Sulfur derivatives as chemokine receptor modulators
First Claim
Patent Images
1. A compound having Formula I, its enantiomers, diastereoisomers, hydrates, solvates, and individual isomers, tautomers or a pharmaceutically acceptable salt thereof:
1 Assignment
0 Petitions
Accused Products
Abstract
The present invention relates to novel sulfur derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of chemokine receptors.
17 Citations
14 Claims
-
1. A compound having Formula I, its enantiomers, diastereoisomers, hydrates, solvates, and individual isomers, tautomers or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14)
-
2. A compound according to claim 1, wherein:
R5 is —
S—
.
-
3. A compound according to claim 1, wherein:
R5 is —
S(O)—
.
-
4. A compound according to claim 1, wherein:
R5 is —
S(O)2—
.
-
5. A compound according to claim 1, wherein:
R2 is methyl, isopropyl, 2-hydroxyethyl, methylpropionate, 2-methylpyridine, 3-methylpyridine, ethylacetate, N,N-dimethylpropanamide, N-isopropylpropanamide, N-(propan-2-yl)propanamide, propanamide hydroxycyclopent-3-yl, ethyl, N,N-dimethylacetamide, N-methylacetamide, 2-aminoethyl, 1H-imidazol-2-ylmethyl, 1H-imidazol-4-ylmethyl or ethyl-acetamide.
-
6. A compound according to claim 1, wherein:
-
R17 is H, substituted or unsubstituted C1-6 alkyl or halogen; R18 is H, substituted or unsubstituted C1-6 alkyl or halogen; R7 is halogen, CN, —
OC1-6 alkyl, substituted or unsubstituted C1-6 alkyl or substituted or unsubstituted C3-8 cycloalkyl; andR8 is H, substituted or unsubstituted C1-6 alkyl or halogen.
-
-
7. A compound according to claim 1, wherein:
-
R17 is H; R18 is H; R7 is halogen, CN or —
OC1-6 alkyl; andR8 is H.
-
-
8. A compound according to claim 1, wherein:
-
R2 is methyl, isopropyl, 2-hydroxyethyl, methylpropionate, 2-methylpyridine, 3-methylpyridine, ethylacetate, N,N-dimethylpropanamide, N-isopropylpropanamide, N-(propan-2-yl)propanamide, propanamide hydroxycyclopent-3-yl, ethyl, N,N-dimethylacetamide, N-methylacetamide, 2-aminoethyl, 1H-imidazol-2-ylmethyl, 1H-imidazol-4-ylmethyl or ethyl-acetamide; R5 is —
S—
, —
S(O)—
, or —
S(O)2—
;R17 is H; R18 is H; R7 is halogen, CN or —
OC1-6 alkyl; andR8 is H.
-
-
9. A compound according to claim 8, wherein:
R5 is —
S(O)—
.
-
10. A compound according to claim 8, wherein:
R5 is —
S(O)2—
.
-
11. A compound according to claim 8, wherein:
R5 is —
S—
.
-
12. A compound according to claim 1, selected from:
-
4-chloro-N-[5-chloro-2-(methylsulfinyl)phenyl]-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-[5-chloro-2-(methylsulfonyl)phenyl]-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-[5-chloro-2-(methylsulfanyl)phenyl]-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-[5-chloro-2-(propan-2-ylsulfanyl)phenyl]-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(2-hydroxyethyl)sulfanyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(2-hydroxyethyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(2-hydroxyethyl)sulfonyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; methyl 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}propanoate; 4-chloro-N-{5-chloro-2-[(pyridin-2-ylmethyl)sulfanyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(pyridin-3-ylmethyl)sulfanyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(pyridin-2-ylmethyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(pyridin-3-ylmethyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; ethyl{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}acetate; 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfanyl}-N-(propan-2-yl)propanamide; 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfanyl}-N,N-dimethylpropanamide; 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}-N-(propan-2-yl)propanamide; 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}-N,N-dimethylpropanamide; 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}propanamide; 4-chloro-N-{5-chloro-2-[(3-nitrophenyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(3-hydroxycyclopentyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(3-hydroxycyclopentyl)sulfonyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-[5-chloro-2-(ethylsulfanyl)phenyl]-3-(trifluoromethyl)benzene sulfonamide; 4-chloro-N-[5-chloro-2-(ethylsulfinyl)phenyl]-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-[5-chloro-2-(ethylsulfonyl)phenyl]-3-(trifluoromethyl)benzene sulfonamide; 2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfanyl}-N,N-dimethylacetamide; 2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}-N,N-dimethylacetamide; 2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfonyl}-N,N-dimethylacetamide; 2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}-N-methylacetamide; 2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfonyl}-N-methylacetamide; N-{2-[(2-aminoethyl)sulfanyl]-5-chlorophenyl}-4-chloro-3-(trifluoromethyl)benzenesulfonamide; 3-chloro-N-[5-chloro-2-(methylsulfanyl)phenyl]-2-fluorobenzenesulfonamide; N-{2-[(2-aminoethyl)sulfinyl]-5-chlorophenyl}-4-chloro-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-2-ylmethyl)sulfanyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-2-ylmethyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-2-ylmethyl)sulfonyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-4-ylmethyl)sulfanyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-4-ylmethyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-4-ylmethyl)sulfonyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; N-(2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfonyl}ethyl)acetamide; N-(2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}ethyl)acetamide; and 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfonyl}-N,N-dimethylpropanamide.
-
-
13. A pharmaceutical composition comprising as active ingredient a therapeutically effective amount of a compound according to claim 1, and a pharmaceutically acceptable adjuvant, diluents or carrier.
-
14. A pharmaceutical composition according to claim 1, wherein the compound is selected from:
-
4-chloro-N-[5-chloro-2-(methylsulfinyl)phenyl]-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-[5-chloro-2-(methylsulfonyl)phenyl]-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-[5-chloro-2-(methylsulfanyl)phenyl]-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-[5-chloro-2-(propan-2-ylsulfanyl)phenyl]-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(2-hydroxyethyl)sulfanyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(2-hydroxyethyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(2-hydroxyethyl)sulfonyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; methyl 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}propanoate; 4-chloro-N-{5-chloro-2-[(pyridin-2-ylmethyl)sulfanyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(pyridin-3-ylmethyl)sulfanyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(pyridin-2-ylmethyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(pyridin-3-ylmethyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; ethyl{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}acetate; 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfanyl}-N-(propan-2-yl)propanamide; 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfanyl}-N,N-dimethylpropanamide; 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}-N-(propan-2-yl)propanamide; 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}-N,N-dimethylpropanamide; 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}propanamide; 4-chloro-N-{5-chloro-2-[(3-nitrophenyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(3-hydroxycyclopentyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(3-hydroxycyclopentyl)sulfonyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-[5-chloro-2-(ethylsulfanyl)phenyl]-3-(trifluoromethyl)benzene sulfonamide; 4-chloro-N-[5-chloro-2-(ethylsulfinyl)phenyl]-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-[5-chloro-2-(ethylsulfonyl)phenyl]-3-(trifluoromethyl)benzene sulfonamide; 2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfanyl}-N,N-dimethylacetamide; 2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}-N,N-dimethylacetamide; 2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfonyl}-N,N-dimethylacetamide; 2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}-N-methylacetamide; 2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfonyl}-N-methylacetamide; N-{2-[(2-aminoethyl)sulfanyl]-5-chlorophenyl}-4-chloro-3-(trifluoromethyl)benzenesulfonamide; 3-chloro-N-[5-chloro-2-(methylsulfanyl)phenyl]-2-fluorobenzenesulfonamide; N-{2-[(2-aminoethyl)sulfinyl]-5-chlorophenyl}-4-chloro-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-2-ylmethyl)sulfanyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-2-ylmethyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-2-ylmethyl)sulfonyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-4-ylmethyl)sulfanyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-4-ylmethyl)sulfinyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; 4-chloro-N-{5-chloro-2-[(1H-imidazol-4-ylmethyl)sulfonyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide; N-(2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfonyl}ethyl)acetamide; N-(2-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfinyl}ethyl)acetamide; and 3-{[4-chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfonyl}-N,N-dimethylpropanamide.
-
-
2. A compound according to claim 1, wherein:
Specification
- Resources
Thank you for your request. You will receive a custom alert email when the Litigation Campaign Assessment is available.
×
-
Current AssigneeAllergan, Inc. (Canada) (Abbvie Incorporated)
-
Original AssigneeAllergan, Inc. (Canada) (Abbvie Incorporated)
-
InventorsYuan, Haiqing, Beard, Richard L., Garst, Michael E., Donello, John E., Liu, Xiaoxia, Viswanath, Veena
-
Primary Examiner(s)Padmanabhan, Sreeni
-
Assistant Examiner(s)Neagu, Irina
-
Application NumberUS13/772,188Publication NumberTime in Patent Office524 DaysField of Search514/604, 514/712, 514/708, 514/709, 564/92, 546/339, 548/342.1US Class Current514/604CPC Class CodesA61P 17/00 Drugs for dermatological di...A61P 27/02 Ophthalmic agentsA61P 29/00 Non-central analgesic, anti...A61P 31/00 Antiinfectives, i.e. antibi...A61P 43/00 Drugs for specific purposes...C07C 2601/08 the ring being saturatedC07C 311/21 having the nitrogen atom of...C07C 317/34 having sulfone or sulfoxide...C07C 317/36 with the nitrogen atoms of ...C07C 317/42 Y being a hetero atomC07C 317/44 having sulfone or sulfoxide...C07C 317/50 at least one of the nitroge...C07C 321/30 Sulfides having the sulfur ...C07C 323/49 to sulfur atomsC07C 323/52 the carbon skeleton being a...C07C 323/56 the carbon skeleton contain...C07C 323/60 with the carbon atom of at ...C07C 323/67 containing sulfur atoms of ...C07D 207/09 Radicals substituted by nit...C07D 207/46 with hetero atoms directly ...C07D 213/32 : Sulfur atomsC07D 213/52 : Sulfur atomsC07D 233/64 : with substituted hydrocarbo...C07D 277/40 : Unsubstituted amino or imin...C07D 295/13 : to an acyclic saturated chainC07D 295/185 : from aliphatic carboxylic a...C07D 295/24 : Oxygen atomsC07D 307/64 : Sulfur atomsC07D 307/82 : with hetero atoms or with c...C07D 333/34 : Sulfur atomsC07D 405/12 : linked by a chain containin...C07D 413/12 : linked by a chain containin...C07D 417/12 : linked by a chain containin...C07F 9/304 : Aromatic acids (P-C aromati...C07F 9/3229 : Esters of aromatic acids (P...C07F 9/4021 : Esters of aromatic acids (P...C07F 9/5325 : Aromatic phosphine oxides o...C07F 9/59 : Hydrogenated pyridine ringsC07F 9/6533 : Six-membered rings