CA2801031A1 - Substituted imidazopyrazines - Google Patents

Info

Publication number

CA2801031A1

CA2801031A1 CA2801031A CA2801031A CA2801031A1 CA 2801031 A1 CA2801031 A1 CA 2801031A1 CA 2801031 A CA2801031 A CA 2801031A CA 2801031 A CA2801031 A CA 2801031A CA 2801031 A1 CA2801031 A1 CA 2801031A1

Authority

CA

Canada

Prior art keywords

alkyl

alkoxy

pyrazin

halo

imidazo

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000005235 imidazopyrazines Chemical class 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 292
• 238000000034 method Methods 0.000 claims abstract description 52
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 51
• 238000011282 treatment Methods 0.000 claims abstract description 34
• 201000010099 disease Diseases 0.000 claims abstract description 31
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 238000011321 prophylaxis Methods 0.000 claims abstract description 14
• 238000002360 preparation method Methods 0.000 claims abstract description 13
• -1 cyano- Chemical class 0.000 claims description 298
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 215
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 139
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 101
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 99
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 96
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 95
• 239000000203 mixture Substances 0.000 claims description 90
• 125000001072 heteroaryl group Chemical group 0.000 claims description 69
• 206010028980 Neoplasm Diseases 0.000 claims description 68
• 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 66
• 125000005843 halogen group Chemical group 0.000 claims description 65
• 229910052739 hydrogen Inorganic materials 0.000 claims description 59
• 150000003839 salts Chemical class 0.000 claims description 55
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 52
• 125000003118 aryl group Chemical group 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 41
• 229910052799 carbon Inorganic materials 0.000 claims description 40
• 125000004432 carbon atom Chemical group C* 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 239000012453 solvate Substances 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 25
• 125000005418 aryl aryl group Chemical group 0.000 claims description 23
• 150000001204 N-oxides Chemical class 0.000 claims description 21
• 239000003795 chemical substances by application Substances 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 230000004663 cell proliferation Effects 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
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• 230000024932 T cell mediated immunity Effects 0.000 claims description 16
• 230000001413 cellular effect Effects 0.000 claims description 16
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• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 14
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• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 4
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• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 4
• 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 4
• 229930013356 epothilone Natural products 0.000 claims description 4
• 150000003883 epothilone derivatives Chemical class 0.000 claims description 4
• 229960002949 fluorouracil Drugs 0.000 claims description 4
• WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 108010006654 Bleomycin Proteins 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
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 3
• 229960004562 carboplatin Drugs 0.000 claims description 3
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 3
• 229960004630 chlorambucil Drugs 0.000 claims description 3
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 3
• 229960004316 cisplatin Drugs 0.000 claims description 3
• 229960004397 cyclophosphamide Drugs 0.000 claims description 3
• 229960000684 cytarabine Drugs 0.000 claims description 3
• 229960003668 docetaxel Drugs 0.000 claims description 3
• 229960004679 doxorubicin Drugs 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
• 229960002074 flutamide Drugs 0.000 claims description 3
• MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-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
• 229960000485 methotrexate 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
• 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
• MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims description 3
• 229960003087 tioguanine Drugs 0.000 claims description 3
• 229960003048 vinblastine Drugs 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
• CGHHWITVXBIQFI-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-[3-(1,1-dioxo-1,4-thiazinan-4-yl)prop-1-ynyl]-n-(3,3,3-trifluoropropyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C=1N=C2C(NCCC(F)(F)F)=NC(C#CCN3CCS(=O)(=O)CC3)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 CGHHWITVXBIQFI-UHFFFAOYSA-N 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
• 229940123237 Taxane Drugs 0.000 claims description 2
• 150000001345 alkine derivatives Chemical class 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
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• UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 claims description 2
• 229960000978 cyproterone acetate Drugs 0.000 claims description 2
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• 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 2
• 229960000390 fludarabine Drugs 0.000 claims description 2
• FABUFPQFXZVHFB-CFWQTKTJSA-N ixabepilone Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@H](C)C(=O)C(C)(C)[C@H](O)CC(=O)N1)O)C)=C\C1=CSC(C)=N1 FABUFPQFXZVHFB-CFWQTKTJSA-N 0.000 claims description 2
• 229960002014 ixabepilone Drugs 0.000 claims description 2
• VJBGLKMXWDAFMR-UHFFFAOYSA-N n-cyclopropyl-4-[8-(2-methylpropylamino)-6-(2-phenylethynyl)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 VJBGLKMXWDAFMR-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
• YCKPEFHLYWVLJA-UHFFFAOYSA-N n-cyclopropyl-4-[8-(4-hydroxybutylamino)-6-(3-hydroxy-3-methylbut-1-ynyl)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCCCCO)=NC(C#CC(C)(O)C)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 YCKPEFHLYWVLJA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 15
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
• OUMSKHMBCCDZKG-IBGZPJMESA-N (2s)-3-[[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-(3-hydroxyprop-1-ynyl)imidazo[1,2-a]pyrazin-8-yl]amino]propane-1,2-diol Chemical compound C=1N=C2C(NC[C@H](O)CO)=NC(C#CCO)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 OUMSKHMBCCDZKG-IBGZPJMESA-N 0.000 claims 1
• LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• WOMIAIYWIPRARA-UHFFFAOYSA-N 3-[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-6-yl]prop-2-yn-1-ol Chemical compound C=1N=C2C(NCCC(F)(F)F)=NC(C#CCO)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 WOMIAIYWIPRARA-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• YQPHGJXCHXNTMG-UHFFFAOYSA-N 3-[8-(cyclobutylmethylamino)-3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]prop-2-yn-1-ol Chemical compound N=1C(C#CCO)=CN2C(C=3C=CC(=CC=3)C=3NC(=NC=3)C3CC3)=CN=C2C=1NCC1CCC1 YQPHGJXCHXNTMG-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• VHQGSJZKTKAZKM-UHFFFAOYSA-N 4-[6-(3-aminoprop-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCN)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 VHQGSJZKTKAZKM-UHFFFAOYSA-N 0.000 claims 1
• BPBRGYAWEYXCDB-UHFFFAOYSA-N 4-[6-(3-hydroxyprop-1-ynyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methyl-n-(1-methylcyclopropyl)benzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C#CCO)=CC=C1C(=O)NC1(C)CC1 BPBRGYAWEYXCDB-UHFFFAOYSA-N 0.000 claims 1
• SOUQUOHQWXWZBP-UHFFFAOYSA-N 4-[6-(3-hydroxyprop-1-ynyl)-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#CCO)N=C2NCCC(F)(F)F SOUQUOHQWXWZBP-UHFFFAOYSA-N 0.000 claims 1
• OFOQCVBSBBRMRB-UHFFFAOYSA-N 4-[6-(3-hydroxyprop-1-ynyl)-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#CCO)C=C(C)C=1C(=O)NC1(OC)CC1 OFOQCVBSBBRMRB-UHFFFAOYSA-N 0.000 claims 1
• NZRVNQXILCXBFD-UHFFFAOYSA-N 4-[6-(5-cyanopent-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCCCC#N)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 NZRVNQXILCXBFD-UHFFFAOYSA-N 0.000 claims 1
• RCEZMIMDUAGMNW-UHFFFAOYSA-N 4-[6-(5-cyclohexylpent-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCCCC3CCCCC3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 RCEZMIMDUAGMNW-UHFFFAOYSA-N 0.000 claims 1
• DNAPUPZAPABKLH-UHFFFAOYSA-N 4-[6-[3-(carbamoylamino)prop-1-ynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCNC(N)=O)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 DNAPUPZAPABKLH-UHFFFAOYSA-N 0.000 claims 1
• IECCARXOIHHPPG-UHFFFAOYSA-N 4-[6-[3-[benzyl(methyl)amino]prop-1-ynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCN(C)CC=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 IECCARXOIHHPPG-UHFFFAOYSA-N 0.000 claims 1
