KR20120047939A - 융합된 이미다졸, 및 기생충 질환, 예컨대 말라리아의 치료를 위한 상기 화합물을 포함하는 조성물 - Google Patents
융합된 이미다졸, 및 기생충 질환, 예컨대 말라리아의 치료를 위한 상기 화합물을 포함하는 조성물 Download PDFInfo
- Publication number
- KR20120047939A KR20120047939A KR1020127003375A KR20127003375A KR20120047939A KR 20120047939 A KR20120047939 A KR 20120047939A KR 1020127003375 A KR1020127003375 A KR 1020127003375A KR 20127003375 A KR20127003375 A KR 20127003375A KR 20120047939 A KR20120047939 A KR 20120047939A
- Authority
- KR
- South Korea
- Prior art keywords
- amino
- fluorophenyl
- imidazo
- pyrazin
- methylphenyl
- Prior art date
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- 201000004792 malaria Diseases 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title description 51
- 238000011282 treatment Methods 0.000 title description 19
- 208000030852 Parasitic disease Diseases 0.000 title description 7
- 150000002460 imidazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 266
- 238000000034 method Methods 0.000 claims abstract description 48
- -1 substituted Chemical class 0.000 claims description 190
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 132
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 131
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 112
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- 229910052739 hydrogen Inorganic materials 0.000 claims description 76
- 239000001257 hydrogen Substances 0.000 claims description 74
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 38
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 150000003254 radicals Chemical class 0.000 claims description 31
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- WGKXETUOZHHSRI-UHFFFAOYSA-N 2-amino-1-[3-(3,4-difluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C(F)=C1 WGKXETUOZHHSRI-UHFFFAOYSA-N 0.000 claims description 13
- BUPRVECGWBHCQV-UHFFFAOYSA-N 2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC=C(F)C=C1 BUPRVECGWBHCQV-UHFFFAOYSA-N 0.000 claims description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000003386 piperidinyl group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000003430 antimalarial agent Substances 0.000 claims description 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims description 6
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 6
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 208000024891 symptom Diseases 0.000 claims description 5
- XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 claims description 4
- KFSKTWYDIHJITF-UHFFFAOYSA-N 2-amino-1-[3-(4-chloroanilino)-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC=C(Cl)C=C1 KFSKTWYDIHJITF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229960004191 artemisinin Drugs 0.000 claims description 4
- 229930101531 artemisinin Natural products 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 229940043355 kinase inhibitor Drugs 0.000 claims description 4
- 229960001962 mefloquine Drugs 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 claims description 3
- UWJIGFUMWLBZAJ-UHFFFAOYSA-N 1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-hydroxyethanone Chemical compound C1N(C(=O)CO)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1 UWJIGFUMWLBZAJ-UHFFFAOYSA-N 0.000 claims description 3
- QWTDABCVIVKPKT-UHFFFAOYSA-N 2-(3-methylphenyl)-n-(4-methylphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-amine Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(C)C=CC=2)N=C2N1CCNC2 QWTDABCVIVKPKT-UHFFFAOYSA-N 0.000 claims description 3
- XOTIYMSEBVGTAS-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(4-methylphenyl)imidazo[1,2-a]pyrazin-3-amine Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1C=CN=C2 XOTIYMSEBVGTAS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
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- 125000004122 cyclic group Chemical group 0.000 claims description 3
- SXYIRMFQILZOAM-HVNFFKDJSA-N dihydroartemisinin methyl ether Chemical compound C1C[C@H]2[C@H](C)CC[C@H]3[C@@H](C)[C@@H](OC)O[C@H]4[C@]32OO[C@@]1(C)O4 SXYIRMFQILZOAM-HVNFFKDJSA-N 0.000 claims description 3
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- 230000002401 inhibitory effect Effects 0.000 claims description 3
- PNUNNNKTJAYRDW-UHFFFAOYSA-N n,2-bis(4-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-amine Chemical compound C1=CC(F)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCNC2 PNUNNNKTJAYRDW-UHFFFAOYSA-N 0.000 claims description 3
- HQFFCJXXPZDRJY-UHFFFAOYSA-N n,2-bis(4-fluorophenyl)imidazo[1,2-a]pyrazin-3-amine Chemical compound C1=CC(F)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1C=CN=C2 HQFFCJXXPZDRJY-UHFFFAOYSA-N 0.000 claims description 3
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- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims description 3
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- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- HGZGANOZPYDWRC-UHFFFAOYSA-N (1-aminocyclobutyl)-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)C1(N)CCC1)C2 HGZGANOZPYDWRC-UHFFFAOYSA-N 0.000 claims description 2
- BCIPSVDKSFBIKP-UHFFFAOYSA-N (1-aminocyclohexyl)-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)C1(N)CCCCC1)C2 BCIPSVDKSFBIKP-UHFFFAOYSA-N 0.000 claims description 2
- WDGBSZVDSDOMAT-UHFFFAOYSA-N (1-aminocyclopentyl)-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)C1(N)CCCC1)C2 WDGBSZVDSDOMAT-UHFFFAOYSA-N 0.000 claims description 2
- ZFMHCMNSFVNNDD-UHFFFAOYSA-N (1-aminocyclopropyl)-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]methanone Chemical compound C1CN(C(=C(N=2)C=3C=CC(F)=CC=3)NC=3C=CC(F)=CC=3)C=2CN1C(=O)C1(N)CC1 ZFMHCMNSFVNNDD-UHFFFAOYSA-N 0.000 claims description 2
- IVFQUVZPOMUFBW-JOCHJYFZSA-N (2r)-1-[2-(3,4-difluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-hydroxy-3-methylbutan-1-one Chemical compound C1N(C(=O)[C@H](O)C(C)C)CCN2C1=NC(C=1C=C(F)C(F)=CC=1)=C2NC1=CC=C(C)C=C1 IVFQUVZPOMUFBW-JOCHJYFZSA-N 0.000 claims description 2
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- RTZOAPJWFRDBHI-FQEVSTJZSA-N (2s)-2-amino-1-[3-(4-chloroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-(1,3-thiazol-4-yl)propan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(Cl)=CC=2)CC1)C1=CSC=N1 RTZOAPJWFRDBHI-FQEVSTJZSA-N 0.000 claims description 2
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- RLMUJGOAERMWFV-QHCPKHFHSA-N (2s)-2-amino-1-[3-(4-chloroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-(4-fluorophenyl)propan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(Cl)=CC=2)CC1)C1=CC=C(F)C=C1 RLMUJGOAERMWFV-QHCPKHFHSA-N 0.000 claims description 2
- SDOQAKSDEIWMGS-DEOSSOPVSA-N (2s)-2-amino-1-[3-(4-chloroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-(4-methylphenyl)propan-1-one Chemical compound C1=CC(C)=CC=C1C[C@H](N)C(=O)N1CC2=NC(C=3C=CC(F)=CC=3)=C(NC=3C=CC(Cl)=CC=3)N2CC1 SDOQAKSDEIWMGS-DEOSSOPVSA-N 0.000 claims description 2
- RVAWPJMSOQMNSG-NRFANRHFSA-N (2s)-2-amino-1-[3-(4-chloroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-cyclobutylpropan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(Cl)=CC=2)CC1)C1CCC1 RVAWPJMSOQMNSG-NRFANRHFSA-N 0.000 claims description 2
- TZXDJTXNOYSOAF-FQEVSTJZSA-N (2s)-2-amino-1-[3-(4-chloroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-cyclopropylpropan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(Cl)=CC=2)CC1)C1CC1 TZXDJTXNOYSOAF-FQEVSTJZSA-N 0.000 claims description 2
- IYJAIBQIPFLOFM-FQEVSTJZSA-N (2s)-2-amino-1-[3-(4-chloroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-methylbutan-1-one Chemical compound C1N(C(=O)[C@@H](N)C(C)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(Cl)C=C1 IYJAIBQIPFLOFM-FQEVSTJZSA-N 0.000 claims description 2
- BGHKUFXNBCQSJL-FQEVSTJZSA-N (2s)-2-amino-1-[3-(4-chloroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-4-methylpentan-1-one Chemical compound C1N(C(=O)[C@@H](N)CC(C)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(Cl)C=C1 BGHKUFXNBCQSJL-FQEVSTJZSA-N 0.000 claims description 2
- TVKQASPLBDLNNX-ZDUSSCGKSA-N (2s)-2-amino-1-[3-(4-chloroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1N(C(=O)[C@@H](N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(Cl)C=C1 TVKQASPLBDLNNX-ZDUSSCGKSA-N 0.000 claims description 2
- HABZAFMSPVSAQV-QHCPKHFHSA-N (2s)-2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-(4-fluorophenyl)ethanone Chemical compound O=C([C@@H](N)C=1C=CC(F)=CC=1)N(C1)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1 HABZAFMSPVSAQV-QHCPKHFHSA-N 0.000 claims description 2
- NHCQFVNKWKAOPM-OAQYLSRUSA-N (2s)-2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3,3-dimethylbutan-1-one Chemical compound C1N(C(=O)[C@@H](N)C(C)(C)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1 NHCQFVNKWKAOPM-OAQYLSRUSA-N 0.000 claims description 2
- GXHGCHVLXLVIER-FQEVSTJZSA-N (2s)-2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-(1,3-thiazol-4-yl)propan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(F)=CC=2)CC1)C1=CSC=N1 GXHGCHVLXLVIER-FQEVSTJZSA-N 0.000 claims description 2
- ROKDYEBLQXXHGO-QHCPKHFHSA-N (2s)-2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-(4-fluorophenyl)propan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(F)=CC=2)CC1)C1=CC=C(F)C=C1 ROKDYEBLQXXHGO-QHCPKHFHSA-N 0.000 claims description 2
- XFJLDEIMUKXQJU-DEOSSOPVSA-N (2s)-2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-(4-methylphenyl)propan-1-one Chemical compound C1=CC(C)=CC=C1C[C@H](N)C(=O)N1CC2=NC(C=3C=CC(F)=CC=3)=C(NC=3C=CC(F)=CC=3)N2CC1 XFJLDEIMUKXQJU-DEOSSOPVSA-N 0.000 claims description 2
- SIYUXOXQDXHEDO-FQEVSTJZSA-N (2s)-2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-methylbutan-1-one Chemical compound C1N(C(=O)[C@@H](N)C(C)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1 SIYUXOXQDXHEDO-FQEVSTJZSA-N 0.000 claims description 2
- YUULYOUHULYCKJ-QHCPKHFHSA-N (2s)-2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-phenylpropan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(F)=CC=2)CC1)C1=CC=CC=C1 YUULYOUHULYCKJ-QHCPKHFHSA-N 0.000 claims description 2
- FPGHOOSHFDOJCG-FQEVSTJZSA-N (2s)-2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-4-methylpentan-1-one Chemical compound C1N(C(=O)[C@@H](N)CC(C)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1 FPGHOOSHFDOJCG-FQEVSTJZSA-N 0.000 claims description 2
- PLPBUDLQQFEQLJ-ZDUSSCGKSA-N (2s)-2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1N(C(=O)[C@@H](N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1 PLPBUDLQQFEQLJ-ZDUSSCGKSA-N 0.000 claims description 2
- ALFKGAUBJVTNRL-DEOSSOPVSA-N (2s)-2-amino-2-(4-fluorophenyl)-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H](N)C=1C=CC(F)=CC=1)C2 ALFKGAUBJVTNRL-DEOSSOPVSA-N 0.000 claims description 2
- VAYGKOSGJXUIEL-FQEVSTJZSA-N (2s)-2-amino-2-cyclopropyl-1-[3-(3,4-difluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1([C@H](N)C(=O)N2CC=3N(C(=C(N=3)C=3C=CC(F)=CC=3)NC=3C=C(F)C(F)=CC=3)CC2)CC1 VAYGKOSGJXUIEL-FQEVSTJZSA-N 0.000 claims description 2
- AUAUCCKZFDXRHJ-FQEVSTJZSA-N (2s)-2-amino-2-cyclopropyl-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1([C@H](N)C(=O)N2CC=3N(C(=C(N=3)C=3C=CC(F)=CC=3)NC=3C=CC(F)=CC=3)CC2)CC1 AUAUCCKZFDXRHJ-FQEVSTJZSA-N 0.000 claims description 2
- NTVXVMHVNXQFOC-SFHVURJKSA-N (2s)-2-amino-3,3,3-trifluoro-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1N(C(=O)[C@H](N)C(F)(F)F)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1 NTVXVMHVNXQFOC-SFHVURJKSA-N 0.000 claims description 2
- JNDBROPSFYFSST-DEOSSOPVSA-N (2s)-2-amino-3-(3,4-difluorophenyl)-1-[2-(3,4-difluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(F)C(F)=CC=2)N=C2N1CCN(C(=O)[C@@H](N)CC=1C=C(F)C(F)=CC=1)C2 JNDBROPSFYFSST-DEOSSOPVSA-N 0.000 claims description 2
- AJUPGRJARYIRTK-DEOSSOPVSA-N (2s)-2-amino-3-(3,4-difluorophenyl)-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H](N)CC=1C=C(F)C(F)=CC=1)C2 AJUPGRJARYIRTK-DEOSSOPVSA-N 0.000 claims description 2
- FGXXEONUVUTGJL-QHCPKHFHSA-N (2s)-2-amino-3-(3,4-difluorophenyl)-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(F)=CC=2)CC1)C1=CC=C(F)C(F)=C1 FGXXEONUVUTGJL-QHCPKHFHSA-N 0.000 claims description 2
- UVJLABVXEWXLKJ-DEOSSOPVSA-N (2s)-2-amino-3-(4-aminophenyl)-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H](N)CC=1C=CC(N)=CC=1)C2 UVJLABVXEWXLKJ-DEOSSOPVSA-N 0.000 claims description 2
- XDBITHUFCOEZQB-LJAQVGFWSA-N (2s)-2-amino-3-(4-fluorophenyl)-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@](C)(N)CC=1C=CC(F)=CC=1)C2 XDBITHUFCOEZQB-LJAQVGFWSA-N 0.000 claims description 2
- YJGKKNVZKHEXJF-DEOSSOPVSA-N (2s)-2-amino-3-(4-fluorophenyl)-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H](N)CC=1C=CC(F)=CC=1)C2 YJGKKNVZKHEXJF-DEOSSOPVSA-N 0.000 claims description 2
- XSDJIGIPZDDJQN-VWLOTQADSA-N (2s)-2-amino-3-[4-(aminomethyl)phenyl]-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H](N)CC=1C=CC(CN)=CC=1)C2 XSDJIGIPZDDJQN-VWLOTQADSA-N 0.000 claims description 2
- QCNDDGRGZBYLRB-QFIPXVFZSA-N (2s)-2-amino-3-cyclobutyl-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H](N)CC1CCC1)C2 QCNDDGRGZBYLRB-QFIPXVFZSA-N 0.000 claims description 2
- WNJWJTUDPOKQHN-NRFANRHFSA-N (2s)-2-amino-3-cyclobutyl-1-[3-(3,4-difluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=C(F)C(F)=CC=2)CC1)C1CCC1 WNJWJTUDPOKQHN-NRFANRHFSA-N 0.000 claims description 2
- BNSABHPMIMLIMS-NRFANRHFSA-N (2s)-2-amino-3-cyclobutyl-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(F)=CC=2)CC1)C1CCC1 BNSABHPMIMLIMS-NRFANRHFSA-N 0.000 claims description 2
- XQGGRSCSLPJEHO-NRFANRHFSA-N (2s)-2-amino-3-cyclopropyl-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H](N)CC1CC1)C2 XQGGRSCSLPJEHO-NRFANRHFSA-N 0.000 claims description 2
- PBFUSWVZKUDETH-FQEVSTJZSA-N (2s)-2-amino-3-cyclopropyl-1-[3-(3,4-difluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=C(F)C(F)=CC=2)CC1)C1CC1 PBFUSWVZKUDETH-FQEVSTJZSA-N 0.000 claims description 2
- WAZLJPNFUJYLON-FQEVSTJZSA-N (2s)-2-amino-3-cyclopropyl-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C([C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(F)=CC=2)CC1)C1CC1 WAZLJPNFUJYLON-FQEVSTJZSA-N 0.000 claims description 2
- UZDCWVMDAHGZTJ-VWLOTQADSA-N (2s)-2-cyclohexyl-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-hydroxyethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H](O)C1CCCCC1)C2 UZDCWVMDAHGZTJ-VWLOTQADSA-N 0.000 claims description 2
- RVXZKTQEKJIVHS-SANMLTNESA-N (2s)-2-ethoxy-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound C([C@H](OCC)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(C)=CC=2)CC1)C1=CC=C(O)C=C1 RVXZKTQEKJIVHS-SANMLTNESA-N 0.000 claims description 2
- PSYHIHKMWPYWKY-VWLOTQADSA-N (2s)-3-(4-chlorophenyl)-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-(methylamino)propan-1-one Chemical compound C([C@H](NC)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=CC(C)=CC=2)CC1)C1=CC=C(Cl)C=C1 PSYHIHKMWPYWKY-VWLOTQADSA-N 0.000 claims description 2
- BBSKLDIZTKLRRP-DEOSSOPVSA-N (2s)-3-cyclohexyl-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-hydroxypropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H](O)CC1CCCCC1)C2 BBSKLDIZTKLRRP-DEOSSOPVSA-N 0.000 claims description 2
- ZZQMTWLOAGMFQW-QKKBWIMNSA-N (2s,3s)-2-amino-1-[3-(3,4-difluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-methylpentan-1-one Chemical compound C1N(C(=O)[C@@H](N)[C@@H](C)CC)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C(F)=C1 ZZQMTWLOAGMFQW-QKKBWIMNSA-N 0.000 claims description 2
- XPEITXJTNMZOQR-QKKBWIMNSA-N (2s,3s)-2-amino-1-[3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-methylpentan-1-one Chemical compound C1N(C(=O)[C@@H](N)[C@@H](C)CC)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(Cl)C(F)=C1 XPEITXJTNMZOQR-QKKBWIMNSA-N 0.000 claims description 2
- GWMRNPJBHZMFAS-QYBDOPJKSA-N (2s,3s)-2-amino-1-[3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-phenylmethoxybutan-1-one Chemical compound O([C@@H](C)[C@H](N)C(=O)N1CC=2N(C(=C(N=2)C=2C=CC(F)=CC=2)NC=2C=C(F)C(Cl)=CC=2)CC1)CC1=CC=CC=C1 GWMRNPJBHZMFAS-QYBDOPJKSA-N 0.000 claims description 2
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- GBWIICLLLHZRTE-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(4-methylphenyl)-7-[(4-pyridin-4-ylphenyl)methyl]-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-3-amine Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(CC=1C=CC(=CC=1)C=1C=CN=CC=1)C2 GBWIICLLLHZRTE-UHFFFAOYSA-N 0.000 claims description 2
- CPVSRBHTNOWJLD-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(4-methylphenyl)-7-[[4-(4-methylpiperazin-1-yl)phenyl]methyl]-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-3-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1CN1CC2=NC(C=3C=CC(F)=CC=3)=C(NC=3C=CC(C)=CC=3)N2CC1 CPVSRBHTNOWJLD-UHFFFAOYSA-N 0.000 claims description 2
- VUJMEEMQVJBEEO-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(4-methylphenyl)imidazo[1,2-a]pyridin-3-amine Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1C=CC=C2 VUJMEEMQVJBEEO-UHFFFAOYSA-N 0.000 claims description 2
- BFYQCTQYPPPGBP-UHFFFAOYSA-N 2-(benzylamino)-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)CNCC=1C=CC=CC=1)C2 BFYQCTQYPPPGBP-UHFFFAOYSA-N 0.000 claims description 2
- JZXHFTXVDOGKLV-UHFFFAOYSA-N 2-(cyclopropylamino)-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)CNC1CC1)C2 JZXHFTXVDOGKLV-UHFFFAOYSA-N 0.000 claims description 2
- HNLJOUQXXSJJGA-UHFFFAOYSA-N 2-(cyclopropylamino)-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(F)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)CNC1CC1)C2 HNLJOUQXXSJJGA-UHFFFAOYSA-N 0.000 claims description 2
- MBLNXXSXIPPGKA-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1N(C(=O)CN(C)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1 MBLNXXSXIPPGKA-UHFFFAOYSA-N 0.000 claims description 2
- TUIYRZVQLXTFTF-UHFFFAOYSA-N 2-(dipropylamino)-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1N(C(=O)CN(CCC)CCC)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(C)C=C1 TUIYRZVQLXTFTF-UHFFFAOYSA-N 0.000 claims description 2
- MUOQWDOSRLBUDD-UHFFFAOYSA-N 2-(tert-butylamino)-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)CNC(C)(C)C)C2 MUOQWDOSRLBUDD-UHFFFAOYSA-N 0.000 claims description 2
- QPNGGZATIAGKMK-UHFFFAOYSA-N 2-[2-(difluoromethoxy)phenyl]-n-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine Chemical compound N1=C2C=CC=CN2C(NC(C)(C)CC(C)(C)C)=C1C1=CC=CC=C1OC(F)F QPNGGZATIAGKMK-UHFFFAOYSA-N 0.000 claims description 2
- IJSXMNSBQIHYQG-UHFFFAOYSA-N 2-[2-(furan-2-yl)phenyl]-n-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine Chemical compound N1=C2C=CC=CN2C(NC(C)(C)CC(C)(C)C)=C1C1=CC=CC=C1C1=CC=CO1 IJSXMNSBQIHYQG-UHFFFAOYSA-N 0.000 claims description 2
- LKXDTRBFDJAGQG-UHFFFAOYSA-N 2-[2-(trifluoromethyl)phenyl]-n-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine Chemical compound N1=C2C=CC=CN2C(NC(C)(C)CC(C)(C)C)=C1C1=CC=CC=C1C(F)(F)F LKXDTRBFDJAGQG-UHFFFAOYSA-N 0.000 claims description 2
- OQGFXVPMYDEAMN-UHFFFAOYSA-N 2-[2-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-oxoethyl]guanidine Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)CNC(N)=N)C2 OQGFXVPMYDEAMN-UHFFFAOYSA-N 0.000 claims description 2
- UHAXDYJQYKXGPL-UHFFFAOYSA-N 2-[2-[2-(diethylamino)ethoxy]phenyl]-n-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine Chemical compound CCN(CC)CCOC1=CC=CC=C1C1=C(NC(C)(C)CC(C)(C)C)N2C=CC=CC2=N1 UHAXDYJQYKXGPL-UHFFFAOYSA-N 0.000 claims description 2
- YDVKILHUMKNOCV-UHFFFAOYSA-N 2-[2-[3-(2,4,4-trimethylpentan-2-ylamino)imidazo[1,2-a]pyridin-2-yl]phenoxy]ethanol Chemical compound N1=C2C=CC=CN2C(NC(C)(C)CC(C)(C)C)=C1C1=CC=CC=C1OCCO YDVKILHUMKNOCV-UHFFFAOYSA-N 0.000 claims description 2
- SVWZQALTCCSHQE-UHFFFAOYSA-N 2-[3-(4-chloroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-1-(4-fluorophenyl)ethanone Chemical compound C1=CC(F)=CC=C1C(=O)CN1CC2=NC(C=3C=CC(F)=CC=3)=C(NC=3C=CC(Cl)=CC=3)N2CC1 SVWZQALTCCSHQE-UHFFFAOYSA-N 0.000 claims description 2
- HOYAVZZZPKTKOQ-UHFFFAOYSA-N 2-[4-(2-aminoethyl)piperidin-1-yl]-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)CN1CCC(CCN)CC1)C2 HOYAVZZZPKTKOQ-UHFFFAOYSA-N 0.000 claims description 2
- JTRPPMBFLBRBNS-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)CN(CCO)CCO)C2 JTRPPMBFLBRBNS-UHFFFAOYSA-N 0.000 claims description 2
- ROIACFBAFFGYDF-UHFFFAOYSA-N 2-amino-1-(3-anilino-2-phenyl-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl)-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC=CC=1)=C2NC1=CC=CC=C1 ROIACFBAFFGYDF-UHFFFAOYSA-N 0.000 claims description 2
- CBQREQZBYMQOQS-GFCCVEGCSA-N 2-amino-1-[(8r)-3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-8-methyl-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound NCC(=O)N([C@@H](C1=NC=2C=3C=CC(F)=CC=3)C)CCN1C=2NC1=CC=C(Cl)C(F)=C1 CBQREQZBYMQOQS-GFCCVEGCSA-N 0.000 claims description 2
- GIRUSYKPXOSDQE-OAQYLSRUSA-N 2-amino-1-[(8r)-3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-8-propan-2-yl-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound NCC(=O)N([C@@H](C1=NC=2C=3C=CC(F)=CC=3)C(C)C)CCN1C=2NC1=CC=C(Cl)C(F)=C1 GIRUSYKPXOSDQE-OAQYLSRUSA-N 0.000 claims description 2
- CBQREQZBYMQOQS-LBPRGKRZSA-N 2-amino-1-[(8s)-3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-8-methyl-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound NCC(=O)N([C@H](C1=NC=2C=3C=CC(F)=CC=3)C)CCN1C=2NC1=CC=C(Cl)C(F)=C1 CBQREQZBYMQOQS-LBPRGKRZSA-N 0.000 claims description 2
- GIRUSYKPXOSDQE-NRFANRHFSA-N 2-amino-1-[(8s)-3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-8-propan-2-yl-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound NCC(=O)N([C@H](C1=NC=2C=3C=CC(F)=CC=3)C(C)C)CCN1C=2NC1=CC=C(Cl)C(F)=C1 GIRUSYKPXOSDQE-NRFANRHFSA-N 0.000 claims description 2
- CVHKTGGLGIHCSV-UHFFFAOYSA-N 2-amino-1-[2,3-bis(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2C1=CC=C(F)C=C1 CVHKTGGLGIHCSV-UHFFFAOYSA-N 0.000 claims description 2
- CQTJOGLAQDYFOX-UHFFFAOYSA-N 2-amino-1-[2,3-bis(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound CC1(C)N(C(=O)CN)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2C1=CC=C(F)C=C1 CQTJOGLAQDYFOX-UHFFFAOYSA-N 0.000 claims description 2
- DBDYXYHGOQQBTM-UHFFFAOYSA-N 2-amino-1-[2-(2,4-difluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C(=CC(F)=CC=2)F)N=C2N1CCN(C(=O)C(C)(C)N)C2 DBDYXYHGOQQBTM-UHFFFAOYSA-N 0.000 claims description 2
- CAKUKKYNIVYENG-UHFFFAOYSA-N 2-amino-1-[2-(2,4-difluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C(=CC(F)=CC=2)F)N=C2N1CCN(C(=O)CN)C2 CAKUKKYNIVYENG-UHFFFAOYSA-N 0.000 claims description 2
- CFGLGNRDATUEIH-UHFFFAOYSA-N 2-amino-1-[2-(2,5-difluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C(=CC=C(F)C=2)F)N=C2N1CCN(C(=O)C(C)(C)N)C2 CFGLGNRDATUEIH-UHFFFAOYSA-N 0.000 claims description 2
- BFDILZYRYLPWSB-UHFFFAOYSA-N 2-amino-1-[2-(2,5-difluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C(=CC=C(F)C=2)F)N=C2N1CCN(C(=O)CN)C2 BFDILZYRYLPWSB-UHFFFAOYSA-N 0.000 claims description 2
- PHIMBLDBGGWVPS-UHFFFAOYSA-N 2-amino-1-[2-(2-methoxyphenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound COC1=CC=CC=C1C1=C(NC=2C=CC(C)=CC=2)N2CCN(C(=O)CN)CC2=N1 PHIMBLDBGGWVPS-UHFFFAOYSA-N 0.000 claims description 2
- CLDHVNABSWDGEA-UHFFFAOYSA-N 2-amino-1-[2-(3,4-difluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(F)C(F)=CC=2)N=C2N1CCN(C(=O)CN)C2 CLDHVNABSWDGEA-UHFFFAOYSA-N 0.000 claims description 2
- QOXFBQKZHHDZEL-UHFFFAOYSA-N 2-amino-1-[2-(3,5-difluorophenyl)-3-(4-fluoroanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=C(F)C=C(F)C=1)=C2NC1=CC=C(F)C=C1 QOXFBQKZHHDZEL-UHFFFAOYSA-N 0.000 claims description 2
- BLDFKWZNFBZPMF-UHFFFAOYSA-N 2-amino-1-[2-(3-chloro-4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(Cl)C(F)=CC=2)N=C2N1CCN(C(=O)CN)C2 BLDFKWZNFBZPMF-UHFFFAOYSA-N 0.000 claims description 2
- QKSCQGQDPXRZNZ-UHFFFAOYSA-N 2-amino-1-[2-(3-chlorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(Cl)C=CC=2)N=C2N1CCN(C(=O)C(C)(C)N)C2 QKSCQGQDPXRZNZ-UHFFFAOYSA-N 0.000 claims description 2
- WVMLQSKENDJIEZ-UHFFFAOYSA-N 2-amino-1-[2-(3-chlorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(Cl)C=CC=2)N=C2N1CCN(C(=O)CN)C2 WVMLQSKENDJIEZ-UHFFFAOYSA-N 0.000 claims description 2
- PABCQIGNPNWLFI-UHFFFAOYSA-N 2-amino-1-[2-(3-fluorophenyl)-3-[4-fluoro-2-(trifluoromethyl)anilino]-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=C(F)C=CC=1)=C2NC1=CC=C(F)C=C1C(F)(F)F PABCQIGNPNWLFI-UHFFFAOYSA-N 0.000 claims description 2
- NGHYBFUYKGQLMW-UHFFFAOYSA-N 2-amino-1-[2-(3-fluorophenyl)-5,5-dimethyl-3-(4-methylanilino)-6,8-dihydroimidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(F)C=CC=2)N=C2N1C(C)(C)CN(C(=O)C(C)(C)N)C2 NGHYBFUYKGQLMW-UHFFFAOYSA-N 0.000 claims description 2
- MSQHLLLDGKFJBC-UHFFFAOYSA-N 2-amino-1-[2-(3-fluorophenyl)-5,5-dimethyl-3-(4-methylanilino)-6,8-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(F)C=CC=2)N=C2N1C(C)(C)CN(C(=O)CN)C2 MSQHLLLDGKFJBC-UHFFFAOYSA-N 0.000 claims description 2
- NIHLETCIFKPVCV-UHFFFAOYSA-N 2-amino-1-[2-(4-bromophenyl)-3-(4-fluoroanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1N(C(=O)CN)CCN2C1=NC(C=1C=CC(Br)=CC=1)=C2NC1=CC=C(F)C=C1 NIHLETCIFKPVCV-UHFFFAOYSA-N 0.000 claims description 2
- QZZRKHVESVLXLK-UHFFFAOYSA-N 2-amino-1-[2-(4-chloro-3-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(F)C(Cl)=CC=2)N=C2N1CCN(C(=O)C(C)(C)N)C2 QZZRKHVESVLXLK-UHFFFAOYSA-N 0.000 claims description 2
- VMJIHCJHYHBWST-UHFFFAOYSA-N 2-amino-1-[2-(4-chloro-3-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(F)C(Cl)=CC=2)N=C2N1CCN(C(=O)CN)C2 VMJIHCJHYHBWST-UHFFFAOYSA-N 0.000 claims description 2
- MNRGBQRWXKQHQW-UHFFFAOYSA-N 2-amino-1-[2-(4-chlorophenyl)-3-(4-fluoroanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1N(C(=O)CN)CCN2C1=NC(C=1C=CC(Cl)=CC=1)=C2NC1=CC=C(F)C=C1 MNRGBQRWXKQHQW-UHFFFAOYSA-N 0.000 claims description 2
- LQOPJWSZEZFZKL-UHFFFAOYSA-N 2-amino-1-[2-(4-chlorophenyl)-3-(4-methylphenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C2N1CCN(C(=O)C(C)(C)N)C2 LQOPJWSZEZFZKL-UHFFFAOYSA-N 0.000 claims description 2
- PNLXKKWDVIBQPV-UHFFFAOYSA-N 2-amino-1-[2-(4-fluoro-3-methylphenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(C)C(F)=CC=2)N=C2N1CCN(C(=O)C(C)(C)N)C2 PNLXKKWDVIBQPV-UHFFFAOYSA-N 0.000 claims description 2
- SDRQQAYMCLYXFK-UHFFFAOYSA-N 2-amino-1-[2-(4-fluoro-3-methylphenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=C(C)C(F)=CC=2)N=C2N1CCN(C(=O)CN)C2 SDRQQAYMCLYXFK-UHFFFAOYSA-N 0.000 claims description 2
- SNTZJJNKHKTJIG-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-(3-fluorophenyl)sulfanyl-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1SC1=CC=CC(F)=C1 SNTZJJNKHKTJIG-UHFFFAOYSA-N 0.000 claims description 2
- NEBHCBMZTIQOBJ-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-(3-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound CC1=CC=CC(NC=2N3CCN(CC3=NC=2C=2C=CC(F)=CC=2)C(=O)C(C)(C)N)=C1 NEBHCBMZTIQOBJ-UHFFFAOYSA-N 0.000 claims description 2
- AWSQWXJSFJJNIE-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-(4-fluorophenyl)sulfanyl-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1SC1=CC=C(F)C=C1 AWSQWXJSFJJNIE-UHFFFAOYSA-N 0.000 claims description 2
- ANQMOPOKTOSNOY-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2,4-dimethylpentan-1-one Chemical compound C1N(C(=O)C(C)(N)CC(C)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(C)C=C1 ANQMOPOKTOSNOY-UHFFFAOYSA-N 0.000 claims description 2
- VGNRSBSIGNJLFZ-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)C(C)(C)N)C2 VGNRSBSIGNJLFZ-UHFFFAOYSA-N 0.000 claims description 2
- BZDHEWHVYUHAFX-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)CN)C2 BZDHEWHVYUHAFX-UHFFFAOYSA-N 0.000 claims description 2
- LLVCSBQXVLWSIT-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-(pyridin-3-ylamino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=CN=C1 LLVCSBQXVLWSIT-UHFFFAOYSA-N 0.000 claims description 2
- KTCKRGWEAGEQEE-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-[(4-fluorophenyl)methyl]-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2CC1=CC=C(F)C=C1 KTCKRGWEAGEQEE-UHFFFAOYSA-N 0.000 claims description 2
- ASMMVKDHFGHZSS-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-[(4-fluorophenyl)methyl]-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1CC1=CC=C(F)C=C1 ASMMVKDHFGHZSS-UHFFFAOYSA-N 0.000 claims description 2
- HMCAXJFLAZJQSZ-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-[(4-methoxyphenyl)methyl]-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CC1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)CN)CCN12 HMCAXJFLAZJQSZ-UHFFFAOYSA-N 0.000 claims description 2
- FRZPGNMRWKGDNL-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-[4-(trifluoromethoxy)anilino]-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(OC(F)(F)F)C=C1 FRZPGNMRWKGDNL-UHFFFAOYSA-N 0.000 claims description 2
- FDCYIRXGSMMDBE-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-[4-(trifluoromethyl)anilino]-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(C(F)(F)F)C=C1 FDCYIRXGSMMDBE-UHFFFAOYSA-N 0.000 claims description 2
- AAONVZUILZWZMH-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-[4-(trifluoromethyl)anilino]-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1N(C(=O)CN)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(C(F)(F)F)C=C1 AAONVZUILZWZMH-UHFFFAOYSA-N 0.000 claims description 2
- CYYROELHFHTEEQ-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-[4-fluoro-3-(trifluoromethyl)anilino]-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C(C(F)(F)F)=C1 CYYROELHFHTEEQ-UHFFFAOYSA-N 0.000 claims description 2
- NXVHXQWOLMYIQB-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-3-[4-fluoro-3-(trifluoromethyl)anilino]-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC=C(F)C(C(F)(F)F)=C1 NXVHXQWOLMYIQB-UHFFFAOYSA-N 0.000 claims description 2
- HTQSYIITGZOBJR-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-5,5-dimethyl-3-(4-methylanilino)-6,8-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1C(C)(C)CN(C(=O)CN)C2 HTQSYIITGZOBJR-UHFFFAOYSA-N 0.000 claims description 2
- SKGXKJYXJLGFKP-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-6,6-dimethyl-3-(4-methylanilino)-5,8-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CC(C)(C)N(C(=O)CN)C2 SKGXKJYXJLGFKP-UHFFFAOYSA-N 0.000 claims description 2
- ZVDCUXWEVUAUEH-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-6-methyl-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1N(C(=O)CN)C(C)CN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(C)C=C1 ZVDCUXWEVUAUEH-UHFFFAOYSA-N 0.000 claims description 2
