JP5775871B2 - ヘテロ環式オキシム化合物 - Google Patents
ヘテロ環式オキシム化合物 Download PDFInfo
- Publication number
- JP5775871B2 JP5775871B2 JP2012525167A JP2012525167A JP5775871B2 JP 5775871 B2 JP5775871 B2 JP 5775871B2 JP 2012525167 A JP2012525167 A JP 2012525167A JP 2012525167 A JP2012525167 A JP 2012525167A JP 5775871 B2 JP5775871 B2 JP 5775871B2
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- ethanone
- pyridazin
- mmol
- methyl
- 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.)
- Expired - Fee Related
Links
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- 125000001424 substituent group Chemical group 0.000 claims description 44
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 229920006395 saturated elastomer Polymers 0.000 claims description 30
- 229910052805 deuterium Inorganic materials 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
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- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
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- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 11
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- YFCXQUJKPIVRBF-STBIYBPSSA-N 2-[(e)-1-[3-[[3-(4-methylpiperazin-1-yl)quinolin-6-yl]methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]oxyethanol Chemical compound C1CN(C)CCN1C1=CN=C(C=CC(CC=2N3N=C(C=CC3=NN=2)C(\C)=N\OCCO)=C2)C2=C1 YFCXQUJKPIVRBF-STBIYBPSSA-N 0.000 claims description 5
- SAJJGVDFEGSGMW-RPPGKUMJSA-N 2-[(e)-1-[3-[difluoro(quinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]oxyethanol Chemical compound N1=CC=CC2=CC(C(F)(F)C3=NN=C4C=CC(=NN43)C(=N/OCCO)/C)=CC=C21 SAJJGVDFEGSGMW-RPPGKUMJSA-N 0.000 claims description 5
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- 125000002950 monocyclic group Chemical group 0.000 claims description 4
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- FZENGILVLUJGJX-UHFFFAOYSA-N acetaldehyde oxime Chemical compound CC=NO FZENGILVLUJGJX-UHFFFAOYSA-N 0.000 claims description 3
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- XNFDWVKEAJHRAH-PWIIRVQRSA-N (NE)-N-[1-[3-[(1R)-1-(5,7-difluoroquinolin-6-yl)ethyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylidene]hydroxylamine Chemical compound N1=CC=CC2=C(F)C([C@H](C=3N4N=C(C=CC4=NN=3)C(\C)=N\O)C)=C(F)C=C21 XNFDWVKEAJHRAH-PWIIRVQRSA-N 0.000 claims description 2
- BRFNRXMYOPKJPW-PGGKNCGUSA-N (NE)-N-[1-[3-[(5,7-difluoroquinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylidene]hydroxylamine Chemical compound N1=CC=CC2=C(F)C(CC3=NN=C4C=CC(=NN43)C(=N/O)/C)=C(F)C=C21 BRFNRXMYOPKJPW-PGGKNCGUSA-N 0.000 claims description 2
- NECGVPOFFRUOAT-LUOAPIJWSA-N (e)-1-[3-[(5,7-difluoroquinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-n-(2-fluoroethoxy)ethanimine Chemical compound N1=CC=CC2=C(F)C(CC3=NN=C4C=CC(=NN43)C(=N/OCCF)/C)=C(F)C=C21 NECGVPOFFRUOAT-LUOAPIJWSA-N 0.000 claims description 2
- SXXYIJSASWDISL-BRJLIKDPSA-N 2-[(e)-1-[3-[(5-fluoroquinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]oxyethanol Chemical compound N1=CC=CC2=C(F)C(CC3=NN=C4C=CC(=NN43)C(=N/OCCO)/C)=CC=C21 SXXYIJSASWDISL-BRJLIKDPSA-N 0.000 claims description 2
