JPWO2019191092A5 - - Google Patents
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- Publication number
- JPWO2019191092A5 JPWO2019191092A5 JP2020552026A JP2020552026A JPWO2019191092A5 JP WO2019191092 A5 JPWO2019191092 A5 JP WO2019191092A5 JP 2020552026 A JP2020552026 A JP 2020552026A JP 2020552026 A JP2020552026 A JP 2020552026A JP WO2019191092 A5 JPWO2019191092 A5 JP WO2019191092A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazine
- amino
- phenol
- pyrazole
- tetramethylpiperidine
- 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
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- -1 1,2-dihydropyridinyl Chemical group 0.000 claims 93
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000004076 pyridyl group Chemical group 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims 1
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims 1
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 claims 1
- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims 1
- IKNUIKBFNNJXQD-UHFFFAOYSA-N 2-(5-piperidin-4-yloxypyrazin-2-yl)-5-(1H-pyrazol-4-yl)phenol Chemical compound N1CCC(CC1)OC=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O IKNUIKBFNNJXQD-UHFFFAOYSA-N 0.000 claims 1
- OASPCOJIXLTDNU-UHFFFAOYSA-N 2-(5-piperidin-4-yloxypyrazin-2-yl)-5-(1H-pyrazol-4-yl)phenol trihydrochloride Chemical compound Cl.Cl.Cl.N1CCC(CC1)OC=1N=CC(=NC1)C1=C(C=C(C=C1)C=1C=NNC1)O OASPCOJIXLTDNU-UHFFFAOYSA-N 0.000 claims 1
- DIGMVIFWRARWAA-UHFFFAOYSA-N 2-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]-5-(2,2,6,6-tetramethylpiperidin-4-yl)oxypyrazine Chemical compound FC1=C(C=CC(=C1F)C=1C=NNC=1)C1=NC=C(N=C1)OC1CC(NC(C1)(C)C)(C)C DIGMVIFWRARWAA-UHFFFAOYSA-N 0.000 claims 1
- DZQBYXJNUAVIBZ-UHFFFAOYSA-N 2-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]-5-(2,2,6,6-tetramethylpiperidin-4-yl)oxypyrazine trihydrochloride Chemical compound CC1(CC(CC(N1)(C)C)OC2=NC=C(N=C2)C3=C(C(=C(C=C3)C4=CNN=C4)F)F)C.Cl.Cl.Cl DZQBYXJNUAVIBZ-UHFFFAOYSA-N 0.000 claims 1
- PGJONQZOJFKMDI-UHFFFAOYSA-N 2-[5-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C1N(CC2C1CNC2)C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O PGJONQZOJFKMDI-UHFFFAOYSA-N 0.000 claims 1
- AQPVVBVWDFPJIS-UHFFFAOYSA-N 2-[5-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol tetrahydrochloride Chemical compound C1C2CN(CC2CN1)C3=NC=C(N=C3)C4=C(C=C(C=C4)C5=CNN=C5)O.Cl.Cl.Cl.Cl AQPVVBVWDFPJIS-UHFFFAOYSA-N 0.000 claims 1
- GGRSYZQGVRWXPJ-UHFFFAOYSA-N 2-[5-(2,7-diazaspiro[3.4]octan-2-yl)pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C1N(CC11CNCC1)C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O GGRSYZQGVRWXPJ-UHFFFAOYSA-N 0.000 claims 1
- ZZCFEUQEEVGWKB-UHFFFAOYSA-N 2-[5-(piperidin-4-ylamino)pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound N1CCC(CC1)NC=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O ZZCFEUQEEVGWKB-UHFFFAOYSA-N 0.000 claims 1
- GSDATBBMDNCKCT-UHFFFAOYSA-N 2-[5-(piperidin-4-ylamino)pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol tetrahydrochloride Chemical compound C1CNCCC1NC2=NC=C(N=C2)C3=C(C=C(C=C3)C4=CNN=C4)O.Cl.Cl.Cl.Cl GSDATBBMDNCKCT-UHFFFAOYSA-N 0.000 claims 1
- DJUDFYVWPSROQV-UHFFFAOYSA-N 2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-(triazol-2-yl)phenol Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=C1)C1=C(O)C=C(C=C1)N1N=CC=N1 DJUDFYVWPSROQV-UHFFFAOYSA-N 0.000 claims 1