• QIXRMVWRWDWWOH-UHFFFAOYSA-N 4-[6-ethynyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methyl-n-(1-methylcyclopropyl)benzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C#C)=CC=C1C(=O)NC1(C)CC1 QIXRMVWRWDWWOH-UHFFFAOYSA-N 0.000 claims 1
• 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 1
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• VSBWTEAIJSJNCM-UHFFFAOYSA-N 4-[8-(3-aminopropylamino)-6-(3-hydroxyprop-1-ynyl)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropyl-3-methoxybenzamide Chemical compound C=1C=C(C=2N3C=C(N=C(NCCCN)C3=NC=2)C#CCO)C(OC)=CC=1C(=O)NC1CC1 VSBWTEAIJSJNCM-UHFFFAOYSA-N 0.000 claims 1
• MMOMUAYEDFRYSJ-UHFFFAOYSA-N 4-[[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-(3-hydroxyprop-1-ynyl)imidazo[1,2-a]pyrazin-8-yl]amino]butan-1-ol Chemical compound C=1N=C2C(NCCCCO)=NC(C#CCO)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 MMOMUAYEDFRYSJ-UHFFFAOYSA-N 0.000 claims 1
• JFVNUJZVJBUSGM-UHFFFAOYSA-N 6-[3-[4-(cyclopropylcarbamoyl)phenyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-6-yl]hex-5-ynoic acid Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCCCC(O)=O)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 JFVNUJZVJBUSGM-UHFFFAOYSA-N 0.000 claims 1
• KVNMTYPSRSVZIP-UHFFFAOYSA-N 9-[3-[4-(cyclopropylcarbamoyl)phenyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-6-yl]non-8-ynoic acid Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCCCCCCC(O)=O)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 KVNMTYPSRSVZIP-UHFFFAOYSA-N 0.000 claims 1
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
• BFZKMNSQCNVFGM-UCEYFQQTSA-N Sagopilone Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](CC=C)[C@@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@H]1C1=CC=C(SC(C)=N2)C2=C1 BFZKMNSQCNVFGM-UCEYFQQTSA-N 0.000 claims 1
• 229940009456 adriamycin Drugs 0.000 claims 1
• 230000002280 anti-androgenic effect Effects 0.000 claims 1
• 239000000051 antiandrogen Substances 0.000 claims 1
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• 229960003957 dexamethasone Drugs 0.000 claims 1
• HESCAJZNRMSMJG-HGYUPSKWSA-N epothilone A Natural products O=C1[C@H](C)[C@H](O)[C@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C HESCAJZNRMSMJG-HGYUPSKWSA-N 0.000 claims 1
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• FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 claims 1
• USQBFIZCNSURRO-UHFFFAOYSA-N methyl 6-[3-[4-(cyclopropylcarbamoyl)phenyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-6-yl]hex-5-ynoate Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCCCC(=O)OC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 USQBFIZCNSURRO-UHFFFAOYSA-N 0.000 claims 1
• UUBGMIJNXGBZCE-UHFFFAOYSA-N n-(1-cyanocyclopropyl)-4-[6-(3-hydroxyprop-1-ynyl)-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#CCO)=CC=C1C(=O)NC1(C#N)CC1 UUBGMIJNXGBZCE-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• DATDSDSXVSAMRO-UHFFFAOYSA-N n-(2,2-difluoroethyl)-4-[6-(3-hydroxyprop-1-ynyl)-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#CCO)=C1 DATDSDSXVSAMRO-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• MOFCEFOYLIOQQL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,3-dimethylbut-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC(C)(C)C)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 MOFCEFOYLIOQQL-UHFFFAOYSA-N 0.000 claims 1
• DQSNKOKEIBNIQI-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-hydroxy-3-methylbut-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC(C)(C)O)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 DQSNKOKEIBNIQI-UHFFFAOYSA-N 0.000 claims 1
• UEDDSSFXCLDVKS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-hydroxybut-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC(C)O)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 UEDDSSFXCLDVKS-UHFFFAOYSA-N 0.000 claims 1
• DYCTVEIJZLRMRC-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-hydroxyhex-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC(O)CCC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 DYCTVEIJZLRMRC-UHFFFAOYSA-N 0.000 claims 1
• RXOIVVZPBVVMAB-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-hydroxypent-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC(O)CC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 RXOIVVZPBVVMAB-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• NDAAMFQWAXOJPM-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-methoxyprop-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCOC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 NDAAMFQWAXOJPM-UHFFFAOYSA-N 0.000 claims 1
• CCXGEIAITMPFPN-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-hydroxybut-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCCO)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 CCXGEIAITMPFPN-UHFFFAOYSA-N 0.000 claims 1
• GBCFLGAIDRSQPU-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-hydroxypent-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCC(C)O)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 GBCFLGAIDRSQPU-UHFFFAOYSA-N 0.000 claims 1
• XEVZWBIMTOQUAY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-methylpent-1-ynyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCC(C)C)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 XEVZWBIMTOQUAY-UHFFFAOYSA-N 0.000 claims 1
• QHVPTEROMDCLGB-DEOSSOPVSA-N n-cyclopropyl-4-[6-[(3s)-3-hydroxyoct-1-ynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#C[C@@H](O)CCCCC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 QHVPTEROMDCLGB-DEOSSOPVSA-N 0.000 claims 1
• PMWKCIGJSKSVMC-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(1-hydroxycyclopentyl)ethynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC3(O)CCCC3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 PMWKCIGJSKSVMC-UHFFFAOYSA-N 0.000 claims 1
• KLKHINUDBYMHMF-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(2-fluorophenyl)ethynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC=3C(=CC=CC=3)F)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 KLKHINUDBYMHMF-UHFFFAOYSA-N 0.000 claims 1
• DXZAHPGQIBUTEG-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(2-fluorophenyl)ethynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzenesulfonamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC=3C(=CC=CC=3)F)=CN2C=1C(C=C1)=CC=C1S(=O)(=O)NC1CC1 DXZAHPGQIBUTEG-UHFFFAOYSA-N 0.000 claims 1
• YBTBSJJURDABOD-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(3-hydroxyphenyl)ethynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC=3C=C(O)C=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 YBTBSJJURDABOD-UHFFFAOYSA-N 0.000 claims 1
• VMNSEWPXOHTQCO-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(4-fluorophenyl)ethynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CC=3C=CC(F)=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 VMNSEWPXOHTQCO-UHFFFAOYSA-N 0.000 claims 1
• RVKRMWPRHIZFKN-UHFFFAOYSA-N n-cyclopropyl-4-[6-[3-(1,1-dioxo-1,4-thiazinan-4-yl)prop-1-ynyl]-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#CCN2CCS(=O)(=O)CC2)=CC=C1C(=O)NC1CC1 RVKRMWPRHIZFKN-UHFFFAOYSA-N 0.000 claims 1
• AUNRPDDMGDKPJT-UHFFFAOYSA-N n-cyclopropyl-4-[6-[3-(dimethylamino)prop-1-ynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCN(C)C)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 AUNRPDDMGDKPJT-UHFFFAOYSA-N 0.000 claims 1
• OJVALAFYQWPUGQ-UHFFFAOYSA-N n-cyclopropyl-4-[6-[3-(methylcarbamoylamino)prop-1-ynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCNC(=O)NC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 OJVALAFYQWPUGQ-UHFFFAOYSA-N 0.000 claims 1
• KDLBXZGAMSEQJP-UHFFFAOYSA-N n-cyclopropyl-4-[6-[3-[methyl(methylcarbamoyl)amino]prop-1-ynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCN(C)C(=O)NC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 KDLBXZGAMSEQJP-UHFFFAOYSA-N 0.000 claims 1
• WIVAVCDAENECOT-UHFFFAOYSA-N n-cyclopropyl-4-[6-[4-(methylcarbamoylamino)but-1-ynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCCNC(=O)NC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 WIVAVCDAENECOT-UHFFFAOYSA-N 0.000 claims 1
• VCVUVVNOSISFMD-UHFFFAOYSA-N n-cyclopropyl-4-[6-[4-[methyl(methylcarbamoyl)amino]but-1-ynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCCN(C)C(=O)NC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 VCVUVVNOSISFMD-UHFFFAOYSA-N 0.000 claims 1
• MMDPYNFJFGHILL-UHFFFAOYSA-N n-cyclopropyl-4-[6-[5-(methylamino)-5-oxopent-1-ynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCCC(=O)NC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 MMDPYNFJFGHILL-UHFFFAOYSA-N 0.000 claims 1
• ZTCOGZAOWGZHJA-UHFFFAOYSA-N n-cyclopropyl-4-[6-[6-(methylamino)-6-oxohex-1-ynyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#CCCCC(=O)NC)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 ZTCOGZAOWGZHJA-UHFFFAOYSA-N 0.000 claims 1
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