JP7014736B2 - がんの処置のためのピラゾロピリジン誘導体 - Google Patents
がんの処置のためのピラゾロピリジン誘導体 Download PDFInfo
- Publication number
- JP7014736B2 JP7014736B2 JP2018561557A JP2018561557A JP7014736B2 JP 7014736 B2 JP7014736 B2 JP 7014736B2 JP 2018561557 A JP2018561557 A JP 2018561557A JP 2018561557 A JP2018561557 A JP 2018561557A JP 7014736 B2 JP7014736 B2 JP 7014736B2
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- compound
- salt
- pharmaceutically acceptable
- mixture
- 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.)
- Expired - Fee Related
Links
- 0 C*C1COCC1 Chemical compound C*C1COCC1 0.000 description 76
- SRNHIKMFWZGWNB-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)cc2-c1cccc2c1cnc(-c1c[n](C)nc1)c2)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)cc2-c1cccc2c1cnc(-c1c[n](C)nc1)c2)=O SRNHIKMFWZGWNB-UHFFFAOYSA-N 0.000 description 3
- OKEVZKONDSHWMX-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(c(C)nc(-c2c[n](C)nc2)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(c(C)nc(-c2c[n](C)nc2)c2)c2ccc1)=O OKEVZKONDSHWMX-UHFFFAOYSA-N 0.000 description 3
- AXZGDIGHFALXJO-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cncc2)c2cc(C)c1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cncc2)c2cc(C)c1)=O AXZGDIGHFALXJO-UHFFFAOYSA-N 0.000 description 3
- CIYRZKAFRJELFC-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cc(OC)cc2ccncc12)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cc(OC)cc2ccncc12)=O CIYRZKAFRJELFC-UHFFFAOYSA-N 0.000 description 3
- RZIHZCYAORMMHN-UHFFFAOYSA-N CCc1cc2cc(-c3c[n](C)nc3)ncc2c(-c2n[n](C3CCOCC3)c(CC3)c2CN3C(C)=O)c1 Chemical compound CCc1cc2cc(-c3c[n](C)nc3)ncc2c(-c2n[n](C3CCOCC3)c(CC3)c2CN3C(C)=O)c1 RZIHZCYAORMMHN-UHFFFAOYSA-N 0.000 description 3
- PADNYDZCLZVHIS-UHFFFAOYSA-N CNC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(CCCN(C2)c3c[n](C)nc3)c2ccc1)=O Chemical compound CNC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(CCCN(C2)c3c[n](C)nc3)c2ccc1)=O PADNYDZCLZVHIS-UHFFFAOYSA-N 0.000 description 3
- WBDWGCSHMUMUHC-UHFFFAOYSA-N C[n]1ncc(-c(cc2)cc3c2[nH]cc3I)c1 Chemical compound C[n]1ncc(-c(cc2)cc3c2[nH]cc3I)c1 WBDWGCSHMUMUHC-UHFFFAOYSA-N 0.000 description 3
- NIQGFSVBASCUJR-UHFFFAOYSA-N CC(C)N(Cc1cccc(-c2n[n](C3CCOCC3)c(CC3)c2CN3C(C)=O)c1C1)C1=O Chemical compound CC(C)N(Cc1cccc(-c2n[n](C3CCOCC3)c(CC3)c2CN3C(C)=O)c1C1)C1=O NIQGFSVBASCUJR-UHFFFAOYSA-N 0.000 description 2
- VOMPVIXWBVPHTE-UHFFFAOYSA-N CC(Cc1c(C2)cccc1-c1n[n](C3CCOCC3)c(CC3)c1CN3C(NC)=O)N2c1c[n](C)nc1 Chemical compound CC(Cc1c(C2)cccc1-c1n[n](C3CCOCC3)c(CC3)c1CN3C(NC)=O)N2c1c[n](C)nc1 VOMPVIXWBVPHTE-UHFFFAOYSA-N 0.000 description 2
- PVZWQEHRVVPKKT-UHFFFAOYSA-O CC(N(CC1)CC(C(c2cc(CO)cc3ccncc23)=[NH2+])=C1NC1CCOCC1)=O Chemical compound CC(N(CC1)CC(C(c2cc(CO)cc3ccncc23)=[NH2+])=C1NC1CCOCC1)=O PVZWQEHRVVPKKT-UHFFFAOYSA-O 0.000 description 2
- FDNJLZUECFSVCR-UHFFFAOYSA-N CC(N(CC1)CCC1[n](c(CC1)c2CN1C(NC)=O)nc2-c1c(cnc(-c2cnc(C)[s]2)c2)c2ccc1)=O Chemical compound CC(N(CC1)CCC1[n](c(CC1)c2CN1C(NC)=O)nc2-c1c(cnc(-c2cnc(C)[s]2)c2)c2ccc1)=O FDNJLZUECFSVCR-UHFFFAOYSA-N 0.000 description 2
- XWVNKTANUYLREY-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C)nc2-c1c[nH]c2c1ccc(-c1c[n](C)nc1)c2)=O Chemical compound CC(N(CC1)Cc2c1[n](C)nc2-c1c[nH]c2c1ccc(-c1c[n](C)nc1)c2)=O XWVNKTANUYLREY-UHFFFAOYSA-N 0.000 description 2
- LHZWFOVJEWVOSF-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C)nc2-c1c[nH]c2c1cccc2)=O Chemical compound CC(N(CC1)Cc2c1[n](C)nc2-c1c[nH]c2c1cccc2)=O LHZWFOVJEWVOSF-UHFFFAOYSA-N 0.000 description 2
- QRHSMFNSBKWHNZ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c(c1cnc2)cccc1c2Cl)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c(c1cnc2)cccc1c2Cl)=O QRHSMFNSBKWHNZ-UHFFFAOYSA-N 0.000 description 2
- CDCPBDAXFCXTMF-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(CC(N(C2)C3CCCCC3)=O)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(CC(N(C2)C3CCCCC3)=O)c2ccc1)=O CDCPBDAXFCXTMF-UHFFFAOYSA-N 0.000 description 2
- MCUHPQVRVOUVII-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(CCN(c2c[n](C)nc2)C2=O)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(CCN(c2c[n](C)nc2)C2=O)c2ccc1)=O MCUHPQVRVOUVII-UHFFFAOYSA-N 0.000 description 2
- ZOPJHOPWZQBLIM-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cccc2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cccc2)c2ccc1)=O ZOPJHOPWZQBLIM-UHFFFAOYSA-N 0.000 description 2
- PBPJDDDAIOSZOQ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(-c2c[n](C)nc2)c2)c2c(C)cc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(-c2c[n](C)nc2)c2)c2c(C)cc1)=O PBPJDDDAIOSZOQ-UHFFFAOYSA-N 0.000 description 2
- MURDGIZINCTSAI-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N2CCCCC2)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N2CCCCC2)c2)c2ccc1)=O MURDGIZINCTSAI-UHFFFAOYSA-N 0.000 description 2
- FXGWPWRNOMGUEL-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N2CCN(C)CC2)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N2CCN(C)CC2)c2)c2ccc1)=O FXGWPWRNOMGUEL-UHFFFAOYSA-N 0.000 description 2
- LFPQCVDWDPNIER-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N2CCOCC2)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N2CCOCC2)c2)c2ccc1)=O LFPQCVDWDPNIER-UHFFFAOYSA-N 0.000 description 2
- FRFVHJFMSJYFOB-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cc(C=C)cc2ccncc12)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cc(C=C)cc2ccncc12)=O FRFVHJFMSJYFOB-UHFFFAOYSA-N 0.000 description 2
- JEJLXAUUWSWJGH-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cc(Cl)cc2c1cnc(-c1c[n](C)nc1)c2)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cc(Cl)cc2c1cnc(-c1c[n](C)nc1)c2)=O JEJLXAUUWSWJGH-UHFFFAOYSA-N 0.000 description 2
- CEKRNAIUIRPGKF-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1ccc(cc[nH]2)c2c1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1ccc(cc[nH]2)c2c1)=O CEKRNAIUIRPGKF-UHFFFAOYSA-N 0.000 description 2
- MDIGEBROHMJKOB-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc(CN2c(cc3)ccc3OC)c1C2=O)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc(CN2c(cc3)ccc3OC)c1C2=O)=O MDIGEBROHMJKOB-UHFFFAOYSA-N 0.000 description 2
- XJAYQWZRDYTMBJ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc2c(C)c(-c3c[n](C)nc3)ncc12)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc2c(C)c(-c3c[n](C)nc3)ncc12)=O XJAYQWZRDYTMBJ-UHFFFAOYSA-N 0.000 description 2
- RMGKFRLSFSRTJN-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc2ccc3[n](C)ncc3c2)=O)ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc2ccc3[n](C)ncc3c2)=O)ccc1)=O RMGKFRLSFSRTJN-UHFFFAOYSA-N 0.000 description 2
- GPXHMFHTDYQOCA-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc2cccnc2)=O)ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc2cccnc2)=O)ccc1)=O GPXHMFHTDYQOCA-UHFFFAOYSA-N 0.000 description 2
- UEFJFQPLVYIOOV-SFHVURJKSA-N CC(N(CC1)Cc2c1[n]([C@@H]1COCC1)nc2-c1cccc2c1ccc(-c1c[n](C)nc1)n2)=O Chemical compound CC(N(CC1)Cc2c1[n]([C@@H]1COCC1)nc2-c1cccc2c1ccc(-c1c[n](C)nc1)n2)=O UEFJFQPLVYIOOV-SFHVURJKSA-N 0.000 description 2
- MUSHSSGZXVTTRI-UHFFFAOYSA-N CCc1cc(ccnc2)c2c(-c2n[n](C3CCOCC3)c(CC3)c2CN3C(C)=O)c1 Chemical compound CCc1cc(ccnc2)c2c(-c2n[n](C3CCOCC3)c(CC3)c2CN3C(C)=O)c1 MUSHSSGZXVTTRI-UHFFFAOYSA-N 0.000 description 2
