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Generated: December 13, 2017

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Title:S-triazolyl .alpha.-mercaptoacetanilides 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 (Aliso Viejo, CA), Koh; Yung-Hyo (Irvine, CA), De La Rosa; Martha (Fountain Valley, CA), Gunic; Esmir (Irvine, CA), Hong; Zhi (Chapel Hill, NC), Lang; Stanley (Laguna Niguel, CA), Kim; Woo-Hong (Irvine, CA)
Assignee: Ardes Biosciences Inc. (San Diego, CA)
Filing Date:Aug 25, 2005
Application Number:11/661,079
Claims:1. A compound of formula A ##STR00329## wherein: Q is selected from the group consisting of a salt of COOH, CONR'R'', SO.sub.3H or a salt thereof, and SO.sub.2NR'R''; P is selected from the group consisting of (a), (b), (c) and (d) ##STR00330## R.sup.1 is selected from the group consisting of Cl, Br, I, CH.sub.3, CF.sub.3, CHF.sub.2, and CH.sub.2F; R.sup.3 is H or CH.sub.3; R' and R'' are independently selected from the group consisting of H, lower alkyl, and lower alkyl substituted with one or more OR, CO.sub.2R, NHR, NR.sub.2, or CF.sub.3 groups wherein R is H or lower alkyl, or R' and R'' together with the nitrogen atom to which they are attached form a 4-, 5-, or 6-membered heterocyclic ring; R.sup.O is selected from the group consisting of Cl, Br, CF.sub.3 and methyl; R.sup.P is selected from the group consisting of halogen, methyl, ethyl, propyl, isopropyl, cyclopropylmethyl, and C.sub.3-C.sub.6 eyeloalkyl; R.sup.4, R.sup.5 and R.sup.6 are independently selected from the group consisting of H, F, Cl, Br, CH.sub.3, CF.sub.3, CFH.sub.2, CF.sub.2H, isopropyl, cyclopropyl, OCH.sub.3, OH, OCF.sub.3, NH.sub.2 and NHCH.sub.3; U and U' are independently selected from N and CH; R.sup.7 is selected from the group consisting of Cl, Br, I, CH.sub.3, CF.sub.3, OCH.sub.3, isopropyl, cyclopropyl, tert-butyl, and cyclohutyl; and R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently H or CH.sub.3; with the provisos that, when Q is SO.sub.2NH.sub.2, R.sup.1 is not methyl unless R.sup.P is halogen, cyclopropylmethyl or C.sub.3-C.sub.6 cycloalkyl, and R.sup.7 is methyl only if R.sup.6 is methyl.

2. The compound of claim 1, wherein P is a substituted naphthyl and R.sup.1 is selected from the group consisting of Br, CF.sub.3, CFH.sub.2, and CF.sub.2H.

3. The compound of claim 2, wherein each of R.sup.4, R.sup.5, and R.sup.6 is H.

4. The compound of claim 2, wherein R.sup.P is cyclopropyl.

5. The compound of claim 2, wherein R.sup.1 is Br and R.sup.O is Cl.

6. The compound of claim 1, wherein P is a substituted quinoline or isoquinoline and R.sup.1 is selected from the group consisting of Br, CF.sub.3, CFH.sub.2, and CF.sub.2H.

7. The compound of claim 6, wherein each of R.sup.4, R.sup.5, and R.sup.6 is H.

8. The compound of claim 6, wherein R.sup.P is cyclopropyl.

9. The compound of claim 6, wherein R.sup.1 is Br and R.sup.O is Cl.

10. The compound of claim 1, wherein Q is a salt of COOH and wherein the salt is Na+, K+, Ca++, Mg++, or DABCO salt.

11. A pharmaceutical composition comprising a compound of claim 1 in combination with one or more pharmaceutically acceptable carriers.

12. The compound of claim 1, 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)-acetamidc or 2-[5-bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfan- yl]-N-(2-chloro-4-carbamoyl-phenyl)-acetamide.

13. The compound of claim 1, 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-ylsulfan- yl]-N-(2-methyl-4-carbamoyl-phenyl)-acetamide.
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