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US 9,040,526 B2Granted
Benzylpyrrolidinone derivatives as modulators of chemokine receptor activity
AssigneeBristol-Myers Squibb Company
InventorsIan K. Mangion, Percy H. Carter, Jingwu Duan, Andrew J. Tebben
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Abstract
The present application describes modulators of MCP-1 or CCR-2 of formula or stereoisomers or prodrugs or pharmaceutically acceptable salts thereof, wherein m, n, W, X, R1 and R6, are defined herein. In addition, methods of treating and preventing inflammatory diseases such as asthma and allergic diseases, as well as autoimmune pathologies such as rheumatoid arthritis and transplant rejection using modulators of formula (I) are disclosed.
Claims12
A compound of formula (I):
- or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein:
- X is O;
- W is a —NR2R3 or a 3- to 20-membered nitrogen containing ring, wherein the ring is
- (i) attached through the nitrogen atom, (ii) may optionally contain 1-4 heteroatoms selected from N, O, and S and (iii) be optionally substituted with one or more R10a's;
- m is 1-4;
- n is 0-2;
- R1 is H or alkyl;
- R2 is H, alkyl, cycloalkyl, aryl, heteroaryl or heterocyclyl, wherein the cycloalkyl, aryl, heteroaryl or heterocyclyl may be optionally substituted with may be optionally substituted with be optionally substituted with one or more R9a's;
- R3 is H, alkyl, cycloalkyl, aryl, heteroaryl or heterocyclyl, wherein the cycloalkyl, aryl, heteroaryl or heterocyclyl may be optionally substituted with may be optionally substituted with be optionally substituted with one or more R9a's;
- R6, at each occurrence, is independently selected from halo, alkyl, haloalkyl, haloalkoxy, and aryl optionally substituted with halo;
- R9a, at each occurrence, is independently selected from alkyl, haloalkyl, aryl, cycloalkyl, heteroaryl, heterocyclyl, halo, —CN, —NO2, —C(═O)OR14, —OCF3, —OR14, ═O, —NR14R14 or arylalkyl;
- R10a, at each occurrence, is independently selected from alkyl, haloalkyl, aryl, cycloalkyl, heteroaryl, heterocyclyl, halo, —CN, —NO2, —C(═O)OR14, —OCF3, —OR14, ═O, —NR14R14 or arylalkyl, wherein the aryl, cycloalkyl, heteroaryl, and heterocyclyl may be optionally substituted with on or more R14a'S;
- R14, at each occurrence, is independently selected from hydrogen, alkyl, cycloalkyl, aryl, heteroaryl or heterocyclyl, wherein the alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with be optionally substituted with 0-3 R14a;
- R14a, at each occurrence, is independently selected from alkyl, haloalkyl, aryl, cycloalkyl, heteroaryl, heterocyclyl, halo, —CN, —NO2, —C(═O)OR24, —OCF3, —OR24, ═O, —NR24R24 or arylalkyl;
- and
- R24, at each occurrence, is independently selected from hydrogen, alkyl, cycloalkyl, aryl, heteroaryl or heterocyclyl.
13 more elements
A compound, enantiomer, diastereomer, or salt thereof, selected from the group consisting of:
Dependencies are inferred from the claim text.