JP2016536333A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016536333A5 JP2016536333A5 JP2016540311A JP2016540311A JP2016536333A5 JP 2016536333 A5 JP2016536333 A5 JP 2016536333A5 JP 2016540311 A JP2016540311 A JP 2016540311A JP 2016540311 A JP2016540311 A JP 2016540311A JP 2016536333 A5 JP2016536333 A5 JP 2016536333A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- methoxy
- phenylphenyl
- phenyl
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 hydroxy cyclopentyl Chemical group 0.000 claims 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 4
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- PRHPXJYSSYNNAX-UHFFFAOYSA-N CC1=C(C=CC=C1COC=1C=C2CCN(CC2=CC=1)CC(=O)O)C1=CC=CC=C1 Chemical compound CC1=C(C=CC=C1COC=1C=C2CCN(CC2=CC=1)CC(=O)O)C1=CC=CC=C1 PRHPXJYSSYNNAX-UHFFFAOYSA-N 0.000 claims 3
- PUGUDYHVJKDRHT-QGZVFWFLSA-N COc1cc(F)cc(c1)-c1cccc(COc2cc(OC)c(CN[C@H](C)C(O)=O)c(OC)c2)c1C Chemical compound COc1cc(F)cc(c1)-c1cccc(COc2cc(OC)c(CN[C@H](C)C(O)=O)c(OC)c2)c1C PUGUDYHVJKDRHT-QGZVFWFLSA-N 0.000 claims 3
- RUJGJXQLELAMPZ-UHFFFAOYSA-N Cc1cc(CN2CCC2)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCC2)ccc1OCc1cccc(c1C)-c1ccccc1 RUJGJXQLELAMPZ-UHFFFAOYSA-N 0.000 claims 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 235000019260 propionic acid Nutrition 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- LFDAMPXTOMYVDL-ZWAGFTRDSA-N (1R)-2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]cyclohexane-1-carboxylic acid Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CC1CCCC[C@H]1C(O)=O LFDAMPXTOMYVDL-ZWAGFTRDSA-N 0.000 claims 2
- VVAYTZXEIIASOX-SANMLTNESA-N (2S)-1-[[2-methoxy-3-methyl-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound COc1c(CN2CCCC[C@H]2C(O)=O)ccc(OCc2cccc(c2C)-c2ccccc2)c1C VVAYTZXEIIASOX-SANMLTNESA-N 0.000 claims 2
- RJPOZTIAWSYFDH-RDGATRHJSA-N (2S,4R)-1-[[3-chloro-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]-4-methoxypyrrolidine-2-carboxylic acid Chemical compound CO[C@@H]1C[C@H](N(Cc2ccc(OCc3cccc(c3C)-c3ccccc3)c(Cl)c2)C1)C(O)=O RJPOZTIAWSYFDH-RDGATRHJSA-N 0.000 claims 2
- XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims 2
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims 2
- ZHJPFAIDYVOVEG-UHFFFAOYSA-N 1-[3-[[3-methyl-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]propyl]pyrrolidin-2-one Chemical compound CC=1C=C(C=CC=1OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)CNCCCN1C(CCC1)=O ZHJPFAIDYVOVEG-UHFFFAOYSA-N 0.000 claims 2
- XPASSMHSTYAUCI-UHFFFAOYSA-N 4-[[3-methyl-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]butan-2-one Chemical compound CC(=O)CCNCC1=CC=C(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)C(C)=C1 XPASSMHSTYAUCI-UHFFFAOYSA-N 0.000 claims 2
- QVXDKKPKMDXRDR-UHFFFAOYSA-N C(C)(=O)NCCNC(C)C1=CC(=C(C=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)Cl Chemical compound C(C)(=O)NCCNC(C)C1=CC(=C(C=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)Cl QVXDKKPKMDXRDR-UHFFFAOYSA-N 0.000 claims 2
- VRIBDHIYQYBONN-UHFFFAOYSA-N CC(=O)NCCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Br)c1 Chemical compound CC(=O)NCCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Br)c1 VRIBDHIYQYBONN-UHFFFAOYSA-N 0.000 claims 2
- QLENBQSZSCUQNF-UHFFFAOYSA-N CC(=O)NCCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(F)c1 Chemical compound CC(=O)NCCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(F)c1 QLENBQSZSCUQNF-UHFFFAOYSA-N 0.000 claims 2
- UTWMGLWCXLEDIM-VPUSJEBWSA-N CC(=O)O[C@@H]1C[C@H](N(Cc2ccc(OCc3cccc(c3C)-c3ccccc3)c(C)c2)C1)C(O)=O Chemical compound CC(=O)O[C@@H]1C[C@H](N(Cc2ccc(OCc3cccc(c3C)-c3ccccc3)c(C)c2)C1)C(O)=O UTWMGLWCXLEDIM-VPUSJEBWSA-N 0.000 claims 2
- LTYRRNPMUQCLPK-UHFFFAOYSA-N CC(CC(O)=O)NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1 Chemical compound CC(CC(O)=O)NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1 LTYRRNPMUQCLPK-UHFFFAOYSA-N 0.000 claims 2
- DITGSNOUXGPVNN-UHFFFAOYSA-N CC1=C(C=CC=C1C1=CC=CC=C1)COC1=CC=C(C=C1)CN1C(CCCC1)C(=O)O Chemical compound CC1=C(C=CC=C1C1=CC=CC=C1)COC1=CC=C(C=C1)CN1C(CCCC1)C(=O)O DITGSNOUXGPVNN-UHFFFAOYSA-N 0.000 claims 2
- RSILUGRGGAUUNL-UHFFFAOYSA-N CC=1C=C(C=CC=1OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)CN1CC(=CCC1)C(=O)O Chemical compound CC=1C=C(C=CC=1OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)CN1CC(=CCC1)C(=O)O RSILUGRGGAUUNL-UHFFFAOYSA-N 0.000 claims 2
- MPWXPHXWSZZJSZ-UHFFFAOYSA-N CCN1CCCC(C1)NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC Chemical compound CCN1CCCC(C1)NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC MPWXPHXWSZZJSZ-UHFFFAOYSA-N 0.000 claims 2
- NGWARGISBMFXGR-UHFFFAOYSA-N CN(CC(O)=O)Cc1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1 Chemical compound CN(CC(O)=O)Cc1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1 NGWARGISBMFXGR-UHFFFAOYSA-N 0.000 claims 2
- UQQACMJMIXWAQX-UHFFFAOYSA-N CN(CC(O)=O)Cc1cccc(OCc2cccc(c2C)-c2ccccc2)c1 Chemical compound CN(CC(O)=O)Cc1cccc(OCc2cccc(c2C)-c2ccccc2)c1 UQQACMJMIXWAQX-UHFFFAOYSA-N 0.000 claims 2
- GIYKJGPKVFLPMA-RSXGOPAZSA-N CO[C@@H]1C[C@H](N(Cc2ccc(OCc3cccc(c3C)-c3ccccc3)c(C)c2)C1)C(O)=O Chemical compound CO[C@@H]1C[C@H](N(Cc2ccc(OCc3cccc(c3C)-c3ccccc3)c(C)c2)C1)C(O)=O GIYKJGPKVFLPMA-RSXGOPAZSA-N 0.000 claims 2
- MVXPOSMNRSCJMP-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CC(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CC(O)=O MVXPOSMNRSCJMP-UHFFFAOYSA-N 0.000 claims 2
- ZBOYJODMIAUJHH-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN1CCCCC1C(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN1CCCCC1C(O)=O ZBOYJODMIAUJHH-UHFFFAOYSA-N 0.000 claims 2
- YCCDVBIIHLIURK-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(C)(C)CN1CCN(C)CC1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(C)(C)CN1CCN(C)CC1 YCCDVBIIHLIURK-UHFFFAOYSA-N 0.000 claims 2
- DJTHSGNSQOGZGD-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(C)CC(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(C)CC(O)=O DJTHSGNSQOGZGD-UHFFFAOYSA-N 0.000 claims 2
- XYLDJCADECMWKP-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC1CCC1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC1CCC1 XYLDJCADECMWKP-UHFFFAOYSA-N 0.000 claims 2
- YOSNCHLACPIBHY-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC1CCCN(C)C1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC1CCCN(C)C1 YOSNCHLACPIBHY-UHFFFAOYSA-N 0.000 claims 2
- DRFLXZNAAKEZGT-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(=O)N(C)C Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(=O)N(C)C DRFLXZNAAKEZGT-UHFFFAOYSA-N 0.000 claims 2
- MFEHNRXGUMAKJB-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCCC1=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCCC1=O MFEHNRXGUMAKJB-UHFFFAOYSA-N 0.000 claims 2
- YZASPJDRTJDVGZ-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCCCC1=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCCCC1=O YZASPJDRTJDVGZ-UHFFFAOYSA-N 0.000 claims 2
- MDRNRIAYLGGFKE-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCNC(=O)C1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCNC(=O)C1 MDRNRIAYLGGFKE-UHFFFAOYSA-N 0.000 claims 2
- OYNIISWIMDFFAF-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCNC(C)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCNC(C)=O OYNIISWIMDFFAF-UHFFFAOYSA-N 0.000 claims 2
- RWOWRLYCKOPZHJ-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCO Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCO RWOWRLYCKOPZHJ-UHFFFAOYSA-N 0.000 claims 2
- WMWOLWGPDHWGGI-NRFANRHFSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC[C@@H](O)CC(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC[C@@H](O)CC(O)=O WMWOLWGPDHWGGI-NRFANRHFSA-N 0.000 claims 2
- JAVOOZFIZRTIMB-SFHVURJKSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H](C)C(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H](C)C(O)=O JAVOOZFIZRTIMB-SFHVURJKSA-N 0.000 claims 2
- IDRDYZSWSKCIGO-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)ccc1CN1CCC1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)ccc1CN1CCC1 IDRDYZSWSKCIGO-UHFFFAOYSA-N 0.000 claims 2
- KRAIGCXDUYJGCN-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)ccc1CN1CCCCC1C(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)ccc1CN1CCCCC1C(O)=O KRAIGCXDUYJGCN-UHFFFAOYSA-N 0.000 claims 2
- IHJYMBHZPIGMGK-SFHVURJKSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)ccc1CN[C@@H](C)C(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)ccc1CN[C@@H](C)C(O)=O IHJYMBHZPIGMGK-SFHVURJKSA-N 0.000 claims 2
- ZTXIVEFSDGYDHN-GOSISDBHSA-N COc1cccc(c1)-c1cccc(COc2cc(OC)c(CN[C@H](C)C(O)=O)c(OC)c2)c1C Chemical compound COc1cccc(c1)-c1cccc(COc2cc(OC)c(CN[C@H](C)C(O)=O)c(OC)c2)c1C ZTXIVEFSDGYDHN-GOSISDBHSA-N 0.000 claims 2
- RUUNMWXKBFSZIJ-LJQANCHMSA-N C[C@@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1)C(O)=O Chemical compound C[C@@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1)C(O)=O RUUNMWXKBFSZIJ-LJQANCHMSA-N 0.000 claims 2
- QGXJVELKPSMEGB-QGZVFWFLSA-N C[C@@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1)C(O)=O Chemical compound C[C@@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1)C(O)=O QGXJVELKPSMEGB-QGZVFWFLSA-N 0.000 claims 2
- WJLRWTHTEIJWTE-NIYFSFCBSA-N C[C@@H]1C[C@@H](N(Cc2ccc(OCc3cccc(c3C)-c3ccccc3)c(C)c2)C1)C(O)=O Chemical compound C[C@@H]1C[C@@H](N(Cc2ccc(OCc3cccc(c3C)-c3ccccc3)c(C)c2)C1)C(O)=O WJLRWTHTEIJWTE-NIYFSFCBSA-N 0.000 claims 2
- RUUNMWXKBFSZIJ-IBGZPJMESA-N C[C@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1)C(O)=O Chemical compound C[C@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1)C(O)=O RUUNMWXKBFSZIJ-IBGZPJMESA-N 0.000 claims 2
- QGXJVELKPSMEGB-KRWDZBQOSA-N C[C@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1)C(O)=O Chemical compound C[C@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1)C(O)=O QGXJVELKPSMEGB-KRWDZBQOSA-N 0.000 claims 2
- MZGKXSZRBMIMLW-SFHVURJKSA-N C[C@H](NCc1cccc(OCc2cccc(c2C)-c2ccccc2)c1)C(O)=O Chemical compound C[C@H](NCc1cccc(OCc2cccc(c2C)-c2ccccc2)c1)C(O)=O MZGKXSZRBMIMLW-SFHVURJKSA-N 0.000 claims 2
- KQDCXYBUWMBUSN-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCC(CC3)C(O)=O)cc2Cl)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCC(CC3)C(O)=O)cc2Cl)cccc1-c1ccccc1 KQDCXYBUWMBUSN-UHFFFAOYSA-N 0.000 claims 2
- GNYIPNWZSMMUFQ-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCC3)cc2)cccc1-c1ccccc1F Chemical compound Cc1c(COc2ccc(CN3CCC3)cc2)cccc1-c1ccccc1F GNYIPNWZSMMUFQ-UHFFFAOYSA-N 0.000 claims 2
- PRRWLKVPTPBWHS-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCC3)cc2Br)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCC3)cc2Br)cccc1-c1ccccc1 PRRWLKVPTPBWHS-UHFFFAOYSA-N 0.000 claims 2
- QRXBPPWUGITQLE-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCCCC3C(O)=O)cc2Br)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCCCC3C(O)=O)cc2Br)cccc1-c1ccccc1 QRXBPPWUGITQLE-UHFFFAOYSA-N 0.000 claims 2
- MYHXPAKFKMMKMZ-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCCCC3C(O)=O)cc2F)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCCCC3C(O)=O)cc2F)cccc1-c1ccccc1 MYHXPAKFKMMKMZ-UHFFFAOYSA-N 0.000 claims 2
- AAEIUZHZXCPBCS-VWLOTQADSA-N Cc1c(COc2ccc(CN3CCCC[C@H]3C(O)=O)cc2Cl)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCCC[C@H]3C(O)=O)cc2Cl)cccc1-c1ccccc1 AAEIUZHZXCPBCS-VWLOTQADSA-N 0.000 claims 2
