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
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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
- C07D401/14—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
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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
- C07D403/12—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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- 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
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- 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
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- 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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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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| Application Number | Title | Priority Date | Filing Date |
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| ZA200602189A ZA200602189B (en) | 2003-09-16 | 2006-03-15 | Quinazoline derivatives as antitumor agents |
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Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE60231230D1 (de) * | 2001-11-03 | 2009-04-02 | Astrazeneca Ab | Quinazolin derivate als antitumor-mittel |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| 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 |
| KR20070027487A (ko) * | 2003-09-16 | 2007-03-09 | 아스트라제네카 아베 | 퀴나졸린 유도체 |
| BRPI0414489A8 (pt) * | 2003-09-16 | 2019-01-15 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, e, processo para a preparação de um derivado de quinazolina |
| 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 |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005075439A1 (en) * | 2004-02-03 | 2005-08-18 | Astrazeneca Ab | Quinazoline derivatives |
| CN1993349A (zh) * | 2004-06-04 | 2007-07-04 | 阿斯利康(瑞典)有限公司 | 作为erbb受体酪氨酸激酶的喹唑啉衍生物 |
| DE602005026865D1 (de) * | 2004-12-14 | 2011-04-21 | 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 |
| KR20080027253A (ko) * | 2005-06-16 | 2008-03-26 | 미리어드 제네틱스, 인크. | 약제학적 조성물 및 이의 용도 |
| JP2009508917A (ja) * | 2005-09-20 | 2009-03-05 | アストラゼネカ アクチボラグ | 抗癌剤としてのキナゾリン誘導体 |
| ATE488513T1 (de) * | 2005-09-20 | 2010-12-15 | Astrazeneca Ab | 4-(1h-indazol-5-ylamino)chinazolinverbindungen als inhibitoren der erbb-rezeptortyrosinkinase zur behandlung von krebs |
| WO2007059257A2 (en) * | 2005-11-15 | 2007-05-24 | Array Biopharma Inc. | N4-phenyl-quinaz0line-4 -amine derivatives and related compounds as erbb type i receptor tyrosine kinase inhibitors for the treatment of hyperproliferative diseases |
| EP1960371B1 (en) * | 2005-12-02 | 2009-09-16 | AstraZeneca AB | Quinazoleine derivatives used as inhibitors of erbb tyrosine kinase |
| US20100222344A1 (en) * | 2005-12-02 | 2010-09-02 | 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 |
| BRPI0807234A2 (pt) | 2007-02-06 | 2014-06-03 | Boehringer Ingelheim Int | Heterociclos bicíclicos, composições farmacêuticas que contêm estes compostos, o uso dos mesmos e processos para a preparação dos mesmos |
| WO2008124824A1 (en) * | 2007-04-10 | 2008-10-16 | Myriad Genetics, Inc. | Dosages and methods for the treatment of cancer |
| WO2008124828A1 (en) * | 2007-04-10 | 2008-10-16 | Myriad Genetics, Inc. | Methods for treating vascular disruption disorders |
| JP2010523696A (ja) * | 2007-04-10 | 2010-07-15 | ミリアド ファーマシューティカルズ， インコーポレイテッド | 脳腫瘍を治療する方法 |
| CA2720983A1 (en) * | 2007-04-10 | 2008-10-16 | Myrexis, Inc. | Method of treating melanoma |
| NZ580869A (en) * | 2007-04-10 | 2011-02-25 | Myriad Pharmaceuticals Inc | Methods for treating cancer |
| KR20100111291A (ko) | 2008-02-07 | 2010-10-14 | 베링거 인겔하임 인터내셔날 게엠베하 | 스피로사이클릭 헤테로사이클, 상기 화합물을 함유하는 약제, 이의 용도 및 이의 제조 방법 |
| MY183041A (en) | 2008-05-13 | 2021-02-08 | Astrazeneca Ab | Fumarate salt of 4- (3-chloro-2-fluoroanilino) -7-methoxy-6- {[1- (n-methylcarbamoylmethyl) piperidin- 4-yl] oxy}quinazoline |
| CA2733153C (en) | 2008-08-08 | 2016-11-08 | Boehringer Ingelheim International Gmbh | Cyclohexyloxy substituted heterocycles, pharmaceutical compositions containing these compounds and processes for preparing them |
