JPWO2020005877A5 - - Google Patents
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- Publication number
- JPWO2020005877A5 JPWO2020005877A5 JP2020572894A JP2020572894A JPWO2020005877A5 JP WO2020005877 A5 JPWO2020005877 A5 JP WO2020005877A5 JP 2020572894 A JP2020572894 A JP 2020572894A JP 2020572894 A JP2020572894 A JP 2020572894A JP WO2020005877 A5 JPWO2020005877 A5 JP WO2020005877A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- thiazolo
- benzothiazole
- fluoro
- indazole
- 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
- -1 phenyl-oxy Chemical group 0.000 claims 304
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 89
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 84
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 66
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 38
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 32
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 26
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 22
- WFJZBOIOPMOUCB-UHFFFAOYSA-N pyridazine;hydrochloride Chemical compound Cl.C1=CC=NN=C1 WFJZBOIOPMOUCB-UHFFFAOYSA-N 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 16
- JELQZSVKOONUKD-UHFFFAOYSA-N phenol dihydrochloride Chemical compound Cl.Cl.OC1=CC=CC=C1.OC1=CC=CC=C1 JELQZSVKOONUKD-UHFFFAOYSA-N 0.000 claims 15
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 13
- OSHXRTVCVNSLPD-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]pyridin-2-amine Chemical compound N1=CC=C2SC(N)=NC2=C1 OSHXRTVCVNSLPD-UHFFFAOYSA-N 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 7
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 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 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- GEOWCLRLLWTHDN-UHFFFAOYSA-N phenyl formate Chemical compound O=COC1=CC=CC=C1 GEOWCLRLLWTHDN-UHFFFAOYSA-N 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- HAOKKJHTFUZWIM-UHFFFAOYSA-N pyridin-1-ium-2-amine;chloride Chemical compound Cl.NC1=CC=CC=N1 HAOKKJHTFUZWIM-UHFFFAOYSA-N 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 3
- GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 claims 3
- 125000000033 alkoxyamino group Chemical group 0.000 claims 3
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 2
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- WCTIANMEZMXTPH-UHFFFAOYSA-N Cl.S1C(=NC=2C=NC=CC21)N Chemical compound Cl.S1C(=NC=2C=NC=CC21)N WCTIANMEZMXTPH-UHFFFAOYSA-N 0.000 claims 2
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 2
- FIPLAFRCDDWERW-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]pyridine Chemical compound N1=CC=C2SC=NC2=C1 FIPLAFRCDDWERW-UHFFFAOYSA-N 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- MYTKOOVOBCDRPN-UHFFFAOYSA-N imidazo[1,2-a]pyridine-8-carbonitrile Chemical compound N#CC1=CC=CN2C=CN=C12 MYTKOOVOBCDRPN-UHFFFAOYSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- OXDLBBKNAAFZNI-UHFFFAOYSA-N phenol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC1=CC=CC=C1 OXDLBBKNAAFZNI-UHFFFAOYSA-N 0.000 claims 2
