JPWO2020081848A5 - - Google Patents
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- Publication number
- JPWO2020081848A5 JPWO2020081848A5 JP2021520556A JP2021520556A JPWO2020081848A5 JP WO2020081848 A5 JPWO2020081848 A5 JP WO2020081848A5 JP 2021520556 A JP2021520556 A JP 2021520556A JP 2021520556 A JP2021520556 A JP 2021520556A JP WO2020081848 A5 JPWO2020081848 A5 JP WO2020081848A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrido
- thio
- pyrazin
- amine
- amino
- 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 bicyclic aryl Chemical group 0.000 claims 74
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000002619 bicyclic group Chemical group 0.000 claims 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 230000003463 hyperproliferative effect Effects 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- XSYWQEZOMDPGFT-UHFFFAOYSA-N 3-chloro-4-[2-(3,8-diazabicyclo[3.2.1]octan-8-yl)pyrido[2,3-b]pyrazin-6-yl]sulfanylpyridin-2-amine Chemical compound C1CC2CNCC1N2C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)N)Cl XSYWQEZOMDPGFT-UHFFFAOYSA-N 0.000 claims 2
- JYRWFZZKEKTMSK-UHFFFAOYSA-N decan-4-amine Chemical compound CCCCCCC(N)CCC JYRWFZZKEKTMSK-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 210000004214 philadelphia chromosome Anatomy 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- VRQDPNKOUPEWOC-UHFFFAOYSA-N spiro[bicyclo[2.2.2]octane-3,3'-piperidine] Chemical compound C1CCNCC21C(CC1)CCC1C2 VRQDPNKOUPEWOC-UHFFFAOYSA-N 0.000 claims 2
- OZSKKNLHNCVVTE-QFIPXVFZSA-N (1R)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-4-chlorospiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@H](C2=CC=CC(=C2C3)Cl)N)N=1 OZSKKNLHNCVVTE-QFIPXVFZSA-N 0.000 claims 1
- LARREPGAAVKCCX-QHCPKHFHSA-N (1R)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-4-methylspiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound CC1=C2CC3(CCN(CC3)C4=CN=C5C(=N4)C=CC(=N5)SC6=C(C(=NC=C6)N)Cl)[C@H](C2=CC=C1)N LARREPGAAVKCCX-QHCPKHFHSA-N 0.000 claims 1
- YPLHAXDRIIJALD-QFIPXVFZSA-N (1R)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-5-chlorospiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound C1CN(CCC12CC3=C([C@@H]2N)C=CC(=C3)Cl)C4=CN=C5C(=N4)C=CC(=N5)SC6=C(C(=NC=C6)N)Cl YPLHAXDRIIJALD-QFIPXVFZSA-N 0.000 claims 1
- ZJCWKDUZVMTXRX-QHCPKHFHSA-N (1R)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-6-methylspiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound CC1=CC2=C(CC3([C@H]2N)CCN(CC3)C4=CN=C5C(=N4)C=CC(=N5)SC6=C(C(=NC=C6)N)Cl)C=C1 ZJCWKDUZVMTXRX-QHCPKHFHSA-N 0.000 claims 1
- DMGHTRNPFCSYPI-HXUWFJFHSA-N (1R)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[1,3-dihydroindene-2,3'-azetidine]-1-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CC3([C@@H](C4=CC=CC=C4C3)N)C2)N=1 DMGHTRNPFCSYPI-HXUWFJFHSA-N 0.000 claims 1
