ES2891528T3 - Compuestos útiles como inmunomoduladores - Google Patents
Compuestos útiles como inmunomoduladores Download PDFInfo
- Publication number
- ES2891528T3 ES2891528T3 ES17829456T ES17829456T ES2891528T3 ES 2891528 T3 ES2891528 T3 ES 2891528T3 ES 17829456 T ES17829456 T ES 17829456T ES 17829456 T ES17829456 T ES 17829456T ES 2891528 T3 ES2891528 T3 ES 2891528T3
- Authority
- ES
- Spain
- Prior art keywords
- benzyl
- methyl
- oxy
- chloro
- benzo
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 131
- 239000002955 immunomodulating agent Substances 0.000 title description 2
- 229940121354 immunomodulator Drugs 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 75
- -1 cyano, formyl Chemical group 0.000 claims abstract description 56
- 239000001257 hydrogen Substances 0.000 claims abstract description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 31
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 30
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 125000005843 halogen group Chemical group 0.000 claims abstract description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 14
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 11
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 10
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 229910052760 oxygen Chemical group 0.000 claims abstract description 6
- 239000001301 oxygen Chemical group 0.000 claims abstract description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 5
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000003368 amide group Chemical group 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 76
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 52
- 239000002253 acid Substances 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 18
- 201000011510 cancer Diseases 0.000 claims description 17
- 125000005605 benzo group Chemical group 0.000 claims description 16
- 230000028993 immune response Effects 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims description 14
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims description 14
- 208000015181 infectious disease Diseases 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 241000700605 Viruses Species 0.000 claims description 11
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 208000035473 Communicable disease Diseases 0.000 claims description 8
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 7
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 230000012010 growth Effects 0.000 claims description 7
- 230000001965 increasing effect Effects 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
- 206010040070 Septic Shock Diseases 0.000 claims description 5
- 230000036303 septic shock Effects 0.000 claims description 5
- XTWVJNQUBVYXMF-UHFFFAOYSA-N 5-[[4-chloro-2-formyl-5-[[2-methyl-3-[2-(1-methylpiperidin-4-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CCN(CC2)C)C=1)C)C=O XTWVJNQUBVYXMF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 230000035755 proliferation Effects 0.000 claims description 3
- RFFNGZCDGSQVPC-AOYODBLASA-N (2S)-1-[[4-[[3-[2-(3-amino-1-bicyclo[1.1.1]pentanyl)-1,3-benzoxazol-5-yl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound Cc1c(COc2cc(OCc3cncc(c3)C#N)c(CN3CCCC[C@H]3C(O)=O)cc2Cl)cccc1-c1ccc2oc(nc2c1)C12CC(N)(C1)C2 RFFNGZCDGSQVPC-AOYODBLASA-N 0.000 claims description 2
- NNNALYKWNJLNNL-DHMSSXBRSA-N (2S)-1-[[4-[[3-[2-(4-carboxycyclohexyl)-1,3-benzoxazol-5-yl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)C1CCC(CC1)C=1OC2=C(N=1)C=C(C=C2)C=1C(=C(COC2=CC(=C(CN3[C@@H](CCCC3)C(=O)O)C=C2Cl)OCC=2C=NC=C(C=2)C#N)C=CC=1)C NNNALYKWNJLNNL-DHMSSXBRSA-N 0.000 claims description 2
