JP2019527228A5 - - Google Patents
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- Publication number
- JP2019527228A5 JP2019527228A5 JP2019503748A JP2019503748A JP2019527228A5 JP 2019527228 A5 JP2019527228 A5 JP 2019527228A5 JP 2019503748 A JP2019503748 A JP 2019503748A JP 2019503748 A JP2019503748 A JP 2019503748A JP 2019527228 A5 JP2019527228 A5 JP 2019527228A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- hydrogen
- alkyl group
- base
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- -1 nitrile compound Chemical class 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 31
- 238000000034 method Methods 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical group [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 2
- 229910052808 lithium carbonate Inorganic materials 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000001632 sodium acetate Substances 0.000 claims 2
- 235000017281 sodium acetate Nutrition 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 1
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 claims 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 235000011056 potassium acetate Nutrition 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002823 nitrates Chemical group 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical group 0.000 description 1
- 150000003014 phosphoric acid esters Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1613054.4A GB201613054D0 (en) | 2016-07-28 | 2016-07-28 | New compound and process |
| GB1613054.4 | 2016-07-28 | ||
| PCT/GB2017/052190 WO2018020249A1 (en) | 2016-07-28 | 2017-07-27 | New compound and process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019527228A JP2019527228A (ja) | 2019-09-26 |
| JP2019527228A5 true JP2019527228A5 (enExample) | 2021-06-17 |
| JP6985367B2 JP6985367B2 (ja) | 2021-12-22 |
Family
ID=56936838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019503748A Active JP6985367B2 (ja) | 2016-07-28 | 2017-07-27 | 新規化合物および方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US10710998B2 (enExample) |
| EP (1) | EP3490988B1 (enExample) |
| JP (1) | JP6985367B2 (enExample) |
| KR (1) | KR102396059B1 (enExample) |
| CN (1) | CN109641891B (enExample) |
| CY (1) | CY1122138T1 (enExample) |
| DK (1) | DK3490988T3 (enExample) |
| ES (1) | ES2751948T3 (enExample) |
| GB (1) | GB201613054D0 (enExample) |
| HR (1) | HRP20192109T1 (enExample) |
| HU (1) | HUE046509T2 (enExample) |
| LT (1) | LT3490988T (enExample) |
| PL (1) | PL3490988T3 (enExample) |
| PT (1) | PT3490988T (enExample) |
| RS (1) | RS59566B1 (enExample) |
| SI (1) | SI3490988T1 (enExample) |
| SM (1) | SMT201900582T1 (enExample) |
| TW (1) | TWI739871B (enExample) |
| WO (1) | WO2018020249A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI3231444T1 (sl) | 2014-05-12 | 2020-04-30 | Verona Pharma Plc | Novo zdravljenje |
| GB201502260D0 (en) | 2015-02-11 | 2015-04-01 | Verona Pharma Plc | Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound |
| EP4090654B1 (en) * | 2020-01-17 | 2025-07-09 | Lupin Limited | Methods, processes and intermediates for preparing chroman compounds |
| JP2024517583A (ja) | 2021-04-29 | 2024-04-23 | ▲蘇▼州盛迪▲亞▼生物医▲薬▼有限公司 | イソキノリノン系化合物及びその用途 |
| 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 |
| EP4378942A1 (en) | 2022-12-02 | 2024-06-05 | Sandoz AG | Crystal form of a pde3/4 inhibitor |
