JP2007505878A5 - - Google Patents
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- JP2007505878A5 JP2007505878A5 JP2006526702A JP2006526702A JP2007505878A5 JP 2007505878 A5 JP2007505878 A5 JP 2007505878A5 JP 2006526702 A JP2006526702 A JP 2006526702A JP 2006526702 A JP2006526702 A JP 2006526702A JP 2007505878 A5 JP2007505878 A5 JP 2007505878A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- quinazoline derivative
- quinazoline
- alkyl
- 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.)
- Pending
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- 150000003246 quinazolines Chemical class 0.000 claims 53
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 238000000034 method Methods 0.000 claims 21
- -1 cyano, nitro, hydroxy, amino, carboxy, sulfamoyl Chemical group 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 125000001153 fluoro group Chemical group F* 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000000524 functional group Chemical group 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 230000001028 anti-proliverative effect Effects 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- CGMPCBYTPCIRJU-UHFFFAOYSA-N 2-(4-methylpiperidin-1-yl)ethyl 4-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OCCN3CCC(C)CC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F CGMPCBYTPCIRJU-UHFFFAOYSA-N 0.000 claims 1
- LLOAHEIQGBGGTQ-UHFFFAOYSA-N 2-(diethylamino)ethyl 4-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCCN(CC)CC)CCC1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(Cl)=C1F LLOAHEIQGBGGTQ-UHFFFAOYSA-N 0.000 claims 1
- BWYJJZBRYSADRP-UHFFFAOYSA-N 2-methoxyquinazoline Chemical class C1=CC=CC2=NC(OC)=NC=C21 BWYJJZBRYSADRP-UHFFFAOYSA-N 0.000 claims 1
- UGPGIBUJVVDLOA-UHFFFAOYSA-N 2-morpholin-4-ylethyl 4-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F UGPGIBUJVVDLOA-UHFFFAOYSA-N 0.000 claims 1
- MGTBTQYQBPWHRY-UHFFFAOYSA-N 2-piperidin-1-ylethyl 4-[4-(3-chloro-2,4-difluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OCCN3CCCCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1F MGTBTQYQBPWHRY-UHFFFAOYSA-N 0.000 claims 1
- CFYLMJJPWKHYLO-UHFFFAOYSA-N 2-piperidin-1-ylethyl 4-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OCCN3CCCCC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F CFYLMJJPWKHYLO-UHFFFAOYSA-N 0.000 claims 1
- MTUHLNORBDFEJP-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl 4-[4-(3-chloro-2,4-difluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OCCN3CCCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1F MTUHLNORBDFEJP-UHFFFAOYSA-N 0.000 claims 1
- OPBJJFYRTBAOMF-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl 4-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OCCN3CCCC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F OPBJJFYRTBAOMF-UHFFFAOYSA-N 0.000 claims 1
- QAKBRNPYOXEUPZ-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl 4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OCCN3CCCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 QAKBRNPYOXEUPZ-UHFFFAOYSA-N 0.000 claims 1
- RQZNUDVCDCQOEL-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl 4-[4-(3-chloroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OCCN3CCCC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1 RQZNUDVCDCQOEL-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- NDXVVVPOQKIUGG-UHFFFAOYSA-N methyl 4-[4-(3-chloro-2,4-difluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1F NDXVVVPOQKIUGG-UHFFFAOYSA-N 0.000 claims 1