- CAUDLGLYRRDHAP-UHFFFAOYSA-N pyrazin-2-amine;hydrochloride Chemical compound Cl.NC1=CN=CC=N1 CAUDLGLYRRDHAP-UHFFFAOYSA-N 0.000 claims 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims 1
- BTEDMKYHAOWQLQ-UHFFFAOYSA-N 1-[6-(2-methylindazol-5-yl)-1,3-benzothiazol-2-yl]piperidin-4-amine Chemical compound CN1N=C2C=CC(=CC2=C1)C1=CC2=C(N=C(S2)N2CCC(CC2)N)C=C1 BTEDMKYHAOWQLQ-UHFFFAOYSA-N 0.000 claims 1
- SPLFOCXQLPTLKA-UHFFFAOYSA-N 1-[6-(2-methylindazol-5-yl)-1,3-benzothiazol-2-yl]piperidin-4-amine hydrochloride Chemical compound Cl.CN1N=C2C=CC(=CC2=C1)C1=CC2=C(N=C(S2)N2CCC(CC2)N)C=C1 SPLFOCXQLPTLKA-UHFFFAOYSA-N 0.000 claims 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- ZFYUCIPARAFUGP-UHFFFAOYSA-N 1h-pyridazin-2-amine Chemical compound NN1NC=CC=C1 ZFYUCIPARAFUGP-UHFFFAOYSA-N 0.000 claims 1
- CTMSOFOKNIMUGF-UHFFFAOYSA-N 2-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-6-(2-methylindazol-5-yl)-1,3-benzothiazole Chemical compound CN1N=C2C=CC(=CC2=C1)C1=CC2=C(N=C(S2)C=2CCN(CC=2)C)C=C1 CTMSOFOKNIMUGF-UHFFFAOYSA-N 0.000 claims 1
- LKDJMULCGZIZFN-UHFFFAOYSA-N 2-(2,2-dimethylpiperidin-4-yl)-6-(2-methylindazol-5-yl)-1,3-benzothiazole Chemical compound CC1(NCCC(C1)C=1SC2=C(N=1)C=CC(=C2)C1=CC2=CN(N=C2C=C1)C)C LKDJMULCGZIZFN-UHFFFAOYSA-N 0.000 claims 1
- XUDFVANTXAROLL-UHFFFAOYSA-N 2-(2,2-dimethylpiperidin-4-yl)-6-(2-methylindazol-5-yl)-1,3-benzothiazole hydrochloride Chemical compound Cl.CC1(NCCC(C1)C=1SC2=C(N1)C=CC(=C2)C2=CC1=CN(N=C1C=C2)C)C XUDFVANTXAROLL-UHFFFAOYSA-N 0.000 claims 1
- ARNFJVMDSFJECB-UHFFFAOYSA-N 2-(2,6-dimethylpiperidin-4-yl)-6-(2-methylindazol-5-yl)-1,3-benzothiazole hydrochloride Chemical compound Cl.CC1NC(CC(C1)C=1SC2=C(N=1)C=CC(=C2)C1=CC2=CN(N=C2C=C1)C)C ARNFJVMDSFJECB-UHFFFAOYSA-N 0.000 claims 1
- TWQHQRPMDKDCJS-UHFFFAOYSA-N 2-(2,7-dimethylindazol-5-yl)-6-(1,2,3,6-tetrahydropyridin-4-yl)-1,3-benzothiazole Chemical compound CN1N=C2C(=CC(=CC2=C1)C=1SC2=C(N=1)C=CC(=C2)C=1CCNCC=1)C TWQHQRPMDKDCJS-UHFFFAOYSA-N 0.000 claims 1
- JJEWWGLGZFXCNS-UHFFFAOYSA-N 2-(2,7-dimethylindazol-5-yl)-6-(1,2,3,6-tetrahydropyridin-4-yl)-1,3-benzothiazole hydrochloride Chemical compound Cl.CN1N=C2C(=CC(=CC2=C1)C=1SC2=C(N=1)C=CC(=C2)C=1CCNCC=1)C JJEWWGLGZFXCNS-UHFFFAOYSA-N 0.000 claims 1
- GVAZNJARQUNTJA-UHFFFAOYSA-N 2-(2,7-dimethylindazol-5-yl)-6-piperidin-4-yl-1,3-benzothiazole Chemical compound CN1N=C2C(=CC(=CC2=C1)C=1SC2=C(N=1)C=CC(=C2)C1CCNCC1)C GVAZNJARQUNTJA-UHFFFAOYSA-N 0.000 claims 1
- VVJMYLNBDBXPAM-UHFFFAOYSA-N 2-(2,7-dimethylindazol-5-yl)-6-piperidin-4-yl-1,3-benzothiazole hydrochloride Chemical compound Cl.CN1N=C2C(=CC(=CC2=C1)C=1SC2=C(N1)C=CC(=C2)C2CCNCC2)C VVJMYLNBDBXPAM-UHFFFAOYSA-N 0.000 claims 1