- JUWNDJASLZSLMP-BRJLIKDPSA-N 2-[(e)-1-[3-[(7-fluoroquinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]oxyethanol Chemical compound C1=CN=C2C=C(F)C(CC3=NN=C4C=CC(=NN43)C(=N/OCCO)/C)=CC2=C1 JUWNDJASLZSLMP-BRJLIKDPSA-N 0.000 claims description 2
- LGLDQGOCKHCCSQ-KKMKTNMSSA-N 3-[(e)-1-[3-[(5,7-difluoroquinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]oxypropan-1-ol Chemical compound N1=CC=CC2=C(F)C(CC3=NN=C4C=CC(=NN43)C(=N/OCCCO)/C)=C(F)C=C21 LGLDQGOCKHCCSQ-KKMKTNMSSA-N 0.000 claims description 2
- BFKVBBCTXJHDSX-XODNFHPESA-N 4-[(e)-1-[3-[(5,7-difluoroquinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]oxybutan-1-ol Chemical compound N1=CC=CC2=C(F)C(CC3=NN=C4C=CC(=NN43)C(=N/OCCCCO)/C)=C(F)C=C21 BFKVBBCTXJHDSX-XODNFHPESA-N 0.000 claims description 2
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- YWAXTNRXOLQHMU-HRNIQNSLSA-N [(e)-1-[3-[(1r)-1-(5,7-difluoroquinolin-6-yl)ethyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino] carbamate Chemical compound N1=CC=CC2=C(F)C([C@H](C=3N4N=C(C=CC4=NN=3)C(\C)=N\OC(N)=O)C)=C(F)C=C21 YWAXTNRXOLQHMU-HRNIQNSLSA-N 0.000 claims description 2
- YWAXTNRXOLQHMU-ILEJBRPTSA-N [(e)-1-[3-[(1s)-1-(5,7-difluoroquinolin-6-yl)ethyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino] carbamate Chemical compound N1=CC=CC2=C(F)C([C@@H](C=3N4N=C(C=CC4=NN=3)C(\C)=N\OC(N)=O)C)=C(F)C=C21 YWAXTNRXOLQHMU-ILEJBRPTSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
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- JLJSJVGAIRCSCT-ZMOGYAJESA-N (e)-n-ethoxy-1-[3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethanimine Chemical compound N1=CC=CC2=CC(CC3=NN=C4C=CC(=NN43)C(/C)=N/OCC)=CC=C21 JLJSJVGAIRCSCT-ZMOGYAJESA-N 0.000 claims 2
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- TYELNEXHOJMZBY-XODNFHPESA-N (e)-1-[3-[1-(5,7-difluoroquinolin-6-yl)ethyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-n-(2-methoxyethoxy)ethanimine Chemical compound N1=CC=CC2=C(F)C(C(C)C3=NN=C4C=CC(=NN43)C(/C)=N/OCCOC)=C(F)C=C21 TYELNEXHOJMZBY-XODNFHPESA-N 0.000 claims 1
- MQFWBFIXBQBIIU-YEAWRNRESA-N (e)-n-(cyclopropylmethoxy)-1-[3-[(1s)-1-(5,7-difluoroquinolin-6-yl)ethyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethanimine Chemical compound N=1N2C([C@@H](C)C=3C(=C4C=CC=NC4=CC=3F)F)=NN=C2C=CC=1C(\C)=N\OCC1CC1 MQFWBFIXBQBIIU-YEAWRNRESA-N 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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EP2464649A1 (en) | 2009-08-12 | 2012-06-20 | Novartis AG | Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation |
PL2719699T3 (pl) | 2009-12-31 | 2016-01-29 | Hutchison Medipharma Ltd | Pewne triazolopirazyny, ich kompozycje i sposoby ich stosowania |
WO2011145035A1 (en) | 2010-05-17 | 2011-11-24 | Indian Incozen Therapeutics Pvt. Ltd. | Novel 3,5-disubstitued-3h-imidazo[4,5-b]pyridine and 3,5- disubstitued -3h-[1,2,3]triazolo[4,5-b] pyridine compounds as modulators of protein kinases |
CN103459396B (zh) * | 2011-02-10 | 2015-08-19 | 诺瓦提斯公司 | 作为c-Met酪氨酸激酶抑制剂的[1,2,4]三唑并[4,3-b]哒嗪化合物 |
JP2014505088A (ja) * | 2011-02-10 | 2014-02-27 | ノバルティス アーゲー | C−METチロシンキナーゼ阻害剤としての[1,2,4]トリアゾロ[4,3−b]ピリダジン化合物 |
CN103958509B (zh) * | 2011-09-15 | 2015-12-23 | 诺华股份有限公司 | 作为酪氨酸激酶抑制剂的6-取代的3-(喹啉-6-基硫代)-[1,2,4]三唑并[4,3-a]吡啶化合物 |
UY34329A (es) * | 2011-09-15 | 2013-04-30 | Novartis Ag | Compuestos de triazolopiridina |
