CA2527788A1 - 2-(6-amino-pyridin-3-yl)-2-hydroxyethylamine derivatives as beta 2-adrenoceptors agonists - Google Patents

Info

Publication number

CA2527788A1

CA2527788A1 CA002527788A CA2527788A CA2527788A1 CA 2527788 A1 CA2527788 A1 CA 2527788A1 CA 002527788 A CA002527788 A CA 002527788A CA 2527788 A CA2527788 A CA 2527788A CA 2527788 A1 CA2527788 A1 CA 2527788A1

Authority

CA

Canada

Prior art keywords

propyl

amino

hydroxy

aminopyridin

phenyl

Prior art date

2003-06-04

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

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000000556 agonist Substances 0.000 title claims description 31
• CVRVRWYCBRWOLQ-UHFFFAOYSA-N 2-amino-1-(6-aminopyridin-3-yl)ethanol Chemical class NCC(O)C1=CC=C(N)N=C1 CVRVRWYCBRWOLQ-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 297
• 238000002360 preparation method Methods 0.000 claims abstract description 273
• 238000000034 method Methods 0.000 claims abstract description 131
• 239000000203 mixture Substances 0.000 claims abstract description 84
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 37
• 201000010099 disease Diseases 0.000 claims abstract description 28
• 208000035475 disorder Diseases 0.000 claims abstract description 9
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 9
• 230000008569 process Effects 0.000 claims abstract description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 132
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 129
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 115
• -1 SR9 Chemical group 0.000 claims description 110
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 104
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 99
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 70
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 66
• 150000001412 amines Chemical class 0.000 claims description 65
• 239000002253 acid Substances 0.000 claims description 55
• 125000000217 alkyl group Chemical group 0.000 claims description 44
• 208000006673 asthma Diseases 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 38
• 206010006451 bronchitis Diseases 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 28
• 238000011282 treatment Methods 0.000 claims description 25
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
• 201000009267 bronchiectasis Diseases 0.000 claims description 18
• 102000005962 receptors Human genes 0.000 claims description 18
• 108020003175 receptors Proteins 0.000 claims description 18
• 229940079593 drug Drugs 0.000 claims description 16
• 230000000694 effects Effects 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 239000005557 antagonist Substances 0.000 claims description 12
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 11
• 125000006239 protecting group Chemical group 0.000 claims description 11
• 229940124597 therapeutic agent Drugs 0.000 claims description 11
• 150000003930 2-aminopyridines Chemical class 0.000 claims description 10
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 239000003112 inhibitor Substances 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 201000010659 intrinsic asthma Diseases 0.000 claims description 8
• 230000008506 pathogenesis Effects 0.000 claims description 8
• 239000012453 solvate Substances 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 6
• 206010006482 Bronchospasm Diseases 0.000 claims description 5
• 230000007885 bronchoconstriction Effects 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 5
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
• 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims description 4
• 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims description 4
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 4
• 206010014561 Emphysema Diseases 0.000 claims description 4
• 229940122694 Muscarinic M3 receptor antagonist Drugs 0.000 claims description 4
• 208000027771 Obstructive airways disease Diseases 0.000 claims description 4
• 230000001154 acute effect Effects 0.000 claims description 4
• 239000000812 cholinergic antagonist Substances 0.000 claims description 4
• 208000007451 chronic bronchitis Diseases 0.000 claims description 4