- GUSXUQCDCIJVQA-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-6-(1,2,3,6-tetrahydropyridin-4-yl)-1,3-benzothiazole Chemical compound CN1N=C2C=CC(=CC2=C1)C=1SC2=C(N=1)C=CC(=C2)C=1CCNCC=1 GUSXUQCDCIJVQA-UHFFFAOYSA-N 0.000 claims 1
- HOAIIJHHRPXTMG-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-6-(1,2,3,6-tetrahydropyridin-4-yl)-1,3-benzothiazole hydrochloride Chemical compound Cl.CN1N=C2C=CC(=CC2=C1)C=1SC2=C(N1)C=CC(=C2)C=2CCNCC2 HOAIIJHHRPXTMG-UHFFFAOYSA-N 0.000 claims 1
- CSXIGAPKNDLHCE-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-6-(1,2,3,6-tetrahydropyridin-4-yl)-[1,3]thiazolo[4,5-b]pyridine Chemical compound CN1N=C2C=CC(=CC2=C1)C=1SC=2C(=NC=C(C=2)C=2CCNCC=2)N=1 CSXIGAPKNDLHCE-UHFFFAOYSA-N 0.000 claims 1
- GQQADPJOBWRHCU-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-6-(1,2,3,6-tetrahydropyridin-4-yl)-[1,3]thiazolo[4,5-b]pyridine hydrochloride Chemical compound Cl.CN1N=C2C=CC(=CC2=C1)C=1SC=2C(=NC=C(C=2)C=2CCNCC=2)N=1 GQQADPJOBWRHCU-UHFFFAOYSA-N 0.000 claims 1
- HTMSBGNZFJDULR-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-6-(1-methylpiperidin-4-yl)-1,3-benzothiazole Chemical compound CN1N=C2C=CC(=CC2=C1)C=1SC2=C(N=1)C=CC(=C2)C1CCN(CC1)C HTMSBGNZFJDULR-UHFFFAOYSA-N 0.000 claims 1
- BVPXTUAIEMCARN-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-6-piperidin-4-yl-1,3-benzothiazole Chemical compound CN1N=C2C=CC(=CC2=C1)C=1SC2=C(N=1)C=CC(=C2)C1CCNCC1 BVPXTUAIEMCARN-UHFFFAOYSA-N 0.000 claims 1
- LVIXUPFCMRNCFR-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-6-piperidin-4-yl-1,3-benzothiazole hydrochloride Chemical compound Cl.CN1N=C2C=CC(=CC2=C1)C=1SC2=C(N1)C=CC(=C2)C2CCNCC2 LVIXUPFCMRNCFR-UHFFFAOYSA-N 0.000 claims 1
- KJYQTUIXRKKTJY-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-6-piperidin-4-yl-[1,3]thiazolo[4,5-b]pyridine Chemical compound CN1N=C2C=CC(=CC2=C1)C=1SC=2C(=NC=C(C=2)C2CCNCC2)N=1 KJYQTUIXRKKTJY-UHFFFAOYSA-N 0.000 claims 1
- WVPNNPRJCJGYRS-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-6-piperidin-4-yl-[1,3]thiazolo[4,5-b]pyridine hydrochloride Chemical compound Cl.CN1N=C2C=CC(=CC2=C1)C=1SC=2C(=NC=C(C=2)C2CCNCC2)N=1 WVPNNPRJCJGYRS-UHFFFAOYSA-N 0.000 claims 1
- BMQJPZWFTREIHG-UHFFFAOYSA-N 2-(4-fluoropiperidin-4-yl)-6-(2-methylindazol-5-yl)-1,3-benzothiazole Chemical compound FC1(CCNCC1)C=1SC2=C(N=1)C=CC(=C2)C1=CC2=CN(N=C2C=C1)C BMQJPZWFTREIHG-UHFFFAOYSA-N 0.000 claims 1
- MUNWHCBVAKIQGK-UHFFFAOYSA-N 2-(4-fluoropiperidin-4-yl)-6-(2-methylindazol-5-yl)-1,3-benzothiazole hydrochloride Chemical compound Cl.FC1(CCNCC1)C=1SC2=C(N=1)C=CC(=C2)C1=CC2=CN(N=C2C=C1)C MUNWHCBVAKIQGK-UHFFFAOYSA-N 0.000 claims 1
- QLTLSTDYGQGDHT-UHFFFAOYSA-N 2-(6-piperazin-1-yl-[1,3]thiazolo[4,5-c]pyridazin-3-yl)-5-(1H-pyrazol-4-yl)phenol Chemical compound N1(CCNCC1)C=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 QLTLSTDYGQGDHT-UHFFFAOYSA-N 0.000 claims 1
- UVVXKCVCRHBAHK-UHFFFAOYSA-N 2-(azepan-4-yl)-6-(2-methylindazol-5-yl)-1,3-benzothiazole Chemical compound N1CCC(CCC1)C=1SC2=C(N=1)C=CC(=C2)C1=CC2=CN(N=C2C=C1)C UVVXKCVCRHBAHK-UHFFFAOYSA-N 0.000 claims 1
