JP2008523130A5 - - Google Patents
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- Publication number
- JP2008523130A5 JP2008523130A5 JP2007545917A JP2007545917A JP2008523130A5 JP 2008523130 A5 JP2008523130 A5 JP 2008523130A5 JP 2007545917 A JP2007545917 A JP 2007545917A JP 2007545917 A JP2007545917 A JP 2007545917A JP 2008523130 A5 JP2008523130 A5 JP 2008523130A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- thf
- phenyl
- solvent
- reduced pressure
- 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.)
- Pending
Links
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XFMFNVYEANZUHC-UHFFFAOYSA-N (3-methylsulfonylphenyl)methanol Chemical compound CS(=O)(=O)C1=CC=CC(CO)=C1 XFMFNVYEANZUHC-UHFFFAOYSA-N 0.000 description 1
- YDGCCGPGWJYIHF-UHFFFAOYSA-N 2-[3-cyano-4-(3-methylsulfonylphenyl)pyrrol-1-yl]acetic acid Chemical compound CS(=O)(=O)C1=CC=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 YDGCCGPGWJYIHF-UHFFFAOYSA-N 0.000 description 1
- QWZPBEIRGTXIII-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)prop-2-enenitrile Chemical compound ClC1=CC(Cl)=CC(C=CC#N)=C1 QWZPBEIRGTXIII-UHFFFAOYSA-N 0.000 description 1
- KUTBMATZUQWFSR-UHFFFAOYSA-N 3-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC(C(O)=O)=C1 KUTBMATZUQWFSR-UHFFFAOYSA-N 0.000 description 1
- KSKAIUPCFPOCPI-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-1h-pyrrole-3-carbonitrile Chemical compound ClC1=CC(Cl)=CC(C=2C(=CNC=2)C#N)=C1 KSKAIUPCFPOCPI-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0427381.9A GB0427381D0 (en) | 2004-12-14 | 2004-12-14 | Organic compounds |
| PCT/EP2005/013297 WO2006063763A1 (en) | 2004-12-14 | 2005-12-12 | Pyrrole derivatives having crth2 receptor antagonist activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008523130A JP2008523130A (ja) | 2008-07-03 |
| JP2008523130A5 true JP2008523130A5 (https=) | 2009-02-05 |
Family
ID=34090028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007545917A Pending JP2008523130A (ja) | 2004-12-14 | 2005-12-12 | Ｃｒｔｈ２受容体アンタゴニスト活性を有するピロール誘導体 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20100087432A1 (https=) |
| EP (1) | EP1828172B1 (https=) |
| JP (1) | JP2008523130A (https=) |
| KR (1) | KR20070087605A (https=) |
| CN (1) | CN101072773B (https=) |
| AR (1) | AR052266A1 (https=) |
| AT (1) | ATE449772T1 (https=) |
| AU (1) | AU2005315881C1 (https=) |
| BR (1) | BRPI0518607A2 (https=) |
| CA (1) | CA2587934A1 (https=) |
| DE (1) | DE602005017935D1 (https=) |
| ES (1) | ES2335519T3 (https=) |
| GB (1) | GB0427381D0 (https=) |
| GT (1) | GT200500360A (https=) |
| MX (1) | MX2007007098A (https=) |
| PE (1) | PE20060736A1 (https=) |
| PL (1) | PL1828172T3 (https=) |
| PT (1) | PT1828172E (https=) |
| RU (1) | RU2007126761A (https=) |
| TW (1) | TW200635921A (https=) |
| WO (1) | WO2006063763A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0611695D0 (en) * | 2006-06-13 | 2006-07-26 | Novartis Ag | Organic compounds |
| TW200848019A (en) * | 2007-03-06 | 2008-12-16 | Wyeth Corp | Aryl sulfonamides useful for modulation of the progesterone receptor |
| DK2229358T3 (da) | 2007-12-14 | 2011-07-04 | Pulmagen Therapeutics Asthma Ltd | Indoler og deres terapeutiske anvendelse |
| CA2752981C (en) * | 2009-02-24 | 2013-11-12 | Merck Sharp & Dohme Corp. | Indole derivatives as crth2 receptor antagonists |
| JP5731538B2 (ja) | 2009-12-23 | 2015-06-10 | アイアンウッド ファーマシューティカルズ インコーポレイテッド | Ｃｒｔｈ２モジュレーター |
| AR080703A1 (es) | 2010-03-22 | 2012-05-02 | Actelion Pharmaceuticals Ltd | Derivados de 3-(heteroaril-amino)-1,2,3,4-tetrahidro-9h-carbazol, moduladores de receptores de prostaglandina d2, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento de trastornos alergicos o inmunitarios tales como asma. |
| WO2011117184A1 (de) | 2010-03-24 | 2011-09-29 | Bayer Cropscience Ag | Fludioxonil-derivate |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| WO2012078210A1 (en) * | 2010-12-08 | 2012-06-14 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators and preparation thereof |
| DK2697223T3 (en) | 2011-04-14 | 2016-09-05 | Actelion Pharmaceuticals Ltd | 7- (heteroaryl-amino) -6,7,8,9-tetrahydro-pyrido [1,2-a] indole-acetic acid derivatives and their use as prostaglandin D2 receptor |
| 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 |
| TW201331179A (zh) | 2011-12-21 | 2013-08-01 | Actelion Pharmaceuticals Ltd | 雜環衍生物及其作為前列腺素ｄ２受體調節劑之用途 |
| US20150080381A1 (en) * | 2012-04-12 | 2015-03-19 | Ironwood Pharmaceuticals, Inc. | Methods of treating alopecia and acne |
| CA2876808A1 (en) | 2012-07-05 | 2014-01-09 | Actelion Pharmaceuticals Ltd | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| ES2461415B1 (es) * | 2012-10-16 | 2015-03-16 | Consejo Superior De Investigaciones Científicas (Csic) | Derivados funcionalizados e inmunorreactivos para el fungicida fludioxonil |
| CN103553990B (zh) * | 2013-11-08 | 2016-01-20 | 苏州诚和医药化学有限公司 | 用卤素卤化合成2－甲氧基－4－氨基－5－乙砜基苯甲酸甲酯的方法 |
| CN103588686B (zh) * | 2013-11-08 | 2016-01-20 | 苏州诚和医药化学有限公司 | 一种用卤素卤化制备2－甲氧基－4－氨基－5－乙砜基苯甲酸甲酯的方法 |
| CN103553991B (zh) * | 2013-11-08 | 2016-01-20 | 苏州诚和医药化学有限公司 | 一种制备2－甲氧基－4－氨基－5－乙砜基苯甲酸甲酯的方法 |
| PE20161177A1 (es) | 2014-03-17 | 2016-11-18 | Actelion Pharmaceuticals Ltd | Derivados del acido acetico azaindol y su uso como moduladores del receptor de prostaglandina d2 |
| WO2015140701A1 (en) | 2014-03-18 | 2015-09-24 | Actelion Pharmaceuticals Ltd | Azaindole acetic acid derivatives and their use as prostaglandin d2 receptor modulators |
| KR20180053345A (ko) | 2015-09-15 | 2018-05-21 | 이도르시아 파마슈티컬스 리미티드 | 결정질 형태 |
| CN108164502B (zh) * | 2018-03-06 | 2021-04-13 | 苏州华一新能源科技有限公司 | 1,3-丙烷磺酸内酯的制备方法 |
| CN112602714B (zh) * | 2020-12-23 | 2021-11-16 | 华南农业大学 | 一类咯菌腈羧酸衍生物在用于植物维管组织靶向药剂中的应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0182737A3 (de) * | 1984-10-16 | 1986-10-08 | Ciba-Geigy Ag | 3-Phenylpyrrolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| EP0386681A1 (de) * | 1989-03-08 | 1990-09-12 | Ciba-Geigy Ag | 3-Aryl-4-cyano-pyrrol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende mikrobiozide Mittel |
| AU2002367424A1 (en) * | 2001-12-28 | 2003-07-24 | Takeda Chemical Industries, Ltd. | Androgen receptor antagonists |
| JP4316232B2 (ja) * | 2001-12-28 | 2009-08-19 | 武田薬品工業株式会社 | アンドロゲン受容体拮抗剤 |
| TW200307542A (en) * | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
| SE0301010D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| GB0308466D0 (en) * | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| EP1758874A1 (en) * | 2004-05-29 | 2007-03-07 | 7TM Pharma A/S | Substituted thiazoleacetic acids as crth2 ligands |
-
2004
- 2004-12-14 GB GBGB0427381.9A patent/GB0427381D0/en not_active Ceased
-
2005
- 2005-12-07 GT GT200500360A patent/GT200500360A/es unknown
- 2005-12-12 CN CN2005800416868A patent/CN101072773B/zh not_active Expired - Fee Related
- 2005-12-12 MX MX2007007098A patent/MX2007007098A/es active IP Right Grant
- 2005-12-12 BR BRPI0518607-2A patent/BRPI0518607A2/pt not_active IP Right Cessation
- 2005-12-12 AU AU2005315881A patent/AU2005315881C1/en not_active Ceased
- 2005-12-12 JP JP2007545917A patent/JP2008523130A/ja active Pending
- 2005-12-12 PT PT05815747T patent/PT1828172E/pt unknown
- 2005-12-12 US US11/720,786 patent/US20100087432A1/en not_active Abandoned
- 2005-12-12 EP EP05815747A patent/EP1828172B1/en not_active Expired - Lifetime
- 2005-12-12 ES ES05815747T patent/ES2335519T3/es not_active Expired - Lifetime
- 2005-12-12 RU RU2007126761/04A patent/RU2007126761A/ru not_active Application Discontinuation
- 2005-12-12 AT AT05815747T patent/ATE449772T1/de not_active IP Right Cessation
- 2005-12-12 AR ARP050105197A patent/AR052266A1/es not_active Application Discontinuation
- 2005-12-12 PL PL05815747T patent/PL1828172T3/pl unknown
- 2005-12-12 WO PCT/EP2005/013297 patent/WO2006063763A1/en not_active Ceased
- 2005-12-12 PE PE2005001434A patent/PE20060736A1/es not_active Application Discontinuation
- 2005-12-12 DE DE602005017935T patent/DE602005017935D1/de not_active Expired - Lifetime
- 2005-12-12 CA CA002587934A patent/CA2587934A1/en not_active Abandoned
- 2005-12-12 KR KR1020077013302A patent/KR20070087605A/ko not_active Abandoned
- 2005-12-13 TW TW094143970A patent/TW200635921A/zh unknown
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