Claims
- 1. A compound having the formula: ##STR76## wherein: R.sup.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
- R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, mono-, di- or tri-halomethyl, trifluoromethoxy, methylthio, nitro, cyano, acetoxy or dimethylamino;
- R.sup.3 is --CO.sub.2 R.sup.5 wherein
- R.sup.5 is an alkyl, C.sub.3 -C.sub.6 alkenyl or alkynyl, a one to six haloalkyl, an alkoxyalkyl, an alkylthioalkyl, a carboxyalkyl, an alkylcarboxyalkyl, a C.sub.6 -C.sub.12 arylcarboxyalkyl, an alkylaminoalkyl or dialkylaminoalkyl, a trialkylsilylalkyl, each of the aforementioned alkyl moieties having from one to eight carbon atoms; a phenyl, a naphthyl, a C.sub.1 -C.sub.6 alkylphenyl, a C.sub.7 -C.sub.12 arylalkyl or alkarylalkyl, a C.sub.3 -C.sub.8 carbocyclyl, a C.sub.1 -C.sub.4 alkyl C.sub.3 -C.sub.8 carbocyclyl;
- R.sup.4 is hydrogen, halo, methyl or mono-, di- or tri-halomethyl;
- R is ##STR77## wherein Z.sup.2 is S; and
- R.sup.A is R.sup.10 --W-- wherein
- W is O; and
- R.sup.10 is a linear or branched, unsubstituted or halo-substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl; a C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloalkyl C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkenyl unsubstituted or substituted by C.sub.1 -C.sub.6 alkyl; an unsubstituted phenyl or phenyl substituted by halo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, carboxyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.8 alkylthio, phenyl, nitro, amino, hydroxyl, acetyl acetyloxy, phenoxy, C.sub.1 -C.sub.8 alkoxycarbonyl, C.sub.1 -C.sub.8 alkylcarbonyl.
- 2. A compound having the formula: ##STR78## wherein Z is S;
- R.sup.A is a C.sub.1 -C.sub.8 alkoxy; a C.sub.2 -C.sub.8 alkenyloxy; a C.sub.2 -C.sub.8 alkynyloxy; a C.sub.3 -C.sub.8 cycloalkyloxy; a C.sub.3 -C.sub.8 cycloalkyl- alkoxy; a C.sub.7 -C.sub.8 phenoxyalkyl or a phenoxy;
- R.sup.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
- R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, mono-, di- or tri-halomethyl, trifluoromethoxy, methylthio, nitro, cyano, acetoxy or dimethylamino;
- R.sup.3 is --CO.sub.2 R.sup.5 wherein
- R.sup.5 is an alkyl, a C.sub.3 -C.sub.6 alkenyl or alkynyl, a one to six haloalkyl, an alkoxyalkyl, an alkylthioalkyl, a carboxyalkyl, an alkylcarboxyalkyl, a C.sub.6 -C.sub.12 arylcarboxyalkyl, an alkylaminoalkyl or dialkylaminoalkyl, a trialkylsilylalkyl, each of the aforementioned alkyl moieties having from one to eight carbon atoms; a phenyl, a naphthyl, a C.sub.1 -C.sub.6 alkylphenyl, a C.sub.7 -C.sub.12 arylalkyl or alkarylalkyl, a C.sub.3 -C.sub.8 carbocyclyl, a C.sub.1 -C.sub.4 alkyl C.sub.3 -C.sub.8 carbocyclyl;
- R.sup.4 is hydrogen, halo, methyl or mono-, di- or tri-halomethyl.