- OZYCXOXQSURAGX-UHFFFAOYSA-N 2-[5-[2-hydroxy-4-(1H-pyrazol-4-yl)phenyl]pyrazin-2-yl]-2-(2,2,6,6-tetramethylpiperidin-4-yl)acetonitrile Chemical compound OC1=C(C=CC(=C1)C=1C=NNC=1)C=1N=CC(=NC=1)C(C#N)C1CC(NC(C1)(C)C)(C)C OZYCXOXQSURAGX-UHFFFAOYSA-N 0.000 claims 1
- HHTJEPSYVJFJSQ-UHFFFAOYSA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NN(C=1)C)O HHTJEPSYVJFJSQ-UHFFFAOYSA-N 0.000 claims 1
- FLYPXFRSCMKLHG-UHFFFAOYSA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-(1-methylpyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Cn1cc(cn1)-c1ccc(c(O)c1)-c1cnc(cn1)N1CCC(C1)NC(C)(C)C FLYPXFRSCMKLHG-UHFFFAOYSA-N 0.000 claims 1
- YPKUJWIGUBMAOC-UHFFFAOYSA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O YPKUJWIGUBMAOC-UHFFFAOYSA-N 0.000 claims 1
- MJBABKMSSYHMCO-UHFFFAOYSA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1cnc(cn1)-c1ccc(cc1O)-c1cn[nH]c1 MJBABKMSSYHMCO-UHFFFAOYSA-N 0.000 claims 1
- HHTJEPSYVJFJSQ-GKOSEXJESA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-[1-(trideuteriomethyl)pyrazol-4-yl]phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NN(C=1)C([2H])([2H])[2H])O HHTJEPSYVJFJSQ-GKOSEXJESA-N 0.000 claims 1
- FLYPXFRSCMKLHG-DULOSRJUSA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-[1-(trideuteriomethyl)pyrazol-4-yl]phenol dihydrochloride Chemical compound Cl.Cl.[2H]C([2H])([2H])n1cc(cn1)-c1ccc(c(O)c1)-c1cnc(cn1)N1CCC(C1)NC(C)(C)C FLYPXFRSCMKLHG-DULOSRJUSA-N 0.000 claims 1
- SVZIYQDLLKCYFU-UHFFFAOYSA-N 2-[5-[amino-(2,2,6,6-tetramethylpiperidin-4-yl)methyl]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound NC(C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C1CC(NC(C1)(C)C)(C)C SVZIYQDLLKCYFU-UHFFFAOYSA-N 0.000 claims 1
- FKEBCGSHHBRTPF-UHFFFAOYSA-N 2-[5-[methyl(piperidin-4-yl)amino]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN(C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C1CCNCC1 FKEBCGSHHBRTPF-UHFFFAOYSA-N 0.000 claims 1
- KYLQBJVOMJMWGU-UHFFFAOYSA-N 2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol hydrobromide Chemical compound Br.CN(C1CC(C)(C)NC(C)(C)C1)c1cnc(cn1)-c1ccc(cc1O)-c1cn[nH]c1 KYLQBJVOMJMWGU-UHFFFAOYSA-N 0.000 claims 1
- XXCBCHUIECDYDQ-UHFFFAOYSA-N 2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-(triazol-2-yl)phenol Chemical compound CN(C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1N=CC=N1)O)C1CC(NC(C1)(C)C)(C)C XXCBCHUIECDYDQ-UHFFFAOYSA-N 0.000 claims 1
- CJBAWWOUMQLVHW-VPYROQPTSA-N 2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-[1-(trideuteriomethyl)pyrazol-4-yl]phenol Chemical compound C(N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C)([2H])([2H])[2H] CJBAWWOUMQLVHW-VPYROQPTSA-N 0.000 claims 1
- NXJUVYCMVOOVJT-UHFFFAOYSA-N 2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-pyrazol-1-ylphenol Chemical compound CN(C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1N=CC=C1)O)C1CC(NC(C1)(C)C)(C)C NXJUVYCMVOOVJT-UHFFFAOYSA-N 0.000 claims 1
- AIPSUZCQFPSGLV-UHFFFAOYSA-N 4-[3-hydroxy-4-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl]-1H-pyrazole-5-carbonitrile Chemical compound OC=1C=C(C=CC=1C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C)C=1C=NNC=1C#N AIPSUZCQFPSGLV-UHFFFAOYSA-N 0.000 claims 1
- GTAYBMVFMPMRCY-UHFFFAOYSA-N 4-[3-hydroxy-4-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl]-1H-pyridin-2-one Chemical compound OC=1C=C(C=CC=1C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C)C1=CC(=NC=C1)O GTAYBMVFMPMRCY-UHFFFAOYSA-N 0.000 claims 1
