RU2600927C2 - Бензоксазепиновые ингибиторы pi3k и способы применения - Google Patents

Info

Publication number

RU2600927C2

RU2600927C2 RU2012117398/04A RU2012117398A RU2600927C2 RU 2600927 C2 RU2600927 C2 RU 2600927C2 RU 2012117398/04 A RU2012117398/04 A RU 2012117398/04A RU 2012117398 A RU2012117398 A RU 2012117398A RU 2600927 C2 RU2600927 C2 RU 2600927C2

Authority

RU

Russia

Prior art keywords

triazol

dihydrobenzo

isopropyl

imidazo

oxazepin

Prior art date

2009-09-28

Links

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• Global Dossier
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• ZCXLTWVZYXBHJS-UHFFFAOYSA-N 1,2-benzoxazepine Chemical compound O1N=CC=CC2=CC=CC=C12 ZCXLTWVZYXBHJS-UHFFFAOYSA-N 0.000 title abstract description 12
• 238000000034 method Methods 0.000 title description 80
• 239000012828 PI3K inhibitor Substances 0.000 title description 6
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 365
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 106
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 61
• 238000011282 treatment Methods 0.000 claims abstract description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 35
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 35
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 33
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 31
• 201000011510 cancer Diseases 0.000 claims abstract description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 18
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims abstract description 14
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims abstract description 14
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 14
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 11
• 108091007960 PI3Ks Proteins 0.000 claims abstract description 9
• 230000001404 mediated effect Effects 0.000 claims abstract description 9
• 102000038030 PI3Ks Human genes 0.000 claims abstract 4
• LWZYUACNWRVDDJ-UHFFFAOYSA-N 1-benzoxepine Chemical compound O1C=CC=CC2=CC=CC=C12 LWZYUACNWRVDDJ-UHFFFAOYSA-N 0.000 claims abstract 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
• -1 1- (2-methanesulfonylethyl) azetidin-3-yl Chemical group 0.000 claims description 705
• 125000002947 alkylene group Chemical group 0.000 claims description 149
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 86
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 86
• 125000000217 alkyl group Chemical group 0.000 claims description 71
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 63
• VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims description 60
• 239000000460 chlorine Substances 0.000 claims description 46
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 45
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 38
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 35
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 31
• 150000003839 salts Chemical class 0.000 claims description 29
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 28
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 24
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 17
• 125000004043 oxo group Chemical group O=* 0.000 claims description 15
• 230000001225 therapeutic effect Effects 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 239000010802 sludge Substances 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 11
• 150000002431 hydrogen Chemical class 0.000 claims description 11
• 150000004702 methyl esters Chemical class 0.000 claims description 10
• STYKXHWOJFVEDT-UHFFFAOYSA-N pyrido[3,4-f][1,4]oxazepine Chemical compound O1C=CN=CC2=C1C=CN=C2 STYKXHWOJFVEDT-UHFFFAOYSA-N 0.000 claims description 10
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 8
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
• XIMBESZRBTVIOD-UHFFFAOYSA-N piperidine-2-carboxamide Chemical compound NC(=O)C1CCCCN1 XIMBESZRBTVIOD-UHFFFAOYSA-N 0.000 claims description 8
• AQSJJWPFUXSPDO-UHFFFAOYSA-N 2-methyl-2-[[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]oxy]propanamide Chemical compound C=1N2CCOC3=CC(OC(C)(C)C(N)=O)=CC=C3C2=NC=1C1=NC=NN1CC(F)(F)F AQSJJWPFUXSPDO-UHFFFAOYSA-N 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 claims description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
• AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
• KKCWBKUOPJMUQV-UHFFFAOYSA-N azetidine-2-carboxamide Chemical compound NC(=O)C1CCN1 KKCWBKUOPJMUQV-UHFFFAOYSA-N 0.000 claims description 5
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• SIKYDKLGPWRPMZ-LBPRGKRZSA-N (2s)-2-[[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]oxy]propanamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(O[C@@H](C)C(N)=O)C=2)C3=N1 SIKYDKLGPWRPMZ-LBPRGKRZSA-N 0.000 claims description 4
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
• NAGHPTITPJFKLN-GHTZIAJQSA-N 2-[(3s,4s)-3-hydroxy-4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]-n,n-dimethylacetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)[C@H]2[C@@H](CN(CC(=O)N(C)C)CC2)O)C3=N1 NAGHPTITPJFKLN-GHTZIAJQSA-N 0.000 claims description 4
• ZKZKTQFKMLSWQV-UHFFFAOYSA-N 2-[3-hydroxy-4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]-n,2-dimethylpropanamide Chemical compound OC1CN(C(C)(C)C(=O)NC)CCC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=C1 ZKZKTQFKMLSWQV-UHFFFAOYSA-N 0.000 claims description 4
• 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 4
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
• 125000004494 ethyl ester group Chemical group 0.000 claims description 4
• JCWRLHAZPLLRSC-UHFFFAOYSA-N imidazo[1,2-d][1,4]oxazepine-9-carbonitrile Chemical compound N#CC1=COC=CN2C=CN=C12 JCWRLHAZPLLRSC-UHFFFAOYSA-N 0.000 claims description 4
• IPHUZOSVEIFLQT-UHFFFAOYSA-N pyrido[3,4-f][1,4]oxazepin-9-amine Chemical compound C1=NC=COC2=C1C=NC=C2N IPHUZOSVEIFLQT-UHFFFAOYSA-N 0.000 claims description 4
• LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• DGQYBZHMCOYOGK-UHFFFAOYSA-N 12-chloro-4-[1-(propan-2-yl)-1h-1,2,4-triazol-5-yl]-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(Cl)C=2)C3=N1 DGQYBZHMCOYOGK-UHFFFAOYSA-N 0.000 claims description 3
• JCPSQARQKUAPFR-UHFFFAOYSA-N 2-(2-propan-2-yl-1,2,4-triazol-3-yl)-9-[1-(pyridin-4-ylmethyl)azetidin-3-yl]-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=NN2C3=CC(C4CN(CC=5C=CN=CC=5)C4)=CC=C3OCCC2=C1 JCPSQARQKUAPFR-UHFFFAOYSA-N 0.000 claims description 3
• ZEUGICSMFHPFGZ-UHFFFAOYSA-N 2-[1-(2-chlorophenyl)imidazol-2-yl]-n-(1-hydroxy-2-methylpropan-2-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carboxamide Chemical compound N1=C2C3=CC(C(=O)NC(C)(CO)C)=CC=C3OCCN2C=C1C1=NC=CN1C1=CC=CC=C1Cl ZEUGICSMFHPFGZ-UHFFFAOYSA-N 0.000 claims description 3