• 208000024711 extrinsic asthma Diseases 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 239000003681 muscarinic M3 receptor antagonist Substances 0.000 claims description 4
• 230000000414 obstructive effect Effects 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 229940044551 receptor antagonist Drugs 0.000 claims description 4
• 239000002464 receptor antagonist Substances 0.000 claims description 4
• 125000000565 sulfonamide group Chemical group 0.000 claims description 4
• UJVLSKFICSPQNU-VXLWULRPSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(4-hydroxy-3-methoxyphenyl)methyl]acetamide Chemical compound C1=C(O)C(OC)=CC(CNC(=O)CC=2C=C(CC(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 UJVLSKFICSPQNU-VXLWULRPSA-N 0.000 claims description 3
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
• 208000000059 Dyspnea Diseases 0.000 claims description 3
• 206010013975 Dyspnoeas Diseases 0.000 claims description 3
• 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 3
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 3
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
• 229910006074 SO2NH2 Inorganic materials 0.000 claims description 3
• 101100545004 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YSP2 gene Proteins 0.000 claims description 3
• 239000002465 adenosine A2a receptor agonist Substances 0.000 claims description 3
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 3
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 3
• 239000013566 allergen Substances 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 230000008878 coupling Effects 0.000 claims description 3
• 238000010168 coupling process Methods 0.000 claims description 3
• 238000005859 coupling reaction Methods 0.000 claims description 3
• VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 claims description 3
• GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 claims description 3
• OTZRAYGBFWZKMX-JUDRUQEKSA-N leukotriene E4 Chemical compound CCCCCC=CCC=C\C=C\C=C\[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O OTZRAYGBFWZKMX-JUDRUQEKSA-N 0.000 claims description 3
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 229960000278 theophylline Drugs 0.000 claims description 3
• YSKQGPMDXPBBJY-HXOBKFHXSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(2-hydroxy-5-methylphenyl)acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1=CC(C)=CC=C1O YSKQGPMDXPBBJY-HXOBKFHXSA-N 0.000 claims description 2
• NURBGMGWUKIAHK-MWTRTKDXSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(3-hydroxy-2-methylphenyl)acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1=CC=CC(O)=C1C NURBGMGWUKIAHK-MWTRTKDXSA-N 0.000 claims description 2
• UUIIWUKNVUTSNE-ZHRRBRCNSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(3-hydroxy-4-methoxyphenyl)acetamide Chemical compound C1=C(O)C(OC)=CC=C1NC(=O)CC1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 UUIIWUKNVUTSNE-ZHRRBRCNSA-N 0.000 claims description 2
• CTDHMZSZPKBCHL-HXOBKFHXSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(3-hydroxy-4-methylphenyl)acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1=CC=C(C)C(O)=C1 CTDHMZSZPKBCHL-HXOBKFHXSA-N 0.000 claims description 2
• XESNJJXNSNRFDW-NLFFAJNJSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(3-phenylpropyl)acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCCCC1=CC=CC=C1 XESNJJXNSNRFDW-NLFFAJNJSA-N 0.000 claims description 2
• IGKRIIXFWGRSBG-ZHRRBRCNSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(4-hydroxyphenyl)acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1=CC=C(O)C=C1 IGKRIIXFWGRSBG-ZHRRBRCNSA-N 0.000 claims description 2
• DEBJXINLCPCOPT-ZNSGIYGDSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(5-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(CC(=O)NC3C4=CC=CC(O)=C4CCC3)C=CC=2)C)=CC=C(N)N=C1 DEBJXINLCPCOPT-ZNSGIYGDSA-N 0.000 claims description 2
• RSNFSUNKQNRTED-CJAUYULYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(5-tert-butyl-2-hydroxyphenyl)acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1=CC(C(C)(C)C)=CC=C1O RSNFSUNKQNRTED-CJAUYULYSA-N 0.000 claims description 2
