CN1939910A - 氨基嘧啶类化合物及其盐和其制备方法与药物用途 - Google Patents
氨基嘧啶类化合物及其盐和其制备方法与药物用途 Download PDFInfo
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- CN1939910A CN1939910A CNA2005101074022A CN200510107402A CN1939910A CN 1939910 A CN1939910 A CN 1939910A CN A2005101074022 A CNA2005101074022 A CN A2005101074022A CN 200510107402 A CN200510107402 A CN 200510107402A CN 1939910 A CN1939910 A CN 1939910A
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- 125000005843 halogen group Chemical group 0.000 claims description 42
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- 238000000034 method Methods 0.000 claims description 26
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2005101074022A CN1939910A (zh) | 2004-12-31 | 2005-09-30 | 氨基嘧啶类化合物及其盐和其制备方法与药物用途 |
| ES05822296.9T ES2436758T3 (es) | 2004-12-31 | 2005-12-26 | Compuestos de aminopirimidina y sus sales, proceso de preparación y su uso farmacéutico |
| HK07102609.2A HK1095146B (en) | 2004-12-31 | 2005-12-26 | Aminopyrimidine compounds and their salts, process for preparation and pharmaceutical use thereof |
| PCT/CN2005/002308 WO2006069525A1 (en) | 2004-12-31 | 2005-12-26 | Aminopyrimidine compounds and their salts, process for preparation and pharmaceutical use thereof |
| CA2602738A CA2602738C (en) | 2004-12-31 | 2005-12-26 | Aminopyrimidine compounds and their salts, process for preparation and pharmaceutical use thereof |
| JP2007548675A JP4698681B2 (ja) | 2004-12-31 | 2005-12-26 | アミノピリミジン類の化合物及びその塩の調製方法と薬物の用途 |
| US11/794,250 US8183242B2 (en) | 2004-12-31 | 2005-12-26 | Aminopyrimidine compounds and their salts, process for preparation and pharmaceutical use thereof |
| CN2005800208831A CN1972917B (zh) | 2004-12-31 | 2005-12-26 | 氨基嘧啶类化合物及其盐和其制备方法与药物用途 |
| EP05822296.9A EP1840122B1 (en) | 2004-12-31 | 2005-12-26 | Aminopyrimidine compounds and their salts, process for preparation and pharmaceutical use thereof |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200410103077.8 | 2004-12-31 | ||
| CN200410103077 | 2004-12-31 | ||
| CNA2005101074022A CN1939910A (zh) | 2004-12-31 | 2005-09-30 | 氨基嘧啶类化合物及其盐和其制备方法与药物用途 |
| PCT/CN2005/002308 WO2006069525A1 (en) | 2004-12-31 | 2005-12-26 | Aminopyrimidine compounds and their salts, process for preparation and pharmaceutical use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1939910A true CN1939910A (zh) | 2007-04-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2005101074022A Pending CN1939910A (zh) | 2004-12-31 | 2005-09-30 | 氨基嘧啶类化合物及其盐和其制备方法与药物用途 |
Country Status (7)
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| CN102816146A (zh) * | 2011-06-10 | 2012-12-12 | 江苏豪森医药集团连云港宏创医药有限公司 | 甲磺酸氟马替尼晶型a及其制备方法和用途 |
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| CN107652269A (zh) * | 2016-07-26 | 2018-02-02 | 江苏豪森药业集团有限公司 | 甲磺酸氟马替尼中间体纯化方法 |
| CN109438365A (zh) * | 2018-12-06 | 2019-03-08 | 华南师范大学 | N-(3-((4-三氟甲基)-2-嘧啶基)氨基苯基)-2,6-二氟苯磺酰胺衍生物 |
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Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1043531A (zh) | 1988-12-12 | 1990-07-04 | 衡阳市动力配件厂 | 合金铸铁气缸套 |
| TW225528B (cg-RX-API-DMAC7.html) * | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| GB9610044D0 (en) | 1996-05-14 | 1996-07-17 | Sandoz Ltd | Improvements in or relating to organic compounds |