US9375009B2 (en) | 2011-12-27 | 2016-06-28 | Bayer Intellectual Property Gmbh | Heteroarylpiperidine and piperazine derivatives as fungicides |
KR20150070348A (ko) | 2012-10-16 | 2015-06-24 | 얀센 파마슈티카 엔.브이. | RoRγt의 헤테로아릴 결합 퀴놀리닐 조절제 |
SG11201502935VA (en) | 2012-10-16 | 2015-09-29 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of ror-gamma-t |
BR112015008308A2 (pt) | 2012-10-16 | 2017-12-05 | Janssen Pharmaceutica Nv | moduladores de quinolinila ligados por metileno do ror-gama-t |
EP2917210B1 (en) | 2012-11-06 | 2019-02-27 | Shanghai Fochon Pharmaceutical Co. Ltd | Alk kinase inhibitors |
US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
JP6423423B2 (ja) | 2013-10-15 | 2018-11-14 | ヤンセン ファーマシューティカ エヌ.ベー. | Rorγtのアルキル結合キノリニルモジュレーター |
US9403816B2 (en) | 2013-10-15 | 2016-08-02 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of RORγt |
US9284308B2 (en) | 2013-10-15 | 2016-03-15 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of RORγt |
KR20160068956A (ko) | 2013-10-15 | 2016-06-15 | 얀센 파마슈티카 엔.브이. | RORyT의 퀴놀리닐 조절제 |
US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
US9328095B2 (en) | 2013-10-15 | 2016-05-03 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORgammat |
GB201321736D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
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- 2010-08-18 WO PCT/EP2010/062057 patent/WO2011020861A1/en active Application Filing
- 2010-08-18 JP JP2012525167A patent/JP5775871B2/ja not_active Expired - Fee Related
- 2010-08-18 AU AU2010284972A patent/AU2010284972A1/en not_active Abandoned
- 2010-08-18 EP EP10762878A patent/EP2467383A1/en not_active Withdrawn
- 2010-08-18 BR BR112012008061A patent/BR112012008061A2/pt not_active Application Discontinuation
- 2010-08-18 KR KR1020127007032A patent/KR20120089463A/ko not_active Application Discontinuation
- 2010-08-18 MX MX2012002179A patent/MX2012002179A/es not_active Application Discontinuation
- 2010-08-18 EA EA201200318A patent/EA201200318A1/ru unknown
- 2010-08-18 IN IN1453DEN2012 patent/IN2012DN01453A/en unknown
- 2010-08-19 TW TW099127805A patent/TW201113284A/zh unknown
- 2010-08-19 UY UY0001032848A patent/UY32848A/es unknown
- 2010-08-19 US US12/859,653 patent/US8410264B2/en not_active Expired - Fee Related
- 2010-08-19 AR ARP100103038A patent/AR079486A1/es unknown
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2012
- 2012-08-06 US US13/567,386 patent/US8507676B2/en not_active Expired - Fee Related
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US8410264B2 (en) | 2013-04-02 |
EP2467383A1 (en) | 2012-06-27 |
WO2011020861A1 (en) | 2011-02-24 |
BR112012008061A2 (pt) | 2016-03-01 |
AR079486A1 (es) | 2012-02-01 |
US8507676B2 (en) | 2013-08-13 |
CA2771432A1 (en) | 2011-02-24 |
US20110065708A1 (en) | 2011-03-17 |
TW201113284A (en) | 2011-04-16 |
KR20120089463A (ko) | 2012-08-10 |
MX2012002179A (es) | 2012-03-16 |
AU2010284972A1 (en) | 2012-03-08 |
UY32848A (es) | 2011-03-31 |
IN2012DN01453A (US07122547-20061017-C00074.png) | 2015-06-05 |
JP2013502396A (ja) | 2013-01-24 |
US20120302570A1 (en) | 2012-11-29 |
EA201200318A1 (ru) | 2012-09-28 |
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