JP2015500325A5 - - Google Patents
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- JP2015500325A5 JP2015500325A5 JP2014546621A JP2014546621A JP2015500325A5 JP 2015500325 A5 JP2015500325 A5 JP 2015500325A5 JP 2014546621 A JP2014546621 A JP 2014546621A JP 2014546621 A JP2014546621 A JP 2014546621A JP 2015500325 A5 JP2015500325 A5 JP 2015500325A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
- iii
- reaction
- process according
- 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 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 16
- 238000004519 manufacturing process Methods 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- JJIUISYYTFDATN-UHFFFAOYSA-N 5-fluoro-2-methyl-1h-indole Chemical compound FC1=CC=C2NC(C)=CC2=C1 JJIUISYYTFDATN-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 239000012535 impurity Substances 0.000 claims 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 2
- FATGTHLOZSXOBC-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 FATGTHLOZSXOBC-UHFFFAOYSA-N 0.000 claims 1
- 239000003125 aqueous solvent Substances 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
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- OAIDTHUQTAVCPS-UHFFFAOYSA-N ethyl 2-[5-fluoro-2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetate Chemical compound C12=CC(F)=CC=C2N(CC(=O)OCC)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 OAIDTHUQTAVCPS-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- XCVUPRULBFEFCC-UHFFFAOYSA-N ethyl 2-(5-fluoro-2-methylindol-1-yl)acetate Chemical compound FC1=CC=C2N(CC(=O)OCC)C(C)=CC2=C1 XCVUPRULBFEFCC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical compound CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1121557.1 | 2011-12-15 | ||
| GB201121557A GB201121557D0 (en) | 2011-12-15 | 2011-12-15 | Process |
| PCT/GB2012/000903 WO2013088108A1 (en) | 2011-12-15 | 2012-12-14 | Process for the preparation of (5-fluoro-2-methyl-3-quinolin-2-ylmethyl-indol-1-yl)-acetic acid esters |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017146700A Division JP2018008985A (ja) | 2011-12-15 | 2017-07-28 | （５−フルオロ−２−メチル−３−キノリン−２−イルメチル−インドール−１−イル）−酢酸エステルの製造のための方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015500325A JP2015500325A (ja) | 2015-01-05 |
| JP2015500325A5 true JP2015500325A5 (enExample) | 2018-02-08 |
| JP6300277B2 JP6300277B2 (ja) | 2018-03-28 |
Family
ID=45560499
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014546621A Expired - Fee Related JP6300277B2 (ja) | 2011-12-15 | 2012-12-14 | （５−フルオロ−２−メチル−３−キノリン−２−イルメチル−インドール−１−イル）−酢酸エステルの製造のための方法 |
| JP2017146700A Pending JP2018008985A (ja) | 2011-12-15 | 2017-07-28 | （５−フルオロ−２−メチル−３−キノリン−２−イルメチル−インドール−１−イル）−酢酸エステルの製造のための方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017146700A Pending JP2018008985A (ja) | 2011-12-15 | 2017-07-28 | （５−フルオロ−２−メチル−３−キノリン−２−イルメチル−インドール−１−イル）−酢酸エステルの製造のための方法 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US9102658B2 (enExample) |
| EP (1) | EP2791129B1 (enExample) |
| JP (2) | JP6300277B2 (enExample) |
| KR (1) | KR102018929B1 (enExample) |
| CN (1) | CN104114548B (enExample) |
| AU (1) | AU2012351341B2 (enExample) |
| BR (1) | BR112014014604B1 (enExample) |
| CA (1) | CA2859281C (enExample) |
| CY (1) | CY1117087T1 (enExample) |
| DK (1) | DK2791129T3 (enExample) |
| EA (1) | EA026617B1 (enExample) |
| ES (1) | ES2557762T3 (enExample) |
| GB (1) | GB201121557D0 (enExample) |
| HR (1) | HRP20151422T1 (enExample) |
| HU (1) | HUE028257T2 (enExample) |
| IL (1) | IL233132A (enExample) |
| ME (1) | ME02348B (enExample) |
| MX (1) | MX342273B (enExample) |
| PL (1) | PL2791129T3 (enExample) |
| PT (1) | PT2791129E (enExample) |
| RS (1) | RS54523B1 (enExample) |
| SG (1) | SG11201402798RA (enExample) |
| SI (1) | SI2791129T1 (enExample) |
| SM (1) | SMT201500327B (enExample) |
| UA (1) | UA111868C2 (enExample) |
| WO (1) | WO2013088108A1 (enExample) |
| ZA (1) | ZA201404246B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201103837D0 (en) | 2011-03-07 | 2011-04-20 | Oxagen Ltd | Amorphous (5-Fluoro-2-Methyl-3-Quinolin-2-Ylmethyl-Indol-1-Yl)-acetic acid |
| GB201121557D0 (en) | 2011-12-15 | 2012-01-25 | Oxagen Ltd | Process |
| GB201322273D0 (en) * | 2013-12-17 | 2014-01-29 | Atopix Therapeutics Ltd | Process |
