AU2016338874A1 - Compounds useful as immunomodulators - Google Patents
Compounds useful as immunomodulators Download PDFInfo
- Publication number
- AU2016338874A1 AU2016338874A1 AU2016338874A AU2016338874A AU2016338874A1 AU 2016338874 A1 AU2016338874 A1 AU 2016338874A1 AU 2016338874 A AU2016338874 A AU 2016338874A AU 2016338874 A AU2016338874 A AU 2016338874A AU 2016338874 A1 AU2016338874 A1 AU 2016338874A1
- Authority
- AU
- Australia
- Prior art keywords
- methoxy
- chloro
- methyl
- biphenyl
- propoxy
- 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.)
- Abandoned
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- 150000001875 compounds Chemical class 0.000 title claims abstract 28
- 239000002955 immunomodulating agent Substances 0.000 title claims abstract 3
- 229940121354 immunomodulator Drugs 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 claims abstract description 43
- 208000035473 Communicable disease Diseases 0.000 claims abstract 3
- 206010028980 Neoplasm Diseases 0.000 claims abstract 3
- 201000011510 cancer Diseases 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 239000004305 biphenyl Substances 0.000 claims description 488
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 271
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 237
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 225
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 180
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 138
- -1 -CLb Chemical group 0.000 claims description 135
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 125
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims description 105
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims description 104
- 235000010290 biphenyl Nutrition 0.000 claims description 90
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 73
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- IADUEWIQBXOCDZ-UHFFFAOYSA-N azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 claims description 4
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- IADUEWIQBXOCDZ-VKHMYHEASA-N Azetidine-2-carboxylic acid Natural products OC(=O)[C@@H]1CCN1 IADUEWIQBXOCDZ-VKHMYHEASA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 48
- 239000001257 hydrogen Substances 0.000 claims 48
- 150000002431 hydrogen Chemical group 0.000 claims 28
- 125000005843 halogen group Chemical group 0.000 claims 27
- 150000003839 salts Chemical class 0.000 claims 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000003368 amide group Chemical group 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- DBXBTMSZEOQQDU-UHFFFAOYSA-N 3-hydroxyisobutyric acid Chemical compound OCC(C)C(O)=O DBXBTMSZEOQQDU-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- JUNOWSHJELIDQP-UHFFFAOYSA-N morpholin-4-ium-3-carboxylate Chemical compound OC(=O)C1COCCN1 JUNOWSHJELIDQP-UHFFFAOYSA-N 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 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
- 235000019260 propionic acid Nutrition 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical compound OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N 4-hydroxyproline Chemical compound OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims 2
- OJAADWOGFSLPLH-WDYNHAJCSA-N 5-[[4-chloro-5-[[2-chloro-3-[2-chloro-3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]phenyl]phenyl]methoxy]-2-[[[(2S)-2,3-dihydroxypropyl]amino]methyl]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)Cl)Cl)CNC[C@@H](CO)O OJAADWOGFSLPLH-WDYNHAJCSA-N 0.000 claims 2
- VUVWUBKUDHAFSA-NSOVKSMOSA-N 5-[[4-chloro-5-[[2-chloro-3-[2-chloro-3-[3-[[(2S)-2,3-dihydroxypropyl]amino]propoxy]phenyl]phenyl]methoxy]-2-[[[(2S)-2,3-dihydroxypropyl]amino]methyl]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNC[C@@H](CO)O)Cl)Cl)CNC[C@@H](CO)O VUVWUBKUDHAFSA-NSOVKSMOSA-N 0.000 claims 2
- HXNNRBHASOSVPG-GUBZILKMSA-N Ala-Glu-Leu Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(O)=O HXNNRBHASOSVPG-GUBZILKMSA-N 0.000 claims 2
- 241000282414 Homo sapiens Species 0.000 claims 2
- YBAFDPFAUTYYRW-UHFFFAOYSA-N N-L-alpha-glutamyl-L-leucine Natural products CC(C)CC(C(O)=O)NC(=O)C(N)CCC(O)=O YBAFDPFAUTYYRW-UHFFFAOYSA-N 0.000 claims 2
- SITLTJHOQZFJGG-UHFFFAOYSA-N N-L-alpha-glutamyl-L-valine Natural products CC(C)C(C(O)=O)NC(=O)C(N)CCC(O)=O SITLTJHOQZFJGG-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- IHCXPSYCHXFXKT-DCAQKATOSA-N Pro-Arg-Glu Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O IHCXPSYCHXFXKT-DCAQKATOSA-N 0.000 claims 2
- FDMKYQQYJKYCLV-GUBZILKMSA-N Pro-Pro-Ser Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1NCCC1 FDMKYQQYJKYCLV-GUBZILKMSA-N 0.000 claims 2
- RHAPJNVNWDBFQI-BQBZGAKWSA-N Ser-Pro-Gly Chemical compound OC[C@H](N)C(=O)N1CCC[C@H]1C(=O)NCC(O)=O RHAPJNVNWDBFQI-BQBZGAKWSA-N 0.000 claims 2
- 241000700605 Viruses Species 0.000 claims 2
- 108010087924 alanylproline Proteins 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 108010092854 aspartyllysine Proteins 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 108010078144 glutaminyl-glycine Proteins 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 108010077112 prolyl-proline Proteins 0.000 claims 2
- 108010031719 prolyl-serine Proteins 0.000 claims 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 2
- 108010026333 seryl-proline Proteins 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- LCTSZQLRZRZQHG-WXUYMIOXSA-N (2R)-2-[[4-[[3-[3-[[(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methylamino]-3-hydroxypropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@H](C(=O)O)CO)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OC[C@@H]1CCCN2CCCC[C@H]12)C)C LCTSZQLRZRZQHG-WXUYMIOXSA-N 0.000 claims 1
- QVTPURFKWDNZNE-RYCFQHDISA-N (2R)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[2-[(3S)-3-hydroxypyrrolidin-1-yl]-2-oxoethoxy]phenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxypropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@H](C(=O)O)CO)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCC(=O)N1C[C@H](CC1)O)C QVTPURFKWDNZNE-RYCFQHDISA-N 0.000 claims 1
- SMHQPTNZWZREJK-ODYCNIDGSA-N (2R)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(3-hydroxy-3-phenylpyrrolidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(CC1)(C1=CC=CC=C1)O)C)C SMHQPTNZWZREJK-ODYCNIDGSA-N 0.000 claims 1
