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Last Updated: December 12, 2025

Claims for Patent: 9,732,092


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Summary for Patent: 9,732,092
Title:Substituted 2,3,4,5,7,9,13,13a-octahydropyrido[1′,2′:4,5]pyrazino[2,1-b][1,3]OXAZEPINES and methods for treating viral infections
Abstract:Compounds for use in the treatment of human immunodeficiency virus (HIV) infection are disclosed. The compounds have the following Formula (I): including stereoisomers and pharmaceutically acceptable salts thereof, wherein R1, X, W, Y1, Y2, Z1, and Z4 are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.
Inventor(s):Haolun Jin, Scott E. Lazerwith, Hyung-Jung Pyun, Elizabeth M. Bacon, Philip Anthony Morganelli, Mingzhe Ji
Assignee:Gilead Sciences Inc
Application Number:US15/349,934
Patent Claims: 1. A compound having Formula (I): or a stereoisomer or pharmaceutically acceptable salt thereof, wherein: X is —O—; W is —CHZ2—; Z1 and Z2, taken together, form -L- wherein L is —C(Ra)2C(Ra)2—; Z4 is —CH2—; Y1 and Y2 are each independently hydrogen, C1-3alkyl or C1-3haloalkyl; R1 is phenyl substituted with one, two or three halogens; and each Ra is independently hydrogen, halo, hydroxy or C1-4alkyl.

2. The compound of claim 1, wherein R1 is substituted with one halogen.

3. The compound of claim 2, wherein R1 is 4-fluorophenyl or 2-fluorophenyl.

4. The compound of claim 1, wherein R1 is substituted with two halogens.

5. The compound of claim 4, wherein R1 is 2,4-difluorophenyl, 2,3-difluorophenyl, 2,6-difluorophenyl, 3-fluoro-4-chlorophenyl, 3,4-difluorophenyl, 2-fluoro-4-chlorophenyl, or 3,5-difluorophenyl.

6. The compound of claim 5, wherein R1 is 2,4-difluorophenyl.

7. The compound of claim 1, wherein R1 is substituted with three halogens.

8. The compound of claim 7, wherein R1 is 2,4,6-trifluorophenyl or 2,3,4-trifluorophenyl.

9. The compound of claim 8, wherein R1 is 2,4,6-trifluorophenyl.

10. The compound of claim 1, wherein Y1 and Y2 are each independently hydrogen, methyl or trifluoromethyl.

11. The compound of claim 1, having Formula (II-A):

12. The compound of claim 1, wherein the compound is selected from the group consisting of:

13. A pharmaceutical composition comprising a compound of claim 1, or a stereoisomer or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent or excipient.

14. RAE pharmaceutical composition of claim 13, further comprising one or more additional therapeutic agents.

15. The pharmaceutical composition of claim 14, wherein the one or more one additional therapeutic agents is an anti-human immunodeficiency virus agent.

16. The pharmaceutical composition of claim 15, wherein the one or more additional therapeutic agents is selected from the group consisting of a human immunodeficiency virus protease inhibitor, a human immunodeficiency virus non-nucleoside inhibitor of reverse transcriptase, a human immunodeficiency virus nucleoside inhibitor of reverse transcriptase and a human immunodeficiency virus nucleotide inhibitor of reverse transcriptase, or a combination thereof.

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