- MMICXKYPEGUTAI-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(2-methylbutylamino)-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound N1=C(C(N(C(=O)CN)CC2)(C)C)N2C(NCC(C)CC)=C1C1=CC=C(F)C=C1 MMICXKYPEGUTAI-UHFFFAOYSA-N 0.000 claims description 2
- IXSJCIMEZLNRIG-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(3,4,5-trifluoroanilino)-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC(F)=C(F)C(F)=C1 IXSJCIMEZLNRIG-UHFFFAOYSA-N 0.000 claims description 2
- JAWWEPMONMJRGK-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(3-methylanilino)-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound CC1=CC=CC(NC=2N3C(C(N(C(=O)CN)CC3)(C)C)=NC=2C=2C=CC(F)=CC=2)=C1 JAWWEPMONMJRGK-UHFFFAOYSA-N 0.000 claims description 2
- QIZBBXZGNNKGNT-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(4-methylanilino)-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)C(C)(C)N)CCN12 QIZBBXZGNNKGNT-UHFFFAOYSA-N 0.000 claims description 2
- ZSDOPJQRXBSGSX-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(4-methylanilino)-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)CN)CCN12 ZSDOPJQRXBSGSX-UHFFFAOYSA-N 0.000 claims description 2
- HGXCTZGMWNPUFJ-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(4-methylphenyl)-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)CN)CCN12 HGXCTZGMWNPUFJ-UHFFFAOYSA-N 0.000 claims description 2
- DYOUALBEKPRDBL-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(4-methylphenyl)sulfanyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1SC1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)CN)CCN12 DYOUALBEKPRDBL-UHFFFAOYSA-N 0.000 claims description 2
- PBBZPGOXDKMGEG-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(4-methylsulfonylanilino)-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC=C(S(C)(=O)=O)C=C1 PBBZPGOXDKMGEG-UHFFFAOYSA-N 0.000 claims description 2
- YANDNCATHOLZGI-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(4-phenylanilino)-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC(C=C1)=CC=C1C1=CC=CC=C1 YANDNCATHOLZGI-UHFFFAOYSA-N 0.000 claims description 2
- RDCNONRHPNBMQR-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(4-piperidin-1-ylpiperidin-1-yl)-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound CC1(C)N(C(=O)CN)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2N(CC1)CCC1N1CCCCC1 RDCNONRHPNBMQR-UHFFFAOYSA-N 0.000 claims description 2
- SZFUYKLETFRZKK-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-(oxan-4-ylamino)-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1CCOCC1 SZFUYKLETFRZKK-UHFFFAOYSA-N 0.000 claims description 2
- INTUMPHOQSEAEO-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-[(2-methylcyclohexyl)amino]-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound CC1CCCCC1NC1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)CN)CCN12 INTUMPHOQSEAEO-UHFFFAOYSA-N 0.000 claims description 2
- LRZYCOCJRHVFHY-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-[(3,3,5-trimethylcyclohexyl)amino]-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1C(C)(C)CC(C)CC1NC1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)CN)CCN12 LRZYCOCJRHVFHY-UHFFFAOYSA-N 0.000 claims description 2
- WGOCZKUJPWNPPC-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-[(4-methylphenyl)methyl]-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1CC1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)CN)CCN12 WGOCZKUJPWNPPC-UHFFFAOYSA-N 0.000 claims description 2
- HVOGPSIBRSSKQN-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-[(4-methylpiperazin-1-yl)methyl]-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1CN(C)CCN1CC1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)CN)CCN12 HVOGPSIBRSSKQN-UHFFFAOYSA-N 0.000 claims description 2
- SUGQHGBUMUEOTO-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-[(4-phenylcyclohexyl)amino]-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC(CC1)CCC1C1=CC=CC=C1 SUGQHGBUMUEOTO-UHFFFAOYSA-N 0.000 claims description 2
- LLFYGSFBMKBNNC-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-[3-(trifluoromethoxy)anilino]-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC=CC(OC(F)(F)F)=C1 LLFYGSFBMKBNNC-UHFFFAOYSA-N 0.000 claims description 2
- SYAFKEFTBOUSOP-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-[3-(trifluoromethyl)anilino]-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC=CC(C(F)(F)F)=C1 SYAFKEFTBOUSOP-UHFFFAOYSA-N 0.000 claims description 2
- OTOZTERYBJYOBZ-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1CN(C)CCC1N1CCN(C=2N3C(C(N(C(=O)CN)CC3)(C)C)=NC=2C=2C=CC(F)=CC=2)CC1 OTOZTERYBJYOBZ-UHFFFAOYSA-N 0.000 claims description 2
- XFTSAKQSFVROFO-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-[4-(4-methylpiperazin-1-yl)anilino]-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)CN)CCN12 XFTSAKQSFVROFO-UHFFFAOYSA-N 0.000 claims description 2
- POUCBXHANCUPHR-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-3-[4-(trifluoromethoxy)anilino]-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC=C(OC(F)(F)F)C=C1 POUCBXHANCUPHR-UHFFFAOYSA-N 0.000 claims description 2
- ZTRGOWVOCYIOER-UHFFFAOYSA-N 2-amino-1-[2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]-3-(4-methylphenyl)propan-1-one Chemical compound C1=CC(C)=CC=C1CC(N)C(=O)N1C(C)(C)C2=NC(C=3C=CC(F)=CC=3)=CN2CC1 ZTRGOWVOCYIOER-UHFFFAOYSA-N 0.000 claims description 2
- UZTJMZQSBOYSMO-UHFFFAOYSA-N 2-amino-1-[2-cyclohexyl-3-(4-fluoroanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN(C=2NC=3C=CC(F)=CC=3)C1=NC=2C1CCCCC1 UZTJMZQSBOYSMO-UHFFFAOYSA-N 0.000 claims description 2
- XOEQCRSTQCJSDZ-UHFFFAOYSA-N 2-amino-1-[3-(1,3-benzodioxol-5-ylamino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN(C=2NC=3C=C4OCOC4=CC=3)C1=NC=2C1=CC=C(F)C=C1 XOEQCRSTQCJSDZ-UHFFFAOYSA-N 0.000 claims description 2
- BYLGMXUNERRZLL-UHFFFAOYSA-N 2-amino-1-[3-(2,4-difluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1F BYLGMXUNERRZLL-UHFFFAOYSA-N 0.000 claims description 2
- OINKJECGQPNTCV-UHFFFAOYSA-N 2-amino-1-[3-(2,4-difluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1N(C(=O)CN)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1F OINKJECGQPNTCV-UHFFFAOYSA-N 0.000 claims description 2
- FZPNGLXOHOHAOL-UHFFFAOYSA-N 2-amino-1-[3-(3,4-dichloroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(Cl)C(Cl)=C1 FZPNGLXOHOHAOL-UHFFFAOYSA-N 0.000 claims description 2
- XFVQXPQCEKHCOO-UHFFFAOYSA-N 2-amino-1-[3-(3,4-dichloroanilino)-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)C(C)(N)C)CCN2C=1NC1=CC=C(Cl)C(Cl)=C1 XFVQXPQCEKHCOO-UHFFFAOYSA-N 0.000 claims description 2
- VYCRNQLSPHJYCR-UHFFFAOYSA-N 2-amino-1-[3-(3,4-difluoro-5-methoxyanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound FC1=C(F)C(OC)=CC(NC=2N3CCN(CC3=NC=2C=2C=CC(F)=CC=2)C(=O)C(C)(C)N)=C1 VYCRNQLSPHJYCR-UHFFFAOYSA-N 0.000 claims description 2
- VJGFETSRYCJXMW-UHFFFAOYSA-N 2-amino-1-[3-(3,4-difluoroanilino)-2-(3-fluorophenyl)-5,5-dimethyl-6,8-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound N12C(C)(C)CN(C(=O)CN)CC2=NC(C=2C=C(F)C=CC=2)=C1NC1=CC=C(F)C(F)=C1 VJGFETSRYCJXMW-UHFFFAOYSA-N 0.000 claims description 2
- WSZQTDFVLWRMRF-UHFFFAOYSA-N 2-amino-1-[3-(3,4-difluoroanilino)-2-(4-fluorophenyl)-6,6-dimethyl-5,8-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1N(C(=O)CN)C(C)(C)CN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C(F)=C1 WSZQTDFVLWRMRF-UHFFFAOYSA-N 0.000 claims description 2
- CLKQZPRZINRQOP-UHFFFAOYSA-N 2-amino-1-[3-(3,4-difluoroanilino)-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)C(C)(N)C)CCN2C=1NC1=CC=C(F)C(F)=C1 CLKQZPRZINRQOP-UHFFFAOYSA-N 0.000 claims description 2
- ROGAYXJGTZEBOA-UHFFFAOYSA-N 2-amino-1-[3-(3,4-difluoroanilino)-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC=C(F)C(F)=C1 ROGAYXJGTZEBOA-UHFFFAOYSA-N 0.000 claims description 2
- ATSWYFCMMSTSFA-UHFFFAOYSA-N 2-amino-1-[3-(3,4-difluorophenoxy)-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1OC1=CC=C(F)C(F)=C1 ATSWYFCMMSTSFA-UHFFFAOYSA-N 0.000 claims description 2
- SZHFFLSLPQRCNW-UHFFFAOYSA-N 2-amino-1-[3-(3,4-dimethylanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=C(C)C(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)C(C)(C)N)C2 SZHFFLSLPQRCNW-UHFFFAOYSA-N 0.000 claims description 2
- BNFWDTXSWZWYHX-UHFFFAOYSA-N 2-amino-1-[3-(3,4-dimethylanilino)-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1=C(C)C(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2C(C)(C)N(C(=O)CN)CCN12 BNFWDTXSWZWYHX-UHFFFAOYSA-N 0.000 claims description 2
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- JQXIUZLCSGVRDS-UHFFFAOYSA-N 2-amino-1-[3-(4-fluoroanilino)-2-(4-pentylphenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(CCCCC)=CC=C1C1=C(NC=2C=CC(F)=CC=2)N2CCN(C(=O)C(C)(C)N)CC2=N1 JQXIUZLCSGVRDS-UHFFFAOYSA-N 0.000 claims description 2
- ZJQOMUFAPNLITL-UHFFFAOYSA-N 2-amino-1-[3-(4-fluoroanilino)-2-phenyl-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC=CC=1)=C2NC1=CC=C(F)C=C1 ZJQOMUFAPNLITL-UHFFFAOYSA-N 0.000 claims description 2
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- YCALWNTYINXFOM-UHFFFAOYSA-N 2-amino-1-[3-(benzylamino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NCC1=CC=CC=C1 YCALWNTYINXFOM-UHFFFAOYSA-N 0.000 claims description 2
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- COVKEPBJTHKDAT-UHFFFAOYSA-N 2-amino-1-[3-(cyclopentylamino)-2-phenyl-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C1N(C(=O)CN)CCN2C1=NC(C=1C=CC=CC=1)=C2NC1CCCC1 COVKEPBJTHKDAT-UHFFFAOYSA-N 0.000 claims description 2
- OTUUKUDYOUEDRK-UHFFFAOYSA-N 2-amino-1-[3-[(1,5-dimethylpyrazol-3-yl)amino]-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound CN1C(C)=CC(NC=2N3C(C(N(C(=O)CN)CC3)(C)C)=NC=2C=2C=CC(F)=CC=2)=N1 OTUUKUDYOUEDRK-UHFFFAOYSA-N 0.000 claims description 2
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- OCGWGWQJTBNHTO-UHFFFAOYSA-N 2-amino-1-[3-[(3,4-difluorophenyl)methyl]-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1CC1=CC=C(F)C(F)=C1 OCGWGWQJTBNHTO-UHFFFAOYSA-N 0.000 claims description 2
- NUYUZJCIDWLKDG-UHFFFAOYSA-N 2-amino-1-[3-[(4,4-difluorocyclohexyl)amino]-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1CCC(F)(F)CC1 NUYUZJCIDWLKDG-UHFFFAOYSA-N 0.000 claims description 2
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- QGTQENRAPSWYAD-UHFFFAOYSA-N 2-amino-1-[3-[3-chloro-4-(trifluoromethyl)anilino]-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(C(F)(F)F)C(Cl)=C1 QGTQENRAPSWYAD-UHFFFAOYSA-N 0.000 claims description 2
- ZADYRFPVCBUOAZ-UHFFFAOYSA-N 2-amino-1-[3-[3-chloro-4-(trifluoromethyl)anilino]-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC=C(C(F)(F)F)C(Cl)=C1 ZADYRFPVCBUOAZ-UHFFFAOYSA-N 0.000 claims description 2
- YPZWLUFAYYKXAC-UHFFFAOYSA-N 2-amino-1-[3-[4-(difluoromethoxy)anilino]-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)(N)C)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(OC(F)F)C=C1 YPZWLUFAYYKXAC-UHFFFAOYSA-N 0.000 claims description 2
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- GRHRVNMZMQYEQU-UHFFFAOYSA-N 2-amino-3,3,3-trifluoro-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-methylpropan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)C(C)(N)C(F)(F)F)C2 GRHRVNMZMQYEQU-UHFFFAOYSA-N 0.000 claims description 2
- PWOAKGBXXXIDDX-UHFFFAOYSA-N 2-amino-3,3,3-trifluoro-1-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)C(N)C(F)(F)F)C2 PWOAKGBXXXIDDX-UHFFFAOYSA-N 0.000 claims description 2
- NTVXVMHVNXQFOC-UHFFFAOYSA-N 2-amino-3,3,3-trifluoro-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]propan-1-one Chemical compound C1N(C(=O)C(N)C(F)(F)F)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1 NTVXVMHVNXQFOC-UHFFFAOYSA-N 0.000 claims description 2
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- ZCUUVMJMDHGNBP-UHFFFAOYSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-(oxolan-3-yl)methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)C1COCC1)C2 ZCUUVMJMDHGNBP-UHFFFAOYSA-N 0.000 claims description 2
- KVDZWHZYGNYTBF-SFTDATJTSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(1s,2s)-2-hydroxycyclopentyl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H]1[C@H](CCC1)O)C2 KVDZWHZYGNYTBF-SFTDATJTSA-N 0.000 claims description 2
- DHHLDCNWSQNJLS-HXUWFJFHSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(2r)-oxolan-2-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H]1OCCC1)C2 DHHLDCNWSQNJLS-HXUWFJFHSA-N 0.000 claims description 2
- JUUSMUXETVKQLO-OAQYLSRUSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(2r)-piperidin-2-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H]1NCCCC1)C2 JUUSMUXETVKQLO-OAQYLSRUSA-N 0.000 claims description 2
- MVPBFNDUTUSHMH-HXUWFJFHSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(2r)-pyrrolidin-2-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H]1NCCC1)C2 MVPBFNDUTUSHMH-HXUWFJFHSA-N 0.000 claims description 2
- DHHLDCNWSQNJLS-FQEVSTJZSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(2s)-oxolan-2-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@H]1OCCC1)C2 DHHLDCNWSQNJLS-FQEVSTJZSA-N 0.000 claims description 2
- JUUSMUXETVKQLO-NRFANRHFSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(2s)-piperidin-2-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@H]1NCCCC1)C2 JUUSMUXETVKQLO-NRFANRHFSA-N 0.000 claims description 2
- MVPBFNDUTUSHMH-FQEVSTJZSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(2s)-pyrrolidin-2-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@H]1NCCC1)C2 MVPBFNDUTUSHMH-FQEVSTJZSA-N 0.000 claims description 2
- VEFUICPPQMGYCI-LJQANCHMSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(3r)-piperidin-3-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@H]1CNCCC1)C2 VEFUICPPQMGYCI-LJQANCHMSA-N 0.000 claims description 2
- MBTQVGIVTWCVDA-GOSISDBHSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(3r)-pyrrolidin-3-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@H]1CNCC1)C2 MBTQVGIVTWCVDA-GOSISDBHSA-N 0.000 claims description 2
- VEFUICPPQMGYCI-IBGZPJMESA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(3s)-piperidin-3-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H]1CNCCC1)C2 VEFUICPPQMGYCI-IBGZPJMESA-N 0.000 claims description 2
- MBTQVGIVTWCVDA-SFHVURJKSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(3s)-pyrrolidin-3-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@@H]1CNCC1)C2 MBTQVGIVTWCVDA-SFHVURJKSA-N 0.000 claims description 2
- MAQABSBWHQSFPS-NRFANRHFSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(6s)-4,5,6,7-tetrahydro-3h-imidazo[4,5-c]pyridin-6-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@H]1NCC=3N=CNC=3C1)C2 MAQABSBWHQSFPS-NRFANRHFSA-N 0.000 claims description 2
- SKKYQCGKZWHTJY-UHFFFAOYSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[4-(3-methylpiperidin-1-yl)piperidin-1-yl]methanone Chemical compound C1C(C)CCCN1C1CCN(C(=O)N2CC=3N(C(=C(N=3)C=3C=CC(F)=CC=3)NC=3C=CC(C)=CC=3)CC2)CC1 SKKYQCGKZWHTJY-UHFFFAOYSA-N 0.000 claims description 2
- PEBXLWFVIQYDSS-UHFFFAOYSA-N [2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[4-(4-fluorophenyl)piperidin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)N1CCC(CC1)C=1C=CC(F)=CC=1)C2 PEBXLWFVIQYDSS-UHFFFAOYSA-N 0.000 claims description 2
- GJKINRGJOPGUHN-UHFFFAOYSA-N [2-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-oxo-1-phenylethyl] butanoate Chemical compound C=1C=CC=CC=1C(OC(=O)CCC)C(=O)N(C1)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(C)C=C1 GJKINRGJOPGUHN-UHFFFAOYSA-N 0.000 claims description 2
- WVVFELYFXSUHBR-UHFFFAOYSA-N [2-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-oxo-1-phenylethyl] pentanoate Chemical compound C=1C=CC=CC=1C(OC(=O)CCCC)C(=O)N(C1)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(C)C=C1 WVVFELYFXSUHBR-UHFFFAOYSA-N 0.000 claims description 2
- UJHMBAARXSPCLM-UHFFFAOYSA-N [2-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-oxo-1-phenylethyl] propanoate Chemical compound C=1C=CC=CC=1C(OC(=O)CC)C(=O)N(C1)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(C)C=C1 UJHMBAARXSPCLM-UHFFFAOYSA-N 0.000 claims description 2
- ZWUDQOJKPLUUBU-UHFFFAOYSA-N [2-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-2-oxoethyl]urea Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)CNC(N)=O)C2 ZWUDQOJKPLUUBU-UHFFFAOYSA-N 0.000 claims description 2
- LXBXASXKXXGZMZ-UHFFFAOYSA-N [3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-(2,3-dihydro-1h-isoindol-1-yl)methanone Chemical compound C1=CC(F)=CC=C1C1=C(NC=2C=C(F)C(Cl)=CC=2)N2CCN(C(=O)C3C4=CC=CC=C4CN3)CC2=N1 LXBXASXKXXGZMZ-UHFFFAOYSA-N 0.000 claims description 2
- MQHLYYUDZOZTET-UHFFFAOYSA-N [3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-(4-methylmorpholin-2-yl)methanone Chemical compound C1N(C)CCOC1C(=O)N1CC2=NC(C=3C=CC(F)=CC=3)=C(NC=3C=C(F)C(Cl)=CC=3)N2CC1 MQHLYYUDZOZTET-UHFFFAOYSA-N 0.000 claims description 2
- FZXBQWLHTJBCMU-LJQANCHMSA-N [3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(2r)-oxolan-2-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=C(NC=2C=C(F)C(Cl)=CC=2)N2CCN(C(=O)[C@@H]3OCCC3)CC2=N1 FZXBQWLHTJBCMU-LJQANCHMSA-N 0.000 claims description 2
- GWFDXIABMXOHKR-QHCPKHFHSA-N [3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(2s)-2,3-dihydro-1h-indol-2-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=C(NC=2C=C(F)C(Cl)=CC=2)N2CCN(C(=O)[C@H]3NC4=CC=CC=C4C3)CC2=N1 GWFDXIABMXOHKR-QHCPKHFHSA-N 0.000 claims description 2
- QNTFQOJBBPARNI-IBGZPJMESA-N [3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(2s)-pyrrolidin-2-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=C(NC=2C=C(F)C(Cl)=CC=2)N2CCN(C(=O)[C@H]3NCCC3)CC2=N1 QNTFQOJBBPARNI-IBGZPJMESA-N 0.000 claims description 2
- XYKLCQWZRSLLNP-XMMPIXPASA-N [3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(3r)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=C(NC=2C=C(F)C(Cl)=CC=2)N2CCN(C(=O)[C@@H]3NCC4=CC=CC=C4C3)CC2=N1 XYKLCQWZRSLLNP-XMMPIXPASA-N 0.000 claims description 2
- QVLAHGDAVIYZIA-HNNXBMFYSA-N [3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-[(3s)-pyrrolidin-3-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=C(NC=2C=C(F)C(Cl)=CC=2)N2CCN(C(=O)[C@@H]3CNCC3)CC2=N1 QVLAHGDAVIYZIA-HNNXBMFYSA-N 0.000 claims description 2
- SGDRWAOXKIIQDJ-UHFFFAOYSA-N [3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-morpholin-2-ylmethanone Chemical compound C1=CC(F)=CC=C1C1=C(NC=2C=C(F)C(Cl)=CC=2)N2CCN(C(=O)C3OCCNC3)CC2=N1 SGDRWAOXKIIQDJ-UHFFFAOYSA-N 0.000 claims description 2
- DUAYXAHKJZMVAS-UHFFFAOYSA-N [3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-morpholin-3-ylmethanone Chemical compound C1=CC(F)=CC=C1C1=C(NC=2C=C(F)C(Cl)=CC=2)N2CCN(C(=O)C3NCCOC3)CC2=N1 DUAYXAHKJZMVAS-UHFFFAOYSA-N 0.000 claims description 2
- YSJCFDLXKIBKAA-UHFFFAOYSA-N [3-(4-chloro-3-fluoroanilino)-2-(4-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-quinolin-6-ylmethanone Chemical compound C1=CC(F)=CC=C1C1=C(NC=2C=C(F)C(Cl)=CC=2)N2CCN(C(=O)C=3C=C4C=CC=NC4=CC=3)CC2=N1 YSJCFDLXKIBKAA-UHFFFAOYSA-N 0.000 claims description 2
- JORSBIRLNMRKMV-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)N1CC2=NC(C=3C=CC(F)=CC=3)=C(NC=3C=CC(C)=CC=3)N2CC1 JORSBIRLNMRKMV-UHFFFAOYSA-N 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- MNVFUMXIHMJUKX-NDEPHWFRSA-N benzyl (3s)-4-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@H](CC(=O)OCC=1C=CC=CC=1)NC(=O)OC(C)(C)C)C2 MNVFUMXIHMJUKX-NDEPHWFRSA-N 0.000 claims description 2
- WVMLFHIGAWYZAL-MHZLTWQESA-N benzyl (3s)-4-[3-(4-chloro-3-fluoroanilino)-2-(3-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate Chemical compound C([C@H](NC(=O)OC(C)(C)C)C(=O)N1CC=2N(C(=C(N=2)C=2C=C(F)C=CC=2)NC=2C=C(F)C(Cl)=CC=2)CC1)C(=O)OCC1=CC=CC=C1 WVMLFHIGAWYZAL-MHZLTWQESA-N 0.000 claims description 2
- KDNOOVMZPGKYJP-MHZLTWQESA-N benzyl (3s)-4-[3-(4-fluoroanilino)-2-(3-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate Chemical compound C([C@H](NC(=O)OC(C)(C)C)C(=O)N1CC=2N(C(=C(N=2)C=2C=C(F)C=CC=2)NC=2C=CC(F)=CC=2)CC1)C(=O)OCC1=CC=CC=C1 KDNOOVMZPGKYJP-MHZLTWQESA-N 0.000 claims description 2
- NMTFZQNPWQJAIS-LJAQVGFWSA-N benzyl (4s)-5-[2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC(F)=CC=2)N=C2N1CCN(C(=O)[C@H](CCC(=O)OCC=1C=CC=CC=1)NC(=O)OC(C)(C)C)C2 NMTFZQNPWQJAIS-LJAQVGFWSA-N 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000006226 butoxyethyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- ZRLIXXDUULIIKL-UHFFFAOYSA-N n,2-bis(4-fluorophenyl)-5,5,7,8,8-pentamethyl-6h-imidazo[1,2-a]pyrazin-3-amine Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C)CC(C)(C)N2C=1NC1=CC=C(F)C=C1 ZRLIXXDUULIIKL-UHFFFAOYSA-N 0.000 claims description 2
- RPXUWCJFWMBWKJ-UHFFFAOYSA-N n,2-bis(4-fluorophenyl)-6,6-dimethyl-7,8-dihydro-5h-imidazo[1,2-a]pyrazin-3-amine Chemical compound C1NC(C)(C)CN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C=C1 RPXUWCJFWMBWKJ-UHFFFAOYSA-N 0.000 claims description 2
- WHUQOYBGOGBGRV-UHFFFAOYSA-N n,2-bis(4-fluorophenyl)-7,8,8-trimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-3-amine Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C)CCN2C=1NC1=CC=C(F)C=C1 WHUQOYBGOGBGRV-UHFFFAOYSA-N 0.000 claims description 2
- ZELGCKFGDPUFBX-UHFFFAOYSA-N n,2-bis(4-fluorophenyl)-8,8-dimethyl-6,7-dihydro-5h-imidazo[1,2-a]pyrazin-3-amine Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)NCCN2C=1NC1=CC=C(F)C=C1 ZELGCKFGDPUFBX-UHFFFAOYSA-N 0.000 claims description 2
- CAACHJLJFBTNIE-UHFFFAOYSA-N n,2-bis(4-fluorophenyl)-8,8-dimethyl-6,7-dihydro-5h-imidazo[1,2-a]pyrazine-3-carboxamide Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)NCCN2C=1C(=O)NC1=CC=C(F)C=C1 CAACHJLJFBTNIE-UHFFFAOYSA-N 0.000 claims description 2
- OLVFLAGXHYNTAP-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-(4-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-amine Chemical compound C1=CC(F)=CC=C1C1=C(NC=2C=C(Cl)C(Cl)=CC=2)N2CCNCC2=N1 OLVFLAGXHYNTAP-UHFFFAOYSA-N 0.000 claims description 2
- WQEHLIOWXSUKLV-UHFFFAOYSA-N n-(3,4-difluorophenyl)-2-(4-fluorophenyl)-5,5,7-trimethyl-6,8-dihydroimidazo[1,2-a]pyrazin-3-amine Chemical compound N12C(C)(C)CN(C)CC2=NC(C=2C=CC(F)=CC=2)=C1NC1=CC=C(F)C(F)=C1 WQEHLIOWXSUKLV-UHFFFAOYSA-N 0.000 claims description 2
- MGDUMCYLEPUKAD-UHFFFAOYSA-N n-(3,4-difluorophenyl)-2-(4-fluorophenyl)-6,6-dimethyl-7,8-dihydro-5h-imidazo[1,2-a]pyrazin-3-amine Chemical compound C1NC(C)(C)CN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(F)C(F)=C1 MGDUMCYLEPUKAD-UHFFFAOYSA-N 0.000 claims description 2
- SRPXKZMVZFRKIQ-UHFFFAOYSA-N n-(3,4-difluorophenyl)-2-(4-fluorophenyl)-8,8-dimethyl-6,7-dihydro-5h-imidazo[1,2-a]pyrazin-3-amine Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)NCCN2C=1NC1=CC=C(F)C(F)=C1 SRPXKZMVZFRKIQ-UHFFFAOYSA-N 0.000 claims description 2
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- XRKCCRUNXMITGN-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-(4-fluorophenyl)-3-(4-methylanilino)-6,8-dihydro-5h-imidazo[1,2-a]pyrazine-7-carboxamide Chemical compound C1N(C(=O)NCCN(CC)CC)CCN2C1=NC(C=1C=CC(F)=CC=1)=C2NC1=CC=C(C)C=C1 XRKCCRUNXMITGN-UHFFFAOYSA-N 0.000 claims description 2
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- ZMXLCHRRIPJEPZ-UHFFFAOYSA-N n-[3-[[7-(2-aminoacetyl)-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-3-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=C(F)C=CC=1C=1N=C2C(C)(C)N(C(=O)CN)CCN2C=1NC1=CC=CC(NS(C)(=O)=O)=C1 ZMXLCHRRIPJEPZ-UHFFFAOYSA-N 0.000 claims description 2
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- QNCKSSKSZOFJNX-MHZLTWQESA-N n-[4-[(2s)-2-amino-3-[3-(4-fluoroanilino)-2-(3-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-oxopropyl]phenyl]pentanamide Chemical compound C1=CC(NC(=O)CCCC)=CC=C1C[C@H](N)C(=O)N1CC2=NC(C=3C=C(F)C=CC=3)=C(NC=3C=CC(F)=CC=3)N2CC1 QNCKSSKSZOFJNX-MHZLTWQESA-N 0.000 claims description 2
- VSSKPIUBRNUBBV-VWLOTQADSA-N n-[4-[(2s)-2-amino-3-[3-(4-fluoroanilino)-2-(3-fluorophenyl)-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl]-3-oxopropyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C[C@H](N)C(=O)N1CC2=NC(C=3C=C(F)C=CC=3)=C(NC=3C=CC(F)=CC=3)N2CC1 VSSKPIUBRNUBBV-VWLOTQADSA-N 0.000 claims description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
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Classifications
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- Nitrogen Condensed Heterocyclic Rings (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
본 발명은 한 부류의 화합물, 상기 화합물을 포함하는 제약 조성물, 및 말라리아를 치료 또는 예방하기 위한 상기 화합물의 사용 방법을 제공한다.
Description
<관련 출원에 대한 상호 참조>
본 출원은 2008년 7월 9일에 출원된 미국 가특허 출원 제61/224,433호에 대하여 우선권의 이익을 주장한다. 상기 출원의 모든 개시내용은 그 전체로 모든 목적을 위해 본원에 참조로 포함된다.
<본 발명의 분야>
본 발명은 한 부류의 화합물, 상기 화합물을 포함하는 제약 조성물, 및 말라리아를 치료 또는 예방하기 위한 상기 화합물의 사용 방법을 제공한다.
말라리아는 4가지 원생 기생충, 즉 열대열원충 (Plasmodium falciparum); 삼일열원충 (Plasmodium vivax); 난형열원충 (Plasmodium ovale); 및 사일열원충 (Plasmodium malaria)에 의해 유발되는 감염성 질환이다. 이들 4가지 기생충은 통상 감염된 암컷 학질모기가 물어 전파된다. 말라리아는 세계 여러 곳에서 문제를 일으키며, 최근 수 십년에 걸쳐 말라리아 부담은 꾸준히 증가하였다. 어림잡아 1 내지 3백만명의 사람들이 매년 말라리아로 사망하며, 대부분 5세 미만의 어린이이다. 말라리아 사망자 수의 증가는, 치명적인 말라리아 기생충인 열대열원충이 아르테미시닌 유도체를 제외하고는 거의 모든 이용가능한 항말라리아 약물에 대해 내성을 획득하였다는 사실에 일부 기인한다.
리슈만편모충증 (Leishmaniasis)은 리슈마니아속 (genus Leishmania)에 속하는 20종 초과의 기생 원충에 의해 유발되며, 암컷 응애가 물어 전파된다. 리슈만편모충증은 여러 열대 및 아열대 지역을 포함한 약 88개국에서 풍토적이다.
리슈만편모충증의 4가지 주요 형태가 있다. 칼라-아자르 (kala-azar)로도 불리는 내장리슈만편모충증이 가장 심각한 형태이며, 기생충 리슈마니아 도노바니 (Leishmania donovani)에 의해 유발된다. 내장리슈만편모충증이 발병한 환자는 치료를 받지 않는 경우 수 개월 이내에 사망할 수 있다. 내장리슈만편모충증에 대한 2가지 주요 요법은 안티몬 유도체 나트륨 스티보글루코네이트 (펜토스탐 (Pentostam)®) 및 메글루민 안티모니에이트 (글루칸팀 (Glucantim)®)이다. 나트륨 스티보글루코네이트는 약 70여년간 사용되어 왔으며, 상기 약물에 대한 내성이 점점 문제가 된다. 또한, 치료는 비교적 장기간이며, 고통스럽고, 원치 않는 부작용을 일으킬 수 있다.
수면병으로도 알려져 있는 인간 아프리카 트리파노소마증 (Human African Trypanosomiasis)은 매개체-감염 기생충 질환이다. 관련 기생충은 트리파노소마속 (Trypanosoma Genus)에 속하는 원충이다. 이들은 인간 병원성 기생충을 보유한 인간 또는 동물로부터 감염된 체체파리 (글로시나속 (Glossina Genus))가 물어 인간에게 전파된다.
샤가스병 (Chagas disease) (아메리카 트리파노소마증으로도 불림)은 아메리카 대륙의 가난한 집단 사이에서 고질적인 또 다른 인간 기생충 질환이다. 상기 질환은 원생 기생충인 트리파노소마 크루지 (Trypanosoma cruzi)에 의해 유발되며, 이는 흡혈 곤충에 의해 인간에게 전파된다. 상기 인간 질환은 감염 후 빠르게 발생하는 급성 단계 및 수 년에 걸쳐 발병할 수 있는 만성 단계의 2단계로 발생한다. 만성 감염은 치매, 심근 손상 및 때때로 소화관 팽창, 및 또한 체중 감소를 비롯하여 다양한 신경학적 장애를 일으킨다. 치료되지 않은 만성 질환은 종종 치명적이다.
샤가스병의 치료에 대해 현재 이용가능한 약물은 니푸르티목스 (Nifurtimox) 및 벤즈니다졸이다. 그러나, 이러한 현행 요법의 문제로는 그들의 다양한 부작용, 치료 기간, 및 치료 중 의학적 관리에 대한 요구를 들 수 있다. 게다가, 치료는 실제로 질환의 급성 단계 중에 제공된 경우에만 효과적이다. 2가지 1차 (frontline) 약물에 대한 내성은 이미 발생하였다. 항진균제인 암포테리신 b (Amphotericin b)가 2차 (second-line) 약물로 제안된 바 있지만, 상기 약물은 고가이며 비교적 독성이 있다.
상기를 고려하여, 항기생충제로서 신규한 화합물을 개발하는 것이 요망된다.
<본 발명의 요약>
제1 측면에서, 본 발명은 하기 화학식 Ia, Ib 및 Ic의 화합물로부터 선택되는 화합물, 및 이들의 N-옥시드 유도체, 전구약물 유도체, 보호된 유도체, 개별 이성질체 및 이성질체 혼합물; 및 상기 화합물의 제약상 허용되는 염 및 용매화물 (예를 들어, 수화물)을 제공한다.
<화학식 Ia>
<화학식 Ib>
<화학식 Ic>
식 중,
n은 0, 1, 2, 3 및 4로부터 선택되고;
m은 0, 1, 2, 3 및 4로부터 선택되고;
Ra는 수소, 할로, -X3NR7R8, -X3OR8, -X3S(O)0-2R8, -X3C(O)NR7R8, -X3R8, 벤질, 및 할로, C1 - 4알킬, 할로-치환된-C1 - 4알킬, C1 - 4알콕시 및 할로-치환된-C1 - 4알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되는 C6 - 10아릴로부터 선택되며; 여기서 X3은 결합 및 C1 - 4알킬렌으로부터 선택되고;
Rb는 수소 및 C1 - 4알킬로부터 선택되고;
R1은 할로, -OR13, -C(O)OR13, -NR13R14, C6 - 10아릴, 및 3개 이하의 질소를 함유하는 포화, 불포화 또는 부분 불포화 4원 내지 9원 헤테로시클릭 고리로부터 선택되며; 여기서 R13은 수소, C1 - 6알킬, 할로-치환된-C1 - 6알킬, 히드록시-치환된-C1 - 6알킬, C6-10아릴-C0 - 4알킬, C3 - 8시클로알킬-C0 - 4알킬, -X1NHC(O)R15, -X1C(NH)NHR15, -X1C(O)NHR15, -X1NHR15, -X1OR15, -C(O)R15 및 -C(O)OR15로부터 선택되며; 여기서 X1은 결합 및 C1 - 4알킬렌으로부터 선택되며; R15는 수소, C1 - 6알킬, 할로-치환된-C1 - 6알킬 및 벤질로부터 선택되며; R14는 수소, C1 - 6알킬 및 히드록시-치환된-C1 - 6알킬로부터 선택되며; 여기서 R1의 임의의 아릴 또는 헤테로시클릭은 할로, C1 - 6알킬, 할로-치환된-C1 - 6알킬, C1-6알콕시 및 할로-치환된-C1 - 6알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되거나; 또는
R13 및 R14는 이들이 부착된 질소와 함께 N, NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자를 함유하는 포화, 불포화 또는 부분 불포화 5원 내지 9원 헤테로시클릭 고리를 형성하며; 여기서 R30은 수소 및 C1 - 6알킬로부터 선택되며; 여기서 상기 R13 및 R14의 조합에 의해 형성되는 헤테로시클릭 고리는 할로, 히드록시, C1 - 6알킬, 아미노-치환된-C1 - 6알킬 및 할로-치환된-C1 - 6알킬로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되고;
R2는 수소, C1 - 6알킬, 아미노, C3 - 8시클로알킬-C0 - 4알킬, C6 - 10아릴-C0 - 4알킬, 할로-치환된-C1 - 6알킬, 히드록시-치환된-C1 - 6알킬 및 헤테로시클릴-C0 - 4알킬로부터 선택되며; 여기서 상기 헤테로시클릴은 N, NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자를 함유하는 포화, 불포화 또는 부분 불포화 5원 내지 9원 헤테로시클릭 고리이며; 여기서 R30은 수소 및 C1 - 6알킬로부터 선택되며; 여기서 상기 R2의 C6-10아릴 또는 헤테로시클릭은 할로, 히드록시, 시아노, 니트로, -NHR17, -(CH2)0-2NHC(O)R17, C1 - 6알킬, 할로-치환된-C1 - 6알킬, 아미노-치환된-C1 - 6알킬 및 C1 - 6알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되며; 여기서 R17은 수소 및 C1 - 6알킬로부터 선택되고;
R3은 수소, C1 - 6알킬, C6 - 10아릴-C0 - 4알킬, -X2C(O)OR16, -X2S(O)0-2R16, -X2OR16, -X2C(O)NHR16 및 -X2NHC(O)R16으로부터 선택되며; 여기서 X2는 결합 및 C1 - 4알킬렌으로부터 선택되며; R16은 수소, C1 - 6알킬 및 C6 - 10아릴-C0 - 4알킬로부터 선택되며; 여기서 상기 R16의 아릴은 할로, C1 - 6알킬, 할로-치환된-C1 - 6알킬, C1 - 6알콕시 및 할로-치환된-C1 - 6알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되거나; 또는
R2 및 R3은 이들이 부착된 탄소 원자와 함께 C3 - 8시클로알킬을 형성하거나; 또는
R2 및 R13은 이들이 부착된 원자와 함께 C3 - 8시클로알킬, 및 N, C(O), NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자 또는 기를 함유하는 포화, 불포화 또는 부분 불포화 5원 내지 9원 모노 또는 융합 헤테로시클릭 고리로부터 선택되는 고리를 형성하며; 여기서 R30은 수소 및 C1 - 6알킬로부터 선택되며; 여기서 상기 R2 및 R13의 조합으로부터의 헤테로시클릭은 할로, 히드록시, C1 - 6알킬 및 할로-치환된-C1 - 6알킬로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되고;
R4는 수소 및 C1 - 6알킬로부터 선택되고;
R5는 수소 및 C1 - 6알킬로부터 선택되거나; 또는 R4 및 R5는 이들이 부착된 탄소 원자와 함께 C3 - 8시클로알킬을 형성하고;
R6은 C6 - 10아릴, C3 - 8시클로알킬, 및 N, C(O), NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자 또는 기를 함유하는 포화, 불포화 또는 부분 불포화 5원 내지 9원 모노 또는 융합 헤테로시클릭 고리로부터 선택되며; 여기서 R30은 수소 및 C1-6알킬로부터 선택되며; 여기서 상기 R6의 아릴 또는 헤테로시클릭은 할로, 히드록시, C1 - 6알킬 및 C1 - 6알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼에 의해 임의로 치환되고;
R7은 수소 및 C1 - 3알킬로부터 선택되고;
R8은 C1 - 10알킬 (직쇄 또는 분지쇄), C6 - 10아릴-C0 - 4알킬, C3 - 8시클로알킬, 및 N, C(O), NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자 또는 기를 함유하는 포화, 불포화 또는 부분 불포화 5원 내지 9원 모노 또는 융합 헤테로시클릭 고리로부터 선택되며; 여기서 R30은 수소 및 C1 - 6알킬로부터 선택되며; 여기서 상기 R8의 아릴 또는 헤테로시클릭은 할로, 시아노, 히드록시, C1 - 6알킬, 할로-치환된-C1 - 6알킬, 할로-치환된-C1 - 6알콕시, C1 - 6알콕시, -C(O)OR18, -S(O)0-2R18, -C(O)NHR18, -NHS(O)0-2R18, 페닐, 및 N, C(O), NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자 또는 기를 함유하는 포화, 불포화 또는 부분 불포화 5원 또는 6원 헤테로시클릭 고리로부터 독립적으로 선택되는 1개 내지 3개 라디칼에 의해 임의로 치환되며; 여기서 R30은 수소 및 C1 - 6알킬로부터 선택되며; 여기서 상기 R8의 아릴 또는 헤테로시클릭 치환기는 할로, 시아노, 히드록시, C1 - 6알킬, 할로-치환된-C1 - 6알킬 및 할로-치환된-C1 - 6알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼에 의해 임의로 치환되며; 여기서 R18은 수소 및 C1 - 6알킬로부터 선택되고;
R9는 수소 및 C1 - 6알킬로부터 선택되고;
R10은 수소 및 C1 - 6알킬로부터 선택되고;
R11은 수소 및 C1 - 6알킬로부터 선택되고;
R12는 수소 및 C1 - 6알킬로부터 선택되거나; 또는 R11 및 R12는 조합하여 C(O)를 형성하되;
단, 하기 화합물은 본 발명으로부터 배재된다:
2-아미노-1-(3-(벤조[d][1,3]디옥솔-5-일아미노)-2-페닐-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)에탄온; 2-(2-메톡시페닐)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-페닐-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(피리딘-3-일)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 및 2-(4-플루오로페닐)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민.
