JP2013508406A5 - - Google Patents
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- JP2013508406A5 JP2013508406A5 JP2012535392A JP2012535392A JP2013508406A5 JP 2013508406 A5 JP2013508406 A5 JP 2013508406A5 JP 2012535392 A JP2012535392 A JP 2012535392A JP 2012535392 A JP2012535392 A JP 2012535392A JP 2013508406 A5 JP2013508406 A5 JP 2013508406A5
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- JP
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- Prior art keywords
- compound
- hcl
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- 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.)
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- 238000000034 method Methods 0.000 claims 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 10
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 5
- 229940125782 compound 2 Drugs 0.000 claims 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 229940126214 compound 3 Drugs 0.000 claims 4
- 239000007822 coupling agent Substances 0.000 claims 4
- 239000003880 polar aprotic solvent Substances 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 229940125904 compound 1 Drugs 0.000 claims 3
- 235000019439 ethyl acetate Nutrition 0.000 claims 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 2
- GPIQOFWTZXXOOV-UHFFFAOYSA-N 2-chloro-4,6-dimethoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(OC)=N1 GPIQOFWTZXXOOV-UHFFFAOYSA-N 0.000 claims 2
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims 2
- 239000007821 HATU Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 238000007664 blowing Methods 0.000 claims 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 claims 1
- 239000012065 filter cake Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- HZKKQOCNNKDBRA-UHFFFAOYSA-N CCOC(C1=CNc(c(Cl)ccc2C(F)(F)F)c2C1=O)=O Chemical compound CCOC(C1=CNc(c(Cl)ccc2C(F)(F)F)c2C1=O)=O HZKKQOCNNKDBRA-UHFFFAOYSA-N 0.000 description 1
- GIFDDEUMMLLKIL-UHFFFAOYSA-N Nc(cc1)c(C(F)(F)F)cc1N1C2CCC1CC2 Chemical compound Nc(cc1)c(C(F)(F)F)cc1N1C2CCC1CC2 GIFDDEUMMLLKIL-UHFFFAOYSA-N 0.000 description 1
- VKTTYIXIDXWHKW-UHFFFAOYSA-N Nc1cc(C(F)(F)F)ccc1Cl Chemical compound Nc1cc(C(F)(F)F)ccc1Cl VKTTYIXIDXWHKW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25463409P | 2009-10-23 | 2009-10-23 | |
| US61/254,634 | 2009-10-23 | ||
| PCT/US2010/053628 WO2011050215A1 (en) | 2009-10-23 | 2010-10-21 | Process for preparing modulators of cystic fibrosis transmembrane conductance regulator |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013508406A JP2013508406A (ja) | 2013-03-07 |
| JP2013508406A5 true JP2013508406A5 (enExample) | 2013-11-21 |
| JP5789611B2 JP5789611B2 (ja) | 2015-10-07 |
Family
ID=43530872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012535392A Expired - Fee Related JP5789611B2 (ja) | 2009-10-23 | 2010-10-21 | 嚢胞性線維症膜コンダクタンス制御因子のモジュレーターを調製するためのプロセス |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US8344147B2 (enExample) |
| EP (1) | EP2491018A1 (enExample) |
| JP (1) | JP5789611B2 (enExample) |
| KR (1) | KR20120104554A (enExample) |
| CN (1) | CN102648182A (enExample) |
| AR (1) | AR080065A1 (enExample) |
| AU (1) | AU2010310612A1 (enExample) |
| BR (1) | BR112012009583A2 (enExample) |
| CA (1) | CA2778492A1 (enExample) |
| IL (1) | IL219326A0 (enExample) |
| MX (1) | MX2012004790A (enExample) |
| NZ (1) | NZ600172A (enExample) |
| RU (1) | RU2553989C2 (enExample) |
