US 2012/0238543 A1Published application

Antiviral Compounds

AssigneeProsetta Antiviral Inc.

InventorsClarence Hurt, Beverly Freeman, Vishwanath Lingappa, Andy Atuegbu, Anatoliy Kitaygorodskyy

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Abstract

Novel compounds, methods, and compositions for treating various viral infections are described. In some embodiments the novel compounds of the invention are 3-oxo-phenothiazine derivatives; more specific embodiments include 3-oxo-phenothiazine derivatives having substituents at the 1-, 7-, and 9-positions of the phenothiazine parent ring. In other embodiments, the invention provides compositions and methods for treating viral infections, especially HIV.

Claims20

Dependent claims

A compound having the structure:

and its pharmaceutically acceptable salts, hydrates, and coordination compounds, wherein:
R4, R2, R4, R5, R8, and R9 are selected independently from the group consisting of:
hydrogen, halo, cyano, nitro, thio, amino, carboxyl, formyl, sulfo, sulfinyl, sulfeno, sulfenamoyl, sulfonamino, and optionally substituted loweralkyl, loweralkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, cycloalkylcarbonyloxy, cycloheteroalkylcarbonyloxy, aralkycarbonyloxy, heteroaralkylcarbonyloxy, (cycloalkyl)alkylcarbonyloxy, (cycloheteroalkyl)alkylcarbonyloxy, loweralkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, cycloalkycarbonyl, cycloheteroalkycarbonyl, aralkycarbonyl, heteroaralkylcarbonyl, (cycloalkyl)alkylcarbonyl, (cycloheteroalkyl)alkylcarbonyl, loweralkylaminocarbonyl, arylaminocarbonyl, aralkylaminocarbonyl, heteroarylaminocarbonyl, heteroaralkylamino carbonyl, loweralkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, cycloalkyl carbonylamino, cycloheteroalkylcarbonylamino, aralkylcarbonylamino, heteroaralkylcarbonylamino, (cycloalkyl)alkylcarbonylamino, (cycloheteroalkyl)alkylcarbonylamino, diloweralkylamino, arylamino, diarylamino, aralkylamino, diaralkylamino, heteroarylamino, diheteroarylamino, heteroaralkylamino, diheteroaralkylamino, loweralkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, loweralkylsulfonyldioxy, arylsulfonyldioxy, heteroarylsulfonyldioxy, loweralkylsulfo, arylsulfo, heteroarylsulfo, cycloalkylsulfo, loweralkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, loweralkylsulfeno, arylsulfeno, heteroarylsulfeno, cycloalkylsulfeno, loweralkylsulfoamino, arylsulfoamino, heteroarylsulfoamino, cycloalkylsulfoamino, sulfonaloweralkylcarbonylsulfenamoyl, arylcarbonylsulfenamoyl, heteroarylcarbonylsulfenamoyl, cycloalkyl