- RVDAEQRWSPNFRG-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCOCC3C(O)=O)cc2Cl)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCOCC3C(O)=O)cc2Cl)cccc1-c1ccccc1 RVDAEQRWSPNFRG-UHFFFAOYSA-N 0.000 claims 2
- UXRQTAOAPRKWDQ-UHFFFAOYSA-N Cc1c(COc2ccc(CNC(C)(C)C(O)=O)cc2Cl)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNC(C)(C)C(O)=O)cc2Cl)cccc1-c1ccccc1 UXRQTAOAPRKWDQ-UHFFFAOYSA-N 0.000 claims 2
- NIVJEFTUALCIHL-UHFFFAOYSA-N Cc1c(COc2ccc(CNCC3CCC(=O)N3)cc2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNCC3CCC(=O)N3)cc2)cccc1-c1ccccc1 NIVJEFTUALCIHL-UHFFFAOYSA-N 0.000 claims 2
- BJJAFOSFOJOZOO-UHFFFAOYSA-N Cc1c(COc2ccc(CNCCC(N)=O)cc2Br)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNCCC(N)=O)cc2Br)cccc1-c1ccccc1 BJJAFOSFOJOZOO-UHFFFAOYSA-N 0.000 claims 2
- NUYRSTFEAVNXBY-UHFFFAOYSA-N Cc1c(COc2ccc3CNCCc3c2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc3CNCCc3c2)cccc1-c1ccccc1 NUYRSTFEAVNXBY-UHFFFAOYSA-N 0.000 claims 2
- XQIVBIQDGUDOIA-UHFFFAOYSA-N Cc1c(COc2cccc(CN3CCC3)c2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2cccc(CN3CCC3)c2)cccc1-c1ccccc1 XQIVBIQDGUDOIA-UHFFFAOYSA-N 0.000 claims 2
- VWBHFLZEKIIMQK-UHFFFAOYSA-N Cc1c(COc2cccc(CN3CCCCC3C(O)=O)c2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2cccc(CN3CCCCC3C(O)=O)c2)cccc1-c1ccccc1 VWBHFLZEKIIMQK-UHFFFAOYSA-N 0.000 claims 2
- NZDOPZPDFMPHBL-UHFFFAOYSA-N Cc1c(COc2cccc(CNCCC(N)=O)c2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2cccc(CNCCC(N)=O)c2)cccc1-c1ccccc1 NZDOPZPDFMPHBL-UHFFFAOYSA-N 0.000 claims 2
- CUVBOKMETMPOEM-UHFFFAOYSA-N Cc1cc(CN2CCC(CC2)C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCC(CC2)C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 CUVBOKMETMPOEM-UHFFFAOYSA-N 0.000 claims 2
- YWANNZJYJLPFKV-UHFFFAOYSA-N Cc1cc(CN2CCCC2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCCC2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 YWANNZJYJLPFKV-UHFFFAOYSA-N 0.000 claims 2
- DIEFHARFEOYRCE-UHFFFAOYSA-N Cc1cc(CN2CCCCC2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCCCC2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 DIEFHARFEOYRCE-UHFFFAOYSA-N 0.000 claims 2
- CWKDBXPHEHNUTI-UHFFFAOYSA-N Cc1cc(CN2CCCCC2CC(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCCCC2CC(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 CWKDBXPHEHNUTI-UHFFFAOYSA-N 0.000 claims 2
- YSKRXTFVLTYIRJ-UHFFFAOYSA-N Cc1cc(CN2CCCCCC2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCCCCC2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 YSKRXTFVLTYIRJ-UHFFFAOYSA-N 0.000 claims 2
- DIEFHARFEOYRCE-AREMUKBSSA-N Cc1cc(CN2CCCC[C@@H]2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCCC[C@@H]2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 DIEFHARFEOYRCE-AREMUKBSSA-N 0.000 claims 2
- DIEFHARFEOYRCE-SANMLTNESA-N Cc1cc(CN2CCCC[C@H]2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCCC[C@H]2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 DIEFHARFEOYRCE-SANMLTNESA-N 0.000 claims 2
- YWANNZJYJLPFKV-RUZDIDTESA-N Cc1cc(CN2CCC[C@@H]2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCC[C@@H]2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 YWANNZJYJLPFKV-RUZDIDTESA-N 0.000 claims 2
- CSGXVUMLNZXMMP-XMMPIXPASA-N Cc1cc(CN2CCC[C@H](C2)C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCC[C@H](C2)C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 CSGXVUMLNZXMMP-XMMPIXPASA-N 0.000 claims 2
- RJBDMKDUAKYPMJ-VWLOTQADSA-N Cc1cc(CN2CCC[C@H]2CO)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCC[C@H]2CO)ccc1OCc1cccc(c1C)-c1ccccc1 RJBDMKDUAKYPMJ-VWLOTQADSA-N 0.000 claims 2
- CORBBPZHTZEDTN-DEOSSOPVSA-N Cc1cc(CN2CC[C@H]2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CC[C@H]2C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 CORBBPZHTZEDTN-DEOSSOPVSA-N 0.000 claims 2
- IDIOAIIUPDWEBC-UHFFFAOYSA-N Cc1cc(CNCC2CCC(=O)N2)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CNCC2CCC(=O)N2)ccc1OCc1cccc(c1C)-c1ccccc1 IDIOAIIUPDWEBC-UHFFFAOYSA-N 0.000 claims 2
- MRKKHKMPJRIIPU-UHFFFAOYSA-N Cc1cc(CNCCO)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CNCCO)ccc1OCc1cccc(c1C)-c1ccccc1 MRKKHKMPJRIIPU-UHFFFAOYSA-N 0.000 claims 2
- OAHMJAXIBOFXIV-UHFFFAOYSA-N Cc1cc(OCc2cccc(c2C)-c2ccccc2)cc(C)c1CN1CCCCC1C(O)=O Chemical compound Cc1cc(OCc2cccc(c2C)-c2ccccc2)cc(C)c1CN1CCCCC1C(O)=O OAHMJAXIBOFXIV-UHFFFAOYSA-N 0.000 claims 2
- XVKKAAVWQFLMPI-UHFFFAOYSA-N Cc1cc(OCc2cccc(c2C)-c2ccccc2)cc(C)c1CNCCC(N)=O Chemical compound Cc1cc(OCc2cccc(c2C)-c2ccccc2)cc(C)c1CNCCC(N)=O XVKKAAVWQFLMPI-UHFFFAOYSA-N 0.000 claims 2
- JKXLTFJHXCHRMA-UHFFFAOYSA-N N-(2-hydroxyethyl)-1-[[2-methoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]piperidine-4-carboxamide Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC=C1CN1CCC(CC1)C(=O)NCCO JKXLTFJHXCHRMA-UHFFFAOYSA-N 0.000 claims 2
- GOBRMVNDDYLBKD-UHFFFAOYSA-N N-[2-[1-[3-methyl-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]ethylamino]ethyl]acetamide Chemical compound CC(NCCNC(C)=O)c1ccc(OCc2cccc(c2C)-c2ccccc2)c(C)c1 GOBRMVNDDYLBKD-UHFFFAOYSA-N 0.000 claims 2
- ZFZHQQVOKKIXPI-UHFFFAOYSA-N N-[2-[[2,6-dimethyl-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]ethyl]acetamide Chemical compound CC(=O)NCCNCc1c(C)cc(OCc2cccc(c2C)-c2ccccc2)cc1C ZFZHQQVOKKIXPI-UHFFFAOYSA-N 0.000 claims 2
- KHSZKUGLGOCHDC-UHFFFAOYSA-N N-[2-[[3-chloro-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]ethyl]acetamide Chemical compound CC(=O)NCCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1 KHSZKUGLGOCHDC-UHFFFAOYSA-N 0.000 claims 2
- JOQZFJRPPIMBNA-UHFFFAOYSA-N N-[2-[[4-methyl-3-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]ethyl]acetamide Chemical compound CC(=O)NCCNCc1ccc(C)c(OCc2cccc(c2C)-c2ccccc2)c1 JOQZFJRPPIMBNA-UHFFFAOYSA-N 0.000 claims 2
- KIUSCCDCOPAXCS-UHFFFAOYSA-N N-[2-[[5-[(2-methyl-3-phenylphenyl)methoxy]-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl]amino]ethyl]acetamide Chemical compound CC(=O)NCCNC1CCCC2C(CCCC12)OCc1cccc(c1C)-c1ccccc1 KIUSCCDCOPAXCS-UHFFFAOYSA-N 0.000 claims 2
- UAKMDFGBYWWAOW-UHFFFAOYSA-N N-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]-2-(4-methylpiperazin-1-yl)ethanamine Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNCCN1CCN(C)CC1 UAKMDFGBYWWAOW-UHFFFAOYSA-N 0.000 claims 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims 2
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- SFVBPSWRCHUWMF-LJAQVGFWSA-N (1R)-2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]-1-phenylethanol Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC[C@H](O)c1ccccc1 SFVBPSWRCHUWMF-LJAQVGFWSA-N 0.000 claims 1
- WRWPUUKELJIWHM-KAYWLYCHSA-N (1R,2R)-2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]cyclohexan-1-ol Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H]1CCCC[C@H]1O WRWPUUKELJIWHM-KAYWLYCHSA-N 0.000 claims 1
- VQHLTBODBCNTSO-CLJLJLNGSA-N (1R,2R)-2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]cyclopentan-1-ol Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@H]1[C@@H](CCC1)O VQHLTBODBCNTSO-CLJLJLNGSA-N 0.000 claims 1
- AKJGZMYBHGRGOU-KAYWLYCHSA-N (1R,2R)-2-[[3-methyl-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]cyclohexan-1-ol Chemical compound Cc1cc(CN[C@@H]2CCCC[C@H]2O)ccc1OCc1cccc(c1C)-c1ccccc1 AKJGZMYBHGRGOU-KAYWLYCHSA-N 0.000 claims 1
- VQHLTBODBCNTSO-IZZNHLLZSA-N (1R,2S)-2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]cyclopentan-1-ol Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@@H]1[C@@H](CCC1)O VQHLTBODBCNTSO-IZZNHLLZSA-N 0.000 claims 1
- SFVBPSWRCHUWMF-GDLZYMKVSA-N (1S)-2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]-1-phenylethanol Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNC[C@@H](O)C1=CC=CC=C1 SFVBPSWRCHUWMF-GDLZYMKVSA-N 0.000 claims 1
- WRWPUUKELJIWHM-SXOMAYOGSA-N (1S,2R)-2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]cyclohexan-1-ol Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@H]1[C@H](CCCC1)O WRWPUUKELJIWHM-SXOMAYOGSA-N 0.000 claims 1
- VQHLTBODBCNTSO-UIOOFZCWSA-N (1S,2S)-2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]cyclopentan-1-ol Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@@H]1[C@H](CCC1)O VQHLTBODBCNTSO-UIOOFZCWSA-N 0.000 claims 1
- CEENJLDDMBNKDX-SFHVURJKSA-N (2S)-1-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]propan-2-ol Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC[C@H](C)O CEENJLDDMBNKDX-SFHVURJKSA-N 0.000 claims 1
- WIPLIOVSJOEWFD-SANMLTNESA-N (2S)-1-[[4-[(2-cyano-3-phenylphenyl)methoxy]-2,6-dimethoxyphenyl]methyl]piperidine-2-carboxylic acid Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC[C@H]1C(O)=O WIPLIOVSJOEWFD-SANMLTNESA-N 0.000 claims 1
- DUQNSDJAPIRMFA-VWLOTQADSA-N (2S)-1-[[4-[(2-cyano-3-phenylphenyl)methoxy]-2,6-dimethoxyphenyl]methyl]pyrrolidine-2-carboxamide Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCC[C@H]1C(N)=O DUQNSDJAPIRMFA-VWLOTQADSA-N 0.000 claims 1
- OLSHCRHDCVPQRJ-VWLOTQADSA-N (2S)-1-[[4-[[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy]-2,5-difluorophenyl]methyl]piperidine-2-carboxylic acid Chemical compound Cc1c(COc2cc(F)c(CN3CCCC[C@H]3C(O)=O)cc2F)cccc1-c1ccc2OCCOc2c1 OLSHCRHDCVPQRJ-VWLOTQADSA-N 0.000 claims 1
- BXTVOBAMQXQEKX-NRFANRHFSA-N (3S)-4-[[3-[[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy]-4-(trifluoromethyl)phenyl]methylamino]-3-hydroxybutanoic acid Chemical compound C1=C(C=CC2=C1OCCO2)C1=C(C)C(COC2=C(C(F)(F)F)C=CC(CNC[C@@H](O)CC(=O)O)=C2)=CC=C1 BXTVOBAMQXQEKX-NRFANRHFSA-N 0.000 claims 1
- SSNAOTQAARBFBK-QHCPKHFHSA-N (5S)-6-[[3-chloro-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]-1,2,6-triazaspiro[2.4]hept-1-ene-5-carboxylic acid Chemical compound Cc1c(COc2ccc(CN3CC4(C[C@H]3C(O)=O)N=N4)cc2Cl)cccc1-c1ccccc1 SSNAOTQAARBFBK-QHCPKHFHSA-N 0.000 claims 1
- RZNHHGMCDDENDY-UHFFFAOYSA-N 1-(1-methylimidazol-2-yl)ethanol Chemical compound CC(O)C1=NC=CN1C RZNHHGMCDDENDY-UHFFFAOYSA-N 0.000 claims 1
- DTUSUTVQIDPUBP-UHFFFAOYSA-N 1-(3,3-difluorocyclobutyl)-N-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]methanamine Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC1CC(F)(F)C1 DTUSUTVQIDPUBP-UHFFFAOYSA-N 0.000 claims 1
- KQJHCDPRKVWRIW-UHFFFAOYSA-N 1-[2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]ethyl]piperidin-4-ol Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNCCN1CCC(O)CC1 KQJHCDPRKVWRIW-UHFFFAOYSA-N 0.000 claims 1
- DJUFRQIDQIJLHB-UHFFFAOYSA-N 1-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]-2,3-dihydro-1H-inden-2-ol Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC1C(O)Cc2ccccc12 DJUFRQIDQIJLHB-UHFFFAOYSA-N 0.000 claims 1
- TWZSQHIJRXGXTC-UHFFFAOYSA-N 1-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]-3-(dimethylamino)propan-2-ol Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNCC(O)CN(C)C TWZSQHIJRXGXTC-UHFFFAOYSA-N 0.000 claims 1
- SNCZXWJNFAMFMM-UHFFFAOYSA-N 1-[[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]methyl]cyclobutan-1-ol Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNCC1(CCC1)O SNCZXWJNFAMFMM-UHFFFAOYSA-N 0.000 claims 1
- DXRWTYQYYIQFFT-UHFFFAOYSA-N 1-[[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]methyl]cyclohexan-1-ol Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNCC1(CCCCC1)O DXRWTYQYYIQFFT-UHFFFAOYSA-N 0.000 claims 1
- JZEMKIVQTLMDHR-UHFFFAOYSA-N 2-[2-[2-[2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNCCOCCOCCOCCO JZEMKIVQTLMDHR-UHFFFAOYSA-N 0.000 claims 1
