JP2011502141A - 抗癌剤としての４‐（テトラゾール‐５‐イル）‐キナゾリン誘導体 - Google Patents
抗癌剤としての４‐（テトラゾール‐５‐イル）‐キナゾリン誘導体 Download PDFInfo
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- JP2011502141A JP2011502141A JP2010531646A JP2010531646A JP2011502141A JP 2011502141 A JP2011502141 A JP 2011502141A JP 2010531646 A JP2010531646 A JP 2010531646A JP 2010531646 A JP2010531646 A JP 2010531646A JP 2011502141 A JP2011502141 A JP 2011502141A
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- Prior art keywords
- formula
- compound
- tetrazol
- quinazoline
- substituted
- Prior art date
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- AOTAXPQFHSKSIZ-UHFFFAOYSA-N 4-(2h-tetrazol-5-yl)quinazoline Chemical class N=1C=NC2=CC=CC=C2C=1C1=NN=NN1 AOTAXPQFHSKSIZ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000002246 antineoplastic agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 238000000034 method Methods 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 72
- -1 hydroxy, amino, hydroxylamino, carboxy, nitro, guanidino, ureido Chemical group 0.000 claims description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 48
- 210000004027 cell Anatomy 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- 150000003246 quinazolines Chemical class 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 206010028980 Neoplasm Diseases 0.000 claims description 21
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 19
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 13
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 12
- 201000011510 cancer Diseases 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 239000008096 xylene Substances 0.000 claims description 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052721 tungsten Inorganic materials 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 7
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 7
- 230000002140 halogenating effect Effects 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000004703 alkoxides Chemical class 0.000 claims description 6
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 5
- 229910052987 metal hydride Inorganic materials 0.000 claims description 5
- 150000004681 metal hydrides Chemical class 0.000 claims description 5
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 5
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 5
- FCEBCZMVZSJVCA-UHFFFAOYSA-N 3-[[5-(6,7-dimethoxyquinazolin-4-yl)tetrazol-1-yl]methyl]aniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1C1=NN=NN1CC1=CC=CC(N)=C1 FCEBCZMVZSJVCA-UHFFFAOYSA-N 0.000 claims description 4
- RYUBYXNEIODQQO-UHFFFAOYSA-N 6,7-dimethoxy-4-[1-(pyridin-2-ylmethyl)tetrazol-5-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1C1=NN=NN1CC1=CC=CC=N1 RYUBYXNEIODQQO-UHFFFAOYSA-N 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical class C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000005270 trialkylamine group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- VYEGAEUUQMJXTM-UHFFFAOYSA-N 2-(chloromethyl)-1-methylimidazole Chemical compound CN1C=CN=C1CCl VYEGAEUUQMJXTM-UHFFFAOYSA-N 0.000 claims description 3
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 claims description 3
- DSHFCNBUHWTUCC-UHFFFAOYSA-N 6,7-dimethoxy-4-[1-[(1-methylimidazol-2-yl)methyl]tetrazol-5-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1C1=NN=NN1CC1=NC=CN1C DSHFCNBUHWTUCC-UHFFFAOYSA-N 0.000 claims description 3
- TVKKJQLSHMSYNN-UHFFFAOYSA-N 6,7-dimethoxy-4-[1-[(3-nitrophenyl)methyl]tetrazol-5-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1C1=NN=NN1CC1=CC=CC([N+]([O-])=O)=C1 TVKKJQLSHMSYNN-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 210000003739 neck Anatomy 0.000 claims description 3
- 238000004237 preparative chromatography Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
