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US 2003/0149026 A1Published application
Heterocyclo-alkylsulfonyl pyrazoles
AssigneePfizer Inc.
InventorsSubas M. Sayka, Martha L. Minich
Life of this patent
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Abstract
The present invention relates to heterocyclo alkylsulfonyl pyrazoles of the formula I: 1 wherein the ring of the formula (R5)-A-(SOmR4), m, X, R1 through R5 are as defined in the specification, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the invention are useful in the treatment or alleviation of inflammation and other inflammation associated disorders, such as arthritis, colon cancer, and Alzheimer's disease in mammals, preferably humans, dogs, cats and livestock animals.
Claims14
A compound of the formula I:
- 26
- or a pharmaceutically acceptable salt thereof;
- wherein the ring of the formula (R5)-A-(SOmR4) is selected from the group consisting of
- 27
- m is 0, 1 or 2;
- X is >CR5 or >N;
- R1 is a radical selected from the group consisting of H, —NO2, —CN, (C1-C6)alkyl, (C1-C6)alkyl-SO2—, (C6-C10)aryl-SO2—, H—(C═O)—, (C1-C6)alkyl-(C═O)—, (C1-C6)alkyl-O—(C═O)—, (C1-C9)heteroaryl-(C═O)—, (C1-C9)heterocyclyl-(C═O)—, H2N—(C═O)—, (C1-C6)alkyl-NH—(C═O)—, [(C1-C6)alkyl]2—N—(C═O)—, [(C6-C10)aryl]-NH—(C═O)—, [(C1-C6)alkyl]-[((C6-C10)aryl)-N]—(C═O)—, HO—NH—(C═O)—, and (C1-C6)alkyl-O—NH—(C═O)—;
- R2 is a radical selected from the group consisting of H, —NO2, —CN, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C7)cycloalkyl, (C6-C10)aryl, (C1-C9)heteroaryl, (C1-C9)heterocyclyl, (C1-C6)alkyl-O—, (C3-C7)cycloalkyl-O—, (C6-C10)aryl-O—, (C1-C9)heteroaryl-O—, (C1-C9)heterocyclyl-O—, H—(C═O)—, (C1-C6)alkyl-(C═O)—, (C3-C7)cycloalkyl-(C═O)—, (C6-C10)aryl-(C═O)—, (C1-C9)heteroaryl-(C═O)—, (C1-C9)heterocyclyl-(C═O)—, (C1-C6)alkyl-O—(C═O)—, (C3-C7)cycloalkyl-O—(C═O)—, (C6-C10)aryl-O—(C═O)—, (C1-C9)heteroaryl-O—(C═O)—, (C1-C9)heterocyclyl-O—(C═O)—, (C1-C6)alkyl-(C═O)—O—, (C3-C7)cycloalkyl-(C═O)—O—, (C6-C10)aryl-(C═O)—O—, (C1-C9)heteroaryl-(C═O)—O—, (C1-C9)heterocyclyl-(C═O)—O—, (C1-C6)alkyl-(C═O)—NH—, (C3-C7)cycloalkyl-(C═O)—NH—, (C6-C10)aryl-(C═O)—N H—, (C1-C9)heteroaryl-(C═O)—N H—, (C1-C9)heterocyclyl-(C═O)—N H—, (C1-C6)alkyl-O—(C═O)—NH—, (C1-C6)alkyl-NH, [(C1-C6)alkyl]2—N—, (C3-C7)cycloalkyl-NH—, [(C3-C7)cycloalkyl]2—N—, [(C6-C10)aryl]-NH—, [(C6-C10)aryl]2—N—, [(C1-C6)alkyl]-[((C6-C10)aryl)-N]—, [(C1-C9)heteroaryl]-NH—, [(C1-C9)heteroaryl]2—N—, [(C1-C9)heterocyclyl]-NH—, [(C1-C9)heterocyclyl]2—N—, H2N—(C═O)—, HO—NH—(C═O)—, (C1-C6)alkyl-O—NH—(C═O)—, [(C1-C6)alkyl]-NH—(C═O)—, [(C1-C6)alkyl]2—N—(C═O)—, [(C3-C7)cycloalkyl]-NH—(C═O)—, [(C3-C7)cycloalkyl]2—N—(C═O)—, [(C6-C10)aryl]-NH—(C═O)—, [(C6-C10)aryl]2—N—(C═O)—, [(C1-C6)alkyl]-[((C6-C10)aryl)-N]—(C═O)—, [(C1-C9)heteroaryl]-NH—(C═O)—, [(C1-C9)heteroaryl]2—N—(C═O)—, [(C1-C9)heterocyclyl]-NH—(C═O)—, (C1-C6)alkyl-S— and (C1-C6)alkyl optionally substituted by one —OH substituent or by one to four fluoro substituents;
