JPWO2021064570A5 - - Google Patents
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- Publication number
- JPWO2021064570A5 JPWO2021064570A5 JP2022520238A JP2022520238A JPWO2021064570A5 JP WO2021064570 A5 JPWO2021064570 A5 JP WO2021064570A5 JP 2022520238 A JP2022520238 A JP 2022520238A JP 2022520238 A JP2022520238 A JP 2022520238A JP WO2021064570 A5 JPWO2021064570 A5 JP WO2021064570A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- alkyl
- optionally substituted
- pharmaceutical composition
- fluorines
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 23
- -1 -CH 3 and -OCH 3 Chemical compound 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims 17
- 235000019000 fluorine Nutrition 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- 239000000460 chlorine Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 208000031886 HIV Infections Diseases 0.000 claims 4
- 208000037357 HIV infectious disease Diseases 0.000 claims 4
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 238000010255 intramuscular injection Methods 0.000 claims 2
- 239000007927 intramuscular injection Substances 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229950004159 bictegravir Drugs 0.000 claims 1
- SOLUWJRYJLAZCX-LYOVBCGYSA-N bictegravir Chemical compound C([C@H]1O[C@@H]2CC[C@@H](C2)N1C(=O)C1=C(C2=O)O)N1C=C2C(=O)NCC1=C(F)C=C(F)C=C1F SOLUWJRYJLAZCX-LYOVBCGYSA-N 0.000 claims 1
- 229950005928 cabotegravir Drugs 0.000 claims 1
- WCWSTNLSLKSJPK-LKFCYVNXSA-N cabotegravir Chemical compound C([C@H]1OC[C@@H](N1C(=O)C1=C(O)C2=O)C)N1C=C2C(=O)NCC1=CC=C(F)C=C1F WCWSTNLSLKSJPK-LKFCYVNXSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 229960002542 dolutegravir Drugs 0.000 claims 1
- RHWKPHLQXYSBKR-BMIGLBTASA-N dolutegravir Chemical compound C([C@@H]1OCC[C@H](N1C(=O)C1=C(O)C2=O)C)N1C=C2C(=O)NCC1=CC=C(F)C=C1F RHWKPHLQXYSBKR-BMIGLBTASA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- SWMDAPWAQQTBOG-UHFFFAOYSA-N fostemsavir Chemical compound C1=2N(COP(O)(O)=O)C=C(C(=O)C(=O)N3CCN(CC3)C(=O)C=3C=CC=CC=3)C=2C(OC)=CN=C1N1C=NC(C)=N1 SWMDAPWAQQTBOG-UHFFFAOYSA-N 0.000 claims 1
- 229950010812 fostemsavir Drugs 0.000 claims 1
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims 1
- 229960001627 lamivudine Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000010254 subcutaneous injection Methods 0.000 claims 1
- 239000007929 subcutaneous injection Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- FXLFSLGEPUVFNN-UHFFFAOYSA-N 2-pyrimidin-4-ylpyrimidine Chemical compound N1=CC=CN=C1C1=CC=NC=N1 FXLFSLGEPUVFNN-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 239000007819 coupling partner Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- WJUIBBUNTDEGNX-UHFFFAOYSA-N 2-(4-tributylstannyl-1,3-thiazol-2-yl)propan-2-ol Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CSC(C(C)(C)O)=N1 WJUIBBUNTDEGNX-UHFFFAOYSA-N 0.000 description 1
- PFPXDRMYWSWAGQ-UHFFFAOYSA-N FC(C)(F)C=1SC(=CN=1)[Sn](CCCC)(CCCC)CCCC Chemical compound FC(C)(F)C=1SC(=CN=1)[Sn](CCCC)(CCCC)CCCC PFPXDRMYWSWAGQ-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962908677P | 2019-10-01 | 2019-10-01 | |
| US62/908,677 | 2019-10-01 | ||
| US201962924781P | 2019-10-23 | 2019-10-23 | |
| US62/924,781 | 2019-10-23 | ||
| US202062967761P | 2020-01-30 | 2020-01-30 | |
| US62/967,761 | 2020-01-30 | ||
