
N-[4-Chloro-2-(pyridine-3-carbonyl)-phenyl]-4-methoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-dimethylamino-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-fluoro-benzenesulfonamide
4-Chloro-N-[4-chloro-2-(2-fluoro-benzoyl)-phenyl]-benzenesulfonamide
N-[4-Chloro-2-(2-fluoro-benzoyl)-phenyl]-4-methoxy-benzenesulfonamide
Thiophene-3-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
5-Bromo-thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
5-Chloro-thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-[4-Chloro-2-(2-fluoro-benzoyl)-phenyl]-4-nitro-benzenesulfonamide
N-[4-Chloro-2-(2-fluoro-benzoyl)-phenyl]-4-methyl-benzenesulfonamide
4-Chloro-N-[4-chloro-2-(pyridine-2-carbonyl)-phenyl]-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-benzenesulfonamide
N-[4-(2-Benzoyl-4-chloro-phenylsulfamoyl)-phenyl]-acetamide
N-[4-Chloro-2-(pyridine-2-carbonyl)-phenyl]-4-methoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridine-2-carbonyl)-phenyl]-4-methyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-cyano-benzenesulfonamide
4,5-Dibromo-thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-[4-Chloro-2-(pyridine-3-sulfonyl)-phenyl]-4-nitro-benzenesulfonamide
Naphthalene-2-sulfonic acid [4-chloro-2-(pyridine-3-carbonyl)-phenyl]-amide
N-(2-Benzoyl-4-chloro-phenyl)-3-bromo-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-methyl-3-nitro-benzenesulfonamide
N-[4-Chloro-2-(2-methoxy-benzoyl)-phenyl]-4-nitro-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-2-trifluoromethyl-benzenesulfonamide
5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-
amide
N-(2-Benzoyl-phenyl)-4-nitro-benzenesulfonamide
5-Isoxazol-3-yl-thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-(2-Benzoyl-phenyl)-4-methyl-benzenesulfonamide
Benzo[b]thiophene-3-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-(4-Chloro-2-phenylsulfanyl-phenyl)-4-isopropoxy-benzenesulfonamide
N-(2-Benzenesulfonyl-4-chloro-phenyl)-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridine-4-carbonyl)-phenyl]-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(1-oxy-pyridine-4-carbonyl)-phenyl]-4-isopropoxy-benzenesulfonamide
4-Isopropoxy-N-[2-(pyridine-4-carbonyl)-4-trifluoromethyl-phenyl]-
benzenesulfonamide
4-Ethoxy-N-[2-(pyridine-4-carbonyl)-4-trifluoromethyl-phenyl]-benzenesulfonamide
N-[5-Chloro-3-(3-fluoro-benzoyl)-pyridin-2-yl]-4-isopropyl-benzenesulfonamide
N-[5-Chloro-3-(3-fluoro-benzoyl)-pyridin-2-yl]-4-isopropoxy-benzenesulfonamide
N-[5-Chloro-3-(thiophene-2-carbonyl)-pyridin-2-yl]-4-isopropoxy-benzenesulfonamide
5-Oxazol-5-yl-thiophene-2-sulfonic acid [5-chloro-3-(3-fluoro-benzoyl)-pyridin-2-yl]-
amide
N-[3-(Benzofuran-2-carbonyl)-5-chloro-pyridin-2-yl]-4-isopropoxy-
benzenesulfonamide
N-(2-Benzoyl-4-trifluoromethyl-phenyl)-4-isopropoxy-benzenesulfonamide
N-(3-Benzoyl-pyridin-4-yl)-4-isopropoxy-benzenes
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-isopropyl-benzenesulfonamide
N-(3-Benzoyl-5-nitro-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
5-Oxazol-5-yl-thiophene-2-sulfonic acid (3-benzoyl-5-chloro-pyridin-2-yl)-amide
N-(2-Benzoyl-4-chloro-phenyl)-4-isopropylamino-benzenesulfonamide
N-(4-Benzoyl-pyridin-3-yl)-4-isopropyl-benzenesulfonamide
N-(4-Benzoyl-pyridin-3-yl)-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridin-3-yloxy)-phenyl]-4-isopropyl-benzenesulfonamide
N-(2-Benzoyl-pyridin-3-yl)-4-isopropoxy-benzenesulfonamide
N-[3-(3-Fluoro-benzoyl)-pyridin-2-yl]-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridin-3-yloxy)-phenyl]-4-isopropoxy-benzenesulfonamide
4-Isopropoxy-N-[3-(pyridine-4-carbonyl)-pyridin-4-yl]-benzenesulfonamide
6-Isopropoxy-pyridine-3-sulfonic acid (3-benzoyl-5-chloro-pyridin-2-yl)-amide
6-Isopropoxy-pyridine-3-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-[4-Chloro-2-(pyridin-2-ylsulfanyl)-phenyl]-4-isopropyl-benzenesulfonamide
N-(2-Benzoyl-phenyl)-4-isopropoxy-benzenesulfonamide; and pharmaceutically
acceptable salts, solvates, and hydrates thereof.
