Claims
- 1. A method of treating subjects suffering from HIV-1 infection which comprises administering to said subjects an effective anti-HIV-1 amount of a compound of the formula: ##STR25## a pharmaceutically acceptable acid addition salt form or a stereochemically isomeric form thereof, wherein:
- R.sup.5 and R.sup.6 each independently are hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, nitro, trifluoromethyl, cyano, aminomethyl, carboxyl; C.sub.1-4 alkyloxycarbonyl, C.sub.1-4 alkylcarbonyl, aminocarbonyl or hydroxy;
- R.sup.7 is hydrogen or halo;
- R.sup.8 represents C.sub.1-6 alkyloxy, nitro, trifluoromethoxy, 2,2,2-trifluoroethoxy, (trifluoromethyl)carbonyl, aminocarbonyl, (cyclopropyl)carbonyl, or a radical of the formula C.sub.1-6 alkyl-(C.dbd.Y)-- wherein .dbd.Y represents .dbd.O, .dbd.N--OH, .dbd.N--OCH.sub.3, .dbd.N--NH.sub.2, or .dbd.N--N(CH.sub.3).sub.2 ;
- R.sup.9 and R.sup.10 each independently are hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, nitro, hydroxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, (trifluoromethyl)carbonyl, aminocarbonyl, (cyclopropyl)carbonyl or a radical of the formula C.sub.1-6 alkyl-(C.dbd.Y)-- wherein .dbd.Y represents .dbd.O, .dbd.N--OH, .dbd.N--OCH.sub.3, .dbd.N--NH.sub.2, or .dbd.N--N(CH.sub.3).sub.2,
- provided that
- R.sup.8 is other than 2-methoxy when R.sup.5 is 6-chloro, R.sup.6, R.sup.7 and R.sup.9 are hydrogen and R.sup.10 is hydrogen or 5-methyl.
- 2. A method as claimed in claim 1 wherein R.sup.5 and R.sup.6 are each independently hydrogen, halo, C.sub.1-6 alkyloxy or nitro; R.sup.7 is hydrogen; R.sup.8 is C.sub.1-6 alkyloxy, nitro, trifluoromethoxy or C.sub.1-6 alkylcarbonyl; and R.sup.9 and R.sup.10 are each independently hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, nitro, trifluoromethoxy or C.sub.1-6 alkylcarbonyl.
- 3. A method as claimed in claim 2 wherein R.sup.5 and R.sup.6 are each independently hydrogen, halo, methoxy or nitro; R.sup.8 is methoxy, nitro, trifluoromethoxy or methylcarbonyl; and R.sup.9 and R.sup.10 are each independently hydrogen, halo, methyl, methoxy, nitro, trifluoromethoxy or methylcarbonyl.
- 4. A method as claimed in claim 3 wherein R.sup.5 represents 6-chloro, and R.sup.6 and R.sup.7 represent hydrogen;
- or
- R.sup.5 and R.sup.6 represent 3,6-dichloro and R.sup.7 represents hydrogen.
- 5. A method as claimed in claim 4 wherein R.sup.8 represents 2-methoxy, 2-nitro, 2-methylcarbonyl, or 2-trifluoromethyl; and R.sup.9 and R.sup.10 represent hydrogen;
- or
- R.sup.8 and R.sup.9 represent 2-methoxy-5-methyl, 2-nitro-5-chloro, 2-nitro-5-methyl, 2-methoxy-5-chloro, 2-methylcarbonyl-5-methyl, 2-methylcarbonyl-5-fluoro or 2-methylcarbonyl-5-chloro; and R.sup.10 represents hydrogen.
- 6. The method of claim 1 wherein the compound is (.+-.)-.alpha.-[(2-acetyl-5-methylphenyl)amino]-2,6-dichlorobenzeneacetamide.
- 7. The method of claim 1 wherein the compound is (-)-.alpha.-[(2-acetyl-5-methylphenyl)amino]-2,6-dichlorobenzeneacetamide.
- 8. A method as defined in claim 1 wherein said compound is selected from the group consisting of:
- (-)-.alpha.-[(2-nitrophenyl)amino]-2,6-dichlorobenzeneacetamide;
- (-)-.alpha.-[(5-methyl-2-nitrophenyl)amino]-2,6-dichlorobenzeneacetamide;
- (-)-.alpha.-[(2-acetylphenyl)amino]-2,6-dichlorobenzeneacetamide;
- (-)-.alpha.-[(2-acetyl-5-methylphenyl)amino]-2,6-dichlorobenzeneacetamide;
- .alpha.-[(2-acetyl-5-chlorophenyl)amino]-2,6-dichlorobenzeneacetamide;
- .alpha.-[(5-chloro-2-nitrophenyl)amino]-2,6-dichlorobenzeneacetamide; and
- .alpha.-[(2-acetyl-5-fluorophenyl)amino]-2,6-dichlorobenzeneacetamide.
- 9. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and as active ingredient an anti-HIV-1 effective amount of a compound as defined in claim 1.
- 10. A pharmaceutical composition as defined in claim 9 wherein said compound is selected from the group consisting of:
- (-)-.alpha.-[(2-nitrophenyl)amino]-2,6-dichlorobenzeneacetamide;
- (-)-.alpha.-[(5-methyl-2-nitrophenyl)amino]-2,6-dichlorobenzeneacetamide;
- (-)-.alpha.-[(2-acetylphenyl)amino]-2,6-dichlorobenzeneacetamide;
- (-)-.alpha.-[(2-acetyl-5-methylphenyl)amino]-2,6-dichlorobenzeneacetamide;
- .alpha.-[(2-acetyl-5-chlorophenyl)amino]-2,6-dichlorobenzeneacetamide;
- .alpha.-[(5-chloro-2-nitrophenyl)amino]-2,6-dichlorobenzene-acetamide; and
- .alpha.-[(2-acetyl-5-fluorophenyl)amino]-2,6-dichlorobenzeneacetamide.
- 11. The pharmaceutical composition of claim 9 wherein said compound is (.+-.)-.alpha.-[(2-acetyl-5-methylphenyl)amino]-2,6-dichlorobenzeneacetamide.
- 12. The pharmaceutical composition of claim 9 wherein said compound is (-)-.alpha.-[(2-acetyl-5-methylphenyl)amino]-2,6-dichlorobenzeneacetamide.
Priority Claims (2)
Number |
Date |
Country |
Kind |
90201857 |
Jul 1990 |
EPX |
|
91200646 |
Mar 1991 |
EPX |
|
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a divisional of copending application Ser. No. 07/956,777, filed Dec. 17, 1992, which in turn was based upon PCT application PCT/EP 91/01254, filed Jul. 4, 1991, which claimed priority from EP 90.201.857.1, filed Jul. 10, 1990, and EP 91.200.646.7, filed Mar. 22, 1991.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4246429 |
Van Daele |
Jan 1981 |
|
Divisions (1)
|
Number |
Date |
Country |
Parent |
956777 |
Dec 1992 |
|