- KFGVVLYYXUEFDP-UHFFFAOYSA-N 2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]-1-morpholin-4-ylethanone Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(=O)N1CCOCC1 KFGVVLYYXUEFDP-UHFFFAOYSA-N 0.000 claims 1
- UNAUEYAHPNNWAF-UHFFFAOYSA-N 2-[[2-[[2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]acetyl]amino]acetyl]amino]-4-methylpentanoic acid Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNCC(=O)NCC(=O)NC(CC(C)C)C(O)=O UNAUEYAHPNNWAF-UHFFFAOYSA-N 0.000 claims 1
- QRMQMJWZVFRNAG-UHFFFAOYSA-N 2-[[3,5-dimethoxy-4-[(2-morpholin-4-ylethylamino)methyl]phenoxy]methyl]-6-phenylbenzonitrile Chemical compound COC1=CC(OCC2=C(C#N)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNCCN1CCOCC1 QRMQMJWZVFRNAG-UHFFFAOYSA-N 0.000 claims 1
- BOJXYPQIHZTTTA-UHFFFAOYSA-N 2-[[4-[[(3-hydroxyphenyl)methylamino]methyl]-3,5-dimethoxyphenoxy]methyl]-6-phenylbenzonitrile Chemical compound OC=1C=C(C=CC1)CNCC1=C(C=C(OCC2=C(C#N)C(=CC=C2)C2=CC=CC=C2)C=C1OC)OC BOJXYPQIHZTTTA-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001845 4 membered carbocyclic group Chemical group 0.000 claims 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- 102000008096 B7-H1 Antigen Human genes 0.000 claims 1
- 108010074708 B7-H1 Antigen Proteins 0.000 claims 1
- DKIHTVJLLXJMSG-UHFFFAOYSA-N C(C)OC=1C=C(C=CC1)C=1C(=C(C=CC1)COC1=CC(=C(C(=C1)OC)CNCCO)OC)C Chemical compound C(C)OC=1C=C(C=CC1)C=1C(=C(C=CC1)COC1=CC(=C(C(=C1)OC)CNCCO)OC)C DKIHTVJLLXJMSG-UHFFFAOYSA-N 0.000 claims 1
- WSXQIOJWUBTTFX-UHFFFAOYSA-N CC(=O)NCCNCc1cc(F)c(OCc2cccc(c2C)-c2ccc3OCCOc3c2)cc1F Chemical compound CC(=O)NCCNCc1cc(F)c(OCc2cccc(c2C)-c2ccc3OCCOc3c2)cc1F WSXQIOJWUBTTFX-UHFFFAOYSA-N 0.000 claims 1
- UUSQAZRMMMADQG-UHFFFAOYSA-N CC(=O)NCCNCc1ccc(OCc2cccc(-c3ccsc3)c2C)c(Cl)c1 Chemical compound CC(=O)NCCNCc1ccc(OCc2cccc(-c3ccsc3)c2C)c(Cl)c1 UUSQAZRMMMADQG-UHFFFAOYSA-N 0.000 claims 1
- NCBPLPAJPNAHOU-UHFFFAOYSA-N CC(=O)NCCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(c1)C#N Chemical compound CC(=O)NCCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(c1)C#N NCBPLPAJPNAHOU-UHFFFAOYSA-N 0.000 claims 1
- VEKXNMUQKQJTPG-DEOSSOPVSA-N CC(=O)N[C@H]1CCN(Cc2ccc(OCc3cccc(c3C)-c3ccccc3)nc2)C1 Chemical compound CC(=O)N[C@H]1CCN(Cc2ccc(OCc3cccc(c3C)-c3ccccc3)nc2)C1 VEKXNMUQKQJTPG-DEOSSOPVSA-N 0.000 claims 1
- QOWSWLSZQBUTJS-UHFFFAOYSA-N CC(C)NCc1ccc(OCc2cccc(c2C)-c2ccccc2)nc1 Chemical compound CC(C)NCc1ccc(OCc2cccc(c2C)-c2ccccc2)nc1 QOWSWLSZQBUTJS-UHFFFAOYSA-N 0.000 claims 1
- XHPSMNJXCNQKAI-UHFFFAOYSA-N CC1=C(C=CC=C1C1=CC=CC=C1)COC1=CC=C(C=N1)CN1CC(CCC1)CO Chemical compound CC1=C(C=CC=C1C1=CC=CC=C1)COC1=CC=C(C=N1)CN1CC(CCC1)CO XHPSMNJXCNQKAI-UHFFFAOYSA-N 0.000 claims 1
- IYJOLXWUSHNQMX-UHFFFAOYSA-N CC1=C(C=CC=C1C1=CC=CC=C1)COC1=CC=C(C=N1)CNCC1CCC(N1)=O Chemical compound CC1=C(C=CC=C1C1=CC=CC=C1)COC1=CC=C(C=N1)CNCC1CCC(N1)=O IYJOLXWUSHNQMX-UHFFFAOYSA-N 0.000 claims 1
- IANIEFFEUVFFNI-UHFFFAOYSA-N CC1=C(C=CC=C1C1=CC=CC=C1)COC=1C=CC(=NC1)CNCC1CCC(N1)=O Chemical compound CC1=C(C=CC=C1C1=CC=CC=C1)COC=1C=CC(=NC1)CNCC1CCC(N1)=O IANIEFFEUVFFNI-UHFFFAOYSA-N 0.000 claims 1
- VMPHLMLKSUYKMI-UHFFFAOYSA-N CC1=C(COC2=NC=C(CNCCC3=CC=CC=N3)C=C2)C=CC=C1C1=CC=CC=C1 Chemical compound CC1=C(COC2=NC=C(CNCCC3=CC=CC=N3)C=C2)C=CC=C1C1=CC=CC=C1 VMPHLMLKSUYKMI-UHFFFAOYSA-N 0.000 claims 1
- MCUFBZCYIIVJOM-UHFFFAOYSA-N CC1CCCN1Cc1ccc(OCc2cccc(c2C)-c2ccccc2)nc1 Chemical compound CC1CCCN1Cc1ccc(OCc2cccc(c2C)-c2ccccc2)nc1 MCUFBZCYIIVJOM-UHFFFAOYSA-N 0.000 claims 1
- XDCCQJYWWJAQMF-UHFFFAOYSA-N CCC(CO)(CO)NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC Chemical compound CCC(CO)(CO)NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC XDCCQJYWWJAQMF-UHFFFAOYSA-N 0.000 claims 1
- IYWXJKHOWWHWCT-QHCPKHFHSA-N CCC[C@@H](CO)NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC Chemical compound CCC[C@@H](CO)NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC IYWXJKHOWWHWCT-QHCPKHFHSA-N 0.000 claims 1
- BNGQQIPGCOKIDI-UHFFFAOYSA-N CCN(Cc1ccncc1)Cc1c(OC)cc(OCc2cccc(-c3ccccc3)c2C#N)cc1OC Chemical compound CCN(Cc1ccncc1)Cc1c(OC)cc(OCc2cccc(-c3ccccc3)c2C#N)cc1OC BNGQQIPGCOKIDI-UHFFFAOYSA-N 0.000 claims 1
- DIRXBWVQQFYQNE-QFIPXVFZSA-N CC[C@@H](CO)NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC Chemical compound CC[C@@H](CO)NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC DIRXBWVQQFYQNE-QFIPXVFZSA-N 0.000 claims 1
- YVKQJGZGAFOCNM-MUUNZHRXSA-N CC[C@@](C)(NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC)C(O)=O Chemical compound CC[C@@](C)(NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC)C(O)=O YVKQJGZGAFOCNM-MUUNZHRXSA-N 0.000 claims 1
- DIRXBWVQQFYQNE-JOCHJYFZSA-N CC[C@H](CO)NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC Chemical compound CC[C@H](CO)NCc1c(OC)cc(OCc2cccc(c2C)-c2ccccc2)cc1OC DIRXBWVQQFYQNE-JOCHJYFZSA-N 0.000 claims 1
- SILBJAGFZQLCDJ-UHFFFAOYSA-N CN(C)CCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)nc1 Chemical compound CN(C)CCNCc1ccc(OCc2cccc(c2C)-c2ccccc2)nc1 SILBJAGFZQLCDJ-UHFFFAOYSA-N 0.000 claims 1
- ZMKNXRAVJZZCKX-UHFFFAOYSA-N CNCC1=NC=C(C=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C Chemical compound CNCC1=NC=C(C=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C ZMKNXRAVJZZCKX-UHFFFAOYSA-N 0.000 claims 1
- KIDRVOUEZVIKBH-UHFFFAOYSA-N CNCC=1C=NC(=CC1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C Chemical compound CNCC=1C=NC(=CC1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C KIDRVOUEZVIKBH-UHFFFAOYSA-N 0.000 claims 1
- WJZZOTQYDJBATG-UHFFFAOYSA-N CNCc1c(OC)cc(OCc2cccc(-c3ccccc3)c2C#N)cc1OC Chemical compound CNCc1c(OC)cc(OCc2cccc(-c3ccccc3)c2C#N)cc1OC WJZZOTQYDJBATG-UHFFFAOYSA-N 0.000 claims 1
- CTJHSDXJXRVNNY-UHFFFAOYSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC(=CC=C1)OC)C)OC)CNCCNC(C)=O Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC(=CC=C1)OC)C)OC)CNCCNC(C)=O CTJHSDXJXRVNNY-UHFFFAOYSA-N 0.000 claims 1
- UAQKTBHPBCTFAG-UHFFFAOYSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC(=CC=C1)OCCC)C)OC)CNCCO Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC(=CC=C1)OCCC)C)OC)CNCCO UAQKTBHPBCTFAG-UHFFFAOYSA-N 0.000 claims 1
- POGRFIHBWGRXKQ-DEOSSOPVSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN1CC2(N=N2)C[C@H]1C(=O)O Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN1CC2(N=N2)C[C@H]1C(=O)O POGRFIHBWGRXKQ-DEOSSOPVSA-N 0.000 claims 1
- ZUNMRCWDGXBLHY-UHFFFAOYSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNC(C(C)(O)C)C Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNC(C(C)(O)C)C ZUNMRCWDGXBLHY-UHFFFAOYSA-N 0.000 claims 1
- JUKIXKGNADUBQZ-UHFFFAOYSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNC(C(C)O)C Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNC(C(C)O)C JUKIXKGNADUBQZ-UHFFFAOYSA-N 0.000 claims 1
- FDNLSOYPUAARJN-UHFFFAOYSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNC1(CCCC1)CO Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNC1(CCCC1)CO FDNLSOYPUAARJN-UHFFFAOYSA-N 0.000 claims 1
- ZMJPFJUFCAOCCS-UHFFFAOYSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNCC(CC)O Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CNCC(CC)O ZMJPFJUFCAOCCS-UHFFFAOYSA-N 0.000 claims 1
- BBYOBMYDDHSXDT-LJAQVGFWSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@@H](CO)C1=CC=CC=C1 Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@@H](CO)C1=CC=CC=C1 BBYOBMYDDHSXDT-LJAQVGFWSA-N 0.000 claims 1
- BBYOBMYDDHSXDT-GDLZYMKVSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@H](CO)C1=CC=CC=C1 Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@H](CO)C1=CC=CC=C1 BBYOBMYDDHSXDT-GDLZYMKVSA-N 0.000 claims 1
- RKUORYVPLXYDFJ-DEOSSOPVSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@H](CO)CC(C)C Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@H](CO)CC(C)C RKUORYVPLXYDFJ-DEOSSOPVSA-N 0.000 claims 1
- FVRCXSDISSVNBG-CCLHPLFOSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@H](CO)[C@H](CC)C Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN[C@H](CO)[C@H](CC)C FVRCXSDISSVNBG-CCLHPLFOSA-N 0.000 claims 1
- HIUGGNBVKQUYKF-UHFFFAOYSA-N COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CN1CCC(O)(CC1)C(N)=O Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CN1CCC(O)(CC1)C(N)=O HIUGGNBVKQUYKF-UHFFFAOYSA-N 0.000 claims 1
- RLERFXIAHSTVIC-UHFFFAOYSA-N COC=1C=C(OCC2=C(C#N)C(=CC=C2)C2=CC=CC=C2)C=C(C=1CNCCCN1C(CCC1)=O)OC Chemical compound COC=1C=C(OCC2=C(C#N)C(=CC=C2)C2=CC=CC=C2)C=C(C=1CNCCCN1C(CCC1)=O)OC RLERFXIAHSTVIC-UHFFFAOYSA-N 0.000 claims 1
- AJXZPCIOBVYETD-UHFFFAOYSA-N COCCNCc1c(OC)cc(OCc2cccc(-c3ccccc3)c2C#N)cc1OC Chemical compound COCCNCc1c(OC)cc(OCc2cccc(-c3ccccc3)c2C#N)cc1OC AJXZPCIOBVYETD-UHFFFAOYSA-N 0.000 claims 1
- JPKMBXLSPLEASY-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1C(C)CCC1C Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1C(C)CCC1C JPKMBXLSPLEASY-UHFFFAOYSA-N 0.000 claims 1
- SWFHZGGDTJIWSZ-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCC1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCC1 SWFHZGGDTJIWSZ-UHFFFAOYSA-N 0.000 claims 1
- MERHIOAGOUDOLD-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC(C)C1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC(C)C1 MERHIOAGOUDOLD-UHFFFAOYSA-N 0.000 claims 1
- QHXJQISIDOZJGJ-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC(C1)C(O)=O Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC(C1)C(O)=O QHXJQISIDOZJGJ-UHFFFAOYSA-N 0.000 claims 1
- KXYPOJZVZOGBNM-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC(CO)C1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC(CO)C1 KXYPOJZVZOGBNM-UHFFFAOYSA-N 0.000 claims 1
- LFGLHVLFNPRWNU-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC(O)C1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC(O)C1 LFGLHVLFNPRWNU-UHFFFAOYSA-N 0.000 claims 1
- FDGUMKDXNMDZDZ-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC1 FDGUMKDXNMDZDZ-UHFFFAOYSA-N 0.000 claims 1
- XWUQRTVSRZAOHT-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC1C Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCC1C XWUQRTVSRZAOHT-UHFFFAOYSA-N 0.000 claims 1
- VOUQQSDINWYWOT-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCN(CC1)C(C)=O Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCCN(CC1)C(C)=O VOUQQSDINWYWOT-UHFFFAOYSA-N 0.000 claims 1
- HOWNMIDVPXVJME-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCN(CC1)C(C)=O Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CCN(CC1)C(C)=O HOWNMIDVPXVJME-UHFFFAOYSA-N 0.000 claims 1
- JCRRGWHYBLZCAI-QHCPKHFHSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CC[C@@H](C1)NC(C)=O Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CN1CC[C@@H](C1)NC(C)=O JCRRGWHYBLZCAI-QHCPKHFHSA-N 0.000 claims 1
- HXEHEBWGBFEGHH-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC(C)C Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC(C)C HXEHEBWGBFEGHH-UHFFFAOYSA-N 0.000 claims 1
- AAJPIEJWNVYMGO-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1(CO)CCCC1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1(CO)CCCC1 AAJPIEJWNVYMGO-UHFFFAOYSA-N 0.000 claims 1
- WXUVTCGMSMFVBQ-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1CC1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1CC1 WXUVTCGMSMFVBQ-UHFFFAOYSA-N 0.000 claims 1
- GVKRIBKIAGEUGE-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1CCC(O)CC1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1CCC(O)CC1 GVKRIBKIAGEUGE-UHFFFAOYSA-N 0.000 claims 1
