JP2009541455A5 - - Google Patents
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- Publication number
- JP2009541455A5 JP2009541455A5 JP2009517241A JP2009517241A JP2009541455A5 JP 2009541455 A5 JP2009541455 A5 JP 2009541455A5 JP 2009517241 A JP2009517241 A JP 2009517241A JP 2009517241 A JP2009517241 A JP 2009517241A JP 2009541455 A5 JP2009541455 A5 JP 2009541455A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- hydroxy
- ray diffraction
- diffraction pattern
- 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
- 150000001875 compounds Chemical class 0.000 claims description 13
- -1 5,6-diethyl-indan-2-ylamino Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000003839 salts Chemical group 0.000 claims description 4
- 229950000339 xinafoate Drugs 0.000 claims description 4
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 230000000414 obstructive effect Effects 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- 238000002441 X-ray diffraction Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000012458 free base Substances 0.000 claims 2
- FWTRBCFPXQDGJV-UHFFFAOYSA-N C(C)(=O)O.OC=1C=CC=C2C=CC(NC12)=O Chemical compound C(C)(=O)O.OC=1C=CC=C2C=CC(NC12)=O FWTRBCFPXQDGJV-UHFFFAOYSA-N 0.000 claims 1
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940015042 glycopyrrolate Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 claims 1
- 229960001664 mometasone Drugs 0.000 claims 1
- ZXZKYYHTWHJHFT-UHFFFAOYSA-N quinoline-2,8-diol Chemical compound C1=CC(=O)NC2=C1C=CC=C2O ZXZKYYHTWHJHFT-UHFFFAOYSA-N 0.000 claims 1
- 239000012453 solvate Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000003814 drug Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000013557 residual solvent Substances 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 230000009286 beneficial effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000011067 equilibration Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 3
- 206010011224 Cough Diseases 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 230000003326 anti-histaminergic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- QZZUEBNBZAPZLX-QFIPXVFZSA-N indacaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 QZZUEBNBZAPZLX-QFIPXVFZSA-N 0.000 description 2
- 239000002700 tablet coating Substances 0.000 description 2
- 238000009492 tablet coating Methods 0.000 description 2
- HVZUDFLGWUBMMZ-FTBISJDPSA-N 5-[(1r)-2-[(5,6-diethyl-2,3-dihydro-1h-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one;2-hydroxyacetic acid Chemical compound OCC(O)=O.N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 HVZUDFLGWUBMMZ-FTBISJDPSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000018569 Respiratory Tract disease Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- HZHXFIDENGBQFQ-FTBISJDPSA-N acetic acid;5-[(1r)-2-[(5,6-diethyl-2,3-dihydro-1h-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound CC(O)=O.N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 HZHXFIDENGBQFQ-FTBISJDPSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000000294 tussive effect Effects 0.000 description 1
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0613156.9 | 2006-06-30 | ||
| GB0613158.5 | 2006-06-30 | ||
| GB0613158A GB0613158D0 (en) | 2006-06-30 | 2006-06-30 | Organic compounds |
| GB0613160.1 | 2006-06-30 | ||
| GB0613159.3 | 2006-06-30 | ||
| GB0613159A GB0613159D0 (en) | 2006-06-30 | 2006-06-30 | Organic Compounds |
| GB0613160A GB0613160D0 (en) | 2006-06-30 | 2006-06-30 | Organic Compounds |
| GB0613156A GB0613156D0 (en) | 2006-06-30 | 2006-06-30 | Organic Compounds |
| EP06117129.4 | 2006-07-13 | ||
| EP06117129A EP1878722A1 (en) | 2006-07-13 | 2006-07-13 | Quinolinone derivatives and their pharmaceutical compositions |
