MXPA06014125A - Derivados de quinazolina en la forma de cinasas de tirosina de receptor erbb. - Google Patents

Info

Publication number

MXPA06014125A

MXPA06014125A MXPA06014125A MXPA06014125A MXPA06014125A MX PA06014125 A MXPA06014125 A MX PA06014125A MX PA06014125 A MXPA06014125 A MX PA06014125A MX PA06014125 A MXPA06014125 A MX PA06014125A MX PA06014125 A MXPA06014125 A MX PA06014125A

Authority

MX

Mexico

Prior art keywords

oxy

alkyl

methyl

quinazolin

phenyl

Prior art date

2004-06-04

Links

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• 102000001301 EGF receptor Human genes 0.000 title claims abstract description 14
• 108060006698 EGF receptor Proteins 0.000 title claims abstract description 14
• 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title abstract description 115
• 238000000034 method Methods 0.000 claims abstract description 88
• 230000008569 process Effects 0.000 claims abstract description 71
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 29
• 238000011282 treatment Methods 0.000 claims abstract description 13
• 230000005764 inhibitory process Effects 0.000 claims abstract description 10
• 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 7
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
• 238000004519 manufacturing process Methods 0.000 claims abstract description 7
• 238000002360 preparation method Methods 0.000 claims abstract description 6
• 239000003814 drug Substances 0.000 claims abstract description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
• 230000002265 prevention Effects 0.000 claims abstract description 3
• -1 cyano, nitro, hydroxy, amino, carboxy, carbamoyl Chemical group 0.000 claims description 917
• 125000000217 alkyl group Chemical group 0.000 claims description 787
• 125000001424 substituent group Chemical group 0.000 claims description 331
• 229910052757 nitrogen Inorganic materials 0.000 claims description 282
• 125000000623 heterocyclic group Chemical group 0.000 claims description 276
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 265
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 223
• 239000001257 hydrogen Substances 0.000 claims description 180
• 229910052739 hydrogen Inorganic materials 0.000 claims description 180
• 125000003545 alkoxy group Chemical group 0.000 claims description 164
• 229910052736 halogen Inorganic materials 0.000 claims description 137
• 150000002367 halogens Chemical class 0.000 claims description 136
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 129
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 127
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 118
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 113
• 125000000304 alkynyl group Chemical group 0.000 claims description 107
• 229910052760 oxygen Inorganic materials 0.000 claims description 99
• 125000003342 alkenyl group Chemical group 0.000 claims description 98
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 98
• 125000003282 alkyl amino group Chemical group 0.000 claims description 96
• 238000006243 chemical reaction Methods 0.000 claims description 91
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 71
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 66
• 125000001589 carboacyl group Chemical group 0.000 claims description 64
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 61
• 125000005842 heteroatom Chemical group 0.000 claims description 57
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 54
• 239000001301 oxygen Substances 0.000 claims description 53
• 125000001153 fluoro group Chemical group F* 0.000 claims description 52
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 50
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
• 229910052717 sulfur Inorganic materials 0.000 claims description 49
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 48
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 48
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 46
• 150000001875 compounds Chemical class 0.000 claims description 46
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 44
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 39
• 125000004423 acyloxy group Chemical group 0.000 claims description 37
• 125000004043 oxo group Chemical group O=* 0.000 claims description 37
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 35
