ES2784244T3 - Reguladores de Nrf2 - Google Patents
Reguladores de Nrf2 Download PDFInfo
- Publication number
- ES2784244T3 ES2784244T3 ES14827868T ES14827868T ES2784244T3 ES 2784244 T3 ES2784244 T3 ES 2784244T3 ES 14827868 T ES14827868 T ES 14827868T ES 14827868 T ES14827868 T ES 14827868T ES 2784244 T3 ES2784244 T3 ES 2784244T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- benzo
- acid
- dioxide
- triazo
- 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.)
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- 101000588302 Homo sapiens Nuclear factor erythroid 2-related factor 2 Proteins 0.000 title description 59
- 102100031701 Nuclear factor erythroid 2-related factor 2 Human genes 0.000 title description 59
- -1 Tetrahydro-2H-pyranyl Chemical group 0.000 claims abstract description 1013
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 646
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 318
- 150000001875 compounds Chemical class 0.000 claims abstract description 151
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 108
- 239000001257 hydrogen Substances 0.000 claims abstract description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 65
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 125000005936 piperidyl group Chemical group 0.000 claims abstract description 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 125000002541 furyl group Chemical group 0.000 claims abstract description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 5
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims description 364
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 55
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 54
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 47
- 125000005605 benzo group Chemical group 0.000 claims description 43
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
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- 229950010765 pivalate Drugs 0.000 claims description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 19
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 claims 4
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- HXQHRUJXQJEGER-UHFFFAOYSA-N 1-methylbenzotriazole Chemical compound C1=CC=C2N(C)N=NC2=C1 HXQHRUJXQJEGER-UHFFFAOYSA-N 0.000 claims 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 2
- VGCWCUQMEWJQSU-UHFFFAOYSA-N 1-ethylbenzotriazole Chemical compound C1=CC=C2N(CC)N=NC2=C1 VGCWCUQMEWJQSU-UHFFFAOYSA-N 0.000 claims 1
- 241000518994 Conta Species 0.000 claims 1
- 240000007313 Tilia cordata Species 0.000 claims 1
- 125000003943 azolyl group Chemical group 0.000 claims 1
- 239000012964 benzotriazole Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 27
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract description 12
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 abstract description 11
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- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 abstract description 4
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- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract description 4
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| ES2908941T3 (es) * | 2016-12-15 | 2022-05-04 | Glaxosmithkline Ip Dev Ltd | Triazoles unidos a éter como reguladores de NRF2 |
| EP3555104B1 (en) | 2016-12-15 | 2021-11-24 | GlaxoSmithKline Intellectual Property Development Limited | Nrf2 compounds |
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