| TW (1) | TWI475023B (enExample) |
| WO (1) | WO2011050215A1 (enExample) |
| ZA (1) | ZA201202915B (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1898221A (zh) | 2003-09-06 | 2007-01-17 | 沃泰克斯药物股份有限公司 | Atp－结合弹夹转运蛋白的调控剂 |
| US7977322B2 (en) | 2004-08-20 | 2011-07-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| HUE032540T2 (en) | 2004-06-24 | 2017-09-28 | Vertex Pharma | Modulators of ATP-binding cassette transporters |
| ATE512145T1 (de) | 2005-08-11 | 2011-06-15 | Vertex Pharma | Modulatoren des cystic fibrosis transmembrane conductance regulators |
| EP2395002B1 (en) | 2005-11-08 | 2014-06-18 | Vertex Pharmaceuticals Inc. | Pharmaceutical composition containing a heterocyclic modulator of atp-binding cassette transporters. |
| CA2635581C (en) | 2005-12-28 | 2017-02-28 | Vertex Pharmaceuticals Incorporated | Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| CN101395147B (zh) | 2005-12-28 | 2013-05-29 | 弗特克斯药品有限公司 | 作为atp-结合盒转运蛋白调节剂用于治疗囊性纤维化的1-(苯并[d][1,3]间二氧杂环戊烯-5-基)-n-(苯基)环丙烷-甲酰胺衍生物及相关化合物 |
| PT2674428T (pt) | 2006-04-07 | 2016-07-14 | Vertex Pharma | Modeladores de transportadores de cassetes de ligação de atp |
| US7645789B2 (en) | 2006-04-07 | 2010-01-12 | Vertex Pharmaceuticals Incorporated | Indole derivatives as CFTR modulators |
| USRE50453E1 (en) | 2006-04-07 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Indole derivatives as CFTR modulators |
| US10022352B2 (en) | 2006-04-07 | 2018-07-17 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| US8563573B2 (en) | 2007-11-02 | 2013-10-22 | Vertex Pharmaceuticals Incorporated | Azaindole derivatives as CFTR modulators |
| NZ581259A (en) | 2007-05-09 | 2012-07-27 | Vertex Pharma | Modulators of cystic fibrosis transmembrane conductance regulator |
| HUE028426T2 (en) | 2007-08-24 | 2016-12-28 | Vertex Pharma | Isothiazolopyridinones for (inter alia) treating cystic fibrosis |
| ES2556080T3 (es) | 2007-11-16 | 2016-01-12 | Vertex Pharmaceuticals Incorporated | Moduladores de isoquinolina de transportadores de casete de unión a ATP |
| UA102534C2 (xx) | 2007-12-07 | 2013-07-25 | Вертекс Фармасьютикалз Инкорпорейтед | ТВЕРДА ФОРМА 3-(6-(1-(2,2-ДИФТОРБЕНЗО$d]$1,3]-ДІОКСОЛ-5-ІЛ)-ЦИКЛОПРОПАНКАРБОКСАМІДО)-3-МЕТИЛПІРИДИН-2-ІЛ)БЕНЗОЙНОЇ КИСЛОТИ (ВАРІАНТИ)$ТВЕРДАЯ ФОРМА 3-(6-(1-(2,2-ДИФТОРБЕНЗО$d]$1,3]-ДИОКСОЛ-5-ИЛ)-ЦИКЛОПРОПАНКАРБОКСАМИДО)-3-МЕТИЛПИРИДИН-2-ИЛ)БЕНЗОЙНОЙ КИСЛОТЫ (ВАРИАНТЫ) |
| UA95199C2 (en) * | 2007-12-07 | 2011-07-11 | Вертекс Фармасьютикалз Инкорпорейтед | Aqueous formulation of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| LT2639223T (lt) | 2007-12-07 | 2017-06-26 | Vertex Pharmaceuticals Incorporated | Cikloalkilkarboksiamido-piridino benzenkarboksirūgščių gamybos būdas |
| US20100036130A1 (en) | 2007-12-07 | 2010-02-11 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxamido-pyridine benzoic acids |
| NZ602030A (en) | 2008-02-28 | 2014-02-28 | Vertex Pharma | Heteroaryl derivatives as cftr modulators |
| NZ616097A (en) | 2008-03-31 | 2015-04-24 | Vertex Pharma | Pyridyl derivatives as cftr modulators |
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| US12458635B2 (en) | 2008-08-13 | 2025-11-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| MX2011003249A (es) * | 2008-09-29 | 2011-05-19 | Vertex Pharma | Unidades de dosificacion del acido 3-(6-(1-(2,2-difluorobenzo[d][1 ,3]dioxol-5-il)ciclopropancarboxamido)-3-metilpiridin-2-il)benzoi co. |
