JP2013511475A5 - - Google Patents
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- Publication number
- JP2013511475A5 JP2013511475A5 JP2012539175A JP2012539175A JP2013511475A5 JP 2013511475 A5 JP2013511475 A5 JP 2013511475A5 JP 2012539175 A JP2012539175 A JP 2012539175A JP 2012539175 A JP2012539175 A JP 2012539175A JP 2013511475 A5 JP2013511475 A5 JP 2013511475A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- oxy
- dimethylamino
- phenyl
- amino
- 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
- 238000000034 method Methods 0.000 claims 32
- -1 2- (dimethylamino) ethyl Chemical group 0.000 claims 31
- 239000003814 drug Substances 0.000 claims 24
- 229940124597 therapeutic agent Drugs 0.000 claims 24
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 9
- TTZSNFLLYPYKIL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-1-[3-[[4-[(2-methyl-1h-indol-5-yl)oxy]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound CN(C)CCNS(=O)(=O)CC1=CC=CC(NC=2N=C(OC=3C=C4C=C(C)NC4=CC=3)C=CN=2)=C1 TTZSNFLLYPYKIL-UHFFFAOYSA-N 0.000 claims 8
- ZEOWTGPWHLSLOG-UHFFFAOYSA-N Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F Chemical compound Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F ZEOWTGPWHLSLOG-UHFFFAOYSA-N 0.000 claims 6
- 102100023593 Fibroblast growth factor receptor 1 Human genes 0.000 claims 6
- 101710182386 Fibroblast growth factor receptor 1 Proteins 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 230000033115 angiogenesis Effects 0.000 claims 6
- 239000000010 aprotic solvent Substances 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 238000001816 cooling Methods 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 238000004090 dissolution Methods 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 238000010992 reflux Methods 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- SMRKYYXMQGTANS-UHFFFAOYSA-N N,N-dimethyl-N'-[4-[(2-methyl-1H-indol-5-yl)oxy]pyrimidin-2-yl]-N'-(3-methylphenyl)ethane-1,2-diamine Chemical compound CN(C)CCN(c1cccc(C)c1)c1nccc(Oc2ccc3[nH]c(C)cc3c2)n1 SMRKYYXMQGTANS-UHFFFAOYSA-N 0.000 claims 4
- 230000005764 inhibitory process Effects 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229940124530 sulfonamide Drugs 0.000 claims 4
- 150000003456 sulfonamides Chemical class 0.000 claims 4
- 206010064930 age-related macular degeneration Diseases 0.000 claims 3
- 150000001298 alcohols Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 208000002780 macular degeneration Diseases 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 239000008186 active pharmaceutical agent Substances 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000009257 reactivity Effects 0.000 claims 2
- 230000004043 responsiveness Effects 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
- 238000010899 nucleation Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000009331 sowing Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101992592A CN102070618B (zh) | 2009-11-23 | 2009-11-23 | 一种化合物及其晶体 |
| CN200910199259.2 | 2009-11-23 | ||
| PCT/CN2010/078997 WO2011060746A1 (en) | 2009-11-23 | 2010-11-23 | Compound, certain novel forms thereof, pharmaceutical compositions thereof and methods for preparation and use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013511475A JP2013511475A (ja) | 2013-04-04 |
| JP2013511475A5 true JP2013511475A5 (enExample) | 2014-01-16 |
| JP5758399B2 JP5758399B2 (ja) | 2015-08-05 |
Family
ID=44029398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012539175A Active JP5758399B2 (ja) | 2009-11-23 | 2010-11-23 | 化合物、その一定の新形態、その医薬組成物ならびに製剤化および使用の方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US8658658B2 (enExample) |
| EP (1) | EP2504331B1 (enExample) |
| JP (1) | JP5758399B2 (enExample) |
