JPWO2020205934A5 - - Google Patents
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- JPWO2020205934A5 JPWO2020205934A5 JP2021559054A JP2021559054A JPWO2020205934A5 JP WO2020205934 A5 JPWO2020205934 A5 JP WO2020205934A5 JP 2021559054 A JP2021559054 A JP 2021559054A JP 2021559054 A JP2021559054 A JP 2021559054A JP WO2020205934 A5 JPWO2020205934 A5 JP WO2020205934A5
- Authority
- JP
- Japan
- Prior art keywords
- unsubstituted
- substituted
- alkyl
- monocyclic
- cycloalkyl
- 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 122
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 125000002950 monocyclic group Chemical class 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000010452 phosphate Substances 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 208000005331 Hepatitis D Diseases 0.000 claims description 5
- 208000002672 hepatitis B Diseases 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 108010078049 Interferon alpha-2 Proteins 0.000 claims description 4
- 108010047761 Interferon-alpha Proteins 0.000 claims description 4
- 102000006992 Interferon-alpha Human genes 0.000 claims description 4
- 108010050904 Interferons Proteins 0.000 claims description 4
- 102000014150 Interferons Human genes 0.000 claims description 4
- 108091034117 Oligonucleotide Proteins 0.000 claims description 4
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 4
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 claims description 4
- 229960003205 adefovir dipivoxil Drugs 0.000 claims description 4
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 claims description 4
- 229960005338 clevudine Drugs 0.000 claims description 4
- GBBJCSTXCAQSSJ-XQXXSGGOSA-N clevudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H](F)[C@@H](O)[C@H](CO)O1 GBBJCSTXCAQSSJ-XQXXSGGOSA-N 0.000 claims description 4
- 229960000980 entecavir Drugs 0.000 claims description 4
- YXPVEXCTPGULBZ-WQYNNSOESA-N entecavir hydrate Chemical compound O.C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)C1=C YXPVEXCTPGULBZ-WQYNNSOESA-N 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 229940047124 interferons Drugs 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
- OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 claims description 4
- 108020004707 nucleic acids Proteins 0.000 claims description 4
- 150000007523 nucleic acids Chemical class 0.000 claims description 4
- 102000039446 nucleic acids Human genes 0.000 claims description 4
- 125000003729 nucleotide group Chemical group 0.000 claims description 4
- 108010092853 peginterferon alfa-2a Proteins 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 150000003384 small molecules Chemical class 0.000 claims description 4
- 229960005311 telbivudine Drugs 0.000 claims description 4
- IQFYYKKMVGJFEH-CSMHCCOUSA-N telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 claims description 4
- LDEKQSIMHVQZJK-CAQYMETFSA-N tenofovir alafenamide Chemical compound O([P@@](=O)(CO[C@H](C)CN1C2=NC=NC(N)=C2N=C1)N[C@@H](C)C(=O)OC(C)C)C1=CC=CC=C1 LDEKQSIMHVQZJK-CAQYMETFSA-N 0.000 claims description 4
- 229960004946 tenofovir alafenamide Drugs 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 150000002921 oxetanes Chemical class 0.000 claims description 3
- 230000002519 immonomodulatory effect Effects 0.000 claims description 2
- 229960001355 tenofovir disoproxil Drugs 0.000 claims description 2
- JFVZFKDSXNQEJW-CQSZACIVSA-N tenofovir disoproxil Chemical compound N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N JFVZFKDSXNQEJW-CQSZACIVSA-N 0.000 claims description 2
- 150000003552 thietanes Chemical class 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 2
- 235000001014 amino acid Nutrition 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229940127073 nucleoside analogue Drugs 0.000 claims 1
- 239000000126 substance Substances 0.000 description 24
- 239000003814 drug Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002777 nucleoside Substances 0.000 description 3
- 150000003833 nucleoside derivatives Chemical class 0.000 description 3
- 229940079593 drug Drugs 0.000 description 2
- 239000002955 immunomodulating agent Substances 0.000 description 2
- 229940121354 immunomodulator Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229960004556 tenofovir Drugs 0.000 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 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024101773A JP7710215B2 (ja) | 2019-04-03 | 2024-06-25 | ピロール化合物 |
| JP2025110439A JP7811768B2 (ja) | 2019-04-03 | 2025-06-30 | ピロール化合物 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962828919P | 2019-04-03 | 2019-04-03 | |
| US62/828,919 | 2019-04-03 | ||
| US201962932686P | 2019-11-08 | 2019-11-08 | |
| US62/932,686 | 2019-11-08 | ||
