Bacterial efflux pump inhibitors
US-2016271081-A1 · Sep 22, 2016 · US
US9926261B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9926261-B2 |
| Application number | US-201615066911-A |
| Country | US |
| Kind code | B2 |
| Filing date | Mar 10, 2016 |
| Priority date | Mar 10, 2015 |
| Publication date | Mar 27, 2018 |
| Grant date | Mar 27, 2018 |
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Disclosed herein are compounds of formula I: and salts thereof. Also disclosed are compositions comprising of compounds of formula I and methods using compounds of formula I.
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The invention claimed is: 1. A compound of formula I: wherein: R 1 is (C 3 -C 8 )alkyl substituted with two or more groups selected from —NR b1 R c1 ; R 2 is hydrogen or (C 1 -C 3 )alkyl; each R 3 is independently hydrogen, halo or (C 1 -C 4 )alkyl; R 4 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 5 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 6 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 7 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 8 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; each R b1 and R c1 is independently hydrogen or (C 1 -C 4 )alkyl; and n is 0 or 1; or a salt thereof; provided at least one of R 4 , R 5 , or R 6 is not hydrogen. 2. The compound of claim 1 , wherein R 2 is hydrogen and each R 3 is hydrogen. 3. The compound of claim 1 , wherein R 8 is hydrogen. 4. The compound of claim 1 , wherein R 4 is hydrogen, (C 1 -C 6 )haloalkyl or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy. 5. The compound of claim 1 , wherein R 6 is (C 1 -C 6 )haloalkyl or hydrogen. 6. The compound of claim 1 , wherein R 5 is (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, or phenyl wherein phenyl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy. 7. The compound of claim 1 , wherein R 7 is (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, or phenyl wherein phenyl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy. 8. The compound of claim 1 , wherein the moiety: of the compound of formula I is: 9. The compound of claim 1 , wherein R 1 is (C 3 -C 8 )alkyl substituted with two groups independently selected from —NR b1 R c1 . 10. The compound of claim 1 , wherein R 1 is: 11. The compound of claim 1 , wherein n is 0. 12. The compound of claim 1 which is: or a salt thereof. 13. A compound of formula I: wherein: R 1 is (C 3 -C 8 )alkyl substituted with two or more groups selected from —NR b1 R c1 ; R 2 is hydrogen or (C 1 -C 3 )alkyl; each R 3 is independently hydrogen, halo or (C 1 -C 4 )alkyl; R 4 is halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 5 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 6 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 7 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 8 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; each R b1 and R c1 is independently hydrogen or (C 1 -C 4 )alkyl; and n is 0 or 1; or a salt thereof. 14. A compound of formula I: wherein: R 1 is (C 3 -C 8 )alkyl substituted with two or more groups selected from —NR b1 R c1 ; R 2 is hydrogen or (C 1 -C 3 )alkyl; each R 3 is independently hydrogen, halo or (C 1 -C 4 )alkyl; R 4 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 5 is halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 6 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy; R 7 is hydrogen, halo, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 4 )haloalkoxy, or aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloa
Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title
with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom · CPC title
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