JP2020520356A5 - - Google Patents
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- Publication number
- JP2020520356A5 JP2020520356A5 JP2019563491A JP2019563491A JP2020520356A5 JP 2020520356 A5 JP2020520356 A5 JP 2020520356A5 JP 2019563491 A JP2019563491 A JP 2019563491A JP 2019563491 A JP2019563491 A JP 2019563491A JP 2020520356 A5 JP2020520356 A5 JP 2020520356A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyrimidine
- ethylamino
- ethoxy
- bromo
- 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 cyano, hydroxy Chemical group 0.000 claims 134
- 125000000217 alkyl group Chemical group 0.000 claims 99
- 229910052739 hydrogen Inorganic materials 0.000 claims 37
- 239000001257 hydrogen Substances 0.000 claims 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000004430 oxygen atom Chemical group O* 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 20
- 125000002947 alkylene group Chemical group 0.000 claims 17
- 206010028980 Neoplasm Diseases 0.000 claims 15
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 201000011510 cancer Diseases 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- CTQPPUPWHLGKOB-UHFFFAOYSA-N 4h-oxadiazol-5-one Chemical compound O=C1CN=NO1 CTQPPUPWHLGKOB-UHFFFAOYSA-N 0.000 claims 3
- 206010005003 Bladder cancer Diseases 0.000 claims 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 229940127089 cytotoxic agent Drugs 0.000 claims 3
- 230000028993 immune response Effects 0.000 claims 3
- 210000000987 immune system Anatomy 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000001959 radiotherapy Methods 0.000 claims 3
- 238000002626 targeted therapy Methods 0.000 claims 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims 3
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- QJGLOGMNORETMH-UHFFFAOYSA-N 3-[3-ethoxy-5-[6-[2-(2,4,6-trifluorophenyl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=C(C=C1F)F)F)C1=NOC(N1)=O QJGLOGMNORETMH-UHFFFAOYSA-N 0.000 claims 2
- QBXRJYJOLLINKR-UHFFFAOYSA-N 3-[3-ethoxy-5-[6-[2-(2-ethoxy-4-fluorophenyl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=C(C=C1)F)OCC)C1=NOC(N1)=O QBXRJYJOLLINKR-UHFFFAOYSA-N 0.000 claims 2
- XLDCYMRZFRLVNW-UHFFFAOYSA-N 3-[3-ethoxy-5-[6-[2-(2-ethyl-4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=C(C=C1)OC)CC)C1=NOC(N1)=O XLDCYMRZFRLVNW-UHFFFAOYSA-N 0.000 claims 2
- BWAJWJWTQHXEEH-UHFFFAOYSA-N 3-[3-ethoxy-5-[6-[2-(2-fluoro-4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=C(C=C1)OC)F)C1=NOC(N1)=O BWAJWJWTQHXEEH-UHFFFAOYSA-N 0.000 claims 2
- ZXFCHOFSTUKCOJ-UHFFFAOYSA-N 3-[3-ethoxy-5-[6-[2-[2-ethoxy-4-(trifluoromethyl)phenyl]ethylamino]pyrimidin-4-yl]thiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=C(C=C1)C(F)(F)F)OCC)C1=NOC(N1)=O ZXFCHOFSTUKCOJ-UHFFFAOYSA-N 0.000 claims 2
- VQJPXXKFYYMECV-UHFFFAOYSA-N 3-[3-ethoxy-5-[6-[2-[2-fluoro-4-(trifluoromethyl)phenyl]ethylamino]pyrimidin-4-yl]thiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=C(C=C1)C(F)(F)F)F)C1=NOC(N1)=O VQJPXXKFYYMECV-UHFFFAOYSA-N 0.000 claims 2
- ZONNJMNMMNSKOJ-UHFFFAOYSA-N 3-[5-[6-[2-(2,4-dichlorophenyl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound ClC1=C(C=CC(=C1)Cl)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC ZONNJMNMMNSKOJ-UHFFFAOYSA-N 0.000 claims 2
- GNYYWFUXPSBBRU-UHFFFAOYSA-N 3-[5-[6-[2-(3,4-dichlorophenyl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound ClC=1C=C(C=CC=1Cl)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC GNYYWFUXPSBBRU-UHFFFAOYSA-N 0.000 claims 2
- BJCIBKZOVPPABF-UHFFFAOYSA-N 3-[5-[6-[2-(4-bromo-2-chlorophenyl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound BrC1=CC(=C(C=C1)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC)Cl BJCIBKZOVPPABF-UHFFFAOYSA-N 0.000 claims 2
- CCDDZTDNMKMWIV-UHFFFAOYSA-N 3-[5-[6-[2-(4-bromo-2-ethoxyphenyl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound BrC1=CC(=C(C=C1)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC)OCC CCDDZTDNMKMWIV-UHFFFAOYSA-N 0.000 claims 2
