AU2017258187B2 - Isoquinolin-3-yl carboxamides and preparation and use thereof - Google Patents
Isoquinolin-3-yl carboxamides and preparation and use thereof Download PDFInfo
- Publication number
- AU2017258187B2 AU2017258187B2 AU2017258187A AU2017258187A AU2017258187B2 AU 2017258187 B2 AU2017258187 B2 AU 2017258187B2 AU 2017258187 A AU2017258187 A AU 2017258187A AU 2017258187 A AU2017258187 A AU 2017258187A AU 2017258187 B2 AU2017258187 B2 AU 2017258187B2
- Authority
- AU
- Australia
- Prior art keywords
- isoquinolin
- methyl
- carboxamide
- pyrazol
- piperidine
- 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.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/02—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing not further condensed quinolizine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662328210P | 2016-04-27 | 2016-04-27 | |
| US62/328,210 | 2016-04-27 | ||
| PCT/US2017/029797 WO2017189823A2 (en) | 2016-04-27 | 2017-04-27 | Isoquinolin-3-yl carboxamides and preparation and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2017258187A1 AU2017258187A1 (en) | 2018-11-15 |
| AU2017258187B2 true AU2017258187B2 (en) | 2021-08-26 |
Family
ID=60157342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2017258187A Ceased AU2017258187B2 (en) | 2016-04-27 | 2017-04-27 | Isoquinolin-3-yl carboxamides and preparation and use thereof |
Country Status (19)
| Country | Link |
|---|---|
| US (5) | US10508099B2 (enExample) |
| EP (2) | EP3943086A1 (enExample) |
| JP (1) | JP7023243B2 (enExample) |
| KR (1) | KR102399206B1 (enExample) |
| CN (1) | CN109311819B (enExample) |
| AR (1) | AR108326A1 (enExample) |
| AU (1) | AU2017258187B2 (enExample) |
| BR (1) | BR112018072190A2 (enExample) |
| CA (1) | CA3022044A1 (enExample) |
| CL (2) | CL2018003050A1 (enExample) |
| CO (1) | CO2018012655A2 (enExample) |
| IL (1) | IL262495B (enExample) |
| MA (1) | MA43605B1 (enExample) |
| MX (1) | MX386319B (enExample) |
| PE (1) | PE20190260A1 (enExample) |
| PH (1) | PH12018502259A1 (enExample) |
| RU (1) | RU2018141379A (enExample) |
| SG (2) | SG11201809310PA (enExample) |
| WO (1) | WO2017189823A2 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP3498701B1 (en) | 2012-12-21 | 2023-02-22 | Epizyme Inc | Prmt5 inhibitors and uses thereof |
| TW201803869A (zh) | 2016-04-27 | 2018-02-01 | 健生藥品公司 | 作為RORγT調節劑之6-胺基吡啶-3-基噻唑 |
| AR108325A1 (es) | 2016-04-27 | 2018-08-08 | Samumed Llc | Isoquinolin-3-il carboxamidas y preparación y uso de las mismas |
| AR108326A1 (es) | 2016-04-27 | 2018-08-08 | Samumed Llc | Isoquinolin-3-il carboxamidas y preparación y uso de las mismas |
| CN115028617A (zh) * | 2016-05-24 | 2022-09-09 | 基因泰克公司 | Cbp/ep300的杂环抑制剂及其在治疗癌症中的用途 |
| US20180282282A1 (en) | 2017-03-30 | 2018-10-04 | Genentech, Inc. | Isoquinolines as inhibitors of hpk1 |
| AU2018352828A1 (en) * | 2017-10-17 | 2020-04-23 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| US10604514B2 (en) | 2017-10-19 | 2020-03-31 | Samumed, Llc | 6-(5-membered heteroaryl)isoquinolin-3-yl carboxamides and preparation and use thereof |
| US10653688B2 (en) | 2017-10-27 | 2020-05-19 | Samumed, Llc | 6-(6-membered heteroaryl and aryl)isoquinolin-3-yl carboxamides and preparation and use thereof |
| US10413537B2 (en) | 2017-10-27 | 2019-09-17 | Samumed, Llc | 6-(5-membered heteroaryl)isoquinolin-3-yl-(5-membered heteroaryl) carboxamides and preparation and use thereof |
| WO2019089835A1 (en) * | 2017-10-31 | 2019-05-09 | Samumed, Llc | Diazanaphthalen-3-yl carboxamides and preparation and use thereof |
| ES2928246T3 (es) | 2018-06-18 | 2022-11-16 | Janssen Pharmaceutica Nv | 6-aminopiridin-3-il pirazoles como moduladores de RORyt |