- KNVNWHNPGYYFHJ-UHFFFAOYSA-N 2-(azepan-4-yl)-6-(2-methylindazol-5-yl)-1,3-benzothiazole hydrochloride Chemical compound Cl.N1CCC(CCC1)C=1SC2=C(N1)C=CC(=C2)C2=CC1=CN(N=C1C=C2)C KNVNWHNPGYYFHJ-UHFFFAOYSA-N 0.000 claims 1
- GRMUYKUSAWATMY-UHFFFAOYSA-N 2-[2-[methyl(piperidin-4-yl)amino]-[1,3]thiazolo[4,5-b]pyrazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN(C=1SC=2C(=NC=C(N=2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1)C1CCNCC1 GRMUYKUSAWATMY-UHFFFAOYSA-N 0.000 claims 1
- VXIOUDGRGWJOIX-UHFFFAOYSA-N 2-[2-[methyl(piperidin-4-yl)amino]-[1,3]thiazolo[4,5-b]pyrazin-6-yl]-5-(1H-pyrazol-4-yl)phenol hydrochloride Chemical compound Cl.CN(C=1SC=2C(=NC=C(N=2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1)C1CCNCC1 VXIOUDGRGWJOIX-UHFFFAOYSA-N 0.000 claims 1
- MACUKHPDJFPASL-UHFFFAOYSA-N 2-[6-(piperidin-4-ylamino)-[1,3]thiazolo[4,5-c]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound N1CCC(CC1)NC=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 MACUKHPDJFPASL-UHFFFAOYSA-N 0.000 claims 1
- PBWJIEYITRJFRQ-UHFFFAOYSA-N 2-[6-[(1-methylpiperidin-4-yl)amino]-[1,3]thiazolo[4,5-c]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN1CCC(CC1)NC=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 PBWJIEYITRJFRQ-UHFFFAOYSA-N 0.000 claims 1
- LCMPNNMPADIYHP-UHFFFAOYSA-N 2-[6-[(1-methylpyrrolidin-3-yl)amino]-[1,3]thiazolo[4,5-c]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN1CC(CC1)NC=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 LCMPNNMPADIYHP-UHFFFAOYSA-N 0.000 claims 1
- DOLPEIBEKXLENB-LRDDRELGSA-N 2-[6-[(1R,6S)-3,8-diazabicyclo[4.2.0]octan-8-yl]-[1,3]thiazolo[4,5-c]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C1CNC[C@H]2[C@@H]1CN2C3=NC4=NN=C(C=C4S3)C5=C(C=C(C=C5)C6=CNN=C6)O DOLPEIBEKXLENB-LRDDRELGSA-N 0.000 claims 1
- DOLPEIBEKXLENB-MLGOLLRUSA-N 2-[6-[(1S,6R)-3,8-diazabicyclo[4.2.0]octan-8-yl]-[1,3]thiazolo[4,5-c]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound [C@H]12CNCC[C@@H]2CN1C=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 DOLPEIBEKXLENB-MLGOLLRUSA-N 0.000 claims 1
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- QEVJLOCIWZULKC-UHFFFAOYSA-N N-methyl-6-[2-methyl-7-(trifluoromethyl)indazol-5-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3-benzothiazol-2-amine Chemical compound CN(C=1SC2=C(N=1)C=CC(=C2)C1=CC2=CN(N=C2C(=C1)C(F)(F)F)C)C1CC(NC(C1)(C)C)(C)C QEVJLOCIWZULKC-UHFFFAOYSA-N 0.000 claims 1
- PKDZTMXFVOZKCC-UHFFFAOYSA-N N-methyl-6-[2-methyl-7-(trifluoromethyl)indazol-5-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3-benzothiazol-2-amine hydrochloride Chemical compound Cl.CN(C=1SC2=C(N1)C=CC(=C2)C2=CC1=CN(N=C1C(=C2)C(F)(F)F)C)C2CC(NC(C2)(C)C)(C)C PKDZTMXFVOZKCC-UHFFFAOYSA-N 0.000 claims 1
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- HEIZPACCIHXHKV-UHFFFAOYSA-N [1,3]thiazolo[4,5-b]pyrazine Chemical compound C1=CN=C2SC=NC2=N1 HEIZPACCIHXHKV-UHFFFAOYSA-N 0.000 claims 1