| WO2025003643A1 (en) | 2023-06-26 | 2025-01-02 | Verona Pharma Plc | Particulate composition comprising ensifetrine |
| TW202506117A (zh) | 2023-06-26 | 2025-02-16 | 英商維羅納製藥Ｐｌｃ公司 | 顆粒組成物 |
| US20250073240A1 (en) | 2023-09-06 | 2025-03-06 | Verona Pharma Plc | New treatment |
| US20250249008A1 (en) | 2024-02-07 | 2025-08-07 | Verona Pharma Plc | Pharmaceutical compositions of ensifentrine for chronic obstructive pulmonary disease |
| WO2025168706A1 (en) | 2024-02-07 | 2025-08-14 | Verona Pharma Plc | Pharmaceutical compositions of ensifentrine for chronic obstructive pulmonary disease |
| WO2025176871A1 (en) | 2024-02-23 | 2025-08-28 | Inke, S.A. | Process for preparing pyrimido[6,1-a]isoquinoline-4-ones |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ185900A (en) | 1976-12-10 | 1981-04-24 | Hoechst Ag | Pyrimido (6,1-a) isoquinolin-4-ones medicaments intermediate isoquinolines |
| FI64370C (fi) | 1977-05-05 | 1983-11-10 | Hoechst Ag | Foerfarande foer framstaellning av terapeutiskt anvaendbara pyimido-(6,1-a)isokinolin-2-imino-4-onderivat |
| DE2847693A1 (de) | 1978-11-03 | 1980-05-22 | Hoechst Ag | Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen |
| DE3135831A1 (de) | 1981-09-10 | 1983-04-28 | Hoechst Ag, 6230 Frankfurt | 9,10-substituierte 2-mesitylimino-3-alkyl-3,4,6,7-tetrahydro-2h-pyrimido(6,1-a)isochinolin-4-one, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| CA1237429A (en) | 1983-05-05 | 1988-05-31 | Frank Kienzle | Pyrimidone derivatives |
| EP1165558B1 (en) | 1999-03-31 | 2003-09-24 | Vernalis Limited | Derivatives of pyrimido[6,1-a]isoquinolin-4-one |
| PH12013500261A1 (en) | 2010-08-09 | 2013-03-04 | Verona Pharma Plc | Crystalline form of pyrimidio[6,1-a]isoquinolin-4-one compound |
| PT2968313T (pt) | 2013-03-15 | 2018-02-21 | Verona Pharma Plc | Combinação de fármacos |
| SI3231444T1 (sl) | 2014-05-12 | 2020-04-30 | Verona Pharma Plc | Novo zdravljenje |
| DK3494962T3 (da) | 2014-09-15 | 2021-06-21 | Verona Pharma Plc | Flydende inhalationsformulering omfattende RPL554 |
| GB201502260D0 (en) | 2015-02-11 | 2015-04-01 | Verona Pharma Plc | Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound |
-
2016
- 2016-07-28 GB GBGB1613054.4A patent/GB201613054D0/en not_active Ceased
-
2017
- 2017-07-27 KR KR1020197004436A patent/KR102396059B1/ko active Active
- 2017-07-27 ES ES17748880T patent/ES2751948T3/es active Active
- 2017-07-27 US US16/309,435 patent/US10710998B2/en active Active
- 2017-07-27 LT LTEP17748880.6T patent/LT3490988T/lt unknown
- 2017-07-27 TW TW106125312A patent/TWI739871B/zh active
- 2017-07-27 RS RS20191474A patent/RS59566B1/sr unknown
- 2017-07-27 JP JP2019503748A patent/JP6985367B2/ja active Active
- 2017-07-27 HU HUE17748880A patent/HUE046509T2/hu unknown
- 2017-07-27 DK DK17748880T patent/DK3490988T3/da active
- 2017-07-27 WO PCT/GB2017/052190 patent/WO2018020249A1/en not_active Ceased
- 2017-07-27 PT PT177488806T patent/PT3490988T/pt unknown
- 2017-07-27 EP EP17748880.6A patent/EP3490988B1/en active Active
- 2017-07-27 SI SI201730098T patent/SI3490988T1/sl unknown
- 2017-07-27 PL PL17748880T patent/PL3490988T3/pl unknown
- 2017-07-27 SM SM20190582T patent/SMT201900582T1/it unknown
- 2017-07-27 CN CN201780046788.1A patent/CN109641891B/zh active Active
- 2017-07-27 HR HRP20192109TT patent/HRP20192109T1/hr unknown
-
2019
- 2019-10-04 CY CY20191101046T patent/CY1122138T1/el unknown
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