• PDJGWJMYBHXWOF-CJAUYULYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(2-chloro-4-hydroxyphenyl)methyl]-n-ethylacetamide Chemical compound C=1C=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1CC(=O)N(CC)CC1=CC=C(O)C=C1Cl PDJGWJMYBHXWOF-CJAUYULYSA-N 0.000 claims description 2
• GBNGHGSNFITVQS-HXOBKFHXSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(2-hydroxyphenyl)methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC=CC=C1O GBNGHGSNFITVQS-HXOBKFHXSA-N 0.000 claims description 2
• SDKKMCFUSCHVHO-QRQCRPRQSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(3,5-dichloro-2-hydroxyphenyl)methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC(Cl)=CC(Cl)=C1O SDKKMCFUSCHVHO-QRQCRPRQSA-N 0.000 claims description 2
• CRXLBXIEPHJAOV-CJAUYULYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(3-chloro-5-hydroxyphenyl)methyl]-n-ethylacetamide Chemical compound C=1C=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1CC(=O)N(CC)CC1=CC(O)=CC(Cl)=C1 CRXLBXIEPHJAOV-CJAUYULYSA-N 0.000 claims description 2
• UGEOCVYJZQATPV-MWTRTKDXSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(3-chloro-5-hydroxyphenyl)methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC(O)=CC(Cl)=C1 UGEOCVYJZQATPV-MWTRTKDXSA-N 0.000 claims description 2
• LYSWMYHCMHWIHP-HXOBKFHXSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(4-hydroxyphenyl)methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC=C(O)C=C1 LYSWMYHCMHWIHP-HXOBKFHXSA-N 0.000 claims description 2
• FIEGIBKRZRJPSL-MWTRTKDXSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(5-chloro-2-hydroxyphenyl)methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC(Cl)=CC=C1O FIEGIBKRZRJPSL-MWTRTKDXSA-N 0.000 claims description 2
• BOBQZGKXKNTVCI-CLOONOSVSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-(3-ethoxy-4-hydroxyphenyl)ethyl]acetamide Chemical compound C1=C(O)C(OCC)=CC(CCNC(=O)CC=2C=C(C[C@@H](C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 BOBQZGKXKNTVCI-CLOONOSVSA-N 0.000 claims description 2
• YSWKWILLLWJXAR-KOSHJBKYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-(3-hydroxy-4-methoxyphenyl)ethyl]acetamide Chemical compound C1=C(O)C(OC)=CC=C1CCNC(=O)CC1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 YSWKWILLLWJXAR-KOSHJBKYSA-N 0.000 claims description 2
• ICCCLQJQCUTXGH-KOSHJBKYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-(3-hydroxyphenyl)ethyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCCC1=CC=CC(O)=C1 ICCCLQJQCUTXGH-KOSHJBKYSA-N 0.000 claims description 2
• CFMCVVNBOUEDMY-KOSHJBKYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide Chemical compound C1=C(O)C(OC)=CC(CCNC(=O)CC=2C=C(C[C@@H](C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 CFMCVVNBOUEDMY-KOSHJBKYSA-N 0.000 claims description 2
• NDFUIKXWIDLZFV-KOSHJBKYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-(4-hydroxyphenyl)ethyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCCC1=CC=C(O)C=C1 NDFUIKXWIDLZFV-KOSHJBKYSA-N 0.000 claims description 2
• MQIBAVICCOQAET-GBTGNHPCSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]-n-methylacetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)N(C)CC(O)C1=CC=CC(O)=C1 MQIBAVICCOQAET-GBTGNHPCSA-N 0.000 claims description 2
• JLGQTJOFCNKMEQ-IBVKSMDESA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[4-(4-hydroxyphenyl)butyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCCCCC1=CC=C(O)C=C1 JLGQTJOFCNKMEQ-IBVKSMDESA-N 0.000 claims description 2
• DXCPZASPISEJCT-PBBNMVCDSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[2-(2-hydroxyphenyl)phenyl]methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC=CC=C1C1=CC=CC=C1O DXCPZASPISEJCT-PBBNMVCDSA-N 0.000 claims description 2
• NPTFLVHSXDIXEA-OLILMLBXSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[2-fluoro-4-(4-hydroxyphenyl)phenyl]methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC(C(=C1)F)=CC=C1C1=CC=C(O)C=C1 NPTFLVHSXDIXEA-OLILMLBXSA-N 0.000 claims description 2
• RXEPLXSDJNWOJZ-PBBNMVCDSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[3-(4-hydroxyphenyl)phenyl]methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC(C=1)=CC=CC=1C1=CC=C(O)C=C1 RXEPLXSDJNWOJZ-PBBNMVCDSA-N 0.000 claims description 2
• DQFSEGULSMTBPF-RCRUUEGKSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[3-[4-(hydroxymethyl)phenyl]phenyl]methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC(C=1)=CC=CC=1C1=CC=C(CO)C=C1 DQFSEGULSMTBPF-RCRUUEGKSA-N 0.000 claims description 2
