JP2017518961A5

JP2017518961A5 -

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Publication number: JP2017518961A5
Authority: JP; Japan
Prior art keywords: oxy; benzyl; dihydrobenzo; dioxin; amino
Prior art date: 2015-04-10
Legal status : Granted

Application number

JP2016562537A

Other languages

English (en)

Japanese (ja)

Other versions

JP6556755B2 (ja

JP2017518961A (ja

Filing date

2015-04-10

Publication date

2018-05-31

2015-04-08 Priority claimed from US14/681,772 external-priority patent/US9850225B2/en

2015-04-10 Application filed filed Critical

2017-07-13 Publication of JP2017518961A publication Critical patent/JP2017518961A/ja

2018-05-31 Publication of JP2017518961A5 publication Critical patent/JP2017518961A5/ja

2019-08-07 Application granted granted Critical

2019-08-07 Publication of JP6556755B2 publication Critical patent/JP6556755B2/ja

Status Expired - Fee Related legal-status Critical Current

2035-04-10 Anticipated expiration legal-status Critical

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-1 benzodioxanyl Chemical group 0.000 claims 35
150000003839 salts Chemical class 0.000 claims 15
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 13
239000008194 pharmaceutical composition Substances 0.000 claims 10
229910052739 hydrogen Inorganic materials 0.000 claims 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
125000005843 halogen group Chemical group 0.000 claims 7
239000001257 hydrogen Substances 0.000 claims 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
CTLCXWMADMXNOP-UHFFFAOYSA-N CC(C(NCC1=CC=C(C=C1)OCC2=C(C(=CC=C2)C3=CC4=C(C=C3)OCCO4)Cl)O)(C(=O)O)OCC5=CC(=CC=C5)C#N Chemical compound CC(C(NCC1=CC=C(C=C1)OCC2=C(C(=CC=C2)C3=CC4=C(C=C3)OCCO4)Cl)O)(C(=O)O)OCC5=CC(=CC=C5)C#N CTLCXWMADMXNOP-UHFFFAOYSA-N 0.000 claims 4
150000001875 compounds Chemical class 0.000 claims 4
150000002431 hydrogen Chemical group 0.000 claims 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
206010028980 Neoplasm Diseases 0.000 claims 3
201000011510 cancer Diseases 0.000 claims 3
125000004093 cyano group Chemical group *C#N 0.000 claims 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
208000002154 non-small cell lung carcinoma Diseases 0.000 claims 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 3
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
QRFZGYMIMILCRD-UHFFFAOYSA-N BrC1=CC(=C(OCC=2C=NC=C(C#N)C2)C=C1OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)CNCCO Chemical compound BrC1=CC(=C(OCC=2C=NC=C(C#N)C2)C=C1OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)CNCCO QRFZGYMIMILCRD-UHFFFAOYSA-N 0.000 claims 2
HMPBAHKGBGJLPU-YTTGMZPUSA-N BrC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C HMPBAHKGBGJLPU-YTTGMZPUSA-N 0.000 claims 2
