HRP20160356T1 - Kristalni solvati 6-(piperidin-4-iloksi)-2h-izokinolin-1-on hidroklorida - Google Patents
Kristalni solvati 6-(piperidin-4-iloksi)-2h-izokinolin-1-on hidroklorida Download PDFInfo
- Publication number
- HRP20160356T1 HRP20160356T1 HRP20160356TT HRP20160356T HRP20160356T1 HR P20160356 T1 HRP20160356 T1 HR P20160356T1 HR P20160356T T HRP20160356T T HR P20160356TT HR P20160356 T HRP20160356 T HR P20160356T HR P20160356 T1 HRP20160356 T1 HR P20160356T1
- Authority
- HR
- Croatia
- Prior art keywords
- hydrate
- nephropathy
- isoquinolin
- yloxy
- piperidin
- 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 6
- 239000012453 solvate Substances 0.000 title 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 8
- 239000004480 active ingredient Substances 0.000 claims 7
- 208000017169 kidney disease Diseases 0.000 claims 6
- 206010020880 Hypertrophy Diseases 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 239000000843 powder Substances 0.000 claims 3
- 230000005855 radiation Effects 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
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- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
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- 208000010228 Erectile Dysfunction Diseases 0.000 claims 2
- -1 Galopamil Chemical compound 0.000 claims 2
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- 102000004270 Peptidyl-Dipeptidase A Human genes 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
- LDHGRQSOEGKRHX-UHFFFAOYSA-N 6-piperidin-4-yloxy-2h-isoquinolin-1-one;hydrate;hydrochloride Chemical compound O.Cl.C=1C=C2C(=O)NC=CC2=CC=1OC1CCNCC1 LDHGRQSOEGKRHX-UHFFFAOYSA-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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- 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
- 208000005107 Premature Birth Diseases 0.000 claims 1
- 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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- ANEBWFXPVPTEET-UHFFFAOYSA-N manidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ANEBWFXPVPTEET-UHFFFAOYSA-N 0.000 claims 1
- 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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- 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
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
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Claims (21)
1. Kristalni hidrat 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida koji ima formulu
[image]
naznačen time da hidrat sadrži 1.85 do 2.2 molekula vode po molekuli (I).
2. Hidrat prema zahtjevu 1, naznačen time da hidrat sadrži 2.0 molekula vode po molekuli (I).
3. Hidrat prema zahtjevu 1, naznačen time da hidrat sadrži 10.5 - 12.5 % (t/t) vode.
4. Kristalni hidrat 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida koji ima formulu
[image]
naznačen time da ima refleksiju u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja kod 7.7 ± 0.2 stupnjeva 2theta.
5. Hidrat prema zahtjevu 4, naznačen time da ima refleksije u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja kod 7.7, 15.2 i 16.8 stupnjeva 2theta ± 0.2 stupnjeva 2theta,
6. Hidrat prema zahtjevu 4, naznačen time da ima refleksije u difraktogramu X-zraka na prahu korištenjem CuKα1 zračenja kod 7.7, 15.2, 16.8, 22.4, 25.0, i 26.6 stupnjeva 2theta ± 0.2 stupnjeva 2theta.
7. Hidrat 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema bilo kojem od zahtjeva 1 do 6 naznačen time da je za uporabu kao lijek.
8. Hidrat 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema bilo kojem od zahtjeva 1 do 6 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.
9. Hidrat 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema zahtjevu 7 ili 8, naznačen time da je za uporabu kao lijek za liječenje i/ili sprječavanje nefropatije.
10. Hidrat za uporabu prema zahtjevu 9, naznačen time da nefropatija je dijabetička nefropatija.
11. Kruti farmaceutski pripravak naznačen time da sadrži hidrat 6-(piperidin-4-iloksi)-2H-izokinolin-1-on hidroklorida prema bilo kojem od zahtjeva 1 do 6 i jednu ili više farmaceutski prihvatljivih pomoćnih tvari.
12. Pripravak prema zahtjevu 11 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.
13. Pripravak u skladu sa zahtjevom 11 ili zahtjevom 12, naznačen time da je za liječenje i/ili sprječavanje nefropatije.
14. Pripravak u skladu sa zahtjevom 13, naznačen time da nefropatija je dijabetička nefropatija.
15. Farmaceutski pripravak naznačen time da sadrži jedan ili više spojeva kako je zatraženo u jednom ili više zahtjeva 1 do 6 i barem jedan dodatni aktivni sastojak.
16. Farmaceutski pripravak prema zahtjevu 15, naznačen time da, kao dodatni aktivni sastojak, sadrži, jedno ili više antidijabetičkih sredstava, aktivne hipoglikemijske sastojke ili anti-hipertenzijska sredstva.
17. Farmaceutski pripravak prema zahtjevu 15, naznačen time da, kao dodatni aktivni sastojak, sadrži, jedan ili više blokatora beta receptora, blokatora kalcijevih kanala ili renin-angiotenzin inhibitora.
18. Farmaceutski pripravak prema zahtjevu 17, 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.
19. Farmaceutski pripravak prema zahtjevu 18, naznačen time da kao dodatni aktivni sastojak sadrži Amlodipin.
20. Farmaceutski pripravak prema zahtjevu 15, naznačen time da kao dodatni aktivni sastojak sadrži, jedan ili više inhibitora ACE (angiotenzin konvertirajući enzim).
