JP2021518395A5 - - Google Patents
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- JP2021518395A5 JP2021518395A5 JP2020550667A JP2020550667A JP2021518395A5 JP 2021518395 A5 JP2021518395 A5 JP 2021518395A5 JP 2020550667 A JP2020550667 A JP 2020550667A JP 2020550667 A JP2020550667 A JP 2020550667A JP 2021518395 A5 JP2021518395 A5 JP 2021518395A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- oxo
- amino
- thio
- pyrazine
- Prior art date
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- -1 naphthalene-1-yl group Chemical group 0.000 claims 171
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 13
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 7
- LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 4
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 2
- XQXXOWKUJRCUGZ-UHFFFAOYSA-N (4-methylpiperidin-4-yl)methanamine Chemical compound NCC1(C)CCNCC1 XQXXOWKUJRCUGZ-UHFFFAOYSA-N 0.000 claims 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- IBHIUPPGDYCBSV-UHFFFAOYSA-N 1,2-dihydroimidazol-5-one Chemical compound O=C1NCN=C1 IBHIUPPGDYCBSV-UHFFFAOYSA-N 0.000 claims 1
- SCDFILPFVOPDMQ-UHFFFAOYSA-N 1-(3-aminocyclohexyl)-4-(2,3-dichlorophenyl)pyridin-2-one Chemical compound NC1CC(CCC1)N1C(C=C(C=C1)C1=C(C(=CC=C1)Cl)Cl)=O SCDFILPFVOPDMQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- IFOXEIWAOZTLPH-APPDUMDISA-N 2-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-5-(2,3-dichloroanilino)-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1NC(C2=C(N=1)NC=C2NC1=C(C(=CC=C1)Cl)Cl)=O)C IFOXEIWAOZTLPH-APPDUMDISA-N 0.000 claims 1
- KKVLZJPXYUIIIF-KPZWWZAWSA-N 2-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-5-(2,3-dichloroanilino)-3-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-one Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1N(C(C2=C(N=1)NC=C2NC1=C(C(=CC=C1)Cl)Cl)=O)C)C KKVLZJPXYUIIIF-KPZWWZAWSA-N 0.000 claims 1
- AFVYHLNMSBZECS-KPZWWZAWSA-N 2-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-5-(2,3-dichlorophenoxy)-3-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-one Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1N(C(C2=C(N=1)NC=C2OC1=C(C(=CC=C1)Cl)Cl)=O)C)C AFVYHLNMSBZECS-KPZWWZAWSA-N 0.000 claims 1
- NRTBXUFMVUIAAD-UHFFFAOYSA-N 2-[4-(aminomethyl)-4-methylpiperidin-1-yl]-5-(2,3-dichlorophenyl)-1-methyl-6-oxopyrimidine-4-carbonitrile Chemical compound NCC1(CCN(CC1)C=1N(C(C(=C(N=1)C#N)C1=C(C(=CC=C1)Cl)Cl)=O)C)C NRTBXUFMVUIAAD-UHFFFAOYSA-N 0.000 claims 1
- PFWXRXTXRFAYGY-UHFFFAOYSA-N 2-[4-(aminomethyl)-4-methylpiperidin-1-yl]-5-(2,3-dichlorophenyl)sulfanyl-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound NCC1(CCN(CC1)C=1NC(C2=C(N=1)C=NC=C2SC1=C(C(=CC=C1)Cl)Cl)=O)C PFWXRXTXRFAYGY-UHFFFAOYSA-N 0.000 claims 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- SYWOGGKKFGSXNS-UHFFFAOYSA-N 3-(2-aminospiro[bicyclo[3.1.0]hexane-3,4'-piperidine]-1'-yl)-6-(2,3-dichlorophenyl)sulfanyl-1-methylpyrazin-2-one Chemical compound NC1C2CC2CC11CCN(CC1)C=1C(N(C(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)C)=O SYWOGGKKFGSXNS-UHFFFAOYSA-N 0.000 claims 1
- CBTBEOJTLGXQBZ-UHFFFAOYSA-N 3-(4-amino-2-oxa-8-azaspiro[4.5]decan-8-yl)-6-(2,3-dichlorophenyl)sulfanyl-1-methylpyrazin-2-one Chemical compound NC1COCC11CCN(CC1)C=1C(N(C(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)C)=O CBTBEOJTLGXQBZ-UHFFFAOYSA-N 0.000 claims 1