제2 측면에서, 본 발명은 화학식 Ia, Ib 및 Ic로부터 선택되는 화합물, 또는 이들의 N-옥시드 유도체, 개별 이성질체 및 이성질체 혼합물; 또는 이들의 제약상 허용되는 염을 1종 이상의 적합한 부형제와의 혼합 상태로 함유하는 제약 조성물을 제공한다.
제3 측면에서, 본 발명은 치료 유효량의 화학식 Ia, Ib 및 Ic로부터 선택되는 화합물, 또는 이들의 N-옥시드 유도체, 개별 이성질체 및 이성질체 혼합물, 또는 이들의 제약상 허용되는 염을 동물에게 투여하는 것을 포함하는, 기생충 (예를 들어, 열대열원충, 삼일열원충, 난형열원충, 사일열원충, 트리파노소마 크루지, 또는 리슈마니아속의 기생충, 예컨대 리슈마니아 도노바니)에 의해 유발되는 질환의 병태 및/또는 증상을 본 발명의 화합물이 예방, 억제 또는 완화시킬 수 있는 동물에서의 질환을 치료하는 방법을 제공한다.
제4 측면에서, 본 발명은 동물에서 기생충에 의해 유발되는 질환을 치료하기 위한 의약의 제조에서의 화학식 Ia, Ib 및 Ic로부터 선택되는 화합물의 용도를 제공한다. 상기 질환은 말라리아, 리슈만편모충증 및/또는 샤가스병일 수 있다.
제5 측면에서, 본 발명은 화학식 Ia, Ib 및 Ic로부터 선택되는 화합물, 및 이들의 N-옥시드 유도체, 전구약물 유도체, 개별 이성질체 및 이성질체 혼합물, 및 이들의 제약상 허용되는 염의 제조 방법을 제공한다.
정의
"알킬"은 하나의 기로서, 그리고 다른 기, 예를 들어 할로-치환-알킬 및 알콕시의 구조적 요소로서 직쇄 또는 분지쇄일 수 있다. C1 -4-알콕시에는 메톡시, 에톡시 등이 포함된다. 할로-치환된 알킬에는 트리플루오로메틸, 펜타플루오로에틸 등이 포함된다.
"아릴"은 6개 내지 10개 고리 탄소 원자를 함유하는 모노시클릭 또는 융합된 비시클릭 방향족 고리단을 의미한다. 예를 들어, 아릴은 페닐 또는 나프틸, 바람직하게는 페닐일 수 있다. "아릴렌"은 아릴기로부터 유도된 2가 라디칼을 의미한다.
"헤테로아릴"은 아릴에 대해 정의된 바와 같고, 여기서 고리 구성원 중 하나 이상이 N, O, C(O) 및 S(O)0-2로부터 선택되는 헤테로원자이다. 예를 들어, 5원 내지 10원 헤테로아릴에는 피리딜, 인돌릴, 인다졸릴, 퀴녹살리닐, 퀴놀리닐, 벤조푸라닐, 벤조피라닐, 벤조티오피라닐, 벤조[1,3]디옥솔, 이미다졸릴, 벤조-이미다졸릴, 피리미디닐, 푸라닐, 옥사졸릴, 이속사졸릴, 트리아졸릴, 테트라졸릴, 피라졸릴, 티에닐 등이 포함된다.
"시클로알킬"은 지정된 개수의 고리 원자를 함유하는 포화 또는 부분 불포화, 모노시클릭, 융합된 비시클릭 또는 가교된 폴리시클릭 고리단을 의미한다. 예를 들어, C3 - 10시클로알킬에는 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실 등이 포함된다.
"헤테로시클릭"은 본 출원에서 정의된 바와 같되, 단 지정된 고리 탄소 중 하나 이상이 -O-, -N=, -NR-, -C(O)-, -S-, -S(O)- 또는 -S(O)2- (여기서, R은 수소, C1 - 4알킬 또는 질소 보호기임)로부터 선택되는 잔기로 대체되는 시클로알킬을 의미한다. 예를 들어, 본 발명의 화합물을 기술하기 위해서 본 출원에서 사용되는 바와 같은 3원 내지 8원 헤테로시클로알킬에는 모르폴리노, 피롤리디닐, 피페라지닐, 피페리디닐, 피페리디닐론, 1,4-디옥사-8-아자-스피로[4.5]데스-8-일 등이 포함된다.
"할로겐" (또는 할로)은 클로로, 플루오로, 브로모 또는 아이오도를 나타낸다.
치료하다", "치료하는" 및 "치료"는 질환 및/또는 그에 수반되는 증상을 완화 또는 경감시키는 방법을 지칭한다. 본 명세서에서, 용어 "치료"는, 질환에 걸릴 위험이 있는 환자 또는 질환에 걸린 것으로 의심되는 환자, 및 또한 아픈 환자의 치료를 포함하여, 치유적 또는 질환 억제적 치료 뿐만 아니라 예방적 또는 방지적 치료 모두를 포함한다. 추가적으로, 상기 용어는 질환의 진행의 지연을 위한 치료가 포함된다.
바람직한 실시양태의 기술
본 발명은 신규한 부류의 화합물, 상기 화합물을 포함하는 제약 조성물, 및 기생충과 관련된 질환 또는 장애를 치료 또는 예방하기 위한 상기 화합물의 사용 방법을 제공한다. 특히, 상기 화합물은 말라리아, 리슈만편모충증 및/또는 샤가스병을 치료하는 데 사용될 수 있다.
한 실시양태에서, 화학식 Ia, Ib 및 Ic의 화합물과 관련하여: R1은 -OR13, -C(O)OR13, -NR13R14, 페닐, 피리디닐, 인돌릴, 아제티디닐, 1H-인다졸릴, 피페리디닐 및 피리미디닐로부터 선택되며; 여기서 R13은 수소, 메틸, 에틸, 프로필, 부틸, 펜틸, 시클로프로필, 페닐, 벤질, 아미노-부틸, 히드록시-에틸, 메톡시-에틸, 부톡시-에틸, 메톡시-프로필, -C(O)R15, -C(O)OR15, -X1OR15, -X1C(NH)NHR15, -X1NHC(O)R15 및 X1C(O)NHR15로부터 선택되며; 여기서 X1은 결합 또는 C1 - 4알킬렌으로부터 선택되며; R15는 수소, 메틸, 에틸, 프로필, 부틸, t-부틸, 트리플루오로메틸 및 트리플루오로메틸-카르보닐로부터 선택되며; R14는 수소, 메틸, 에틸, 프로필, 부틸, 펜틸, 이소부틸, 히드록시-에틸, 디플루오로에틸 및 이소부틸로부터 선택되며; 여기서 R1의 임의의 페닐, 벤질 또는 헤테로시클릭은 할로, 메틸, 에틸, 트리플루오로메톡시 및 트리플루오로메틸로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되거나; 또는 R13 및 R14는 이들이 부착된 질소와 함께 피롤리디닐, 모르폴리노, 티오모르폴리노 및 피페리디닐을 형성하며; 여기서 R13 및 R14의 조합으로부터의 상기 헤테로시클릭은 할로, 트리플루오로메틸, 히드록시 및 아미노-에틸로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환된다.
또 다른 실시양태에서, R2는 수소, 메틸, 에틸, 이소프로필, 프로필, 이소부틸, 부틸, t-부틸, 트리플루오로메틸, 트리플루오로-에틸, 페닐, 벤질, 페네틸, 시클로부틸-메틸, 시클로펜틸, 시클로헥실, 시클로헥실-메틸, 히드록시-메틸 및 1-히드록시-에틸로부터 선택되며; 여기서 상기 R2의 페닐, 벤질 또는 페네틸은 할로, 메톡시, 트리플루오로메틸, 히드록시, 아미노, 니트로, 시아노, 아미노-메틸, 메틸-술포닐-에틸, 메틸-카르보닐-아미노, -NHR17, -CH2NHC(O)R17 및 -NHC(O)R17로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되며; 여기서 R17은 수소, 에틸, 프로필, 부틸 및 펜틸로부터 선택된다.
또 다른 실시양태에서, R3은 수소, 메틸, 메틸-카르보닐-아미노-부틸, 프로필-아미노-카르보닐-메틸, 카르복시-메틸, 프로필-아미노-카르보닐-메틸, 부틸-아미노-카르보닐-메틸, 펜틸-아미노-카르보닐-메틸, 프로필-아미노-카르보닐-에틸, 트리플루오로메틸-카르보닐-아미노-부틸, 페닐, 벤질-술파닐-메틸, 벤족시-카르보닐-메틸, 메틸-술포닐-메틸, 1-(벤질옥시)에틸, 벤족시-카르보닐-에틸 및 벤족시-카르보닐-아미노로부터 선택된다.
또 다른 실시양태에서, R2 및 R3은 이들이 부착된 탄소 원자와 함께 시클로프로필, 시클로부틸, 시클로펜틸 또는 시클로헥실을 형성한다.
또 다른 실시양태에서, R2 및 R13은 이들이 부착된 원자와 함께 피페리디닐, 시클로부틸, 피롤리디닐, 모르폴리노, 피페리디닐, 테트라히드로푸라닐, 테트라히드로-2H-피란-4-일, 4-옥소아제티딘-2-일, 인돌릴, 2,6-디옥소-1,2,3,6-테트라히드로피리미딘-4-일, 1,2,3,4-테트라히드로이소퀴놀린-3-일, 옥소피페리딘-3-일 또는 4,5,6,7-테트라히드로-3H-이미다조[4,5-c]피리딘-6-일을 형성한다.
추가의 실시양태에서, R4, R5, R9 및 R10은 수소 및 메틸로부터 독립적으로 선택되고; R11 및 R12는 둘 다 수소이거나; 또는 R11 및 R12는 조합하여 C(O)를 형성한다.
추가의 실시양태에서, R6은 페닐, 시클로헥실 및 피리디닐로부터 선택되며; 여기서 상기 R6의 페닐 또는 피리디닐은 할로, 펜틸, 히드록시, 메틸 및 메톡시로부터 독립적으로 선택되는 1개 내지 3개 라디칼에 의해 임의로 치환된다.
추가의 실시양태에서, R7은 수소, 메틸, 에틸 및 이소프로필로부터 선택되고; R8은 페닐, 벤질, 벤조[d][1,3]디옥솔-5-일, 시클로부틸, 시클로펜틸, 시클로헵틸, 시클로헥실, 비시클로[2.2.1]헵틸, 테트라히드로-2H-피라닐, 피리디닐, 피페리디닐, 피페라지닐, 퀴놀리닐, 피롤리디닐 및 피라졸릴로부터 선택되며; 여기서 상기 R8의 페닐, 벤질, 벤조[d][1,3]디옥솔-5-일, 시클로부틸, 시클로펜틸, 시클로헵틸, 시클로헥실, 비시클로[2.2.1]헵틸, 테트라히드로-2H-피라닐, 피리디닐, 피페리디닐, 피페라지닐, 퀴놀리닐, 피롤리디닐 또는 피라졸릴은 할로, 시아노, 메틸, 에틸, t-부틸, 트리플루오로메틸, 트리플루오로메톡시, 디메틸-아미노, 디플루오로메톡시, 카르복시, 메톡시-카르보닐, 메틸-술포닐-아미노, 메틸-술포닐, 메틸-아미노-카르보닐, 페닐, 피페리디닐, 피페리디닐-메틸, 피페라지닐 및 피페라지닐-메틸로부터 독립적으로 선택되는 1개 내지 3개 라디칼에 의해 임의로 치환된다.
또 다른 실시양태는 하기 화학식 Id의 화합물이다.
<화학식 Id>
식 중, R1은 -NH2이고; R2 및 R3은 수소 및 메틸로부터 독립적으로 선택되고; R4 및 R5는 수소 및 메틸로부터 독립적으로 선택되고; R6은 플루오로로 치환된 페닐이고; R8은 클로로 및 플루오로로부터 독립적으로 선택되는 1개 내지 2개 라디칼로 치환된 페닐이다.
추가의 실시양태는 하기로부터 선택되는 화합물이다: 2-아미노-1-(2-(4-플루오로페닐)-3-(4-플루오로페닐아미노)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)에탄온; 2-아미노-1-(3-(3,4-디플루오로페닐아미노)-2-(4-플루오로페닐)-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)-2-메틸프로판-1-온; 및 2-아미노-1-(3-(4-클로로페닐아미노)-2-(4-플루오로페닐)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)에탄온.
추가의 실시양태는 하기로부터 선택되는 화합물이다: 2-아미노-1-{3-[(3,5-디메틸페닐)아미노]-2-페닐-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(2H-1,3-벤조디옥솔-5-일아미노)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[3-(시클로펜틸아미노)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(시클로펜틸아미노)-2-페닐-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-2-메틸-1-[2-페닐-3-(페닐아미노)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 메틸 4-{[7-(2-아미노-2-메틸프로파노일)-2-페닐-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조에이트; 2-아미노-1-[2-(2-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-플루오로페닐)아미노]-2-페닐-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-플루오로페닐)아미노]-2-(2,4,6-트리플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-[2-(3,5-디플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-플루오로페닐)아미노]-2-(4-펜틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{2-시클로헥실-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-(피리딘-3-일아미노)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 4-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-페닐프로판-1-온; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-페닐프로판-1-온; 2-아미노-1-{3-[(4-브로모페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-(디메틸아미노)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(벤질아미노)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-(4-클로로페닐)-3-(4-메틸페닐)이미다조[1,2-a]피라진; N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}아세트아미드; N,2-비스(4-플루오로페닐)이미다조[1,2-a]피라진-3-아민; 2-아미노-1-[3-(시클로헥실아미노)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; N,2-비스(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2,3-비스(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(피롤리딘-1-일)에탄-1-온; 3-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(3-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(3-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(모르폴린-4-일)에탄-1-온; 4-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}-1$l^{6},4-티오모르폴린-1,1-디온; 2-(3,3-디플루오로피페리딘-1-일)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 7-[(1-아미노시클로프로필)카르보닐]-N,2-비스(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-{1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸-1-옥소프로판-2-일}아세트아미드; 2-아미노-1-[2-(4-클로로페닐)-3-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 7-벤질-N,2-비스(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 벤질 N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}카르바메이트; 2-아미노-3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-아미노-1-[2-(4-플루오로-2-히드록시페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-플루오로페닐)아미노]-2-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-플루오로페닐)아미노]-2-(4-메톡시페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-브로모페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-클로로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(3,3-디플루오로피롤리딘-1-일)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(3R)-3-플루오로피롤리딘-1-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(3S)-3-플루오로피롤리딘-1-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(4-플루오로피페리딘-1-일)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[4-(트리플루오로메틸)피페리딘-1-일]에탄-1-온; 2-(4,4-디플루오로피페리딘-1-일)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[3-(트리플루오로메틸)피페리딘-1-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(3-히드록시피페리딘-1-일)에탄-1-온; 2-[(2,2-디플루오로에틸)아미노]-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,5-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3,5-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-(시클로프로필아미노)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(2-메틸프로필)아미노]에탄-1-온; 2-아미노-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-{[4-(트리플루오로메틸)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-{[4-(트리플루오로메틸)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(3,3-디플루오로피페리딘-1-일)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)에탄-1-온; 1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(3,3-디플루오로피페리딘-1-일)에탄-1-온; 1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(메틸아미노)에탄-1-온; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(2,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(2,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-페닐에탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(3R)-피페리딘-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(3S)-피페리딘-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-[2-(디에틸아미노)에틸]-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-{[(2S)-아제티딘-2-일]카르보닐}-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2R)-피롤리딘-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2S)-피롤리딘-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2S)-피페리딘-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2R)-피페리딘-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(3R)-피롤리딘-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(3S)-피롤리딘-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐에탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐에탄-1-온; 1-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}시클로프로판-1-올; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-3-메틸부탄-1-온; N-[(5S)-5-아미노-6-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-6-옥소헥실]아세트아미드; N-[(5S)-5-아미노-6-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-6-옥소헥실]-2,2,2-트리플루오로아세트아미드; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; (1S,2S)-2-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}시클로펜탄-1-올; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-페닐프로판-1-온; 2-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시부탄-1-온; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-페닐프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3,3-디메틸부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-페닐프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2,2-디페닐에탄-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-(트리플루오로메틸)부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-메틸프로판-1-온; 1-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}시클로펜탄-1-올; 1-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}시클로헥산-1-올; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-4-페닐부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-2,2-디메틸-3-(4-메틸페닐)프로판-1-온; 4,4,4-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-3-메틸부탄-1-온; (2S)-2-시클로헥실-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-(4-메톡시페닐)에탄-1-온; 2-(3,5-디플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-[3-(트리플루오로메틸)페닐]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메톡시-2-페닐에탄-1-온; 2-(4-브로모페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-[4-(트리플루오로메틸)페닐]에탄-1-온; 3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메톡시-2-페닐프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-(3-히드록시페닐)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-(4-히드록시페닐)에탄-1-온; 2-(2-클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 2-(4-브로모-2-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 2-(4-클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-4-메틸펜탄-1-온; (3S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-3-페닐프로판-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)이미다조[1,2-a]피라진-3-아민; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-페닐에탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-페닐에탄-1-온; 7-[(1-아미노시클로부틸)카르보닐]-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-[(1-아미노시클로펜틸)카르보닐]-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-[(1-아미노시클로헥실)카르보닐]-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-4,4,4-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-3-메틸펜탄-1-온; 2-아미노-3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-3-시클로헥실-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시프로판-1-온; 2-(벤질아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(디프로필아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-(디프로필아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)-3-페닐프로판-1-온; 벤질 (4S)-4-{[(tert-부톡시)카르보닐]아미노}-5-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-5-옥소펜타노에이트; 벤질 (3S)-3-{[(tert-부톡시)카르보닐]아미노}-4-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소부타노에이트; tert-부틸 N-[(5S)-5-{[(벤질옥시)카르보닐]아미노}-6-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-6-옥소헥실]카르바메이트; 2-(시클로프로필아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; N-[4-({2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}아미노)부틸]아세트아미드; 2-(4-플루오로페닐)-7-{2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에틸}-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2,6-디아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]헥산-1-온; (2S)-2-아미노-3-(4-아미노페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; N-[(5S)-5-아미노-6-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-6-옥소헥실]부탄아미드; N-[(5S)-5-아미노-6-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-6-옥소헥실]-1-(5-{2-옥소-헥사히드로-1H-티에노[3,4-d]이미다졸리딘-4-일}펜탄아미도)-3,6,9,12-테트라옥사펜타데칸-15-아미드; N-{4-[(2S)-2-아미노-3-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}아세트아미드; 2-[비스(2-히드록시에틸)아미노]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (4S)-4-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}아제티딘-2-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시프로판-1-온; 2,2,2-트리플루오로-N-[(2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-1-옥소프로판-2-일]아세트아미드; 6-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}-1,2,3,4-테트라히드로피리미딘-2,4-디온; {2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}우레아; 1-{2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}구아니딘; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(페닐아미노)에탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸부탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3,3-디메틸부탄-1-온; (3S)-3-아미노-4-(4-브로모페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; (3S)-3-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-(2,4,5-트리플루오로페닐)부탄-1-온; 2-(4-클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-(4-클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐프로판-1-온; 2-(4-플루오로페닐)-7-{[(6S)-1H,4H,5H,6H,7H-이미다조[4,5-c]피리딘-6-일]카르보닐}-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-(디메틸아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-페닐프로판-1-온; 2-[4-(2-아미노에틸)피페리딘-1-일]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(4-플루오로페닐)-7-[(4-메탄술포닐페닐)메틸]-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[4-(모르폴린-4-일)페닐]메틸}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[4-(4-메틸피페라진-1-일)페닐]메틸}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-{[4-(디에틸아미노)페닐]메틸}-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-({4-[3-(디메틸아미노)프로폭시]페닐}메틸)-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[4-(피리딘-4-일)페닐]메틸}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; tert-부틸 N-[(2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-(4-프로판아미도페닐)프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-(프로필카르바모일)프로판-2-일]카르바메이트; N-{4-[(2S)-2-아미노-3-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}프로판아미드; (4S)-4-아미노-5-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-5-옥소-N-프로필펜탄아미드; (3S)-3-아미노-4-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소-N-프로필부탄아미드; 3-아미노-4,4,4-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; 2-(3-플루오로페닐)-N-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-{[(1S,2R)-2-아미노시클로펜틸]카르보닐}-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3,3,3-트리플루오로프로판-1-온; (2R)-2-아미노-3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; N-{4-[(2S)-2-아미노-3-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}부탄아미드; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메톡시프로판-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2R)-옥솔란-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2S)-옥솔란-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페녹시부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페녹시프로판-1-온; 2-(3-클로로페녹시)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(피리미딘-4-일)에탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(3-플루오로페닐)이미다조[1,2-a]피라진-3-아민; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸-2-(2-메틸페녹시)부탄-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-[(옥산-4-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-에톡시-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(4-히드록시페닐)프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(옥솔란-2-일)에탄-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-[(옥솔란-3-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-3-[4-(아미노메틸)페닐]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-(1-에틸피페리딘-4-일)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(옥솔란-3-일)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(옥산-2-일)에탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-({4-[(2S)-2-아미노-3-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}메틸)부탄아미드; N-({4-[(2S)-2-아미노-3-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}메틸)프로판아미드; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(피페리딘-4-일)에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3,3,3-트리플루오로프로판-1-온; (2R)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-페닐프로판-1-온; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-페닐프로판-1-온; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐부탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐부탄-1-온; 2-시클로펜틸-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(피리딘-4-일)에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-(3,5-디클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸-2-페닐부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(4-메틸페닐)에탄-1-온; 2-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-히드록시-3-메틸부탄-1-온; 1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-3-메틸부탄-1-온; 벤질 (3S)-3-{[(tert-부톡시)카르보닐]아미노}-4-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-옥소부타노에이트; 벤질 (3S)-3-{[(tert-부톡시)카르보닐]아미노}-4-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소부타노에이트; tert-부틸 N-[(2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-니트로페닐)-1-옥소프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(4-니트로페닐)-1-옥소프로판-2-일]카르바메이트; (3S)-3-{[(tert-부톡시)카르보닐]아미노}-4-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-옥소부탄산; (3S)-3-{[(tert-부톡시)카르보닐]아미노}-4-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소부탄산; tert-부틸 N-[(2S)-3-(4-아미노페닐)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-1-옥소프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-3-(4-아미노페닐)-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소프로판-2-일]카르바메이트; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-2,2-디메틸프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-2-(히드록시메틸)-2-메틸프로판-1-온; tert-부틸 N-[(2S)-3-(3-아미노페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-1-옥소-3-(프로필카르바모일)프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-(프로필카르바모일)프로판-2-일]카르바메이트; 4-{[2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; tert-부틸 N-[(2S)-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-(펜틸카르바모일)프로판-2-일]카르바메이트; 1-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}-N,N-디메틸피롤리딘-3-아민; tert-부틸 N-[(2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-1-옥소-3-(4-펜탄아미도페닐)프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-1-옥소-3-(4-프로판아미도페닐)프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-(4-펜탄아미도페닐)프로판-2-일]카르바메이트; (3S)-3-아미노-4-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-옥소-N-프로필부탄아미드; (3S)-3-아미노-4-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소-N-프로필부탄아미드; (3S)-3-아미노-4-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소-N-펜틸부탄아미드; N-{4-[(2S)-2-아미노-3-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-옥소프로필]페닐}펜탄아미드; N-{4-[(2S)-2-아미노-3-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-옥소프로필]페닐}프로판아미드; N-{4-[(2S)-2-아미노-3-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}펜탄아미드; N-{4-[(2S)-2-아미노-3-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}프로판아미드; N-(4-클로로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 4-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 4-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 4-{[2-(4-플루오로페닐)-7-(3-히드록시-3-메틸부타노일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 2-(3-메틸페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; tert-부틸 N-[(2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-[4-(펜틸아미노)페닐]프로판-2-일]카르바메이트; 2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸 프로파노에이트; 2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸 부타노에이트; 2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸 펜타노에이트; 2-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-1-(4-플루오로페닐)에탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-[4-(펜틸아미노)페닐]프로판-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[4-(3-메틸피페리딘-1-일)피페리딘-1-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[4-(피페리딘-1-일)피페리딘-1-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-7-{[4-(4-플루오로페닐)피페리딘-1-일]카르보닐}-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 에틸 1-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}피페리딘-3-카르복실레이트; N-[2-(디에틸아미노)에틸]-2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-카르복스아미드; 2-(3,4-디플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(3-클로로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(2,4-디플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-[(2-히드록시프로필)아미노]-3-페닐프로판-1-온; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-[(2-메톡시에틸)아미노]-3-페닐프로판-1-온; 3-{[(5R,8S)-2,8-디벤질-3-메틸-5-(2-페닐에틸)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}피리딘; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시프로판-1-온; (2R,3S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시부탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-메탄술포닐부탄-1-온; (3R)-3-아미노-4-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소부탄산; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메탄술포닐프로판-1-온; (5R,8R)-2,8-디벤질-3-메틸-5-(2-페닐에틸)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; N-[(1S)-2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸]프로판아미드; N-[(1S)-2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸]부탄아미드; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-N-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)(메틸)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)(메틸)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; (2S)-2-(부틸아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐에탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(펜틸아미노)-2-페닐에탄-1-온; N-tert-부틸-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-[(1S)-2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸]-1-(5-{2-옥소-헥사히드로-1H-티에노[3,4-d]이미다졸리딘-4-일}펜탄아미도)-3,6,9,12-테트라옥사펜타데칸-15-아미드; 3-아미노-2-(4-플루오로페닐)-7-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메톡시프로판-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(피리딘-4-일)에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(1H-인돌-1-일)에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(1-에틸피페리딘-4-일)에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(페닐아미노)에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(1H-인다졸-3-일)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(프로필아미노)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(펜틸아미노)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(2-메톡시에틸)아미노]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(3-메톡시프로필)아미노]에탄-1-온; (2R)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-페닐프로판-1-온; (2S,3S)-2-아미노-3-(벤질옥시)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(1,3-티아졸-4-일)프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-플루오로페닐)프로판-1-온; (2S,3S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸펜탄-1-온; (2R)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(3,4-디플루오로페닐)프로판-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸-2-(메틸아미노)프로판-1-온; 7-{[(2S)-아제티딘-2-일]카르보닐}-N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-메틸펜탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-[(모르폴린-3-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-페닐프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-시클로부틸프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3,3-디메틸부탄-1-온; (2R)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; 4-[(2S)-2-아미노-3-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-옥소프로필]벤조니트릴; 2-(4-플루오로페닐)-6-메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(2,5-디플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3,4-디플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-페닐-2-(페닐아미노)에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-[2-(트리플루오로메톡시)페닐]에탄-1-온; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-페닐프로판-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-[4-플루오로-3-(트리플루오로메틸)페닐]에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-페녹시에탄-1-온; 5-({3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}카르보닐)피페리딘-2-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-{[(2S)-피롤리딘-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 3-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4,4,4-트리플루오로부탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-{[(3S)-피롤리딘-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-메틸페닐)프로판-1-온; N-(4-클로로-3-플루오로페닐)-7-[(2,3-디히드로-1H-이소인돌-1-일)카르보닐]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로-3-플루오로페닐)-7-{[(2S)-2,3-디히드로-1H-인돌-2-일]카르보닐}-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (3S)-3-아미노-4-(4-브로모페닐)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}부탄-1-온; (2R)-2-아미노-3-(4-브로모페닐)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-{[(4-메톡시페닐)메틸]술파닐}프로판-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-{[(3R)-1,2,3,4-테트라히드로이소퀴놀린-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4,4,4-트리플루오로부탄-1-온; 2-(2-부톡시에톡시)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-에톡시-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(2-메톡시에톡시)에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-6-메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 5-{[7-(2-아미노-2-메틸프로파노일)-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-플루오로벤조니트릴; N-(4-메틸페닐)-2-(피리딘-4-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-{[2-클로로-4-(트리플루오로메틸)페닐]아미노}-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸부탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-{[(2R)-옥솔란-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(1-메틸-1H-인돌-3-일)에탄-1-온; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-4-메틸펜탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(2-플루오로페닐)프로판-1-온; (2R)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; 2-[(3-클로로페닐)아미노]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(4-메틸페닐)아미노]에탄-1-온; 2-(4-클로로-3-플루오로페닐)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(4-메톡시페닐)아미노]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(3,4-디클로로페닐)에탄-1-온; 2-아미노-3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-[(모르폴린-2-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-[4-(트리플루오로메틸)페닐]에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(4-클로로페닐)에탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-[(퀴놀린-6-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(4-메틸페닐)아미노]-2-페닐에탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-[(4-메틸모르폴린-2-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(2-플루오로페닐)아미노]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸-2-(페닐아미노)프로판-1-온; 2-아미노-1-(3-{[4-플루오로-2-(트리플루오로메틸)페닐]아미노}-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)-2-메틸프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸-2-(메틸아미노)부탄-1-온; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-메틸-2-(메틸아미노)펜탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-메틸-2-(메틸아미노)펜탄-1-온; 2-아미노-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-[(2,6-디메틸페닐)아미노]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-아미노-1-[2-(2-메톡시페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-메틸페닐)아미노]-2-(피리딘-4-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(3-클로로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-[(2,4-디메틸페닐)아미노]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸-2-[(4-메틸페닐)아미노]프로판-1-온; 2-아미노-1-[2-(2,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-[벤질(메틸)아미노]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)헥산-1-온; 1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(4-메틸페닐)에탄-1-온; (2R)-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)펜탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}부탄-1-온; (2R)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-메틸펜탄-1-온; 2-아미노-1-[2-(2,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; (2S)-2-아미노-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸부탄-1-온; 2-아미노-1-[2-(3-클로로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-2-메틸-1-{3-[(4-메틸페닐)아미노]-2-(피리딘-4-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; 2-(tert-부틸아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-3-(4-클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)프로판-1-온; (2S)-2-아미노-3-시클로프로필-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2R)-2-(벤질아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-(벤질아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-2-시클로프로필-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-아미노-3-(3,4-디플루오로페닐)-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(4-메틸페닐)아미노]프로판-1-온; 2-아미노-1-[2-(2,5-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,4-디클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; N-(3,4-디클로로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; N-(4-클로로-3-플루오로페닐)-N-에틸-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸-2-(메틸아미노)부탄-1-온; 2-(4-플루오로페닐)-8,8-디메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(2,5-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; N-(3,4-디플루오로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; N-(3-클로로-4-플루오로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 4-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 4-{[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 2-아미노-1-{3-[(3,4-디플루오로-5-메톡시페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-플루오로-3,5-디메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; (2S)-2-아미노-3-시클로부틸-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2R)-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(1,3-티아졸-4-일)프로판-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-메틸페닐)프로판-1-온; (2S)-2-아미노-3-(3,4-디플루오로페닐)-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(4-플루오로페닐)에탄-1-온; (2S)-2-아미노-2-시클로프로필-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; (2S)-2-아미노-3-시클로프로필-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-메틸펜탄-1-온; (2S)-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; 7-{[(2S)-아제티딘-2-일]카르보닐}-N-(3,4-디플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S,3S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸펜탄-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-플루오로페닐)프로판-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-N-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3-플루오로페닐)-2-(4-플루오로페닐)-N-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-에틸-N-(3-플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3-클로로-4-플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-시클로프로필에탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-시클로프로필프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-시클로부틸프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-메틸펜탄-1-온; (2S,3S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸펜탄-1-온; (2S)-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; (2R)-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(4-플루오로페닐)에탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-플루오로페닐)프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-메틸페닐)프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(3,4-디플루오로페닐)프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(1,3-티아졸-4-일)프로판-1-온; 7-{[(2S)-아제티딘-2-일]카르보닐}-N-(4-클로로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3,3-디메틸부탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸부탄-1-온; (2S)-2-아미노-2-시클로프로필-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-아미노-3-시클로프로필-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-3-시클로부틸-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-메틸펜탄-1-온; (2S,3S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸펜탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; (2R)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; (2S)-2-아미노-2-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-아미노-3-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(4-메틸페닐)프로판-1-온; (2S)-2-아미노-3-(3,4-디플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(1,3-티아졸-4-일)프로판-1-온; 7-{[(2S)-아제티딘-2-일]카르보닐}-N,2-비스(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3,3-디메틸부탄-1-온; (2S)-2-아미노-3-시클로부틸-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-메틸펜탄-1-온; (2S,3S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸펜탄-1-온; (2S)-2-아미노-2-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(4-메틸페닐)프로판-1-온; (2S)-2-아미노-3-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-3-(3,4-디플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(1,3-티아졸-4-일)프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-시클로프로필에탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-시클로프로필프로판-1-온; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(4-플루오로페닐)에탄-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3,3-디메틸부탄-1-온; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; N,2-비스(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로-3-메틸페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-(3-클로로-4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-클로로-3-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(3-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(4-플루오로페닐)-8,8-디메틸-3-{[3-(트리플루오로메틸)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(3-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (2S)-2-아미노-3-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2,4-디메틸펜탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-2-메틸프로판-1-온; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-2-메틸프로판-1-온; 3-[(3,4-디클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 4-{[2-(4-플루오로페닐)-8,8-디메틸-6-옥소-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; N-(3-플루오로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-8,8-디메틸-N-[3-(트리플루오로메틸)페닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2,2,2-트리플루오로-1-[2-(4-플루오로페닐)-3-[(3-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로-3-메틸페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로-3-메틸페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(3-클로로-4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-클로로-3-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-클로로-3-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 5-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-플루오로벤조니트릴; 2-플루오로-5-{[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조산; 2-플루오로-5-{[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 5-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; 5-{[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조산; 5-{[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; 2,2,2-트리플루오로-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[3-(트리플루오로메틸)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; tert-부틸 N-{1-[3-브로모-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸-1-옥소프로판-2-일}카르바메이트; 2-아미노-1-[3-(시클로헥실아미노)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3-클로로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3-플루오로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 4-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-클로로벤조니트릴; 5-{[2-(4-플루오로페닐)-8,8-디메틸-6-옥소-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; N,2-비스(4-플루오로페닐)-5,5,7,8,8-펜타메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-플루오로-5-{[2-(4-플루오로페닐)-8,8-디메틸-6-옥소-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 2-(4-플루오로페닐)-5,5,7,8,8-펜타메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-5,5,7,8,8-펜타메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; tert-부틸 N-{2-[2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}카르바메이트; N-(3-플루오로-4-메틸페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3-클로로-4-메틸페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-8,8-디메틸-3-[(3,4,5-트리플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(6-메톡시피리딘-3-일)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(3-클로로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸피리딘-2-일)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-클로로-4-{[2-(4-플루오로페닐)-8,8-디메틸-6-옥소-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; (8R)-3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (8R)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(3,4-디플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; N-(3-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}페닐)메탄술폰아미드; 3-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-N-메틸벤즈아미드; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(3,4,5-트리플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(4-플루오로페닐)-8,8-디메틸-N-(3,4,5-트리플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로페닐)-2-(4-플루오로페닐)-6,6,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; N-(4-클로로페닐)-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (8S)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(1,5-디메틸-1H-피라졸-3-일)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-({[(2S)-1-에틸피롤리딘-2-일]메틸}아미노)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (8S)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (8S)-3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (8R)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (8R)-3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-8,8-디메틸-3-(퀴놀린-3-일아미노)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(4-메탄술포닐페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-8,8-디메틸-3-{[4-(4-메틸피페라진-1-일)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-8,8-디메틸-3-({3-[(4-메틸피페라진-1-일)메틸]페닐}아미노)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메탄술포닐페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[4-(4-메틸피페라진-1-일)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(4-플루오로페닐)-8,8-디메틸-N-[4-(4-메틸피페라진-1-일)페닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-[2-(4-플루오로페닐)-6,6-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 5-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-플루오로벤조니트릴; 2-(4-플루오로페닐)-6,6-디메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N,2-비스(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3,4-디플루오로페닐)-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-플루오로-5-{[2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 2-(3-플루오로페닐)-7-[(4-메톡시페닐)메틸]-5,5-디메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3,4-디클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 5-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; 4-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-클로로벤조니트릴; (2S)-1-[2-(3-플루오로페닐)-5,5-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; 2-아미노-1-[2-(3-플루오로페닐)-5,5-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(3-플루오로페닐)-5,5-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[(8S)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[(8R)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[(8S)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 3-[(3-플루오로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (2S)-1-[2-(3-플루오로페닐)-5,5-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-페닐프로판-1-온; 2-아미노-1-{3-[(1,5-디메틸-1H-피라졸-3-일)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(1-에틸-1H-피라졸-5-일)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[(8R)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 3-[(3-플루오로-4-메틸페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(3-클로로-4-메틸페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; N,2-비스(4-플루오로페닐)-7,8,8-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로페닐)-2-(4-플루오로페닐)-7,8,8-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로페닐)-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로-3-메틸페닐)-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3,4-디플루오로페닐)-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 5-{[2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-7-[(4-메톡시페닐)메틸]-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-7-[(4-메톡시페닐)메틸]-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; N-(3-클로로-4-플루오로페닐)-2-(4-플루오로페닐)-7,8,8-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 5-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; 2-아미노-1-{3-[(3-플루오로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3-클로로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-(3-{[3-클로로-4-(트리플루오로메틸)페닐]아미노}-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)-2-메틸프로판-1-온; 2-아미노-1-(3-{[4-플루오로-3-(트리플루오로메틸)페닐]아미노}-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)-2-메틸프로판-1-온; 4-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-(트리플루오로메틸)벤조니트릴; 5-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-플루오로벤조니트릴; 2-아미노-1-{3-[(3,4-디메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(3-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(3-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-{[3-(트리플루오로메톡시)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-에틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-(3-{[4-(디플루오로메톡시)페닐]아미노}-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-{[4-(트리플루오로메톡시)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(3,5-디클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 10-[(3,4-디플루오로페닐)아미노]-11-(4-플루오로페닐)-4,4-디메틸-3,6,9,12-테트라아자트리시클로[7.3.0.0{2,6}]도데카-1(12),2,10-트리엔-5-온; 10-[(3,4-디플루오로페닐)아미노]-11-(4-플루오로페닐)-4,4-디메틸-3,6,9,12-테트라아자트리시클로[7.3.0.0{2,6}]도데카-1(12),10-디엔-5-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-페닐페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-에틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[4-(트리플루오로메톡시)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[3-(트리플루오로메톡시)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3-클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[3-(트리플루오로메틸)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 3-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 2-아미노-1-{3-[(3,4-디메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 4-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-(트리플루오로메틸)벤조니트릴; 2-아미노-1-{3-[(3,5-디메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-(3-{[4-플루오로-3-(트리플루오로메틸)페닐]아미노}-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)에탄-1-온; 2-아미노-1-(3-{[3-클로로-4-(트리플루오로메틸)페닐]아미노}-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4,4-디플루오로시클로헥실)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-페닐시클로헥실)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[4-(트리플루오로메틸)시클로헥실]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-tert-부틸시클로헥실)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(2-메틸시클로헥실)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(시클로헵틸아미노)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(3,3,5-트리메틸시클로헥실)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(1R,2R,4S)-비시클로[2.2.1]헵탄-2-일아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[3-(디메틸아미노)피롤리딘-1-일]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[4-(피페리딘-1-일)피페리딘-1-일]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(시클로펜틸아미노)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(시클로부틸아미노)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-(옥산-4-일아미노)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[4-(1-메틸피페리딘-4-일)피페라진-1-일]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(2-메틸부틸)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-5,5-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로페닐)(메틸)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 7-[2-(디메틸아미노)에틸]-2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 7-[2-(디메틸아미노)에틸]-3-[(3-플루오로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(3-클로로-4-메틸페닐)아미노]-7-[2-(디메틸아미노)에틸]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 7-[2-(디메틸아미노)에틸]-3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-메틸페닐)아미노]-7-[2-(디메틸아미노)에틸]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-플루오로페닐)아미노]-7-[2-(디메틸아미노)에틸]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 7-(아제티딘-3-일메틸)-3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 7-(2-아미노에틸)-2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-7-(2-히드록시에틸)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 7-(3-아미노프로필)-3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-7-(3-히드록시프로필)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-7-(3-메톡시프로필)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 4-{3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-6-옥소-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}부탄산; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)메틸]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)메틸]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메톡시페닐)메틸]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)메틸]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)메틸]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸피페라진-1-일)메틸]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(시클로헥실메틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(4-메틸페닐)프로판-1-온; 2-아미노-4-(3-플루오로페닐)-1-[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; 2-아미노-4-(4-클로로페닐)-1-[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; 2-아미노-3-시클로헥실-1-[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2,3-비스(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(3-클로로-4-플루오로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; N,2-비스(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-카르복스아미드; 7-(2-아미노아세틸)-N,2-비스(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-카르복스아미드; 2-아미노-1-[3-(4-플루오로페녹시)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(4-클로로페녹시)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(3,4-디플루오로페녹시)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(4-플루오로-3-메틸페녹시)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)술파닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(3-플루오로페닐)술파닐]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)술파닐]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-클로로페닐)술파닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3,5-디메틸페닐)술파닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)술파닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3-플루오로벤젠)술피닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-플루오로벤젠)술피닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸벤젠)술피닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,5-디메틸벤젠)술피닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3,4-디플루오로벤젠)술피닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로벤젠)술피닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 및 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸벤젠)술포닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온.
