ZA200602189B - Quinazoline derivatives as antitumor agents - Google Patents
Quinazoline derivatives as antitumor agents Download PDFInfo
- Publication number
- ZA200602189B ZA200602189B ZA200602189A ZA200602189A ZA200602189B ZA 200602189 B ZA200602189 B ZA 200602189B ZA 200602189 A ZA200602189 A ZA 200602189A ZA 200602189 A ZA200602189 A ZA 200602189A ZA 200602189 B ZA200602189 B ZA 200602189B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- amino
- quinazolin
- formula
- chloro
- Prior art date
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- 239000002246 antineoplastic agent Substances 0.000 title description 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 342
- -1 hydroxy, cyano, amino, carboxy, carbamoyl Chemical group 0.000 claims description 309
- 125000003545 alkoxy group Chemical group 0.000 claims description 86
- 150000003246 quinazolines Chemical class 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 73
- 229910052757 nitrogen Inorganic materials 0.000 claims description 62
- 125000005843 halogen group Chemical group 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 38
- 125000003282 alkyl amino group Chemical group 0.000 claims description 37
- 125000000304 alkynyl group Chemical group 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 24
- 125000004423 acyloxy group Chemical group 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 23
- 125000001589 carboacyl group Chemical group 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 20
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 17
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 239000011593 sulfur Chemical group 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims description 9
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 8
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 238000003780 insertion Methods 0.000 claims description 7
- 230000037431 insertion Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 5
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 230000001028 anti-proliverative effect Effects 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 2
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000003551 oxepanyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 22
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims 18
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 14
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 9
- 125000000524 functional group Chemical group 0.000 claims 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- AESKUPWTDDMLAL-HXUWFJFHSA-N 1-[(2r)-2-[[4-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CSC=4)=CC=3)=C12 AESKUPWTDDMLAL-HXUWFJFHSA-N 0.000 claims 1
- OZACVFLDNVJDRR-QGZVFWFLSA-N 1-[(2r)-2-[[4-[3-chloro-4-(1,3-thiazol-5-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4SC=NC=4)=CC=3)=C12 OZACVFLDNVJDRR-QGZVFWFLSA-N 0.000 claims 1
- NTJPTMMEHGYIGG-OAQYLSRUSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)=C12 NTJPTMMEHGYIGG-OAQYLSRUSA-N 0.000 claims 1
- SNLRBQMQODFNMA-JOCHJYFZSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]morpholin-4-yl]-2-(dimethylamino)ethanone Chemical compound C1N(C(=O)CN(C)C)CCO[C@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 SNLRBQMQODFNMA-JOCHJYFZSA-N 0.000 claims 1
- MXIWNBPAJCAGDV-HSZRJFAPSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 MXIWNBPAJCAGDV-HSZRJFAPSA-N 0.000 claims 1
- WRSLJTGCVMSOMP-JOCHJYFZSA-N 1-[(2r)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-3-hydroxy-2,2-dimethylpropan-1-one Chemical compound OCC(C)(C)C(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 WRSLJTGCVMSOMP-JOCHJYFZSA-N 0.000 claims 1
- GRYACOOCWFNQOX-OAQYLSRUSA-N 1-[(2r)-2-[[4-[3-chloro-4-[(5-methyl-1,2-oxazol-3-yl)methoxy]anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(Cl)C(OCC4=NOC(C)=C4)=CC=3)=C12 GRYACOOCWFNQOX-OAQYLSRUSA-N 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- OHXWAHWLPJWMBZ-HSZRJFAPSA-N 2-(dimethylamino)-1-[(2r)-2-[[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1COC1=CC=CC2=NC=NC(NC=3C=C(C)C(OC=4C=NC(C)=CC=4)=CC=3)=C12 OHXWAHWLPJWMBZ-HSZRJFAPSA-N 0.000 claims 1
- 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
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
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- NCKOFAVIRYQKKM-OAQYLSRUSA-N 2-hydroxy-1-[(2r)-2-[[4-[3-methyl-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-5-yl]oxymethyl]pyrrolidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2N=CC=NC=2)C(C)=CC=1NC(C=12)=NC=NC2=CC=CC=1OC[C@H]1CCCN1C(=O)CO NCKOFAVIRYQKKM-OAQYLSRUSA-N 0.000 claims 1
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