carbonylsulfenamoyl, cycloheteroalkylcarbonylsulfenamoyl, aralkylcarbonylsulfenamoyl, heteroaralkylcarbonylsulfenamoyl, (cycloalkyl)alkylcarbonylsulfenamoyl, (cycloheteroalkyl)alkylcarbonylsulfenamoyl, diloweralkylsulfenamoyl, arylsulfenamoyl, diarylsulfenamoyl, aralkylsulfenamoyl, diaralkylsulfenamoyl, heteroarylsulfenamoyl, diheteroarylsulfenamoyl, heteroaralkylsulfenamoyl, diheteroaralkylsulfenamoyl, loweralkylcarbonylsulfinamoyl, arylcarbonylsulfinamoyl, heteroarylcarbonylsulfinamoyl, cycloalkyl carbonylsulfinamoyl, cycloheteroalkylcarbonylsulfinamoyl, aralkylcarbonylsulfinamoyl, heteroaralkylcarbonylsulfinamoyl, (cycloalkyl)alkylcarbonylsulfinamoyl, (cycloheteroalkyl)alkylcarbonylsulfinamoyl, diloweralkylsulfinamoyl, arylsulfinamoyl, diarylsulfinamoyl, aralkylsulfinamoyl, diaralkylsulfinamoyl, heteroarylsulfinamoyl, diheteroarylsulfinamoyl, heteroaralkylsulfinamoyl, diheteroaralkylsulfinamoyl, aralkycarbonylthioooxy, carbonylthio, heteroaralkylcarbonylthio, (cycloalkyloxy)carbonylthio, (cycloheteroalkyl)alkylcarbonylthio, loweralkyloxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, cycloalkyloxycarbonyl, cycloheteroalkyloxycarbonyl, aralyoxycarbonyloxloxycarbonyl, heteroaralkyloxycarbonyl, (cycloalkyl)alkyloxycarbonyl, (cycloheteroalkyl)alkyloxycarbonyl, iminoloweralkyl, iminocycloalkyl, iminocycloheteroalkyl, iminoaralkyl, iminoheteroaralkyl, (cycloalkyl)iminoalkyl, and (cycloheteroalkyl)iminoalkyl;
R3 is selected from the group consisting of:
halo, oxo, thio, imino, iminoloweralkyl, iminocycloalkyl, iminocycloheteroalkyl, iminoaralkyl, iminoheteroaralkyl, (cycloalkyl)iminoalkyl, and (cycloheteroalkyl)iminoalkyl;
and
R6 and R7 are selected independently from the group consisting of:
hydrogen and optionally substitued loweralkyl, loweralkyloxyloweralkyl, aminoloweralkyl, loweralkylaminoloweralkyl, diloweralkylaminoloweralkyl, loweralkylthioloweralkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, arylcarbonyl, alkylcarbonyl, aralkylcarbonyl, heteroarylcarbonyl, and heteroaralkylcarbonyl;
in addition, R6 and R7, together with the nitrogen atom to which each is attached, can form an optionally substitued 4-, 5-, 6-, or 7-membered ring that can include one or more ring heteroatoms, e.g., an optionally substitued cycloalkylamino or cycloheteroalkylamino ring, such as, but not limited to, optionally substituted pyrrolidinyl, piperidyl, morpholinyl, piperazinyl, azetidinyl, quinuclidinyl, and azepanyl.