- IFPLNSCZTCWWOT-UUWRZZSWSA-N (2R)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(3-hydroxyazetidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxypropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@H](C(=O)O)CO)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(C1)O)C)C IFPLNSCZTCWWOT-UUWRZZSWSA-N 0.000 claims 1
- BSIUOHOAFJTSTG-PSXMRANNSA-N (2R)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(4-hydroxy-4-methoxycarbonylpiperidin-1-yl)propoxy]phenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxypropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@H](C(=O)O)CO)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCCCN1CCC(CC1)(C(=O)OC)O)C BSIUOHOAFJTSTG-PSXMRANNSA-N 0.000 claims 1
- XHOCJJIDJHWBSO-VQJSHJPSSA-N (2R)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(4-hydroxypiperidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)O)C)C XHOCJJIDJHWBSO-VQJSHJPSSA-N 0.000 claims 1
- OQXSISXJJCMQMU-PSXMRANNSA-N (2R)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(4-hydroxypiperidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxypropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@H](C(=O)O)CO)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)O)C)C OQXSISXJJCMQMU-PSXMRANNSA-N 0.000 claims 1
- MFVYTOYCNBDLTR-RRHRGVEJSA-N (2R)-2-[[5-chloro-4-[[3-[2-chloro-3-(3-piperidin-1-ylpropoxy)phenyl]-2-methylphenyl]methoxy]-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCCCC1)Cl)C MFVYTOYCNBDLTR-RRHRGVEJSA-N 0.000 claims 1
- DIDCEGQNCOWHOW-OKAAYDHYSA-N (2R)-2-[[5-chloro-4-[[3-[2-chloro-3-[3-[(3R,4R)-4-(4-chlorophenyl)-3,4-dihydroxy-3-methylpiperidin-1-yl]propoxy]phenyl]-2-methylphenyl]methoxy]-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methylamino]-3-hydroxypropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@H](CO)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@]([C@](CC1)(O)C1=CC=C(C=C1)Cl)(C)O)Cl)C DIDCEGQNCOWHOW-OKAAYDHYSA-N 0.000 claims 1
- RJHPQZAUOYLXPF-YDAXCOIMSA-N (2S)-1-[3-[3-[3-[[4-[[(2S)-2-carboxypiperidin-1-yl]methyl]-2-chloro-5-[(5-cyanopyridin-3-yl)methoxy]phenoxy]methyl]-2-methylphenyl]-2-methylphenoxy]propyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)[C@H]1N(CCCC1)CC1=CC(=C(OCC=2C(=C(C=CC=2)C2=C(C(=CC=C2)OCCCN2[C@@H](CCCC2)C(=O)O)C)C)C=C1OCC=1C=NC=C(C=1)C#N)Cl RJHPQZAUOYLXPF-YDAXCOIMSA-N 0.000 claims 1
- BALIPHPNKCLCAW-JJQXXVEZSA-N (2S)-1-[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]benzoyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(C(=O)N2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C BALIPHPNKCLCAW-JJQXXVEZSA-N 0.000 claims 1
- IMWSNNNDZGXKDB-SMRXGSKTSA-N (2S)-1-[[2-[(5-carbamoylpyridin-3-yl)methoxy]-4-[[3-[3-[3-[3-carboxy-3-(hydroxymethyl)pyrrolidin-1-yl]propoxy]-2-chlorophenyl]-2-methylphenyl]methoxy]-5-chlorophenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(N)(=O)C=1C=C(C=NC=1)COC1=C(CN2[C@@H](CCCC2)C(=O)O)C=C(C(=C1)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(CC1)(CO)C(=O)O)Cl)C)Cl IMWSNNNDZGXKDB-SMRXGSKTSA-N 0.000 claims 1
- MHROUOKMFZCXOO-UMSFTDKQSA-N (2S)-1-[[4-[[3-[3-(aziridine-1-carbonyl)-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound N1(CC1)C(=O)C=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C MHROUOKMFZCXOO-UMSFTDKQSA-N 0.000 claims 1
- UNEOUUZDANHSJM-RVFUZGKFSA-N (2S)-1-[[4-[[3-[3-[3-(2-carbamoylpiperidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(N)(=O)C1N(CCCC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C UNEOUUZDANHSJM-RVFUZGKFSA-N 0.000 claims 1
- MMSRSPMCVFPNHD-XGVPZFSMSA-N (2S)-1-[[4-[[3-[3-[3-(3-acetamidopyrrolidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(C)(=O)NC1CN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C MMSRSPMCVFPNHD-XGVPZFSMSA-N 0.000 claims 1
- MGVRBHLMFPSNAO-ULQZDSGLSA-N (2S)-1-[[4-[[3-[3-[3-(3-carbamoylpiperidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(N)(=O)C1CN(CCC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C MGVRBHLMFPSNAO-ULQZDSGLSA-N 0.000 claims 1
- MKCICFRCCDHRCH-KDXMTYKHSA-N (2S)-1-[[4-[[3-[3-[3-(4-carboxypiperidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)C1CCN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C MKCICFRCCDHRCH-KDXMTYKHSA-N 0.000 claims 1
- JPZCGVIIZHLGHG-KBGXGDJFSA-N (2S)-1-[[4-[[3-[3-[3-[(2S,4R)-2-carboxy-4-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)[C@H]1N(C[C@@H](C1)O)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C JPZCGVIIZHLGHG-KBGXGDJFSA-N 0.000 claims 1
- JPZCGVIIZHLGHG-ZWGRPSGYSA-N (2S)-1-[[4-[[3-[3-[3-[(2S,4S)-2-carboxy-4-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)[C@H]1N(C[C@H](C1)O)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C JPZCGVIIZHLGHG-ZWGRPSGYSA-N 0.000 claims 1
- MMSRSPMCVFPNHD-PGSXYRMZSA-N (2S)-1-[[4-[[3-[3-[3-[(3R)-3-acetamidopyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(C)(=O)N[C@H]1CN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C MMSRSPMCVFPNHD-PGSXYRMZSA-N 0.000 claims 1
- OHAWKVICVDCVIK-GDYKHXCGSA-N (2S)-1-[[4-[[3-[3-[3-[(3R)-3-carboxypiperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)[C@H]1CN(CCC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C OHAWKVICVDCVIK-GDYKHXCGSA-N 0.000 claims 1
- VNAFJIWKABYMFS-YSJGZBICSA-N (2S)-1-[[4-[[3-[3-[3-[(3R)-3-carboxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-methylsulfonylpyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)[C@H]1CN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)S(=O)(=O)C)C)C VNAFJIWKABYMFS-YSJGZBICSA-N 0.000 claims 1
- OHAWKVICVDCVIK-AJCPBJRWSA-N (2S)-1-[[4-[[3-[3-[3-[(3S)-3-carboxypiperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)[C@@H]1CN(CCC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C OHAWKVICVDCVIK-AJCPBJRWSA-N 0.000 claims 1
- IUJWKIZOBOUHGU-XGVPZFSMSA-N (2S)-1-[[4-[[3-[3-[3-[2-(carboxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)CC1N(CCCC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C IUJWKIZOBOUHGU-XGVPZFSMSA-N 0.000 claims 1
- BNHMREYDCLOVMV-YATWDLPUSA-N (2S)-1-[[4-[[3-[3-[3-[[(1S)-1-carboxy-2-pyridin-4-ylethyl]amino]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)[C@H](CC1=CC=NC=C1)NCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C BNHMREYDCLOVMV-YATWDLPUSA-N 0.000 claims 1
