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US 10,829,427 B2Granted
Naphthoquinones, pro-drugs, and methods of use thereof
AssigneeBoard of Regents, The University of Texas System
InventorsJinming Gao, Yuliang Liu, Qi Wei, Xinpeng Ma, Gang Huang
Life of this patent
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Abstract
Provided herein are naphthoquinones compounds such as those with a hydrogen bond donating group of the formula (I): wherein: R1, R2, R3, R4, R5, and n are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.
Claims18
A compound of the formula:
- wherein:
- R1 is halo, nitro, substituted alkyl(C≤8), substituted alkoxy(C≤8), or —NRaRb, wherein:
- Ra or Rb are each independently hydrogen or —C(O)-alkoxy(C≤12), alkyl(C≤12), acyl(C≤12), alkylsulfonyl(C≤12), arylsulfonyl(C≤12), or a substituted version of any of these groups;
- or
- when n is more than 1, then both R1 are taken together and are an alkoxydiyl(C≤6) or substituted alkoxydiyl(C≤6);
- or
- —O-alkanediyl(C≤6)-Rc, wherein:
- Rc is amino, alkylamino(C≤8), dialkylamino(C≤8), heterocycloalkyl(C≤8), or a substituted version of any of these groups;
- R2 is absent or alkyl(C≤12), cycloalkyl(C≤12), acyl(C≤12), -alkanediyl(C≤6)-Rc, or a substituted version of any of these groups;
- wherein:
- Rc is amino, alkylamino(C≤8), dialkylamino(C≤8), heterocycloalkyl(C≤8), or a substituted version of any of these groups;
- provided that R2 is absent when the atom to which R2 is bound is a part of a double bond, and when the atom to which R2 is bound is part of a double bond, then R2 is absent;
- R3 is absent or alkyl(C≤12), cycloalkyl(C≤12), acyl(C≤12), -alkanediyl(C≤6)-Rc, —(CH2CH2O)mRd, or a substituted version of any of these groups;
- wherein:
- Rc is amino, alkylamino(C≤8), dialkylamino(C≤8), heterocycloalkyl(C≤8), or a substituted version of any of these groups;
- Rd is hydrogen, alkyl(C≤6), or substituted alkyl(C≤6);
- and
- m is 1, 2, 3, 4, or 5;
- provided that R3 is absent when the atom to which R3 is bound is a part of a double bond, and when the atom to which R3 is bound is part of a double bond, then R3 is absent;
- R4 is hydrogen, halo, alkyl(C≤6), or substituted alkyl(C≤6);
- R5 is absent or alkyl(C≤12), acyl(C≤12), or a substituted version of either of these groups;
- provided that R5 is absent when the atom to which R5 is bound is a part of a double bond, and when the atom to which R5 is bound is part of a double bond, then R5 is absent;
- and
- n is 1, 2, 3, or 4;
- provided that when R2 and R5 are acyl(C≤12) or substituted acyl(C≤12), then R3 is alkyl(C≤12) or substituted alkyl(C≤12);
- or a pharmaceutically acceptable salt thereof.
23 more elements
Dependencies are inferred from the claim text.