CN101787019A - 喹唑啉衍生物 - Google Patents
喹唑啉衍生物 Download PDFInfo
- Publication number
- CN101787019A CN101787019A CN201010119887A CN201010119887A CN101787019A CN 101787019 A CN101787019 A CN 101787019A CN 201010119887 A CN201010119887 A CN 201010119887A CN 201010119887 A CN201010119887 A CN 201010119887A CN 101787019 A CN101787019 A CN 101787019A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- group
- amino
- quinazoline
- oxygen base
- 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.)
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 241001597008 Nomeidae Species 0.000 title claims abstract description 46
- 241001465754 Metazoa Species 0.000 claims abstract description 6
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims abstract description 6
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims abstract description 6
- 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 1214
- -1 heterocyclic radical Chemical class 0.000 claims description 839
- 239000002585 base Substances 0.000 claims description 424
- 229910052760 oxygen Inorganic materials 0.000 claims description 314
- 239000001257 hydrogen Substances 0.000 claims description 313
- 229910052739 hydrogen Inorganic materials 0.000 claims description 313
- 125000003545 alkoxy group Chemical group 0.000 claims description 279
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 249
- 239000001301 oxygen Substances 0.000 claims description 219
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 216
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 198
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 186
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 165
- 125000003342 alkenyl group Chemical group 0.000 claims description 153
- 125000000304 alkynyl group Chemical group 0.000 claims description 153
- 125000003282 alkyl amino group Chemical group 0.000 claims description 137
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 125
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 112
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 111
- 229910052757 nitrogen Inorganic materials 0.000 claims description 97
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 87
- 229930195733 hydrocarbon Natural products 0.000 claims description 82
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 81
- 239000000460 chlorine Substances 0.000 claims description 80
- 229910052801 chlorine Inorganic materials 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 76
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 75
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000000623 heterocyclic group Chemical group 0.000 claims description 69
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 67
- 125000004414 alkyl thio group Chemical group 0.000 claims description 67
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 67
- 125000004423 acyloxy group Chemical group 0.000 claims description 66
- 150000002431 hydrogen Chemical class 0.000 claims description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 63
- 229910005965 SO 2 Inorganic materials 0.000 claims description 60
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 60
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 56
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 53
- 229910052799 carbon Inorganic materials 0.000 claims description 47
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 47
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 40
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 35
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 26
- 239000005864 Sulphur Substances 0.000 claims description 24
- 150000003254 radicals Chemical group 0.000 claims description 23
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 22
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 20
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 17
- 125000001118 alkylidene group Chemical group 0.000 claims description 14
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 11
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 30
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 15
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 14
- 125000006239 protecting group Chemical group 0.000 claims 13
- 239000003513 alkali Substances 0.000 claims 4
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- IHPHPGLJYCDONF-UHFFFAOYSA-N n-propylacetamide Chemical compound CCCNC(C)=O IHPHPGLJYCDONF-UHFFFAOYSA-N 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 230000009257 reactivity Effects 0.000 claims 2
- 230000000452 restraining effect Effects 0.000 claims 2
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 claims 1
- GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 claims 1
- FWIBCWKHNZBDLS-UHFFFAOYSA-N 3-hydroxyoxolan-2-one Chemical compound OC1CCOC1=O FWIBCWKHNZBDLS-UHFFFAOYSA-N 0.000 claims 1
- BSDGZUDFPKIYQG-UHFFFAOYSA-N 4-bromopyridine Chemical compound BrC1=CC=NC=C1 BSDGZUDFPKIYQG-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 description 162
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 65
- 239000011737 fluorine Substances 0.000 description 59
- 229910052731 fluorine Inorganic materials 0.000 description 59
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 57
- 125000004043 oxo group Chemical group O=* 0.000 description 43
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 39
- 150000001721 carbon Chemical group 0.000 description 32
- 206010028980 Neoplasm Diseases 0.000 description 28
