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.)
- Pending
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- -1 phenyl-oxy Chemical group 0.000 claims 386
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 84
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 75
- 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
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1H-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 27
- PBMFSQRYOILNGV-UHFFFAOYSA-N Pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 23
- WFJZBOIOPMOUCB-UHFFFAOYSA-N pyridazine;hydrochloride Chemical compound Cl.C1=CC=NN=C1 WFJZBOIOPMOUCB-UHFFFAOYSA-N 0.000 claims 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 15
- PUBSMDUBHLYMIX-UHFFFAOYSA-N phenol;dihydrochloride Chemical compound Cl.Cl.OC1=CC=CC=C1 PUBSMDUBHLYMIX-UHFFFAOYSA-N 0.000 claims 15
- 125000003277 amino group Chemical compound 0.000 claims 13
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 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 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
- 239000011780 sodium chloride Substances 0.000 claims 8
- 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 heteroatoms 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
- 150000003839 salts Chemical class 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
- 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
- 150000003840 hydrochlorides 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
- 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
- KYQCOXFCLRTKLS-UHFFFAOYSA-N pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-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
- 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
- 230000002730 additional Effects 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
- 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 pharmaceutic aid Substances 0.000 claims 2
- HYHBKLWDTGTBME-UHFFFAOYSA-N pyrazin-1-ium;chloride Chemical compound Cl.C1=CN=CC=N1 HYHBKLWDTGTBME-UHFFFAOYSA-N 0.000 claims 2
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 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
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-Methylimidazole 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- DDGWISNTVRLANS-UHFFFAOYSA-N C(#N)C1=CC(=CC2=CN(N=C12)C)C=1C=C2C(N=C(S2)C=2CCNCC=2)=C(C=1)C#N Chemical compound C(#N)C1=CC(=CC2=CN(N=C12)C)C=1C=C2C(N=C(S2)C=2CCNCC=2)=C(C=1)C#N DDGWISNTVRLANS-UHFFFAOYSA-N 0.000 claims 1
- FDGKUYKUXOBBNK-UHFFFAOYSA-N C(=O)OC1=C(C=CC(=C1)C=1C=NNC=1)C1=CC2=C(N=N1)N=C(S2)N1CCNCC1 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
- HHCHFNIJJJJYOC-UHFFFAOYSA-N C(=O)OC1=C(C=CC(=C1)C=1C=NNC=1)C1=CC2=C(N=N1)N=C(S2)NC1CNCC1 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
- HBBKMZBGPMTCED-GOEBONIOSA-N 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 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 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 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
- UJJRFNCZESXEJE-UHFFFAOYSA-N C(=O)OC1=C(C=CC(=C1)N1C=NC=C1)C1=CC2=C(N=N1)N=C(S2)N(C1CCNCC1)C 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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- BHWFUEFUAQQSQR-UHFFFAOYSA-N C(C)C1=CC(=CC2=CN(N=C12)C)C1=CC2=C(N=C(S2)N(C2CC(NC(C2)(C)C)(C)C)C)C=C1 Chemical compound C(C)C1=CC(=CC2=CN(N=C12)C)C1=CC2=C(N=C(S2)N(C2CC(NC(C2)(C)C)(C)C)C)C=C1 BHWFUEFUAQQSQR-UHFFFAOYSA-N 0.000 claims 1
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- PDAJSGMFDOPMGC-DZGCQCFKSA-N F[C@@H]1[C@@H](CN(C1)C)NC=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 Chemical compound F[C@@H]1[C@@H](CN(C1)C)NC=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 PDAJSGMFDOPMGC-DZGCQCFKSA-N 0.000 claims 1
- UNMMMJYHCNWTLE-HOCLYGCPSA-N F[C@@H]1[C@H](CN(C1)C)N(C=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1)C Chemical compound F[C@@H]1[C@H](CN(C1)C)N(C=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1)C UNMMMJYHCNWTLE-HOCLYGCPSA-N 0.000 claims 1