9 . A pharmaceutical composition, comprising a pharmaceutically acceptable carrier and the compound of claim 1 .
10 . A method of inhibiting a CCR9 receptor function in a subject in need thereof, comprising the step of administering to the subject an effective amount of a compound represented by the following structural formula:
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein:
Y is C(O), S, O, S(O) or S(O) 2 ;
X 1 , X 2 , and X 3 are each, independently, N or CR, provided that at least one of X 1 , X 2 , or X 3 is CR;
R, for each occurrence, and R 1 are each, independently, H or a substituent;
R 6 is H, an aliphatic carbonyl group, or an aliphatic ester; and
ring A is substituted or unsubstituted;
Ar 1 and Ar 2 are each, independently, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
11 . The method of claim 10 , wherein the compound is represented by a structural formula selected from the group consisting of A, B, C, and D:
A.
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein: R 19 and R 20 are each, independently, H or a substituent;
B.
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein: R 1 , R 2 , R 3 , R 4 , R 5 , and each R are, independently, H, an aliphatic group, haloalkyl, a halo, COOH, NO 2 , alkoxy, or haloalkoxy; and
X 4 is CR, N or N + —O − ;
C.
or pharmaceutically acceptable salts, solvates or hydrates thereof, wherein:
X 4 is CR, N or N + —O − ;
R 8 is H or an electron withdrawing group;
m and n are each, independently, 0 or an integer from 1 to 3;
each R 9 is, independently, an aliphatic group, haloalkyl, aryl, arylalkyl, alkoxy, cycloalkoxy, haloalkoxy, aryloxy, arylalkoxy, alkylthio, halo, nitro, cyano, hydroxy, NR 11 CO 2 R 12 , C(O)N(R 11 ) 2 , C(O)R 12 , CO 2 R 12 , OC(O)N(R 11 ) 2 , OC(O)R 12 , N(R 11 ) 2 , or NR 11 C(O)R 12 ; or two adjacent R 9 groups taken together with the atoms to which they are attached form a fused, saturated, unsaturated or partially unsaturated 5 to 7 membered ring having 0, 1 or 2 heteroatoms selected from the group consisting of N, O, and S;
each R 10 is, independently, halo, aliphatic group, alkoxy, or haloalkyl; or two adjacent R 10 groups taken together with the atoms to which they are attached form a fused, saturated, unsaturated or partially unsaturated 5 to 7 membered ring having 0, 1 or 2 heteroatoms selected from the group consisting of N, O, and S;
each R 11 is, independently, H or an aliphatic group; and
R 12 is an aliphatic group; and
D.
or pharmaceutically acceptable salts, solvates or hydrates thereof, wherein:
R 8 is halo, nitro, alkylcarbonyl or trihaloalkyl;
p is 0 or an integer from 1 to 3; and
each R 13 is, independently, a halo, a substituted or unsubstituted heterocycle, or a substituted or unsubstituted heteroaryl.
12 . The method of claim 10 wherein the subject is being treated for an inflammatory disease or condition.
