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US 5,681,832 AGranted
Aroylaniline compounds, pharmaceutical compositions, and methods of using same to inhibit viral activity
AssigneesThe United States of America as represented by the Department of Health and Human Services, Georgia Tech Research Corporation
InventorsRudiger D. Haugwitz, Leon Zalkow, Ewa Gruszecka-Kowalik, Edward Burgess
Life of this patent
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Abstract
Aroylaniline compounds which exhibit anti-retroviral activity, pharmaceutical compositions containing such aroylaniline compounds, and methods for treating a retroviral-infected host comprising administering an antiviral effective amount of an aroylaniline compound to a host.
Claims31
An aroylaniline compound having the formula:
- ##STR20## wherein R is --H, --SO.sub.3.E, --CO.sub.2.E, --PO(O).sub.2 2.E, --NO.sub.2, or a halogen;
- Q is ##STR21## Y is ##STR22## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently --H , --OH, a halogen, --NH.sub.2, --NHCH.sub.3, --N(CH.sub.3).sub.2, --CHO, CH.sub.3 O--, --SO.sub.3.E, --NO.sub.2, --CO.sub.2.E, --PO(O).sub.2 2.E, --CH.sub.2 OH, --CH.sub.2 SCH.sub.2 COR.sup.7, --CH.sub.2 S--C.sub.2 H.sub.4 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SCH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SC.sub.2 H.sub.4 CO.sub.2 R.sup.7 or ##STR23## wherein E represents H, lithium, sodium, potassium, ammonium, magnesium, (HOC.sub.2 H.sub.4).sub.3 NH, (CH.sub.3).sub.3 NH, CH.sub.3 NH(C.sub.2 H.sub.4 OH).sub.2, (CH.sub.3).sub.4 N--, or HN-methylglucamine and wherein R.sup.7 is H, methyl, ethyl, benzyl, --NH.sub.2, --NHCH.sub.3, or --NHC.sub.2 H.sub.5 ;
- X is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CONH--, --NHCONH--, --NHCSNH--, --S--, --SO--, --SO.sub.2 --, --NH--, --CH.sub.2 -- or cyclopropyl;
- Z is oxygen or sulfur;
- and
- n is 1 or 2, but when n is 1, Y is H, ##STR24## and when n is 2, Y is --CO or --CS.
3 more elements
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and an aroylaniline compound having the structural formula:
- ##STR31## wherein R is --H, --SO.sub.3.E, --CO.sub.2.E, --PO(O).sub.2.2E, --NO.sub.2, or a halogen;
- Q is ##STR32## Y is ##STR33## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently --H, --OH, a halogen, --NH.sub.2, --NHCH.sub.3, --N(CH.sub.3).sub.2, --CHO, CH.sub.3 O--, --SO.sub.3.E, --NO.sub.2, --CO.sub.2.E, --PO(O).sub.2.2E, --CH.sub.2 OH, --CH.sub.2 SCH.sub.2 COR.sup.7, --CH.sub.2 S--C.sub.2 H.sub.4 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SCH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SC.sub.2 H.sub.4 CO.sub.2 R.sup.7 or ##STR34## wherein E represents H, lithium, sodium, potassium, ammonium, magnesium, (HOC.sub.2 H.sub.4).sub.3 NH, (CH.sub.3).sub.3 NH, CH.sub.3 NH(C.sub.2 H.sub.4 OH).sub.2, (CH.sub.3).sub.4 N--, or HN-methylglucamine and wherein R.sup.7 is H, methyl, ethyl, benzyl, --NH.sub.2, --NHCH.sub.3, or --NHC.sub.2 H.sub.5 ;
- X is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CONH--, --NHCONH--, --NHCSNH--, --S--, --SO--, --SO.sub.2 --, --NH--, --CH.sub.2 -- or cyclopropyl;
- Z is oxygen or sulfur;
- and
- n is 1 or 2, but when n is 1, Y is H, ##STR35## and when n is 2, Y is --CO or --CS.
