JP2007523072A5 - - Google Patents
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- JP2007523072A5 JP2007523072A5 JP2006551898A JP2006551898A JP2007523072A5 JP 2007523072 A5 JP2007523072 A5 JP 2007523072A5 JP 2006551898 A JP2006551898 A JP 2006551898A JP 2006551898 A JP2006551898 A JP 2006551898A JP 2007523072 A5 JP2007523072 A5 JP 2007523072A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- group
- formula
- methyl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 138
- 125000001424 substituent group Chemical group 0.000 claims 44
- 125000000623 heterocyclic group Chemical group 0.000 claims 37
- -1 carboxy, carbamoyl Chemical group 0.000 claims 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 36
- 239000001257 hydrogen Substances 0.000 claims 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 31
- 229910052799 carbon Inorganic materials 0.000 claims 30
- 229910052757 nitrogen Inorganic materials 0.000 claims 25
- 150000003246 quinazolines Chemical class 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 22
- 125000001589 carboacyl group Chemical group 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 13
- 150000001721 carbon Chemical group 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 125000000304 alkynyl group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 11
- 238000000034 method Methods 0.000 claims 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 10
- 125000005236 alkanoylamino group Chemical group 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 8
- 125000000524 functional group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 7
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 241001465754 Metazoa Species 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 238000003780 insertion Methods 0.000 claims 3
- 230000037431 insertion Effects 0.000 claims 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 2
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- GVUGERXCDIPSLL-OAQYLSRUSA-N (2R)-2-[[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]methyl]-3-methoxy-2-(methylamino)propanamide Chemical compound ClC=1C(=C(C=CC=1)NC1=NC=NC2=CC(=C(C=C12)C[C@@](NC)(COC)C(=O)N)OC)F GVUGERXCDIPSLL-OAQYLSRUSA-N 0.000 claims 1
- BHVAKJBKJSVSDR-IBGZPJMESA-N (2S)-2-amino-3-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]-2-methylpropanamide Chemical compound ClC=1C(=C(C=CC=1)NC1=NC=NC2=CC(=C(C=C12)C[C@@](N)(C)C(=O)N)OC)F BHVAKJBKJSVSDR-IBGZPJMESA-N 0.000 claims 1
- IRCSMVSKUWTDJU-QFIPXVFZSA-N (2S)-3-[4-(3-chloro-2-fluoroanilino)-7-(2-methoxyethoxy)quinazolin-6-yl]-2-methyl-2-(methylamino)propanamide Chemical compound ClC=1C(=C(C=CC=1)NC1=NC=NC2=CC(=C(C=C12)C[C@@](NC)(C)C(=O)N)OCCOC)F IRCSMVSKUWTDJU-QFIPXVFZSA-N 0.000 claims 1
- NOUPFVBLDOHUPJ-NRFANRHFSA-N (2S)-3-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]-2-(ethylamino)-2-methylpropanamide Chemical compound ClC=1C(=C(C=CC=1)NC1=NC=NC2=CC(=C(C=C12)C[C@@](NCC)(C)C(=O)N)OC)F NOUPFVBLDOHUPJ-NRFANRHFSA-N 0.000 claims 1
- WBFNVNILPDYQMM-FQEVSTJZSA-N (2S)-3-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]-2-methyl-2-(methylamino)propanamide Chemical compound ClC=1C(=C(C=CC=1)NC1=NC=NC2=CC(=C(C=C12)C[C@@](NC)(C)C(=O)N)OC)F WBFNVNILPDYQMM-FQEVSTJZSA-N 0.000 claims 1
- BZFIWVPQDDVKDV-NRFANRHFSA-N (2S)-3-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]-N,2-dimethyl-2-(methylamino)propanamide Chemical compound ClC=1C(=C(C=CC=1)NC1=NC=NC2=CC(=C(C=C12)C[C@@](NC)(C)C(=O)NC)OC)F BZFIWVPQDDVKDV-NRFANRHFSA-N 0.000 claims 1
