ES2555261T3 - Imidazopirazinas sustituidas - Google Patents
Imidazopirazinas sustituidas Download PDFInfo
- Publication number
- ES2555261T3 ES2555261T3 ES11725886.3T ES11725886T ES2555261T3 ES 2555261 T3 ES2555261 T3 ES 2555261T3 ES 11725886 T ES11725886 T ES 11725886T ES 2555261 T3 ES2555261 T3 ES 2555261T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- imidazo
- pyrazin
- amino
- cyclopropyl
- 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.)
- Active
Links
- 150000005235 imidazopyrazines Chemical group 0.000 title description 3
- -1 cyano- Chemical class 0.000 claims abstract description 282
- 150000001875 compounds Chemical class 0.000 claims abstract description 260
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 127
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 60
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 35
- 125000005843 halogen group Chemical group 0.000 claims abstract description 33
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 239000012453 solvate Substances 0.000 claims abstract description 19
- 125000001424 substituent group Chemical group 0.000 claims abstract description 18
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 12
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 113
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 89
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 66
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000011321 prophylaxis Methods 0.000 claims description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 9
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 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 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 229960004063 propylene glycol Drugs 0.000 claims description 7
- 235000013772 propylene glycol Nutrition 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229960001592 paclitaxel Drugs 0.000 claims description 6
- 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 description 6
- 229930012538 Paclitaxel Natural products 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-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
- 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 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
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 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
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-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
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229960004562 carboplatin 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
- 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
- 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 3
- 229960003668 docetaxel Drugs 0.000 claims description 3
- 229930013356 epothilone Natural products 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
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 3
- 229960001101 ifosfamide Drugs 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
- 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
- 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
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 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
- 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
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004146 Propane-1,2-diol Substances 0.000 claims description 2
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- 150000001345 alkine derivatives Chemical class 0.000 claims description 2
- 125000005055 alkyl alkoxy group Chemical group 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
- 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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- 229960004679 doxorubicin Drugs 0.000 claims description 2
- 150000003883 epothilone derivatives Chemical class 0.000 claims description 2
- 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 2
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- 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 2
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- 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
- 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
- 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 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
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Hematology (AREA)
- Pain & Pain Management (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10164587 | 2010-06-01 | ||
| EP10164587 | 2010-06-01 | ||
| PCT/EP2011/058713 WO2011151259A1 (en) | 2010-06-01 | 2011-05-27 | Substituted imidazopyrazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2555261T3 true ES2555261T3 (es) | 2015-12-30 |
Family
ID=44359555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11725886.3T Active ES2555261T3 (es) | 2010-06-01 | 2011-05-27 | Imidazopirazinas sustituidas |
Country Status (7)
| Country | Link |
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| US (1) | US9199999B2 (enExample) |
| EP (1) | EP2576560B1 (enExample) |
| JP (1) | JP5824040B2 (enExample) |
| CN (1) | CN103038235B (enExample) |
| CA (1) | CA2801031A1 (enExample) |
| ES (1) | ES2555261T3 (enExample) |
| WO (1) | WO2011151259A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| US9212184B2 (en) * | 2010-12-17 | 2015-12-15 | Bayer Intellectual Property Gmbh | 6-thio-substituted imidazo[1,2-a]pyrazines as Mps-1 inhibitors |
| CA2821834A1 (en) * | 2010-12-17 | 2012-06-21 | Bayer Intellectual Property Gmbh | 6 substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| WO2012080236A1 (en) * | 2010-12-17 | 2012-06-21 | Bayer Pharma Aktiengesellschaft | 6-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| ES2556458T3 (es) * | 2010-12-17 | 2016-01-18 | Bayer Intellectual Property Gmbh | 6-Imidazopirazinas sustituidas para uso como inhibidores de Mps-1 y TKK en el tratamiento de trastornos hiperproliferativos |
| WO2013135612A1 (en) | 2012-03-14 | 2013-09-19 | Bayer Intellectual Property Gmbh | Substituted imidazopyridazines |
| WO2014020041A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| WO2014020043A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| AU2013344716B2 (en) | 2012-11-16 | 2018-03-01 | University Health Network | Pyrazolopyrimidine compounds |
| EA029372B1 (ru) * | 2013-11-15 | 2018-03-30 | Юниверсити Хелс Нетуорк | Пиразолопиримидиновые соединения |
| WO2016166255A1 (en) | 2015-04-17 | 2016-10-20 | Netherlands Translational Research Center B.V. | Prognostic biomarkers for ttk inhibitor chemotherapy |
| WO2019245590A1 (en) | 2018-06-18 | 2019-12-26 | Avista Pharma Solutions, Inc. | Chemical compounds |
| EP3917932A4 (en) | 2019-01-30 | 2022-09-28 | Avista Pharma Solutions, Inc. | CHEMICAL COMPOUNDS |
| CA3128346A1 (en) | 2019-01-30 | 2020-08-06 | Avista Pharma Solutions, Inc. | Synthetic process and novel intermediates |
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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 |
| US7576085B2 (en) | 2002-09-23 | 2009-08-18 | Schering Corporation | Imidazopyrazines as cyclin dependent kinase inhibitors |
| TW200413378A (en) | 2002-09-23 | 2004-08-01 | Schering Corp | Novel imidazopyrazines as cyclin dependent kinase inhibitors |
| US7157460B2 (en) | 2003-02-20 | 2007-01-02 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| US7186832B2 (en) | 2003-02-20 | 2007-03-06 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| EP1945216A1 (en) | 2005-11-10 | 2008-07-23 | Schering Corporation | Methods for inhibiting protein kinases |
| WO2007058942A2 (en) * | 2005-11-10 | 2007-05-24 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| 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 |
| MX2008015747A (es) * | 2006-06-06 | 2008-12-19 | Schering Corp | Imidazopirazinas como inhibidores de la proteina quinasa. |
| JP5600004B2 (ja) | 2006-09-05 | 2014-10-01 | エモリー ユニバーシティー | 感染の予防または治療のためのチロシンキナーゼ阻害剤 |
| WO2008030795A2 (en) | 2006-09-05 | 2008-03-13 | Boards Of Regents, The University Of Texas System | Compositions and methods for inhibition of tyrosine kinases |
| AR063581A1 (es) * | 2006-11-08 | 2009-02-04 | Schering Corp | Imidazopirazinas como inhibidores de proteina quinasa |
| US20100298314A1 (en) | 2006-12-20 | 2010-11-25 | Schering Corporation | Novel jnk inhibitors |
| CA2690557A1 (en) * | 2007-06-14 | 2008-12-24 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| AU2008282885A1 (en) | 2007-07-31 | 2009-02-05 | Schering Corporation | Anti-mitotic agent and aurora kinase inhibitor combination as anti-cancer treatment |
| 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 |
| JP2010111624A (ja) * | 2008-11-06 | 2010-05-20 | Shionogi & Co Ltd | Ｔｔｋ阻害作用を有するインダゾール誘導体 |
| GB0822981D0 (en) * | 2008-12-17 | 2009-01-21 | Summit Corp Plc | Compounds for treatment of duchenne muscular dystrophy |
| JP6168773B2 (ja) | 2009-04-29 | 2017-07-26 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換イミダゾキノキサリン |
| TW201107329A (en) * | 2009-07-30 | 2011-03-01 | Oncotherapy Science Inc | Fused imidazole derivative having ttk inhibitory action |
| WO2011026579A1 (en) | 2009-09-04 | 2011-03-10 | Bayer Schering Pharma Aktiengesellschaft | Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors |
| AU2010326268B2 (en) * | 2009-12-04 | 2016-11-03 | Senhwa Biosciences, Inc. | Pyrazolopyrimidines and related heterocycles as CK2 inhibitors |
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2011
- 2011-05-27 EP EP11725886.3A patent/EP2576560B1/en active Active
- 2011-05-27 CA CA2801031A patent/CA2801031A1/en not_active Abandoned
- 2011-05-27 ES ES11725886.3T patent/ES2555261T3/es active Active
- 2011-05-27 JP JP2013512850A patent/JP5824040B2/ja not_active Expired - Fee Related
- 2011-05-27 WO PCT/EP2011/058713 patent/WO2011151259A1/en not_active Ceased
- 2011-05-27 US US13/700,956 patent/US9199999B2/en not_active Expired - Fee Related
- 2011-05-27 CN CN201180038047.1A patent/CN103038235B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US9199999B2 (en) | 2015-12-01 |
| JP5824040B2 (ja) | 2015-11-25 |
| JP2013528610A (ja) | 2013-07-11 |
| WO2011151259A1 (en) | 2011-12-08 |
| EP2576560A1 (en) | 2013-04-10 |
| CA2801031A1 (en) | 2011-12-08 |
| US20130210815A1 (en) | 2013-08-15 |
| CN103038235A (zh) | 2013-04-10 |
| HK1179249A1 (en) | 2013-09-27 |
| CN103038235B (zh) | 2015-07-29 |
| EP2576560B1 (en) | 2015-09-30 |
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