JP2013503875A5 - - Google Patents
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- Publication number
- JP2013503875A5 JP2013503875A5 JP2012527985A JP2012527985A JP2013503875A5 JP 2013503875 A5 JP2013503875 A5 JP 2013503875A5 JP 2012527985 A JP2012527985 A JP 2012527985A JP 2012527985 A JP2012527985 A JP 2012527985A JP 2013503875 A5 JP2013503875 A5 JP 2013503875A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- heterocyclyl
- heteroaryl
- conr
- cycloalkyl
- Prior art date
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 902
- 125000000623 heterocyclic group Chemical group 0.000 claims 704
- 125000001072 heteroaryl group Chemical group 0.000 claims 701
- 125000003118 aryl group Chemical group 0.000 claims 461
- 125000003342 alkenyl group Chemical group 0.000 claims 383
- 125000003545 alkoxy group Chemical group 0.000 claims 375
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 255
- 229910052757 nitrogen Inorganic materials 0.000 claims 253
- 229910052717 sulfur Inorganic materials 0.000 claims 252
- 125000005842 heteroatom Chemical group 0.000 claims 251
- 229910052760 oxygen Inorganic materials 0.000 claims 248
- 229910052799 carbon Inorganic materials 0.000 claims 238
- 125000004432 carbon atom Chemical group C* 0.000 claims 237
- 125000005843 halogen group Chemical group 0.000 claims 233
- 229910052794 bromium Inorganic materials 0.000 claims 231
- 229910052740 iodine Inorganic materials 0.000 claims 231
- 229910052801 chlorine Inorganic materials 0.000 claims 225
- 125000000753 cycloalkyl group Chemical group 0.000 claims 206
- 125000004093 cyano group Chemical group *C#N 0.000 claims 203
- 125000000304 alkynyl group Chemical group 0.000 claims 138
- 229910052739 hydrogen Inorganic materials 0.000 claims 65
- 239000003814 drug Substances 0.000 claims 49
- 229940079593 drug Drugs 0.000 claims 42
- 239000003795 chemical substances by application Substances 0.000 claims 25
- 239000001257 hydrogen Substances 0.000 claims 24
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 17
- 239000003146 anticoagulant agent Substances 0.000 claims 14
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 14
- 125000004122 cyclic group Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 12
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 10
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 9
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 7
- 229940083712 aldosterone antagonist Drugs 0.000 claims 7
- 229940127003 anti-diabetic drug Drugs 0.000 claims 7
- 239000000883 anti-obesity agent Substances 0.000 claims 7
- 229940124605 anti-osteoporosis drug Drugs 0.000 claims 7
- 230000001028 anti-proliverative effect Effects 0.000 claims 7
- 230000002785 anti-thrombosis Effects 0.000 claims 7
- 230000000767 anti-ulcer Effects 0.000 claims 7
- 239000003416 antiarrhythmic agent Substances 0.000 claims 7
- 229940127219 anticoagulant drug Drugs 0.000 claims 7
- 239000000935 antidepressant agent Substances 0.000 claims 7
- 229940005513 antidepressants Drugs 0.000 claims 7
- 229940127088 antihypertensive drug Drugs 0.000 claims 7
- 239000002246 antineoplastic agent Substances 0.000 claims 7
- 229940041181 antineoplastic drug Drugs 0.000 claims 7
- 229940127218 antiplatelet drug Drugs 0.000 claims 7
- 239000003420 antiserotonin agent Substances 0.000 claims 7
