JP2012501296A5 - - Google Patents
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- Publication number
- JP2012501296A5 JP2012501296A5 JP2011508745A JP2011508745A JP2012501296A5 JP 2012501296 A5 JP2012501296 A5 JP 2012501296A5 JP 2011508745 A JP2011508745 A JP 2011508745A JP 2011508745 A JP2011508745 A JP 2011508745A JP 2012501296 A5 JP2012501296 A5 JP 2012501296A5
- Authority
- JP
- Japan
- Prior art keywords
- salt
- stress
- fluoropyridin
- gastritis
- ulcers
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- JDCBSVKVFVIKHL-UHFFFAOYSA-N 1-[4-fluoro-5-(2-fluoropyridin-3-yl)-1-(4-methylpyridin-2-yl)sulfonylpyrrol-3-yl]-n-methylmethanamine Chemical compound FC=1C(CNC)=CN(S(=O)(=O)C=2N=CC=C(C)C=2)C=1C1=CC=CN=C1F JDCBSVKVFVIKHL-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 7
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 6
- 208000008469 Peptic Ulcer Diseases 0.000 claims 4
- 208000025865 Ulcer Diseases 0.000 claims 4
- 208000011906 peptic ulcer disease Diseases 0.000 claims 4
- 230000035882 stress Effects 0.000 claims 4
- 231100000397 ulcer Toxicity 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 208000007882 Gastritis Diseases 0.000 claims 2
- 206010017866 Gastritis haemorrhagic Diseases 0.000 claims 2
- 206010020601 Hyperchlorhydria Diseases 0.000 claims 2
- 206010042220 Stress ulcer Diseases 0.000 claims 2
- 206010046274 Upper gastrointestinal haemorrhage Diseases 0.000 claims 2
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims 2
- 230000037328 acute stress Effects 0.000 claims 2
- 208000000718 duodenal ulcer Diseases 0.000 claims 2
- 210000003238 esophagus Anatomy 0.000 claims 2
- 230000002496 gastric effect Effects 0.000 claims 2
- 208000017215 gastric mucosa-associated lymphoid tissue lymphoma Diseases 0.000 claims 2
- 201000000052 gastrinoma Diseases 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 208000000689 peptic esophagitis Diseases 0.000 claims 2
- 230000002980 postoperative effect Effects 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- DPRWORPFTHSTIE-UHFFFAOYSA-N 1-[4-fluoro-5-(2-fluoropyridin-3-yl)-1-(4-methoxypyridin-2-yl)sulfonylpyrrol-3-yl]-n-methylmethanamine Chemical compound FC=1C(CNC)=CN(S(=O)(=O)C=2N=CC=C(OC)C=2)C=1C1=CC=CN=C1F DPRWORPFTHSTIE-UHFFFAOYSA-N 0.000 claims 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000009858 acid secretion Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000002860 competitive effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940126535 potassium competitive acid blocker Drugs 0.000 claims 1
- 229910001414 potassium ion Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- -1 2-fluoropyridin-3-yl Chemical group 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000001548 androgenic effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- WNFZZBXZGQNHQE-UHFFFAOYSA-N 1-[4-fluoro-5-(2-fluoropyridin-3-yl)-1-(4-methylpyridin-2-yl)sulfonylpyrrol-3-yl]-n-methylmethanamine;hydrochloride Chemical compound Cl.FC=1C(CNC)=CN(S(=O)(=O)C=2N=CC=C(C)C=2)C=1C1=CC=CN=C1F WNFZZBXZGQNHQE-UHFFFAOYSA-N 0.000 description 1
- PKVQYVUTTKAEBW-UHFFFAOYSA-N 1-[4-fluoro-5-(2-fluoropyridin-3-yl)-1-(5-fluoropyridin-3-yl)sulfonylpyrrol-3-yl]-n-methylmethanamine Chemical compound FC=1C(CNC)=CN(S(=O)(=O)C=2C=C(F)C=NC=2)C=1C1=CC=CN=C1F PKVQYVUTTKAEBW-UHFFFAOYSA-N 0.000 description 1
- ASDZKCNDAHKXPO-UHFFFAOYSA-N 1-[4-fluoro-5-(2-fluoropyridin-3-yl)-1-(5-fluoropyridin-3-yl)sulfonylpyrrol-3-yl]-n-methylmethanamine;hydrochloride Chemical compound Cl.FC=1C(CNC)=CN(S(=O)(=O)C=2C=C(F)C=NC=2)C=1C1=CC=CN=C1F ASDZKCNDAHKXPO-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- FIDJLNBSSLXRLL-UHFFFAOYSA-N butanedioic acid;1-[4-fluoro-5-(2-fluoropyridin-3-yl)-1-(5-fluoropyridin-3-yl)sulfonylpyrrol-3-yl]-n-methylmethanamine Chemical compound OC(=O)CCC(O)=O.FC=1C(CNC)=CN(S(=O)(=O)C=2C=C(F)C=NC=2)C=1C1=CC=CN=C1F FIDJLNBSSLXRLL-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011508745A JP5638515B2 (ja) | 2008-08-27 | 2009-08-26 | ピロール化合物 |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008218851 | 2008-08-27 | ||
| JP2008218851 | 2008-08-27 | ||
| JP2008269099 | 2008-10-17 | ||
| JP2008269099 | 2008-10-17 | ||
| PCT/JP2009/065279 WO2010024451A1 (en) | 2008-08-27 | 2009-08-26 | Pyrrole compounds |
| JP2011508745A JP5638515B2 (ja) | 2008-08-27 | 2009-08-26 | ピロール化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012501296A JP2012501296A (ja) | 2012-01-19 |
| JP2012501296A5 true JP2012501296A5 (enExample) | 2012-09-13 |
| JP5638515B2 JP5638515B2 (ja) | 2014-12-10 |
Family
ID=41508823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011508745A Active JP5638515B2 (ja) | 2008-08-27 | 2009-08-26 | ピロール化合物 |
Country Status (38)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20110300A1 (es) * | 2008-08-27 | 2011-06-16 | Takeda Pharmaceutical | Compuestos de pirrol como inhibidores de la bomba de protones |
| US20110229879A1 (en) * | 2010-03-19 | 2011-09-22 | University Of Rochester | Methods and compositions for nuclear staining |
| CN102452979B (zh) * | 2010-11-03 | 2015-04-01 | 天津药明康德新药开发有限公司 | 5-氟-3-吡啶磺酰氯的合成方法 |
| CN102863371B (zh) * | 2011-07-06 | 2016-04-13 | 中国科学院上海有机化学研究所 | 氟代二氢吡咯或氟代吡咯 |
| US10039813B2 (en) | 2012-02-07 | 2018-08-07 | Massachusetts Institute Of Technology | Use of antagonists of ghrelin or ghrelin receptor to prevent or treat stress-sensitive psychiatric illness |
| JP6216338B2 (ja) | 2012-06-27 | 2017-10-18 | 武田薬品工業株式会社 | 塩により安定化されたアミンおよび有機酸の液状製剤 |
| WO2014133059A1 (ja) * | 2013-02-28 | 2014-09-04 | 武田薬品工業株式会社 | スルホニルクロライド化合物の製造法 |
| US9724396B2 (en) | 2013-03-15 | 2017-08-08 | Massachusetts Institute Of Technology | Use of antagonists of growth hormone or growth hormone receptor to prevent or treat stress-sensitive psychiatric illness |
| KR102084185B1 (ko) | 2013-08-29 | 2020-03-04 | 주식회사 대웅제약 | 테트라히드로사이클로펜타피롤 유도체 및 이의 제조방법 |
| CN105367550A (zh) * | 2014-08-11 | 2016-03-02 | 江苏柯菲平医药股份有限公司 | 四氢环戊二烯并[c]吡咯类衍生物、其制备方法及其在医药上的应用 |
| UY36547A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
| US10317418B2 (en) | 2015-02-24 | 2019-06-11 | Massachusetts Institute Of Technology | Use of ghrelin or functional ghrelin receptor agonists to prevent and treat stress-sensitive psychiatric illness |
| JP6778680B2 (ja) | 2015-07-30 | 2020-11-04 | 武田薬品工業株式会社 | 錠剤 |
| CN108137548A (zh) | 2015-08-07 | 2018-06-08 | 拜耳作物科学股份公司 | 作为农药的2-(杂)芳基取代的稠合杂环衍生物 |
| CN106430006B (zh) * | 2016-08-18 | 2018-06-12 | 国网湖南省电力公司带电作业中心 | 配电线路移动式绝缘登高作业装置及方法 |
| CN108203430A (zh) * | 2016-12-16 | 2018-06-26 | 天地人和生物科技有限公司 | 一种新型可逆性质子泵抑制剂及其制备方法和用途 |
| JP7228535B2 (ja) | 2017-07-10 | 2023-02-24 | 武田薬品工業株式会社 | ボノプラザン含有製剤 |
| KR102126576B1 (ko) | 2018-09-19 | 2020-06-24 | 주식회사 대웅제약 | 4-메톡시 피롤 유도체의 제조 방법 |
| CN113527536B (zh) * | 2020-04-21 | 2024-03-22 | 杭州德柯医疗科技有限公司 | 一种含氟多糖高分子化合物及其制备方法 |
| KR20210156235A (ko) * | 2020-06-17 | 2021-12-24 | 일동제약(주) | 신규한 산 분비 억제제 및 이의 용도 |
| EP4074317A1 (en) | 2021-04-14 | 2022-10-19 | Bayer AG | Phosphorus derivatives as novel sos1 inhibitors |
| CN113620930B (zh) * | 2021-07-12 | 2022-08-16 | 南京烁慧医药科技有限公司 | 一种含磺酰胺结构的化合物及其制备方法和应用、一种药物组合物及应用 |
| WO2023113474A1 (ko) * | 2021-12-15 | 2023-06-22 | 일동제약(주) | 1-설포닐 피롤 유도체의 신규 염, 이의 제조 방법 및 이를 포함하는 약학 조성물 |
| US20250084026A1 (en) * | 2021-12-15 | 2025-03-13 | Ildong Pharmaceutical Co., Ltd. | Novel salt of 1-sulfonyl pyrrole derivative, preparation method thereof and pharmaceutical composition comprising thereof |
| KR20230102353A (ko) * | 2021-12-30 | 2023-07-07 | 주식회사 대웅제약 | 삼중음성유방암의 예방 또는 치료용 약학적 조성물 |
| WO2026029625A1 (ko) * | 2024-08-02 | 2026-02-05 | 일양약품주식회사 | 4-사이클로프로필 피롤 유도체 및 이의 용도 |
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| EP1655284A1 (en) | 2004-10-26 | 2006-05-10 | Aponetics AG | 2-Phenylsulfopyrroles |
| EP2327692B9 (en) | 2005-08-30 | 2014-06-04 | Takeda Pharmaceutical Company Limited | 1-heterocyclylsulfonyl, 2-aminomethyl, 5-(hetero-)aryl substituted 1-H-pyrrole derivatives as acid secretion inhibitors |
| US8512761B2 (en) * | 2006-01-27 | 2013-08-20 | Yale University | Fast acting inhibitor of gastric acid secretion |
| EP2005957B1 (en) | 2006-03-31 | 2012-05-30 | Takeda Pharmaceutical Company Limited | Acid secretion inhibitor |
| US8933105B2 (en) | 2007-02-28 | 2015-01-13 | Takeda Pharmaceutical Company Limited | Pyrrole compounds |
| PE20090709A1 (es) | 2007-09-28 | 2009-07-15 | Takeda Pharmaceutical | Compuestos heterociclico de 5 miembros |
| US20090318429A1 (en) * | 2008-04-28 | 2009-12-24 | Institute For Oneworld Health | Compounds, Compositions and Methods Comprising Heteroaromatic Derivatives |
| EA018988B1 (ru) | 2008-05-16 | 2013-12-30 | Такеда Калифорния, Инк. | Активаторы глюкокиназы |
| PE20110300A1 (es) * | 2008-08-27 | 2011-06-16 | Takeda Pharmaceutical | Compuestos de pirrol como inhibidores de la bomba de protones |
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