- OQJHFEOXMDSFMI-UHFFFAOYSA-N 3-(4-amino-2-oxa-8-azaspiro[4.5]decan-8-yl)-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound NC1COCC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O OQJHFEOXMDSFMI-UHFFFAOYSA-N 0.000 claims 1
- TVNBISXYSAIDKO-UHFFFAOYSA-N 3-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound NC1C2CN(CC12)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O TVNBISXYSAIDKO-UHFFFAOYSA-N 0.000 claims 1
- UJRCFTNATREODD-OAQYLSRUSA-N 3-[(1S)-1-amino-4-methoxyspiro[1,3-dihydroindene-2,4'-piperidine]-1'-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1C2=CC=CC(=C2CC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O)OC UJRCFTNATREODD-OAQYLSRUSA-N 0.000 claims 1
- UNRCWEPFQCACOS-HXUWFJFHSA-N 3-[(1S)-1-aminospiro[1,3-dihydroindene-2,4'-piperidine]-1'-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1C2=CC=CC=C2CC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O UNRCWEPFQCACOS-HXUWFJFHSA-N 0.000 claims 1
- QUDYOUIUXBQJBP-XJKSGUPXSA-N 3-[(2R,4R)-4-amino-2-methyl-8-azaspiro[4.5]decan-8-yl]-6-(2,3-dichlorophenyl)sulfanyl-1-methylpyrazin-2-one Chemical compound N[C@@H]1C[C@@H](CC11CCN(CC1)C=1C(N(C(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)C)=O)C QUDYOUIUXBQJBP-XJKSGUPXSA-N 0.000 claims 1
- KUOXDSAASAJNGS-IINYFYTJSA-N 3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-(2,3-dichloropyridin-4-yl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=NC=C1)Cl)Cl)=O)C KUOXDSAASAJNGS-IINYFYTJSA-N 0.000 claims 1
- NXGCMWDNLSXJON-MEDUHNTESA-N 3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-(2-chloro-3-fluorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)F)Cl)=O)C NXGCMWDNLSXJON-MEDUHNTESA-N 0.000 claims 1
- CDCDRNUWELNRQH-XHDPSFHLSA-N 3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-(3-chloro-1-methyl-2-oxopyridin-4-yl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(N(C=C1)C)=O)Cl)=O)C CDCDRNUWELNRQH-XHDPSFHLSA-N 0.000 claims 1
- FGOMPCFISFVIAW-XHDPSFHLSA-N 3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-(3-chloro-2-methoxypyridin-4-yl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=NC=C1)OC)Cl)=O)C FGOMPCFISFVIAW-XHDPSFHLSA-N 0.000 claims 1
- SXRNTXDHSFPIIM-IINYFYTJSA-N 3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-[(3-chloro-2-oxo-1H-pyridin-4-yl)sulfanyl]-1H-pyrazin-2-one Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(NC=C1)=O)Cl)=O)C SXRNTXDHSFPIIM-IINYFYTJSA-N 0.000 claims 1
- ILPTXIJRMXVQQY-CYBMUJFWSA-N 3-[(4R)-4-amino-2,2-difluoro-8-azaspiro[4.5]decan-8-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1CC(CC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O)(F)F ILPTXIJRMXVQQY-CYBMUJFWSA-N 0.000 claims 1
- SIULRGIDMNPONH-SBXXRYSUSA-N 3-[(4R)-4-amino-2-fluoro-8-azaspiro[4.5]decan-8-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1CC(CC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O)F SIULRGIDMNPONH-SBXXRYSUSA-N 0.000 claims 1
- OQJHFEOXMDSFMI-ZDUSSCGKSA-N 3-[(4R)-4-amino-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@H]1COCC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O OQJHFEOXMDSFMI-ZDUSSCGKSA-N 0.000 claims 1
- YGFOFLRRLIUMBV-CQSZACIVSA-N 3-[(4R)-4-amino-8-azaspiro[4.5]decan-8-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1CCCC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O YGFOFLRRLIUMBV-CQSZACIVSA-N 0.000 claims 1