본 발명의 소정의 실시양태는 하기로부터 선택되는 화합물이다: N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}-3-페닐프로판아미드; N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}-3-{8-옥사트리시클로[7.4.0.0{2,7}]트리데카-1(9),2,4,6,10,12-헥사엔-4-일}프로판아미드; N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}-3-(3-페닐프로판아미도)프로판아미드; N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}-3-(3-{8-옥사트리시클로[7.4.0.0{2,7}]트리데카-1(9),2,4,6,10,12-헥사엔-4-일}프로판아미도)프로판아미드; N-[3-({2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}아미노)프로필]-3-페닐프로판아미드; 5,5-디플루오로-3-(3-(2-(2-(4-플루오로페닐)-3-(4-플루오로페닐아미노)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)-2-옥소에틸아미노)-3-옥소프로필)-7-페닐-5H-디피롤로[1,2-c:1',2'-f][1,3,2]디아자보리닌-4-이움-5-우이드; 및 5,5-디플루오로-2-(3-(6-(2-(2-(4-플루오로페닐)-3-(4-플루오로페닐아미노)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)-2-옥소에틸아미노)-6-옥소헥실아미노)-3-옥소프로필)-7-(4-메톡시페닐)-1,3-디메틸-5H-디피롤로[1,2-c:1',2'-f][1,3,2]디아자보리닌-4-이움-5-우이드.
본 발명의 소정의 실시양태는 하기로부터 선택되는 화합물이다: N-(4-메틸페닐)-2-(피리딘-3-일)-5H,6H,7H,8H-이미다조[1,2-a]피리딘-3-아민; 2-시클로헥실-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(디페닐메틸)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(2-니트로페닐)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-[2-(티오펜-2-일)페닐]-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-[2-(디플루오로메톡시)페닐]-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(2-브로모페닐)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-{2-[2-(디에틸아미노)에톡시]페닐}-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-[2-(트리플루오로메틸)페닐]-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(2-{3-[(2,4,4-트리메틸펜탄-2-일)아미노]이미다조[1,2-a]피리딘-2-일}페녹시)에탄-1-올; 2-[2-(푸란-2-일)페닐]-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(4-플루오로페닐)-6-메틸-N-(4-메틸페닐)이미다조[1,2-a]피리딘-3-아민; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피리딘-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피리딘-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)이미다조[1,2-a]피리딘-3-아민; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-6-메틸이미다조[1,2-a]피리딘-3-아민; 2-(4-플루오로페닐)-6-메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피리딘-3-아민; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-6-메틸-5H,6H,7H,8H-이미다조[1,2-a]피리딘-3-아민; 8-(3,4-디플루오로페닐아미노)-9-(4-플루오로페닐)-2,2-디메틸-5,6-디히드로디이미다조[1,2-a:2',1'-c]피라진-3(2H)-온; 및 8-(3,4-디플루오로페닐아미노)-9-(4-플루오로페닐)-2,2-디메틸-1,2,5,6-테트라히드로디이미다조[1,2-a:2',1'-c]피라진-3(10bH)-온.
본 발명의 추가 실시양태는, 치료 유효량의 본 발명의 화합물을 단독으로 또는 제2 작용제와 조합하여 대상체에게 생체내 또는 시험관내 투여하는 것을 포함하는, 열원충 관련 질환의 병태 및/또는 증상을 예방, 억제 또는 완화시키기 위한 대상체에서의 열원충 관련 질환의 치료 방법이다.
추가의 실시양태에서, 치료 유효량의 소정 화합물을 단독으로 또는 제2 작용제와 조합하여 대상체에게 생체내 또는 시험관내 투여하는 것을 포함하는, 열원충 관련 질환의 병태 및/또는 증상을 예방, 억제 또는 완화시키기 위한 대상체에서의 열원충 관련 질환의 치료 방법이며, 여기서 상기 화합물은 하기로부터 선택된다: 2-아미노-1-(3-(벤조[d][1,3]디옥솔-5-일아미노)-2-페닐-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)에탄온; 2-(2-메톡시페닐)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-페닐-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(피리딘-3-일)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 및 2-(4-플루오로페닐)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민.
추가의 실시양태에서, 열원충 관련 질환은 말라리아이다.
추가의 실시양태에서, 제2 작용제는 키나제 억제제, 항말라리아 약물 및 소염제로부터 선택된다. 항말라리아 약물은 프로구아닐, 클로르프로구아닐, 트리메토프림, 클로로퀸, 메플로퀸, 루메판트린, 아토바쿠온, 피리메타민-술파독신, 피리메타민-다프손, 할로판트린, 퀴닌, 퀴니딘, 아모디아퀸, 아모피로퀸, 술폰아미드, 아르테미시닌, 아르테플렌, 아르테메테르, 아르테수네이트, 프리마퀸 및 피로나리딘으로부터 선택된다.
추가의 실시양태에서, 본 발명의 화합물은 제2 작용제 전에, 이와 동시에 또는 후에 투여될 수 있다.
추가의 실시양태에서, 대상체는 인간이다.
약리 및 효용
본 발명의 화합물은 열대열원충, 삼일열원충, 난형열원충 및 사일열원충; 트리파노소마 크루지; 및 리슈마니아속의 기생충, 예컨대 리슈마니아 도노바니에 의해 유발되는 것과 같은 감염의 치료 및/또는 예방에 유용하다.
말라리아는 4가지 원생 기생충, 즉, 열대열원충; 삼일열원충; 난형열원충; 및 사일열원충에 의해 유발되는 감염성 질환이다. 이들 4가지 기생충은 통상 감염된 암컷 학질모기가 물어 전파된다. 말라리아는 세계 여러 곳에서 문제를 일으키며, 최근 수 십년에 걸쳐 말라리아 부담은 꾸준히 증가하였다. 어림잡아 1 내지 3백만명의 사람들이 매년 말라리아로 사망하며, 대부분 5세 미만의 어린이이다. 말라리아 사망자 수의 증가는, 치명적인 말라리아 기생충인 열대열원충이 아르테미시닌 유도체를 제외하고는 거의 모든 이용가능한 항말라리아 약물에 대해 내성을 획득하였다는 사실에 일부 기인한다.
리슈만편모충증은 리슈마니아속에 속하는 20종 초과의 기생 원충에 의해 유발되며, 암컷 응애가 물어 전파된다. 리슈만편모충증은 여러 열대 및 아열대 지역을 포함한 약 88개국에서 풍토적이다.
리슈만편모충증의 4가지 주요 형태가 있다. 칼라-아자르로도 불리는 내장리슈만편모충증이 가장 심각한 형태이며, 기생충 리슈마니아 도노바니에 의해 유발된다. 내장리슈만편모충증이 발병한 환자는 치료를 받지 않는 경우 수 개월 이내에 사망할 수 있다. 내장리슈만편모충증에 대한 2가지 주요 요법은 안티몬 유도체 나트륨 스티보글루코네이트 (펜토스탐®) 및 메글루민 안티모니에이트 (글루칸팀®)이다. 나트륨 스티보글루코네이트는 약 70여년간 사용되어 왔으며, 상기 약물에 대한 내성이 점점 문제가 된다. 또한, 치료는 비교적 장기간이며, 고통스럽고, 원치 않는 부작용을 일으킬 수 있다.
수면병으로도 알려져 있는 인간 아프리카 트리파노소마증은 매개체-감염 기생충 질환이다. 관련 기생충은 트리파노소마속에 속하는 원충이다. 이들은 인간 병원성 기생충을 보유한 인간 또는 동물로부터 감염된 체체파리 (글로시나속)가 물어 인간에게 전파된다.
샤가스병 (아메리카 트리파노소마증으로도 불림)은 아메리카 대륙의 가난한 집단 사이에서 고질적인 또 다른 인간 기생충 질환이다. 상기 질환은 원생 기생충인 트리파노소마 크루지에 의해 유발되며, 이는 흡혈 곤충에 의해 인간에게 전파된다. 상기 인간 질환은 감염 후 빠르게 발생하는 급성 단계 및 수 년에 걸쳐 발병할 수 있는 만성 단계의 2단계로 발생한다. 만성 감염은 치매, 심근 손상 및 때때로 소화관 팽창, 및 또한 체중 감소를 비롯하여 다양한 신경학적 장애를 일으킨다. 치료되지 않은 만성 질환은 종종 치명적이다.
샤가스병의 치료에 대해 현재 이용가능한 약물은 니푸르티목스 및 벤즈니다졸이다. 그러나, 이러한 현행 요법의 문제로는 그들의 다양한 부작용, 치료 기간, 및 치료 중 의학적 관리에 대한 요구를 들 수 있다. 게다가, 치료는 실제로 질환의 급성 단계 중에 제공된 경우에만 효과적이다. 2가지 1차 약물에 대한 내성은 이미 발생하였다. 항진균제인 암포테리신 b가 2차 약물로 제안된 바 있지만, 상기 약물은 고가이며 비교적 독성이 있다.
정복합체포자동물문은, 이들로 한정되지는 않지만, 열원충속 (Plasmodium spp.) (말라리아), 톡소플라즈마원충 (Toxoplasma gondii) (인간에서의 선천적인 신경계 장애), 아이메리아속 (Eimeria spp .) (가금류 및 축우 병원체), 크립토스포리디아 (Cryptosporidia) (기회감염성 인간 및 동물 병원체), 바베시아 (Babesia) (축우 기생충) 및 연안열원충 (Theileria) (축우 기생충)을 비롯하여 인간 또는 동물 병원체인 다수의 구성원을 함유한다. 이들 기생충 질환과 연관된 발병기전은 숙주-세포 침입, 세포내 복제 및 숙주-세포 용균의 반복 주기에 기인한다. 따라서, 이해하고 있는 기생충 증식이, 예를 들어 말라리아를 치료하기 위한 신규 약물 및 백신의 개발에 필수적이다.
척추동물 숙주에서, 기생충은 간세포기 및 적혈구기의 2가지 주요 발생 단계를 겪지만, 그의 생활 주기 중 적혈구기가 심한 병리를 유발한다. 적혈구기 동안, 기생충이 복잡하지만 잘 동기화된 일련의 단계를 거치는 것은 엄격히 조절된 신호전달 경로가 있음을 시사한다.
칼슘은 적혈구 생활 단계에서 동기화 및 발생을 제어하는 세포내 메신저로서의 역할을 한다. 열원충속 게놈은 Pf39, 칼모듈린 및 칼슘 의존성 단백질 키나제 (CDPK)를 포함하는 칼슘 결합/감지 단백질 모티프와 많은 서열 동일성을 나타낸다. 열원충 CDPK, 열원충 CDPK3 및 4는 모기 감염과 관련된 것으로 밝혀졌다. CDPK4는 칼슘 신호를 세포 반응으로 옮기고, 수컷 생식 세포에서 세포 주기 진행을 조절함으로써 모기의 중장에서의 유성생식에 필수적인 것으로 입증되었다. CDPK3은 오키네트 (ookinete) 활주 운동 및 중장 상피를 덮고 있는 층의 침투를 조절한다. 열대열원충 CDPK1 (PfCDPK1)은 혈액 단계의 후기 분열생식 중에 및 감염성 포자소체 단계에서 발현되며, 아실화-의존성 기작에 의해 기생충 공포 (parasitophorous vacuole)로 분비된다. 이는 미리스토일화될 수 있고, 분열생식-단계 기생충으로부터 단리된 계면활성제-내성 막 부분에서 풍부하게 발견된다. 온톨로지-기재 패턴 확인 분석 결과, PfCDPK1은 기생충 배출 또는 적혈구 침습과 관련된 유전자와 함께 무리를 이루는 것으로 나타난다. PfCDPK1의 직접적 억제는 후기 분열생식 단계에서 기생충 적혈구 생활 주기 진행을 중지시킬 수 있다.
따라서, 키나제 활성은 열대열원충 기생충 돌연변이의 모든 단계에서 분포할 수 있고, 본 발명의 키나제 억제제는 열원충 관련 질환을 치료하는 데 사용할 수 있다. 특히, 본 발명의 키나제 억제제는 키나제 PfCDPK1를 억제함으로써 말라리아의 치료 수단이 될 수 있다. 하기 시험관내 세포 분석을 이용하여 다양한 말라리아 기생충 균주에 대한 본 발명의 화합물의 활성을 평가할 수 있다.
본 발명의 화합물은 미토겐-활성화 단백질 키나제-활성화 단백질 키나제 2 (MapKap2 또는 MK-2)에 대해 활성이 없다. 예를 들어, 2-아미노-1-(2-(4-플루오로페닐)-3-(4-플루오로페닐아미노)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)에탄온 (실시예 412) 및 2-아미노-1-(3-(3,4-디플루오로페닐아미노)-2-(4-플루오로페닐)-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)-2-메틸프로판-1-온 (실시예 29)는 이 효소에 대한 단일 지점 농도에서 단지 각각 7% 및 15% 억제를 나타낸다.
본 발명의 화합물은 칸나비노이드 수용체 1 (CB1)에 대하여 상대적으로 활성이 없다. 예를 들어, 2-아미노-1-(2-(4-플루오로페닐)-3-(4-플루오로페닐아미노)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)에탄온 (실시예 412) 및 2-아미노-1-(3-(3,4-디플루오로페닐아미노)-2-(4-플루오로페닐)-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)-2-메틸프로판-1-온 (실시예 29)은 각각 24 μM 및 30 μM 초과의 IC50을 갖는다.
상기에 따라, 본 발명은, 말라리아의 치료를 필요로 하는 대상체에게 치료 유효량의 화학식 Ia, Ib, Ic로부터 선택되는 화합물, 또는 이들의 제약상 허용되는 염을 투여하는 것을 포함하는, 상기 대상체에서 말라리아를 예방 또는 치료하는 방법을 추가로 제공한다. 요구 투여량은 투여 방식, 치료될 특정 조건 및 목적 효과에 따라 달라질 것이다.
투여 및 제약 조성물
일반적으로, 본 발명의 화합물은 당업계에 공지된 통상의 허용되는 임의의 방식을 통해서, 단독으로 또는 1종 이상의 치료제와 함께 치료 유효량으로 투여될 것이다. 치료 유효량은 질환의 중증도, 대상체의 연령 및 상대적인 건강상태, 사용하는 화합물의 효능 및 기타 요소에 따라 광범위하게 바뀔 수 있다. 일반적으로, 약 0.03 내지 2.5 ㎎/체중 ㎏의 1일 투여량에서 전신적으로 만족스러운 결과가 수득되는 것으로 나타난다. 대형 포유류, 예를 들어 인간에서, 지시되는 1일 투여량은 약 0.5 ㎎ 내지 약 100 ㎎ 범위이며, 편의상 예를 들어 1일 4회 이하의 분할 용량으로 또는 서방형으로 투여된다. 경구 투여에 적합한 단위 투여 형태는 약 1 내지 50 ㎎의 활성 성분을 포함한다.
본 발명의 화합물은 임의의 통상적인 경로, 특히 장관으로, 예를 들어 경구로, 예를 들어 정제 또는 캡슐제의 형태로, 또는 비경구로, 예를 들어 주사가능한 용액제 또는 현탁액제의 형태로, 국소적으로, 예를 들어 로션, 겔, 연고 또는 크림의 형태로, 또는 비강제 또는 좌제 형태로 제약 조성물로서 투여될 수 있다. 유리 형태 또는 제약상 허용되는 염 형태의 본 발명의 화합물을 1종 이상의 제약상 허용되는 담체 또는 희석제와 함께 포함하는 제약 조성물은 혼합, 과립화 또는 코팅법에 의하여 통상의 방법으로 제조할 수 있다. 예를 들어, 경구 조성물은 활성 성분과 함께 a) 희석제, 예를 들어 락토스, 덱스트로스, 수크로스, 만니톨, 소르비톨, 셀룰로스 및/또는 글리신; b) 윤활제, 예를 들어 실리카, 탈크, 스테아르산, 그의 마그네슘 또는 칼슘 염 및/또는 폴리에틸렌글리콜; 정제에 있어서는 또한 c) 결합제, 예를 들어 마그네슘 알루미늄 실리케이트, 전분 페이스트, 젤라틴, 트래거캔스, 메틸셀룰로스, 나트륨 카르복시메틸셀룰로스 및/또는 폴리비닐피롤리돈; 경우에 따라 d) 붕해제, 예를 들어 전분, 아가, 알긴산 또는 그의 나트륨 염, 또는 발포성 혼합물; 및/또는 e) 흡수제, 착색제, 향미제 및 감미제를 포함하는 정제 또는 젤라틴 캡슐제일 수 있다. 주사가능한 조성물은 등장성 수용액제 또는 수현탁액제일 수 있고, 좌제는 지방 에멀션 또는 현탁액제로부터 제조할 수 있다. 조성물은 멸균되고/되거나 보조제, 예컨대 보존제, 안정화제, 습윤화제 또는 유화제, 용액 촉진제, 삼투압 조절용 염 및/또는 완충제를 함유할 수 있다. 또한, 기타 치료적으로 가치있는 물질도 함유할 수 있다. 경피 적용에 적합한 제제는 유효량의 본 발명의 화합물을 담체와 함께 포함한다. 담체는 숙주의 피부를 통과하는데 도움이 되는 약리학적으로 허용되는 흡수성 용매를 포함할 수 있다. 예를 들어, 경피 장치는 지지재, 화합물을 임의로 담체와 함께 함유하는 저장고, 임의로 상기 화합물을 숙주의 피부에 조절된 소정의 속도로 장기간에 걸쳐 전달하기 위한 속도 조절 배리어, 및 피부에 장치를 고정하는 수단을 포함하는 붕대 형태이다. 매트릭스 경피 제제 또한 사용할 수 있다. 예를 들어, 피부 및 안구에 대한 국소 적용에 적합한 제제는 바람직하게는 당업계에 널리 공지된 수용액제, 연고, 크림 또는 겔이다. 이들은 가용화제, 안정화제, 삼투성 증강제, 완충제 및 보존제를 함유할 수 있다.
본 발명의 화합물은 치료 유효량으로 1종 이상의 치료제와 조합하여 투여될 수 있다 (제약 조합물). 본 발명의 화합물과 조합하여 사용될 수 있는 화합물의 비제한적인 예는 공지된 항말라리아 약물, 예를 들어 프로구아닐, 클로르프로구아닐, 트리메토프림, 클로로퀸, 메플로퀸, 루메판트린, 아토바쿠온, 피리메타민-술파독신, 피리메타민-다프손, 할로판트린, 퀴닌, 퀴니딘, 아모디아퀸, 아모피로퀸, 술폰아미드, 아르테미시닌, 아르테플렌, 아르테메테르, 아르테수네이트, 프리마퀸, 피로나리딘 등이다.
본 발명의 화합물이 다른 요법과 함께 투여되는 경우, 병용-투여되는 화합물의 투여량은 이용하는 병용-약물의 유형, 이용하는 특정 약물, 치료할 병태 등에 따라 물론 달라질 것이다.
본 발명은 또한 제약 조합물, 예를 들어 a) 유리 형태 또는 제약상 허용되는 염 형태의 본원에 개시된 바와 같은 본 발명의 화합물인 제1 작용제, 및 b) 1종 이상의 병용제를 포함하는 키트를 제공한다. 상기 키트는 투여를 위한 지침서를 포함할 수 있다.
본원에서 사용되는 바와 같은 "병용-투여" 또는 "조합 투여" 등의 용어는 단일 환자에 대한 선택된 치료제의 투여를 포괄하기 위한 의미이며, 작용제들이 반드시 동일한 투여 경로로 또는 동시에 투여될 필요는 없는 치료 처방을 포함하고자 한다.
본원에서 사용되는 용어 "제약 조합물"은 하나를 초과하는 활성 성분을 혼합 또는 조합하여 생성된 산물을 의미하며, 활성 성분들의 고정적 및 비-고정적 조합물 둘 다를 포함한다. "고정적 조합물"이라는 용어는 활성 성분, 예를 들어 화학식 I의 화합물 및 병용제가 둘 다 단일체 또는 단일 투여 형태로 환자에게 동시에 투여됨을 의미한다. "비-고정적 조합물"이라는 용어는 활성 성분, 예를 들어 화학식 I의 화합물 및 병용제가 둘 다 별개체로서 특정의 시간 제한 없이 일제히, 동시에 또는 순차적으로 환자에게 투여됨을 의미하며, 여기서 상기의 투여는 환자의 체내에 치료적으로 유효한 수준의 2종의 화합물을 제공한다. 후자는 칵테일 요법, 예를 들어 3종 이상의 활성 성분의 투여에도 적용된다.
본 발명의 화합물의 제조 방법
본 발명은 또한 본 발명의 화합물의 제조 방법을 포함한다. 기술되는 반응에서, 최종 생성물에서 필요한 경우에 반응성 관능기, 예를 들어 히드록시, 아미노, 이미노, 티오 또는 카르복시기를 이들의 원치않는 반응 참여를 피하기 위해서 보호하는 것이 필요할 수 있다. 통상의 보호기를 표준 실무에 따라 사용할 수 있으며, 예를 들어 문헌 [T. W. Greene and P. G. M. Wuts in "Protective Groups in Organic Chemistry", John Wiley and Sons, 1991]을 참조한다.
하기 반응식 1 내지 5에서와 같이 진행하여 화학식 I의 화합물을 제조할 수 있으며, 여기서 R2, R3, R4, R5, R6, R8, R9, R10, R11 및 R12는 본 발명의 요약 부분에 정의된 것과 같다. 하기 반응식은 예시적이며, 제한하지는 않는 본 발명의 화합물의 합성의 설명인 것으로 주어진다.
반응식 1: 3 성분
우기
반응 (
Ugi
Reaction
)에 의한 일반 합성
경로
시약 및 조건: (a) HClO4, MeOH, rt; (b) Pd/C (또는 PtO2), H2, MeOH, rt; (c) HATU, DIEA, DMF, rt; (d) TFA, DCM, rt
반응식 2:
아미노화에
의해 코어를 획득하기 위한 또 다른 합성 경로
시약 및 조건: (a) HClO4, MeOH, rt; (b) TFA, DCM, rt; (c) Pd2(dba)3, 크산트포스 (XantPhos), Cs2CO3, 디옥산, 140℃.
반응식 3:
이미다졸
형성 - 8,8 디메틸 변형에 의한 일반 합성 경로
시약 및 조건: (a) Cs2CO3, DMF, rt; (b) NH4OAc, 딘-스탁 (Dean-Stark), 톨루엔, 환류; (c) 에틸 2-브로모아세테이트, Cs2CO3, DMF, rt; (d) Pd/C, H2, MeOH, rt; (e) LAH 또는 BH3·Me2S, THF, 환류; (f) N-Boc-글리신, HATU, DIEA, DMF, rt; (g) Br2, DCM/AcOH, rt; (h) p-톨루이딘, Pd2(dba)3, 크산트포스, Cs2CO3, 디옥산, 140℃; (i) TFA, DCM, rt.
반응식 4:
이미다졸
형성 - 6,6 디메틸 변형에 의한 일반 합성 경로
시약 및 조건: (a) Cs2CO3, DMF, rt; (b) NH4OAc, 딘-스탁, 톨루엔, 환류; (c) 3-브로모-2-메틸프로프-1-엔, Cs2CO3, DMF, rt; (d) 마이크로웨이브, AcOH/MsOH, 210℃; (e) N-Boc-글리신, HATU, DIEA, DMF, rt; (f) Br2, DCM/AcOH, rt; (g) 4-클로로아닐린, Pd2(dba)3, 크산트포스, Cs2CO3, 디옥산, 140℃; (h) 6 N HCl, 디옥산, 환류.
반응식 5:
이미다졸
형성 - 5,5 디메틸 변형에 의한 일반 합성 경로
시약 및 조건: (a) Cs2CO3, DMF, rt; (b) NH4OAc, 딘-스탁, 톨루엔, 환류; (c) 에틸 2-브로모아세테이트, Cs2CO3, DMF, rt; (d) Pd/C, H2, MeOH, rt; (e) PMBCl, KOH, THF, rt; (f) MeI, NaH, DMF, rt; (g) BH3·Me2S, THF, 환류; (h) Br2, DCM/AcOH, rt; (i) p-톨루이딘, Pd2(dba)3, 크산트포스, Cs2CO3, 디옥산, 150℃; (j) TFA, 70℃; (k) N-Boc-글리신, HATU, DIEA, DMF, rt; (l) TFA, DCM, rt.
본 발명의 화합물의 합성의 상세한 설명은 하기 실시예에서 제공된다.
본 발명의 화합물의 추가 제조 방법
본 발명의 화합물은, 화합물의 유리 염기 형태를 제약상 허용되는 무기 또는 유기 산과 반응시켜 제약상 허용되는 산 부가염으로 제조할 수 있다. 다르게는, 본 발명의 화합물의 제약상 허용되는 염기 부가염은 화합물의 유리 산 형태를 제약상 허용되는 무기 또는 유기 염기와 반응시켜 제조할 수 있다. 다르게는, 본 발명의 화합물의 염 형태, 예를 들어 푸마레이트 염은 출발 물질 또는 중간체의 염을 사용하여 제조할 수 있다.
본 발명의 화합물의 유리 산 또는 유리 염기 형태는 각각 상응하는 염기 부가염 또는 산 부가염 형태로부터 제조할 수 있다. 예를 들어, 산 부가염 형태의 본 발명의 화합물은 적합한 염기 (예를 들어, 수산화암모늄 용액, 수산화나트륨 등)로 처리하여 상응하는 유리 염기로 전환시킬 수 있다. 염기 부가염 형태의 본 발명의 화합물은 적합한 산 (예를 들어, 염산 등)으로 처리하여 상응하는 유리 산으로 전환시킬 수 있다.
산화되지 않은 형태의 본 발명의 화합물은 0 내지 80℃의 적합한 불활성 유기 용매 (예를 들어, 아세토니트릴, 에탄올, 수성 디옥산 등) 중에서 환원제 (예를 들어, 황, 이산화황, 트리페닐 포스핀, 수소화붕소리튬, 수소화붕소나트륨, 삼염화인, 트리브로마이드 등)로 처리하여 본 발명의 화합물의 N-옥시드로부터 제조할 수 있다.
본 발명의 화합물의 전구약물 유도체는 당업계에 공지된 방법 (예를 들어, 추가의 상세사항은 문헌 [Saulnier et al., (1994), Bioorganic and Medicinal Chemistry Letters, Vol. 4, p. 1985] 참조)으로 제조할 수 있다. 예를 들어, 적절한 전구약물은 본 발명의 비-유도체화된 화합물을 적합한 카르바밀화제 (예를 들어, 1,1-아실옥시알킬카르바노클로리데이트, 파라-니트로페닐 카보네이트 등)와 반응시켜 제조할 수 있다.
본 발명의 화합물의 보호된 유도체는 당업계에 공지된 방법으로 제조할 수 있다. 보호기의 생성 및 그의 제거에 적용가능한 기술에 대한 상세한 설명은 문헌 [T. W. Greene, "Protecting Groups in Organic Chemistry", 3rd edition, John Wiley and Sons, Inc., 1999]에서 찾을 수 있다.
본 발명의 화합물은 편리하게는 본 발명의 진행 도중 용매화물 (예를 들어, 수화물)로서 제조 또는 형성될 수 있다. 본 발명의 화합물의 수화물은 편리하게는 디옥신, 테트라히드로푸란 또는 메탄올과 같은 유기 용매를 사용하여 수성/유기 용매 혼합물로부터의 재결정화에 의하여 제조할 수 있다.
본 발명의 화합물은, 화합물의 라세미 혼합물을 광학 활성 분할제와 반응시켜 부분입체이성질체 화합물 쌍을 형성하고, 부분입체이성질체들을 분리하고, 광학적으로 순수한 거울상이성질체를 회수함으로써 그의 개별 입체이성질체로 제조할 수 있다. 거울상이성질체의 분할은 본 발명의 화합물의 공유 부분입체이성질성 유도체를 사용하여 수행할 수 있지만, 분리가능한 복합체가 바람직하다 (예를 들어, 결정성 부분입체이성질성 염). 부분입체이성질체는 별개의 물성 (예를 들어, 융점, 비점, 용해도, 반응성 등)을 갖고, 이러한 차이점을 이용하여 쉽게 분리할 수 있다. 부분입체이성질체는 크로마토그래피에 의하여, 또는 바람직하게는 용해도 차이에 기초하는 분리/분할 기술에 의하여 분리될 수 있다. 이때 광학적으로 순수한 거울상이성질체는 라세미화를 일으키지 않을 임의의 실무적 방법에 의해서 분할제와 함께 회수된다. 화합물의 라세미 혼합물로부터의 그의 입체이성질체의 분할에 적용가능한 기술의 보다 상세한 설명은 문헌 [Jean Jacques, Andre Collet, Samuel H. Wilen, "Enantiomers, Racemates and Resolutions", John Wiley And Sons, Inc., 1981]에서 찾을 수 있다.
요약하면, 화학식 I의 화합물은 하기의 단계를 포함하는 방법에 의하여 제조할 수 있다:
(a) 반응식 1, 2, 3, 4 및/또는 5의 단계; 및
(b) 임의로, 본 발명의 화합물을 제약상 허용되는 염으로 전환시키는 단계;
(c) 임의로, 본 발명의 화합물의 염 형태를 염이 아닌 형태로 전환시키는 단계;
(d) 임의로, 본 발명의 화합물의 산화되지 않은 형태를 제약상 허용되는 N-옥시드로 전환시키는 단계;
(e) 임의로, 본 발명의 화합물의 N-옥시드 형태를 그의 산화되지 않은 형태로 전환시키는 단계;
(f) 임의로, 본 발명의 화합물의 이성질체 혼합물로부터 개별 이성질체를 분할하는 단계;
(g) 임의로, 본 발명의 비-유도체화된 화합물을 제약상 허용되는 전구약물 유도체로 전환시키는 단계; 및
(h) 임의로, 본 발명의 화합물의 전구약물 유도체를 그의 비-유도체화된 형태로 전환시키는 단계.
출발 물질의 제법을 특별히 기재하지 않는 한, 그 화합물들은 공지되어 있거나, 당업계에 공지된 방법과 유사하게 또는 이후의 실시예에 개시되는 바와 같이 제조할 수 있다.
당업자는, 상기 변형이 단지 본 발명의 화합물의 제조 방법을 대표하는 것일 뿐이며 다른 널리 공지된 방법도 유사하게 사용될 수 있음을 알 것이다.
<실시예>
본 발명은 본 발명의 화합물의 제법을 예시하는 하기 실시예 (표 2) 및 중간체 (기준 화합물 - 표 1)로 추가 예시되지만, 이에 한정되지 않는다.
<표 1>
기준 화합물 1
N-(
벤조[d][1,3]디옥솔
-5-일)-2-
페닐
-5,6,7,8-테트라히드로이미다조[1,2-a]피라진-3-아민
하기 방식으로 기준 화합물 1을 제조하였다.
에틸 포르메이트 10 mL 중 화합물 1-1 (685 mg, 10 mmol)의 교반된 용액을 마이크로웨이브 오븐에서 2시간 동안 120℃로 가열하였다. 용매를 제거하고, 잔류물을 MS-유발 HPLC 정제하여, 중화 후 갈색 오일로서 화합물 1-2 728 mg을 얻었다. DCM 20 mL 중 화합물 1-2 (728 mg, 4.4 mmol)의 용액에 DIEA (2.30 mL, 13.2 mmol) 및 POCl3 (0.45 mL, 4.84 mmol)을 0℃에서 첨가하였다. 반응 혼합물을 동일한 온도에서 2시간 동안 교반하고, 실온에서 추가 2시간 동안 교반하였다. 용매를 제거하고, 잔류물을 MS-유발 HPLC 정제하여, 중화 후 황색 고체로서 화합물 1-3 281 mg을 얻었다.
MeOH 10 mL 중 화합물 1-3 (158 mg, 1.66 mmol)의 교반된 용액에 벤즈알데히드 (0.25 mL, 2.49 mmol), 2-아미노피라진 (281 mg, 1.91 mmol), 이어서 MeOH 중 1.0 N HClO4 (0.17 mL, 0.17 mmol)를 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다. 반응 혼합물을 바로 질량-유발 HPLC 정제하였다. 수집된 MeCN/물 용액을 농축시키고, 동결건조기에서 건조시켜, 분말 생성물로서 화합물 1-4 296 mg을 얻었다.
MeOH 10 mL 중 화합물 1-4 (181 mg, 0.54 mmol)의 교반된 용액에 Pd/C (58 mg, 0.054 mmol)를 첨가하였다. 반응 혼합물을 탈기시키고, H2로 역충전하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 고체를 여과하고, 용매를 제거하였다. 조생성물의 400 MHz 양성자 NMR은 조생성물이 표제 화합물인 것을 입증하였다.
