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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Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH068949B2 (ja) | 1985-09-20 | 1994-02-02 | 富士写真フイルム株式会社 | ハロゲン化銀カラ−写真感光材料 |
| EA021113B1 (ru) * | 2009-09-03 | 2015-04-30 | Бристол-Майерс Сквибб Кампани | Хиназолины в качестве ингибиторов калиевых каналов |
| AR079814A1 (es) * | 2009-12-31 | 2012-02-22 | Otsuka Pharma Co Ltd | Compuestos heterociclicos, composiciones farmaceuticas que los contienen y sus usos |
| JP6121658B2 (ja) * | 2011-06-29 | 2017-04-26 | 大塚製薬株式会社 | 治療用化合物、及び関連する使用の方法 |
| CA2840627A1 (en) * | 2011-06-29 | 2013-01-03 | Otsuka Pharmaceutical Co., Ltd. | Quinazolines as therapeutic compounds and related methods of use |
| CN103360382B (zh) * | 2012-03-26 | 2016-04-27 | 中国科学院福建物质结构研究所 | 喹唑啉衍生物及其用途 |
| LT2858987T (lt) * | 2012-06-11 | 2018-07-10 | Bristol-Myers Squibb Company | Fosforamido rūgšties provaistai iš 5-[5-fenil-4-(piridin-2-ilmetilamino)chinazolin-2-il]piridin-3-sulfonamido |
| WO2014133059A1 (ja) | 2013-02-28 | 2014-09-04 | 武田薬品工業株式会社 | スルホニルクロライド化合物の製造法 |
| WO2014143606A1 (en) * | 2013-03-11 | 2014-09-18 | Bristol-Myers Squibb Company | Pyrrolotriazines as potassium ion channel inhibitors |
| JP6386527B2 (ja) * | 2013-03-11 | 2018-09-05 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | カリウムイオンチャネル阻害剤としてのピロロピリダジン |
| US9242966B2 (en) * | 2013-03-11 | 2016-01-26 | Bristol-Myers Squibb Company | Phthalazines as potassium ion channel inhibitors |
| US9050345B2 (en) * | 2013-03-11 | 2015-06-09 | Bristol-Myers Squibb Company | Pyrrolotriazines as potassium ion channel inhibitors |
| WO2014143609A1 (en) | 2013-03-11 | 2014-09-18 | Bristol-Myers Squibb Company | Isoquinolines as potassium ion channel inhibitors |
| WO2015056811A1 (ja) * | 2013-10-17 | 2015-04-23 | 住友化学株式会社 | テトラゾリノン化合物及びその用途 |
| US10774072B2 (en) | 2014-06-10 | 2020-09-15 | Ube Industries, Ltd. | Crystal of N-substituted sulfonamide compound |
| KR20170013994A (ko) | 2014-06-10 | 2017-02-07 | 우베 고산 가부시키가이샤 | N-치환 술폰아미드 화합물 및 그의 제조 방법 |
| US10519112B2 (en) | 2014-06-10 | 2019-12-31 | Ube Industries, Ltd. | Method for producing heteroaromatic sulfonamide compound |
| EP3226868A4 (en) | 2014-12-05 | 2018-08-15 | Subramaniam Ananthan | Novel quinazolines as biogenic amine transport modulators |
| CA2969839A1 (en) * | 2014-12-05 | 2016-06-09 | Subramaniam Ananthan | Heterocyclic compounds as biogenic amine transport modulators |
| US20180338980A1 (en) * | 2015-06-10 | 2018-11-29 | Bayer Pharma Aktiengesellschaft | Aromatic sulfonamide derivatives |
| PL3458443T3 (pl) | 2016-05-03 | 2021-03-08 | Bayer Pharma Aktiengesellschaft | Aromatyczne pochodne sulfonamidowe |
| CN106432067B (zh) * | 2016-09-18 | 2019-04-19 | 北京天弘天达医药科技有限公司 | 一种3-吡啶磺酰氯的绿色化学合成方法 |
| US20210179577A1 (en) * | 2017-10-29 | 2021-06-17 | Bayer Aktiengesellschaft | Aromatic sulfonamide derivatives for the treatment of ischemic stroke |
