MXPA06002963A - Derivados de quinazolina como inhibidores de cinasa de tirosina. - Google Patents
Derivados de quinazolina como inhibidores de cinasa de tirosina.Info
- Publication number
- MXPA06002963A MXPA06002963A MXPA06002963A MXPA06002963A MXPA06002963A MX PA06002963 A MXPA06002963 A MX PA06002963A MX PA06002963 A MXPA06002963 A MX PA06002963A MX PA06002963 A MXPA06002963 A MX PA06002963A MX PA06002963 A MXPA06002963 A MX PA06002963A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- alkyl
- formula
- group
- amino
- Prior art date
Links
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title abstract description 3
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 2
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 2
- 125000001424 substituent group Chemical group 0.000 claims abstract description 262
- 230000000694 effects Effects 0.000 claims abstract description 13
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
- 241001465754 Metazoa Species 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 3
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims abstract 4
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2212
- -1 cyano, nitro, hydroxy, amino, carboxy, carbamoyl Chemical group 0.000 claims description 521
- 125000000217 alkyl group Chemical group 0.000 claims description 456
- 229910052799 carbon Inorganic materials 0.000 claims description 428
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 412
- 125000003545 alkoxy group Chemical group 0.000 claims description 271
- 229910052739 hydrogen Inorganic materials 0.000 claims description 215
- 239000001257 hydrogen Substances 0.000 claims description 215
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 147
- 125000000623 heterocyclic group Chemical group 0.000 claims description 140
- 229910052757 nitrogen Inorganic materials 0.000 claims description 138
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 137
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 117
- 229910052760 oxygen Inorganic materials 0.000 claims description 114
- 229910052736 halogen Inorganic materials 0.000 claims description 99
- 125000003282 alkyl amino group Chemical group 0.000 claims description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
- 125000004429 atom Chemical group 0.000 claims description 82
- 150000002367 halogens Chemical group 0.000 claims description 80
- 125000000304 alkynyl group Chemical group 0.000 claims description 75
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 75
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 70
- 229910052717 sulfur Inorganic materials 0.000 claims description 70
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 68
- 125000001153 fluoro group Chemical group F* 0.000 claims description 67
- 150000003246 quinazolines Chemical class 0.000 claims description 65
- 125000003342 alkenyl group Chemical group 0.000 claims description 64
- 125000004423 acyloxy group Chemical group 0.000 claims description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 57
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 57
- 125000004414 alkyl thio group Chemical group 0.000 claims description 55
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 55
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 52
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 52
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 50
- 125000005843 halogen group Chemical group 0.000 claims description 47
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 45
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 44
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 42
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 40
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 35
- 125000001188 haloalkyl group Chemical group 0.000 claims description 30
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 29
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 29
- 125000004043 oxo group Chemical group O=* 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 239000011593 sulfur Substances 0.000 claims description 24
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 22
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 21
- 238000003780 insertion Methods 0.000 claims description 21
- 230000037431 insertion Effects 0.000 claims description 21
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 20
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 20
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 19
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000003386 piperidinyl group Chemical group 0.000 claims description 17
