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US 9,695,135 B2Granted
Therapeutic catechols
AssigneeRutgers, The State University of New Jersey
InventorsEdmond J. LaVoie, Eddy Arnold, Joseph D. Bauman, John E. Kerrigan, Ajit K. Parhi, Kalyan Das, Cody Kelley, Dishaben V. Patel
Life of this patent
Estimating the term…
Abstract
The invention provides compounds of formula I: and salts thereof wherein R1-R4 have any of the meanings defined in the specification, as well as pharmaceutical compositions comprising the compounds or salts, and methods for their use in therapy. The compounds have useful antiviral properties.
Claims16
A method to promote an antiviral effect in an animal comprising administering a compound of formula I:
- wherein:
- R1 is H or NO2;
- one of R2 and R3 is Ra;
- and the other of R2 and R3 is phenyl, naphthyl, or a 5-6 membered heteroaryl, wherein any phenyl, naphthyl, and 5-6 membered heteroaryl is optionally substituted with one or more Rb;
- R4 is H or (C1-C4)alkyl that is optionally substituted with one or more Rd;
- Ra is halo, aryl, heteroaryl, aryl(C1-C4)alkyl, or heteroaryl(C1-C4)alkyl, wherein any aryl and heteroaryl is optionally substituted with one or more Rc, and wherein any (C1-C4)alkyl is optionally substituted with one or more Rk;
- each Rb is independently selected from the group consisting of halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, tetrazole, carboxy, phenyl, naphthyl, —NReRf, —C(═O)NReRf, and nitro, wherein each (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, phenyl, naphthyl, and (C1-C6)alkoxy, are optionally substituted with one or more groups independently selected from halo, hydroxy, —NReRf, carboxy, heterocycle, and —C(═O)NReRf;
- each Rc is independently selected from the group consisting of halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, aryl, heteroaryl, and nitro, wherein each (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, and (C1-C6)alkoxy, are optionally substituted with one or more groups independently selected from halo, hydroxy, carboxy, heterocycle, and —C(═O)NReRf, and wherein any aryl and heteroaryl is optionally substituted with one or more groups independently selected from halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, tetrazole, nitro, —NReRf, carboxy, heterocycle, and —C(═O)NReRf;
- each Rd is independently selected from the group consisting of halo, hydroxy, cyano, carboxy, heterocycle, —NReRf, and —C(═O)NReRf;
- each Re and Rf is independently selected from hydrogen, (C1-C6)alkyl, and (C1-C6)alkanoyl;
- or Re and Rf together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino;
- and
- each Rk is independently selected from the group consisting of hydroxy, (C1-C6)alkyl, carboxy, and —C(═O)NReRf, wherein each (C1-C6)alkyl is optionally substituted with one or more groups independently selected from halo, hydroxy, —NReRf, cyano, carboxy, and —C(═O)NReRf;
- or a pharmaceutically acceptable salt or prodrug thereof, to the animal.
11 more elements
A method to promote an antiviral effect in an animal comprising administering a compound of formula I:
- wherein:
- R1 is H or NO2;
- R3 is Ra;
- and R2 is phenyl that is substituted with tetrazole;
- R4 is H or (C1-C4)alkyl that is optionally substituted with one or more Rd;
- Ra is H, halo, aryl, heteroaryl, aryl(C1-C4)alkyl, heteroaryl(C1-C4)alkyl, or (C1-C6)alkyl, wherein any aryl and heteroaryl is optionally substituted with one or more Rc, and wherein any (C1-C4)alkyl and (C1-C6)alkyl is optionally substituted with one or more Rk;
- each Rc is independently selected from the group consisting of halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, aryl, heteroaryl, and nitro, wherein each (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, and (C1-C6)alkoxy, are optionally substituted with one or more groups independently selected from halo, hydroxy, —NReRf, carboxy, heterocycle, and —C(═O)NReRf, and wherein any aryl and heteroaryl is optionally substituted with one or more groups independently selected from halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, tetrazole, nitro, —NReRf, carboxy, heterocycle, and —C(═O)NReRf;
- each Rd is independently selected from the group consisting of halo, hydroxy, cyano, carboxy, heterocycle, —NReRf, and —C(═O)NReRf;
- each Re and Rf is independently selected from hydrogen, (C1-C6)alkyl, and (C1-C6)alkanoyl;
- or Re and Rf together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino;
- and
- each Rk is independently selected from the group consisting of hydroxy, (C1-C6)alkyl, carboxy, and —C(═O)NReRf, wherein each (C1-C6)alkyl is optionally substituted with one or more groups independently selected from halo, hydroxy, —NReRf, cyano, carboxy, and —C(═O)NReRf;
- or a pharmaceutically acceptable salt or prodrug thereof, to the animal.