- NYADKSCWULBOJD-JFGNBEQYSA-N (1R,5R,6S)-3-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-8-oxa-3-azabicyclo[3.2.1]octan-6-amine Chemical compound C1[C@@H]2CN(C[C@H]([C@H]1N)O2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)N)Cl NYADKSCWULBOJD-JFGNBEQYSA-N 0.000 claims 1
- OZSKKNLHNCVVTE-JOCHJYFZSA-N (1S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-4-chlorospiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C2=CC=CC(=C2C3)Cl)N)N=1 OZSKKNLHNCVVTE-JOCHJYFZSA-N 0.000 claims 1
- LARREPGAAVKCCX-HSZRJFAPSA-N (1S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-4-methylspiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C2=CC=CC(=C2C3)C)N)N=1 LARREPGAAVKCCX-HSZRJFAPSA-N 0.000 claims 1
- LCDKHVMBHOTRTK-JOCHJYFZSA-N (1S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-5-fluorospiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C2=CC=C(C=C2C3)F)N)N=1 LCDKHVMBHOTRTK-JOCHJYFZSA-N 0.000 claims 1
- XSVLQUPXLDCENB-HSZRJFAPSA-N (1S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-6-methoxyspiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound COC1=CC2=C(CC3([C@@H]2N)CCN(CC3)C4=CN=C5C(=N4)C=CC(=N5)SC6=C(C(=NC=C6)N)Cl)C=C1 XSVLQUPXLDCENB-HSZRJFAPSA-N 0.000 claims 1
- ZJCWKDUZVMTXRX-HSZRJFAPSA-N (1S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-6-methylspiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound CC1=CC2=C(CC3([C@@H]2N)CCN(CC3)C4=CN=C5C(=N4)C=CC(=N5)SC6=C(C(=NC=C6)N)Cl)C=C1 ZJCWKDUZVMTXRX-HSZRJFAPSA-N 0.000 claims 1
- DMGHTRNPFCSYPI-FQEVSTJZSA-N (1S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[1,3-dihydroindene-2,3'-azetidine]-1-amine Chemical compound C1C2=CC=CC=C2[C@@H](C13CN(C3)C4=CN=C5C(=N4)C=CC(=N5)SC6=C(C(=NC=C6)N)Cl)N DMGHTRNPFCSYPI-FQEVSTJZSA-N 0.000 claims 1
- XNIYTWAJXXHCLG-JOCHJYFZSA-N (1S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C2=CC=CC=C2C3)N)N=1 XNIYTWAJXXHCLG-JOCHJYFZSA-N 0.000 claims 1
- ULUKTOYTLCREPI-HSZRJFAPSA-N (1S)-1'-[6-(6-amino-3-chloro-2-methoxypyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound COC1=C(C(=CC(=N1)N)SC2=NC3=NC=C(N=C3C=C2)N4CCC5(CC4)CC6=CC=CC=C6[C@H]5N)Cl ULUKTOYTLCREPI-HSZRJFAPSA-N 0.000 claims 1
- WFBKCTDJMVCMAR-JOCHJYFZSA-N (1S)-1'-[6-(6-amino-4,5-dichloropyridin-3-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound NC1=C(C(=C(C=N1)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C2=CC=CC=C2C3)N)N=1)Cl)Cl WFBKCTDJMVCMAR-JOCHJYFZSA-N 0.000 claims 1
- ZMTQXYGXNBYNLQ-RUZDIDTESA-N (1S)-1'-[6-(6-chloroimidazo[1,2-a]pyridin-3-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound ClC=1C=CC=2N(C=1)C(=CN=2)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C2=CC=CC=C2C3)N)N=1 ZMTQXYGXNBYNLQ-RUZDIDTESA-N 0.000 claims 1