- NAGODULBRRMYTM-UHFFFAOYSA-N 4-[3-hydroxy-4-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl]-2-methylpyrazole-3-carbonitrile Chemical compound OC=1C=C(C=CC=1C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C)C=1C=NN(C=1C#N)C NAGODULBRRMYTM-UHFFFAOYSA-N 0.000 claims 1
- BYRFQNHNCDBMBE-UHFFFAOYSA-N 4-fluoro-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound FC1=CC(=C(C=C1C=1C=NNC=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C BYRFQNHNCDBMBE-UHFFFAOYSA-N 0.000 claims 1
- ZVLBHUOHQNYWPZ-UHFFFAOYSA-N 4-fluoro-5-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-2-(1H-pyrazol-4-yl)benzonitrile Chemical compound FC1=CC(=C(C#N)C=C1C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C)C=1C=NNC=1 ZVLBHUOHQNYWPZ-UHFFFAOYSA-N 0.000 claims 1
- CMDFZHYVQPQELQ-UHFFFAOYSA-N 5-(1,5-dimethylpyrazol-4-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CN1N=CC(=C1C)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C CMDFZHYVQPQELQ-UHFFFAOYSA-N 0.000 claims 1
- PQWKSBIYLLJDAM-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CN1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C PQWKSBIYLLJDAM-UHFFFAOYSA-N 0.000 claims 1
- CJBAWWOUMQLVHW-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CN1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C CJBAWWOUMQLVHW-UHFFFAOYSA-N 0.000 claims 1
- MCYFRMAVSYYRBB-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[5-(2,2,6,6-tetramethylpiperidin-4-yl)oxypyrazin-2-yl]phenol Chemical compound N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)OC1CC(NC(C1)(C)C)(C)C MCYFRMAVSYYRBB-UHFFFAOYSA-N 0.000 claims 1
- QUOQPMKZWUYSKF-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[5-(2,2,6,6-tetramethylpiperidin-4-yl)oxypyrazin-2-yl]phenol hydrochloride Chemical compound Cl.CC1(C)CC(CC(C)(C)N1)Oc1cnc(cn1)-c1ccc(cc1O)-c1cn[nH]c1 QUOQPMKZWUYSKF-UHFFFAOYSA-N 0.000 claims 1
- DUMYCWDXIVSOQM-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C DUMYCWDXIVSOQM-UHFFFAOYSA-N 0.000 claims 1
- LGHAGLPDIOJZSQ-UHFFFAOYSA-N 5-(1H-pyrazol-5-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1O)-c1ccn[nH]1 LGHAGLPDIOJZSQ-UHFFFAOYSA-N 0.000 claims 1
- LMFIWTZDOGYPQO-UHFFFAOYSA-N 5-(3-aminopyrazol-1-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound NC1=NN(C=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C LMFIWTZDOGYPQO-UHFFFAOYSA-N 0.000 claims 1
- DNADVCPATWWFGM-UHFFFAOYSA-N 5-(4-fluoropyrazol-1-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1O)-n1cc(F)cn1 DNADVCPATWWFGM-UHFFFAOYSA-N 0.000 claims 1
- LNZKMSFMFQYFAO-UHFFFAOYSA-N 5-(5-chloro-1H-pyrazol-4-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound ClC1=C(C=NN1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C LNZKMSFMFQYFAO-UHFFFAOYSA-N 0.000 claims 1
- UQMXADBFKHOXAR-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1O)-c1cn[nH]c1F UQMXADBFKHOXAR-UHFFFAOYSA-N 0.000 claims 1
- PHFTVBJWFCBELW-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound FC1=NNC=C1C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C PHFTVBJWFCBELW-UHFFFAOYSA-N 0.000 claims 1
- VTYVULOWLCPDAE-UHFFFAOYSA-N 5-(5-methyl-1H-pyrazol-4-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1=C(C=NN1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C VTYVULOWLCPDAE-UHFFFAOYSA-N 0.000 claims 1
- PXCHKBILLARLLX-UHFFFAOYSA-N 5-(6-methoxypyrimidin-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound COC1=CC(=NC=N1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C PXCHKBILLARLLX-UHFFFAOYSA-N 0.000 claims 1
- WBWIUOYKHMWYFU-UHFFFAOYSA-N 5-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC1=C(C=CC(=C1F)C=1C=NNC=1)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C WBWIUOYKHMWYFU-UHFFFAOYSA-N 0.000 claims 1