• YDNXPEDFUKMLGZ-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1,2,4-triazol-3-yl]-n-(1-hydroxy-2-methylpropan-2-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound C=1N2CCOC3=CC(C(=O)NC(C)(CO)C)=CC=C3C2=NC=1C1=NC=NN1C1=CC=CC=C1Cl YDNXPEDFUKMLGZ-UHFFFAOYSA-N 0.000 claims description 3
• WCFWHXBNRCLMCM-UHFFFAOYSA-N 2-[3-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepin-9-yl]azetidin-1-yl]ethanol Chemical compound CC(C)N1N=CN=C1C1=NN2C3=CC(C4CN(CCO)C4)=CC=C3OCCC2=C1 WCFWHXBNRCLMCM-UHFFFAOYSA-N 0.000 claims description 3
• ZZMMFFFSXXINPH-UHFFFAOYSA-N 2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]imidazol-1-yl]ethanol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2N=CN(CCO)C=2)C3=N1 ZZMMFFFSXXINPH-UHFFFAOYSA-N 0.000 claims description 3
• FSGDNSSAEHNEAS-UHFFFAOYSA-N 2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]ethanol Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(CCO)N=C2)C3=N1 FSGDNSSAEHNEAS-UHFFFAOYSA-N 0.000 claims description 3
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
• QKZHALLNBLDACB-UHFFFAOYSA-N 2-methyl-1-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]propan-2-ol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(CC(C)(C)O)N=C2)C3=N1 QKZHALLNBLDACB-UHFFFAOYSA-N 0.000 claims description 3
• OAKACXCSCSMXAO-UHFFFAOYSA-N 2-methyl-2-[3-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepin-9-yl]azetidin-1-yl]propan-1-ol Chemical compound CC(C)N1N=CN=C1C1=NN2C3=CC(C4CN(C4)C(C)(C)CO)=CC=C3OCCC2=C1 OAKACXCSCSMXAO-UHFFFAOYSA-N 0.000 claims description 3
• MKHFQOOVKRVVHR-UHFFFAOYSA-N 2-methyl-2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]propan-1-ol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CC2)C(C)(C)CO)C3=N1 MKHFQOOVKRVVHR-UHFFFAOYSA-N 0.000 claims description 3
• BEUQXVWXFDOSAQ-UHFFFAOYSA-N 2-methyl-2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]propanamide Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(N=C2)C(C)(C)C(N)=O)C3=N1 BEUQXVWXFDOSAQ-UHFFFAOYSA-N 0.000 claims description 3
• HFHGVIBGEFYIFU-UHFFFAOYSA-N 3h-oxazepine-2-carboxamide Chemical compound NC(=O)N1CC=CC=CO1 HFHGVIBGEFYIFU-UHFFFAOYSA-N 0.000 claims description 3
• RMOUVUGQFOCMLH-UHFFFAOYSA-N 9-(1-propan-2-ylpiperidin-4-yl)-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound C1CN(C(C)C)CCC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=C1 RMOUVUGQFOCMLH-UHFFFAOYSA-N 0.000 claims description 3
• APDHHYSWMALGRO-UHFFFAOYSA-N 9-[1-[2-(dimethylamino)-2-oxoethyl]piperidin-4-yl]-n-(2-hydroxyethyl)-n-propan-2-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide Chemical compound C=1C=C2C3=NC(C(=O)N(CCO)C(C)C)=CN3CCOC2=CC=1C1CCN(CC(=O)N(C)C)CC1 APDHHYSWMALGRO-UHFFFAOYSA-N 0.000 claims description 3
• QETYFXJUQZUKJS-UHFFFAOYSA-N 9-bromo-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(Br)C=2)C3=N1 QETYFXJUQZUKJS-UHFFFAOYSA-N 0.000 claims description 3
• WLTNPZPMVAIRRH-UHFFFAOYSA-N 9-bromo-2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(Br)C=2)C3=N1 WLTNPZPMVAIRRH-UHFFFAOYSA-N 0.000 claims description 3
• XQVWEGWAQKXDCG-UHFFFAOYSA-N [2-[2-(2,4-difluorophenyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-10-yl]-[4-(2-hydroxyethyl)piperazin-1-yl]methanone Chemical compound C1CN(CCO)CCN1C(=O)C1=CC=C(OCCN2C3=NC(=C2)C=2N(N=CN=2)C=2C(=CC(F)=CC=2)F)C3=C1 XQVWEGWAQKXDCG-UHFFFAOYSA-N 0.000 claims description 3
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• OQCZWRABLTVBHX-UHFFFAOYSA-N n-(1-propan-2-ylazetidin-3-yl)-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepine-9-carboxamide Chemical compound C1N(C(C)C)CC1NC(=O)C1=CC=C(OCCC=2N3N=C(C=2)C=2N(N=CN=2)C(C)C)C3=C1 OQCZWRABLTVBHX-UHFFFAOYSA-N 0.000 claims description 3
• WPJZUWGCFYZZIY-UHFFFAOYSA-N n-hydroxy-2-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]acetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(CC(=O)NO)C=2)C3=N1 WPJZUWGCFYZZIY-UHFFFAOYSA-N 0.000 claims description 3
• AVHACHCDPSWEDL-UHFFFAOYSA-N n-methoxy-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound C=1N2CCOC3=CC(C(=O)NOC)=CC=C3C2=NC=1C1=NC=NN1C(C)C AVHACHCDPSWEDL-UHFFFAOYSA-N 0.000 claims description 3
• ABPGIOCDUSJVRC-UHFFFAOYSA-N n-methyl-2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound C=1N2CCOC3=CC(C(=O)NC)=CC=C3C2=NC=1C1=NC=NN1CC(F)(F)F ABPGIOCDUSJVRC-UHFFFAOYSA-N 0.000 claims description 3
• 230000000069 prophylactic effect Effects 0.000 claims description 3
• DNTVKOMHCDKATN-UHFFFAOYSA-N pyrazolidine-3,5-dione Chemical compound O=C1CC(=O)NN1 DNTVKOMHCDKATN-UHFFFAOYSA-N 0.000 claims description 3
• OMIZXLNVXIAFTA-UHFFFAOYSA-N (1-aminocyclopropyl)-[3-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]azetidin-1-yl]methanone Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CN(C2)C(=O)C2(N)CC2)C3=N1 OMIZXLNVXIAFTA-UHFFFAOYSA-N 0.000 claims description 2
• ISKQWZOKWLUBNW-OAHLLOKOSA-N (2r)-1-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)-2,5-dihydro-1h-pyrrole-2-carboxamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(C=2)N2[C@H](C=CC2)C(N)=O)C3=N1 ISKQWZOKWLUBNW-OAHLLOKOSA-N 0.000 claims description 2
• SIKYDKLGPWRPMZ-GFCCVEGCSA-N (2r)-2-[[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]oxy]propanamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(O[C@H](C)C(N)=O)C=2)C3=N1 SIKYDKLGPWRPMZ-GFCCVEGCSA-N 0.000 claims description 2
• OXCSFUYZGQVPBC-CQSZACIVSA-N (2r)-2-[[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]oxy]butanamide Chemical compound C=1N2CCOC3=CC(O[C@H](CC)C(N)=O)=CC=C3C2=NC=1C1=NC=NN1CC(F)(F)F OXCSFUYZGQVPBC-CQSZACIVSA-N 0.000 claims description 2
• BLCVYWUNXXAHGY-SNVBAGLBSA-N (2r)-2-[[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]oxy]propanamide Chemical compound C=1N2CCOC3=CC(O[C@H](C)C(N)=O)=CC=C3C2=NC=1C1=NC=NN1CC(F)(F)F BLCVYWUNXXAHGY-SNVBAGLBSA-N 0.000 claims description 2
• ISKQWZOKWLUBNW-HNNXBMFYSA-N (2s)-1-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)-2,5-dihydro-1h-pyrrole-2-carboxamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(C=2)N2[C@@H](C=CC2)C(N)=O)C3=N1 ISKQWZOKWLUBNW-HNNXBMFYSA-N 0.000 claims description 2
• HFPNVOHXZPPIPA-NSHDSACASA-N (2s)-2-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-ylamino)propanamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(N[C@@H](C)C(N)=O)C=2)C3=N1 HFPNVOHXZPPIPA-NSHDSACASA-N 0.000 claims description 2
• AHNACMAJVLLNSG-JTQLQIEISA-N (2s)-2-[[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound C=1N2CCOC3=CC(N[C@@H](C)C(N)=O)=CC=C3C2=NC=1C1=NC=NN1CC(F)(F)F AHNACMAJVLLNSG-JTQLQIEISA-N 0.000 claims description 2
• BLCVYWUNXXAHGY-JTQLQIEISA-N (2s)-2-[[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]oxy]propanamide Chemical compound C=1N2CCOC3=CC(O[C@@H](C)C(N)=O)=CC=C3C2=NC=1C1=NC=NN1CC(F)(F)F BLCVYWUNXXAHGY-JTQLQIEISA-N 0.000 claims description 2
