CN1993349A - 作为erbb受体酪氨酸激酶的喹唑啉衍生物 - Google Patents
作为erbb受体酪氨酸激酶的喹唑啉衍生物 Download PDFInfo
- Publication number
- CN1993349A CN1993349A CNA200580025966XA CN200580025966A CN1993349A CN 1993349 A CN1993349 A CN 1993349A CN A200580025966X A CNA200580025966X A CN A200580025966XA CN 200580025966 A CN200580025966 A CN 200580025966A CN 1993349 A CN1993349 A CN 1993349A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- methyl
- quinazoline
- group
- 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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- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title abstract description 20
- 102000001301 EGF receptor Human genes 0.000 title abstract description 11
- 108060006698 EGF receptor Proteins 0.000 title abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 18
- 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 797
- -1 (2-8C) thiazolinyl Chemical group 0.000 claims description 794
- 229910052760 oxygen Inorganic materials 0.000 claims description 563
- 239000001301 oxygen Substances 0.000 claims description 520
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 508
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 244
- 125000000623 heterocyclic group Chemical group 0.000 claims description 207
- 125000003545 alkoxy group Chemical group 0.000 claims description 193
- 239000001257 hydrogen Substances 0.000 claims description 175
- 229910052739 hydrogen Inorganic materials 0.000 claims description 175
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 155
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 139
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 137
- 229910052757 nitrogen Inorganic materials 0.000 claims description 130
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 126
- 229910052736 halogen Inorganic materials 0.000 claims description 123
- 150000002367 halogens Chemical class 0.000 claims description 123
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 119
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 114
- 241001597008 Nomeidae Species 0.000 claims description 103
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 103
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 101
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 100
- 125000000304 alkynyl group Chemical group 0.000 claims description 100
- 125000003282 alkyl amino group Chemical group 0.000 claims description 92
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 87
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims description 74
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 59
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 59
- 239000000460 chlorine Substances 0.000 claims description 59
- 229910052801 chlorine Inorganic materials 0.000 claims description 59
- 229910052731 fluorine Inorganic materials 0.000 claims description 58
- 239000011737 fluorine Substances 0.000 claims description 58
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 56
- 125000005842 heteroatom Chemical group 0.000 claims description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 50
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 47
- 229910005965 SO 2 Inorganic materials 0.000 claims description 47
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 46
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 46
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 43
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 40
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 39
- 125000004414 alkyl thio group Chemical group 0.000 claims description 39
- 125000004423 acyloxy group Chemical group 0.000 claims description 38
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 37
- 229920006395 saturated elastomer Polymers 0.000 claims description 36
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
- 239000005864 Sulphur Substances 0.000 claims description 29
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 29
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 28
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000004076 pyridyl group Chemical group 0.000 claims description 25
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 20
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 15
- 125000005936 piperidyl group Chemical group 0.000 claims description 15
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 14
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 125000004193 piperazinyl group Chemical group 0.000 claims description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 11
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000002393 azetidinyl group Chemical group 0.000 claims description 10
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 10
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims description 9
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 9
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims description 8
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 claims description 8
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 claims description 7
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 7
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 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 description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 6
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 5
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- 230000000452 restraining effect Effects 0.000 claims description 5
- 150000003527 tetrahydropyrans Chemical class 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 2
- WRLSNQXIGKWPGJ-UHFFFAOYSA-N 2-methylpropanamide Chemical compound C[C](C)C(N)=O WRLSNQXIGKWPGJ-UHFFFAOYSA-N 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 2