- CIGGZONISFOWHB-ZPGRZCPFSA-N (2S)-1-[[4-[[3-[3-[3-[[(2S)-2-carboxy-2-hydroxyethyl]amino]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(=O)(O)[C@H](CNCCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C)O CIGGZONISFOWHB-ZPGRZCPFSA-N 0.000 claims 1
- NOBIDEYNKLFIEC-VZWFPNHASA-N (2S)-1-[[5-chloro-2-[(3,4-difluorophenyl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC1=CC(=C(C=C1)F)F)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C NOBIDEYNKLFIEC-VZWFPNHASA-N 0.000 claims 1
- OZEVFSUEYYDYEO-BYYXFNHRSA-N (2S)-1-[[5-chloro-2-[(3,5-difluorophenyl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC1=CC(=CC(=C1)F)F)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C OZEVFSUEYYDYEO-BYYXFNHRSA-N 0.000 claims 1
- BDFHDYNLCAJUCA-LHEWISCISA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-(3-morpholin-4-ylpropoxy)phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCOCC1)C)C BDFHDYNLCAJUCA-LHEWISCISA-N 0.000 claims 1
- IGVJNRVXOVQREB-KDXMTYKHSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-(3-piperidin-1-ylpropoxy)phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCCCC1)C)C IGVJNRVXOVQREB-KDXMTYKHSA-N 0.000 claims 1
- BIOSAVHNJPXIAE-QNGWXLTQSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-(4-methylpiperazine-1-carbonyl)phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)C(=O)N1CCN(CC1)C)C)C BIOSAVHNJPXIAE-QNGWXLTQSA-N 0.000 claims 1
- VJFHFNCQHDJZLF-BHVANESWSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-(pyrrolidine-1-carbonyl)phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)C(=O)N1CCCC1)C)C VJFHFNCQHDJZLF-BHVANESWSA-N 0.000 claims 1
- NBVPPJKRDBCXMQ-MOVAXLSESA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-(2-methylpiperidin-1-yl)propoxy]phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C(CCCC1)C)C)C NBVPPJKRDBCXMQ-MOVAXLSESA-N 0.000 claims 1
- BOQCHJCGAXGRCT-RWYGWLOXSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-(2-pyridin-2-ylethylamino)propoxy]phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNCCC1=NC=CC=C1)C)C BOQCHJCGAXGRCT-RWYGWLOXSA-N 0.000 claims 1
- TZXGREGZJJUVTG-RWYGWLOXSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-(2-pyridin-4-ylethylamino)propoxy]phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNCCC1=CC=NC=C1)C)C TZXGREGZJJUVTG-RWYGWLOXSA-N 0.000 claims 1
- OWMXWQAILNOUIR-QLKFWGTOSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-(4-morpholin-4-ylpiperidin-1-yl)propoxy]phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)N1CCOCC1)C)C OWMXWQAILNOUIR-QLKFWGTOSA-N 0.000 claims 1
- CQAQLGJCFCDGJA-WBCKFURZSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-(4-pyridin-2-ylpiperazin-1-yl)propoxy]phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCN(CC1)C1=NC=CC=C1)C)C CQAQLGJCFCDGJA-WBCKFURZSA-N 0.000 claims 1
- GVIIELCZPCVLJE-FAIXQHPJSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-[4-(methylamino)piperidin-1-yl]propoxy]phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)NC)C)C GVIIELCZPCVLJE-FAIXQHPJSA-N 0.000 claims 1
- XOVQPDHZNJPVGB-WBCKFURZSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-[4-[2-oxo-2-(propan-2-ylamino)ethyl]piperazin-1-yl]propoxy]phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCN(CC1)CC(=O)NC(C)C)C)C XOVQPDHZNJPVGB-WBCKFURZSA-N 0.000 claims 1
- GSQZIYQFJPODMN-QLKFWGTOSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-[4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]piperidin-1-yl]propoxy]phenyl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(C)(C)(C)OC(=O)N(C1CCN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C)C GSQZIYQFJPODMN-QLKFWGTOSA-N 0.000 claims 1
- KPLBELSFDLGEAH-QLKFWGTOSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-[methyl(2-phenylethyl)amino]propoxy]phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN(CCC1=CC=CC=C1)C)C)C KPLBELSFDLGEAH-QLKFWGTOSA-N 0.000 claims 1
- AXVQVISFVUMSJY-RWYGWLOXSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-[methyl(pyridin-2-ylmethyl)amino]propoxy]phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN(CC1=NC=CC=C1)C)C)C AXVQVISFVUMSJY-RWYGWLOXSA-N 0.000 claims 1
- ZJMRHKKOBIFKPB-RWYGWLOXSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-[methyl(pyridin-3-ylmethyl)amino]propoxy]phenyl]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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN(CC=1C=NC=CC=1)C)C)C ZJMRHKKOBIFKPB-RWYGWLOXSA-N 0.000 claims 1
- RXWADWRKAYZIAZ-BHVANESWSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[3-[3-(prop-2-enoylamino)propoxy]phenyl]phenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C(C=C)(=O)NCCCOC=1C=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C RXWADWRKAYZIAZ-BHVANESWSA-N 0.000 claims 1
- YMLLRVAMQZCDKZ-GOJCVTOHSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[2-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]phenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C=CC=C1)OCCCN1C[C@@H](CC1)O)C YMLLRVAMQZCDKZ-GOJCVTOHSA-N 0.000 claims 1
- ZKUYIALYCLKUMH-YVQIVWGDSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[(E)-4-[(3R)-3-hydroxypyrrolidin-1-yl]but-2-enoxy]phenyl]-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)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OC\C=C\CN1C[C@@H](CC1)O)C ZKUYIALYCLKUMH-YVQIVWGDSA-N 0.000 claims 1
- VIDJPSBOTXVECU-KUFVUHJUSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[2-[(3R)-3-hydroxypyrrolidin-1-yl]-2-oxoethoxy]phenyl]-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)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCC(=O)N1C[C@@H](CC1)O)C VIDJPSBOTXVECU-KUFVUHJUSA-N 0.000 claims 1
- CJMGYAAEHAAUNI-RIEGYYRVSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[2-[(3R)-3-hydroxypyrrolidin-1-yl]ethoxymethyl]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COCCN1C[C@@H](CC1)O)C)C CJMGYAAEHAAUNI-RIEGYYRVSA-N 0.000 claims 1
- VFBKDFVKHXKODD-XLWWBGEVSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[2-[(3R)-3-hydroxypyrrolidin-1-yl]ethylcarbamoyl]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)C(NCCN1C[C@@H](CC1)O)=O)C)C VFBKDFVKHXKODD-XLWWBGEVSA-N 0.000 claims 1
- VIDJPSBOTXVECU-IKYOIFQTSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[2-[(3S)-3-hydroxypyrrolidin-1-yl]-2-oxoethoxy]phenyl]-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)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCC(=O)N1C[C@H](CC1)O)C VIDJPSBOTXVECU-IKYOIFQTSA-N 0.000 claims 1
