NANOMATERIALS COMPRISING ACETALS

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Patent No.: US None
App. No.: 18/211,822

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Abstract

The present disclosure describes compositions, preparations, nanoparticles (such as lipid nanoparticles), and/or nanomaterials and methods of their use.

Claims (64)

1 . A compound of Formula I′:

or its N-oxide, or a pharmaceutically acceptable salt thereof, wherein

L 1 is absent, C 1-6 alkylenyl, or C 2-6 heteroalkylenyl;

each L 2 is independently optionally substituted C 2-15 alkylenyl or optionally substituted C 3-15 heteroalkylenyl;

L 3 is absent, optionally substituted C 1-10 alkylenyl, or optionally substituted C 2-10 heteroalkylenyl;

X is absent, —OC(O)—, —C(O)O—, or —OC(O)O—;

each R′ is independently an optionally substituted group selected from C 4-12 aliphatic, 3- to 12-membered cycloaliphatic, 7- to 12-membered bridged bicyclic comprising 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, 1-adamantyl, 2-adamantyl, sterolyl, and phenyl;

R is hydrogen,

or an optionally substituted group selected from C 6-20 aliphatic, 3- to 12-membered cycloaliphatic, 7- to 12-membered bridged bicyclic comprising 0-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, 1-adamantyl, 2-adamantyl, sterolyl, and phenyl;

R 1 is hydrogen, optionally substituted phenyl, optionally substituted 3- to 7-membered cycloaliphatic, optionally substituted 3- to 7-membered heterocyclyl comprising 1-3 heteroatoms independently selected from nitrogen, oxygen, and sulfur, optionally substituted 5- to 6-membered monocyclic heteroaryl comprising 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, optionally substituted 8- to 10-membered bicyclic heteroaryl comprising 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, —OR 2 , —C(O)OR 2 , —C(O)SR 2 , —OC(O)R 2 , —OC(O)OR 2 , —CN, —N(R 2 ) 2 , —C(O)N(R 2 ) 2 , —S(O) 2 N(R 2 ) 2 , —NR 2 C(O)R 2 , —OC(O)N(R 2 ) 2 , —N(R 2 )C(O)OR 2 , —NR 2 S(O) 2 R 2 , —NR 2 C(O)N(R 2 ) 2 , —NR 2 C(S)N(R 2 ) 2 , —NR 2 C(NR 2 )N(R 2 ) 2 , —NR 2 C(CHR 2 )N(R 2 ) 2 , —N(OR 2 )C(O)R 2 , —N(OR 2 )S(O) 2 R 2 , —N(OR 2 )C(O)OR 2 , —N(OR 2 )C(O)N(R 2 ) 2 , —N(OR 2 )C(S)N(R 2 ) 2 , —N(OR 2 )C(NR 2 )N(R 2 ) 2 , —N(OR 2 )C(CHR 2 )N(R 2 ) 2 , —C(NR 2 )N(R 2 ) 2 , —C(NR 2 )R 2 , —C(O)N(R 2 )OR 2 , —C(R 2 )N(R 2 ) 2 C(O)OR 2 , —CR 2 (R 3 ) 2 , —OP(O)(OR 2 ) 2 , or —P(O)(OR 2 ) 2 ; or

R 1 is

or a ring selected from 3- to 7-membered cycloaliphatic and 3- to 7-membered heterocyclyl comprising 1-3 heteroatoms independently selected from nitrogen, oxygen, and sulfur, wherein the cycloaliphatic or heterocyclyl ring is optionally substituted with 1-4 R 2 or R 3 groups;

each R 2 is independently hydrogen, oxo, —CN, —NO 2 , —OR 4 , —S(O) 2 R 4 , —S(O) 2 N(R 4 ) 2 , —(CH 2 ) n —R 4 , or an optionally substituted group selected from C 1-6 aliphatic, phenyl, 3- to 7-membered cycloaliphatic, 5- to 6-membered monocyclic heteroaryl comprising 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, and 3- to 7-membered heterocyclyl comprising 1-3 heteroatoms independently selected from nitrogen, oxygen, and sulfur; or

two occurrences of R 2 , taken together with the atom(s) to which they are attached, form optionally substituted 4- to 7-membered heterocyclyl comprising 0-1 additional heteroatom selected from nitrogen, oxygen, and sulfur;

each R 3 is independently —(CH 2 ) n —R 4 ; or

two occurrences of R 3 , taken together with the atom(s) to which they are attached, form optionally substituted 5- to 6-membered heterocyclyl comprising 0-1 additional heteroatom selected from nitrogen, oxygen, and sulfur;

each R 4 is independently hydrogen, —OR 5 , —N(R 5 ) 2 , —OC(O)R 5 , —OC(O)OR 5 , —CN, —C(O)N(R 5 ) 2 , —NR 5 C(O)R 5 , —OC(O)N(R 5 ) 2 , —N(R 5 )C(O)OR 5 , —NR 5 S(O) 2 R 5 , —NR 5 C(O)N(R 5 ) 2 , —NR 5 C(S)N(R 5 ) 2 , —NR 5 C(NR 5 )N(R 5 ) 2 , or

each R 5 is independently hydrogen or optionally substituted C 1-6 aliphatic; or

two occurrences of R 5 , taken together with the atom(s) to which they are attached, form optionally substituted 4- to 7-membered heterocyclyl comprising 0-1 additional heteroatom selected from nitrogen, oxygen, and sulfur;

each R 6 is independently C 4-12 aliphatic; and

each n is independently 0 to 4.

2 . The compound according to claim 1 , wherein the compound is of Formula I-a: