JP5663699B2 - ピラゾール誘導体及びその医薬用途 - Google Patents
ピラゾール誘導体及びその医薬用途 Download PDFInfo
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- JP5663699B2 JP5663699B2 JP2014514708A JP2014514708A JP5663699B2 JP 5663699 B2 JP5663699 B2 JP 5663699B2 JP 2014514708 A JP2014514708 A JP 2014514708A JP 2014514708 A JP2014514708 A JP 2014514708A JP 5663699 B2 JP5663699 B2 JP 5663699B2
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- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- C—CHEMISTRY; METALLURGY
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
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| EP2848254B1 (en) * | 2012-05-07 | 2016-08-03 | Kissei Pharmaceutical Co., Ltd. | Pyrazole derivative and use thereof for medical purposes |
| JP5807767B2 (ja) | 2013-02-04 | 2015-11-10 | 大正製薬株式会社 | 便秘症の予防又は治療薬 |
| KR102296314B1 (ko) * | 2014-06-25 | 2021-09-01 | 이에이 파마 가부시키가이샤 | 고형 제제 및 그의 안정화 방법 |
| CN106659726A (zh) | 2014-06-25 | 2017-05-10 | Ea制药株式会社 | 固体制剂及其着色防止或着色减少方法 |
| CN112469407B (zh) | 2018-03-28 | 2024-10-01 | 阿沃林特有限公司 | 用于治疗餐后低血糖症的方法 |
| JP7391048B2 (ja) | 2018-06-05 | 2023-12-04 | アルビレオ・アクチボラグ | ベンゾチア（ジ）アゼピン化合物及び胆汁酸モジュレータとしてのそれらの使用 |
| US11801226B2 (en) | 2018-06-20 | 2023-10-31 | Albireo Ab | Pharmaceutical formulation of odevixibat |
| HRP20250427T1 (hr) | 2018-06-20 | 2025-06-06 | Albireo Ab | Kristalne modifikacije odeviksibata |
| US11007142B2 (en) | 2018-08-09 | 2021-05-18 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US11549878B2 (en) | 2018-08-09 | 2023-01-10 | Albireo Ab | In vitro method for determining the adsorbing capacity of an insoluble adsorbant |
| CR20210458A (es) | 2019-02-06 | 2021-11-04 | Albireo Ab | Compuestos de benzotiadiazepina y su uso como moduladores del ácido biliar |
| US10941127B2 (en) | 2019-02-06 | 2021-03-09 | Albireo Ab | Benzothiadiazepine compounds and their use as bile acid modulators |
| US10975045B2 (en) | 2019-02-06 | 2021-04-13 | Aibireo AB | Benzothiazepine compounds and their use as bile acid modulators |
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| CA3158181A1 (en) | 2019-12-04 | 2021-06-10 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| US11014898B1 (en) | 2020-12-04 | 2021-05-25 | Albireo Ab | Benzothiazepine compounds and their use as bile acid modulators |
| ES3029063T3 (en) | 2019-12-04 | 2025-06-23 | Albireo Ab | Benzothiadiazepine compounds and their use as bile acid modulators |
| EP4188541B1 (en) | 2020-08-03 | 2024-12-25 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| JP2023549226A (ja) | 2020-11-12 | 2023-11-22 | アルビレオ エービー | 進行性家族性肝内胆汁うっ滞症（ｐｆｉｃ）を処置するためのオデビキシバット |
| KR20230117393A (ko) | 2020-12-04 | 2023-08-08 | 알비레오 에이비 | 벤조티아(디)아제핀 화합물 및 담즙산 조절제로서의용도 |
| TW202313579A (zh) | 2021-06-03 | 2023-04-01 | 瑞典商艾爾比瑞歐公司 | 苯并噻(二)氮呯(benzothia(di)azepine)化合物及其作為膽酸調節劑之用途 |
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| WO2009128421A1 (ja) * | 2008-04-16 | 2009-10-22 | キッセイ薬品工業株式会社 | ピラゾール誘導体の１／２フマル酸塩 |
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| MX2008013583A (es) * | 2006-04-26 | 2008-10-31 | Genentech Inc | Compuestos del inhibidor de fosfoinositido 3-cinasa y composiciones farmaceuticas que los contienen. |
| AR087701A1 (es) | 2011-08-31 | 2014-04-09 | Japan Tobacco Inc | Derivados de pirazol con actividad inhibidora de sglt1 |
| EP2848254B1 (en) * | 2012-05-07 | 2016-08-03 | Kissei Pharmaceutical Co., Ltd. | Pyrazole derivative and use thereof for medical purposes |
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| WO2009084531A1 (ja) * | 2007-12-27 | 2009-07-09 | Kissei Pharmaceutical Co., Ltd. | ピラゾール誘導体のモノセバシン酸塩 |
| WO2009128421A1 (ja) * | 2008-04-16 | 2009-10-22 | キッセイ薬品工業株式会社 | ピラゾール誘導体の１／２フマル酸塩 |
Non-Patent Citations (2)
| Title |
|---|
| JPN6014047874; Ｄｉａｂｅｔｅｓ Ｊｏｕｒｎａｌ Ｖｏｌ．３１， Ｎｏ．３, 2003, ｐ．８６-９１ * |
| JPN6014047875; モダンフィジシャン Ｖｏｌ．１８， Ｎｏ．６, 1998, ｐ．７１７-７１９ * |
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| WO2013168671A1 (ja) | 2013-11-14 |
| MX2014013696A (es) | 2015-02-05 |
| KR101868991B1 (ko) | 2018-06-19 |
| BR112014027841B1 (pt) | 2022-08-09 |
| CA2872002A1 (en) | 2013-11-14 |
| BR112014027841A8 (pt) | 2021-09-28 |
| US9694027B2 (en) | 2017-07-04 |
| JP6105546B2 (ja) | 2017-03-29 |
| US20150141631A1 (en) | 2015-05-21 |
| CN104284665B (zh) | 2016-11-16 |
| HK1204773A1 (en) | 2015-12-04 |
| BR112014027841A2 (pt) | 2017-06-27 |
| EP2848254A1 (en) | 2015-03-18 |
| CN104284665A (zh) | 2015-01-14 |
| DK2848254T3 (en) | 2016-10-31 |
| EP2848254A4 (en) | 2015-07-15 |
| US9273085B2 (en) | 2016-03-01 |
| CA2872002C (en) | 2019-01-15 |
| JP2015083580A (ja) | 2015-04-30 |
| ES2601127T3 (es) | 2017-02-14 |
| EP2848254B1 (en) | 2016-08-03 |
| PT2848254T (pt) | 2016-10-05 |
| MX359988B (es) | 2018-10-18 |
| RU2014149181A (ru) | 2016-06-27 |
| US20160129031A1 (en) | 2016-05-12 |
| AU2013258566A1 (en) | 2014-11-27 |
| RU2602739C2 (ru) | 2016-11-20 |
| AU2013258566B2 (en) | 2017-03-16 |
| JPWO2013168671A1 (ja) | 2016-01-07 |
| KR20150013671A (ko) | 2015-02-05 |
| PL2848254T3 (pl) | 2017-03-31 |
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