- HRQAEZQBAMRCSA-UHFFFAOYSA-N methyl 4-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(Cl)=C1F HRQAEZQBAMRCSA-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- DQORBCOTYYJLTB-UHFFFAOYSA-N propan-2-yl 4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OC(C)C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 DQORBCOTYYJLTB-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- LLTCDTSMNWDXIP-UHFFFAOYSA-N tert-butyl 4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical group C=12C=C(OC3CCN(CC3)C(=O)OC(C)(C)C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 LLTCDTSMNWDXIP-UHFFFAOYSA-N 0.000 claims 1
- QJQCSXAKSADYBA-UHFFFAOYSA-N tert-butyl 4-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OC(C)(C)C)C(OC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 QJQCSXAKSADYBA-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03292308 | 2003-09-19 | ||
| EP04291249 | 2004-05-14 | ||
| PCT/GB2004/004109 WO2005028470A1 (en) | 2003-09-19 | 2004-09-15 | Quinazoline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007505878A JP2007505878A (ja) | 2007-03-15 |
| JP2007505878A5 true JP2007505878A5 (enExample) | 2007-07-12 |
Family
ID=34379391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006526702A Pending JP2007505878A (ja) | 2003-09-19 | 2004-09-15 | キナゾリン誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20070037837A1 (enExample) |
| EP (1) | EP1670782B1 (enExample) |
| JP (1) | JP2007505878A (enExample) |
| CN (1) | CN1882570B (enExample) |
| AT (1) | ATE353888T1 (enExample) |
| DE (1) | DE602004004811T2 (enExample) |
| ES (1) | ES2281007T3 (enExample) |
| WO (1) | WO2005028470A1 (enExample) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| RU2004116911A (ru) * | 2001-11-03 | 2005-11-10 | Астразенека Аб (Se) | Производные хиназолина в качестве противоопухолевых средств |
| TW200813014A (en) * | 2002-03-28 | 2008-03-16 | Astrazeneca Ab | Quinazoline derivatives |
| US6924285B2 (en) | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| GB0317665D0 (en) | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| WO2005026150A1 (en) | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| WO2005026156A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| 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 |
| MXPA06002963A (es) * | 2003-09-16 | 2006-06-14 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de cinasa de tirosina. |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| BRPI0414532B1 (pt) * | 2003-09-19 | 2018-06-05 | Astrazeneca Ab | Composto derivado de quinazolina, processo para preparar 0 mesmo, composição farmaceutica, e, uso de um composto derivado de quinazolina |
| MXPA06003341A (es) * | 2003-09-25 | 2006-06-08 | Astrazeneca Ab | Derivados de quinazolina. |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| ATE413389T1 (de) | 2004-02-03 | 2008-11-15 | Astrazeneca Ab | Chinazolinderivate |
| CA2567832A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
| ATE501148T1 (de) * | 2004-12-14 | 2011-03-15 | Astrazeneca Ab | Pyrazolopyrimidinverbindungen als antitumormittel |
| AU2006217738A1 (en) * | 2005-02-26 | 2006-08-31 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| 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 |
| ES2354457T3 (es) * | 2005-09-20 | 2011-03-15 | Astrazeneca Ab | Compuestos de 4-(1h-indazol-5-il-amino)-quinazolina como inhibidores del receptor erbb de la tirosina quinasa para el tratamiento del cáncer. |
| WO2007034143A1 (en) * | 2005-09-20 | 2007-03-29 | Astrazeneca Ab | Quinazoline derivatives as anticancer agents |
| CA2833706C (en) | 2005-11-11 | 2014-10-21 | Boehringer Ingelheim International Gmbh | Quinazoline derivatives for the treatment of cancer diseases |