- NAOLLIGRUXXKCO-NYZBEGEVSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(2,3-dihydroxypropylamino)propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNCC(CO)O)C)C NAOLLIGRUXXKCO-NYZBEGEVSA-N 0.000 claims 1
- AAARHRDBKUOBIO-QNGWXLTQSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(3,3-difluoropyrrolidin-1-yl)propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(CC1)(F)F)C)C AAARHRDBKUOBIO-QNGWXLTQSA-N 0.000 claims 1
- VDKPFVAEXSRQOY-KDXMTYKHSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(4-hydroxypiperidin-1-yl)propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)O)C)C VDKPFVAEXSRQOY-KDXMTYKHSA-N 0.000 claims 1
- DVULIVIWSFELQV-BHVANESWSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(dimethylamino)propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN(C)C)C)C DVULIVIWSFELQV-BHVANESWSA-N 0.000 claims 1
- AQAFKVDDDQIXNM-KCXVWBLISA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(2-hydroxy-2-pyridin-2-ylethyl)amino]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNCC(C1=NC=CC=C1)O)C)C AQAFKVDDDQIXNM-KCXVWBLISA-N 0.000 claims 1
- HDIOROQLSZLKIQ-RIEGYYRVSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(2R)-2-(hydroxymethyl)morpholin-4-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](OCC1)CO)C)C HDIOROQLSZLKIQ-RIEGYYRVSA-N 0.000 claims 1
- WXHZGLMRZMSFOM-ZAQUEYBZSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(2S)-2-methoxycarbonylpiperidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1[C@@H](CCCC1)C(=O)OC)C)C WXHZGLMRZMSFOM-ZAQUEYBZSA-N 0.000 claims 1
- CXZFQWWKVYVDEJ-LHEWISCISA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3-hydroxy-2,2-dimethylpropyl)amino]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNCC(CO)(C)C)C)C CXZFQWWKVYVDEJ-LHEWISCISA-N 0.000 claims 1
- ZURPRYQOLDKANX-RIEGYYRVSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypiperidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CCC1)O)C)C ZURPRYQOLDKANX-RIEGYYRVSA-N 0.000 claims 1
- KXDXZSWBCDBUQV-RIEGYYRVSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypiperidin-1-yl]propoxy]phenyl]-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)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCCCN1C[C@@H](CCC1)O)C KXDXZSWBCDBUQV-RIEGYYRVSA-N 0.000 claims 1
- ZTPYUOVTPWEUJL-UXMGRTHOSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2,6-dimethylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1C)OCCCN1C[C@@H](CC1)O)C)C ZTPYUOVTPWEUJL-UXMGRTHOSA-N 0.000 claims 1
- HIGUSMXBJIJTDI-KUFVUHJUSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-(trifluoromethyl)phenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C(F)(F)F)C HIGUSMXBJIJTDI-KUFVUHJUSA-N 0.000 claims 1
- IASOPXWKCIJCMJ-BYYXFNHRSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C IASOPXWKCIJCMJ-BYYXFNHRSA-N 0.000 claims 1
- WRFHSRZKYYBXRR-BYYXFNHRSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]phenyl]-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)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCCCN1C[C@@H](CC1)O)C WRFHSRZKYYBXRR-BYYXFNHRSA-N 0.000 claims 1
- IUHSREMYTCKVTL-UVNLRBHVSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3S)-3-fluoropyrrolidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@H](CC1)F)C)C IUHSREMYTCKVTL-UVNLRBHVSA-N 0.000 claims 1
- KXDXZSWBCDBUQV-HMIRPBQQSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3S)-3-hydroxypiperidin-1-yl]propoxy]phenyl]-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)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCCCN1C[C@H](CCC1)O)C KXDXZSWBCDBUQV-HMIRPBQQSA-N 0.000 claims 1
- UQSPHVPIEBKTCP-FOMDDGNBSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3S,4R)-3-hydroxy-4-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@H]([C@H](CC1)CO)O)C)C UQSPHVPIEBKTCP-FOMDDGNBSA-N 0.000 claims 1
- YYZVZHJPNYTUFR-XGVPZFSMSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[2-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C(CCCC1)CO)C)C YYZVZHJPNYTUFR-XGVPZFSMSA-N 0.000 claims 1
- VBQLCFCEWKEGNN-QNGWXLTQSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[2-hydroxyethyl(methyl)amino]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN(C)CCO)C)C VBQLCFCEWKEGNN-QNGWXLTQSA-N 0.000 claims 1
- CAKKIQUPVQWPQU-GPQVWERHSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[3-(diethylcarbamoyl)piperidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(CCC1)C(N(CC)CC)=O)C)C CAKKIQUPVQWPQU-GPQVWERHSA-N 0.000 claims 1
- CFNUWXAYVRYVMF-KDXMTYKHSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[3-(dimethylamino)azetidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(C1)N(C)C)C)C CFNUWXAYVRYVMF-KDXMTYKHSA-N 0.000 claims 1
- XEPKQYXAWGXOHP-AARGLWAYSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[3-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(CCC1)CO)C)C XEPKQYXAWGXOHP-AARGLWAYSA-N 0.000 claims 1
- UPMXLWCLUBKATG-FAIXQHPJSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCN(CC1)CCO)C)C UPMXLWCLUBKATG-FAIXQHPJSA-N 0.000 claims 1
- WVHSLYJUGKJPMM-SJARJILFSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCN(CC1)C1=C(C=CC=C1)OC)C)C WVHSLYJUGKJPMM-SJARJILFSA-N 0.000 claims 1
- OAONCUFYLAGCBV-FAIXQHPJSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[4-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)CO)C)C OAONCUFYLAGCBV-FAIXQHPJSA-N 0.000 claims 1
- OPPKIIRGQHHCIK-COCZKOEFSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[[(2R)-2-hydroxy-2-phenylethyl]amino]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNC[C@@H](C1=CC=CC=C1)O)C)C OPPKIIRGQHHCIK-COCZKOEFSA-N 0.000 claims 1
- WPUISKYHMYDKHF-RGULYWFUSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[[(2S)-1-hydroxy-3-methylbutan-2-yl]amino]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN[C@H](CO)C(C)C)C)C WPUISKYHMYDKHF-RGULYWFUSA-N 0.000 claims 1
- NAOLLIGRUXXKCO-WNOXWKSXSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[[(2S)-2,3-dihydroxypropyl]amino]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNC[C@@H](CO)O)C)C NAOLLIGRUXXKCO-WNOXWKSXSA-N 0.000 claims 1
- OPPKIIRGQHHCIK-ACEXITHZSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[[(2S)-2-hydroxy-2-phenylethyl]amino]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNC[C@H](C1=CC=CC=C1)O)C)C OPPKIIRGQHHCIK-ACEXITHZSA-N 0.000 claims 1
