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US 2026/0256723 A1Published application
Thiol-based compounds and compositions and uses thereof
OwnerStephen J. Lewis, Benjamin Gaston +1inventors
InventorsStephen J. Lewis, Benjamin Gaston, James N. Bates
Life of this patent
Estimating the term…
Abstract
A method of attenuating opioid induced ventilatory and/or respiratory depression and/or reducing opioid induced constipation and/or anuria and/or treating brain injury in a subject in need thereof includes administering to the subject a therapeutically effective amount of a composition comprising a compound having the structure of the formulas (I-VIII).
Claims21
1:
- A pharmaceutical composition comprising:
- a compound having a structure of formulas:
- or an adduct, a pharmaceutically acceptable salt, a tautomer, or a solvate thereof;
- wherein:
- X is OR2 or N(R3)2;
- X1 is OR5 or N(R6)2;
- X2 is OR8 or N(R9)2;
- R1, R4, and R7 are each independently H, alkyl optionally substituted with one or more halogen, or —C(O)-alkyl optionally substituted with one or more halogen;
- R2, R5, and R8 are each independently H or alkyl optionally substituted with one or more halogen;
- each R3, R6, and R9 are independently H or alkyl optionally substituted with one or more halogen;
- X is not OR2 if R1 is H;
- and
- X2 is not OR8 if X1 is OR5 and R4 and R7 are H.
10 more elements
2:
- The composition of claim 1, wherein the adduct of the compound of formulas I or II is biologically active and includes at least one of an albumin adduct, a glucose adduct, an L-cysteine adduct, an L-glutathione adduct, an D-cysteine adduct, or an S-nitroso adduct.
3:
- The composition of claim 1, wherein R1, R4, and R7 are each independently H, C1-C6 alkyl optionally substituted with one or more halogen, or —C(O)—(C1-C6 alkyl) optionally substituted with one or more halogen.
4:
- The composition of claim 1, wherein R1, R4, and R7 are each independently H, methyl, ethyl, propyl, butyl, —C(O)— methyl, —C(O)-ethyl, —C(O)-propyl, or —C(O)-butyl, each optionally substituted with one or more halogen.
5:
- The composition of claim 1, wherein R2, R5, and R8 are each independently H or C1-C6 alkyl optionally substituted with one or more halogen.
6:
- The composition of claim 1, wherein R2, R5, and R8 are each independently H, methyl, ethyl, or propyl, or butyl, each optionally substituted with one or more halogen.
7:
- The composition of claim 1, wherein each R3, R6, and R9 is independently H or C1-C6 alkyl optionally substituted with one or more halogen.
8:
- The composition of claim 1, wherein one of each R3, R6, and R9 is H and the other of R3, R6, and R9 is methyl, ethyl, or propyl, or butyl, each optionally substituted with one or more halogen.
9:
- The composition of claim 1, wherein X is OR2, R1 is H, C1-C6 alkyl optionally substituted with one or more halogen, or —C(O)—(C1-C6 alkyl) optionally substituted with one or more halogen, and R2 is H or C1-C6 alkyl optionally substituted with one or more halogen.
10:
- The composition of claim 1, wherein X is OR2, R1 is H, methyl, ethyl, propyl, butyl, —C(O)-methyl, —C(O)-ethyl, —C(O)-propyl, or —C(O)-butyl, each optionally substituted with one or more halogen, and R2 is H, methyl, ethyl, or propyl, or butyl, each optionally substituted with one or more halogen.
11:
- The composition of claim 1, wherein X is N(R3)2;
- R1 is H, C1-C6 alkyl optionally substituted with one or more halogen, or —C(O)—(C1-C6 alkyl) optionally substituted with one or more halogen;
- and each R3 is independently H or C1-C6 alkyl optionally substituted with one or more halogen.
12:
- The composition of claim 1, wherein X is N(R3)2, R1 is H, methyl, ethyl, propyl, butyl, —C(O)-methyl, —C(O)-ethyl, —C(O)-propyl, or —C(O)-butyl, each optionally substituted with one or more halogen, and one R3 is H and the other R3 is methyl, ethyl, or propyl, or butyl, each optionally substituted with one or more halogen.
13:
- The composition of claim 1, wherein X1 is OR5, R4 is H, C1-C6 alkyl optionally substituted with one or more halogen, or —C(O)—(C1-C6 alkyl) optionally substituted with one or more halogen, R5 is H or C1-C6 alkyl optionally substituted with one or more halogen;
- X2 is OR8, R7 is H, C1-C6 alkyl optionally substituted with one or more halogen, or —C(O)—(C1-C6 alkyl) optionally substituted with one or more halogen, and R8 is H or C1-C6 alkyl optionally substituted with one or more halogen.
14:
- The composition of claim 1, wherein X1 is OR5, R4 is H, methyl, ethyl, propyl, butyl, —C(O)-methyl, —C(O)-ethyl, —C(O)-propyl, or —C(O)-butyl, each optionally substituted with one or more halogen, R5 is H, methyl, ethyl, or propyl, or butyl, each optionally substituted with one or more halogen, X2 is OR8;
- R7 is H, methyl, ethyl, propyl, butyl, —C(O)-methyl, —C(O)-ethyl, —C(O)-propyl, or —C(O)-butyl, each optionally substituted with one or more halogen, and R8 is H, methyl, ethyl, or propyl, or butyl, each optionally substituted with one or more halogen.
15:
- The composition of claim 1, wherein X1 is N(R6)2, R4 is H, C1-C6 alkyl optionally substituted with one or more halogen, or —C(O)—(C1-C6 alkyl) optionally substituted with one or more halogen, each R6 is independently H or C1-C6 alkyl optionally substituted with one or more halogen, X2 is N(R9)2, R7 is H, C1-C6 alkyl optionally substituted with one or more halogen, or —C(O)—(C1-C6 alkyl) optionally substituted with one or more halogen, and R9 is H or C1-C6 alkyl optionally substituted with one or more halogen.
16:
- The composition of claim 1, wherein X1 is N(R3)2, R4 is H, methyl, ethyl, propyl, butyl, —C(O)-methyl, —C(O)-ethyl, —C(O)-propyl, or —C(O)-butyl, each optionally substituted with one or more halogen, one R6 is H and the other R6 is methyl, ethyl, or propyl, or butyl, each optionally substituted with one or more halogen, X1 is N(R9)2;
- R7 is H, methyl, ethyl, propyl, butyl, —C(O)-methyl, —C(O)-ethyl, —C(O)-propyl, or —C(O)-butyl, each optionally substituted with one or more halogen, and one R9 is H and the other R9 is methyl, ethyl, or propyl, or butyl, each optionally substituted with one or more halogen.
17:
- The composition of claim 1, wherein the compound is not cysteine, cystine, a cysteine alkylester, or cystine dialkylester.
18-71. (canceled)
72:
- The composition of claim 1, further comprising a pharmaceutically acceptable carrier or excipient.
73:
- A method of attenuating opioid induced ventilatory and/or respiratory depression in a subject in need thereof, the method comprising:
- administering to the subject a therapeutically effective amount of a composition of claim 1.
74-89. (canceled)