- CYIGQRURNVPKFK-UHFFFAOYSA-N 3-[5-[6-[2-(4-bromo-3-chlorophenyl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophen-2-yl]-4H-1,2,4-oxadiazol-5-one Chemical compound BrC1=C(C=C(C=C1)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC)Cl CYIGQRURNVPKFK-UHFFFAOYSA-N 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- KPCBRVFEMIFEJW-UHFFFAOYSA-N 5-[4-[6-[2-(4-bromo-2,6-difluorophenyl)ethylamino]pyrimidin-4-yl]-2-methoxyphenyl]-1,2-oxazol-3-one Chemical compound BrC1=CC(=C(C(=C1)F)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)C1=CC(=NO1)O)OC)F KPCBRVFEMIFEJW-UHFFFAOYSA-N 0.000 claims 2
- ZCHNCEWRBASKAC-UHFFFAOYSA-N 5-[5-[6-[2-(4-bromo-2,6-difluorophenyl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophen-2-yl]-3H-1,3,4-oxadiazol-2-one Chemical compound CCOc1cc(sc1-c1n[nH]c(=O)o1)-c1cc(NCCc2c(F)cc(Br)cc2F)ncn1 ZCHNCEWRBASKAC-UHFFFAOYSA-N 0.000 claims 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000010061 Autosomal Dominant Polycystic Kidney Diseases 0.000 claims 2
- BQCLVOBRRWQCTM-UHFFFAOYSA-N BrC1=C(C=C(C=C1)Cl)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC Chemical compound BrC1=C(C=C(C=C1)Cl)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC BQCLVOBRRWQCTM-UHFFFAOYSA-N 0.000 claims 2
- ABTIJEQHHVCFBA-UHFFFAOYSA-N BrC1=CC(=C(C(=C1)F)CCNC1=CC(=NC(=N1)C)C1=CC(=C(S1)C1=NOC(N1)=O)OCC)F Chemical compound BrC1=CC(=C(C(=C1)F)CCNC1=CC(=NC(=N1)C)C1=CC(=C(S1)C1=NOC(N1)=O)OCC)F ABTIJEQHHVCFBA-UHFFFAOYSA-N 0.000 claims 2
- FOFKQTVWIRYJIL-UHFFFAOYSA-N BrC1=CC(=C(C=C1)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC)F Chemical compound BrC1=CC(=C(C=C1)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC)F FOFKQTVWIRYJIL-UHFFFAOYSA-N 0.000 claims 2
- HNSLOVZJVRHJNB-UHFFFAOYSA-N C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC(=C(C=C1)O)OC)C1=NOC(N1)=O Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC(=C(C=C1)O)OC)C1=NOC(N1)=O HNSLOVZJVRHJNB-UHFFFAOYSA-N 0.000 claims 2
- DMRVMUKPEWYJIE-UHFFFAOYSA-N C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC(=C(C=C1)OC)O)C1=NOC(N1)=O Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC(=C(C=C1)OC)O)C1=NOC(N1)=O DMRVMUKPEWYJIE-UHFFFAOYSA-N 0.000 claims 2
- GOBGCXSMLFKIOV-UHFFFAOYSA-N C(C)OC=1C=C(SC=1C1=NOC(N1)=O)C1=CC(=NC=N1)NCCC1=C(C#N)C=C(C=C1)F Chemical compound C(C)OC=1C=C(SC=1C1=NOC(N1)=O)C1=CC(=NC=N1)NCCC1=C(C#N)C=C(C=C1)F GOBGCXSMLFKIOV-UHFFFAOYSA-N 0.000 claims 2
- JPZFVNWNJMAJJZ-UHFFFAOYSA-N CC(C)Oc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Br)cc2F)ncn1 Chemical compound CC(C)Oc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Br)cc2F)ncn1 JPZFVNWNJMAJJZ-UHFFFAOYSA-N 0.000 claims 2
- CFHTYTITSCAMJO-UHFFFAOYSA-N CCCOc1cc(Br)ccc1CCNc1cc(ncn1)-c1cc(OCC)c(s1)-c1nc(=O)o[nH]1 Chemical compound CCCOc1cc(Br)ccc1CCNc1cc(ncn1)-c1cc(OCC)c(s1)-c1nc(=O)o[nH]1 CFHTYTITSCAMJO-UHFFFAOYSA-N 0.000 claims 2
- YZBLXDGRXJUMST-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Br)cc2F)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Br)cc2F)ncn1 YZBLXDGRXJUMST-UHFFFAOYSA-N 0.000 claims 2
- ZUCGPYSNZVAQIC-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Br)cc2OC)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Br)cc2OC)ncn1 ZUCGPYSNZVAQIC-UHFFFAOYSA-N 0.000 claims 2
- WUPMIHQBWMCPMJ-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Cl)cc2F)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Cl)cc2F)ncn1 WUPMIHQBWMCPMJ-UHFFFAOYSA-N 0.000 claims 2
- TXDYFXUYEGNEOD-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Cl)cc2OC)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Cl)cc2OC)ncn1 TXDYFXUYEGNEOD-UHFFFAOYSA-N 0.000 claims 2
- RVIRCDAIZVACJY-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)ccc(Cl)c2F)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)ccc(Cl)c2F)ncn1 RVIRCDAIZVACJY-UHFFFAOYSA-N 0.000 claims 2
- SCNUSBVKWLHESZ-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)ccc(F)c2Cl)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)ccc(F)c2Cl)ncn1 SCNUSBVKWLHESZ-UHFFFAOYSA-N 0.000 claims 2