• SGTJRXWMOGYPAU-INIZCTEOSA-N (2s)-2-hydroxy-1-[3-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]azetidin-1-yl]propan-1-one Chemical compound C1N(C(=O)[C@@H](O)C)CC1N1N=CC(C=2C=C3OCCN4C=C(N=C4C3=CC=2)C=2N(N=C(C)N=2)C(C)C)=C1 SGTJRXWMOGYPAU-INIZCTEOSA-N 0.000 claims description 2
• BFUFHXYCOJWPEA-AWEZNQCLSA-N (2s)-3-hydroxy-2-[[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]oxy]propanamide Chemical compound C=1N2CCOC3=CC(O[C@@H](CO)C(=O)N)=CC=C3C2=NC=1C1=NC=NN1CC(F)(F)F BFUFHXYCOJWPEA-AWEZNQCLSA-N 0.000 claims description 2
• PPEGSWIZGVHBLO-CYBMUJFWSA-N (3r)-1-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)pyrrolidin-3-ol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(C=2)N2C[C@H](O)CC2)C3=N1 PPEGSWIZGVHBLO-CYBMUJFWSA-N 0.000 claims description 2
• NHERVSOPGZWWEN-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-10-yl]methanone Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(OCCN2C3=NC(=C2)C=2N(N=CN=2)CC(F)(F)F)C3=C1 NHERVSOPGZWWEN-UHFFFAOYSA-N 0.000 claims description 2
• QSSHUOWAVUKAFT-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-10-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC=C(OCCN2C3=NC(=C2)C=2N(N=CN=2)CC(F)(F)F)C3=C1 QSSHUOWAVUKAFT-UHFFFAOYSA-N 0.000 claims description 2
• FMGDFTULYHJMIN-UHFFFAOYSA-N (5-(9-(3,3-difluoroazetidin-1-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-2-yl)-1-isopropyl-1h-1,2,4-triazol-3-yl)methanol Chemical compound CC(C)N1N=C(CO)N=C1C1=CN(CCOC=2C3=CN=C(C=2)N2CC(F)(F)C2)C3=N1 FMGDFTULYHJMIN-UHFFFAOYSA-N 0.000 claims description 2
• BCYOYASGXQTNAB-UHFFFAOYSA-N (5-(9-(dimethylamino)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-2-yl)-1-(2,2,2-trifluoro ethyl)-1h-1,2,4-triazol-3-yl)methanol Chemical compound N1=C2C=3C=NC(N(C)C)=CC=3OCCN2C=C1C1=NC(CO)=NN1CC(F)(F)F BCYOYASGXQTNAB-UHFFFAOYSA-N 0.000 claims description 2
• LPLPFZSOIOEMLJ-UHFFFAOYSA-N (5-(9-(dimethylamino)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-2-yl)-1-isopropyl-1h-1,2,4-triazol-3-yl)methanol Chemical compound CC(C)N1N=C(CO)N=C1C1=CN(CCOC=2C3=CN=C(C=2)N(C)C)C3=N1 LPLPFZSOIOEMLJ-UHFFFAOYSA-N 0.000 claims description 2
• VCNRSVGGEZNJNU-UHFFFAOYSA-N (5-(9-(pyrrolidin-1-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-2-yl)-1-(2,2,2-trifluoroethyl)-1h-1,2,4-triazol-3-yl)methanol Chemical compound FC(F)(F)CN1N=C(CO)N=C1C1=CN(CCOC=2C3=CN=C(C=2)N2CCCC2)C3=N1 VCNRSVGGEZNJNU-UHFFFAOYSA-N 0.000 claims description 2
• VJOZXXWCUPTTMC-LLVKDONJSA-N (r)-2-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yloxy)propanamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(O[C@H](C)C(N)=O)C=2)C3=N1 VJOZXXWCUPTTMC-LLVKDONJSA-N 0.000 claims description 2
• FXVHSEQMNFVQRW-UHFFFAOYSA-N 1-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)azetidin-3-ol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(C=2)N2CC(O)C2)C3=N1 FXVHSEQMNFVQRW-UHFFFAOYSA-N 0.000 claims description 2
• OYCLTIZHJSPKBP-UHFFFAOYSA-N 1-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)piperidin-4-ol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(C=2)N2CCC(O)CC2)C3=N1 OYCLTIZHJSPKBP-UHFFFAOYSA-N 0.000 claims description 2
• ZTZULMJUEUTMEO-UHFFFAOYSA-N 1-[3-[2-[2-(2,4-difluorophenyl)-1,2,4-triazol-3-yl]-4,5-dihydro-[1]benzoxepino[5,4-c]pyrazol-8-yl]azetidin-1-yl]-2-methylpropan-2-ol Chemical compound C1N(CC(C)(O)C)CC1C1=CC=C(C=2C(=CN(N=2)C=2N(N=CN=2)C=2C(=CC(F)=CC=2)F)CCO2)C2=C1 ZTZULMJUEUTMEO-UHFFFAOYSA-N 0.000 claims description 2
• UTCSHCLQJFMNOT-UHFFFAOYSA-N 1-[4-[2-(5-amino-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound CC(C)N1N=C(N)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(CC(C)(C)O)N=C2)C3=N1 UTCSHCLQJFMNOT-UHFFFAOYSA-N 0.000 claims description 2
• CCSAMCDQMKBBLW-UHFFFAOYSA-N 1-[4-[2-[2-(2,4-difluorophenyl)-1,2,4-triazol-3-yl]-4,5-dihydro-[1]benzoxepino[5,4-c]pyrazol-9-yl]piperidin-1-yl]-2-methylpropan-2-ol Chemical compound C1CN(CC(C)(O)C)CCC1C1=CC=C(OCCC=2C3=NN(C=2)C=2N(N=CN=2)C=2C(=CC(F)=CC=2)F)C3=C1 CCSAMCDQMKBBLW-UHFFFAOYSA-N 0.000 claims description 2
• ITGLFBCWMFWYOW-UHFFFAOYSA-N 1-[4-[2-[5-(hydroxymethyl)-2-propan-2-yl-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound CC(C)N1N=C(CO)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(CC(C)(C)O)N=C2)C3=N1 ITGLFBCWMFWYOW-UHFFFAOYSA-N 0.000 claims description 2
• OFMJUBYHACLFDA-UHFFFAOYSA-N 1-[4-[2-[5-(methoxymethyl)-2-propan-2-yl-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound CC(C)N1N=C(COC)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(CC(C)(C)O)N=C2)C3=N1 OFMJUBYHACLFDA-UHFFFAOYSA-N 0.000 claims description 2
• OOGFWRKSKOVZJZ-UHFFFAOYSA-N 1-[[2-[2-(2,4-difluorophenyl)-5-methyl-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]methylamino]-2-methylpropan-2-ol Chemical compound N1=C(C)N=C(C=2N=C3C4=CC=C(CNCC(C)(C)O)C=C4OCCN3C=2)N1C1=CC=C(F)C=C1F OOGFWRKSKOVZJZ-UHFFFAOYSA-N 0.000 claims description 2
• KOWBZUFEWULWGO-UHFFFAOYSA-N 10-(4-chlorophenyl)-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC(=CC=2)C=2C=CC(Cl)=CC=2)C3=N1 KOWBZUFEWULWGO-UHFFFAOYSA-N 0.000 claims description 2
• AQUAOBAAXOZENT-UHFFFAOYSA-N 10-(4-chlorophenyl)-2-[2-(2-chlorophenyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(OCCN2C3=NC(=C2)C=2N(N=CN=2)C=2C(=CC=CC=2)Cl)C3=C1 AQUAOBAAXOZENT-UHFFFAOYSA-N 0.000 claims description 2
• BRGMNCXDYSCNNA-UHFFFAOYSA-N 10-bromo-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC(Br)=CC=2)C3=N1 BRGMNCXDYSCNNA-UHFFFAOYSA-N 0.000 claims description 2
• ATGAMSJXCAWLNO-UHFFFAOYSA-N 10-fluoro-2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC(F)=CC=2)C3=N1 ATGAMSJXCAWLNO-UHFFFAOYSA-N 0.000 claims description 2
• SLVRPGRTPAWVSH-UHFFFAOYSA-N 10-methyl-2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC(C)=CC=2)C3=N1 SLVRPGRTPAWVSH-UHFFFAOYSA-N 0.000 claims description 2
• RKDNWQHUMNLMLW-UHFFFAOYSA-N 10-phenyl-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC(=CC=2)C=2C=CC=CC=2)C3=N1 RKDNWQHUMNLMLW-UHFFFAOYSA-N 0.000 claims description 2
• IIKZRFCIODWNRK-UHFFFAOYSA-N 2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-10-(4-methylpiperazin-1-yl)-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC(=NC=2)N2CCN(C)CC2)C3=N1 IIKZRFCIODWNRK-UHFFFAOYSA-N 0.000 claims description 2
• UXXNHFLKSGPANK-UHFFFAOYSA-N 2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=CC=2)C3=N1 UXXNHFLKSGPANK-UHFFFAOYSA-N 0.000 claims description 2
• BDQFAPFRHRKEII-UHFFFAOYSA-N 2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=NC=2)C3=N1 BDQFAPFRHRKEII-UHFFFAOYSA-N 0.000 claims description 2
• YJHBDCQDZSGSNB-UHFFFAOYSA-N 2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-9-(4-methylpiperazin-1-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,2-f][1,4]oxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(N=2)N2CCN(C)CC2)C3=N1 YJHBDCQDZSGSNB-UHFFFAOYSA-N 0.000 claims description 2