10 more elements
A method to promote an antiviral effect in an animal comprising administering a compound of formula I:
- wherein:
- R1 is H or NO2;
- R3 is Ra;
- and R2 is
- R4 is H or (C1-C4)alkyl that is optionally substituted with one or more Rd;
- Ra is H, halo, aryl, heteroaryl, aryl(C1-C4)alkyl, heteroaryl(C1-C4)alkyl, or (C1-C6)alkyl, wherein any aryl and heteroaryl is optionally substituted with one or more Rc, and wherein any (C1-C4)alkyl and (C1-C6)alkyl is optionally substituted with one or more Rk;
- each Rc is independently selected from the group consisting of halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, aryl, heteroaryl, and nitro, wherein each (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, and (C1-C6)alkoxy, are optionally substituted with one or more groups independently selected from halo, hydroxy, —NReRf, carboxy, heterocycle, and —C(═O)NReRf, and wherein any aryl and heteroaryl is optionally substituted with one or more groups independently selected from halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, tetrazole, nitro, —NReRf, carboxy, heterocycle, and —C(═O)NReRf;
- each Rd is independently selected from the group consisting of halo, hydroxy, cyano, carboxy, heterocycle, —NReRf, and —C(═O)NReRf;
- each Re and Rf is independently selected from hydrogen, (C1-C6)alkyl, and (C1-C6)alkanoyl;
- or Re and Rf together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino;
- and
- each Rk is independently selected from the group consisting of hydroxy, (C1-C6)alkyl, carboxy, and —C(═O)NReRf, wherein each (C1-C6)alkyl is optionally substituted with one or more groups independently selected from halo, hydroxy, —NReRf, cyano, carboxy, and —C(═O)NReRf;
- or a pharmaceutically acceptable salt or prodrug thereof, to the animal.
10 more elements
A method to promote an antiviral effect in an animal comprising administering a compound of formula I:
- wherein:
- R1 is H or NO2;
- R2 is Ra;
- and R3 is phenyl that is substituted with tetrazole;
- R4 is H or (C1-C4)alkyl that is optionally substituted with one or more Rd;
- Ra is H, halo, aryl, heteroaryl, aryl(C1-C4)alkyl, heteroaryl(C1-C4)alkyl, or (C1-C6)alkyl, wherein any aryl and heteroaryl is optionally substituted with one or more Rc, and wherein any (C1-C4)alkyl and (C1-C6)alkyl is optionally substituted with one or more Rk;
- each Rc is independently selected from the group consisting of halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, aryl, heteroaryl, and nitro, wherein each (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, and (C1-C6)alkoxy, are optionally substituted with one or more groups independently selected from halo, hydroxy, —NReRf, carboxy, heterocycle, and —C(═O)NReRf, and wherein any aryl and heteroaryl is optionally substituted with one or more groups independently selected from halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, tetrazole, nitro, —NReRf, carboxy, heterocycle, and —C(═O)NReRf;
- each Rd is independently selected from the group consisting of halo, hydroxy, cyano, carboxy, heterocycle, —NReRf, and —C(═O)NReRf;
- each Re and Rf is independently selected from hydrogen, (C1-C6)alkyl, and (C1-C6)alkanoyl;
- or Re and Rf together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino;
- and
- each Rk is independently selected from the group consisting of hydroxy, (C1-C6)alkyl, carboxy, and —C(═O)NReRf, wherein each (C1-C6)alkyl is optionally substituted with one or more groups independently selected from halo, hydroxy, —NReRf, cyano, carboxy, and —C(═O)NReRf;
- or a pharmaceutically acceptable salt or prodrug thereof, to the animal.
10 more elements
A method to promote an antiviral effect in an animal comprising administering a compound of formula I:
- wherein:
- R1 is H or NO2;
- R2 is Ra;
- and R3 is
- R4 is H or (C1-C4)alkyl that is optionally substituted with one or more Rd;
- Ra is H, halo, aryl, heteroaryl, aryl(C1-C4)alkyl, heteroaryl(C1-C4)alkyl, or (C1-C6)alkyl, wherein any aryl and heteroaryl is optionally substituted with one or more Rc, and wherein any (C1-C4)alkyl and (C1-C6)alkyl is optionally substituted with one or more Rk;
- each Rc is independently selected from the group consisting of halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, aryl, heteroaryl, and nitro, wherein each (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, and (C1-C6)alkoxy, are optionally substituted with one or more groups independently selected from halo, hydroxy, —NReRf, carboxy, heterocycle, and —C(═O)NReRf, and wherein any aryl and heteroaryl is optionally substituted with one or more groups independently selected from halo, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, cyano, tetrazole, nitro, —NReRf, carboxy, heterocycle, and —C(═O)NReRf;
- each Rd is independently selected from the group consisting of halo, hydroxy, cyano, carboxy, heterocycle, —NReRf, and —C(═O)NReRf;
- each Re and Rf is independently selected from hydrogen, (C1-C6)alkyl, and (C1-C6)alkanoyl;
- or Re and Rf together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino;
- and
- each Rk is independently selected from the group consisting of hydroxy, (C1-C6)alkyl, carboxy, and —C(═O)NReRf, wherein each (C1-C6)alkyl is optionally substituted with one or more groups independently selected from halo, hydroxy, —NReRf, cyano, carboxy, and —C(═O)NReRf;
- or a pharmaceutically acceptable salt or prodrug thereof, to the animal.
10 more elements
A method to promote an antiviral effect in an animal comprising administering a compound selected from the group consisting of:
- or a pharmaceutically acceptable salt or prodrug thereof is administered.
Dependencies are inferred from the claim text.