JP2018505192A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018505192A5 JP2018505192A5 JP2017541901A JP2017541901A JP2018505192A5 JP 2018505192 A5 JP2018505192 A5 JP 2018505192A5 JP 2017541901 A JP2017541901 A JP 2017541901A JP 2017541901 A JP2017541901 A JP 2017541901A JP 2018505192 A5 JP2018505192 A5 JP 2018505192A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- pharmaceutically acceptable
- solvate
- addition salt
- rpl554
- 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
Links
- 239000002253 acid Substances 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 239000012453 solvate Substances 0.000 claims 14
- CSOBIBXVIYAXFM-BYNJWEBRSA-N ensifentrine Chemical compound c-12cc(OC)c(OC)cc2CCn(c(n2CCNC(N)=O)=O)c-1c\c2=N/c1c(C)cc(C)cc1C CSOBIBXVIYAXFM-BYNJWEBRSA-N 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 6
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 5
- 239000007864 aqueous solution Substances 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 3
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- CSOBIBXVIYAXFM-UHFFFAOYSA-N rpl-554 Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C(N2CCNC(N)=O)=O)C1=CC2=NC1=C(C)C=C(C)C=C1C CSOBIBXVIYAXFM-UHFFFAOYSA-N 0.000 claims 2
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 206010015943 Eye inflammation Diseases 0.000 claims 1
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 201000009961 allergic asthma Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 230000005784 autoimmunity Effects 0.000 claims 1
- 201000009267 bronchiectasis Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 239000000872 buffer Substances 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 208000029771 childhood onset asthma Diseases 0.000 claims 1
- 239000007979 citrate buffer Substances 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 239000008363 phosphate buffer Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB201502260A GB201502260D0 (en) | 2015-02-11 | 2015-02-11 | Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound |
| GB1502260.1 | 2015-02-11 | ||
| PCT/GB2016/050313 WO2016128742A1 (en) | 2015-02-11 | 2016-02-10 | Salt of a pyrimido[6,1-a]isoquinolin-4-one compound |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020186284A Division JP7110303B2 (ja) | 2015-02-11 | 2020-11-09 | ピリミド［６，１－ａ］イソキノリン－４－オン化合物の塩 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018505192A JP2018505192A (ja) | 2018-02-22 |
| JP2018505192A5 true JP2018505192A5 (enExample) | 2019-02-28 |
| JP7089366B2 JP7089366B2 (ja) | 2022-06-22 |
Family
ID=52781414
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017541901A Active JP7089366B2 (ja) | 2015-02-11 | 2016-02-10 | ピリミド［６，１－ａ］イソキノリン－４－オン化合物の塩 |
| JP2020186284A Active JP7110303B2 (ja) | 2015-02-11 | 2020-11-09 | ピリミド［６，１－ａ］イソキノリン－４－オン化合物の塩 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020186284A Active JP7110303B2 (ja) | 2015-02-11 | 2020-11-09 | ピリミド［６，１－ａ］イソキノリン－４－オン化合物の塩 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US10463665B2 (enExample) |
| EP (2) | EP4461358A3 (enExample) |
| JP (2) | JP7089366B2 (enExample) |
| CN (2) | CN113105453A (enExample) |
| AU (2) | AU2016217674B2 (enExample) |
| CA (1) | CA2974605C (enExample) |
| ES (1) | ES3018557T3 (enExample) |
| GB (1) | GB201502260D0 (enExample) |
| IL (1) | IL253595B (enExample) |
| MX (1) | MX382019B (enExample) |
| PT (1) | PT3256472T (enExample) |
| WO (1) | WO2016128742A1 (enExample) |
| ZA (1) | ZA201705112B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3231444T3 (pl) | 2014-05-12 | 2020-05-18 | Verona Pharma Plc | Nowe leczenie |