13 . A method of treating or preventing an inflammatory disease or condition in a subject in need thereof, comprising administering to the subject an effective amount of a compound represented by the following structural formula:
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein:
Y is C(O), S, O, S(O) or S(O) 2 ;
X 1 , X 2 , and X 3 are each, independently, N or CR, provided that at least one of X 1 , X 2 , or X 3 is CR;
R, for each occurrence, and R 1 are each, independently, H or a substituent; and
ring A is substituted or unsubstituted;
R 6 is H, an aliphatic group, an aryl group or an aliphatic carbonyl group; and
Ar 1 and Ar 2 are each, independently, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
14 . The method of claim 13 , wherein the compound is represented by a structural formula selected from the group consisting of A, B, C, and D:
A.
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein: R 19 and R 20 are each, independently, H or a substituent.
B.
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein: R 1 , R 2 , R 3 , R 4 , R 5 , and each R are, independently, H, an aliphatic group, haloalkyl, halo, COOH, NO 2 , alkoxy, or haloalkoxy; and
X 4 is CR, N or N + —O − ;
C.
or pharmaceutically acceptable salts, solvates or hydrates thereof, wherein:
X 4 is CR, N or N + —O − ;
R 8 is H or an electron withdrawing group;
m and n are each, independently, 0 or an integer from 1 to 3;
each R 9 is, independently, aliphatic group, haloalkyl, aryl, arylalkyl, alkoxy, cycloalkoxy, haloalkoxy, aryloxy, arylalkoxy, alkylthio, halo, nitro, cyano, hydroxy, NR 11 CO 2 R 12 , C(O)N(R 11 ) 2 , C(O)R 12 , CO 2 R 12 , OC(O)N(R 11 ) 2 , OC(O)R 12 , N(R 11 ) 2 , or NR 11 C(O)R 12 ; or two adjacent R 9 groups taken together with the atoms to which they are attached form a fused, saturated, unsaturated or partially unsaturated 5 to 7 membered ring having 0, 1 or 2 heteroatoms selected from the group consisting of N, O, and S;
each R 10 is, independently, halo, aliphatic group, alkoxy, or haloalkyl; or two adjacent R 10 groups taken together with the atoms to which they are attached form a fused, saturated, unsaturated or partially unsaturated 5 to 7 membered ring having 0, 1 or 2 heteroatoms selected from the group consisting of N, O, and S;
each R 11 is, independently, H or an aliphatic group; and
R 12 is an aliphatic group; and
D.
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein:
R 8 is a halo, nitro, alkylcarbonyl or trihaloalkyl;
p is 0 or an integer from 1 to 3; and
each R 13 is, independently, a halo, a substituted or unsubstituted heterocycle, or a substituted or unsubstituted heteroaryl.
15 . The method of claim 13 , wherein the compound is selected from the group consisting of:
N-[4-Chloro-2-(2-chloro-benzoyl)-phenyl]-4-nitro-benzenesulfonamide
Thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-(2-Benzoyl-4-chloro-phenyl)-4-iodo-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-chloro-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-tert-butyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-propyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-ethyl-benzenesulfonamide
N-(2-Benzoyl-4-nitro-phenyl)-4-ethyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-isopropyl-benzenesulfonamide
N-(2-Benzoyl-4-bromo-phenyl)-4-ethyl-benzenesulfonamide
N-(2-Benzoyl-4-bromo-phenyl)-4-methoxy-benzenesulfonamide
N-(2-Benzoyl-4-bromo-phenyl)-4-isopropyl-benzenesulfonamide
4-Ethyl-N-[4-nitro-2-(3-trifluoromethyl-benzoyl)-phenyl]-benzenesulfonamide
N-[4-Chloro-2-(3-methyl-benzoyl)-phenyl]-4-ethyl-benzenesulfonamide