- CMFWOJVHVWLDQX-JOCHJYFZSA-N (1S)-1'-[6-[2-(trifluoromethyl)pyridin-3-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[1,3-dihydroindene-2,4'-piperidine]-1-amine Chemical compound C1CN(CCC12CC3=CC=CC=C3[C@H]2N)C4=CN=C5C(=N4)C=CC(=N5)SC6=C(N=CC=C6)C(F)(F)F CMFWOJVHVWLDQX-JOCHJYFZSA-N 0.000 claims 1
- NSEIQYVDCNVFFR-XMMPIXPASA-N (1S)-1-amino-1'-[6-(3-chloro-2-methylpyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[1,3-dihydroindene-2,4'-piperidine]-5-ol Chemical compound N[C@@H]1C2=CC=C(C=C2CC11CCN(CC1)C=1N=C2C(=NC=1)N=C(C=C2)SC1=C(C(=NC=C1)C)Cl)O NSEIQYVDCNVFFR-XMMPIXPASA-N 0.000 claims 1
- LANVDWAEBRQKDI-SWLSCSKDSA-N (2R,4R)-4-amino-8-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-8-azaspiro[4.5]decan-2-ol Chemical compound C1CN(CCC12C[C@H](C[C@H]2N)O)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)N)Cl LANVDWAEBRQKDI-SWLSCSKDSA-N 0.000 claims 1
- GYKBBFLZXIYTLN-OAQYLSRUSA-N (3R)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[3H-1-benzofuran-2,4'-piperidine]-3-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)OC2=C([C@H]3N)C=CC=C2)N=1 GYKBBFLZXIYTLN-OAQYLSRUSA-N 0.000 claims 1
- VPJXWCALBDMBRW-WJONJSRFSA-N (3R)-1-[4-[2-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]pyrido[2,3-b]pyrazin-6-yl]sulfanyl-3-chloropyridin-2-yl]pyrrolidin-3-ol Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)N6CC[C@H](C6)O)Cl)CO1)N VPJXWCALBDMBRW-WJONJSRFSA-N 0.000 claims 1
- CXAJPNYARDLNEG-QHCPKHFHSA-N (3R)-3-amino-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[1,3-dihydroindene-2,4'-piperidine]-5-carbonitrile Chemical compound N[C@H]1C2=CC(=CC=C2CC11CCN(CC1)C=1N=C2C(=NC=1)N=C(C=C2)SC1=C(C(=NC=C1)N)Cl)C#N CXAJPNYARDLNEG-QHCPKHFHSA-N 0.000 claims 1
- VPJXWCALBDMBRW-PONJGIIJSA-N (3S)-1-[4-[2-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]pyrido[2,3-b]pyrazin-6-yl]sulfanyl-3-chloropyridin-2-yl]pyrrolidin-3-ol Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1N=C2C(=NC=1)N=C(C=C2)SC1=C(C(=NC=C1)N1C[C@H](CC1)O)Cl)C VPJXWCALBDMBRW-PONJGIIJSA-N 0.000 claims 1
- CXAJPNYARDLNEG-HSZRJFAPSA-N (3S)-3-amino-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[1,3-dihydroindene-2,4'-piperidine]-5-carbonitrile Chemical compound N[C@@H]1C2=CC(=CC=C2CC11CCN(CC1)C=1N=C2C(=NC=1)N=C(C=C2)SC1=C(C(=NC=C1)N)Cl)C#N CXAJPNYARDLNEG-HSZRJFAPSA-N 0.000 claims 1
- QDHGFXBJOHKTTK-YCRPNKLZSA-N (3S,4S)-3-methyl-8-[6-(1-methylpyrrolo[2,3-b]pyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C6C=CN(C6=NC=C5)C)CO1)N QDHGFXBJOHKTTK-YCRPNKLZSA-N 0.000 claims 1
- LXGHMQNLASTXAL-VBKZILBWSA-N (3S,4S)-3-methyl-8-[6-(1H-pyrrolo[2,3-b]pyridin-4-ylsulfanyl)pyrido[2,3-b]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C6C=CNC6=NC=C5)CO1)N LXGHMQNLASTXAL-VBKZILBWSA-N 0.000 claims 1
- RWSIRNVELKSHRS-YCRPNKLZSA-N (3S,4S)-3-methyl-8-[6-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrido[2,3-b]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@@H]1OCC2([C@@H]1N)CCN(CC2)C=1N=C2C(=NC=1)N=C(C=C2)SC1=C2C(=NC=C1)NC=C2C RWSIRNVELKSHRS-YCRPNKLZSA-N 0.000 claims 1