| PCT/IB2020/059101 WO2021064570A1 (en) | 2019-10-01 | 2020-09-29 | N-substututed-6-oxo-1,6-dihydropyrimidine-2-yl derivatives as inhibitors of the human immunodeficiency virus replication |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022551256A JP2022551256A (ja) | 2022-12-08 |
| JPWO2021064570A5 true JPWO2021064570A5 (https=) | 2023-10-10 |
| JP2022551256A5 JP2022551256A5 (https=) | 2023-10-10 |
Family
ID=72811912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022520238A Pending JP2022551256A (ja) | 2019-10-01 | 2020-09-29 | ヒト免疫不全ウイルスの複製阻害剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20220409619A1 (https=) |
| EP (1) | EP4038064B1 (https=) |
| JP (1) | JP2022551256A (https=) |
| ES (1) | ES2974657T3 (https=) |
| WO (1) | WO2021064570A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2021004593A (es) | 2018-10-24 | 2021-06-15 | Viiv Healthcare Uk No 5 Ltd | Inhibidores de la replicacion del virus de la inmunodeficiencia humana. |
| TW202128648A (zh) * | 2019-10-04 | 2021-08-01 | 英商Ｖｉｉｖ醫療保健英國(Ｎｏ 5)有限公司 | 人類免疫不全病毒複製之抑制劑 |
| US20250042926A1 (en) | 2023-05-31 | 2025-02-06 | Gilead Sciences, Inc. | Therapeutic compounds for hiv |
| AR132951A1 (es) | 2023-06-15 | 2025-08-13 | Viiv Healthcare Uk No 5 Ltd | Métodos e intermedios para preparar compuestos |
| US12594276B2 (en) | 2024-02-05 | 2026-04-07 | Viiv Healthcare Uk (No. 5) Limited | Inhibitors of human immunodeficiency virus replication |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464654B (zh) | 2010-11-12 | 2016-01-13 | 上海泓博智源医药技术有限公司 | 抗病毒化合物 |
| EP2729448B1 (en) | 2011-07-06 | 2015-09-09 | Gilead Sciences, Inc. | Compounds for the treatment of hiv |
| CN102863512B (zh) | 2011-07-07 | 2016-04-20 | 上海泓博智源医药技术有限公司 | 抗病毒化合物 |
| CA2897268C (en) | 2013-01-09 | 2018-12-04 | Gilead Sciences, Inc. | Therapeutic compounds for the treatment of viral infections |
| TW201443037A (zh) * | 2013-01-09 | 2014-11-16 | Gilead Sciences Inc | 治療用化合物 |
| CA2896244C (en) | 2013-01-09 | 2017-07-04 | Gilead Sciences, Inc. | 5-membered heteroaryls and their use as antiviral agents |
| TWI694071B (zh) | 2013-03-01 | 2020-05-21 | 美商基利科學股份有限公司 | 治療反轉錄病毒科(Retroviridae)病毒感染之治療性化合物 |
| WO2015130964A1 (en) | 2014-02-28 | 2015-09-03 | Gilead Sciences, Inc. | Therapeutic compounds |
| WO2015130966A1 (en) | 2014-02-28 | 2015-09-03 | Gilead Sciences, Inc. | Antiviral agents |
| PT3186239T (pt) | 2014-08-29 | 2019-01-10 | Gilead Sciences Inc | Agentes antirretrovirais |
| KR20230011471A (ko) * | 2016-08-19 | 2023-01-20 | 길리애드 사이언시즈, 인코포레이티드 | Hiv 바이러스 감염의 예방적 또는 치유적 치료에 유용한 치료 화합물 |
| TW201906834A (zh) * | 2017-05-02 | 2019-02-16 | 英商Viiv醫療保健英國(No.5)有限公司 | 人類免疫不全病毒複製之抑制劑 |
| US10836746B2 (en) | 2018-02-15 | 2020-11-17 | Gilead Sciences, Inc. | Therapeutic compounds |
| WO2019161280A1 (en) | 2018-02-16 | 2019-08-22 | Gilead Sciences, Inc. | Methods and intermediates for preparing a therapeutic compound useful in the treatment of retroviridae viral infection |
-
2020
- 2020-09-29 ES ES20789276T patent/ES2974657T3/es active Active
- 2020-09-29 US US17/763,317 patent/US20220409619A1/en not_active Abandoned
- 2020-09-29 EP EP20789276.1A patent/EP4038064B1/en active Active
- 2020-09-29 JP JP2022520238A patent/JP2022551256A/ja active Pending
- 2020-09-29 WO PCT/IB2020/059101 patent/WO2021064570A1/en not_active Ceased
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