JP2020504766A5 - - Google Patents
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- JP2020504766A5 JP2020504766A5 JP2019554486A JP2019554486A JP2020504766A5 JP 2020504766 A5 JP2020504766 A5 JP 2020504766A5 JP 2019554486 A JP2019554486 A JP 2019554486A JP 2019554486 A JP2019554486 A JP 2019554486A JP 2020504766 A5 JP2020504766 A5 JP 2020504766A5
- Authority
- JP
- Japan
- Prior art keywords
- benzyl
- methyl
- oxy
- chloro
- oxazole
- 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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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 52
- -1 cyano, formyl Chemical group 0.000 claims 49
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims 23
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 4
- 125000005605 benzo group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 230000002708 enhancing effect Effects 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Chemical group 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 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 1
- 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 1
- LCPBGYNRWJBHPD-BHVANESWSA-N (2S)-1-[[4-[[3-[2-[1-(carboxymethyl)piperidin-4-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 C(=O)(O)CN1CCC(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 LCPBGYNRWJBHPD-BHVANESWSA-N 0.000 claims 1
- 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 1
- IOIOJFKMYGBHGF-LHEWISCISA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-(1-propan-2-ylpiperidin-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)C)C=1)C IOIOJFKMYGBHGF-LHEWISCISA-N 0.000 claims 1
- 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 1
- 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 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- AQDIORAYAFJBDK-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-1,3-benzoxazole Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2O1 AQDIORAYAFJBDK-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 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 1
- 102000008096 B7-H1 Antigen Human genes 0.000 claims 1
- 108010074708 B7-H1 Antigen Proteins 0.000 claims 1
- 101000914484 Homo sapiens T-lymphocyte activation antigen CD80 Proteins 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 102100027222 T-lymphocyte activation antigen CD80 Human genes 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 230000028993 immune response Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 230000004936 stimulating effect Effects 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662436674P | 2016-12-20 | 2016-12-20 | |
| US62/436,674 | 2016-12-20 | ||
| PCT/US2017/067198 WO2018118848A1 (en) | 2016-12-20 | 2017-12-19 | Compounds useful as immunomodulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020504766A JP2020504766A (ja) | 2020-02-13 |
| JP2020504766A5 true JP2020504766A5 (cg-RX-API-DMAC7.html) | 2021-01-28 |
| JP7106572B2 JP7106572B2 (ja) | 2022-07-26 |
Family
ID=60972418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019554486A Active JP7106572B2 (ja) | 2016-12-20 | 2017-12-19 | 免疫調節剤として有用な化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10882844B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3558970B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP7106572B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102599339B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN110072860B (cg-RX-API-DMAC7.html) |
| ES (1) | ES2891528T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2018118848A1 (cg-RX-API-DMAC7.html) |
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2017
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- 2017-12-19 WO PCT/US2017/067198 patent/WO2018118848A1/en not_active Ceased
- 2017-12-19 ES ES17829456T patent/ES2891528T3/es active Active
- 2017-12-19 JP JP2019554486A patent/JP7106572B2/ja active Active
- 2017-12-19 EP EP17829456.7A patent/EP3558970B1/en active Active
- 2017-12-19 CN CN201780079156.5A patent/CN110072860B/zh active Active
- 2017-12-19 US US16/471,531 patent/US10882844B2/en active Active
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