• DVDLFFFJRPSGBQ-OSPHWJPCSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[3-hydroxy-5-(trifluoromethyl)phenyl]methyl]-n-methylacetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)N(C)CC1=CC(O)=CC(C(F)(F)F)=C1 DVDLFFFJRPSGBQ-OSPHWJPCSA-N 0.000 claims description 2
• IUZSDOUNIYBSKH-PBBNMVCDSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[4-(4-hydroxyphenyl)phenyl]methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC(C=C1)=CC=C1C1=CC=C(O)C=C1 IUZSDOUNIYBSKH-PBBNMVCDSA-N 0.000 claims description 2
• FTFZJGUKLJRXDO-JPYJTQIMSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-benzylacetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC=CC=C1 FTFZJGUKLJRXDO-JPYJTQIMSA-N 0.000 claims description 2
• LQBJKTDDUSJZEW-VWLOTQADSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(2,3-dihydro-1h-inden-2-yl)acetamide Chemical compound C1([C@@H](O)CNC(C)(CC=2C=C(CC(=O)NC3CC4=CC=CC=C4C3)C=CC=2)C)=CC=C(N)N=C1 LQBJKTDDUSJZEW-VWLOTQADSA-N 0.000 claims description 2
• YSMQNXNKVKMIEO-QFIPXVFZSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(2-chloro-4-hydroxyphenyl)acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NC1=CC=C(O)C=C1Cl YSMQNXNKVKMIEO-QFIPXVFZSA-N 0.000 claims description 2
• UGOVZVKGYPLUHL-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(2-hydroxy-5-methylphenyl)acetamide Chemical compound CC1=CC=C(O)C(NC(=O)CC=2C=C(CC(C)(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 UGOVZVKGYPLUHL-QHCPKHFHSA-N 0.000 claims description 2
• FRSKICZSOVEZJD-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(2-phenylethyl)acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCCC1=CC=CC=C1 FRSKICZSOVEZJD-DEOSSOPVSA-N 0.000 claims description 2
• HBVGZGDXVFDMMT-QFIPXVFZSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(3-hydroxy-4-methoxyphenyl)acetamide Chemical compound C1=C(O)C(OC)=CC=C1NC(=O)CC1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 HBVGZGDXVFDMMT-QFIPXVFZSA-N 0.000 claims description 2
• GDMGRJIFDPWGIY-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(3-hydroxy-4-methylphenyl)acetamide Chemical compound C1=C(O)C(C)=CC=C1NC(=O)CC1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 GDMGRJIFDPWGIY-QHCPKHFHSA-N 0.000 claims description 2
• CLWHSZIEGPPJNF-QFIPXVFZSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(3-hydroxyphenyl)acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NC1=CC=CC(O)=C1 CLWHSZIEGPPJNF-QFIPXVFZSA-N 0.000 claims description 2
• KANMKKLTVIMZTE-VWLOTQADSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(3-phenylpropyl)acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCCCC1=CC=CC=C1 KANMKKLTVIMZTE-VWLOTQADSA-N 0.000 claims description 2
• MWJAGEGDPNOWTH-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(5-ethylsulfonyl-2-hydroxyphenyl)acetamide Chemical compound CCS(=O)(=O)C1=CC=C(O)C(NC(=O)CC=2C=C(CC(C)(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 MWJAGEGDPNOWTH-DEOSSOPVSA-N 0.000 claims description 2
• KQFXVXPYMVEIQG-VWLOTQADSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(5-tert-butyl-2-hydroxyphenyl)acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NC1=CC(C(C)(C)C)=CC=C1O KQFXVXPYMVEIQG-VWLOTQADSA-N 0.000 claims description 2
• XKWFZRDOLVRRPS-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(3,5-dichlorophenyl)methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC(Cl)=CC(Cl)=C1 XKWFZRDOLVRRPS-QHCPKHFHSA-N 0.000 claims description 2
• MXQFFUMAHVUEDV-VWLOTQADSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(3-chloro-5-hydroxyphenyl)methyl]-n-ethylacetamide Chemical compound C=1C=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1CC(=O)N(CC)CC1=CC(O)=CC(Cl)=C1 MXQFFUMAHVUEDV-VWLOTQADSA-N 0.000 claims description 2
• VTZWAUHEMGTHIH-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(3-chloro-5-hydroxyphenyl)methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC(O)=CC(Cl)=C1 VTZWAUHEMGTHIH-QHCPKHFHSA-N 0.000 claims description 2
• RRLWLBPLXJRHKE-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(4-sulfamoylphenyl)methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 RRLWLBPLXJRHKE-QHCPKHFHSA-N 0.000 claims description 2
