JP5824040B2 - 置換イミダゾピラジン - Google Patents

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Publication number

JP5824040B2

JP5824040B2 JP2013512850A JP2013512850A JP5824040B2 JP 5824040 B2 JP5824040 B2 JP 5824040B2 JP 2013512850 A JP2013512850 A JP 2013512850A JP 2013512850 A JP2013512850 A JP 2013512850A JP 5824040 B2 JP5824040 B2 JP 5824040B2

Authority

JP

Japan

Prior art keywords

alkyl

alkoxy

halo

imidazo

cycloalkyl

Prior art date

2010-06-01

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

Expired - Fee Related

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• 150000005235 imidazopyrazines Chemical class 0.000 title description 2
• -1 cyano - Chemical class 0.000 claims description 334
• 150000001875 compounds Chemical class 0.000 claims description 289
• 125000005843 halogen group Chemical group 0.000 claims description 154
• 125000001072 heteroaryl group Chemical group 0.000 claims description 135
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 132
• 125000003118 aryl group Chemical group 0.000 claims description 126
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 121
• 229910052799 carbon Inorganic materials 0.000 claims description 95
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 88
• 239000000203 mixture Substances 0.000 claims description 87
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 76
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims description 55
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 51
• 150000003839 salts Chemical class 0.000 claims description 48
• 238000000034 method Methods 0.000 claims description 46
• 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 42
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
• 239000001257 hydrogen Substances 0.000 claims description 38
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• 239000012453 solvate Substances 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 22
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 18
• 150000001204 N-oxides Chemical class 0.000 claims description 17
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 125000005418 aryl aryl group Chemical group 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 13
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 13
• 238000002360 preparation method Methods 0.000 claims description 13
• 150000004677 hydrates Chemical class 0.000 claims description 10
• 235000013772 propylene glycol Nutrition 0.000 claims description 9
• 229960004063 propylene glycol Drugs 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• MBVAHHOKMIRXLP-UHFFFAOYSA-N imidazo[1,2-a]pyrazine Chemical compound C1=CN=CC2=NC=CN21 MBVAHHOKMIRXLP-UHFFFAOYSA-N 0.000 claims description 7
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
• 125000000524 functional group Chemical group 0.000 claims description 5
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 4
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 4
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 4
• 229960002949 fluorouracil Drugs 0.000 claims description 4
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
• 229960004641 rituximab Drugs 0.000 claims description 4
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
• WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 3
• PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims description 3
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
• XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 claims description 3
• XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims description 3
• 239000004146 Propane-1,2-diol Substances 0.000 claims description 3
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 3
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
• 229960004397 cyclophosphamide Drugs 0.000 claims description 3
• 229960000684 cytarabine Drugs 0.000 claims description 3
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 3
• 229960005420 etoposide Drugs 0.000 claims description 3
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
• GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 claims description 3
• 229960000908 idarubicin Drugs 0.000 claims description 3
• 229960001101 ifosfamide Drugs 0.000 claims description 3
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 3
• SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims description 3
• 229960001924 melphalan Drugs 0.000 claims description 3
• 229960001156 mitoxantrone Drugs 0.000 claims description 3
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 3
• HJWBJUAGCYPSDP-UHFFFAOYSA-N n-(2,2-difluoroethyl)-4-[6-ethynyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C(=O)NCC(F)F)C(C)=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C#C)=C1 HJWBJUAGCYPSDP-UHFFFAOYSA-N 0.000 claims description 3
• CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims description 3
• 229960000624 procarbazine Drugs 0.000 claims description 3
• 229960003087 tioguanine Drugs 0.000 claims description 3
• 229960003048 vinblastine Drugs 0.000 claims description 3
• JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 3
• 229960004528 vincristine Drugs 0.000 claims description 3
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
• WSHPFVZKPKNXLP-UHFFFAOYSA-N 2-(1-methylcyclopropyl)benzamide Chemical compound C=1C=CC=C(C(N)=O)C=1C1(C)CC1 WSHPFVZKPKNXLP-UHFFFAOYSA-N 0.000 claims description 2
• 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 2
• YBLDVQUSKXSUAN-UHFFFAOYSA-N 3-[3-[3-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-6-yl]prop-2-yn-1-ol Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCO)=CN2C=1C(C=1)=CC=CC=1C(N1)=CN=C1C1CC1 YBLDVQUSKXSUAN-UHFFFAOYSA-N 0.000 claims description 2
• GMMFTXWDTNSPRY-UHFFFAOYSA-N 3-[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-8-(2-methylprop-2-enylamino)imidazo[1,2-a]pyrazin-6-yl]prop-2-yn-1-ol Chemical compound C=1N=C2C(NCC(=C)C)=NC(C#CCO)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 GMMFTXWDTNSPRY-UHFFFAOYSA-N 0.000 claims description 2
• ARVIRXHDEZDSCW-UHFFFAOYSA-N 3-[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-6-yl]prop-2-yn-1-ol Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCO)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 ARVIRXHDEZDSCW-UHFFFAOYSA-N 0.000 claims description 2
• SLIXJNVGBFXHJA-UHFFFAOYSA-N 3-[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-8-(4,4,4-trifluorobutylamino)imidazo[1,2-a]pyrazin-6-yl]prop-2-yn-1-ol Chemical compound C=1N=C2C(NCCCC(F)(F)F)=NC(C#CCO)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 SLIXJNVGBFXHJA-UHFFFAOYSA-N 0.000 claims description 2
• JVFKDSIXLPVWOS-UHFFFAOYSA-N 3-[8-(3-aminopropylamino)-3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]prop-2-yn-1-ol Chemical compound C=1N=C2C(NCCCN)=NC(C#CCO)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 JVFKDSIXLPVWOS-UHFFFAOYSA-N 0.000 claims description 2
• OAKUUSQUHCULEY-UHFFFAOYSA-N 3-[[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-(3-hydroxyprop-1-ynyl)imidazo[1,2-a]pyrazin-8-yl]amino]propan-1-ol Chemical compound C=1N=C2C(NCCCO)=NC(C#CCO)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 OAKUUSQUHCULEY-UHFFFAOYSA-N 0.000 claims description 2
• KJFNGLXJZCVBGE-UHFFFAOYSA-N 4-[6-ethynyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1C=C(C#C)N=C2NCCC(F)(F)F KJFNGLXJZCVBGE-UHFFFAOYSA-N 0.000 claims description 2
• PVYMNPSRPPVKPQ-UHFFFAOYSA-N 4-[6-ethynyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-(1-methoxycyclopropyl)-2-methylbenzamide Chemical compound C=1C=C(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C#C)C=C(C)C=1C(=O)NC1(OC)CC1 PVYMNPSRPPVKPQ-UHFFFAOYSA-N 0.000 claims description 2
• STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 2
• 108010006654 Bleomycin Proteins 0.000 claims description 2
• GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 2
• GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims description 2
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 2
• 229960001561 bleomycin Drugs 0.000 claims description 2
• OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 2
• GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims description 2
• 229960001467 bortezomib Drugs 0.000 claims description 2
• 229960004117 capecitabine Drugs 0.000 claims description 2
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 2
• 229960004630 chlorambucil Drugs 0.000 claims description 2
• STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 2
• 229960000975 daunorubicin Drugs 0.000 claims description 2
• 229960000390 fludarabine Drugs 0.000 claims description 2
• 229960000485 methotrexate Drugs 0.000 claims description 2
• LTDPIZXAJBAEDR-UHFFFAOYSA-N n-(1-cyanocyclopropyl)-4-[6-ethynyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C#C)=CC=C1C(=O)NC1(C#N)CC1 LTDPIZXAJBAEDR-UHFFFAOYSA-N 0.000 claims description 2
• JPPWNRNUVNDHIA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-hydroxyprop-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCO)=CN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 JPPWNRNUVNDHIA-UHFFFAOYSA-N 0.000 claims description 2
• YGGKXUZAZYKVLR-UHFFFAOYSA-N n-cyclopropyl-4-[8-(2-methylpropylamino)-6-(2-phenylethynyl)imidazo[1,2-a]pyrazin-3-yl]benzenesulfonamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1S(=O)(=O)NC1CC1 YGGKXUZAZYKVLR-UHFFFAOYSA-N 0.000 claims description 2
• VPJBMBIMMBMVTG-UHFFFAOYSA-N n-ethyl-4-[6-ethynyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1C=C(C#C)N=C2NCCC(F)(F)F VPJBMBIMMBMVTG-UHFFFAOYSA-N 0.000 claims description 2
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
• VOXBZHOHGGBLCQ-UHFFFAOYSA-N 2-amino-3,7-dihydropurine-6-thione;hydrate Chemical compound O.N1C(N)=NC(=S)C2=C1N=CN2.N1C(N)=NC(=S)C2=C1N=CN2 VOXBZHOHGGBLCQ-UHFFFAOYSA-N 0.000 claims 1
• LOPVAUAMTOQZMH-UHFFFAOYSA-N 4-[2-[3-[4-(cyclopropylcarbamoyl)phenyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-6-yl]ethynyl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC=3C=CC(=CC=3)C(N)=O)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 LOPVAUAMTOQZMH-UHFFFAOYSA-N 0.000 claims 1
• NECFVPYNODMISP-UHFFFAOYSA-N 4-[6-(2-cyclohexylethynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC3CCCCC3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 NECFVPYNODMISP-UHFFFAOYSA-N 0.000 claims 1
• PNNPELOXIAYGKY-UHFFFAOYSA-N 4-[6-(2-cyclopentylethynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC3CCCC3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 PNNPELOXIAYGKY-UHFFFAOYSA-N 0.000 claims 1
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