JPWO2020053811A5 - - Google Patents
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- JPWO2020053811A5 JPWO2020053811A5 JP2021514019A JP2021514019A JPWO2020053811A5 JP WO2020053811 A5 JPWO2020053811 A5 JP WO2020053811A5 JP 2021514019 A JP2021514019 A JP 2021514019A JP 2021514019 A JP2021514019 A JP 2021514019A JP WO2020053811 A5 JPWO2020053811 A5 JP WO2020053811A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- alkyl
- hydrogen
- methyl
- pharmaceutical composition
- 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.)
- Granted
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- 150000003839 salts Chemical class 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 14
- 235000019000 fluorine Nutrition 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 208000031886 HIV Infections Diseases 0.000 claims description 7
- 208000037357 HIV infectious disease Diseases 0.000 claims description 7
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims description 4
- 229950005928 cabotegravir Drugs 0.000 claims description 4
- 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 description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 229960002542 dolutegravir Drugs 0.000 claims description 4
- 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 description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229950010812 fostemsavir Drugs 0.000 claims description 4
- 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 description 4
- 229960001627 lamivudine Drugs 0.000 claims description 4
- 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 description 4
- 239000002777 nucleoside Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
- ZIAOVIPSKUPPQW-UHFFFAOYSA-N 3-chloro-5-[1-[(4-methyl-5-oxo-1h-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)pyridin-3-yl]oxybenzonitrile Chemical compound N1C(=O)N(C)C(CN2C(C(OC=3C=C(C=C(Cl)C=3)C#N)=C(C=C2)C(F)(F)F)=O)=N1 ZIAOVIPSKUPPQW-UHFFFAOYSA-N 0.000 claims description 2
- 208000030507 AIDS Diseases 0.000 claims description 2
- 108010019625 Atazanavir Sulfate Proteins 0.000 claims description 2
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 2
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 2
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims description 2
- AXRYRYVKAWYZBR-GASGPIRDSA-N atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 claims description 2
- CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229950003141 doravirine Drugs 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000002835 hiv fusion inhibitor Substances 0.000 claims description 2
- 239000004030 hiv protease inhibitor Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229960004710 maraviroc Drugs 0.000 claims description 2
- GSNHKUDZZFZSJB-QYOOZWMWSA-N maraviroc Chemical compound CC(C)C1=NN=C(C)N1[C@@H]1C[C@H](N2CC[C@H](NC(=O)C3CCC(F)(F)CC3)C=3C=CC=CC=3)CC[C@H]2C1 GSNHKUDZZFZSJB-QYOOZWMWSA-N 0.000 claims description 2
- 230000035800 maturation Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229940068586 prezista Drugs 0.000 claims description 2
- 229940107904 reyataz Drugs 0.000 claims description 2
- 229960002814 rilpivirine Drugs 0.000 claims description 2
- YIBOMRUWOWDFLG-ONEGZZNKSA-N rilpivirine Chemical compound CC1=CC(\C=C\C#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-ONEGZZNKSA-N 0.000 claims description 2
- 229960004556 tenofovir Drugs 0.000 claims description 2
- VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 108010002459 HIV Integrase Proteins 0.000 claims 1
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 2
- 229940099797 HIV integrase inhibitor Drugs 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
- 239000003084 hiv integrase inhibitor Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862731196P | 2018-09-14 | 2018-09-14 | |
| US62/731,196 | 2018-09-14 | ||
| US201862733259P | 2018-09-19 | 2018-09-19 | |
| US62/733,259 | 2018-09-19 | ||
| PCT/IB2019/057710 WO2020053811A1 (en) | 2018-09-14 | 2019-09-12 | Inhibitors of human immunodeficiency virus replication |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2022500425A JP2022500425A (ja) | 2022-01-04 |
| JPWO2020053811A5 true JPWO2020053811A5 (https=) | 2022-08-09 |
| JP2022500425A5 JP2022500425A5 (https=) | 2022-08-09 |
| JP7361766B2 JP7361766B2 (ja) | 2023-10-16 |
Family
ID=68240777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021514019A Active JP7361766B2 (ja) | 2018-09-14 | 2019-09-12 | ヒト免疫不全ウイルス複製の阻害剤 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20220089598A1 (https=) |
| EP (1) | EP3849982A1 (https=) |
| JP (1) | JP7361766B2 (https=) |
| WO (1) | WO2020053811A1 (https=) |
Families Citing this family (11)
| 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. |
| US20210395262A1 (en) * | 2018-10-24 | 2021-12-23 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| EP3873607B1 (en) * | 2018-10-29 | 2023-11-29 | VIIV Healthcare UK (No.5) Limited | Quinazolinyl-indazole derivatives and their use as inhibitors of human immunodeficiency virus replication |
| SG11202107145SA (en) | 2019-01-25 | 2021-08-30 | Univ Brown | Compositions and methods for treating, preventing or reversing age-associated inflammation and disorders |
| 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 |
| TWI902729B (zh) | 2019-11-28 | 2025-11-01 | 日商鹽野義製藥股份有限公司 | 以組合整合酶阻礙劑及抗ｈｉｖ藥為特徵之ｈｉｖ感染症的預防及治療用醫藥 |
| WO2024175044A2 (en) * | 2023-02-23 | 2024-08-29 | Ascletis Bioscience Co., Ltd. | Inhibitors of human immunodeficiency virus replication, method of making and method of using thereof |
| 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 (16)
| 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 |
| WO2015130966A1 (en) | 2014-02-28 | 2015-09-03 | Gilead Sciences, Inc. | Antiviral agents |
| WO2015130964A1 (en) | 2014-02-28 | 2015-09-03 | Gilead Sciences, Inc. | Therapeutic compounds |
| 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 |
| JP7386230B2 (ja) | 2018-08-09 | 2023-11-24 | 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 |
-
2019
- 2019-09-12 WO PCT/IB2019/057710 patent/WO2020053811A1/en not_active Ceased
- 2019-09-12 EP EP19787072.8A patent/EP3849982A1/en active Pending
- 2019-09-12 US US17/272,377 patent/US20220089598A1/en not_active Abandoned
- 2019-09-12 JP JP2021514019A patent/JP7361766B2/ja active Active