| PCT/US2020/026116 WO2020205934A1 (en) | 2019-04-03 | 2020-04-01 | Pyrrole compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024101773A Division JP7710215B2 (ja) | 2019-04-03 | 2024-06-25 | ピロール化合物 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2022522312A JP2022522312A (ja) | 2022-04-15 |
| JPWO2020205934A5 true JPWO2020205934A5 (https=) | 2023-04-11 |
| JP2022522312A5 JP2022522312A5 (https=) | 2023-04-11 |
| JP7627008B2 JP7627008B2 (ja) | 2025-02-05 |
Family
ID=72667046
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021559054A Active JP7627008B2 (ja) | 2019-04-03 | 2020-04-01 | ピロール化合物 |
| JP2024101773A Active JP7710215B2 (ja) | 2019-04-03 | 2024-06-25 | ピロール化合物 |
| JP2025110439A Active JP7811768B2 (ja) | 2019-04-03 | 2025-06-30 | ピロール化合物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024101773A Active JP7710215B2 (ja) | 2019-04-03 | 2024-06-25 | ピロール化合物 |
| JP2025110439A Active JP7811768B2 (ja) | 2019-04-03 | 2025-06-30 | ピロール化合物 |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US11191747B2 (https=) |
| EP (2) | EP4733305A2 (https=) |
| JP (3) | JP7627008B2 (https=) |
| KR (2) | KR20260036605A (https=) |
| CN (4) | CN121108187A (https=) |
| AU (2) | AU2020253444C1 (https=) |
| BR (1) | BR112021019817A2 (https=) |
| CA (1) | CA3134635A1 (https=) |
| CL (1) | CL2021002575A1 (https=) |
| CO (1) | CO2021014210A2 (https=) |
| DK (1) | DK3947349T3 (https=) |
| FI (1) | FI3947349T3 (https=) |
| GE (2) | GEP20257772B (https=) |
| IL (1) | IL286902B2 (https=) |
| MA (1) | MA55564A (https=) |
| MX (1) | MX2021012105A (https=) |
| PE (1) | PE20220252A1 (https=) |
| PH (1) | PH12021552513A1 (https=) |
| SG (1) | SG11202110718PA (https=) |
| TW (1) | TWI846853B (https=) |
| UA (1) | UA129029C2 (https=) |
| WO (1) | WO2020205934A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN121108187A (zh) | 2019-04-03 | 2025-12-12 | 阿里戈斯治疗公司 | 吡咯化合物 |
| CN114685514A (zh) * | 2020-12-29 | 2022-07-01 | 广东东阳光药业有限公司 | 新型酰胺吡咯类化合物及其在药物中的应用 |
| WO2022156758A1 (zh) * | 2021-01-22 | 2022-07-28 | 广东东阳光药业有限公司 | 新型酰胺吡咯类化合物及其在药物中的用途 |
| CA3231695A1 (en) | 2021-09-08 | 2023-03-16 | Aligos Therapeutics, Inc. | Modified short interfering nucleic acid (sina) molecules and uses thereof |
| CN118974014B (zh) * | 2022-03-17 | 2026-01-27 | 成都微芯药业有限公司 | 吡咯酰胺类化合物及其制备方法和用途 |
| CN116120219A (zh) * | 2022-12-27 | 2023-05-16 | 吉斯凯(苏州)制药有限公司 | 一种多取代吡咯类化合物及其制备方法和在制备hbv衣壳蛋白抑制剂中的应用 |
| JP2026503674A (ja) * | 2023-01-26 | 2026-01-29 | アリゴス セラピューティクス インコーポレイテッド | Ｂ型肝炎併用療法 |
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| EP1389209B1 (en) | 2001-04-24 | 2009-04-08 | Purdue Research Foundation | Folate mimetics and folate-receptor binding conjugates thereof |
| US6956040B2 (en) | 2001-07-16 | 2005-10-18 | Ranbaxy Laboratories Limited | Oxazolidinone piperazinyl derivatives as potential antimicrobials |
| GB0119172D0 (en) | 2001-08-06 | 2001-09-26 | Melacure Therapeutics Ab | Phenyl pyrrole derivatives |
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| US7202257B2 (en) | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| GB2398299A (en) | 2003-02-13 | 2004-08-18 | Melacure Therapeutics Ab | Pharmaceutically active phenyl-pyrrole derivatives |
| US20070191336A1 (en) | 2003-12-24 | 2007-08-16 | Flynn Daniel L | Anti-inflammatory medicaments |
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| KR101726059B1 (ko) | 2015-07-28 | 2017-04-12 | 한양대학교 산학협력단 | 디피롤 유도체와 암모늄 염을 포함하는 브롬화수소 가스 검출용 조성물 및 이를 포함하는 브롬화수소 가스 검출용 색변환 센서 |
| KR101726060B1 (ko) | 2015-07-28 | 2017-04-12 | 한양대학교 산학협력단 | 디피롤 유도체와 금속 염을 포함하는 염화수소 가스 검출용 조성물 및 이를 포함하는 염화수소 가스 검출용 색변환 센서 |
| WO2017081615A1 (en) | 2015-11-09 | 2017-05-18 | Wockhardt Limited | 7-oxo -6-(sulfooxy)- 1,6-diazabicyclo [3.2.1] octane containing compounds and their use in treatment of bacterial infections |
| US10752584B2 (en) * | 2016-03-09 | 2020-08-25 | Emory University | Elimination of hepatitis B virus with antiviral agents |
| JOP20190024A1 (ar) * | 2016-08-26 | 2019-02-19 | Gilead Sciences Inc | مركبات بيروليزين بها استبدال واستخداماتها |
| CN108250121A (zh) | 2016-12-28 | 2018-07-06 | 上海长森药业有限公司 | 磺酰胺-芳基酰胺类化合物及其治疗乙型肝炎的药物用途 |
| CN115974753A (zh) | 2018-03-30 | 2023-04-18 | 正大天晴药业集团股份有限公司 | 含有n杂五元环化合物和用途 |
| BR112021006403A2 (pt) | 2018-10-05 | 2021-07-06 | Univ Emory | agentes monômeros e multiméricos anti-hbv |
| MX2021010145A (es) | 2019-02-22 | 2021-09-14 | Janssen Sciences Ireland Unlimited Co | Derivados de amida utiles en el tratamiento de una infeccion por vhb o de enfermedades inducidas por vhb. |
| CN121108187A (zh) | 2019-04-03 | 2025-12-12 | 阿里戈斯治疗公司 | 吡咯化合物 |
| AU2020385034B2 (en) | 2019-11-13 | 2024-11-14 | Xi'an Xintong Pharmaceutical Research Co., Ltd. | HBV inhibitor and use thereof |
| CN114685514A (zh) | 2020-12-29 | 2022-07-01 | 广东东阳光药业有限公司 | 新型酰胺吡咯类化合物及其在药物中的应用 |
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