• NRZPJXCLLQBCAH-UHFFFAOYSA-N 2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-9-morpholino-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(C=2)N2CCOCC2)C3=N1 NRZPJXCLLQBCAH-UHFFFAOYSA-N 0.000 claims description 2
• KCFFJQFFHDAFFY-UHFFFAOYSA-N 2-(1-isopropyl-1h-imidazol-2-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine Chemical compound CC(C)N1C=CN=C1C1=CN(CCOC=2C3=CN=CC=2)C3=N1 KCFFJQFFHDAFFY-UHFFFAOYSA-N 0.000 claims description 2
• AAMIDBWPEQPCRK-UHFFFAOYSA-N 2-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-ylamino)acetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(NCC(N)=O)C=2)C3=N1 AAMIDBWPEQPCRK-UHFFFAOYSA-N 0.000 claims description 2
• NIHIVEAPCNKKQR-UHFFFAOYSA-N 2-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yloxy)-3-methylbutanamide Chemical compound N1=C2C=3C=NC(OC(C(C)C)C(N)=O)=CC=3OCCN2C=C1C1=NC=NN1C(C)C NIHIVEAPCNKKQR-UHFFFAOYSA-N 0.000 claims description 2
• XXRLAERJARJLQV-UHFFFAOYSA-N 2-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yloxy)acetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(OCC(N)=O)C=2)C3=N1 XXRLAERJARJLQV-UHFFFAOYSA-N 0.000 claims description 2
• PNACIUHHIOZPSV-UHFFFAOYSA-N 2-(2-(1-isopropyl-3-methyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-ylamino)acetamide Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CN=C(NCC(N)=O)C=2)C3=N1 PNACIUHHIOZPSV-UHFFFAOYSA-N 0.000 claims description 2
• MUZMBOPNKLFIEE-UHFFFAOYSA-N 2-(2-propan-2-yl-1,2,4-triazol-3-yl)-10-pyrimidin-5-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC(=CC=2)C=2C=NC=NC=2)C3=N1 MUZMBOPNKLFIEE-UHFFFAOYSA-N 0.000 claims description 2
• GMRFLGRDFGEHCS-UHFFFAOYSA-N 2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-ol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(O)C=2)C3=N1 GMRFLGRDFGEHCS-UHFFFAOYSA-N 0.000 claims description 2
• GNCJJRXCELYPRJ-UHFFFAOYSA-N 2-(2-propan-2-yl-1,2,4-triazol-3-yl)-9-(1h-pyrazol-4-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CNN=C2)C3=N1 GNCJJRXCELYPRJ-UHFFFAOYSA-N 0.000 claims description 2
• UQCBCIHVDOBZQN-UHFFFAOYSA-N 2-(2-propan-2-yl-1,2,4-triazol-3-yl)-9-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CC(F)(F)F)CC2)C3=N1 UQCBCIHVDOBZQN-UHFFFAOYSA-N 0.000 claims description 2
• ZHOKDYGXJPBQCB-UHFFFAOYSA-N 2-(2-propan-2-ylpyrazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carboxamide Chemical compound CC(C)N1N=CC=C1C1=CN(CCOC=2C3=CC(=CC=2)C(N)=O)C3=N1 ZHOKDYGXJPBQCB-UHFFFAOYSA-N 0.000 claims description 2
• LIZPVSMVZNZBMF-UHFFFAOYSA-N 2-(2-propan-2-ylpyrazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound CC(C)N1N=CC=C1C1=CN(CCOC=2C3=CC=C(C=2)C(N)=O)C3=N1 LIZPVSMVZNZBMF-UHFFFAOYSA-N 0.000 claims description 2
• ZAOOEKLTDLHVNT-UHFFFAOYSA-N 2-(3-methyl-1-(2,2,2-trifluoroethyl)-1h-1,2,4-triazol-5-yl)-9-(2-(2-methylbenzyl)pyrrolidin-1-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine Chemical compound FC(F)(F)CN1N=C(C)N=C1C1=CN(CCOC=2C3=CN=C(C=2)N2C(CCC2)CC=2C(=CC=CC=2)C)C3=N1 ZAOOEKLTDLHVNT-UHFFFAOYSA-N 0.000 claims description 2
• KTCWLHXIKVWFSU-UHFFFAOYSA-N 2-(4-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,2-f][1,4]ox azepin-9-yl)piperazin-1-yl)-n-methylacetamide Chemical compound C1CN(CC(=O)NC)CCN1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=N1 KTCWLHXIKVWFSU-UHFFFAOYSA-N 0.000 claims description 2
• IPFNUAZWISLAOI-UHFFFAOYSA-N 2-(4-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,2-f][1,4]oxazepin-9-yl)piperazin-1-yl)-n,n-dimethylacetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(N=2)N2CCN(CC(=O)N(C)C)CC2)C3=N1 IPFNUAZWISLAOI-UHFFFAOYSA-N 0.000 claims description 2
• UYPLNXNRTVGJAK-UHFFFAOYSA-N 2-(4-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)piperazin-1-yl)-n,n-dimethylacetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(C=2)N2CCN(CC(=O)N(C)C)CC2)C3=N1 UYPLNXNRTVGJAK-UHFFFAOYSA-N 0.000 claims description 2
• WHXSJBOGJXZMHH-UHFFFAOYSA-N 2-(4-cyano-2-propan-2-ylpyrazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound CC(C)N1N=CC(C#N)=C1C1=CN(CCOC=2C3=CC=C(C=2)C(N)=O)C3=N1 WHXSJBOGJXZMHH-UHFFFAOYSA-N 0.000 claims description 2
• WROVEKYHJXCCAB-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-10-(1-methylpyrazol-4-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC(=CC=2)C2=CN(C)N=C2)C3=N1 WROVEKYHJXCCAB-UHFFFAOYSA-N 0.000 claims description 2
• RBTUJOURVREIFG-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=CC=2)C3=N1 RBTUJOURVREIFG-UHFFFAOYSA-N 0.000 claims description 2
• QBYKURVSZLPNIH-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carbonitrile Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC(=CC=2)C#N)C3=N1 QBYKURVSZLPNIH-UHFFFAOYSA-N 0.000 claims description 2
• NAALSROZEGYKED-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carbonitrile Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C#N)C3=N1 NAALSROZEGYKED-UHFFFAOYSA-N 0.000 claims description 2
• MPFNMPYHBKESAO-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-9-(1-methylpyrazol-4-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(C)N=C2)C3=N1 MPFNMPYHBKESAO-UHFFFAOYSA-N 0.000 claims description 2
• LUWSDNOWEOJXFK-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-9-pyridin-3-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2C=NC=CC=2)C3=N1 LUWSDNOWEOJXFK-UHFFFAOYSA-N 0.000 claims description 2
• FMZWNURLDICCHO-UHFFFAOYSA-N 2-[2-(2,4-difluorophenyl)-1,2,4-triazol-3-yl]-9-[1-(2-methylsulfonylethyl)piperidin-4-yl]-4,5-dihydro-[1]benzoxepino[5,4-c]pyrazole Chemical compound C1CN(CCS(=O)(=O)C)CCC1C1=CC=C(OCCC=2C3=NN(C=2)C=2N(N=CN=2)C=2C(=CC(F)=CC=2)F)C3=C1 FMZWNURLDICCHO-UHFFFAOYSA-N 0.000 claims description 2
• JMTOEIQEXSLRSH-UHFFFAOYSA-N 2-[2-(2,4-difluorophenyl)-1,2,4-triazol-3-yl]-n-(1-hydroxy-2-methylpropan-2-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carboxamide Chemical compound N1=C2C3=CC(C(=O)NC(C)(CO)C)=CC=C3OCCN2C=C1C1=NC=NN1C1=CC=C(F)C=C1F JMTOEIQEXSLRSH-UHFFFAOYSA-N 0.000 claims description 2
• DEVYAKYXGVYHEN-UHFFFAOYSA-N 2-[2-(2,4-difluorophenyl)-1,2,4-triazol-3-yl]-n-methyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound C=1N2CCOC3=CC(C(=O)NC)=CC=C3C2=NC=1C1=NC=NN1C1=CC=C(F)C=C1F DEVYAKYXGVYHEN-UHFFFAOYSA-N 0.000 claims description 2
• KHIXKMRPHAEGOI-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1,2,4-triazol-3-yl]-10-phenyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound ClC1=CC=CC=C1N1C(C=2N=C3C4=CC(=CC=C4OCCN3C=2)C=2C=CC=CC=2)=NC=N1 KHIXKMRPHAEGOI-UHFFFAOYSA-N 0.000 claims description 2
• QAEVNJGBHNVZQG-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1,2,4-triazol-3-yl]-10-pyrimidin-5-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound ClC1=CC=CC=C1N1C(C=2N=C3C4=CC(=CC=C4OCCN3C=2)C=2C=NC=NC=2)=NC=N1 QAEVNJGBHNVZQG-UHFFFAOYSA-N 0.000 claims description 2