- FHDSEZXJVYUDBE-UHFFFAOYSA-N CNC(N(CC1)Cc2c1[n](C1CCOCC1)c(C#N)c2-c1c(cnc(-c2c[n](C)nc2)c2)c2ccc1)=O Chemical compound CNC(N(CC1)Cc2c1[n](C1CCOCC1)c(C#N)c2-c1c(cnc(-c2c[n](C)nc2)c2)c2ccc1)=O FHDSEZXJVYUDBE-UHFFFAOYSA-N 0.000 description 2
- XVZRWTORWQTWOV-UHFFFAOYSA-N CNC(N(CC1)Cc2c1[n](C1CCOCC1)c(C#N)c2C1=CC=CC2C=C(c3c[n](CCNC(N(CC4)Cc5c4[n](C4CCOCC4)nc5-c4c(CCCN(C5)c6c[n](C)nc6)c5ccc4)=O)nc3)N=CC12)=O Chemical compound CNC(N(CC1)Cc2c1[n](C1CCOCC1)c(C#N)c2C1=CC=CC2C=C(c3c[n](CCNC(N(CC4)Cc5c4[n](C4CCOCC4)nc5-c4c(CCCN(C5)c6c[n](C)nc6)c5ccc4)=O)nc3)N=CC12)=O XVZRWTORWQTWOV-UHFFFAOYSA-N 0.000 description 2
- INLQCBQKBWUHTJ-UHFFFAOYSA-N C[n]1ncc2c1ccc(NC(c1cccc(I)c1)=O)c2 Chemical compound C[n]1ncc2c1ccc(NC(c1cccc(I)c1)=O)c2 INLQCBQKBWUHTJ-UHFFFAOYSA-N 0.000 description 2
- IPWVATCRLKASLP-UHFFFAOYSA-N Cc(c1ccc2)c(-c3c[n](C)nc3)ncc1c2-c1n[n](C2CCOCC2)c(CC2)c1CN2C(NC)=O Chemical compound Cc(c1ccc2)c(-c3c[n](C)nc3)ncc1c2-c1n[n](C2CCOCC2)c(CC2)c1CN2C(NC)=O IPWVATCRLKASLP-UHFFFAOYSA-N 0.000 description 2
- HHNIUXAAKCJGCV-UHFFFAOYSA-N Cc1cc(C(Nc2c[n](C)nc2)=O)ccc1 Chemical compound Cc1cc(C(Nc2c[n](C)nc2)=O)ccc1 HHNIUXAAKCJGCV-UHFFFAOYSA-N 0.000 description 2
- RISCYXHDESAFEA-UHFFFAOYSA-N Cc1ccc(-c2n[n](C3CCOCC3)c(CC3)c2CN3C(NC)=O)c2c1cc(-c1c[n](C)nc1)nc2 Chemical compound Cc1ccc(-c2n[n](C3CCOCC3)c(CC3)c2CN3C(NC)=O)c2c1cc(-c1c[n](C)nc1)nc2 RISCYXHDESAFEA-UHFFFAOYSA-N 0.000 description 2
- VMRKBNODHCRUNG-UHFFFAOYSA-N Cc1cccc2cc(-c3c[n](C)nc3)ccc12 Chemical compound Cc1cccc2cc(-c3c[n](C)nc3)ccc12 VMRKBNODHCRUNG-UHFFFAOYSA-N 0.000 description 2
- ZHCWBVCTJXADOA-UHFFFAOYSA-N Cc1ncc(-c2cc3cccc(-c4n[n](C(CC5)CCS5=O)c(CC5)c4CN5C(NC)=O)c3cn2)[s]1 Chemical compound Cc1ncc(-c2cc3cccc(-c4n[n](C(CC5)CCS5=O)c(CC5)c4CN5C(NC)=O)c3cn2)[s]1 ZHCWBVCTJXADOA-UHFFFAOYSA-N 0.000 description 2
- CGAISMUVYCGODJ-UHFFFAOYSA-N O=C(c1cccc(I)c1)Nc1cc2ccccc2nc1 Chemical compound O=C(c1cccc(I)c1)Nc1cc2ccccc2nc1 CGAISMUVYCGODJ-UHFFFAOYSA-N 0.000 description 2
- FTUGLRZTWANTCQ-UHFFFAOYSA-N Brc(c1c2ccnc1)ccc2OCc1ccccc1 Chemical compound Brc(c1c2ccnc1)ccc2OCc1ccccc1 FTUGLRZTWANTCQ-UHFFFAOYSA-N 0.000 description 1
- VFLUFKYWBJSYKA-UHFFFAOYSA-O C/C(/N(CC1)CC(C(c2cccc3c2cnc(-c2c[n](C)nc2C#N)c3)=[NH2+])=C1NC1CCOCC1)=[O]\C[n]1ncc(-c(nc2)cc3c2c(-c2n[n](C4CCOCC4)c(CC4)c2CN4C(NC)=O)ccc3C)c1 Chemical compound C/C(/N(CC1)CC(C(c2cccc3c2cnc(-c2c[n](C)nc2C#N)c3)=[NH2+])=C1NC1CCOCC1)=[O]\C[n]1ncc(-c(nc2)cc3c2c(-c2n[n](C4CCOCC4)c(CC4)c2CN4C(NC)=O)ccc3C)c1 VFLUFKYWBJSYKA-UHFFFAOYSA-O 0.000 description 1
- GAROCIDDWUKPQO-UHFFFAOYSA-N C/C(/N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1ccc[n]2c1nc(C(O)=O)c2)=[O]\C[n]1ncc(-c2cc3cccc(-c4c(C#N)[n](C5CCOCC5)c(CC5)c4CN5C(NC)=O)c3cn2)c1 Chemical compound C/C(/N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1ccc[n]2c1nc(C(O)=O)c2)=[O]\C[n]1ncc(-c2cc3cccc(-c4c(C#N)[n](C5CCOCC5)c(CC5)c4CN5C(NC)=O)c3cn2)c1 GAROCIDDWUKPQO-UHFFFAOYSA-N 0.000 description 1
- ACZFXRUNQALRBG-VVHNFQOZSA-N C/C=N\c(cc(cc1)-c2c[nH]nc2)c1C#N Chemical compound C/C=N\c(cc(cc1)-c2c[nH]nc2)c1C#N ACZFXRUNQALRBG-VVHNFQOZSA-N 0.000 description 1
- KHUXEBQJOZIEFV-UHFFFAOYSA-N CC(C(CCc1cccc(C(C(CCC(CCC(NC)=O)CC2)=C2NC2CCOCC2)=N)c1C1)C1=O)c1c[n](C)nc1 Chemical compound CC(C(CCc1cccc(C(C(CCC(CCC(NC)=O)CC2)=C2NC2CCOCC2)=N)c1C1)C1=O)c1c[n](C)nc1 KHUXEBQJOZIEFV-UHFFFAOYSA-N 0.000 description 1
- BXFJQPYHAZJMBT-UHFFFAOYSA-O CC(C)(C)OC(N(CC1)CC(C(Br)=[NH2+])=C1NC1COCC1)=O Chemical compound CC(C)(C)OC(N(CC1)CC(C(Br)=[NH2+])=C1NC1COCC1)=O BXFJQPYHAZJMBT-UHFFFAOYSA-O 0.000 description 1
- AHGNLFYXPZBDMS-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)Cc2c1[nH]nc2N)=O Chemical compound CC(C)(C)OC(N(CC1)Cc2c1[nH]nc2N)=O AHGNLFYXPZBDMS-UHFFFAOYSA-N 0.000 description 1
- YVADPHBFNASQCC-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)Cc2c1[n](C(CC1)CCN1C(C)=O)nc2Br)=O Chemical compound CC(C)(C)OC(N(CC1)Cc2c1[n](C(CC1)CCN1C(C)=O)nc2Br)=O YVADPHBFNASQCC-UHFFFAOYSA-N 0.000 description 1
- ABYPGKFTAJWZDO-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)Cc2c1[n](C(CC1)CCS1=O)nc2Br)=O Chemical compound CC(C)(C)OC(N(CC1)Cc2c1[n](C(CC1)CCS1=O)nc2Br)=O ABYPGKFTAJWZDO-UHFFFAOYSA-N 0.000 description 1
- SGYXFZKQAFMMQX-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)Cc2c1[n](C)nc2Br)=O Chemical compound CC(C)(C)OC(N(CC1)Cc2c1[n](C)nc2Br)=O SGYXFZKQAFMMQX-UHFFFAOYSA-N 0.000 description 1
- AZSNXHIRFFTRFJ-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)Cc2c1[n](C)nc2C(c(cc1)ccc1-c1c[n](C)nc1)=O)=O Chemical compound CC(C)(C)OC(N(CC1)Cc2c1[n](C)nc2C(c(cc1)ccc1-c1c[n](C)nc1)=O)=O AZSNXHIRFFTRFJ-UHFFFAOYSA-N 0.000 description 1
- SMIUYVRHBRQRNU-HNYPQAEJSA-O CC(C)(C)OC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-[n](c(C)c1)c2c1cc(/C(/C=[NH2+])=C/NC)nc2)=O Chemical compound CC(C)(C)OC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-[n](c(C)c1)c2c1cc(/C(/C=[NH2+])=C/NC)nc2)=O SMIUYVRHBRQRNU-HNYPQAEJSA-O 0.000 description 1
- FKVQKSOVYNNOTO-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)Cc2c1[n](C1COCC1)nc2Br)=O Chemical compound CC(C)(C)OC(N(CC1)Cc2c1[n](C1COCC1)nc2Br)=O FKVQKSOVYNNOTO-UHFFFAOYSA-N 0.000 description 1
- FKVQKSOVYNNOTO-JTQLQIEISA-N CC(C)(C)OC(N(CC1)Cc2c1[n]([C@@H]1COCC1)nc2Br)=O Chemical compound CC(C)(C)OC(N(CC1)Cc2c1[n]([C@@H]1COCC1)nc2Br)=O FKVQKSOVYNNOTO-JTQLQIEISA-N 0.000 description 1
- SBXBBQMBQFVYSZ-UHFFFAOYSA-N CC(C)(C)OC([n]1c2cc(-c3c[n](C)nc3)ccc2c(B2OC(C)(C)C(C)(C)O2)c1)=O Chemical compound CC(C)(C)OC([n]1c2cc(-c3c[n](C)nc3)ccc2c(B2OC(C)(C)C(C)(C)O2)c1)=O SBXBBQMBQFVYSZ-UHFFFAOYSA-N 0.000 description 1
- YQFUMZZCTYXSBL-UHFFFAOYSA-N CC(C)(C)OC([n]1c2cc(-c3c[n](C)nc3)ccc2c(Br)c1)=O Chemical compound CC(C)(C)OC([n]1c2cc(-c3c[n](C)nc3)ccc2c(Br)c1)=O YQFUMZZCTYXSBL-UHFFFAOYSA-N 0.000 description 1
- OUOWFTDOMYJYKB-UHFFFAOYSA-N CC(C)(C)OC([n]1c2cc(Br)ccc2cc1)=O Chemical compound CC(C)(C)OC([n]1c2cc(Br)ccc2cc1)=O OUOWFTDOMYJYKB-UHFFFAOYSA-N 0.000 description 1
- SVUNENGHCGJDMH-UHFFFAOYSA-N CC(C)(C1(C)C)OS(c2c(ccc(-c3c[n](C)nc3)c3)c3ccc2)[O]1=C Chemical compound CC(C)(C1(C)C)OS(c2c(ccc(-c3c[n](C)nc3)c3)c3ccc2)[O]1=C SVUNENGHCGJDMH-UHFFFAOYSA-N 0.000 description 1
- JYDQTCYQTMVONL-UHFFFAOYSA-N CC(C)SC(C)CCC(C)C[n]1c(CCNC2)c2cc1 Chemical compound CC(C)SC(C)CCC(C)C[n]1c(CCNC2)c2cc1 JYDQTCYQTMVONL-UHFFFAOYSA-N 0.000 description 1
- CGCAKNOKWWIOQL-UHFFFAOYSA-O CC(C)[SH+]C(C)CCC(C)C[n]1c(CCN(Cc2ccccc2)C2)c2cc1 Chemical compound CC(C)[SH+]C(C)CCC(C)C[n]1c(CCN(Cc2ccccc2)C2)c2cc1 CGCAKNOKWWIOQL-UHFFFAOYSA-O 0.000 description 1
- HMZPDEOOVHIABF-OFLPRAFFSA-O CC(C)[SH+]C(C)CCC(C)[C@@H](C)[n]1c(CCN(C2)C(C)=O)c2cc1 Chemical compound CC(C)[SH+]C(C)CCC(C)[C@@H](C)[n]1c(CCN(C2)C(C)=O)c2cc1 HMZPDEOOVHIABF-OFLPRAFFSA-O 0.000 description 1
- HCJFUTKOOJKIFR-UHFFFAOYSA-N CC(C)[n]1c(cccc2)c2c(C)c1 Chemical compound CC(C)[n]1c(cccc2)c2c(C)c1 HCJFUTKOOJKIFR-UHFFFAOYSA-N 0.000 description 1
- HFHLOKNBISBYHG-UHFFFAOYSA-N CC(C)c(c(CC1)c2CN1C(NC)=O)n[n]2-c1c(cnc(-c2c[n](C)nc2)c2)c2ccc1 Chemical compound CC(C)c(c(CC1)c2CN1C(NC)=O)n[n]2-c1c(cnc(-c2c[n](C)nc2)c2)c2ccc1 HFHLOKNBISBYHG-UHFFFAOYSA-N 0.000 description 1