| GB9619284D0 (en) * | 1996-09-16 | 1996-10-30 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9919778D0 (en) * | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| GB0021726D0 (en) * | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| GB0022438D0 (en) * | 2000-09-13 | 2000-11-01 | Novartis Ag | Organic Compounds |
| EP1377572A1 (en) * | 2001-04-10 | 2004-01-07 | Vertex Pharmaceuticals Incorporated | Isoxaxole derivatives as inhibitors of src and other protein kinases |
| US6884804B2 (en) * | 2001-05-16 | 2005-04-26 | Vertex Pharmaceuticals Incorporated | Inhibitors of Src and other protein kinases |
| MXPA03011652A (es) * | 2001-06-15 | 2004-05-31 | Vertex Pharma | 5-(2-aminopirimidin-4-il) benzioxazoles como inhibidores de proteinas cinasa. |
| US7288547B2 (en) * | 2002-03-11 | 2007-10-30 | Schering Ag | CDK-inhibitory 2-heteroaryl-pyrimidines, their production and use as pharmaceutical agents |
| GB0215676D0 (en) * | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
| GB0222514D0 (en) | 2002-09-27 | 2002-11-06 | Novartis Ag | Organic compounds |
| AU2003232650A1 (en) * | 2003-05-06 | 2004-11-26 | Il Yang Pharm Co., Ltd. | N-phenyl-2-pyrimidine-amine derivatives and process for the preparation thereof |
| CN1805748B (zh) * | 2003-06-13 | 2010-05-26 | 诺瓦提斯公司 | 作为raf激酶抑制剂的2-氨基嘧啶衍生物 |
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2005
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- 2005-12-26 CA CA2602738A patent/CA2602738C/en not_active Expired - Fee Related
- 2005-12-26 EP EP05822296.9A patent/EP1840122B1/en not_active Expired - Lifetime
- 2005-12-26 WO PCT/CN2005/002308 patent/WO2006069525A1/zh not_active Ceased
- 2005-12-26 JP JP2007548675A patent/JP4698681B2/ja not_active Expired - Fee Related
- 2005-12-26 ES ES05822296.9T patent/ES2436758T3/es not_active Expired - Lifetime
- 2005-12-26 US US11/794,250 patent/US8183242B2/en active Active
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| CN103396395A (zh) * | 2013-07-26 | 2013-11-20 | 天津法莫西医药科技有限公司 | 一种合成n-（5-硝基-2-甲基吡啶基-3-）-4-（3-吡啶基）-2-嘧啶胺及其中间体的方法 |
| CN103396395B (zh) * | 2013-07-26 | 2014-09-03 | 天津法莫西医药科技有限公司 | 一种合成n-（5-硝基-2-甲基吡啶基-3-）-4-（3-吡啶基）-2-嘧啶胺及其中间体的方法 |
| CN103360366B (zh) * | 2013-07-26 | 2015-04-01 | 天津禾盛医药技术开发有限公司 | N-(5-硝基-2-甲基吡啶基-3-)-4-(3-吡啶基)-2-嘧啶胺及其中间体的制备方法 |
| CN107652269A (zh) * | 2016-07-26 | 2018-02-02 | 江苏豪森药业集团有限公司 | 甲磺酸氟马替尼中间体纯化方法 |
| CN109438365A (zh) * | 2018-12-06 | 2019-03-08 | 华南师范大学 | N-(3-((4-三氟甲基)-2-嘧啶基)氨基苯基)-2,6-二氟苯磺酰胺衍生物 |
| CN109438365B (zh) * | 2018-12-06 | 2022-04-05 | 华南师范大学 | N-(3-((4-三氟甲基)-2-嘧啶基)氨基苯基)-2,6-二氟苯磺酰胺衍生物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2602738C (en) | 2011-12-20 |
| EP1840122A4 (en) | 2011-03-09 |
| JP4698681B2 (ja) | 2011-06-08 |
| HK1095146A1 (en) | 2007-04-27 |
| JP2008526692A (ja) | 2008-07-24 |
| US8183242B2 (en) | 2012-05-22 |
| ES2436758T3 (es) | 2014-01-07 |
| EP1840122A1 (en) | 2007-10-03 |
| US20080312251A1 (en) | 2008-12-18 |
| EP1840122B1 (en) | 2013-08-28 |
| CA2602738A1 (en) | 2006-07-06 |
| WO2006069525A1 (en) | 2006-07-06 |
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