3 more elements
A method for treating a viral infection of a host which comprises administering to said host an antiviral effective amount of an aroylaniline compound having the structural formula:
- ##STR36## wherein R is --H, --SO.sub.3.E, --CO.sub.2.E, --PO(O).sub.2.2E, --NO.sub.2, or a halogen;
- Q is ##STR37## Y is ##STR38## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently --H, --OH, a halogen, --NH.sub.2, --NHCH.sub.3, --N(CH.sub.3).sub.2, --CHO, CH.sub.3 O--, --SO.sub.3.E, --NO.sub.2, --CO.sub.2.E, --PO(O).sub.2.2E, --CH.sub.2 OH, --CH.sub.2 SCH.sub.2 COR.sup.7, --CH.sub.2 S--C.sub.2 H.sub.4 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SCH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SC.sub.2 H.sub.4 CO.sub.2 R.sup.7 or ##STR39## wherein E represents H, lithium, sodium, potassium, ammonium, magnesium, (HOC.sub.2 H.sub.4).sub.3 NH, (CH.sub.3).sub.3 NH, CH.sub.3 NH(C.sub.2 H.sub.4 OH).sub.2, (CH.sub.3).sub.4 N--, or HN-methylglucamine and wherein R.sup.7 is H, methyl, ethyl, benzyl, --NH.sub.2, --NHCH.sub.3, or --NHC.sub.2 H.sub.5 ;
- X is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CONH--, --NHCONH--, --NHCSNH--, --S--, --SO--, --SO.sub.2 --, --NH--, --CH.sub.2 -- or cyclopropyl;
- Z is oxygen or sulfur;
- and
- n is 1 or 2, but when n is 1, Y is H, ##STR40## and when n is 2, Y is --CO or --CS.
3 more elements
A method for inhibiting replication of a retrovirus comprising contacting said retrovirus with a retrovirally effective amount of an aroylaniline compound having the structural formula:
- ##STR41## wherein R is --H, --SO.sub.3.E, --CO.sub.2.E, --PO(O).sub.2.2E, --NO.sub.2, or a halogen;
- Q is ##STR42## Y is ##STR43## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently --H, --OH, a halogen, --NH.sub.2, --NHCH.sub.3, --N(CH.sub.3).sub.2, --CHO, CH.sub.3 O--, --SO.sub.3.E, --NO.sub.2, --CO.sub.2.E, --PO(O).sub.2.2E, --CH.sub.2 OH, --CH.sub.3 SCH.sub.2 COR.sup.7, --CH.sub.2 S--C.sub.2 H.sub.4 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SCH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SC.sub.2 H.sub.4 CO.sub.2 R.sup.7 or ##STR44## wherein E represents H, lithium, sodium, potassium, ammonium, magnesium, (HOC.sub.2 H.sub.4).sub.3 NH, (CH.sub.3).sub.3 NH, CH.sub.3 NH(C.sub.2 H.sub.4 OH).sub.2, (CH.sub.3).sub.4 N--, or HN-methylglucamine and wherein R.sup.7 is H, methyl, ethyl, benzyl, --NH.sub.2, --NHCH.sub.3, or --NHC.sub.2 H.sub.5 ;
- X is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CONH--, --NHCONH--, --NHCSNH--, --S--, --SO--, --SO.sub.2 --, --NH--, --CH.sub.2 -- or cyclopropyl;
- Z is oxygen or sulfur;
- and
- n is 1 or 2, but when n is 1, Y is H, ##STR45## and when n is 2, Y is --CO or --CS.
3 more elements
A method for treating a retroviral infection in a mammal comprising administering a retrovirally effective amount of an aroylanilline compound having the structural formula:
- ##STR51## where R is --H, --SO.sub.3.E, --CO.sub.2.E, --PO(O).sub.2.2E, --NO.sub.2, or a halogen;
- Q is ##STR52## Y is ##STR53## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently --H, --OH, a halogen, --NH.sub.2, --NHCH.sub.3, --N(CH.sub.3).sub.2, --CHO, CH.sub.3 O--, --SO.sub.3.E, --NO.sub.2, --CO.sub.2.E, --PO(O).sub.2.2E, --CH.sub.2 OH, --CH.sub.2 SCH.sub.2 COR.sup.7, --CH.sub.2 S--C.sub.2 H.sub.4 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SCH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SC.sub.2 H.sub.4 CO.sub.2 R.sup.7 or ##STR54## wherein E represents H, lithium, sodium, potassium, ammonium, magnesium, (HOC.sub.2 H.sub.4).sub.3 NH, (CH.sub.3).sub.3 NH, CH.sub.3 NH(C.sub.2 H.sub.4 OH).sub.2, (CH.sub.3).sub.4 N--, or HN-methylglucamine and wherein R.sup.7 is H, methyl, ethyl, benzyl, --NH.sub.2, --NHCH.sub.3, or --NHC.sub.2 H.sub.5 ;
- X is --CH.dbd.CH--, --CH.sub.2 CH.sub.2, --CONH--, --NHCONH--, --NHCSNH--, --S--, --SO--, --SO.sub.2 --, --NH--, --CH.sub.2 -- or cyclopropyl;
- Z is oxygen or sulfur;
- and
- n is 1 or 2, but when n is 1, Y is H, ##STR55## and when n is 2, Y is --CO or --CS.