적절한 출발 물질을 사용하여, 기준 화합물 1을 제조하기 위해 사용되는 동일한 3 성분 우기 반응, 이어서 Pd/C 매개 수소화에 의해 하기 기준 화합물을 제조하였다: 기준 화합물 2를 2-아미노피리딘, 벤즈알데히드 및 1-이소시아노-3,5-디메틸벤젠으로부터 제조하였고; 기준 화합물 3을 2-아미노피라진, 4-플루오로벤즈알데히드 및 이소시아노시클로펜탄으로부터 제조하였고; 기준 화합물 4를 2-아미노피라진, 벤즈알데히드 및 이소시아노시클로펜탄으로부터 제조하였고; 기준 화합물 5를 2-아미노피라진, 벤즈알데히드 및 이소시아노벤젠으로부터 제조하였고; 기준 화합물 6을 2-아미노피라진, 벤즈알데히드 및 메틸 4-이소시아노벤조에이트로부터 제조하였고; 기준 화합물 7을 2-아미노피라진, 2-플루오로벤즈알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 8을 2-아미노피라진, 벤즈알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 9를 2-아미노피라진, 2,4,6-트리플루오로벤즈알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 10을 2-아미노피라진, 3,5-디플루오로벤즈알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 11을 2-아미노피라진, 4-펜틸벤즈알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 12를 2-아미노피라진, 시클로헥산카르브알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 13을 2-아미노피라진, 4-플루오로벤즈알데히드 및 3-이소시아노피리딘으로부터 제조하였고; 기준 화합물 14를 2-아미노피라진, 4-플루오로벤즈알데히드 및 이소시아노시클로헥산으로부터 제조하였고; 기준 화합물 15를 2-아미노피라진, 4-플루오로벤즈알데히드 및 1-브로모-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 16을 2-아미노피라진, 4-플루오로벤즈알데히드 및 (이소시아노메틸)벤젠으로부터 제조하였고; 기준 화합물 17을 2-아미노피라진, 4-플루오로벤즈알데히드 및 (이소시아노플루오로)벤젠으로부터 제조하였고; 기준 화합물 22를 2-아미노피라진, 4-플루오로-2-히드록시 벤즈알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 23을 2-아미노피라진, 4-메틸벤즈알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 24를 2-아미노피라진, 4-메톡시벤즈알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 25를 2-아미노피라진, 4-브로모벤즈알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 26을 2-아미노피라진, 4-클로로벤즈알데히드 및 1-플루오로-4-이소시아노벤젠으로부터 제조하였고; 기준 화합물 29를 2-아미노피라진, 4-플루오로벤즈알데히드 및 1-메틸-4-이소시아노벤젠으로부터 제조하였다.
기준 화합물 18
2,3-
비스
(4-
플루오로페닐
)-5,6,7,8-
테트라히드로이미다조[1,2-a]피라진
하기 방식에 의해 기준 화합물 18을 제조하였다.
무수 DCM 30 mL 중 2-(4-플루오로페닐)아세트산 (1.54 g, 10 mmol)의 용액에 SOCl2 (2.18 mL, 30 mmol)를 서서히 첨가하고, 2방울의 DMF를 첨가하였다. 반응 혼합물을 1시간 동안 환류 하에 교반하고, 이후 용매를 제거하였다. 잔류물을 DCM 30 mL에 용해시키고, AlCl3 (2.67 g, 22 mmol)을 0℃에서 첨가하였다. 반응 혼합물을 실온에서 10분 동안 교반하였다. DCM 2 mL 중 플루오로벤젠 (0.94 mL, 10 mmol)을 0℃에서 적가하였다. 반응 혼합물을 동일한 온도에서 2시간 동안 교반하도록 하였다. 반응 혼합물을 0.1 M HCl 30 mL 및 분쇄된 얼음 50 g의 혼합물에 부었다. 얻어진 혼합물을 분리시키고, 수성 층을 DCM으로 세척하였다. 합쳐진 DCM 용액을 건조시키고 농축시켰다. 잔류물을 플래시 크로마토그래피 정제하여, 밝은 황색 고체로서 화합물 18-1 983 mg을 얻었다.
DCM 6 mL 중 화합물 18-1 (232 mg, 1.0 mmol)의 용액에 아세트산 12 mL 중 Br2 (61 μL, 1.2 mmol)를 첨가하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 반응 혼합물을 농축시키고, 잔류물을 바로 질량-유발 HPLC 정제하여, 황색 고체 181 mg을 얻었다. 정제용 HPLC에서의 목적 생성물의 질량은 정확하지 않았으며, 브로민화물의 특징적인 피크 패턴을 나타내지 않았다. 그 질량에 의해 피크를 수집하고, 화합물을 분석용 HPLC에서, 및 또한 400 MHz 양성자 NMR에 의해 정확한 질량이 되는지 확인하였다.
EtOH 5 mL 중 2-아미노피라진 (57 mg, 0.60 mmol), 화합물 18-2 (156 mg, 0.50 mmol) 및 K2CO3 (83 mg, 0.60 mmol)의 용액을 120℃에서 3시간 동안 교반하였다. 용매를 제거하고, 잔류물을 MS-유발 HPLC 정제하였다. 수집된 MeCN/물 용액을 중화시켰다. 유기 용액을 건조시키고, 농축시켜, 황색 오일로서 화합물 18-3을 얻었다.
MeOH 6 mL 중 화합물 18-3 (10 mg, 0.033 mmol)의 교반된 용액에 Pd/C (4 mg, 0.0033 mmol)를 첨가하였다. 반응 혼합물을 탈기시키고, H2로 역충전하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 고체를 여과하고, 용매를 제거하였다. 생성물을 질량-유발 HPLC 정제 하여, 중화 후 황색 오일로서 표제 화합물을 얻었다.
기준 화합물 19
2-(4-
플루오로페닐
)
이미다조
[1,2-a]피라진-3-아민
다음 방식에 의해 기준 화합물 19를 제조하였다.
MeOH 10 mL 중 2-아미노피라진 (571 mg, 6.0 mmol)의 교반된 용액에 4-플루오로벤즈알데히드 (0.97 mL, 9.0 mmol), 2-이소시아노-2-메틸프로판 (0.78 mL, 6.9 mmol), 이어서 MeOH 중 1.0 N HClO4 (0.60 mL, 0.60 mmol)를 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다. 용매를 제거하고, 잔류물을 플래시 크로마토그래피 정제하여, 백색 고체로서 화합물 19-1을 얻었다.
4:1 DCM 및 TFA 10 mL 중 화합물 19-1 (284 mg, 1.0 mmol)의 용액을 실온에서 2시간 동안 교반하였다. 용매를 제거하고, 생성물을 중화 후 다음 단계에서 바로 사용하였다.
기준 화합물 20
N-(3-
플루오로페닐
)-2-(4-
플루오로페닐
)-5,6,7,8-테트라히드로이미다조[
1,2-a]피라진
-3-아민
하기 방식에 의해 기준 화합물 20을 제조하였다. 디옥산 6 mL 중 기준 화합물 19 (69 mg, 0.30 mmol)의 용액에 1-브로모-3-플루오로벤젠 (66 μL, 0.60 mmol), Pd2(dba)3 (8 mg, 0.009 mmol), 크산트포스 (11 mg, 0.018 mmol) 및 Cs2CO3 (196 mg, 0.60 mmol)을 실온에서 첨가하였다. 반응 혼합물을 탈기시키고, 120℃에서 5시간 동안 N2 하에 교반하였다. 반응 혼합물을 실온으로 냉각시키고, 고체를 여과하였다. 얻어진 여액을 농축시켰다. 잔류물을 질량-유발 HPLC 정제하여, 중화 후 황색 오일을 얻었다. MeOH 5 mL 중 얻어진 부가생성물 (64 mg, 0.20 mmol)의 교반된 용액에 Pd/C (21 mg, 0.02 mmol)를 첨가하였다. 반응 혼합물을 탈기시키고, H2로 역충전하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, 황색 고체를 얻었다.
1-브로모-3,5-디플루오로벤젠과의 아미노화 반응, 이어서 Pd/C 매개 수소화에 의해 기준 화합물 19로부터 기준 화합물 27을 제조하였으며; 1-브로모-4-(트리플루오로메틸)벤젠과의 아미노화 반응, 이어서 Pd/C 매개 수소화에 의해 기준 화합물 19로부터 기준 화합물 28을 제조하였으며; 1-브로모-4-(트리플루오로메틸)벤젠과의 아미노화 반응, 이어서 Pd/C 매개 수소화에 의해 기준 화합물 19로부터 기준 화합물 30을 제조하였으며; 1-브로모-2,4-디플루오로벤젠과의 아미노화 반응, 이어서 Pd/C 매개 수소화에 의해 기준 화합물 11로부터 기준 화합물 31을 제조하였으며; 기준 화합물 19가 제조되는 것과 동일한 방식, 즉 2-아미노피라진, 3-플루오로벤즈알데히드 및 2-이소시아노-2-메틸프로판 사이의 3 성분 우기 반응, 이어서 TFA 매개 탈보호에 의해 기준 화합물 32를 제조하였으며; 2-아미노피라진, 3-플루오로벤즈알데히드 및 2-이소시아노-2-메틸프로판 사이의 3 성분 우기 반응, 이어서 2-(벤질옥시카르보닐아미노)-2-메틸프로판산과의 HATU 매개 아미드화 및 HCl 매개 탈보호에 의해 기준 화합물 34를 제조하였다.
기준 화합물 33
2-(4-
플루오로페닐
)-6-
메틸이미다조[1,2-a]피라진
-3-아민
기준 화합물 1을 제조하는 것과 동일한 방식에 의해 기준 화합물 33을 제조하였다.
MeOH 20 mL 중 5-브로모피라진-2-아민 (313 mg, 1.8 mmol)의 교반된 용액에 4-플루오로벤즈알데히드 (191 μL, 1.8 mmol), 이어서 MeOH 중 1.0 N HClO4 (0.15 mL, 0.15 mmol)를 첨가하였다. 반응 혼합물을 실온에서 0.5시간 동안 교반하였으며, 이후 2-이소시아노-2-메틸프로판 (170 μL, 1.5 mmol)을 첨가하였다. 실온에서 밤새 교반을 계속하였다. 반응 혼합물을 바로 질량-유발 HPLC 정제하여, 황색 고체로서 화합물 33-1 299 mg을 얻었다.
디옥산 10 mL 중 화합물 33-1 (131 mg, 0.36 mmol)의 교반된 용액에 톨루엔 중 2.0 M Me2Zn (0.75 mL, 1.5 mmol) 및 Ni(DPPP)2Cl2 (98 mg, 0.18 mmol)를 첨가하였다. 반응 혼합물을 탈기시키고, N2로 역충전하였다. 반응 혼합물을 밤새 환류 하에 교반하였다. 반응 혼합물을 메탄올로 켄칭시켰다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, 황색 오일로서 화합물 33-2를 얻었다.
DCM 2 mL 중 화합물 33-2 (9 mg, 0.03 mmol)의 용액에 TFA 4 mL를 첨가하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 반응 혼합물을 농축시키고, 잔류물을 질량-유발 HPLC 정제하여, 중화 후 표제 화합물을 정량적 수율로 얻었다.
기준 화합물 35
2-(4-
플루오로페닐
)-6-
메틸이미다조[1,2-a]피라진
-3-아민
하기 방식에 의해 기준 화합물 35를 제조하였다.
DMF (400 mL) 중 2-브로모-1-(4-플루오로페닐)에탄온 (46.5 g, 214.29 mmol)의 용액에 2-(벤질옥시카르보닐)-2-메틸프로판산 (55.8 g, 236.4 mmol) 및 탄산칼륨 (35.4 g, 256.5 mmol)을 첨가하였다. 얻어진 용액을 실온에서 4시간 동안 교반하였다. 얻어진 용액을 물 1000 mL로 희석시켰다. 얻어진 용액을 에틸 아세테이트 (2×800 mL)로 추출하고, 합쳐진 유기 층을 물 (2×800 mL), 염수 (1×800 mL)로 세척하였다. 얻어진 혼합물을 진공 하에 농축시켰다. 백색 고체로서 화합물 35-1 67 g (84%)이 생성되었다.
톨루엔 (700 mL) 중 화합물 35-1 (70 g, 187.7 mmol)의 용액에 NH4OAc (144.5 g, 1.88 mol)를 첨가하였다. 얻어진 용액을 오일 조에서 3시간 동안 가열 환류시켰다. 얻어진 혼합물을 진공 하에 농축시켰다. 잔류물을 물 800 mL에 용해시켰다. 얻어진 용액을 에틸 아세테이트 (2×500 mL)로 추출하고, 합쳐진 유기 층을 물 (2×800 mL) 및 염수 (1×800 mL)로 세척하였다. 얻어진 혼합물을 진공 하에 농축시켰다. 백색 고체로서 화합물 35-2 58 g (88%)이 생성되었다.
DMF (400 mL) 중 화합물 35-2 (58 g, 164.3 mmol)의 용액에 탄산세슘 (134 g, 411.0 mmol)을 첨가하였다. 이에 이어서 실온에서 30분 동안 교반하면서 에틸 2-브로모아세테이트 (33 g, 197.6 mmol)를 적가하였다. 얻어진 용액을 실온에서 2시간 동안 교반하였다. 얻어진 용액을 물/얼음 1000 mL로 희석시켰다. 얻어진 용액을 에틸 아세테이트 (2×700 mL)로 추출하고, 합쳐진 유기 층을 물 (2×800 mL) 및 염수 (1×800 mL)로 세척하였다. 얻어진 혼합물을 진공 하에 농축시켰다. 황색 고체로서 화합물 35-3 60 g (83%)이 생성되었다.
메탄올 (800 mL) 중 화합물 35-3 (70 g, 159.4 mmol)의 용액에 10% Pd/C (10 g)를 첨가하였다. 얻어진 용액을 탈기시키고, 수소로 역충전하였다. 용액을 35℃에서 3일 동안 교반하였다. 고체를 여과하였다. 여액을 감압 하에 농축시켰다. 백색 고체로서 화합물 35-4가 생성되었다.
THF (300 mL) 중 화합물 40-4 (15 g, 57.9 mmol)의 교반된 용액에 BH3 Me2S 착물 (144.2 mL, 2 M)을 실온에서 30분 동안 적가하였다. 얻어진 용액을 4시간 동안 환류시켰다. 실온으로 냉각시킨 후, 얻어진 용액을 메탄올 100 mL로 희석시켰다. 염산 (12 N)으로 pH를 1 내지 2로 조절하였다. 혼합물을 1시간 동안 환류시켰다. 얻어진 혼합물을 진공 하에 농축시켰다. 잔류물을 물 100 mL에 용해시켰다. 수성 탄산칼륨 (40%)으로 pH를 9 내지 10으로 조절하였다. 얻어진 용액을 DCM 3×200 mL로 추출하고, 유기 층을 합하고, 무수 황산나트륨에서 건조시키고, 진공 하에 농축시켰다. 백색 고체로서 화합물 35-5가 생성되었다.
DMF (150 mL) 중 화합물 35-5 (7.3 g, 29.8 mmol)의 교반된 용액에 N-Boc-글리신 (17 g, 89.4 mmol), 이어서 HATU (37.2 g, 122 mmol) 및 DIEA (25.3 g, 178 mmol)를 첨가하였다. 얻어진 용액을 실온에서 3시간 동안 교반하였다. 얻어진 혼합물을 에틸 아세테이트 600 mL로 희석시키고, 포화 수성 NaHCO3 (30 mL×6), 염수 (30 mL×3)로 세척하고, 무수 Na2SO4에서 건조시키고, 진공 하에 농축시켰다. 조생성물이 생성되었으며, 이를 분쇄시키고, 에테르 (20 mL×3)와 함께 초음파처리하여, 화합물 35-6을 얻었다.
DCM 30 mL 중 화합물 35-6 (3.02 g, 7.51 mmol)의 교반된 용액에 아세트산 3 mL 중 Br2 (0.43 mL, 8.26 mmol)를 첨가하였다. 반응 혼합물을 실온에서 30분 동안 교반하였다. HPLC/MS 시험은 목적 생성물 (II)가 유일한 피크였음을 나타내었다. 용매를 20℃ 이하의 온도에서 회전 증발기를 통해 제거하였다. 중화 후, 백색 고체 3.76 g을 얻었다. 400 MHz 양성자 NMR에 의해 생성물이 표제 화합물인 것으로 확인되었다. 생성물을 추가 정제 없이 다음 단계에서 사용하였다.
N-Cbz-글리신을 단계 (f)에서 사용한 것을 제외하고는 기준 화합물 35가 제조되는 것과 유사한 방식에 의해 기준 화합물 36을 제조하였다. 2-아미노피라진, 4-플루오로벤즈알데히드 및 2-이소시아노-2-메틸프로판 사이의 3 성분 우기 반응, 이어서 2-(벤질옥시카르보닐아미노)-2-메틸프로판산과의 HATU 매개 아미드화 반응 및 HCl 매개 탈보호에 의해 기준 화합물 37을 제조하였다. 2-아미노피라진, 4-플루오로-3-메틸벤즈알데히드 및 2-이소시아노-2-메틸프로판 사이의 3 성분 우기 반응, 이어서 TFA 매개 탈보호에 의해, 기준 화합물 19에서와 동일한 방식으로 기준 화합물 38을 제조하였다. 유사하게, 2-아미노피라진, 3-클로로-4-플루오로벤즈알데히드 및 2-이소시아노-2-메틸프로판 사이의 3 성분 우기 반응, 이어서 TFA 매개 탈보호에 의해, 기준 화합물 19로부터 기준 화합물 39를 제조하였다. 기준 화합물 19가 제조되는 것과 동일한 방식, 즉 2-아미노피라진, 4-클로로-3-플루오로벤즈알데히드 및 2-이소시아노-2-메틸프로판 사이의 3 성분 우기 반응, 이어서 TFA 매개 탈보호에 의해 기준 화합물 40을 제조하였다.
기준 화합물 41
2-(4-
플루오로페닐
)-6,6,7-
트리메틸
-5,6,7,8-테트라히드로이미다조
[1,2-a]피라진
하기 방식에 의해 화합물 42-2로부터 기준 화합물 41을 제조하였다.
CH3CN (10 mL) 중 화합물 42-2 (500 mg, 2.04 mmol, 1.00 equiv)의 교반된 용액에 포르말린 (5 mL)을 첨가하였다. 반응 혼합물을 실온에서 20분 동안 교반하고, 이어서 NaBH3CN (400 mg, 6.35 mmol, 3.00 equiv) 및 아세트산 (1 mL, 1.00 equiv)을 첨가하였다. 반응 혼합물을 실온에서 추가 1시간 동안 교반하였다. 수산화나트륨 (1 N 수성)을 첨가하여 혼합물을 중화시켰다. 용액을 에틸 아세테이트 (3×10 ml)로 추출하고, 합쳐진 유기 층을 염수 (3×10 mL)로 세척하고, 무수 황산나트륨에서 건조시켰다. 혼합물을 진공 하에 농축시켰다. 잔류물을 실리카 겔 컬럼 (디클로로메탄/메탄올 (40:1))에 적용하였다. 밝은 황색 고체로서 표제 화합물이 생성되었다.
기준 화합물 42
tert
-부틸 2-(3-
브로모
-2-(4-
플루오로페닐
)-6,6-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)-2-
옥소에틸카르바메이트
하기 방식에 의해 화합물 51-2로부터 기준 화합물 42를 제조하였다.
DMF (30 mL) 중 화합물 51-2 (1.1 g, 3.38 mmol, 1.00 equiv)의 교반된 용액에 3-클로로-2-메틸프로프-1-엔 (500 mg, 5.49 mmol, 1.50 equiv), 탄산칼륨 (560 mg, 4.06 mmol, 1.10 equiv) 및 KI (1.12 g, 6.75 mmol, 2.00 equiv)를 실온에서 첨가하였다. 반응 혼합물을 40℃에서 48시간 동안 교반하였다. 반응 혼합물을 에틸 아세테이트 100 ml로 희석시켰다. 혼합물을 염수 (3×10 mL)로 세척하고, 황산나트륨에서 건조시키고, 진공 하에 농축시켰다. 잔류물을 실리카 겔 컬럼 (석유 에테르/EtOAc (5:1))에 적용하여, 밝은 황색 고체로서 화합물 42-1를 얻었다.
30 mL 밀봉된 튜브에, 화합물 42-1 (2.0 g, 5.28 mmol, 1.00 equiv), AcOH (12 mL), MsOH (2 mL)를 두었다. 반응 혼합물을 260℃ (모래조 온도)에서 12시간 동안 교반하였다. 반응 혼합물을 실온으로 냉각시켰다. 혼합물을 물 20 ml에 부었다. 수성 층을 에틸 아세테이트 (3×10 mL)로 세척하였다. 수성 수산화나트륨 (1 N)을 첨가하여 pH를 8로 조절하였다. 수성 층을 에틸 아세테이트 (3×10 mL)로 추출하였다. 합쳐진 유기 층을 염수 (3×10 ml)로 세척하고, 황산나트륨에서 건조시키고, 진공 하에 농축시켰다. 고체를 여과에 의해 수집하고, n-헥산 5 mL로 세척하여, 백색 고체로서 화합물 42-2를 얻었다.
DMF (10 mL) 중 화합물 42-2 (280 mg, 1.14 mmol, 1.00 equiv)의 교반된 용액에 2-(tert-부톡시카르보닐)아세트산 (600 mg, 3.43 mmol, 3.00 equiv), HATU (1.3 g, 3.42 mmol, 3.00 equiv) 및 DIEA (880 mg, 6.82 mmol, 6.00 equiv)를 실온에서 첨가하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 반응 혼합물을 에틸 아세테이트 100 ml로 희석시켰다. 유기 층을 염수 (3×10 mL)로 세척하고, 황산나트륨에서 건조시키고, 진공 하에 농축시켰다. 잔류물을 실리카 겔 컬럼 (DCM/MeOH (10:1))에 적용하여, 갈색 고체로서 화합물 42-3을 얻었다.
DCM 6 mL 중 화합물 42-3 (386 g, 0.96 mmol)의 교반된 용액에 아세트산 2 mL 중 Br2 (55 μL, 1.06 mmol)를 첨가하였다. 반응 혼합물을 실온에서 30분 동안 교반하였다. 용매를 20℃ 이하의 온도에서 회전 증발기를 통해 제거하였다. 중화 후, 잔류물을 플래시 크로마토그래피 (40 g, 헥산 중 0-100% 에틸 아세테이트, 50분, 건조 로딩 (dry loading)) 정제하여, 무색 오일로서 표제 화합물을 얻었다.
기준 화합물 43
3-
브로모
-2-(3-
플루오로페닐
)-7-(4-메톡시벤질)-5,5-디메틸-5,6,7,8-
테트라히드로이미다조[1,2-a]피라진
하기 방식에 의해 화합물 51-2로부터 기준 화합물 43을 제조하였다.
DMF 10 mL 중 화합물 43-1 (231 mg, 1.0 mmol)의 용액에 KOH (168 mg, 3.0 mmol) 및 PMBCl (405 μL, 3.0 mmol)을 0℃에서 첨가하였다. 반응 혼합물을 동일한 온도에서 2시간 동안 교반하고, 실온에서 추가 2시간 동안 교반하였다. 반응 혼합물을 바로 LC/MS 정제하여, 중화 후 백색 고체로서 화합물 43-2를 얻었다.
DMF 15 mL 중 화합물 43-2 (253 mg, 0.72 mmol)의 용액에 60% NaH (87 mg, 0.085 mmol) 및 MeI (0.45 mL, 7.2 mmol)를 실온에서 첨가하였다. 반응 혼합물을 실온에서 2시간 동안 교반하였다. 반응 혼합물을 메탄올로 켄칭시키고, 바로 질량-유발 HPLC 정제하여, 중화 후 백색 고체로서 화합물 43-3 mg을 얻었다.
THF 9 mL 중 화합물 43-3 (170 mg, 0.45 mmol)의 용액에 1.0 N BH3·THF (2.70 mL, 2.70 mmol)를 실온에서 첨가하였다. 반응 혼합물을 2시간 동안 환류 하에 교반하였다. Pd/C를 첨가하였다 (기체가 생성됨). 반응 혼합물을 1시간 동안 교반하였다. 고체를 여과하고, 용매를 제거하였다. 조질의 화합물 43-4를 바로 400 MHz 양성자 NMR로 시험하여, 생성물이 정확한 것이었음을 입증하였다. 생성물은 100% 수율인 것으로 가정하였으며, 추가 정제 없이 다음 단계에서 사용하였다.
DCM 6 mL 중 화합물 43-4 (164 g, 0.45 mmol)의 교반된 용액에 아세트산 2 mL 중 Br2 (26 μL, 0.50 mmol)를 첨가하였다. 반응 혼합물을 실온에서 30분 동안 교반하였다. 용매를 20℃ 이하의 온도에서 회전 증발기를 통해 제거하였다. 중화 후, 잔류물을 ISCO (24 g, 헥산 중 0-100% 에틸 아세테이트, 25분, 건조 로딩) 정제하여, 백색 고체로서 표제 화합물을 얻었다.
기준 화합물 44
tert
-부틸 1-(3-
브로모
-2-(4-
플루오로페닐
)-8,8-디메틸-5,6-디히드로이미다
조[1,2-a]피라진
-7(8H)-일)-2-
메틸
-1-
옥소프로판
-2-
일카르바메이트
하기 방식에 의해 화합물 40-5로부터 기준 화합물 44를 제조하였다.
DCM (20 mL) 중 화합물 35-5 (1.48 g, 6.04 mmol) 및 NEt3 (6.0 g, 59.4 mmol)의 교반된 용액에 2-브로모-2-메틸프로파노일 브로마이드 (14 g, 60.9 mmol)를 실온에서 적가하였다. 실온에서 3시간 동안 교반한 후, 물 30 mL의 첨가에 의해 반응물을 켄칭시켰다. 얻어진 용액을 에틸 아세테이트 3×30 mL로 추출하였다. 합쳐진 유기 층을 염수로 세척하고, 무수 황산나트륨에서 건조시키고, 진공 하에 농축시켰다. 암색 고체로서 조생성물이 생성되었으며, 이를 EtOAc:석유 에테르 (1:10)로 세척하여 불순물을 제거하여, 회색 고체로서 화합물 44-1이 생성되었다.
DMF (10 mL) 중 화합물 44-1 (2.0 g, 5.08 mmol, 1.00 equiv)의 용액에 NaN3 (1.0 g, 15.38 mmol, 3.00 equiv)을 실온에서 첨가하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 얻어진 용액을 에틸 아세테이트 300 mL로 희석시켰다. 얻어진 혼합물을 염수 3×20 mL로 세척하고, 무수 황산나트륨에서 건조시키고, 진공 하에 농축시켰다. 잔류물을 실리카 겔 컬럼 (석유 에테르/EtOAc (5:1))에 적용하여, 백색 고체로서 화합물 44-2를 얻었다.
메탄올 (20 mL) 중 화합물 44-2 (1.2 g, 3.37 mmol, 1.00 equiv)의 교반된 용액에 Pd/C (80 mg, 0.75 mmol, 0.20 equiv)를 실온에서 첨가하였다. 반응 혼합물을 탈기시키고, H2로 역충전하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 고체를 여과하였다. 얻어진 혼합물을 진공 하에 농축시켰다. 고체를 석유 에테르로 세척하였다. 백색 고체로서 화합물 44-3이 생성되었다.
THF (50 mL) 중 화합물 44-3 (910 mg, 2.76 mmol, 1.00 equiv)의 교반된 용액에 BOC 무수물 (3.2 g, 14.68 mmol, 5.00 equiv), 이어서 수성 NaOH (1 N, 6 ml, 2.00 equiv)를 실온에서 첨가하였다. 얻어진 용액을 40℃에서 24시간 동안 교반하였다. 얻어진 용액을 진공 하에 농축시켰다. 혼합물을 EtOAc 60 ml로 희석시켰다. 유기 층을 염수 3×10 ml로 세척하고, Na2SO4에서 건조시키고, 진공 하에 농축시켰다. 고체를 여과에 의해 수집하고, n-헥산 (5 ml)으로 세척하여, 백색 고체로서 화합물 44-4를 얻었다.
DCM 3 mL 중 화합물 44-4 (32 mg, 0.074 mmol)의 교반된 용액에 아세트산 1 mL 중 Br2 (4.2 μL, 0.082 mmol)를 첨가하였다. 반응 혼합물을 실온에서 30분 동안 교반하였다. 용매를 20℃ 이하의 온도에서 회전 증발기를 통해 제거하였다. 중화 후, 잔류물을 플래시 크로마토그래피 (4 g, 핵산 중 0-60% 에틸 아세테이트, 16분) 정제하여, 무색 오일로서 표제 화합물을 얻었다.
기준 화합물 45
2-(3-
플루오로페닐
)-5,5-디메틸-N-p-
톨릴
-5,6,7,8-테트라히드로이미다조[1,2-a]피라진-3-아민
하기 방식으로 기준 화합물 43으로부터 기준 화합물 45를 제조하였다. 디옥산 8 mL 중 기준 화합물 43 (116 mg, 0.26 mmol)의 용액에 4-메틸아닐린 (84 mg, 0.78 mmol), Pd2(dba)3 (24 mg, 0.026 mmol), 크산트포스 (30 mg, 0.052 mmol) 및 Cs2CO3 (169 mg, 0.52 mmol)을 실온에서 첨가하였다. 반응 혼합물을 탈기시키고, 150℃에서 6시간 동안 N2 하에 교반하였다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, TFA 염으로서 황색 고체 116 mg을 얻었다. TFA 2 mL 중 부가생성물 (108 mg, 0.23 mmol)의 용액을 70℃에서 90분 동안 마이크로웨이브 오븐에서 교반하였다. HPLC 시험은 출발 물질이 없어지며, 목적 생성물이 주요 피크였음을 나타냈다. TFA를 제거하고, 잔류물을 바로 플래시 크로마토그래피 정제 (12 g, DCM 중 0-10% 메탄올 (NH3 변형), 30분)하여, 투명한 오일로서 표제 화합물을 얻었다.
TFA 매개 탈보호, 이어서 알킬화에 의해 화합물 43-4로부터 기준 화합물 46을 제조하였다. 화합물 48-3을 제조하고, 이어서 브롬화 (기준 화합물 51이 단계 (a)에서 사용된 것 제외)하는 것과 동일한 방식으로 기준 화합물 47을 제조하였다.
기준 화합물 48
2-(4-
플루오로페닐
)-5,5,7-
트리메틸
-7,8-
디히드로이미다조[1,2-a]피라진-
6(5H)-온
하기 방식에 의해 기준 화합물 51로부터 기준 화합물 48을 제조하였다. DMF 20 mL 중 기준 화합물 51 (694 mg, 3.0 mmol)의 용액에 60% NaH (600 mg, 15 mmol) 및 MeI (1.87 mL, 30 mmol)를 0℃에서 첨가하였다. 반응 혼합물을 동일한 온도에서 2시간 동안 교반하고, 실온에서 추가 2시간 동안 교반하였다. 반응 혼합물을 에틸 아세테이트로 희석시키고, 물로 세척하였다. 유기 용액을 건조시키고, 농축시켜, 플래시 크로마토그래피 정제 이후 메틸화된 생성물 백색 고체를 얻었다.
DCM 6 mL 중 (I) (216 mg, 0.79 mmol)의 교반된 용액에 아세트산 2 mL 중 Br2 (45 μL, 0.87 mmol)를 첨가하였다. 반응 혼합물을 실온에서 30분 동안 교반하였다. 용매를 20℃ 이하의 온도에서 회전 증발기를 통해 제거하였다. 중화 후, 잔류물을 추가 정제 없이 다음 단계에서 사용하였다.
기준 화합물 49
tert
-부틸 2-(3-
브로모
-2-(3-
플루오로페닐
)-5,5-디메틸-5,6-디히드로이미다
조[1,2-a]피라진
-7(8H)-일)-2-
옥소에틸카르바메이트
하기 방식에 의해 화합물 43-4로부터 기준 화합물 49를 제조하였다.
TFA 10 mL 중 (I) (365 mg, 1.0 mmol)의 용액을 70℃에서 20분 동안 교반하였다. HPLC 시험은 출발 물질이 남아있었으며, 소량의 목적 생성물이 검출되었음을 나타내었다. 반응 혼합물을 75℃에서 30분 동안 마이크로웨이브 오븐에서 교반하였다. TFA를 제거하고, 잔류물을 중화시켜, 황색 오일로서 화합물 49-1 약 252 mg (100%)을 얻었다.
DMF 10 mL 중 화합물 49-1 (245 mg, 1.0 mmol) 및 N-Boc-글리신 (350 mg, 2.0 mmol)의 교반된 용액에 HATU (760 mg, 2.0 mmol) 및 DIEA (0.52 mL, 3.0 mmol)를 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다.
반응 혼합물을 에틸 아세테이트로 희석시키고, 물로 세척하였다. 유기 용액을 건조시키고, 농축시켰다. 잔류물을 플래시 크로마토그래피 정제 (24 g, 헥산 중 0-100% 에틸 아세테이트, 36분)하여, 투명한 오일로서 화합물 49-2를 얻었다.
DCM 6 mL 중 화합물 49-2 (312 mg, 0.78 mmol)의 교반된 용액에 아세트산 2 mL 중 Br2 (57 μL, 1.1 mmol)를 첨가하였다. 반응 혼합물을 실온에서 30분 동안 교반하였다. 용매를 20℃ 이하의 온도에서 회전 증발기를 통해 제거하였다. 중화 후, 잔류물을 플래시 크로마토그래피 (25 g, 헥산 중 0-100% 에틸 아세테이트, 32분, 건조 로딩) 정제하여, 무색 오일로서 표제 화합물을 얻었다.
기준 화합물 50
3-
브로모
-2-(4-
플루오로페닐
)-7,8,8-
트리메틸
-5,6,7,8-테트라히드로이미다조
[1,2-a]피라진
하기 방식에 의해 화합물 35-5로부터 기준 화합물 50을 제조하였다.
CH3CN (50 ml) 중 화합물 35-5 (2.4 g, 9.80 mmol, 1.00 equiv)의 교반된 용액에 포르말린 (1.71 g, 21.09 mmol, 2.00 equiv, 37%)을 첨가하였다. 혼합물을 30℃에서 30분 동안 교반하였다. 이에 NaCNBH3 (1.85 g, 29.37 mmol, 3.00 equiv), 아세트산 (590 mg, 9.83 mmol, 1.00 equiv)을 첨가하였다. 얻어진 용액을 실온에서 2시간 동안 교반하였다. 얻어진 혼합물을 진공 하에 농축시켰다. 얻어진 용액을 물 10 ml로 희석시켰다. 탄산나트륨 (포화)으로 용액의 pH 값을 8 내지 9로 조절하였다. 얻어진 용액을 DCM (3×100 ml)으로 추출하고, 합쳐진 유기 층을 무수 황산나트륨에서 건조시키고, 농축시켰다. 잔류물을 실리카 겔 컬럼 (에틸 아세테이트/석유 에테르 (1:7))에 적용하여, 백색 고체로서 화합물 50-1을 얻었다.
DCM 6 mL 중 화합물 50-1 (933 mg, 3.60 mmol)의 교반된 용액에 아세트산 2 mL 중 Br2 (204 μL, 3.96 mmol)를 첨가하였다. 반응 혼합물을 실온에서 30분 동안 교반하였다. 용매를 20℃ 이하의 온도에서 회전 증발기를 통해 제거하였다. 중화 후, 잔류물을 플래시 크로마토그래피 (40 g, DCM 중 0-10% 메탄올, 50분, 건조 로딩) 정제하여, 백색 고체로서 표제 화합물 998 mg (82%)을 얻었다.
기준 화합물 51
2-(4-
플루오로페닐
)-7,8-
디히드로이미다조[1,2-a]피라진
-6(5H)-온
하기 방식에 의해 기준 화합물 51을 제조하였다.
DMF (30 mL) 중 2-브로모-1-(4-플루오로페닐)에탄온 (3.0 g, 13.82 mmol)의 교반된 용액에 2-(tert-부톡시카르보닐)아세트산 (2.5 g, 14.29 mmol) 및 Cs2CO3 (5.0 g, 15.34 mmol)을 첨가하였다. 얻어진 용액을 30℃에서 밤새 교반하였다. 얻어진 용액을 물 40 ml에 부었다. 수성 층을 에틸 아세테이트 (3×20 mL)로 추출하고, 합쳐진 유기 층을 염수 (3×20 mL)로 세척하고, 무수 황산나트륨에서 건조시키고, 진공 하에 농축시켰다. 고체를 n-헥산/에틸 아세테이트 (10:1)의 혼합물로 세척하였다. 백색 고체로서 화합물 51-1이 생성되었다.
톨루엔 (200 mL) 중 화합물 51-1 (25.95 g, 75.14 mmol)의 교반된 용액에 NH4OAc (110 g, 20.00 equiv)를 첨가하였다. 얻어진 용액을 4시간 동안 가열 환류시켰다. 혼합물을 실온으로 냉각시키고, 진공 하에 농축시켰다. 잔류물을 에틸 아세테이트 800 mL로 희석시켰다. 얻어진 혼합물을 염수 (3×30 mL)로 세척하고, 무수 황산나트륨에서 건조시키고, 진공 하에 농축시켰다. 잔류물을 석유 에테르/EtOAc (20:1) 10 mL로 세척하여, 백색 고체로서 화합물 51-2를 얻었다.
DMF (30 mL) 중 화합물 51-2 (2.58 g, 8.87 mmol)의 교반된 용액에 에틸 2-브로모아세테이트 (4.4 g, 26.35 mmol, 3.00 equiv) 및 Cs2CO3 (8.7 g, 26.69 mmol, 3.00 equiv)을 첨가하였다. 얻어진 용액을 30℃에서 밤새 교반하였다. 얻어진 용액을 에틸 아세테이트 30 mL로 희석시키고, 합쳐진 유기 층을 염수 (3×20 mL)로 세척하고, 무수 황산나트륨에서 건조시키고, 진공 하에 농축시켰다. 잔류물을 실리카 겔 컬럼 (에틸 아세테이트/석유 에테르 (1:10))에 적용하였다. 밝은 백색 고체로서 화합물 51-3이 생성되었다.
메탄올 (200 mL) 중 화합물 51-3 (8 g, 19.46 mmol)의 교반된 용액에 Pd/C (0.8 g)를 첨가하였다. 얻어진 용액을 탈기시키고, 수소로 역충전하였다. 혼합물을 실온에서 밤새 교반하였다. 고체를 여과하였다. 얻어진 혼합물을 진공 하에 농축시켰다. 얻어진 조질의 고체를 석유 에테르/EtOAc (1:10) 100 mL로 세척하였다. 백색 고체로서 표제 화합물이 생성되었다.
TFA 중 발연 질산으로의 니트로화에 의해 기준 화합물 51로부터 기준 화합물 52를 제조하였다. 기준 화합물 19를 제조하는 것과 동일한 방식, 즉 2-아미노피라진, 이소니코틴알데히드 및 2-이소시아노-2-메틸프로판 사이의 3 성분 우기 반응, 이어서 TFA 매개 탈보호로 기준 화합물 53을 제조하였다. 유리 아민을 1-브로모-4-메틸벤젠과 Pd2(dba)3 매개 아미노화 반응시키고, 이어서 PtO2 매개 수소화시켰다. 2-아미노피라진, 2-메톡시벤즈알데히드, 1-이소시아노-4-메틸벤젠으로부터 기준 화합물 1의 제조와 동일한 3 성분 우기 반응, 이어서 PtO2 매개 수소화에 의해 기준 화합물 54를 제조하였다.