- WYHIHFMIMJWJKF-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1CCC1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1CCC1 WYHIHFMIMJWJKF-UHFFFAOYSA-N 0.000 claims 1
- MLGYDLQNIZYLAH-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1CCCC1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1CCCC1 MLGYDLQNIZYLAH-UHFFFAOYSA-N 0.000 claims 1
- IOUNFTFULVKAND-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1CCCCC1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC1CCCCC1 IOUNFTFULVKAND-UHFFFAOYSA-N 0.000 claims 1
- FKVGEVWPIYZSRP-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCC(N)=O Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCC(N)=O FKVGEVWPIYZSRP-UHFFFAOYSA-N 0.000 claims 1
- FOQIRHYDHROHMG-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCN(C)C Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCN(C)C FOQIRHYDHROHMG-UHFFFAOYSA-N 0.000 claims 1
- AQMDRMVAHPBQKI-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCN1CCCC1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCN1CCCC1 AQMDRMVAHPBQKI-UHFFFAOYSA-N 0.000 claims 1
- KXDLFZSSQMCMOM-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCNC(C)=O Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCNC(C)=O KXDLFZSSQMCMOM-UHFFFAOYSA-N 0.000 claims 1
- CRXMIYGHZKOKII-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCO Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCO CRXMIYGHZKOKII-UHFFFAOYSA-N 0.000 claims 1
- AVTPGUBVEFQMJW-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCc1ccccn1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCCc1ccccn1 AVTPGUBVEFQMJW-UHFFFAOYSA-N 0.000 claims 1
- SGRJFBMMKOAXCG-FQEVSTJZSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC[C@@H](O)CC(O)=O Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNC[C@@H](O)CC(O)=O SGRJFBMMKOAXCG-FQEVSTJZSA-N 0.000 claims 1
- PQKOCOSLDBIXGO-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCc1ccc(O)cc1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCc1ccc(O)cc1 PQKOCOSLDBIXGO-UHFFFAOYSA-N 0.000 claims 1
- CEZBHLMYSJAGKM-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCc1ccccc1O Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCc1ccccc1O CEZBHLMYSJAGKM-UHFFFAOYSA-N 0.000 claims 1
- LCRFCTGUHUMZMO-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCc1ccccn1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCc1ccccn1 LCRFCTGUHUMZMO-UHFFFAOYSA-N 0.000 claims 1
- GDZHIPBAWRVMMO-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCc1cccnc1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCc1cccnc1 GDZHIPBAWRVMMO-UHFFFAOYSA-N 0.000 claims 1
- IMQYUPOKVQUSJL-UHFFFAOYSA-N COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCc1ccncc1 Chemical compound COc1cc(OCc2cccc(-c3ccccc3)c2C#N)cc(OC)c1CNCc1ccncc1 IMQYUPOKVQUSJL-UHFFFAOYSA-N 0.000 claims 1
- HPRGLYMHZHSKBH-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccc3OCOc3c2)cc(OC)c1CNCCNC(C)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccc3OCOc3c2)cc(OC)c1CNCCNC(C)=O HPRGLYMHZHSKBH-UHFFFAOYSA-N 0.000 claims 1
- YBEKTEZOCIZYAS-QGZVFWFLSA-N COc1cc(OCc2cccc(c2C)-c2ccc3OCOc3c2)cc(OC)c1CN[C@H](C)C(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccc3OCOc3c2)cc(OC)c1CN[C@H](C)C(O)=O YBEKTEZOCIZYAS-QGZVFWFLSA-N 0.000 claims 1
- RREDZXHJHHGGPH-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2cccc(OCCN3CCCCC3)c2)cc(OC)c1CNCCO Chemical compound COc1cc(OCc2cccc(c2C)-c2cccc(OCCN3CCCCC3)c2)cc(OC)c1CNCCO RREDZXHJHHGGPH-UHFFFAOYSA-N 0.000 claims 1
- DRWOHNQSHPINSR-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CCN Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CCN DRWOHNQSHPINSR-UHFFFAOYSA-N 0.000 claims 1
- PIDMKJMRHQPMGX-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CCNC(=O)C=C Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CCNC(=O)C=C PIDMKJMRHQPMGX-UHFFFAOYSA-N 0.000 claims 1
- RZHFWCSDOHHISF-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CCNC(=O)Nc1ccccc1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CCNC(=O)Nc1ccccc1 RZHFWCSDOHHISF-UHFFFAOYSA-N 0.000 claims 1
- AQRBSBISBBOZLF-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CCNS(=O)(=O)c1ccc2oc(=O)ccc2c1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN(C)CCNS(=O)(=O)c1ccc2oc(=O)ccc2c1 AQRBSBISBBOZLF-UHFFFAOYSA-N 0.000 claims 1
- OMUATABPOVWGRI-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(C)(CO)CO Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(C)(CO)CO OMUATABPOVWGRI-UHFFFAOYSA-N 0.000 claims 1
- FBYCPLYEOZCMPR-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(CO)(CO)CO Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(CO)(CO)CO FBYCPLYEOZCMPR-UHFFFAOYSA-N 0.000 claims 1
- AIKKOMTXOJSVJD-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(CO)CO Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC(CO)CO AIKKOMTXOJSVJD-UHFFFAOYSA-N 0.000 claims 1
- HRMDXCZCDYGFEF-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC1(CO)CCOCC1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC1(CO)CCOCC1 HRMDXCZCDYGFEF-UHFFFAOYSA-N 0.000 claims 1
- WRWPUUKELJIWHM-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC1CCCCC1O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC1CCCCC1O WRWPUUKELJIWHM-UHFFFAOYSA-N 0.000 claims 1
- QEIVNKBIQAKCGX-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(=O)NCC(=O)NCC(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(=O)NCC(=O)NCC(O)=O QEIVNKBIQAKCGX-UHFFFAOYSA-N 0.000 claims 1
- OGRUEURUYCNGAA-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(C)(C)O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(C)(C)O OGRUEURUYCNGAA-UHFFFAOYSA-N 0.000 claims 1
- CEENJLDDMBNKDX-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(C)O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(C)O CEENJLDDMBNKDX-UHFFFAOYSA-N 0.000 claims 1
- QDARKWLJSKZFNV-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(O)C(C)C Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(O)C(C)C QDARKWLJSKZFNV-UHFFFAOYSA-N 0.000 claims 1
- YZWKTZFBUDURFM-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(O)c1cccnc1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(O)c1cccnc1 YZWKTZFBUDURFM-UHFFFAOYSA-N 0.000 claims 1
- MMFLNKBJUGWDQC-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(O)c1ccncc1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC(O)c1ccncc1 MMFLNKBJUGWDQC-UHFFFAOYSA-N 0.000 claims 1
- JODQGIBYHKTBAA-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC1(O)CCN(C)CC1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC1(O)CCN(C)CC1 JODQGIBYHKTBAA-UHFFFAOYSA-N 0.000 claims 1
- YLXAVKAGODUILD-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC1CC(=O)N1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC1CC(=O)N1 YLXAVKAGODUILD-UHFFFAOYSA-N 0.000 claims 1
- UZBQQSTXSUBWFF-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC1CCC1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCC1CCC1 UZBQQSTXSUBWFF-UHFFFAOYSA-N 0.000 claims 1
- GHTNSXNGIZIYJB-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCC(O)C(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCC(O)C(O)=O GHTNSXNGIZIYJB-UHFFFAOYSA-N 0.000 claims 1
- MGQKIZFIOMOWMD-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCCN1CCN(CC1)c1cccc(O)c1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCCN1CCN(CC1)c1cccc(O)c1 MGQKIZFIOMOWMD-UHFFFAOYSA-N 0.000 claims 1
- PXHVWPGAGILTTG-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCCOc1ccccc1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCCOc1ccccc1 PXHVWPGAGILTTG-UHFFFAOYSA-N 0.000 claims 1
- WNARALDDNLKHFU-MHZLTWQESA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCC[C@H](NC(C)=O)C(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCC[C@H](NC(C)=O)C(O)=O WNARALDDNLKHFU-MHZLTWQESA-N 0.000 claims 1
- CFFIILWPZHKSCO-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCN(CC1)C(=O)OC(C)(C)C Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCN(CC1)C(=O)OC(C)(C)C CFFIILWPZHKSCO-UHFFFAOYSA-N 0.000 claims 1
- SWMNFNVUAKGATC-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCN(CC1)c1ccccc1OC Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCN1CCN(CC1)c1ccccc1OC SWMNFNVUAKGATC-UHFFFAOYSA-N 0.000 claims 1
- JOHCBQBSUVPKAW-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCOCCOCCN Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCOCCOCCN JOHCBQBSUVPKAW-UHFFFAOYSA-N 0.000 claims 1
- OUCOGLNFTKCDMI-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCOCCOCCO Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCOCCOCCO OUCOGLNFTKCDMI-UHFFFAOYSA-N 0.000 claims 1
- PEYVGLXZBYCPLJ-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCOCc1ccccc1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCOCc1ccccc1 PEYVGLXZBYCPLJ-UHFFFAOYSA-N 0.000 claims 1
- NNZVWHMFBUDHRL-OAQYLSRUSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC[C@@H](O)CO Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC[C@@H](O)CO NNZVWHMFBUDHRL-OAQYLSRUSA-N 0.000 claims 1
- WMWOLWGPDHWGGI-OAQYLSRUSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC[C@H](O)CC(O)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC[C@H](O)CC(O)=O WMWOLWGPDHWGGI-OAQYLSRUSA-N 0.000 claims 1
- NNZVWHMFBUDHRL-NRFANRHFSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC[C@H](O)CO Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNC[C@H](O)CO NNZVWHMFBUDHRL-NRFANRHFSA-N 0.000 claims 1
- MWIRGLMFWXSACP-SANMLTNESA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H](CO)C(C)C Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H](CO)C(C)C MWIRGLMFWXSACP-SANMLTNESA-N 0.000 claims 1
- JVYRNZHCZWYZPD-SANMLTNESA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H](CO)C1CC1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H](CO)C1CC1 JVYRNZHCZWYZPD-SANMLTNESA-N 0.000 claims 1
- RKUORYVPLXYDFJ-XMMPIXPASA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H](CO)CC(C)C Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H](CO)CC(C)C RKUORYVPLXYDFJ-XMMPIXPASA-N 0.000 claims 1
- VHIHIYBGLOLLDB-CLOONOSVSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H](CO)[C@@H](C)O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@@H](CO)[C@@H](C)O VHIHIYBGLOLLDB-CLOONOSVSA-N 0.000 claims 1
- LRRMSBQHICMFIV-GOSISDBHSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@H](C)CO Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@H](C)CO LRRMSBQHICMFIV-GOSISDBHSA-N 0.000 claims 1
- MWIRGLMFWXSACP-AREMUKBSSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@H](CO)C(C)C Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@H](CO)C(C)C MWIRGLMFWXSACP-AREMUKBSSA-N 0.000 claims 1
- OTXLGVRXIVTOLT-GDLZYMKVSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@H](CO)C1CCCCC1 Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@H](CO)C1CCCCC1 OTXLGVRXIVTOLT-GDLZYMKVSA-N 0.000 claims 1
- VHIHIYBGLOLLDB-UQBPGWFLSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@H](CO)[C@H](C)O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@H](CO)[C@H](C)O VHIHIYBGLOLLDB-UQBPGWFLSA-N 0.000 claims 1
- OPKHCRVDVMEODN-DQEYMECFSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@H]1COC[C@@H]1O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CN[C@H]1COC[C@@H]1O OPKHCRVDVMEODN-DQEYMECFSA-N 0.000 claims 1
- JEDPSOYOYVELLZ-UHFFFAOYSA-N COc1nc(OCc2cccc(c2C)-c2ccccc2)ccc1CNCCNC(C)=O Chemical compound COc1nc(OCc2cccc(c2C)-c2ccccc2)ccc1CNCCNC(C)=O JEDPSOYOYVELLZ-UHFFFAOYSA-N 0.000 claims 1
- NOWGSSVVPIBQKA-MZNJEOGPSA-N C[C@@H](O)[C@@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1)C(O)=O Chemical compound C[C@@H](O)[C@@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1)C(O)=O NOWGSSVVPIBQKA-MZNJEOGPSA-N 0.000 claims 1
- USVJTTKELNGEFF-KRWDZBQOSA-N C[C@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)nc1)C(O)=O Chemical compound C[C@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)nc1)C(O)=O USVJTTKELNGEFF-KRWDZBQOSA-N 0.000 claims 1
- NOWGSSVVPIBQKA-BXKMTCNYSA-N C[C@H](O)[C@@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1)C(O)=O Chemical compound C[C@H](O)[C@@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1)C(O)=O NOWGSSVVPIBQKA-BXKMTCNYSA-N 0.000 claims 1
- NOWGSSVVPIBQKA-XDHUDOTRSA-N C[C@H](O)[C@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1)C(O)=O Chemical compound C[C@H](O)[C@H](NCc1ccc(OCc2cccc(c2C)-c2ccccc2)c(Cl)c1)C(O)=O NOWGSSVVPIBQKA-XDHUDOTRSA-N 0.000 claims 1
- JICCJBHDBUCHOF-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCC(O)CC3)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCC(O)CC3)cn2)cccc1-c1ccccc1 JICCJBHDBUCHOF-UHFFFAOYSA-N 0.000 claims 1
- SSGIGFXOTXBIPP-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCCC(C3)C(O)=O)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCCC(C3)C(O)=O)cn2)cccc1-c1ccccc1 SSGIGFXOTXBIPP-UHFFFAOYSA-N 0.000 claims 1
- ZXAATNQIZOFNLF-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCCC3)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCCC3)cn2)cccc1-c1ccccc1 ZXAATNQIZOFNLF-UHFFFAOYSA-N 0.000 claims 1
- UDVVLOMZVSOUAM-UHFFFAOYSA-N Cc1c(COc2ccc(CN3CCCCC3C(O)=O)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCCCC3C(O)=O)cn2)cccc1-c1ccccc1 UDVVLOMZVSOUAM-UHFFFAOYSA-N 0.000 claims 1
- XXYDHIIDTLWPFT-VWLOTQADSA-N Cc1c(COc2ccc(CN3CCCC[C@H]3C(O)=O)cc2C(F)(F)F)cccc1-c1ccc2OCCOc2c1 Chemical compound Cc1c(COc2ccc(CN3CCCC[C@H]3C(O)=O)cc2C(F)(F)F)cccc1-c1ccc2OCCOc2c1 XXYDHIIDTLWPFT-VWLOTQADSA-N 0.000 claims 1
- WZMGGUAUPLVMPY-QHCPKHFHSA-N Cc1c(COc2ccc(CN3CCC[C@H]3CO)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CN3CCC[C@H]3CO)cn2)cccc1-c1ccccc1 WZMGGUAUPLVMPY-QHCPKHFHSA-N 0.000 claims 1
- RYXUHXJUIBOETL-UHFFFAOYSA-N Cc1c(COc2ccc(CNC3CCC(O)CC3)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNC3CCC(O)CC3)cn2)cccc1-c1ccccc1 RYXUHXJUIBOETL-UHFFFAOYSA-N 0.000 claims 1
- GIZCZRKYQADVIK-UHFFFAOYSA-N Cc1c(COc2ccc(CNC3CCC3)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNC3CCC3)cn2)cccc1-c1ccccc1 GIZCZRKYQADVIK-UHFFFAOYSA-N 0.000 claims 1
- AAWOJJXSGBUHTG-UHFFFAOYSA-N Cc1c(COc2ccc(CNC3CCCC3)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNC3CCCC3)cn2)cccc1-c1ccccc1 AAWOJJXSGBUHTG-UHFFFAOYSA-N 0.000 claims 1
- CFNHHYMSHMXMOX-UHFFFAOYSA-N Cc1c(COc2ccc(CNCCC(N)=O)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNCCC(N)=O)cn2)cccc1-c1ccccc1 CFNHHYMSHMXMOX-UHFFFAOYSA-N 0.000 claims 1
- YAIMPABYXBNRID-UHFFFAOYSA-N Cc1c(COc2ccc(CNCCCN3CCCC3=O)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNCCCN3CCCC3=O)cn2)cccc1-c1ccccc1 YAIMPABYXBNRID-UHFFFAOYSA-N 0.000 claims 1
- LGQGKOFPLMUHLN-UHFFFAOYSA-N Cc1c(COc2ccc(CNCCO)cn2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNCCO)cn2)cccc1-c1ccccc1 LGQGKOFPLMUHLN-UHFFFAOYSA-N 0.000 claims 1
- ZVTRRWCFOKYGKX-UHFFFAOYSA-N Cc1c(COc2ccc(CNCCO)nc2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNCCO)nc2)cccc1-c1ccccc1 ZVTRRWCFOKYGKX-UHFFFAOYSA-N 0.000 claims 1
- GYHIFFSNTRFUJT-UHFFFAOYSA-N Cc1c(COc2ccc(CNCCO)s2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNCCO)s2)cccc1-c1ccccc1 GYHIFFSNTRFUJT-UHFFFAOYSA-N 0.000 claims 1
- SICPIRDFYMJNER-NRFANRHFSA-N Cc1c(COc2ccc(CNC[C@@H](O)CC(O)=O)nc2)cccc1-c1ccccc1 Chemical compound Cc1c(COc2ccc(CNC[C@@H](O)CC(O)=O)nc2)cccc1-c1ccccc1 SICPIRDFYMJNER-NRFANRHFSA-N 0.000 claims 1
- KPSVKGKVOMDLMS-SSEXGKCCSA-N Cc1cc(CN2CCC[C@]2(CC=C)C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CN2CCC[C@]2(CC=C)C(O)=O)ccc1OCc1cccc(c1C)-c1ccccc1 KPSVKGKVOMDLMS-SSEXGKCCSA-N 0.000 claims 1
- OBGIWFZKATUROZ-UHFFFAOYSA-N Cc1cc(CNCC2CC(=O)N2)ccc1OCc1cccc(c1C)-c1ccccc1 Chemical compound Cc1cc(CNCC2CC(=O)N2)ccc1OCc1cccc(c1C)-c1ccccc1 OBGIWFZKATUROZ-UHFFFAOYSA-N 0.000 claims 1
- PGANARHJTRHDSQ-NRFANRHFSA-N ClC=1C=C(C=CC1OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)CNC[C@H](CC(=O)O)O Chemical compound ClC=1C=C(C=CC1OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)CNC[C@H](CC(=O)O)O PGANARHJTRHDSQ-NRFANRHFSA-N 0.000 claims 1
- OYXRERUYWOJCDX-UHFFFAOYSA-N FC1=C(C=C(C=C1)OCCOC)C=1C(=C(C=CC=1)COC1=CC(=C(C(=C1)OC)CNC(CN1CCN(CC1)C)(C)C)OC)C Chemical compound FC1=C(C=C(C=C1)OCCOC)C=1C(=C(C=CC=1)COC1=CC(=C(C(=C1)OC)CNC(CN1CCN(CC1)C)(C)C)OC)C OYXRERUYWOJCDX-UHFFFAOYSA-N 0.000 claims 1
- XTAJWTVMGCFGRZ-UHFFFAOYSA-N N-[2-[[3-[[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy]-4-(trifluoromethyl)phenyl]methylamino]ethyl]acetamide Chemical compound C1(C=2C(C)=C(COC3=C(C(F)(F)F)C=CC(CNCCNC(=O)C)=C3)C=CC=2)=CC=2OCCOC=2C=C1 XTAJWTVMGCFGRZ-UHFFFAOYSA-N 0.000 claims 1
- UGMDKQKZCHHEKB-UHFFFAOYSA-N N-[2-[[4-[(2-methyl-3-phenylphenyl)methoxy]-2,3-dihydro-1H-inden-1-yl]amino]ethyl]acetamide Chemical compound CC(=O)NCCNC1CCc2c1cccc2OCc1cccc(c1C)-c1ccccc1 UGMDKQKZCHHEKB-UHFFFAOYSA-N 0.000 claims 1
- HUDCMLVCJUTNQL-UHFFFAOYSA-N N-[2-[[4-[[3-(3-ethoxyphenyl)-2-methylphenyl]methoxy]-2,6-dimethoxyphenyl]methylamino]ethyl]acetamide Chemical compound C(C)OC=1C=C(C=CC=1)C=1C(=C(C=CC=1)COC1=CC(=C(C(=C1)OC)CNCCNC(C)=O)OC)C HUDCMLVCJUTNQL-UHFFFAOYSA-N 0.000 claims 1
- OLDRYSNASSVDEG-UHFFFAOYSA-N N-[2-[[6-[(2-methyl-3-phenylphenyl)methoxy]pyridin-3-yl]methylamino]ethyl]acetamide Chemical compound CC1=C(C=CC=C1C1=CC=CC=C1)COC1=CC=C(C=N1)CNCCNC(C)=O OLDRYSNASSVDEG-UHFFFAOYSA-N 0.000 claims 1
- PHDDLHUMRHBWAM-UHFFFAOYSA-N N-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]-2-(1,1-dioxo-1,4-thiazinan-4-yl)ethanamine Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNCCN1CCS(=O)(=O)CC1 PHDDLHUMRHBWAM-UHFFFAOYSA-N 0.000 claims 1
- RXMHMSRAKLMRGR-UHFFFAOYSA-N N-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]-3-(4-methylpiperazin-1-yl)propan-1-amine Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNCCCN1CCN(C)CC1 RXMHMSRAKLMRGR-UHFFFAOYSA-N 0.000 claims 1
- YJJMLDZYDIHRJF-UHFFFAOYSA-N N-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]-3-imidazol-1-ylpropan-1-amine Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNCCCN1C=CN=C1 YJJMLDZYDIHRJF-UHFFFAOYSA-N 0.000 claims 1
- UDRCZSWXLQLTRT-UHFFFAOYSA-N N-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]-3-morpholin-4-ylpropan-1-amine Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNCCCN1CCOCC1 UDRCZSWXLQLTRT-UHFFFAOYSA-N 0.000 claims 1
- CBVOKWYQTMLEPM-UHFFFAOYSA-N N-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]-4-methylthiolan-3-amine Chemical compound COC1=CC(OCC2=C(C)C(=CC=C2)C2=CC=CC=C2)=CC(OC)=C1CNC1CSCC1C CBVOKWYQTMLEPM-UHFFFAOYSA-N 0.000 claims 1
- HPBRGWJOQDUMOA-UHFFFAOYSA-N N-[[2,6-dimethoxy-4-[[2-methyl-3-(3-prop-2-enoxyphenyl)phenyl]methoxy]phenyl]methyl]-2-methyl-1-(4-methylpiperazin-1-yl)propan-2-amine Chemical compound COc1cc(OCc2cccc(c2C)-c2cccc(OCC=C)c2)cc(OC)c1CNC(C)(C)CN1CCN(C)CC1 HPBRGWJOQDUMOA-UHFFFAOYSA-N 0.000 claims 1
- ZZFWZTXEDHHLIK-UHFFFAOYSA-N N-[[4-[[3-(1,3-benzodioxol-5-yl)-2-methylphenyl]methoxy]-2,6-dimethoxyphenyl]methyl]-2-methyl-1-(4-methylpiperazin-1-yl)propan-2-amine Chemical compound O1COC2=C1C=CC(=C2)C=1C(=C(C=CC=1)COC1=CC(=C(C(=C1)OC)CNC(CN1CCN(CC1)C)(C)C)OC)C ZZFWZTXEDHHLIK-UHFFFAOYSA-N 0.000 claims 1
- PQZJBVBUXJOKLY-UHFFFAOYSA-N N-[[4-[[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy]-2,6-dimethoxyphenyl]methyl]-2-methyl-1-(4-methylpiperazin-1-yl)propan-2-amine Chemical compound COc1cc(OCc2cccc(c2C)-c2ccc3OCCOc3c2)cc(OC)c1CNC(C)(C)CN1CCN(C)CC1 PQZJBVBUXJOKLY-UHFFFAOYSA-N 0.000 claims 1
- PUKRVBFSODQFHJ-UHFFFAOYSA-N N1(CCC1)CC=1C=CC(=NC1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C Chemical compound N1(CCC1)CC=1C=CC(=NC1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C PUKRVBFSODQFHJ-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- NJNHXAIEMSPCHN-UHFFFAOYSA-N O1CCOC2=C1C=CC(=C2)C=1C(=C(C=CC=1)COC1=CC(=C(C(=C1)OC)CNCCNC(C)=O)OC)C Chemical compound O1CCOC2=C1C=CC(=C2)C=1C(=C(C=CC=1)COC1=CC(=C(C(=C1)OC)CNCCNC(C)=O)OC)C NJNHXAIEMSPCHN-UHFFFAOYSA-N 0.000 claims 1
- YKYUYSHZIOQSPA-UHFFFAOYSA-N OCCNCC1=C(C=C(OCC=2C(=C(C=CC=2)C=2C=C(C=CC=2)O)C)C=C1OC)OC Chemical compound OCCNCC1=C(C=C(OCC=2C(=C(C=CC=2)C=2C=C(C=CC=2)O)C)C=C1OC)OC YKYUYSHZIOQSPA-UHFFFAOYSA-N 0.000 claims 1
- XKPLUFKYCZERKI-QFIPXVFZSA-N OC[C@H]1N(CCC1)CC1=C(C=C(OCC2=C(C#N)C(=CC=C2)C2=CC=CC=C2)C=C1OC)OC Chemical compound OC[C@H]1N(CCC1)CC1=C(C=C(OCC2=C(C#N)C(=CC=C2)C2=CC=CC=C2)C=C1OC)OC XKPLUFKYCZERKI-QFIPXVFZSA-N 0.000 claims 1
- VYPCCNKMGFVEHQ-UHFFFAOYSA-N [1-[[5-[(2-methyl-3-phenylphenyl)methoxy]pyridin-2-yl]methylamino]cyclopentyl]methanol Chemical compound CC1=C(C=CC=C1C1=CC=CC=C1)COC=1C=CC(=NC1)CNC1(CCCC1)CO VYPCCNKMGFVEHQ-UHFFFAOYSA-N 0.000 claims 1
- WAEJPUPLURAWGG-UHFFFAOYSA-N [1-[[6-[(2-methyl-3-phenylphenyl)methoxy]pyridin-3-yl]methylamino]cyclopentyl]methanol Chemical compound CC1=C(C=CC=C1C1=CC=CC=C1)COC1=CC=C(C=N1)CNC1(CCCC1)CO WAEJPUPLURAWGG-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- BKRRXUDJPUGALD-UHFFFAOYSA-N benzyl N-[2-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]ethyl]carbamate Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)cc(OC)c1CNCCNC(=O)OCc1ccccc1 BKRRXUDJPUGALD-UHFFFAOYSA-N 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361873398P | 2013-09-04 | 2013-09-04 | |
| US61/873,398 | 2013-09-04 | ||
| PCT/US2014/053695 WO2015034820A1 (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016536333A JP2016536333A (ja) | 2016-11-24 |
| JP2016536333A5 true JP2016536333A5 (https=) | 2017-10-05 |
| JP6417419B2 JP6417419B2 (ja) | 2018-11-07 |
Family
ID=51539384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016540311A Expired - Fee Related JP6417419B2 (ja) | 2013-09-04 | 2014-09-02 | 免疫調節剤として有用な化合物 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9872852B2 (https=) |
| EP (1) | EP3041822B1 (https=) |
| JP (1) | JP6417419B2 (https=) |
| KR (1) | KR102276644B1 (https=) |
| CN (1) | CN105705489B (https=) |
| AU (1) | AU2014315457B2 (https=) |
| BR (1) | BR112016004194A8 (https=) |
| CA (1) | CA2923184A1 (https=) |
| CL (2) | CL2016000508A1 (https=) |
| EA (1) | EA029901B1 (https=) |
| ES (1) | ES2642074T3 (https=) |
| IL (1) | IL244346B (https=) |
| MX (1) | MX2016002544A (https=) |
| PE (1) | PE20160432A1 (https=) |
| SG (1) | SG11201601225RA (https=) |
| WO (1) | WO2015034820A1 (https=) |
Families Citing this family (252)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2928474B1 (en) | 2012-12-07 | 2018-11-14 | ChemoCentryx, Inc. | Diazole lactams |
| US9850225B2 (en) * | 2014-04-14 | 2017-12-26 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| DK3297438T3 (da) | 2015-05-21 | 2022-01-17 | Chemocentryx Inc | Ccr2-modulatorer |
| CN107709314A (zh) | 2015-06-11 | 2018-02-16 | 巴斯利尔药物国际股份公司 | 外排泵抑制剂及其治疗性用途 |
| US10745382B2 (en) * | 2015-10-15 | 2020-08-18 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG10202004618TA (en) * | 2015-11-19 | 2020-06-29 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| CR20180323A (es) | 2015-11-20 | 2018-08-06 | Idorsia Pharmaceuticals Ltd | Derivados de indol n-sustituídos como moduladores de los receptores de pge2 |
