JPWO2021064571A5 - - Google Patents
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- JPWO2021064571A5 JPWO2021064571A5 JP2022520234A JP2022520234A JPWO2021064571A5 JP WO2021064571 A5 JPWO2021064571 A5 JP WO2021064571A5 JP 2022520234 A JP2022520234 A JP 2022520234A JP 2022520234 A JP2022520234 A JP 2022520234A JP WO2021064571 A5 JPWO2021064571 A5 JP WO2021064571A5
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- JP
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- Prior art keywords
- compound
- following
- alkyl
- salt according
- salt
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims 38
- 235000019000 fluorine Nutrition 0.000 claims 14
- 125000001153 fluoro group Chemical group F* 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 208000031886 HIV Infections Diseases 0.000 claims 4
- 208000037357 HIV infectious disease Diseases 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000010255 intramuscular injection Methods 0.000 claims 2
- 239000007927 intramuscular injection Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 238000010254 subcutaneous injection Methods 0.000 claims 2
- 239000007929 subcutaneous injection Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- -1 G8 is H Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- 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
- 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
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- HEYONDYPXIUDCK-UHFFFAOYSA-L (5-diphenylphosphanyl-9,9-dimethylxanthen-4-yl)-diphenylphosphane;palladium(2+);dichloride Chemical compound Cl[Pd]Cl.C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 HEYONDYPXIUDCK-UHFFFAOYSA-L 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VWENLWUOIPCRRJ-UHFFFAOYSA-N (3-methyl-1h-pyrazol-5-yl)boronic acid Chemical compound CC=1C=C(B(O)O)NN=1 VWENLWUOIPCRRJ-UHFFFAOYSA-N 0.000 description 1
- DXLQEJHUQKKSRB-UHFFFAOYSA-N 1,1,1-trifluoro-n-pyridin-2-yl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=N1 DXLQEJHUQKKSRB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GEWFNXUSWMETAI-UHFFFAOYSA-N [3-(trifluoromethyl)-1h-pyrazol-5-yl]boronic acid Chemical compound OB(O)C=1C=C(C(F)(F)F)NN=1 GEWFNXUSWMETAI-UHFFFAOYSA-N 0.000 description 1
- SWUPLEAGZOKLNX-UHFFFAOYSA-N [4-fluoro-2-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(F)C=C1C(F)(F)F SWUPLEAGZOKLNX-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000007819 coupling partner Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962908715P | 2019-10-01 | 2019-10-01 | |
| US62/908,715 | 2019-10-01 | ||
| US201962925300P | 2019-10-24 | 2019-10-24 | |
| US62/925,300 | 2019-10-24 | ||
| PCT/IB2020/059103 WO2021064571A1 (en) | 2019-10-01 | 2020-09-29 | N-substituted-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-2-yl derivatives as inhibitors of the human immunodeficiency virus replication |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022551254A JP2022551254A (ja) | 2022-12-08 |
| JPWO2021064571A5 true JPWO2021064571A5 (https=) | 2023-10-10 |
| JP2022551254A5 JP2022551254A5 (https=) | 2023-10-10 |
Family
ID=72811913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022520234A Pending JP2022551254A (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 (4)
| Country | Link |
|---|---|
| US (1) | US20220389007A1 (https=) |
| EP (1) | EP4038068A1 (https=) |
| JP (1) | JP2022551254A (https=) |
| WO (1) | WO2021064571A1 (https=) |
Families Citing this family (6)
| 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 |
| WO2021070054A1 (en) * | 2019-10-08 | 2021-04-15 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| 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 US US17/763,133 patent/US20220389007A1/en not_active Abandoned
- 2020-09-29 WO PCT/IB2020/059103 patent/WO2021064571A1/en not_active Ceased
- 2020-09-29 EP EP20789277.9A patent/EP4038068A1/en not_active Withdrawn
- 2020-09-29 JP JP2022520234A patent/JP2022551254A/ja active Pending
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