CA2909310A1 - Quinazolines and azaquinazolines as dual inhibitors of ras/raf/mek/erk and pi3k/akt/pten/mtor pathways - Google Patents

Info

Publication number

CA2909310A1

CA2909310A1 CA2909310A CA2909310A CA2909310A1 CA 2909310 A1 CA2909310 A1 CA 2909310A1 CA 2909310 A CA2909310 A CA 2909310A CA 2909310 A CA2909310 A CA 2909310A CA 2909310 A1 CA2909310 A1 CA 2909310A1

Authority

CA

Canada

Prior art keywords

sulfonamide

fluoropropane

fluorophenyl

morpholinoquinazolin

methoxy

Prior art date

2013-04-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 230000037361 pathway Effects 0.000 title claims abstract description 63
• 150000003246 quinazolines Chemical class 0.000 title abstract 2
• 239000003112 inhibitor Substances 0.000 title description 12
• 230000009977 dual effect Effects 0.000 title description 5
• 101150097381 Mtor gene Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 421
• 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims abstract description 66
• 108091007960 PI3Ks Proteins 0.000 claims abstract description 66
• 238000000034 method Methods 0.000 claims abstract description 65
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 61
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims abstract description 58
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims abstract description 58
• 108010011536 PTEN Phosphohydrolase Proteins 0.000 claims abstract description 45
• 102000014160 PTEN Phosphohydrolase Human genes 0.000 claims abstract description 44
• 201000011510 cancer Diseases 0.000 claims abstract description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 201000010099 disease Diseases 0.000 claims abstract description 15
• 150000003839 salts Chemical class 0.000 claims abstract description 15
• 230000002159 abnormal effect Effects 0.000 claims abstract description 11
• 230000004663 cell proliferation Effects 0.000 claims abstract description 10
• -1 pyridine-4-yl Chemical group 0.000 claims description 145
• 239000000203 mixture Substances 0.000 claims description 120
• 230000000694 effects Effects 0.000 claims description 91
• 230000002829 reductive effect Effects 0.000 claims description 84
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 69
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 56
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 56
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims description 46
• 230000005764 inhibitory process Effects 0.000 claims description 34
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 150000002367 halogens Chemical class 0.000 claims description 29
• 108010091528 Proto-Oncogene Proteins B-raf Proteins 0.000 claims description 28
• 102000018471 Proto-Oncogene Proteins B-raf Human genes 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
• 230000035772 mutation Effects 0.000 claims description 24
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 230000002401 inhibitory effect Effects 0.000 claims description 15
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 210000004369 blood Anatomy 0.000 claims description 8
• 239000008280 blood Substances 0.000 claims description 8
• 210000003800 pharynx Anatomy 0.000 claims description 8
• 210000003491 skin Anatomy 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 238000012544 monitoring process Methods 0.000 claims description 7
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