- XJWLUMIGMIGLLC-UHFFFAOYSA-N 5-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine hydrochloride Chemical compound Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1cnc(cn1)-c1ccc(-c2cn[nH]c2)c(F)c1F XJWLUMIGMIGLLC-UHFFFAOYSA-N 0.000 claims 1
- XSUNNOLPPMCQNM-UHFFFAOYSA-N 5-[2,3-difluoro-4-(4-methylimidazol-1-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC1=C(C=CC(=C1F)N1C=NC(=C1)C)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C XSUNNOLPPMCQNM-UHFFFAOYSA-N 0.000 claims 1
- BEMFMPBESBUDOW-UHFFFAOYSA-N 5-[2,5-dichloro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound ClC1=C(C=C(C(=C1)C=1C=NNC=1)Cl)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C BEMFMPBESBUDOW-UHFFFAOYSA-N 0.000 claims 1
- ZVTDOQWCYFJQAL-UHFFFAOYSA-N 5-[2,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC1=C(C=C(C(=C1)C=1C=NNC=1)F)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C ZVTDOQWCYFJQAL-UHFFFAOYSA-N 0.000 claims 1
- GQXWQGYXNSISOF-UHFFFAOYSA-N 5-[2-fluoro-5-methyl-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC1=C(C=C(C(=C1)C=1C=NNC=1)C)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C GQXWQGYXNSISOF-UHFFFAOYSA-N 0.000 claims 1
- ZNFRTMGFKOPSIR-UHFFFAOYSA-N 5-[3,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC=1C=C(C=C(C=1C=1C=NNC=1)F)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C ZNFRTMGFKOPSIR-UHFFFAOYSA-N 0.000 claims 1
- NIBRAOVIPJXQHW-UHFFFAOYSA-N 5-[3-fluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC=1C=C(C=CC=1C=1C=NNC=1)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C NIBRAOVIPJXQHW-UHFFFAOYSA-N 0.000 claims 1
- QFBTZAZRFWCMTG-UHFFFAOYSA-N 5-[5-chloro-2-fluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound ClC=1C(=CC(=C(C=1)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C)F)C=1C=NNC=1 QFBTZAZRFWCMTG-UHFFFAOYSA-N 0.000 claims 1
- AAJPZNKNQJJTKH-UHFFFAOYSA-N 5-imidazo[1,2-a]pyrazin-6-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=C1)C1=C(O)C=C(C=C1)C1=CN2C=CN=C2C=N1 AAJPZNKNQJJTKH-UHFFFAOYSA-N 0.000 claims 1
- YOURWMUJBGHWJG-UHFFFAOYSA-N 5-imidazo[1,2-b]pyridazin-6-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=C1)C1=C(O)C=C(C=C1)C1=NN2C=CN=C2C=C1 YOURWMUJBGHWJG-UHFFFAOYSA-N 0.000 claims 1
- HPEBYVKMECBKSL-UHFFFAOYSA-N 5-imidazol-1-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1(C=NC=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C HPEBYVKMECBKSL-UHFFFAOYSA-N 0.000 claims 1
- RTELLJFZTFWNSE-UHFFFAOYSA-N 5-imidazol-1-yl-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)c1cnc(cn1)-c1ccc(cc1O)-n1ccnc1 RTELLJFZTFWNSE-UHFFFAOYSA-N 0.000 claims 1
- ZCILNELTDVTXEM-UHFFFAOYSA-N 5-pyridin-2-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1=C(C=CC=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C ZCILNELTDVTXEM-UHFFFAOYSA-N 0.000 claims 1
- GSNOMESXIOXXJF-UHFFFAOYSA-N 5-pyridin-3-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1=CC(=CC=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C GSNOMESXIOXXJF-UHFFFAOYSA-N 0.000 claims 1
- PHVQAAMYKMYCFZ-UHFFFAOYSA-N 5-pyridin-4-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1=CC=C(C=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C PHVQAAMYKMYCFZ-UHFFFAOYSA-N 0.000 claims 1
- KLRZPNFBFXYMIL-UHFFFAOYSA-N 5-pyrimidin-2-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1=C(N=CC=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C KLRZPNFBFXYMIL-UHFFFAOYSA-N 0.000 claims 1