3 more elements
A method for inhibiting replication of a virus in vitro comprising contacting said virus with an anti-virally effective amount of an aroylaniline compound having the structural formula:
- ##STR56## wherein R is --H, --SO.sub.3.E, --CO.sub.2.E, --PO(O).sub.2.2E, --NO.sub.2, or a halogen;
- Q is ##STR57## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently --H, --OH, a halogen, --NH.sub.2, --NHCH.sub.3, --N(CH.sub.3).sub.2, --CHO, CH.sub.3 O--, --SO.sub.3.E, --NO.sub.2, --CO.sub.2.E, --PO(O).sub.2.2E, --CH.sub.2 OH, --CH.sub.2 SCH.sub.2 COR.sup.7, --CH.sub.2 S--C.sub.2 H.sub.4 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SCH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SC.sub.2 H.sub.4 CO.sub.2 R.sup.7 or ##STR58## wherein E represents H, lithium, sodium, potassium, ammonium, magnesium, (HOC.sub.2 H.sub.4).sub.3 NH, (CH.sub.3).sub.3 NH, CH.sub.3 NH(C.sub.2 H.sub.4 OH).sub.2, (CH.sub.3).sub.4 N--, or HN-methylglucamine and wherein R.sup.7 is H, methyl, ethyl, benzyl, --NH.sub.2, --NHCH.sub.3, or --NHC.sub.2 H.sub.5 ;
- X is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CONH--, --NHCONH--, --NHCSNH--, --S--, --SO--, --SO.sub.2 --, --NH--, --CH.sub.2 -- or cyclopropyl;
- Z is oxygen or sulfur;
- and
- n is 1 or 2, but when n is 1, Y is H, ##STR59## and when n is 2, Y is --CO or --CS.
3 more elements
A method for preventing a mammal from being infected by a herpes virus comprising administering a prophylactively effective amount of an aroylaniline compound having the structural formula:
- ##STR60## wherein R is --H, --SO.sub.3.E, --CO.sub.2.E, --PO(O).sub.2.2E, --NO.sub.2, or a halogen;
- Q is ##STR61## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently --H, --OH, a halogen, --NH.sub.2, --NHCH.sub.3, --N(CH.sub.3).sub.2, --CHO, CH.sub.3 O--, --SO.sub.3.E, --NO.sub.2, --CO.sub.2.E, --PO(O).sub.2.2E, --CH.sub.2 OH, --CH.sub.2 SCH.sub.2 COR.sup.7, --CH.sub.2 S--C.sub.2 H.sub.4 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 COR.sup.7, --CH.sub.2 S--CH(CO.sub.2 H)CH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SCH.sub.2 CO.sub.2 R.sup.7, --CH.sub.2 SC.sub.2 H.sub.4 CO.sub.2 R.sup.7 or ##STR62## wherein E represents H, lithium, sodium, potassium, ammonium, magnesium, (HOC.sub.2 H.sub.4).sub.3 NH, (CH.sub.3).sub.3 NH, CH.sub.3 NH(C.sub.2 H.sub.4 OH).sub.2, (CH.sub.3).sub.4 N--, or HN-methylglucamine and wherein R.sup.7 is H, methyl, ethyl, benzyl, --NH.sub.2, --NHCH.sub.3, or --NHC.sub.2 H.sub.5 ;
- X is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CONH--, --NHCONH--, --NHCSNH--, --S--, --SO--, --SO.sub.2 --, --NH--, --CH.sub.2 -- or cyclopropyl;
- Z is oxygen or sulfur;
- and
- n is 1 or 2, but when n is 1, Y is H, ##STR63## and when n is 2, Y is --CO or --CS.
3 more elements
Dependencies are inferred from the claim text.