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- 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
-
- 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
- C07D403/02—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
-
- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Oncology (AREA)
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- Vascular Medicine (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0321648.8A GB0321648D0 (en) | 2003-09-16 | 2003-09-16 | Quinazoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200602189B true ZA200602189B (en) | 2007-11-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200602189A ZA200602189B (en) | 2003-09-16 | 2006-03-15 | Quinazoline derivatives as antitumor agents |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20070015743A1 (enExample) |
| EP (1) | EP1664029B1 (enExample) |
| JP (1) | JP2007505874A (enExample) |
| CN (1) | CN1882572A (enExample) |
| AR (1) | AR045752A1 (enExample) |
| AT (1) | ATE450528T1 (enExample) |
| AU (1) | AU2004272351A1 (enExample) |
| BR (1) | BRPI0414486A (enExample) |
| CA (1) | CA2539024A1 (enExample) |
| DE (1) | DE602004024420D1 (enExample) |
| GB (1) | GB0321648D0 (enExample) |
| IL (1) | IL174260A0 (enExample) |
| MX (1) | MXPA06002965A (enExample) |
| NO (1) | NO20061320L (enExample) |
| TW (1) | TW200526628A (enExample) |
| WO (1) | WO2005026152A1 (enExample) |
| ZA (1) | ZA200602189B (enExample) |
Families Citing this family (37)
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| 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 |
| 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 |
| MXPA06002963A (es) * | 2003-09-16 | 2006-06-14 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de cinasa de tirosina. |
| WO2005026156A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005026150A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| BRPI0414488A (pt) * | 2003-09-16 | 2006-11-14 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, métodos para produzir um efeito anti - proliferativo em um animal de sangue quente, para prevenção ou tratamento de tumores em um aminal de sangue quente, para fornecer um efeito inibidor da tirosina quinase de egfr seletivo em um animal de sangue quente e para tratar um cáncer em um animal de sangue quente e, processo para a preparação de um derivado de quinazolina |
| 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 |
| 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 |
| CN102772358A (zh) * | 2005-06-16 | 2012-11-14 | 美瑞德生物工程公司 | 药物组合物及其用途 |
| 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 |
| DE602006021645D1 (de) | 2005-11-15 | 2011-06-09 | Array Biopharma Inc | Verfahren und Zwischenverbindungen zur Herstellung von N4-Phenyl-Quinazolin-4-Amin Derivaten |
| 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 |
| 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 |
| KR20100016385A (ko) * | 2007-04-10 | 2010-02-12 | 미리어드 파마슈티칼스, 인코포레이티드 | 뇌종양 치료방법 |
| CA2720989A1 (en) * | 2007-04-10 | 2008-10-16 | Myrexis, Inc. | Methods for treating cancer |
| WO2008124828A1 (en) * | 2007-04-10 | 2008-10-16 | Myriad Genetics, Inc. | Methods for treating vascular disruption disorders |
| NZ580867A (en) * | 2007-04-10 | 2011-02-25 | Myriad Pharmaceuticals Inc | Method of treating melanoma |
| EP2144887A4 (en) * | 2007-04-10 | 2012-10-03 | Myrexis Inc | PHARMACEUTICAL FORMS AND METHOD FOR THE TREATMENT OF CANCER |
| 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 |
| GB0820819D0 (en) | 2008-11-13 | 2008-12-24 | Sareum Ltd | Pharmaceutical compounds |
| KR102000312B1 (ko) | 2011-10-14 | 2019-07-15 | 어레이 바이오파마 인크. | Erb2 (her2) 저해제의 고체 분산물 |
| US9168254B2 (en) | 2011-10-14 | 2015-10-27 | Array Biopharma Inc. | Polymorphs of ARRY-380, a selective HER 2 inhibitor and pharmaceutical compositions containing them |
| TWI811358B (zh) * | 2018-05-08 | 2023-08-11 | 大陸商迪哲（江蘇）醫藥股份有限公司 | ＥｒｂＢ受體抑制劑 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS5538325A (en) * | 1978-09-11 | 1980-03-17 | Sankyo Co Ltd | 4-anilinoquinazoline derivative and its preparation |
| US4335127A (en) * | 1979-01-08 | 1982-06-15 | Janssen Pharmaceutica, N.V. | Piperidinylalkyl quinazoline compounds, composition and method of use |
| GB2160201B (en) * | 1984-06-14 | 1988-05-11 | Wyeth John & Brother Ltd | Quinazoline and cinnoline derivatives |
| US4921863A (en) * | 1988-02-17 | 1990-05-01 | Eisai Co., Ltd. | Cyclic amine derivatives |
| CA1340821C (en) * | 1988-10-06 | 1999-11-16 | Nobuyuki Fukazawa | Heterocyclic compounds and anticancer-drug reinforcing agents containing them as effective components |