- PDAJSGMFDOPMGC-ZFWWWQNUSA-N F[C@@H]1[C@H](CN(C1)C)NC=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 Chemical compound F[C@@H]1[C@H](CN(C1)C)NC=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 PDAJSGMFDOPMGC-ZFWWWQNUSA-N 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N Hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- GJNOHSCBUFXPJP-UHFFFAOYSA-N N1(C=NC=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N=C(S2)N(C1CCN(CC1)C)C Chemical compound N1(C=NC=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N=C(S2)N(C1CCN(CC1)C)C GJNOHSCBUFXPJP-UHFFFAOYSA-N 0.000 claims 1
- KNCOZIJRCOKEDA-UHFFFAOYSA-N N1(C=NC=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N=C(S2)N(C1CCNCC1)C Chemical compound N1(C=NC=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N=C(S2)N(C1CCNCC1)C KNCOZIJRCOKEDA-UHFFFAOYSA-N 0.000 claims 1
- QLTLSTDYGQGDHT-UHFFFAOYSA-N N1(CCNCC1)C=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 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
- AEKMJOCLDYLNRK-UHFFFAOYSA-N N1=CC=C2SC(N)=NC2=N1 Chemical compound N1=CC=C2SC(N)=NC2=N1 AEKMJOCLDYLNRK-UHFFFAOYSA-N 0.000 claims 1
- TZJBQDLCDFHHNB-UHFFFAOYSA-N N1CC(C1)N(C=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1)C Chemical compound N1CC(C1)N(C=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1)C TZJBQDLCDFHHNB-UHFFFAOYSA-N 0.000 claims 1
- MACUKHPDJFPASL-UHFFFAOYSA-N N1CCC(CC1)NC=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 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
- UVVXKCVCRHBAHK-UHFFFAOYSA-N N1CCC(CCC1)C=1SC2=C(N=1)C=CC(=C2)C1=CC2=CN(N=C2C=C1)C 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
- GARDRQLMPWPBNF-UHFFFAOYSA-N N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N=C(S2)NC1CNCC1 Chemical compound N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CC2=C(N=N1)N=C(S2)NC1CNCC1 GARDRQLMPWPBNF-UHFFFAOYSA-N 0.000 claims 1
- RDNKWONEJBCEFB-UHFFFAOYSA-N N1N=CC(=C1)C=1C=CC(=C(C=1)O)C=1SC2=C(C=NC(=C2)C=2CC(NC(C=2)(C)C)(C)C)N=1 Chemical compound N1N=CC(=C1)C=1C=CC(=C(C=1)O)C=1SC2=C(C=NC(=C2)C=2CC(NC(C=2)(C)C)(C)C)N=1 RDNKWONEJBCEFB-UHFFFAOYSA-N 0.000 claims 1
- PBOKZSRCQRUJNW-UHFFFAOYSA-N N1N=CC2=CC(=CC=C12)C1=CC2=C(N=C(S2)N(C2CC(NC(C2)(C)C)(C)C)C)C=C1 Chemical compound N1N=CC2=CC(=CC=C12)C1=CC2=C(N=C(S2)N(C2CC(NC(C2)(C)C)(C)C)C)C=C1 PBOKZSRCQRUJNW-UHFFFAOYSA-N 0.000 claims 1
- NSFSKUWCAVCBMA-GJZGRUSLSA-N OC[C@H]1NCC[C@@H](C1)N(C=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1)C Chemical compound OC[C@H]1NCC[C@@H](C1)N(C=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1)C NSFSKUWCAVCBMA-GJZGRUSLSA-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
- DOLPEIBEKXLENB-MLGOLLRUSA-N [C@H]12CNCC[C@@H]2CN1C=1SC2=C(N=NC(=C2)C2=C(C=C(C=C2)C=2C=NNC=2)O)N=1 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
- DVXBPURNDGTXII-UHFFFAOYSA-N [Cl-].S1C=[NH+]C=2C=NC=CC=21 Chemical compound [Cl-].S1C=[NH+]C=2C=NC=CC=21 DVXBPURNDGTXII-UHFFFAOYSA-N 0.000 claims 1
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 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
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 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
- 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 1
- 150000002989 phenols Chemical compound 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
- 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
- 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
- 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862690540P | 2018-06-27 | 2018-06-27 | |
| US62/690,540 | 2018-06-27 | ||
| PCT/US2019/038895 WO2020005877A1 (en) | 2018-06-27 | 2019-06-25 | Heteroaryl compounds for treating huntington's disease |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021528466A JP2021528466A (ja) | 2021-10-21 |
| JPWO2020005877A5 true JPWO2020005877A5 (fi) | 2022-06-21 |
| JP7515415B2 JP7515415B2 (ja) | 2024-07-12 |
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