- LUUDQBCPMCEOKS-SCLBCKFNSA-N (3S,4S)-3-methyl-8-[6-[2-(trifluoromethyl)pyridin-3-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(N=CC=C5)C(F)(F)F)CO1)N LUUDQBCPMCEOKS-SCLBCKFNSA-N 0.000 claims 1
- IRWAOMZOLYCRJH-ORAYPTAESA-N (3S,4S)-3-methyl-8-[6-[2-(trifluoromethyl)pyridin-4-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=CC(=NC=C5)C(F)(F)F)CO1)N IRWAOMZOLYCRJH-ORAYPTAESA-N 0.000 claims 1
- GXWAZAAAKHRHCN-ORAYPTAESA-N (3S,4S)-3-methyl-8-[6-[3-(trifluoromethyl)pyridin-4-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C=NC=C5)C(F)(F)F)CO1)N GXWAZAAAKHRHCN-ORAYPTAESA-N 0.000 claims 1
- GMLFRCSSZBAEEL-RNODOKPDSA-N (3S,4S)-3-methyl-8-[6-[[5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]sulfanyl]pyrido[2,3-b]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C6C=CNC6=NC=C5C(F)(F)F)CO1)N GMLFRCSSZBAEEL-RNODOKPDSA-N 0.000 claims 1
- FGWGNCYBMDTWKY-ORAYPTAESA-N (3S,4S)-8-[6-(1H-imidazo[4,5-b]pyridin-7-ylsulfanyl)pyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound N1=CNC2=NC=CC(=C21)SC=1C=CC=2C(=NC=C(N=2)N2CCC3([C@@H]([C@@H](OC3)C)N)CC2)N=1 FGWGNCYBMDTWKY-ORAYPTAESA-N 0.000 claims 1
- FXXHWOXEFPTYFG-KPZWWZAWSA-N (3S,4S)-8-[6-(2,3-dichloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)Cl)Cl)CO1)N FXXHWOXEFPTYFG-KPZWWZAWSA-N 0.000 claims 1
- LBDMGVFWRXPVGX-HRAATJIYSA-N (3S,4S)-8-[6-(2,3-dimethylpyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)C)C)CO1)N LBDMGVFWRXPVGX-HRAATJIYSA-N 0.000 claims 1
- CNWPAKCFVFDYQN-KPZWWZAWSA-N (3S,4S)-8-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3([C@@H]([C@@H](OC3)C)N)CC2)N=1 CNWPAKCFVFDYQN-KPZWWZAWSA-N 0.000 claims 1
- KWECHTNMZUVGJX-KPZWWZAWSA-N (3S,4S)-8-[6-(2-amino-3-fluoropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)N)F)CO1)N KWECHTNMZUVGJX-KPZWWZAWSA-N 0.000 claims 1
- YUDIARZXLVJNKY-ORAYPTAESA-N (3S,4S)-8-[6-(2-amino-3-methoxypyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound NC1=NC=CC(=C1OC)SC=1C=CC=2C(=NC=C(N=2)N2CCC3([C@@H]([C@@H](OC3)C)N)CC2)N=1 YUDIARZXLVJNKY-ORAYPTAESA-N 0.000 claims 1
- YXVJUSOEWJOJLQ-IFXJQAMLSA-N (3S,4S)-8-[6-(2-amino-3-methylpyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound NC1=NC=CC(=C1C)SC=1C=CC=2C(=NC=C(N=2)N2CCC3([C@@H]([C@@H](OC3)C)N)CC2)N=1 YXVJUSOEWJOJLQ-IFXJQAMLSA-N 0.000 claims 1
- FRMOYPZKSNSGRE-HXPMCKFVSA-N (3S,4S)-8-[6-(2-amino-5-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound NC1=NC=C(C(=C1)SC=1C=CC=2C(=NC=C(N=2)N2CCC3([C@@H]([C@@H](OC3)C)N)CC2)N=1)Cl FRMOYPZKSNSGRE-HXPMCKFVSA-N 0.000 claims 1
- WZJVWFHSVVHPOS-KSFYIVLOSA-N (3S,4S)-8-[6-(3-chloro-2-morpholin-4-ylpyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound ClC=1C(=NC=CC=1SC=1C=CC=2C(=NC=C(N=2)N2CCC3([C@@H]([C@@H](OC3)C)N)CC2)N=1)N1CCOCC1 WZJVWFHSVVHPOS-KSFYIVLOSA-N 0.000 claims 1