| MA44075A (fr) * | 2015-12-17 | 2021-05-19 | Incyte Corp | Dérivés de n-phényl-pyridine-2-carboxamide et leur utilisation en tant que modulateurs des interactions protéine/protéine pd-1/pd-l1 |
| AU2016379372A1 (en) * | 2015-12-22 | 2018-08-02 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EP3190103A1 (en) * | 2016-01-08 | 2017-07-12 | Rijksuniversiteit Groningen | Inhibitors of the pd-1/pd-l1 protein/protein interaction |
| SG11201808626WA (en) | 2016-04-07 | 2018-10-30 | Chemocentryx Inc | Reducing tumor burden by administering ccr1 antagonists in combination with pd-1 inhibitors or pd-l1 inhibitors |
| AR108396A1 (es) | 2016-05-06 | 2018-08-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| WO2017202275A1 (zh) * | 2016-05-23 | 2017-11-30 | 中国医学科学院药物研究所 | 溴代苄醚衍生物、及其制法和药物组合物与用途 |
| WO2017205464A1 (en) * | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| HUE060256T2 (hu) | 2016-06-20 | 2023-02-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| WO2017220516A1 (en) * | 2016-06-23 | 2017-12-28 | F. Hoffmann-La Roche Ag | Novel [1,2,3]triazolo[4,5-d]pyrimidine derivatives |
| US10639284B2 (en) | 2016-06-27 | 2020-05-05 | Chemocentryx, Inc. | Immunomodulator compounds |
| KR102482673B1 (ko) * | 2016-07-05 | 2022-12-30 | 광저우 맥시노벨 파마수티컬스 씨오., 엘티디. | 방향족 아세틸렌 또는 방향족 에틸렌계 화합물, 그의 중간체, 제조 방법, 약물 조성물 및 용도 |
| EA201990221A1 (ru) * | 2016-07-08 | 2019-06-28 | Бристол-Маерс Сквибб Компани | 1,3-дигидроксифенильные производные, применимые в качестве иммуномодуляторов |
| EP3484866B1 (en) * | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MA45782B1 (fr) | 2016-07-28 | 2021-12-31 | Idorsia Pharmaceuticals Ltd | Modulateurs du récepteur de cxcr7 pipéridine |
| JP2019530732A (ja) * | 2016-08-03 | 2019-10-24 | アライジング・インターナショナル・インコーポレイテッドＡｒｉｓｉｎｇ Ｉｎｔｅｒｎａｔｉｏｎａｌ， Ｉｎｃ． | 免疫モジュレータとして有用な対称または半対称化合物 |
| WO2018044783A1 (en) | 2016-08-29 | 2018-03-08 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| US10144706B2 (en) * | 2016-09-01 | 2018-12-04 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| BR112019004470A2 (pt) * | 2016-09-06 | 2019-09-03 | Incelldx, Inc. | métodos para detectar a expressão de pd-l1 por células e usos do mesmo |
| US11726089B2 (en) | 2016-09-06 | 2023-08-15 | Incelldx, Inc. | Methods of assaying neoplastic and neoplasia-related cells and uses thereof |
| US12298309B2 (en) | 2016-09-06 | 2025-05-13 | Incelldx, Inc. | Methods of assaying neoplastic and neoplasia-related cells and uses thereof |
| KR20230010826A (ko) | 2016-10-14 | 2023-01-19 | 프리시젼 바이오사이언시스 인코포레이티드 | B형 간염 바이러스 게놈 내의 인식 서열에 대해 특이적인 조작된 메가뉴클레아제 |
| WO2018098352A2 (en) | 2016-11-22 | 2018-05-31 | Jun Oishi | Targeting kras induced immune checkpoint expression |
| EP3558970B1 (en) | 2016-12-20 | 2021-09-01 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| LT3558990T (lt) * | 2016-12-22 | 2022-12-27 | Incyte Corporation | Tetrahidroimidazo[4,5-c]piridino dariniai kaip pd-l1 internalizavimo induktoriai |
| WO2018119221A1 (en) * | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| JP7101678B2 (ja) | 2016-12-22 | 2022-07-15 | インサイト・コーポレイション | 免疫調節剤としての複素環式化合物 |
| WO2018119263A1 (en) * | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds derivatives as pd-l1 internalization inducers |
| US20180179202A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| ES2874756T3 (es) | 2016-12-22 | 2021-11-05 | Incyte Corp | Derivados de triazolo[1,5-A]piridina como inmunomoduladores |
| EP3567049A4 (en) | 2016-12-28 | 2020-08-26 | Green Cross Lab Cell Corporation | CHEMERICAL ANTIGENIC RECEPTOR AND NATURAL KILLER CELLS EXPRESSING THE SAME |
| EP3564237A4 (en) * | 2016-12-29 | 2020-06-10 | Shenzhen Chipscreen Biosciences Co., Ltd. | UREA COMPOUND AND PRODUCTION METHOD AND USE THEREOF |
| EP3565841A1 (en) * | 2017-01-06 | 2019-11-13 | Crescendo Biologics Limited | Single domain antibodies to programmed cell death (pd-1) |
| CN110461829B (zh) * | 2017-03-27 | 2023-02-28 | 百时美施贵宝公司 | 作为免疫调节剂的取代的异喹啉衍生物 |
| BR102018007822A2 (pt) * | 2017-04-20 | 2018-11-06 | Gilead Sciences, Inc. | composto, métodos para inibir pd-1, pd-l1 e/ou interação de pd-1/pd-l1 e para tratamento de câncer, composição farmacêutica, e, kit para tratamento de ou prevenção de câncer ou uma doença ou condição |
| WO2018200571A1 (en) | 2017-04-25 | 2018-11-01 | Arbutus Biopharma Corporation | Substituted 2,3-dihydro-1h-indene analogs and methods using same |
| US11839613B2 (en) | 2017-05-18 | 2023-12-12 | Idorsia Pharmaceuticals Ltd | Pyrimidine derivatives as PGE2 receptor modulators |
| TW201900179A (zh) | 2017-05-18 | 2019-01-01 | 瑞士商愛杜西亞製藥有限公司 | 作為pge2受體調節劑之苯并呋喃及苯并噻吩衍生物 |
| TWI768043B (zh) | 2017-05-18 | 2022-06-21 | 瑞士商愛杜西亞製藥有限公司 | N-取代吲哚衍生物 |
| KR102612140B1 (ko) | 2017-05-18 | 2023-12-08 | 이도르시아 파마슈티컬스 리미티드 | 피리미딘 유도체 |
| PE20191814A1 (es) | 2017-05-18 | 2019-12-27 | Idorsia Pharmaceuticals Ltd | Derivados de pirimidina como moduladores del receptor de pge2 |
| KR20200041834A (ko) | 2017-06-01 | 2020-04-22 | 젠코어 인코포레이티드 | Cd123 및 cd3에 결합하는 이중특이성 항체 |
| WO2018223004A1 (en) | 2017-06-01 | 2018-12-06 | Xencor, Inc. | Bispecific antibodies that bind cd20 and cd3 |
| WO2019008156A1 (en) | 2017-07-07 | 2019-01-10 | Rijksuniversiteit Groningen | INHIBITORS OF PROTEIN / PROTEIN INTERACTION PD-1 / PD-L1 |
| WO2019008152A1 (en) | 2017-07-07 | 2019-01-10 | Rijksuniversiteit Groningen | 3-CYANOTHIOPHENE DERIVATIVES AS INHIBITORS OF PROTEIN / PROTEIN INTERACTION PD-1 / PD-L1 |
| WO2019008154A1 (en) | 2017-07-07 | 2019-01-10 | Rijksuniversiteit Groningen | 3- (AZOLYLMETHOXY) BIPHENYL DERIVATIVES AS INHIBITORS OF PROTEIN / PROTEIN INTERACTION PD-1 / PD-L1 |
| US10919852B2 (en) | 2017-07-28 | 2021-02-16 | Chemocentryx, Inc. | Immunomodulator compounds |
| US10392405B2 (en) | 2017-08-08 | 2019-08-27 | Chemocentryx, Inc. | Macrocyclic immunomodulators |
| TW201920202A (zh) | 2017-08-17 | 2019-06-01 | 瑞士商愛杜西亞製藥有限公司 | 吲哚胺2,3-二氧酶及/或色胺酸2,3-二氧酶的抑制劑 |
| EP3669872A4 (en) * | 2017-08-18 | 2021-05-05 | Shanghai Ennovabio Pharmaceuticals Co., Ltd. | FORMYL PYRIDINE DERIVATIVE WITH PD-L1 INHIBITORING EFFECT, MANUFACTURING METHOD FOR IT AND USE THEREOF |
| RU2764243C2 (ru) | 2017-09-22 | 2022-01-14 | ДЖУБИЛАНТ ЭПИПЭД ЭлЭлСи | Гетероциклические соединения в качестве ингибиторов PAD |
| CA3293051A1 (en) | 2017-09-25 | 2026-03-02 | Chemocentryx, Inc. | Combination therapy using a chemokine receptor 2 (ccr2) antagonist and a pd-1/pd-l1 inhibitor |
| CN109665968B (zh) * | 2017-10-16 | 2022-02-22 | 四川科伦博泰生物医药股份有限公司 | 并环化合物及其制备方法和用途 |
| AU2018352142B2 (en) | 2017-10-18 | 2022-08-25 | Jubilant Epipad LLC | Imidazo-pyridine compounds as PAD inhibitors |
| CN109721527B (zh) * | 2017-10-27 | 2024-03-12 | 广州丹康医药生物有限公司 | 一种新型抗pd-l1化合物、其应用及含其的组合物 |
| US11629135B2 (en) * | 2017-11-06 | 2023-04-18 | Jubilant Prodell Llc | Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation |
| US20200353050A1 (en) | 2017-11-10 | 2020-11-12 | Armo Biosciences, Inc. | Compositions and methods of use of interleukin-10 in combination with immune check-point pathway inhibitors |
| EP3710478A1 (en) | 2017-11-13 | 2020-09-23 | Crescendo Biologics Limited | Molecules that bind to cd137 and psma |
| US11649294B2 (en) | 2017-11-14 | 2023-05-16 | GC Cell Corporation | Anti-HER2 antibody or antigen-binding fragment thereof, and chimeric antigen receptor comprising same |
| KR102774451B1 (ko) | 2017-11-14 | 2025-02-28 | 앱클론(주) | 항-her2 항체 또는 그의 항원 결합 단편, 및 이를 포함하는 키메라 항원 수용체 |
| PT3704120T (pt) | 2017-11-24 | 2024-07-03 | Jubilant Episcribe Llc | Compostos heterocíclicos como inibidores de prmt5 |
| EP3728283B1 (en) | 2017-12-20 | 2023-11-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 3'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| WO2019123339A1 (en) | 2017-12-20 | 2019-06-27 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| CN109956898B (zh) * | 2017-12-22 | 2021-03-26 | 上海海雁医药科技有限公司 | 免疫调节剂及其制法与医药上的用途 |
| CN109988144B (zh) * | 2017-12-29 | 2024-07-05 | 广州再极医药科技有限公司 | 芳香乙烯或芳香乙基类衍生物、其制备方法、中间体、药物组合物及应用 |
| US20190269664A1 (en) | 2018-01-08 | 2019-09-05 | Chemocentryx, Inc. | Methods of treating solid tumors with ccr2 antagonists |
| CN112105353B (zh) | 2018-01-08 | 2024-04-19 | 凯莫森特里克斯股份有限公司 | Ccr2拮抗剂治疗实体瘤的方法 |
| CN112004537A (zh) * | 2018-01-09 | 2020-11-27 | 穿梭药业公司 | 用于治疗人疾病的选择性组蛋白去乙酰化酶抑制剂 |
| WO2019137927A1 (en) | 2018-01-10 | 2019-07-18 | Idorsia Pharmaceuticals Ltd | 2,4,6,7-tetrahydro-pyrazolo[4,3-d]pyrimidin-5-one derivatives and related compounds as c5a receptor modulators for treating vasculitis and inflammatory diseases |
| ES2907282T3 (es) | 2018-01-15 | 2022-04-22 | Idorsia Pharmaceuticals Ltd | Inhibidores de la indoleamina 2,3-dioxigenasa y/o de la triptófano dioxigenasa |
| EP3740477A1 (en) | 2018-01-19 | 2020-11-25 | Idorsia Pharmaceuticals Ltd | C5a receptor modulators |
| WO2019141803A1 (en) | 2018-01-19 | 2019-07-25 | Idorsia Pharmaceuticals Ltd | C5a receptor modulators |
| KR102738303B1 (ko) | 2018-01-23 | 2024-12-03 | 브리스톨-마이어스 스큅 컴퍼니 | 면역조정제로서 유용한 2,8-디아실-2,8-디아자스피로[5.5]운데칸 화합물 |
| WO2019145460A1 (en) | 2018-01-26 | 2019-08-01 | Idorsia Pharmaceuticals Ltd | Crystalline forms of the cxcr7 receptor antagonist (3s,4s)-1-cyclopropylmethyl-4-{[5-(2,4-difluoro-phenyl)-isoxazole-3-carbonyl]-amino}-piperidine-3-carboxylic acid (1-pyrimidin-2-yl-cyclopropyl)-amide |
| CN110092779B (zh) * | 2018-01-29 | 2022-07-12 | 广州丹康医药生物有限公司 | 一种取代的苯基化合物及其应用 |
| CN110092740B (zh) * | 2018-01-29 | 2022-10-14 | 广州丹康医药生物有限公司 | 一种稠环化合物及其应用 |
| WO2019149183A1 (zh) | 2018-02-05 | 2019-08-08 | 上海和誉生物医药科技有限公司 | 一种联芳基衍生物、其制备方法和在药学上的应用 |
| CR20200347A (es) * | 2018-02-13 | 2020-09-23 | Gilead Sciences Inc | Inhibidores pd-1/pd-l1 |
| GB201802573D0 (en) | 2018-02-16 | 2018-04-04 | Crescendo Biologics Ltd | Therapeutic molecules that bind to LAG3 |
| US10568874B2 (en) | 2018-02-22 | 2020-02-25 | Chemocentryx, Inc. | Indane-amines as PD-L1 antagonists |
| JP7050165B2 (ja) | 2018-02-26 | 2022-04-07 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｂｖ複製阻害剤としての置換ピロリジン化合物 |
| CN112041312A (zh) | 2018-03-01 | 2020-12-04 | 百时美施贵宝公司 | 用作免疫调节剂的化合物 |
| CN110240587B (zh) * | 2018-03-08 | 2022-01-04 | 中国科学院上海药物研究所 | 一类芳基二氟苄基醚类化合物、制备方法及用途 |
| MX2020009517A (es) * | 2018-03-13 | 2021-01-20 | Jubilant Prodel LLC | Compuestos biciclicos como inhibidores de la interaccion/activacio n de pdl/pd-l1. |
| CN111788193B (zh) * | 2018-03-13 | 2023-04-04 | 广东东阳光药业有限公司 | Pd-1/pd-l1类小分子抑制剂及其在药物中的应用 |
| SMT202500157T1 (it) | 2018-03-30 | 2025-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
| US10870691B2 (en) | 2018-04-05 | 2020-12-22 | Gilead Sciences, Inc. | Antibodies and fragments thereof that bind hepatitis B virus protein X |
| TWI833744B (zh) | 2018-04-06 | 2024-03-01 | 捷克科學院有機化學與生物化學研究所 | 3'3'-環二核苷酸 |
| TWI818007B (zh) | 2018-04-06 | 2023-10-11 | 捷克科學院有機化學與生物化學研究所 | 2'3'-環二核苷酸 |
| TW202005654A (zh) | 2018-04-06 | 2020-02-01 | 捷克科學院有機化學與生物化學研究所 | ２，２，─環二核苷酸 |
| US11142750B2 (en) | 2018-04-12 | 2021-10-12 | Precision Biosciences, Inc. | Optimized engineered meganucleases having specificity for a recognition sequence in the Hepatitis B virus genome |
| TWI712412B (zh) | 2018-04-19 | 2020-12-11 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
