JPWO2020150366A5 - - Google Patents
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- Publication number
- JPWO2020150366A5 JPWO2020150366A5 JP2021541219A JP2021541219A JPWO2020150366A5 JP WO2020150366 A5 JPWO2020150366 A5 JP WO2020150366A5 JP 2021541219 A JP2021541219 A JP 2021541219A JP 2021541219 A JP2021541219 A JP 2021541219A JP WO2020150366 A5 JPWO2020150366 A5 JP WO2020150366A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- group
- tert
- carboxylic acid
- butyl
- 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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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- -1 2,5- Dioxo-pyrimidine-1-yl Chemical group 0.000 claims description 21
- 241000700721 Hepatitis B virus Species 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims description 16
- 208000037262 Hepatitis delta Diseases 0.000 claims description 15
- 241000724709 Hepatitis delta virus Species 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 10
- 208000006454 hepatitis Diseases 0.000 claims description 10
- 231100000283 hepatitis Toxicity 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000002773 nucleotide Substances 0.000 claims description 8
- 125000003729 nucleotide group Chemical group 0.000 claims description 8
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 230000009385 viral infection Effects 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000000427 antigen Substances 0.000 claims description 6
- 208000002672 hepatitis B Diseases 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 108091036055 CccDNA Proteins 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 108020004459 Small interfering RNA Proteins 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 229940124765 capsid inhibitor Drugs 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000000203 mixture 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
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 4
- 101710132601 Capsid protein Proteins 0.000 claims description 3
- 102000036639 antigens Human genes 0.000 claims description 3
- 108091007433 antigens Proteins 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 2
- NJVJBGCBUPEAHU-UHFFFAOYSA-N 1-acetyl-6-tert-butyl-12-(difluoromethoxy)-9-oxo-2,3,4,5,6,10-hexahydroquinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound CC(=O)N1CCCC2=C3CC(C4=C(C3=CC(=C21)OC(F)F)NC(=O)C(=C4)C(=O)O)C(C)(C)C NJVJBGCBUPEAHU-UHFFFAOYSA-N 0.000 claims description 2
- JUXOCWXHUWKTTN-UHFFFAOYSA-N 12-tert-butyl-6-chloro-4-methyl-3-oxo-11,12-dihydrobenzo[c][1,10]phenanthroline-2-carboxylic acid Chemical compound CC(C)(C)C1CC2=C(C3=C1C=C(C(=O)N3C)C(=O)O)N=C(C4=CC=CC=C24)Cl JUXOCWXHUWKTTN-UHFFFAOYSA-N 0.000 claims description 2
- NGCGQBZIHUSODO-UHFFFAOYSA-N 12-tert-butyl-6-methoxy-4-methyl-3-oxo-11,12-dihydrobenzo[c][1,10]phenanthroline-2-carboxylic acid Chemical compound C(C)(C)(C)C1CC=2C3=C(C(=NC2C=2N(C(C(=CC12)C(=O)O)=O)C)OC)C=CC=C3 NGCGQBZIHUSODO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- UDBJOIQAPGQZHA-UHFFFAOYSA-N 6-tert-butyl-12-(difluoromethoxy)-1-(3-methoxypropyl)-9-oxo-2,3,4,5,6,10-hexahydroquinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound C(C)(C)(C)C1C=2C=C(C(NC2C=2C(=C3CCCN(C3=C(C2)OC(F)F)CCCOC)C1)=O)C(=O)O UDBJOIQAPGQZHA-UHFFFAOYSA-N 0.000 claims description 2
- DNLLDHOQDUTUSV-UHFFFAOYSA-N 6-tert-butyl-12-(difluoromethoxy)-1-ethyl-9-oxo-2,3,4,5,6,10-hexahydroquinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound CCN1CCCC2=C3CC(C4=C(C3=CC(=C21)OC(F)F)NC(=O)C(=C4)C(=O)O)C(C)(C)C DNLLDHOQDUTUSV-UHFFFAOYSA-N 0.000 claims description 2