- APDFJOANMZAJSH-XHNMUALFSA-N (2S)-1-[[4-[[3-[2-(8-azabicyclo[3.2.1]octan-3-yl)-1,3-benzoxazol-5-yl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C12CC(CC(CC1)N2)C=1OC2=C(N=1)C=C(C=C2)C=1C(=C(COC2=CC(=C(CN3[C@@H](CCCC3)C(=O)O)C=C2Cl)OCC=2C=NC=C(C=2)C#N)C=CC=1)C APDFJOANMZAJSH-XHNMUALFSA-N 0.000 claims description 2
- SZLIUHMLWHFJOR-VCWBJQSESA-N (2S)-1-[[4-[[3-[3-(8-azabicyclo[3.2.1]oct-2-en-3-yl)quinoxalin-6-yl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C12C=C(CC(CC1)N2)C=1C=NC2=CC=C(C=C2N=1)C=1C(=C(COC2=CC(=C(CN3[C@@H](CCCC3)C(=O)O)C=C2Cl)OCC=2C=NC=C(C=2)C#N)C=CC=1)C SZLIUHMLWHFJOR-VCWBJQSESA-N 0.000 claims description 2
- YMDCOTOPCUHBGY-IYBQEVONSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-(1-methylpiperidin-3-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CN(CCC2)C)C=1)C YMDCOTOPCUHBGY-IYBQEVONSA-N 0.000 claims description 2
- PRYLNBSTWUYPNJ-BHVANESWSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-(1-methylpiperidin-4-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CCN(CC2)C)C=1)C PRYLNBSTWUYPNJ-BHVANESWSA-N 0.000 claims description 2
- JTAKSSCPIVUIIH-BHVANESWSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-(1-methylpiperidin-4-yl)-1,3-benzoxazol-6-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(N=C(O2)C2CCN(CC2)C)C=C1)C JTAKSSCPIVUIIH-BHVANESWSA-N 0.000 claims description 2
- NNYHBMWJWIMLLK-KEPYVBBOSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-(1-methylpyrrolidin-3-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CN(CC2)C)C=1)C NNYHBMWJWIMLLK-KEPYVBBOSA-N 0.000 claims description 2
- VMKQKGDQXROCPJ-RWYGWLOXSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-(1-phenylpiperidin-4-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CCN(CC2)C2=CC=CC=C2)C=1)C VMKQKGDQXROCPJ-RWYGWLOXSA-N 0.000 claims description 2
- CJMCRTHWPOQROF-DHUJRADRSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-(4-methylpiperazin-1-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)N2CCN(CC2)C)C=1)C CJMCRTHWPOQROF-DHUJRADRSA-N 0.000 claims description 2
- VTBVMMIMWXWNHB-APXLDGQGSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CC3CCC(C2)N3C)C=1)C VTBVMMIMWXWNHB-APXLDGQGSA-N 0.000 claims description 2
- YZZZQJDDXDSCSF-XHNMUALFSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-(8-oxabicyclo[3.2.1]octan-3-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C12CC(CC(CC1)O2)C=1OC2=C(N=1)C=C(C=C2)C=1C(=C(COC2=CC(=C(CN3[C@@H](CCCC3)C(=O)O)C=C2Cl)OCC=2C=NC=C(C=2)C#N)C=CC=1)C YZZZQJDDXDSCSF-XHNMUALFSA-N 0.000 claims description 2
- FGEKRZYVQDOSRU-QOVAEWSBSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)N2[C@@H]3CN([C@H](C2)C3)C)C=1)C FGEKRZYVQDOSRU-QOVAEWSBSA-N 0.000 claims description 2
- IPVNDSHCCLSORR-BHVANESWSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[4-methyl-2-(1-methylpiperidin-4-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CCN(CC2)C)C=1C)C IPVNDSHCCLSORR-BHVANESWSA-N 0.000 claims description 2
- FXOBLIWBGUCVNN-QNGWXLTQSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[7-methyl-2-(1-methylpiperidin-4-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=C(C2=C(N=C(O2)C2CCN(CC2)C)C=1)C)C FXOBLIWBGUCVNN-QNGWXLTQSA-N 0.000 claims description 2
- JTNPCCAJVWEZHN-CNZQJSNXSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[2-(4-methoxycarbonylcyclohexyl)-1,3-benzoxazol-5-yl]-2-methylphenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CCC(CC2)C(=O)OC)C=1)C JTNPCCAJVWEZHN-CNZQJSNXSA-N 0.000 claims description 2