21. Farmaceutski pripravak prema zahtjevu 20, naznačen time da kao dodatni aktivni sastojak sadrži Benazepril, Kaptopril, Cilazapril, Enalapril, Fosinopril, Imidapril, Lizinopril, Moeksipril, Perindopril, Kinapril, Ramipril, Spirapril, Trandolapril ili Zofenopril,
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11305890 | 2011-07-08 | ||
| EP11306033 | 2011-12-29 | ||
| PCT/EP2012/062431 WO2013007518A1 (en) | 2011-07-08 | 2012-06-27 | Crystalline solvates of 6-(piperidin-4-yloxy)-2h-isoquinolin-1-one hydrochloride |
| EP12730523.3A EP2729460B1 (en) | 2011-07-08 | 2012-06-27 | Crystalline solvates of 6-(piperidin-4-yloxy)-2h-isoquinolin-1-one hydrochloride |
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| HRP20160356T1 true HRP20160356T1 (hr) | 2016-05-06 |
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| HRP20160356TT HRP20160356T1 (hr) | 2011-07-08 | 2016-04-07 | Kristalni solvati 6-(piperidin-4-iloksi)-2h-izokinolin-1-on hidroklorida |
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| US (2) | US8710078B2 (hr) |
| EP (1) | EP2729460B1 (hr) |
| JP (1) | JP6357100B2 (hr) |
| KR (1) | KR102013566B1 (hr) |
| CN (1) | CN103781778B (hr) |
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| CO (1) | CO6870040A2 (hr) |
| CY (1) | CY1118326T1 (hr) |
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| HK (1) | HK1192546A1 (hr) |
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| IN (1) | IN2014CN00817A (hr) |
| MA (1) | MA35340B1 (hr) |
| PL (1) | PL2729460T3 (hr) |
| RU (1) | RU2619129C2 (hr) |
| SG (1) | SG2014007520A (hr) |
| SI (1) | SI2729460T1 (hr) |
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| HUE027309T2 (en) * | 2011-07-08 | 2016-10-28 | Sanofi Sa | Crystalline solvates of 6- (Piperidin-4-ylix) -2H-isoquinolin-1-one hydrochloride |
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| US20020048610A1 (en) * | 2000-01-07 | 2002-04-25 | Cima Michael J. | High-throughput formation, identification, and analysis of diverse solid-forms |
| KR101373535B1 (ko) | 2005-07-26 | 2014-03-12 | 사노피 | Ｒｈｏ-키나제 억제제로서의 피페리디닐-치환된 이소퀴놀론유도체 |
| TW200738682A (en) | 2005-12-08 | 2007-10-16 | Organon Nv | Isoquinoline derivatives |
| WO2007101242A1 (en) | 2006-02-28 | 2007-09-07 | Meadwestvaco Packaging Systems Llc | Carton for tapered and cylindrical articles and blank therefor |
| MX2009005825A (es) * | 2006-12-27 | 2009-06-16 | Sanofi Aventis | Derivados de isoquinolina e isoquinolinona sustituidos en calidad de inhibidores de rho-quinasa. |
| RU2009128690A (ru) * | 2006-12-27 | 2011-02-10 | Санофи-Авентис (Fr) | Новые замещенные производные изохинолина и изохинолинона |
| RU2010131010A (ru) * | 2007-12-26 | 2012-02-10 | Санофи-Авентис (Fr) | Способ получения 6-замещенных-1-(2н)-изохинолинонов |
| HUE027309T2 (en) * | 2011-07-08 | 2016-10-28 | Sanofi Sa | Crystalline solvates of 6- (Piperidin-4-ylix) -2H-isoquinolin-1-one hydrochloride |
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Also Published As
| Publication number | Publication date |
|---|---|
| PL2729460T3 (pl) | 2016-07-29 |
| SI2729460T1 (sl) | 2016-05-31 |
| JP6357100B2 (ja) | 2018-07-11 |
| KR20140045550A (ko) | 2014-04-16 |
| WO2013007518A1 (en) | 2013-01-17 |
| CA2843773A1 (en) | 2013-01-17 |
| CA2843773C (en) | 2018-11-06 |
| SG2014007520A (en) | 2014-07-30 |
| RU2014104358A (ru) | 2015-08-20 |
| CN103781778B (zh) | 2015-10-07 |
| US8710078B2 (en) | 2014-04-29 |
| JP2014518235A (ja) | 2014-07-28 |
| US20140221656A1 (en) | 2014-08-07 |
| CO6870040A2 (es) | 2014-02-20 |
| IN2014CN00817A (hr) | 2015-04-03 |
| DK2729460T3 (en) | 2016-04-18 |
| AU2012283276B2 (en) | 2014-07-24 |
| ES2568245T3 (es) | 2016-04-28 |
| EP2729460B1 (en) | 2016-01-13 |
| AU2012283276A1 (en) | 2014-02-27 |
| CN103781778A (zh) | 2014-05-07 |
| KR102013566B1 (ko) | 2019-08-23 |
| HK1192546A1 (zh) | 2014-08-22 |
| MA35340B1 (fr) | 2014-08-01 |
| US20130012444A1 (en) | 2013-01-10 |
| EP2729460A1 (en) | 2014-05-14 |
| ZA201400941B (en) | 2015-05-27 |
| CY1118326T1 (el) | 2017-06-28 |
| HUE027309T2 (en) | 2016-10-28 |
| NZ620864A (en) | 2015-08-28 |
| RU2619129C2 (ru) | 2017-05-12 |
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