- JSHRRIDKNPDAEB-KSFYIVLOSA-N (3S,4S)-8-[6-(3-chloro-2-pyrrolidin-1-ylpyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)N6CCCC6)Cl)CO1)N JSHRRIDKNPDAEB-KSFYIVLOSA-N 0.000 claims 1
- TYNAIVGURYTUIF-ORAYPTAESA-N (3S,4S)-8-[6-(3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C=NC=C5)Cl)CO1)N TYNAIVGURYTUIF-ORAYPTAESA-N 0.000 claims 1
- ISLMPGAQDNQHAQ-ORAYPTAESA-N (3S,4S)-8-[6-(3-fluoropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C=NC=C5)F)CO1)N ISLMPGAQDNQHAQ-ORAYPTAESA-N 0.000 claims 1
- NVXSXSPUVVVHID-BBATYDOGSA-N (3S,4S)-8-[6-(6-amino-2,3-dichloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound NC1=CC(=C(C(=N1)Cl)Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3([C@@H]([C@@H](OC3)C)N)CC2)N=1 NVXSXSPUVVVHID-BBATYDOGSA-N 0.000 claims 1
- MIXKRLZSTGZOTJ-KPZWWZAWSA-N (3S,4S)-8-[6-(6-amino-2-chloropyridin-3-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(N=C(C=C5)N)Cl)CO1)N MIXKRLZSTGZOTJ-KPZWWZAWSA-N 0.000 claims 1
- YPEHLJMUFJTGOE-MEDUHNTESA-N (3S,4S)-8-[6-(6-amino-5-chloropyrimidin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=NC=NC(=C5Cl)N)CO1)N YPEHLJMUFJTGOE-MEDUHNTESA-N 0.000 claims 1
- KRMALMVEPLKLKV-RNODOKPDSA-N (3S,4S)-8-[6-[(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C6C=CNC6=NC=C5Cl)CO1)N KRMALMVEPLKLKV-RNODOKPDSA-N 0.000 claims 1
- WCGYCOKDOPJEDY-RNODOKPDSA-N (3S,4S)-8-[6-[(5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound FC=1C(=C2C(=NC=1)NC=C2)SC=1C=CC=2C(=NC=C(N=2)N2CCC3([C@@H]([C@@H](OC3)C)N)CC2)N=1 WCGYCOKDOPJEDY-RNODOKPDSA-N 0.000 claims 1
- VSFPSZKXWKIBDM-RNODOKPDSA-N (3S,4S)-8-[6-[(6-amino-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound NC1=CC(=C2C(=N1)NC=C2)SC=1C=CC=2C(=NC=C(N=2)N2CCC3([C@@H]([C@@H](OC3)C)N)CC2)N=1 VSFPSZKXWKIBDM-RNODOKPDSA-N 0.000 claims 1
- IOCAWKYQBONCDW-KPZWWZAWSA-N (3S,4S)-8-[6-[2-amino-3-(trifluoromethyl)pyridin-4-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound NC1=NC=CC(=C1C(F)(F)F)SC=1C=CC=2C(=NC=C(N=2)N2CCC3([C@@H]([C@@H](OC3)C)N)CC2)N=1 IOCAWKYQBONCDW-KPZWWZAWSA-N 0.000 claims 1
- SOVXIBFUINKCQA-KSFYIVLOSA-N (3S,4S)-8-[6-[3-chloro-2-(1,1-dioxo-1,4-thiazinan-4-yl)pyridin-4-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1N=C2C(=NC=1)N=C(C=C2)SC1=C(C(=NC=C1)N1CCS(CC1)(=O)=O)Cl)C SOVXIBFUINKCQA-KSFYIVLOSA-N 0.000 claims 1
- IRZMBGVQAVOUHZ-YCRPNKLZSA-N (3S,4S)-8-[6-[3-chloro-2-(2-methoxyethylamino)pyridin-4-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)NCCOC)Cl)CO1)N IRZMBGVQAVOUHZ-YCRPNKLZSA-N 0.000 claims 1
- XINAXVKXQPQSFK-LHSJRXKWSA-N (3S,4S)-8-[6-[3-chloro-2-(cyclopropylamino)pyridin-4-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)NC6CC6)Cl)CO1)N XINAXVKXQPQSFK-LHSJRXKWSA-N 0.000 claims 1
- FCHPLJDSLAZVNU-ORAYPTAESA-N (3S,4S)-8-[6-[3-chloro-2-(methylamino)pyridin-4-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)NC)Cl)CO1)N FCHPLJDSLAZVNU-ORAYPTAESA-N 0.000 claims 1