• 210000000481 breast Anatomy 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 150000002780 morpholines Chemical class 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 5
• 206010025323 Lymphomas Diseases 0.000 claims description 5
• 150000001721 carbon Chemical group 0.000 claims description 5
• 210000004072 lung Anatomy 0.000 claims description 5
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• 210000004100 adrenal gland Anatomy 0.000 claims description 4
• 210000000988 bone and bone Anatomy 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
• 210000000621 bronchi Anatomy 0.000 claims description 4
• 210000003169 central nervous system Anatomy 0.000 claims description 4
• 210000003679 cervix uteri Anatomy 0.000 claims description 4
• 210000000038 chest Anatomy 0.000 claims description 4
• 210000001072 colon Anatomy 0.000 claims description 4
• 210000003238 esophagus Anatomy 0.000 claims description 4
• 210000001508 eye Anatomy 0.000 claims description 4
• 210000003128 head Anatomy 0.000 claims description 4
• 210000000936 intestine Anatomy 0.000 claims description 4
• 210000003734 kidney Anatomy 0.000 claims description 4
• 210000000867 larynx Anatomy 0.000 claims description 4
• 208000032839 leukemia Diseases 0.000 claims description 4
• 210000004185 liver Anatomy 0.000 claims description 4
• 210000001165 lymph node Anatomy 0.000 claims description 4
• 210000000214 mouth Anatomy 0.000 claims description 4
• 210000003739 neck Anatomy 0.000 claims description 4
• 210000001672 ovary Anatomy 0.000 claims description 4
• 210000000496 pancreas Anatomy 0.000 claims description 4
• 210000000664 rectum Anatomy 0.000 claims description 4
• 210000002784 stomach Anatomy 0.000 claims description 4
• 210000001550 testis Anatomy 0.000 claims description 4
• 210000001685 thyroid gland Anatomy 0.000 claims description 4
• 210000003932 urinary bladder Anatomy 0.000 claims description 4
• 210000004291 uterus Anatomy 0.000 claims description 4
• 210000001215 vagina Anatomy 0.000 claims description 4
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 239000011734 sodium Substances 0.000 claims description 3
• 229910052708 sodium Inorganic materials 0.000 claims description 3
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
• 229930192474 thiophene Natural products 0.000 claims description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
• 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 2
• RXYPXQSKLGGKOL-UHFFFAOYSA-O 1,4-dimethylpiperazin-1-ium Chemical compound CN1CC[NH+](C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-O 0.000 claims description 2
• AXWLKJWVMMAXBD-UHFFFAOYSA-N 1-butylpiperidine Chemical compound CCCCN1CCCCC1 AXWLKJWVMMAXBD-UHFFFAOYSA-N 0.000 claims description 2
• LPCWDBCEHWHJGX-UHFFFAOYSA-N 1-ethyl-2-methylpiperidine Chemical compound CCN1CCCCC1C LPCWDBCEHWHJGX-UHFFFAOYSA-N 0.000 claims description 2
• YQOPNAOQGQSUHF-UHFFFAOYSA-N 1-propan-2-ylpyrrolidine Chemical compound CC(C)N1CCCC1 YQOPNAOQGQSUHF-UHFFFAOYSA-N 0.000 claims description 2
• NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 claims description 2
• HVCNXQOWACZAFN-UHFFFAOYSA-O 4-ethylmorpholin-4-ium Chemical compound CC[NH+]1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-O 0.000 claims description 2
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 2
• BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
• RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 claims description 2
• 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 claims description 2
• 150000001556 benzimidazoles Chemical class 0.000 claims description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 230000000973 chemotherapeutic effect Effects 0.000 claims description 2
• WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 claims description 2
• PAFZNILMFXTMIY-UHFFFAOYSA-O cyclohexylammonium Chemical compound [NH3+]C1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-O 0.000 claims description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-O hydron piperazine Chemical compound [H+].C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-O 0.000 claims description 2
• 150000002473 indoazoles Chemical class 0.000 claims description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 229910052744 lithium Inorganic materials 0.000 claims description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 claims description 2
• DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 239000011591 potassium Substances 0.000 claims description 2
• 229910052700 potassium Inorganic materials 0.000 claims description 2
• 150000003222 pyridines Chemical class 0.000 claims description 2
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 2
• 150000003230 pyrimidines Chemical class 0.000 claims description 2
• 150000003233 pyrroles Chemical class 0.000 claims description 2
• 125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims description 2
• GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 claims description 2
• ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
• DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical compound OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 claims description 2
• 102000007665 Extracellular Signal-Regulated MAP Kinases Human genes 0.000 claims 7
• 210000002307 prostate Anatomy 0.000 claims 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• GRZLPWDCAOYDJI-UHFFFAOYSA-N 1-[4-[6-[2-fluoro-3-(propylsulfonylamino)phenyl]-8-methoxy-4-morpholin-4-ylquinazolin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=CC(NC(=O)NC=3C=CN=CC=3)=CC=2)=C1F GRZLPWDCAOYDJI-UHFFFAOYSA-N 0.000 claims 1
• OUGVIUBGWBVONY-UHFFFAOYSA-N 1-[4-[6-[3-[(2,6-difluorophenyl)sulfonylamino]-2-fluorophenyl]-8-methoxy-4-morpholin-4-ylquinazolin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound N1=C2C(OC)=CC(C=3C(=C(NS(=O)(=O)C=4C(=CC=CC=4F)F)C=CC=3)F)=CC2=C(N2CCOCC2)N=C1C1=CC=C(NC(=O)NCCO)C=C1 OUGVIUBGWBVONY-UHFFFAOYSA-N 0.000 claims 1
• PONJYXCDURJRQT-UHFFFAOYSA-N 1-[4-[6-[3-[(2,6-difluorophenyl)sulfonylamino]-2-fluorophenyl]-8-methoxy-4-morpholin-4-ylquinazolin-2-yl]phenyl]-3-methylurea Chemical compound CNC(=O)Nc1ccc(cc1)-c1nc(N2CCOCC2)c2cc(cc(OC)c2n1)-c1cccc(NS(=O)(=O)c2c(F)cccc2F)c1F PONJYXCDURJRQT-UHFFFAOYSA-N 0.000 claims 1
• PAMIQIKDUOTOBW-UHFFFAOYSA-O 1-methylpiperidin-1-ium Chemical compound C[NH+]1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-O 0.000 claims 1
• KPXDBHOHENZITF-UHFFFAOYSA-N 2,6-difluoro-n-[2-fluoro-3-[8-methoxy-4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)quinazolin-6-yl]phenyl]benzenesulfonamide Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(OC)=CC(C=3C(=C(NS(=O)(=O)C=4C(=CC=CC=4F)F)C=CC=3)F)=CC2=C1N1CCOCC1 KPXDBHOHENZITF-UHFFFAOYSA-N 0.000 claims 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