- PNPVCEVEUHJUKA-GTZDIBSYSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[4-[(3R)-3-hydroxypyrrolidin-1-yl]butyl]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methyl]-4-[(2-methylpropan-2-yl)oxycarbonyl]piperazine-2-carboxylic acid Chemical compound C(C)(C)(C)OC(=O)N1C[C@H](N(CC1)CC1=C(C=C(C(=C1)Cl)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)CCCCN1C[C@@H](CC1)O)C)C)OCC=1C=NC=C(C=1)C#N)C(=O)O PNPVCEVEUHJUKA-GTZDIBSYSA-N 0.000 claims 1
- RWKSQDWZNUVNCZ-RIEGYYRVSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[4-[(3R)-3-hydroxypyrrolidin-1-yl]butyl]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methyl]piperazine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CNCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)CCCCN1C[C@@H](CC1)O)C)C RWKSQDWZNUVNCZ-RIEGYYRVSA-N 0.000 claims 1
- CBYRPLDLVNQWRU-PGSXYRMZSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[4-[(3R)-3-hydroxypyrrolidin-1-yl]butyl]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)CCCCN1C[C@@H](CC1)O)C)C CBYRPLDLVNQWRU-PGSXYRMZSA-N 0.000 claims 1
- HAAUPLYODRMWIC-BYHBGFKFSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[4-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C=C(C=C1)OCCCN1C[C@@H](CC1)O)C)C HAAUPLYODRMWIC-BYHBGFKFSA-N 0.000 claims 1
- TZOUEWKPBPNGNU-VQOCUYOESA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[4-[4-[(3R)-3-hydroxypyrrolidin-1-yl]butoxy]-2-methylphenyl]-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)OCC=1C(=C(C=CC=1)C1=C(C=C(C=C1)OCCCCN1C[C@@H](CC1)O)C)C TZOUEWKPBPNGNU-VQOCUYOESA-N 0.000 claims 1
- LVFZEKDGYTZOGN-BHVANESWSA-N (2S)-1-[[5-chloro-4-[[2-chloro-3-[2-methyl-3-(3-morpholin-4-ylpropoxy)phenyl]phenyl]methoxy]-2-[(5-cyanopyridin-3-yl)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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCOCC1)C)Cl LVFZEKDGYTZOGN-BHVANESWSA-N 0.000 claims 1
- VSMHDLTZFRFSOK-QNGWXLTQSA-N (2S)-1-[[5-chloro-4-[[2-chloro-3-[2-methyl-3-(3-piperidin-1-ylpropoxy)phenyl]phenyl]methoxy]-2-[(5-cyanopyridin-3-yl)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)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCCCC1)C)Cl VSMHDLTZFRFSOK-QNGWXLTQSA-N 0.000 claims 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 1
- KIIBYFYYECADQV-JEXREGNNSA-N (2S)-2-[[4-[[3-[3-[3-[(3R)-3-acetamidopyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound C(C)(=O)N[C@H]1CN(CC1)CCCOC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COC1=CC(=C(CN[C@](C(=O)O)(CO)C)C=C1Cl)OCC=1C=NC=C(C=1)C#N)C)C KIIBYFYYECADQV-JEXREGNNSA-N 0.000 claims 1
- XAPDNYDIEMIHMG-RWYGWLOXSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[2-methyl-3-[2-methyl-3-[3-(4-methyl-3-oxopiperazin-1-yl)propoxy]phenyl]phenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(N(CC1)C)=O)C)C XAPDNYDIEMIHMG-RWYGWLOXSA-N 0.000 claims 1
- RTCGTDDMMCKTKN-DKFWVONXSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[2-[(3R)-3-hydroxypyrrolidin-1-yl]ethoxymethyl]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COCCN1C[C@@H](CC1)O)C)C RTCGTDDMMCKTKN-DKFWVONXSA-N 0.000 claims 1
- DHGYYEVYHDNHRC-BFXRBFBZSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[2-[(3S)-3-hydroxypyrrolidin-1-yl]-2-oxoethoxy]phenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCC(=O)N1C[C@H](CC1)O)C DHGYYEVYHDNHRC-BFXRBFBZSA-N 0.000 claims 1
- NYQWMFFCWZLQCH-FAIXQHPJSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(3,3-difluoropyrrolidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methyl-methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN([C@](C(=O)O)(CO)C)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(CC1)(F)F)C)C NYQWMFFCWZLQCH-FAIXQHPJSA-N 0.000 claims 1
- XVYVXAOMZSJWOC-KDXMTYKHSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(3,3-difluoropyrrolidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(CC1)(F)F)C)C XVYVXAOMZSJWOC-KDXMTYKHSA-N 0.000 claims 1
- SMHQPTNZWZREJK-QNEOAKRWSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(3-hydroxy-3-phenylpyrrolidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(CC1)(C1=CC=CC=C1)O)C)C SMHQPTNZWZREJK-QNEOAKRWSA-N 0.000 claims 1
- CJZVSHIUZICREW-BMJIBKAESA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-(3-hydroxy-3-phenylpyrrolidin-1-yl)propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxypropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@H](C(=O)O)CO)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CC(CC1)(C1=CC=CC=C1)O)C)C CJZVSHIUZICREW-BMJIBKAESA-N 0.000 claims 1
- WEKBXCGNASPSSU-IKJNGIHHSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2,6-dimethylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1C)OCCCN1C[C@@H](CC1)O)C)C WEKBXCGNASPSSU-IKJNGIHHSA-N 0.000 claims 1
- LNLWCYUXZHQIDS-LDNVYYCDSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2,6-dimethylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxypropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@H](C(=O)O)CO)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1C)OCCCN1C[C@@H](CC1)O)C)C LNLWCYUXZHQIDS-LDNVYYCDSA-N 0.000 claims 1
- DLWAOTVYTSDDHG-CPBHLAHYSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-(trifluoromethyl)phenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxypropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@H](C(=O)O)CO)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C(F)(F)F)C DLWAOTVYTSDDHG-CPBHLAHYSA-N 0.000 claims 1
- WBCGLYLFLOMKIV-JEXREGNNSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methyl-ethylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN([C@](C(=O)O)(CO)C)CC)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C WBCGLYLFLOMKIV-JEXREGNNSA-N 0.000 claims 1
- SMXOEHRPIYYLEG-IKJNGIHHSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methyl-methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN([C@](C(=O)O)(CO)C)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C SMXOEHRPIYYLEG-IKJNGIHHSA-N 0.000 claims 1
- HAYCFMPDJSGSJZ-GOJCVTOHSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methyl-methylamino]butanoic acid Chemical compound ClC=1C(=CC(=C(CN([C@H](C(=O)O)CC)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C HAYCFMPDJSGSJZ-GOJCVTOHSA-N 0.000 claims 1
- YMLIXFKBOMUHPS-JEVSUUQRSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-2-phenylacetic acid Chemical compound ClC=1C(=CC(=C(CN[C@H](C(=O)O)C2=CC=CC=C2)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C YMLIXFKBOMUHPS-JEVSUUQRSA-N 0.000 claims 1
