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US 12,552,827 B2Granted
Synthesis of an antiviral azasugar triphosphate
AssigneeBioCryst Pharmaceuticals, Inc.
InventorsPravin L. Kotian, Zhao Dang, Minwan Wu
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Abstract
Provided are methods of making the active 5′-triphosphate form of galidesivir (compound 1) and the active 5′-triphosphate form of azasugar nucleoside analogues (compound 2): a potent anti-viral compound useful for broad spectrum treatment, suppression, and prevention of viral infections. The syntheses of compound 1 and compound 2 can be achieved via selective formation of protected intermediate 1b and protected intermediate 2b, respectively:
Claims33
A method of preparing compound 2b1 or a salt thereof:
- comprising combining compound 2b or a salt thereof and a phosphorylation reagent, thereby producing compound 2b1 or a salt thereof;
- wherein:
- compound 2b is represented by
- B is a heterocyclic base;
- R0, independently for each occurrence, is selected from the group consisting of H, C1-C6alkyl, and C(O)—C1-C6alkyl;
- R2 and R3 are each independently H, halide, azide, C1-C6alkyl, C1-C6alkenyl, C1-C6alkynyl, CN, OR0, —C(O)OR10, or SR0;
- or R2 and R3, taken together with the intervening atoms, form an optionally substituted fused heterocycloalkyl;
- R10, independently for each occurrence, is selected from the group consisting of H, C1-C6alkyl, aryl, heteroaryl, aralkyl, and heteroaralkyl;
- R11 is selected from the group consisting of H, C1-C6alkyl, C1-C6alkenyl, C1-C6alkynyl, OR0, and CN;
- R12 and R13 are each independently selected from the group consisting of H, C1-C6alkyl, OR0, C1-C6alkenyl, C1-C6alkynyl, CN, azide, and halide;
- and
- R14 is selected from the group consisting of H, C1-C6alkyl, OR0, C1-C6alkynyl, CN, azide, and halide.
9 more elements
A compound having the structure:
- wherein:
- B is a heterocyclic base;
- R0, independently for each occurrence, is selected from the group consisting of H, C1-C6alkyl, and C(O)—C1-C6alkyl;
- R2 and R3 are each independently H, halide, azide, C1-C6alkyl, C1-C6alkenyl, C1-C6alkynyl, CN, OR0, —C(O)OR10, or SR0;
- or R2 and R3, taken together with the intervening atoms, form an optionally substituted fused heterocycloalkyl;
- R10, independently for each occurrence, is selected from the group consisting of H, C1-C6alkyl, aryl, heteroaryl, aralkyl, and heteroaralkyl;
- R11 is selected from the group consisting of H, C1-C6alkyl, C1-C6alkenyl, C1-C6alkynyl, OR0, and CN;
- R12 and R13 are each independently selected from the group consisting of H, C1-C6alkyl, OR0, C1-C6alkenyl, C1-C6alkynyl, CN, azide, and halide;
- and
- R14 is selected from the group consisting of H, C1-C6alkyl, OR0, C1-C6alkynyl, CN, azide, and halide.
7 more elements
A compound having the structure:
- wherein:
- B is a heterocyclic base.
Dependencies are inferred from the claim text.