• WHOWLCMSTNDPTP-UHFFFAOYSA-N 2-[2-(6-aminopyridin-3-yl)-6-[2-fluoro-3-(3-fluoropropylsulfonylamino)phenyl]-4-morpholin-4-ylquinazolin-8-yl]oxyacetamide Chemical compound N1=C2C(OCC(=O)N)=CC(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)=CC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 WHOWLCMSTNDPTP-UHFFFAOYSA-N 0.000 claims 1
• CKAGEKRKCUKMLU-UHFFFAOYSA-N 2-[2-(6-aminopyridin-3-yl)-6-[2-fluoro-3-(3-fluoropropylsulfonylamino)phenyl]-4-morpholin-4-ylquinazolin-8-yl]oxyacetic acid 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.NC1=CC=C(C=N1)C1=NC2=C(C=C(C=C2C(=N1)N1CCOCC1)C1=C(C(=CC=C1)NS(=O)(=O)CCCF)F)OCC(=O)O CKAGEKRKCUKMLU-UHFFFAOYSA-N 0.000 claims 1
• VBKTZVRNZUNCOK-UHFFFAOYSA-N 3-fluoro-N-[2-fluoro-3-[2-(1H-indazol-4-yl)-8-methyl-4-morpholin-4-ylquinazolin-6-yl]phenyl]propane-1-sulfonamide Chemical compound Cc1cc(cc2c(nc(nc12)-c1cccc2[nH]ncc12)N1CCOCC1)-c1cccc(NS(=O)(=O)CCCF)c1F VBKTZVRNZUNCOK-UHFFFAOYSA-N 0.000 claims 1
• HMTTWIOLWKEWCU-UHFFFAOYSA-N 3-fluoro-N-[2-fluoro-3-[2-[2-(3-hydroxypropylamino)pyrimidin-5-yl]-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]phenyl]propane-1-sulfonamide Chemical compound OCCCNc1ncc(cn1)-c1nc(N2CCOCC2)c2nc(ccc2n1)-c1cccc(NS(=O)(=O)CCCF)c1F HMTTWIOLWKEWCU-UHFFFAOYSA-N 0.000 claims 1
• XZZOSDWIUMLDIC-UHFFFAOYSA-N 3-fluoro-N-[2-fluoro-3-[2-[2-(methylamino)pyrimidin-5-yl]-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]phenyl]propane-1-sulfonamide Chemical compound CNc1ncc(cn1)-c1nc(N2CCOCC2)c2nc(ccc2n1)-c1cccc(NS(=O)(=O)CCCF)c1F XZZOSDWIUMLDIC-UHFFFAOYSA-N 0.000 claims 1
• VBLJEGGZVBIVSA-UHFFFAOYSA-N 3-fluoro-N-[2-fluoro-3-[2-[4-(methanesulfonamido)phenyl]-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]phenyl]propane-1-sulfonamide Chemical compound COc1cc(cc2c(nc(nc12)-c1ccc(NS(C)(=O)=O)cc1)N1CCOCC1)-c1cccc(NS(=O)(=O)CCCF)c1F VBLJEGGZVBIVSA-UHFFFAOYSA-N 0.000 claims 1
• KJIOMOVRUDJUJF-UHFFFAOYSA-N 3-fluoro-N-[2-fluoro-3-[2-[6-(3-hydroxypropylamino)pyridin-3-yl]-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]phenyl]propane-1-sulfonamide Chemical compound FCCCS(=O)(=O)NC1=C(C(=CC=C1)C=1C=CC=2N=C(N=C(C=2N=1)N1CCOCC1)C=1C=NC(=CC=1)NCCCO)F KJIOMOVRUDJUJF-UHFFFAOYSA-N 0.000 claims 1
• ZSQZEIWTLAMWQL-UHFFFAOYSA-N 3-fluoro-N-[2-fluoro-3-[2-[6-(methylamino)pyridin-3-yl]-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]phenyl]propane-1-sulfonamide Chemical compound CNc1ccc(cn1)-c1nc(N2CCOCC2)c2nc(ccc2n1)-c1cccc(NS(=O)(=O)CCCF)c1F ZSQZEIWTLAMWQL-UHFFFAOYSA-N 0.000 claims 1
• BEPTZYZPIRBCPS-UHFFFAOYSA-N 3-fluoro-N-[2-fluoro-3-[4-morpholin-4-yl-2-[2-(propylamino)pyrimidin-5-yl]pyrido[3,2-d]pyrimidin-6-yl]phenyl]propane-1-sulfonamide Chemical compound CCCNc1ncc(cn1)-c1nc(N2CCOCC2)c2nc(ccc2n1)-c1cccc(NS(=O)(=O)CCCF)c1F BEPTZYZPIRBCPS-UHFFFAOYSA-N 0.000 claims 1
• JZESEEIETMQRAR-UHFFFAOYSA-N 3-fluoro-N-[2-fluoro-3-[4-morpholin-4-yl-2-[6-(propan-2-ylamino)pyridin-3-yl]pyrido[3,2-d]pyrimidin-6-yl]phenyl]propane-1-sulfonamide Chemical compound CC(C)Nc1ccc(cn1)-c1nc(N2CCOCC2)c2nc(ccc2n1)-c1cccc(NS(=O)(=O)CCCF)c1F JZESEEIETMQRAR-UHFFFAOYSA-N 0.000 claims 1
• XAKYAWDLGDQDRQ-UHFFFAOYSA-N 3-fluoro-N-[2-fluoro-3-[4-morpholin-4-yl-2-[6-(propylamino)pyridin-3-yl]pyrido[3,2-d]pyrimidin-6-yl]phenyl]propane-1-sulfonamide Chemical compound CCCNc1ccc(cn1)-c1nc(N2CCOCC2)c2nc(ccc2n1)-c1cccc(NS(=O)(=O)CCCF)c1F XAKYAWDLGDQDRQ-UHFFFAOYSA-N 0.000 claims 1
