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US 2019/0202774 A1Published application
Biaryl compounds as antimicrobial and chemotherapeutic agents
AssigneesWilliam Marsh Rice University, The Texas A&M University System, Board of Regents, The University of Texas System
InventorsHongyin GAO, Laszlo KURTI, Kush SHAH, Parth SHAH, Carolyn L CANNON
Life of this patent
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Abstract
In one aspect, the present disclosure provides diaryl compounds of the formula presented herein. The application also provides compositions and methods of treatment thereof. In some embodiments, these compounds are used in the treatment of bacterial infections or in the treatment of cancer.
Claims25
A compound of the formula:
- wherein:
- X1 is amino or alkylamino(C≤8), dialkylamino(C≤8), amido(C≤8), or a substituted version of any of these groups;
- or —N(Ra)Rb, wherein:
- Ra is a monovalent amino protecting group or is taken together with Rb and form a divalent amino protecting group;
- and
- Rb is hydrogen, a monovalent amino protecting group;
- or is taken together with Ra and form a divalent amino protecting group;
- X2 is hydroxy or alkoxy(C≤8), acyloxy(C≤8), or a substituted version of any of these groups;
- or —ORc wherein:
- Rc is a hydroxy protecting group;
- Y1 is halo;
- Y2 is hydrogen or halo;
- A1 and A2 are each independently hydrogen, halo, alkyl(C≤8), substituted alkyl(C≤8), cycloalkyl(C≤8), substituted cycloalkyl(C≤8), alkoxy(C≤8), or substituted alkoxy(C≤8);
- R1 and R2 are each independently hydrogen, halo, alkyl(C≤8), substituted alkyl(C≤8), cycloalkyl(C≤8), substituted cycloalkyl(C≤8), alkoxy(C≤8), or substituted alkoxy(C≤8);
- or R1 and R2 are taken together and are alkenediyl(C≤8) or substituted alkenediyl(C≤8);
- and
- R3 and R4 are each independently hydrogen, halo, alkyl(C≤8), substituted alkyl(C≤8), cycloalkyl(C≤8), substituted cycloalkyl(C≤8), alkoxy(C≤8), or substituted alkoxy(C≤8);
- or R3 and R4 are taken together and are alkenediyl(C≤8) or substituted alkenediyl(C≤8);
- or
- a compound of the formula:
- wherein:
- X3 is —ORd or —NReRf, wherein:
- Rd is hydrogen, alkyl(C≤8), cycloalkyl(C≤8), acyl(C≤8), or a substituted version of any of these groups;
- or a hydroxy protecting group;
- Re and Rf are each independently hydrogen, alkyl(C≤8), cycloalkyl(C≤8), acyl(C≤8), or a substituted version of any of these groups;
- or a monovalent amino protecting group, or Re and Rf are taken together and are a divalent amino protecting group;
- R6 is hydrogen or alkyl(C≤8), cycloalkyl(C≤8), or a substituted version of either of these groups;
- R7, R8, and R9 are each independently hydrogen, halo, or alkyl(C≤8), cycloalkyl(C≤8), alkoxy(C≤8), or a substituted version of any of these groups;
- or R7 and R8 are taken together and are alkenediyl(C≤8) or substituted alkenediyl(C≤8);
- and
- Y3, Y4, Y5, and Y6 are each independently hydrogen, halo, hydroxy, or alkyl(C≤8), cycloalkyl(C≤8), alkoxy(C≤8), or a substituted version of any of these groups;
- or Y3 and Y4 are taken together and are alkenediyl(C≤8) or substituted alkenediyl(C≤8), or Y4 and Y5 are taken together and are alkenediyl(C≤8) or substituted alkenediyl(C≤8), or Y5 and Y6 are taken together and are alkenediyl(C≤8) or substituted alkenediyl(C≤8);
- or a pharmaceutically acceptable salt thereof.
30 more elements
12-125. (canceled)
128-133. (canceled)
A pharmaceutical composition comprising:
- (a) a compound of the formula:
- wherein:
- R1, R2, R3, and R4 are each halo;
- X1 and X2 are OAc or O−M+;
- wherein:
- M+ is a monovalent cations or the M+ associated with X1 and X2 are taken together and are a divalent cation;
- and
- (b) a pharmaceutically acceptable carrier.
5 more elements
(canceled)
(canceled)
141-146. (canceled)
148-180. (canceled)
Dependencies are inferred from the claim text.