기준 화합물 55
3-
브로모
-2-(4-
플루오로페닐
)-8,8-디메틸-7,8-
디히드로이미다조
[1,2-a]피라진-6(5H)-온
하기 방식으로 화합물 35-4로부터 기준 화합물 55를 제조하였다. DCM (20 mL) 중 화합물 35-4 (390 mg, 1.51 mmol, 1.00 equiv)의 교반된 용액에 NBS (0.28 g, 1.00 equiv)를 첨가하였다. 얻어진 용액을 실온에서 2시간 동안 교반하였다. 고체를 여과하고, 혼합물을 포화 Na2S2O3 용액으로 세척하고, Na2SO4에서 건조시켰다. 혼합물을 진공 하에 농축시켰다. 고체를 실리카 겔 크로마토그래피 (석유 에테르/EtOAc = 1:2)에 의해 정제하여, 백색 고체로서 표제 화합물이 생성되었다.
50℃에서 THF 중 Boc-OSu와의 반응에 의해 화합물 35-5로부터 기준 화합물 56을 제조하였다. NaH/MeI를 사용하는 알킬화에 의해 화합물 35-4로부터 기준 화합물 57을 제조하였다. (R)-2-(벤질옥시카르보닐)-3-메틸부탄산을 단계 (a)에서 사용한 것을 제외하고는 화합물 35-4에서와 동일한 방식에 의해 기준 화합물 58을 제조하였다. 2-브로모-1-(3,4-디플루오로페닐)에탄온을 단계 (a)에서 사용한 것을 제외하고는 화합물 35-4에서와 동일한 방식으로 기준 화합물 59를 제조하였다. (S)-2-(벤질옥시카르보닐)프로판산을 단계 (a)에서 사용한 것을 제외하고는 화합물 35-4를 제조하는 것과 동일한 방식에 의해 기준 화합물 60을 제조하였다. (S)-2-(벤질옥시카르보닐) 3-메틸부탄산을 단계 (a)에서 사용한 것을 제외하고는 화합물 35-4를 제조하는 것과 동일한 방식에 의해 기준 화합물 61을 제조하였다. (R)-2-(벤질옥시카르보닐)프로판산을 단계 (a)에서 사용한 것을 제외하고는 화합물 35-4를 제조하는 것과 동일한 방식에 의해 기준 화합물 62를 제조하였다. (S)-2-(벤질옥시카르보닐)-3-메틸부탄산을 단계 (a)에서 사용한 것을 제외하고는 기준 화합물 35를 제조하는 것과 동일한 방법에 의해 기준 화합물 63을 제조하였다. (R)-2-(벤질옥시카르보닐)-3-메틸부탄산을 단계 (a)에서 사용한 것을 제외하고는 기준 화합물 35를 제조하는 것과 동일한 방법에 의해 기준 화합물 64를 제조하였다. (S)-2-(벤질옥시카르보닐)-3-메틸부탄산을 단계 (a)에서 사용한 것을 제외하고는 기준 화합물 35를 제조하는 것과 동일한 방법에 의해 기준 화합물 65를 제조하였다. (R)-2-(벤질옥시카르보닐)-3-메틸부탄산을 단계 (a)에서 사용한 것을 제외하고는 기준 화합물 35를 제조하는 것과 동일한 방법에 의해 기준 화합물 66을 제조하였다. 2-브로모-1-(3-플루오로페닐)에탄온을 단계 (a)에서 사용한 것을 제외하고는 기준 화합물 55를 제조하는 것과 동일한 방식으로 기준 화합물 67을 제조하였다. 1-브로모-2,4-디플루오로벤젠과의 아미노화 반응, 이어서 Pd/C 매개 수소화에 의해 기준 화합물 19로부터 기준 화합물 68을 제조하였다. 1-브로모-3-플루오로-4-클로로벤젠과의 아미노화 반응, 이어서 PtO2 매개 수소화로부터 제조되는 것인, 기준 화합물 32로부터 기준 화합물 69를 합성하였다. 1-브로모-3-플루오로-4-클로로벤젠과의 아미노화 반응, 이어서 PtO2 매개 수소화로부터 제조되는 것인, 기준 화합물 11로부터 기준 화합물 70을 합성하였다. 기준 화합물 49가 제조되는 것과 유사한 방식으로 기준 화합물 51로부터 기준 화합물 71을 합성하였다.
기준 화합물 72
3-
브로모
-7-(2-(디메틸아미노)에틸)-2-(4-
플루오로페닐
)-8,8-디메틸-7,8-
디히드로이미다조[1,2-a]피라진
-6(5H)-온
하기 반응에 의해 화합물 35-4로부터 기준 화합물 72를 제조하였다.
DMF 5 mL 중 화합물 35-4 (259 mg, 1.0 mmol)의 용액에 60% NaH (60 mg, 1.5 mmol) 및 2-브로모-N,N-디메틸에탄아민 (228 mg, 1.5 mmol)을 실온에서 첨가하였다. 반응 혼합물을 실온에서 6시간 동안 교반하였다. LC/MS 시험은 화합물 35-4가 없어졌으며, 목적 생성물 ([M+1] = 331)은 하나의 주요 피크였음을 나타내었다.
반응 혼합물을 에틸 아세테이트로 희석시키고, 물로 2회 세척하였다. 유기 용액을 건조시키고, 농축시켰다. 얻어진 조생성물을 추가 정제 없이 다음 단계에서 사용하였다.
DCM 3 mL 중 이전 단계로부터 얻어진 조생성물 (198 mg, 0.60 mmol)의 교반된 용액에 아세트산 1 mL 중 Br2 (34 μL, 0.66 mmol)를 첨가하였다. 반응 혼합물을 실온에서 30분 동안 교반하였다. HPLC/MS 시험은 출발 물질이 없어졌으며, 기준 화합물 72가 주요 생성물이었음을 나타내었다.
용매를 20℃ 이하의 온도에서 회전 증발기를 통해 제거하였다. 잔류물을 질량-유발 HPLC 정제하여 기준 화합물 72 110 mg을 얻었다.
기준 화합물 73: 4-플루오로-3-메틸아닐린과의 Pd2(dba)3 매개 아미노화 반응에 의해 기준 화합물 67로부터 3-(4-플루오로-3-메틸페닐아미노)-2-(3-플루오로페닐)-8,8-디메틸-7,8-디히드로이미다조[1,2-a]피라진-6(5H)-온을 합성하였다. 기준 화합물 74: Br2와의 브로민화 반응에 의해 기준 화합물 56으로부터 tert-부틸 3-브로모-2-(4-플루오로페닐)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-카르복실레이트를 제조하였다. 기준 화합물 75: 2-브로모아세틸 브로마이드와의 아미드화 반응에 의해 실시예 493으로부터 2-브로모-1-(2-(4-플루오로페닐)-3-(4-플루오로페닐아미노)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)에탄온을 제조하였다.
기준 화합물 76
2-(4-
플루오로페닐
)-6-
메틸이미다조[1,2-a]피리딘
-3-아민
하기 단계에 의해 기준 화합물 76을 제조하였다.
MeOH 20 mL 중 5-메틸피리딘-2-아민 (260 mg, 2.4 mmol)의 교반된 용액에 4-플루오로벤즈알데히드 (0.26 mL, 2.40 mmol), 이어서 MeOH 중 1.0 N HClO4 (0.20 mL, 0.20 mmol)를 첨가하였다. 반응 혼합물을 실온에서 0.5시간 동안 교반하고, 이어서 2-이소시아노-2-메틸프로판 (0.23 mL, 2.0 mmol)을 첨가하였다. 실온에서 밤새 교반을 계속하였다. HPLC/MS 시험은 목적 생성물인 기준 화합물 76-1이 주요 피크였음을 나타내었다.
반응 혼합물을 바로 질량-유발 HPLC 정제하였다. 황색 고체로서 우기 부가생성물 62 mg을 얻었다.
DCM 5 mL 중 우기 부가생성물 (366 mg, 1.23 mmol)의 용액에 TFA 5 mL를 첨가하였다. 반응 혼합물을 실온에서 교반하였다. LC/MS 시험은 [M+1] = 338을 갖는 주요 피크를 나타내었으며, 이는 기준 화합물 76-2에 해당하였다. 반응 혼합물을 농축시켜 황색 고체 431 mg을 얻었다.
MeOH 3 mL 및 물 3 mL 중 기준 화합물 76-2 (101 mg, 0.30 mmol)의 용액에 KOH (168 mg, 3.0 mmol)를 첨가하였다. 반응 혼합물을 60℃에서 3시간 동안 교반하였다. LC/MS 시험은 [M+1] = 242를 갖는 주요 피크를 나타내었으며, 이는 목적 생성물인 기준 화합물 76에 해당하였다. 반응 혼합물을 농축시키고, 잔류물을 DCM에 용해시켰다. 유기 용액을 NaHCO3으로 세척하고, 건조시키고, 농축시켰다. 생성물을 추가 정제 없이 사용하였다.
기준 화합물 77: 기준 화합물 76에서와 동일한 단계에 의해 2-(4-플루오로페닐)이미다조[1,2-a]피리딘-3-아민을 제조하였다.
실시예
1
2-아미노-1-(3-(
벤조[d][1,3]디옥솔
-5-
일아미노
)-2-
페닐
-5,6-
디히드로이미다조[1,2-a]피라진
-7(8H)-일)
에탄온
하기 방식으로 실시예 1을 제조하였다. DMF 2 mL 중 N-BOC-글리신 (142 mg, 0.81 mmol)의 교반된 용액에 HATU (308 mg, 0.81 mmol) 및 DIEA (0.28 mL, 1.62 mmol)를 첨가하였다. 10분 동안 교반한 이후, 기준 화합물 1 (180 mg, 0.54 mmol)을 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다.
용매를 제거하고, 조생성물을 MS-유발 HPLC 정제하였다. MeCN이 더 이상 남아있지 않을 때까지 수집된 MeCN/물 용액을 농축시켰다. 남아있는 수용액을 NaHCO3으로 중화시키고, DCM으로 추출하였다. 유기 용액을 건조시키고, 농축시켰다. 잔류물을 1:1 MeCN/물 용매에 용해시키고, 동결건조기에서 건조시켜, 분말 생성물 192 mg을 얻었다.
4:1 DCM 및 TFA 10 mL 중 상기 얻어진 아미드 (265 mg, 0.54 mmol)의 용액을 실온에서 2시간 동안 교반하였다. 용매를 제거하고, 조생성물을 MS-유발 HPLC 정제하였다. MeCN이 더 이상 남아있지 않을 때까지 수집된 MeCN/물 용액을 농축시켰다. 남아있는 수용액을 NaHCO3으로 중화시키고, DCM으로 추출하였다. 유기 용액을 건조시키고, 농축시켰다. 이후, 1:1 MeCN/물 용매에 용해시키고, 동결건조기에서 건조시켜, 분말 생성물을 얻었다.
실시예
26
N,2-비스(4-
플루오로페닐
)
이미다조
[1,2-a]피라진-3-아민
하기 방식에 의해 실시예 26을 합성하였다. MeOH 50 mL 중 2-아미노피라진 (683 mg, 7.18 mmol)의 교반된 용액에 4-플루오로벤즈알데히드 (1.16 mL, 10.8 mmol), 1-플루오로-4-이소시아노벤젠 (1.0 g, 8.25 mmol), 이어서 MeOH 중 1.0 N HClO4 (0.72 mL, 0.72 mmol)를 첨가하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 반응 혼합물을 농축시키고, 잔류물을 플래시 크로마토그래피 정제하였다. 수집된 유기 용액을 농축시켜, 황색 오일로서 표제 화합물을 얻었다.
실시예
28
N,2-
비스
(4-
플루오로페닐
)-5,6,7,8-
테트라히드로이미다조[1,2-a]피라진
-3-아민
하기 방식에 의해 실시예 28을 합성하였다. MeOH 10 mL 중 실시예 26 (761 mg, 2.36 mmol)의 교반된 용액에 Pd/C (258 mg, 0.24 mmol)를 첨가하였다. 반응 혼합물을 탈기시키고, H2로 역충전하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 고체를 여과하고, 용매를 제거하였다. 생성물을 질량-유발 HPLC 정제하였다. 얻어진 MeCN/물 용액을 합하고, 농축시켜, 중화 후 황색 오일로서 최종 생성물을 얻었다.
실시예
29
2-아미노-1-(3-(3,4-
디플루오로페닐아미노
)-2-(4-
플루오로페닐
)-5,6-
디히드
로이미다조[1,2-a]피라진-7(8H)-일)-2-
메틸프로판
-1-온
하기 방식에 의해 실시예 29를 합성하였다. DMF 2 mL 중 2-(tert-부톡시카르보닐아미노)-2-메틸프로판산 (25 mg, 0.12 mmol)의 교반된 용액에 HATU (46 mg, 0.12 mmol) 및 DIEA (63 μL, 0.36 mmol)를 첨가하였다. 10분 동안 교반한 후, 실시예 331 (21 mg, 0.06 mmol)을 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다. 반응 혼합물을 바로 질량-유발 HPLC 정제하였다. 수집된 MeCN/물 용액을 농축시키고, 중화시켰다. 4:1 DCM 및 TFA 5 mL 중 얻어진 생성물 (26 mg, 0.05 mmol)을 실온에서 2시간 동안 교반하였다. 반응 혼합물을 농축시키고, 잔류물을 질량-유발 HPLC 정제하였다. 수집된 MeCN/물 용액을 합하고, MeCN을 제거하였다.
실시예
32
1-(2-(4-
플루오로페닐
)-3-(4-
플루오로페닐아미노
)-5,6-디히드로이미다조[
1,2-a]피라진
-7(8H)-일)-2-(
메틸아미노
)
에탄온
하기 방식에 의해 실시예 28로부터 실시예 32를 제조하였다.
DCM 10 mL 중 실시예 28 (33 mg, 0.10 mmol)에 Et3N (84 μL, 0.60 mmol) 및 2-클로로아세틸 클로라이드 (24 μL, 0.30 mmol)를 0℃에서 첨가하였다. 반응 혼합물을 동일한 온도에서 2시간 동안 교반하고, 실온에서 추가 2시간 동안 교반하였다. 용매를 제거하고, 잔류물을 MS-유발 HPLC 정제하여, 중화 후 황색 고체로서 화합물 32-1 40 mg (100%)을 얻었다.
DMF 5 mL 중 화합물 32-1 (20 mg, 0.05 mmol)에 K2CO3 (21 mg, 0.15 mmol) 및 2.0 M MeNH2 (0.30 mL, 0.60 mmol)를 실온에서 첨가하였다. 반응 혼합물을 동일한 온도에서 밤새 교반하였다. 용매를 제거하고, 잔류물을 MS-유발 HPLC 정제하여, 중화 후 황색 고체로서 표제 화합물을 얻었다.
실시예
44
1-(2-(4-
플루오로페닐
)-3-(4-
플루오로페닐아미노
)-5,6-디히드로이미다조[
1,2-a]피라진
-7(8H)-일)-2-
히드록시에탄온
하기 방식에 의해 실시예 44를 합성하였다. DMF 5 mL 중 화합물 32-1 (20 mg, 0.05 mmol)의 용액에 KI (8 mg, 0.05 mmol) 및 AcOK (15 mg, 0.15 mmol)를 실온에서 첨가하였다. 반응 혼합물을 동일한 온도에서 밤새 교반하였다. 용매를 제거하고, 잔류물을 MS-유발 HPLC 정제하여, 황색 고체를 얻었다. 메탄올 3 mL 및 물 1 mL 중 고체 (21 mg, 0.05 mmol)의 용액에 LiOH (6 mg, 0.25 mmol)를 첨가하였다. 반응 혼합물을 40℃에서 2시간 동안 교반하였다. 반응 혼합물을 실온으로 냉각시키고, 유기 용매를 제거하였다. 잔류물을 질량-유발 HPLC 분리하였다. 수집된 MeCN/물 용액을 농축시켜, 황색빛 오일로서 표제 화합물을 얻었다.
실시예
113
2-(4-
플루오로페닐
)-N-p-
톨릴
-5,6,7,8-
테트라히드로이미다조[1,2-a]피라진
-3-아민
하기 방식에 의해 실시예 113을 제조하였다. MeOH 5 mL 중 실시예 136 (64 mg, 0.20 mmol)의 교반된 용액에 Pd/C (21 mg, 0.02 mmol)를 첨가하였다. 반응 혼합물을 탈기시키고, H2로 역충전하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, 황색 고체를 얻었다.
실시예
136
2-(4-
플루오로페닐
)-N-p-
톨릴이미다조[1,2-a]피라진
-3-아민
하기 방식에 의해 실시예 136을 제조하였다. 디옥산 6 mL 중 기준 화합물 19 (69 mg, 0.30 mmol)의 용액에 4-브로모톨루엔 (74 μL, 0.60 mmol), Pd2(dba)3 (8 mg, 0.009 mmol), 크산트포스 (11 mg, 0.018 mmol) 및 Cs2CO3 (196 mg, 0.60 mmol)을 실온에서 첨가하였다. 반응 혼합물을 탈기시키고, 120℃에서 5시간 동안 N2 하에 교반하였다. 반응 혼합물을 실온으로 냉각시키고, 고체를 여과하였다. 얻어진 여액을 농축시켰다. 잔류물을 질량-유발 HPLC 정제하여, 중화 후 황색 오일로서 표제 화합물 약 72 mg (75%)을 얻었다.
실시예
251
(3-(디메틸아미노)
피롤리딘
-1-일)(2-(4-
플루오로페닐
)-3-(p-톨릴아미노)-5,6-
디히드로이미다조[1,2-a]피라진
-7(8H)-일)
메탄온
하기 방식에 의해 실시예 113으로부터 실시예 251을 제조하였다.
DCM 10 mL 중 실시예 113 (161 mg, 0.50 mmol) 및 Et3N (139 μL, 1.5 mmol)의 교반된 용액에 4-니트로페닐 카르보노클로리데이트 (202 mg, 1.0 mmol)를 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다. 반응 혼합물을 MS-유발 HPLC 분리하였다. 수집된 MeCN/물 용액을 합하고, 농축시켜, 황색 오일로서 화합물 251-1을 얻었다.
NMP 2 mL 중 화합물 251-1 (20 mg, 0.041 mmol) 및 Et3N (17 μL, 0.123 mmol)에 N,N-디메틸피롤리딘-3-아민 (15 μL, 0.123 mmol)을 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다. 반응 혼합물을 MS-유발 HPLC 정제하였다. 수집된 MeCN/물 용액을 합하고, 농축시켜, 황색 오일로서 표제 화합물을 얻었다.
실시예
262
N-(4-
클로로페닐
)-2-(4-
플루오로페닐
)-5,6,7,8-
테트라히드로이미다조[1,2-a]피라진
-3-아민
하기 방식에 의해 실시예 262를 제조하였다. 디옥산 6 mL 중 기준 화합물 19 (69 mg, 0.30 mmol)의 용액에 1-브로모-4-클로로벤젠 (115 mg, 0.60 mmol), Pd2(dba)3 (8 mg, 0.009 mmol), 크산트포스 (11 mg, 0.018 mmol) 및 Cs2CO3 (196 mg, 0.60 mmol)을 실온에서 첨가하였다. 반응 혼합물을 탈기시키고, 120℃에서 5시간 동안 N2 하에 교반하였다. 반응 혼합물을 실온으로 냉각시키고, 고체를 여과하였다. 얻어진 여액을 농축시켰다. 잔류물을 질량-유발 HPLC 정제하여, 중화 후 황색 오일을 얻었다. MeOH 5 mL 중 얻어진 부가생성물 (68 mg, 0.20 mmol)의 교반된 용액에 Pd/C (21 mg, 0.02 mmol)를 첨가하였다. 반응 혼합물을 탈기시키고, H2로 역충전하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, 황색 고체로서 표제 화합물 39 mg (57%)을 얻었다.
실시예
266
2-m-
톨릴
-N-p-
톨릴
-5,6,7,8-
테트라히드로이미다조[1,2-a]피라진
-3-아민
하기 방식에 의해 실시예 266을 합성하였다. 100 mL 둥근 바닥 플라스크에, 메탄올 (10 mL) 중 피라진-2-아민 (1.2 g, 12.6 mmol), 3-메틸벤즈알데히드 (1.44 g, 12.0 mmol) 및 HClO4 (200 mg, 2.0 mmol)의 용액을 두었다. 반응 혼합물을 실온에서 30분 동안 교반하고, 이후 혼합물에 1-이소시아노-4-메틸벤젠 (1.2 g, 10.3 mmol)을 첨가하였다. 얻어진 용액을 실온에서 12시간 동안 교반하였다. 용매를 제거한 후, 잔류물을 실리카 겔 컬럼 (디클로로메탄/메탄올 (10:1))에 적용하여, 우기 부가생성물 1.1 g이 생성되었다. 메탄올 (50 mL) 중 얻어진 우기 부가생성물 (1.0 g, 3.18 mmol)의 용액에 PtO2 (72 mg, 0.32 mmol)를 첨가하였다. 이후, 반응 혼합물을 탈기시키고, H2로 역충전하였다. 반응 혼합물을 실온에서 밤새 교반하였다. 고체를 여과하고, 여액을 진공 하에 농축시켜, 백색 고체로서 표제 화합물을 얻었다.
실시예
267
(S)-
tert
-부틸 1-(2-(4-
플루오로페닐
)-3-(p-
톨릴아미노
)-5,6-
디히드로이미다
조[
1,2-a]피라진
-7(8H)-일)-1-옥소-3-(4-(
펜틸아미노
)
페닐
)프로판-2-
일카르바메이트
(S)-2-(tert-부톡시카르보닐아미노)-3-(4-니트로페닐)프로판산과의 HATU 매개된 커플링, 이어서 아닐린 유도체에 대한 Pd/C 매개 수소화에 의해 실시예 113으로부터 실시예 267을 합성하였다. 무수 THF 5 mL 중 아닐린 유도체 (33 mg, 0.056 mmol)의 교반된 용액에 펜탄알 (18 μL, 0.168 mmol)을 실온에서 질소 하에 첨가하였다. 30분 후 NaBH4 (6 mg, 0.168 mmol)를 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다. 용매를 제거하였다. 잔류물을 메탄올에 용해시키고, 질량-유발 HPLC 정제하였다. 얻어진 MeCN/물 용액을 합하고, 농축시켜, 황색 오일을 얻었다.
실시예
289
(5R,8R)-2,8-
디벤질
-3-
메틸
-5-
페네틸
-7,8-
디히드로이미다조[1,2-a]피라진
-6(5H)-온
하기 방식으로 실시예 289를 제조하였다.
DMF 30 mL 중 (R)-2-(벤질옥시카르보닐아미노)-3-페닐프로판산 (5 gm, 1.0 eq.) 및 (R)-에틸 2-아미노-3-페닐프로파노에이트 히드로클로라이드 (3.83 gm, 1.0 eq.)의 교반된 용액에 HATU (6.98 gm, 1.1 eq.) 및 DIEA (3.44 ml, 1.1 eq.)를 첨가하였다. 반응 혼합물을 실온에서 6시간 동안 교반하였다. HPLC/MS 시험은 목적 생성물인 화합물 289-1이 유일한 생성물이었지만 다른 피크로 오염되었음을 나타내었다. 반응물을 EtOAc/물 사이에서 분배시키고, 이후 조생성물을 플래시 크로마토그래피로 정제하여, 화합물 289-1을 얻었다.
화합물 289-1 (3 gm, 1.0 eq.) 및 2 N NaOH 9.5 ml 및 THF 30 ml의 교반된 용액을 혼합하였다. 반응 혼합물을 실온에서 6시간 동안 교반하였다. 반응 혼합물을 산성화시키고, 이후 EtOAc/물 사이에 분배시켰으며, 이후 조생성물을 다음 단계에서 그 자체로 사용하였다.
디클로로메탄 (25 ml) 중 화합물 289-2 (1 gm, 1.0 eq.) 및 아세트산 무수물 (0.254 ml, 1.2 eq.)의 교반된 용액에 DIEA (0.756 ml, 4.4 eq.) 및 DMAP (13.4 mg, 5m%)를 첨가하였다. 반응 혼합물을 실온에서 8시간 동안 교반하였다. LCMS는 목적 생성물이 형성되었음을 나타내었다. 유기 층을 MeOH로 켄칭시키고, 농축시켰다. 유기 층을 물/EtOAc로 세척하고, 다음 단계에서 조생성물로서 사용하였다.
화합물 289-3 (0.8 gm, 1.0 eq.) 및 (R)-에틸 2-아미노-4-페닐부타노에이트 (0.596 gm, 1.6 eq.)를 PTSA (10 m%)와 함께 혼합하였다. 반응물을 딘-스탁 장치에서 130℃로 가열하였다. 격렬한 환류를 얻도록 약간의 진공을 상부로부터 적용하였다. 반응물을 2시간 동안 가열하였다. 톨루엔을 측면 암 (side arm)으로부터 제거하고, 부피가 주 용기에 3회 내지 4회 다시 보충되어 반응의 완료를 초래하였다. LCMS는 신규 피크의 형성에 의해 나타난 것과 같이 반응의 완료를 나타내었다. 신규 피크는 질량이 없었다. 반응물을 농축시키고, 조생성물을 다음 단계에 공급하였다.
화합물 289-4를 피리딘에 용해시키고, POCl3을 첨가하고, 반응물을 48시간 동안 교반하였다. LCMS는 목적 생성물이 형성되었음을 나타내었다. 반응물을 농축시켰다. 오일을 포화 NaHCO3으로 중화시키고, 디클로로메탄으로 추출하였다. 유기 층을 건조/농축시키고, 컬럼 크로마토그래피하였다.
MeOH 30 mL 중 화합물 289-5 (0.7 g, 1.0 eq.)의 교반된 용액에 Pd/C (0.007 g)를 첨가하였다. 반응 혼합물을 탈기시키고, H2로 역충전하였다. 반응 혼합물을 실온에서 밤새 교반하였다. HPLC 시험은 출발 물질이 모두 없어졌으며, (II)가 주요 피크였음을 나타내었다. 고체를 여과하고, 용매를 제거하여, 표제 화합물을 얻었다. LCMS는 반응물이 라세미화되었음을 나타내었다 (2 피크).
실시예
292
N-(4-
클로로
-3-
플루오로페닐
)-2-(4-
플루오로페닐
)-N-
메틸
-5,6,7,8-테트라히드로이미다조
[1,2-a]피라진
-3-아민
하기 방식에 의해 실시예 292를 제조하였다. MeOH 20 ml 중 피라진-2-아민 (2.4 g, 25.26 mmol)의 교반된 용액에 4-플루오로벤즈알데히드 (3.0 g, 24.19 mmol) 및 HClO4 (70%, 0.4 g)를 첨가하고, 이후 혼합물을 실온에서 30분 동안 교반하고, 이어서 1-클로로-2-플루오로-4-이소시아노벤젠 (3.2 g, 20.58 mmol)을 첨가하였다. 실온에서 밤새 교반을 계속하고, 이후 용매를 진공 하에 제거하였으며, 조생성물을 실리카 겔 크로마토그래피 (디클로로메탄/메탄올)에 의해 정제하여, 황색 고체로서 우기 부가생성물을 수득하였다.
DMF (10 mL) 중 얻어진 우기 부가생성물 (1.2 g, 3.36 mmol, 1.00 equiv)의 용액에 수소화나트륨 (1.0 g, 25.00 mmol, 1.20 equiv, 60%)을 0℃에서 첨가하였다. 반응 혼합물을 이 온도에서 30분 동안 교반하였으며, 이어서 아이오도메탄 (1.7 g, 11.97 mmol, 3.56 equiv)을 첨가하였다. 얻어진 용액을 0℃에서 30분 동안 교반하면서 반응하도록 하였다. 반응 혼합물을 얼음물 20 ml에 부었다. 고체를 여과에 의해 수집하고, 물 10 ml로 세척하여, N-메틸 생성물 1.1 g (88%)이 생성되었다.
메탄올 (100 mL) 중 N-메틸 생성물 (1.0 g, 2.70 mmol, 1.00 equiv)의 용액에 PtO2 (30 mg, 0.13 mmol, 0.10 equiv)를 첨가하였다. 얻어진 용액을 실온에서 8시간 동안 교반하면서 반응하도록 하였다. 고체를 여과하고, 얻어진 용액을 진공 하에 농축시켰다. 잔류물을 실리카 겔 크로마토그래피 (디클로로메탄/메탄올 (20:1))에 적용하여, 백색 고체로서 표제 화합물 500 mg (49%)이 생성되었다.
실시예
297
N-
tert
-부틸-2-(4-
플루오로페닐
)-5,6,7,8-
테트라히드로이미다조[1,2-a]피라진
-3-아민
하기 방식에 의해 기준 화합물 19-1의 전구체로부터 실시예 297을 합성하였다. 메탄올 (20 mL) 중 기준 화합물 19-1 (1.0 g, 3.52 mmol, 1.00 equiv)의 용액에 PtO2 (80 mg, 0.35 mmol, 0.10 equiv)를 첨가하였다. 얻어진 용액을 탈기시키고, 수소로 역충전하고, 실온에서 밤새 교반을 계속하였다. 고체를 여과하고, 용매를 진공 하에 증발시켰다. 잔류물을 실리카 겔 크로마토그래피 (디클로로메탄/메탄올 (50:1))에 적용하여, 백색 고체로서 표제 화합물 837 mg (83.7%)을 얻었다.
실시예
412
2-아미노-1-(2-(4-
플루오로페닐
)-3-(4-
플루오로페닐아미노
)-8,8-디메틸-5,6-디히드로이미다조[
1,2-a]피라진
-7(8H)-일)
에탄온
p-톨루이딘과의 Pd2(dba)3 매개 아미노화 반응, 이어서 TFA 매개 탈보호에 의해 기준 화합물 35로부터 실시예 412를 제조하였다.
기준 화합물 35-4의 합성: 메탄올 (800 mL) 중 기준 화합물 35-3 (70 g, 159.45 mmol, 1.00 equiv.)의 교반된 용액에 탄소상 팔라듐 (10 g)을 첨가하였다. 얻어진 용액을 탈기시키고, 수소로 역충전하였다. 용액을 25℃에서 3일 동안 교반하였다. 고체를 여과하고, MeOH로 세척하였다. 여액을 감압 하에 농축시켰다. 백색 고체로서 기준 화합물 35-4 (38 g, 145.56 mmol, 91%)이 생성되었다.
기준 화합물 35-5의 합성: 기준 화합물 35-4 (5 g, 19.2 mmol, 1 equiv.)을 THF 50 mL에 용해시키고, 1 M 보란/THF 착물 (57 ml, 57 mmol, 3 equiv.)을 서서히 첨가하고, 반응물을 밤새 환류시켰다. LCMS는 반응이 완료되었음을 나타내었다. THF를 감압 하에 제거하였다. 반응물을 MeOH로 켄칭시켰다. 기준 화합물 35-5의 조생성물 (4.5 g, 18.3 mmol, 95%)을 다음 단계에서 사용하였다.
기준 화합물 35-6의 합성: 디클로로메탄 15 mL 중 기준 화합물 35-5 (2.9 g, 11.82 mmol, 1.1 equiv.) 및 2-(tert-부톡시카르보닐아미노)아세트산 (2.27 g, 13 mmol, 1.1 equiv.)의 교반된 용액에 DIEA (2.47 ml, 14.18 mmol, 1.2 equiv.), HATU (5.39 gm, 14.18 mmol, 1.2 equiv.)를 첨가하였다. 반응 혼합물을 실온에서 8시간 동안 교반하였다. HPLC/MS 분석은 목적 생성물인 기준 화합물 35-6이 주요 생성물이었음을 나타내었다. 반응물을 디클로로메탄 70 ml로 희석시켰다. 유기 층을 물 (1×30 ml)로, 이어서 포화 NaHCO3 (1×30 ml)으로, 최종적으로 염수 (1×30 ml)로 세척하였다. 이후, 유기 층을 무수 Na2SO4에서 건조시키고, 진공 하에 농축시켰다. 얻어진 오일을 용리액으로서 사용되는 헥산/에틸 아세테이트 (0-100% 선형 구배)로 컬럼 크로마토그래피를 사용하여 정제하였다. 오일로서 목적 생성물인 기준 화합물 35-6을 얻었다 (3.3 g, 8.27 mmol, 70%).
기준 화합물 36의 합성: MeCN (20 mL) 중 기준 화합물 35-6 (2.0 g, 4.97 mmol, 1.00 equiv.)의 용액에 NBS (0.88 g, 1.00 equiv)를 첨가하였다. 얻어진 용액을 실온에서 15분 동안 교반하였다. HPLC/MS는 목적 생성물인 기준 화합물 36이 배타적으로 형성되었음을 나타내었다. 반응물을 감압 하에 증발시켰다. 고체를 디클로로메탄 50 ml에 용해시켰다. 이후, 유기 층을 무수 Na2SO4에서 건조시키고, 진공 하에 농축시켰다. 얻어진 고체를 용리액으로서 헥산/에틸 아세테이트 (0-100%)를 사용하여 컬럼 크로마토그래피로 정제하였다. 회백색/유리질 고체로서 목적 화합물인 기준 화합물 36을 얻었다 (1.9 g, 3.96 mmol, 80%).
실시예 412의 합성: 유리 바이알에서, Cs2CO3, 4F-아닐린 (0.462 g, 4.1 mmol, 2.0 equiv.), Pd2(dba)3 (0.095 g, 0.104 mmol, 0.05 equiv.), 크산트포스 (0.120 g, 0.208 mmol, 0.1 equiv.) 및 디옥산을 실온에서 5분 동안 교반하였다. 기준 화합물 36 (1 g, 2.08 mmol, 1.0 equiv.)을 반응 혼합물에 첨가하고, 이후 반응 혼합물을 15분 동안 탈기시키고, 이후 120℃에서 8시간 동안 N2 하에 교반하였다. HPLC/MS 시험은 출발 물질인 기준 화합물 36이 소모되었으며, 목적 생성물이 일부 기준 화합물 화합물 35-6과 함께 우세하게 형성되었음을 나타내었다. 반응물을 여과하여 고체를 제거하였다. 반응 혼합물을 농축시키고, 이후 100%-0 -> 0-100% 헥산:EtOAc의 구배를 사용하여 정상 컬럼 크로마토그래피 (실리카겔 80 gm)에 의해 정제하였다. 목적 생성물은 60:40 EtOAc:헥산에서 용리한다. 유기 층을 감압에서 농축시켜, Boc 유도체 (950 mg, 89.3% 수율)를 수득하였다.
Boc-화합물을 CH2Cl2 중 20% TFA (50 ml)로 처리하고, 반응물을 4시간 동안 교반하고, 혼합물에 첨가하였다. 이 반응의 완료 후 (LCMS에 의해 모니터링됨), 얻어진 혼합물을 감압 하에 농축시켰다. 얻어진 잔류물을 역상 HPLC에 의해 정제하여, TFA 염으로서 생성물을 수득하였다. ACN-물 층을 농축시켜 모든 용매를 제거하였다. 잔류물을 디클로로메탄에 용해시키고, 포화 NaHCO3에 의해 조심스럽게 중화시켰다. 유기 층을 염수, 이어서 물로 연속적으로 세척하였다. 유기 층을 농축시켜 실시예 412를 수득하였다 (450 mg, 2 단계 동안 52%).
실시예
417
2-아미노-1-(3-(4-
클로로페닐아미노
)-2-(4-
플루오로페닐
)-8,8-디메틸-5,6-
디히드로이미다조[1,2-a]피라진
-7(8H)-일)
에탄온
4-클로로아닐린과의 Pd2(dba)3 매개 아미노화 반응, 이어서 6 N HCl 매개 탈보호에 의해 기준 화합물 36으로부터 실시예 417을 제조하였다.
실시예
331
N-(3,4-
디플루오로페닐
)-2-(4-
플루오로페닐
)-5,6,7,8-테트라히드로이미다조[
1,2-a]피라진
-3-아민
하기 방식에 의해 기준 화합물 19로부터 실시예 331을 합성하였다. 불활성 질소 분위기로 퍼징되고 유지되는 250 mL 3구 둥근 바닥 플라스크에 1,4-디옥산 (100 mL) 중 기준 화합물 19 (1.5 g, 6.12 mmol) 및 4-브로모-1,2-디플루오로벤젠 (2.4 g, 12.44 mmol)의 용액을 두고, Pd2(dba)3 (170 mg, 0.19 mmol), X-Phos (175 mg, 0.37 mmol) 및 Cs2CO3 (4 g, 12.28 mmol)을 질소 하에 첨가하였다. 얻어진 용액을 120℃로 가열하고, 밤새 교반하였다. 고체를 여과하고, 얻어진 혼합물을 진공 하에 농축시켰다. 잔류물을 실리카 겔 컬럼 (에틸 아세테이트/석유 에테르 (1:2))에 적용하여, 갈색 고체로서 디아릴 아민 1.9 g (87%)이 생성되었다.
메탄올 (50 mL) 중 얻어진 디아릴 아민 (1.9 g, 5.33 mmol)의 용액에 PtO2 (130 mg, 0.57 mmol)를 첨가하였다. 혼합물을 탈기시키고, 수소로 역충전하였다. 얻어진 용액을 실온에서 밤새 교반하면서 반응시켰다. 고체를 여과하고, 얻어진 혼합물을 진공 하에 농축시켰다. 잔류물을 실리카 겔 컬럼 (DCM/MeOH (50:1))에 적용하여, 갈색 고체로서 표제 화합물이 생성되었다.
실시예
529
2-아미노-1-(2-(4-
플루오로페닐
)-8,8-디메틸-3-(p-
톨릴아미노
)-5,6-디히드로이미다조[
1,2-a]피라진
-7(8H)-일)-2-
메틸프로판
-1-온
하기 방식에 의해 실시예 415로부터 실시예 529를 제조하였다.
무수 DCM 6 mL 중 실시예 415 (21 mg, 0.06 mmol) 및 Et3N (83 μL, 0.60 mmol)의 교반된 용액에 2-브로모-2-메틸프로파노일 브로마이드 (71 μL, 0.60 mmol)를 첨가하였다. 반응 혼합물을 실온에서 5시간 동안 교반하였다. 반응 혼합물을 농축시키고, 바로 질량-유발 LC/MS 정제하였다. 얻어진 용액을 농축시켜, 중화 후 황색 오일로서 화합물 529-1 22 mg (73%)을 얻었다.