• STKCCHQPMXXXPZ-UHFFFAOYSA-N 3-fluoro-n-[2-fluoro-3-[2-[6-(2-hydroxyethylamino)pyridin-3-yl]-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]phenyl]propane-1-sulfonamide Chemical compound C1=NC(NCCO)=CC=C1C1=NC(N2CCOCC2)=C(N=C(C=C2)C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)C2=N1 STKCCHQPMXXXPZ-UHFFFAOYSA-N 0.000 claims 1
• HCAUATRKBGECLJ-UHFFFAOYSA-N 3-fluoro-n-[2-fluoro-3-[4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)pyrido[3,2-d]pyrimidin-6-yl]phenyl]propane-1-sulfonamide Chemical compound FCCCS(=O)(=O)NC1=CC=CC(C=2N=C3C(N4CCOCC4)=NC(=NC3=CC=2)C=2C=C3C=CNC3=NC=2)=C1F HCAUATRKBGECLJ-UHFFFAOYSA-N 0.000 claims 1
• DIAMMAIIQWKBTP-GOSISDBHSA-N 3-fluoro-n-[2-fluoro-3-[8-methoxy-4-[(3r)-3-methylmorpholin-4-yl]-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)quinazolin-6-yl]phenyl]propane-1-sulfonamide Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(OC)=CC(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)=CC2=C1N1CCOC[C@H]1C DIAMMAIIQWKBTP-GOSISDBHSA-N 0.000 claims 1
• FJZIEDDVXBNATJ-UHFFFAOYSA-N 3-fluoro-n-[2-fluoro-3-[8-methoxy-4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)quinazolin-6-yl]phenyl]propane-1-sulfonamide Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(OC)=CC(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)=CC2=C1N1CCOCC1 FJZIEDDVXBNATJ-UHFFFAOYSA-N 0.000 claims 1
• GBVAWUHESPWWDF-UHFFFAOYSA-N 3-fluoro-n-[2-fluoro-3-[8-methoxy-4-morpholin-4-yl-2-[6-(propylamino)pyridin-3-yl]quinazolin-6-yl]phenyl]propane-1-sulfonamide Chemical compound C1=NC(NCCC)=CC=C1C1=NC(N2CCOCC2)=C(C=C(C=C2OC)C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)C2=N1 GBVAWUHESPWWDF-UHFFFAOYSA-N 0.000 claims 1
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
• BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims 1
• AZEFSIAYOQKQFU-HNNXBMFYSA-N N-[3-[2-(2-amino-4-methylpyrimidin-5-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-2,5-difluorobenzenesulfonamide Chemical compound NC1=NC=C(C(=N1)C)C=1N=C(C2=C(N=1)C=CC(=N2)C=1C(=C(C=CC=1)NS(=O)(=O)C1=C(C=CC(=C1)F)F)F)N1[C@H](COCC1)C AZEFSIAYOQKQFU-HNNXBMFYSA-N 0.000 claims 1
• HNNSHBLYLKUEKC-HNNXBMFYSA-N N-[3-[2-(2-amino-4-methylpyrimidin-5-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@H]1COCCN1c1nc(nc2ccc(nc12)-c1cccc(NS(=O)(=O)CCCF)c1F)-c1cnc(N)nc1C HNNSHBLYLKUEKC-HNNXBMFYSA-N 0.000 claims 1
• GOYNWVKPYAPRGK-UHFFFAOYSA-N N-[3-[2-(2-amino-4-methylpyrimidin-5-yl)-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=NC=C(C(=N1)C)C=1N=C(C2=C(N=1)C=CC(=N2)C=1C(=C(C=CC=1)NS(=O)(=O)CCCF)F)N1CCOCC1 GOYNWVKPYAPRGK-UHFFFAOYSA-N 0.000 claims 1
• HVSPLUAKXSNPDJ-HNNXBMFYSA-N N-[3-[2-(2-aminopyrimidin-5-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@H]1COCCN1C1=C2N=C(C=CC2=NC(=N1)C1=CN=C(N)N=C1)C1=CC=CC(NS(=O)(=O)CCCF)=C1F HVSPLUAKXSNPDJ-HNNXBMFYSA-N 0.000 claims 1
• LJBHECWTFYXMLM-UHFFFAOYSA-N N-[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-yl-8-pyrrolidin-1-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound Nc1ncc(cn1)-c1nc(N2CCOCC2)c2cc(cc(N3CCCC3)c2n1)-c1cccc(NS(=O)(=O)CCCF)c1F LJBHECWTFYXMLM-UHFFFAOYSA-N 0.000 claims 1
• SSZKHFIPLIWYMR-QGZVFWFLSA-N N-[3-[2-(2-aminopyrimidin-5-yl)-8-ethyl-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound CCc1cc(cc2c(nc(nc12)-c1cnc(N)nc1)N1CCOC[C@H]1C)-c1cccc(NS(=O)(=O)CCCF)c1F SSZKHFIPLIWYMR-QGZVFWFLSA-N 0.000 claims 1
• HUIYTCHPWYKQRE-UHFFFAOYSA-N N-[3-[2-(2-aminopyrimidin-5-yl)-8-methyl-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound Cc1cc(cc2c(nc(nc12)-c1cnc(N)nc1)N1CCOCC1)-c1cccc(NS(=O)(=O)CCCF)c1F HUIYTCHPWYKQRE-UHFFFAOYSA-N 0.000 claims 1