- RUNHBRSIPPHFAM-DVYFPZHKSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C RUNHBRSIPPHFAM-DVYFPZHKSA-N 0.000 claims 1
- HRCCOQQFKFFDJQ-NQVJXQQZSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxypropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@H](C(=O)O)CO)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C HRCCOQQFKFFDJQ-NQVJXQQZSA-N 0.000 claims 1
- VVHMZZJGAJVZCV-BYYXFNHRSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]hexanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@H](C(=O)O)CCCC)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C VVHMZZJGAJVZCV-BYYXFNHRSA-N 0.000 claims 1
- AOERJEUNJATIBU-GOJCVTOHSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]pent-4-enoic acid Chemical compound ClC=1C(=CC(=C(CN[C@H](C(=O)O)CC=C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C AOERJEUNJATIBU-GOJCVTOHSA-N 0.000 claims 1
- LWVLYIZSDXSJCX-YSVKQWHRSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]phenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCCCN1C[C@@H](CC1)O)C LWVLYIZSDXSJCX-YSVKQWHRSA-N 0.000 claims 1
- LUHKZMWGXSUBCR-GOJCVTOHSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]phenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@H](C(=O)O)CCCNC(=N)N)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCCCN1C[C@@H](CC1)O)C LUHKZMWGXSUBCR-GOJCVTOHSA-N 0.000 claims 1
- MJMZAKHCJNMKHC-GCBNJDDTSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3S)-3-hydroxypiperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@H](CCC1)O)C)C MJMZAKHCJNMKHC-GCBNJDDTSA-N 0.000 claims 1
- PNJUFWHVYBZTRW-CBRAACIVSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3S,4R)-3-hydroxy-4-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound CC1=C(COC2=C(Cl)C=C(CN[C@@](C)(CO)C(O)=O)C(OCC3=CC(=CN=C3)C#N)=C2)C=CC=C1C1=CC=CC(OCCCN2CC[C@H](CO)[C@H](O)C2)=C1C PNJUFWHVYBZTRW-CBRAACIVSA-N 0.000 claims 1
- RDSGBZVHTMMSJY-WBCKFURZSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCN(CC1)CCO)C)C RDSGBZVHTMMSJY-WBCKFURZSA-N 0.000 claims 1
- BKLQZJVNTLGJDU-WBCKFURZSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[4-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)CO)C)C BKLQZJVNTLGJDU-WBCKFURZSA-N 0.000 claims 1
- MSWKIJNRFIGWIT-XSEQESSCSA-N (2S)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[[(2S)-2,3-dihydroxypropyl]amino]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNC[C@@H](CO)O)C)C MSWKIJNRFIGWIT-XSEQESSCSA-N 0.000 claims 1
- HTBNKJGYDDLXGS-GOJCVTOHSA-N (2S)-3-amino-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[4-[(3R)-3-hydroxypyrrolidin-1-yl]butyl]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]propanoic acid Chemical compound NC[C@@H](C(=O)O)NCC1=C(C=C(C(=C1)Cl)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)CCCCN1C[C@@H](CC1)O)C)C)OCC=1C=NC=C(C=1)C#N HTBNKJGYDDLXGS-GOJCVTOHSA-N 0.000 claims 1
- AXFMEGAFCUULFV-BLFANLJRSA-N (2s)-2-[[(2s)-1-[(2s,3r)-2-amino-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]pentanedioic acid Chemical compound CC[C@@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(O)=O)C(O)=O AXFMEGAFCUULFV-BLFANLJRSA-N 0.000 claims 1
- PZTFMTHLCBLARN-SSEXGKCCSA-N (3R)-1-[3-[3-[3-[[2-chloro-5-[(3,5-difluorophenyl)methoxy]-4-(hydroxymethyl)phenoxy]methyl]-2-methylphenyl]-2-methylphenoxy]propyl]pyrrolidin-3-ol Chemical compound ClC1=C(OCC=2C(=C(C=CC=2)C2=C(C(=CC=C2)OCCCN2C[C@@H](CC2)O)C)C)C=C(C(=C1)CO)OCC1=CC(=CC(=C1)F)F PZTFMTHLCBLARN-SSEXGKCCSA-N 0.000 claims 1
- CTOIVUMLXCUIST-QWQZQCCPSA-N (3R)-1-[3-[3-[3-[[4-[[[(2S)-2-carboxy-1-hydroxypropan-2-yl]amino]methyl]-2-chloro-5-[(5-cyanopyridin-3-yl)methoxy]phenoxy]methyl]-2-methylphenyl]-2-methylphenoxy]propyl]piperidine-3-carboxylic acid Chemical compound C(=O)(O)[C@@](CO)(C)NCC1=CC(=C(OCC=2C(=C(C=CC=2)C2=C(C(=CC=C2)OCCCN2C[C@@H](CCC2)C(=O)O)C)C)C=C1OCC=1C=NC=C(C=1)C#N)Cl CTOIVUMLXCUIST-QWQZQCCPSA-N 0.000 claims 1
- DKSNZNFMXRJNCF-HEVIKAOCSA-N (3S)-1-[3-[3-[3-[[4-[[(3S)-3-carboxypiperidin-1-yl]methyl]-2-chloro-5-[(5-cyanopyridin-3-yl)methoxy]phenoxy]methyl]-2-methylphenyl]-2-methylphenoxy]propyl]piperidine-3-carboxylic acid Chemical compound C(=O)(O)[C@@H]1CN(CCC1)CC1=CC(=C(OCC=2C(=C(C=CC=2)C2=C(C(=CC=C2)OCCCN2C[C@H](CCC2)C(=O)O)C)C)C=C1OCC=1C=NC=C(C=1)C#N)Cl DKSNZNFMXRJNCF-HEVIKAOCSA-N 0.000 claims 1
- CTOIVUMLXCUIST-SBIBQKHLSA-N (3S)-1-[3-[3-[3-[[4-[[[(2S)-2-carboxy-1-hydroxypropan-2-yl]amino]methyl]-2-chloro-5-[(5-cyanopyridin-3-yl)methoxy]phenoxy]methyl]-2-methylphenyl]-2-methylphenoxy]propyl]piperidine-3-carboxylic acid Chemical compound C(=O)(O)[C@@](CO)(C)NCC1=CC(=C(OCC=2C(=C(C=CC=2)C2=C(C(=CC=C2)OCCCN2C[C@H](CCC2)C(=O)O)C)C)C=C1OCC=1C=NC=C(C=1)C#N)Cl CTOIVUMLXCUIST-SBIBQKHLSA-N 0.000 claims 1
- JXSQLYGGBUYKRS-SAIUNTKASA-N (3S)-4-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]phenyl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxybutanoic acid Chemical compound ClC=1C(=CC(=C(CNC[C@H](CC(=O)O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCCCN1C[C@@H](CC1)O)C JXSQLYGGBUYKRS-SAIUNTKASA-N 0.000 claims 1
- ZIVNTPMYYKIGCC-JFMFZUJVSA-N (4-nitrophenyl) (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methyl]piperidine-2-carboxylate Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)OC2=CC=C(C=C2)[N+](=O)[O-])C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C ZIVNTPMYYKIGCC-JFMFZUJVSA-N 0.000 claims 1
- XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims 1
- CVFMQNFPFOQOQF-BHVANESWSA-N 1-[3-[3-[3-[[5-[(5-carbamoylpyridin-3-yl)methoxy]-4-[[(2S)-2-carboxypiperidin-1-yl]methyl]-2-chlorophenoxy]methyl]-2-methylphenyl]-2-chlorophenoxy]propyl]-4-(hydroxymethyl)piperidine-4-carboxylic acid Chemical compound C(N)(=O)C=1C=C(C=NC=1)COC1=C(CN2[C@@H](CCCC2)C(=O)O)C=C(C(=C1)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)(CO)C(=O)O)Cl)C)Cl CVFMQNFPFOQOQF-BHVANESWSA-N 0.000 claims 1
- JGMHLFSEAURIBP-LHEWISCISA-N 1-[3-[3-[3-[[5-[(5-carbamoylpyridin-3-yl)methoxy]-4-[[(2S)-2-carboxypiperidin-1-yl]methyl]-2-chlorophenoxy]methyl]-2-methylphenyl]-2-methylphenoxy]propyl]-4-(hydroxymethyl)piperidine-4-carboxylic acid Chemical compound C(N)(=O)C=1C=C(C=NC=1)COC1=C(CN2[C@@H](CCCC2)C(=O)O)C=C(C(=C1)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)(CO)C(=O)O)C)C)Cl JGMHLFSEAURIBP-LHEWISCISA-N 0.000 claims 1
