JP2012528824A - アルファ−炭酸脱水酵素アイソフォームにより媒介される哺乳動物の障害の処置 - Google Patents
アルファ−炭酸脱水酵素アイソフォームにより媒介される哺乳動物の障害の処置 Download PDFInfo
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- JP2012528824A JP2012528824A JP2012513590A JP2012513590A JP2012528824A JP 2012528824 A JP2012528824 A JP 2012528824A JP 2012513590 A JP2012513590 A JP 2012513590A JP 2012513590 A JP2012513590 A JP 2012513590A JP 2012528824 A JP2012528824 A JP 2012528824A
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- methyl
- treatment
- pharmaceutically acceptable
- carbonic anhydrase
- acceptable salt
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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| JP2017146753A Withdrawn JP2017203037A (ja) | 2009-06-02 | 2017-07-28 | アルファ−炭酸脱水酵素アイソフォームにより媒介される哺乳動物の障害の処置 |
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| KR101778004B1 (ko) * | 2015-06-22 | 2017-09-15 | (주) 에빅스젠 | 이마티닙을 유효성분으로 포함하는 안구 건조 질환 예방 및 치료용 약학 조성물 |
| WO2018211474A1 (en) | 2017-05-19 | 2018-11-22 | Trudell Medical International | Positive expiratory pressure device |
| USD874064S1 (en) | 2018-05-18 | 2020-01-28 | Trudell Medical International | Mask |
| USD903097S1 (en) | 2018-05-18 | 2020-11-24 | Trudell Medical International | Mask |
| TWI787523B (zh) | 2018-06-15 | 2022-12-21 | 漢達生技醫藥股份有限公司 | 達沙替尼十二烷基硫酸鹽之結晶 |
| USD893806S1 (en) | 2018-11-09 | 2020-08-18 | Trudell Medical Internationl | Mask and shroud |
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| WO2008130704A2 (en) * | 2007-04-17 | 2008-10-30 | Imclone Llc | PDGFRβ-SPECIFIC INHIBITORS |
| WO2008155387A2 (en) * | 2007-06-19 | 2008-12-24 | Boehringer Ingelheim International Gmbh | Anti-igf antibodies that bind to igf-1 and igf-2 but not to insulin |
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| US5521184A (en) | 1992-04-03 | 1996-05-28 | Ciba-Geigy Corporation | Pyrimidine derivatives and processes for the preparation thereof |
| US5798380A (en) * | 1996-02-21 | 1998-08-25 | Wisconsin Alumni Research Foundation | Cytoskeletal active agents for glaucoma therapy |
| CO4940418A1 (es) * | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| GB0215676D0 (en) * | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
| BRPI0510485A (pt) * | 2004-04-30 | 2007-11-13 | Allergan Inc | implantes inibidores de tirosina cinase intravìtreos biodegradáveis |
| DK1893213T3 (da) * | 2005-06-03 | 2010-06-07 | Novartis Ag | Kombination af pyrimidylaminobenzamidforbindelser og imatinib til behandling eller forebyggelse af proliferative sygdomme |
| GT200600316A (es) | 2005-07-20 | 2007-04-02 | Sales de 4-metilo-n-(3-(4-metilo-imidazol-1-ilo)-5-trifluorometilo-fenilo)-3-(4-piridina-3-ilo-pirimidina-2-iloamino)- benzamida. | |
| GT200600315A (es) | 2005-07-20 | 2007-03-19 | Formas cristalinas de 4-metilo-n-[3-(4-metilo-imidazol-1-ilo)-5-trifluorometilo-fenilo]-3-(4-pyridina-3-ilo-pirimidina-2-iloamino)-benzamida | |
| JP6623812B2 (ja) * | 2016-02-17 | 2019-12-25 | セイコーエプソン株式会社 | 位置検出装置、及び、そのコントラスト調整方法 |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005526048A (ja) * | 2002-02-27 | 2005-09-02 | アブ サイエンス | Ｃｎｓ疾患を治療するためのチロシンキナーゼ阻害剤の使用方法 |
| WO2008130704A2 (en) * | 2007-04-17 | 2008-10-30 | Imclone Llc | PDGFRβ-SPECIFIC INHIBITORS |
| WO2008155387A2 (en) * | 2007-06-19 | 2008-12-24 | Boehringer Ingelheim International Gmbh | Anti-igf antibodies that bind to igf-1 and igf-2 but not to insulin |
Non-Patent Citations (4)
| Title |
|---|
| JPN6014027371; Ｎａｔｕｒｅ Ｒｅｖｉｅｗｓ Ｄｒｕｇ Ｄｉｓｃｏｖｅｒｙ ７（２）, 2008, ｐ．１６８-１８１ * |
| JPN6014027373; Ｂｉｏｏｒｇａｎｉｃ ＆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ Ｌｅｔｔｅｒｓ １９, 200908, ｐ．４１０２-４１０６ * |
| JPN6015020218; Ｌｅｕｋｅｍｉａ Ｒｅｓｅａｒｃｈ ３２, 2008, ｐ．１０２２-１０２５ * |
| JPN6015020219; Ｈｅｍａｔｏｌ．Ｏｎｃｏｌ．Ｃｌｉｎ．Ｎ．Ａｍ． ２３（１）, 200902, ｐ．１０９-１１４ * |
Also Published As
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| WO2010141427A1 (en) | 2010-12-09 |
| EP2437745A1 (en) | 2012-04-11 |
| EP2437745B1 (en) | 2017-08-23 |
| TWI565466B (zh) | 2017-01-11 |
| US9623025B2 (en) | 2017-04-18 |
| US20120088776A1 (en) | 2012-04-12 |
| TW201102069A (en) | 2011-01-16 |
| WO2010139678A1 (en) | 2010-12-09 |
| JP2017203037A (ja) | 2017-11-16 |
| JP2016020375A (ja) | 2016-02-04 |
| TW201102068A (en) | 2011-01-16 |
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