- DFQYRLUFRMGRQD-UHFFFAOYSA-N CC(C)c(c(CC1)c2CN1C(NC)=O)n[n]2-c1c(cnc(-c2c[n](CCNC(N(CC3)Cc4c3c(N3CCOCC3)n[n]4-c3c(cnc(-c4c[n](C)nc4)c4)c4ccc3)=O)nc2)c2)c2ccc1 Chemical compound CC(C)c(c(CC1)c2CN1C(NC)=O)n[n]2-c1c(cnc(-c2c[n](CCNC(N(CC3)Cc4c3c(N3CCOCC3)n[n]4-c3c(cnc(-c4c[n](C)nc4)c4)c4ccc3)=O)nc2)c2)c2ccc1 DFQYRLUFRMGRQD-UHFFFAOYSA-N 0.000 description 1
- AFDFSJAUBGJNGS-UHFFFAOYSA-N CC(C)c1c(cnc(-c2c[n](C)nc2)c2)c2ccc1C Chemical compound CC(C)c1c(cnc(-c2c[n](C)nc2)c2)c2ccc1C AFDFSJAUBGJNGS-UHFFFAOYSA-N 0.000 description 1
- DQBVCTNEDNTKLD-UHFFFAOYSA-N CC(Cc(c(C1)ccc2)c2I)N1c1c[n](C)nc1 Chemical compound CC(Cc(c(C1)ccc2)c2I)N1c1c[n](C)nc1 DQBVCTNEDNTKLD-UHFFFAOYSA-N 0.000 description 1
- LQQJMMJJTQVVQB-UHFFFAOYSA-N CC(N(CC1)CC(C(C(c(cc2)ccc2-c2c[n](C)nc2)=O)=N)=C1NC)=O Chemical compound CC(N(CC1)CC(C(C(c(cc2)ccc2-c2c[n](C)nc2)=O)=N)=C1NC)=O LQQJMMJJTQVVQB-UHFFFAOYSA-N 0.000 description 1
- XBRQIBHHJPSFEP-UHFFFAOYSA-O CC(N(CC1)CC(C([n](c(C)c2)c3c2cc(-c2c[n](C)nc2)c(C#N)c3)=[NH2+])=C1NC1CCOCC1)=O Chemical compound CC(N(CC1)CC(C([n](c(C)c2)c3c2cc(-c2c[n](C)nc2)c(C#N)c3)=[NH2+])=C1NC1CCOCC1)=O XBRQIBHHJPSFEP-UHFFFAOYSA-O 0.000 description 1
- DNBNUFOMVPZPQQ-WKEKJZSLSA-O CC(N(CC1)CC(C([n](c(C)c2)c3c2cc(/C(/C=N\C)=C/NC)nc3)=[NH2+])=C1NC1CCOCC1)=O Chemical compound CC(N(CC1)CC(C([n](c(C)c2)c3c2cc(/C(/C=N\C)=C/NC)nc3)=[NH2+])=C1NC1CCOCC1)=O DNBNUFOMVPZPQQ-WKEKJZSLSA-O 0.000 description 1
- GSGFUJNUHRGDLF-UHFFFAOYSA-O CC(N(CC1)CC(C(c(c2c3ccnc2)ccc3F)=[NH2+])=C1NC1CCOCC1)=O Chemical compound CC(N(CC1)CC(C(c(c2c3ccnc2)ccc3F)=[NH2+])=C1NC1CCOCC1)=O GSGFUJNUHRGDLF-UHFFFAOYSA-O 0.000 description 1
- QJXQYIOOASQROE-UHFFFAOYSA-O CC(N(CC1)CC(C(c2c(cnc(-c3c[n](C)nc3C#N)c3)c3ccc2)=[NH2+])=C1NC1CCOCC1)=O Chemical compound CC(N(CC1)CC(C(c2c(cnc(-c3c[n](C)nc3C#N)c3)c3ccc2)=[NH2+])=C1NC1CCOCC1)=O QJXQYIOOASQROE-UHFFFAOYSA-O 0.000 description 1
- JHLUQWDELJFYRE-UHFFFAOYSA-O CC(N(CC1)CC(C(c2c(cnc(N3CCCC3)c3)c3ccc2)=[NH2+])=C1NC1CCOCC1)=O Chemical compound CC(N(CC1)CC(C(c2c(cnc(N3CCCC3)c3)c3ccc2)=[NH2+])=C1NC1CCOCC1)=O JHLUQWDELJFYRE-UHFFFAOYSA-O 0.000 description 1
- FATDXMGBWVCMSB-UHFFFAOYSA-N CC(N(CC1)CC(C(c2cc(C(Nc(cc3)ccc3-[n]3c(/[O]=C(/C)\N(CC4)Cc5c4[n](C4COCC4)nc5-c4cccc(C(Nc5ccc(C[n]6ncnc6)cc5)=O)c4)cnc3)=O)ccc2)=N)=C1NC1COCC1)=O Chemical compound CC(N(CC1)CC(C(c2cc(C(Nc(cc3)ccc3-[n]3c(/[O]=C(/C)\N(CC4)Cc5c4[n](C4COCC4)nc5-c4cccc(C(Nc5ccc(C[n]6ncnc6)cc5)=O)c4)cnc3)=O)ccc2)=N)=C1NC1COCC1)=O FATDXMGBWVCMSB-UHFFFAOYSA-N 0.000 description 1
- XDMYAKFHFPTMPJ-UHFFFAOYSA-N CC(N(CC1)CC(C(c2cc(C(Nc3ncc(-c4ccccc4)[n]3C)=O)ccc2)=N)=C1NC1COCC1)=O Chemical compound CC(N(CC1)CC(C(c2cc(C(Nc3ncc(-c4ccccc4)[n]3C)=O)ccc2)=N)=C1NC1COCC1)=O XDMYAKFHFPTMPJ-UHFFFAOYSA-N 0.000 description 1
- OVPOCQBLAJMEDN-UHFFFAOYSA-O CC(N(CC1)CC(C(c2cccc3c2CCCC3)=[NH2+])=C1NC1CCOCC1)=O Chemical compound CC(N(CC1)CC(C(c2cccc3c2CCCC3)=[NH2+])=C1NC1CCOCC1)=O OVPOCQBLAJMEDN-UHFFFAOYSA-O 0.000 description 1
- NLHBHVGPMMXWIM-UHFFFAOYSA-N CC(N(CC1)CCC1N)=O Chemical compound CC(N(CC1)CCC1N)=O NLHBHVGPMMXWIM-UHFFFAOYSA-N 0.000 description 1
- HMTRVUXLBPVHRV-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C)nc2-c1c[n](C)c2c1cccc2)=O Chemical compound CC(N(CC1)Cc2c1[n](C)nc2-c1c[n](C)c2c1cccc2)=O HMTRVUXLBPVHRV-UHFFFAOYSA-N 0.000 description 1
- WHKKMMDVJLFKFP-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C)nc2-c1cccc2c1cn[nH]2)=O Chemical compound CC(N(CC1)Cc2c1[n](C)nc2-c1cccc2c1cn[nH]2)=O WHKKMMDVJLFKFP-UHFFFAOYSA-N 0.000 description 1
- JWQGNJLAPXAWFU-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCCCC1)nc2-c1ccnc2c1cccc2)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCCCC1)nc2-c1ccnc2c1cccc2)=O JWQGNJLAPXAWFU-UHFFFAOYSA-N 0.000 description 1
- UNSOLAMOWLJBFZ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-[n](c(C)c1)c2c1cc(-c1c[n](C)nc1)c(C(F)F)c2)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-[n](c(C)c1)c2c1cc(-c1c[n](C)nc1)c(C(F)F)c2)=O UNSOLAMOWLJBFZ-UHFFFAOYSA-N 0.000 description 1
- FFQXJFYBGRFVHW-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-[n](cc1)c2c1ccc(-c(cc1)ccc1OC)c2)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-[n](cc1)c2c1ccc(-c(cc1)ccc1OC)c2)=O FFQXJFYBGRFVHW-UHFFFAOYSA-N 0.000 description 1
- WCBTYHJUDDZYOV-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c(c1c2ccnc1)ccc2Cl)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c(c1c2ccnc1)ccc2Cl)=O WCBTYHJUDDZYOV-UHFFFAOYSA-N 0.000 description 1
- SOVQTDYFKLKSIT-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c(c1c2ccnc1)ccc2F)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c(c1c2ccnc1)ccc2F)=O SOVQTDYFKLKSIT-UHFFFAOYSA-N 0.000 description 1
- XGLAIMCDIMBGPK-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c(c1c2ccnc1)ccc2OC)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c(c1c2ccnc1)ccc2OC)=O XGLAIMCDIMBGPK-UHFFFAOYSA-N 0.000 description 1
- GAVVBDXGDAIREU-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c(c1cnc2)cccc1c2OC)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c(c1cnc2)cccc1c2OC)=O GAVVBDXGDAIREU-UHFFFAOYSA-N 0.000 description 1
- HGFHSXDDULLHEJ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cc[nH]2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cc[nH]2)c2ccc1)=O HGFHSXDDULLHEJ-UHFFFAOYSA-N 0.000 description 1
- JSXHUXWRIHXDFS-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cn[nH]2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cn[nH]2)c2ccc1)=O JSXHUXWRIHXDFS-UHFFFAOYSA-N 0.000 description 1
- DBONMQBRYYLAOJ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(-c2c[n](C)nc2)c2)c2cc(C=C)c1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(-c2c[n](C)nc2)c2)c2cc(C=C)c1)=O DBONMQBRYYLAOJ-UHFFFAOYSA-N 0.000 description 1
- IHBLVUOMYJSFGF-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(-c2c[n](C)nc2)c2C#N)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(-c2c[n](C)nc2)c2C#N)c2ccc1)=O IHBLVUOMYJSFGF-UHFFFAOYSA-N 0.000 description 1
- CIFDKAKCZSECHS-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(-c2c[n](C)nc2C#N)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(-c2c[n](C)nc2C#N)c2)c2ccc1)=O CIFDKAKCZSECHS-UHFFFAOYSA-N 0.000 description 1
- IUPRGOJCGLKFIM-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(C2C(C(F)[F]CC(N(CC3)Cc4c3[n](C3CCOCC3)nc4-c3cccc4c3cnc(-c3c(C(F)F)[n](C)nc3)c4)=O)=NN(C)C2)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(C2C(C(F)[F]CC(N(CC3)Cc4c3[n](C3CCOCC3)nc4-c3cccc4c3cnc(-c3c(C(F)F)[n](C)nc3)c4)=O)=NN(C)C2)c2)c2ccc1)=O IUPRGOJCGLKFIM-UHFFFAOYSA-N 0.000 description 1
- FSKVTCOJKJFQSQ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N(CC2)CC2(F)F)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N(CC2)CC2(F)F)c2)c2ccc1)=O FSKVTCOJKJFQSQ-UHFFFAOYSA-N 0.000 description 1
- DJSHZSFSVVWRLV-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N(CC2)CC2C#N)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N(CC2)CC2C#N)c2)c2ccc1)=O DJSHZSFSVVWRLV-UHFFFAOYSA-N 0.000 description 1
- LPQGZWOPIPZQLS-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N2CC=CC2)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N2CC=CC2)c2)c2ccc1)=O LPQGZWOPIPZQLS-UHFFFAOYSA-N 0.000 description 1
- IQKIODVRVSJPCU-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N2CCCC2)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(N2CCCC2)c2)c2ccc1)=O IQKIODVRVSJPCU-UHFFFAOYSA-N 0.000 description 1