- OQJHFEOXMDSFMI-CYBMUJFWSA-N 3-[(4S)-4-amino-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1COCC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O OQJHFEOXMDSFMI-CYBMUJFWSA-N 0.000 claims 1
- VFNBGRKGBQBPJF-LJQANCHMSA-N 3-[(5S)-5-aminospiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-1'-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1C=2C(=NC=CC=2)CC11CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O VFNBGRKGBQBPJF-LJQANCHMSA-N 0.000 claims 1
- DXEIVWFORALKLE-SNVBAGLBSA-N 3-[(6R)-6-amino-2-azaspiro[3.4]octan-2-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@H]1CC2(CN(C2)C=2C(NC(=CN=2)SC2=C(C(=CC=C2)Cl)Cl)=O)CC1 DXEIVWFORALKLE-SNVBAGLBSA-N 0.000 claims 1
- DXEIVWFORALKLE-JTQLQIEISA-N 3-[(6S)-6-amino-2-azaspiro[3.4]octan-2-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound N[C@@H]1CC2(CN(C2)C=2C(NC(=CN=2)SC2=C(C(=CC=C2)Cl)Cl)=O)CC1 DXEIVWFORALKLE-JTQLQIEISA-N 0.000 claims 1
- CUCPROKEXAIMCC-UHFFFAOYSA-N 3-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound NCC1(CN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O)C CUCPROKEXAIMCC-UHFFFAOYSA-N 0.000 claims 1
- LNZNZGGVJFERLM-UHFFFAOYSA-N 3-[4-(aminomethyl)-4-fluoropiperidin-1-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound NCC1(CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O)F LNZNZGGVJFERLM-UHFFFAOYSA-N 0.000 claims 1
- WHUNDUIZDAWWGK-UHFFFAOYSA-N 3-[4-(aminomethyl)-4-hydroxypiperidin-1-yl]-6-(2,3-dichlorophenyl)sulfanyl-1H-pyrazin-2-one Chemical compound NCC1(CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)Cl)Cl)=O)O WHUNDUIZDAWWGK-UHFFFAOYSA-N 0.000 claims 1
- NAKPYWCEFBAGEU-UHFFFAOYSA-N 3-[4-(aminomethyl)-4-methylpiperidin-1-yl]-6-(2,3-dichlorophenyl)-1H-pyrazin-2-one Chemical compound NCC1(CCN(CC1)C=1C(NC(=CN=1)C1=C(C(=CC=C1)Cl)Cl)=O)C NAKPYWCEFBAGEU-UHFFFAOYSA-N 0.000 claims 1
- HAAAXABVIGQBOT-UHFFFAOYSA-N 3-[4-(aminomethyl)-4-methylpiperidin-1-yl]-6-(2-chloro-3-methoxyphenyl)sulfanyl-1H-pyrazin-2-one Chemical compound NCC1(CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=CC=C1)OC)Cl)=O)C HAAAXABVIGQBOT-UHFFFAOYSA-N 0.000 claims 1
- IGWAIPLFFIMTAQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-4-methylpiperidin-1-yl]-6-(3-chloro-2-methoxypyridin-4-yl)sulfanyl-1H-pyrazin-2-one Chemical compound NCC1(CCN(CC1)C=1C(NC(=CN=1)SC1=C(C(=NC=C1)OC)Cl)=O)C IGWAIPLFFIMTAQ-UHFFFAOYSA-N 0.000 claims 1
- VCHHVKLUGGQAET-UHFFFAOYSA-N 3-[4-(aminomethyl)-4-methylpiperidin-1-yl]-6-[2-(trifluoromethyl)phenyl]sulfanyl-1H-pyrazin-2-one Chemical compound NCC1(CCN(CC1)C=1C(NC(=CN=1)SC1=C(C=CC=C1)C(F)(F)F)=O)C VCHHVKLUGGQAET-UHFFFAOYSA-N 0.000 claims 1
- SVRUKQKRAHSRTQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-4-methylpiperidin-1-yl]-6-[2-(trifluoromethyl)pyridin-3-yl]sulfanyl-1H-pyrazin-2-one Chemical compound NCC1(CCN(CC1)C=1C(NC(=CN=1)SC=1C(=NC=CC=1)C(F)(F)F)=O)C SVRUKQKRAHSRTQ-UHFFFAOYSA-N 0.000 claims 1
- VGNPATCUBXRDBE-UHFFFAOYSA-N 3-[4-(aminomethyl)-4-methylpiperidin-1-yl]-6-naphthalen-1-ylsulfanyl-1H-pyrazin-2-one Chemical compound NCC1(CCN(CC1)C=1C(NC(=CN=1)SC1=CC=CC2=CC=CC=C12)=O)C VGNPATCUBXRDBE-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- SQDOXGXCLKGIAT-UHFFFAOYSA-N 4-amino-2-(6-amino-2-azaspiro[3.4]octan-2-yl)-5-(2,3-dichlorophenyl)sulfanyl-1H-pyrimidin-6-one Chemical compound NC1=C(C(NC(=N1)N1CC2(C1)CC(CC2)N)=O)SC1=C(C(=CC=C1)Cl)Cl SQDOXGXCLKGIAT-UHFFFAOYSA-N 0.000 claims 1
- FGTDIEOPGHWZOR-UHFFFAOYSA-N 4-amino-2-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-5-(2,3-dichlorophenyl)sulfanyl-1H-pyrimidin-6-one Chemical compound NC1=C(C(NC(=N1)N1CC2C(C2C1)N)=O)SC1=C(C(=CC=C1)Cl)Cl FGTDIEOPGHWZOR-UHFFFAOYSA-N 0.000 claims 1
- MGSZQRPSSXLWIN-UHFFFAOYSA-N 4-amino-2-(6-amino-3-azabicyclo[3.2.0]heptan-3-yl)-5-(2,3-dichlorophenyl)sulfanyl-1H-pyrimidin-6-one Chemical compound NC1=C(C(NC(=N1)N1CC2CC(C2C1)N)=O)SC1=C(C(=CC=C1)Cl)Cl MGSZQRPSSXLWIN-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- IQVNXICBINOVNT-UHFFFAOYSA-N 5-[1-(1-aminopropan-2-yl)piperidin-4-yl]-3-(2,3-dichlorophenyl)sulfanyl-1,6-dihydropyrazolo[4,3-d]pyrimidin-7-one Chemical compound NCC(C)N1CCC(CC1)C=1NC(C2=C(N=1)C(=NN2)SC1=C(C(=CC=C1)Cl)Cl)=O IQVNXICBINOVNT-UHFFFAOYSA-N 0.000 claims 1
- QEESQKCQMWEXCC-UHFFFAOYSA-N 6-(2,3-dichlorophenyl)sulfanyl-3-(piperidin-4-ylamino)-1H-pyrazin-2-one Chemical compound ClC1=C(C=CC=C1Cl)SC1=CN=C(C(N1)=O)NC1CCNCC1 QEESQKCQMWEXCC-UHFFFAOYSA-N 0.000 claims 1
- OYYXDXFCUKNPSW-UHFFFAOYSA-N 6-(2-amino-3-chloropyridin-4-yl)sulfanyl-3-[4-(aminomethyl)-4-methylpiperidin-1-yl]-1H-pyrazin-2-one Chemical compound NC1=NC=CC(=C1Cl)SC1=CN=C(C(N1)=O)N1CCC(CC1)(C)CN OYYXDXFCUKNPSW-UHFFFAOYSA-N 0.000 claims 1
- PNLMLGLYVFMTEO-UHFFFAOYSA-N 6-(5-amino-2-chlorophenyl)sulfanyl-3-[4-(aminomethyl)-4-methylpiperidin-1-yl]-1H-pyrazin-2-one Chemical compound NC=1C=CC(=C(C=1)SC1=CN=C(C(N1)=O)N1CCC(CC1)(C)CN)Cl PNLMLGLYVFMTEO-UHFFFAOYSA-N 0.000 claims 1
- BRGIDJLKNGSBSX-MEDUHNTESA-N 6-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-3-(2,3-dichloroanilino)-4-methyl-2H-pyrazolo[3,4-b]pyrazin-5-one Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1C(N(C2=C(N=1)NN=C2NC1=C(C(=CC=C1)Cl)Cl)C)=O)C BRGIDJLKNGSBSX-MEDUHNTESA-N 0.000 claims 1
- MSOFATSUYQHEEW-UHFFFAOYSA-N 6-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-3-(2,3-dichlorophenoxy)-2,5-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical compound NCC1(CN(CC1)C=1NC(C2=C(N=1)NN=C2OC1=C(C(=CC=C1)Cl)Cl)=O)C MSOFATSUYQHEEW-UHFFFAOYSA-N 0.000 claims 1
- MXRKHCMUIGDXSN-UHFFFAOYSA-N 6-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-3-(2,3-dichlorophenoxy)-5-methyl-2H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound NCC1(CN(CC1)C=1N(C(C2=C(N=1)NN=C2OC1=C(C(=CC=C1)Cl)Cl)=O)C)C MXRKHCMUIGDXSN-UHFFFAOYSA-N 0.000 claims 1
- NFJWKKZRQXOAOG-UHFFFAOYSA-N 6-[4-(aminomethyl)-4-methylpiperidin-1-yl]-3-(2,3-dichloroanilino)-2,5-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical compound NCC1(CCN(CC1)C=1NC(C2=C(N=1)NN=C2NC1=C(C(=CC=C1)Cl)Cl)=O)C NFJWKKZRQXOAOG-UHFFFAOYSA-N 0.000 claims 1
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2019
- 2019-03-18 RU RU2020133727A patent/RU2020133727A/ru unknown
- 2019-03-18 JP JP2020550667A patent/JP7265275B2/ja active Active
- 2019-03-18 EP EP19771115.3A patent/EP3768664B1/en active Active
- 2019-03-18 AU AU2019239658A patent/AU2019239658A1/en not_active Abandoned
- 2019-03-18 US US16/356,360 patent/US10561655B2/en active Active
- 2019-03-18 KR KR1020207030224A patent/KR102724968B1/ko active Active
- 2019-03-18 WO PCT/US2019/022717 patent/WO2019182960A1/en not_active Ceased
- 2019-03-18 CA CA3097709A patent/CA3097709A1/en not_active Abandoned
- 2019-03-18 TW TW108109165A patent/TW201940167A/zh unknown
- 2019-03-18 CN CN201980031603.9A patent/CN112368272B/zh active Active
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