• WABCFZZOZXDKOQ-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carboxamide Chemical compound N1=C2C3=CC(C(=O)N)=CC=C3OCCN2C=C1C1=NC=NN1C1=CC=CC=C1Cl WABCFZZOZXDKOQ-UHFFFAOYSA-N 0.000 claims description 2
• HGRICAGVHYMPQC-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound C=1N2CCOC3=CC(C(=O)N)=CC=C3C2=NC=1C1=NC=NN1C1=CC=CC=C1Cl HGRICAGVHYMPQC-UHFFFAOYSA-N 0.000 claims description 2
• BXQZVKGOEAMETR-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1,2,4-triazol-3-yl]-n-(2-methylsulfonylethyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound C=1N2CCOC3=CC(C(=O)NCCS(=O)(=O)C)=CC=C3C2=NC=1C1=NC=NN1C1=CC=CC=C1Cl BXQZVKGOEAMETR-UHFFFAOYSA-N 0.000 claims description 2
• XMPKCIJGUQHEOG-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1,2,4-triazol-3-yl]-n-methyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound C=1N2CCOC3=CC(C(=O)NC)=CC=C3C2=NC=1C1=NC=NN1C1=CC=CC=C1Cl XMPKCIJGUQHEOG-UHFFFAOYSA-N 0.000 claims description 2
• SYWGXTSMYNHNJU-UHFFFAOYSA-N 2-[2-[9-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-2-yl]imidazol-1-yl]-n-methylacetamide Chemical compound CNC(=O)CN1C=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(CC(C)(C)O)N=C2)C3=N1 SYWGXTSMYNHNJU-UHFFFAOYSA-N 0.000 claims description 2
• QUUGEEWRVAGATH-UHFFFAOYSA-N 2-[2-methyl-4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]imidazol-1-yl]ethanol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2N=C(C)N(CCO)C=2)C3=N1 QUUGEEWRVAGATH-UHFFFAOYSA-N 0.000 claims description 2
• XUJGAWJCUSXSNC-UHFFFAOYSA-N 2-[3-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]azetidin-1-yl]ethanol Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(N=C2)C2CN(CCO)C2)C3=N1 XUJGAWJCUSXSNC-UHFFFAOYSA-N 0.000 claims description 2
• NAGHPTITPJFKLN-UHFFFAOYSA-N 2-[3-hydroxy-4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]-n,n-dimethylacetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2C(CN(CC(=O)N(C)C)CC2)O)C3=N1 NAGHPTITPJFKLN-UHFFFAOYSA-N 0.000 claims description 2
• XGQMJABNHZKYEN-UHFFFAOYSA-N 2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydro-[1]benzoxepino[5,4-c]pyrazol-8-yl]pyrazol-1-yl]ethanol Chemical compound CC(C)N1N=CN=C1N1N=C2C3=CC=C(C4=CN(CCO)N=C4)C=C3OCCC2=C1 XGQMJABNHZKYEN-UHFFFAOYSA-N 0.000 claims description 2
• LAJOOHPVYUKEEJ-UHFFFAOYSA-N 2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]ethanol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CCO)CC2)C3=N1 LAJOOHPVYUKEEJ-UHFFFAOYSA-N 0.000 claims description 2
• OXQIENYMRYNJKX-UHFFFAOYSA-N 2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]ethanol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(CCO)N=C2)C3=N1 OXQIENYMRYNJKX-UHFFFAOYSA-N 0.000 claims description 2
• LAENNKGRGNADTP-UHFFFAOYSA-N 2-[4-[2-(5-amino-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]imidazol-1-yl]ethanol Chemical compound CC(C)N1N=C(N)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2N=CN(CCO)C=2)C3=N1 LAENNKGRGNADTP-UHFFFAOYSA-N 0.000 claims description 2
• DDRRVMBAHALKPP-UHFFFAOYSA-N 2-[4-[2-(5-methyl-1h-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]ethanol Chemical compound CC1=NNC(C=2N=C3C4=CC=C(C=C4OCCN3C=2)C2=CN(CCO)N=C2)=N1 DDRRVMBAHALKPP-UHFFFAOYSA-N 0.000 claims description 2
• HRWITLQTGQUEKB-UHFFFAOYSA-N 2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]-n-propan-2-ylacetamide Chemical compound C1CN(CC(=O)NC(C)C)CCC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=C(C)N=2)C(C)C)CCO2)C2=C1 HRWITLQTGQUEKB-UHFFFAOYSA-N 0.000 claims description 2
• GTQBUIYKAXUNFW-UHFFFAOYSA-N 2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]acetamide Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CC(N)=O)CC2)C3=N1 GTQBUIYKAXUNFW-UHFFFAOYSA-N 0.000 claims description 2
• YDTNRMHDGKBXJK-UHFFFAOYSA-N 2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]ethanol Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CCO)CC2)C3=N1 YDTNRMHDGKBXJK-UHFFFAOYSA-N 0.000 claims description 2
• SRVFZFLOOADICX-UHFFFAOYSA-N 2-[4-[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)CC(F)(F)F)CCO2)C2=C1 SRVFZFLOOADICX-UHFFFAOYSA-N 0.000 claims description 2
• OAYDGVMSCLSOOI-UHFFFAOYSA-N 2-[4-[2-[2-(2,4-difluorophenyl)-1,2,4-triazol-3-yl]-4,5-dihydro-[1]benzoxepino[5,4-c]pyrazol-9-yl]piperidin-1-yl]acetamide Chemical compound C1CN(CC(=O)N)CCC1C1=CC=C(OCCC=2C3=NN(C=2)C=2N(N=CN=2)C=2C(=CC(F)=CC=2)F)C3=C1 OAYDGVMSCLSOOI-UHFFFAOYSA-N 0.000 claims description 2
• FGWCNDKKYBUBSG-UHFFFAOYSA-N 2-[4-[2-[2-(2,4-difluorophenyl)-1,2,4-triazol-3-yl]-4,5-dihydro-[1]benzoxepino[5,4-c]pyrazol-9-yl]piperidin-1-yl]ethanol Chemical compound C1CN(CCO)CCC1C1=CC=C(OCCC=2C3=NN(C=2)C=2N(N=CN=2)C=2C(=CC(F)=CC=2)F)C3=C1 FGWCNDKKYBUBSG-UHFFFAOYSA-N 0.000 claims description 2
• HICACBRDNPLTCW-UHFFFAOYSA-N 2-[4-[2-[5-(methoxymethyl)-2-propan-2-yl-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]acetamide Chemical compound CC(C)N1N=C(COC)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CC(N)=O)CC2)C3=N1 HICACBRDNPLTCW-UHFFFAOYSA-N 0.000 claims description 2
• AMQFJPQCXKXWHL-UHFFFAOYSA-N 2-[5-(methoxymethyl)-2-propan-2-yl-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=C(COC)N=C1C1=CN(CCOC=2C3=CC=CC=2)C3=N1 AMQFJPQCXKXWHL-UHFFFAOYSA-N 0.000 claims description 2
• HVDBJKLIPIANMW-UHFFFAOYSA-N 2-[5-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]imidazol-1-yl]ethanol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2N(C=NC=2)CCO)C3=N1 HVDBJKLIPIANMW-UHFFFAOYSA-N 0.000 claims description 2
• GFOJWGYPLGSKOJ-UHFFFAOYSA-N 2-cyclopropyl-2-[[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]oxy]acetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(OC(C4CC4)C(N)=O)C=2)C3=N1 GFOJWGYPLGSKOJ-UHFFFAOYSA-N 0.000 claims description 2
• HHYCTJGSSRDWCS-UHFFFAOYSA-N 2-hydroxy-1-[3-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepin-9-yl]azetidin-1-yl]ethanone Chemical compound CC(C)N1N=CN=C1C1=NN2C3=CC(C4CN(C4)C(=O)CO)=CC=C3OCCC2=C1 HHYCTJGSSRDWCS-UHFFFAOYSA-N 0.000 claims description 2
• KYQHZWOECHMXAX-UHFFFAOYSA-N 2-hydroxy-1-[4-[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepin-9-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CO)CCC1C1=CC=C(OCCC=2N3N=C(C=2)C=2N(N=CN=2)CC(F)(F)F)C3=C1 KYQHZWOECHMXAX-UHFFFAOYSA-N 0.000 claims description 2
• MXDKMKYBNPFLJT-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]propan-1-one Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CC2)C(=O)C(C)(C)O)C3=N1 MXDKMKYBNPFLJT-UHFFFAOYSA-N 0.000 claims description 2
• JFOFKJVQOSQEGN-UHFFFAOYSA-N 2-methyl-1-[2-methyl-4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]imidazol-1-yl]propan-2-ol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2N=C(C)N(CC(C)(C)O)C=2)C3=N1 JFOFKJVQOSQEGN-UHFFFAOYSA-N 0.000 claims description 2