- DDSJIKNKLWJWLY-UHFFFAOYSA-N 6-tert-butyl-12-(difluoromethoxy)-1-methyl-9-oxo-2,3,4,5,6,10-hexahydroquinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound CC(C)(C)C1CC2=C3CCCN(C3=C(C=C2C4=C1C=C(C(=O)N4)C(=O)O)OC(F)F)C DDSJIKNKLWJWLY-UHFFFAOYSA-N 0.000 claims description 2
- QRWDKLPPLBLZIC-UHFFFAOYSA-N 6-tert-butyl-12-(difluoromethoxy)-10-methyl-9-oxo-5,6-dihydroquinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound N1=CC=CC2=C1C(OC(F)F)=CC=1C=3N(C(=O)C(=CC=3C(C(C)(C)C)CC2=1)C(=O)O)C QRWDKLPPLBLZIC-UHFFFAOYSA-N 0.000 claims description 2
- KGBOSAQRERCGSQ-UHFFFAOYSA-N 6-tert-butyl-12-(difluoromethoxy)-7-hydroxy-9-oxo-2,3,4,5,6,10-hexahydro-1H-quinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound CC(C)(C)C1CC2=C3CCCNC3=C(C=C2C4=C1C(=C(C(=O)N4)C(=O)O)O)OC(F)F KGBOSAQRERCGSQ-UHFFFAOYSA-N 0.000 claims description 2
- PTUVUHUWLMXGSP-UHFFFAOYSA-N 6-tert-butyl-12-(difluoromethoxy)-7-hydroxy-9-oxo-6,10-dihydro-5H-quinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound C(C)(C)(C)C1C=2C(=C(C(NC=2C=2C(=C3C=CC=NC3=C(C=2)OC(F)F)C1)=O)C(=O)O)O PTUVUHUWLMXGSP-UHFFFAOYSA-N 0.000 claims description 2
- DDNZMKLKCVVVKK-UHFFFAOYSA-N 6-tert-butyl-12-(difluoromethoxy)-9-methoxy-10-methyl-7-oxo-5,6-dihydroquinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound CC(C)(C)C1CC2=C3C=CC=NC3=C(C=C2C4=C1C(=O)C(=C(N4C)OC)C(=O)O)OC(F)F DDNZMKLKCVVVKK-UHFFFAOYSA-N 0.000 claims description 2
- CPVNVXKCHHLCCA-UHFFFAOYSA-N 6-tert-butyl-12-(difluoromethoxy)-9-methoxy-7-oxo-6,10-dihydro-5H-quinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound C(C)(C)(C)C1C=2C(C(=C(NC=2C=2C(=C3C=CC=NC3=C(C=2)OC(F)F)C1)OC)C(=O)O)=O CPVNVXKCHHLCCA-UHFFFAOYSA-N 0.000 claims description 2
- UEJWFVYEXFXWGO-UHFFFAOYSA-N 6-tert-butyl-12-(difluoromethoxy)-9-oxo-6,10-dihydro-5H-quinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound C(C)(C)(C)C1C=2C=C(C(NC=2C=2C(=C3C=CC=NC3=C(C=2)OC(F)F)C1)=O)C(=O)O UEJWFVYEXFXWGO-UHFFFAOYSA-N 0.000 claims description 2
- ZDRLWGPSBYQBET-UHFFFAOYSA-N 6-tert-butyl-12-methoxy-9-oxo-6,10-dihydro-5H-quinolino[7,8-f]quinoline-8-carboxylic acid Chemical compound CC(C)(C)C1CC2=C3C=CC=NC3=C(C=C2C4=C1C=C(C(=O)N4)C(=O)O)OC ZDRLWGPSBYQBET-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- BLFJCJKTSCOLEY-UHFFFAOYSA-N cinnoline-3-carboxylic acid Chemical compound C1=CC=C2N=NC(C(=O)O)=CC2=C1 BLFJCJKTSCOLEY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000003566 oxetanyl group Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- MTAHTDBOMUECCQ-UHFFFAOYSA-N 1,10-phenanthroline-2-carboxylic acid Chemical compound C1=CN=C2C3=NC(C(=O)O)=CC=C3C=CC2=C1 MTAHTDBOMUECCQ-UHFFFAOYSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962793578P | 2019-01-17 | 2019-01-17 | |
| US62/793,578 | 2019-01-17 | ||
| PCT/US2020/013701 WO2020150366A1 (en) | 2019-01-17 | 2020-01-15 | Substituted polycyclic carboxylic acids, analogues thereof, and methods using same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022518456A JP2022518456A (ja) | 2022-03-15 |
| JP2022518456A5 JP2022518456A5 (https=) | 2022-06-08 |
| JPWO2020150366A5 true JPWO2020150366A5 (https=) | 2022-06-08 |
Family
ID=71613992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021541219A Pending JP2022518456A (ja) | 2019-01-17 | 2020-01-15 | 置換多環式カルボン酸、その類似体、およびそれらの使用法 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20220125771A1 (https=) |
| EP (1) | EP3911653A4 (https=) |
| JP (1) | JP2022518456A (https=) |
| KR (1) | KR20210121044A (https=) |
| CN (1) | CN113825756A (https=) |
| AU (1) | AU2020208371A1 (https=) |
| BR (1) | BR112021014079A2 (https=) |
| CA (1) | CA3126102A1 (https=) |
| EA (1) | EA202191967A1 (https=) |
| IL (1) | IL284845A (https=) |
| MX (1) | MX2021008646A (https=) |
| PH (1) | PH12021551718A1 (https=) |