- ITJMWTVBSFFWRB-DHUJRADRSA-N (2S)-1-[[5-chloro-2-methoxy-4-[[2-methyl-3-[2-(1-phenylpiperidin-4-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OC)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CCN(CC2)C2=CC=CC=C2)C=1)C ITJMWTVBSFFWRB-DHUJRADRSA-N 0.000 claims description 2
- FZMZPRFVHFUXML-UHFFFAOYSA-N 5-[[4-chloro-2-(hydroxymethyl)-5-[[2-methyl-3-[2-(1-methylpiperidin-4-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CCN(CC2)C)C=1)C)CO FZMZPRFVHFUXML-UHFFFAOYSA-N 0.000 claims description 2
- ZCNMMMGYQIGBBA-UHFFFAOYSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[2-methyl-3-[2-(4-methylpiperazin-1-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)N2CCN(CC2)C)C=1)C)CNC(CO)CO ZCNMMMGYQIGBBA-UHFFFAOYSA-N 0.000 claims description 2
- GUYHISWJRSVFST-UHFFFAOYSA-N 5-[[4-chloro-2-[[(1,3-dihydroxy-2-methylpropan-2-yl)-methylamino]methyl]-5-[[2-methyl-3-[2-(4-methylpiperazin-1-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)N2CCN(CC2)C)C=1)C)CN(C)C(CO)(CO)C GUYHISWJRSVFST-UHFFFAOYSA-N 0.000 claims description 2
- XLQNLUVSDVJPJN-UHFFFAOYSA-N 5-[[4-chloro-2-[[(1,3-dihydroxy-2-methylpropan-2-yl)amino]methyl]-5-[[2-methyl-3-[2-(4-methylpiperazin-1-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)N2CCN(CC2)C)C=1)C)CNC(CO)(CO)C XLQNLUVSDVJPJN-UHFFFAOYSA-N 0.000 claims description 2
- CRXWYBOGQDHONW-UHFFFAOYSA-N 5-[[4-chloro-2-[[1,3-dihydroxypropan-2-yl(methyl)amino]methyl]-5-[[2-methyl-3-[2-(4-methylpiperazin-1-yl)-1,3-benzoxazol-5-yl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)N2CCN(CC2)C)C=1)C)CN(C)C(CO)CO CRXWYBOGQDHONW-UHFFFAOYSA-N 0.000 claims description 2
- BIGHFDXMARSQIL-KYJUHHDHSA-N 5-[[4-chloro-5-[[3-[2-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,3-benzoxazol-5-yl]-2-methylphenyl]methoxy]-2-[[(1,3-dihydroxy-2-methylpropan-2-yl)amino]methyl]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound CC1=C(C=CC=C1C2=CC3=C(C=C2)OC(=N3)N4C[C@@H]5C[C@H]4CN5)COC6=C(C=C(C(=C6)OCC7=CC(=CN=C7)C#N)CNC(C)(CO)CO)Cl BIGHFDXMARSQIL-KYJUHHDHSA-N 0.000 claims description 2
- 206010027476 Metastases Diseases 0.000 claims description 2
- 230000009401 metastasis Effects 0.000 claims description 2
- 230000004936 stimulating effect Effects 0.000 claims description 2
- DIRZDIHMAJEZQX-DHUJRADRSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-(2-piperidin-4-yl-1,3-benzoxazol-5-yl)phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)C2CCNCC2)C=1)C DIRZDIHMAJEZQX-DHUJRADRSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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| AU2017292758A1 (en) | 2016-07-08 | 2019-02-21 | Bristol-Myers Squibb Company | 1,3-dihydroxy-phenyl derivatives useful as immunomodulators |
| US10144706B2 (en) | 2016-09-01 | 2018-12-04 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| KR20190133714A (ko) | 2017-03-27 | 2019-12-03 | 브리스톨-마이어스 스큅 컴퍼니 | 면역조정제로서 유용한 치환된 이소퀴놀린 유도체 |
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2017
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- 2017-12-19 JP JP2019554486A patent/JP7106572B2/ja active Active
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| KR20190092565A (ko) | 2019-08-07 |
| CN110072860B (zh) | 2022-09-02 |
| KR102599339B1 (ko) | 2023-11-08 |
| US10882844B2 (en) | 2021-01-05 |
| WO2018118848A1 (en) | 2018-06-28 |
| US20190352280A1 (en) | 2019-11-21 |
| JP2020504766A (ja) | 2020-02-13 |
| JP7106572B2 (ja) | 2022-07-26 |
| CN110072860A (zh) | 2019-07-30 |
| EP3558970A1 (en) | 2019-10-30 |
| EP3558970B1 (en) | 2021-09-01 |
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