• RFSCGOIKLNVVNR-UHFFFAOYSA-N 2-methyl-1-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]imidazol-1-yl]propan-2-ol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2N=CN(CC(C)(C)O)C=2)C3=N1 RFSCGOIKLNVVNR-UHFFFAOYSA-N 0.000 claims description 2
• IAPGUUHIBSIFNT-UHFFFAOYSA-N 2-methyl-1-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]propan-2-ol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CC(C)(C)O)CC2)C3=N1 IAPGUUHIBSIFNT-UHFFFAOYSA-N 0.000 claims description 2
• PRHJVUJDDAUMOZ-UHFFFAOYSA-N 2-methyl-1-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]imidazol-1-yl]propan-2-ol Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2N=CN(CC(C)(C)O)C=2)C3=N1 PRHJVUJDDAUMOZ-UHFFFAOYSA-N 0.000 claims description 2
• ZVIONAUHZKUKOR-UHFFFAOYSA-N 2-methyl-1-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]propan-2-ol Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(CC(C)(C)O)N=C2)C3=N1 ZVIONAUHZKUKOR-UHFFFAOYSA-N 0.000 claims description 2
• ANOJWKHOJDYCCX-UHFFFAOYSA-N 2-methyl-1-[5-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]-1h-imidazol-2-yl]propan-2-ol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2NC(CC(C)(C)O)=NC=2)C3=N1 ANOJWKHOJDYCCX-UHFFFAOYSA-N 0.000 claims description 2
• QOHVGYSJCCLWPM-UHFFFAOYSA-N 2-methyl-2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]propanamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(N=C2)C(C)(C)C(N)=O)C3=N1 QOHVGYSJCCLWPM-UHFFFAOYSA-N 0.000 claims description 2
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• ILOMLTAEBJUVGT-UHFFFAOYSA-N 2-methyl-2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]propanamide Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CC2)C(C)(C)C(N)=O)C3=N1 ILOMLTAEBJUVGT-UHFFFAOYSA-N 0.000 claims description 2
• DFLUNRVFVAAWSG-UHFFFAOYSA-N 2-methyl-2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]propanoic acid Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(N=C2)C(C)(C)C(O)=O)C3=N1 DFLUNRVFVAAWSG-UHFFFAOYSA-N 0.000 claims description 2
• VHXXSAZIOFDBMI-UHFFFAOYSA-N 3-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepin-10-yl)pyridin-2(1h)-one Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC(=NC=2)C=2C(NC=CC=2)=O)C3=N1 VHXXSAZIOFDBMI-UHFFFAOYSA-N 0.000 claims description 2
• XILYGSAROZNXNT-UHFFFAOYSA-N 3-methyl-2-[[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]oxy]butanamide Chemical compound C=1N2CCOC3=CC(OC(C(C)C)C(N)=O)=CC=C3C2=NC=1C1=NC=NN1CC(F)(F)F XILYGSAROZNXNT-UHFFFAOYSA-N 0.000 claims description 2
• VKMQIABSPCWGQV-UHFFFAOYSA-N 4-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,2-f][1,4]oxazepin-9-yl)piperazin-2-one Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(N=2)N2CC(=O)NCC2)C3=N1 VKMQIABSPCWGQV-UHFFFAOYSA-N 0.000 claims description 2
• QXNTUVPYBHLTOP-UHFFFAOYSA-N 4-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepin-10-yl)piperazin-2-one Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC(=NC=2)N2CC(=O)NCC2)C3=N1 QXNTUVPYBHLTOP-UHFFFAOYSA-N 0.000 claims description 2
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• RHNCYWGPWRFBRI-UHFFFAOYSA-N 5-(10-phenyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-2-yl)-1-propan-2-yl-1,2,4-triazol-3-amine Chemical compound CC(C)N1N=C(N)N=C1C1=CN(CCOC=2C3=CC(=CC=2)C=2C=CC=CC=2)C3=N1 RHNCYWGPWRFBRI-UHFFFAOYSA-N 0.000 claims description 2
• GJFCIESGVCWMDT-UHFFFAOYSA-N 5-(5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-2-yl)-1-propan-2-yl-1,2,4-triazol-3-amine Chemical compound CC(C)N1N=C(N)N=C1C1=CN(CCOC=2C3=CC=CC=2)C3=N1 GJFCIESGVCWMDT-UHFFFAOYSA-N 0.000 claims description 2
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• FGANCDHKJAIPJV-UHFFFAOYSA-N 5-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrimidin-2-amine Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2C=NC(N)=NC=2)C3=N1 FGANCDHKJAIPJV-UHFFFAOYSA-N 0.000 claims description 2
• XSYUTUKYODWGOQ-UHFFFAOYSA-N 8-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)-3,8-diazabicyclo[3.2.1]octan-2-one Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(C=2)N2C4CCC2CNC4=O)C3=N1 XSYUTUKYODWGOQ-UHFFFAOYSA-N 0.000 claims description 2
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• QOJWFTNYMZCBEK-UHFFFAOYSA-N 9-(2-ethylphenyl)-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CCC1=CC=CC=C1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=C1 QOJWFTNYMZCBEK-UHFFFAOYSA-N 0.000 claims description 2
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• GXPQJKFNZQXNLM-UHFFFAOYSA-N 9-(4-chlorophenyl)-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2C=CC(Cl)=CC=2)C3=N1 GXPQJKFNZQXNLM-UHFFFAOYSA-N 0.000 claims description 2
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• POUUCQHARUWIBM-UHFFFAOYSA-N 9-(difluoromethoxy)-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(OC(F)F)C=2)C3=N1 POUUCQHARUWIBM-UHFFFAOYSA-N 0.000 claims description 2
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• NTOPVOFAXHFMIW-UHFFFAOYSA-N 9-[1-(2-methoxyethyl)piperidin-4-yl]-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound C1CN(CCOC)CCC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=C1 NTOPVOFAXHFMIW-UHFFFAOYSA-N 0.000 claims description 2
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• UXNCNBABSKOOFR-UHFFFAOYSA-N 9-chloro-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydro-[1,2,4]triazolo[1,5-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=NN2CCOC3=CC(Cl)=CC=C3C2=N1 UXNCNBABSKOOFR-UHFFFAOYSA-N 0.000 claims description 2
• AXZLZNQSEHKNQX-UHFFFAOYSA-N 9-ethyl-2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound C=1N2CCOC3=CC(CC)=CC=C3C2=NC=1C1=NC(C)=NN1C(C)C AXZLZNQSEHKNQX-UHFFFAOYSA-N 0.000 claims description 2
• OGJYNZYWHJMRKL-UHFFFAOYSA-N 9-piperidin-4-yl-2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepine Chemical compound FC(F)(F)CN1N=CN=C1C1=NN2C3=CC(C4CCNCC4)=CC=C3OCCC2=C1 OGJYNZYWHJMRKL-UHFFFAOYSA-N 0.000 claims description 2
• OJAOSPGMWPNXQM-UHFFFAOYSA-N [1,2,4]triazolo[1,5-d][1,4]oxazepine Chemical compound N=1C=NN2C=COC=CC21 OJAOSPGMWPNXQM-UHFFFAOYSA-N 0.000 claims description 2
• WHTXMXLGTDUKGF-UHFFFAOYSA-N [2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]methyl carbamate Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(COC(N)=O)C=2)C3=N1 WHTXMXLGTDUKGF-UHFFFAOYSA-N 0.000 claims description 2
• MMPUDTBKRIMRRU-UHFFFAOYSA-N [3-amino-1-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]azetidin-3-yl]methanol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)N2CC(N)(CO)C2)C3=N1 MMPUDTBKRIMRRU-UHFFFAOYSA-N 0.000 claims description 2