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 16
- 150000001721 carbon Chemical group 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 15
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 14
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001589 carboacyl group Chemical group 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 10
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 9
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 8
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 7
- 125000002393 azetidinyl group Chemical group 0.000 claims description 7
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims description 7
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000003547 cyclohexylalkoxy group Chemical group 0.000 claims description 3
- 125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims 13
- 150000002431 hydrogen Chemical group 0.000 claims 10
- QZVUZUMUSUTSSD-UHFFFAOYSA-N 2-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound CS(=O)(=O)N1CCC(CC1)OC1=NC2=CC=CC=C2C(=N1)N QZVUZUMUSUTSSD-UHFFFAOYSA-N 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- REHCWAJWIQRJSL-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)C2=C1 REHCWAJWIQRJSL-UHFFFAOYSA-N 0.000 claims 1
- DLTYTEJYAVHQND-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(C)=O)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DLTYTEJYAVHQND-UHFFFAOYSA-N 0.000 claims 1
- NWTXVZUXGGJITM-UHFFFAOYSA-N 2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]-7-methoxyquinazolin-4-amine Chemical compound N=1C2=CC(OC)=CC=C2C(N)=NC=1C(C=C1OC)=CC=C1OCC1=CC=CC(F)=C1 NWTXVZUXGGJITM-UHFFFAOYSA-N 0.000 claims 1
- ALDKMUMLEZDDDX-UHFFFAOYSA-N 2-hydroxy-1-[3-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-6-yl]oxyazetidin-1-yl]ethanone Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC(C1=C2)=NC=NC1=CC=C2OC1CN(C(=O)CO)C1 ALDKMUMLEZDDDX-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 241000370985 Parides Species 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000001819 mass spectrum Methods 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 229940015212 parid Drugs 0.000 claims 1
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 133
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 60
- 125000002252 acyl group Chemical group 0.000 description 54
- 229960005419 nitrogen Drugs 0.000 description 34
- 206010028980 Neoplasm Diseases 0.000 description 24
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 19
- 201000011510 cancer Diseases 0.000 description 15
- 239000000460 chlorine Chemical group 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 14
- 102000005962 receptors Human genes 0.000 description 14
- 108020003175 receptors Proteins 0.000 description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 10
- 125000002950 monocyclic group Chemical group 0.000 description 10
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 9
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 9
- 125000003551 oxepanyl group Chemical group 0.000 description 8
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 8
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 8
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 8
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 7
- 108700020796 Oncogene Proteins 0.000 description 7
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 7
- 125000004980 cyclopropylene group Chemical group 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- 102000001301 EGF receptor Human genes 0.000 description 6
- 108060006698 EGF receptor Proteins 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 6
- 125000005724 cycloalkenylene group Chemical group 0.000 description 6
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 6
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- 108091000080 Phosphotransferase Proteins 0.000 description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 102000020233 phosphotransferase Human genes 0.000 description 5
- 230000035755 proliferation Effects 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 210000004881 tumor cell Anatomy 0.000 description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 4
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 230000019491 signal transduction Effects 0.000 description 4
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Chemical compound OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 206010006187 Breast cancer Diseases 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 210000000170 cell membrane Anatomy 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 230000026731 phosphorylation Effects 0.000 description 3
