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
- C04B35/632—Organic additives
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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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- Engineering & Computer Science (AREA)
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- Manufacturing & Machinery (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Hematology (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 (https=) |
| EP (1) | EP1664028A1 (https=) |
| JP (1) | JP2007505873A (https=) |
| CN (1) | CN1882573A (https=) |
| AU (1) | AU2004272350A1 (https=) |
| BR (1) | BRPI0414447A (https=) |
| CA (1) | CA2539022A1 (https=) |
| IL (1) | IL174258A0 (https=) |
| MX (1) | MXPA06002963A (https=) |
| NO (1) | NO20061321L (https=) |
| WO (1) | WO2005026151A1 (https=) |
| ZA (1) | ZA200602190B (https=) |
Families Citing this family (39)
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| 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 |
| 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 |
| AU2004272345A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| AU2004272346A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| ES2305844T3 (es) * | 2003-09-16 | 2008-11-01 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de tirosina cinasa. |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| CN1882570B (zh) * | 2003-09-19 | 2010-12-08 | 阿斯利康(瑞典)有限公司 | 喹唑啉衍生物 |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| JP5032851B2 (ja) * | 2004-02-03 | 2012-09-26 | アストラゼネカ アクチボラグ | キナゾリン誘導体 |
| AU2005250224A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as ERBB receptor tyrosine kinases |
| EP1838712B8 (en) * | 2004-12-14 | 2011-10-12 | AstraZeneca AB | Pyrazolopyrimidine compounds as antitumor agents |
| GB0504474D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| GB0508715D0 (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 |
| CA2619037A1 (en) * | 2005-08-22 | 2007-03-01 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles medicaments comprising said compounds use and method for production thereof |
| 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 |
| WO2007034144A1 (en) * | 2005-09-20 | 2007-03-29 | Astrazeneca Ab | 4- (ih-indazol-s-yl-amino)-quinazoline compounds as erbb receptor tyrosine kinase inhibitors for the treatment of cancer |
| ES2364901T3 (es) | 2005-11-15 | 2011-09-16 | Array Biopharma, Inc. | Procesos e intermedios para la preparación de derivados de n4-fenil-quinazolin-4-amina. |
| JP2009517450A (ja) * | 2005-12-02 | 2009-04-30 | アストラゼネカ アクチボラグ | チロシンキナーゼ阻害薬としての４−アニリノ置換キナゾリン誘導体 |
| 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 |
| EP2118075A1 (de) | 2007-02-06 | 2009-11-18 | Boehringer Ingelheim International GmbH | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| TWI377944B (en) * | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
| CA2711582A1 (en) | 2008-02-07 | 2009-08-13 | Boehringer Ingelheim International Gmbh | Spirocyclic heterocycles, formulations containing said compounds, use thereof and processes for the preparation thereof |
| EP2303276B1 (en) | 2008-05-13 | 2013-11-13 | 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 |
| RU2629116C2 (ru) | 2011-10-14 | 2017-08-24 | Эррэй Биофарма Инк. | Полиморфы arry-380, селективного ингибитора erbb2, и фармацевтические составы, содержащие их |
| 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 |
| 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 |
| AR113451A1 (es) * | 2017-10-18 | 2020-05-06 | 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 |
| US20240116921A1 (en) * | 2020-12-22 | 2024-04-11 | Enliven Therapeutics, Inc. | Lactam (hetero)arylfusedpyrimidine derivatives as inhibitors of erbb2 |
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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 |
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| GB9603095D0 (en) * | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
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| 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 |
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| 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 |
| JPWO2002094790A1 (ja) * | 2001-05-23 | 2004-09-09 | 三菱ウェルファーマ株式会社 | 縮合ヘテロ環化合物およびその医薬用途 |
| 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 |
| TWI324597B (en) * | 2002-03-28 | 2010-05-11 | Astrazeneca Ab | Quinazoline derivatives |
| CA2476008C (en) * | 2002-03-30 | 2011-12-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| 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 |
| JP2007500177A (ja) * | 2003-07-29 | 2007-01-11 | アストラゼネカ アクチボラグ | チロシンキナーゼ阻害剤としてのピペリジルキナゾリン誘導体 |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| AU2004272346A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| ES2305844T3 (es) * | 2003-09-16 | 2008-11-01 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de tirosina cinasa. |
| CN1882570B (zh) * | 2003-09-19 | 2010-12-08 | 阿斯利康(瑞典)有限公司 | 喹唑啉衍生物 |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| KR20060100388A (ko) * | 2003-09-25 | 2006-09-20 | 아스트라제네카 아베 | 퀴나졸린 유도체 |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| JP5032851B2 (ja) * | 2004-02-03 | 2012-09-26 | アストラゼネカ アクチボラグ | キナゾリン誘導体 |
| AU2005250224A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as ERBB receptor tyrosine kinases |
-
2004
- 2004-09-14 US US10/571,851 patent/US20070032508A1/en not_active Abandoned
- 2004-09-14 CA CA002539022A patent/CA2539022A1/en not_active Abandoned
- 2004-09-14 EP EP04768477A patent/EP1664028A1/en not_active Withdrawn
- 2004-09-14 BR BRPI0414447-3A patent/BRPI0414447A/pt not_active Application Discontinuation
- 2004-09-14 AU AU2004272350A patent/AU2004272350A1/en not_active Abandoned
- 2004-09-14 JP JP2006526684A patent/JP2007505873A/ja active Pending
- 2004-09-14 MX MXPA06002963A patent/MXPA06002963A/es unknown
- 2004-09-14 CN CNA2004800335692A patent/CN1882573A/zh active Pending
- 2004-09-14 WO PCT/GB2004/003931 patent/WO2005026151A1/en not_active Ceased
-
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 |
|---|---|
| US20070032508A1 (en) | 2007-02-08 |
| EP1664028A1 (en) | 2006-06-07 |
| BRPI0414447A (pt) | 2006-11-14 |
| CA2539022A1 (en) | 2005-03-24 |
| NO20061321L (no) | 2006-04-26 |
| IL174258A0 (en) | 2006-08-01 |
| ZA200602190B (en) | 2007-09-26 |
| AU2004272350A1 (en) | 2005-03-24 |
| JP2007505873A (ja) | 2007-03-15 |
| CN1882573A (zh) | 2006-12-20 |
| WO2005026151A1 (en) | 2005-03-24 |
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