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US 2026/0176274 A1Published application
Enamine n-oxide tools for target identification applications
AssigneeDana-Farber Cancer Institute, Inc.
InventorsJustin KIM, Surached SIRIWONGSUP
Life of this patent
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Abstract
Disclosed are compounds and pharmaceutically acceptable salts and stereoisomers thereof that are suitable for cellular labeling. Also disclosed are pharmaceutical compositions containing same, and methods of making and using the compounds.
Claims52
A compound having a structure represented by any one of formulas I-VI:
- or a pharmaceutically acceptable salt or stereoisomer thereof,
- wherein:
- each of L1 and L2 is independently absent or a linking group, which may be the same or different;
- R1′ is absent, or
- R1′ and R1, together with the nitrogen atom to which they are bound, form an optionally substituted 4- or 10-membered heterocyclyl comprising 1 to 3 heteroatoms selected from O, N, and S;
- each R1 is independently (C1-C8) alkyl, (C3-C10) carbocyclyl, or 4- or 10-membered heterocyclyl comprising 1 to 3 heteroatoms selected from O, N, and S, wherein said alkyl, carbocyclyl or heterocyclyl is further optionally substituted, or
- two R1 groups, together with the nitrogen atom to which they are bound, form an optionally substituted 4- or 10-membered heterocyclyl comprising 1 to 3 heteroatoms selected from O, N, and S;
- R2 is halo or alkoxy;
- R3 is a leaving group;
- R4 is a ligand that binds a cellular protein or a nucleic acid;
- R5 is a bioorthogonal handle, an affinity handle, or a reporter;
- and
- R6 and R6′ are independently hydrogen, (C1-C6) alkyl, or optionally substituted aryl, provided that P3 is not halo for the compound of formula VI.
10 more elements
(canceled)
-13. (canceled)
A compound having a structure represented by formula VII:
- or a pharmaceutically acceptable salt or stereoisomer thereof,
- wherein:
- L is a linking group;
- R1 and R1′ are independently (C1-C8) alkyl, (C3-C10) carbocyclyl, or 4- or 10-membered heterocyclyl comprising 1 to 3 heteroatoms selected from O, N, and S, wherein said alkyl, carbocyclyl or heterocyclyl is further optionally substituted, or R1 and R1′ together with the nitrogen atom to which they are attached, form a 4- to 7-membered heterocyclyl comprising 1 to 3 heteroatoms selected from O, N, and S;
- R2 is halo or alkoxy;
- R3 is absent, OC(O), C(O)O, OC(O)O, OC(O)NR′, NR′C(O)O, S(O), S(O)2, OS(O)2, S(O)2O, OP(OR′)O2, or a leaving group, wherein each R′ is independently hydrogen, (C1-C6) alkyl, (C3-C10) carbocyclyl, 4- or 7-membered heterocyclyl, and wherein said alkyl, carbocyclyl, or heterocyclyl is optionally substituted;
- R3′ is hydrogen, (C1-C6) alkyl, (C3-C10) carbocyclyl, or 4- or 10-membered heterocyclyl comprising 1 to 3 heteroatoms selected from O, N, and S, or a leaving group, wherein said alkyl, carbocyclyl or heterocyclyl is further optionally substituted;
- and
- R5 is a bioorthogonal handle, an affinity handle, a reporter, or a ligand that binds a cellular protein or a nucleic acid,
- provided that one of R3 or R3′ is a leaving group.
7 more elements
-39. (canceled)
A process of preparing a compound of formula I:
- comprising reacting a compound of formula VIII:
- with a compound of formula IX:
- or
- a compound of formula II:
- comprising reacting a compound of formula X:
- with a compound of formula XI:
- or
- a compound of formula III:
- comprising reacting a compound of formula X:
- with a compound of formula XII:
- a compound of formula IV:
- comprising reacting a compound of formula XIII:
- with a compound of formula XIV:
- or
- a compound of formula V:
- comprising reacting a compound of formula XV:
- with a compound of formula XIV:
- or
- a compound of formula VI:
- comprising reacting a compound of formula VIII:
- with a compound of formula XV:
18 more elements
-65. (canceled)
Dependencies are inferred from the claim text.