| PT3332767T (pt) | 2014-09-15 | 2019-06-27 | Verona Pharma Plc | Formulação por inalação líquida compreendendo rpl554 |
| GB201502260D0 (en) | 2015-02-11 | 2015-04-01 | Verona Pharma Plc | Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound |
| GB201613054D0 (en) | 2016-07-28 | 2016-09-14 | Verona Pharma Plc | New compound and process |
| GB2578093B (en) * | 2018-10-09 | 2020-11-18 | Verona Pharma Plc | Liquid pharmaceutical composition comprising RPL554 and HFA-134A |
| GB201911517D0 (en) * | 2019-08-12 | 2019-09-25 | Verona Pharma Plc | Pharmaceutical composition |
| CA3167378A1 (en) * | 2020-01-15 | 2021-07-22 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd | Pharmaceutical composition of tricyclic pde3/pde4 dual inhibitor compound |
| WO2021213945A1 (en) * | 2020-04-22 | 2021-10-28 | Pfizer Inc. | Coronavirus vaccine |
| WO2023076205A1 (en) | 2021-10-29 | 2023-05-04 | Teva Pharmaceuticals International Gmbh | Solid state forms of ensifentrine and process for preparation thereof |
| WO2023109802A1 (zh) * | 2021-12-14 | 2023-06-22 | 海思科医药集团股份有限公司 | 三环稠杂环类pde3/4双重抑制及其用途 |
| GB202202297D0 (en) | 2022-02-21 | 2022-04-06 | Verona Pharma Plc | Formulation production process |
| EP4568677A1 (en) * | 2022-08-08 | 2025-06-18 | Verona Pharma PLC | Ensifentrine (rpl-554) for increasing trough lung function |
| EP4609864A4 (en) * | 2022-10-28 | 2026-02-18 | Jiangsu Hengrui Pharmaceuticals Co Ltd | PHARMACEUTICAL COMPOSITION CONTAINING AN ISOQUINOLINONE COMPOUND AND RELATED PREPARATION PROCESS |
| EP4378942A1 (en) | 2022-12-02 | 2024-06-05 | Sandoz AG | Crystal form of a pde3/4 inhibitor |
| CN121620356A (zh) | 2023-06-26 | 2026-03-06 | 维罗纳制药公司 | 包含恩塞芬汀的颗粒组合物 |
| WO2025176871A1 (en) | 2024-02-23 | 2025-08-28 | Inke, S.A. | Process for preparing pyrimido[6,1-a]isoquinoline-4-ones |
| WO2025223528A1 (zh) * | 2024-04-27 | 2025-10-30 | 苏州君健一方生物医药有限公司 | 嘧啶并[6,1-a]异喹啉-4-酮衍生物 |
| WO2026003867A1 (en) * | 2024-06-24 | 2026-01-02 | Neuland Laboratories Limited | An improved process for the preparation of ensifentrine and its purification thereof |
| CN121226374A (zh) * | 2025-12-03 | 2025-12-30 | 长风药业股份有限公司 | 一种恩塞芬汀盐型化合物及其成盐方法和应用 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZW6284A1 (en) | 1983-05-05 | 1985-10-30 | Hoffmann La Roche | Novel pyrimidone derivatives |
| DE3816995A1 (de) | 1988-05-19 | 1989-11-23 | Hoechst Ag | Verwendung von pyrimido-(6,1-a)-isochinolin-4-on-derivaten und medizinische zubereitungen auf basis dieser verbindungen |
| CA2368413C (en) | 1999-03-31 | 2008-07-29 | Verona Pharma Plc | Derivatives of pyrimido[6,1-a]isoquinolin-4-one |
| US20030235631A1 (en) * | 2002-06-17 | 2003-12-25 | Pfizer Inc. | Combination treatment for depression and anxiety |
| JP5009799B2 (ja) * | 2004-09-08 | 2012-08-22 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規の３−オキサ−１０−アザ−フェナントレン |
| AU2008316284A1 (en) | 2007-10-25 | 2009-04-30 | Merck Frosst Canada Ltd. | Novel crystalline salts of montelukast |
| CA2796280A1 (en) | 2010-04-15 | 2011-10-20 | The Royal Institution For The Advancement Of Learning / Mcgill Universit Y | Topical treatments for pain |
| PT2603509E (pt) | 2010-08-09 | 2014-08-29 | Verona Pharma Plc | Forma cristalina de um composto pirimidio[6,1-a]isoquinolin-4-ona |
| EP2647627A1 (en) * | 2012-04-02 | 2013-10-09 | Almirall, S.A. | Salts of 5-[(1r)-2-({2-[4-(2,2-difluoro-2-phenylethoxy)phenyl] ethyl}amino)-1-hydroxyethyl]-8-hydroxyquinolin-2(1h)-one. |
| TWI643853B (zh) | 2013-02-27 | 2018-12-11 | 阿爾米雷爾有限公司 | 同時具有β2腎上腺素受體促效劑和M3毒蕈鹼受體拮抗劑活性之2-氨基-1-羥乙基-8-羥基喹啉-2(1H)-酮衍生物之鹽類 |