• USMLUHAPDOPVGW-UHFFFAOYSA-N [4-(2-hydroxyethyl)piperazin-1-yl]-[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-10-yl]methanone Chemical compound C1CN(CCO)CCN1C(=O)C1=CC=C(OCCN2C3=NC(=C2)C=2N(N=CN=2)CC(F)(F)F)C3=C1 USMLUHAPDOPVGW-UHFFFAOYSA-N 0.000 claims description 2
• FEFGNEFROIESEL-UHFFFAOYSA-N [4-(2-hydroxypropan-2-yl)piperidin-1-yl]-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-10-yl]methanone Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC(=CC=2)C(=O)N2CCC(CC2)C(C)(C)O)C3=N1 FEFGNEFROIESEL-UHFFFAOYSA-N 0.000 claims description 2
• VALZSZJVEFACEZ-UHFFFAOYSA-N azetidine-3-carboxamide Chemical compound NC(=O)C1CNC1 VALZSZJVEFACEZ-UHFFFAOYSA-N 0.000 claims description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
• ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 2
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 2
• LFRUHWPPVWXPGM-UHFFFAOYSA-N morpholin-4-yl-[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-10-yl]methanone Chemical compound FC(F)(F)CN1N=CN=C1C1=CN(CCOC=2C3=CC(=CC=2)C(=O)N2CCOCC2)C3=N1 LFRUHWPPVWXPGM-UHFFFAOYSA-N 0.000 claims description 2
• YPSPPJRTCRMQGD-UHFFFAOYSA-N morpholine-3-carboxamide Chemical compound NC(=O)C1COCCN1 YPSPPJRTCRMQGD-UHFFFAOYSA-N 0.000 claims description 2
• IBKXOWUBGLAQQS-UHFFFAOYSA-N n,n-diethyl-2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]ethanamine Chemical compound C1=NN(CCN(CC)CC)C=C1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=C1 IBKXOWUBGLAQQS-UHFFFAOYSA-N 0.000 claims description 2
• XHPJYHAOHAZQDQ-UHFFFAOYSA-N n,n-dimethyl-2-[3-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]azetidin-1-yl]acetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CN(CC(=O)N(C)C)C2)C3=N1 XHPJYHAOHAZQDQ-UHFFFAOYSA-N 0.000 claims description 2
• OQLXYYZBHASOHB-UHFFFAOYSA-N n,n-dimethyl-2-[3-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]azetidin-1-yl]ethanesulfonamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CN(CCS(=O)(=O)N(C)C)C2)C3=N1 OQLXYYZBHASOHB-UHFFFAOYSA-N 0.000 claims description 2
• ATRCTDPONUWJEO-UHFFFAOYSA-N n,n-dimethyl-2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]acetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CC(=O)N(C)C)CC2)C3=N1 ATRCTDPONUWJEO-UHFFFAOYSA-N 0.000 claims description 2
• AGXQWNOOVLFZKI-UHFFFAOYSA-N n,n-dimethyl-2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]ethanesulfonamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CCS(=O)(=O)N(C)C)CC2)C3=N1 AGXQWNOOVLFZKI-UHFFFAOYSA-N 0.000 claims description 2
• KRAWCAAGHVLCNZ-UHFFFAOYSA-N n,n-dimethyl-2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]acetamide Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CC(=O)N(C)C)CC2)C3=N1 KRAWCAAGHVLCNZ-UHFFFAOYSA-N 0.000 claims description 2
• CJAIQIDHBRBRII-UHFFFAOYSA-N n,n-dimethyl-5-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrimidin-2-amine Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2C=NC(=NC=2)N(C)C)C3=N1 CJAIQIDHBRBRII-UHFFFAOYSA-N 0.000 claims description 2
• XVXMKRMIMSZVEK-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)-2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carboxamide Chemical compound N1=C2C3=CC(C(=O)NC(C)(CO)C)=CC=C3OCCN2C=C1C1=NC=NN1CC(F)(F)F XVXMKRMIMSZVEK-UHFFFAOYSA-N 0.000 claims description 2
• CVUKJRIWOWTHNY-UHFFFAOYSA-N n-(2-methylsulfonylethyl)-2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carboxamide Chemical compound N1=C2C3=CC(C(=O)NCCS(=O)(=O)C)=CC=C3OCCN2C=C1C1=NC=NN1CC(F)(F)F CVUKJRIWOWTHNY-UHFFFAOYSA-N 0.000 claims description 2
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
• LFEMQJSGEOIQCV-UHFFFAOYSA-N n-(azetidin-3-yl)-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepine-9-carboxamide Chemical compound CC(C)N1N=CN=C1C1=NN2C3=CC(C(=O)NC4CNC4)=CC=C3OCCC2=C1 LFEMQJSGEOIQCV-UHFFFAOYSA-N 0.000 claims description 2
• IGDKXOFEPZFRJB-UHFFFAOYSA-N n-[(3-aminooxetan-3-yl)methyl]-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-amine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(NCC4(N)COC4)C=2)C3=N1 IGDKXOFEPZFRJB-UHFFFAOYSA-N 0.000 claims description 2
• SPZYHHNZALRYIU-UHFFFAOYSA-N n-[5-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyridin-2-yl]acetamide Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2C=NC(NC(C)=O)=CC=2)C3=N1 SPZYHHNZALRYIU-UHFFFAOYSA-N 0.000 claims description 2
• HMVIBBLSJJVZPI-UHFFFAOYSA-N n-ethyl-2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]acetamide Chemical compound C1CN(CC(=O)NCC)CCC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=C(C)N=2)C(C)C)CCO2)C2=C1 HMVIBBLSJJVZPI-UHFFFAOYSA-N 0.000 claims description 2
• ZLFLDVDGVSPUGA-UHFFFAOYSA-N n-methyl-2-[3-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]azetidin-1-yl]acetamide Chemical compound C1N(CC(=O)NC)CC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=C1 ZLFLDVDGVSPUGA-UHFFFAOYSA-N 0.000 claims description 2
• SEZRPZYUVONUSX-UHFFFAOYSA-N n-methyl-2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]acetamide Chemical compound C1CN(CC(=O)NC)CCC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=C1 SEZRPZYUVONUSX-UHFFFAOYSA-N 0.000 claims description 2
• RMBWBNILCGZTRS-UHFFFAOYSA-N n-methyl-2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]acetamide Chemical compound C1CN(CC(=O)NC)CCC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=C(C)N=2)C(C)C)CCO2)C2=C1 RMBWBNILCGZTRS-UHFFFAOYSA-N 0.000 claims description 2
• WCNYAGDVKYYDEZ-UHFFFAOYSA-N n-propan-2-yl-2-[3-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]azetidin-1-yl]acetamide Chemical compound C1N(CC(=O)NC(C)C)CC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=C1 WCNYAGDVKYYDEZ-UHFFFAOYSA-N 0.000 claims description 2
• NXRKDDRTZGEJGI-UHFFFAOYSA-N n-propan-2-yl-2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]acetamide Chemical compound C1CN(CC(=O)NC(C)C)CCC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=C1 NXRKDDRTZGEJGI-UHFFFAOYSA-N 0.000 claims description 2
• NMAJAMPLNJSDFL-UHFFFAOYSA-N n-tert-butyl-2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]acetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CC(=O)NC(C)(C)C)CC2)C3=N1 NMAJAMPLNJSDFL-UHFFFAOYSA-N 0.000 claims description 2
• BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims description 2
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 2
• IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 2
• BRYCUMKDWMEGMK-UHFFFAOYSA-N piperazine-2-carboxamide Chemical compound NC(=O)C1CNCCN1 BRYCUMKDWMEGMK-UHFFFAOYSA-N 0.000 claims description 2
• BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 235000019260 propionic acid Nutrition 0.000 claims description 2
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 2
• DATJETPTDKFEEF-UHFFFAOYSA-N pyrrolidine-3-carbonitrile Chemical compound N#CC1CCNC1 DATJETPTDKFEEF-UHFFFAOYSA-N 0.000 claims description 2
