JP2016516670A5 - - Google Patents
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- Publication number
- JP2016516670A5 JP2016516670A5 JP2015559311A JP2015559311A JP2016516670A5 JP 2016516670 A5 JP2016516670 A5 JP 2016516670A5 JP 2015559311 A JP2015559311 A JP 2015559311A JP 2015559311 A JP2015559311 A JP 2015559311A JP 2016516670 A5 JP2016516670 A5 JP 2016516670A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- alkali metal
- base
- copper catalyst
- 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
- 238000000034 method Methods 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 21
- 239000010949 copper Substances 0.000 claims 14
- 239000002585 base Substances 0.000 claims 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 8
- -1 alkali metal bicarbonate Chemical class 0.000 claims 8
- 239000003054 catalyst Substances 0.000 claims 8
- 229910052802 copper Inorganic materials 0.000 claims 8
- OJTMHIMQUQOLJV-UHFFFAOYSA-N 2,5-difluorobenzonitrile Chemical compound FC1=CC=C(F)C(C#N)=C1 OJTMHIMQUQOLJV-UHFFFAOYSA-N 0.000 claims 4
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 4
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 4
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 4
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims 4
- 239000012535 impurity Substances 0.000 claims 4
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
- 229910000318 alkali metal phosphate Inorganic materials 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 2
- 150000004985 diamines Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 125000002560 nitrile group Chemical group 0.000 claims 2
- DCKPHSCJNMZJON-UHFFFAOYSA-N 2-[5-[2-(aminomethyl)phenoxy]indazol-1-yl]ethanol Chemical compound NCC1=CC=CC=C1OC1=CC=C(N(CCO)N=C2)C2=C1 DCKPHSCJNMZJON-UHFFFAOYSA-N 0.000 claims 1
- MNRQFKJOIVOQQH-UHFFFAOYSA-N 2-[5-[4-fluoro-2-(hydroxymethyl)phenoxy]indazol-1-yl]ethanol Chemical compound C=1C=C2N(CCO)N=CC2=CC=1OC1=CC=C(F)C=C1CO MNRQFKJOIVOQQH-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 230000001268 conjugating effect Effects 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361770031P | 2013-02-27 | 2013-02-27 | |
| US61/770,031 | 2013-02-27 | ||
| PCT/US2014/019039 WO2014134313A1 (en) | 2013-02-27 | 2014-02-27 | Intermediates for use in the preparation of indazole derivatives and processes for the preparation thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016516670A JP2016516670A (ja) | 2016-06-09 |
| JP2016516670A5 true JP2016516670A5 (enExample) | 2017-03-23 |
| JP6433922B2 JP6433922B2 (ja) | 2018-12-05 |
Family
ID=50288305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015559311A Active JP6433922B2 (ja) | 2013-02-27 | 2014-02-27 | インダゾール誘導体の調製に使用するための中間体およびその調製方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9790206B2 (enExample) |
| EP (1) | EP2961744B1 (enExample) |
| JP (1) | JP6433922B2 (enExample) |
| CN (1) | CN105073739B (enExample) |
| WO (1) | WO2014134313A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT3691620T (pt) | 2017-10-05 | 2022-10-06 | Fulcrum Therapeutics Inc | Os inibidores da quinase p38 reduzem a expressão de dux4 e genes a jusante para o tratamento de fshd |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL214032B1 (pl) | 2003-03-03 | 2013-06-28 | Array Biopharma | Zwiazki bedace inhibitorami kinazy p38, kompozycja farmaceutyczna je zawierajaca oraz ich zastosowanie do wytwarzania leku do leczenia stanu, w którym posredniczy kinaza p38 |
| WO2007089646A1 (en) * | 2006-01-31 | 2007-08-09 | Array Biopharma Inc. | Kinase inhibitors and methods of use thereof |
| CA2647949A1 (en) * | 2006-03-29 | 2007-11-08 | Array Biopharma Inc. | P38 inhibitors and methods of use thereof |
| TWI365185B (en) * | 2008-07-24 | 2012-06-01 | Lilly Co Eli | Amidophenoxyindazoles useful as inhibitors of c-met |
| KR20120104512A (ko) * | 2009-07-14 | 2012-09-21 | 알바니 몰레큘라 리써치, 인크. | 5-ｈｔ3 수용체 조절체, 이의 제조 방법, 및 그의 용도 |
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2014
- 2014-02-27 CN CN201480009452.4A patent/CN105073739B/zh active Active
- 2014-02-27 EP EP14710725.4A patent/EP2961744B1/en active Active
- 2014-02-27 JP JP2015559311A patent/JP6433922B2/ja active Active
- 2014-02-27 US US14/770,035 patent/US9790206B2/en active Active
- 2014-02-27 WO PCT/US2014/019039 patent/WO2014134313A1/en not_active Ceased