- HWMVZUDOEQIIJA-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cncc2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cncc2)c2ccc1)=O HWMVZUDOEQIIJA-UHFFFAOYSA-N 0.000 description 1
- IZPACEJNRRRHNL-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cncc2C=C)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cncc2C=C)c2ccc1)=O IZPACEJNRRRHNL-UHFFFAOYSA-N 0.000 description 1
- TYSZOEJURJYWAB-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c2nc(-c(cc3)ccc3OC)[o]c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c2nc(-c(cc3)ccc3OC)[o]c2ccc1)=O TYSZOEJURJYWAB-UHFFFAOYSA-N 0.000 description 1
- KRSNMXSWHQJHSE-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c2nc(-c3cnccc3)[nH]c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c2nc(-c3cnccc3)[nH]c2ccc1)=O KRSNMXSWHQJHSE-UHFFFAOYSA-N 0.000 description 1
- YMJZTJARHXMQNO-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1ccc(C)c2c1cncc2)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1ccc(C)c2c1cncc2)=O YMJZTJARHXMQNO-UHFFFAOYSA-N 0.000 description 1
- UHNWSNQEYDVJCQ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1ccc(CO)c2c1cncc2)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1ccc(CO)c2c1cncc2)=O UHNWSNQEYDVJCQ-UHFFFAOYSA-N 0.000 description 1
- BDTSRYSWKDSLCK-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc(CN2C)c1CC2=O)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc(CN2C)c1CC2=O)=O BDTSRYSWKDSLCK-UHFFFAOYSA-N 0.000 description 1
- YKJCGHAYZPQUNB-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc2c1[nH]cc2)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc2c1[nH]cc2)=O YKJCGHAYZPQUNB-UHFFFAOYSA-N 0.000 description 1
- RJBWYWPUTZHUHJ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc2c1cnc(N)n2)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc2c1cnc(N)n2)=O RJBWYWPUTZHUHJ-UHFFFAOYSA-N 0.000 description 1
- OYAMQWZKBNTDQO-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc2cc(O)ncc12)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cccc2cc(O)ncc12)=O OYAMQWZKBNTDQO-UHFFFAOYSA-N 0.000 description 1
- NAEZVAXBVFHAKF-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cncc2c1cccc2)=O Chemical compound CC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1cncc2c1cccc2)=O NAEZVAXBVFHAKF-UHFFFAOYSA-N 0.000 description 1
- HUEWZFKMROXUHZ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1COC1)nc2Br)=O Chemical compound CC(N(CC1)Cc2c1[n](C1COC1)nc2Br)=O HUEWZFKMROXUHZ-UHFFFAOYSA-N 0.000 description 1
- FXTYPTQDJKBKRJ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(NC(CC=C2)C=C2C#N)=O)ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(NC(CC=C2)C=C2C#N)=O)ccc1)=O FXTYPTQDJKBKRJ-UHFFFAOYSA-N 0.000 description 1
- KYCSAVGOUZIXNW-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc([n](C)c2ccc3)nc2c3/[O]=C(\C)/N(CC2)Cc3c2[n](C2COCC2)nc3-c2cc(C(Nc3cnc(cccc4)c4c3)=O)ccc2)=O)ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc([n](C)c2ccc3)nc2c3/[O]=C(\C)/N(CC2)Cc3c2[n](C2COCC2)nc3-c2cc(C(Nc3cnc(cccc4)c4c3)=O)ccc2)=O)ccc1)=O KYCSAVGOUZIXNW-UHFFFAOYSA-N 0.000 description 1
- ZDQINNTYJCCXSG-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc2ccc(cn[n]3C)c3c2)=O)ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc2ccc(cn[n]3C)c3c2)=O)ccc1)=O ZDQINNTYJCCXSG-UHFFFAOYSA-N 0.000 description 1
- NVENTYSAEHPDDJ-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc2ccnc(CCC(N(CC3)Cc4c3[n](C3COCC3)nc4-c3cc(C(Nc4cncnc4)=O)ccc3)=O)c2)=O)ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc2ccnc(CCC(N(CC3)Cc4c3[n](C3COCC3)nc4-c3cc(C(Nc4cncnc4)=O)ccc3)=O)c2)=O)ccc1)=O NVENTYSAEHPDDJ-UHFFFAOYSA-N 0.000 description 1
- HWKVQJKKSOBRKE-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc2ccnc(CCC(N(CC3)Cc4c3[n](C3COCC3)nc4C(C3)=CC=CC3C(Nc3cncnc3)=O)=O)c2)=O)ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n](C1COCC1)nc2-c1cc(C(Nc2ccnc(CCC(N(CC3)Cc4c3[n](C3COCC3)nc4C(C3)=CC=CC3C(Nc3cncnc3)=O)=O)c2)=O)ccc1)=O HWKVQJKKSOBRKE-UHFFFAOYSA-N 0.000 description 1
- ASVAOPYXBJBJLG-UHFFFAOYSA-N CC(N(CC1)Cc2c1[n](C1COCC1)nc2Br)=O Chemical compound CC(N(CC1)Cc2c1[n](C1COCC1)nc2Br)=O ASVAOPYXBJBJLG-UHFFFAOYSA-N 0.000 description 1
- FTAJMIWEBHWZEB-NRFANRHFSA-N CC(N(CC1)Cc2c1[n]([C@@H]1COCC1)nc2-c1c(ccc(-c2c[n](C)nc2)c2)c2ccc1)=O Chemical compound CC(N(CC1)Cc2c1[n]([C@@H]1COCC1)nc2-c1c(ccc(-c2c[n](C)nc2)c2)c2ccc1)=O FTAJMIWEBHWZEB-NRFANRHFSA-N 0.000 description 1
- YUXRHEXBKMCLLL-NRFANRHFSA-N CC(N(CC1)Cc2c1[n]([C@@H]1COCC1)nc2C1=CCCc2cc(-c3c[n](C)nc3)ccc12)=O Chemical compound CC(N(CC1)Cc2c1[n]([C@@H]1COCC1)nc2C1=CCCc2cc(-c3c[n](C)nc3)ccc12)=O YUXRHEXBKMCLLL-NRFANRHFSA-N 0.000 description 1
- DMOAAPWMTONJPG-UHFFFAOYSA-N CC(c(cc(c(cc1C)c2)[n]1S(c1ccccc1)(=O)=O)c2-c1c[n](C)nc1)F Chemical compound CC(c(cc(c(cc1C)c2)[n]1S(c1ccccc1)(=O)=O)c2-c1c[n](C)nc1)F DMOAAPWMTONJPG-UHFFFAOYSA-N 0.000 description 1
- XRVFNIKPPRDFDR-UHFFFAOYSA-N CC(c1cccc(-c2c[n](cccc3[I](C(CCC4)N4c(cc4)ccc4-c4c[n](cccc5)c5n4)I)c3n2)c1)(F)F Chemical compound CC(c1cccc(-c2c[n](cccc3[I](C(CCC4)N4c(cc4)ccc4-c4c[n](cccc5)c5n4)I)c3n2)c1)(F)F XRVFNIKPPRDFDR-UHFFFAOYSA-N 0.000 description 1
- GWUZFJQGKVCBHJ-UHFFFAOYSA-N CC1(C)OB(c2cccc3cc(-c4c[n](C)nc4)ncc23)OC1(C)C Chemical compound CC1(C)OB(c2cccc3cc(-c4c[n](C)nc4)ncc23)OC1(C)C GWUZFJQGKVCBHJ-UHFFFAOYSA-N 0.000 description 1
- KAAOTNUTFKZZLO-UHFFFAOYSA-N CC1C=CC(S(N(CC(OC)OC)Cc2cc(Br)c(C)cc2)(=O)=O)=CC1 Chemical compound CC1C=CC(S(N(CC(OC)OC)Cc2cc(Br)c(C)cc2)(=O)=O)=CC1 KAAOTNUTFKZZLO-UHFFFAOYSA-N 0.000 description 1
- ZWKCLWOFJUHEDD-UHFFFAOYSA-N CCC(CCc1cccc(-c2n[n](C3CCOCC3)c(CC3)c2CN3C(C)=O)c1C1)C1=O Chemical compound CCC(CCc1cccc(-c2n[n](C3CCOCC3)c(CC3)c2CN3C(C)=O)c1C1)C1=O ZWKCLWOFJUHEDD-UHFFFAOYSA-N 0.000 description 1
- VMBHGULVGJUHSZ-UHFFFAOYSA-N CCC1=CN=CC2C(c3n[n](C4CCOCC4)c(CC4)c3CN4C(C)=O)=CC=CC12 Chemical compound CCC1=CN=CC2C(c3n[n](C4CCOCC4)c(CC4)c3CN4C(C)=O)=CC=CC12 VMBHGULVGJUHSZ-UHFFFAOYSA-N 0.000 description 1
- XWHYVUVAMWGJMR-UHFFFAOYSA-N CCOC(CC(CCCCCC#N)C(OC(C)(C)C)=O)=O Chemical compound CCOC(CC(CCCCCC#N)C(OC(C)(C)C)=O)=O XWHYVUVAMWGJMR-UHFFFAOYSA-N 0.000 description 1
- MXHUQURQEHIPAP-UHFFFAOYSA-N CCc1c(ccnc2)c2c(C)cc1 Chemical compound CCc1c(ccnc2)c2c(C)cc1 MXHUQURQEHIPAP-UHFFFAOYSA-N 0.000 description 1
- HSCWUDSMSUNTHX-UHFFFAOYSA-N CCc1cc(cc(c(Cl)c2)Br)c2[n]1S(c1ccccc1)(=O)=O Chemical compound CCc1cc(cc(c(Cl)c2)Br)c2[n]1S(c1ccccc1)(=O)=O HSCWUDSMSUNTHX-UHFFFAOYSA-N 0.000 description 1
- WOYWXGYZDNIWRD-UHFFFAOYSA-O CCc1ccc(C(C(CN(CC2)C(C)=O)=C2NC2CCOCC2)=[NH2+])c2c1ccnc2 Chemical compound CCc1ccc(C(C(CN(CC2)C(C)=O)=C2NC2CCOCC2)=[NH2+])c2c1ccnc2 WOYWXGYZDNIWRD-UHFFFAOYSA-O 0.000 description 1
- HOCQEOCBKYSMNC-UHFFFAOYSA-N CN(C(c(cc1)ccc1-c1c[n](C)nc1)=O)OC Chemical compound CN(C(c(cc1)ccc1-c1c[n](C)nc1)=O)OC HOCQEOCBKYSMNC-UHFFFAOYSA-N 0.000 description 1
- YQWSWVWFGCVXRQ-UHFFFAOYSA-N CN(C1)N=CC1c1cc2cnccc2cc1C(C1)C1=O Chemical compound CN(C1)N=CC1c1cc2cnccc2cc1C(C1)C1=O YQWSWVWFGCVXRQ-UHFFFAOYSA-N 0.000 description 1
- HZGOSFYDGHLXMI-UHFFFAOYSA-N CN(C1=CC2)N=CC1=CC2NC(c1cccc(I)c1)=O Chemical compound CN(C1=CC2)N=CC1=CC2NC(c1cccc(I)c1)=O HZGOSFYDGHLXMI-UHFFFAOYSA-N 0.000 description 1
- XNXYDWVECWZPRP-UHFFFAOYSA-N CNC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(CCN(C2)c3c[n](C)nc3)c2ccc1)=O Chemical compound CNC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(CCN(C2)c3c[n](C)nc3)c2ccc1)=O XNXYDWVECWZPRP-UHFFFAOYSA-N 0.000 description 1
