HRP20160358T1 - Polimorfi 6-(piperidin-4-iloksi)-2h-izokinolin-1-on hidroklorida - Google Patents
Polimorfi 6-(piperidin-4-iloksi)-2h-izokinolin-1-on hidroklorida Download PDFInfo
- Publication number
- HRP20160358T1 HRP20160358T1 HRP20160358TT HRP20160358T HRP20160358T1 HR P20160358 T1 HRP20160358 T1 HR P20160358T1 HR P20160358T T HRP20160358T T HR P20160358TT HR P20160358 T HRP20160358 T HR P20160358T HR P20160358 T1 HRP20160358 T1 HR P20160358T1
- Authority
- HR
- Croatia
- Prior art keywords
- polymorph
- isoquinolin
- yloxy
- piperidin
- degrees 2theta
- Prior art date
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- KMNVOGVCCZNVNU-UHFFFAOYSA-N 6-piperidin-4-yloxy-2h-isoquinolin-1-one;hydrochloride Chemical compound Cl.C=1C=C2C(=O)NC=CC2=CC=1OC1CCNCC1 KMNVOGVCCZNVNU-UHFFFAOYSA-N 0.000 title claims 15
- 239000000843 powder Substances 0.000 claims 9
- 230000005855 radiation Effects 0.000 claims 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims 8
- 239000004480 active ingredient Substances 0.000 claims 7
- 206010020880 Hypertrophy Diseases 0.000 claims 4
- 208000017169 kidney disease Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 200000000007 Arterial disease Diseases 0.000 claims 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 208000006029 Cardiomegaly Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
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- -1 Galopamil Chemical compound 0.000 claims 2
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- 229960000528 amlodipine Drugs 0.000 claims 2
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims 2
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- HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 claims 1
- BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 claims 1
- PVHUJELLJLJGLN-INIZCTEOSA-N (S)-nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-INIZCTEOSA-N 0.000 claims 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims 1
- NMKSAYKQLCHXDK-UHFFFAOYSA-N 3,3-diphenyl-N-(1-phenylethyl)-1-propanamine Chemical compound C=1C=CC=CC=1C(C)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 NMKSAYKQLCHXDK-UHFFFAOYSA-N 0.000 claims 1
- UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 claims 1
- RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 claims 1
- XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 claims 1
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- PWAMEVPXZAHDET-UHFFFAOYSA-N C1CNCCC1OC2=CC3=C(C=C2)C(=O)NC=C3.O.O Chemical compound C1CNCCC1OC2=CC3=C(C=C2)C(=O)NC=C3.O.O PWAMEVPXZAHDET-UHFFFAOYSA-N 0.000 claims 1
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- UWWDHYUMIORJTA-HSQYWUDLSA-N Moexipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 UWWDHYUMIORJTA-HSQYWUDLSA-N 0.000 claims 1
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 claims 1
- FAIIFDPAEUKBEP-UHFFFAOYSA-N Nilvadipine Chemical compound COC(=O)C1=C(C#N)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 FAIIFDPAEUKBEP-UHFFFAOYSA-N 0.000 claims 1
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- 206010036590 Premature baby Diseases 0.000 claims 1
- VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 claims 1
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- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 claims 1
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- HHHKFGXWKKUNCY-FHWLQOOXSA-N cilazapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 HHHKFGXWKKUNCY-FHWLQOOXSA-N 0.000 claims 1
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- ZDXUKAKRHYTAKV-UHFFFAOYSA-N lercanidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZDXUKAKRHYTAKV-UHFFFAOYSA-N 0.000 claims 1
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- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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Claims (23)
1. Kristalni polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida koji ima formulu
[image]
naznačen time da polimorf iskazuje u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja refleksije barem unutar dva raspona koji su odabrani od
1) 15.4 - 15.8 i
2) 16.5 -16.8 ± 0.2 stupnjeva 2theta.
2. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema zahtjevu 1, naznačen time da je polimorf 2 i ima refleksiju u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja barem kod 8.1, 15.8 i 16.5 stupnjeva 2theta ± 0.2 stupnjeva 2theta.
3. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema zahtjevu 2, naznačen time da je polimorf 2 i ima refleksiju u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja barem kod 8.1, 15.8, 16.5, 22.2, 25,0 i 26.6 stupnjeva 2theta ± 0.2 stupnjeva 2theta.
4. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema zahtjevu 1, naznačen time da je polimorf 1 i ima refleksije u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja barem kod 4.5, 15.4, 16.8, 21.7 i 24.7 stupnjeva 2theta ± 0.2 stupnjeva 2theta.
5. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema zahtjevu 4, naznačen time da je polimorf 1 i ima refleksije u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja barem kod 4.5, 15.4, 16.8, 21.7, 22.8 i 24.7 stupnjeva 2theta ± 0.2 stupnjeva 2theta.
6. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema zahtjevu 1, naznačen time da je polimorf 3 i ima refleksije u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja barem kod 4.5, 15.4, 16.7, 21.7 i 25.5 stupnjeva 2theta ± 0.2 stupnjeva 2theta.
7. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema zahtjevu 6, naznačen time da je polimorf 3 i ima refleksije u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja barem kod 4.5, 15.4, 16.7, 21.7, 22.3 i 25.5 stupnjeva 2theta ± 0.2 stupnjeva 2theta.
8. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema zahtjevu 1, naznačen time da je polimorf 4 i ima refleksije u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja barem kod 15.4, 18.7, 21.5 i 30.7 stupnjeva 2theta ± 0.2 stupnjeva 2theta.
9. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema zahtjevu 8, naznačen time da je polimorf 4 i ima refleksije u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja barem kod 15.4, 16.7, 16.9, 21.5, 22.4, i 30.7 stupnjeva 2theta ± 0.2 stupnjeva 2theta.
10. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema bilo kojem od zahtjeva 1 do 9 naznačen time da je za uporabu kao medikament.
11. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema bilo kojem od zahtjeva 1 do 9 naznačen time da je za uporabu kao lijek za liječenje i/ili sprječavanje hipertenzije, plućne hipertenzije, očne hipertenzije, retinopatije, glaukoma, poremećaja perifernog krvotoka, periferne okluzivne arterijske bolesti (PAOD), koronarne bolesti srca, angine pektoris, hipertrofije srca, zatajenja srca, ishemijskih bolesti, krajnjeg oštećenja organa, plućne fibroze, fibroze jetre, zatajenja jetre, nefropatije, zatajenja bubrega, fibroze bubrega, glomeruloskleroze bubrega, hipertrofije organa, astme, kronične opstruktivne plućne bolesti (KOPD), sindroma respiratornog distresa kod odraslih, trombotičnih poremećaja, kapi, cerebralnog vazospazma, cerebralne ishemije, boli, neuronske degeneracije, ozljede leđne moždine, Alzheimerove bolesti, prijevremenog poroda, erektilne disfunkcije, endokrinih disfunkcija, arterioskleroze, hipertrofije prostate, dijabetesa i komplikacija kod dijabetesa, metaboličkog sindroma, restenoze krvnih žila, ateroskleroze, upale, autoimunih bolesti, osteopatije, infekcije probavnog sustava s bakterijama, sepse ili razvoja i napredovanja raka.
12. Kruti farmaceutski pripravak naznačen time da sadrži polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema bilo kojem od zahtjeva 1 do 9 i jednu ili više farmaceutski prihvatljivih pomoćnih tvari.
13. Pripravak prema zahtjevu 12 naznačen time da je za liječenje i/ili sprječavanje hipertenzije, plućne hipertenzije, očne hipertenzije, retinopatije, glaukoma, poremećaja perifernog krvotoka, periferne okluzivne arterijske bolesti (PAOD), koronarne bolesti srca, angine pektoris, hipertrofije srca, zatajenja srca, ishemijskih bolesti, krajnjeg oštećenja organa, plućne fibroze, fibroze jetre, zatajenja jetre, nefropatije, zatajenja bubrega, fibroze bubrega, glomeruloskleroze bubrega, hipertrofije organa, astme, kronične opstruktivne plućne bolesti (KOPD), sindroma respiratornog distresa kod odraslih, trombotičnih poremećaja, kapi, cerebralnog vazospazma, cerebralne ishemije, boli, neuronske degeneracije, ozljede leđne moždine, Alzheimerove bolesti, prijevremenog poroda, erektilne disfunkcije, endokrinih disfunkcija, arterioskleroze, hipertrofije prostate, dijabetesa i komplikacija kod dijabetesa, metaboličkog sindroma, restenoze krvnih žila, ateroskleroze, upale, autoimunih bolesti, osteopatije, infekcije probavnog sustava s bakterijama, sepse ili razvoja i napredovanja raka.