| KR (1) | KR101513784B1 (enExample) |
| CN (2) | CN102070618B (enExample) |
| AU (1) | AU2010321366B2 (enExample) |
| BR (1) | BR112012012138B1 (enExample) |
| CA (1) | CA2781066C (enExample) |
| DK (1) | DK2504331T3 (enExample) |
| ES (1) | ES2529105T3 (enExample) |
| IN (1) | IN2012DN04868A (enExample) |
| MX (1) | MX2012005926A (enExample) |
| MY (1) | MY161749A (enExample) |
| NZ (1) | NZ600266A (enExample) |
| PH (1) | PH12012500992A1 (enExample) |
| PL (1) | PL2504331T3 (enExample) |
| PT (1) | PT2504331E (enExample) |
| RU (1) | RU2507203C1 (enExample) |
| WO (1) | WO2011060746A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070618B (zh) * | 2009-11-23 | 2013-08-21 | 和记黄埔医药（上海）有限公司 | 一种化合物及其晶体 |
| CA2952857A1 (en) * | 2014-06-19 | 2015-12-23 | Merial, Inc. | Parasiticidal compositions comprising indole derivatives, methods and uses thereof |
| CN105985326B (zh) * | 2015-02-16 | 2020-04-14 | 上海宣创生物科技有限公司 | 嘧啶衍生物晶型ⅲ及其制备方法和用途 |
| WO2016187767A1 (en) * | 2015-05-25 | 2016-12-01 | Hutchison Medipharma Limited | Pharmaceutical compositions and use thereof |
| WO2018090324A1 (en) * | 2016-11-18 | 2018-05-24 | Hutchison Medipharma Limited | Method of treating solid tumors |
| JP2020164434A (ja) * | 2019-03-28 | 2020-10-08 | 上野製薬株式会社 | ２，６−ナフタレンビス（２−オキサゾリン）の製造方法 |
| WO2021180027A1 (zh) * | 2020-03-09 | 2021-09-16 | 和记黄埔医药（上海）有限公司 | 抗pd-1抗体和多受体酪氨酸激酶抑制剂的药物组合及其使用方法 |
| BR112023021066A2 (pt) * | 2021-04-12 | 2023-12-12 | Mitoimmune Therapeutics Inc | Forma cristalina a, método para preparar a forma cristalina a, composição farmacêutica, e, composição |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA200607639B (en) * | 2004-03-30 | 2008-05-28 | Taisho Pharmaceutical Co Ltd | Pyrimidine derivatives and methods of treatment related to the use thereof |
| US20090149467A1 (en) | 2005-09-15 | 2009-06-11 | Merck & Co., Inc. | Tyrosine Kinase Inhibitors |
| CA2684470C (en) * | 2007-04-16 | 2016-02-09 | Hutchison Medipharma Enterprises Limited | Pyrimidine derivatives |
| CN101289444B (zh) * | 2007-04-16 | 2012-01-04 | 和记黄埔医药（上海）有限公司 | 一种嘧啶衍生物及其医药用途 |
| TW201008933A (en) * | 2008-08-29 | 2010-03-01 | Hutchison Medipharma Entpr Ltd | Pyrimidine compounds |
| CN102070618B (zh) * | 2009-11-23 | 2013-08-21 | 和记黄埔医药（上海）有限公司 | 一种化合物及其晶体 |
-
2009
- 2009-11-23 CN CN2009101992592A patent/CN102070618B/zh active Active
-
2010
- 2010-11-23 IN IN4868DEN2012 patent/IN2012DN04868A/en unknown
- 2010-11-23 NZ NZ600266A patent/NZ600266A/en unknown
- 2010-11-23 PH PH1/2012/500992A patent/PH12012500992A1/en unknown
- 2010-11-23 BR BR112012012138-3A patent/BR112012012138B1/pt active IP Right Grant
- 2010-11-23 CA CA2781066A patent/CA2781066C/en active Active
- 2010-11-23 EP EP10831161.4A patent/EP2504331B1/en active Active
- 2010-11-23 WO PCT/CN2010/078997 patent/WO2011060746A1/en not_active Ceased
- 2010-11-23 CN CN201080052921.2A patent/CN102648194B/zh active Active
- 2010-11-23 MY MYPI2012002250A patent/MY161749A/en unknown
- 2010-11-23 PT PT108311614T patent/PT2504331E/pt unknown
- 2010-11-23 JP JP2012539175A patent/JP5758399B2/ja active Active
- 2010-11-23 PL PL10831161T patent/PL2504331T3/pl unknown
- 2010-11-23 KR KR1020127015836A patent/KR101513784B1/ko active Active
- 2010-11-23 AU AU2010321366A patent/AU2010321366B2/en active Active
- 2010-11-23 ES ES10831161.4T patent/ES2529105T3/es active Active
- 2010-11-23 DK DK10831161.4T patent/DK2504331T3/en active
- 2010-11-23 MX MX2012005926A patent/MX2012005926A/es active IP Right Grant
- 2010-11-23 US US13/510,249 patent/US8658658B2/en active Active
- 2010-11-23 RU RU2012126112/04A patent/RU2507203C1/ru active
-
2013
- 2013-12-12 US US14/104,954 patent/US8946249B2/en active Active
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