N-(2-Benzoyl-4-bromo-phenyl)-4-chloro-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-ethoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-propoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-isopropoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-butoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-benzyloxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-phenoxy-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridine-4-carbonyl)-phenyl]-4-ethoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridine-4-carbonyl)-phenyl]-4-isopropyl-benzenesulfonamide
N-[4-Chloro-2-(pyridine-4-carbonyl)-phenyl]-4-isobutyl-benzenesulfonamide
N-[5-Chloro-3-(pyridine-4-carbonyl)-pyridin-2-yl]-4-ethoxy-benzenesulfonamide
N-[5-Chloro-3-(pyridine-4-carbonyl)-pyridin-2-yl]-4-isopropoxy-benzenesulfonamide
N-(3-Benzoyl-5-trifluoromethyl-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-(2-Benzoyl-4-nitro-phenyl)-4-chloro-benzenesulfonamide
5-Benzoyl-6-(4-isopropoxy-benzenesulfonylamino)-nicotinic acid
N-(2-Benzoyl-4-chloro-phenyl)-2-nitro-benzenesulfonamide
N-(3-Benzoyl-5-nitro-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-(5-Benzoyl-pyrimidin-4-yl)-4-isopropoxy-benzenesulfonamide
N-(3-Benzoyl-5-trifluoromethoxy-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-(5-Benzoyl-2-trifluoromethyl-pyrimidin-4-yl)-4-isopropoxy-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-cyclopropoxy-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-cyclobutyl-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-tert-butoxy-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-cyclopentyl-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-isopropylsulfanyl-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-isopropylamino-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-cyclopropyl-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-cyclohexyl-benzenesulfonamide
N-(3-Benzenesulfinyl-5-chloro-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-(3-Benzenesulfonyl-5-chloro-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyrimidine-5-carbonyl)-phenyl]-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridazine-4-carbonyl)-phenyl]-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(2-trifluoromethyl-pyrimidine-5-carbonyl)-phenyl]-4-isopropoxy-
benzenesulfonamide
N-[4-Chloro-2-(6-trifluoromethyl-pyridazine-4-carbonyl)-phenyl]-4-isopropoxy-
benzenesulfonamide
N-[4-Chloro-2-(2-trifluoromethyl-pyrimidine-5-carbonyl)-phenyl]-4-isopropoxy-
benzenesulfonamide
N-[4-Chloro-2-(6-trifluoromethyl-pyridazine-4-carbonyl)-phenyl]-4-isopropoxy-
benzenesulfonamide
N-(2-Benzoyl-4-nitro-phenyl)-4-isopropyl-benzenesulfonamide
N-(2-Benzoyl-4-nitro-phenyl)-4-isopropoxy-benzenesulfonamide
N-(2-Benzoyl-4-nitro-phenyl)-4-methoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-trifluoromethoxy-benzenesulfonamide
5-Oxazol-5-yl-thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-[4-Chloro-2-(3-chloro-benzoyl)-phenyl]-4-methoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-methoxy-benzenesulfonamide
N-[4-Chloro-2-(3-chloro-benzoyl)-phenyl]-4-ethyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-ethylamino-benzenesulfonamide
5-(1-Methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-thiophene-2-sulfonic acid (2-benzoyl-4-
chloro-phenyl)-amide
N-(2-Benzoyl-4-iodo-phenyl)-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(3-fluoro-benzoyl)-phenyl]-4-methyl-benzenesulfonamide
N-[4-Chloro-2-(3-chloro-benzoyl)-phenyl]-4-isopropyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-nitro-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-diethylamino-benzenesulfonamide
N-(2-Benzoyl-4-fluoro-phenyl)-4-methoxy-benzenesulfonamide
4-Chloro-N-[4-chloro-2-(pyridine-3-carbonyl)-phenyl]-benzenesulfonamide
N-(2-Benzoyl-4-bromo-phenyl)-4-methyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-bromo-benzenesulfonamide
N-[4-Chloro-2-(pyridine-3-carbonyl)-phenyl]-4-methoxy-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-dimethylamino-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-fluoro-benzenesulfonamide