- 239000002249 anxiolytic agent Substances 0.000 claims 7
- 230000000949 anxiolytic effect Effects 0.000 claims 7
- 229940005530 anxiolytics Drugs 0.000 claims 7
- 229940097217 cardiac glycoside Drugs 0.000 claims 7
- 239000002368 cardiac glycoside Substances 0.000 claims 7
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 claims 7
- 235000012000 cholesterol Nutrition 0.000 claims 7
- 239000002934 diuretic Substances 0.000 claims 7
- 229940030606 diuretics Drugs 0.000 claims 7
- ZQTNQVWKHCQYLQ-UHFFFAOYSA-N dronedarone Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(NS(C)(=O)=O)C=C12 ZQTNQVWKHCQYLQ-UHFFFAOYSA-N 0.000 claims 7
- 229960002084 dronedarone Drugs 0.000 claims 7
- 239000003527 fibrinolytic agent Substances 0.000 claims 7
- 239000003324 growth hormone secretagogue Substances 0.000 claims 7
- 238000002657 hormone replacement therapy Methods 0.000 claims 7
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 7
- 150000002632 lipids Chemical class 0.000 claims 7
- 239000002394 mineralocorticoid antagonist Substances 0.000 claims 7
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims 7
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 7
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims 7
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 claims 7
- 229930002534 steroid glycoside Natural products 0.000 claims 7
- 150000008143 steroidal glycosides Chemical class 0.000 claims 7
- 229940124597 therapeutic agent Drugs 0.000 claims 7
- 210000001685 thyroid gland Anatomy 0.000 claims 7
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims 7
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 5
- 239000003472 antidiabetic agent Substances 0.000 claims 5
- 239000002220 antihypertensive agent Substances 0.000 claims 5
- 239000000480 calcium channel blocker Substances 0.000 claims 5
- -1 (4-aminopiperidinyl) sulfonyl Chemical group 0.000 claims 4
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims 4
- 206010003119 arrhythmia Diseases 0.000 claims 4
- 230000006793 arrhythmia Effects 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 229940127234 oral contraceptive Drugs 0.000 claims 4
- 239000003539 oral contraceptive agent Substances 0.000 claims 4
- 230000003637 steroidlike Effects 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 108090000312 Calcium Channels Proteins 0.000 claims 2
- 102000003922 Calcium Channels Human genes 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 206010010774 Constipation Diseases 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000006549 dyspepsia Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 208000000689 peptic esophagitis Diseases 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims 2
- WNKYTCDVQGQNGF-UHFFFAOYSA-N (4-aminopiperidin-1-yl)-[3-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]-1,2,4-oxadiazol-5-yl]methanone Chemical compound C1CC(N)CCN1C(=O)C1=NC(C=2C=C(C=NC=2)C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=NO1 WNKYTCDVQGQNGF-UHFFFAOYSA-N 0.000 claims 1
- KCMPNIHDCHNBLR-UHFFFAOYSA-N 1-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]-4,5-dihydro-1,2-oxazol-3-yl]butan-1-one Chemical compound C1C(C(=O)CCC)=NOC1C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 KCMPNIHDCHNBLR-UHFFFAOYSA-N 0.000 claims 1