- OPQZQPVWLKFNEX-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(OC)cc(Br)cc2OC)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(OC)cc(Br)cc2OC)ncn1 OPQZQPVWLKFNEX-UHFFFAOYSA-N 0.000 claims 2
- KXHVBNVHUDENBB-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cc(Br)ccc2OC)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cc(Br)ccc2OC)ncn1 KXHVBNVHUDENBB-UHFFFAOYSA-N 0.000 claims 2
- CPOOEZIRKAQMNY-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cc(Br)ccc2SC)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cc(Br)ccc2SC)ncn1 CPOOEZIRKAQMNY-UHFFFAOYSA-N 0.000 claims 2
- PQTCZKGSFJBZDE-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cc(C)c(Br)cc2F)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cc(C)c(Br)cc2F)ncn1 PQTCZKGSFJBZDE-UHFFFAOYSA-N 0.000 claims 2
- SFPPOLYJLCGTTH-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cc(F)c(Br)cc2C)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cc(F)c(Br)cc2C)ncn1 SFPPOLYJLCGTTH-UHFFFAOYSA-N 0.000 claims 2
- CKSMZXUBYYRCDE-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cc(F)c(Br)cc2F)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cc(F)c(Br)cc2F)ncn1 CKSMZXUBYYRCDE-UHFFFAOYSA-N 0.000 claims 2
- GMGVAJQAPSHSQY-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)c(C)c2)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)c(C)c2)ncn1 GMGVAJQAPSHSQY-UHFFFAOYSA-N 0.000 claims 2
- OIFKKSNOGUYHTN-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)c(F)c2)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)c(F)c2)ncn1 OIFKKSNOGUYHTN-UHFFFAOYSA-N 0.000 claims 2
- NZHLLPGMJXMIMG-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)c(OC)c2)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)c(OC)c2)ncn1 NZHLLPGMJXMIMG-UHFFFAOYSA-N 0.000 claims 2
- TYPROPXGGIXTSL-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)cc2)nc(C)n1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)cc2)nc(C)n1 TYPROPXGGIXTSL-UHFFFAOYSA-N 0.000 claims 2
- KJGXATJADPBWQG-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)cc2C)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)cc2C)ncn1 KJGXATJADPBWQG-UHFFFAOYSA-N 0.000 claims 2
- AQXNCPATZYQJGJ-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)cc2OC)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(Br)cc2OC)ncn1 AQXNCPATZYQJGJ-UHFFFAOYSA-N 0.000 claims 2
- RJMNOJSFWLQMDK-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(C)c(C)c2)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(C)c(C)c2)ncn1 RJMNOJSFWLQMDK-UHFFFAOYSA-N 0.000 claims 2
- LSIWUEBJGBSNQC-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(OC)c(Cl)c2)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(OC)c(Cl)c2)ncn1 LSIWUEBJGBSNQC-UHFFFAOYSA-N 0.000 claims 2
- WWBYVLRDLXFHLU-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(OC)cc2OC)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(OC)cc2OC)ncn1 WWBYVLRDLXFHLU-UHFFFAOYSA-N 0.000 claims 2
- HBLHCAZBELMRGY-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(cc2F)N(C)C)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc(cc2F)N(C)C)ncn1 HBLHCAZBELMRGY-UHFFFAOYSA-N 0.000 claims 2
- ZLEWETBNRXECTR-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cccc(OC)c2OC)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2cccc(OC)c2OC)ncn1 ZLEWETBNRXECTR-UHFFFAOYSA-N 0.000 claims 2
- MCYZOGQNPSVEGA-UHFFFAOYSA-N CCOc1nc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Br)cc2F)ncn1 Chemical compound CCOc1nc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Br)cc2F)ncn1 MCYZOGQNPSVEGA-UHFFFAOYSA-N 0.000 claims 2
- WZCGEZVZOGHCNO-UHFFFAOYSA-N CCc1nc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Br)cc2F)ncn1 Chemical compound CCc1nc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2c(F)cc(Br)cc2F)ncn1 WZCGEZVZOGHCNO-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
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| CN110621671A (zh) | 2017-05-18 | 2019-12-27 | 爱杜西亚药品有限公司 | 作为pge2受体调节剂的苯并呋喃及苯并噻吩衍生物 |
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