- RNKVBMKFYWSEAQ-KPZWWZAWSA-N (3S,4S)-8-[6-[6-amino-2-(trifluoromethyl)pyridin-3-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine Chemical compound C[C@H]1[C@H](C2(CCN(CC2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(N=C(C=C5)N)C(F)(F)F)CO1)N RNKVBMKFYWSEAQ-KPZWWZAWSA-N 0.000 claims 1
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- MODFWBDEFHGHST-QGZVFWFLSA-N (4R)-8-[6-(2,3-dichlorophenyl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-8-azaspiro[4.5]decan-4-amine Chemical compound ClC1=C(C=CC=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CCC[C@H]3N)CC2)N=1 MODFWBDEFHGHST-QGZVFWFLSA-N 0.000 claims 1
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- ZSLYUFDRBWEENT-QFIPXVFZSA-N (5R)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-2-methoxyspiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-5-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@H](C=2C(=NC(=CC=2)OC)C3)N)N=1 ZSLYUFDRBWEENT-QFIPXVFZSA-N 0.000 claims 1
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- URLQCJFKEIJEMW-NRFANRHFSA-N (5R)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-fluorospiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-5-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@H](C=2C(=NC=C(C=2)F)C3)N)N=1 URLQCJFKEIJEMW-NRFANRHFSA-N 0.000 claims 1
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- RFYWVDVFMZNBBB-JOCHJYFZSA-N (5S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-2-methylspiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-5-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C=2C(=NC(=CC=2)C)C3)N)N=1 RFYWVDVFMZNBBB-JOCHJYFZSA-N 0.000 claims 1
- URLQCJFKEIJEMW-OAQYLSRUSA-N (5S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-fluorospiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-5-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C=2C(=NC=C(C=2)F)C3)N)N=1 URLQCJFKEIJEMW-OAQYLSRUSA-N 0.000 claims 1
- BBHOXURWAZHPOP-JOCHJYFZSA-N (5S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3-methoxyspiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-5-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C=2C(=NC=C(C=2)OC)C3)N)N=1 BBHOXURWAZHPOP-JOCHJYFZSA-N 0.000 claims 1
- BWQAQACZKDLJAW-OAQYLSRUSA-N (5S)-1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-5-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C=2C(=NC=CC=2)C3)N)N=1 BWQAQACZKDLJAW-OAQYLSRUSA-N 0.000 claims 1
- QZDIZZWLGDHWLW-JOCHJYFZSA-N (5S)-1'-[6-(2-amino-5-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-5-amine Chemical compound NC1=NC=C(C(=C1)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)[C@@H](C=2C(=NC=CC=2)C3)N)N=1)Cl QZDIZZWLGDHWLW-JOCHJYFZSA-N 0.000 claims 1
- QOGBWRCHPIOLJU-OAQYLSRUSA-N (5S)-1'-[6-[2-(trifluoromethyl)pyridin-3-yl]sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-5-amine Chemical compound C1CN(CCC12CC3=C([C@H]2N)C=CC=N3)C4=CN=C5C(=N4)C=CC(=N5)SC6=C(N=CC=C6)C(F)(F)F QOGBWRCHPIOLJU-OAQYLSRUSA-N 0.000 claims 1
- QMIMHUDEVKGOTQ-DVQDXYAYSA-N (e)-n-[(1s)-1-(3-morpholin-4-ylphenyl)ethyl]-3-phenylprop-2-enamide Chemical compound N([C@@H](C)C=1C=C(C=CC=1)N1CCOCC1)C(=O)\C=C\C1=CC=CC=C1 QMIMHUDEVKGOTQ-DVQDXYAYSA-N 0.000 claims 1
- RQTAAUPFFCLFOR-UHFFFAOYSA-N 1'-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]spiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-7-amine Chemical compound NC1=NC=CC(=C1Cl)SC=1C=CC=2C(=NC=C(N=2)N2CCC3(CC2)CC=2C(=NC=CC=2)C3N)N=1 RQTAAUPFFCLFOR-UHFFFAOYSA-N 0.000 claims 1
- GPJJNZUUUIPEMK-UHFFFAOYSA-N 1-(6-isoquinolin-8-ylsulfanylpyrido[2,3-b]pyrazin-2-yl)-4-methylpiperidin-4-amine Chemical compound CC1(CCN(CC1)C2=CN=C3C(=N2)C=CC(=N3)SC4=CC=CC5=C4C=NC=C5)N GPJJNZUUUIPEMK-UHFFFAOYSA-N 0.000 claims 1
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- CXPZZFXDJJNRRZ-QMHKHESXSA-N 1-[4-[2-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]pyrido[2,3-b]pyrazin-6-yl]sulfanyl-3-chloropyridin-2-yl]piperidin-4-ol Chemical compound N[C@@H]1[C@@H](OCC11CCN(CC1)C=1N=C2C(=NC=1)N=C(C=C2)SC1=C(C(=NC=C1)N1CCC(CC1)O)Cl)C CXPZZFXDJJNRRZ-QMHKHESXSA-N 0.000 claims 1
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- HMAGSPHSAACAHH-AREMUKBSSA-N 1-[4-[2-[(5S)-5-aminospiro[5,7-dihydrocyclopenta[b]pyridine-6,4'-piperidine]-1'-yl]pyrido[2,3-b]pyrazin-6-yl]sulfanyl-3-chloropyridin-2-yl]piperidin-4-ol Chemical compound C1CN(CCC1O)C2=NC=CC(=C2Cl)SC3=NC4=NC=C(N=C4C=C3)N5CCC6(CC5)CC7=C([C@H]6N)C=CC=N7 HMAGSPHSAACAHH-AREMUKBSSA-N 0.000 claims 1
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- MIIQIFPBEYQHGO-UHFFFAOYSA-N 1-[6-(2-chloro-6-methylpyridin-3-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-4-methylpiperidin-4-amine Chemical compound CC1=NC(=C(C=C1)SC2=NC3=NC=C(N=C3C=C2)N4CCC(CC4)(C)N)Cl MIIQIFPBEYQHGO-UHFFFAOYSA-N 0.000 claims 1
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- WRENRJMJIHUTIX-UHFFFAOYSA-N 2-[1-[6-(2,3-dichlorophenyl)sulfanylpyrido[2,3-b]pyrazin-2-yl]piperidin-4-yl]propan-2-amine Chemical compound CC(C)(C1CCN(CC1)C2=CN=C3C(=N2)C=CC(=N3)SC4=C(C(=CC=C4)Cl)Cl)N WRENRJMJIHUTIX-UHFFFAOYSA-N 0.000 claims 1
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- QWZOMAKYROFRHU-UHFFFAOYSA-N 2-[6-(2-amino-3-chloropyridin-4-yl)sulfanylpyrido[2,3-b]pyrazin-2-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-amine Chemical compound C1CC(C2C1CN(C2)C3=CN=C4C(=N3)C=CC(=N4)SC5=C(C(=NC=C5)N)Cl)N QWZOMAKYROFRHU-UHFFFAOYSA-N 0.000 claims 1
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| TW202003471A (zh) | 2018-03-21 | 2020-01-16 | 美商傳達治療有限公司 | Shp2磷酸酶抑制劑及其使用方法 |
| US11179397B2 (en) | 2018-10-03 | 2021-11-23 | Gilead Sciences, Inc. | Imidazopyrimidine derivatives |
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