FIGDDEFZKIEMPU-YTTGMZPUSA-N BrC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C#N Chemical compound BrC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C#N FIGDDEFZKIEMPU-YTTGMZPUSA-N 0.000 claims 2
FKHBHFXNNBCRCQ-HKBQPEDESA-N BrC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C FKHBHFXNNBCRCQ-HKBQPEDESA-N 0.000 claims 2
IWSHPAFBIFAYNV-HKBQPEDESA-N BrC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C1)OCC=1C=NC=C(C1)C#N)OCC=1C(=C(C=CC1)C1=CC=CC=C1)C Chemical compound BrC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C1)OCC=1C=NC=C(C1)C#N)OCC=1C(=C(C=CC1)C1=CC=CC=C1)C IWSHPAFBIFAYNV-HKBQPEDESA-N 0.000 claims 2
FKHBHFXNNBCRCQ-WJOKGBTCSA-N BrC=1C(=CC(=C(CN2[C@H](CCCC2)C(=O)O)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CN2[C@H](CCCC2)C(=O)O)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C FKHBHFXNNBCRCQ-WJOKGBTCSA-N 0.000 claims 2
ZJMRDMXXHNPVID-UHFFFAOYSA-N BrC=1C(=CC(=C(CNCCNC(C)=O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CNCCNC(C)=O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C ZJMRDMXXHNPVID-UHFFFAOYSA-N 0.000 claims 2
OOQBRRLRXWBSIG-UHFFFAOYSA-N BrC=1C(=CC(=C(CNCCNC(C)=O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C#N Chemical compound BrC=1C(=CC(=C(CNCCNC(C)=O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C#N OOQBRRLRXWBSIG-UHFFFAOYSA-N 0.000 claims 2
OGKWCZSSKAICFQ-UHFFFAOYSA-N BrC=1C(=CC(=C(CNCCNC(C)=O)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CNCCNC(C)=O)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C OGKWCZSSKAICFQ-UHFFFAOYSA-N 0.000 claims 2
HDLZBRJSTJBMBE-NDEPHWFRSA-N BrC=1C(=CC(=C(CNC[C@H](CC(=O)O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CNC[C@H](CC(=O)O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C HDLZBRJSTJBMBE-NDEPHWFRSA-N 0.000 claims 2
WCQRFVWNVPNFQT-MHZLTWQESA-N BrC=1C(=CC(=C(CNC[C@H](CC(=O)O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C#N Chemical compound BrC=1C(=CC(=C(CNC[C@H](CC(=O)O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C#N WCQRFVWNVPNFQT-MHZLTWQESA-N 0.000 claims 2
LHZDWJSQSPEZFZ-MHZLTWQESA-N BrC=1C(=CC(=C(CNC[C@H](CC(=O)O)O)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CNC[C@H](CC(=O)O)O)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C LHZDWJSQSPEZFZ-MHZLTWQESA-N 0.000 claims 2
SIRHWYRCEWTBSE-PGUFJCEWSA-N BrC=1C(=CC(=C(CN[C@@](C(=O)O)(CO)C)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CN[C@@](C(=O)O)(CO)C)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C SIRHWYRCEWTBSE-PGUFJCEWSA-N 0.000 claims 2
KAZHPUZHQBTIRT-UUWRZZSWSA-N BrC=1C(=CC(=C(CN[C@@](C(=O)O)(CO)C)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CN[C@@](C(=O)O)(CO)C)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C KAZHPUZHQBTIRT-UUWRZZSWSA-N 0.000 claims 2
