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US 2026/0209164 A1Published application
Prodrugs of itaconate and methyl itaconate
AssigneesThe Johns Hopkins University, Institute of Organic Chemistry and Biochemistry of the AS CR, V.V.I.
InventorsBarbara Slusher, Mohameed Islam, Rana Rais, Luis Garza, Benjamin Bell, Pavel Majer, Lukas Tenora, Ivan Snajdr, Marcela Krecmerova
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Abstract
Prodrugs of itaconic acid and 1- and 4-methyl itaconic acid and their use for treating a disease, disorder, or condition associated with inflammation are disclosed.
Claims9
A method for treating a disease, disorder, or condition associated with inflammation, the method comprising administering to a subject in need of treatment thereof a compound of formula (I) or a pharmaceutical composition comprising the compound of formula (I):
- wherein:
- R1 and R2 can be the same or different and are each independently selected from one or more of the following and combinations thereof:
- (a) —OR3, wherein R3 is H or C1-C6 straight-chain or branched unsubstituted or substituted alkyl;
- (b)
- wherein n is an integer selected from 1, 2, 3, and 4;
- R4 is C1-C6 straight-chain or branched unsubstituted or substituted alkyl or —OR5, wherein R5 is C1-C6 straight-chain or branched unsubstituted or substituted alkyl;
- (c)
- wherein m is an integer selected from 1, 2, 3, and 4;
- p is an integer selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20;
- and R6 is C1-C6 straight-chain or branched unsubstituted or substituted alkyl;
- (d)
- wherein R7 is selected from:
- (i) —C(═O)—O—R8, wherein R8 is C1-C6 straight-chain or branched unsubstituted or substituted alkyl;
- (ii)
- wherein R9 is H or C1-C4 straight-chain or branched unsubstituted or substituted alkyl;
- R10 is C1-C6 straight-chain or branched unsubstituted or substituted alkyl;
- R11 and R12 are each independently H or a protecting group;
- and R13 is C1-C6 straight-chain or branched unsubstituted or substituted alkyl;
- (iii)
- wherein q is an integer selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10;
- R11 and R12 are each independently H or a protecting group;
- R14 is H or C1-C4 straightchain or branched unsubstituted or substituted alkyl;
- and R15 is C1-C6 straight-chain or branched unsubstituted or substituted alkyl;
- and
- (iv)
- wherein R16 and R17 are each independently selected from H, C1-C4 straight-chain or branched unsubstituted or substituted alkyl, and a protecting group;
- R18 is aryl;
- (e)
- wherein R19 is C1-C4 straight-chain or branched unsubstituted or substituted alkyl;
- (f)
- wherein u is an integer selected from 1, 2, 3, and 4;
- R20 is H or C1-C4 straight-chain or branched unsubstituted or substituted alkyl;
- and R21 is —OR22, wherein R22 is C1-C6 straightchain or branched unsubstituted or substituted alkyl or —NR23R24, wherein R23 and R24 are each independently H or C1-C4 straightchain or branched unsubstituted or substituted alkyl;
- provided that R1 and R2 cannot both be —OH or both be —OR3 at the same time;
- and pharmaceutically acceptable salts thereof.
32 more elements
Dependencies are inferred from the claim text.