| US20190359645A1 (en) | 2018-05-03 | 2019-11-28 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2'3'-cyclic dinucleotides comprising carbocyclic nucleotide |
| HUE061503T2 (hu) | 2018-05-11 | 2023-07-28 | Incyte Corp | Tetrahidro-imidazo[4,5-C]piridin-származékok mint PD-L1 immunmodulátorok |
| EP3804758A4 (en) | 2018-05-31 | 2022-03-02 | ONO Pharmaceutical Co., Ltd. | BIOMARKERS TO EVALUATE THE EFFECTIVENESS OF AN IMMUNE CHECKPOINT INHIBITOR |
| EP3801617A1 (en) | 2018-06-01 | 2021-04-14 | Novartis Ag | Dosing of a bispecific antibody that bind cd123 and cd3 |
| WO2019245817A1 (en) | 2018-06-19 | 2019-12-26 | Armo Biosciences, Inc. | Compositions and methods of use of il-10 agents in conjunction with chimeric antigen receptor cell therapy |
| SG11202012425QA (en) | 2018-07-13 | 2021-01-28 | Gilead Sciences Inc | Pd-1/pd-l1 inhibitors |
| WO2020028097A1 (en) | 2018-08-01 | 2020-02-06 | Gilead Sciences, Inc. | Solid forms of (r)-11-(methoxymethyl)-12-(3-methoxypropoxy)-3,3-dimethyl-8-0x0-2,3,8,13b-tetrahydro-1h-pyrido[2,1-a]pyrrolo[1,2-c] phthalazine-7-c arboxylic acid |
| CN109305934A (zh) * | 2018-08-07 | 2019-02-05 | 成都海博锐药业有限公司 | 苯醚类衍生物及可药用盐、医药上的用途 |
| CN111960985A (zh) * | 2018-08-08 | 2020-11-20 | 中国人民解放军总医院 | 抗肿瘤化合物 |
| CN110872275A (zh) * | 2018-08-31 | 2020-03-10 | 深圳微芯生物科技股份有限公司 | 作为免疫调节剂的联苯化合物及其用途 |
| TWI855000B (zh) | 2018-10-11 | 2024-09-11 | 日商小野藥品工業股份有限公司 | Ｓｔｉｎｇ促效化合物 |
| WO2020086556A1 (en) * | 2018-10-24 | 2020-04-30 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| US11203591B2 (en) | 2018-10-31 | 2021-12-21 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds |
| WO2020092528A1 (en) | 2018-10-31 | 2020-05-07 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds having hpk1 inhibitory activity |
| AU2019373702A1 (en) | 2018-11-02 | 2021-06-24 | Shanghai Maxinovel Pharmaceuticals Co., Ltd. | Diphenyl-like compound, intermediate thereof, preparation method therefor, pharmaceutical composition thereof and uses thereof |
| CN109456284A (zh) * | 2018-11-13 | 2019-03-12 | 南方医科大学 | 一种含取代联苯的查尔酮及其应用 |
| CN109438263A (zh) * | 2018-11-28 | 2019-03-08 | 南方医科大学 | 一种含取代联苯的萘及其应用 |
| WO2020118208A1 (en) | 2018-12-07 | 2020-06-11 | Arizona Board Of Regents On Behalf Of The University Of Arizona | A method of determining risk for skin cancer development and skin cancer therapeutic prevention by measuring pd-1/pd-l1 signaling pathway members |
| CN109503546A (zh) * | 2019-01-10 | 2019-03-22 | 南方医科大学 | 一种间苯二酚二苯甲醚及其应用 |
| WO2020161125A1 (en) | 2019-02-05 | 2020-08-13 | Ventana Medical Systems, Inc. | Methods and systems for evaluation of immune cell infiltrate in stage iv colorectal cancer |
| WO2020169058A1 (zh) * | 2019-02-21 | 2020-08-27 | 杭州阿诺生物医药科技有限公司 | Pd-l1拮抗剂化合物 |
| WO2020178768A1 (en) | 2019-03-07 | 2020-09-10 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3'-cyclic dinucleotide analogue comprising a cyclopentanyl modified nucleotide as sting modulator |
| EP3934757B1 (en) | 2019-03-07 | 2023-02-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 2'3'-cyclic dinucleotides and prodrugs thereof |
| WO2020178770A1 (en) | 2019-03-07 | 2020-09-10 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3'-cyclic dinucleotides and prodrugs thereof |
| EP3943083A4 (en) | 2019-03-22 | 2023-06-07 | Guangzhou Maxinovel Pharmaceuticals Co., Ltd. | SMALL MOLECULE PD-1/PD-L1 INHIBITOR, PHARMACEUTICAL COMPOSITION THEREOF WITH PD-L1 ANTIBODY, AND USES THEREOF |
| KR20210146348A (ko) | 2019-03-28 | 2021-12-03 | 브리스톨-마이어스 스큅 컴퍼니 | 종양을 치료하는 방법 |
| WO2020198676A1 (en) | 2019-03-28 | 2020-10-01 | Bristol-Myers Squibb Company | Methods of treating tumor |
| CN111747927B (zh) * | 2019-03-29 | 2023-08-18 | 广州丹康医药生物有限公司 | 作为免疫调节剂的化合物及其应用 |
| JP7592621B2 (ja) | 2019-04-02 | 2024-12-02 | イミュネチューン・ベー・フェー | 免疫刺激組成物及びその使用 |
| TW202212339A (zh) | 2019-04-17 | 2022-04-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TWI751516B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| WO2020225077A1 (en) | 2019-05-03 | 2020-11-12 | Idorsia Pharmaceuticals Ltd | Pyrimido[4,5-b]indol derivatives as pdhk1 inhibitors |
| CN112566905B (zh) * | 2019-05-10 | 2024-07-30 | 上海海雁医药科技有限公司 | 取代的苯基丙烯基吡啶类衍生物，其制法与医药上的用途 |
| WO2020232256A1 (en) | 2019-05-15 | 2020-11-19 | Chemocentryx, Inc. | Triaryl compounds for treatment of pd-l1 diseases |
| EP3972695A1 (en) | 2019-05-23 | 2022-03-30 | Gilead Sciences, Inc. | Substituted exo-methylene-oxindoles which are hpk1/map4k1 inhibitors |
| WO2020243570A1 (en) | 2019-05-30 | 2020-12-03 | Bristol-Myers Squibb Company | Cell localization signature and combination therapy |
| US20220363760A1 (en) | 2019-05-30 | 2022-11-17 | Bristol-Myers Squibb Company | Multi-tumor gene signature for suitability to immuno-oncology therapy |
| KR20220016155A (ko) | 2019-05-30 | 2022-02-08 | 브리스톨-마이어스 스큅 컴퍼니 | 면역-종양학 (i-o) 요법에 적합한 대상체를 확인하는 방법 |
| WO2020244518A1 (zh) * | 2019-06-04 | 2020-12-10 | 中国科学院上海药物研究所 | 一种具有苄氧基芳环结构的化合物，其制备方法和用途 |
| JP7768770B2 (ja) * | 2019-06-07 | 2025-11-12 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | Ｐｄｌ１チェックポイント阻害剤としての複素環式免疫調節剤 |
| WO2020248908A1 (zh) * | 2019-06-10 | 2020-12-17 | 中国科学院广州生物医药与健康研究院 | 一种双功能免疫调节剂及其在药学上可接受的盐、药物组合物 |
| EP3982922A1 (en) | 2019-06-12 | 2022-04-20 | Technical University of Denmark | Dissacharide formulations for controlled drug release |
| WO2020257549A2 (en) | 2019-06-20 | 2020-12-24 | Chemocentryx, Inc. | Compounds for treatment of pd-l1 diseases |
| CN112121169B (zh) * | 2019-06-24 | 2023-10-24 | 广州再极医药科技有限公司 | 用于治疗具有高间质压力的肿瘤受试者的癌症的小分子抑制剂 |
| RS65511B1 (sr) | 2019-07-09 | 2024-06-28 | Idorsia Pharmaceuticals Ltd | Farmaceutska kompozicija koja sadrži jedinjenje tetrahidropirazolopirimidinon |
| BR112021025888A2 (pt) | 2019-07-10 | 2022-04-26 | Chemocentryx Inc | Indanos como inibidores de pd-l1 |
| EP3997083A1 (en) | 2019-07-11 | 2022-05-18 | Idorsia Pharmaceuticals Ltd | Inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan 2,3-dioxygenase |
| WO2021025554A1 (en) | 2019-08-02 | 2021-02-11 | Stichting Het Nederlands Kanker Instituut-Antoni van Leeuwenhoek Ziekenhuis | Combination comprising an activator of the glucocorticoid receptor and an inhibitor of ifg-1 signaling for carcinoma treatment |
| KR20220041099A (ko) | 2019-08-05 | 2022-03-31 | 오노 야꾸힝 고교 가부시키가이샤 | 면역 체크포인트 저해약의 유효성 판정 바이오마커 |
| JP7665593B2 (ja) | 2019-08-09 | 2025-04-21 | インサイト・コーポレイション | Ｐｄ－１／ｐｄ－ｌ１阻害剤の塩 |
| WO2021034804A1 (en) | 2019-08-19 | 2021-02-25 | Gilead Sciences, Inc. | Pharmaceutical formulations of tenofovir alafenamide |
| CN111909108B (zh) * | 2019-09-02 | 2023-05-02 | 中国药科大学 | 联苯类化合物及其制备方法和医药用途 |
| WO2021055994A1 (en) | 2019-09-22 | 2021-03-25 | Bristol-Myers Squibb Company | Quantitative spatial profiling for lag-3 antagonist therapy |
| CN112574183B (zh) * | 2019-09-29 | 2022-07-08 | 南京华威医药科技集团有限公司 | 一种pd-1抑制剂及其制备方法和用途 |
| KR20220059517A (ko) | 2019-09-30 | 2022-05-10 | 메드샤인 디스커버리 아이엔씨. | 소분자 pd-1/pd-l1 억제제로서의 화합물 및 이의 용도 |
| PE20221038A1 (es) | 2019-09-30 | 2022-06-17 | Incyte Corp | Compuestos de pirido[3,2-d] pirimidina como inmunomoduladores |
| DK4037708T3 (da) | 2019-09-30 | 2024-09-30 | Gilead Sciences Inc | HBV-vacciner og fremgangsmåder til at behandle HBV |
| CN114761085A (zh) * | 2019-10-04 | 2022-07-15 | 百时美施贵宝公司 | 可用作免疫调节剂的化合物 |
| WO2021076565A1 (en) | 2019-10-16 | 2021-04-22 | Corcept Therapeutics Incorporated | Method of normalizing the neutrophil to lymphocyte ratio in cancer patients with a selective glucocorticoid receptor antagonist |
| ES3064674T3 (en) | 2019-10-16 | 2026-04-28 | Chemocentryx Inc | Heteroaryl-biphenyl amines for the treatment of pd-l1 diseases |
| JP7736678B2 (ja) | 2019-10-16 | 2025-09-09 | ケモセントリックス，インコーポレイティド | Ｐｄ－ｌ１疾患の処置のためのヘテロアリール－ビフェニルアミド |
| US20220280499A1 (en) | 2019-10-21 | 2022-09-08 | Stichting Het Nederlands Kanker Instituue-Antoni van Leeuwenhoek Ziekenhuis | Novel drug combinations for treatment of a carcinoma |
| US20220411499A1 (en) | 2019-11-08 | 2022-12-29 | Bristol-Myers Squibb Company | LAG-3 Antagonist Therapy for Melanoma |
| CA3160131A1 (en) | 2019-11-11 | 2021-05-20 | Incyte Corporation | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| DK4069729T3 (da) | 2019-12-06 | 2025-04-07 | Prec Biosciences Inc | Optimerede, modificerede meganukleaser med specificitet for en genkendelsessekvens i hepatitis b-virusgenomet |
| IL294209A (en) | 2019-12-26 | 2022-08-01 | Adlai Nortye Biopharma Co Ltd | pd-1 antagonist |
| WO2021136354A1 (zh) | 2020-01-03 | 2021-07-08 | 上海翰森生物医药科技有限公司 | 联苯类衍生物抑制剂、其制备方法和应用 |
| WO2021146436A2 (en) | 2020-01-14 | 2021-07-22 | Synthekine, Inc. | Biased il2 muteins methods and compositions |
| CN111187172B (zh) * | 2020-01-20 | 2021-10-29 | 中国药科大学 | 硝基苯醚类化合物、其制备方法和药物组合物与用途 |
| BR112022015011A2 (pt) | 2020-01-29 | 2022-09-20 | Corcept Therapeutics Inc | Método para tratar um sujeito que sofre de tumor de carcinoma adrenocortical e tendo excesso de cortisol, e, composição farmacêutica para tratar carcinoma adrenocortical |
| WO2021171264A1 (en) | 2020-02-28 | 2021-09-02 | Novartis Ag | Dosing of a bispecific antibody that binds cd123 and cd3 |
| JP7796032B2 (ja) * | 2020-03-11 | 2026-01-08 | パーデュー・リサーチ・ファウンデーション | 免疫調節活性を持つ化合物およびその治療的使用 |
| WO2021188959A1 (en) | 2020-03-20 | 2021-09-23 | Gilead Sciences, Inc. | Prodrugs of 4'-c-substituted-2-halo-2'-deoxyadenosine nucleosides and methods of making and using the same |
| CN111303122A (zh) * | 2020-04-07 | 2020-06-19 | 南方医科大学 | 一种泊马度胺衍生物及其用途 |
| US20230151024A1 (en) | 2020-04-10 | 2023-05-18 | Ono Pharmaceutical Co., Ltd. | Sting agonistic compound |
| TW202200136A (zh) | 2020-04-10 | 2022-01-01 | 日商小野藥品工業股份有限公司 | 癌治療方法 |
| CN111333629B (zh) * | 2020-04-10 | 2021-03-05 | 颜建发 | 苯基-1h-吡唑类衍生物及其在抗肿瘤药物中的应用 |
| CN111559981B (zh) * | 2020-04-15 | 2023-08-01 | 杭州庆正鸿科技有限公司 | 一种联苯-嘧啶偶联物及其制备方法和应用 |
| EP4143344A1 (en) | 2020-04-27 | 2023-03-08 | Agendia N.V. | Treatment of her2 negative, mammaprint high risk 2 breast cancer |
| CN113563260A (zh) * | 2020-04-28 | 2021-10-29 | 药康众拓(江苏)医药科技有限公司 | 苯甲酰胺类化合物、制备方法及用途 |
| CN113582971B (zh) * | 2020-04-30 | 2023-10-20 | 北京康辰药业股份有限公司 | 一种小分子免疫抑制剂、其制备方法及其应用 |
| CN113943330A (zh) * | 2020-07-17 | 2022-01-18 | 中国科学院上海药物研究所 | 一类含糖结构化合物、其制备方法、药物组合物和用途 |
| CN114075123B (zh) * | 2020-08-11 | 2023-06-06 | 中国人民解放军军事科学院军事医学研究院 | 苄胺类衍生物及其制备方法与用途 |
| IL300813A (en) | 2020-08-28 | 2023-04-01 | Bristol Myers Squibb Co | LAG-3 antagonist therapy for hepatocellular carcinoma |
| AU2021334361A1 (en) | 2020-08-31 | 2023-05-11 | Bristol-Myers Squibb Company | Cell localization signature and immunotherapy |
| US12577621B2 (en) | 2020-09-08 | 2026-03-17 | Duke University | LRRK2 mutations as biomarkers for the prediction of immune checkpoint response in cancer |
| JP7810700B2 (ja) | 2020-09-09 | 2026-02-03 | ベイジン マキシノベル ファーマシューティカルズ カンパニー リミテッド | 芳香族エチレン系化合物、その製造方法、中間体、医薬組成物及びその使用 |
| KR20230066582A (ko) | 2020-09-10 | 2023-05-16 | 남미 테라퓨틱스, 인크. | 암의 치료에 유용한 pd-1 길항제 전구약물을 함유하는 제제화된 및/또는 공동-제제화된 리포솜 조성물 및 그의 방법 |
| KR20230093282A (ko) | 2020-10-23 | 2023-06-27 | 브리스톨-마이어스 스큅 컴퍼니 | 폐암에 대한 lag-3 길항제 요법 |
| CA3197685A1 (en) | 2020-10-29 | 2022-05-05 | Shenzhen Chipscreen Biosciences Co., Ltd. | Biphenyl compound as immunomodulator, preparation method therefor and application thereof |