| US5721237A (en) * | 1991-05-10 | 1998-02-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Protein tyrosine kinase aryl and heteroaryl quinazoline compounds having selective inhibition of HER-2 autophosphorylation properties |
| US5747498A (en) * | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| US6046206A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having a precancerous lesions with amide quinazoline derivatives |
| GB9624482D0 (en) * | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| ID18666A (id) * | 1996-01-31 | 1998-04-30 | Gist Brocades Bv | Penggunaan komposisi komposisi yang terdiri dari senyawa senyawa stabil yang efektif secara biologi |
| US6004967A (en) * | 1996-09-13 | 1999-12-21 | Sugen, Inc. | Psoriasis treatment with quinazoline compounds |
| US5929080A (en) * | 1997-05-06 | 1999-07-27 | American Cyanamid Company | Method of treating polycystic kidney disease |
| US6148197A (en) * | 1998-03-06 | 2000-11-14 | Sbc Technology Resources, Inc. | Intelligent roaming system with over the air programming |
| US6384223B1 (en) * | 1998-07-30 | 2002-05-07 | American Home Products Corporation | Substituted quinazoline derivatives |
| US6297258B1 (en) * | 1998-09-29 | 2001-10-02 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| TR200102505T2 (tr) * | 1999-02-27 | 2003-01-21 | Boehringer Ingelheim Pharma Kg | 4-amino-kinazolin ve kinolin türevleri. |
| US6080747A (en) * | 1999-03-05 | 2000-06-27 | Hughes Institute | JAK-3 inhibitors for treating allergic disorders |
| US20020082270A1 (en) * | 2000-08-26 | 2002-06-27 | Frank Himmelsbach | Aminoquinazolines which inhibit signal transduction mediated by tyrosine kinases |
| US6562319B2 (en) * | 2001-03-12 | 2003-05-13 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Radiolabeled irreversible inhibitors of epidermal growth factor receptor tyrosine kinase and their use in radioimaging and radiotherapy |
| US20040176361A1 (en) * | 2001-05-23 | 2004-09-09 | Masakazu Fujio | Fused heterocyclic compound and medicinal use thereof |
| RU2004116911A (ru) * | 2001-11-03 | 2005-11-10 | Астразенека Аб (Se) | Производные хиназолина в качестве противоопухолевых средств |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| 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 |
| CA2533345A1 (en) * | 2003-07-29 | 2005-02-10 | Astrazeneca Ab | Piperidyl-quinazoline derivatives as tyrosine kinase inhibitors |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline 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 |
| WO2005026150A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| MXPA06002963A (es) * | 2003-09-16 | 2006-06-14 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de cinasa de tirosina. |
| DE602004004811T2 (de) * | 2003-09-19 | 2007-11-22 | Astrazeneca Ab | Chinazolinderivate |
| 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 |
-
2003
- 2003-09-16 GB GBGB0321648.8A patent/GB0321648D0/en not_active Ceased
-
2004
- 2004-09-14 WO PCT/GB2004/003936 patent/WO2005026152A1/en not_active Ceased
- 2004-09-14 BR BRPI0414486-4A patent/BRPI0414486A/pt not_active Application Discontinuation
- 2004-09-14 AT AT04768482T patent/ATE450528T1/de not_active IP Right Cessation
- 2004-09-14 CA CA002539024A patent/CA2539024A1/en not_active Abandoned
- 2004-09-14 CN CNA2004800335283A patent/CN1882572A/zh active Pending
- 2004-09-14 US US10/572,262 patent/US20070015743A1/en not_active Abandoned
- 2004-09-14 JP JP2006526685A patent/JP2007505874A/ja active Pending
- 2004-09-14 EP EP04768482A patent/EP1664029B1/en not_active Expired - Lifetime
- 2004-09-14 MX MXPA06002965A patent/MXPA06002965A/es unknown
- 2004-09-14 AU AU2004272351A patent/AU2004272351A1/en not_active Abandoned
- 2004-09-14 DE DE602004024420T patent/DE602004024420D1/de not_active Expired - Lifetime
- 2004-09-16 TW TW093128079A patent/TW200526628A/zh unknown
- 2004-09-16 AR ARP040103319A patent/AR045752A1/es unknown
-
2006
- 2006-03-12 IL IL174260A patent/IL174260A0/en unknown
- 2006-03-15 ZA ZA200602189A patent/ZA200602189B/en unknown
- 2006-03-23 NO NO20061320A patent/NO20061320L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL174260A0 (en) | 2006-08-01 |
| NO20061320L (no) | 2006-04-26 |
| EP1664029B1 (en) | 2009-12-02 |
| GB0321648D0 (en) | 2003-10-15 |
| JP2007505874A (ja) | 2007-03-15 |
| MXPA06002965A (es) | 2006-06-14 |
| TW200526628A (en) | 2005-08-16 |
| AU2004272351A1 (en) | 2005-03-24 |
| WO2005026152A1 (en) | 2005-03-24 |
| US20070015743A1 (en) | 2007-01-18 |
| ATE450528T1 (de) | 2009-12-15 |
| BRPI0414486A (pt) | 2006-11-14 |
| DE602004024420D1 (de) | 2010-01-14 |
| CN1882572A (zh) | 2006-12-20 |
| EP1664029A1 (en) | 2006-06-07 |
| AR045752A1 (es) | 2005-11-09 |
| CA2539024A1 (en) | 2005-03-24 |
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