- 238000006366 phosphorylation reaction Methods 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000001963 4 membered heterocyclic group Chemical group 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 102000001332 SRC Human genes 0.000 description 2
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- 230000002159 abnormal effect Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 230000010307 cell transformation Effects 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000004652 decahydroisoquinolinyl group Chemical group C1(NCCC2CCCCC12)* 0.000 description 2
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- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
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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
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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
- 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
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- Manufacturing & Machinery (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Inorganic Chemistry (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03292279 | 2003-09-16 | ||
| PCT/GB2004/003931 WO2005026151A1 (en) | 2003-09-16 | 2004-09-14 | Quinazoline derivatives as tyrosine kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06002963A true MXPA06002963A (es) | 2006-06-14 |
Family
ID=34307005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06002963A MXPA06002963A (es) | 2003-09-16 | 2004-09-14 | Derivados de quinazolina como inhibidores de cinasa de tirosina. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20070032508A1 (enExample) |
| EP (1) | EP1664028A1 (enExample) |
| JP (1) | JP2007505873A (enExample) |
| CN (1) | CN1882573A (enExample) |
| AU (1) | AU2004272350A1 (enExample) |
| BR (1) | BRPI0414447A (enExample) |
| CA (1) | CA2539022A1 (enExample) |
| IL (1) | IL174258A0 (enExample) |
| MX (1) | MXPA06002963A (enExample) |
| NO (1) | NO20061321L (enExample) |
| WO (1) | WO2005026151A1 (enExample) |
| ZA (1) | ZA200602190B (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005515176A (ja) * | 2001-11-03 | 2005-05-26 | アストラゼネカ アクチボラグ | 抗腫瘍剤としてのキナゾリン誘導体 |
| 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 |
| 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 |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| EP1664030A1 (en) * | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives |
| US7569577B2 (en) * | 2003-09-16 | 2009-08-04 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| DE602004004811T2 (de) * | 2003-09-19 | 2007-11-22 | Astrazeneca Ab | Chinazolinderivate |
| 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 |
| CN101124228B (zh) * | 2004-12-14 | 2011-06-15 | 阿斯利康(瑞典)有限公司 | 用作抗肿瘤药物的吡唑并嘧啶化合物 |
| 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 |
| CA2627590A1 (en) * | 2005-07-04 | 2007-01-11 | Boehringer Ingelheim International Gmbh | Method for the production of quinazolinone derivatives |
| US20100234371A1 (en) * | 2005-08-22 | 2010-09-16 | Frank Himmelsbach | Bicyclic heterocycles, pharmaceutical compositions containing these compounds, the use thereof and processes for the preparation thereof |
| US7820683B2 (en) * | 2005-09-20 | 2010-10-26 | Astrazeneca Ab | 4-(1H-indazol-5-yl-amino)-quinazoline compounds as erbB receptor tyrosine kinase inhibitors for the treatment of cancer |
| US20090239861A1 (en) * | 2005-09-20 | 2009-09-24 | Robert Hugh Bradbury | Quinazoline derivatives as anticancer agents |
| PL2090575T3 (pl) | 2005-11-15 | 2011-09-30 | Array Biopharma Inc | Sposoby i związki pośrednie do otrzymywania pochodnych N4-fenylo-chinazolino-4-aminy |
| WO2007063291A1 (en) * | 2005-12-02 | 2007-06-07 | Astrazeneca Ab | 4-anilino-substituted quinazoline derivatives as tyrosine kinase inhibitors |
| WO2008041118A2 (en) * | 2006-10-04 | 2008-04-10 | Pfizer Products Inc. | Pyrido[4,3-d]pyrimidin-4(3h)-one derivatives as calcium receptor antagonists |
| 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 |
| EA200901041A1 (ru) | 2007-02-06 | 2010-02-26 | Бёрингер Ингельхайм Интернациональ Гмбх | Бициклические гетероциклы, содержащие эти соединения лекарственные средства, их применение и способ их получения |
| TWI377944B (en) * | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
| RS52573B (sr) | 2008-02-07 | 2013-04-30 | Boehringer Ingelheim International Gmbh | Spirociklični heterocikli, lekovi koji sadrže navedeno jedinjenje, njihova primena i postupak za njihovu proizvodnju |