- CFIPTVYHUSQTPE-UHFFFAOYSA-N 1-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]cyclopropane-1-carbonitrile Chemical compound C=1N=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=CC=1C1(C#N)CC1 CFIPTVYHUSQTPE-UHFFFAOYSA-N 0.000 claims 1
- YFHBVPJJSPKCBC-UHFFFAOYSA-N 1-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]ethanol Chemical compound CC(O)C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 YFHBVPJJSPKCBC-UHFFFAOYSA-N 0.000 claims 1
- WRQMKFLJGNZAMX-UHFFFAOYSA-N 1-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]cyclopropane-1-carbonitrile Chemical compound N=1C(NCC=2N=CC=CC=2)=C2C(C=3C=CC=CC=3)=CC=CC2=NC=1C1(C#N)CC1 WRQMKFLJGNZAMX-UHFFFAOYSA-N 0.000 claims 1
- BJMGXMYXAHQFBO-UHFFFAOYSA-N 1-methyl-2-oxo-5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide Chemical compound C1=C(S(N)(=O)=O)C(=O)N(C)C=C1C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 BJMGXMYXAHQFBO-UHFFFAOYSA-N 0.000 claims 1
- RAEQCNSUDIRZQO-UHFFFAOYSA-N 2-(2-aminopyrimidin-5-yl)-5-phenyl-n-(pyridin-2-ylmethyl)quinazolin-4-amine Chemical compound C1=NC(N)=NC=C1C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 RAEQCNSUDIRZQO-UHFFFAOYSA-N 0.000 claims 1
- VBVACLJOGCQGTG-UHFFFAOYSA-N 2-(2-methoxypyrimidin-5-yl)-5-phenyl-n-(pyridin-2-ylmethyl)quinazolin-4-amine Chemical compound C1=NC(OC)=NC=C1C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 VBVACLJOGCQGTG-UHFFFAOYSA-N 0.000 claims 1
- QHIYHJYIEGGUOX-UHFFFAOYSA-N 2-(5-aminopyridin-3-yl)-5-phenyl-n-(pyridin-2-ylmethyl)quinazolin-4-amine Chemical compound NC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 QHIYHJYIEGGUOX-UHFFFAOYSA-N 0.000 claims 1
- XYSIEZSDRWTZEA-UHFFFAOYSA-N 2-[5-(1,2,4-oxadiazol-3-yl)pyridin-3-yl]-5-phenyl-n-(pyridin-2-ylmethyl)quinazolin-4-amine Chemical compound C=1C=CC=NC=1CNC(C=12)=NC(C=3C=C(C=NC=3)C3=NOC=N3)=NC2=CC=CC=1C1=CC=CC=C1 XYSIEZSDRWTZEA-UHFFFAOYSA-N 0.000 claims 1
- ZEETZZJMRKEACQ-UHFFFAOYSA-N 2-[5-(1,3,4-oxadiazol-2-yl)pyridin-3-yl]-5-phenyl-n-(pyridin-2-ylmethyl)quinazolin-4-amine Chemical compound C=1C=CC=NC=1CNC(C=12)=NC(C=3C=C(C=NC=3)C=3OC=NN=3)=NC2=CC=CC=1C1=CC=CC=C1 ZEETZZJMRKEACQ-UHFFFAOYSA-N 0.000 claims 1
- CKHRJXSBXGIPIU-UHFFFAOYSA-N 2-[5-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-3-yl]-5-phenyl-n-(pyridin-2-ylmethyl)quinazolin-4-amine Chemical compound CC1=NOC(C)=C1C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 CKHRJXSBXGIPIU-UHFFFAOYSA-N 0.000 claims 1
- IZKJBTRAWREWFD-UHFFFAOYSA-N 2-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]acetamide Chemical compound NC(=O)CC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 IZKJBTRAWREWFD-UHFFFAOYSA-N 0.000 claims 1
- FVMLHPCDJCQAPK-UHFFFAOYSA-N 2-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]acetonitrile Chemical compound N#CCC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 FVMLHPCDJCQAPK-UHFFFAOYSA-N 0.000 claims 1
- DCZRNAOHORCJCS-UHFFFAOYSA-N 2-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]ethanesulfonamide Chemical compound NS(=O)(=O)CCC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 DCZRNAOHORCJCS-UHFFFAOYSA-N 0.000 claims 1
- ORAPDKIAZMXQNT-UHFFFAOYSA-N 2-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]propan-2-ol Chemical compound CC(C)(O)C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 ORAPDKIAZMXQNT-UHFFFAOYSA-N 0.000 claims 1
- VPKRECDQVAXWPK-UHFFFAOYSA-N 2-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]propanamide Chemical compound NC(=O)C(C)C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 VPKRECDQVAXWPK-UHFFFAOYSA-N 0.000 claims 1