| JP2021527660A (ja) | 2018-06-18 | 2021-10-14 | ヤンセン ファーマシューティカ エヌ.ベー. | RORγtのモジュレータとしてのフェニル及びピリジニル置換イミダゾール |
| ES2925473T3 (es) | 2018-06-18 | 2022-10-18 | Janssen Pharmaceutica Nv | Pirazoles de piridinilo como moduladores de RORyt |
| EP3790865A1 (en) | 2018-06-18 | 2021-03-17 | Janssen Pharmaceutica NV | Phenyl substituted pyrazoles as modulators of roryt |
| TW202019905A (zh) | 2018-07-24 | 2020-06-01 | 瑞士商赫孚孟拉羅股份公司 | 異喹啉化合物及其用途 |
| TW202024053A (zh) | 2018-10-02 | 2020-07-01 | 美商建南德克公司 | 異喹啉化合物及其用途 |
| US11612606B2 (en) | 2018-10-03 | 2023-03-28 | Genentech, Inc. | 8-aminoisoquinoline compounds and uses thereof |
| WO2021004547A1 (en) * | 2019-07-11 | 2021-01-14 | Guangdong Newopp Biopharmaceuticals Co., Ltd. | Heterocyclic compounds as inhibitors of hpk1 |
| JP7749540B2 (ja) * | 2019-09-05 | 2025-10-06 | 魯南製薬集団股▲分▼有限公司 | Magl阻害剤とその製造方法および使用 |
| US20230303552A1 (en) * | 2020-06-19 | 2023-09-28 | Vanderbilt University | Arylsulfonyl derivatives and their use as muscarinic acetylcholine receptor m5 inhibitors |
| KR20230097093A (ko) * | 2020-10-29 | 2023-06-30 | 머크 샤프 앤드 돔 엘엘씨 | Lrrk2 억제제로서의 n-연결된 이소퀴놀린 아미드, 제약 조성물 및 그의 용도 |
| WO2022175675A1 (en) * | 2021-02-19 | 2022-08-25 | Kalvista Pharmaceuticals Limited | Factor xiia inhibitors |
| WO2023055679A1 (en) * | 2021-10-01 | 2023-04-06 | Merck Sharp & Dohme Llc | C-linked isoquinoline amides as lrrk2 inhibitors, pharmaceutical compositions, and uses thereof |
| KR20240133695A (ko) * | 2021-12-10 | 2024-09-04 | 프로테나 바이오사이언시즈 리미티드 | Dyrk1a 억제제로서의 헤테로시클릭 화합물 |
| TW202506660A (zh) * | 2023-04-27 | 2025-02-16 | 美商塞普特納公司 | Mrgprx2拮抗劑及其使用方法 |
| KR20240162928A (ko) | 2023-05-09 | 2024-11-18 | 주식회사 베노바이오 | Bet 단백질을 저해하는 신규한 벤조사이오펜 유도체 및 이를 이용한 암 치료용 조성물 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007125405A2 (en) * | 2006-05-01 | 2007-11-08 | Pfizer Products Inc. | Substituted 2-amino-fused heterocyclic compounds |
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| US4474752A (en) | 1983-05-16 | 1984-10-02 | Merck & Co., Inc. | Drug delivery system utilizing thermosetting gels |
| US4783443A (en) | 1986-03-03 | 1988-11-08 | The University Of Chicago | Amino acyl cephalosporin derivatives |
| ES2131463B1 (es) * | 1997-04-08 | 2000-03-01 | Lilly Sa | Derivados de ciclopropilglicina con propiedades farmaceuticas. |
| DE19746287A1 (de) | 1997-10-20 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| US6440102B1 (en) | 1998-07-23 | 2002-08-27 | Durect Corporation | Fluid transfer and diagnostic system for treating the inner ear |
| DE19853299C2 (de) | 1998-11-19 | 2003-04-03 | Thomas Lenarz | Katheter zur Applikation von Medikamenten in Flüssigkeitsräumen des menschlichen Innenohrs |
| US6120484A (en) | 1999-02-17 | 2000-09-19 | Silverstein; Herbert | Otological implant for delivery of medicament and method of using same |
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| US6648873B2 (en) | 2001-09-21 | 2003-11-18 | Durect Corp. | Aural catheter system including anchor balloon and balloon inflation device |
| GB0310867D0 (en) | 2003-05-12 | 2003-06-18 | Novartis Ag | Organic compounds |
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| EP1861161A4 (en) | 2005-01-24 | 2012-05-16 | Neurosystec Corp | APPARATUS AND METHOD FOR DISPENSING THERAPEUTIC AND / OR OTHER AGENTS IN THE INTERNAL EAR AND OTHER FABRICS |
| EP2195328A4 (en) | 2007-08-15 | 2011-06-15 | Cytokinetics Inc | PARTICULAR CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS |
| WO2011019651A1 (en) * | 2009-08-10 | 2011-02-17 | Epitherix, Llc | Indazole inhibitors of the wnt signal pathway and therapeutic uses thereof |