• QFVLPPPNRMHZJH-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(5-chloro-2-hydroxyphenyl)methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC(Cl)=CC=C1O QFVLPPPNRMHZJH-QHCPKHFHSA-N 0.000 claims description 2
• WEQZENBWJGNVDE-VWLOTQADSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[2-(3-ethoxy-4-hydroxyphenyl)ethyl]acetamide Chemical compound C1=C(O)C(OCC)=CC(CCNC(=O)CC=2C=C(CC(C)(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 WEQZENBWJGNVDE-VWLOTQADSA-N 0.000 claims description 2
• BPDKQVGOGABPQR-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[2-(3-hydroxyphenyl)ethyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCCC1=CC=CC(O)=C1 BPDKQVGOGABPQR-DEOSSOPVSA-N 0.000 claims description 2
• PEKSPLVVZVXYLE-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide Chemical compound C1=C(O)C(OC)=CC(CCNC(=O)CC=2C=C(CC(C)(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 PEKSPLVVZVXYLE-DEOSSOPVSA-N 0.000 claims description 2
• WBCALGARQBBOKQ-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[2-(4-hydroxyphenyl)ethyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCCC1=CC=C(O)C=C1 WBCALGARQBBOKQ-DEOSSOPVSA-N 0.000 claims description 2
• GANZKMBUEUASFX-SKCDSABHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]-n-methylacetamide Chemical compound C=1C=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1CC(=O)N(C)CC(O)C1=CC=CC(O)=C1 GANZKMBUEUASFX-SKCDSABHSA-N 0.000 claims description 2
• FEARBQOUKDOHBL-LJAQVGFWSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[[3-(4-hydroxyphenyl)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC(C=1)=CC=CC=1C1=CC=C(O)C=C1 FEARBQOUKDOHBL-LJAQVGFWSA-N 0.000 claims description 2
• CTCGYXRSAALLDF-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[[3-hydroxy-5-(trifluoromethyl)phenyl]methyl]-n-methylacetamide Chemical compound C=1C=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1CC(=O)N(C)CC1=CC(O)=CC(C(F)(F)F)=C1 CTCGYXRSAALLDF-DEOSSOPVSA-N 0.000 claims description 2
• RJEOZSVBWMVGDN-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-ethyl-n-(3-hydroxyphenyl)acetamide Chemical compound C1([C@@H](O)CNC(C)(C)CC=2C=CC=C(C=2)CC(=O)N(CC)C=2C=C(O)C=CC=2)=CC=C(N)N=C1 RJEOZSVBWMVGDN-DEOSSOPVSA-N 0.000 claims description 2
• XIUIDNNUSWLERE-IMMUGOHXSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(3,4,5-trimethoxyphenyl)methyl]acetamide Chemical compound COC1=C(OC)C(OC)=CC(CNC(=O)CC=2C=C(CC(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 XIUIDNNUSWLERE-IMMUGOHXSA-N 0.000 claims description 2
• GSYFRMJARSANCF-KESSSICBSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC(C(F)(F)F)=CC=C1F GSYFRMJARSANCF-KESSSICBSA-N 0.000 claims description 2
• GVXZASNOAYOREY-KESSSICBSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[4-fluoro-2-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=C(F)C=C1C(F)(F)F GVXZASNOAYOREY-KESSSICBSA-N 0.000 claims description 2
• VLQAVCAPEAIPRO-QHCPKHFHSA-N 2-[4-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(2,6-dimethoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC(OC)=C1CNC(=O)CC(C=C1)=CC=C1CC(C)(C)NC[C@H](O)C1=CC=C(N)N=C1 VLQAVCAPEAIPRO-QHCPKHFHSA-N 0.000 claims description 2
• PJBCMWNFRRXAKY-DEOSSOPVSA-N 2-[4-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(3-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC(CNC(=O)CC=2C=CC(CC(C)(C)NC[C@H](O)C=3C=NC(N)=CC=3)=CC=2)=C1 PJBCMWNFRRXAKY-DEOSSOPVSA-N 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• UVFVAKJMQXHLIL-ZHRRBRCNSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(2-hydroxy-5-methylphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC(C)=CC=C1O UVFVAKJMQXHLIL-ZHRRBRCNSA-N 0.000 claims description 2
• QTINNCGAARTPJK-QRQCRPRQSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(3-hydroxy-2-methylphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC=CC(O)=C1C QTINNCGAARTPJK-QRQCRPRQSA-N 0.000 claims description 2
• BXTQSBJWMMSWBU-VFNWGFHPSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(3-hydroxy-4-methoxyphenyl)benzamide Chemical compound C1=C(O)C(OC)=CC=C1NC(=O)C1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 BXTQSBJWMMSWBU-VFNWGFHPSA-N 0.000 claims description 2