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 35
• 125000004414 alkyl thio group Chemical group 0.000 claims description 34
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 32
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 31
• 125000004076 pyridyl group Chemical group 0.000 claims description 31
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
• 125000000524 functional group Chemical group 0.000 claims description 30
• 239000011593 sulfur Chemical group 0.000 claims description 30
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 29
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 29
• 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 29
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 25
• 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 24
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 23
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 23
• DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 19
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 19
• 229920006395 saturated elastomer Polymers 0.000 claims description 19
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 18
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 18
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 18
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 18
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 17
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
• 125000006319 alkynyl amino group Chemical group 0.000 claims description 16
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 125000003386 piperidinyl group Chemical group 0.000 claims description 15
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 14
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 13
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 230000000694 effects Effects 0.000 claims description 12
• 150000002431 hydrogen Chemical class 0.000 claims description 12
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 11
• 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 11
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 11
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
• 125000002393 azetidinyl group Chemical group 0.000 claims description 10
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 108091008598 receptor tyrosine kinases Proteins 0.000 claims description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 9
• 102000027426 receptor tyrosine kinases Human genes 0.000 claims description 9
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
• 229920002554 vinyl polymer Polymers 0.000 claims description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 8
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 6
• 239000007822 coupling agent Substances 0.000 claims description 6
• 125000005053 dihydropyrimidinyl group Chemical group N1(CN=CC=C1)* 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 claims description 6
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 6
• 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 6
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 6
• 241001465754 Metazoa Species 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 5
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 5
• 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 5
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 5
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
• 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 claims description 5
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims description 4
• 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims description 4
• 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 4
• 238000005859 coupling reaction Methods 0.000 claims description 4
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
• 230000004913 activation Effects 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 230000008878 coupling Effects 0.000 claims description 3
• 238000010168 coupling process Methods 0.000 claims description 3
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 3
• FXXHVBFLCDJJCF-QGZVFWFLSA-N (2R)-2-[4-amino-2-[3-fluoro-4-(6-methylpyridin-3-yl)oxyphenyl]quinazolin-5-yl]oxy-1-morpholin-4-ylpropan-1-one Chemical compound FC=1C=C(C=CC1OC=1C=NC(=CC1)C)C1=NC2=CC=CC(=C2C(=N1)N)O[C@@H](C(=O)N1CCOCC1)C FXXHVBFLCDJJCF-QGZVFWFLSA-N 0.000 claims description 2