| PCT/EP2007/056632 WO2008000839A1 (en) | 2006-06-30 | 2007-07-02 | Quinolinone derivatives and their pharmaceutical compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009541455A JP2009541455A (ja) | 2009-11-26 |
| JP2009541455A5 true JP2009541455A5 (enExample) | 2010-08-19 |
| JP5253392B2 JP5253392B2 (ja) | 2013-07-31 |
Family
ID=38610531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009517241A Active JP5253392B2 (ja) | 2006-06-30 | 2007-07-02 | キノリノン誘導体およびその医薬組成物 |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US8198450B2 (enExample) |
| EP (1) | EP2044025B1 (enExample) |
| JP (1) | JP5253392B2 (enExample) |
| KR (1) | KR101402398B1 (enExample) |
| CN (1) | CN101479245B (enExample) |
| AU (1) | AU2007264946B2 (enExample) |
| BR (1) | BRPI0713951B8 (enExample) |
| CA (1) | CA2654801C (enExample) |
| CY (3) | CY1113733T1 (enExample) |
| DK (1) | DK2044025T3 (enExample) |
| ES (1) | ES2396987T3 (enExample) |
| FI (2) | FIC20200047I1 (enExample) |
| FR (2) | FR20C1054I1 (enExample) |
| HR (1) | HRP20121074T1 (enExample) |
| HU (2) | HUS2000043I1 (enExample) |
| IL (1) | IL195796A (enExample) |
| LT (2) | LTC2044025I2 (enExample) |
| LU (2) | LUC00185I2 (enExample) |
| MA (1) | MA30540B1 (enExample) |
| MX (1) | MX2008016542A (enExample) |
| MY (1) | MY150468A (enExample) |
| NO (3) | NO341709B1 (enExample) |
| NZ (1) | NZ573292A (enExample) |
| PL (1) | PL2044025T3 (enExample) |
| PT (1) | PT2044025E (enExample) |
| SI (1) | SI2044025T1 (enExample) |
| WO (1) | WO2008000839A1 (enExample) |
| ZA (1) | ZA200809948B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0935659A1 (en) | 1996-09-17 | 1999-08-18 | Chiron Corporation | Compositions and methods for treating intracellular diseases |
| ES2452965T3 (es) * | 2007-09-05 | 2014-04-03 | Rigel Pharmaceuticals, Inc. | Sal de xinafoato de N4-[(2,2-difluoro-4H-benzo[1,4]oxazin-3-ona)-6-il]-5-fluoro-N2-[3-(metilaminocarbonilmetilenoxi)fenil]-2,4-pirimidindiamina |
| JOP20120023B1 (ar) | 2011-02-04 | 2022-03-14 | Novartis Ag | صياغات مساحيق جافة من جسيمات تحتوي على واحد أو اثنين من المواد الفعالة لعلاج امراض ممرات الهواء الانسدادية او الالتهابية |
| CA2898700C (en) | 2013-03-14 | 2022-07-19 | Novartis Ag | Deamorphization of spray-dried formulations via spray-blending |
| US9452139B2 (en) | 2013-03-14 | 2016-09-27 | Novartis Ag | Respirable agglomerates of porous carrier particles and micronized drug |
| ES2747905T3 (es) | 2015-09-29 | 2020-03-12 | Inke Sa | Solvato mixto de L-tartrato de (R)-5-[2-(5,6-dietilindan-2-ilamino)-1-hidroxietil]-8-hidroxi-1H-quinolin-2-ona |
| CN110724095B (zh) * | 2019-09-12 | 2023-06-09 | 上海方予健康医药科技有限公司 | 一种茚达特罗乙酸盐的制备方法 |
| WO2026027448A1 (en) | 2024-07-29 | 2026-02-05 | Inke, S.A. | Micronization process of indacaterol acetate |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05202301A (ja) * | 1991-08-29 | 1993-08-10 | Yamamoto Chem Inc | ２−アニリノ−３−メチル−６−（Ｎ−ｎ−ブチル−Ｎ−シクロヘキシルアミノ）フルオランの結晶変態、その製造方法及びこの結晶変態を含有する記録材料 |
| EP0688871A3 (en) * | 1994-06-24 | 1998-07-08 | Quest International B.V. | Preparation of phytosphingosine derivative |
| FR2777279B1 (fr) * | 1998-04-08 | 2004-08-13 | Hoechst Marion Roussel Inc | Nouvelles formes cristallines du 1s-[1alpha(2s*,3r*), 9 alpha] 6,10-dioxo-n-(2-ethoxy-5-oxo-tetrahydro-3-furanyl) -9[[(1-isoquinolyl)carbonyl]amino]octohydro-6h-pyridazino [1,2-a][1,2]diazepine-1-carboxamide |
| GB9913083D0 (en) * | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| GB0029562D0 (en) * | 2000-12-04 | 2001-01-17 | Novartis Ag | Organic compounds |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| GB0127430D0 (en) | 2001-11-15 | 2002-01-09 | Smithkline Beecham Corp | Compounds |
| US7417051B2 (en) * | 2002-04-12 | 2008-08-26 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Medicaments comprising betamimetics and a novel anticholinergic |