DMF 3 mL 중 화합물 529-1 (22 mg, 0.044 mmol)의 용액에 NaN3 (8.6 mg, 0.132 mmol)을 실온에서 첨가하였다. 반응 혼합물을 실온에서 2시간 동안 교반하였다. 반응 혼합물을 바로 질량-유발 LC/MS 정제하였다. 얻어진 MeCN/수용액을 합하고, 농축시켜, 중화 후 황색 오일로서 화합물 529-2 15 mg (75%)을 얻었다.
MeOH 3 mL 중 화합물 529-2 (15 mg, 0.033 mmol)의 용액에 10% Pd/C (4 mg, 0.003 mmol)를 실온에서 첨가하였다. 공기를 제거하고 H2를 충전하였다. 반응 혼합물을 실온에서 2시간 동안 교반하였다. 고체를 여과하고, 용매를 제거하였다. 반응 혼합물을 바로 질량-유발 HPLC 정제하여, 표제 화합물인 황색 오일 15 mg (100%)을 얻었다.
실시예
530
tert
-부틸 1-(2-(4-
플루오로페닐
)-5,6-
디히드로이미다조[1,2-a]피라진
-7(8H)-일)-2-
메틸
-1-
옥소프로판
-2-
일카르바메이트
하기 방식에 의해 화합물 540-1로부터 실시예 530을 제조하였다.
DMF (20 mL) 중 화합물 540-1 (1.0 g, 4.61 mmol, 1.00 equiv)의 교반된 용액에 2-(tert-부톡시카르보닐)-2-메틸프로판산 (1.12 g, 5.52 mmol, 1.20 equiv), EDC (1.06 g, 5.52 mmol, 1.20 equiv), HOBT (1.8 g, 13.24 mmol, 2.87 equiv), DIEA (1.78 g, 13.80 mmol, 2.99 equiv)를 첨가하였다. 얻어진 용액을 60℃에서 밤새 교반하였다. 얻어진 혼합물을 진공 하에 농축시켰다. 얻어진 용액을 물 100 mL로 희석시켰다. 얻어진 용액을 에틸 아세테이트 (2×150 mL)로 추출하고, 합쳐진 유기 층을 농축시켰다. 잔류물을 실리카 겔 컬럼 (에틸 아세테이트/석유 에테르 (1:10 ~ 1:2 ~ 1))에 적용하였다. 황색 고체로서 표제 화합물이 생성되었다.
실시예
540
tert
-부틸 2-(2-(4-
플루오로페닐
)-5,6-
디히드로이미다조[1,2-a]피라진
-7(8H)-일)-2-
옥소에틸카르바메이트
하기 방식에 의해 기준 화합물 51로부터 실시예 540을 제조하였다.
THF (150 mL) 중 기준 화합물 51 (4.2 g, 18.18 mmol, 1.00 equiv)의 교반된 용액에 BH3Me2S (45 mL, 2 M)를 실온에서 10분 적가하였다. 얻어진 용액을 밤새 가열 환류시켰다. 얻어진 혼합물을 진공 하에 농축시켰다. 얻어진 용액을 메탄올 100 mL로 희석시켰다. 진한 HCl로 용액의 pH 값을 1로 조절하고, 혼합물을 1시간 동안 환류시켰다. 얻어진 혼합물을 진공 하에 농축시켰다. 잔류물을 물 100 mL에 용해시켰다. 탄산칼륨을 이용하여 pH를 10으로 조절하였다. 얻어진 용액을 THF (4×200 mL)로 추출하고, 합쳐진 유기 층을 염수 (2×200 mL)로 세척하고, 무수 황산나트륨에서 건조시키고, 진공 하에 농축시켰다. 백색 고체로서 화합물 540-1 3 g (76%)이 생성되었다.
DMF (20 mL) 중 화합물 540-1 (1.0 g, 4.61 mmol, 1.00 equiv)의 교반된 용액에 2-(tert-부톡시카르보닐)아세트산 (1.2 g, 6.86 mmol, 1.49 equiv) 및 HATU (5.2 g, 13.68 mmol, 2.97 equiv)를 첨가하였다. 얻어진 용액을 실온에서 4시간 동안 교반하였다. 얻어진 혼합물을 진공 하에 농축시켰다. 잔류물을 실리카 겔 컬럼 (에틸 아세테이트/석유 에테르 (1:1))에 적용하였다. 백색 고체로서 표제 화합물 300 mg (17%)이 생성되었다.
실시예
556
N-(4-
클로로페닐
)-2-(4-
플루오로페닐
)-6,6,7-
트리메틸
-5,6,7,8-
테트라히드로이미다조[1,2-a]피라진
-3-아민
브로민화, 이어서 4-클로로아닐린과의 Pd2(dba)3 매개 아미노화 반응에 의해 기준 화합물 41로부터 실시예 556을 제조하였다. 브로민화 절차는 하기 나타나 있다.
DCM 6 mL 중 화합물 41-1 (52 mg, 0.20 mmol)의 교반된 용액에 아세트산 2 mL 중 Br2 (11.3 μL, 0.22 mmol)를 첨가하였다. 반응 혼합물을 실온에서 30분 동안 교반하였다. 용매를 20℃ 이하의 온도에서 회전 증발기를 통해 제거하였다. 중화 후, 잔류물을 플래시 크로마토그래피 (40 g, DCM 중 0-10% 메탄올, 50분, 건조 로딩) 정제하여, 백색 고체로서 표제 화합물 59 mg (87%)을 얻었다.
실시예
645
8-(3,4-
디플루오로페닐아미노
)-9-(4-
플루오로페닐
)-2,2-디메틸-5,6-
디히드로디이미다조[1,2-a:2',1'-c]피라진
-3(2H)-온
하기 방법에 의해 실시예 29로부터 실시예 645를 제조하였다. 실시예 29 (12 mg, 0.03 mmol)의 교반된 용액에 MnO2 (52 mg, 0.60 mmol)를 첨가하였다. 반응 혼합물을 실온에서 2시간 동안 교반하였다. LC/MS 시험은 실시예 29가 거의 없어졌으며, 목적 생성물 ([M+1] = 526)이 주요 피크 중 하나로서 검출되었음을 나타내었다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여 실시예 645를 얻었다.
실시예
646
8-(3,4-
디플루오로페닐아미노
)-9-(4-
플루오로페닐
)-2,2-디메틸-1,2,5,6-테트라히드로디이미다조[
1,2-a:2',1'-c]피라진
-3(10
bH
)-온
하기 방법에 의해 실시예 29로부터 실시예 646을 제조하였다. 실시예 29 (12 mg, 0.03 mmol)의 교반된 용액에 MnO2 (52 mg, 0.60 mmol)를 첨가하였다. 반응 혼합물을 실온에서 2시간 동안 교반하였다. LC/MS 시험은 실시예 29가 거의 없어졌으며 목적 생성물 ([M+1] = 528)이 주요 피크 중 하나로서 검출되었음을 나타내었다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여 실시예 646을 얻었다.
실시예
687
7-(2-
아미노에틸
)-2-(4-
플루오로페닐
)-3-(4-
플루오로페닐아미노
)-8,8-디메틸-7,8-
디히드로이미다조[1,2-a]피라진
-6(5H)-온
하기 단계에 의해 실시예 688로부터 실시예 687을 제조하였다.
DCM 3 mL 중 실시예 688 (22 mg, 0.05 mmol) 및 Et3N (42 μL, 0.30 mmol)의 교반된 용액에 MsCl (12 μL, 0.15 mmol)을 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다. HPLC/MS 시험은 실시예 688이 모두 없어졌으며, 목적 생성물 ([M+1] = 519)이 유일한 주요 피크로서 형성되었음을 나타내었다. 용매를 제거하고, 잔류물을 질량-유발 HPLC 정제하여 메실레이트 18 mg을 얻었다. MeOH 2 mL 중 메실레이트 (5 mg, 0.01 mmol)의 교반된 용액에 MeOH 중 5 M 1 mL를 첨가하였다. 반응 혼합물을 120℃에서 20분 동안 마이크로웨이브 오븐에서 교반하였다. HPLC/MS 시험은 메실레이트가 모두 없어졌으며, 실시예 687 ([M+1] = 440)이 주요 피크 중 하나로서 형성되었음을 나타내었다. 용매를 제거하고, 잔류물을 질량-유발 HPLC 정제하여 실시예 687 3 mg을 얻었다.
실시예
692
4-(3-(4-
플루오로
-3-
메틸페닐아미노
)-2-(3-
플루오로페닐
)-8,8-디메틸-6-옥소-5,6-
디히드로이미다조[1,2-a]피라진
-7(8H)-일)부탄산
하기 단계에 의해 기준 화합물 73으로부터 실시예 692를 제조하였다.
DMF 3 mL 중 기준 화합물 73 (10 mg, 0.03 mmol)의 용액에 KOH (8 mg, 0.12 mmol) 및 에틸 4-브로모부타노에이트 (24 mg, 0.12 mmol)를 실온에서 첨가하였다. 반응 혼합물을 90℃에서 20분 동안 마이크로웨이브 오븐에서 교반하였다. LC/MS 시험은 출발 물질의 50%가 남아있었으며, 목적 생성물인 에스테르 ([M+1] = 497)가 주요 생성물이었음을 나타내었다. 반응 혼합물을 여과하고, 질량-유발 HPLC 정제하여 무색 오일로서 에스테르를 얻었다. 얻어진 에스테르를 LiOH에 의해 가수분해하여 실시예 692를 얻었다.
실시예
695
2-아미노-1-(2-(4-
플루오로페닐
)-3-(4-메톡시벤질)-8,8-디메틸-5,6-
디히드로이미다조[1,2-a]피라진
-7(8H)-일)
에탄온
하기 단계에 의해 기준 화합물 74로부터 실시예 695를 제조하였다.
무수 THF 3 mL 중 기준 화합물 74 (21 mg, 0.05 mmol)의 용액에 2.5 N (0.025 mL, 0.06 mmol)을 -78℃에서 첨가하였다. 반응 혼합물을 동일한 온도에서 20분 동안 교반하고, 무수 THF 1 mL 중 (II) (41 mg, 0.30 mmol)를 첨가하였다. 온도를 실온으로 상승시키면서 반응 혼합물을 또 다른 5시간 동안 교반하였다. LC/MS 시험은 출발 물질이 모두 없어졌으며, 목적 부가생성물인 실시예 695-1 (20 mg, 84%)이 주요 생성물로서 단리되었음을 나타내었다.
i-PrOH 3 mL 중 실시예 695-1 (10 mg, 0.021 mmol)의 용액에 10% Pd/C (3 mg, 0.004 mmol) 및 1,4-시클로헥사디엔 (20 μL, 0.21 mmol)을 첨가하였다. 반응 혼합물을 120℃에서 3시간 동안 큐-튜브 (Q-tube)에서 교반하였다. LC/MS 시험은 출발 물질이 없어졌으며, [M+1] = 466의 주요 피크가 있음을 나타내었으며, 이는 목적 생성물에 해당하였다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, 갈색 오일로서 조질의 실시예 695-2 16 mg을 얻었다. 실시예 695-2를 TFA 매개 탈보호하여, 실시예 695-3 3 mg을 얻었다 ([M+1] = 366).
DMF 2 mL 중 실시예 695-3 (4 mg, 0.01 mmol) 및 2-(tert-부톡시카르보닐아미노)아세트산 (5.2 mg, 0.03 mmol)의 교반된 용액에 HATU (12 mg, 0.03 mmol) 및 DIEA (5.2 μL, 0.03 mmol)를 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다. LC/MS 시험은 출발 물질이 거의 없어졌으며, 목적 부가생성물 ([M+1] = 523)이 주요 피크 중 하나로서 형성되었음을 나타내었다. 반응물을 질량-유발 HPLC 정제하여, 부가생성물을 얻었으며, 이를 TFA 매개 탈보호하여 실시예 695 6 mg을 얻었다 ([M+1] = 422).
실시예
700
2-아미노-1-(2-(4-
플루오로페닐
)-8,8-디메틸-5,6-
디히드로이미다조[1,2-a]피라진
-7(8H)-일)-3-p-
톨루일프로판
-1-온
하기 단계에 의해 기준 화합물 35로부터 실시예 700을 제조하였다.
무수 THF 3 mL 중 기준 화합물 35 (48 mg, 0.10 mmol)의 용액에 2.2 N n-BuLi (0.11 mL, 0.24 mmol)를 -78℃에서 첨가하였다. 반응 혼합물을 동일한 온도에서 20분 동안 교반하고, 무수 THF 1 mL 중 1-(브로모메틸)-4-메틸벤젠 (111 mg, 0.60 mmol)을 첨가하였다. 온도를 실온으로 상승시키면서 반응 혼합물을 또 다른 5시간 동안 교반하였다. LC/MS 시험은 출발 물질이 모두 없어졌으며, 부가생성물임을 나타내었다. 반응 혼합물을 NH4Cl 수용액으로 켄칭시키고, 에틸 아세테이트로 희석시켰다. 유기 용액을 분리하고, 건조시키고, 농축시켰다. 잔류물을 질량-유발 HPLC 정제하여, 투명한 오일로서 부가생성물 28 mg을 얻었다. 이를 TFA 매개 탈보호하여 실시예 700을 얻었다.
실시예
704
2-아미노-1-(2-(4-
플루오로페닐
)-8,8-디메틸-3-p-
톨릴
-5,6-디히드로이미다조-[1,2-a]피라진-7(8H)-일)
에탄온
하기 단계에서 기준 화합물 35로부터 실시예 704를 제조하였다.
기준 화합물 35 (48 mg, 0.10 mmol), p-톨릴보론산 (27 mg, 0.20 mmol), Pd(PPh3)4 (12 mg, 0.01 mmol) 및 1.0 N Na2CO3 (0.20 mL, 0.20 mmol)을 40 mL 바이알에서 합하였다. THF 5 mL를 첨가하였다. 반응 혼합물을, 배기 및 질소로의 재충전을 반복하여 탈기시켰다. 반응 혼합물을 70℃에서 2시간 동안 교반하였다. LC/MS 시험은 기준 화합물 35가 거의 없어졌으며, 목적 부가생성물이 주요 피크 중 하나로서 검출되었음을 나타내었다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, 목적 부가생성물 22 mg을 얻었다. 이를 TFA 매개 탈보호하여 실시예 704를 얻었다.
실시예
707
N,2-
비스
(4-
플루오로페닐
)-8,8-디메틸-5,6,7,8-
테트라히드로이미다조[1,2-a]피라진
-3-
카르복스아미드
하기 단계에 의해 기준 화합물 74로부터 실시예 707을 제조하였다.
무수 THF 3 mL 중 기준 화합물 74 (21 mg, 0.05 mmol)의 용액에 2.5 N n-BuLi (0.04 mL, 0.10 mmol)를 -78℃에서 첨가하였다. 반응 혼합물을 동일한 온도에서 20분 동안 교반하고, 무수 THF 1 mL 중 1-플루오로-4-이소시아네이토벤젠 (33 μL, 0.30 mmol)을 첨가하였다. 온도를 실온으로 상승시키면서 반응 혼합물을 또 다른 5시간 동안 교반하였다. LC/MS 시험은 출발 물질이 모두 없어졌으며, 목적 부가생성물이 주요 피크로서 검출되었음을 나타내었다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, 갈색 오일로서 목적 부가생성물 56 mg을 얻었다. 부가생성물을 TFA 매개 탈보호하여, 황색 고체로서 실시예 707 22 mg ([M+1] = 393)을 얻었다.
실시예
709
2-아미노-1-(3-(4-
플루오로페녹시
)-2-(4-
플루오로페닐
)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)
에탄온
하기 단계에서 기준 화합물 35로부터 실시예 709를 제조하였다.
디옥산 5 mL 중 기준 화합물 35 (48 mg, 0.10 mmol)의 용액에 4-플루오로페놀 (34 mg, 0.30 mmol), CuI (3.8 mg, 0.02 mmol), N,N-디메틸글리신 (4.1 mg, 0.04 mmol) 및 Cs2CO3 (98 mg, 0.30 mmol)을 실온에서 첨가하였다. 반응 혼합물을 탈기시키고, 120℃에서 밤새 N2 하에 교반하였다. LC/MS 시험은 출발 물질이 모두 없어졌으며, 목적 부가생성물 ([M+1] = 513)이 주요 피크로서 검출되었음을 나타내었다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, 목적 부가생성물 28 mg을 얻었다. 이를 TFA로 탈보호하여 실시예 709를 얻었다.
실시예
713
2-아미노-1-(2-(4-
플루오로페닐
)-8,8-디메틸-3-(p-
톨릴티오
)-5,6-디히드로이미다조[
1,2-a]피라진
-7(8H)-일)
에탄온
하기 단계에서 기준 화합물 35로부터 실시예 713을 제조하였다.
디옥산 3 mL 중 기준 화합물 35 (24 mg, 0.05 mmol)의 용액에 4-메틸벤젠티올 (17 mg, 0.15 mmol), Pd2(dba)3 (9.2 mg, 0.01 mmol), 크산트포스 (12 mg, 0.02 mmol) 및 Cs2CO3 (33 mg, 0.10 mmol)을 실온에서 첨가하였다. 반응 혼합물을 탈기시키고, 150℃에서 밤새 N2 하에 교반하였다. LC/MS 시험은 출발 물질의 약 50%가 남아있었으며, 목적 부가생성물이 주요 피크 중 하나 ([M+1] = 525)였음을 나타내었다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, 갈색 오일로서 부가생성물 32 mg을 얻었다. 이를 TFA로 탈보호하여 실시예 713을 얻었다.
실시예
721
2-아미노-1-(2-(4-
플루오로페닐
)-8,8-디메틸-3-(p-
톨릴술피닐
)-5,6-
디히드로이미다조[1,2-a]피라진
-7(8H)-일)
에탄온
하기 단계에서 기준 화합물 35로부터 실시예 721을 제조하였다.
디옥산 3 mL 중 기준 화합물 35 (24 mg, 0.05 mmol)의 용액에 4-메틸벤젠티올 (17 mg, 0.15 mmol), Pd2(dba)3 (9.2 mg, 0.01 mmol), 크산트포스 (12 mg, 0.02 mmol) 및 Cs2CO3 (33 mg, 0.10 mmol)을 실온에서 첨가하였다. 반응 혼합물을 탈기시키고, 150℃에서 밤새 N2 하에 교반하였다. LC/MS 시험은 출발 물질의 약 50%가 남아있었으며, 목적 부가생성물이 주요 피크 중 하나 ([M+1] = 525)였음을 나타내었다. 고체를 여과하고, 용매를 제거하였다. 잔류물을 질량-유발 HPLC 정제하여, 갈색 오일로서 부가생성물 32 mg을 얻었다. DCM 10 mL 중 부가생성물 (32 mg, 0.061 mmol)의 용액에 mCPBA (63 mg, 0.37 mmol)를 0℃에서 첨가하였다. 반응 혼합물을 동일한 온도에서 20분 동안 교반하고, 실온으로 가온시켰다. LC/MS 시험은 출발 물질이 모두 없어졌으며, 목적 술폭시드 ([M+1] = 557)가 주요 피크였음을 나타내었다. 반응 혼합물을 NH4Cl 수용액으로 켄칭시키고, 에틸 아세테이트로 희석시켰다. 유기 용액을 분리시키고, 건조시키고, 농축시켰다. 잔류물을 질량-유발 HPLC 정제하여, 투명한 오일로서 목적 술폭시드 27 mg을 얻었다. 이를 TFA로 탈보호하여 실시예 721을 얻었다.
실시예
730
N-(3-(2-(2-(4-
플루오로페닐
)-3-(4-
플루오로페닐아미노
)-8,8-디메틸-5,6-디히드로이미다조[
1,2-a]피라진
-7(8H)-일)-2-
옥소에틸아미노
)프로필)-3-
페닐프로판아미드
하기 방식에 의해 기준 화합물 75로부터 실시예 730을 제조하였다.
DMF 2 mL 중 기준 화합물 75 (10 mg, 0.02 mmol)의 용액에 N-(3-아미노프로필)-3-페닐프로판아미드 (9 mg, 0.04 mmol) 및 Et3N (21 μL, 0.15 mmol)을 실온에서 첨가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다. HPLC/MS 시험은 출발 물질이 없어졌으며, 목적 생성물 ([M+1] = 601)이 주요 피크로서 검출되었음을 나타내었다. 반응 혼합물을 질량-유발 HPLC 정제하여, 실시예 730 8 mg을 얻었다.
적절한 출발 물질을 사용하여 상기 실시예에 기재된 절차를 반복하여, 하기 표 2에서 확인되는 것과 같은 하기 화학식 Ia, Ib 또는 Ic의 화합물들을 얻었다. 또한, 하기 표 2에는 상기 관련된 실시예로부터 얻어진 물리적 데이터가 기록되어 있다.
<표 2>
분석
본 발명의 화합물을 분석하여 감염된 적혈구에서의 기생충혈증의 증식을 억제하는 그의 능력을 측정할 수 있다. 이중 가닥 DNA에 대해 높은 친화력을 갖는 SYBR 그린 I (인비트로겐 (INVITROGEN))® 염료를 첨가하여 상기 증식을 정량하였다.
하기 분석은 본 발명의 범주를 어떠한 방식으로든 제한하지 않으면서 본 발명을 예시한다. 이 기생충 증식 분석은 DNA 개재 염료인 SYBR 그린®을 사용하여 기생충 DNA 함량의 증가를 측정한다.
3D7 열대열원충 균주를 기생충혈증이 3% 내지 8%에 도달할 때까지 O+ 인간 적혈구와 함께 완전 배양 배지에서 성장시켰다. 20 μl의 스크리닝 배지를 384웰 분석 플레이트에 분배하였다. 이후, 항말라리아 대조군 (메플로퀸, 피리메타민 및 아르테미시닌)을 포함한 50 nl의 본 발명의 화합물 (DMSO 중)을 분석 플레이트에 옮겼으며, DMSO 단독은 억제에 대한 음성 대조군으로서 기능하였다. 이어서, 스크리닝 배지 중 3D7 열대열원충 감염된 적혈구의 현탁액 30 μl를, 최종 헤마토크리트가 0.3%의 최종 기생충혈증과 함께 2.5%가 되도록 상기 분석 플레이트에 분배하였다. 상기 플레이트를 93% N2, 4% CO2 및 3% O2 기체 혼합물을 함유하는 저산소 환경에서 72시간 동안 37℃의 인큐베이터에 두었다. RPMI 배지 중 SYBR 그린 I®의 10X 용액을 함유하는 용혈 완충액 (lysis buffer) (사포닌, 트리톤-X, EDTA) 10 μl를 상기 플레이트에 분배하였다. 플레이트를 밀봉하고, 감염된 적혈구의 용혈을 위해 실온에서 밤새 방치하였다. 형광 강도를 엔비젼 (Envision)™ 시스템 (퍼킨 엘머 (Perkin Elmer))을 사용하여 측정하였다 (425 nm에서 여기, 530 nm에서 방출). 50% 억제 백분율인 EC50을 각각의 화합물에 대해 계산하였다.
본 발명의 화합물의 EC50은 10 μM 이하, 바람직하게는 1 μM, 750 nM, 500 nM, 400 nM, 300 nM, 200 nM, 100 nM 및 50 nM 미만이었다. 본 발명의 화합물은 기생충혈증의 증가를 유의하게 지연시킬 수 있다.
본 발명의 화합물을 분석하여 운동핵편모충목 (kinetoplastid) 기생충 트리파노소마 브루세이 (Trypanosoma brucei)의 증식을 억제하는 그의 능력을 측정할 수 있다. 대사적으로 활성인 세포의 지표인 세포 ATP 양의 정량을 기준으로 배양물에서 살아있는 세포의 수를 측정하는 발광 세포 생존율 분석인 셀 타이터 글로 (Cell Titer Glo) (프로메가 (Promega)®)의 첨가에 의해 증식을 정량하였다.
하기 분석은 본 발명의 범주를 어떠한 방식으로든 제한하지 않으면서 본 발명을 예시한다. 이 기생충 증식 분석은 ATP 활성을 측정하는 분석인 셀 타이터 글로®를 사용하여 기생충 성장의 증가를 측정한다.
트리파노소마 브루세이 리스터 (Lister) 427 균주를 트리파노소마 브루세이 혈류 형태에 대한 HMI-9 트리파노솜 (Trypanosome) 배지에서 성장시켰다. 30 μl의 HMI-9 배지를 384 웰 분석 플레이트에 분배하였다. 이후, 항-트리파노솜 대조군 (펜타미딘 및 수라민)을 포함한 본 발명의 화합물 200 nl (DMSO 중)를 분석 플레이트에 옮겼으며, DMSO 단독은 억제에 대한 음성 대조군으로서 기능하였다. 이후, HMI-9 배지 중 트리파노소마 브루세이 배양물의 현탁액 25 μl를 분석 플레이트에 분배하였다. 배양물 중 기생충의 최종 농도는 HMI-9 배지 내의 셀 타이터 글로®로의 0.5 uM ATP 활성의 1.7%에 해당하였다. 플레이트를 5% CO2를 함유하는 대기 환경에서 48시간 동안 37℃ 인큐베이터에 두었다. 40 μl의 셀 타이터 글로®를 플레이트에 분배하였다. 이후, 플레이트를 발광에 대하여 판독하였다. 50% 억제 백분율인 EC50을 각 화합물에 대해 계산하였다.
본 발명의 화합물의 EC50은 10 μM 이하, 바람직하게는 1 μM, 750 nM, 500 nM, 400 nM, 300 nM, 200 nM, 100 nM 및 50 nM 미만이었다. 본 발명의 화합물은 트리파노소마 브루세이의 증식을 유의하게 지연시킬 수 있다. 예를 들어, 2-아미노-1-(2-(4-플루오로페닐)-3-(4-플루오로페닐아미노)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)에탄온 (실시예 412) 및 2-아미노-1-(3-(3,4-디플루오로페닐아미노)-2-(4-플루오로페닐)-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)-2-메틸프로판-1-온 (실시예 29)은 각각 10 μM 및 7 μM의 EC50을 가졌다.
본원에 기재된 실시예 및 실시양태는 단지 예시 목적을 위한 것이며, 그것으로 미루어보아 다양한 변경 또는 변화가 당업자에게 제안될 것이고, 그것이 본 출원의 취지 및 범위 그리고 첨부된 특허청구범위의 범주 내에 포함될 것임이 이해된다. 본원에서 언급된 모든 공보, 특허 및 특허 출원은 모든 목적을 위해 본원에 참조로 포함된다.
Claims (17)
- 하기 화학식 Ia, Ib 및 Ic의 화합물, 또는 이들의 제약상 허용되는 염.
<화학식 Ia>
<화학식 Ib>
<화학식 Ic>
식 중,
n은 0, 1, 2, 3 및 4로부터 선택되고;
m은 0, 1, 2, 3 및 4로부터 선택되고;
Ra는 수소, -X3NR7R8, -X3OR8, -X3S(O)0-2R8, -X3C(O)NR7R8, -X3R8, 벤질, 및 할로, C1 - 4알킬, 할로-치환된-C1 - 4알킬, C1 - 4알콕시 및 할로-치환된-C1 - 4알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되는 C6 - 10아릴로부터 선택되며; 여기서 X3은 결합 및 C1 - 4알킬렌으로부터 선택되고;
Rb는 수소 및 C1 - 4알킬로부터 선택되고;
R1은 -OR13, -C(O)OR13, -NR13R14, C6 - 10아릴, 및 3개 이하의 질소를 함유하는 포화, 불포화 또는 부분 불포화 4원 내지 9원 헤테로시클릭 고리로부터 선택되며; 여기서 R13은 수소, C1 - 6알킬, 할로-치환된-C1 - 6알킬, 히드록시-치환된-C1 - 6알킬, C6-10아릴-C0 - 4알킬, C3 - 8시클로알킬-C0 - 4알킬, -X1NHC(O)R15, -X1C(NH)NHR15, -X1C(O)NHR15, -X1NHR15, -X1OR15, -C(O)R15 및 -C(O)OR15로부터 선택되며; 여기서 X1은 결합 및 C1 - 4알킬렌으로부터 선택되며; R15는 수소, C1 - 6알킬, 할로-치환된-C1 - 6알킬 및 벤질로부터 선택되며; R14는 수소, C1 - 6알킬 및 히드록시-치환된-C1 - 6알킬로부터 선택되며; 여기서 R1의 임의의 아릴 또는 헤테로시클릭은 할로, C1 - 6알킬, 할로-치환된-C1 - 6알킬, C1-6알콕시 및 할로-치환된-C1 - 6알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되거나; 또는
R13 및 R14는 이들이 부착된 질소와 함께 N, NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자를 함유하는 포화, 불포화 또는 부분 불포화 5원 내지 9원 헤테로시클릭 고리를 형성하며; 여기서 R30은 수소 및 C1 - 6알킬로부터 선택되며; 여기서 상기 R13 및 R14의 조합으로부터의 헤테로시클릭은 할로, 히드록시, C1 - 6알킬, 아미노-치환된-C1 - 6알킬 및 할로-치환된-C1 - 6알킬로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되고;
R2는 수소, C1 - 6알킬, 아미노, C3 - 8시클로알킬-C0 - 4알킬, C6 - 10아릴-C0 - 4알킬, 할로-치환된-C1 - 6알킬, 히드록시-치환된-C1 - 6알킬 및 헤테로시클릴-C0 - 4알킬로부터 선택되며; 여기서 상기 헤테로시클릴은 N, NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자를 함유하는 포화, 불포화 또는 부분 불포화 5원 내지 9원 헤테로시클릭 고리이며; 여기서 R30은 수소 및 C1 - 6알킬로부터 선택되며; 여기서 상기 R2의 C6-10아릴 또는 헤테로시클릭은 할로, 히드록시, 시아노, 니트로, -NHR17, -(CH2)0-2NHC(O)R17, C1 - 6알킬, 할로-치환된-C1 - 6알킬, 아미노-치환된-C1 - 6알킬 및 C1 -6알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되며; 여기서 R17은 수소 및 C1 - 6알킬로부터 선택되고;
R3은 수소, C1 - 6알킬, C6 - 10아릴-C0 - 4알킬, -X2C(O)OR16, -X2S(O)0-2R16, -X2OR16, -X2C(O)NHR16 및 -X2NHC(O)R16으로부터 선택되며; 여기서 X2는 결합 및 C1 - 4알킬렌으로부터 선택되며; R16은 수소, C1 - 6알킬 및 C6 - 10아릴-C0 - 4알킬로부터 선택되며; 여기서 상기 R16의 아릴은 할로, C1 - 6알킬, 할로-치환된-C1 - 6알킬, C1 - 6알콕시 및 할로-치환된-C1 - 6알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되거나; 또는
R2 및 R3은 이들이 부착된 탄소 원자와 함께 C3 - 8시클로알킬을 형성하거나; 또는
R2 및 R13은 이들이 부착된 원자와 함께 C3 - 8시클로알킬, 및 N, C(O), NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자 또는 기를 함유하는 포화, 불포화 또는 부분 불포화 5원 내지 9원 모노 또는 융합 헤테로시클릭 고리로부터 선택되는 고리를 형성하며; 여기서 R30은 수소 및 C1 - 6알킬로부터 선택되며; 여기서 상기 R2 및 R13의 조합으로부터의 헤테로시클릭은 할로, 히드록시, C1 - 6알킬 및 할로-치환된-C1 - 6알킬로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되고;
R4는 수소 및 C1 - 6알킬로부터 선택되고;
R5는 수소 및 C1 - 6알킬로부터 선택되거나; 또는 R4 및 R5는 이들이 부착된 탄소 원자와 함께 C3 - 8시클로알킬을 형성하고;
R6은 C6 - 10아릴, C3 - 8시클로알킬, 및 N, C(O), NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자 또는 기를 함유하는 포화, 불포화 또는 부분 불포화 5원 내지 9원 모노 또는 융합 헤테로시클릭 고리로부터 선택되며; 여기서 R30은 수소 및 C1-6알킬로부터 선택되며; 여기서 상기 R6의 아릴 또는 헤테로시클릭은 할로, 히드록시, C1 - 6알킬 및 C1 - 6알콕시로부터 독립적으로 선택되는 1개 내지 3개 라디칼에 의해 임의로 치환되고;
R7은 수소 및 C1 - 3알킬로부터 선택되고;
R8은 C1 - 10알킬, C6 - 10아릴-C0 - 4알킬, C3 - 8시클로알킬, 및 N, C(O), NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자 또는 기를 함유하는 포화, 불포화 또는 부분 불포화 5원 내지 9원 모노 또는 융합 헤테로시클릭 고리로부터 선택되며; 여기서 R30은 수소 및 C1 - 6알킬로부터 선택되며; 여기서 상기 R8의 아릴 또는 헤테로시클릭은 할로, 시아노, 히드록시, C1 - 6알킬, 할로-치환된-C1 - 6알킬, 할로-치환된-C1 - 6알콕시, C1 - 6알콕시, -C(O)OR18, -S(O)0-2R18, -C(O)NHR18, -NHS(O)0-2R18, 페닐, 및 N, C(O), NR30, S(O)0-2 및 O로부터 선택되는 3개 이하의 헤테로원자 또는 기를 함유하는 포화, 불포화 또는 부분 불포화 5원 또는 6원 헤테로시클릭 고리로부터 독립적으로 선택되는 1개 내지 3개 라디칼에 의해 임의로 치환되며; 여기서 R30은 수소 및 C1 - 6알킬로부터 선택되며; 여기서 상기 R8의 아릴 또는 헤테로시클릭 치환기는 할로, 시아노, 히드록시, C1 - 6알킬 및 할로-치환된-C1 - 6알킬로부터 독립적으로 선택되는 1개 내지 3개 라디칼에 의해 임의로 치환되며; 여기서 R18은 수소 및 C1 - 6알킬로부터 선택되고;
R9는 수소 및 C1 - 6알킬로부터 선택되고;
R10은 수소 및 C1 - 6알킬로부터 선택되고;
R11은 수소 및 C1 - 6알킬로부터 선택되고;
R12는 수소 및 C1 - 6알킬로부터 선택되거나; 또는 R11 및 R12는 조합하여 C(O)를 형성한다. - 제1항에 있어서,
R1이 -OR13, -C(O)OR13, -NR13R14, 페닐, 피리디닐, 인돌릴, 아제티디닐, 1H-인다졸릴, 피페리디닐 및 피리미디닐로부터 선택되며; 여기서 R13은 수소, 메틸, 에틸, 프로필, 부틸, 펜틸, 시클로프로필, 페닐, 벤질, 아미노-부틸, 히드록시-에틸, 메톡시-에틸, 부톡시-에틸, 메톡시-프로필, -C(O)R15, -C(O)OR15, -X1OR15, -X1C(NH)NHR15, -X1NHC(O)R15 및 X1C(O)NHR15로부터 선택되며; 여기서 X1은 결합 및 C1 - 4알킬렌으로부터 선택되며; R15는 수소, 메틸, 에틸, 프로필, 부틸, t-부틸, 트리플루오로메틸 및 트리플루오로메틸-카르보닐로부터 선택되며; R14는 수소, 메틸, 에틸, 프로필, 부틸, 펜틸, 이소부틸, 히드록시-에틸, 디플루오로에틸 및 이소부틸로부터 선택되며; 여기서 R1의 임의의 페닐, 벤질 또는 헤테로시클릭은 할로, 메틸, 에틸, 트리플루오로메톡시 및 트리플루오로메틸로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되거나; 또는 R13 및 R14는 이들이 부착된 질소와 함께 피롤리디닐, 모르폴리노, 티오모르폴리노 및 피페리디닐을 형성하며; 여기서 상기 R13 및 R14의 조합으로부터의 헤테로시클릭은 할로, 트리플루오로메틸, 히드록시 및 아미노-에틸로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되고;
R2가 수소, 메틸, 에틸, 이소프로필, 프로필, 이소부틸, 부틸, t-부틸, 트리플루오로메틸, 트리플루오로-에틸, 페닐, 벤질, 페네틸, 시클로부틸-메틸, 시클로펜틸, 시클로헥실, 시클로헥실-메틸, 히드록시-메틸 및 1-히드록시-에틸로부터 선택되며; 여기서 상기 R2의 페닐, 벤질 또는 페네틸은 할로, 메톡시, 트리플루오로메틸, 히드록시, 아미노, 니트로, 시아노, 아미노-메틸, 메틸-술포닐-에틸, 메틸-카르보닐-아미노, -NHR17, -CH2NHC(O)R17 및 -NHC(O)R17로부터 독립적으로 선택되는 1개 내지 3개 라디칼로 임의로 치환되며; 여기서 R17은 수소, 에틸, 프로필, 부틸 및 펜틸로부터 선택되고;
R3이 수소, 메틸, 메틸-카르보닐-아미노-부틸, 프로필-아미노-카르보닐-메틸, 카르복시-메틸, 프로필-아미노-카르보닐-메틸, 부틸-아미노-카르보닐-메틸, 펜틸-아미노-카르보닐-메틸, 프로필-아미노-카르보닐-에틸, 트리플루오로메틸-카르보닐-아미노-부틸, 페닐, 벤질-술파닐-메틸, 벤족시-카르보닐-메틸, 메틸-술포닐-메틸, 1-(벤질옥시)에틸, 벤족시-카르보닐-에틸 및 벤족시-카르보닐-아미노로부터 선택되거나; 또는
R2 및 R3이 이들이 부착된 탄소 원자와 함께 시클로프로필, 시클로부틸, 시클로펜틸 또는 시클로헥실을 형성하거나; 또는
R2 및 R13이 이들이 부착된 원자와 함께 피페리디닐, 시클로부틸, 피롤리디닐, 모르폴리노, 피페리디닐, 테트라히드로푸라닐, 테트라히드로-2H-피란-4-일, 4-옥소아제티딘-2-일, 인돌릴, 2,6-디옥소-1,2,3,6-테트라히드로피리미딘-4-일, 1,2,3,4-테트라히드로이소퀴놀린-3-일, 옥소피페리딘-3-일 또는 4,5,6,7-테트라히드로-3H-이미다조[4,5-c]피리딘-6-일을 형성하는 것인 화합물. - 제2항에 있어서, R4, R5, R9 및 R10이 수소 및 메틸로부터 독립적으로 선택되고; R11 및 R12가 둘 다 수소이거나; 또는 R11 및 R12가 조합하여 C(O)를 형성하는 것인 화합물.