- MYBLIFOJNJJVAR-UUWRZZSWSA-N 1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[2-[(3R)-3-hydroxypyrrolidin-1-yl]ethoxymethyl]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methyl-methylamino]cyclopropane-1-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN(C2(CC2)C(=O)O)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COCCN1C[C@@H](CC1)O)C)C MYBLIFOJNJJVAR-UUWRZZSWSA-N 0.000 claims 1
- QICPADIOCLJYPP-MGBGTMOVSA-N 1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[2-[(3R)-3-hydroxypyrrolidin-1-yl]ethoxymethyl]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]cyclopropane-1-carboxylic acid Chemical compound ClC=1C(=CC(=C(CNC2(CC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COCCN1C[C@@H](CC1)O)C)C QICPADIOCLJYPP-MGBGTMOVSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- JGCZCDAQHLVPJW-WJOKGBTCSA-N 2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenyl]methylamino]acetic acid Chemical compound ClC=1C(=CC(=C(CNCC(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C JGCZCDAQHLVPJW-WJOKGBTCSA-N 0.000 claims 1
- BWQMPTCLWJOKDW-GDLZYMKVSA-N 2-[[5-chloro-4-[[2-chloro-3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]phenyl]methoxy]-2-(3-methylbut-2-enoxy)phenyl]methylamino]propane-1,3-diol Chemical compound ClC=1C(=CC(=C(CNC(CO)CO)C=1)OCC=C(C)C)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)Cl BWQMPTCLWJOKDW-GDLZYMKVSA-N 0.000 claims 1
- NSMIWYKGAGRRMZ-UHFFFAOYSA-N 3-[3-[3-[3-[[4-[[(3-amino-3-oxopropyl)-methylamino]methyl]-2-chloro-5-[(5-cyanopyridin-3-yl)methoxy]phenoxy]methyl]-2-methylphenyl]-2-methylphenoxy]propyl-methylamino]propanamide Chemical compound NC(CCN(C)CC1=CC(=C(OCC=2C(=C(C=CC=2)C2=C(C(=CC=C2)OCCCN(CCC(=O)N)C)C)C)C=C1OCC=1C=NC=C(C=1)C#N)Cl)=O NSMIWYKGAGRRMZ-UHFFFAOYSA-N 0.000 claims 1
- ASXVTPJQTHQDSC-UHFFFAOYSA-N 3-[3-[[2-chloro-5-[(3,5-difluorophenyl)methoxy]-4-formylphenoxy]methyl]-2-methylphenyl]-N,2-dimethylbenzamide Chemical compound ClC1=C(OCC=2C(=C(C=CC=2)C2=C(C(=CC=C2)C(=O)NC)C)C)C=C(C(=C1)C=O)OCC1=CC(=CC(=C1)F)F ASXVTPJQTHQDSC-UHFFFAOYSA-N 0.000 claims 1
- HZSAPNSHGPNDHF-UHFFFAOYSA-N 3-methylsulfonylpyridine Chemical compound CS(=O)(=O)C1=CC=CN=C1 HZSAPNSHGPNDHF-UHFFFAOYSA-N 0.000 claims 1
- URLGWNKGOJVMCN-UHFFFAOYSA-N 4-chloro-5-[[3-[2-chloro-3-(3-piperidin-1-ylpropoxy)phenyl]-2-methylphenyl]methoxy]-2-(hydroxymethyl)phenol Chemical compound ClC1=CC(=C(C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCCCC1)Cl)C)O)CO URLGWNKGOJVMCN-UHFFFAOYSA-N 0.000 claims 1
- JZXUTRPKGQJMKT-UUWRZZSWSA-N 5-[[2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-3-methylphenoxy]methyl]pyridine-3-carbonitrile Chemical compound OCC(CO)NCC1=C(OCC=2C=NC=C(C#N)C=2)C=C(C=C1C)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C JZXUTRPKGQJMKT-UUWRZZSWSA-N 0.000 claims 1
- DCLSTBUPDVVSDU-UUWRZZSWSA-N 5-[[2-[[bis(2-hydroxyethyl)amino]methyl]-4-chloro-5-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-3-methylphenoxy]methyl]pyridine-3-carbonitrile Chemical compound OCCN(CCO)CC1=C(OCC=2C=NC=C(C#N)C=2)C=C(C(=C1C)Cl)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C DCLSTBUPDVVSDU-UUWRZZSWSA-N 0.000 claims 1
- ICMFHFUUKTUFKB-UHFFFAOYSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[2-methyl-3-[2-methyl-3-(3-piperidin-1-ylpropoxy)phenyl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCCCC1)C)C)CNC(CO)CO ICMFHFUUKTUFKB-UHFFFAOYSA-N 0.000 claims 1
- YZHDNOAHTFBXFD-UHFFFAOYSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[2-methyl-3-[2-methyl-3-(pyrrolidine-1-carbonyl)phenyl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)C(=O)N1CCCC1)C)C)CNC(CO)CO YZHDNOAHTFBXFD-UHFFFAOYSA-N 0.000 claims 1
- SJUZMHJGZNOEAB-UHFFFAOYSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[2-methyl-3-[2-methyl-3-[(6-morpholin-4-ylpyrimidin-4-yl)amino]phenyl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)NC1=NC=NC(=C1)N1CCOCC1)C)C)CNC(CO)CO SJUZMHJGZNOEAB-UHFFFAOYSA-N 0.000 claims 1
- BRQYJIYNEDCRTG-UUWRZZSWSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[3-[3-[2-[(3R)-3-hydroxypyrrolidin-1-yl]ethoxymethyl]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)COCCN1C[C@@H](CC1)O)C)C)CNC(CO)CO BRQYJIYNEDCRTG-UUWRZZSWSA-N 0.000 claims 1
- NADAUFDJCVQDPI-SSEXGKCCSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[3-[3-[3-[(3R)-3-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CCC1)CO)C)C)CNC(CO)CO NADAUFDJCVQDPI-SSEXGKCCSA-N 0.000 claims 1
- VZKFSVITLBJFNM-MGBGTMOVSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-3-methylphenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=C(C(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)CNC(CO)CO)C VZKFSVITLBJFNM-MGBGTMOVSA-N 0.000 claims 1
- NADAUFDJCVQDPI-PMERELPUSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[3-[3-[3-[(3S)-3-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@H](CCC1)CO)C)C)CNC(CO)CO NADAUFDJCVQDPI-PMERELPUSA-N 0.000 claims 1
- PYOGWDNVXVTUKA-UHFFFAOYSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[3-[3-[3-[4-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)CO)C)C)CNC(CO)CO PYOGWDNVXVTUKA-UHFFFAOYSA-N 0.000 claims 1
- CGJVBCCXZHZIMS-YTTGMZPUSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[3-[3-[3-[[(2S)-2,3-dihydroxypropyl]amino]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCNC[C@@H](CO)O)C)C)CNC(CO)CO CGJVBCCXZHZIMS-YTTGMZPUSA-N 0.000 claims 1
- HYRVAEAZLUOXCB-PGUFJCEWSA-N 5-[[4-chloro-2-[(1,3-dihydroxypropan-2-ylamino)methyl]-5-[[3-[3-[4-[(3R)-3-hydroxypyrrolidin-1-yl]butyl]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)CCCCN1C[C@@H](CC1)O)C)C)CNC(CO)CO HYRVAEAZLUOXCB-PGUFJCEWSA-N 0.000 claims 1
- AOBVAUUMLQNOTK-JGCGQSQUSA-N 5-[[4-chloro-2-[(3,5-dioxopiperazin-1-yl)methyl]-5-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)CN1CC(NC(C1)=O)=O AOBVAUUMLQNOTK-JGCGQSQUSA-N 0.000 claims 1
- GUAGGPLWXNGDJZ-ZBAKNJOASA-N 5-[[4-chloro-2-[1-(1,3-dihydroxypropan-2-ylamino)ethyl]-5-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)C(C)NC(CO)CO GUAGGPLWXNGDJZ-ZBAKNJOASA-N 0.000 claims 1
- JOHOUTOVUFYNAN-UHFFFAOYSA-N 5-[[4-chloro-2-[[(1,3-dihydroxy-2-methylpropan-2-yl)amino]methyl]-5-[[2-methyl-3-[2-methyl-3-(3-piperidin-1-ylpropoxy)phenyl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCCCC1)C)C)CNC(CO)(CO)C JOHOUTOVUFYNAN-UHFFFAOYSA-N 0.000 claims 1
- HBKGKVUKXDTGND-UHFFFAOYSA-N 5-[[4-chloro-2-[[(1,3-dihydroxy-2-methylpropan-2-yl)amino]methyl]-5-[[2-methyl-3-[2-methyl-3-(pyrrolidine-1-carbonyl)phenyl]phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)C(=O)N1CCCC1)C)C)CNC(CO)(CO)C HBKGKVUKXDTGND-UHFFFAOYSA-N 0.000 claims 1
