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US 10,590,088 B2Granted
4-(benzimidazol-2-ylamino)benzamide derivatives and methods of synthesis thereof
AssigneeTranslational Drug Development, LLC
InventorsTong Wang, Stephen Gately
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Abstract
Disclosed are 4-(benzimidazol-2-ylamino)benzamide derivatives useful in slowing the expansion of cancer cells and methods of synthesizing derivatives of formula 5 or formula 7: wherein R and R′ are defined herein.
Claims17
A compound of formula:
- wherein X is selected from the group consisting of H, halo, —C1-C6 alkyl, aryl, —C3-C7 cycloalkyl, and -3-to 10-membered heterocycle;
- wherein Y is selected from the group consisting of H, —C1-C6 alkyl, —C3-C7 cycloalkyl, and —C1-C6 alkyl substituted with O—(C1-C6 alkyl);
- wherein Z is selected from the group consisting of:
- NHOH,
- and phenylene diamine group (II) of structure
- and wherein Q is selected from the group consisting of H, F and Cl;
- or a pharmaceutically acceptable salt or solvate thereof.
4 more elements
A method of synthesizing a pharmaceutical compound of formula 5 or formula 7, the method comprising:
- wherein
- R is selected from the group consisting of H, halo, —C1-C6 alkyl, aryl, —C3-C7 cycloalkyl, and -3-to 10-membered heterocycle, wherein the —C1-C6 alkyl, aryl, —C3-C7 cycloalkyl, and -3- to 10-membered heterocycle may be unsubstituted or substituted;
- R′ is 2-isopropoxyethyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl or cycloheptylmethyl;
- compound 9 is selected from the group consisting of 2-isopropoxyethanamine, cyclopropylmethylamine, cyclobutylmethylamine, cyclopentylmethylamine, cyclohexylmethylamine, and cycloheptylmethylamine;
- with the proviso that only when R is an aromatic ring is the 2-fluoronitrobenzene of formula 1 prepared from the corresponding bromide of formula 8 through a Suzuki cross coupling reaction.
2 more elements
Dependencies are inferred from the claim text.