- DJUCIYJITXCSLS-FQEVSTJZSA-N (2S)-3-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]-2-methyl-2-(methylamino)propanamide Chemical compound ClC=1C=C(C=CC=1F)NC1=NC=NC2=CC(=C(C=C12)C[C@@](NC)(C)C(=O)N)OC DJUCIYJITXCSLS-FQEVSTJZSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- IKXPVMNZZLUFCI-UHFFFAOYSA-N 3-[[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]methyl-methylamino]-1-(2-methoxyethyl)azetidine-3-carboxamide Chemical compound C1N(CCOC)CC1(C(N)=O)N(C)CC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(Cl)=C1F IKXPVMNZZLUFCI-UHFFFAOYSA-N 0.000 claims 1
- SGSZBDPHZWMJPU-UHFFFAOYSA-N 3-[[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]methyl-methylamino]-1-methylazetidine-3-carboxamide Chemical compound C=12C=C(CN(C)C3(CN(C)C3)C(N)=O)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F SGSZBDPHZWMJPU-UHFFFAOYSA-N 0.000 claims 1
- JLFUYZIWZMFTMH-UHFFFAOYSA-N 3-[[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]methyl-methylamino]-1-methylpiperidine-3-carboxamide Chemical compound C=12C=C(CN(C)C3(CN(C)CCC3)C(N)=O)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F JLFUYZIWZMFTMH-UHFFFAOYSA-N 0.000 claims 1
- VUWJAUDVPQZJHG-UHFFFAOYSA-N 3-[[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]methyl-methylamino]-1-propan-2-ylazetidine-3-carboxamide Chemical compound C=12C=C(CN(C)C3(CN(C3)C(C)C)C(N)=O)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F VUWJAUDVPQZJHG-UHFFFAOYSA-N 0.000 claims 1
- XRUQVQJWTQESAB-UHFFFAOYSA-N 4-[[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]methyl-methylamino]-1-methylpiperidine-4-carboxamide Chemical compound C=12C=C(CN(C)C3(CCN(C)CC3)C(N)=O)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F XRUQVQJWTQESAB-UHFFFAOYSA-N 0.000 claims 1
- OJXVSOYHWKXTRW-UHFFFAOYSA-N 4-[[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]methyl-methylamino]-n,1-dimethylpiperidine-4-carboxamide Chemical compound C=1C2=C(NC=3C(=C(Cl)C=CC=3)F)N=CN=C2C=C(OC)C=1CN(C)C1(C(=O)NC)CCN(C)CC1 OJXVSOYHWKXTRW-UHFFFAOYSA-N 0.000 claims 1
- FXQBMHQIDXOJPW-UHFFFAOYSA-N N'-[[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]methyl]-N'-ethylcyclopropanecarbohydrazide Chemical compound C1(CC1)C(=O)NN(CC)CC=1C=C2C(=NC=NC2=CC1OC)NC1=C(C(=CC=C1)Cl)F FXQBMHQIDXOJPW-UHFFFAOYSA-N 0.000 claims 1
- CVFXKZZCTHUDRF-UHFFFAOYSA-N N'-[[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]methyl]-N'-methylcyclopent-3-ene-1-carbohydrazide Chemical compound C1(CC=CC1)C(=O)NN(C)CC=1C=C2C(=NC=NC2=CC1OC)NC1=C(C(=CC=C1)Cl)F CVFXKZZCTHUDRF-UHFFFAOYSA-N 0.000 claims 1
- PURZOLAIZPYHSS-UHFFFAOYSA-N N'-[[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]methyl]-N'-methylcyclopropanecarbohydrazide Chemical compound C1(CC1)C(=O)NN(C)CC=1C=C2C(=NC=NC2=CC=1OC)NC1=C(C(=CC=C1)Cl)F PURZOLAIZPYHSS-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 1
- 108010077895 Sarcosine Proteins 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims 1
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04290274 | 2004-02-03 | ||
| EP04290274.2 | 2004-02-03 | ||
| PCT/GB2005/000237 WO2005075439A1 (en) | 2004-02-03 | 2005-01-31 | Quinazoline derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007523072A JP2007523072A (ja) | 2007-08-16 |
| JP2007523072A5 true JP2007523072A5 (enExample) | 2008-03-21 |
| JP5032851B2 JP5032851B2 (ja) | 2012-09-26 |
Family
ID=34833782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006551898A Expired - Fee Related JP5032851B2 (ja) | 2004-02-03 | 2005-01-31 | キナゾリン誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7632840B2 (enExample) |
| EP (1) | EP1713781B1 (enExample) |
| JP (1) | JP5032851B2 (enExample) |
| CN (1) | CN1914182B (enExample) |
| AR (1) | AR047703A1 (enExample) |
| AT (1) | ATE413389T1 (enExample) |
| DE (1) | DE602005010824D1 (enExample) |
| ES (1) | ES2315834T3 (enExample) |
| TW (1) | TW200529851A (enExample) |
| UY (1) | UY28736A1 (enExample) |
