JP2018505192A5 - - Google Patents
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- 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 |
|---|---|---|---|
| GB1502260.1 | 2015-02-11 | ||
| GB201502260A GB201502260D0 (en) | 2015-02-11 | 2015-02-11 | Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound |
| 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) | EP3256472B1 (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 |
|---|---|---|---|---|
| SI3142701T1 (en) | 2014-05-12 | 2018-08-31 | Verona Pharma Plc | NEW TREATMENT |
| HUE055527T2 (hu) | 2014-09-15 | 2021-12-28 | Verona Pharma Plc | RPL554-t tartalmazó folyékony inhalációs készítmény |
| 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 |
| EP4092025B9 (en) * | 2020-01-15 | 2024-11-06 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Pharmaceutical composition of tricyclic pde3/pde4 dual inhibitor compound |
| KR20230015351A (ko) * | 2020-04-22 | 2023-01-31 | 화이자 인코포레이티드 | 코로나바이러스 백신 |
| EP4423085A1 (en) | 2021-10-29 | 2024-09-04 | Teva Pharmaceuticals International GmbH | Solid state forms of ensifentrine and process for preparation thereof |
| EP4450500A4 (en) * | 2021-12-14 | 2025-10-15 | Xizang Haisco Pharmaceutical Co Ltd | TRICYCLIC FUSED HETEROCYCLIC PDE3/4 DUAL INHIBITOR AND ITS USE |
| GB202202297D0 (en) | 2022-02-21 | 2022-04-06 | Verona Pharma Plc | Formulation production process |
| CN119816309A (zh) * | 2022-08-08 | 2025-04-11 | 维罗纳制药公司 | 用于治疗中度慢性阻塞性肺病(copd)的恩塞芬汀(rpl-554) |
| 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 |
| TW202506117A (zh) | 2023-06-26 | 2025-02-16 | 英商維羅納製藥Ｐｌｃ公司 | 顆粒組成物 |
| 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 |
|---|---|---|---|---|
| CA1237429A (en) | 1983-05-05 | 1988-05-31 | Frank Kienzle | 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 |
| CN100415743C (zh) * | 1999-03-31 | 2008-09-03 | 韦尔纳利斯有限公司 | 嘧啶并[6,1-a] 异喹啉-4-酮衍生物 |
| 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 |
| CA2701723A1 (en) | 2007-10-25 | 2009-04-30 | Merck Frosst Canada Ltd. | Novel crystalline salts of montelukast |
| WO2011127586A1 (en) | 2010-04-15 | 2011-10-20 | The Royal Institution For The Advancement Of Learning / Mcgill University | Topical treatments for pain |
| AR082601A1 (es) * | 2010-08-09 | 2012-12-19 | Verona Pharma Plc | Formas cristalinas de compuestos de pirimido[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 |
| US9700558B2 (en) | 2013-03-15 | 2017-07-11 | Verona Pharma Plc | Drug combination of PDE3/PDE4 inhibitor and muscarinic receptor antagonist |
| SI3142701T1 (en) | 2014-05-12 | 2018-08-31 | Verona Pharma Plc | NEW TREATMENT |
| HUE055527T2 (hu) | 2014-09-15 | 2021-12-28 | Verona Pharma Plc | RPL554-t tartalmazó folyékony inhalációs készítmény |
| 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 |
| EP4423085A1 (en) | 2021-10-29 | 2024-09-04 | 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 US US15/549,500 patent/US10463665B2/en active Active
- 2016-02-10 MX MX2017010195A patent/MX382019B/es unknown
- 2016-02-10 JP JP2017541901A patent/JP7089366B2/ja active Active
- 2016-02-10 CN CN202110415666.3A patent/CN113105453A/zh active Pending
- 2016-02-10 CA CA2974605A patent/CA2974605C/en active Active
- 2016-02-10 EP EP16704896.6A patent/EP3256472B1/en active Active
- 2016-02-10 AU AU2016217674A patent/AU2016217674B2/en active Active
- 2016-02-10 PT PT167048966T patent/PT3256472T/pt unknown
- 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 EP EP24189714.9A patent/EP4461358A3/en active Pending
- 2016-02-10 CN CN201680009645.9A patent/CN107406446B/zh 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
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