• LFAONIZWKJTNQP-HNNXBMFYSA-N N-[3-[2-(6-amino-4-fluoropyridin-3-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@H]1COCCN1c1nc(nc2ccc(nc12)-c1cccc(NS(=O)(=O)CCCF)c1F)-c1cnc(N)cc1F LFAONIZWKJTNQP-HNNXBMFYSA-N 0.000 claims 1
• VSYCXHPMCJAWEN-MRXNPFEDSA-N N-[3-[2-(6-amino-4-fluoropyridin-3-yl)-8-methoxy-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=CC(=C(C=N1)C1=NC2=C(C=C(C=C2C(=N1)N1[C@@H](COCC1)C)C=1C(=C(C=CC=1)NS(=O)(=O)CCCF)F)OC)F VSYCXHPMCJAWEN-MRXNPFEDSA-N 0.000 claims 1
• SAEYUAYUMCLKCT-KRWDZBQOSA-N N-[3-[2-(6-amino-4-methylpyridin-3-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=CC(=C(C=N1)C=1N=C(C2=C(N=1)C=CC(=N2)C=1C(=C(C=CC=1)NS(=O)(=O)CCCF)F)N1[C@H](COCC1)C)C SAEYUAYUMCLKCT-KRWDZBQOSA-N 0.000 claims 1
• HKHWEKMHOSDGTA-HXUWFJFHSA-N N-[3-[2-(6-aminopyridin-3-yl)-4-[(3R)-3-methylmorpholin-4-yl]-8-pyrrolidin-1-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@@H]1COCCN1c1nc(nc2c(cc(cc12)-c1cccc(NS(=O)(=O)CCCF)c1F)N1CCCC1)-c1ccc(N)nc1 HKHWEKMHOSDGTA-HXUWFJFHSA-N 0.000 claims 1
• IOPPHACWXKLSDE-INIZCTEOSA-N N-[3-[2-(6-aminopyridin-3-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@H]1COCCN1c1nc(nc2ccc(nc12)-c1cccc(NS(=O)(=O)CCCF)c1F)-c1ccc(N)nc1 IOPPHACWXKLSDE-INIZCTEOSA-N 0.000 claims 1
• UPGDRBBAEXKCRW-UHFFFAOYSA-N N-[3-[2-(6-aminopyridin-3-yl)-7-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound COc1cc2nc(nc(N3CCOCC3)c2cc1-c1cccc(NS(=O)(=O)CCCF)c1F)-c1ccc(N)nc1 UPGDRBBAEXKCRW-UHFFFAOYSA-N 0.000 claims 1
• KWKYMTIODSCPKX-UHFFFAOYSA-N N-[3-[2-(6-aminopyridin-3-yl)-8-methyl-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound Cc1cc(cc2c(nc(nc12)-c1ccc(N)nc1)N1CCOCC1)-c1cccc(NS(=O)(=O)CCCF)c1F KWKYMTIODSCPKX-UHFFFAOYSA-N 0.000 claims 1
• AGPHORFBYJGWFU-UHFFFAOYSA-N N-[3-[2-[2-(ethylamino)pyrimidin-5-yl]-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound CCNc1ncc(cn1)-c1nc(N2CCOCC2)c2nc(ccc2n1)-c1cccc(NS(=O)(=O)CCCF)c1F AGPHORFBYJGWFU-UHFFFAOYSA-N 0.000 claims 1
• HDEIGXYUSWFPCU-UHFFFAOYSA-N N-[3-[2-[6-(ethylamino)pyridin-3-yl]-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound CCNc1ccc(cn1)-c1nc(N2CCOCC2)c2nc(ccc2n1)-c1cccc(NS(=O)(=O)CCCF)c1F HDEIGXYUSWFPCU-UHFFFAOYSA-N 0.000 claims 1
• DVGGRJLRAMFKKA-UHFFFAOYSA-N N-[4-[6-[2-fluoro-3-(3-fluoropropylsulfonylamino)phenyl]-8-methoxy-4-morpholin-4-ylquinazolin-2-yl]phenyl]acetamide Chemical compound FC1=C(C=CC=C1NS(=O)(=O)CCCF)C=1C=C2C(=NC(=NC2=C(C=1)OC)C1=CC=C(C=C1)NC(C)=O)N1CCOCC1 DVGGRJLRAMFKKA-UHFFFAOYSA-N 0.000 claims 1
• XWRHMVYXGFTVIT-UHFFFAOYSA-N N-[5-[6-[2-fluoro-3-(3-fluoropropylsulfonylamino)phenyl]-8-methoxy-4-morpholin-4-ylquinazolin-2-yl]pyridin-2-yl]acetamide Chemical compound COc1cc(cc2c(nc(nc12)-c1ccc(NC(C)=O)nc1)N1CCOCC1)-c1cccc(NS(=O)(=O)CCCF)c1F XWRHMVYXGFTVIT-UHFFFAOYSA-N 0.000 claims 1
• HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 claims 1
• XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims 1
• WEHWNAOGRSTTBQ-UHFFFAOYSA-O dipropylazanium Chemical compound CCC[NH2+]CCC WEHWNAOGRSTTBQ-UHFFFAOYSA-O 0.000 claims 1
• VDKGVOWNYNGLJT-UHFFFAOYSA-N n-[2,4-difluoro-3-[2-(1h-indazol-4-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]phenyl]-3-fluoropropane-1-sulfonamide Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2C(OC)=CC(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3F)F)=CC2=C1N1CCOCC1 VDKGVOWNYNGLJT-UHFFFAOYSA-N 0.000 claims 1