| WO2019202077A1 (en) * | 2018-04-20 | 2019-10-24 | Bayer Aktiengesellschaft | Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides |
| WO2020234103A1 (en) | 2019-05-21 | 2020-11-26 | Bayer Aktiengesellschaft | Identification and use of kras inhibitors |
| US20230357239A1 (en) | 2020-09-18 | 2023-11-09 | Bayer Aktiengesellschaft | Pyrido[2,3-d]pyrimidin-4-amines as sos1 inhibitors |
| EP4074317A1 (en) | 2021-04-14 | 2022-10-19 | Bayer AG | Phosphorus derivatives as novel sos1 inhibitors |
| US20250289806A1 (en) * | 2022-04-28 | 2025-09-18 | University Of Miami | Compounds for proliferative disorders |
| WO2024056782A1 (en) | 2022-09-16 | 2024-03-21 | Bayer Aktiengesellschaft | Sulfone-substituted pyrido[3,4-d]pyrimidine derivatives for the treatment of cancer |
| EP4602049A1 (en) | 2022-10-13 | 2025-08-20 | Bayer Aktiengesellschaft | Sos1 inhibitors |
| WO2025202022A1 (en) | 2024-03-27 | 2025-10-02 | Bayer Aktiengesellschaft | Anticancer macrocyclic quinazoline-based inhibitors of the ineraction between ras and sos1 |
Family Cites Families (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3843791A (en) | 1973-01-11 | 1974-10-22 | Pfizer | Method of killing insects with quinazolinones and quinazoline-thiones |
| ES2104862T3 (es) | 1991-02-07 | 1997-10-16 | Roussel Uclaf | Derivados biciclicos nitrogenados, su procedimiento de preparacion, sus productos intermedios obtenidos, su aplicacion como medicamentos y composiciones farmaceuticas que los contienen. |
| US6645969B1 (en) | 1991-05-10 | 2003-11-11 | Aventis Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| GB9300059D0 (en) | 1992-01-20 | 1993-03-03 | Zeneca Ltd | Quinazoline derivatives |
| JP2657760B2 (ja) | 1992-07-15 | 1997-09-24 | 小野薬品工業株式会社 | ４−アミノキナゾリン誘導体およびそれを含有する医薬品 |
| GB9323290D0 (en) | 1992-12-10 | 1994-01-05 | Zeneca Ltd | Quinazoline derivatives |
| WO1995000524A1 (fr) * | 1993-06-17 | 1995-01-05 | Otsuka Pharmaceutical Factory, Inc. | Derive de diester phosphonique |
| GB9314884D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Tricyclic derivatives |
| GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| IL112248A0 (en) | 1994-01-25 | 1995-03-30 | Warner Lambert Co | Tricyclic heteroaromatic compounds and pharmaceutical compositions containing them |
| IL112249A (en) | 1994-01-25 | 2001-11-25 | Warner Lambert Co | Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds |
| US5654307A (en) | 1994-01-25 | 1997-08-05 | Warner-Lambert Company | Bicyclic compounds capable of inhibiting tyrosine kinases of the epidermal growth factor receptor family |
| JPH083144A (ja) | 1994-06-21 | 1996-01-09 | Chugai Pharmaceut Co Ltd | キナゾリン及びキノリン誘導体 |
| TW414798B (en) | 1994-09-07 | 2000-12-11 | Thomae Gmbh Dr K | Pyrimido (5,4-d) pyrimidines, medicaments comprising these compounds, their use and processes for their preparation |
| GB9510757D0 (en) | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