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 20
- 201000011510 cancer Diseases 0.000 description 18
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 17
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 16
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 15
- 125000004193 piperazinyl group Chemical group 0.000 description 15
- 125000005936 piperidyl group Chemical group 0.000 description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
- 229910052794 bromium Inorganic materials 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 13
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 11
- 125000000335 thiazolyl group Chemical group 0.000 description 11
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 10
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 9
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 8
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 8
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 8
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 8
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 8
- 125000002393 azetidinyl group Chemical group 0.000 description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 8
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 8
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 8
- 206010020718 hyperplasia Diseases 0.000 description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 8
- 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 description 8
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 8
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 7
- 108700020796 Oncogene Proteins 0.000 description 7
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 7
- 125000002757 morpholinyl group Chemical group 0.000 description 7
- 125000001422 pyrrolinyl group Chemical group 0.000 description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 6
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 6
- 102000001301 EGF receptor Human genes 0.000 description 6
- 108060006698 EGF receptor Proteins 0.000 description 6
- 108091000080 Phosphotransferase Proteins 0.000 description 6
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- 239000003112 inhibitor Substances 0.000 description 6
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- 102000020233 phosphotransferase Human genes 0.000 description 6
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- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 5
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 230000002018 overexpression Effects 0.000 description 5
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0326459.5A GB0326459D0 (en) | 2003-11-13 | 2003-11-13 | Quinazoline derivatives |
| GB0326459.5 | 2003-11-13 |
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|---|---|---|---|
| CNA2004800404156A Division CN1906178A (zh) | 2003-11-13 | 2004-11-11 | 喹唑啉衍生物 |
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| CN101787019A true CN101787019A (zh) | 2010-07-28 |
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| CNA2004800404156A Pending CN1906178A (zh) | 2003-11-13 | 2004-11-11 | 喹唑啉衍生物 |
| CN201010119887A Pending CN101787019A (zh) | 2003-11-13 | 2004-11-11 | 喹唑啉衍生物 |
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| CNA2004800404156A Pending CN1906178A (zh) | 2003-11-13 | 2004-11-11 | 喹唑啉衍生物 |
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| EP (1) | EP1685116A1 (enExample) |
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| AR (1) | AR046452A1 (enExample) |
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| BR (1) | BRPI0416479A (enExample) |
| CA (1) | CA2545262A1 (enExample) |
| GB (1) | GB0326459D0 (enExample) |
| IL (1) | IL175421A0 (enExample) |
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| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| BR0213842A (pt) * | 2001-11-03 | 2004-08-31 | Astrazeneca Ab | Derivado de quinazolina ou um sal deste farmaceuticamente aceitável, processo para a preparação do mesmo, composição farmacêutica, e, uso do derivado de quinazolina ou de um sal deste farmaceuticamente aceitável |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005026156A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| EP1664028A1 (en) * | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives as tyrosine kinase inhibitors |
| US7569577B2 (en) * | 2003-09-16 | 2009-08-04 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| WO2005026157A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| EP1713781B1 (en) * | 2004-02-03 | 2008-11-05 | AstraZeneca AB | Quinazoline derivatives |
| WO2005118572A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
| US7947676B2 (en) * | 2004-12-14 | 2011-05-24 | Astrazeneca Ab | Pyrazolo[3,4-d]pyrimidine compounds as antitumor agents |
| 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 |
| JP2009508918A (ja) * | 2005-09-20 | 2009-03-05 | アストラゼネカ アクチボラグ | 癌治療のためのｅｒｂＢ受容体チロシンキナーゼ阻害剤としての４−（１Ｈ−インダゾール−５−イル］アミノ）キナゾリン化合物 |
| US20090239861A1 (en) * | 2005-09-20 | 2009-09-24 | Robert Hugh Bradbury | Quinazoline derivatives as anticancer agents |
| EP1957499A1 (en) * | 2005-12-02 | 2008-08-20 | AstraZeneca AB | 4-anilino-substituted quinazoline derivatives as tyrosine kinase inhibitors |
| WO2007063293A1 (en) * | 2005-12-02 | 2007-06-07 | Astrazeneca Ab | Quinazoleine derivatives used as inhibitors of erbb tyrosine kinase |
| KR101129868B1 (ko) | 2006-10-04 | 2012-04-12 | 화이자 프로덕츠 인코포레이티드 | 칼슘 수용체 길항제로서의 피리도［4,3-ｄ］피리미딘-4(3Ｈ)-온 유도체 |
