JP5841078B2 - イミダゾピラジン - Google Patents

Info

Publication number

JP5841078B2

JP5841078B2 JP2012557540A JP2012557540A JP5841078B2 JP 5841078 B2 JP5841078 B2 JP 5841078B2 JP 2012557540 A JP2012557540 A JP 2012557540A JP 2012557540 A JP2012557540 A JP 2012557540A JP 5841078 B2 JP5841078 B2 JP 5841078B2

Authority

JP

Japan

Prior art keywords

alkyl

pyrazin

cyclopropyl

phenylimidazo

benzamide

Prior art date

2010-03-18

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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• ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 301
• -1 (RS) tert-butyl [2-({3- [4- (cyclopropylcarbamoyl) phenyl] -6-phenylimidazo [1,2-a] pyrazin-8-yl} sulfinyl) ethyl] Chemical class 0.000 claims description 232
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 84
• 239000000203 mixture Substances 0.000 claims description 76
• 125000005843 halogen group Chemical group 0.000 claims description 70
• 125000003118 aryl group Chemical group 0.000 claims description 58
• 125000001072 heteroaryl group Chemical group 0.000 claims description 54
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 54
• 150000003839 salts Chemical class 0.000 claims description 47
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 45
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 44
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 36
• 201000010099 disease Diseases 0.000 claims description 32
• 238000011282 treatment Methods 0.000 claims description 32
• 206010028980 Neoplasm Diseases 0.000 claims description 31
• 108091000080 Phosphotransferase Proteins 0.000 claims description 26
• 102000020233 phosphotransferase Human genes 0.000 claims description 26
• 239000012453 solvate Substances 0.000 claims description 19
• 230000004663 cell proliferation Effects 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 17
• 230000004083 survival effect Effects 0.000 claims description 17
• 230000001413 cellular effect Effects 0.000 claims description 16
• 206010027476 Metastases Diseases 0.000 claims description 15
• 230000024932 T cell mediated immunity Effects 0.000 claims description 15
• 230000010261 cell growth Effects 0.000 claims description 15
• 230000028709 inflammatory response Effects 0.000 claims description 15
• TXILQOPEAQHTBA-UHFFFAOYSA-N n-cyclopropyl-4-(8-methylsulfonyl-6-phenylimidazo[1,2-a]pyrazin-3-yl)benzamide Chemical compound C=1N=C2C(S(=O)(=O)C)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 TXILQOPEAQHTBA-UHFFFAOYSA-N 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 14
• 150000001204 N-oxides Chemical class 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 230000002265 prevention Effects 0.000 claims description 8
• 230000009401 metastasis Effects 0.000 claims description 7
• 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 description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
• 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 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
• 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
• 230000006806 disease prevention Effects 0.000 claims description 4
• 229930013356 epothilone Natural products 0.000 claims description 4
• 150000003883 epothilone derivatives Chemical class 0.000 claims description 4
• NKIRJIJEJNGXHL-UHFFFAOYSA-N 4-(6-bromo-8-methylsulfanylimidazo[1,2-a]pyrazin-3-yl)-n-cyclopropylbenzamide Chemical compound C=1N=C2C(SC)=NC(Br)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 NKIRJIJEJNGXHL-UHFFFAOYSA-N 0.000 claims description 3
• IDRWISSEXBWWKB-UHFFFAOYSA-N 4-(8-butylsulfanyl-6-phenylimidazo[1,2-a]pyrazin-3-yl)-n-cyclopropylbenzamide Chemical compound C=1N=C2C(SCCCC)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 IDRWISSEXBWWKB-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
• 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
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-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
• 229940123237 Taxane Drugs 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
• 229960000684 cytarabine Drugs 0.000 claims description 3
• 229960003668 docetaxel Drugs 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
• 229960002949 fluorouracil Drugs 0.000 claims description 3
• 229960000908 idarubicin Drugs 0.000 claims description 3
• 230000001404 mediated effect Effects 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
• 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
• 229960001156 mitoxantrone Drugs 0.000 claims description 3
• KHYYDBOJAJOGDO-UHFFFAOYSA-N n-cyclopropyl-4-(8-ethylsulfanyl-6-phenylimidazo[1,2-a]pyrazin-3-yl)benzamide Chemical compound C=1N=C2C(SCC)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 KHYYDBOJAJOGDO-UHFFFAOYSA-N 0.000 claims description 3
• RZVCKJUHTUVKEW-UHFFFAOYSA-N n-cyclopropyl-4-(8-methylsulfanyl-6-phenylimidazo[1,2-a]pyrazin-3-yl)benzamide Chemical compound C=1N=C2C(SC)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 RZVCKJUHTUVKEW-UHFFFAOYSA-N 0.000 claims description 3
• IXXKUJAASUWHGP-UHFFFAOYSA-N tert-butyl n-[2-[3-[4-(cyclopropylcarbamoyl)phenyl]-6-phenylimidazo[1,2-a]pyrazin-8-yl]sulfanylethyl]carbamate Chemical compound C=1N=C2C(SCCNC(=O)OC(C)(C)C)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 IXXKUJAASUWHGP-UHFFFAOYSA-N 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
• 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
• CJFQCFRTZUDOFX-UHFFFAOYSA-N 2-[4-[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-8-methylsulfanylimidazo[1,2-a]pyrazin-6-yl]phenyl]ethanol Chemical compound C=1N=C2C(SC)=NC(C=3C=CC(CCO)=CC=3)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 CJFQCFRTZUDOFX-UHFFFAOYSA-N 0.000 claims description 2
• HZVLASCHPLSLBB-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-(4-ethenylphenyl)-8-methylsulfanylimidazo[1,2-a]pyrazine Chemical compound C=1N=C2C(SC)=NC(C=3C=CC(C=C)=CC=3)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 HZVLASCHPLSLBB-UHFFFAOYSA-N 0.000 claims description 2
• HTGAVFKNHNDUIQ-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-8-methylsulfanyl-6-phenylimidazo[1,2-a]pyrazine Chemical compound C=1N=C2C(SC)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 HTGAVFKNHNDUIQ-UHFFFAOYSA-N 0.000 claims description 2
• HVRRMGYCTNBKBG-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-8-methylsulfanyl-6-pyridin-4-ylimidazo[1,2-a]pyrazine Chemical compound C=1N=C2C(SC)=NC(C=3C=CN=CC=3)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 HVRRMGYCTNBKBG-UHFFFAOYSA-N 0.000 claims description 2
• WUGXJCOUMCFTSN-UHFFFAOYSA-N 4-(6-bromo-8-methylsulfonylimidazo[1,2-a]pyrazin-3-yl)-n-cyclopropylbenzamide Chemical compound C=1N=C2C(S(=O)(=O)C)=NC(Br)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 WUGXJCOUMCFTSN-UHFFFAOYSA-N 0.000 claims description 2
• BDQFRDXIOGEWQL-UHFFFAOYSA-N 4-(8-butylsulfinyl-6-phenylimidazo[1,2-a]pyrazin-3-yl)-n-cyclopropylbenzamide Chemical compound C=1N=C2C(S(=O)CCCC)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 BDQFRDXIOGEWQL-UHFFFAOYSA-N 0.000 claims description 2
• CPBCEJZCAZPZPM-UHFFFAOYSA-N 4-(8-butylsulfonyl-6-phenylimidazo[1,2-a]pyrazin-3-yl)-n-cyclopropylbenzamide Chemical compound C=1N=C2C(S(=O)(=O)CCCC)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 CPBCEJZCAZPZPM-UHFFFAOYSA-N 0.000 claims description 2
• VMUXBUYKAGHSRR-UHFFFAOYSA-N 4-[8-(2-aminoethylsulfanyl)-6-phenylimidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(SCCN)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 VMUXBUYKAGHSRR-UHFFFAOYSA-N 0.000 claims description 2
• FROUDDSNSUOWFM-UHFFFAOYSA-N 4-[8-(2-aminoethylsulfonyl)-6-phenylimidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(S(=O)(=O)CCN)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 FROUDDSNSUOWFM-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
• 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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• 229960000975 daunorubicin Drugs 0.000 claims description 2
• 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
• 229960004679 doxorubicin Drugs 0.000 claims description 2
• 229960001842 estramustine Drugs 0.000 claims description 2
• 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 description 2
• 229960000390 fludarabine Drugs 0.000 claims description 2
• GFJDNEOCSLOIPG-UHFFFAOYSA-N n-[2-[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-phenylimidazo[1,2-a]pyrazin-8-yl]sulfanylethyl]acetamide Chemical compound C=1N=C2C(SCCNC(=O)C)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 GFJDNEOCSLOIPG-UHFFFAOYSA-N 0.000 claims description 2
• KMYPWGAYBHUAMT-UHFFFAOYSA-N n-cyclopropyl-4-(8-methylsulfinyl-6-phenylimidazo[1,2-a]pyrazin-3-yl)benzamide Chemical compound C=1N=C2C(S(=O)C)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 KMYPWGAYBHUAMT-UHFFFAOYSA-N 0.000 claims description 2
• AUIYCKXTCBSVSZ-UHFFFAOYSA-N n-cyclopropyl-4-[8-[s-methyl-n-(2,2,2-trifluoroacetyl)sulfonimidoyl]-6-phenylimidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(S(=O)(=NC(=O)C(F)(F)F)C)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 AUIYCKXTCBSVSZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
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• 125000004432 carbon atom Chemical group C* 0.000 description 25
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• 239000002904 solvent Substances 0.000 description 24
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