| GB9424233D0 (en) | 1994-11-30 | 1995-01-18 | Zeneca Ltd | Quinazoline derivatives |
| GB9514265D0 (en) | 1995-07-13 | 1995-09-13 | Wellcome Found | Hetrocyclic compounds |
| AU7692996A (en) * | 1995-12-01 | 1997-06-27 | Ciba-Geigy Ag | Receptor antagonists |
| NZ325248A (en) * | 1995-12-23 | 1999-09-29 | Pfizer Res & Dev | Quinoline and quinazoline compounds useful in therapy |
| AR007857A1 (es) | 1996-07-13 | 1999-11-24 | Glaxo Group Ltd | Compuestos heterociclicos fusionados como inhibidores de proteina tirosina quinasa, sus metodos de preparacion, intermediarios uso en medicina ycomposiciones farmaceuticas que los contienen. |
| WO1998029397A1 (en) | 1996-12-27 | 1998-07-09 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused pyrimidine compounds and medicinal use thereof |
| AU743024B2 (en) | 1997-03-05 | 2002-01-17 | Sugen, Inc. | Formulations for hydrophobic pharmaceutical agents |
| US6184226B1 (en) | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
| CA2384291A1 (en) | 1999-09-21 | 2001-03-29 | Astrazeneca Ab | Quinazoline derivatives and their use as pharmaceuticals |
| PL354784A1 (en) * | 1999-09-30 | 2004-02-23 | Neurogen Corporation | Certain alkylene diamine-substituted heterocycles |
| US6605615B2 (en) | 2000-03-01 | 2003-08-12 | Tularik Inc. | Hydrazones and analogs as cholesterol lowering agents |
| KR100774855B1 (ko) | 2000-04-27 | 2007-11-08 | 아스텔라스세이야쿠 가부시키가이샤 | 축합 헤테로아릴 유도체 |
| JP2004509876A (ja) | 2000-09-20 | 2004-04-02 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | ４−アミノ−キナゾリン |
| EP1318985A2 (en) | 2000-09-20 | 2003-06-18 | MERCK PATENT GmbH | 4-amino-quinazolines |
| WO2002062767A1 (en) | 2001-02-07 | 2002-08-15 | Sumitomo Pharmaceuticals Company, Limited | Novel quinazoline derivatives |
| WO2002092579A1 (en) | 2001-05-14 | 2002-11-21 | Astrazeneca Ab | 4-anilinoquinazoline derivatives |
| US7829566B2 (en) | 2001-09-17 | 2010-11-09 | Werner Mederski | 4-amino-quinazolines |
| US7645878B2 (en) | 2002-03-22 | 2010-01-12 | Bayer Healthcare Llc | Process for preparing quinazoline Rho-kinase inhibitors and intermediates thereof |
| AU2003255845A1 (en) | 2002-08-22 | 2004-03-11 | Piramed Limited | Phosphadidylinositol 3,5-biphosphate inhibitors as anti-viral agents |
| WO2004030672A1 (en) | 2002-10-02 | 2004-04-15 | Merck Patent Gmbh | Use of 4 amino-quinazolines as anti cancer agents |
| AU2003258662A1 (en) | 2002-10-02 | 2004-04-23 | Merck Patent Gmbh | Use of 4-amino-quinazolines as anti cancer agents |
| AU2003292435A1 (en) | 2002-12-23 | 2004-07-14 | Astrazeneca Ab | 4- (pyridin-4-ylamino) -quinazoline derivatives as anti-tumor agents |
| AU2003290279A1 (en) | 2002-12-23 | 2004-07-14 | Astrazeneca Ab | Quinazoline derivatives |
| WO2004069145A2 (en) | 2003-02-07 | 2004-08-19 | Dr. Reddy's Laboratories Ltd. | Anticancer compounds, process for their preparation and pharmaceutical compositions containing them |