- AEKMJOCLDYLNRK-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]pyridazin-6-amine Chemical compound N1=CC=C2SC(N)=NC2=N1 AEKMJOCLDYLNRK-UHFFFAOYSA-N 0.000 claims 1
- FDGKUYKUXOBBNK-UHFFFAOYSA-N [2-(6-piperazin-1-yl-[1,3]thiazolo[4,5-c]pyridazin-3-yl)-5-(1H-pyrazol-4-yl)phenyl] formate Chemical compound C(=O)OC1=C(C=CC(=C1)C=1C=NNC=1)C1=CC2=C(N=N1)N=C(S2)N1CCNCC1 FDGKUYKUXOBBNK-UHFFFAOYSA-N 0.000 claims 1
- HBBKMZBGPMTCED-GOEBONIOSA-N [2-[6-[[(3R,4S)-4-fluoro-1-methylpyrrolidin-3-yl]amino]-[1,3]thiazolo[4,5-c]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenyl] formate Chemical compound C(=O)OC1=C(C=CC(=C1)C=1C=NNC=1)C1=CC2=C(N=N1)N=C(S2)N[C@@H]1CN(C[C@@H]1F)C HBBKMZBGPMTCED-GOEBONIOSA-N 0.000 claims 1
- HBBKMZBGPMTCED-HOCLYGCPSA-N [2-[6-[[(3S,4S)-4-fluoro-1-methylpyrrolidin-3-yl]amino]-[1,3]thiazolo[4,5-c]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenyl] formate Chemical compound C(=O)OC1=C(C=CC(=C1)C=1C=NNC=1)C1=CC2=C(N=N1)N=C(S2)N[C@H]1CN(C[C@@H]1F)C HBBKMZBGPMTCED-HOCLYGCPSA-N 0.000 claims 1
- HHCHFNIJJJJYOC-UHFFFAOYSA-N [5-(1H-pyrazol-4-yl)-2-[6-(pyrrolidin-3-ylamino)-[1,3]thiazolo[4,5-c]pyridazin-3-yl]phenyl] formate Chemical compound C(=O)OC1=C(C=CC(=C1)C=1C=NNC=1)C1=CC2=C(N=N1)N=C(S2)NC1CNCC1 HHCHFNIJJJJYOC-UHFFFAOYSA-N 0.000 claims 1
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- XHQKEQDCIWISGM-UHFFFAOYSA-N [5-(4-fluoro-2-piperidin-4-yl-1,3-benzothiazol-6-yl)-2-methylindazol-7-yl]methanamine dihydrochloride Chemical compound CN1C=C2C=C(C=C(C2=N1)CN)C3=CC(=C4C(=C3)SC(=N4)C5CCNCC5)F.Cl.Cl XHQKEQDCIWISGM-UHFFFAOYSA-N 0.000 claims 1
- UJJRFNCZESXEJE-UHFFFAOYSA-N [5-imidazol-1-yl-2-[6-[methyl(piperidin-4-yl)amino]-[1,3]thiazolo[4,5-c]pyridazin-3-yl]phenyl] formate Chemical compound C(=O)OC1=C(C=CC(=C1)N1C=NC=C1)C1=CC2=C(N=N1)N=C(S2)N(C1CCNCC1)C UJJRFNCZESXEJE-UHFFFAOYSA-N 0.000 claims 1
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- 239000002253 acid Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000003725 azepanyl group Chemical group 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- ZXRCAYWYTOIRQS-UHFFFAOYSA-N hydron;phenol;chloride Chemical compound Cl.OC1=CC=CC=C1 ZXRCAYWYTOIRQS-UHFFFAOYSA-N 0.000 claims 1
- GCRUEXFJNQVIJM-UHFFFAOYSA-N hydron;pyridazin-3-amine;chloride Chemical compound Cl.NC1=CC=CN=N1 GCRUEXFJNQVIJM-UHFFFAOYSA-N 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- HYHBKLWDTGTBME-UHFFFAOYSA-N pyrazin-1-ium;chloride Chemical compound Cl.C1=CN=CC=N1 HYHBKLWDTGTBME-UHFFFAOYSA-N 0.000 claims 1
- LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical compound NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
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| PCT/US2019/038895 WO2020005877A1 (en) | 2018-06-27 | 2019-06-25 | Heteroaryl compounds for treating huntington's disease |