- 3. A compound according to claim 1 wherein said compound has the formula: ##STR79## wherein R.sup.15 is a C.sub.1 -C.sub.8 alkoxy; a C.sub.2 -C.sub.8 alkenyloxy or alkynyloxy; a C.sub.1 -C.sub.8 aryloxy; a C.sub.3 -C.sub.8 cycloalkyloxy, cycloalkylalkyloxy, cycloalkylaryloxy;
- Z is S;
- R.sup.1 is hydrogen, halo or C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
- R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, mono-, di- or tri-halomethyl, trifluoromethoxy, methylthio, nitro, cyano, acetoxy or dimethylamino;
- R.sup.3 is --CO.sub.2 R.sup.5 wherein
- R.sup.5 is an alkyl, a C.sub.3 -C.sub.6 alkenyl or alkynyl, a one to six haloalkyl, an alkoxyalkyl, an alkylthioalkyl, a carboxyalkyl, an alkylcarboxyalkyl, a C.sub.6 -C.sub.12 arylcarboxyalkyl, an alkylaminoalkyl or dialkylaminoalkyl, a trialkylsilylalkyl, each of the aforementioned alkyl moieties having from one to eight carbon atoms; a phenyl, a naphthyl, a C.sub.1 -C.sub.6 alkylphenyl, a C.sub.7 -C.sub.12 arylalkyl or alkarylalkyl, a C.sub.3 -C.sub.8 carbocyclyl, a C.sub.1 -C.sub.4 alkyl C.sub.3 -C.sub.8 carbocyclyl;
- R.sup.4 is hydrogen, halo, methyl or mono-, di- or tri-halomethyl.
- 4. A compound according to claim 3 wherein
- R.sup.1 is hydrogen or a fluoro;
- R.sup.4 is hydrogen; and
- R.sup.15 is a C.sub.1 -C.sub.8 alkoxy; a C.sub.2 -C.sub.8 alkenyloxy or alkynyloxy; phenoxy; C.sub.3 -C.sub.8 cycloalkoxy or cycloalkylalkyloxy; cycloalkylphenyloxy.
- 5. A compound of claim 1 wherein said compound is selected from the group consisting of:
- (1) 1-methylethyl 2-chloro-5-[[(1-methylethoxy)thioxomethyl]amino]benzoate;
- (2) 1-methylethyl 2-chloro-5-[(ethoxythioxomethyl]amino]benzoate;
- (3) 1-methylethyl 5-[(butoxythioxomethyl]amino]2-chlorobenzoate;
- (4) 1-methylethyl 2-chloro-5-[(propoxythioxomethyl]amino]benzoate;
- (5) 1-methylethyl 2-chloro-5-[[(pentyloxy)thioxomethyl]amino]benzoate;
- (6) 1-methylethyl 2-chloro-5-[[(2-propenyloxy)thioxomethyl]amino]benzoate;
- (7) 1-methylethyl 2-chloro-5-[[(2-cyclohexen-1-yloxy)thioxomethyl]amino]benzoate;
- (8) 1-methylethyl 2-chloro-5-[[(cyclohexyloxy)thioxomethyl]amino]benzoate;
- (9) 1-methylethyl 2-chloro-5-[[(cyclopropylmethoxy)thioxomethyl]amino]benzoate; and
- (10) 1-methylethyl 2-chloro-5-[[(2-methoxyethoxy)thioxomethyl]amino]benzoate.
- 6. The intermediate compound 2-chloro-5-[[(1-methylethoxy)thioxomethyl]amino]benzoic acid.
- 7. A compound of claim 5 wherein said compound is 1-methylethyl 2-chloro-5-[[(1-methylethoxy)thioxomethyl]amino]benzoate.
- 8. A pharmaceutical formulation for inhibiting the growth or replication of HIV which comprises an effective amount of the compound of claim 1 in a pharmaceutically acceptable carrier.
Parent Case Info
This is a Continuation-In-Part of U.S. Ser. No. 567,982 filed Aug. 15 ,1990 now abandoned, which is a Continuation-In-Part of U.S. Ser. No. 421,155 filed 16 October, 1989, now abandoned.
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
4861759 |
Mitsuya et al. |
Aug 1989 |
|
4880782 |
Eckstein et al. |
Nov 1989 |
|
4971977 |
Turano |
Nov 1990 |
|
4980371 |
Parker et al. |
Dec 1990 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
0104070 |
Sep 1983 |
EPX |
Non-Patent Literature Citations (1)
Entry |
Chemical Abstracts vol. 101, No. 13, Sep. 24, 1984, Abstract No. 110567b. |
Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
567982 |
Aug 1990 |
|
Parent |
421155 |
Oct 1989 |
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