14. Polimorf 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema bilo kojem od zahtjeva 1 do 9, naznačen time da je za uporabu kao lijek za liječenje i/ili sprečavanje nefropatija.
15. Polimorf za uporabu prema zahtjevu 14, naznačen time da nefropatija je dijabetička nefropatija.
16. Farmaceutski pripravak naznačen time da sadrži jedan ili više spojeva kako je zatraženo u jednom ili više zahtjeva 1 do 9 i barem jedan dodatni aktivni sastojak.
17. Farmaceutski pripravak prema zahtjevu 16, naznačen time da, kao dodatni aktivni sastojak, sadrži, jedno ili više antidijabetičkih sredstava, aktivne hipoglikemijske sastojke ili anti-hipertenzijska sredstva.
18. Farmaceutski pripravak prema zahtjevu 16, naznačen time da, kao dodatni aktivni sastojak, sadrži, jedan ili više blokatora beta receptora, blokatora kalcijevih kanala ili renin-angiotenzin inhibitora.
19. Farmaceutski pripravak prema zahtjevu 18, naznačen time da kao dodatni aktivni sastojak sadrži Verapamil, Galopamil, Fendilin, Diltiazem, Nitrendipin, Felodipin, Amlodipin, Nifedipin, Lerkanidipin, Nimodipin, Nikardipin, Lakidipin, Isradipin, Nisoldipin, Nilvadipin ili Manidipin.
20. Farmaceutski pripravak prema zahtjevu 19, naznačen time da kao dodatni aktivni sastojak sadrži Amlodipin.
21. Farmaceutski pripravak prema zahtjevu 16, naznačen time da kao dodatni aktivni sastojak sadrži, jedan ili više inhibitora ACE (angiotenzin konvertirajući enzim).
22. Farmaceutski pripravak prema zahtjevu 21, naznačen time da kao dodatni aktivni sastojak sadrži Benazepril, Kaptopril, Cilazapril, Enalapril, Fosinopril, Imidapril, Lizinopril, Moeksipril, Perindopril, Kinapril, Ramipril, Spirapril, Trandolapril ili Zofenopril,
23. Uporaba polimorfa 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema zahtjevima 1-9, koji su polimorf 1, polimorf 2, polimorf 3 ili polimorf 4 naznačena time da je za pripremanje dihidrata 6-(piperidin-4-iloksi)-2H-izokinolin-1-ona.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11305891 | 2011-07-08 | ||
| EP11306034 | 2011-12-29 | ||
| PCT/EP2012/062444 WO2013007519A1 (en) | 2011-07-08 | 2012-06-27 | Polymorphs of 6-(piperidin-4-yloxy)-2h-isoquinolin-1-one hydrochloride |
| EP12730525.8A EP2729461B1 (en) | 2011-07-08 | 2012-06-27 | Polymorphs of 6-(piperidin-4-yloxy)-2h-isoquinolin-1-one hydrochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160358T1 true HRP20160358T1 (hr) | 2016-05-06 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160358TT HRP20160358T1 (hr) | 2011-07-08 | 2016-04-07 | Polimorfi 6-(piperidin-4-iloksi)-2h-izokinolin-1-on hidroklorida |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8598201B2 (hr) |
| EP (1) | EP2729461B1 (hr) |
| JP (1) | JP2014518236A (hr) |
| KR (1) | KR102013567B1 (hr) |
| CN (1) | CN103781777A (hr) |
| AU (1) | AU2012283277B2 (hr) |
| CA (1) | CA2843777C (hr) |
| CY (1) | CY1117545T1 (hr) |
| DK (1) | DK2729461T3 (hr) |
| ES (1) | ES2567317T3 (hr) |
| HK (1) | HK1192234A1 (hr) |
| HR (1) | HRP20160358T1 (hr) |
| HU (1) | HUE028550T2 (hr) |
