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US 2025/0059231 A1Published application
Protease inhibitors
AssigneeProtinhi B.V.
InventorsDaniel Gironés Delgado-Ureña, Cindy Elisabeth Johanna Dieteren, Bernd Nicodemus Maria van Buuren, Martinus Christiaan Feiters, Lorenzo Cavina, Montse Llinas Brunet, Peter Harold Han Hermkens
Life of this patent
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Abstract
The present invention relates to a new class of compounds based on alkylated oligopeptides featuring distinct head and tail modifications at their termini. The compounds are useful as inhibitors of viral proteases, particularly of flaviviral proteases, and can therefore be used for treatment of viral infections.
Claims27
A compound of general formula (0) or a salt thereof:
- wherein
- m is 3 or 2;
- link is —C(O)—or is absent;
- tail is H or C1-24alkyl;
- head is —NH2, —NH-C1-24alkyl, —C(O)—NH2, —C(O)—NH-C1-24alkyl, or5-6-membered (hetero)aryl;
- AA1 is an amino acid residue that is connected to its neighbouring AAn via an amide bond to which it contributes a donor carboxylic acid, and that via its amine is connected to link;
- AAn is for each instance independently an amino acid residue.
4 more elements
A compound of general formula (1) or a salt thereof:
- wherein
- tail is C1-24alkyl, —O—C1-24alkyl, 5-20-membered (hetero)aryl, or 3-20-membered (hetero)cycloalkyl, wherein tail is optionally unsaturated, wherein tail is optionally substituted with halogen, C1-3 (halo)alkyl, or C1-3 (halo)alkoxyl;
- head is —H, -h1, —O-h1, —C(O)-h1, —C(O)—N(H)h1, —N(h2) h1, or head is -C1-24alkyl, —(NH)0-1-5-20-membered (hetero)aryl, or —(NH)0-1-3-20-membered (hetero)cycloalkyl, wherein head is optionally unsaturated, wherein head is optionally substituted with halogen, C1-3 (halo)alkyl, or C1-3 (halo)alkoxyl;
- h1 is —H, —OH, —S(O)0-2—OH, C1-8 (halo)alkyl, C1-8 (halo)alkoxyl, —S(O)0-2-C1-8 (halo)alkyl, 3-8-membered (hetero)cycloalkyl, —S(O)0-2-[3-8-membered (hetero)cycloalkyl], -C1-4alkyl-[3-8-membered (hetero)cycloalkyl], 5-6-membered (hetero)aryl, —S(O)0-2-[5-6-membered (hetero)aryl], or C1-4alkyl[5-6-membered (hetero)aryl], wherein h1 is optionally substituted with halogen, C1-3 (halo)alkyl, or C1-3 (halo)alkoxyl;
- h2 is —H, —OH, —S(O)0-2—OH, C1-8 (halo)alkyl, C1-8 (halo)alkoxyl, —S(O)0-2-C1-8 (halo)alkyl, 3-8-membered (hetero)cycloalkyl, —S(O)0-2-[3-8-membered (hetero)cycloalkyl], -C1-4alkyl-[3-8-membered (hetero)cycloalkyl], 5-6-membered (hetero)aryl, —S(O)0-2-[5-6-membered (hetero)aryl], or C1-4alkyl[5-6-membered (hetero)aryl], wherein h2 is optionally substituted with halogen, C1-3 (halo)alkyl, or C1-3 (halo)alkoxyl;
- AA1 is an amino acid residue that is connected to its neighbouring AAn via an amide bond to which it contributes a donor carboxylic acid, and that is connected to tail via an amide bond of a secondary amide to which it contributes a donor amine;
- AAn is for each instance independently an amino acid residue, wherein the carbonyl moiety in the residue adjacent to head can instead together with head be replaced by —B(OH)2 or a C1-6alkyl ester thereof, —P(O)(OH)2 or a C1-6alkyl ester thereof, —S(O)2-halogen, or 5-12 membered (hetero)aryl that is optionally substituted with halogen, C1-3 (halo)alkyl, or C1-3 (halo)alkoxy;
- m is 1, 2, 3, 4, or 5.
5 more elements
Dependencies are inferred from the claim text.