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US 2021/0230202 A1Published application
Dithiolsaccharide mucolytic agents and uses thereof
AssigneesThe Regents of the University of California, University College Dublin
InventorsStefan Oscarson, John Vincent Fahy, Irina Gitlin, Wilfred Raymond
Life of this patent
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Abstract
There are provided, inter alia, methods for decreasing mucus elasticity or decreasing mucus viscosity in a subject in need thereof, the methods including administering to the subject an effective amount of a dithiolsaccharide mucolytic agent, and compounds and pharmaceutical compositions useful for the methods.
Claims71
A compound having the formula:
- wherein,
- R2 is —SR2A, —OR2A, —NR2BR2C, —NR2BC(O)R2C, —NR2BC(O)OR2C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R3 is —SR3A, —OR3A, —NR3BR3C, —NR3BC(O)R3C, —NR3BC(O)OR3C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R4 is —SR4A, —SC(O)R4A, —OR4A, —NR4BR4C, —NR4BC(O)R4C, —NR4BC(O)OR4C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R5 is hydrogen, —SR5A, —OR5A, —NR5BR5C, —NR5BC(O)R5C, —NR5BC(O)OR5C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R6 is —SR6A, —OR6A, —NR6BR6C, —NR6BC(O)R6C, —NR6BC(O)OR6C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R7 is —SR7A, —OR7A, —NR7BR7C, —NR7BC(O)R7C, —NR7BC(O)OR7C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R8 is —SR8A, —OR8A, —NR8BR8C, —NR8BC(O)R8C, —NR8BC(O)OR8C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R9 is —SR9A, —SC(O)R9A, —OR9A, —NR9BR9C, —NR9BC(O)R9C, —NR9BC(O)OR9C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R10 is hydrogen, —SR10A, —OR10A, —NR10BR10C, —NR10BC(O)R10C, —NR10BC(O)OR10C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R11 is —SR11A, —OR11A, —NR11BR11C, —NR11BC(O)R11C, —NR11BC(O)OR11C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R12 is —SR12A, —OR12A, —NR12BR12C, —NR12BC(O)R12C, —NR12BC(O)OR12C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- and
- R2A, R3A, R4A, R5A, R6A, R7A, R8A, R9A, R10A, R11A, R12A, R2B, R3B, R4B, R5B, R6B, R7B, R8B, R9B, R10B, R11B, R12B, R2C, R3C, R4C, R5C, R6C, R7C, R8C, R9C, R10C, R11C, and R12C are each independently hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- provided the compound comprises at least two thiol moieties;
- wherein the compound is not
- or a pharmaceutically acceptable salt thereof.
14 more elements
A compound having the formula:
- wherein,
- R1 is —SR1A, —OR1A, —NR1BR1C, —NR1BC(O)R1C, —NR1BC(O)OR1C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R2 is —SR2A, —OR2A, —NR2BR2C, —NR2BC(O)R2C, —NR2BC(O)OR2C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R3 is —SR3A, —OR3A, —NR3BR3C, —NR3BC(O)R3C, —NR3BC(O)OR3C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R4 is —SR4A, —SC(O)R4A, —OR4A, —NR4BR4C, —NR4BC(O)R4C, —NR4BC(O)OR4C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R5 is hydrogen, —SR5A, —OR5A, —NR5BR5C, —NR5BC(O)R5C, —NR5BC(O)OR5C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R6 is —SR6A, —OR6A, —NR6BR6C, —NR6BC(O)R6C, —NR6BC(O)OR6C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- and
- R1A, R2A, R3A, R4A, R5A, R6A, R1B, R2B, R3B, R4B, R5B, R6B, R1C, R2C, R3C, R4C, R5C, and R6C are each independently hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- provided the compound comprises at least two thiol moieties;
- wherein the compound is not
- or a pharmaceutically acceptable salt thereof.
9 more elements
A compound having the formula:
- wherein,
- R13 is hydrogen, —SR13A, —OR13A, —NR13BR13C, —NR13BC(O)R13C, —NR13BC(O)OR13C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R14 is —SR14A, —OR14A, —NR14BR14C, —NR14BC(O)R14C, —NR14BC(O)OR14C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R15 is —SR15A, —OR15A, —NR15BR15C, —NR15BC(O)R15C, —NR15BC(O)OR15C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R16 is hydrogen, —SR16A, —OR16A, —NR16BR16C, —NR16BC(O)R16C, —NR16BC(O)OR16C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R17 is hydrogen, —SR17A, —OR17A, —NR17BR17C, —NR17BC(O)R17C, —NR17BC(O)OR17C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R18 is —SR18A, —OR18A, —NR18BR18C, —NR18BC(O)R18C, —NR18BC(O)OR18C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R19 is hydrogen, —SR19A, —OR19A, —NR19BR19C, —NR19BC(O)R19C, —NR19BC(O)OR19C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R20 is —SR20A, —OR20A, —NR20BR20C, —NR20BC(O)R20C, —NR20BC(O)OR20C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R13A, R14A, R15A, R16A, R17A, R18A, R19A, R20A, R13B, R14B, R15B, R16B, R17B, R18B, R19B, R20B, R13C, R14C, R15C, R16C, R17C, R18C, R19C, and R20C are each independently hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- provided the compound comprises at least two thiol moieties
- or a pharmaceutically acceptable salt thereof.
9 more elements
A compound having the formula:
- wherein,
- R2 is —SR2A, —OR2A, —NR2BR2C, —NR2BC(O)R2C, —NR2BC(O)OR2C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R3 is —SR3A, —OR3A, —NR3BR3C, —NR3BC(O)R3C, —NR3BC(O)OR3C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R4 is —SR4A, —SC(O)R4A, —OR4A, —NR4BR4C, —NR4BC(O)R4C, —NR4BC(O)OR4C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R5 is hydrogen, —SR5A, —OR5A, —NR5BR5C, —NR5BC(O)R5C, —NR5BC(O)OR5C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R6 is —SR6A, —OR6A, —NR6BR6C, —NR6BC(O)R6C, —NR6BC(O)OR6C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R13 is hydrogen, —SR13A, —OR13A, —NR13BR13C, —NR13BC(O)R13C, —NR13BC(O)OR13C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R14 is —SR14A, —OR14A, —NR14BR14C, —NR14BC(O)R14C, —NR14BC(O)OR14C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R15 is —SR15A, —OR15A, —NR15BR15C, —NR15BC(O)R15C, —NR15BC(O)OR15C, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R17 is hydrogen, —SR17A, —OR17A, —NR17BR17C, —NR17BC(O)R17C, —NR17BC(O)OR17C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R18 is —SR18A, —OR18A, —NR18BR18C, —NR18BC(O)R18C, —NR18BC(O)OR18C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R19 is hydrogen, —SR19A, —OR19A, —NR19BR19C, —NR19BC(O)R19C, —NR19BC(O)OR19C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- R20 is —SR20A, —OR20A, —NR20BR20C, —NR20BC(O)R20C, —NR20BC(O)OR20C, or substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- and
- R2A, R3A, R4A, R5A, R6A, R2B, R3B, R4B, R5B, R6B, R2C, R3C, R4C, R5C, R6C, R13A, R14A, R15A, R17A, R18A, R19A, R20A, R13B, R14B, R15B, R17B, R18B, R19B, R20B, R13C, R14C, R15C, R17C, R18C, R19C, and R20C are each independently hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted 2 to 10 membered heteroalkyl;
- provided the compound comprises at least two thiol moieties, wherein the compound is not
- or a pharmaceutically acceptable salt thereof.
14 more elements
Dependencies are inferred from the claim text.