Claims for Patent: 9,688,711

Summary for Patent: 9,688,711

Title:	Antibacterial aminoglycoside analogs
Abstract:	Compounds having antibacterial activity are disclosed. The compounds have the following structure (I): ##STR00001## including stereoisomers, pharmaceutically acceptable salts and prodrugs thereof, wherein Q.sub.1, Q.sub.2, Q.sub.3, R.sub.8 and R.sub.9 are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.
Inventor(s):	Aggen; James Bradley (Burlingame, CA), Goldblum; Adam Aaron (Berkeley, CA), Linsell; Martin Sheringham (San Mateo, CA), Dozzo; Paola (San Francisco, CA), Moser; Heinz Ernst (San Mateo, CA), Hildebrandt; Darin James (Cupertino, CA), Gliedt; Micah James (Sunnyvale, CA)
Assignee:	Achaogen, Inc. (South San Francisco, CA)
Application Number:	15/001,797
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 9,688,711
Patent Claims:	1. A compound having the following structure (I): ##STR00426## or a stereoisomer, pharmaceutically acceptable salt or prodrug thereof, wherein: Q.sub.1 is ##STR00427## Q.sub.2 is hydrogen, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, --C(.dbd.NH)NR.sub.4R.sub.5, --(CR.sub.10R.sub.11).sub.pR.sub.12, ##STR00428## Q.sub.3 is hydrogen, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, --C(.dbd.NH)NR.sub.4R.sub.5, --(CR.sub.10R.sub.11).sub.pR.sub.12, ##STR00429## each R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.8 and R.sub.10 is, independently, hydrogen or C.sub.1-C.sub.6 alkyl, or R.sub.1 and R.sub.2 together with the atoms to which they are attached can form a heterocyclic ring having from 4 to 6 ring atoms, or R.sub.2 and R.sub.3 together with the atoms to which they are attached can form a heterocyclic ring having from 4 to 6 ring atoms, or R.sub.1 and R.sub.3 together with the atoms to which they are attached can form a carbocyclic ring having from 4 to 6 ring atoms, or R.sub.4 and R.sub.5 together with the atom to which they are attached can form a heterocyclic ring having from 4 to 6 ring atoms; each R.sub.6 and R.sub.7 is, independently, hydrogen, hydroxyl, amino or C.sub.1-C.sub.6 alkyl, or R.sub.6 and R.sub.7 together with the atoms to which they are attached can form a heterocyclic ring having from 4 to 6 ring atoms; each R.sub.9 is, independently, hydrogen or methyl; each R.sub.11 is, independently, hydrogen, hydroxyl, amino or C.sub.1-C.sub.6 alkyl; each R.sub.12 is, independently, hydroxyl or amino; each n is, independently, an integer from 0 to 4; each m is, independently, an integer from 0 to 4; and each p is, independently, an integer from 1 to 5, and wherein at least one of Q.sub.2 and Q.sub.3 is other than hydrogen. 2. The compound of claim 1, wherein R.sub.8 is hydrogen and each R.sub.9 is methyl. 3. The compound of claim 1, wherein Q.sub.2 is other than hydrogen and Q.sub.3 is hydrogen. 4. The compound of claim 3, wherein Q.sub.1 is: ##STR00430## wherein: R.sub.1 is hydrogen; R.sub.2 is hydrogen; and each R.sub.3 is hydrogen; or Q.sub.1 is: ##STR00431## or Q.sub.1 is: ##STR00432## wherein: R.sub.1 is hydrogen; and R.sub.2 and R.sub.3 together with the atoms to which they are attached form a heterocyclic ring having from 4 to 6 ring atoms; or Q.sub.1 is: ##STR00433## or Q.sub.1 is: ##STR00434## wherein: R.sub.3 is hydrogen; and R.sub.1 and R.sub.2 together with the atoms to which they are attached form a heterocyclic ring having from 4 to 6 ring atoms; or Q.sub.1 is: ##STR00435## or Q.sub.1 is: ##STR00436## wherein: R.sub.2 is hydrogen; and R.sub.1 and R.sub.3 together with the atoms to which they are attached form a carbocyclic ring having from 4 to 6 ring atoms; or Q.sub.1 is: ##STR00437## 5. The compound of claim 1, wherein Q.sub.2 is --(CR.sub.10R.sub.11).sub.pR.sub.12 and wherein each R.sub.10 is hydrogen and each R.sub.11 is hydrogen. 6. The compound of claim 1, wherein Q.sub.2 is optionally substituted cycloalkylalkyl; or Q.sub.2 is optionally substituted heterocyclylalkyl. 7. The compound of claim 6, wherein Q.sub.2 is unsubstituted; or Q.sub.2 is substituted with hydroxyl or amino. 8. The compound of claim 1, wherein Q.sub.3 is other than hydrogen and Q.sub.2 is hydrogen. 9. The compound of claim 8 wherein Q.sub.1 is: ##STR00438## wherein: R.sub.1 is hydrogen; R.sub.2 is hydrogen; and each R.sub.3 is hydrogen; or Q.sub.1 is: ##STR00439## or Q.sub.1 is: ##STR00440## wherein: R.sub.1 is hydrogen; and R.sub.2 and R.sub.3 together with the atoms to which they are attached form a heterocyclic ring having from 4 to 6 ring atoms; or Q.sub.1 is: ##STR00441## or Q.sub.1 is: ##STR00442## wherein: R.sub.3 is hydrogen; and R.sub.1 and R.sub.2 together with the atoms to which they are attached form a heterocyclic ring having from 4 to 6 ring atoms; or Q.sub.1 is: ##STR00443## or Q.sub.1 is: ##STR00444## wherein: R.sub.2 is hydrogen; and R.sub.1 and R.sub.3 together with the atoms to which they are attached form a carbocyclic ring having from 4 to 6 ring atoms; or Q.sub.1 is: ##STR00445## 10. The compound of claim 9, wherein Q.sub.3 is --(CR.sub.10R.sub.11).sub.pR.sub.12. 11. The compound of claim 10, wherein each R.sub.10 is hydrogen and each R.sub.11 is hydrogen. 12. The compound of claim 9, wherein Q.sub.3 is optionally substituted cycloalkylalkyl; or Q.sub.3 is optionally substituted heterocyclylalkyl; or Q.sub.3 is optionally substituted heterocyclyl. 13. The compound of claim 12, wherein Q.sub.3 is unsubstituted; or Q.sub.3 is substituted with hydroxyl or amino. 14. The compound of claim 9, wherein Q.sub.3 is --C(.dbd.NH)NH.sub.2. 15. A pharmaceutical composition comprising a compound of claim 1, or a stereoisomer, pharmaceutically acceptable salt or prodrug thereof, and a pharmaceutically acceptable carrier, diluent or excipient. 16. A method of treating a bacterial infection in a mammal in need thereof, comprising administering to the mammal an effective amount of a compound of claim 1.