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US 10,836,706 B2Granted
Bacterial efflux pump inhibitors
AssigneeRutgers, The State University of New Jersey
InventorsEdmond J. LaVoie, Ajit Parhi, Gifty A. Blankson, Liping Wang, Xiao Chen, Yongzheng Zhang, Malvika Kaul, Daniel S. Pilch
Life of this patent
Estimating the term…
Abstract
Disclosed herein are compounds of formula I: and salts thereof. Also disclosed are compositions comprising compounds of formula I and methods using compounds of formula I.
Claims19
A compound of formula I:
- wherein:
- X is —O—, Y is —C(H)(NRb1Rc1) and n is 1;
- R1 is (C2-C8)alkyl substituted with two or more groups independently selected from —NRb2Rc2;
- each R2 is independently hydrogen, halo or (C1-C4)alkyl;
- each R3 is independently hydrogen, halo or (C1-C4)alkyl;
- R4 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R5 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R6 is hydrogen;
- R7 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R8 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- Rb1 and Rc1 are each independently hydrogen or (C1-C4)alkyl;
- and
- each Rb2 and Rc2 is independently hydrogen or (C1-C4)alkyl;
- or a salt thereof.
11 more elements
A compound of formula I:
- wherein:
- X is —O—, Y is —C(H)(NRb1Rc1)— and n is 1;
- R1 is (C1-C8)alkyl substituted with one or more groups selected from —NRb2Rc2, —NHNH2, —C(—NRa2)(NRb2Rc2), —NRa2C(—NRa2)(Rd2) and —NRa2C(—NRa2)(NRb2Rc2);
- each R2 is independently hydrogen, halo or (C1-C4)alkyl;
- each R3 is independently hydrogen, halo or (C1-C4)alkyl;
- R4 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R5 is (C1-C6)alkyl, (C1-C6)haloalkyl, or phenyl wherein phenyl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R6 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R7 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R8 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- Rb1 and Rc1 are each independently hydrogen or (C1-C4)alkyl;
- each Ra2 is independently hydrogen or (C1-C4)alkyl;
- each Rb2 and Rc2 is independently hydrogen or (C1-C4)alkyl;
- and
- Rd2 is (C1-C3)alkyl;
- or a salt thereof.
13 more elements
A compound of formula I:
- wherein:
- X is —O—, Y is —C(H)(NRb1Rc1) and n is 1;
- R1 is (C1-C8)alkyl substituted with one or more groups selected from —NRb2Rc2, —NHNH2, —C(—NRa2)(NRb2Rc2), —NRa2C(—NRa2)(Rd2) and —NRa2C(—NRa2)(NRb2Rc2);
- each R2 is independently hydrogen, halo or (C1-C4)alkyl;
- each R3 is independently hydrogen, halo or (C1-C4)alkyl;
- R4 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R5 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R6 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R7 is (C1-C6)alkyl, (C1-C6)haloalkyl, or phenyl wherein phenyl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- R8 is hydrogen, halo, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C4)haloalkoxy, aryl or heteroaryl wherein the aryl or heteroaryl is optionally substituted with one or more groups independently selected from halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy;
- Rb1 and Rc1 are each independently hydrogen or (C1-C4)alkyl;
- each Ra2 is independently hydrogen or (C1-C4)alkyl;
- each Rb2 and Rc2 is independently hydrogen or (C1-C4)alkyl;
- and
- Rd2 is (C1-C3)alkyl;
- or a salt thereof.
13 more elements
A compound that is:
- or a salt thereof.
Dependencies are inferred from the claim text.