WO2015034820A1 - Compounds useful as immunomodulators - Google Patents
Compounds useful as immunomodulators Download PDFInfo
- Publication number
- WO2015034820A1 WO2015034820A1 PCT/US2014/053695 US2014053695W WO2015034820A1 WO 2015034820 A1 WO2015034820 A1 WO 2015034820A1 US 2014053695 W US2014053695 W US 2014053695W WO 2015034820 A1 WO2015034820 A1 WO 2015034820A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- methoxy
- phenylphenyl
- phenyl
- amino
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 234
- 239000002955 immunomodulating agent Substances 0.000 title abstract 2
- 229940121354 immunomodulator Drugs 0.000 title abstract 2
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 81
- 238000000034 method Methods 0.000 claims abstract description 68
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 201000011510 cancer Diseases 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 19
- 208000035475 disorder Diseases 0.000 claims abstract description 7
- 230000003612 virological effect Effects 0.000 claims abstract description 5
- -1 and Rz is -OH Chemical group 0.000 claims description 183
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 87
- 150000003839 salts Chemical class 0.000 claims description 81
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 78
- 239000004305 biphenyl Substances 0.000 claims description 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- 150000001412 amines Chemical class 0.000 claims description 28
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims description 25
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 23
- 125000002757 morpholinyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
- 230000003993 interaction Effects 0.000 claims description 13
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003937 drug carrier Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 208000015181 infectious disease Diseases 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- ZBOYJODMIAUJHH-SANMLTNESA-N (2s)-1-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C=1C(OC)=C(CN2[C@@H](CCCC2)C(O)=O)C(OC)=CC=1OCC(C=1C)=CC=CC=1C1=CC=CC=C1 ZBOYJODMIAUJHH-SANMLTNESA-N 0.000 claims description 8
- NIVJEFTUALCIHL-HSZRJFAPSA-N (5R)-5-[[[4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1=CC(=CC=C1)C1=C(C)C(COC2=CC=C(CNC[C@@H]3NC(=O)CC3)C=C2)=CC=C1 NIVJEFTUALCIHL-HSZRJFAPSA-N 0.000 claims description 8
- 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 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- MDXBUGFUIORMCC-UHFFFAOYSA-N COc1cc(OCc2cccc(c2C)-c2ccccc2)c(Br)c(OC)c1CNCCNC(C)=O Chemical compound COc1cc(OCc2cccc(c2C)-c2ccccc2)c(Br)c(OC)c1CNCCNC(C)=O MDXBUGFUIORMCC-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 235000019260 propionic acid Nutrition 0.000 claims description 7
- 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 description 6
- 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 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 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 description 5
- 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 description 5
- GBADJQGJTQQHGC-UHFFFAOYSA-N 2-methyl-1-(4-methylpiperazin-1-yl)propan-2-amine Chemical compound CN1CCN(CC(C)(C)N)CC1 GBADJQGJTQQHGC-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 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 description 4
- 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 description 4
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- MVYOGUBAUCKKAM-UHFFFAOYSA-N COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN1CCC1 Chemical compound COC1=C(C(=CC(=C1)OCC1=C(C(=CC=C1)C1=CC=CC=C1)C)OC)CN1CCC1 MVYOGUBAUCKKAM-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
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Abstract
Description
Claims
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
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CA2923184A CA2923184A1 (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators |
JP2016540311A JP6417419B2 (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators |
CN201480060895.6A CN105705489B (en) | 2013-09-04 | 2014-09-02 | Compound as immunomodulator |
BR112016004194A BR112016004194A8 (en) | 2013-09-04 | 2014-09-02 | compounds useful as immunomodulators |
AU2014315457A AU2014315457B2 (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators |
MX2016002544A MX2016002544A (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators. |
EP14766086.4A EP3041822B1 (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators |
US14/915,782 US9872852B2 (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators |
SG11201601225RA SG11201601225RA (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators |
ES14766086.4T ES2642074T3 (en) | 2013-09-04 | 2014-09-02 | Useful compounds as immunomodulators |
KR1020167008405A KR102276644B1 (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators |
EA201690316A EA029901B1 (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators |
IL24434616A IL244346B (en) | 2013-09-04 | 2016-02-29 | Compounds useful as immunomodulators |
HK16111624.3A HK1223366A1 (en) | 2013-09-04 | 2016-10-06 | Compounds useful as immunomodulators |
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US201361873398P | 2013-09-04 | 2013-09-04 | |
US61/873,398 | 2013-09-04 |
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PCT/US2014/053695 WO2015034820A1 (en) | 2013-09-04 | 2014-09-02 | Compounds useful as immunomodulators |
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US (1) | US9872852B2 (en) |
EP (1) | EP3041822B1 (en) |
JP (1) | JP6417419B2 (en) |
KR (1) | KR102276644B1 (en) |
CN (1) | CN105705489B (en) |
AU (1) | AU2014315457B2 (en) |
BR (1) | BR112016004194A8 (en) |
CA (1) | CA2923184A1 (en) |
CL (2) | CL2016000508A1 (en) |
EA (1) | EA029901B1 (en) |
ES (1) | ES2642074T3 (en) |
HK (1) | HK1223366A1 (en) |
IL (1) | IL244346B (en) |
MX (1) | MX2016002544A (en) |
PE (1) | PE20160432A1 (en) |
SG (1) | SG11201601225RA (en) |
WO (1) | WO2015034820A1 (en) |
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AU2014315457B2 (en) | 2018-05-10 |
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BR112016004194A8 (en) | 2020-02-11 |
KR102276644B1 (en) | 2021-07-13 |
CN105705489B (en) | 2019-04-26 |
HK1223366A1 (en) | 2017-07-28 |
SG11201601225RA (en) | 2016-03-30 |
CL2018000150A1 (en) | 2018-05-11 |
EP3041822B1 (en) | 2017-08-09 |
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US20160194307A1 (en) | 2016-07-07 |
KR20160048946A (en) | 2016-05-04 |
JP2016536333A (en) | 2016-11-24 |
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AU2014315457A1 (en) | 2016-04-28 |
US9872852B2 (en) | 2018-01-23 |
EP3041822A1 (en) | 2016-07-13 |
CL2016000508A1 (en) | 2016-11-04 |
CN105705489A (en) | 2016-06-22 |
JP6417419B2 (en) | 2018-11-07 |
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