- MFUAVVKXXPSZRT-UHFFFAOYSA-N 3-[[5-(6,7-dimethoxyquinazolin-4-yl)tetrazol-1-yl]methyl]aniline;hydrochloride Chemical compound Cl.C=12C=C(OC)C(OC)=CC2=NC=NC=1C1=NN=NN1CC1=CC=CC(N)=C1 MFUAVVKXXPSZRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 210000003238 esophagus Anatomy 0.000 claims description 2
- 210000003128 head Anatomy 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 210000003932 urinary bladder Anatomy 0.000 claims description 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims 2
- NVVMERNNEDXKSI-UHFFFAOYSA-M (6,7-diethoxyquinazolin-4-yl)-trimethylazanium;chloride Chemical compound [Cl-].C1=NC([N+](C)(C)C)=C2C=C(OCC)C(OCC)=CC2=N1 NVVMERNNEDXKSI-UHFFFAOYSA-M 0.000 claims 1
- RHQWNPQWJJOIDM-UHFFFAOYSA-M (6,7-dimethoxyquinazolin-4-yl)-trimethylazanium;chloride Chemical compound [Cl-].C1=NC([N+](C)(C)C)=C2C=C(OC)C(OC)=CC2=N1 RHQWNPQWJJOIDM-UHFFFAOYSA-M 0.000 claims 1
- LSSZDYKTTANUSZ-UHFFFAOYSA-M (6,7-dipropoxyquinazolin-4-yl)-trimethylazanium;chloride Chemical compound [Cl-].C1=NC([N+](C)(C)C)=C2C=C(OCCC)C(OCCC)=CC2=N1 LSSZDYKTTANUSZ-UHFFFAOYSA-M 0.000 claims 1
- AMIQEOQFLOLPCM-UHFFFAOYSA-N 3-[[5-(6,7-diethoxyquinazolin-4-yl)tetrazol-1-yl]methyl]aniline Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=NC=1C1=NN=NN1CC1=CC=CC(N)=C1 AMIQEOQFLOLPCM-UHFFFAOYSA-N 0.000 claims 1
- IPYQQBIXKCGQRG-UHFFFAOYSA-N 3-[[5-(6,7-dipropoxyquinazolin-4-yl)tetrazol-1-yl]methyl]aniline Chemical compound C=12C=C(OCCC)C(OCCC)=CC2=NC=NC=1C1=NN=NN1CC1=CC=CC(N)=C1 IPYQQBIXKCGQRG-UHFFFAOYSA-N 0.000 claims 1
- VBCAGHWIYIAYBZ-UHFFFAOYSA-N 4-[1-[(1-methylimidazol-2-yl)methyl]tetrazol-5-yl]-6,7-dipropoxyquinazoline Chemical compound C=12C=C(OCCC)C(OCCC)=CC2=NC=NC=1C1=NN=NN1CC1=NC=CN1C VBCAGHWIYIAYBZ-UHFFFAOYSA-N 0.000 claims 1
- PCSGLFRAWWPYIT-UHFFFAOYSA-N 4-[1-[(3-nitrophenyl)methyl]tetrazol-5-yl]-6,7-dipropoxyquinazoline Chemical compound C=12C=C(OCCC)C(OCCC)=CC2=NC=NC=1C1=NN=NN1CC1=CC=CC([N+]([O-])=O)=C1 PCSGLFRAWWPYIT-UHFFFAOYSA-N 0.000 claims 1
- HGMQPDNSSYTATF-UHFFFAOYSA-N 4-chloro-6,7-diethoxyquinazoline Chemical compound C1=NC(Cl)=C2C=C(OCC)C(OCC)=CC2=N1 HGMQPDNSSYTATF-UHFFFAOYSA-N 0.000 claims 1
- USQGNYNAUSUQGV-UHFFFAOYSA-N 4-chloro-6,7-dipropoxyquinazoline Chemical compound C1=NC(Cl)=C2C=C(OCCC)C(OCCC)=CC2=N1 USQGNYNAUSUQGV-UHFFFAOYSA-N 0.000 claims 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
- MVMQVSVKQHUUTK-UHFFFAOYSA-N 6,7-diethoxy-4-(2h-tetrazol-5-yl)quinazoline Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=NC=1C1=NN=NN1 MVMQVSVKQHUUTK-UHFFFAOYSA-N 0.000 claims 1
- MWVSXBJZXARZAY-UHFFFAOYSA-N 6,7-diethoxy-4-[1-(pyridin-2-ylmethyl)tetrazol-5-yl]quinazoline Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=NC=1C1=NN=NN1CC1=CC=CC=N1 MWVSXBJZXARZAY-UHFFFAOYSA-N 0.000 claims 1
- STDRKXRGIRDSEQ-UHFFFAOYSA-N 6,7-diethoxy-4-[1-[(1-methylimidazol-2-yl)methyl]tetrazol-5-yl]quinazoline Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=NC=1C1=NN=NN1CC1=NC=CN1C STDRKXRGIRDSEQ-UHFFFAOYSA-N 0.000 claims 1
- HFJTUQHJGULTMR-UHFFFAOYSA-N 6,7-diethoxy-4-[1-[(3-nitrophenyl)methyl]tetrazol-5-yl]quinazoline Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=NC=1C1=NN=NN1CC1=CC=CC([N+]([O-])=O)=C1 HFJTUQHJGULTMR-UHFFFAOYSA-N 0.000 claims 1
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- JSKBQKOIPQQMJI-UHFFFAOYSA-N 6,7-dipropoxy-4-[1-(pyridin-2-ylmethyl)tetrazol-5-yl]quinazoline Chemical compound C=12C=C(OCCC)C(OCCC)=CC2=NC=NC=1C1=NN=NN1CC1=CC=CC=N1 JSKBQKOIPQQMJI-UHFFFAOYSA-N 0.000 claims 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—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
- 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
- C07D403/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2445CH2007 | 2007-10-29 | ||
| PCT/IN2008/000708 WO2009057139A2 (en) | 2007-10-29 | 2008-10-28 | Novel 4-(tetrazol-5-yl)-quinazoline derivatives as anti cancer agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011502141A true JP2011502141A (ja) | 2011-01-20 |