| US7250426B2 (en) * | 2002-11-29 | 2007-07-31 | Boehringer Ingelheim Pharma Gmbh & Co Kg | Tiotropium-containing pharmaceutical combination for inhalation |
| GB0303910D0 (en) | 2003-02-20 | 2003-03-26 | Merck Sharp & Dohme | Therapeutic agents |
| TWI324150B (en) * | 2003-02-28 | 2010-05-01 | Novartis Ag | Process for preparing 5-[(r)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-8-hydroxy-(1h)-quinolin-2-one salt |
| PE20100399A1 (es) | 2003-04-02 | 2010-06-01 | Novartis Ag | Procedimiento para preparar oxi-(1h)-quinolin-2-onas 5-(alfa-haloacetil)-8-sustituidas |
| JP4516064B2 (ja) * | 2003-04-04 | 2010-08-04 | ノバルティス アーゲー | 気道疾患の処置のためのキノリン−２−オン誘導体 |
| JP2005343889A (ja) | 2004-05-06 | 2005-12-15 | Taisho Pharmaceut Co Ltd | イミダゾピリジン誘導体 |
| GB0411056D0 (en) * | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| GB0413960D0 (en) | 2004-06-22 | 2004-07-28 | Novartis Ag | Organic compounds |
| PL1869049T3 (pl) | 2005-03-21 | 2009-07-31 | Lilly Co Eli | Związki imidazopirydazyny |
| GB0511065D0 (en) | 2005-05-31 | 2005-07-06 | Novartis Ag | Organic compounds |
| EP1910369A1 (en) | 2005-07-29 | 2008-04-16 | Astellas Pharma Inc. | Fused heterocycles as lck inhibitors |
-
2007
- 2007-07-02 BR BRPI0713951A patent/BRPI0713951B8/pt active IP Right Grant
- 2007-07-02 MY MYPI20085146 patent/MY150468A/en unknown
- 2007-07-02 CN CN2007800244042A patent/CN101479245B/zh active Active
- 2007-07-02 JP JP2009517241A patent/JP5253392B2/ja active Active
- 2007-07-02 MX MX2008016542A patent/MX2008016542A/es active IP Right Grant
- 2007-07-02 PL PL07819899T patent/PL2044025T3/pl unknown
- 2007-07-02 DK DK07819899.1T patent/DK2044025T3/da active
- 2007-07-02 AU AU2007264946A patent/AU2007264946B2/en active Active
- 2007-07-02 US US12/304,617 patent/US8198450B2/en active Active
- 2007-07-02 KR KR1020087031819A patent/KR101402398B1/ko active Active
- 2007-07-02 SI SI200731103T patent/SI2044025T1/sl unknown
- 2007-07-02 PT PT78198991T patent/PT2044025E/pt unknown
- 2007-07-02 HR HRP20121074TT patent/HRP20121074T1/hr unknown
- 2007-07-02 WO PCT/EP2007/056632 patent/WO2008000839A1/en not_active Ceased
- 2007-07-02 CA CA2654801A patent/CA2654801C/en active Active
- 2007-07-02 NZ NZ573292A patent/NZ573292A/en unknown
- 2007-07-02 EP EP07819899A patent/EP2044025B1/en active Active
- 2007-07-02 ES ES07819899T patent/ES2396987T3/es active Active
-
2008
- 2008-11-24 ZA ZA2008/09948A patent/ZA200809948B/en unknown
- 2008-12-08 IL IL195796A patent/IL195796A/en active IP Right Grant
- 2008-12-30 MA MA31527A patent/MA30540B1/fr unknown
-
2009
- 2009-01-20 NO NO20090312A patent/NO341709B1/no active Protection Beyond IP Right Term
-
2012
- 2012-05-04 US US13/463,978 patent/US20120316142A1/en not_active Abandoned
- 2012-11-29 CY CY20121101169T patent/CY1113733T1/el unknown
-
2020
- 2020-11-12 FR FR20C1054C patent/FR20C1054I1/fr active Active
- 2020-11-18 HU HUS2000043C patent/HUS2000043I1/hu unknown
- 2020-11-20 LU LU00185C patent/LUC00185I2/fr unknown
- 2020-11-23 NO NO2020041C patent/NO2020041I1/no unknown
- 2020-11-25 LT LTPA2020535C patent/LTC2044025I2/lt unknown
- 2020-11-26 CY CY2020038C patent/CY2020038I2/el unknown
- 2020-11-27 FI FIC20200047C patent/FIC20200047I1/fi unknown
- 2020-12-07 LU LU00188C patent/LUC00188I2/en unknown
- 2020-12-07 NO NO2020044C patent/NO2020044I1/no unknown
- 2020-12-08 FR FR20C1063C patent/FR20C1063I1/fr active Active
- 2020-12-09 HU HUS2000053C patent/HUS2000053I1/hu unknown
- 2020-12-14 CY CY2020041C patent/CY2020041I2/el unknown
- 2020-12-16 LT LTPA2020538C patent/LTPA2020538I1/lt unknown
- 2020-12-16 FI FIC20200050C patent/FIC20200050I1/fi unknown
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