JP2011515421A5 - - Google Patents
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- Publication number
- JP2011515421A5 JP2011515421A5 JP2011501089A JP2011501089A JP2011515421A5 JP 2011515421 A5 JP2011515421 A5 JP 2011515421A5 JP 2011501089 A JP2011501089 A JP 2011501089A JP 2011501089 A JP2011501089 A JP 2011501089A JP 2011515421 A5 JP2011515421 A5 JP 2011515421A5
- Authority
- JP
- Japan
- Prior art keywords
- type
- solution
- crystals
- quinazolin
- phenylamino
- 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
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 20
- 239000013078 crystal Substances 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 239000000010 aprotic solvent Substances 0.000 claims 12
- 239000003586 protic polar solvent Substances 0.000 claims 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 11
- ZMUKJEHWLJBODV-UHFFFAOYSA-N n-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]quinazolin-6-yl]prop-2-enamide;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.FC1=CC=CC(COC=2C(=CC(NC=3C4=CC(NC(=O)C=C)=CC=C4N=CN=3)=CC=2)Cl)=C1 ZMUKJEHWLJBODV-UHFFFAOYSA-N 0.000 claims 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- 238000000634 powder X-ray diffraction Methods 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 238000005406 washing Methods 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000002329 infrared spectrum Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000013128 Squamous cell carcinoma of pancreas Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 201000006691 pancreatic squamous cell carcinoma Diseases 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810043189.7 | 2008-03-25 | ||
| CN200810043189A CN101544609A (zh) | 2008-03-25 | 2008-03-25 | 4-苯胺喹唑啉衍生物的结晶形式 |
| PCT/CN2009/000317 WO2009117899A1 (zh) | 2008-03-25 | 2009-03-25 | 4-苯胺喹唑啉衍生物多晶型物及其制法和应用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011515421A JP2011515421A (ja) | 2011-05-19 |
| JP2011515421A5 true JP2011515421A5 (https=) | 2012-05-17 |
| JP5460689B2 JP5460689B2 (ja) | 2014-04-02 |
Family
ID=41112941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011501089A Active JP5460689B2 (ja) | 2008-03-25 | 2009-03-25 | ４−フェニルアミノキナゾリン誘導体の多形、その調製方法、およびその使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US8338438B2 (https=) |
| EP (1) | EP2269994B1 (https=) |
| JP (1) | JP5460689B2 (https=) |
| KR (1) | KR101579148B1 (https=) |
| CN (4) | CN101544609A (https=) |
| AU (1) | AU2009229433B2 (https=) |
| CA (1) | CA2719523C (https=) |
| WO (1) | WO2009117899A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101584696A (zh) | 2008-05-21 | 2009-11-25 | 上海艾力斯医药科技有限公司 | 包含喹唑啉衍生物的组合物及制备方法、用途 |
| CN104558041B (zh) * | 2015-01-30 | 2017-01-11 | 江苏康缘药业股份有限公司 | 含磷取代的喹唑啉衍生物的新晶型及其制备方法和应用 |
| CN104558040B (zh) * | 2015-01-30 | 2017-04-05 | 江苏康缘药业股份有限公司 | 含磷取代的喹唑啉衍生物的晶型及其制备方法和应用 |
| CN104558043B (zh) * | 2015-01-30 | 2017-01-11 | 江苏康缘药业股份有限公司 | 含磷取代的喹唑啉衍生物的新晶型及其制备方法和应用 |
| CN104610364B (zh) * | 2015-01-30 | 2017-03-29 | 江苏康缘药业股份有限公司 | 含磷取代的喹唑啉衍生物的新晶型及其制备方法和应用 |
| CN104558042B (zh) * | 2015-01-30 | 2017-03-29 | 江苏康缘药业股份有限公司 | 含磷取代的喹唑啉衍生物的新晶型及其制备方法和应用 |
| JP2019521175A (ja) * | 2016-07-22 | 2019-07-25 | メッドシャイン ディスカバリー インコーポレイテッド | ニトロイミダゾール系化合物の結晶形、塩形およびその製造方法 |
| JP7191446B2 (ja) * | 2017-01-30 | 2022-12-19 | 塩野義製薬株式会社 | キナゾリン誘導体を含有する固形製剤 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9707453A (es) | 1995-03-30 | 1997-12-31 | Pfizer | Derivados de quinazolina. |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| ZA986732B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitiors of tyrosine kinases |
| AU5391099A (en) | 1998-07-30 | 2000-02-21 | American Home Products Corporation | Substituted quinazoline derivatives |
| WO2000031048A1 (en) | 1998-11-19 | 2000-06-02 | Warner-Lambert Company | N-[4-(3-chloro-4-fluoro-phenylamino)-7-(3-morpholin-4-yl-propoxy)-quinazolin-6-yl]-acrylamide, an irreversible inhibitor of tyrosine kinases |
| KR100735639B1 (ko) | 2004-12-29 | 2007-07-04 | 한미약품 주식회사 | 암세포 성장 억제 효과를 갖는 퀴나졸린 유도체 및 이의제조방법 |
| CN101003514A (zh) * | 2006-01-20 | 2007-07-25 | 上海艾力斯医药科技有限公司 | 喹唑啉衍生物、其制备方法及用途 |
| CN101245050A (zh) * | 2007-02-14 | 2008-08-20 | 上海艾力斯医药科技有限公司 | 4-苯胺喹唑啉衍生物的盐 |
-
2008
- 2008-03-25 CN CN200810043189A patent/CN101544609A/zh active Pending
-
2009
- 2009-03-25 KR KR1020107023879A patent/KR101579148B1/ko active Active
- 2009-03-25 CN CN200980110404.3A patent/CN102007104B/zh active Active
- 2009-03-25 EP EP09724386.9A patent/EP2269994B1/en active Active
- 2009-03-25 CA CA2719523A patent/CA2719523C/en active Active
- 2009-03-25 JP JP2011501089A patent/JP5460689B2/ja active Active
- 2009-03-25 CN CN201310290989.XA patent/CN103420925B/zh active Active
- 2009-03-25 AU AU2009229433A patent/AU2009229433B2/en active Active
- 2009-03-25 WO PCT/CN2009/000317 patent/WO2009117899A1/zh not_active Ceased
- 2009-03-25 CN CN201310291127.9A patent/CN103382183B/zh active Active
- 2009-03-25 US US12/934,478 patent/US8338438B2/en active Active
-
2012
- 2012-11-19 US US13/680,330 patent/US8937079B2/en active Active
-
2014
- 2014-11-18 US US14/546,451 patent/US9102629B2/en active Active
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