| JP2011502141A5 JP2011502141A5 (enExample) | 2011-12-15 |
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| US (1) | US8080558B2 (enExample) |
| EP (1) | EP2220054A2 (enExample) |
| JP (1) | JP2011502141A (enExample) |
| KR (1) | KR20100087185A (enExample) |
| CN (1) | CN101878203A (enExample) |
| AU (1) | AU2008320342B2 (enExample) |
| CA (1) | CA2703767A1 (enExample) |
| EA (1) | EA018716B1 (enExample) |
| GE (1) | GEP20125603B (enExample) |
| MX (1) | MX2010004625A (enExample) |
| MY (1) | MY150054A (enExample) |
| NZ (1) | NZ585357A (enExample) |
| UA (1) | UA101168C2 (enExample) |
| WO (1) | WO2009057139A2 (enExample) |
| ZA (1) | ZA201002807B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103130729B (zh) * | 2011-12-05 | 2015-07-15 | 齐鲁制药有限公司 | 一种4-氯代-7-甲氧基喹唑啉-6-醇乙酸酯的制备方法 |
| CN104981247A (zh) | 2012-09-06 | 2015-10-14 | 普莱希科公司 | 用于激酶调节的化合物和方法及其适应症 |
| CN102993114B (zh) * | 2012-10-11 | 2015-08-12 | 南通市华峰化工有限责任公司 | 一种1h-四唑-5-乙酸的生产方法 |
| CN103204817B (zh) * | 2013-04-16 | 2018-03-27 | 江西师范大学 | 4‑氰基喹唑啉衍生物的制备方法 |
| DE102013008118A1 (de) * | 2013-05-11 | 2014-11-13 | Merck Patent Gmbh | Arylchinazoline |
| US10231973B2 (en) | 2015-03-20 | 2019-03-19 | Chai Tai Tianqing Pharmaceutical Group Co., Ltd. | Salts of quinazoline derivative and method for preparing the same |
| CN114787151B (zh) * | 2019-11-01 | 2024-04-16 | 正大天晴药业集团股份有限公司 | 喹唑啉衍生物或其盐、或其药物组合物的用途 |
| MX2023005713A (es) * | 2020-11-23 | 2023-05-30 | Hoffmann La Roche | Nuevo proceso para la elaboracion de derivados de tetrazol. |
| CN114437041B (zh) * | 2022-02-25 | 2023-11-10 | 湖北科技学院 | 一类具有抗肿瘤活性的4-四唑基取代-3，4-二氢喹唑啉衍生物及其制备方法和应用 |
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| WO2007022241A2 (en) * | 2005-08-17 | 2007-02-22 | Schering Corporation | Novel high affinity quinoline-based kinase ligands |
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-
2008
- 2008-10-28 CN CN200880118458XA patent/CN101878203A/zh active Pending
- 2008-10-28 MY MYPI2010001916A patent/MY150054A/en unknown
- 2008-10-28 EP EP08844368A patent/EP2220054A2/en not_active Withdrawn
- 2008-10-28 WO PCT/IN2008/000708 patent/WO2009057139A2/en not_active Ceased
- 2008-10-28 KR KR1020107011577A patent/KR20100087185A/ko not_active Withdrawn
- 2008-10-28 AU AU2008320342A patent/AU2008320342B2/en not_active Ceased
- 2008-10-28 MX MX2010004625A patent/MX2010004625A/es unknown
- 2008-10-28 EA EA201070543A patent/EA018716B1/ru not_active IP Right Cessation
- 2008-10-28 CA CA2703767A patent/CA2703767A1/en not_active Abandoned
- 2008-10-28 US US12/740,527 patent/US8080558B2/en not_active Expired - Fee Related
- 2008-10-28 GE GEAP200811821A patent/GEP20125603B/en unknown
- 2008-10-28 JP JP2010531646A patent/JP2011502141A/ja active Pending
- 2008-10-28 NZ NZ585357A patent/NZ585357A/en not_active IP Right Cessation
- 2008-10-28 UA UAA201006435A patent/UA101168C2/ru unknown
-
2010
- 2010-04-21 ZA ZA2010/02807A patent/ZA201002807B/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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Also Published As
| Publication number | Publication date |
|---|---|
| US20100261740A1 (en) | 2010-10-14 |
| EA018716B1 (ru) | 2013-10-30 |
| WO2009057139A2 (en) | 2009-05-07 |
| KR20100087185A (ko) | 2010-08-03 |
| MX2010004625A (es) | 2010-05-20 |
| AU2008320342A2 (en) | 2010-09-02 |
| ZA201002807B (en) | 2011-07-27 |
| GEP20125603B (en) | 2012-08-10 |
| EA201070543A1 (ru) | 2010-12-30 |
| WO2009057139A3 (en) | 2009-09-24 |
| CN101878203A (zh) | 2010-11-03 |
| AU2008320342A1 (en) | 2009-05-07 |
| CA2703767A1 (en) | 2009-05-07 |
| AU2008320342B2 (en) | 2012-07-26 |
| MY150054A (en) | 2013-11-29 |
| EP2220054A2 (en) | 2010-08-25 |
| US8080558B2 (en) | 2011-12-20 |
| NZ585357A (en) | 2012-02-24 |
| UA101168C2 (ru) | 2013-03-11 |
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