JP2016536333A5 - - Google Patents
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- 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
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- -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
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2014
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- 2014-09-02 PE PE2016000338A patent/PE20160432A1/es not_active Application Discontinuation
- 2014-09-02 JP JP2016540311A patent/JP6417419B2/ja not_active Expired - Fee Related
- 2014-09-02 BR BR112016004194A patent/BR112016004194A8/pt not_active Application Discontinuation
- 2014-09-02 KR KR1020167008405A patent/KR102276644B1/ko not_active Expired - Fee Related
- 2014-09-02 CA CA2923184A patent/CA2923184A1/en not_active Abandoned
- 2014-09-02 WO PCT/US2014/053695 patent/WO2015034820A1/en not_active Ceased
- 2014-09-02 AU AU2014315457A patent/AU2014315457B2/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 EP EP14766086.4A patent/EP3041822B1/en not_active Not-in-force
- 2014-09-02 CN CN201480060895.6A patent/CN105705489B/zh not_active Expired - Fee Related
- 2014-09-02 US US14/915,782 patent/US9872852B2/en active Active
- 2014-09-02 SG SG11201601225RA patent/SG11201601225RA/en unknown
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2016
- 2016-02-29 IL IL24434616A patent/IL244346B/en not_active IP Right Cessation
- 2016-03-04 CL CL2016000508A patent/CL2016000508A1/es unknown
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2018
- 2018-01-18 CL CL2018000150A patent/CL2018000150A1/es unknown
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