- CSRQWQAFGUGBMQ-UHFFFAOYSA-N 2-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]propane-1,3-diol Chemical compound OCC(CO)C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 CSRQWQAFGUGBMQ-UHFFFAOYSA-N 0.000 claims 1
- PDIQUSOLRPLOGI-UHFFFAOYSA-N 2-[[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]methylsulfonyl]acetamide Chemical compound NC(=O)CS(=O)(=O)CC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 PDIQUSOLRPLOGI-UHFFFAOYSA-N 0.000 claims 1
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims 1
- SDKFQIYNQXUBFN-UHFFFAOYSA-N 2-amino-5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide Chemical compound C1=C(S(N)(=O)=O)C(N)=NC=C1C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 SDKFQIYNQXUBFN-UHFFFAOYSA-N 0.000 claims 1
- HJAQLGANXHYRSF-UHFFFAOYSA-N 2-chloro-5-phenyl-n-pyridin-2-ylquinazolin-4-amine Chemical compound C=12C(C=3C=CC=CC=3)=CC=CC2=NC(Cl)=NC=1NC1=CC=CC=N1 HJAQLGANXHYRSF-UHFFFAOYSA-N 0.000 claims 1
- YCHLARAVEDTNCP-UHFFFAOYSA-N 2-cyclopropyl-5-phenyl-n-(pyridin-2-ylmethyl)quinazolin-4-amine Chemical compound C=1C=CC=NC=1CNC(C=12)=NC(C3CC3)=NC2=CC=CC=1C1=CC=CC=C1 YCHLARAVEDTNCP-UHFFFAOYSA-N 0.000 claims 1
- ADPOMRGQHUPZED-UHFFFAOYSA-N 2-methoxy-5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide Chemical compound C1=C(S(N)(=O)=O)C(OC)=NC=C1C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 ADPOMRGQHUPZED-UHFFFAOYSA-N 0.000 claims 1
- AIWGUQUXNSMXNH-UHFFFAOYSA-N 2-methyl-1-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]propan-1-ol Chemical compound CC(C)C(O)C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 AIWGUQUXNSMXNH-UHFFFAOYSA-N 0.000 claims 1
- DQDWIXDURRTWQQ-UHFFFAOYSA-N 2-methyl-2-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]propanenitrile Chemical compound N#CC(C)(C)C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 DQDWIXDURRTWQQ-UHFFFAOYSA-N 0.000 claims 1
- VKGUZDMOYVPPLI-UHFFFAOYSA-N 2-methyl-2-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]propane-1,3-diol Chemical compound C=12C(C=3C=CC=CC=3)=CC=CC2=NC(C(CO)(CO)C)=NC=1NCC1=CC=CC=N1 VKGUZDMOYVPPLI-UHFFFAOYSA-N 0.000 claims 1
- KGBPICWXCWNDSD-UHFFFAOYSA-N 2-methyl-6-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]imidazo[1,2-a]pyridine-8-sulfonamide Chemical compound C1=C(S(N)(=O)=O)C2=NC(C)=CN2C=C1C(N=C1C=CC=C(C1=1)C=2C=CC=CC=2)=NC=1NCC1=CC=CC=N1 KGBPICWXCWNDSD-UHFFFAOYSA-N 0.000 claims 1
- ZDRPFFAIGWCFRK-UHFFFAOYSA-N 3-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]-1,2,4-oxadiazole-5-carboxamide Chemical compound O1C(C(=O)N)=NC(C=2C=C(C=NC=2)C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=N1 ZDRPFFAIGWCFRK-UHFFFAOYSA-N 0.000 claims 1
- CRBPVOYQPCSBGD-UHFFFAOYSA-N 3-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]propanamide Chemical compound NC(=O)CCC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 CRBPVOYQPCSBGD-UHFFFAOYSA-N 0.000 claims 1
- WNSUHLRXJPCQQL-UHFFFAOYSA-N 4-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 WNSUHLRXJPCQQL-UHFFFAOYSA-N 0.000 claims 1
- JJQNGYRROPWYJT-UHFFFAOYSA-N 4-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]but-3-yn-1-ol Chemical compound C=12C(C=3C=CC=CC=3)=CC=CC2=NC(C#CCCO)=NC=1NCC1=CC=CC=N1 JJQNGYRROPWYJT-UHFFFAOYSA-N 0.000 claims 1