• AHUXCWLFJLUIHB-UHFFFAOYSA-N n-[2,4-difluoro-3-[8-methoxy-4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)quinazolin-6-yl]phenyl]-3-fluoropropane-1-sulfonamide Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(OC)=CC(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3F)F)=CC2=C1N1CCOCC1 AHUXCWLFJLUIHB-UHFFFAOYSA-N 0.000 claims 1
• QXJWFOHMLMCRFL-UHFFFAOYSA-N n-[2-fluoro-3-[2-(1h-indazol-4-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]phenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=3C=NNC=3C=CC=2)=C1F QXJWFOHMLMCRFL-UHFFFAOYSA-N 0.000 claims 1
• WPKLYMVCZXVITR-UHFFFAOYSA-N n-[2-fluoro-3-[2-[2-(hydroxymethyl)benzimidazol-1-yl]-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]phenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)N2C3=CC=CC=C3N=C2CO)=C1F WPKLYMVCZXVITR-UHFFFAOYSA-N 0.000 claims 1
• AFQCVPHRXNFLQL-UHFFFAOYSA-N n-[3-[2-(2-aminopyrimidin-5-yl)-4,8-dimorpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(C=C2N3CCOCC3)C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)C2=N1 AFQCVPHRXNFLQL-UHFFFAOYSA-N 0.000 claims 1
• ZLWYTUNMJHQFBQ-UHFFFAOYSA-N n-[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-2,6-difluorobenzenesulfonamide Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(C=C2)C=3C(=C(NS(=O)(=O)C=4C(=CC=CC=4F)F)C=CC=3)F)C2=N1 ZLWYTUNMJHQFBQ-UHFFFAOYSA-N 0.000 claims 1
• ZAJIZBJLXUXGLP-UHFFFAOYSA-N n-[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2N=C3C(N4CCOCC4)=NC(=NC3=CC=2)C=2C=NC(N)=NC=2)=C1F ZAJIZBJLXUXGLP-UHFFFAOYSA-N 0.000 claims 1
• YZURFIIRRQTUTO-UHFFFAOYSA-N n-[3-[2-(2-aminopyrimidin-5-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2,4-difluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound N1=C2C(OC)=CC(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3F)F)=CC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 YZURFIIRRQTUTO-UHFFFAOYSA-N 0.000 claims 1
• RJKAALCITLTSAK-UHFFFAOYSA-N n-[3-[2-(2-aminopyrimidin-5-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2,4-difluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=NC(N)=NC=2)=C1F RJKAALCITLTSAK-UHFFFAOYSA-N 0.000 claims 1
• QAUYNFUSVXLBLC-UHFFFAOYSA-N n-[3-[2-(2-aminopyrimidin-5-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]butane-1-sulfonamide Chemical compound CCCCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=NC(N)=NC=2)=C1F QAUYNFUSVXLBLC-UHFFFAOYSA-N 0.000 claims 1
• RMPJXUCQAKDLFL-UHFFFAOYSA-N n-[3-[2-(2-aminopyrimidin-5-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=NC(N)=NC=2)=C1F RMPJXUCQAKDLFL-UHFFFAOYSA-N 0.000 claims 1
• JFGFZMLCNGRWQI-UHFFFAOYSA-N n-[3-[2-(2-aminopyrimidin-5-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=NC(N)=NC=2)=C1F JFGFZMLCNGRWQI-UHFFFAOYSA-N 0.000 claims 1
• RNBTWGNRFPJZCJ-UHFFFAOYSA-N n-[3-[2-(6-amino-4-fluoropyridin-3-yl)-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C1=NC(N)=CC(F)=C1C1=NC(N2CCOCC2)=C(N=C(C=C2)C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)C2=N1 RNBTWGNRFPJZCJ-UHFFFAOYSA-N 0.000 claims 1
• XGDYVLMODDAHPP-UHFFFAOYSA-N n-[3-[2-(6-amino-4-methylpyridin-3-yl)-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound CC1=CC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(C=C2)C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)C2=N1 XGDYVLMODDAHPP-UHFFFAOYSA-N 0.000 claims 1
