CA2867061A1 - Substituted imidazopyridazines - Google Patents
Substituted imidazopyridazines Download PDFInfo
- Publication number
- CA2867061A1 CA2867061A1 CA 2867061 CA2867061A CA2867061A1 CA 2867061 A1 CA2867061 A1 CA 2867061A1 CA 2867061 CA2867061 CA 2867061 CA 2867061 A CA2867061 A CA 2867061A CA 2867061 A1 CA2867061 A1 CA 2867061A1
- Authority
- CA
- Canada
- Prior art keywords
- cyclopropyl
- alkyl
- trifluoropropyl
- methylbenzamide
- pyridazin
- 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.)
- Abandoned
Links
- 150000005233 imidazopyridazines Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 429
- 238000000034 method Methods 0.000 claims abstract description 108
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 72
- 201000010099 disease Diseases 0.000 claims abstract description 41
- 238000011282 treatment Methods 0.000 claims abstract description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
- 238000011321 prophylaxis Methods 0.000 claims abstract description 18
- -1 hydroxy- Chemical class 0.000 claims description 326
- 239000000203 mixture Substances 0.000 claims description 129
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 101
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 86
- 206010028980 Neoplasm Diseases 0.000 claims description 85
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 81
- 150000003839 salts Chemical class 0.000 claims description 72
- 125000005843 halogen group Chemical group 0.000 claims description 70
- 238000006243 chemical reaction Methods 0.000 claims description 57
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 239000012453 solvate Substances 0.000 claims description 45
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 39
- 150000001204 N-oxides Chemical class 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 27
- 230000004663 cell proliferation Effects 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 230000024932 T cell mediated immunity Effects 0.000 claims description 22
- 230000001413 cellular effect Effects 0.000 claims description 22
- 230000028709 inflammatory response Effects 0.000 claims description 22
- 230000004083 survival effect Effects 0.000 claims description 22
- 230000010261 cell growth Effects 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 206010027476 Metastases Diseases 0.000 claims description 20
- 125000005418 aryl aryl group Chemical group 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
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- 125000003118 aryl group Chemical group 0.000 claims description 17
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
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- 125000004429 atom Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
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- 239000001257 hydrogen Substances 0.000 claims description 8
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- 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 6
- 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 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 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 6
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- 229910052740 iodine Inorganic materials 0.000 claims description 6
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- 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 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 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 5
- 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 5
- 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 5
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- 229960005420 etoposide Drugs 0.000 claims description 5
- 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 5
- 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 5
- 229960002949 fluorouracil Drugs 0.000 claims description 5
- 229960002074 flutamide Drugs 0.000 claims description 5
- 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 5
- 229960000908 idarubicin Drugs 0.000 claims description 5
- 229960001101 ifosfamide Drugs 0.000 claims description 5
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 5
- 229960001924 melphalan Drugs 0.000 claims description 5
- 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 5
- 229960000485 methotrexate Drugs 0.000 claims description 5
- 229960001156 mitoxantrone Drugs 0.000 claims description 5
- 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 5
- RRJAROULOCCCAF-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-2-methoxybenzoyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=C(F)C=CC=C1C(=O)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 RRJAROULOCCCAF-UHFFFAOYSA-N 0.000 claims description 5
- HJKXTKURGJYYPT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorobenzoyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCCC(F)(F)F)C3=NC=2)C(=O)C=2C=C(F)C=CC=2)=CC=C1C(=O)NC1CC1 HJKXTKURGJYYPT-UHFFFAOYSA-N 0.000 claims description 5
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims description 5
- 229960000624 procarbazine Drugs 0.000 claims description 5
- MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims description 5
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- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
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- 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 4
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- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 4
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- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 4
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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 4
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- FIRMDHDGJSBPDU-UHFFFAOYSA-N methyl 3-[4-(cyclopropylcarbamoyl)-3-methylphenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazine-6-carboxylate Chemical compound N12N=C(C(=O)OC)C=C(NCCC(F)(F)F)C2=NC=C1C(C=C1C)=CC=C1C(=O)NC1CC1 FIRMDHDGJSBPDU-UHFFFAOYSA-N 0.000 claims description 4
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A—HUMAN NECESSITIES
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| EP13154139.3 | 2013-02-06 | ||
| PCT/EP2013/054841 WO2013135612A1 (en) | 2012-03-14 | 2013-03-11 | Substituted imidazopyridazines |
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| JP2004346016A (ja) | 2003-05-22 | 2004-12-09 | Otsuka Chemical Co Ltd | トリフルオロメチルキノキサリン化合物、その製造方法、及び有害生物防除剤 |
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| EP1799680A2 (en) | 2004-10-07 | 2007-06-27 | Warner-Lambert Company LLC | Triazolopyridine derivatives as antibacterial agents |
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| HRP20100378T1 (hr) | 2006-05-31 | 2010-08-31 | Galapagos N.V. | Spojevi triazolopirazina učinkoviti za tretman degenerativnih i upalnih bolesti |
| CA2658725A1 (en) | 2006-08-16 | 2008-02-21 | Exelixis, Inc. | Using pi3k and mek modulators in treatments of cancer |
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-
2013
- 2013-03-11 JP JP2014561391A patent/JP6166289B2/ja not_active Expired - Fee Related
- 2013-03-11 ES ES13710986.4T patent/ES2605946T3/es active Active
- 2013-03-11 WO PCT/EP2013/054841 patent/WO2013135612A1/en not_active Ceased
- 2013-03-11 EP EP13710986.4A patent/EP2825540B1/en not_active Not-in-force
- 2013-03-11 CN CN201380024787.9A patent/CN104284896B/zh not_active Expired - Fee Related
- 2013-03-11 US US14/384,828 patent/US9512126B2/en not_active Expired - Fee Related
- 2013-03-11 CA CA 2867061 patent/CA2867061A1/en not_active Abandoned
- 2013-03-13 AR ARP130100808 patent/AR090323A1/es unknown
- 2013-03-14 UY UY0001034677A patent/UY34677A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HK1206022A1 (zh) | 2015-12-31 |
| CN104284896B (zh) | 2016-06-01 |
| AR090323A1 (es) | 2014-11-05 |
| US20150104526A1 (en) | 2015-04-16 |
| CN104284896A (zh) | 2015-01-14 |
| WO2013135612A1 (en) | 2013-09-19 |
| JP2015513559A (ja) | 2015-05-14 |
| EP2825540B1 (en) | 2016-09-14 |
| ES2605946T3 (es) | 2017-03-17 |
| EP2825540A1 (en) | 2015-01-21 |
| JP6166289B2 (ja) | 2017-07-19 |
| UY34677A (es) | 2013-10-31 |
| US9512126B2 (en) | 2016-12-06 |
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