- AFCVWMUKMSRAHO-UHFFFAOYSA-N CNC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(-c2c[n](C)nc2)c2)c2ccc1)=O Chemical compound CNC(N(CC1)Cc2c1[n](C1CCOCC1)nc2-c1c(cnc(-c2c[n](C)nc2)c2)c2ccc1)=O AFCVWMUKMSRAHO-UHFFFAOYSA-N 0.000 description 1
- VRVMHHGGFDAADO-UHFFFAOYSA-N CNC(N(CC1)Cc2c1c(N1CCOCC1)n[n]2-c1cccc2c1cnc(-c1c[n](C)nc1)c2)=O Chemical compound CNC(N(CC1)Cc2c1c(N1CCOCC1)n[n]2-c1cccc2c1cnc(-c1c[n](C)nc1)c2)=O VRVMHHGGFDAADO-UHFFFAOYSA-N 0.000 description 1
- PSEROPXQDOPFAM-UHFFFAOYSA-O CNC(c(cc1)ncc1-c(nc1)cc2c1c(C(C(CN(CC1)/C(/NC)=[O]/C[n]3ncc(-c(cc4cc5)ncc4c(-c4n[n](C6CCOCC6)c(CC6)c4CN6C(NC)=O)c5F)c3)=C1NC1CCOCC1)=[NH2+])ccc2)=O Chemical compound CNC(c(cc1)ncc1-c(nc1)cc2c1c(C(C(CN(CC1)/C(/NC)=[O]/C[n]3ncc(-c(cc4cc5)ncc4c(-c4n[n](C6CCOCC6)c(CC6)c4CN6C(NC)=O)c5F)c3)=C1NC1CCOCC1)=[NH2+])ccc2)=O PSEROPXQDOPFAM-UHFFFAOYSA-O 0.000 description 1
- SMALSJZSGXSXAI-UHFFFAOYSA-N COC(C(NCc(ccc(Cl)c1)c1Br)=O)OC Chemical compound COC(C(NCc(ccc(Cl)c1)c1Br)=O)OC SMALSJZSGXSXAI-UHFFFAOYSA-N 0.000 description 1
- FKAQRMCQFPEKBP-MKMNVTDBSA-N COC(C/N=C/c(cc1)cc(Br)c1Cl)OC Chemical compound COC(C/N=C/c(cc1)cc(Br)c1Cl)OC FKAQRMCQFPEKBP-MKMNVTDBSA-N 0.000 description 1
- BZBAYVGIWYQEHU-NSIKDUERSA-N COC(C/N=C\c(ccc(Cl)c1)c1Br)OC Chemical compound COC(C/N=C\c(ccc(Cl)c1)c1Br)OC BZBAYVGIWYQEHU-NSIKDUERSA-N 0.000 description 1
- KWRHWJSMVOOIPU-UHFFFAOYSA-N COC(CNCc(cc1)cc(Br)c1Cl)OC Chemical compound COC(CNCc(cc1)cc(Br)c1Cl)OC KWRHWJSMVOOIPU-UHFFFAOYSA-N 0.000 description 1
- IUTLWBBJOAHSSG-UHFFFAOYSA-N COC(CNCc(ccc(Cl)c1)c1Br)OC Chemical compound COC(CNCc(ccc(Cl)c1)c1Br)OC IUTLWBBJOAHSSG-UHFFFAOYSA-N 0.000 description 1
- VPRUYEWLZFTYCJ-UHFFFAOYSA-N COc(c(C=C)c1)ccc1-c1c[n](cccc2I)c2n1 Chemical compound COc(c(C=C)c1)ccc1-c1c[n](cccc2I)c2n1 VPRUYEWLZFTYCJ-UHFFFAOYSA-N 0.000 description 1
- AOZHIRVTXWVRCY-UHFFFAOYSA-N COc(cc1)ccc1-c1cc([nH]cc2)c2cc1 Chemical compound COc(cc1)ccc1-c1cc([nH]cc2)c2cc1 AOZHIRVTXWVRCY-UHFFFAOYSA-N 0.000 description 1
- IVZBMTISBGEECC-UHFFFAOYSA-N COc(cc1)ccc1-c1nc(cccc2I)c2[o]1 Chemical compound COc(cc1)ccc1-c1nc(cccc2I)c2[o]1 IVZBMTISBGEECC-UHFFFAOYSA-N 0.000 description 1
- DRWVHZPKNZHPFP-UHFFFAOYSA-N COc(cc1)ccc1N(Cc1c2c(I)ccc1)C2=O Chemical compound COc(cc1)ccc1N(Cc1c2c(I)ccc1)C2=O DRWVHZPKNZHPFP-UHFFFAOYSA-N 0.000 description 1
- AZXJOGUEZOBWKX-UHFFFAOYSA-N COc1cc([nH]cc2)c2c(I)c1 Chemical compound COc1cc([nH]cc2)c2c(I)c1 AZXJOGUEZOBWKX-UHFFFAOYSA-N 0.000 description 1
- GSEZHCLWHDZJAB-UHFFFAOYSA-N CS(OC1CCOCC1)(=O)=O Chemical compound CS(OC1CCOCC1)(=O)=O GSEZHCLWHDZJAB-UHFFFAOYSA-N 0.000 description 1
- KHXQGLSTCGSGLW-UHFFFAOYSA-N CS(OC1COCC1)(=O)=O Chemical compound CS(OC1COCC1)(=O)=O KHXQGLSTCGSGLW-UHFFFAOYSA-N 0.000 description 1
- KHXQGLSTCGSGLW-RXMQYKEDSA-N CS(O[C@H]1COCC1)(=O)=O Chemical compound CS(O[C@H]1COCC1)(=O)=O KHXQGLSTCGSGLW-RXMQYKEDSA-N 0.000 description 1
- DHTXKIFSCCLPRR-SFHVURJKSA-N C[C@@H](CC1)CN1c1cc2cccc(-c3n[n](C4CCOCC4)c(CC4)c3CN4C(C)=O)c2cn1 Chemical compound C[C@@H](CC1)CN1c1cc2cccc(-c3n[n](C4CCOCC4)c(CC4)c3CN4C(C)=O)c2cn1 DHTXKIFSCCLPRR-SFHVURJKSA-N 0.000 description 1
- DHTXKIFSCCLPRR-GOSISDBHSA-N C[C@H](CC1)CN1c1cc2cccc(-c3n[n](C4CCOCC4)c(CC4)c3CN4C(C)=O)c2cn1 Chemical compound C[C@H](CC1)CN1c1cc2cccc(-c3n[n](C4CCOCC4)c(CC4)c3CN4C(C)=O)c2cn1 DHTXKIFSCCLPRR-GOSISDBHSA-N 0.000 description 1
- OZAUUUGUHGHZMZ-UHFFFAOYSA-N C[IH]N1CCOCC1 Chemical compound C[IH]N1CCOCC1 OZAUUUGUHGHZMZ-UHFFFAOYSA-N 0.000 description 1
- NQYVZBGMYNJDGA-UHFFFAOYSA-N C[n](cc1)c2c1ccc(-c1c[n](C)nc1)c2 Chemical compound C[n](cc1)c2c1ccc(-c1c[n](C)nc1)c2 NQYVZBGMYNJDGA-UHFFFAOYSA-N 0.000 description 1
- GMKPJZRCBMJGFN-UHFFFAOYSA-N C[n]1c(NC(c2cc(I)ccc2)=O)ncc1-c1ccccc1 Chemical compound C[n]1c(NC(c2cc(I)ccc2)=O)ncc1-c1ccccc1 GMKPJZRCBMJGFN-UHFFFAOYSA-N 0.000 description 1
- XGOPNOIIRMKMJR-UHFFFAOYSA-N C[n]1c(cccc2)c2c(I)c1 Chemical compound C[n]1c(cccc2)c2c(I)c1 XGOPNOIIRMKMJR-UHFFFAOYSA-N 0.000 description 1
- VKHRVZIOXQMWBO-UHFFFAOYSA-N C[n]1ncc(-c(cc2)cc3c2[nH]cc3)c1 Chemical compound C[n]1ncc(-c(cc2)cc3c2[nH]cc3)c1 VKHRVZIOXQMWBO-UHFFFAOYSA-N 0.000 description 1
- MZIDJONTDURZGA-UHFFFAOYSA-N C[n]1ncc(-c(cc2)cc3c2nc[n]3[IH]C)c1 Chemical compound C[n]1ncc(-c(cc2)cc3c2nc[n]3[IH]C)c1 MZIDJONTDURZGA-UHFFFAOYSA-N 0.000 description 1
- JNLQMZREPWAVIE-UHFFFAOYSA-N C[n]1ncc(-c(cc2)ccc2C(O)=O)c1 Chemical compound C[n]1ncc(-c(cc2)ccc2C(O)=O)c1 JNLQMZREPWAVIE-UHFFFAOYSA-N 0.000 description 1
- ZIXDBDYGJMKGEQ-UHFFFAOYSA-N C[n]1ncc(-c(nc2)cc3c2c(-c2c(C#N)[n](C4CCOCC4)c4c2CNCC4)ccc3)c1 Chemical compound C[n]1ncc(-c(nc2)cc3c2c(-c2c(C#N)[n](C4CCOCC4)c4c2CNCC4)ccc3)c1 ZIXDBDYGJMKGEQ-UHFFFAOYSA-N 0.000 description 1
- AUZCPJSYHVZKQZ-UHFFFAOYSA-N C[n]1ncc(-c2ccc(C=O)cc2)c1 Chemical compound C[n]1ncc(-c2ccc(C=O)cc2)c1 AUZCPJSYHVZKQZ-UHFFFAOYSA-N 0.000 description 1
- AFDOYTHGOAARGS-UHFFFAOYSA-N C[n]1ncc(-c2ccc3C(I)=CCCc3c2)c1 Chemical compound C[n]1ncc(-c2ccc3C(I)=CCCc3c2)c1 AFDOYTHGOAARGS-UHFFFAOYSA-N 0.000 description 1
- NZOVMAWNOOEQJP-UHFFFAOYSA-N C[n]1ncc(N(CCc(c2ccc3)c3[IH]C)C2=O)c1 Chemical compound C[n]1ncc(N(CCc(c2ccc3)c3[IH]C)C2=O)c1 NZOVMAWNOOEQJP-UHFFFAOYSA-N 0.000 description 1
- STTJHAHQLUBBDE-UHFFFAOYSA-N C[n]1ncc(N(Cc(c2ccc3)c3I)C2=O)c1 Chemical compound C[n]1ncc(N(Cc(c2ccc3)c3I)C2=O)c1 STTJHAHQLUBBDE-UHFFFAOYSA-N 0.000 description 1
- RZLGPVWNRCQORH-UHFFFAOYSA-N C[n]1ncc(N(Cc2ccccc2C2)C2=O)c1 Chemical compound C[n]1ncc(N(Cc2ccccc2C2)C2=O)c1 RZLGPVWNRCQORH-UHFFFAOYSA-N 0.000 description 1
- ZTPPEWQGGMDBSQ-UHFFFAOYSA-N C[n]1ncc(N2Cc3cccc(-c4n[n](C5CCOCC5)c5c4CNCC5)c3CC2)c1 Chemical compound C[n]1ncc(N2Cc3cccc(-c4n[n](C5CCOCC5)c5c4CNCC5)c3CC2)c1 ZTPPEWQGGMDBSQ-UHFFFAOYSA-N 0.000 description 1
- MFNJLDCPTVOUCZ-UHFFFAOYSA-N C[n]1ncc(N2Cc3cccc(-c4n[n](C5CCOCC5)c5c4CNCC5)c3CCC2)c1 Chemical compound C[n]1ncc(N2Cc3cccc(-c4n[n](C5CCOCC5)c5c4CNCC5)c3CCC2)c1 MFNJLDCPTVOUCZ-UHFFFAOYSA-N 0.000 description 1
- UVDDABQIYPFVRB-UHFFFAOYSA-N C[n]1ncc(N2Cc3cccc(Br)c3CC2)c1 Chemical compound C[n]1ncc(N2Cc3cccc(Br)c3CC2)c1 UVDDABQIYPFVRB-UHFFFAOYSA-N 0.000 description 1
- UYLYFEYQNFLCEX-UHFFFAOYSA-N C[n]1ncc(N2Cc3cccc([IH]C)c3CC2)c1 Chemical compound C[n]1ncc(N2Cc3cccc([IH]C)c3CC2)c1 UYLYFEYQNFLCEX-UHFFFAOYSA-N 0.000 description 1
- VXCOSIIXRKLCGE-UHFFFAOYSA-N Cc([nH]c1c2)cc1cc(-c1c[n](C)nc1)c2Cl Chemical compound Cc([nH]c1c2)cc1cc(-c1c[n](C)nc1)c2Cl VXCOSIIXRKLCGE-UHFFFAOYSA-N 0.000 description 1
- YGIHIAOGNGGTOO-UHFFFAOYSA-N Cc([n](C)nc1)c1-c(nc1)cc2c1c(C)ccc2 Chemical compound Cc([n](C)nc1)c1-c(nc1)cc2c1c(C)ccc2 YGIHIAOGNGGTOO-UHFFFAOYSA-N 0.000 description 1
- VROAZBUBLKHGDJ-UHFFFAOYSA-N Cc(c1c2[nH]cc1)ccc2Cl Chemical compound Cc(c1c2[nH]cc1)ccc2Cl VROAZBUBLKHGDJ-UHFFFAOYSA-N 0.000 description 1
- FVVVRJDPVBLLPY-UHFFFAOYSA-N Cc(cc1)cc(C)c1-c1c[n](cccc2Br)c2n1 Chemical compound Cc(cc1)cc(C)c1-c1c[n](cccc2Br)c2n1 FVVVRJDPVBLLPY-UHFFFAOYSA-N 0.000 description 1
- FTPDFNMKOYXGFX-UHFFFAOYSA-N Cc(cc1CN)ccc1[Cl]=C Chemical compound Cc(cc1CN)ccc1[Cl]=C FTPDFNMKOYXGFX-UHFFFAOYSA-N 0.000 description 1
- MQPVQCUKTCDLKI-UHFFFAOYSA-N Cc1c(CC(N(C)C2)=O)c2ccc1 Chemical compound Cc1c(CC(N(C)C2)=O)c2ccc1 MQPVQCUKTCDLKI-UHFFFAOYSA-N 0.000 description 1