| AR074060A1 (es) | 2008-10-23 | 2010-12-22 | Vertex Pharma | Moduladores del regulador de conductancia transmembrana de la fibrosis quistica |
| NZ592504A (en) * | 2008-10-23 | 2013-04-26 | Vertex Pharma | Solid forms of n-(4-(7-azabicyclo[2.2.1]heptan-7-yl)-2-(trifluoromethyl)phenyl)-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxamide |
| EP2821400B1 (en) | 2009-03-20 | 2017-09-27 | Vertex Pharmaceuticals Incorporated | Process for making modulators of cystic fibrosis transmembrane conductance regulator |
| KR20120083416A (ko) * | 2009-09-17 | 2012-07-25 | 버텍스 파마슈티칼스 인코포레이티드 | 아자비시클릭 화합물의 제조 방법 |
| US8389727B2 (en) * | 2009-10-23 | 2013-03-05 | Vertex Pharmaceuticals Incorporated | Solid forms of N-(4-(7-Azabicyclo[2.2.1]Heptan-7-yl)-2-Trifluoromethyl)Phenyl)-4-Oxo-5-(Trifluoromethyl)-1,4-Dihydroquinoline-3-Carboxamide |
| US8802868B2 (en) | 2010-03-25 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Solid forms of (R)-1(2,2-difluorobenzo[D][1,3]dioxo1-5-yl)-N-(1-(2,3-dihydroxypropyl-6-fluoro-2-(1-hydroxy-2-methylpropan2-yl)-1H-Indol-5-yl)-Cyclopropanecarboxamide |
| CN102917692A (zh) | 2010-04-07 | 2013-02-06 | 弗特克斯药品有限公司 | 3-(6-(1-(2,2-二氟苯并[d][1,3]二氧杂环戊烯-5-基)环丙甲酰胺基)-3-甲基吡啶-2-基)苯甲酸的药物组合物和其给药方法 |
| NZ602795A (en) | 2010-04-07 | 2015-01-30 | Vertex Pharma | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| CA2797118C (en) | 2010-04-22 | 2021-03-30 | Vertex Pharmaceuticals Incorporated | Process of producing cycloalkylcarboxamido-indole compounds |
| US8404849B2 (en) * | 2010-05-20 | 2013-03-26 | Vertex Pharmaceuticals | Processes for producing modulators of cystic fibrosis transmembrane conductance regulator |
| US8563593B2 (en) | 2010-06-08 | 2013-10-22 | Vertex Pharmaceuticals Incorporated | Formulations of (R)-1-(2,2-difluorobenzo[D] [1,3] dioxol-5-yl)-N-(1-(2,3-dihydroxypropyl)-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide |
| AU2012335714B2 (en) | 2011-11-08 | 2017-04-13 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| RU2692779C2 (ru) | 2012-02-27 | 2019-06-27 | Вертекс Фармасьютикалз Инкорпорейтед | Фармацевтическая композиция и ее введения |
| US8674108B2 (en) | 2012-04-20 | 2014-03-18 | Vertex Pharmaceuticals Incorporated | Solid forms of N-[2,4-bis(1,1-dimethylethy)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| AU2013290444B2 (en) | 2012-07-16 | 2018-04-26 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of (R)-1-(2,2-diflurorbenzo[d][1,3]dioxol-5-yl)-N-(1-(2,3-dihydroxypropyl)-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)-1H-indol-5-yl) cyclopropanecarboxamide and administration thereof |
| BR112016010403A2 (pt) | 2013-11-12 | 2017-08-08 | Vertex Pharma | Processo de preparação de composições farmacêuticas para o tratamento de doenças mediadas por cftr |
| CA2944140C (en) | 2014-04-15 | 2022-10-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions for the treatment of cystic fibrosis transmembrane conductance regulator mediated diseases |
| RU2749213C2 (ru) | 2014-10-07 | 2021-06-07 | Вертекс Фармасьютикалз Инкорпорейтед | Сокристаллы модуляторов регулятора трансмембранной проводимости при кистозном фиброзе |
| US10302602B2 (en) | 2014-11-18 | 2019-05-28 | Vertex Pharmaceuticals Incorporated | Process of conducting high throughput testing high performance liquid chromatography |
| JP7158717B2 (ja) * | 2017-11-22 | 2022-10-24 | 国立大学法人九州工業大学 | 求電子的アジド化剤又はジアゾ化剤 |
