Benzothiazolium compounds
OwnerShiow-Ju Lee, Yung-Ning Yanginventors
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Abstract
This invention relates to a method of inhibiting NO production and TNFα and treating coronaviral infection by administering an effective amount of a compound of the following formula: wherein R1, R2, R3, R4, R5, A, and X are as defined herein.
Claims38
A method of inhibiting production of nitric oxide, comprising administering to a subject in need thereof an effective amount of a compound of the following formula:
- wherein
- each of R1, R2, R3, and R4, independently, is H, halo, alkyl, alkenyl, akynyl, alkoxyl, aryl, heteroaryl, cylcyl, heterocyclyl, nitro, cyano, amino, amido, or alkoxycarbonyl, or R1, R2, and the two carbon atoms to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms, or R2, R3, and the two carbon atoms to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms, or R3, R4, and the two carbon atoms to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms;
- R5 is H, alkyl, aryl, heteroaryl, cyclyl, or heterocyclyl;
- A is H, alkyl, aryl, heteroaryl, cyclyl, heterocyclyl, alkoxy, amino, halo, mercapto, thioalkoxy,
- in which m is 0, 1, 2, or 3;
- each of Ra, Rb, Rc, Rd, and Re independently is H, alkyl, akenyl, akynyl, halo, aryl, heteroaryl, cyclyl, heterocylyl, alkoxy, mercapto, thioalkoxy, amino, amido, or Rd, Re, and the carbon atom to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms, which is optionally fused with aryl, heteroaryl, cyclyl, or heterocyclyl;
- optionally A, R5, the N atom to which R5 is attached, and the carbon atom to which A is attached, together form a 4-8 membered ring containing 1, 2, or 3 heteroatoms;
- and
- X is an anion or a negatively charged group attached to an atom of R1, R2, R3, R4, R5, or A.
A method of inhibiting production of TNFα, comprising administering to a subject in need thereof an effective amount of a compound of the following formula:
- wherein
- each of R1, R2, R3, and R4, independently, is H, halo, alkyl, alkenyl, akynyl, alkoxyl, aryl, heteroaryl, cylcyl, heterocyclyl, nitro, cyano, amino, amido, or alkoxycarbonyl, or R1, R2, and the two carbon atoms to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms, or R2, R3, and the two carbon atoms to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms, or R3, R4, and the two carbon atoms to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms;
- R5 is H, alkyl, aryl, heteroaryl, cyclyl, or heterocyclyl;
- A is H, alkyl, aryl, heteroaryl, cyclyl, heterocyclyl, alkoxy, amino, halo, mercapto, thioalkoxy,
- in which m is 0, 1, 2, or 3;
- each of Ra, Rb, Rc, Rd, and Re independently is H, alkyl, akenyl, akynyl, halo, aryl, heteroaryl, cyclyl, heterocylyl, alkoxy, mercapto, thioalkoxy, amino, amido, or Rd, Re, and the carbon atom to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms, which is optionally fused with aryl, heteroaryl, cyclyl, or heterocyclyl;
- optionally A, R5, the N atom to which R5 is attached, and the carbon atom to which A is attached, together form a 4-8 membered ring containing 1, 2, or 3 heteroatoms;
- and
- X is an anion or a negatively charged group attached to an atom of R1, R2, R3, R4, R5, or A.
A method of treating coronaviral infection, comprising administering to a subject in need thereof an effective amount of a compound of the following formula:
- wherein
- each of R1, R2, R3, and R4, independently, is H, halo, alkyl, alkenyl, akynyl, alkoxyl, aryl, heteroaryl, cylcyl, heterocyclyl, nitro, cyano, amino, amido, or alkoxycarbonyl, or R1, R2, and the two carbon atoms to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms, or R2, R3, and the two carbon atoms to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms, or R3, R4, and the two carbon atoms to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms;
- R5 is H, alkyl, aryl, heteroaryl, cyclyl, or heterocyclyl;
- A is H, alkyl, aryl, heteroaryl, cyclyl, heterocyclyl, alkoxy, amino, halo, mercapto, thioalkoxy,
- in which m is 0, 1, 2, or 3;
- each of Ra, Rb, Rc, Rd, and Re independently is H, alkyl, akenyl, akynyl, halo, aryl, heteroaryl, cyclyl, heterocylyl, alkoxy, mercapto, thioalkoxy, amino, amido, or Rd, Re, and the carbon atom to which they are attached, together form a 3-8 membered ring containing 0, 1, 2, or 3 heteroatoms, which is optionally fused with aryl, heteroaryl, cyclyl, or heterocyclyl;
- optionally A, R5, the N atom to which R5 is attached, and the carbon atom to which A is attached, together form a 4-8 membered ring containing 1, 2, or 3 heteroatoms;
- and
- X is an anion or a negatively charged group attached to an atom of R1, R2, R3, R4, R5, or A.
Dependencies are inferred from the claim text.