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| CN113717154A (zh) | 2015-12-10 | 2021-11-30 | Ptc医疗公司 | 用于治疗亨廷顿病的方法 |
| WO2018226622A1 (en) | 2017-06-05 | 2018-12-13 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
| EP3645121A4 (en) | 2017-06-28 | 2021-03-17 | PTC Therapeutics, Inc. | HUNTINGTON'S DISEASE TREATMENT METHODS |
| BR112019027717A2 (pt) | 2017-06-28 | 2020-07-28 | Ptc Therapeutics, Inc. | métodos para tratar a doença de huntington |
| WO2019028440A1 (en) | 2017-08-04 | 2019-02-07 | Skyhawk Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR MODULATING SPLICING |
| KR20210005559A (ko) | 2018-03-27 | 2021-01-14 | 피티씨 테라퓨틱스, 인크. | 헌팅턴병 치료 화합물 |
| WO2020005882A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| CA3103976A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heterocyclic and heteroaryl compounds for treating huntington's disease |
| WO2020163405A1 (en) | 2019-02-05 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| CN113677344A (zh) | 2019-02-06 | 2021-11-19 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
| US11129829B2 (en) | 2019-06-17 | 2021-09-28 | Skyhawk Therapeutics, Inc. | Methods for modulating splicing |
| CA3156848A1 (en) | 2019-11-01 | 2021-05-06 | Novartis Ag | The use of a splicing modulator for a treatment slowing progression of huntington's disease |
| WO2021222366A1 (en) * | 2020-04-28 | 2021-11-04 | Kymera Therapeutics, Inc. | Irak inhibitors and uses thereof |
| CN116997548A (zh) | 2020-05-13 | 2023-11-03 | Chdi基金会股份有限公司 | 用于治疗亨廷顿病的htt调节剂 |
| US20240239811A1 (en) | 2020-07-02 | 2024-07-18 | Remix Therapeutics Inc. | 5-(5-(piperidin-4-yl)thieno[3,2-c]pyrazol-2-yl]indazole derivatives and related compounds as modulators for splicing nucleic acids and for the t |
| MX2023000168A (es) | 2020-07-02 | 2023-04-20 | Remix Therapeutics Inc | Derivados de 2-(indazol-5-il)-6-(piperidin-4-il)-1,7-naftiridina y compuestos relacionados como moduladores para el corte y empalme de ácidos nucleicos y para el tratamiento de enfermedades proliferativas. |
| WO2022194800A1 (en) * | 2021-03-17 | 2022-09-22 | F. Hoffmann-La Roche Ag | New thienopyrimidinone derivatives |
| CN116981673A (zh) * | 2021-03-17 | 2023-10-31 | 豪夫迈·罗氏有限公司 | 新颖噻二唑并嘧啶酮衍生物 |
| IL305203A (en) * | 2021-03-17 | 2023-10-01 | Hoffmann La Roche | New histories of thiazolopyrimidines |
| 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 |
| CN116262758A (zh) * | 2021-12-15 | 2023-06-16 | 上海博悦生物科技有限公司 | 7-甲基噻唑并[5,4-d]嘧啶类化合物、制备方法及其用途 |
| WO2023225244A1 (en) * | 2022-05-20 | 2023-11-23 | Biogen Ma Inc. | Heterocyclic compounds for treating huntington's disease |
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| US7423133B2 (en) | 2002-08-23 | 2008-09-09 | The Board Of Trustees Of The Leland Stanford Junior University | Fluorescent glycosides and methods for their use |