| CN109369798B (zh) * | 2018-12-25 | 2020-09-15 | 苏州天马医药集团天吉生物制药有限公司 | 一种合成索玛鲁肽的方法 |
| CR20230120A (es) | 2020-08-07 | 2023-09-01 | Vertex Pharma | Moduladores del regulador de la conductancia transmembrana de la fibrosis quística |
| US12324802B2 (en) | 2020-11-18 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
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| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5886026A (en) | 1993-07-19 | 1999-03-23 | Angiotech Pharmaceuticals Inc. | Anti-angiogenic compositions and methods of use |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| SK286420B6 (sk) * | 1997-09-15 | 2008-09-05 | The Procter & Gamble Company | Zlúčenina so štruktúrou chinolónu, farmaceutický prostriedok s jej obsahom a jej použitie |
| NZ505362A (en) * | 1997-12-22 | 2004-12-24 | Upjohn Co | 4-hydroxyquinoline-3-carboxamides and -hydrazides useful as antiviral agents |
| HUE032540T2 (en) | 2004-06-24 | 2017-09-28 | Vertex Pharma | Modulators of ATP-binding cassette transporters |
| AU2008298545B2 (en) * | 2007-09-14 | 2013-12-12 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| PL2444120T3 (pl) | 2007-12-10 | 2018-02-28 | Novartis Ag | Spirocyklicze analogi amiloridu jako blokery ENac |
| NZ592504A (en) * | 2008-10-23 | 2013-04-26 | Vertex Pharma | Solid forms of n-(4-(7-azabicyclo[2.2.1]heptan-7-yl)-2-(trifluoromethyl)phenyl)-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxamide |
| AR074060A1 (es) * | 2008-10-23 | 2010-12-22 | Vertex Pharma | Moduladores del regulador de conductancia transmembrana de la fibrosis quistica |
| US8389727B2 (en) * | 2009-10-23 | 2013-03-05 | Vertex Pharmaceuticals Incorporated | Solid forms of N-(4-(7-Azabicyclo[2.2.1]Heptan-7-yl)-2-Trifluoromethyl)Phenyl)-4-Oxo-5-(Trifluoromethyl)-1,4-Dihydroquinoline-3-Carboxamide |
-
2010
- 2010-10-21 JP JP2012535392A patent/JP5789611B2/ja not_active Expired - Fee Related
- 2010-10-21 WO PCT/US2010/053628 patent/WO2011050215A1/en not_active Ceased
- 2010-10-21 CN CN2010800533805A patent/CN102648182A/zh active Pending
- 2010-10-21 CA CA2778492A patent/CA2778492A1/en not_active Abandoned
- 2010-10-21 AU AU2010310612A patent/AU2010310612A1/en not_active Abandoned
- 2010-10-21 BR BR112012009583A patent/BR112012009583A2/pt not_active IP Right Cessation
- 2010-10-21 EP EP10775986A patent/EP2491018A1/en not_active Withdrawn
- 2010-10-21 KR KR1020127013136A patent/KR20120104554A/ko not_active Withdrawn
- 2010-10-21 NZ NZ600172A patent/NZ600172A/en not_active IP Right Cessation
- 2010-10-21 RU RU2012121160/04A patent/RU2553989C2/ru not_active IP Right Cessation
- 2010-10-21 MX MX2012004790A patent/MX2012004790A/es active IP Right Grant
- 2010-10-21 US US12/909,750 patent/US8344147B2/en active Active
- 2010-10-22 TW TW099136180A patent/TWI475023B/zh not_active IP Right Cessation
- 2010-10-25 AR ARP100103914A patent/AR080065A1/es unknown
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2012
- 2012-04-20 ZA ZA2012/02915A patent/ZA201202915B/en unknown
- 2012-04-22 IL IL219326A patent/IL219326A0/en unknown
- 2012-11-16 US US13/678,840 patent/US8754222B2/en active Active
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2014
- 2014-03-07 US US14/200,656 patent/US8884018B2/en active Active
- 2014-07-09 US US14/326,930 patent/US20140336393A1/en not_active Abandoned
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