- IELSEMLBRVDBNR-UHFFFAOYSA-N 5-[[4-chloro-2-[[(1,3-dihydroxy-2-methylpropan-2-yl)amino]methyl]-5-[[3-[3-[3-[4-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1CCC(CC1)CO)C)C)CNC(CO)(CO)C IELSEMLBRVDBNR-UHFFFAOYSA-N 0.000 claims 1
- RYIZBGPWDZXLII-KKLWWLSJSA-N 5-[[4-chloro-2-[[(3R)-3-hydroxypyrrolidin-1-yl]methyl]-5-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)CN1C[C@@H](CC1)O RYIZBGPWDZXLII-KKLWWLSJSA-N 0.000 claims 1
- OFICYWSMCSAWPZ-UHFFFAOYSA-N 5-[[4-chloro-2-[[2,3-dihydroxypropyl(methyl)amino]methyl]-5-[[3-[3-[3-[2,3-dihydroxypropyl(methyl)amino]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN(C)CC(CO)O)C)C)CN(C)CC(CO)O OFICYWSMCSAWPZ-UHFFFAOYSA-N 0.000 claims 1
- WOYKYTSCRUPQQF-BEBVUIBBSA-N 5-[[4-chloro-2-[[2-(hydroxymethyl)piperidin-1-yl]methyl]-5-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C)CN1C(CCCC1)CO WOYKYTSCRUPQQF-BEBVUIBBSA-N 0.000 claims 1
- SESSWVWUJADLNR-UHFFFAOYSA-N 5-[[4-chloro-2-[[2-(hydroxymethyl)piperidin-1-yl]methyl]-5-[[3-[3-[3-[2-(hydroxymethyl)piperidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C(CCCC1)CO)C)C)CN1C(CCCC1)CO SESSWVWUJADLNR-UHFFFAOYSA-N 0.000 claims 1
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- WPDXAMRGYMDTOV-UHFFFAOYSA-N 3-bromo-2-methylphenol Chemical compound CC1=C(O)C=CC=C1Br WPDXAMRGYMDTOV-UHFFFAOYSA-N 0.000 description 1
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
- YZKFMBAOEVINLP-UHFFFAOYSA-N 4-[2-(3-bromophenoxy)ethyl]morpholine Chemical compound BrC1=CC=CC(OCCN2CCOCC2)=C1 YZKFMBAOEVINLP-UHFFFAOYSA-N 0.000 description 1
- HBINCMBIMTYSDN-UHFFFAOYSA-N 5-[[4-chloro-2-formyl-5-[[3-(3-hydroxyphenyl)-2-methylphenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)O)C)C=O HBINCMBIMTYSDN-UHFFFAOYSA-N 0.000 description 1
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- MMTNPBFKACADCT-UHFFFAOYSA-N 5-chloro-4-[[3-[3-(3-chloropropoxy)phenyl]-2-methylphenyl]methoxy]-2-[(5-methylsulfonylpyridin-3-yl)methoxy]benzaldehyde Chemical compound ClC=1C(=CC(=C(C=O)C=1)OCC=1C=NC=C(C=1)S(=O)(=O)C)OCC=1C(=C(C=CC=1)C1=CC(=CC=C1)OCCCCl)C MMTNPBFKACADCT-UHFFFAOYSA-N 0.000 description 1
- DIRCPTYPCLYBEU-GDLZYMKVSA-N 5-chloro-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-2-[(5-methylsulfonylpyridin-3-yl)methoxy]benzaldehyde Chemical compound ClC=1C(=CC(=C(C=O)C=1)OCC=1C=NC=C(C=1)S(=O)(=O)C)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C DIRCPTYPCLYBEU-GDLZYMKVSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 101100063435 Caenorhabditis elegans din-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 description 1
- SVZZLIXGIHBVPC-MGBGTMOVSA-N N-[2-[[5-chloro-4-[[3-[3-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]-2-methylphenyl]-2-methylphenyl]methoxy]-2-[(5-methylsulfonylpyridin-3-yl)methoxy]phenyl]methylamino]ethyl]prop-2-enamide Chemical compound ClC=1C(=CC(=C(CNCCNC(C=C)=O)C=1)OCC=1C=NC=C(C=1)S(=O)(=O)C)OCC=1C(=C(C=CC=1)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)C SVZZLIXGIHBVPC-MGBGTMOVSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- CDUUKBXTEOFITR-UHFFFAOYSA-N alpha-methylserine Natural products OCC([NH3+])(C)C([O-])=O CDUUKBXTEOFITR-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- LADPCMZCENPFGV-UHFFFAOYSA-N chloromethoxymethylbenzene Chemical compound ClCOCC1=CC=CC=C1 LADPCMZCENPFGV-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- OPWULXUAKFTMOT-UHFFFAOYSA-N hydroxymethyl pyrrolidine-3-carboxylate Chemical compound OCOC(=O)C1CNCC1 OPWULXUAKFTMOT-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
- AHJZEZIYOBGVSK-JGVFFNPUSA-N tert-butyl (3s,4s)-3-(aminomethyl)-4-hydroxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@@H](O)[C@@H](CN)C1 AHJZEZIYOBGVSK-JGVFFNPUSA-N 0.000 description 1
- PLZRSYUTLFVTRV-UHFFFAOYSA-N tert-butyl 2-(3-bromophenoxy)acetate Chemical compound CC(C)(C)OC(=O)COC1=CC=CC(Br)=C1 PLZRSYUTLFVTRV-UHFFFAOYSA-N 0.000 description 1
- YDOOOAGJBCQRCM-UHFFFAOYSA-N tert-butyl 2-[3-[3-[[2-chloro-5-[(5-cyanopyridin-3-yl)methoxy]-4-formylphenoxy]methyl]-2-methylphenyl]phenoxy]acetate Chemical compound ClC1=C(OCC=2C(=C(C=CC=2)C2=CC(=CC=C2)OCC(=O)OC(C)(C)C)C)C=C(C(=C1)C=O)OCC=1C=NC=C(C=1)C#N YDOOOAGJBCQRCM-UHFFFAOYSA-N 0.000 description 1
- JKCYPFWATDNFLS-UHFFFAOYSA-N tert-butyl 3-(3-bromophenoxy)propanoate Chemical compound CC(C)(C)OC(=O)CCOC1=CC=CC(Br)=C1 JKCYPFWATDNFLS-UHFFFAOYSA-N 0.000 description 1
- JSOMVCDXPUXKIC-UHFFFAOYSA-N tert-butyl 3-oxopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)C1 JSOMVCDXPUXKIC-UHFFFAOYSA-N 0.000 description 1
- AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
- IOKGWQZQCNXXLD-UHFFFAOYSA-N tert-butyl n-(3-bromopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCBr IOKGWQZQCNXXLD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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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- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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| US20170145025A1 (en) | 2015-11-19 | 2017-05-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| LT3394033T (lt) | 2015-12-22 | 2021-03-10 | Incyte Corporation | Heterocikliniai junginiai, kaip imunomoduliatoriai |
| US20170320875A1 (en) | 2016-05-06 | 2017-11-09 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| US20170342060A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
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| US10745382B2 (en) | 2020-08-18 |
| KR102740320B1 (ko) | 2024-12-10 |
| CO2018004964A2 (es) | 2018-10-10 |
| KR20180061367A (ko) | 2018-06-07 |
| EP3362443B1 (en) | 2021-08-25 |
| CL2018000952A1 (es) | 2018-08-10 |
| PE20181045A1 (es) | 2018-07-03 |
| JP6916783B2 (ja) | 2021-08-11 |
| JP2018534282A (ja) | 2018-11-22 |
| IL258607A (en) | 2018-06-28 |
| US20170107202A1 (en) | 2017-04-20 |
| WO2017066227A1 (en) | 2017-04-20 |
| MA42990A (fr) | 2021-03-31 |
| EP3362443A1 (en) | 2018-08-22 |
| EA201890857A1 (ru) | 2018-09-28 |
| UY36950A (es) | 2017-04-28 |
| ZA201802450B (en) | 2020-01-29 |
| MX2018004347A (es) | 2018-05-01 |
| CN108368090A (zh) | 2018-08-03 |
| TW201726606A (zh) | 2017-08-01 |
| ES2892550T3 (es) | 2022-02-04 |
| CA3002008A1 (en) | 2017-04-20 |
| BR112018007381A2 (pt) | 2018-10-23 |
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