| BRPI0912170A2 (pt) | 2008-05-13 | 2015-10-13 | Astrazeneca Ab | composto, forma a, processo para a preparação da mesma, composição farmacêutica, uso de um composto, e, método para tratar um câncer em um animal de sangue quente |
| 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 |
| UA116875C2 (uk) | 2011-10-14 | 2018-05-25 | Еррей Біофарма Інк. | Поліморфи arry-380 селективного інгібітору erbb2 і фармацевтичні композиції, що їх містять |
| CN105153046A (zh) * | 2015-08-25 | 2015-12-16 | 佛山市赛维斯医药科技有限公司 | 双卤素取代的乙氧基苯并喹唑啉类酪氨酸激酶抑制剂及用途 |
| CN105153047A (zh) * | 2015-08-25 | 2015-12-16 | 佛山市赛维斯医药科技有限公司 | 含新型苯并喹唑啉和邻位氟结构的酪氨酸激酶抑制剂及用途 |
| UY37935A (es) * | 2017-10-18 | 2020-03-31 | Spectrum Pharmaceuticals Inc | Inhibidores de tirosina quinasas de la familia de los egfr mutantes |
| WO2020262998A1 (ko) * | 2019-06-26 | 2020-12-30 | 한미약품 주식회사 | 항 종양 활성을 갖는 신규 퀴나졸린 유도체 및 이를 포함하는 약학 조성물 |
| WO2021231400A1 (en) * | 2020-05-12 | 2021-11-18 | Accutar Biotechnology, Inc. | Bis-aryl ethers containing n-acyl azetidine as egfr/her2 inhibitors |
| WO2022105908A1 (zh) * | 2020-11-23 | 2022-05-27 | 上海和誉生物医药科技有限公司 | Egfr抑制剂及其制备方法与在药学上的应用 |
| EP4267137A4 (en) * | 2020-12-22 | 2024-11-06 | Enliven Inc. | HETEROARYL-LACTAM-FUSION PYRIMIDINE DERIVATIVES AS ERBB2 INHIBITORS |
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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 |
| CA2216169C (en) * | 1996-01-31 | 2007-01-23 | Gist-Brocades B.V. | Use of compositions comprising stabilized biologically effective compounds |
| GB9603095D0 (en) * | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| GB9607729D0 (en) * | 1996-04-13 | 1996-06-19 | Zeneca Ltd | Quinazoline derivatives |
| 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 |
| 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 |
| UA71945C2 (en) * | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
| AU3281600A (en) * | 1999-02-27 | 2000-09-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 4-amino-quinazoline and quinoline derivatives having an inhibitory effect on signal transsduction mediated by tyrosine kinases |
| US6080747A (en) * | 1999-03-05 | 2000-06-27 | Hughes Institute | JAK-3 inhibitors for treating allergic disorders |
| DE19911509A1 (de) * | 1999-03-15 | 2000-09-21 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| 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 |
| JP2005515176A (ja) * | 2001-11-03 | 2005-05-26 | アストラゼネカ アクチボラグ | 抗腫瘍剤としてのキナゾリン誘導体 |
| TWI324597B (en) * | 2002-03-28 | 2010-05-11 | Astrazeneca Ab | Quinazoline derivatives |
| AU2003226705B2 (en) * | 2002-03-30 | 2008-11-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 4-(N-phenylamino)-quinazolines / quinolines as tyrosine kinase inhibitors |
| 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 |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| 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 |
| 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 |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| US7569577B2 (en) * | 2003-09-16 | 2009-08-04 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| DE602004004811T2 (de) * | 2003-09-19 | 2007-11-22 | Astrazeneca Ab | Chinazolinderivate |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| US20070043010A1 (en) * | 2003-09-25 | 2007-02-22 | Astrazeneca Uk Limited | Quinazoline derivatives |
| 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 |
-
2004
- 2004-09-14 AU AU2004272350A patent/AU2004272350A1/en not_active Abandoned
- 2004-09-14 CA CA002539022A patent/CA2539022A1/en not_active Abandoned
- 2004-09-14 JP JP2006526684A patent/JP2007505873A/ja active Pending
- 2004-09-14 CN CNA2004800335692A patent/CN1882573A/zh active Pending
- 2004-09-14 EP EP04768477A patent/EP1664028A1/en not_active Withdrawn
- 2004-09-14 US US10/571,851 patent/US20070032508A1/en not_active Abandoned
- 2004-09-14 WO PCT/GB2004/003931 patent/WO2005026151A1/en not_active Ceased
- 2004-09-14 MX MXPA06002963A patent/MXPA06002963A/es unknown
- 2004-09-14 BR BRPI0414447-3A patent/BRPI0414447A/pt not_active Application Discontinuation
-
2006
- 2006-03-12 IL IL174258A patent/IL174258A0/en unknown
- 2006-03-15 ZA ZA200602190A patent/ZA200602190B/en unknown
- 2006-03-23 NO NO20061321A patent/NO20061321L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004272350A1 (en) | 2005-03-24 |
| NO20061321L (no) | 2006-04-26 |
| IL174258A0 (en) | 2006-08-01 |
| WO2005026151A1 (en) | 2005-03-24 |
| CA2539022A1 (en) | 2005-03-24 |
| BRPI0414447A (pt) | 2006-11-14 |
| JP2007505873A (ja) | 2007-03-15 |
| CN1882573A (zh) | 2006-12-20 |
| ZA200602190B (en) | 2007-09-26 |
| US20070032508A1 (en) | 2007-02-08 |
| EP1664028A1 (en) | 2006-06-07 |
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