4-Chloro-N-[4-chloro-2-(2-fluoro-benzoyl)-phenyl]-benzenesulfonamide
N-[4-Chloro-2-(2-fluoro-benzoyl)-phenyl]-4-methoxy-benzenesulfonamide
Thiophene-3-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
5-Bromo-thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
5-Chloro-thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-[4-Chloro-2-(2-fluoro-benzoyl)-phenyl]-4-nitro-benzenesulfonamide
N-[4-Chloro-2-(2-fluoro-benzoyl)-phenyl]-4-methyl-benzenesulfonamide
4-Chloro-N-[4-chloro-2-(pyridine-2-carbonyl)-phenyl]-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-benzenesulfonamide
N-[4-(2-Benzoyl-4-chloro-phenylsulfamoyl)-phenyl]-acetamide
N-[4-Chloro-2-(pyridine-2-carbonyl)-phenyl]-4-methoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridine-2-carbonyl)-phenyl]-4-methyl-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-cyano-benzenesulfonamide
4,5-Dibromo-thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-[4-Chloro-2-(pyridine-3-sulfonyl)-phenyl]-4-nitro-benzenesulfonamide
Naphthalene-2-sulfonic acid [4-chloro-2-(pyridine-3-carbonyl)-phenyl]-amide
N-(2-Benzoyl-4-chloro-phenyl)-3-bromo-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-4-methyl-3-nitro-benzenesulfonamide
N-[4-Chloro-2-(2-methoxy-benzoyl)-phenyl]-4-nitro-benzenesulfonamide
N-(2-Benzoyl-4-chloro-phenyl)-2-trifluoromethyl-benzenesulfonamide
5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-
amide
N-(2-Benzoyl-phenyl)-4-nitro-benzenesulfonamide
5-Isoxazol-3-yl-thiophene-2-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-(2-Benzoyl-phenyl)-4-methyl-benzenesulfonamide
Benzo[b]thiophene-3-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-(4-Chloro-2-phenylsulfanyl-phenyl)-4-isopropoxy-benzenesulfonamide
N-(2-Benzenesulfonyl-4-chloro-phenyl)-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridine-4-carbonyl)-phenyl]-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(1-oxy-pyridine-4-carbonyl)-phenyl]-4-isopropoxy-benzenesulfonamide
4-Isopropoxy-N-[2-(pyridine-4-carbonyl)-4-trifluoromethyl-phenyl]-
benzenesulfonamide
4-Ethoxy-N-[2-(pyridine-4-carbonyl)-4-trifluoromethyl-phenyl]-benzenesulfonamide
N-[5-Chloro-3-(3-fluoro-benzoyl)-pyridin-2-yl]-4-isopropyl-benzenesulfonamide
N-[5-Chloro-3-(3-fluoro-benzoyl)-pyridin-2-yl]-4-isopropoxy-benzenesulfonamide
N-[5-Chloro-3-(thiophene-2-carbonyl)-pyridin-2-yl]-4-isopropoxy-benzenesulfonamide
5-Oxazol-5-yl-thiophene-2-sulfonic acid [5-chloro-3-(3-fluoro-benzoyl)-pyridin-2-yl]-
amide
N-[3-(Benzofuran-2-carbonyl)-5-chloro-pyridin-2-yl]-4-isopropoxy-
benzenesulfonamide
N-(2-Benzoyl-4-trifluoromethyl-phenyl)-4-isopropoxy-benzenesulfonamide
N-(3-Benzoyl-pyridin-4-yl)-4-isopropoxy-benzenesulfonamide
N-(3-Benzoyl-5-chloro-pyridin-2-yl)-4-isopropyl-benzenesulfonamide
N-(3-Benzoyl-5-nitro-pyridin-2-yl)-4-isopropoxy-benzenesulfonamide
5-Oxazol-5-yl-thiophene-2-sulfonic acid (3-benzoyl-5-chloro-pyridin-2-yl)-amide
N-(2-Benzoyl-4-chloro-phenyl)-4-isopropylamino-benzenesulfonamide
N-(4-Benzoyl-pyridin-3-yl)-4-isopropyl-benzenesulfonamide
N-(4-Benzoyl-pyridin-3-yl)-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridin-3-yloxy)-phenyl]-4-isopropyl-benzenesulfonamide
N-(2-Benzoyl-pyridin-3-yl)-4-isopropoxy-benzenesulfonamide
N-[3-(3-Fluoro-benzoyl)-pyridin-2-yl]-4-isopropoxy-benzenesulfonamide
N-[4-Chloro-2-(pyridin-3-yloxy)-phenyl]-4-isopropoxy-benzenesulfonamide
4-Isopropoxy-N-[3-(pyridine-4-carbonyl)-pyridin-4-yl]-benzenesulfonamide
6-Isopropoxy-pyridine-3-sulfonic acid (3-benzoyl-5-chloro-pyridin-2-yl)-amide
6-Isopropoxy-pyridine-3-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide
N-[4-Chloro-2-(pyridin-2-ylsulfanyl)-phenyl]-4-isopropyl-benzenesulfonamide
N-(2-Benzoyl-phenyl)-4-isopropoxy-benzenesulfonamide; and pharmaceutically
acceptable salts, solvates, and hydrates thereof.