IKPFKGCPHQAIFU-LJAQVGFWSA-N BrC=1C(=CC(=C(CN[C@H](C(=O)O)CO)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CN[C@H](C(=O)O)CO)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C IKPFKGCPHQAIFU-LJAQVGFWSA-N 0.000 claims 2
SDFGMBXEMPWJHT-LJAQVGFWSA-N BrC=1C(=CC(=C(CN[C@H](C(=O)O)CO)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C#N Chemical compound BrC=1C(=CC(=C(CN[C@H](C(=O)O)CO)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C#N SDFGMBXEMPWJHT-LJAQVGFWSA-N 0.000 claims 2
WNYYJIUJMBIELW-NDEPHWFRSA-N BrC=1C(=CC(=C(CN[C@H](C(=O)O)CO)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CN[C@H](C(=O)O)CO)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C WNYYJIUJMBIELW-NDEPHWFRSA-N 0.000 claims 2
SIRHWYRCEWTBSE-DHUJRADRSA-N BrC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C SIRHWYRCEWTBSE-DHUJRADRSA-N 0.000 claims 2
KAZHPUZHQBTIRT-UMSFTDKQSA-N BrC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound BrC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C1)OCC=1C=NC=C(C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C KAZHPUZHQBTIRT-UMSFTDKQSA-N 0.000 claims 2
WQZAVOCQWIMWJG-MGBGTMOVSA-N BrC=1C=C(C=NC1)COC1=C(CN[C@@](C(=O)O)(CO)C)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)Cl Chemical compound BrC=1C=C(C=NC1)COC1=C(CN[C@@](C(=O)O)(CO)C)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)Cl WQZAVOCQWIMWJG-MGBGTMOVSA-N 0.000 claims 2
NSAZPJPBTFONPP-YTTGMZPUSA-N C(#N)C1=C(COC2=CC(=C(CN3[C@@H](CCCC3)C(=O)O)C=C2C)OCC=2C=NC=C(C2)C#N)C=CC=C1C1=CC2=C(OCCO2)C=C1 Chemical compound C(#N)C1=C(COC2=CC(=C(CN3[C@@H](CCCC3)C(=O)O)C=C2C)OCC=2C=NC=C(C2)C#N)C=CC=C1C1=CC2=C(OCCO2)C=C1 NSAZPJPBTFONPP-YTTGMZPUSA-N 0.000 claims 2
DGATVRFUXLVEIL-UHFFFAOYSA-N C(#N)C1=C(COC2=CC(=C(CNCCNC(C)=O)C=C2C)OCC=2C=NC=C(C2)C#N)C=CC=C1C1=CC2=C(OCCO2)C=C1 Chemical compound C(#N)C1=C(COC2=CC(=C(CNCCNC(C)=O)C=C2C)OCC=2C=NC=C(C2)C#N)C=CC=C1C1=CC2=C(OCCO2)C=C1 DGATVRFUXLVEIL-UHFFFAOYSA-N 0.000 claims 2
CQTODQLEFAZBTQ-NDEPHWFRSA-N C(#N)C1=C(COC2=CC(=C(CNC[C@H](CC(=O)O)O)C=C2C)OCC=2C=NC=C(C2)C#N)C=CC=C1C1=CC2=C(OCCO2)C=C1 Chemical compound C(#N)C1=C(COC2=CC(=C(CNC[C@H](CC(=O)O)O)C=C2C)OCC=2C=NC=C(C2)C#N)C=CC=C1C1=CC2=C(OCCO2)C=C1 CQTODQLEFAZBTQ-NDEPHWFRSA-N 0.000 claims 2
GHFCJNWWVKFMNL-GDLZYMKVSA-N C(#N)C1=C(COC2=CC(=C(CN[C@@H](C(=O)O)CO)C=C2C)OCC=2C=NC=C(C2)C#N)C=CC=C1C1=CC2=C(OCCO2)C=C1 Chemical compound C(#N)C1=C(COC2=CC(=C(CN[C@@H](C(=O)O)CO)C=C2C)OCC=2C=NC=C(C2)C#N)C=CC=C1C1=CC2=C(OCCO2)C=C1 GHFCJNWWVKFMNL-GDLZYMKVSA-N 0.000 claims 2
HIJXRNYXGUDWBH-PGUFJCEWSA-N C(#N)C1=C(COC2=CC(=C(CN[C@@](C(=O)O)(CO)C)C=C2C)OCC=2C=NC=C(C2)C#N)C=CC=C1C1=CC2=C(OCCO2)C=C1 Chemical compound C(#N)C1=C(COC2=CC(=C(CN[C@@](C(=O)O)(CO)C)C=C2C)OCC=2C=NC=C(C2)C#N)C=CC=C1C1=CC2=C(OCCO2)C=C1 HIJXRNYXGUDWBH-PGUFJCEWSA-N 0.000 claims 2
FVBJLWQXGQFFJN-UHFFFAOYSA-N C(#N)C1=C(COC=2C(=CC(=C(OCC=3C=NC=C(C#N)C3)C2)CNCCO)C)C=CC=C1C1=CC2=C(OCCO2)C=C1 Chemical compound C(#N)C1=C(COC=2C(=CC(=C(OCC=3C=NC=C(C#N)C3)C2)CNCCO)C)C=CC=C1C1=CC2=C(OCCO2)C=C1 FVBJLWQXGQFFJN-UHFFFAOYSA-N 0.000 claims 2
