CA2935880A1 - Indazole compounds as irak4 inhibitors - Google Patents
Indazole compounds as irak4 inhibitors Download PDFInfo
- Publication number
- CA2935880A1 CA2935880A1 CA2935880A CA2935880A CA2935880A1 CA 2935880 A1 CA2935880 A1 CA 2935880A1 CA 2935880 A CA2935880 A CA 2935880A CA 2935880 A CA2935880 A CA 2935880A CA 2935880 A1 CA2935880 A1 CA 2935880A1
- Authority
- CA
- Canada
- Prior art keywords
- indazol
- compound
- methyl
- lcms
- piperidin
- 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
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- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 230000011664 signaling Effects 0.000 description 1
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- 230000035882 stress Effects 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- DQQJBEAXSOOCPG-SSDOTTSWSA-N tert-butyl n-[(3r)-pyrrolidin-3-yl]carbamate Chemical group CC(C)(C)OC(=O)N[C@@H]1CCNC1 DQQJBEAXSOOCPG-SSDOTTSWSA-N 0.000 description 1
- CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical group CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 1
- GCPNPVFWMHBPNS-UHFFFAOYSA-N tert-butyl-dimethyl-piperidin-4-yloxysilane Chemical compound CC(C)(C)[Si](C)(C)OC1CCNCC1 GCPNPVFWMHBPNS-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
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| IN3018/CHE/2014 | 2014-06-20 | ||
| PCT/IB2015/050119 WO2015104662A1 (en) | 2014-01-10 | 2015-01-07 | Indazole compounds as irak4 inhibitors |
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- 2015-01-07 US US15/110,309 patent/US10160753B2/en not_active Expired - Fee Related
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- 2015-01-07 EP EP15703102.2A patent/EP3092226B1/en not_active Revoked
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- 2015-01-07 BR BR112016015983A patent/BR112016015983A2/pt not_active Application Discontinuation
- 2015-01-07 JP JP2016563277A patent/JP2017505337A/ja not_active Ceased
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2016
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- 2016-07-05 PH PH12016501338A patent/PH12016501338A1/en unknown
- 2016-07-11 CU CUP2016000109A patent/CU20160109A7/es unknown
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| EP3092226B1 (en) | 2019-03-13 |
| KR20160115933A (ko) | 2016-10-06 |
| PH12016501338A1 (en) | 2016-08-15 |
| HK1231480A1 (zh) | 2017-12-22 |
| US20160326151A1 (en) | 2016-11-10 |
| US10160753B2 (en) | 2018-12-25 |
| IL246555A0 (en) | 2016-08-31 |
| AU2015205348A1 (en) | 2016-07-28 |
| WO2015104662A1 (en) | 2015-07-16 |
| SG11201605408RA (en) | 2016-07-28 |
| JP2017505337A (ja) | 2017-02-16 |
| CN106458982A (zh) | 2017-02-22 |
| MX2016009011A (es) | 2017-01-23 |
| CU20160109A7 (es) | 2017-02-02 |
| EA201691401A1 (ru) | 2016-11-30 |
| BR112016015983A2 (pt) | 2017-08-08 |
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