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US 9,040,715 B2Granted
1,2-benzisothiazolinone and isoindolinone derivatives
AssigneeGeorgetown University
InventorsRichard A. Calderone, William C. Groutas, Brent E. Korba
Life of this patent
Estimating the term…
Abstract
Novel classes of 1,2-benzisothiazolinone and isoindolinone compounds and compositions are disclosed. These compounds and compositions are useful in treating, preventing, and/or ameliorating viral, yeast, and fungal infections such as, for example, Hepatitis C Virus, Flavivirus infections, Aspergillus fumigatus, and candidiasis.
Claims16
A compound selected from the group consisting of:
- or a pharmaceutically acceptable salt or prodrug thereof, wherein:
- R1 is hydrogen or methyl;
- W is —C(O)NR2— or —C(O)NR3—NR4C(O)—, wherein R2, R3, and R4 are each independently selected from hydrogen, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, and substituted or unsubstituted heterocycloalkylalkyl;
- and
- Y is hydrogen, hydroxy, alkoxy, substituted or unsubstituted amino, substituted or unsubstituted thiol, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, or substituted or unsubstituted heterocycloalkylalky wherein when W is C(O)NH, Y is selected from the group consisting of phenoxy substituted aryl and unsubstituted aryl;
- or a pharmaceutically acceptable salt or prodrug thereof, wherein:
- R1 is hydrogen or methyl;
- and
- R5 is hydrogen, hydroxy, alkoxy, substituted or unsubstituted amino, substituted or unsubstituted thiol, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, or substituted or unsubstituted heterocycloalkylalkyl;
- or a pharmaceutically acceptable salt or prodrug thereof, wherein:
- R1 is hydrogen or methyl;
- R3 and R4 are each independently selected from hydrogen, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, and substituted or unsubstituted heterocycloalkylalkyl;
- and
- R6 is hydrogen, hydroxy, alkoxy, substituted or unsubstituted amino, substituted or unsubstituted thiol, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, or substituted or unsubstituted heterocycloalkylalkyl;
- or a pharmaceutically acceptable salt or prodrug thereof, wherein:
- R1 is hydrogen or methyl;
- and
- R2 is hydrogen, phenoxy-substituted aryl, or unsubstituted aryl;
- or a pharmaceutically acceptable salt or prodrug thereof, wherein:
- R1 is hydrogen or methyl;
- and
- R5 and R6 are each independently selected from hydrogen, hydroxy, alkoxy, substituted or unsubstituted amino, substituted or unsubstituted thiol, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, and substituted or unsubstituted heterocycloalkylalkyl;
- and
20 more elements
A method of diminishing an infection in a subject comprising administering to the subject a therapeutically effective amount of the compound selected from the group consisting of:
- or a pharmaceutically acceptable salt or prodrug thereof, wherein:
- R1 is hydrogen or methyl;
- W is —C(O)NR2— or —C(O)NR3—NR4C(O)—, wherein R2, R3, and R4 are each independently selected from hydrogen, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, and substituted or unsubstituted heterocycloalkylalkyl;
- X is S;
- Y is hydrogen, hydroxy, alkoxy, substituted or unsubstituted amino, substituted or unsubstituted thiol, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, or substituted or unsubstituted heterocycloalkylalkyl;
- and
- Z is C═O;
- or a pharmaceutically acceptable salt or prodrug thereof, wherein:
- R1 is hydrogen or methyl;
- and
- R5 is hydrogen, hydroxy, alkoxy, substituted or unsubstituted amino, substituted or unsubstituted thiol, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, or substituted or unsubstituted heterocycloalkylalkyl;
- or a pharmaceutically acceptable salt or prodrug thereof, wherein:
- R1 is hydrogen or methyl;
- R3 and R4 are each independently selected from hydrogen, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, and substituted or unsubstituted heterocycloalkylalkyl;
- and
- R6 is hydrogen, hydroxy, alkoxy, substituted or unsubstituted amino, substituted or unsubstituted thiol, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, or substituted or unsubstituted heterocycloalkylalkyl;
- or a pharmaceutically acceptable salt or prodrug thereof, wherein:
- R1 is hydrogen or methyl;
- and
- R2 is hydrogen, phenoxy-substituted aryl, or unsubstituted aryl;
- or a pharmaceutically acceptable salt or prodrug thereof, wherein:
- R1 is hydrogen or methyl;
- and
- R5 and R6 are each independently selected from hydrogen, hydroxy, alkoxy, substituted or unsubstituted amino, substituted or unsubstituted thiol, substituted or unsubstituted C1-12 alkyl, substituted or unsubstituted C1-12 haloalkyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted C2-12 alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkylalkyl, and substituted or unsubstituted heterocycloalkylalkyl;
- and
- wherein the infection is Hepatitis C virus, a fungal infection, or a yeast infection
- wherein when W is C(O)NH, Y is selected from the group consisting of phenoxy substituted aryl and unsubstituted aryl.
24 more elements
Dependencies are inferred from the claim text.