- XPJNIZBBYJXAEK-UHFFFAOYSA-N 4-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]piperidine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N)CCC1C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 XPJNIZBBYJXAEK-UHFFFAOYSA-N 0.000 claims 1
- MJJFPHTURAZWKX-UHFFFAOYSA-N 5-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]-1,3,4-oxadiazol-2-amine Chemical compound O1C(N)=NN=C1C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 MJJFPHTURAZWKX-UHFFFAOYSA-N 0.000 claims 1
- DTWBCZCMEULUNG-UHFFFAOYSA-N 5-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]-1,3,4-oxadiazole-2-carboxamide Chemical compound O1C(C(=O)N)=NN=C1C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 DTWBCZCMEULUNG-UHFFFAOYSA-N 0.000 claims 1
- KITYXUGKWPDMSJ-UHFFFAOYSA-N 5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 KITYXUGKWPDMSJ-UHFFFAOYSA-N 0.000 claims 1
- XGKULQQVQWCASY-UHFFFAOYSA-N 5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 XGKULQQVQWCASY-UHFFFAOYSA-N 0.000 claims 1
- HEDAUIXNFZMILW-UHFFFAOYSA-N 5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyrimidine-2-carbonitrile Chemical compound C1=NC(C#N)=NC=C1C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 HEDAUIXNFZMILW-UHFFFAOYSA-N 0.000 claims 1
- GYEMDCYWSZCBGX-UHFFFAOYSA-N 5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyrimidine-2-carboxamide Chemical compound C1=NC(C(=O)N)=NC=C1C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 GYEMDCYWSZCBGX-UHFFFAOYSA-N 0.000 claims 1
- QPZKONBYBJXIFG-UHFFFAOYSA-N 5-phenyl-4-(pyridin-2-ylmethylamino)-2-[1-[(sulfamoylamino)methyl]cyclopropyl]quinazoline Chemical compound N=1C(NCC=2N=CC=CC=2)=C2C(C=3C=CC=CC=3)=CC=CC2=NC=1C1(CNS(=O)(=O)N)CC1 QPZKONBYBJXIFG-UHFFFAOYSA-N 0.000 claims 1
- GPYUSYNKDNQBNE-UHFFFAOYSA-N 5-phenyl-4-(pyridin-2-ylmethylamino)-2-[5-(sulfamoylamino)pyridin-3-yl]quinazoline Chemical compound NS(=O)(=O)NC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 GPYUSYNKDNQBNE-UHFFFAOYSA-N 0.000 claims 1
- VZKHWWWTMNZHEU-UHFFFAOYSA-N 5-phenyl-N-(pyridin-2-ylmethyl)-2-pyrimidin-5-ylquinazolin-4-amine 5-phenyl-2-pyrimidin-5-yl-3H-quinazolin-4-one Chemical compound O=c1[nH]c(nc2cccc(-c3ccccc3)c12)-c1cncnc1.C(Nc1nc(nc2cccc(-c3ccccc3)c12)-c1cncnc1)c1ccccn1 VZKHWWWTMNZHEU-UHFFFAOYSA-N 0.000 claims 1
- UHUXOLGACMTMER-UHFFFAOYSA-N 5-phenyl-n-(pyridin-2-ylmethyl)-2-(2,2,5-trimethyl-1,3-dioxan-5-yl)quinazolin-4-amine Chemical compound C1OC(C)(C)OCC1(C)C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 UHUXOLGACMTMER-UHFFFAOYSA-N 0.000 claims 1
- ZMTTVRRCZREMLV-UHFFFAOYSA-N 5-phenyl-n-(pyridin-2-ylmethyl)-2-(2h-triazol-4-yl)quinazolin-4-amine Chemical compound C=1C=CC=NC=1CNC(C=12)=NC(C3=NNN=C3)=NC2=CC=CC=1C1=CC=CC=C1 ZMTTVRRCZREMLV-UHFFFAOYSA-N 0.000 claims 1
- DCKQCZSGFVXJQD-UHFFFAOYSA-N 5-phenyl-n-(pyridin-2-ylmethyl)-2-(trifluoromethyl)quinazolin-4-amine Chemical compound C=12C(C=3C=CC=CC=3)=CC=CC2=NC(C(F)(F)F)=NC=1NCC1=CC=CC=N1 DCKQCZSGFVXJQD-UHFFFAOYSA-N 0.000 claims 1
- OVNREXDNGOVHCG-UHFFFAOYSA-N 5-phenyl-n-(pyridin-2-ylmethyl)-2-[5-(1,2,4-triazol-4-yl)pyridin-3-yl]quinazolin-4-amine Chemical compound C=1C=CC=NC=1CNC(C=12)=NC(C=3C=C(C=NC=3)N3C=NN=C3)=NC2=CC=CC=1C1=CC=CC=C1 OVNREXDNGOVHCG-UHFFFAOYSA-N 0.000 claims 1
- ULDPBZLCZOEGTF-UHFFFAOYSA-N 5-phenyl-n-(pyridin-2-ylmethyl)-2-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]quinazolin-4-amine Chemical compound O1C(C(F)(F)F)=NC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=N1 ULDPBZLCZOEGTF-UHFFFAOYSA-N 0.000 claims 1