| IN (1) | IN2014CN00834A (hr) |
| PL (1) | PL2729461T3 (hr) |
| RU (1) | RU2014104357A (hr) |
| SI (1) | SI2729461T1 (hr) |
| WO (1) | WO2013007519A1 (hr) |
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| CN109810173B (zh) * | 2017-11-21 | 2020-11-27 | 首都医科大学 | 二氢异喹啉-3-甲酰-TARGD(aa)aa,其制备,抗静脉血栓活性和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1248869A2 (en) * | 2000-01-07 | 2002-10-16 | Transform Pharmaceuticals, Inc. | High-throughput formation, identification, and analysis of diverse solid-forms |
| BRPI0613861B8 (pt) * | 2005-07-26 | 2021-05-25 | Sanofi Aventis | derivados de isoquinolona piperidinil-substituídos como inibidores de rho-cinase |
| TW200738682A (en) | 2005-12-08 | 2007-10-16 | Organon Nv | Isoquinoline derivatives |
| CN101616909B (zh) * | 2006-12-27 | 2013-09-11 | 塞诺菲-安万特股份有限公司 | 作为Rho-激酶抑制剂的被取代的异喹啉和异喹啉酮衍生物 |
| BRPI0821837A2 (pt) * | 2007-12-26 | 2015-06-16 | Sanofi Aventis | Processo para a preparação de 6-substituídas-1-(2h)-isoquinolinonas |
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2012
- 2012-06-27 HU HUE12730525A patent/HUE028550T2/en unknown
- 2012-06-27 IN IN834CHN2014 patent/IN2014CN00834A/en unknown
- 2012-06-27 KR KR1020147003355A patent/KR102013567B1/ko active IP Right Grant
- 2012-06-27 JP JP2014517676A patent/JP2014518236A/ja active Pending
- 2012-06-27 SI SI201230513A patent/SI2729461T1/sl unknown
- 2012-06-27 EP EP12730525.8A patent/EP2729461B1/en active Active
- 2012-06-27 RU RU2014104357/04A patent/RU2014104357A/ru not_active Application Discontinuation
- 2012-06-27 ES ES12730525.8T patent/ES2567317T3/es active Active
- 2012-06-27 CN CN201280043622.1A patent/CN103781777A/zh active Pending
- 2012-06-27 WO PCT/EP2012/062444 patent/WO2013007519A1/en active Application Filing
- 2012-06-27 DK DK12730525.8T patent/DK2729461T3/en active
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- 2012-06-27 CA CA2843777A patent/CA2843777C/en active Active
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- 2012-06-27 AU AU2012283277A patent/AU2012283277B2/en active Active
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| Publication number | Publication date |
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| KR20140046460A (ko) | 2014-04-18 |
| CA2843777C (en) | 2018-11-06 |
| EP2729461A1 (en) | 2014-05-14 |
| US8598201B2 (en) | 2013-12-03 |
| DK2729461T3 (en) | 2016-04-11 |
| AU2012283277B2 (en) | 2016-07-21 |
| RU2014104357A (ru) | 2015-08-20 |
| AU2012283277A1 (en) | 2014-02-27 |
| CA2843777A1 (en) | 2013-01-17 |
| ES2567317T3 (es) | 2016-04-21 |
| PL2729461T3 (pl) | 2016-06-30 |
| SI2729461T1 (sl) | 2016-06-30 |
| HUE028550T2 (en) | 2016-12-28 |
| WO2013007519A1 (en) | 2013-01-17 |
| KR102013567B1 (ko) | 2019-08-23 |
| IN2014CN00834A (hr) | 2015-04-03 |
| CY1117545T1 (el) | 2017-04-26 |
| CN103781777A (zh) | 2014-05-07 |
| EP2729461B1 (en) | 2016-01-20 |
| JP2014518236A (ja) | 2014-07-28 |
| US20130012479A1 (en) | 2013-01-10 |
| HK1192234A1 (zh) | 2014-08-15 |
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