| SG (1) | SG11202106965RA (https=) |
| TW (1) | TW202033523A (https=) |
| WO (1) | WO2020150366A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10952978B2 (en) | 2017-08-28 | 2021-03-23 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| US11702427B2 (en) | 2018-03-12 | 2023-07-18 | Arbutus Biopharma Corporation | Substituted 2-pyridone tricyclic compounds, analogues thereof, and methods using same |
| CN110862390B (zh) | 2018-08-28 | 2023-05-09 | 广东东阳光药业有限公司 | 稠合三环类化合物及其在药物中的应用 |
| UY38383A (es) | 2018-09-21 | 2020-04-30 | Enanta Pharm Inc | Heterociclos funcionalizados como agentes antivirales |
| CA3111046A1 (en) | 2018-09-30 | 2020-04-02 | Sunshine Lake Pharma Co., Ltd. | Fused tetracyclic compounds and uses thereof in medicine |
| US11198693B2 (en) | 2018-11-21 | 2021-12-14 | Enanta Pharmaceuticals, Inc. | Functionalized heterocycles as antiviral agents |
| US11738019B2 (en) | 2019-07-11 | 2023-08-29 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
| US11236108B2 (en) * | 2019-09-17 | 2022-02-01 | Enanta Pharmaceuticals, Inc. | Functionalized heterocycles as antiviral agents |
| WO2021188414A1 (en) | 2020-03-16 | 2021-09-23 | Enanta Pharmaceuticals, Inc. | Functionalized heterocyclic compounds as antiviral agents |
| TW202304914A (zh) * | 2021-04-05 | 2023-02-01 | 加拿大商愛彼特生物製藥公司 | 經取代之四環羧酸、其類似物及使用其之方法 |
| WO2024038357A1 (en) * | 2022-08-16 | 2024-02-22 | Arbutus Biopharma Corporation | Synthesis of substituted tetracyclic carboxylic acids and analogues thereof |
| CN115819200B (zh) * | 2022-11-28 | 2023-08-29 | 辽宁科技学院 | 一种苊醌的合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA111756C2 (uk) * | 2011-11-03 | 2016-06-10 | Ф. Хоффманн-Ля Рош Аг | Сполуки гетероарилпіридону та азапіридону як інгібітори тирозинкінази брутона |
| WO2014121416A1 (en) * | 2013-02-07 | 2014-08-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c |
| JP6506880B2 (ja) * | 2015-07-27 | 2019-04-24 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｂ型肝炎ウィルス感染症の治療および予防のための新規な四環式４−オキソ−ピリジン−３−カルボン酸誘導体 |
| US20200270265A1 (en) * | 2016-02-19 | 2020-08-27 | Novartis Ag | Tetracyclic pyridone compounds as antivirals |
| WO2018073753A1 (en) * | 2016-10-18 | 2018-04-26 | Novartis Ag | Fused tetracyclic pyridone compounds as antivirals |
| AR111419A1 (es) * | 2017-04-27 | 2019-07-10 | Novartis Ag | Compuestos fusionados de indazol piridona como antivirales |
| CN110066278B (zh) * | 2017-06-01 | 2021-06-08 | 广东东阳光药业有限公司 | 稠合三环类化合物及其在药物中的应用 |
| TWI815887B (zh) * | 2018-05-15 | 2023-09-21 | 美商愛彼特生物製藥股份有限公司 | 經取代的2,2'-雙嘧啶基化合物、其類似物及其使用方法 |
-
2020
- 2020-01-10 TW TW109100934A patent/TW202033523A/zh unknown
- 2020-01-15 JP JP2021541219A patent/JP2022518456A/ja active Pending
- 2020-01-15 BR BR112021014079-4A patent/BR112021014079A2/pt not_active IP Right Cessation
- 2020-01-15 MX MX2021008646A patent/MX2021008646A/es unknown
- 2020-01-15 EP EP20742028.2A patent/EP3911653A4/en not_active Withdrawn
- 2020-01-15 WO PCT/US2020/013701 patent/WO2020150366A1/en not_active Ceased
- 2020-01-15 US US17/423,151 patent/US20220125771A1/en not_active Abandoned
- 2020-01-15 EA EA202191967A patent/EA202191967A1/ru unknown
- 2020-01-15 CN CN202080016321.4A patent/CN113825756A/zh active Pending
- 2020-01-15 CA CA3126102A patent/CA3126102A1/en active Pending
- 2020-01-15 AU AU2020208371A patent/AU2020208371A1/en not_active Abandoned
- 2020-01-15 SG SG11202106965RA patent/SG11202106965RA/en unknown
- 2020-01-15 PH PH1/2021/551718A patent/PH12021551718A1/en unknown
- 2020-01-15 KR KR1020217023731A patent/KR20210121044A/ko not_active Ceased
-
2021
- 2021-07-14 IL IL284845A patent/IL284845A/en unknown
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