| WO (1) | WO2005075439A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| JP2005515176A (ja) * | 2001-11-03 | 2005-05-26 | アストラゼネカ アクチボラグ | 抗腫瘍剤としてのキナゾリン誘導体 |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| AU2004272350A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| US7569577B2 (en) * | 2003-09-16 | 2009-08-04 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| BRPI0414488A (pt) * | 2003-09-16 | 2006-11-14 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, métodos para produzir um efeito anti - proliferativo em um animal de sangue quente, para prevenção ou tratamento de tumores em um aminal de sangue quente, para fornecer um efeito inibidor da tirosina quinase de egfr seletivo em um animal de sangue quente e para tratar um cáncer em um animal de sangue quente e, processo para a preparação de um derivado de quinazolina |
| EP1664030A1 (en) * | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| CA2567832A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
| GB2418427A (en) | 2004-09-02 | 2006-03-29 | Univ Cambridge Tech | Ligands for G-protein coupled receptors |
| CN101124228B (zh) * | 2004-12-14 | 2011-06-15 | 阿斯利康(瑞典)有限公司 | 用作抗肿瘤药物的吡唑并嘧啶化合物 |
| GB0504474D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| GB0508715D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| US7820683B2 (en) * | 2005-09-20 | 2010-10-26 | Astrazeneca Ab | 4-(1H-indazol-5-yl-amino)-quinazoline compounds as erbB receptor tyrosine kinase inhibitors for the treatment of cancer |
| US20090239861A1 (en) * | 2005-09-20 | 2009-09-24 | Robert Hugh Bradbury | Quinazoline derivatives as anticancer agents |
| ATE443053T1 (de) * | 2005-12-02 | 2009-10-15 | Astrazeneca Ab | Als inhibitoren von erbb-tyrosinkinase verwendete chinazoleinderivate |
| WO2007063291A1 (en) * | 2005-12-02 | 2007-06-07 | Astrazeneca Ab | 4-anilino-substituted quinazoline derivatives as tyrosine kinase inhibitors |
| WO2008134048A2 (en) | 2007-04-27 | 2008-11-06 | Paratek Pharmaceuticals, Inc. | Methods for synthesizing and purifying aminoalkyl tetracycline compounds |
| CN101784517A (zh) | 2007-07-06 | 2010-07-21 | 帕拉特克药品公司 | 合成取代的四环素化合物的方法 |
| GB2452696B (en) | 2007-08-02 | 2009-09-23 | Cambridge Entpr Ltd | 3-(2',2'-dimethylpropanoylamino)-tetrahydropyridin-2-one and its use in pharmaceutical compositions |
| US7662967B2 (en) | 2007-08-02 | 2010-02-16 | Cambridge Enterprise Limited | Anti-inflammatory compounds and compositions |
| GB201604329D0 (en) * | 2016-03-14 | 2016-04-27 | Univ Strathclyde | Methods and systems for improving stability of a ship |
| CN111777620A (zh) * | 2019-04-04 | 2020-10-16 | 山东轩竹医药科技有限公司 | 酪氨酸激酶抑制剂的新用途 |
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| GB9514265D0 (en) | 1995-07-13 | 1995-09-13 | Wellcome Found | Hetrocyclic compounds |
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-
2005
- 2005-01-31 AT AT05701999T patent/ATE413389T1/de not_active IP Right Cessation
- 2005-01-31 CN CN2005800038578A patent/CN1914182B/zh not_active Expired - Fee Related
- 2005-01-31 ES ES05701999T patent/ES2315834T3/es not_active Expired - Lifetime
- 2005-01-31 WO PCT/GB2005/000237 patent/WO2005075439A1/en not_active Ceased
- 2005-01-31 EP EP05701999A patent/EP1713781B1/en not_active Expired - Lifetime
- 2005-01-31 US US10/586,965 patent/US7632840B2/en not_active Expired - Fee Related
- 2005-01-31 DE DE602005010824T patent/DE602005010824D1/de not_active Expired - Lifetime
- 2005-01-31 JP JP2006551898A patent/JP5032851B2/ja not_active Expired - Fee Related
- 2005-02-02 UY UY28736A patent/UY28736A1/es unknown
- 2005-02-03 AR ARP050100415A patent/AR047703A1/es unknown
- 2005-02-03 TW TW094103412A patent/TW200529851A/zh unknown
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