| CL2004000409A1 (es) | 2003-03-03 | 2005-01-07 | Vertex Pharma | Compuestos derivados de 2-(cilo sustituido)-1-(amino u oxi sustituido)-quinazolina, inhibidores de canales ionicos de sodio y calcio dependientes de voltaje; composicion farmaceutica; y uso del compuesto en el tratamiento de dolor agudo, cronico, neu |
| ZA200507979B (en) * | 2003-03-03 | 2007-03-28 | Vertex Pharma Inc | Quinazolines useful as modulators of ion channels |
| US7713983B2 (en) * | 2003-03-03 | 2010-05-11 | Vertex Pharmaceuticals Incorporated | Quinazolines useful as modulators of ion channels |
| CN100475793C (zh) | 2003-03-31 | 2009-04-08 | 大正制药株式会社 | 喹唑啉衍生物及其制备药物的用途 |
| ES2324536T7 (es) | 2003-06-11 | 2012-03-16 | Xention Limited | Derivados de tenopirimidina como inhibidores de los canales de potasio. |
| MXPA05013922A (es) | 2003-06-20 | 2006-02-24 | Coley Pharm Group Inc | Antagonistas de receptor tipo toll de molecula pequena. |
| AU2004253967B2 (en) | 2003-07-03 | 2010-02-18 | Cytovia, Inc. | 4-arylamino-quinazolines as activators of caspases and inducers of apoptosis |
| JP4719681B2 (ja) * | 2003-09-23 | 2011-07-06 | メルク・シャープ・エンド・ドーム・コーポレイション | キナゾリンカリウムチャネル阻害剤 |
| JP2007510642A (ja) | 2003-11-03 | 2007-04-26 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 中枢神経系障害の治療のための新規ノルエピネフリン再取込み阻害薬 |
| WO2005080377A1 (ja) | 2004-02-20 | 2005-09-01 | Kirin Beer Kabushiki Kaisha | TGFβ阻害活性を有する化合物およびそれを含んでなる医薬組成物 |
| WO2005087742A1 (en) | 2004-03-08 | 2005-09-22 | Exelixis, Inc. | Metabolic kinase modulators and methods of use as pesticides |
| US20070225308A1 (en) | 2004-03-15 | 2007-09-27 | Kyowa Hakko Kogyo Co.,Ltd. | 2-Amino Quinazoline Derivative |
| MXPA06014256A (es) | 2004-06-10 | 2007-03-12 | Xention Discovery Ltd | Compuestos de furano-pirimidina efectivos como inhibidores del canal de potasio. |
| US20060014705A1 (en) | 2004-06-30 | 2006-01-19 | Howitz Konrad T | Compositions and methods for selectively activating human sirtuins |
| US20060025406A1 (en) | 2004-07-06 | 2006-02-02 | Angion Biomedica Corporation | Modulators of hepatocyte growth factor/c- Met activity |
| ATE476434T1 (de) | 2004-12-09 | 2010-08-15 | Xention Ltd | Thienopyridinderivate als kaliumkanalinhibitoren |
| KR20060079121A (ko) | 2004-12-31 | 2006-07-05 | 에스케이케미칼주식회사 | 당뇨 및 비만 치료예방에 유효한 퀴나졸린 유도체 |
| MX2007010037A (es) | 2005-02-18 | 2008-02-15 | Novartis Vaccines & Diagnostic | Agentes antiangiogenicos con aldesleucina. |
| WO2006097441A1 (en) | 2005-03-14 | 2006-09-21 | Neurosearch A/S | Potassium channel modulating agents and their medical use |
| WO2006099972A1 (en) | 2005-03-23 | 2006-09-28 | F. Hoffmann-La Roche Ag | Acetylenyl-pyrazolo-pvrimidine derivatives as mglur2 antagonists |
| CN101189234B (zh) | 2005-03-25 | 2011-08-17 | 泰博特克药品有限公司 | Hcv的杂二环抑制剂 |
| US8030318B2 (en) | 2005-03-25 | 2011-10-04 | Tibotec Pharmaceuticals Ltd. | Fused bicyclic inhibitors of HCV |