- XXHJACUVXZBAHX-UHFFFAOYSA-N CN(C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C1CC(NC(C1)(C)C)(C)C Chemical compound CN(C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C1CC(NC(C1)(C)C)(C)C XXHJACUVXZBAHX-UHFFFAOYSA-N 0.000 claims 1
- RFYNOSZOQAMUOK-UHFFFAOYSA-N CN1N=C(C=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C Chemical compound CN1N=C(C=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C RFYNOSZOQAMUOK-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- APSLUPXFNWDZNC-UHFFFAOYSA-N N-tert-butyl-1-[5-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]pyrazin-2-yl]pyrrolidin-3-amine Chemical compound C(C)(C)(C)NC1CN(CC1)C1=NC=C(N=C1)C1=C(C(=C(C=C1)C=1C=NNC=1)F)F APSLUPXFNWDZNC-UHFFFAOYSA-N 0.000 claims 1
- PDIDVOFMELOGGH-UHFFFAOYSA-N N-tert-butyl-1-[5-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]pyrazin-2-yl]pyrrolidin-3-amine dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1cnc(cn1)-c1ccc(-c2cn[nH]c2)c(F)c1F PDIDVOFMELOGGH-UHFFFAOYSA-N 0.000 claims 1
- WOIZIPCMOCBZBO-UHFFFAOYSA-N N-tert-butyl-1-[5-[2,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]pyrazin-2-yl]pyrrolidin-3-amine dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1cnc(cn1)-c1cc(F)c(cc1F)-c1cn[nH]c1 WOIZIPCMOCBZBO-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- QIWWIXNCPDYEJP-UHFFFAOYSA-N [2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-(triazol-2-yl)phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=C1)C1=C(OC=O)C=C(C=C1)N1N=CC=N1 QIWWIXNCPDYEJP-UHFFFAOYSA-N 0.000 claims 1
- FXDAWMJWIUPBSD-UHFFFAOYSA-N [5-(1-methylpyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound C(=O)OC1=C(C=CC(=C1)C=1C=NN(C=1)C)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C FXDAWMJWIUPBSD-UHFFFAOYSA-N 0.000 claims 1
- UVBXTCOTFIZBHE-UHFFFAOYSA-N [5-(1H-pyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1cn[nH]c1 UVBXTCOTFIZBHE-UHFFFAOYSA-N 0.000 claims 1
- IBMAILOZWWNVKT-UHFFFAOYSA-N [5-(1H-pyrazol-5-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1ccn[nH]1 IBMAILOZWWNVKT-UHFFFAOYSA-N 0.000 claims 1
- HURNPEQOZUBPSS-UHFFFAOYSA-N [5-(4-fluoropyrazol-1-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-n1cc(F)cn1 HURNPEQOZUBPSS-UHFFFAOYSA-N 0.000 claims 1
- ZDTULKQFWWTJBO-UHFFFAOYSA-N [5-(5-fluoro-1H-pyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1cn[nH]c1F ZDTULKQFWWTJBO-UHFFFAOYSA-N 0.000 claims 1
- NYDUCOVDAAROBE-UHFFFAOYSA-N [5-(6-methoxypyrimidin-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound COc1cc(ncn1)-c1ccc(c(OC=O)c1)-c1cnc(NC2CC(C)(C)NC(C)(C)C2)cn1 NYDUCOVDAAROBE-UHFFFAOYSA-N 0.000 claims 1
- JUILYRQXBWZWDC-UHFFFAOYSA-N [5-imidazo[1,2-a]pyrazin-6-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1cn2ccnc2cn1 JUILYRQXBWZWDC-UHFFFAOYSA-N 0.000 claims 1
- YJKFHESCRFFOIO-UHFFFAOYSA-N [5-imidazo[1,2-b]pyridazin-6-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1ccc2nccn2n1 YJKFHESCRFFOIO-UHFFFAOYSA-N 0.000 claims 1
- UOYQEAQPHOWXSJ-UHFFFAOYSA-N [5-imidazol-1-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-n1ccnc1 UOYQEAQPHOWXSJ-UHFFFAOYSA-N 0.000 claims 1
- SJHTYWAUBLWORY-UHFFFAOYSA-N [5-pyridin-2-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1ccccn1 SJHTYWAUBLWORY-UHFFFAOYSA-N 0.000 claims 1
- VVHBDZBUFVONLN-UHFFFAOYSA-N [5-pyridin-3-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1cccnc1 VVHBDZBUFVONLN-UHFFFAOYSA-N 0.000 claims 1
- QPCHTSAXCSKMHV-UHFFFAOYSA-N [5-pyridin-4-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1ccncc1 QPCHTSAXCSKMHV-UHFFFAOYSA-N 0.000 claims 1