| US7473784B2 (en) * | 2005-08-01 | 2009-01-06 | Bristol-Myers Squibb Company | Benzothiazole and azabenzothiazole compounds useful as kinase inhibitors |
| AU2007229492B2 (en) * | 2006-03-28 | 2011-11-03 | High Point Pharmaceuticals, Llc | Benzothiazoles having histamine H3 receptor activity |
| US8153813B2 (en) | 2007-12-20 | 2012-04-10 | Abbott Laboratories | Benzothiazole and benzooxazole derivatives and methods of use |
| US8993580B2 (en) | 2008-03-14 | 2015-03-31 | Intellikine Llc | Benzothiazole kinase inhibitors and methods of use |
| US20090258907A1 (en) * | 2008-04-09 | 2009-10-15 | Abbott Laboratories | Compounds useful as inhibitors of rock kinases |
| WO2010024903A1 (en) | 2008-08-29 | 2010-03-04 | Yangbo Feng | BENZO[d]OXAZOLES AND BENZO[d]THIAZOLES AS KINASE INHIBITORS |
| WO2010071819A1 (en) * | 2008-12-19 | 2010-06-24 | Schering Corporation | Bicyclic heterocyclic derivatives and methods of use thereof |
| EA201270778A1 (ru) * | 2010-05-06 | 2013-04-30 | Бристол-Майерс Сквибб Компани | Бициклические гетероарильные аналоги в качестве модуляторов рецептора gpr119 |
| US20130046093A1 (en) | 2011-08-18 | 2013-02-21 | Korea Institute Of Science And Technology | Pharmaceutical compositions for preventing or treating degenerative brain disease and method of screening the same |
| EP3227301A1 (de) | 2014-12-02 | 2017-10-11 | Bayer CropScience AG | Bicyclische verbindungen als schädlingsbekämpfungsmittel |
| WO2016144351A1 (en) | 2015-03-11 | 2016-09-15 | E. I. Du Pont De Nemours And Company | Heterocycle-substituted bicyclic azole pesticides |
| CN113717154A (zh) | 2015-12-10 | 2021-11-30 | Ptc医疗公司 | 用于治疗亨廷顿病的方法 |
| CA3015947A1 (en) * | 2016-03-11 | 2017-09-14 | Ac Immune Sa | Bicyclic compounds for diagnosis and therapy of alpha-synuclein associated disorders |
| US10526345B2 (en) * | 2016-04-08 | 2020-01-07 | Mankind Pharma Ltd. | Compounds as GPR119 agonists |
| US10730868B2 (en) * | 2016-07-14 | 2020-08-04 | Bristol-Myers Squibb Company | Bicyclic heteroaryl substituted compounds |
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- 2019-06-25 WO PCT/US2019/038895 patent/WO2020005877A1/en unknown
- 2019-06-25 EA EA202092899A patent/EA202092899A1/ru unknown
- 2019-06-25 CN CN201980050967.1A patent/CN112805280A/zh active Pending
- 2019-06-25 KR KR1020207036998A patent/KR20210038845A/ko not_active Application Discontinuation
- 2019-06-25 MX MX2020014315A patent/MX2020014315A/es unknown
- 2019-06-25 SG SG11202012869SA patent/SG11202012869SA/en unknown
- 2019-06-25 AU AU2019294482A patent/AU2019294482B2/en active Active
- 2019-06-25 EP EP19736947.3A patent/EP3814345A1/en active Pending
- 2019-06-25 JP JP2020572894A patent/JP7515415B2/ja active Active
- 2019-06-25 US US17/254,828 patent/US20210284660A1/en active Pending
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2020
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2022
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