- JYCGXZGGVUKKNQ-UHFFFAOYSA-N tert-butyl formate piperazine Chemical compound C(C)(C)(C)OC=O.N1CCNCC1 JYCGXZGGVUKKNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims 12
- 230000000903 blocking effect Effects 0.000 claims 1
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 18
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- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 16
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- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 10
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 10
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D417/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04291393.9 | 2004-06-04 | ||
| EP04291393 | 2004-06-04 |
Publications (1)
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|---|---|
| CN1993349A true CN1993349A (zh) | 2007-07-04 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNA200580025966XA Pending CN1993349A (zh) | 2004-06-04 | 2005-06-02 | 作为erbb受体酪氨酸激酶的喹唑啉衍生物 |
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|---|---|
| US (1) | US20070232607A1 (enExample) |
| EP (1) | EP1756088A1 (enExample) |
| JP (1) | JP2008501675A (enExample) |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105399733A (zh) * | 2015-12-03 | 2016-03-16 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1504及其制备方法和应用 |
| CN105503835A (zh) * | 2015-12-03 | 2016-04-20 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1510及其制备方法和应用 |
| CN105503836A (zh) * | 2015-12-03 | 2016-04-20 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1502及其制备方法和应用 |
| CN105541807A (zh) * | 2015-12-03 | 2016-05-04 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1506及其制备方法和应用 |
| CN106366020A (zh) * | 2016-08-31 | 2017-02-01 | 京博农化科技股份有限公司 | 一种合成手性稻瘟酰胺的方法 |
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| 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 |
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| EP1664030A1 (en) * | 2003-09-16 | 2006-06-07 | 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 |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
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| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
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| BRPI0413066A (pt) * | 2003-07-29 | 2006-10-17 | Astrazeneca Ab | derivado de quinazolina, ou um sal farmaceuticamente aceitável, ou um éster farmaceuticamente aceitável do mesmo, da fórmula i, uso e processo para a preparação do mesmo, composto, composição farmacêutica, e, métodos para a produção de um efeito antiproliferativo em um animal de sangue quente, para a prevenção ou tratamento de um tumor, para prover um efeito inibitório de tirosina quinase de egfr seletivo, e para tratar um cáncer em um animal de sangue quente |
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| ATE413389T1 (de) * | 2004-02-03 | 2008-11-15 | Astrazeneca Ab | Chinazolinderivate |
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2005
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- 2005-06-02 JP JP2007514135A patent/JP2008501675A/ja active Pending
- 2005-06-02 AU AU2005250224A patent/AU2005250224A1/en not_active Abandoned
- 2005-06-02 BR BRPI0511741-0A patent/BRPI0511741A/pt not_active IP Right Cessation
- 2005-06-02 MX MXPA06014125A patent/MXPA06014125A/es not_active Application Discontinuation
- 2005-06-02 WO PCT/GB2005/002215 patent/WO2005118572A1/en not_active Ceased
- 2005-06-02 US US11/628,011 patent/US20070232607A1/en not_active Abandoned
- 2005-06-02 KR KR1020077000221A patent/KR20070038500A/ko not_active Withdrawn
- 2005-06-02 CN CNA200580025966XA patent/CN1993349A/zh active Pending
- 2005-06-02 EP EP05747243A patent/EP1756088A1/en not_active Withdrawn
- 2005-06-03 UY UY28940A patent/UY28940A1/es not_active Application Discontinuation
- 2005-06-03 TW TW094118285A patent/TW200602328A/zh unknown
- 2005-06-06 AR ARP050102306A patent/AR049294A1/es unknown
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- 2006-11-06 IL IL179081A patent/IL179081A0/en unknown
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- 2006-12-29 NO NO20066081A patent/NO20066081L/no not_active Application Discontinuation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105399733A (zh) * | 2015-12-03 | 2016-03-16 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1504及其制备方法和应用 |
| CN105503835A (zh) * | 2015-12-03 | 2016-04-20 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1510及其制备方法和应用 |
| CN105503836A (zh) * | 2015-12-03 | 2016-04-20 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1502及其制备方法和应用 |
| CN105541807A (zh) * | 2015-12-03 | 2016-05-04 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1506及其制备方法和应用 |
| CN105503835B (zh) * | 2015-12-03 | 2018-04-24 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1510及其制备方法和应用 |
| CN105503836B (zh) * | 2015-12-03 | 2018-04-24 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1502及其制备方法和应用 |
| CN105541807B (zh) * | 2015-12-03 | 2018-04-24 | 中国人民解放军南京军区南京总医院 | 一种新型喹唑啉衍生物lu1506及其制备方法和应用 |
| CN106366020A (zh) * | 2016-08-31 | 2017-02-01 | 京博农化科技股份有限公司 | 一种合成手性稻瘟酰胺的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008501675A (ja) | 2008-01-24 |
| NO20066081L (no) | 2007-02-20 |
| AU2005250224A1 (en) | 2005-12-15 |
| KR20070038500A (ko) | 2007-04-10 |
| US20070232607A1 (en) | 2007-10-04 |
| CA2567832A1 (en) | 2005-12-15 |
| UY28940A1 (es) | 2006-01-31 |
| IL179081A0 (en) | 2007-03-08 |
| AR049294A1 (es) | 2006-07-12 |
| MXPA06014125A (es) | 2007-01-31 |
| ZA200609427B (en) | 2008-08-27 |
| BRPI0511741A (pt) | 2008-01-02 |
| TW200602328A (en) | 2006-01-16 |
| WO2005118572A1 (en) | 2005-12-15 |
| EP1756088A1 (en) | 2007-02-28 |
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