| GB0820819D0 (en) | 2008-11-13 | 2008-12-24 | Sareum Ltd | Pharmaceutical compounds |
| CA2852060A1 (en) | 2011-10-14 | 2013-04-18 | Array Biopharma Inc. | Polymorphs of arry-380, a selective herb2 inhibitor and pharmaceutical compositions containing them |
| CA2852058C (en) | 2011-10-14 | 2021-06-01 | Array Biopharma Inc. | A solid dispersion of n4-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-n6-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)quinazoline-4,6-diamine |
| AR117424A1 (es) * | 2018-05-08 | 2021-08-04 | Dizal Jiangsu Pharmaceutical Co Ltd | Inhibidores de los receptores erbb |
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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 |
| US6117433A (en) * | 1996-01-31 | 2000-09-12 | Dsm N.V. | Use of compositions comprising stabilized biologically effective compounds |
| 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 |
| IL144143A0 (en) * | 1999-02-27 | 2002-05-23 | Boehringer Ingelheim Pharma | 4-amino-quinazoline and quinoline derivatives having an inhibitory effect on signal transduction mediated by tyrosine kinases |
| 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 |
| WO2002094790A1 (en) * | 2001-05-23 | 2002-11-28 | Mitsubishi Pharma Corporation | Fused heterocyclic compound and medicinal use thereof |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| DE60231230D1 (de) * | 2001-11-03 | 2009-04-02 | Astrazeneca Ab | Quinazolin derivate als antitumor-mittel |
| 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 |
| EP1660479A1 (en) * | 2003-07-29 | 2006-05-31 | Astrazeneca AB | Piperidyl-quinazoline derivatives as tyrosine kinase inhibitors |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| KR20070027487A (ko) * | 2003-09-16 | 2007-03-09 | 아스트라제네카 아베 | 퀴나졸린 유도체 |
| EP1664028A1 (en) * | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives as tyrosine kinase inhibitors |
| BRPI0414489A8 (pt) * | 2003-09-16 | 2019-01-15 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, e, processo para a preparação de um derivado de quinazolina |
| ATE353888T1 (de) * | 2003-09-19 | 2007-03-15 | Astrazeneca Ab | Chinazolinderivate |
| CA2540008A1 (en) * | 2003-09-25 | 2005-04-07 | Astrazeneca Ab | Quinazoline derivatives |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005075439A1 (en) * | 2004-02-03 | 2005-08-18 | Astrazeneca Ab | Quinazoline derivatives |
| CN1993349A (zh) * | 2004-06-04 | 2007-07-04 | 阿斯利康(瑞典)有限公司 | 作为erbb受体酪氨酸激酶的喹唑啉衍生物 |
-
2003
- 2003-09-16 GB GBGB0321648.8A patent/GB0321648D0/en not_active Ceased
-
2004
- 2004-09-14 JP JP2006526685A patent/JP2007505874A/ja active Pending
- 2004-09-14 MX MXPA06002965A patent/MXPA06002965A/es unknown
- 2004-09-14 AU AU2004272351A patent/AU2004272351A1/en not_active Abandoned
- 2004-09-14 EP EP04768482A patent/EP1664029B1/en not_active Expired - Lifetime
- 2004-09-14 BR BRPI0414486-4A patent/BRPI0414486A/pt not_active Application Discontinuation
- 2004-09-14 DE DE602004024420T patent/DE602004024420D1/de not_active Expired - Lifetime
- 2004-09-14 WO PCT/GB2004/003936 patent/WO2005026152A1/en not_active Ceased
- 2004-09-14 US US10/572,262 patent/US20070015743A1/en not_active Abandoned
- 2004-09-14 CA CA002539024A patent/CA2539024A1/en not_active Abandoned
- 2004-09-14 CN CNA2004800335283A patent/CN1882572A/zh active Pending
- 2004-09-14 AT AT04768482T patent/ATE450528T1/de not_active IP Right Cessation
- 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 |
|---|---|
| MXPA06002965A (es) | 2006-06-14 |
| EP1664029A1 (en) | 2006-06-07 |
| AR045752A1 (es) | 2005-11-09 |
| DE602004024420D1 (de) | 2010-01-14 |
| GB0321648D0 (en) | 2003-10-15 |
| US20070015743A1 (en) | 2007-01-18 |
| AU2004272351A1 (en) | 2005-03-24 |
| WO2005026152A1 (en) | 2005-03-24 |
| CN1882572A (zh) | 2006-12-20 |
| IL174260A0 (en) | 2006-08-01 |
| JP2007505874A (ja) | 2007-03-15 |
| CA2539024A1 (en) | 2005-03-24 |
| BRPI0414486A (pt) | 2006-11-14 |
| ATE450528T1 (de) | 2009-12-15 |
| EP1664029B1 (en) | 2009-12-02 |
| NO20061320L (no) | 2006-04-26 |
| TW200526628A (en) | 2005-08-16 |
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