- 제3항에 있어서, R6이 페닐, 시클로헥실 및 피리디닐로부터 선택되며; 여기서 상기 R6의 페닐 또는 피리디닐은 할로, 펜틸, 히드록시, 메틸 및 메톡시로부터 독립적으로 선택되는 1개 내지 3개 라디칼에 의해 임의로 치환되는 것인 화합물.
- 제4항에 있어서, R7이 수소, 메틸, 에틸 및 이소프로필로부터 선택되고; R8이 페닐, 벤질, 벤조[d][1,3]디옥솔-5-일, 시클로부틸, 시클로펜틸, 시클로헵틸, 시클로헥실, 비시클로[2.2.1]헵틸, 테트라히드로-2H-피라닐, 피리디닐, 피페리디닐, 피페라지닐, 퀴놀리닐, 피롤리디닐 및 피라졸릴로부터 선택되며; 여기서 상기 R8의 페닐, 벤질, 벤조[d][1,3]디옥솔-5-일, 시클로부틸, 시클로펜틸, 시클로헵틸, 시클로헥실, 비시클로[2.2.1]헵틸, 테트라히드로-2H-피라닐, 피리디닐, 피페리디닐, 피페라지닐, 퀴놀리닐, 피롤리디닐 또는 피라졸릴은 할로, 시아노, 메틸, 에틸, t-부틸, 트리플루오로메틸, 트리플루오로메톡시, 디메틸-아미노, 디플루오로메톡시, 카르복시, 메톡시-카르보닐, 메틸-술포닐-아미노, 메틸-술포닐, 메틸-아미노-카르보닐, 페닐, 피페리디닐, 피페리디닐-메틸, 피페라지닐 및 피페라지닐-메틸로부터 독립적으로 선택되는 1개 내지 3개 라디칼에 의해 임의로 치환되는 것인 화합물.
- 제6항에 있어서, 2-아미노-1-(2-(4-플루오로페닐)-3-(4-플루오로페닐아미노)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)에탄온; 2-아미노-1-(3-(3,4-디플루오로페닐아미노)-2-(4-플루오로페닐)-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)-2-메틸프로판-1-온; 및 2-아미노-1-(3-(4-클로로페닐아미노)-2-(4-플루오로페닐)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)에탄온으로부터 선택되는 화합물.
- 제1항에 있어서, 2-아미노-1-{3-[(3,5-디메틸페닐)아미노]-2-페닐-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(2H-1,3-벤조디옥솔-5-일아미노)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[3-(시클로펜틸아미노)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(시클로펜틸아미노)-2-페닐-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-2-메틸-1-[2-페닐-3-(페닐아미노)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 메틸 4-{[7-(2-아미노-2-메틸프로파노일)-2-페닐-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조에이트; 2-아미노-1-[2-(2-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-플루오로페닐)아미노]-2-페닐-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-플루오로페닐)아미노]-2-(2,4,6-트리플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-[2-(3,5-디플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-플루오로페닐)아미노]-2-(4-펜틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{2-시클로헥실-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-(피리딘-3-일아미노)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 4-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-페닐프로판-1-온; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-페닐프로판-1-온; 2-아미노-1-{3-[(4-브로모페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-(디메틸아미노)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(벤질아미노)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-(4-클로로페닐)-3-(4-메틸페닐)이미다조[1,2-a]피라진; N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}아세트아미드; N,2-비스(4-플루오로페닐)이미다조[1,2-a]피라진-3-아민; 2-아미노-1-[3-(시클로헥실아미노)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; N,2-비스(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2,3-비스(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(피롤리딘-1-일)에탄-1-온; 3-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(3-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(3-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(모르폴린-4-일)에탄-1-온; 4-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}-1$l^{6},4-티오모르폴린-1,1-디온; 2-(3,3-디플루오로피페리딘-1-일)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 7-[(1-아미노시클로프로필)카르보닐]-N,2-비스(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-{1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸-1-옥소프로판-2-일}아세트아미드; 2-아미노-1-[2-(4-클로로페닐)-3-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 7-벤질-N,2-비스(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 벤질 N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}카르바메이트; 2-아미노-3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-아미노-1-[2-(4-플루오로-2-히드록시페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-플루오로페닐)아미노]-2-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-플루오로페닐)아미노]-2-(4-메톡시페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-브로모페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-클로로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(3,3-디플루오로피롤리딘-1-일)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(3R)-3-플루오로피롤리딘-1-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(3S)-3-플루오로피롤리딘-1-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(4-플루오로피페리딘-1-일)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[4-(트리플루오로메틸)피페리딘-1-일]에탄-1-온; 2-(4,4-디플루오로피페리딘-1-일)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[3-(트리플루오로메틸)피페리딘-1-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(3-히드록시피페리딘-1-일)에탄-1-온; 2-[(2,2-디플루오로에틸)아미노]-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,5-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3,5-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-(시클로프로필아미노)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(2-메틸프로필)아미노]에탄-1-온; 2-아미노-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-{[4-(트리플루오로메틸)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-{[4-(트리플루오로메틸)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(3,3-디플루오로피페리딘-1-일)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)에탄-1-온; 1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(3,3-디플루오로피페리딘-1-일)에탄-1-온; 1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(메틸아미노)에탄-1-온; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(2,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(2,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-페닐에탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(3R)-피페리딘-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(3S)-피페리딘-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-[2-(디에틸아미노)에틸]-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-{[(2S)-아제티딘-2-일]카르보닐}-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2R)-피롤리딘-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2S)-피롤리딘-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2S)-피페리딘-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2R)-피페리딘-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(3R)-피롤리딘-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(3S)-피롤리딘-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐에탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐에탄-1-온; 1-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}시클로프로판-1-올; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-3-메틸부탄-1-온; N-[(5S)-5-아미노-6-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-6-옥소헥실]아세트아미드; N-[(5S)-5-아미노-6-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-6-옥소헥실]-2,2,2-트리플루오로아세트아미드; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; (1S,2S)-2-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}시클로펜탄-1-올; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-페닐프로판-1-온; 2-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시부탄-1-온; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-페닐프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3,3-디메틸부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-페닐프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2,2-디페닐에탄-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-(트리플루오로메틸)부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-메틸프로판-1-온; 1-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}시클로펜탄-1-올; 1-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}시클로헥산-1-올; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-4-페닐부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-2,2-디메틸-3-(4-메틸페닐)프로판-1-온; 4,4,4-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-3-메틸부탄-1-온; (2S)-2-시클로헥실-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-(4-메톡시페닐)에탄-1-온; 2-(3,5-디플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-[3-(트리플루오로메틸)페닐]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메톡시-2-페닐에탄-1-온; 2-(4-브로모페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-[4-(트리플루오로메틸)페닐]에탄-1-온; 3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메톡시-2-페닐프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-(3-히드록시페닐)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-(4-히드록시페닐)에탄-1-온; 2-(2-클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 2-(4-브로모-2-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; 2-(4-클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시에탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-4-메틸펜탄-1-온; (3S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-3-페닐프로판-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)이미다조[1,2-a]피라진-3-아민; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-페닐에탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-2-페닐에탄-1-온; 7-[(1-아미노시클로부틸)카르보닐]-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-[(1-아미노시클로펜틸)카르보닐]-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-[(1-아미노시클로헥실)카르보닐]-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-4,4,4-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-3-메틸펜탄-1-온; 2-아미노-3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-3-시클로헥실-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시프로판-1-온; 2-(벤질아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(디프로필아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-(디프로필아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)-3-페닐프로판-1-온; 벤질 (4S)-4-{[(tert-부톡시)카르보닐]아미노}-5-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-5-옥소펜타노에이트; 벤질 (3S)-3-{[(tert-부톡시)카르보닐]아미노}-4-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소부타노에이트; tert-부틸 N-[(5S)-5-{[(벤질옥시)카르보닐]아미노}-6-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-6-옥소헥실]카르바메이트; 2-(시클로프로필아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; N-[4-({2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}아미노)부틸]아세트아미드; 2-(4-플루오로페닐)-7-{2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에틸}-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2,6-디아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]헥산-1-온; (2S)-2-아미노-3-(4-아미노페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; N-[(5S)-5-아미노-6-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-6-옥소헥실]부탄아미드; N-[(5S)-5-아미노-6-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-6-옥소헥실]-1-(5-{2-옥소-헥사히드로-1H-티에노[3,4-d]이미다졸리딘-4-일}펜탄아미도)-3,6,9,12-테트라옥사펜타데칸-15-아미드; N-{4-[(2S)-2-아미노-3-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}아세트아미드; 2-[비스(2-히드록시에틸)아미노]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (4S)-4-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}아제티딘-2-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시프로판-1-온; 2,2,2-트리플루오로-N-[(2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-1-옥소프로판-2-일]아세트아미드; 6-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}-1,2,3,4-테트라히드로피리미딘-2,4-디온; {2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}우레아; 1-{2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}구아니딘; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(페닐아미노)에탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸부탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3,3-디메틸부탄-1-온; (3S)-3-아미노-4-(4-브로모페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; (3S)-3-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-(2,4,5-트리플루오로페닐)부탄-1-온; 2-(4-클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-(4-클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐프로판-1-온; 2-(4-플루오로페닐)-7-{[(6S)-1H,4H,5H,6H,7H-이미다조[4,5-c]피리딘-6-일]카르보닐}-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-(디메틸아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-페닐프로판-1-온; 2-[4-(2-아미노에틸)피페리딘-1-일]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(4-플루오로페닐)-7-[(4-메탄술포닐페닐)메틸]-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[4-(모르폴린-4-일)페닐]메틸}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[4-(4-메틸피페라진-1-일)페닐]메틸}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-{[4-(디에틸아미노)페닐]메틸}-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-({4-[3-(디메틸아미노)프로폭시]페닐}메틸)-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[4-(피리딘-4-일)페닐]메틸}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; tert-부틸 N-[(2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-(4-프로판아미도페닐)프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-(프로필카르바모일)프로판-2-일]카르바메이트; N-{4-[(2S)-2-아미노-3-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}프로판아미드; (4S)-4-아미노-5-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-5-옥소-N-프로필펜탄아미드; (3S)-3-아미노-4-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소-N-프로필부탄아미드; 3-아미노-4,4,4-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; 2-(3-플루오로페닐)-N-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 7-{[(1S,2R)-2-아미노시클로펜틸]카르보닐}-2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3,3,3-트리플루오로프로판-1-온; (2R)-2-아미노-3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; N-{4-[(2S)-2-아미노-3-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}부탄아미드; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메톡시프로판-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2R)-옥솔란-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[(2S)-옥솔란-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페녹시부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페녹시프로판-1-온; 2-(3-클로로페녹시)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(피리미딘-4-일)에탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(3-플루오로페닐)이미다조[1,2-a]피라진-3-아민; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸-2-(2-메틸페녹시)부탄-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-[(옥산-4-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-에톡시-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(4-히드록시페닐)프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(옥솔란-2-일)에탄-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-[(옥솔란-3-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-3-[4-(아미노메틸)페닐]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-(1-에틸피페리딘-4-일)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(옥솔란-3-일)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(옥산-2-일)에탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-({4-[(2S)-2-아미노-3-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}메틸)부탄아미드; N-({4-[(2S)-2-아미노-3-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}메틸)프로판아미드; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(피페리딘-4-일)에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3,3,3-트리플루오로프로판-1-온; (2R)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-페닐프로판-1-온; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-페닐프로판-1-온; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐부탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐부탄-1-온; 2-시클로펜틸-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(피리딘-4-일)에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-(3,5-디클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸-2-페닐부탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(4-메틸페닐)에탄-1-온; 2-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-히드록시-3-메틸부탄-1-온; 1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-3-메틸부탄-1-온; 벤질 (3S)-3-{[(tert-부톡시)카르보닐]아미노}-4-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-옥소부타노에이트; 벤질 (3S)-3-{[(tert-부톡시)카르보닐]아미노}-4-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소부타노에이트; tert-부틸 N-[(2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-니트로페닐)-1-옥소프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(4-니트로페닐)-1-옥소프로판-2-일]카르바메이트; (3S)-3-{[(tert-부톡시)카르보닐]아미노}-4-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-옥소부탄산; (3S)-3-{[(tert-부톡시)카르보닐]아미노}-4-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소부탄산; tert-부틸 N-[(2S)-3-(4-아미노페닐)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-1-옥소프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-3-(4-아미노페닐)-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소프로판-2-일]카르바메이트; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-2,2-디메틸프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-2-(히드록시메틸)-2-메틸프로판-1-온; tert-부틸 N-[(2S)-3-(3-아미노페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-1-옥소-3-(프로필카르바모일)프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-(프로필카르바모일)프로판-2-일]카르바메이트; 4-{[2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; tert-부틸 N-[(2S)-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-(펜틸카르바모일)프로판-2-일]카르바메이트; 1-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}-N,N-디메틸피롤리딘-3-아민; tert-부틸 N-[(2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-1-옥소-3-(4-펜탄아미도페닐)프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-1-옥소-3-(4-프로판아미도페닐)프로판-2-일]카르바메이트; tert-부틸 N-[(2S)-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-(4-펜탄아미도페닐)프로판-2-일]카르바메이트; (3S)-3-아미노-4-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-옥소-N-프로필부탄아미드; (3S)-3-아미노-4-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소-N-프로필부탄아미드; (3S)-3-아미노-4-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소-N-펜틸부탄아미드; N-{4-[(2S)-2-아미노-3-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-옥소프로필]페닐}펜탄아미드; N-{4-[(2S)-2-아미노-3-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-옥소프로필]페닐}프로판아미드; N-{4-[(2S)-2-아미노-3-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}펜탄아미드; N-{4-[(2S)-2-아미노-3-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-옥소프로필]페닐}프로판아미드; N-(4-클로로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 4-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 4-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 4-{[2-(4-플루오로페닐)-7-(3-히드록시-3-메틸부타노일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 2-(3-메틸페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; tert-부틸 N-[(2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-1-옥소-3-[4-(펜틸아미노)페닐]프로판-2-일]카르바메이트; 2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸 프로파노에이트; 2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸 부타노에이트; 2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸 펜타노에이트; 2-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-1-(4-플루오로페닐)에탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-[4-(펜틸아미노)페닐]프로판-1-온; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[4-(3-메틸피페리딘-1-일)피페리딘-1-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-7-{[4-(피페리딘-1-일)피페리딘-1-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-7-{[4-(4-플루오로페닐)피페리딘-1-일]카르보닐}-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 에틸 1-{[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}피페리딘-3-카르복실레이트; N-[2-(디에틸아미노)에틸]-2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-카르복스아미드; 2-(3,4-디플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(3-클로로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(2,4-디플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-[(2-히드록시프로필)아미노]-3-페닐프로판-1-온; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-[(2-메톡시에틸)아미노]-3-페닐프로판-1-온; 3-{[(5R,8S)-2,8-디벤질-3-메틸-5-(2-페닐에틸)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]카르보닐}피리딘; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시프로판-1-온; (2R,3S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시부탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-메탄술포닐부탄-1-온; (3R)-3-아미노-4-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-옥소부탄산; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메탄술포닐프로판-1-온; (5R,8R)-2,8-디벤질-3-메틸-5-(2-페닐에틸)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; N-[(1S)-2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸]프로판아미드; N-[(1S)-2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸]부탄아미드; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-N-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)(메틸)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)(메틸)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; (2S)-2-(부틸아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-페닐에탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(펜틸아미노)-2-페닐에탄-1-온; N-tert-부틸-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-[(1S)-2-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소-1-페닐에틸]-1-(5-{2-옥소-헥사히드로-1H-티에노[3,4-d]이미다졸리딘-4-일}펜탄아미도)-3,6,9,12-테트라옥사펜타데칸-15-아미드; 3-아미노-2-(4-플루오로페닐)-7-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메톡시프로판-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(피리딘-4-일)에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(1H-인돌-1-일)에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(1-에틸피페리딘-4-일)에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(페닐아미노)에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(1H-인다졸-3-일)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(프로필아미노)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(펜틸아미노)에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(2-메톡시에틸)아미노]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(3-메톡시프로필)아미노]에탄-1-온; (2R)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-페닐프로판-1-온; (2S,3S)-2-아미노-3-(벤질옥시)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(1,3-티아졸-4-일)프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-플루오로페닐)프로판-1-온; (2S,3S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸펜탄-1-온; (2R)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(3,4-디플루오로페닐)프로판-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸-2-(메틸아미노)프로판-1-온; 7-{[(2S)-아제티딘-2-일]카르보닐}-N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-메틸펜탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-[(모르폴린-3-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-페닐프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-시클로부틸프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3,3-디메틸부탄-1-온; (2R)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; 4-[(2S)-2-아미노-3-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-옥소프로필]벤조니트릴; 2-(4-플루오로페닐)-6-메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(2,5-디플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3,4-디플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-페닐-2-(페닐아미노)에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-[2-(트리플루오로메톡시)페닐]에탄-1-온; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-페닐프로판-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-[4-플루오로-3-(트리플루오로메틸)페닐]에탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-페녹시에탄-1-온; 5-({3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}카르보닐)피페리딘-2-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-{[(2S)-피롤리딘-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 3-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4,4,4-트리플루오로부탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-{[(3S)-피롤리딘-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-메틸페닐)프로판-1-온; N-(4-클로로-3-플루오로페닐)-7-[(2,3-디히드로-1H-이소인돌-1-일)카르보닐]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로-3-플루오로페닐)-7-{[(2S)-2,3-디히드로-1H-인돌-2-일]카르보닐}-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (3S)-3-아미노-4-(4-브로모페닐)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}부탄-1-온; (2R)-2-아미노-3-(4-브로모페닐)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-{[(4-메톡시페닐)메틸]술파닐}프로판-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-{[(3R)-1,2,3,4-테트라히드로이소퀴놀린-3-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4,4,4-트리플루오로부탄-1-온; 2-(2-부톡시에톡시)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-에톡시-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(2-메톡시에톡시)에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-6-메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 5-{[7-(2-아미노-2-메틸프로파노일)-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-플루오로벤조니트릴; N-(4-메틸페닐)-2-(피리딘-4-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-{[2-클로로-4-(트리플루오로메틸)페닐]아미노}-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸부탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-{[(2R)-옥솔란-2-일]카르보닐}-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(1-메틸-1H-인돌-3-일)에탄-1-온; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-4-메틸펜탄-1-온; 1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(2-플루오로페닐)프로판-1-온; (2R)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; 2-[(3-클로로페닐)아미노]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(4-메틸페닐)아미노]에탄-1-온; 2-(4-클로로-3-플루오로페닐)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(4-메톡시페닐)아미노]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(3,4-디클로로페닐)에탄-1-온; 2-아미노-3,3,3-트리플루오로-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-[(모르폴린-2-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-[4-(트리플루오로메틸)페닐]에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(4-클로로페닐)에탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-[(퀴놀린-6-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(4-메틸페닐)아미노]-2-페닐에탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-7-[(4-메틸모르폴린-2-일)카르보닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(2-플루오로페닐)아미노]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸-2-(페닐아미노)프로판-1-온; 2-아미노-1-(3-{[4-플루오로-2-(트리플루오로메틸)페닐]아미노}-2-(3-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)-2-메틸프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸-2-(메틸아미노)부탄-1-온; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-메틸-2-(메틸아미노)펜탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-메틸-2-(메틸아미노)펜탄-1-온; 2-아미노-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-[(2,6-디메틸페닐)아미노]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-아미노-1-[2-(2-메톡시페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-메틸페닐)아미노]-2-(피리딘-4-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(3-클로로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-[(2,4-디메틸페닐)아미노]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸-2-[(4-메틸페닐)아미노]프로판-1-온; 2-아미노-1-[2-(2,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-[벤질(메틸)아미노]-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)헥산-1-온; 1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(4-메틸페닐)에탄-1-온; (2R)-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)펜탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}부탄-1-온; (2R)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-메틸펜탄-1-온; 2-아미노-1-[2-(2,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; (2S)-2-아미노-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸부탄-1-온; 2-아미노-1-[2-(3-클로로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-2-메틸-1-{3-[(4-메틸페닐)아미노]-2-(피리딘-4-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; 2-(tert-부틸아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-3-(4-클로로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-(메틸아미노)프로판-1-온; (2S)-2-아미노-3-시클로프로필-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2R)-2-(벤질아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-(벤질아미노)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-2-시클로프로필-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-아미노-3-(3,4-디플루오로페닐)-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(3,4-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-[(4-메틸페닐)아미노]프로판-1-온; 2-아미노-1-[2-(2,5-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,4-디클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; N-(3,4-디클로로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; N-(4-클로로-3-플루오로페닐)-N-에틸-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2R)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸-2-(메틸아미노)부탄-1-온; 2-(4-플루오로페닐)-8,8-디메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(2,5-디플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; N-(3,4-디플루오로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; N-(3-클로로-4-플루오로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 4-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 4-{[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 2-아미노-1-{3-[(3,4-디플루오로-5-메톡시페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-플루오로-3,5-디메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; (2S)-2-아미노-3-시클로부틸-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2R)-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(1,3-티아졸-4-일)프로판-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-메틸페닐)프로판-1-온; (2S)-2-아미노-3-(3,4-디플루오로페닐)-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(4-플루오로페닐)에탄-1-온; (2S)-2-아미노-2-시클로프로필-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; (2S)-2-아미노-3-시클로프로필-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-메틸펜탄-1-온; (2S)-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; 7-{[(2S)-아제티딘-2-일]카르보닐}-N-(3,4-디플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S,3S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸펜탄-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-플루오로페닐)프로판-1-온; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-N-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3-플루오로페닐)-2-(4-플루오로페닐)-N-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-에틸-N-(3-플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3-클로로-4-플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-시클로프로필에탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-시클로프로필프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-시클로부틸프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-4-메틸펜탄-1-온; (2S,3S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-메틸펜탄-1-온; (2S)-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; (2R)-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(4-플루오로페닐)에탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-플루오로페닐)프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(4-메틸페닐)프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(3,4-디플루오로페닐)프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-(1,3-티아졸-4-일)프로판-1-온; 7-{[(2S)-아제티딘-2-일]카르보닐}-N-(4-클로로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3,3-디메틸부탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸부탄-1-온; (2S)-2-아미노-2-시클로프로필-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-아미노-3-시클로프로필-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-3-시클로부틸-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-메틸펜탄-1-온; (2S,3S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸펜탄-1-온; (2S)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; (2R)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; (2S)-2-아미노-2-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-아미노-3-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(4-메틸페닐)프로판-1-온; (2S)-2-아미노-3-(3,4-디플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(1,3-티아졸-4-일)프로판-1-온; 7-{[(2S)-아제티딘-2-일]카르보닐}-N,2-비스(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3,3-디메틸부탄-1-온; (2S)-2-아미노-3-시클로부틸-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-4-메틸펜탄-1-온; (2S,3S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-메틸펜탄-1-온; (2S)-2-아미노-2-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(4-메틸페닐)프로판-1-온; (2S)-2-아미노-3-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-3-(3,4-디플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(1,3-티아졸-4-일)프로판-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-시클로프로필에탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3-시클로프로필프로판-1-온; (2S)-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-히드록시-3-메틸부탄-1-온; (2S)-2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-(4-플루오로페닐)에탄-1-온; (2S)-2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-3,3-디메틸부탄-1-온; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; N,2-비스(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로-3-메틸페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-(3-클로로-4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-클로로-3-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(3-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(4-플루오로페닐)-8,8-디메틸-3-{[3-(트리플루오로메틸)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(3-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (2S)-2-아미노-3-(4-플루오로페닐)-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2,4-디메틸펜탄-1-온; (2S)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-2-메틸프로판-1-온; (2R)-2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-히드록시-2-메틸프로판-1-온; 3-[(3,4-디클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 4-{[2-(4-플루오로페닐)-8,8-디메틸-6-옥소-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; N-(3-플루오로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-8,8-디메틸-N-[3-(트리플루오로메틸)페닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2,2,2-트리플루오로-1-[2-(4-플루오로페닐)-3-[(3-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로-3-메틸페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로-3-메틸페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(3-클로로-4-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-클로로-3-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-클로로-3-플루오로페닐)-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 5-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-플루오로벤조니트릴; 2-플루오로-5-{[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조산; 2-플루오로-5-{[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 5-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; 5-{[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조산; 5-{[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; 2,2,2-트리플루오로-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[3-(트리플루오로메틸)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; tert-부틸 N-{1-[3-브로모-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸-1-옥소프로판-2-일}카르바메이트; 2-아미노-1-[3-(시클로헥실아미노)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3-클로로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3-플루오로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 4-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-클로로벤조니트릴; 5-{[2-(4-플루오로페닐)-8,8-디메틸-6-옥소-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; N,2-비스(4-플루오로페닐)-5,5,7,8,8-펜타메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-플루오로-5-{[2-(4-플루오로페닐)-8,8-디메틸-6-옥소-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 2-(4-플루오로페닐)-5,5,7,8,8-펜타메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-5,5,7,8,8-펜타메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; tert-부틸 N-{2-[2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}카르바메이트; N-(3-플루오로-4-메틸페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3-클로로-4-메틸페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-(4-플루오로페닐)-8,8-디메틸-3-[(3,4,5-트리플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(6-메톡시피리딘-3-일)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(3-클로로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸피리딘-2-일)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-클로로-4-{[2-(4-플루오로페닐)-8,8-디메틸-6-옥소-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; (8R)-3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (8R)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(3,4-디플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; N-(3-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}페닐)메탄술폰아미드; 3-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-N-메틸벤즈아미드; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(3,4,5-트리플루오로페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(4-플루오로페닐)-8,8-디메틸-N-(3,4,5-트리플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로페닐)-2-(4-플루오로페닐)-6,6,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; N-(4-클로로페닐)-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; (8S)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(1,5-디메틸-1H-피라졸-3-일)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-({[(2S)-1-에틸피롤리딘-2-일]메틸}아미노)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (8S)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (8S)-3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (8R)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (8R)-3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-8,8-디메틸-3-(퀴놀린-3-일아미노)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(4-메탄술포닐페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-8,8-디메틸-3-{[4-(4-메틸피페라진-1-일)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-8,8-디메틸-3-({3-[(4-메틸피페라진-1-일)메틸]페닐}아미노)-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메탄술포닐페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[4-(4-메틸피페라진-1-일)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-(4-플루오로페닐)-8,8-디메틸-N-[4-(4-메틸피페라진-1-일)페닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-[2-(4-플루오로페닐)-6,6-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 5-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-플루오로벤조니트릴; 2-(4-플루오로페닐)-6,6-디메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N,2-비스(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3,4-디플루오로페닐)-2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-플루오로-5-{[2-(4-플루오로페닐)-6,6-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 2-(3-플루오로페닐)-7-[(4-메톡시페닐)메틸]-5,5-디메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3,4-디클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 5-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; 4-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-클로로벤조니트릴; (2S)-1-[2-(3-플루오로페닐)-5,5-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-메틸부탄-1-온; 2-아미노-1-[2-(3-플루오로페닐)-5,5-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(3-플루오로페닐)-5,5-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[(8S)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[(8R)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[(8S)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 3-[(3-플루오로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; (2S)-1-[2-(3-플루오로페닐)-5,5-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-히드록시-3-페닐프로판-1-온; 2-아미노-1-{3-[(1,5-디메틸-1H-피라졸-3-일)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(1-에틸-1H-피라졸-5-일)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[(8R)-3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-8-(프로판-2-일)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 3-[(3-플루오로-4-메틸페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(3-클로로-4-메틸페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; N,2-비스(4-플루오로페닐)-7,8,8-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로페닐)-2-(4-플루오로페닐)-7,8,8-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로페닐)-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(4-클로로-3-메틸페닐)-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; N-(3,4-디플루오로페닐)-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 5-{[2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-7-[(4-메톡시페닐)메틸]-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-7-[(4-메톡시페닐)메틸]-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5,5,7-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(3-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3-클로로-4-플루오로페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; N-(3-클로로-4-플루오로페닐)-2-(4-플루오로페닐)-7,8,8-트리메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-아민; 2-아미노-1-{3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 5-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-메틸벤조니트릴; 2-아미노-1-{3-[(3-플루오로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-{3-[(3-클로로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-(3-{[3-클로로-4-(트리플루오로메틸)페닐]아미노}-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)-2-메틸프로판-1-온; 2-아미노-1-(3-{[4-플루오로-3-(트리플루오로메틸)페닐]아미노}-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)-2-메틸프로판-1-온; 4-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-(트리플루오로메틸)벤조니트릴; 5-{[7-(2-아미노-2-메틸프로파노일)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-플루오로벤조니트릴; 2-아미노-1-{3-[(3,4-디메틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(3-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(3-클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-{[3-(트리플루오로메톡시)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(4-에틸페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 2-아미노-1-(3-{[4-(디플루오로메톡시)페닐]아미노}-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-{[4-(트리플루오로메톡시)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-{3-[(3,5-디클로로페닐)아미노]-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}-2-메틸프로판-1-온; 10-[(3,4-디플루오로페닐)아미노]-11-(4-플루오로페닐)-4,4-디메틸-3,6,9,12-테트라아자트리시클로[7.3.0.0{2,6}]도데카-1(12),2,10-트리엔-5-온; 10-[(3,4-디플루오로페닐)아미노]-11-(4-플루오로페닐)-4,4-디메틸-3,6,9,12-테트라아자트리시클로[7.3.0.0{2,6}]도데카-1(12),10-디엔-5-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-페닐페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-에틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[4-(트리플루오로메톡시)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[3-(트리플루오로메톡시)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3-클로로페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[3-(트리플루오로메틸)페닐]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 3-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}벤조니트릴; 2-아미노-1-{3-[(3,4-디메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 4-{[7-(2-아미노아세틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-일]아미노}-2-(트리플루오로메틸)벤조니트릴; 2-아미노-1-{3-[(3,5-디메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-(3-{[4-플루오로-3-(트리플루오로메틸)페닐]아미노}-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)에탄-1-온; 2-아미노-1-(3-{[3-클로로-4-(트리플루오로메틸)페닐]아미노}-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일)에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4,4-디플루오로시클로헥실)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-페닐시클로헥실)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-{[4-(트리플루오로메틸)시클로헥실]아미노}-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-tert-부틸시클로헥실)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(2-메틸시클로헥실)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(시클로헵틸아미노)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(3,3,5-트리메틸시클로헥실)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(1R,2R,4S)-비시클로[2.2.1]헵탄-2-일아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[3-(디메틸아미노)피롤리딘-1-일]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[4-(피페리딘-1-일)피페리딘-1-일]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(시클로펜틸아미노)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(시클로부틸아미노)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-(옥산-4-일아미노)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[4-(1-메틸피페리딘-4-일)피페라진-1-일]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(2-메틸부틸)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-클로로-3-플루오로페닐)아미노]-2-(4-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-5,5-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-클로로페닐)아미노]-2-(4-플루오로페닐)-5,5-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로페닐)(메틸)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 7-[2-(디메틸아미노)에틸]-2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)아미노]-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 7-[2-(디메틸아미노)에틸]-3-[(3-플루오로-4-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(3-클로로-4-메틸페닐)아미노]-7-[2-(디메틸아미노)에틸]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 7-[2-(디메틸아미노)에틸]-3-[(4-플루오로-3-메틸페닐)아미노]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-메틸페닐)아미노]-7-[2-(디메틸아미노)에틸]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-클로로-3-플루오로페닐)아미노]-7-[2-(디메틸아미노)에틸]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 7-(아제티딘-3-일메틸)-3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 7-(2-아미노에틸)-2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-7-(2-히드록시에틸)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 7-(3-아미노프로필)-3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-7-(3-히드록시프로필)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-7-(3-메톡시프로필)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-6-온; 4-{3-[(4-플루오로-3-메틸페닐)아미노]-2-(3-플루오로페닐)-8,8-디메틸-6-옥소-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}부탄산; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)메틸]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)메틸]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-메톡시페닐)메틸]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)메틸]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)메틸]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-메틸프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸피페라진-1-일)메틸]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(시클로헥실메틸)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-3-(4-메틸페닐)프로판-1-온; 2-아미노-4-(3-플루오로페닐)-1-[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; 2-아미노-4-(4-클로로페닐)-1-[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]부탄-1-온; 2-아미노-3-시클로헥실-1-[2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]프로판-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2,3-비스(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(3-클로로-4-플루오로페닐)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; N,2-비스(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-카르복스아미드; 7-(2-아미노아세틸)-N,2-비스(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-3-카르복스아미드; 2-아미노-1-[3-(4-플루오로페녹시)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(4-클로로페녹시)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(3,4-디플루오로페녹시)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[3-(4-플루오로-3-메틸페녹시)-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸페닐)술파닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(3-플루오로페닐)술파닐]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)술파닐]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(4-클로로페닐)술파닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3,5-디메틸페닐)술파닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3,4-디플루오로페닐)술파닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3-플루오로벤젠)술피닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-플루오로벤젠)술피닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸벤젠)술피닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온; 2-아미노-1-{3-[(3,5-디메틸벤젠)술피닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(3,4-디플루오로벤젠)술피닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 2-아미노-1-{3-[(4-클로로벤젠)술피닐]-2-(4-플루오로페닐)-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일}에탄-1-온; 및 2-아미노-1-[2-(4-플루오로페닐)-8,8-디메틸-3-[(4-메틸벤젠)술포닐]-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]에탄-1-온으로부터 선택되는 화합물.
- N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}-3-페닐프로판아미드; N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}-3-{8-옥사트리시클로[7.4.0.0{2,7}]트리데카-1(9),2,4,6,10,12-헥사엔-4-일}프로판아미드; N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}-3-(3-페닐프로판아미도)프로판아미드; N-{2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}-3-(3-{8-옥사트리시클로[7.4.0.0{2,7}]트리데카-1(9),2,4,6,10,12-헥사엔-4-일}프로판아미도)프로판아미드; N-[3-({2-[2-(4-플루오로페닐)-3-[(4-플루오로페닐)아미노]-8,8-디메틸-5H,6H,7H,8H-이미다조[1,2-a]피라진-7-일]-2-옥소에틸}아미노)프로필]-3-페닐프로판아미드; 5,5-디플루오로-3-(3-(2-(2-(4-플루오로페닐)-3-(4-플루오로페닐아미노)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)-2-옥소에틸아미노)-3-옥소프로필)-7-페닐-5H-디피롤로[1,2-c:1',2'-f][1,3,2]디아자보리닌-4-이움-5-우이드; 및 5,5-디플루오로-2-(3-(6-(2-(2-(4-플루오로페닐)-3-(4-플루오로페닐아미노)-8,8-디메틸-5,6-디히드로이미다조[1,2-a]피라진-7(8H)-일)-2-옥소에틸아미노)-6-옥소헥실아미노)-3-옥소프로필)-7-(4-메톡시페닐)-1,3-디메틸-5H-디피롤로[1,2-c:1',2'-f][1,3,2]디아자보리닌-4-이움-5-우이드로부터 선택되는 화합물.
- N-(4-메틸페닐)-2-(피리딘-3-일)-5H,6H,7H,8H-이미다조[1,2-a]피리딘-3-아민; 2-시클로헥실-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(디페닐메틸)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(2-니트로페닐)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-[2-(티오펜-2-일)페닐]-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-[2-(디플루오로메톡시)페닐]-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(2-브로모페닐)-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-{2-[2-(디에틸아미노)에톡시]페닐}-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-[2-(트리플루오로메틸)페닐]-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(2-{3-[(2,4,4-트리메틸펜탄-2-일)아미노]이미다조[1,2-a]피리딘-2-일}페녹시)에탄-1-올; 2-[2-(푸란-2-일)페닐]-N-(2,4,4-트리메틸펜탄-2-일)이미다조[1,2-a]피리딘-3-아민; 2-(4-플루오로페닐)-6-메틸-N-(4-메틸페닐)이미다조[1,2-a]피리딘-3-아민; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-5H,6H,7H,8H-이미다조[1,2-a]피리딘-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피리딘-3-아민; 2-(4-플루오로페닐)-N-(4-메틸페닐)이미다조[1,2-a]피리딘-3-아민; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-6-메틸이미다조[1,2-a]피리딘-3-아민; 2-(4-플루오로페닐)-6-메틸-N-(4-메틸페닐)-5H,6H,7H,8H-이미다조[1,2-a]피리딘-3-아민; N-(4-클로로-3-플루오로페닐)-2-(4-플루오로페닐)-6-메틸-5H,6H,7H,8H-이미다조[1,2-a]피리딘-3-아민; 8-(3,4-디플루오로페닐아미노)-9-(4-플루오로페닐)-2,2-디메틸-5,6-디히드로디이미다조[1,2-a:2',1'-c]피라진-3(2H)-온; 및 8-(3,4-디플루오로페닐아미노)-9-(4-플루오로페닐)-2,2-디메틸-1,2,5,6-테트라히드로디이미다조[1,2-a:2',1'-c]피라진-3(10bH)-온으로부터 선택되는 화합물.
- 치료 유효량의 제6항 또는 제7항의 화합물을 임의로 제2 작용제와 조합하여 대상체에게 투여하는 것을 포함하는, 열원충 관련 질환의 병태 및/또는 증상을 예방, 억제 또는 완화시키기 위한 대상체에서의 열원충 관련 질환의 치료 방법.
- 제11항에 있어서, 열원충 관련 질환이 말라리아인 방법.
- 제11항에 있어서, 접촉이 시험관내 또는 생체내에서 발생하는 방법.
- 제11항에 있어서, 제2 작용제가 키나제 억제제, 항말라리아 약물 및 소염제로부터 선택되는 것인 방법.
- 제14항에 있어서, 항말라리아 약물이 프로구아닐, 클로르프로구아닐, 트리메토프림, 클로로퀸, 메플로퀸, 루메판트린, 아토바쿠온, 피리메타민-술파독신, 피리메타민-다프손, 할로판트린, 퀴닌, 퀴니딘, 아모디아퀸, 아모피로퀸, 술폰아미드, 아르테미시닌, 아르테플렌, 아르테메테르, 아르테수네이트, 프리마퀸 및 피로나리딘으로부터 선택되는 것인 방법.
- 제15항에 있어서, 제1항, 제8항, 제9항 또는 제10항의 화합물을 제2 작용제 투여 이전에, 투여와 동시에 또는 투여 이후에 투여하는 방법.
- 제11항에 있어서, 상기 대상체가 인간인 방법.
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KR20190038917A (ko) * | 2016-08-15 | 2019-04-09 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 축합 바이시클릭 헤테로사이클 유도체 |
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