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Generated: February 24, 2018

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Title:S-Triazolyl alpha-mercapto acetanilides as inhibitors of HIV reverse transcriptase
Abstract: A series of S-triazolyl .alpha.-mercaptoacetanilides having general structure (1) are provided, where Q is CO.sub.2H, CONR.sub.2, SO.sub.3H, or SO.sub.2NR.sub.2. The compounds inhibit several variants of the reverse transcriptase of HIV, and are useful in the treatment of HIV infections. ##STR00001##
Inventor(s): Girardet; Jean-Luc (San Diego, CA), Koh; Yung-Hyo (Irvine, CA), De La Rosa; Martha A. (Durham, NC), Gunic; Esmir (San Diego, CA), Hong; Zhi (Irvine, CA), Lang; Stanley (Laguna Niguel, CA), Kim; Woo-Hong (San Diego, CA)
Assignee: Ardea Biosciences, Inc. (San Diego, CA)
Filing Date:Apr 06, 2011
Application Number:13/081,398
Claims:1. A compound of Formula A': ##STR00328## wherein: R.sub.1 is C.sub.1-3 alkyl, CF.sub.3, CHF.sub.2, CH.sub.2F, Cl, Br, NH.sub.2, or hydrogen; R.sub.2 is an aryl or heteroaryl moiety which can be further substituted with alkyl, cycloalkyl, aryl or heteroaryl moieties; Q is C.sub.3-5 cycloalkyl; W is S, O, or an optionally substituted amine; R.sub.3 is C.sub.1-3 alkyl, CF.sub.3, CHF.sub.2, CH.sub.2F, Cl or Br; and R.sub.4 is COR' or S(O).sub.2R', wherein R' is NH.sub.2 or NH(alkyl).

2. The compound of claim 1, wherein R.sub.2 is 4-Q-naphth-1-yl or 4-Q-phen-1-yl.

3. The compound of claim 1, wherein R' is NH.sub.2.

4. The compound of claim 3, wherein Q is cyclopropyl.

5. The compound of claim 3, wherein W is S.

6. The compound of claim 4, wherein W is S.

7. The compound of claim 6, wherein R.sub.1 is other than hydrogen.

8. The compound of claim 7, wherein R.sub.1 is Br, R.sub.2 is naphthyl, and R.sub.3 is methyl or Cl.

9. The compound of claim 8, which is 2-[5-bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfan- yl]-N-(2-chloro-4-sulfamoyl-phenyl)-acetamide or 2[5-bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfany- l]-N-(2-chloro-4-carbamoyl-phenyl)-acetamide.

10. The compound of claim 8, which is 2-[5-bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfan- yl]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide or 2[5-bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfany- l]-N-(2-methyl-4-carbamoyl-phenyl)-acetamide.
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