| BR112012002942A2 (pt) | 2009-08-10 | 2015-10-13 | Epitherix Llc | indazóis como inibidores da trilha de sinalização de wnt/b-catenina e empregos terapêuticos destes. |
| MX2012010666A (es) * | 2010-03-31 | 2012-10-05 | Actelion Pharmaceuticals Ltd | Derivados de isoquinolin-3-ilurea antibacterianos. |
| PH12013501489A1 (en) | 2010-12-17 | 2013-08-28 | Hoffmann La Roche | Substituted 6,6-fused nitrogenous heterocyclic compounds and uses thereof |
| EP3473099A1 (en) | 2011-09-14 | 2019-04-24 | Samumed, LLC | Indazole-3-carboxamides and their use as wnt/b-catenin signaling pathway inhibitors |
| WO2013169793A2 (en) * | 2012-05-09 | 2013-11-14 | Ipierian, Inc. | Methods and compositions for tdp-43 proteinopathies |
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| CA2942687A1 (en) | 2014-03-20 | 2015-09-24 | Samumed, Llc | 5-substituted indazole-3-carboxamides and preparation and use thereof |
| GB201416754D0 (en) | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
| AR108326A1 (es) | 2016-04-27 | 2018-08-08 | Samumed Llc | Isoquinolin-3-il carboxamidas y preparación y uso de las mismas |
| AR108325A1 (es) | 2016-04-27 | 2018-08-08 | Samumed Llc | Isoquinolin-3-il carboxamidas y preparación y uso de las mismas |
| US20220062240A1 (en) | 2018-06-26 | 2022-03-03 | Biosplice Therapeutics, Inc. | Methods of treating cancer using a clk inhibitor |
-
2017
- 2017-04-26 AR ARP170101056A patent/AR108326A1/es unknown
- 2017-04-27 SG SG11201809310PA patent/SG11201809310PA/en unknown
- 2017-04-27 EP EP21181038.7A patent/EP3943086A1/en not_active Withdrawn
- 2017-04-27 PE PE2018002175A patent/PE20190260A1/es unknown
- 2017-04-27 RU RU2018141379A patent/RU2018141379A/ru unknown
- 2017-04-27 CA CA3022044A patent/CA3022044A1/en active Pending
- 2017-04-27 WO PCT/US2017/029797 patent/WO2017189823A2/en not_active Ceased
- 2017-04-27 JP JP2018556921A patent/JP7023243B2/ja active Active
- 2017-04-27 CN CN201780037470.7A patent/CN109311819B/zh active Active
- 2017-04-27 US US15/498,990 patent/US10508099B2/en active Active
- 2017-04-27 MX MX2018013173A patent/MX386319B/es unknown
- 2017-04-27 MA MA43605A patent/MA43605B1/fr unknown
- 2017-04-27 AU AU2017258187A patent/AU2017258187B2/en not_active Ceased
- 2017-04-27 BR BR112018072190-5A patent/BR112018072190A2/pt not_active IP Right Cessation
- 2017-04-27 EP EP17790411.7A patent/EP3448838B1/en active Active
- 2017-04-27 KR KR1020187034080A patent/KR102399206B1/ko active Active
- 2017-04-27 SG SG10201914127PA patent/SG10201914127PA/en unknown
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2018
- 2018-03-19 US US15/925,157 patent/US10287267B2/en active Active
- 2018-04-03 US US15/943,864 patent/US10556885B2/en active Active
- 2018-10-21 IL IL262495A patent/IL262495B/en unknown
- 2018-10-23 PH PH12018502259A patent/PH12018502259A1/en unknown
- 2018-10-26 CL CL2018003050A patent/CL2018003050A1/es unknown
- 2018-11-23 CO CONC2018/0012655A patent/CO2018012655A2/es unknown
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2019
- 2019-07-24 CL CL2019002067A patent/CL2019002067A1/es unknown
- 2019-12-26 US US16/727,053 patent/US11174244B2/en active Active
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2021
- 2021-10-06 US US17/495,281 patent/US11673881B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007125405A2 (en) * | 2006-05-01 | 2007-11-08 | Pfizer Products Inc. | Substituted 2-amino-fused heterocyclic compounds |
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| HK40005208B (en) | Isoquinolin-3-yl carboxamides and preparation and use thereof |
Legal Events
| Date | Code | Title | Description |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |