JP2013522275A5 - - Google Patents
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- Publication number
- JP2013522275A5 JP2013522275A5 JP2012557540A JP2012557540A JP2013522275A5 JP 2013522275 A5 JP2013522275 A5 JP 2013522275A5 JP 2012557540 A JP2012557540 A JP 2012557540A JP 2012557540 A JP2012557540 A JP 2012557540A JP 2013522275 A5 JP2013522275 A5 JP 2013522275A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazin
- cyclopropyl
- alkyl
- phenylimidazo
- benzamide
- Prior art date
- 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.)
- Granted
Links
- 229940123237 Taxane Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 24
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 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
- 150000001875 compounds Chemical class 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 230000024932 T cell mediated immunity Effects 0.000 claims 3
- 230000010261 cell growth Effects 0.000 claims 3
- 230000004663 cell proliferation Effects 0.000 claims 3
- 230000001413 cellular effect Effects 0.000 claims 3
- 230000028709 inflammatory response Effects 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 230000004083 survival effect Effects 0.000 claims 3
- -1 (RS) tert-butyl [2-({3- [4- (cyclopropylcarbamoyl) phenyl] -6-phenylimidazo [1,2-a] pyrazin-8-yl} sulfinyl) ethyl] Chemical class 0.000 claims 2
- 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 2
- 229930012538 Paclitaxel Natural products 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 229960001592 paclitaxel Drugs 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 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 1
- 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
- AMVYPPAWUFGVKM-UHFFFAOYSA-N 3-[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-8-methylsulfanylimidazo[1,2-a]pyrazin-6-yl]prop-2-yn-1-ol Chemical compound C=1N=C2C(SC)=NC(C#CCO)=CN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 AMVYPPAWUFGVKM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 108010006654 Bleomycin Proteins 0.000 claims 1
- 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 1
- 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 1
- 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 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 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 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 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 1
- 229940009456 adriamycin Drugs 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000002280 anti-androgenic effect Effects 0.000 claims 1
- 239000000051 antiandrogen Substances 0.000 claims 1
- 229960001561 bleomycin Drugs 0.000 claims 1
- 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 1
- 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 1
- 229960001467 bortezomib Drugs 0.000 claims 1
- 229960004117 capecitabine Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229960004397 cyclophosphamide Drugs 0.000 claims 1
- 229960000684 cytarabine Drugs 0.000 claims 1
- 229960000975 daunorubicin Drugs 0.000 claims 1
- 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 1
- 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 1
- 229960003957 dexamethasone Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 229960003668 docetaxel Drugs 0.000 claims 1
- 229960004679 doxorubicin Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 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
- 229960001842 estramustine Drugs 0.000 claims 1
- 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 1
- 229960005420 etoposide Drugs 0.000 claims 1
- 229960000390 fludarabine Drugs 0.000 claims 1
- 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 1
- 229960002949 fluorouracil Drugs 0.000 claims 1
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229960000908 idarubicin Drugs 0.000 claims 1
- 229960001101 ifosfamide Drugs 0.000 claims 1
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 229960001924 melphalan Drugs 0.000 claims 1
- 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 1
- 230000009401 metastasis Effects 0.000 claims 1
- 229960001156 mitoxantrone Drugs 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims 1
- 229960000624 procarbazine Drugs 0.000 claims 1
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- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims 1
- 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 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 229960003087 tioguanine Drugs 0.000 claims 1
- 229960003048 vinblastine Drugs 0.000 claims 1
- 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 1
- 229960004528 vincristine Drugs 0.000 claims 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 1
- 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 1
- 210000004027 cell Anatomy 0.000 description 2
- 230000030833 cell death Effects 0.000 description 2
- 230000011278 mitosis Effects 0.000 description 2
- 0 *c1ncc[n]1 Chemical compound *c1ncc[n]1 0.000 description 1
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| TWI541243B (zh) | 2010-09-10 | 2016-07-11 | 拜耳知識產權公司 | 經取代咪唑并嗒 |
| CA2821819A1 (en) * | 2010-12-17 | 2012-06-21 | Marcus Koppitz | 6-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| ES2544609T3 (es) * | 2010-12-17 | 2015-09-02 | Bayer Intellectual Property Gmbh | Imidazopirazinas 2-sustituidas para uso como inhibidores de Mps-1 y TTK en el tratamiento de trastornos hiper-proliferativos |
| EP2651944B1 (en) * | 2010-12-17 | 2015-09-23 | Bayer Intellectual Property GmbH | Substituted 6-imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| WO2014020043A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| WO2014020041A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| EP3392244A1 (en) | 2014-02-13 | 2018-10-24 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| NZ723203A (en) | 2014-02-13 | 2020-08-28 | Incyte Corp | Cyclopropylamines as lsd1 inhibitors |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| KR102421235B1 (ko) | 2014-02-13 | 2022-07-15 | 인사이트 코포레이션 | Lsd1 저해제로서 사이클로프로필아민 |
| US9695180B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,2-a]pyrazines as LSD1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
| WO2016007731A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyridines and imidazopyrazines as lsd1 inhibitors |
| UA122688C2 (uk) | 2015-04-03 | 2020-12-28 | Інсайт Корпорейшн | Гетероциклічні сполуки як інгібітори lsd1 |
| EP3283642B1 (en) | 2015-04-17 | 2023-10-11 | Netherlands Translational Research Center Holding B.V. | Prognostic biomarkers for ttk inhibitor chemotherapy |
| JP7427363B2 (ja) | 2015-08-12 | 2024-02-05 | インサイト・ホールディングス・コーポレイション | Ｌｓｄ１阻害剤の塩 |
| US10166221B2 (en) | 2016-04-22 | 2019-01-01 | Incyte Corporation | Formulations of an LSD1 inhibitor |
| US10239885B1 (en) | 2018-06-18 | 2019-03-26 | Avista Pharma Solutions, Inc. | Compound 1-[2-[4-(2-ethyl-6,8-dimethylimidazo[1,2-α]pyrazin-3-yl)phenyl]ethyl]-3-(p-tolylsulfonyl)urea as a prostaglandin EP4 receptor antagonist |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| EP3917935A4 (en) | 2019-01-30 | 2022-11-16 | Avista Pharma Solutions, Inc. | SYNTHESIS PROCESS AND NEW INTERMEDIATES |
| US11459331B2 (en) | 2019-01-30 | 2022-10-04 | Avista Pharma Solutions, Inc. | Chemical compounds |
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| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| DE60317353T2 (de) | 2002-09-23 | 2008-08-28 | Schering Corp. | Imidazopyrazine als cdk-inhibitoren |
| US7576085B2 (en) | 2002-09-23 | 2009-08-18 | Schering Corporation | Imidazopyrazines as cyclin dependent kinase inhibitors |
| CA2628455A1 (en) | 2005-11-10 | 2007-05-24 | Merck Sharp & Dohme Corp. | Imidazopyrazines as protein kinase inhibitors |
| TW200803863A (en) | 2005-11-10 | 2008-01-16 | Schering Corp | Method for inhibiting protein kinases |
| US7893058B2 (en) | 2006-05-15 | 2011-02-22 | Janssen Pharmaceutica Nv | Imidazolopyrazine compounds useful for the treatment of degenerative and inflammatory diseases |
| US20090175852A1 (en) | 2006-06-06 | 2009-07-09 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| CA2654202A1 (en) | 2006-06-06 | 2007-12-21 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| EP2471529A3 (en) | 2006-09-05 | 2012-10-10 | Emory University | Kinase Inhibitors for Preventing or Treating Pathogen Infection and Method of Use Thereof |
| EP2079746A2 (en) | 2006-11-08 | 2009-07-22 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| WO2008082490A2 (en) | 2006-12-20 | 2008-07-10 | Schering Corporation | Novel jnk inhibitors |
| GB0716292D0 (en) | 2007-08-21 | 2007-09-26 | Biofocus Dpi Ltd | Imidazopyrazine compounds |
| CA2710929A1 (en) | 2008-01-28 | 2009-08-06 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| GB0822981D0 (en) * | 2008-12-17 | 2009-01-21 | Summit Corp Plc | Compounds for treatment of duchenne muscular dystrophy |
| TW201107329A (en) * | 2009-07-30 | 2011-03-01 | Oncotherapy Science Inc | Fused imidazole derivative having ttk inhibitory action |
-
2011
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- 2011-03-16 CN CN201180024369.0A patent/CN102971321B/zh not_active Expired - Fee Related
- 2011-03-16 JP JP2012557540A patent/JP5841078B2/ja not_active Expired - Fee Related
- 2011-03-16 EP EP11708301.4A patent/EP2547680B1/en active Active
- 2011-03-16 CA CA2793279A patent/CA2793279A1/en not_active Abandoned
- 2011-03-16 WO PCT/EP2011/053967 patent/WO2011113862A1/en not_active Ceased
- 2011-03-16 US US13/635,734 patent/US9468642B2/en not_active Expired - Fee Related
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