6 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound having the structure:

and its pharmaceutically acceptable salts, hydrates, and coordination compounds, wherein:
R4, R2, R4, R5, R8, and R9 are selected independently from the group consisting of:
hydrogen, halo, cyano, nitro, thio, amino, carboxyl, formyl, sulfo, sulfinyl, sulfeno, sulfenamoyl, sulfonamino, and optionally substituted loweralkyl, loweralkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, cycloalkylcarbonyloxy, cycloheteroalkylcarbonyloxy, aralkycarbonyloxy, heteroaralkylcarbonyloxy, (cycloalkyl)alkylcarbonyloxy, (cycloheteroalkyl)alkylcarbonyloxy, loweralkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, cycloalkycarbonyl, cycloheteroalkycarbonyl, aralkycarbonyl, heteroaralkylcarbonyl, (cycloalkyl)alkylcarbonyl, (cycloheteroalkyl)alkylcarbonyl, loweralkylaminocarbonyl, arylaminocarbonyl, aralkylaminocarbonyl, heteroarylaminocarbonyl, heteroaralkylamino carbonyl, loweralkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, cycloalkyl carbonylamino, cycloheteroalkylcarbonylamino, aralkylcarbonylamino, heteroaralkylcarbonylamino, (cycloalkyl)alkylcarbonylamino, (cycloheteroalkyl)alkylcarbonylamino, diloweralkylamino, arylamino, diarylamino, aralkylamino, diaralkylamino, heteroarylamino, diheteroarylamino, heteroaralkylamino, diheteroaralkylamino, loweralkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, loweralkylsulfonyldioxy, arylsulfonyldioxy, heteroarylsulfonyldioxy, loweralkylsulfo, arylsulfo, heteroarylsulfo, cycloalkylsulfo, loweralkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, loweralkylsulfeno, arylsulfeno, heteroarylsulfeno, cycloalkylsulfeno, loweralkylsulfoamino, arylsulfoamino, heteroarylsulfoamino, cycloalkylsulfoamino, sulfonaloweralkylcarbonylsulfenamoyl, arylcarbonylsulfenamoyl, heteroarylcarbonylsulfenamoyl, cycloalkyl carbonylsulfenamoyl, cycloheteroalkylcarbonylsulfenamoyl, aralkylcarbonylsulfenamoyl, heteroaralkylcarbonylsulfenamoyl, (cycloalkyl)alkylcarbonylsulfenamoyl, (cycloheteroalkyl)alkylcarbonylsulfenamoyl, diloweralkylsulfenamoyl, arylsulfenamoyl, diarylsulfenamoyl, aralkylsulfenamoyl, diaralkylsulfenamoyl, heteroarylsulfenamoyl, diheteroarylsulfenamoyl, heteroaralkylsulfenamoyl, diheteroaralkylsulfenamoyl, loweralkylcarbonylsulfinamoyl, arylcarbonylsulfinamoyl, heteroarylcarbonylsulfinamoyl, cycloalkyl carbonylsulfinamoyl, cycloheteroalkylcarbonylsulfinamoyl, aralkylcarbonylsulfinamoyl, heteroaralkylcarbonylsulfinamoyl, (cycloalkyl)alkylcarbonylsulfinamoyl, (cycloheteroalkyl)alkylcarbonylsulfinamoyl, diloweralkylsulfinamoyl, arylsulfinamoyl, diarylsulfinamoyl, aralkylsulfinamoyl, diaralkylsulfinamoyl, heteroarylsulfinamoyl, diheteroarylsulfinamoyl, heteroaralkylsulfinamoyl, diheteroaralkylsulfinamoyl, aralkycarbonylthioooxy, carbonylthio, heteroaralkylcarbonylthio, (cycloalkyloxy)carbonylthio, (cycloheteroalkyl)alkylcarbonylthio, loweralkyloxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, cycloalkyloxycarbonyl, cycloheteroalkyloxycarbonyl, aralyoxycarbonyloxloxycarbonyl, heteroaralkyloxycarbonyl, (cycloalkyl)alkyloxycarbonyl, (cycloheteroalkyl)alkyloxycarbonyl, iminoloweralkyl, iminocycloalkyl, iminocycloheteroalkyl, iminoaralkyl, iminoheteroaralkyl, (cycloalkyl)iminoalkyl, and (cycloheteroalkyl)iminoalkyl;
R3 is selected from the group consisting of:
halo, oxo, thio, imino, iminoloweralkyl, iminocycloalkyl, iminocycloheteroalkyl, iminoaralkyl, iminoheteroaralkyl, (cycloalkyl)iminoalkyl, and (cycloheteroalkyl)iminoalkyl;
and
R6 and R7 are selected independently from the group consisting of:
hydrogen and optionally substitued loweralkyl, loweralkyloxyloweralkyl, aminoloweralkyl, loweralkylaminoloweralkyl, diloweralkylaminoloweralkyl, loweralkylthioloweralkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, arylcarbonyl, alkylcarbonyl, aralkylcarbonyl, heteroarylcarbonyl, and heteroaralkylcarbonyl;
in addition, R6 and R7, together with the nitrogen atom to which each is attached, can form an optionally substitued 4-, 5-, 6-, or 7-membered ring that can include one or more ring heteroatoms, e.g., an optionally substitued cycloalkylamino or cycloheteroalkylamino ring, such as, but not limited to, optionally substituted pyrrolidinyl, piperidyl, morpholinyl, piperazinyl, azetidinyl, quinuclidinyl, and azepanyl.

6 more elements