• PTPGHWTWYPGXFI-UHFFFAOYSA-N n-[3-[2-(6-amino-5-chloropyridin-3-yl)-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C1=C(Cl)C(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(C=C2)C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)C2=N1 PTPGHWTWYPGXFI-UHFFFAOYSA-N 0.000 claims 1
• YYLHWTGFSRJQNM-UHFFFAOYSA-N n-[3-[2-(6-amino-5-fluoropyridin-3-yl)-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C1=C(F)C(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(C=C2)C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)C2=N1 YYLHWTGFSRJQNM-UHFFFAOYSA-N 0.000 claims 1
• JZBIKMAGUGEITA-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-yl-8-propan-2-yloxyquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound N1=C2C(OC(C)C)=CC(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)=CC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 JZBIKMAGUGEITA-UHFFFAOYSA-N 0.000 claims 1
• LKQRACJFAPDYAG-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2N=C3C(N4CCOCC4)=NC(=NC3=CC=2)C=2C=NC(N)=CC=2)=C1F LKQRACJFAPDYAG-UHFFFAOYSA-N 0.000 claims 1
• DWOHUURGSMGCTN-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(C=C(C=C2)C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)C2=N1 DWOHUURGSMGCTN-UHFFFAOYSA-N 0.000 claims 1
• SOALWTBJSNZFFE-HXUWFJFHSA-N n-[3-[2-(6-aminopyridin-3-yl)-8-cyclopentyloxy-4-[(3r)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@@H]1COCCN1C(C1=CC(=C2)C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)=NC(C=3C=NC(N)=CC=3)=NC1=C2OC1CCCC1 SOALWTBJSNZFFE-HXUWFJFHSA-N 0.000 claims 1
• HYAZGKVOQNPTBA-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-8-ethoxy-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound N1=C2C(OCC)=CC(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)=CC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 HYAZGKVOQNPTBA-UHFFFAOYSA-N 0.000 claims 1
• KYHPQTWHJQMQGQ-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2,4-difluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=NC(N)=CC=2)=C1F KYHPQTWHJQMQGQ-UHFFFAOYSA-N 0.000 claims 1
• XKCMCAARLGTTHK-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=NC(N)=CC=2)=C1F XKCMCAARLGTTHK-UHFFFAOYSA-N 0.000 claims 1
• FXYHCEPZBOEABL-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]propane-2-sulfonamide Chemical compound N1=C2C(OC)=CC(C=3C(=C(NS(=O)(=O)C(C)C)C=CC=3)F)=CC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 FXYHCEPZBOEABL-UHFFFAOYSA-N 0.000 claims 1
• WRPOFWXOHPGVMB-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]thiophene-2-sulfonamide Chemical compound N1=C2C(OC)=CC(C=3C(=C(NS(=O)(=O)C=4SC=CC=4)C=CC=3)F)=CC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 WRPOFWXOHPGVMB-UHFFFAOYSA-N 0.000 claims 1
• XZIQCBUDUDNDEV-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-4-chloro-2-fluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=C(Cl)C(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=NC(N)=CC=2)=C1F XZIQCBUDUDNDEV-UHFFFAOYSA-N 0.000 claims 1
• GBZBHGCSKIUCSA-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-8-methyl-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(C)C=2)C=2C=NC(N)=CC=2)=C1F GBZBHGCSKIUCSA-UHFFFAOYSA-N 0.000 claims 1
• QAPKBGXCXBKSAH-UHFFFAOYSA-N n-[3-[2-[2-amino-4-(trifluoromethyl)pyrimidin-5-yl]-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound FC(F)(F)C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(C=C2)C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)C2=N1 QAPKBGXCXBKSAH-UHFFFAOYSA-N 0.000 claims 1
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