| CN101878203A (zh) | 2007-10-29 | 2010-11-03 | 纳科法尔马有限公司 | 作为抗癌剂的新的4-(四唑-5-基)喹唑啉衍生物 |
| CN105555781A (zh) * | 2013-09-19 | 2016-05-04 | 皮埃尔法布雷医药公司 | 喹唑啉衍生物和其作为dna甲基转移酶抑制剂的用途 |
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| AU2002339687A1 (en) | 2001-12-12 | 2003-06-23 | Pfizer Products Inc. | Quinazoline derivatives for the treatement of abnormal cell growth |
| 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 |
| IL164167A0 (en) | 2002-03-30 | 2005-12-18 | Boehringer Ingelheim Pharma | 4-(N-phenylamino)-quinazolines/ quinolines as tyrosine kinase inhibitors |
| JP4703183B2 (ja) | 2002-07-15 | 2011-06-15 | シンフォニー エボルーション， インク． | 受容体型キナーゼモジュレーターおよびその使用方法 |
| JP4611745B2 (ja) | 2002-11-20 | 2011-01-12 | アレイ バイオファーマ、インコーポレイテッド | ＥｒｂＢ２及びＥＧＦＲ阻害剤としてのシアノグアニジン及びシアノアミジン |
| KR20050122199A (ko) | 2003-01-23 | 2005-12-28 | 티.케이. 시그널 리미티드 | 표피성장인자 수용체 티로신 키나제의 비가역성 억제제 및 그의 용도 |
| 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 |
| AU2004261477A1 (en) | 2003-07-29 | 2005-02-10 | Astrazeneca Ab | Piperidyl-quinazoline derivatives as tyrosine kinase inhibitors |
| GB0318423D0 (en) | 2003-08-06 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
| US7569577B2 (en) | 2003-09-16 | 2009-08-04 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| EP1664028A1 (en) | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives as tyrosine kinase inhibitors |
| WO2005026156A1 (en) | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| GB0321648D0 (en) | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005026157A1 (en) | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| PL1667992T3 (pl) | 2003-09-19 | 2007-05-31 | Astrazeneca Ab | Pochodne chinazoliny |
| WO2005028470A1 (en) | 2003-09-19 | 2005-03-31 | Astrazeneca Ab | Quinazoline derivatives |
| GB0322409D0 (en) | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| US20070043010A1 (en) | 2003-09-25 | 2007-02-22 | Astrazeneca Uk Limited | Quinazoline derivatives |
| DE10350717A1 (de) | 2003-10-30 | 2005-06-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung von Tyrosinkinase-Inhibitoren zur Behandlung inflammatorischer Prozesse |
| EP1713781B1 (en) | 2004-02-03 | 2008-11-05 | AstraZeneca AB | Quinazoline derivatives |
| WO2005097134A2 (en) | 2004-03-31 | 2005-10-20 | The Scripps Research Institute | Quinazoline based protein kinase inhibitors |
| WO2005118572A1 (en) | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
| MX2007000944A (es) | 2004-07-23 | 2007-04-13 | Astrazeneca Ab | Metodo para pronosticar la sensibilidad de un tumor a farmacos del receptor erbb. |
| US7947676B2 (en) | 2004-12-14 | 2011-05-24 | Astrazeneca Ab | Pyrazolo[3,4-d]pyrimidine compounds as antitumor agents |
| MX2007010399A (es) | 2005-02-26 | 2007-09-25 | Astrazeneca Ab | Derivados de quinazolina en la forma de inhibidores de cinasa de tirosina. |
| GB0504475D0 (en) | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0504474D0 (en) | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0508715D0 (en) | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| US20090239861A1 (en) | 2005-09-20 | 2009-09-24 | Robert Hugh Bradbury | Quinazoline derivatives as anticancer agents |
| JP2009508918A (ja) | 2005-09-20 | 2009-03-05 | アストラゼネカ アクチボラグ | 癌治療のためのｅｒｂＢ受容体チロシンキナーゼ阻害剤としての４−（１Ｈ−インダゾール−５−イル］アミノ）キナゾリン化合物 |
| EP1957499A1 (en) | 2005-12-02 | 2008-08-20 | AstraZeneca AB | 4-anilino-substituted quinazoline derivatives as tyrosine kinase inhibitors |
| WO2007063293A1 (en) | 2005-12-02 | 2007-06-07 | Astrazeneca Ab | Quinazoleine derivatives used as inhibitors of erbb tyrosine kinase |
-
2003
- 2003-11-13 GB GBGB0326459.5A patent/GB0326459D0/en not_active Ceased
-
2004
- 2004-11-11 CA CA002545262A patent/CA2545262A1/en not_active Abandoned
- 2004-11-11 AU AU2004293250A patent/AU2004293250A1/en not_active Abandoned
- 2004-11-11 EP EP04798484A patent/EP1685116A1/en not_active Withdrawn
- 2004-11-11 WO PCT/GB2004/004761 patent/WO2005051923A1/en not_active Ceased
- 2004-11-11 CN CNA2004800404156A patent/CN1906178A/zh active Pending
- 2004-11-11 US US10/578,663 patent/US7625908B2/en not_active Expired - Fee Related
- 2004-11-11 CN CN201010119887A patent/CN101787019A/zh active Pending
- 2004-11-11 BR BRPI0416479-2A patent/BRPI0416479A/pt not_active Application Discontinuation
- 2004-11-11 JP JP2006538946A patent/JP2007511491A/ja active Pending
- 2004-11-11 KR KR1020067011553A patent/KR20060127410A/ko not_active Withdrawn
- 2004-11-11 UY UY28610A patent/UY28610A1/es not_active Application Discontinuation
- 2004-11-12 TW TW093134778A patent/TW200524903A/zh unknown
- 2004-11-12 AR ARP040104181A patent/AR046452A1/es unknown
-
2006
- 2006-05-04 IL IL175421A patent/IL175421A0/en unknown
- 2006-05-12 ZA ZA200603817A patent/ZA200603817B/en unknown
- 2006-05-23 NO NO20062353A patent/NO20062353L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB0326459D0 (en) | 2003-12-17 |
| CN1906178A (zh) | 2007-01-31 |
| BRPI0416479A (pt) | 2007-03-06 |
| KR20060127410A (ko) | 2006-12-12 |
| JP2007511491A (ja) | 2007-05-10 |
| UY28610A1 (es) | 2005-06-30 |
| US20070244136A1 (en) | 2007-10-18 |
| IL175421A0 (en) | 2006-09-05 |
| WO2005051923A1 (en) | 2005-06-09 |
| TW200524903A (en) | 2005-08-01 |
| CA2545262A1 (en) | 2005-06-09 |
| AR046452A1 (es) | 2005-12-07 |
| AU2004293250A1 (en) | 2005-06-09 |
| NO20062353L (no) | 2006-08-09 |
| ZA200603817B (en) | 2007-10-31 |
| EP1685116A1 (en) | 2006-08-02 |
| US7625908B2 (en) | 2009-12-01 |
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