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
• CRVWCMVQQHEUGU-UHFFFAOYSA-N 2-(2-propan-2-yl-1,2,4-triazol-3-yl)-10-(1h-pyrazol-4-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC(=CC=2)C2=CNN=C2)C3=N1 CRVWCMVQQHEUGU-UHFFFAOYSA-N 0.000 claims 2
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
• ORFFVCGJIJWIQB-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C(=O)NC(C)(C)CO)C3=N1 ORFFVCGJIJWIQB-UHFFFAOYSA-N 0.000 claims 2
• NHCSOUAODWJXJW-UHFFFAOYSA-N n-methyl-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxamide Chemical compound C=1N2CCOC3=CC(C(=O)NC)=CC=C3C2=NC=1C1=NC=NN1C(C)C NHCSOUAODWJXJW-UHFFFAOYSA-N 0.000 claims 2
• 125000004434 sulfur atom Chemical group 0.000 claims 2
• VJOZXXWCUPTTMC-NSHDSACASA-N (2s)-2-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yloxy)propanamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(O[C@@H](C)C(N)=O)C=2)C3=N1 VJOZXXWCUPTTMC-NSHDSACASA-N 0.000 claims 1
• OXCSFUYZGQVPBC-AWEZNQCLSA-N (2s)-2-[[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]oxy]butanamide Chemical compound C=1N2CCOC3=CC(O[C@@H](CC)C(N)=O)=CC=C3C2=NC=1C1=NC=NN1CC(F)(F)F OXCSFUYZGQVPBC-AWEZNQCLSA-N 0.000 claims 1
• KPELVEYHYGPSHK-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepin-9-yl]methanone Chemical compound CC(C)N1N=CN=C1C1=NN2C3=CC(C(=O)N4CCC(O)CC4)=CC=C3OCCC2=C1 KPELVEYHYGPSHK-UHFFFAOYSA-N 0.000 claims 1
• RZYGTZLABJBWCO-UHFFFAOYSA-N 1-[2-[[4-[2-(2,4-difluorophenyl)-1,2,4-triazol-3-yl]-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-12-yl]amino]ethyl]pyrrolidin-2-one Chemical compound FC1=CC(F)=CC=C1N1C(C=2N=C3C4=CN=C(NCCN5C(CCC5)=O)C=C4OCCN3C=2)=NC=N1 RZYGTZLABJBWCO-UHFFFAOYSA-N 0.000 claims 1
• KXLBWCPSWZPNLL-UHFFFAOYSA-N 2-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yloxy)-2-methylpropanamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(OC(C)(C)C(N)=O)C=2)C3=N1 KXLBWCPSWZPNLL-UHFFFAOYSA-N 0.000 claims 1
• GBIFGRFSXJUSHK-UHFFFAOYSA-N 2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carboxamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC(=CC=2)C(N)=O)C3=N1 GBIFGRFSXJUSHK-UHFFFAOYSA-N 0.000 claims 1
• NVBXKDJDNDPTJH-UHFFFAOYSA-N 2-(4-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)piperazin-1-yl)acetamide Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(C=2)N2CCN(CC(N)=O)CC2)C3=N1 NVBXKDJDNDPTJH-UHFFFAOYSA-N 0.000 claims 1
• IUNJEPPTIHCMCO-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-9-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(CCN4CCOCC4)N=C2)C3=N1 IUNJEPPTIHCMCO-UHFFFAOYSA-N 0.000 claims 1
• YOMAFTZFXGTVNA-UHFFFAOYSA-N 2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-ol Chemical compound C=1N2CCOC3=CC(O)=CC=C3C2=NC=1C1=NC=NN1CC(F)(F)F YOMAFTZFXGTVNA-UHFFFAOYSA-N 0.000 claims 1
• IHGUZVPHTSOIJR-UHFFFAOYSA-N 2-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]acetamide Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(CC(N)=O)C=2)C3=N1 IHGUZVPHTSOIJR-UHFFFAOYSA-N 0.000 claims 1
• VDFMSHUPXIYJPS-UHFFFAOYSA-N 2-[3-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydro-[1]benzoxepino[5,4-c]pyrazol-8-yl]azetidin-1-yl]acetamide Chemical compound CC(C)N1N=CN=C1N1N=C2C3=CC=C(C4CN(CC(N)=O)C4)C=C3OCCC2=C1 VDFMSHUPXIYJPS-UHFFFAOYSA-N 0.000 claims 1
• UJTRISSJVIBVTH-UHFFFAOYSA-N 2-[3-[2-[2-(2,4-difluorophenyl)-1,2,4-triazol-3-yl]-4,5-dihydro-[1]benzoxepino[5,4-c]pyrazol-8-yl]azetidin-1-yl]ethanol Chemical compound C1N(CCO)CC1C1=CC=C(C=2C(=CN(N=2)C=2N(N=CN=2)C=2C(=CC(F)=CC=2)F)CCO2)C2=C1 UJTRISSJVIBVTH-UHFFFAOYSA-N 0.000 claims 1
• SXKKNZHUYVNGIA-UHFFFAOYSA-N 2-[4-[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepin-9-yl]piperidin-1-yl]acetamide Chemical compound C1CN(CC(=O)N)CCC1C1=CC=C(OCCC=2N3N=C(C=2)C=2N(N=CN=2)CC(F)(F)F)C3=C1 SXKKNZHUYVNGIA-UHFFFAOYSA-N 0.000 claims 1
• NYANBWPIMAKEHY-UHFFFAOYSA-N 2-[4-[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepin-9-yl]piperidin-1-yl]ethanol Chemical compound C1CN(CCO)CCC1C1=CC=C(OCCC=2N3N=C(C=2)C=2N(N=CN=2)CC(F)(F)F)C3=C1 NYANBWPIMAKEHY-UHFFFAOYSA-N 0.000 claims 1
• RDADTGAFKRSDFK-UHFFFAOYSA-N 2-[4-[[2-[2-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepin-9-yl]methyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1CC1=CC=C(OCCC=2N3N=C(C=2)C=2N(N=CN=2)CC(F)(F)F)C3=C1 RDADTGAFKRSDFK-UHFFFAOYSA-N 0.000 claims 1
• MTOMSLSDTNJGJL-UHFFFAOYSA-N 2-hydroxy-1-[4-[[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepin-9-yl]methyl]piperazin-1-yl]ethanone Chemical compound CC(C)N1N=CN=C1C1=NN2C3=CC(CN4CCN(CC4)C(=O)CO)=CC=C3OCCC2=C1 MTOMSLSDTNJGJL-UHFFFAOYSA-N 0.000 claims 1
• NXQXBDJBOUHNDB-UHFFFAOYSA-N 2-methyl-1-[4-[2-(1-propan-2-ylimidazol-2-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]propan-2-ol Chemical compound CC(C)N1C=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(CC(C)(C)O)N=C2)C3=N1 NXQXBDJBOUHNDB-UHFFFAOYSA-N 0.000 claims 1
• DGVWCVAGZPHTCH-UHFFFAOYSA-N 4-(2-(1-isopropyl-1h-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)piperazin-2-one Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CN=C(C=2)N2CC(=O)NCC2)C3=N1 DGVWCVAGZPHTCH-UHFFFAOYSA-N 0.000 claims 1
• WRZVRORDUUAEOM-UHFFFAOYSA-N 9-(1-isopropyl-1h-pyrazol-5-yl)-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-3-carboxamide Chemical compound CC(C)N1N=CC=C1C1=CN2C3=NC=C(C(N)=O)C=C3OCCC2=N1 WRZVRORDUUAEOM-UHFFFAOYSA-N 0.000 claims 1
• YMTJBSBIOWRHBO-UHFFFAOYSA-N 9-(2-methyl-1h-imidazol-5-yl)-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2NC(C)=NC=2)C3=N1 YMTJBSBIOWRHBO-UHFFFAOYSA-N 0.000 claims 1
• JMMJKPPUVYDRDI-UHFFFAOYSA-N 9-(azetidin-3-yl)-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=NN2C3=CC(C4CNC4)=CC=C3OCCC2=C1 JMMJKPPUVYDRDI-UHFFFAOYSA-N 0.000 claims 1
• KWJPPHIQRJNGES-UHFFFAOYSA-N 9-[1-(2-methylsulfonylethyl)azetidin-3-yl]-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CN(CCS(C)(=O)=O)C2)C3=N1 KWJPPHIQRJNGES-UHFFFAOYSA-N 0.000 claims 1
• XSFGIXJCVYTQHD-UHFFFAOYSA-N 9-[1-(2-methylsulfonylethyl)piperidin-4-yl]-2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C2CCN(CCS(C)(=O)=O)CC2)C3=N1 XSFGIXJCVYTQHD-UHFFFAOYSA-N 0.000 claims 1
• NBSBIDFGRFTDQH-UHFFFAOYSA-N [2-(2-propan-2-yl-1,2,4-triazol-3-yl)-4,5-dihydropyrazolo[5,1-d][1,5]benzoxazepin-9-yl]-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]methanone Chemical compound CC(C)N1N=CN=C1C1=NN2C3=CC(C(=O)N4CCN(CC(F)(F)F)CC4)=CC=C3OCCC2=C1 NBSBIDFGRFTDQH-UHFFFAOYSA-N 0.000 claims 1
• WOUOOAHMLTWTAH-UHFFFAOYSA-N n,2-dimethyl-2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]piperidin-1-yl]propanamide Chemical compound C1CN(C(C)(C)C(=O)NC)CCC1C1=CC=C(C=2N(C=C(N=2)C=2N(N=CN=2)C(C)C)CCO2)C2=C1 WOUOOAHMLTWTAH-UHFFFAOYSA-N 0.000 claims 1
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