| US7906522B2 (en) | 2005-04-28 | 2011-03-15 | Kyowa Hakko Kirin Co., Ltd | 2-aminoquinazoline derivatives |
| WO2007002781A2 (en) | 2005-06-28 | 2007-01-04 | Bausch & Lomb Incorporated | Preparations comprising arylazine substituted with a carbonylic moiety to increase the activity of gelatinase a in ocular cells |
| GB0525164D0 (en) | 2005-12-09 | 2006-01-18 | Xention Discovery Ltd | Compounds |
| EP1966184B1 (en) | 2005-12-20 | 2010-08-25 | NeuroSearch A/S | Pyridinyl-quinazoline derivatives and their medical use |
| KR20080089416A (ko) | 2005-12-21 | 2008-10-06 | 페인셉터 파마 코포레이션 | 개폐 이온 통로를 조절하기 위한 조성물 및 방법 |
| DE102006012251A1 (de) | 2006-03-15 | 2007-11-08 | Grünenthal GmbH | Substituierte 4-Amino-chinazolin-Derivate und ihre Verwendung zur Herstellung von Arzneimitteln |
| AU2007271187A1 (en) | 2006-07-03 | 2008-01-10 | Vereniging Voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek En Patientenzorg | Fused bicyclic compounds interacting with the histamine H4 receptor |
| WO2008023357A1 (en) | 2006-08-22 | 2008-02-28 | Technion Research And Development Foundation Ltd. | Heterocyclic derivatives binding to the peripheral-type benzodiazepine receptor (pbr) |
| US20100173332A1 (en) | 2006-09-07 | 2010-07-08 | Auckland Uniservices Limited | Method for the Fluorescent Detection of Nitroreductase Activity Using Nitro-Substituted Aromatic Compounds |
| WO2008045529A1 (en) | 2006-10-12 | 2008-04-17 | Serenex, Inc. | Purine and pyrimidine derivatives for treatment of cancer and inflammatory diseases |
| US8039505B2 (en) | 2007-04-11 | 2011-10-18 | University Of Utah Research Foundation | Compounds for modulating T-cells |
| PE20090717A1 (es) | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| WO2008150827A1 (en) | 2007-05-29 | 2008-12-11 | Smithkline Beecham Corporation | Naphthyridine, derivatives as p13 kinase inhibitors |
| US9603848B2 (en) | 2007-06-08 | 2017-03-28 | Senomyx, Inc. | Modulation of chemosensory receptors and ligands associated therewith |
| WO2009006141A2 (en) | 2007-07-05 | 2009-01-08 | Bausch & Lomb Incorporated | Authority to read as follows: compositions and methods for treating or controlling infections of the eye a sequelae thereof |
| US7829574B2 (en) | 2008-05-09 | 2010-11-09 | Hutchison Medipharma Enterprises Limited | Substituted quinazoline compounds and their use in treating angiogenesis-related diseases |
| CN101575333B (zh) | 2008-05-09 | 2011-06-22 | 和记黄埔医药（上海）有限公司 | 一种喹唑啉衍生物及其医药用途 |
| CN102105449A (zh) | 2008-05-21 | 2011-06-22 | 健泰科生物技术公司 | 芳基磺酰胺化合物、组合物及其使用方法 |
| EA021113B1 (ru) * | 2009-09-03 | 2015-04-30 | Бристол-Майерс Сквибб Кампани | Хиназолины в качестве ингибиторов калиевых каналов |
| CN102984941B (zh) | 2009-09-04 | 2016-08-17 | 密执安大学评议会 | 用于治疗白血病的组合物和方法 |
| AR079814A1 (es) | 2009-12-31 | 2012-02-22 | Otsuka Pharma Co Ltd | Compuestos heterociclicos, composiciones farmaceuticas que los contienen y sus usos |
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