NITFZQZWGZBIIX-JGCGQSQUSA-N C(#N)C=1C=C(C=NC1)COC1=C(CN2[C@H](CCCC2)C(=O)O)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)C Chemical compound C(#N)C=1C=C(C=NC1)COC1=C(CN2[C@H](CCCC2)C(=O)O)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)C NITFZQZWGZBIIX-JGCGQSQUSA-N 0.000 claims 2
AUQQACYTJFRTIL-UHFFFAOYSA-N C(#N)C=1C=C(C=NC1)COC1=C(CNCCNC(C)=O)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)C Chemical compound C(#N)C=1C=C(C=NC1)COC1=C(CNCCNC(C)=O)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)C AUQQACYTJFRTIL-UHFFFAOYSA-N 0.000 claims 2
KNHZRYHBJBCWCI-LJAQVGFWSA-N C(#N)C=1C=C(C=NC1)COC1=C(CNC[C@H](CC(=O)O)O)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)C Chemical compound C(#N)C=1C=C(C=NC1)COC1=C(CNC[C@H](CC(=O)O)O)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)C KNHZRYHBJBCWCI-LJAQVGFWSA-N 0.000 claims 2
NBAJSHKXFFMTLV-GDLZYMKVSA-N C(#N)C=1C=C(C=NC1)COC1=C(CN[C@@H](C(=O)O)CO)C=CC(=C1)OCC=1C(=C(C=CC1)C1=CC=CC=C1)C Chemical compound C(#N)C=1C=C(C=NC1)COC1=C(CN[C@@H](C(=O)O)CO)C=CC(=C1)OCC=1C(=C(C=CC1)C1=CC=CC=C1)C NBAJSHKXFFMTLV-GDLZYMKVSA-N 0.000 claims 2
RJKHYQLXAJIFMD-PGUFJCEWSA-N C(#N)C=1C=C(C=NC1)COC1=C(CN[C@@](C(=O)O)(CO)C)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)C Chemical compound C(#N)C=1C=C(C=NC1)COC1=C(CN[C@@](C(=O)O)(CO)C)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)C RJKHYQLXAJIFMD-PGUFJCEWSA-N 0.000 claims 2
YRACWCUSAGLZCG-LJAQVGFWSA-N C(#N)C=1C=C(C=NC1)COC1=C(CN[C@H](C(=O)O)CO)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)C Chemical compound C(#N)C=1C=C(C=NC1)COC1=C(CN[C@H](C(=O)O)CO)C=C(C(=C1)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C)C YRACWCUSAGLZCG-LJAQVGFWSA-N 0.000 claims 2
YOJUYVRTOWKADA-XIFFEERXSA-N C(#N)C=1C=C(COC2=C(CN3[C@@H](CCCC3)C(=O)O)C=C(C(=C2)OCC2=C(C(=CC=C2)C2=CC3=C(OCCO3)C=C2)C)C)C=CC1 Chemical compound C(#N)C=1C=C(COC2=C(CN3[C@@H](CCCC3)C(=O)O)C=C(C(=C2)OCC2=C(C(=CC=C2)C2=CC3=C(OCCO3)C=C2)C)C)C=CC1 YOJUYVRTOWKADA-XIFFEERXSA-N 0.000 claims 2
ODKHJSFCXLLUME-XIFFEERXSA-N C(#N)C=1C=C(COC2=C(CN3[C@@H](CCCC3)C(=O)O)C=C(C(=C2)OCC2=C(C(=CC=C2)C2=CC3=C(OCCO3)C=C2)C)C)C=CC1F Chemical compound C(#N)C=1C=C(COC2=C(CN3[C@@H](CCCC3)C(=O)O)C=C(C(=C2)OCC2=C(C(=CC=C2)C2=CC3=C(OCCO3)C=C2)C)C)C=CC1F ODKHJSFCXLLUME-XIFFEERXSA-N 0.000 claims 2
KRFPWDMSJMARBJ-UHFFFAOYSA-N C(#N)C=1C=C(COC2=C(CNC(C(=O)O)(CO)C)C(=CC(=C2)OCC=2C(=C(C=CC2)C2=CC=CC=C2)C)OC)C=CC1 Chemical compound C(#N)C=1C=C(COC2=C(CNC(C(=O)O)(CO)C)C(=CC(=C2)OCC=2C(=C(C=CC2)C2=CC=CC=C2)C)OC)C=CC1 KRFPWDMSJMARBJ-UHFFFAOYSA-N 0.000 claims 2
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JP2016562537A 2014-04-14 2015-04-10 免疫調節剤として有用な化合物 Expired - Fee Related JP6556755B2 (ja)