- VIOQLPSVXJWYCC-UHFFFAOYSA-N [5-pyrimidin-2-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound C(=O)OC1=C(C=CC(=C1)C1=NC=CC=N1)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C VIOQLPSVXJWYCC-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- XVQUOJBERHHONY-UHFFFAOYSA-N isometheptene Chemical compound CNC(C)CCC=C(C)C XVQUOJBERHHONY-UHFFFAOYSA-N 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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MX2021001091A (es) | 2015-12-10 | 2022-04-26 | Ptc Therapeutics Inc | Compuestos para usarse en el tratamiento o mejoramiento de la enfermedad de huntington. |
EP3634953B1 (en) | 2017-06-05 | 2024-01-03 | PTC Therapeutics, Inc. | Compounds for treating huntington's disease |
MX2019015580A (es) | 2017-06-28 | 2020-07-28 | Ptc Therapeutics Inc | Metodos para tratar la enfermedad de huntington. |
BR112019027717A2 (pt) | 2017-06-28 | 2020-07-28 | Ptc Therapeutics, Inc. | métodos para tratar a doença de huntington |
RU2020105929A (ru) | 2017-08-04 | 2021-09-06 | Скайхоук Терапьютикс, Инк. | Способы и композиции для модулирования сплайсинга |
JP2021506978A (ja) | 2017-12-22 | 2021-02-22 | ラヴェンナ ファーマシューティカルズ,インコーポレイテッド | ホスファチジルイノシトールリン酸キナーゼ阻害剤としてのアミノピリジン誘導体 |
CA3094703A1 (en) | 2018-03-27 | 2019-10-03 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
EP3814357B1 (en) * | 2018-06-27 | 2024-05-01 | PTC Therapeutics, Inc. | Heterocyclic and heteroaryl compounds for treating huntington's disease |
EP3814360A1 (en) | 2018-06-27 | 2021-05-05 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
JP2022521467A (ja) | 2019-02-05 | 2022-04-08 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
WO2020163409A1 (en) * | 2019-02-05 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
EP3920928A4 (en) | 2019-02-06 | 2022-09-28 | Skyhawk Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR MODULATION OF SPLICING |
US11129829B2 (en) | 2019-06-17 | 2021-09-28 | Skyhawk Therapeutics, Inc. | Methods for modulating splicing |
TW202112767A (zh) | 2019-06-17 | 2021-04-01 | 美商佩特拉製藥公司 | 作為磷脂酸肌醇磷酸激酶抑制劑之胺基吡啶衍生物 |
JP2023500251A (ja) | 2019-11-01 | 2023-01-05 | ノバルティス アーゲー | ハンチントン病の進行を遅らせる処置のためのスプライシングモジュレーターの使用 |
EP4132923A1 (en) | 2020-04-09 | 2023-02-15 | PTC Therapeutics, Inc. | Compounds for treating huntington's disease |
TW202208358A (zh) | 2020-05-13 | 2022-03-01 | 美商Chdi基金會股份有限公司 | 用於治療亨汀頓舞蹈症之htt調節劑 |
TW202216671A (zh) * | 2020-06-25 | 2022-05-01 | 瑞士商諾華公司 | 1,4—二取代的嗒𠯤化合物之製造方法 |
WO2022031998A2 (en) * | 2020-08-05 | 2022-02-10 | Skyhawk Therapeutics, Inc. | Process for the preparation of intermediates useful in the preparation of compounds that modulate splicing |
WO2022032007A2 (en) * | 2020-08-05 | 2022-02-10 | Skyhawk Therapeutics, Inc. | Process for the preparation of intermediates useful in the preparation of compounds that modulate splicing |
WO2022031838A1 (en) * | 2020-08-05 | 2022-02-10 | Skyhawk Therapeutics, Inc. | Compositions for modulating splicing |
TW202304446A (zh) | 2021-03-29 | 2023-02-01 | 瑞士商諾華公司 | 剪接調節子用於減慢杭丁頓氏舞蹈症進展的治療之用途 |
BR112023022451A2 (pt) | 2021-04-28 | 2024-01-02 | Astellas Pharma Inc | Composto triazina substituído |
WO2023028536A1 (en) * | 2021-08-25 | 2023-03-02 | Ptc Therapeutics, Inc. | 1,2,4-triazine derivatives useful as inhibitors of nlrp3 |
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2019
- 2019-03-26 CA CA3094703A patent/CA3094703A1/en active Pending
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