16 . The method of claim 13 , wherein the inflammatory disease or condition is Crohn's disease or colitis.
17 . The method of claim 13 , wherein the inflammatory disease or condition is Celiac's disease.
18 . The method of claim 13 , wherein the compound inhibits the binding of a ligand to CCR9.
19 . The method of claim 18 , wherein the ligand is TECK.
20 . A method of inhibiting CCR9-mediated homing of leukocytes in a subject in need of such treatment comprising administering to the subject an effective amount of at least one compound represented by the following structural formula:
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein:
Y is C(O), S, S(O) or S(O) 2 ;
X 1 , X 2 , and X 3 are each, independently, N or CR, provided that at least one of X 1 , X 2 , or X 3 is CR;
R, for each occurrence, and R 1 are each, independently, H or a substituent;
R 6 is H, an aliphatic group, an aryl group or an aliphatic carbonyl group;
ring A is substituted or unsubstituted; and
Ar 1 and Ar 2 are each, independently, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
21 . The method of claim 20 , wherein the compound is represented by a structural formula selected from the group consisting of A, B, C, and D:
A.
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein: R 19 and R 20 are each, independently, H or a substituent.
B.
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein: R 1 , R 2 , R 3 , R 4 , R 5 , and each R are, independently, H, an aliphatic group, haloalkyl, halo, COOH, NO 2 , alkoxy, or haloalkoxy; and
X 4 is CR, N or N + —O−;
C.
or pharmaceutically acceptable salts, solvates or hydrates thereof, wherein:
X 4 is CR, N or N + —O − ;
R 8 is H or an electron withdrawing group;
m and n are each, independently, 0 or an integer from 1 to 3;
each R 9 is, independently, an aliphatic group, haloalkyl, aryl, arylalkyl, alkoxy, cycloalkoxy, haloalkoxy, aryloxy, arylalkoxy, alkylthio, halo, nitro, cyano, hydroxy, NR 11 CO 2 R 12 , C(O)N(R 11 ) 2 , C(O)R 12 , CO 2 R 12 , OC(O)N(R 11 ) 2 , OC(O)R 12 , N(R 11 ) 2 , or NR 11 C(O)R 12 ; or two adjacent R 9 groups taken together with the atoms to which they are attached form a fused, saturated, unsaturated or partially unsaturated 5 to 7 membered ring having 0, 1 or 2 heteroatoms selected from the group consisting of N, O, and S;
each R 10 is, independently, halo, aliphatic group, alkoxy, or haloalkyl; or two adjacent R 10 groups taken together with the atoms to which they are attached form a fused, saturated, unsaturated or partially unsaturated 5 to 7 membered ring having 0, 1 or 2 heteroatoms selected from the group consisting of N, O, and S;
each R 11 is, independently, H or an aliphatic group; and
R 12 is an aliphatic group; and
D.
or pharmaceutically acceptable salts, solvates or hydrates thereof,
wherein:
R 8 is a halo, nitro, alkylcarbonyl or trihaloalkyl;
p is 0 or an integer from 1 to 3; and
each R 13 is, independently, a halo, a substituted or unsubstituted heterocycle, or a substituted or unsubstituted heteroaryl.
22 . A method of inhibiting homing of leukocytes to mucosal tissue in a subject in need of such treatment, comprising administering to the subject an effective amount of at least one compound represented by the following structural formula:
or pharmaceutically acceptable salts, solvates or hydrates thereof, wherein:
Y is C(O), S, S(O) or S(O) 2 ;
X 1 , X 2 , and X 3 are each, independently, N or CR, provided that at least one of X 1 , X 2 , or X 3 is CR;
R, for each occurrence, and R 1 are each, independently, H or a substituent;
R 6 is H, an aliphatic group, an aryl group or an aliphatic carbonyl group;
ring A is substituted or unsubstituted; and
Ar 1 and Ar 2 are each, independently, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.Join the waitlist — get patent alerts
Track US2010324093A1 — get alerts on status changes and closely related new filings.
We store only your email — no account needed. See our privacy policy.