| CR20230230A (es) | 2020-11-06 | 2023-07-27 | Incyte Corp | Proceso para hacer un inhibidor de pd-1/pdl1 y sales y formas cristalinas del mismo |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| CN114507227B (zh) * | 2020-11-17 | 2024-06-21 | 中国医学科学院药物研究所 | 苯并异噻唑类化合物、及其制法和药物组合物与用途 |
| WO2022114957A1 (en) | 2020-11-26 | 2022-06-02 | Stichting Het Nederlands Kanker Instituut-Antoni van Leeuwenhoek Ziekenhuis | Personalized tumor markers |
| WO2022120179A1 (en) | 2020-12-03 | 2022-06-09 | Bristol-Myers Squibb Company | Multi-tumor gene signatures and uses thereof |
| EP4274616A2 (en) | 2021-01-11 | 2023-11-15 | Synthekine, Inc. | Compositions and methods related to receptor pairing |
| CN117677634A (zh) | 2021-03-05 | 2024-03-08 | 利达提斯有限公司 | 三聚体多肽及其在治疗癌症中的用途 |
| WO2022199578A1 (zh) * | 2021-03-22 | 2022-09-29 | 南京明德新药研发有限公司 | 氟代乙烯基联苯衍生物及其应用 |
| CN113105431B (zh) * | 2021-03-24 | 2022-10-28 | 河北康泰药业有限公司 | 一种蛋白水解靶向嵌合体及其应用 |
| CN117858719A (zh) | 2021-03-29 | 2024-04-09 | 朱诺治疗学股份有限公司 | 使用检查点抑制剂疗法和car t细胞疗法的组合进行给药和治疗的方法 |
| US20240246931A1 (en) * | 2021-04-22 | 2024-07-25 | Jubilant Prodel LLC | Compounds as pd1/pd-l1 inhibitors and methods thereof |
| CN113135895A (zh) * | 2021-04-30 | 2021-07-20 | 中国药科大学 | 一种新型联苯类衍生物及其制备方法与医药用途 |
| KR20240004801A (ko) * | 2021-05-05 | 2024-01-11 | 브리스톨-마이어스 스큅 컴퍼니 | 면역조절제로서 유용한 락톤 및 락탐 함유 화합물 |
| WO2022241134A1 (en) | 2021-05-13 | 2022-11-17 | Gilead Sciences, Inc. | COMBINATION OF A TLR8 MODULATING COMPOUND AND ANTI-HBV siRNA THERAPEUTICS |
| TWI910028B (zh) | 2021-06-11 | 2025-12-21 | 美商基利科學股份有限公司 | Mcl-1抑制劑與抗癌劑之組合 |
| US11931424B2 (en) | 2021-06-11 | 2024-03-19 | Gilead Sciences, Inc. | Combination MCL-1 inhibitors with anti-body drug conjugates |
| EP4337202A4 (en) | 2021-06-18 | 2025-04-02 | Aligos Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR TARGETING PD-L1 |
| AU2022299051B2 (en) | 2021-06-23 | 2025-03-13 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| MX2023014762A (es) | 2021-06-23 | 2024-01-15 | Gilead Sciences Inc | Compuestos moduladores de diacilglicerol quinasa. |
| JP7686091B2 (ja) | 2021-06-23 | 2025-05-30 | ギリアード サイエンシーズ， インコーポレイテッド | ジアシルグリセロールキナーゼ調節化合物 |
| JP7651018B2 (ja) | 2021-06-23 | 2025-03-25 | ギリアード サイエンシーズ， インコーポレイテッド | ジアシルグリセロールキナーゼ調節化合物 |
| IT202100016775A1 (it) * | 2021-06-25 | 2022-12-25 | Univ Degli Studi Milano | Derivati triazinici per il trattamento dei tumori e di disturbi neurodegenerativi |
| US20250288666A1 (en) | 2021-07-14 | 2025-09-18 | Synthekine, Inc. | Methods and compositions for use in cell therapy of neoplastic disease |
| CN114437051A (zh) * | 2021-09-18 | 2022-05-06 | 药康众拓(江苏)医药科技有限公司 | 一类联苯类化合物、其制备方法和用途 |
| WO2023057548A1 (en) | 2021-10-07 | 2023-04-13 | Idorsia Pharmaceuticals Ltd | Ccr6 receptor modulators |
| WO2023072924A1 (en) | 2021-10-26 | 2023-05-04 | Idorsia Pharmaceuticals Ltd | Ccr6 receptor modulators |
| TW202325271A (zh) | 2021-10-28 | 2023-07-01 | 瑞士商愛杜西亞製藥有限公司 | Ccr6受體調節劑 |
| CA3224890A1 (en) | 2021-10-29 | 2023-05-04 | Bristol-Myers Squibb Company | Lag-3 antagonist therapy for hematological cancer |
| WO2023080788A1 (en) | 2021-11-05 | 2023-05-11 | Stichting Het Nederlands Kanker Instituut-Antoni van Leeuwenhoek Ziekenhuis | Tryptophan depletion induces production and presentation of tryptophan to phenylalanine substitutions |
| US20250144253A1 (en) | 2021-12-06 | 2025-05-08 | Helmholtz-Zentrum Dresden-Rossendorf E.V. | 3-((3-([1,1'-biphenyl]-3-ylmethoxy)phenoxy)methyl)benzonitrile derivatives and the use thereof |
| KR20240135661A (ko) | 2022-01-26 | 2024-09-11 | 브리스톨-마이어스 스큅 컴퍼니 | 간세포성 암종에 대한 조합 요법 |
| CN116768870A (zh) * | 2022-03-08 | 2023-09-19 | 中国科学院上海药物研究所 | 具有苄氧基芳基醚结构的化合物及其制备方法和用途 |
| JP2025513724A (ja) | 2022-03-31 | 2025-04-30 | ヴェンタナ メディカル システムズ， インク． | ミスマッチ修復が欠損した結腸直腸腫瘍におけるｐｄ－１軸指向治療薬に対する応答を予測するための方法およびシステム |
| JP7851417B2 (ja) | 2022-04-08 | 2026-04-24 | ブリストル－マイヤーズ スクイブ カンパニー | 三次リンパ組織様構造の機械学習識別、分類、及び定量化 |
| US20260049359A1 (en) | 2022-05-19 | 2026-02-19 | Agendia N.V. | Prediction of response to immune therapy in breast cancer patients |
| EP4282435A1 (en) | 2022-05-23 | 2023-11-29 | Danmarks Tekniske Universitet | Formulations of active pharmaceutical ingredients and excipients in icells via hydrophobic ion pairing |
| EP4282448A1 (en) | 2022-05-23 | 2023-11-29 | Danmarks Tekniske Universitet | Porous expanding biocompatible scaffolds |
| TW202417488A (zh) | 2022-08-23 | 2024-05-01 | 日商小野藥品工業股份有限公司 | 雙特異性抗體 |
| CN116283896B (zh) * | 2022-09-07 | 2024-10-29 | 广东晨康生物科技有限公司 | 一种具有pd-l1抑制活性的联苯类化合物及其用途 |
| CN115417870B (zh) * | 2022-09-20 | 2024-02-27 | 中国药科大学 | Pd-l1＆nampt双靶点抑制剂和用途 |
| CN115477609B (zh) * | 2022-09-26 | 2024-03-12 | 浙江师范大学 | 基于疏水标签技术的pd-l1蛋白降解剂及其应用 |
| WO2024088036A1 (zh) * | 2022-10-26 | 2024-05-02 | 西安新通药物研究股份有限公司 | 一种非对称性联苯衍生物及其制备方法与医药用途 |
| EP4556465A4 (en) * | 2022-11-22 | 2025-10-29 | Xian Xintong Pharmaceutical Res Co Ltd | NEW BICYCLIC PD-L1 INHIBITORS, THEIR PREPARATION PROCESSES AND MEDICINAL USES |
| TW202430180A (zh) | 2022-11-30 | 2024-08-01 | 瑞士商愛杜西亞製藥有限公司 | 作為ccr8調節劑之芳基-及雜芳基-磺醯胺衍生物 |
| TW202440565A (zh) | 2022-12-06 | 2024-10-16 | 瑞士商愛杜西亞製藥有限公司 | 結晶鹽形式 |
| EP4638503A1 (en) | 2022-12-21 | 2025-10-29 | Bristol-Myers Squibb Company | Combination therapy for lung cancer |
| WO2024186917A2 (en) * | 2023-03-06 | 2024-09-12 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Compositions for pd-l1 inhibition and methods of use thereof |
| WO2024183756A1 (zh) * | 2023-03-07 | 2024-09-12 | 上海再极医药科技有限公司 | 一种含苯环类化合物及其制备方法和应用 |
| WO2024196952A1 (en) | 2023-03-20 | 2024-09-26 | Bristol-Myers Squibb Company | Tumor subtype assessment for cancer therapy |
| GB202318675D0 (en) | 2023-12-06 | 2024-01-17 | Oncopeptides Ab | Novel polypeptides |
| WO2025159640A1 (en) | 2024-01-24 | 2025-07-31 | Agendia N.V. | Method for assessing a risk of breast cancer recurrence |
| WO2025198469A1 (en) | 2024-03-18 | 2025-09-25 | Agendia N.V. | Prediction of response to immune therapy in triple negative breast cancer patients. |
| CN117986158A (zh) * | 2024-04-03 | 2024-05-07 | 云南大学 | 取代联苯类化合物、制备方法及应用 |
| WO2025229177A1 (en) | 2024-05-02 | 2025-11-06 | Idorsia Pharmaceuticals Ltd | Crystalline forms of an n-substituted indole derivative |
| WO2025240244A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies comprising bulevirtide and lonafarnib for use in the treatment of hepatitis d virus infection |
| WO2025240243A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with bulevirtide and an inhibitory nucleic acid targeting hepatitis b virus |
| WO2025240246A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| WO2025240242A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| WO2025245489A1 (en) | 2024-05-24 | 2025-11-27 | Bristol-Myers Squibb Company | Treatment of tumors in subjects having fgl-1 positive samples |
| WO2025261989A1 (en) | 2024-06-18 | 2025-12-26 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | 1,2,3-TRIAZOLE DERIVATIVES AS IL4i1 INHIBITORS |
| CN119350185A (zh) * | 2024-10-08 | 2025-01-24 | 聊城大学 | 一种联苯羟肟类衍生物及其制备方法和用途 |
| CN119350297B (zh) * | 2024-12-25 | 2025-04-04 | 浙江大学 | 一种特异性溶酶体靶向嵌合体分子及其制备方法和应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994018167A1 (fr) * | 1993-02-01 | 1994-08-18 | Kaken Pharmaceutical Co., Ltd. | Derive de dibenzylamine substitue |
| US6297239B1 (en) * | 1997-10-08 | 2001-10-02 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| JP4705756B2 (ja) | 2002-02-07 | 2011-06-22 | 仁 遠藤 | 芳香族アミノ酸誘導体及び医薬組成物 |
| JPWO2004007439A1 (ja) * | 2002-07-10 | 2005-11-10 | 住友製薬株式会社 | ビアリール誘導体 |
| CA2505322A1 (en) | 2002-11-08 | 2004-05-21 | Takeda Pharmaceutical Company Limited | Receptor function regulator |
| TW200815377A (en) | 2006-04-24 | 2008-04-01 | Astellas Pharma Inc | Oxadiazolidinedione compound |
| US9321730B2 (en) * | 2007-08-21 | 2016-04-26 | The Hong Kong Polytechnic University | Method of making and administering quinoline derivatives as anti-cancer agents |
| TW200932219A (en) | 2007-10-24 | 2009-08-01 | Astellas Pharma Inc | Oxadiazolidinedione compound |
| WO2010059838A2 (en) * | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Pde4 inhibitors selective for the long form of pde4 for treating inflammation and avoiding side effects |
| WO2011082400A2 (en) * | 2010-01-04 | 2011-07-07 | President And Fellows Of Harvard College | Modulators of immunoinhibitory receptor pd-1, and methods of use thereof |
| US9850225B2 (en) | 2014-04-14 | 2017-12-26 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| US10745382B2 (en) | 2015-10-15 | 2020-08-18 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
-
2014
- 2014-09-02 CN CN201480060895.6A patent/CN105705489B/zh not_active Expired - Fee Related
- 2014-09-02 EP EP14766086.4A patent/EP3041822B1/en not_active Not-in-force
- 2014-09-02 US US14/915,782 patent/US9872852B2/en active Active
- 2014-09-02 WO PCT/US2014/053695 patent/WO2015034820A1/en not_active Ceased
- 2014-09-02 ES ES14766086.4T patent/ES2642074T3/es active Active
- 2014-09-02 EA EA201690316A patent/EA029901B1/ru not_active IP Right Cessation
- 2014-09-02 BR BR112016004194A patent/BR112016004194A8/pt not_active Application Discontinuation
- 2014-09-02 SG SG11201601225RA patent/SG11201601225RA/en unknown
- 2014-09-02 AU AU2014315457A patent/AU2014315457B2/en not_active Ceased
- 2014-09-02 KR KR1020167008405A patent/KR102276644B1/ko not_active Expired - Fee Related
- 2014-09-02 MX MX2016002544A patent/MX2016002544A/es unknown
- 2014-09-02 JP JP2016540311A patent/JP6417419B2/ja not_active Expired - Fee Related
- 2014-09-02 PE PE2016000338A patent/PE20160432A1/es not_active Application Discontinuation
- 2014-09-02 CA CA2923184A patent/CA2923184A1/en not_active Abandoned
-
2016
- 2016-02-29 IL IL24434616A patent/IL244346B/en not_active IP Right Cessation
- 2016-03-04 CL CL2016000508A patent/CL2016000508A1/es unknown
-
2018
- 2018-01-18 CL CL2018000150A patent/CL2018000150A1/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016536333A5 (https=) | ||
| RU2506257C2 (ru) | Замещенные пирролидин-2-карбоксамиды | |
| RU2011127232A (ru) | Апоптоз-индуцирующие средства для лечения рака и иммунных и аутоиммунных заболеваний | |
| JP2017510555A5 (https=) | ||
| RU2013133800A (ru) | Селективные к bcl-2 агенты, вызывающие апоптоз, для лечения рака и иммунных заболеваний | |
| JP2025016684A5 (https=) | ||
| CA2487489A1 (en) | Mitotic kinesin inhibitors | |
| RU2012127790A (ru) | Индуцирующие апоптоз агенты для лечения рака и иммунных и аутоиммунных заболеваний | |
| JP2019525941A5 (https=) | ||
| RU2010106974A (ru) | Ариловые эфиры пирролидина в качестве антагонистов рецепторов nk3 | |
| JP2013510876A5 (https=) | ||
| JP2013512899A5 (https=) | ||
| JP2018534282A5 (https=) | ||
| RU2014108140A (ru) | Соединение на основе хинозолина в качестве ингибиторов серен-треониновых киназ | |
| JP2014510708A5 (https=) | ||
| RU2013157374A (ru) | Производное индазола и пирролопиридина и его фармацевтическое применение | |
| JP2015504093A5 (https=) | ||
| JP2018520201A5 (https=) | ||
| RU2008126391A (ru) | Производные 1,5-замещенного индол-2-иламида | |
| JP2014531436A5 (https=) | ||
| JP2018515489A5 (https=) | ||
| JP2016514709A5 (https=) | ||
| RU2015144485A (ru) | Геминально-замещенные цианоэтилпиразолопиридоны в качестве ингибиторов janus киназ | |
| JP2009504664A5 (https=) | ||
| US9226916B2 (en) | Pyrrolidine derivatives |