- R3 is a saturated (3- to 4-membered)-heterocyclyl ring radical;
- or a saturated, partially saturated or aromatic (7- to 9-membered)-heterocyclyl ring radical;
- wherein said saturated (3- to 4-membered)-heterocyclyl ring radical;
- or said saturated, partially saturated or aromatic (7- to 9-membered)-heterocyclyl ring radical;
- may optionally contain one to four ring heteroatoms independently selected from the groups consisting of —N═, —NH—, —O—, and —S—;
- wherein said saturated (3- to 4-membered)-heterocyclyl ring radical;
- or said saturated, partially saturated or aromatic (7- to 9-membered)-heterocyclyl ring radical;
- may optionally be substituted on any ring carbon atom by one to three substituents per ring independently selected from the group consisting of halo, —OH, —CN, —NO2, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C7)cycloalkyl, (C6-C10)aryl, (C2-C9)heterocyclyl, (C1-C6)alkyl-O—, H—(C═O)—, (C1-C6)alkyl-(C═O)—, HO—(C═O)—, (C1-C6)alkyl-O—(C═O)—, —NH2, (C1-C6)alkyl-NH—, [(C1-C6)alkyl]2—N—, (C3-C7)cycloalkyl-NH—, (C6-C10)aryl-NH—, [(C1-C6)alkyl]-[((C6-C10)aryl)-N]—, (C1-C9)heteroaryl-NH—, H2N—(C═O)—, [(C1-C6)alkyl]-NH—(C═O)—, [(C1-C6)alkyl]2—N—(C═O)—, [(C6-C10)aryl]-NH—(C═O)—, [(C1-C6)alkyl]-[((C6-C10)aryl)-N]—(C═O)—, (C1-C6)alkyl-O—NH—(C═O)—, (C1-C6)alkyl-(C═O)—HN—, (C1-C6)alkyl-(C═O)—[(C1-C6)alkyl-N]—, —SH, (C1-C6)alkyl-S—, (C1-C6)alkyl-(S═O)—, (C1-C6)alkyl-SO2— and (C1-C6)alkyl optionally substituted with one to four fluoro moieties;
- wherein said saturated (3- to 4-membered)-heterocyclyl ring radical;
- or said saturated, partially saturated or aromatic (7- to 9-membered)-heterocyclyl ring radical;
- may also optionally be substituted on any ring nitrogen atom by one to three substituents per ring independently selected from the group consisting of (C3-C7)cycloalkyl, (C6-C10)aryl, (C2-C9)heterocyclyl, H—(C═O)—, (C1-C6)alkyl-(C═O)—, (C1-C6)alkyl-O—(C═O)—, H2N—(C═O)—, [(C1-C6)alkyl]-NH—(C═O)—, [(C1-C6)alkyl]2—N—(C═O)—, [(C6-C10)aryl]-NH—(C═O)—, [(C1-C6)alkyl]-[((C6-C10)aryl)-N]—(C═O)—, (C1-C6)alkyl-O—NH—(C═O)—, and (C1-C6)alkyl optionally substituted with one to four fluoro moieties;
- R4 is an (C1-C6)alkyl radical optionally substituted by one to four fluoro substituents;
- and
- R5 is a radical selected from the group consisting of H, halo, —OH, (C1-C6)alkyl-O—, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C7)cycloalkyl, —CN, H—(C═O)—, (C1-C6)alkyl-(C═O)—, (C1-C6)alkyl-(C═O)—O—, HO—(C═O)—, (C1-C6)alkyl-O—(C═O)—, (C1-C6)alkyl-NH—, [(C1-C6)alkyl]2—N—, (C3-C7)cycloalkyl-NH—, (C6-C10)aryl-NH—, [(C1-C6)alkyl]-[((C6-C10)aryl)-N]—, (C1-C9)heteroaryl-NH—, H2N—(C═O)—, (C1-C6)alkyl-NH—(C═O)—, [(C1-C6)alkyl]2—N—(C═O)—, (C6-C10)aryl-(C═O)—, [(C1-C6)alkyl]-[((C6-C10)aryl)-N]—(C═O)—, (C1-C6)alkyl-O—NH—(C═O)—, (C1-C6)alkyl-S—, and (C1-C6)alkyl optionally substituted by one to four fluoro substituents.
19 more elements
Dependencies are inferred from the claim text.