• AARGIBALUCLPIO-QGZVFWFLSA-N (2R)-2-[4-amino-2-[4-(6-fluoropyridin-3-yl)oxy-3-methylphenyl]quinazolin-5-yl]oxy-1-morpholin-4-ylpropan-1-one Chemical compound FC1=CC=C(C=N1)OC1=C(C=C(C=C1)C1=NC2=CC=CC(=C2C(=N1)N)O[C@@H](C(=O)N1CCOCC1)C)C AARGIBALUCLPIO-QGZVFWFLSA-N 0.000 claims description 2
• CUXVZRKCEYEHCD-TZIWHRDSSA-N (2r)-1-[(3r)-3-hydroxypyrrolidin-1-yl]-2-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-5-yl]oxypropan-1-one Chemical compound O([C@H](C)C(=O)N1C[C@H](O)CC1)C(C=12)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OC1=CC=C(C)N=C1 CUXVZRKCEYEHCD-TZIWHRDSSA-N 0.000 claims description 2
• GQGOLYCZKGIRHT-OAHLLOKOSA-N (2r)-2-[4-(3-chloro-4-pyridin-2-yloxyanilino)quinazolin-5-yl]oxy-n,n-dimethylpropanamide Chemical compound C=12C(O[C@H](C)C(=O)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OC1=CC=CC=N1 GQGOLYCZKGIRHT-OAHLLOKOSA-N 0.000 claims description 2
• ZMAHCPKWJSLWEH-QGZVFWFLSA-N (2r)-2-[4-(3-chloro-4-pyridin-2-yloxyanilino)quinazolin-5-yl]oxy-n-(2-methoxyethyl)-n-methylpropanamide Chemical compound C=12C(O[C@H](C)C(=O)N(C)CCOC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OC1=CC=CC=N1 ZMAHCPKWJSLWEH-QGZVFWFLSA-N 0.000 claims description 2
• MBZYSNYQGXUZAF-LJQANCHMSA-N (2r)-2-[4-(3-methyl-4-pyridin-3-yloxyanilino)quinazolin-5-yl]oxy-1-morpholin-4-ylpropan-1-one Chemical compound O([C@H](C)C(=O)N1CCOCC1)C(C=12)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OC1=CC=CN=C1 MBZYSNYQGXUZAF-LJQANCHMSA-N 0.000 claims description 2
• WMDROLDZARJZNE-LJQANCHMSA-N (2r)-2-[4-(3-methyl-4-pyridin-4-yloxyanilino)quinazolin-5-yl]oxy-1-morpholin-4-ylpropan-1-one Chemical compound O([C@H](C)C(=O)N1CCOCC1)C(C=12)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OC1=CC=NC=C1 WMDROLDZARJZNE-LJQANCHMSA-N 0.000 claims description 2
• CQLYORSHVYBLMS-GOSISDBHSA-N (2r)-2-[4-(3-methyl-4-pyrimidin-5-yloxyanilino)quinazolin-5-yl]oxy-1-morpholin-4-ylpropan-1-one Chemical compound O([C@H](C)C(=O)N1CCOCC1)C(C=12)=CC=CC2=NC=NC=1NC(C=C1C)=CC=C1OC1=CN=CN=C1 CQLYORSHVYBLMS-GOSISDBHSA-N 0.000 claims description 2
• TYPJWHGRDVHRRZ-OAHLLOKOSA-N (2r)-2-[4-[3-chloro-4-(1,3-thiazol-2-yloxy)anilino]quinazolin-5-yl]oxy-1-morpholin-4-ylpropan-1-one Chemical compound O([C@H](C)C(=O)N1CCOCC1)C(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OC1=NC=CS1 TYPJWHGRDVHRRZ-OAHLLOKOSA-N 0.000 claims description 2
• DBSISHZEFSMQPK-GOSISDBHSA-N (2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxy-1-morpholin-4-ylpropan-1-one Chemical compound O([C@H](C)C(=O)N1CCOCC1)C(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DBSISHZEFSMQPK-GOSISDBHSA-N 0.000 claims description 2
• UTHNMKVUDJYYFU-GOSISDBHSA-N (2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxy-1-pyrrolidin-1-ylpropan-1-one Chemical compound O([C@H](C)C(=O)N1CCCC1)C(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 UTHNMKVUDJYYFU-GOSISDBHSA-N 0.000 claims description 2
• KXKMLDJBINFBMA-RUZDIDTESA-N (2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxy-4-hydroxy-1-morpholin-4-ylbutan-1-one Chemical compound O([C@H](CCO)C(=O)N1CCOCC1)C(C=12)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 KXKMLDJBINFBMA-RUZDIDTESA-N 0.000 claims description 2
• UFOUYPHVNFLZQT-HSZRJFAPSA-N (2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxy-4-hydroxy-n,n-dimethylbutanamide Chemical compound C=12C(O[C@H](CCO)C(=O)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 UFOUYPHVNFLZQT-HSZRJFAPSA-N 0.000 claims description 2
• LAOAMPGLBWUUOH-JOCHJYFZSA-N (2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxy-4-hydroxy-n-methylbutanamide Chemical compound C=12C(O[C@H](CCO)C(=O)NC)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 LAOAMPGLBWUUOH-JOCHJYFZSA-N 0.000 claims description 2
• QPPYSOHWFOUKPX-MRXNPFEDSA-N (2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxy-n,n-dimethylpropanamide Chemical compound C=12C(O[C@H](C)C(=O)N(C)C)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 QPPYSOHWFOUKPX-MRXNPFEDSA-N 0.000 claims description 2
• WZEUNGUUUBFSGF-QGZVFWFLSA-N (2r)-2-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-5-yl]oxy-n-(2-hydroxyethyl)-n-methylpropanamide Chemical compound C=12C(O[C@H](C)C(=O)N(C)CCO)=CC=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 WZEUNGUUUBFSGF-QGZVFWFLSA-N 0.000 claims description 2
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