| GB201407807D0 (en) * | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| GB201407820D0 (en) * | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| EP3902795A1 (en) | 2018-12-27 | 2021-11-03 | Chiesi Farmaceutici S.p.A. | Pharmaceutical composition comprising spherical agglomerates of timapiprant |
| CN111978245A (zh) * | 2020-09-15 | 2020-11-24 | 上海毕得医药科技有限公司 | 一种3-氟-2-异丁基吡啶的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0415437A (pt) | 2003-10-14 | 2006-12-05 | Oxagen Ltd | composto, processo para a preparação e uso do mesmo, composição farmacêutica, processo para a preparação da mesma, e, produto |
| GB0324763D0 (en) | 2003-10-23 | 2003-11-26 | Oxagen Ltd | Use of compounds in therapy |
| GB0504150D0 (en) * | 2005-03-01 | 2005-04-06 | Oxagen Ltd | Microcrystalline material |
| GB0505048D0 (en) | 2005-03-11 | 2005-04-20 | Oxagen Ltd | Compounds with PGD antagonist activity |
| US7188489B2 (en) | 2005-04-12 | 2007-03-13 | Martello Russell A | Portable air conditioner |
| GB0605743D0 (en) * | 2006-03-22 | 2006-05-03 | Oxagen Ltd | Salts with CRTH2 antagonist activity |
| MX2009000801A (es) | 2006-07-22 | 2009-02-03 | Oxagen Ltd | Compuestos que tienen actividad antagonista crth2. |
| US20110124683A1 (en) | 2007-11-13 | 2011-05-26 | Oxagen Limited | Use of CRTH2 Antagonist Compounds |
| US7750027B2 (en) | 2008-01-18 | 2010-07-06 | Oxagen Limited | Compounds having CRTH2 antagonist activity |
| DK2250161T3 (da) | 2008-01-18 | 2014-01-27 | Atopix Therapeutics Ltd | Forbindelser med CRTH2-antagonistaktivitet |
| US8168673B2 (en) | 2008-01-22 | 2012-05-01 | Oxagen Limited | Compounds having CRTH2 antagonist activity |
| JP2011509990A (ja) | 2008-01-22 | 2011-03-31 | オキサジェン リミテッド | Ｃｒｔｈ２アンタゴニスト活性を有する化合物 |
| US20130052190A1 (en) | 2011-02-22 | 2013-02-28 | Oxagen Limited | CRTH2 Antagonists for Treatment of Eosinophilic Diseases and Conditions |
| GB201103837D0 (en) | 2011-03-07 | 2011-04-20 | Oxagen Ltd | Amorphous (5-Fluoro-2-Methyl-3-Quinolin-2-Ylmethyl-Indol-1-Yl)-acetic acid |
| GB201121557D0 (en) * | 2011-12-15 | 2012-01-25 | Oxagen Ltd | Process |
| SG11201402796SA (en) | 2011-12-16 | 2014-06-27 | Atopix Therapeutics Ltd | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
-
2011
- 2011-12-15 GB GB201121557A patent/GB201121557D0/en not_active Ceased
-
2012
- 2012-12-14 CA CA2859281A patent/CA2859281C/en active Active
- 2012-12-14 EP EP12805725.4A patent/EP2791129B1/en active Active
- 2012-12-14 ME MEP-2015-218A patent/ME02348B/me unknown
- 2012-12-14 US US14/364,509 patent/US9102658B2/en not_active Expired - Fee Related
- 2012-12-14 MX MX2014007129A patent/MX342273B/es active IP Right Grant
- 2012-12-14 HU HUE12805725A patent/HUE028257T2/en unknown
- 2012-12-14 AU AU2012351341A patent/AU2012351341B2/en not_active Ceased
- 2012-12-14 JP JP2014546621A patent/JP6300277B2/ja not_active Expired - Fee Related
- 2012-12-14 SI SI201230408T patent/SI2791129T1/sl unknown
- 2012-12-14 EA EA201490998A patent/EA026617B1/ru unknown
- 2012-12-14 UA UAA201406835A patent/UA111868C2/uk unknown
- 2012-12-14 DK DK12805725.4T patent/DK2791129T3/en active
- 2012-12-14 PT PT128057254T patent/PT2791129E/pt unknown
- 2012-12-14 WO PCT/GB2012/000903 patent/WO2013088108A1/en not_active Ceased
- 2012-12-14 ES ES12805725.4T patent/ES2557762T3/es active Active
- 2012-12-14 PL PL12805725T patent/PL2791129T3/pl unknown
- 2012-12-14 CN CN201280066207.8A patent/CN104114548B/zh not_active Expired - Fee Related
- 2012-12-14 BR BR112014014604-7A patent/BR112014014604B1/pt not_active IP Right Cessation
- 2012-12-14 KR KR1020147017740A patent/KR102018929B1/ko not_active Expired - Fee Related
- 2012-12-14 HR HRP20151422TT patent/HRP20151422T1/hr unknown
- 2012-12-14 RS RS20150871A patent/RS54523B1/sr unknown
- 2012-12-14 SG SG11201402798RA patent/SG11201402798RA/en unknown
-
2014
- 2014-06-09 ZA ZA2014/04246A patent/ZA201404246B/en unknown
- 2014-06-15 IL IL233132A patent/IL233132A/en active IP Right Grant
-
2015
- 2015-12-23 CY CY20151101189T patent/CY1117087T1/el unknown
- 2015-12-23 SM SM201500327T patent/SMT201500327B/it unknown
-
2017
- 2017-07-28 JP JP2017146700A patent/JP2018008985A/ja active Pending
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