JPWO2021064677A5 - - Google Patents
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- JPWO2021064677A5 JPWO2021064677A5 JP2022520588A JP2022520588A JPWO2021064677A5 JP WO2021064677 A5 JPWO2021064677 A5 JP WO2021064677A5 JP 2022520588 A JP2022520588 A JP 2022520588A JP 2022520588 A JP2022520588 A JP 2022520588A JP WO2021064677 A5 JPWO2021064677 A5 JP WO2021064677A5
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- Prior art keywords
- compound
- alkyl
- salt according
- fluorines
- following
- 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 36
- 150000003839 salts Chemical class 0.000 claims 35
- 235000019000 fluorine Nutrition 0.000 claims 17
- 125000001153 fluoro group Chemical group F* 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004212 difluorophenyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims 2
- 238000010255 intramuscular injection Methods 0.000 claims 2
- 239000007927 intramuscular injection Substances 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
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 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
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-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
- 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
- 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 2
- 239000012071 phase Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JUHYEUAQEZTNJZ-UHFFFAOYSA-N CC1(OB(OC1(C)C)C=1C=CN(N=1)CC(C(F)F)(F)F)C Chemical compound CC1(OB(OC1(C)C)C=1C=CN(N=1)CC(C(F)F)(F)F)C JUHYEUAQEZTNJZ-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
- RSYSOJXBKGAQOX-UHFFFAOYSA-N FC(CN1N=C(C=C1)[Sn](CCCC)(CCCC)CCCC)(C)F Chemical compound FC(CN1N=C(C=C1)[Sn](CCCC)(CCCC)CCCC)(C)F RSYSOJXBKGAQOX-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- MJBMQEOEAFETAK-PMERELPUSA-N tert-butyl N-[(1S)-1-[7-bromo-3-[4-chloro-3-[(4-methoxyphenyl)methyl-methylsulfonylamino]-1-methylindazol-7-yl]-4-oxoquinazolin-2-yl]-2-(3,5-difluorophenyl)ethyl]carbamate Chemical compound BrC1=CC=C2C(N(C(=NC2=C1)[C@H](CC1=CC(=CC(=C1)F)F)NC(OC(C)(C)C)=O)C=1C=CC(=C2C(=NN(C=12)C)N(S(=O)(=O)C)CC1=CC=C(C=C1)OC)Cl)=O MJBMQEOEAFETAK-PMERELPUSA-N 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962910684P | 2019-10-04 | 2019-10-04 | |
| US62/910,684 | 2019-10-04 | ||
| PCT/IB2020/059274 WO2021064677A1 (en) | 2019-10-04 | 2020-10-02 | Inhibitors of human immunodeficiency virus replication |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022552156A JP2022552156A (ja) | 2022-12-15 |
| JP2022552156A5 JP2022552156A5 (https=) | 2023-10-11 |
| JPWO2021064677A5 true JPWO2021064677A5 (https=) | 2023-10-11 |
Family
ID=73014547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022520588A Pending JP2022552156A (ja) | 2019-10-04 | 2020-10-02 | ヒト免疫不全ウイルスの複製阻害剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20230013823A1 (https=) |
| EP (1) | EP4038061A1 (https=) |
| JP (1) | JP2022552156A (https=) |
| AR (1) | AR120150A1 (https=) |
| TW (1) | TW202128648A (https=) |
| WO (1) | WO2021064677A1 (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. |
| 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 (31)
| 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 |
| CA2896244C (en) | 2013-01-09 | 2017-07-04 | Gilead Sciences, Inc. | 5-membered heteroaryls and their use as antiviral agents |
| TW201443037A (zh) | 2013-01-09 | 2014-11-16 | Gilead Sciences Inc | 治療用化合物 |
| CA2897268C (en) | 2013-01-09 | 2018-12-04 | Gilead Sciences, Inc. | Therapeutic compounds for the treatment of viral infections |
| 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 |
| WO2019198024A1 (en) * | 2018-04-11 | 2019-10-17 | VIIV Healthcare UK (No.5) Limited | 4-oxo-3,4-dihydroquinazoline compounds as inhibitors of human immunodeficiency virus replication |
| WO2020053811A1 (en) * | 2018-09-14 | 2020-03-19 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| JP7433303B2 (ja) * | 2018-09-20 | 2024-02-19 | ヴィーブ ヘルスケア ユーケー（ナンバー５）リミテッド | ヒト免疫不全ウイルス複製の阻害剤 |
| US20210395262A1 (en) * | 2018-10-24 | 2021-12-23 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| MX2021004593A (es) * | 2018-10-24 | 2021-06-15 | Viiv Healthcare Uk No 5 Ltd | Inhibidores de la replicacion del virus de la inmunodeficiencia humana. |
| US20210393633A1 (en) * | 2018-10-25 | 2021-12-23 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| US20210379071A1 (en) * | 2018-11-05 | 2021-12-09 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| WO2020095177A1 (en) * | 2018-11-05 | 2020-05-14 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| UY38559A (es) * | 2019-02-01 | 2020-07-31 | Viiv Healthcare Uk No 5 Ltd | Inhibidores de la replicación del virus de la inmunodeficiencia humana |
| ES2974657T3 (es) * | 2019-10-01 | 2024-07-01 | Viiv Healthcare Uk No 5 Ltd | Derivados de n-substituido-6-oxo-1,6-dihidropirimidina-2-ilo como inhibidores de la replicación del virus de inmunodeficiencia humana |
| US20220389007A1 (en) * | 2019-10-01 | 2022-12-08 | Viiv Healthcare Uk (No. 5) Limited | Inhibitors of human immunodeficiency virus replication |
| WO2021070054A1 (en) * | 2019-10-08 | 2021-04-15 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| UY38982A (es) * | 2019-12-09 | 2021-06-30 | Viiv Healthcare Co | Composiciones farmacéuticas |
| JP2023517312A (ja) * | 2020-03-06 | 2023-04-25 | ビーブ、ヘルスケア、ユーケー、（ナンバー５）、リミテッド | ヒト免疫不全ウイルスの複製阻害剤 |
| KR20220151655A (ko) * | 2020-03-06 | 2022-11-15 | 비브 헬스케어 유케이 (넘버5) 리미티드 | 인간 면역결핍 바이러스 복제의 억제제 |
| CN115397424A (zh) * | 2020-04-15 | 2022-11-25 | Viiv保健英国第五有限公司 | 人类免疫缺陷病毒复制的抑制剂 |
| US20240423985A1 (en) * | 2021-10-13 | 2024-12-26 | Viiv Healthcare Uk (No.5) Limit-Ed | Inhibitors of human immunodeficiency virus replication |
-
2020
- 2020-09-30 TW TW109134208A patent/TW202128648A/zh unknown
- 2020-10-02 EP EP20797180.5A patent/EP4038061A1/en not_active Withdrawn
- 2020-10-02 WO PCT/IB2020/059274 patent/WO2021064677A1/en not_active Ceased
- 2020-10-02 AR ARP200102746A patent/AR120150A1/es not_active Application Discontinuation
- 2020-10-02 US US17/763,161 patent/US20230013823A1/en not_active Abandoned
- 2020-10-02 JP JP2022520588A patent/JP2022552156A/ja active Pending
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