- VQGXMSITFWZMRF-UHFFFAOYSA-N 6-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C=1N=C2NC(=O)NC2=CC=1C(N=C1C=CC=C(C1=1)C=2C=CC=CC=2)=NC=1NCC1=CC=CC=N1 VQGXMSITFWZMRF-UHFFFAOYSA-N 0.000 claims 1
- MUQYRIDVHPKYKS-UHFFFAOYSA-N 6-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyrazine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=N1 MUQYRIDVHPKYKS-UHFFFAOYSA-N 0.000 claims 1
- 241000162682 Heterogen Species 0.000 claims 1
- AGBLAKRVOJGRKT-UHFFFAOYSA-N [5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]methanol Chemical compound OCC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 AGBLAKRVOJGRKT-UHFFFAOYSA-N 0.000 claims 1
- USSODORNBVBVFT-UHFFFAOYSA-N [5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]urea Chemical compound NC(=O)NC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 USSODORNBVBVFT-UHFFFAOYSA-N 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- QYBPUCIBGMCKPB-UHFFFAOYSA-N methyl 3-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]-1,2,4-oxadiazole-5-carboxylate Chemical compound O1C(C(=O)OC)=NC(C=2C=C(C=NC=2)C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=N1 QYBPUCIBGMCKPB-UHFFFAOYSA-N 0.000 claims 1
- BKTVVVVSDQVHEI-UHFFFAOYSA-N methyl 3-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]propanoate Chemical compound COC(=O)CCC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 BKTVVVVSDQVHEI-UHFFFAOYSA-N 0.000 claims 1
- NSQNJIOTYOYVPJ-UHFFFAOYSA-N methyl 5-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]-1,3,4-oxadiazole-2-carboxylate Chemical compound O1C(C(=O)OC)=NN=C1C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 NSQNJIOTYOYVPJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- FZILBCDDESQHAI-UHFFFAOYSA-N n-(2-methoxyethyl)-5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide Chemical compound COCCNS(=O)(=O)C1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 FZILBCDDESQHAI-UHFFFAOYSA-N 0.000 claims 1
- LRVVBPZHOLIFKZ-UHFFFAOYSA-N n-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]acetamide Chemical compound CC(=O)NC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 LRVVBPZHOLIFKZ-UHFFFAOYSA-N 0.000 claims 1
- SHRUFOHFMSBOSJ-UHFFFAOYSA-N n-[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 SHRUFOHFMSBOSJ-UHFFFAOYSA-N 0.000 claims 1
- JQUHYGFWCNJOLE-UHFFFAOYSA-N n-[[1-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]cyclopropyl]methyl]methanesulfonamide Chemical compound N=1C(NCC=2N=CC=CC=2)=C2C(C=3C=CC=CC=3)=CC=CC2=NC=1C1(CNS(=O)(=O)C)CC1 JQUHYGFWCNJOLE-UHFFFAOYSA-N 0.000 claims 1
- JPVHKVBAXFJQFG-UHFFFAOYSA-N n-[[5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridin-3-yl]methyl]methanesulfonamide Chemical compound CS(=O)(=O)NCC1=CN=CC(C=2N=C3C=CC=C(C3=C(NCC=3N=CC=CC=3)N=2)C=2C=CC=CC=2)=C1 JPVHKVBAXFJQFG-UHFFFAOYSA-N 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims 1
- PRWJCIOUDJPBJR-UHFFFAOYSA-N tert-butyl 4-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NC(NCC=2N=CC=CC=2)=C(C(=CC=C2)C=3C=CC=CC=3)C2=N1 PRWJCIOUDJPBJR-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 0 C*(c1cccc(-c(cc2)c(*)c(C)c2N)c1C(*(*)*)=*)=C(*)* Chemical compound C*(c1cccc(-c(cc2)c(*)c(C)c2N)c1C(*(*)*)=*)=C(*)* 0.000 description 1
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