| JP2009517451A (ja) * | 2005-12-02 | 2009-04-30 | アストラゼネカ アクチボラグ | Erbbチロシンキナーゼの阻害剤として使用されるキナゾリン誘導体 |
| EP1957499A1 (en) * | 2005-12-02 | 2008-08-20 | AstraZeneca AB | 4-anilino-substituted quinazoline derivatives as tyrosine kinase inhibitors |
| EP1966189A1 (de) * | 2005-12-12 | 2008-09-10 | Boehringer Ingelheim International Gmbh | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| EP1921070A1 (de) * | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| JP5377332B2 (ja) | 2007-02-06 | 2013-12-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 二環式へテロ環、それらの化合物を含む薬剤、その使用及びその製法 |
| WO2009098061A1 (de) | 2008-02-07 | 2009-08-13 | Boehringer Ingelheim International Gmbh | Spirocyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| MX2010012442A (es) * | 2008-05-13 | 2011-10-11 | Astrazeneca Ab | Sal de fumarato de 4-(3-cloro-2-fluoroanilino)-7-metoxi-6-{[1-(n-m etilcarbamoilmetil) piperidin-4-il]oxi}quinazolina. |
| EP2313397B1 (de) | 2008-08-08 | 2016-04-20 | Boehringer Ingelheim International GmbH | Cyclohexyloxy-substituierte heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| SI2451445T1 (sl) | 2009-07-06 | 2019-07-31 | Boehringer Ingelheim International Gmbh | Postopek za sušenje BIBW2992, njegovih soli in trdnih farmacevtskih formulacij, ki obsegajo to aktivno sestavino |
| KR101217526B1 (ko) * | 2010-06-11 | 2013-01-02 | 한미사이언스 주식회사 | 아마이드 유도체 또는 이의 약학적으로 허용 가능한 염을 포함하는 약제학적 조성물 |
| KR101317809B1 (ko) | 2011-06-07 | 2013-10-16 | 한미약품 주식회사 | 암세포의 성장을 억제하는 아마이드 유도체 및 비금속염 활택제를 포함하는 약학 조성물 |
| KR101272613B1 (ko) * | 2011-10-05 | 2013-06-10 | 한미사이언스 주식회사 | 1-(4-(4-(3,4-디클로로-2-플루오로페닐아미노)-7-메톡시퀴나졸린-6-일옥시)피페리딘-1-일)프로프-2-엔-1-온 염산염의 제조 방법 및 이에 사용되는 중간체 |
| US9546179B2 (en) * | 2011-12-20 | 2017-01-17 | Wei Qian | Heterocycle amido alkyloxy substituted quinazoline derivative and use thereof |
| KR20140096571A (ko) * | 2013-01-28 | 2014-08-06 | 한미약품 주식회사 | 1-(4-(4-(3,4-디클로로-2-플루오로페닐아미노)-7-메톡시퀴나졸린-6-일옥시)피페리딘-1-일)프로프-2-엔-1-온의 제조방법 |
| LT2964638T (lt) | 2013-03-06 | 2017-12-27 | Astrazeneca Ab | Epidermio augimo faktoriaus receptoriaus aktyvinančių mutacijų formų chinazolino inhibitoriai |
| US9242965B2 (en) | 2013-12-31 | 2016-01-26 | Boehringer Ingelheim International Gmbh | Process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form and use thereof for synthesis of EGFR tyrosine kinase inhibitors |
| CN108690012A (zh) * | 2017-06-10 | 2018-10-23 | 曹艳 | 一种治疗革兰氏阳性菌引起的感染的药物及其合成方法 |
| CN108558854A (zh) * | 2017-06-10 | 2018-09-21 | 曹艳 | 一种治疗革兰氏阳性菌引起的感染的药物及其合成方法 |
| CN107226815B (zh) * | 2017-06-22 | 2018-07-31 | 徐州市第一人民医院 | 喹唑啉类化合物及其在抗肿瘤药物中的应用 |
| CN110357858B (zh) * | 2018-04-09 | 2022-02-18 | 威尚(上海)生物医药有限公司 | 具有穿过血脑屏障能力的5取代二氟哌啶化合物 |
| CN114031563A (zh) * | 2021-12-01 | 2022-02-11 | 武汉科技大学 | 一种环丁喹噁啉类化合物及其应用 |
| CN118480031B (zh) * | 2024-07-16 | 2024-09-27 | 南京诺源医疗器械有限公司 | 一种用于主动靶向表皮生长因子受体检测的近红外荧光探针及其制备方法与应用 |
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-
2004
- 2004-09-15 DE DE602004004811T patent/DE602004004811T2/de not_active Expired - Lifetime
- 2004-09-15 WO PCT/GB2004/004109 patent/WO2005028470A1/en not_active Ceased
- 2004-09-15 JP JP2006526702A patent/JP2007505878A/ja active Pending
- 2004-09-15 ES ES04768652T patent/ES2281007T3/es not_active Expired - Lifetime
- 2004-09-15 US US10/572,048 patent/US20070037837A1/en not_active Abandoned
- 2004-09-15 AT AT04768652T patent/ATE353888T1/de not_active IP Right Cessation
- 2004-09-15 EP EP04768652A patent/EP1670782B1/en not_active Expired - Lifetime
- 2004-09-15 CN CN2004800339104A patent/CN1882570B/zh not_active Expired - Fee Related
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