• APPVRYWZAFXGQX-VFNWGFHPSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(3-hydroxyphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC=CC(O)=C1 APPVRYWZAFXGQX-VFNWGFHPSA-N 0.000 claims description 2
• CPBMOWXLMAIYRD-VFNWGFHPSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(4-hydroxyphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC=C(O)C=C1 CPBMOWXLMAIYRD-VFNWGFHPSA-N 0.000 claims description 2
• LJUMSTIAXHCMTC-MWTRTKDXSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(5-ethylsulfonyl-2-hydroxyphenyl)benzamide Chemical compound CCS(=O)(=O)C1=CC=C(O)C(NC(=O)C=2C=C(C[C@@H](C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 LJUMSTIAXHCMTC-MWTRTKDXSA-N 0.000 claims description 2
• UUEQNTWXVVSGRW-QFSZVTIDSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(5-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(C=CC=2)C(=O)NC2C3=CC=CC(O)=C3CCC2)C)=CC=C(N)N=C1 UUEQNTWXVVSGRW-QFSZVTIDSA-N 0.000 claims description 2
• VOANYSCQGWUKKD-PEBXRYMYSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(2,4-dichloro-6-hydroxyphenyl)methyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCC1=C(O)C=C(Cl)C=C1Cl VOANYSCQGWUKKD-PEBXRYMYSA-N 0.000 claims description 2
• FBSQYSNPBGQPDZ-HXOBKFHXSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(2-hydroxyphenyl)methyl]-n-methylbenzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)N(C)CC1=CC=CC=C1O FBSQYSNPBGQPDZ-HXOBKFHXSA-N 0.000 claims description 2
• VZGLFVQHHHJMEI-SZNDQCEHSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(3,5-dichloro-2-hydroxyphenyl)methyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCC1=CC(Cl)=CC(Cl)=C1O VZGLFVQHHHJMEI-SZNDQCEHSA-N 0.000 claims description 2
• ICXANKDOKSQUDF-ZHRRBRCNSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(3-hydroxyphenyl)methyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCC1=CC=CC(O)=C1 ICXANKDOKSQUDF-ZHRRBRCNSA-N 0.000 claims description 2
• BNVRMYWFBXNAAS-JPYJTQIMSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(4-hydroxy-3,5-dimethylphenyl)methyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCC1=CC(C)=C(O)C(C)=C1 BNVRMYWFBXNAAS-JPYJTQIMSA-N 0.000 claims description 2
• GXTNGQBQPVCJBT-ZHRRBRCNSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(4-hydroxy-3-methoxyphenyl)methyl]benzamide Chemical compound C1=C(O)C(OC)=CC(CNC(=O)C=2C=C(C[C@@H](C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 GXTNGQBQPVCJBT-ZHRRBRCNSA-N 0.000 claims description 2
• QIWUASSDGUPBBG-QRQCRPRQSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[(5-chloro-2-hydroxyphenyl)methyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCC1=CC(Cl)=CC=C1O QIWUASSDGUPBBG-QRQCRPRQSA-N 0.000 claims description 2
• GEIDDDLGOYNGHJ-HXOBKFHXSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(2-hydroxyphenyl)ethyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCCC1=CC=CC=C1O GEIDDDLGOYNGHJ-HXOBKFHXSA-N 0.000 claims description 2
• RXUAFTFQOLCYMJ-KOSHJBKYSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(3-ethoxy-4-hydroxyphenyl)ethyl]benzamide Chemical compound C1=C(O)C(OCC)=CC(CCNC(=O)C=2C=C(C[C@@H](C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 RXUAFTFQOLCYMJ-KOSHJBKYSA-N 0.000 claims description 2
• FXOIAKRUYZIEHK-HXOBKFHXSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(3-hydroxy-4-methoxyphenyl)ethyl]benzamide Chemical compound C1=C(O)C(OC)=CC=C1CCNC(=O)C1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 FXOIAKRUYZIEHK-HXOBKFHXSA-N 0.000 claims description 2
• GHCFQVHDHQAYQA-NSYGIPOTSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(4-hydroxy-2,3-dimethylphenyl)ethyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCCC1=CC=C(O)C(C)=C1C GHCFQVHDHQAYQA-NSYGIPOTSA-N 0.000 claims description 2
• KMESYZFBQAOLIN-CLOONOSVSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(4-hydroxy-2,5-dimethylphenyl)ethyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCCC1=CC(C)=C(O)C=C1C KMESYZFBQAOLIN-CLOONOSVSA-N 0.000 claims description 2
• WPZMDSKBIBUINL-KOSHJBKYSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(4-hydroxy-2-methylphenyl)ethyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCCC1=CC=C(O)C=C1C WPZMDSKBIBUINL-KOSHJBKYSA-N 0.000 claims description 2
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