- OCUASPRFYOWGNX-UHFFFAOYSA-N Cc1c(CC(N(C2)c3c[n](C)nc3)=O)c2ccc1 Chemical compound Cc1c(CC(N(C2)c3c[n](C)nc3)=O)c2ccc1 OCUASPRFYOWGNX-UHFFFAOYSA-N 0.000 description 1
- ZLPHGLXOPZPNCO-UHFFFAOYSA-N Cc1c(CCCN(C2)c3c[n](C)nc3)c2ccc1 Chemical compound Cc1c(CCCN(C2)c3c[n](C)nc3)c2ccc1 ZLPHGLXOPZPNCO-UHFFFAOYSA-N 0.000 description 1
- CXCNKRSLTYNTBY-UHFFFAOYSA-N Cc1c(cnc(-c2c[n](C)nc2)c2)c2ccc1F Chemical compound Cc1c(cnc(-c2c[n](C)nc2)c2)c2ccc1F CXCNKRSLTYNTBY-UHFFFAOYSA-N 0.000 description 1
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N Cc1c[nH]c2c1cccc2 Chemical compound Cc1c[nH]c2c1cccc2 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 1
- YUYCOIGOXLUAMD-UHFFFAOYSA-N Cc1cc(C(Nc2cc([n](C)nc3)c3cc2)=O)ccc1 Chemical compound Cc1cc(C(Nc2cc([n](C)nc3)c3cc2)=O)ccc1 YUYCOIGOXLUAMD-UHFFFAOYSA-N 0.000 description 1
- YCCQMWNXDPSHKF-UHFFFAOYSA-N Cc1cc(C(Nc2ccnc(C)c2)=O)ccc1 Chemical compound Cc1cc(C(Nc2ccnc(C)c2)=O)ccc1 YCCQMWNXDPSHKF-UHFFFAOYSA-N 0.000 description 1
- DBCREUIMFKGZMA-UHFFFAOYSA-N Cc1cc(C(Nc2cnccc2)=O)ccc1 Chemical compound Cc1cc(C(Nc2cnccc2)=O)ccc1 DBCREUIMFKGZMA-UHFFFAOYSA-N 0.000 description 1
- KNNWFMSGVFFOPV-UHFFFAOYSA-N Cc1cc(C(Nc2cncnc2)=O)ccc1 Chemical compound Cc1cc(C(Nc2cncnc2)=O)ccc1 KNNWFMSGVFFOPV-UHFFFAOYSA-N 0.000 description 1
- XUEXYMCXIFBYTP-UHFFFAOYSA-N Cc1cc(C(Nc2nc(cccc3)c3[n]2C)=O)ccc1 Chemical compound Cc1cc(C(Nc2nc(cccc3)c3[n]2C)=O)ccc1 XUEXYMCXIFBYTP-UHFFFAOYSA-N 0.000 description 1
- CIAZHDFYVBXCTO-UHFFFAOYSA-N Cc1cc(C=C)cc2c1cncc2 Chemical compound Cc1cc(C=C)cc2c1cncc2 CIAZHDFYVBXCTO-UHFFFAOYSA-N 0.000 description 1
- HTKJACOWFNOMJI-UHFFFAOYSA-N Cc1cc(N=C)c(cnc(-c2c[n](C)nc2)c2)c2c1 Chemical compound Cc1cc(N=C)c(cnc(-c2c[n](C)nc2)c2)c2c1 HTKJACOWFNOMJI-UHFFFAOYSA-N 0.000 description 1
- DSMQAJKJXLMWHK-UHFFFAOYSA-N Cc1cc(NC(c2cccc(I)c2)=O)ccn1 Chemical compound Cc1cc(NC(c2cccc(I)c2)=O)ccn1 DSMQAJKJXLMWHK-UHFFFAOYSA-N 0.000 description 1
- QNGOXHWOWAXLCS-UHFFFAOYSA-N Cc1cc(cc(-c2c[n](C)nc2)c(C#N)c2)c2[n]1I Chemical compound Cc1cc(cc(-c2c[n](C)nc2)c(C#N)c2)c2[n]1I QNGOXHWOWAXLCS-UHFFFAOYSA-N 0.000 description 1
- XFRIKIGNDWYHPR-UHFFFAOYSA-N Cc1cc(cc(-c2c[n](C)nc2)c(C(F)F)c2)c2[n]1I Chemical compound Cc1cc(cc(-c2c[n](C)nc2)c(C(F)F)c2)c2[n]1I XFRIKIGNDWYHPR-UHFFFAOYSA-N 0.000 description 1
- UZNRSVWFBAENJJ-UHFFFAOYSA-N Cc1cc(cc(-c2c[n](C)nc2)nc2)c2[n]1-c1n[n](C2CCOCC2)c(CC2)c1CN2C(NC)=O Chemical compound Cc1cc(cc(-c2c[n](C)nc2)nc2)c2[n]1-c1n[n](C2CCOCC2)c(CC2)c1CN2C(NC)=O UZNRSVWFBAENJJ-UHFFFAOYSA-N 0.000 description 1
- XVENQKFIHRSMRG-UHFFFAOYSA-N Cc1cc(cc(-c2c[n](C)nc2)nc2)c2[n]1-c1n[n](C2CCOCC2)c2c1CNCC2 Chemical compound Cc1cc(cc(-c2c[n](C)nc2)nc2)c2[n]1-c1n[n](C2CCOCC2)c2c1CNCC2 XVENQKFIHRSMRG-UHFFFAOYSA-N 0.000 description 1
- CIPAFMWUZISJBW-UHFFFAOYSA-N Cc1cc(cc(-c2c[n](C)nc2)nc2)c2[n]1C Chemical compound Cc1cc(cc(-c2c[n](C)nc2)nc2)c2[n]1C CIPAFMWUZISJBW-UHFFFAOYSA-N 0.000 description 1
- KQGQTSSUGPIXQG-UHFFFAOYSA-N Cc1ccc[n]2c1nc(-c(cc1)ccc1OC(F)(F)F)c2 Chemical compound Cc1ccc[n]2c1nc(-c(cc1)ccc1OC(F)(F)F)c2 KQGQTSSUGPIXQG-UHFFFAOYSA-N 0.000 description 1
- GZSGOOWNEOBWCG-UHFFFAOYSA-N Cc1ccc[n]2c1nc(C(O)=O)c2 Chemical compound Cc1ccc[n]2c1nc(C(O)=O)c2 GZSGOOWNEOBWCG-UHFFFAOYSA-N 0.000 description 1
- XNQLHQHDIYSHHV-UHFFFAOYSA-N Cc1cccc2c1[o]c(-c1cnccc1)n2 Chemical compound Cc1cccc2c1[o]c(-c1cnccc1)n2 XNQLHQHDIYSHHV-UHFFFAOYSA-N 0.000 description 1
- TZPZTDFDCDHPHG-UHFFFAOYSA-N Cc1cccc2c1cnc(-c(cc1)cnc1C(NC)=O)c2F Chemical compound Cc1cccc2c1cnc(-c(cc1)cnc1C(NC)=O)c2F TZPZTDFDCDHPHG-UHFFFAOYSA-N 0.000 description 1
- XRQHRHFTEFQDEM-UHFFFAOYSA-N Cc1cccc2nc(-c(cc3)ccc3OC)c[n]12 Chemical compound Cc1cccc2nc(-c(cc3)ccc3OC)c[n]12 XRQHRHFTEFQDEM-UHFFFAOYSA-N 0.000 description 1
- GPQXDIFDLOKPGO-UHFFFAOYSA-N Cc1nc(-c2c[n](C)nc2)cc2cccc(I)c12 Chemical compound Cc1nc(-c2c[n](C)nc2)cc2cccc(I)c12 GPQXDIFDLOKPGO-UHFFFAOYSA-N 0.000 description 1
- NAVHMWJHGPWYCU-UHFFFAOYSA-N Cc1ncc(-c2cc3cccc(I)c3cn2)[s]1 Chemical compound Cc1ncc(-c2cc3cccc(I)c3cn2)[s]1 NAVHMWJHGPWYCU-UHFFFAOYSA-N 0.000 description 1
- FXXCBVQRZRTLFR-UHFFFAOYSA-N Cc1ncc(-c2ncc(c(C)ccc3)c3c2)[s]1 Chemical compound Cc1ncc(-c2ncc(c(C)ccc3)c3c2)[s]1 FXXCBVQRZRTLFR-UHFFFAOYSA-N 0.000 description 1
- UKFQWACOHOSVGA-UHFFFAOYSA-N Cc1nccc(NC(c2ccccc2)=O)c1 Chemical compound Cc1nccc(NC(c2ccccc2)=O)c1 UKFQWACOHOSVGA-UHFFFAOYSA-N 0.000 description 1
- FGSVFESTSIAXKM-UHFFFAOYSA-N FC(F)(F)SOC1CCOCC1 Chemical compound FC(F)(F)SOC1CCOCC1 FGSVFESTSIAXKM-UHFFFAOYSA-N 0.000 description 1
- OXFWFVMCJNGRCL-UHFFFAOYSA-N Ic1c2nc(-c3cnccc3)[nH]c2ccc1 Chemical compound Ic1c2nc(-c3cnccc3)[nH]c2ccc1 OXFWFVMCJNGRCL-UHFFFAOYSA-N 0.000 description 1
- PSBDRZJULJXNAT-UHFFFAOYSA-N N#Cc1cc(NC(c2cccc(I)c2)=O)ccc1 Chemical compound N#Cc1cc(NC(c2cccc(I)c2)=O)ccc1 PSBDRZJULJXNAT-UHFFFAOYSA-N 0.000 description 1
- YGRWJZJTOHADFF-UHFFFAOYSA-N NC(C1=CC2)=CC=CC1=CC2=O Chemical compound NC(C1=CC2)=CC=CC1=CC2=O YGRWJZJTOHADFF-UHFFFAOYSA-N 0.000 description 1
- RKIWGTSBHLQOOI-UHFFFAOYSA-N Nc(nc1)nc2c1c(I)ccc2 Chemical compound Nc(nc1)nc2c1c(I)ccc2 RKIWGTSBHLQOOI-UHFFFAOYSA-N 0.000 description 1
- TUORBCYNVRXFDX-UHFFFAOYSA-N Nc1c2nc(-c3cnccc3)[nH]c2ccc1 Chemical compound Nc1c2nc(-c3cnccc3)[nH]c2ccc1 TUORBCYNVRXFDX-UHFFFAOYSA-N 0.000 description 1
- OQSTUHDDYDMANO-UHFFFAOYSA-N O=C(Cc(c(C1)ccc2)c2I)N1C1CCCCC1 Chemical compound O=C(Cc(c(C1)ccc2)c2I)N1C1CCCCC1 OQSTUHDDYDMANO-UHFFFAOYSA-N 0.000 description 1
- QRKLKNHKYLIORU-UHFFFAOYSA-N O=C(Cc1c(C2)cccc1I)N2C1CCCC1 Chemical compound O=C(Cc1c(C2)cccc1I)N2C1CCCC1 QRKLKNHKYLIORU-UHFFFAOYSA-N 0.000 description 1
- VRJMTZCRJNWVOF-UHFFFAOYSA-N O=C(c1cc(I)ccc1)Nc1ccc(C[n]2ncnc2)cc1 Chemical compound O=C(c1cc(I)ccc1)Nc1ccc(C[n]2ncnc2)cc1 VRJMTZCRJNWVOF-UHFFFAOYSA-N 0.000 description 1
- FDEBNROIVHAUBJ-UHFFFAOYSA-N O=C(c1cc(I)ccc1)Nc1cncnc1 Chemical compound O=C(c1cc(I)ccc1)Nc1cncnc1 FDEBNROIVHAUBJ-UHFFFAOYSA-N 0.000 description 1
- ZTOCJPKQOZLEJG-UHFFFAOYSA-N O=C(c1cccc(I)c1)Nc(cc1)ccc1-[n]1cncc1 Chemical compound O=C(c1cccc(I)c1)Nc(cc1)ccc1-[n]1cncc1 ZTOCJPKQOZLEJG-UHFFFAOYSA-N 0.000 description 1
- HBUBMVNSVLQQJD-UHFFFAOYSA-N O=C(c1cccc(I)c1)Nc1cnccc1 Chemical compound O=C(c1cccc(I)c1)Nc1cnccc1 HBUBMVNSVLQQJD-UHFFFAOYSA-N 0.000 description 1
- RLWXFOZLWDQROC-UHFFFAOYSA-N O=C1NC=C2C(Br)=CC(Cl)=CC2=C1 Chemical compound O=C1NC=C2C(Br)=CC(Cl)=CC2=C1 RLWXFOZLWDQROC-UHFFFAOYSA-N 0.000 description 1
- PQALDHKLTCQGDF-UHFFFAOYSA-N O=C1NCCCc2c1cccc2Br Chemical compound O=C1NCCCc2c1cccc2Br PQALDHKLTCQGDF-UHFFFAOYSA-N 0.000 description 1
- XDPCNPCKDGQBAN-UHFFFAOYSA-N OC1COCC1 Chemical compound OC1COCC1 XDPCNPCKDGQBAN-UHFFFAOYSA-N 0.000 description 1
- BYOYOQPQKRORTD-UHFFFAOYSA-N OCc1c(cccc2I)c2cnc1 Chemical compound OCc1c(cccc2I)c2cnc1 BYOYOQPQKRORTD-UHFFFAOYSA-N 0.000 description 1
- TVJFLGVQRGFALN-UHFFFAOYSA-N Oc1cccc(-c2c[n](cccc3I)c3n2)c1 Chemical compound Oc1cccc(-c2c[n](cccc3I)c3n2)c1 TVJFLGVQRGFALN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Toxicology (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Gastroenterology & Hepatology (AREA)
- Vascular Medicine (AREA)
- Ophthalmology & Optometry (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2016/083118 | 2016-05-24 | ||
| CN2016083118 | 2016-05-24 | ||
