19 ORGANISATION AFRICAINE DE LA PROPRIETE INTELLECTUELLE 51 8 Inter. CI. A61K 31/517 (2018.01) 11 A61P 31/18 (2018.01) N° 18583 C07D 239/94 (2018.01) C07D 401/12 (2018.01) FASCICULE DE BREVET D'INVENTION 21 Numéro de dépôt : 1201700237 73 Titulaire(s): PCT/US2015/000460 GILEAD SCIENCES, INC., 333 Lakeside Drive, 22 Date de dépôt : 23/12/2015 FOSTER CITY, CA 94404 (US) INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE AS CR, 30 Priorité(s): V.V.I., Flemingovo Nam. 2, 166 10 PRAHA 6 (CZ) US n° 62/096,748 du 24/12/2014 Inventeur(s): 72 HU Yunfeng Eric (US) MACKMAN Richard L. (US) LANSDON Eric (c/o Gilead Sciences, Inc. (US) JANSA Petr (US) SIMON Petr (CZ) BASZCZYNSKI Ondrej (CZ) DEJMEK Milan (CZ) 24 Délivré le : 11/12/2018 74 Mandataire: GAD CONSULTANTS SCP, 45 Publié le : 28.12.2018 B.P. 13448, YAOUNDE (CM). 54 Titre: Quinazoline derivatives used to treat HIV. 57 Abrégé : and tautomers and pharmaceutical salts thereof, compositions and formulations containing such Described herein are compounds of Formula compounds, and methods of using and making such compounds. O.A.P.I. – B.P. 887, YAOUNDE (Cameroun) – Tel. (237) 222 20 57 00 – Site web: http:/www.oapi.int – Email: [email protected] 18583 QUINAZOLINE DERIVATIVES USED TO TREAT IIIV CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application claims priority benefit to U.S. Application Serial No. 62/096,748, filed December 24, 2014, the disclosure of which is herein incorporated by reference in its entirety. BACKGROUND [0002] While progress has been made in treating 111V and AIDS, HIV infection remains a global health concern. As part of such treatments, non-nucleoside reverse transcriptase inhibitors (NNRTIs) have often been employed, particularly as part of highly active antiretroviral therapy (HAART) treatment regimens. Though potent, drawbacks exist for many of the known NNRTIs as their use has been associated with mutations in the 111V virus that may result in drug resistance. As such, there remains a need for further development of potent NNTRIs. [0003] Described herein are compounds of Formula (I) and pharmaceutically acceptable salts thereof, compositions and formulations containing such compounds, or pharmaceutically acceptable salts thereof, and methods of using and making such compounds, or pharmaceutically acceptable salts thereof SUMMARY [0004] In certain embodiments, the present disclosure relates to compounds of Formula (I) or a tautomer thereof, wherein Q is 18583 XI, X2, and X3 are each independently N or C(RII ), provided that, at most 2 of X I, X2, and X3 are N; R' is -H, -CN, -OR', -C(0)0111, halogen, Ci_olkyl, C3-10cycloalkyl, or C1- theteroalkyl, wherein each C14alkyl, C3.1ocycloalkyl, and C14heteroalkyl is optionally substituted with 1, 2, 3, 4, or 5 le2 groups, which may be same or different R2 is -H, -CN, -01e, -Nlele, - C(0)0116, halogen, Cl_talkyl, C3.1ocycloalkyl, or C1.6 heteroalkyl, wherein each C1.6alkyl, C3-tocycloalkyl, and C14heteroalkyl is optionally substituted with 1, 2, 3, 4, or 5 R'2 groups, which may be same or different, R3 is -H, -OR', -SR', -Nlele,-NHC(0)NR°Rb, C1.6alkyl, C3-tocycloalkyl, or C1.6 heteroalkyl, wherein each CI-alkyl, C3-tocycloalkyl, and Ct-theteroalkyl is optionally substituted with 1, 2, 3, 4, or 5 le2 groups, which may be same or different; fe is -H, -OR', halogen, -NO2, -CN, -NHC(0)Nlele, -0C(0)Nlele, - CH2C(0)NR"Rb, C,4alkyl, C3-10cycloalkyl, or CI4 heteroalkyl, wherein each C1-6alkyl, tocycloalkyl, and C1-6 heteroalkyl is optionally substituted with 1, 2, 3, 4, or 5R'2 groups, which may be same or different; R' is -H, -OR', halogen, -NO2, -CN, -Mete, -NHC(0)NR'R b, -0C(0)Nlele, - CH2C(0)Nlele, C14alkyl, C3-tocycloalkyl, or CI4 heteroalkyl, wherein each Cl_talkyl. C3- tocycloalkyl, and C1-6 heteroalkyl is optionally substituted with 1, 2, 3, 4, or 5 R'2 groups, which may be same or different R6 is -H, -OR', halogen, -NO2, -CN, -NR•R b, -NI1C(0)NR'le, -0C(0)N1V1e, - CH2C(0)NR'Rb, Clasalkyl, C3-locycloalkyl, or CI-6 heteroalkyl, wherein each Ct-talkyl, C3. tocycloalkyl, and C14 heteroalkyl is optionally substituted with 1, 2, 3, 4, or 5 102 groups, which may be same or different; R7 is C1.6alkyl, C3-tocycloalkyl, Ct-6heteroalkyl, halogen, -OR', -CN, or wherein each CI-alkyl, C3-tocycloalkyl, and Ct-6 heteroalkyl is optionally substituted with 1, 2, 3, 4, or 5 R' 2 groups, which may be same or different; R8 is Ci_salkyl, C3-iocycloalkyl, Ct4heteroalkyl, halogen, -OR', -CN, or -NO2, wherein each C14alkyl, C3-tocycloalkyl, and C1-6 heteroalkyl is optionally substituted with 1, 2, 3, 4, or 5 R' 2 groups, which may be same or different; R9 is -H, C14alkyl, or C3-10cycloalkyl, wherein each C1.6alkyl and C3-tocycloalkyl is optionally substituted with 1, 2, 3, 4, or 5 R' 2 groups, which may be same or different; 2 18583 R1° is -11, Cialkyl, Or C3.10cycloalkyl, wherein each Clasalkyl and Cl.rocycloalkyl is optionally substituted with 1, 2, 3, 4, or 5 R" groups, which may be same or different; each R" is independently -II, -CN, -OR', -C(0)OR', halogen, Clalkyl, tocycloalkyl, or Ci.sheteroalkyl, which may be same or different, wherein each C,-alkyl, C3- iocycloalkyl, and Ci-sheteroalkyl is optionally substituted with 1, 2, 3, 4, or 5 R" groups, which may be same or different; each R" is independently Ct.6alkyl, Cflocycloalkyl, Cr_sheteroalkyl, 5-10 membered heterocyclyl, C6.1oaryl, 5-10 membered heteroaryl, halogen, -OR', -C(0)R', -C(0)OR', - C(0)NR'Rb, -0C(0)NR'Rb, -NRIC(0)0Rb, -SR', -S(0)1.2125, -S(0)2F, -S(0)2NRIF0,- NR'S(0)212b, -N3, -CN, or -NO2; wherein each Ci.salkyl, C3i0cycloalkyl, Cr4heteroalkyl, and 5-10 membered heterocyclyl is optionally substituted with I, 2, 3, 4, or 5 substituents selected from halogen, -OR', -C(0)W, -C(0)0W, -C(0)NR'R b, -0C(0)NRab, - NR•C(0)01211, -SR', -S(0)1.2R', -S(0)2F, -S(0)2NR•R 1', -NR'S(0)2Rb, -/sb, -CN, and - NO2, groups, which may be same or different; each R' and Rb is independently -II, -Nth CI.6alkyl, C3-iocycloalkyl, Ciaeteroalkyl, 5-10 membered heterocyclyl, C6.10aryl, or 5-10 membered heteroaryl, wherein each CI. &alkyl, C3-Irtcycloalkyl, Claeteroalkyl, 5-10 membered heterocyclyl, C6.10aryl, and 5-10 membered heteroaryl is optionally substituted with 1, 2, 3, 4, or 5 R 13 groups, which may be same or different or R' and Rb together with the atoms to which they are attached form a 5- 10 membered heterocycle; and each R13 is independently -CN, halogen, C1.6alkyl, C3.10cycloalkyl, Cr.sheteroalkyl, or 5-10 membered heterocyclyl; or a pharmaceutically acceptable salt thereof. [0005] In certain embodiments, the current disclosure relates to a pharmaceutical composition comprising a compound of Formula (I), or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. [0006] In certain embodiments, the current disclosure relates to an article of manufacture comprising a unit dosage of a compound of Formula (I), or a pharmaceutically acceptable salt thereof. 3 18583 [0007] In certain embodiments, the current disclosure relates to a method of inhibiting reverse transcriptase in a subject in need thereof, comprising administering a compound of Formula (I), or a pharmaceutically acceptable salt thereof, to the subject [0008] In certain embodiments, the current disclosure relates to a method for treating or preventing an HIV infection in a subject in need thereof, comprising administering to the subject a compound of Formula (I), or a pharmaceutically acceptable salt thereof [0009] In certain embodiments, the current disclosure relates to a method for preventing an HIV infection in a subject, comprising administering to the subject a compound of Formula (I), or a pharmaceutically acceptable salt thereof. In certain embodiments, the subject is at risk of contracting the HIV virus, such as a subject who has one or more risk factors known to be associated with contracting the HIV virus. [0010] In certain embodiments, the current disclosure relates to a method for treating or preventing an HIV infection in a subject in need thereof, comprising administering to the subject a compound of Formula (I), or a pharmaceutically acceptable salt thereof, in combination with a therapeutically effective amount of one or more additional therapeutic agents. [0011] In certain embodiments, the current disclosure relates to a compound of Formula (I), or a pharmaceutically acceptable salt thereof, for use in medical therapy. [0012] In certain embodiments, the current disclosure relates to a compound of Formula (I), or a pharmaceutically acceptable salt thereof, for use in treating or preventing an HIV virus infection in a subject. [0013] In certain embodiments, the current disclosure relates to the use of a compound of Formula (I), or a pharmaceutically acceptable salt thereof, for the manufacture of a medicament for treating or preventing an Illy virus infection in a subject [0014] Additional embodiments of the present disclosure are disclosed herein. BRIEF DESCRIPTION OF THE DRAWINGS [0015] Figure 1 shows results of resistance profile against HIV-I RT (Reverse Transcriptase) mutants of certain compounds. DETAILED DESCRIPTION [0016] The description below is made with the understanding that the present disclosure is to be considered as an exemplification of the claimed subject matter, and is not intended 4 18583 to limit the appended claims to the specific embodiments illustrated. The headings used throughout this disclosure are provided for convenience and are not to be construed to limit the claims in any way. Embodiments illustrated under any heading may be combined with embodiments illustrated under any other heading.