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|Title:||N[S(4-aryl-triazol-3-yl).alpha.-mercaptoacetyl]-p-amino benzoic acids as HIV reverse transcriptase inhibitors|
|Abstract:||A series of S-triazolyl .alpha.-mercaptoacetanilides having N-(.alpha.-mercaptoacetyl) p amino benzoic acid derivatives. ##STR00001## are provided, where Q is CO.sub.2H, or a salt or ester thereof, or a C(O) N-linked amino acid. The compounds inhibit several variants of the reverse transcriptase of HIV, and are useful in the treatment of HIV infections.|
|Inventor(s):||Girardet; Jean-Luc (San Diego, CA), Koh; Yung-Hyo (Irvine, CA), De La Rosa; Martha (Durham, NC), Hong; Zhi (Irvine, CA), Lang; Stanley (Laguna Niguel, CA)|
|Assignee:||Ardea Biosciences, Inc. (San Diego, CA)|
|Filing Date:||Dec 06, 2011|
|Claims:||1. A method of inhibiting HIV reverse transcriptase, the method comprising contacting HIV reverse transcriptase with a compound of formula 1: ##STR00106## wherein: R.sup.1 is Cl, Br, I, CH.sub.3, CF.sub.3, CHF.sub.2 or CH.sub.2F; R.sup.3 is H or CH.sub.3; R.sup.o is Cl, Br, CF.sub.3 or methyl; X is O or NH; R.sup.2 is H, a pharmaceutically acceptable cation or C.sub.1-3 alkyl, when X is O; or XR.sup.2 is NHCH.sub.2CH.sub.2COOR.sup.13 or NHCH(R.sup.12)COOR.sup.13; where R.sup.12 is C.sub.1-4 alkyl or aryl-C.sub.1-4 alkyl; and R.sup.13 is a pharmaceutically acceptable cation or C.sub.1-3 alkyl; Ar is selected from the group consisting of (a), (b), (c) and (d): ##STR00107## wherein R.sup.P is selected from the group consisting of methyl, ethyl, propyl, isopropyl, cyclopropylmethyl, and C.sub.3-6 cycloalkyl; R.sup.4, R.sup.5 and R.sup.6 are independently selected from the group consisting of H, F, Cl, Br, CF.sub.3, CFH.sub.2, CF.sub.2H, ethyl, isopropyl, cyclopropyl, OCH.sub.3, OH, OCF.sub.3, NH.sub.2 and NHCH.sub.3; R.sup.7 is selected from the group consisting of Cl, Br, I, CF.sub.3, OCH.sub.3, isopropyl, cyclopropyl, tent-butyl, and cyclobutyl; and R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently H or CH.sub.3. |
2. The method of claim 1, wherein the HIV reverse transcriptase is a mutated reverse transcriptase.
3. The method of claim 2, wherein the mutated reverse transcriptase is a K103N, Y181C or Y188L mutant.
4. The method of claim 1, wherein the inhibition occurs in vitro.
5. The method of claim 1, wherein the inhibition occurs in vivo.
6. The method of claim 1, wherein the compound of formula 1 is 4-[2-(5-bromo-4-[4-cyclopropyl-7-methoxynaphthalen-l-yl]-4H-1,2,4-triazol- -3-ylthio)acetamido]-3-chlorobenzoic acid.
7. The method of claim 5, wherein the compound of formula 1 is 4-[2-(5-bromo-4-[4-cyclopropyl-7-methoxynaphthalen-l-yl]-4H-1,2,4-triazol- -3-ylthio)acetamido]-3-chlorobenzoic acid.
8. The method of claim 1, wherein the compound of formula 1 is a pharmaceutically acceptable salt of 4-[2-(5-bromo-4-[4-cyclopropyl-7-methoxynaphthalen-1-yl]-4H-1,2,4-triazol- -3-ylthio)acetamido]-3-chlorobenzoic acid, R.sup.2 being a pharmaceutically acceptable cation.
9. The method of claim 1, wherein the compound of formula 1 is a methyl, ethyl or propyl ester of 4-[2-(5-bromo-4-[4-cyclopropyl-7-methoxynaphthalen-l-yl]-4H-1,2,4-triazol- -3-ylthio)acetamido]-3-chlorobenzoic acid, R.sup.2 being methyl, ethyl, or propyl.
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