| SI2968313T1 (en) | 2013-03-15 | 2018-05-31 | Verona Pharma Plc | Combination of medicines |
| PL3231444T3 (pl) | 2014-05-12 | 2020-05-18 | Verona Pharma Plc | Nowe leczenie |
| PT3332767T (pt) | 2014-09-15 | 2019-06-27 | Verona Pharma Plc | Formulação por inalação líquida compreendendo rpl554 |
| GB201502260D0 (en) | 2015-02-11 | 2015-04-01 | Verona Pharma Plc | Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound |
| GB201613054D0 (en) | 2016-07-28 | 2016-09-14 | Verona Pharma Plc | New compound and process |
| GB2578093B (en) | 2018-10-09 | 2020-11-18 | Verona Pharma Plc | Liquid pharmaceutical composition comprising RPL554 and HFA-134A |
| WO2023076205A1 (en) | 2021-10-29 | 2023-05-04 | Teva Pharmaceuticals International Gmbh | Solid state forms of ensifentrine and process for preparation thereof |
-
2015
- 2015-02-11 GB GB201502260A patent/GB201502260D0/en not_active Ceased
-
2016
- 2016-02-10 ES ES16704896T patent/ES3018557T3/es active Active
- 2016-02-10 WO PCT/GB2016/050313 patent/WO2016128742A1/en not_active Ceased
- 2016-02-10 CN CN202110415666.3A patent/CN113105453A/zh active Pending
- 2016-02-10 CN CN201680009645.9A patent/CN107406446B/zh active Active
- 2016-02-10 US US15/549,500 patent/US10463665B2/en active Active
- 2016-02-10 CA CA2974605A patent/CA2974605C/en active Active
- 2016-02-10 EP EP24189714.9A patent/EP4461358A3/en active Pending
- 2016-02-10 EP EP16704896.6A patent/EP3256472B1/en active Active
- 2016-02-10 JP JP2017541901A patent/JP7089366B2/ja active Active
- 2016-02-10 PT PT167048966T patent/PT3256472T/pt unknown
- 2016-02-10 MX MX2017010195A patent/MX382019B/es unknown
- 2016-02-10 AU AU2016217674A patent/AU2016217674B2/en active Active
-
2017
- 2017-07-20 IL IL253595A patent/IL253595B/en active IP Right Grant
- 2017-07-27 ZA ZA2017/05112A patent/ZA201705112B/en unknown
-
2019
- 2019-09-24 US US16/580,515 patent/US11491155B2/en active Active
-
2020
- 2020-07-15 AU AU2020205281A patent/AU2020205281B2/en active Active
- 2020-11-09 JP JP2020186284A patent/JP7110303B2/ja active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017528479A5 (enExample) | ||
| PH12019501098A1 (en) | Pyrrolopyrimidines as cftr potentiators | |
| JP2016510804A5 (enExample) | ||
| JP2022017283A (ja) | エアロゾルのピルフェニドン及びピリドンのアナログの化合物、及び、その使用 | |
| JP2022078126A (ja) | エアロゾルのピルフェニドン及びピリドンのアナログの化合物、及び、その使用 | |
| JP7607335B2 (ja) | 特別に製剤化された吸入ニンテダニブおよびニンテダニブ塩の組成物 | |
| HRP20200429T1 (hr) | 3,5-diamino-6-kloro-n-(n-(4-(4-(2-(heksil(2,3,4,5,6-penta-hidroksiheksil)amino)etoksi)fenil)butil)karbamimidoil)pirazin-2-karboksamid | |
| HRP20191122T1 (hr) | Tekući inhalacijski pripravak koji sadrži rpl554 | |
| CN102946868B (zh) | 包含抗毒蕈碱药的干粉制剂 | |
| RU2015144083A (ru) | Комбинация лекарственных средств | |
| HRP20160285T1 (hr) | Predlijek adrenomedulina na bazi polietilen glikola i njegova uporaba | |
| HRP20171044T1 (hr) | Kemijski i metabolički stabilni dipeptid s potentnom aktivnošću blokatora natrijevog kanala | |
| AU2016284531B2 (en) | Therapeutic agent for fibrosis | |
| JP2013530179A (ja) | 呼吸器合胞体ウイルス（ｒｓｖ）感染の処置に使用するためのウレイド−ピラゾール誘導体 | |
| JP2022513566A5 (enExample) | ||
| JP2022550664A5 (enExample) | ||
| JP2023516630A5 (enExample) | ||
| RU2019121673A (ru) | Активаторы nrf2 | |
| CA3051539A1 (en) | Hydrocarbylsulfonyl-substituted pyridines and their use in the treatment of cancer | |
| CN108601793A (zh) | 使用5′-腺苷二磷酸核糖(adpr)的方法 | |
| JP2015524391A (ja) | ニューモウイルス感染症および感染疾患を治療あるいは予防するための組成物および方法 | |
| JP2013516475A5 (enExample) | ||
| JP2008501722A5 (enExample) | ||
| CN116419754A (zh) | 用于治疗和预防肺部感染的葡萄糖苷酶抑制剂 | |
| JP2008502699A5 (enExample) |