| PCT/US2017/034326 WO2017205538A1 (en) | 2016-05-24 | 2017-05-24 | Pyrazolopyridine derivatives for the treatment of cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019516759A JP2019516759A (ja) | 2019-06-20 |
| JP2019516759A5 JP2019516759A5 (enExample) | 2020-07-02 |
| JP7014736B2 true JP7014736B2 (ja) | 2022-02-01 |
Family
ID=59055277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018561557A Expired - Fee Related JP7014736B2 (ja) | 2016-05-24 | 2017-05-24 | がんの処置のためのピラゾロピリジン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US11247989B2 (enExample) |
| EP (1) | EP3464286B1 (enExample) |
| JP (1) | JP7014736B2 (enExample) |
| CN (1) | CN109476663B (enExample) |
| MA (1) | MA45146A (enExample) |
| WO (1) | WO2017205538A1 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2018209164B2 (en) | 2017-01-17 | 2021-11-04 | Heparegenix Gmbh | Protein kinase inhibitors for promoting liver regeneration or reducing or preventing hepatocyte death |
| CA3095367A1 (en) * | 2018-03-29 | 2019-10-03 | Board Of Regents, The University Of Texas System | Imidazopiperazine inhibitors of transcription activating proteins |
| WO2019195846A1 (en) | 2018-04-06 | 2019-10-10 | Board Of Regents, The University Of Texas System | Imidazopiperazinone inhibitors of transcription activating proteins |
| CN110878042B (zh) * | 2018-09-05 | 2021-06-01 | 新发药业有限公司 | 一种n-取代基哌啶-3-酮的制备方法 |
| CN111320621B (zh) * | 2018-12-14 | 2022-10-04 | 中国科学院广州生物医药与健康研究院 | 一种吲嗪类化合物及其制备方法和应用 |
| EP3930759A4 (en) * | 2019-02-27 | 2023-03-22 | Cullgen (Shanghai), Inc. | CYCLIC AMP-RESPONSIVE ELEMENT BINDING PROTEIN (CBP) AND/OR ADENOVIRAL E1A BINDING PROTEIN OF 300 KDA (P300) DEGRADATION COMPOUNDS AND METHODS OF USE |
| US20220135538A1 (en) * | 2019-02-27 | 2022-05-05 | Constellation Pharmaceuticals, Inc. | P300/cbp hat inhibitors and methods for their use |
| SG11202110714VA (en) * | 2019-04-09 | 2021-10-28 | Plexxikon Inc | Condensed azines for ep300 or cbp modulation and indications therefor |
| WO2021020363A1 (ja) | 2019-07-29 | 2021-02-04 | 武田薬品工業株式会社 | 複素環化合物 |
| TW202120095A (zh) * | 2019-08-05 | 2021-06-01 | 美商美國禮來大藥廠 | 7,8-二氫-4H-吡唑并[4,3-c]氮呯-6-酮化合物 |
| KR20220132592A (ko) * | 2020-01-27 | 2022-09-30 | 브리스톨-마이어스 스큅 컴퍼니 | 톨-유사 수용체 7 (TLR7) 효능제로서의 1H-피라졸로[4,3-d]피리미딘 화합물 |
| CN111440161B (zh) * | 2020-05-15 | 2023-04-14 | 中国药科大学 | 一种具有par4拮抗活性的二环杂芳基类化合物及其应用 |
| CN111819574B (zh) * | 2020-06-10 | 2024-04-16 | 北京小米移动软件有限公司 | 生物特征的验证方法及装置、电子设备及存储介质 |
| WO2021257863A1 (en) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Pyrrolotriazine compounds as jak2 v617f inhibitors |
| US11691971B2 (en) | 2020-06-19 | 2023-07-04 | Incyte Corporation | Naphthyridinone compounds as JAK2 V617F inhibitors |
| US11767323B2 (en) | 2020-07-02 | 2023-09-26 | Incyte Corporation | Tricyclic pyridone compounds as JAK2 V617F inhibitors |
| IL299612A (en) | 2020-07-02 | 2023-03-01 | Incyte Corp | Tricyclic urea compounds as JAK2 V617F inhibitors |
| US11661422B2 (en) | 2020-08-27 | 2023-05-30 | Incyte Corporation | Tricyclic urea compounds as JAK2 V617F inhibitors |
| CN112079826B (zh) * | 2020-09-17 | 2022-07-29 | 广州中医药大学(广州中医药研究院) | 一类甾体合成酶抑制剂及其治疗应用 |
| WO2022093817A1 (en) * | 2020-10-26 | 2022-05-05 | Yale University | Macrophage migration inhibitory factor inhibitors, and methods of making and using same |
| WO2022140231A1 (en) | 2020-12-21 | 2022-06-30 | Incyte Corporation | Deazaguaine compounds as jak2 v617f inhibitors |
| JPWO2022138944A1 (enExample) * | 2020-12-25 | 2022-06-30 | ||
| US11958861B2 (en) | 2021-02-25 | 2024-04-16 | Incyte Corporation | Spirocyclic lactams as JAK2 V617F inhibitors |
| AU2022380979A1 (en) | 2021-11-02 | 2024-06-06 | Flare Therapeutics Inc. | Pparg inverse agonists and uses thereof |
| AU2022386486A1 (en) | 2021-11-12 | 2024-05-09 | Insilico Medicine Ip Limited | Small molecule inhibitors of ubiquitin specific protease 1 (usp1) and uses thereof |
| EP4493558A1 (en) | 2022-03-17 | 2025-01-22 | Incyte Corporation | Tricyclic urea compounds as jak2 v617f inhibitors |
| JP2025524870A (ja) | 2022-07-18 | 2025-08-01 | Jsr株式会社 | α,β不飽和カルボニル化合物およびそれらの中間体の光触媒合成 |
| US20240109868A1 (en) * | 2022-08-29 | 2024-04-04 | Miracure Biotechnology Limited | Ep300/cbp modulator, preparation method therefor and use thereof |
| CN115710249B (zh) * | 2022-11-14 | 2024-11-19 | 广东工业大学 | 一种多取代异喹啉和1,6-萘啶化合物的制备方法及光电材料常见分子骨架 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011526283A (ja) | 2008-06-25 | 2011-10-06 | ブリストル−マイヤーズ スクイブ カンパニー | 抗−hiv薬としてのジケト縮合アゾロピペリジンおよびアゾロピペラジン |
| JP2014526446A (ja) | 2011-09-12 | 2014-10-06 | サノフイ | インダニル置換の4,5,6,7−テトラヒドロ−1H−ピラゾロ[4,3−c]ピリジン、医薬としてのその使用、及びそれらを含む医薬製剤 |
| JP6771464B2 (ja) | 2014-11-27 | 2020-10-21 | ジェネンテック, インコーポレイテッド | Cbpおよび/またはep300インヒビターとしての、4,5,6,7−テトラヒドロ−1h−ピラゾロ[4,3−c]ピリジン−3−アミン化合物 |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CU22545A1 (es) | 1994-11-18 | 1999-03-31 | Centro Inmunologia Molecular | Obtención de un anticuerpo quimérico y humanizado contra el receptor del factor de crecimiento epidérmico para uso diagnóstico y terapéutico |
| DK27383A (da) * | 1982-02-17 | 1983-08-18 | Lepetit Spa | Fremgangsmaade til fremstilling af pyrazol(4,3-c)pyridiner |
| US4943533A (en) | 1984-03-01 | 1990-07-24 | The Regents Of The University Of California | Hybrid cell lines that produce monoclonal antibodies to epidermal growth factor receptor |
| DE69025946T2 (de) | 1989-09-08 | 1996-10-17 | Univ Duke | Modifikationen der struktur des egf-rezeptor-gens in menschlichen glioma |
| AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| ATE207366T1 (de) | 1993-12-24 | 2001-11-15 | Merck Patent Gmbh | Immunokonjugate |
| IL112248A0 (en) | 1994-01-25 | 1995-03-30 | Warner Lambert Co | Tricyclic heteroaromatic compounds and pharmaceutical compositions containing them |
| IL112249A (en) | 1994-01-25 | 2001-11-25 | Warner Lambert Co | Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds |
| US5654307A (en) | 1994-01-25 | 1997-08-05 | Warner-Lambert Company | Bicyclic compounds capable of inhibiting tyrosine kinases of the epidermal growth factor receptor family |
| ATE176910T1 (de) | 1994-07-21 | 1999-03-15 | Akzo Nobel Nv | Zyklische keton peroxyde zubereitungen |
| US5804396A (en) | 1994-10-12 | 1998-09-08 | Sugen, Inc. | Assay for agents active in proliferative disorders |
| EP0817775B1 (en) | 1995-03-30 | 2001-09-12 | Pfizer Inc. | Quinazoline derivatives |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| GB9508565D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quiazoline derivative |
| US5747498A (en) | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| JPH11507535A (ja) | 1995-06-07 | 1999-07-06 | イムクローン システムズ インコーポレイテッド | 腫瘍の成長を抑制する抗体および抗体フラグメント類 |
| ATE212993T1 (de) | 1995-07-06 | 2002-02-15 | Novartis Erfind Verwalt Gmbh | Pyrolopyrimidine und verfahren zu ihrer herstellung |
| US5760041A (en) | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| EP0892789B2 (en) | 1996-04-12 | 2009-11-18 | Warner-Lambert Company LLC | Irreversible inhibitors of tyrosine kinases |
| AR007857A1 (es) | 1996-07-13 | 1999-11-24 | Glaxo Group Ltd | Compuestos heterociclicos fusionados como inhibidores de proteina tirosina quinasa, sus metodos de preparacion, intermediarios uso en medicina ycomposiciones farmaceuticas que los contienen. |
| ID18494A (id) | 1996-10-02 | 1998-04-16 | Novartis Ag | Turunan pirazola leburan dan proses pembuatannya |
| US6002008A (en) | 1997-04-03 | 1999-12-14 | American Cyanamid Company | Substituted 3-cyano quinolines |
| UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| US6235883B1 (en) | 1997-05-05 | 2001-05-22 | Abgenix, Inc. | Human monoclonal antibodies to epidermal growth factor receptor |
| AU7165698A (en) | 1997-05-06 | 1998-11-27 | American Cyanamid Company | Use of quinazoline compounds for the treatment of polycystic kidney disease |
| ZA986732B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitiors of tyrosine kinases |
| ZA986729B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitors of tyrosine kinases |
| TW436485B (en) | 1997-08-01 | 2001-05-28 | American Cyanamid Co | Substituted quinazoline derivatives |
| CN1278176A (zh) | 1997-11-06 | 2000-12-27 | 美国氰胺公司 | 喹唑啉衍生物作为用于治疗结肠息肉的酪氨酸激酶抑制剂的应用 |
| EA003786B1 (ru) | 1998-11-19 | 2003-10-30 | Варнер Ламберт Компани | N-[4-(3-хлор-4-фторфениламино)-7-(3-морфолин-4-илпропокси)хиназолин-6-ил]акриламид - необратимый ингибитор тирозинкиназ |
| CA2493625A1 (en) | 2002-07-25 | 2004-02-19 | Pharmacia Italia S.P.A. | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| MXPA05000945A (es) | 2002-07-25 | 2005-05-16 | Pharmacia Italia Spa | Biciclo-pirazoles activos como inhibidores de la cinasa, procedimientos para su preparacion y composiciones farmaceuticas que los contienen. |
| JP2006519816A (ja) | 2003-03-11 | 2006-08-31 | ファルマシア・イタリア・ソシエタ・ペル・アツィオーニ | キナーゼ阻害剤として活性なビシクロピラゾール誘導体、それらの製造方法、及びそれらを含んでなる医薬組成物 |
| JP4361545B2 (ja) | 2005-05-09 | 2009-11-11 | 小野薬品工業株式会社 | ProgrammedDeath1(PD−1)に対するヒトモノクローナル抗体および抗PD−1抗体単独または他の免疫療法と併用した癌治療方法 |
| HRP20151102T1 (xx) | 2005-07-01 | 2015-11-20 | E. R. Squibb & Sons, L.L.C. | Humana monoklonska antitijela za ligand programirane smrti 1 (pd-l1) |
| JP5219150B2 (ja) | 2005-12-12 | 2013-06-26 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | キナーゼ阻害薬として活性な置換ピラゾロ[4,3−c]ピリジン誘導体 |
| WO2007099166A1 (en) | 2006-03-03 | 2007-09-07 | Nerviano Medical Sciences S.R.L. | Pyrazolo-pyridine derivatives active as kinase inhibitors |
| KR101600634B1 (ko) | 2007-12-28 | 2016-03-07 | 미쓰비시 타나베 파마 코퍼레이션 | 항암제 |
| CA2715166C (en) | 2008-02-11 | 2017-05-16 | Curetech Ltd. | Monoclonal antibodies for tumor treatment |
| WO2009114335A2 (en) | 2008-03-12 | 2009-09-17 | Merck & Co., Inc. | Pd-1 binding proteins |
| CL2009001158A1 (es) | 2008-05-15 | 2009-10-23 | Nerviano Medical Sciences Srl | Compuestos derivados de los acidos carboxilicos, tales como 5,6-dihiro-4h-pirrolo[3,4-c]pirazol, furo[3,2-c]pirazol, tieno[2,3-c]pirazol, 4,5,6,7-tetrahidropirazol[4,3-c]piridina e indazol; composicion farmaceutica; y su uso en el tratamiento de trastornos proliferativos celulares asociados a la actividad de proteina quinasa alterada, tal como el cancer. |
| JP2012510429A (ja) | 2008-08-25 | 2012-05-10 | アンプリミューン、インコーポレーテッド | Pd−1アンタゴニストおよびその使用方法 |
| KR20250091300A (ko) | 2008-12-09 | 2025-06-20 | 제넨테크, 인크. | 항-pd-l1 항체 및 t 세포 기능을 향상시키기 위한 그의 용도 |
| JP2013512251A (ja) | 2009-11-24 | 2013-04-11 | アンプリミューン、インコーポレーテッド | Pd−l1/pd−l2の同時阻害 |
| CN101812063B (zh) | 2010-03-18 | 2012-04-25 | 中国医学科学院医药生物技术研究所 | α-萘磺酰胺基五元杂环类化合物及其抑瘤活性 |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| WO2013148114A1 (en) | 2012-03-30 | 2013-10-03 | University Of Florida Research Foundation, Inc. | P300/cbp inhibitors and methods of use |
| WO2014138727A1 (en) | 2013-03-08 | 2014-09-12 | Board Of Regents, The University Of Texas System | Suppression of malignant mesothelioma by overexpression or stimulation of endothelial protein c receptors (epcr) |
| EP2993174A1 (en) * | 2014-09-08 | 2016-03-09 | Helmholtz Zentrum München Deutsches Forschungszentrum für Gesundheit und Umwelt GmbH | Pyrazolopyridine derivatives and their use in therapy |
-
2017
- 2017-05-24 EP EP17729963.3A patent/EP3464286B1/en active Active
- 2017-05-24 MA MA045146A patent/MA45146A/fr unknown
- 2017-05-24 JP JP2018561557A patent/JP7014736B2/ja not_active Expired - Fee Related
- 2017-05-24 WO PCT/US2017/034326 patent/WO2017205538A1/en not_active Ceased
- 2017-05-24 CN CN201780045658.6A patent/CN109476663B/zh active Active
-
2018
- 2018-11-21 US US16/198,581 patent/US11247989B2/en active Active
-
2022
- 2022-01-06 US US17/570,139 patent/US20220127265A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011526283A (ja) | 2008-06-25 | 2011-10-06 | ブリストル−マイヤーズ スクイブ カンパニー | 抗−hiv薬としてのジケト縮合アゾロピペリジンおよびアゾロピペラジン |
| JP2014526446A (ja) | 2011-09-12 | 2014-10-06 | サノフイ | インダニル置換の4,5,6,7−テトラヒドロ−1H−ピラゾロ[4,3−c]ピリジン、医薬としてのその使用、及びそれらを含む医薬製剤 |
| JP6771464B2 (ja) | 2014-11-27 | 2020-10-21 | ジェネンテック, インコーポレイテッド | Cbpおよび/またはep300インヒビターとしての、4,5,6,7−テトラヒドロ−1h−ピラゾロ[4,3−c]ピリジン−3−アミン化合物 |
Non-Patent Citations (10)
| Title |
|---|
| Bioorganic & Medicinal Chemistry Letters,2005年,15(6),1687-1691 |
| DATABASE REGISTRY on STN,2011年12月05日,RN 1349159-92-7 |
| DATABASE REGISTRY on STN,2011年12月07日,RN 1350101-01-7 |
| DATABASE REGISTRY on STN,2012年04月13日,RN 1367868-74-3 |
| DATABASE REGISTRY on STN,2015年06月26日,RN 1789047-56-8 |
| DATABASE REGISTRY on STN,2015年06月28日,RN 1790521-91-3 |
| DATABASE REGISTRY on STN,2015年06月28日,RN 1790521-98-0 |
| DATABASE REGISTRY on STN,2015年06月28日,RN 1790625-75-0 |
| European Journal of Medicinal Chemistry,2014年,71,168-184 |
| Journal of Medicinal Chemstry,1985年,28(7),934-940 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109476663A (zh) | 2019-03-15 |
| EP3464286B1 (en) | 2021-08-18 |
| US20220127265A1 (en) | 2022-04-28 |
| US20190241558A1 (en) | 2019-08-08 |
| MA45146A (fr) | 2021-03-24 |
| CN109476663B (zh) | 2021-11-09 |
| US11247989B2 (en) | 2022-02-15 |
| JP2019516759A (ja) | 2019-06-20 |
| EP3464286A1 (en) | 2019-04-10 |
| WO2017205538A1 (en) | 2017-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7014736B2 (ja) | がんの処置のためのピラゾロピリジン誘導体 | |
| US11168070B2 (en) | Therapeutic compounds and uses thereof | |
| JP6771464B2 (ja) | Cbpおよび/またはep300インヒビターとしての、4,5,6,7−テトラヒドロ−1h−ピラゾロ[4,3−c]ピリジン−3−アミン化合物 | |
| JP6847844B2 (ja) | 治療用ピリダジン化合物およびその使用 | |
| JP6820254B2 (ja) | 治療用化合物およびその使用 | |
| US10150767B2 (en) | Therapeutic compounds and uses thereof | |
| JP6669744B2 (ja) | ブロモドメインのインヒビターとしての置換ピロロピリジン | |
| US20170340604A1 (en) | Therapeutic compounds and uses thereof | |
| JP6709792B2 (ja) | 治療用化合物およびその使用 | |
| HK40005958B (zh) | 用於治疗癌症的吡唑并吡啶衍生物 | |
| HK40005958A (en) | Pyrazolopyridine derivatives for the treatment of cancer | |
| HK1243073B (zh) | 治療性化合物及其用途 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190314 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200525 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20200525 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20210422 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20210430 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210802 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20211223 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20220120 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 7014736 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |