DE60201437T2 - 2,6-substituierte chromanderivate und ihre verwendung als beta-3 adrenorezeptor agonisten - Google Patents

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Publication number

DE60201437T2

DE60201437T2 DE60201437T DE60201437T DE60201437T2 DE 60201437 T2 DE60201437 T2 DE 60201437T2 DE 60201437 T DE60201437 T DE 60201437T DE 60201437 T DE60201437 T DE 60201437T DE 60201437 T2 DE60201437 T2 DE 60201437T2

Authority

DE

Germany

Prior art keywords

amino

methyl

dihydro

chromen

pyridinyl

Prior art date

2001-04-23

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.)

Expired - Fee Related

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• 239000000018 receptor agonist Substances 0.000 title 1
• 229940044601 receptor agonist Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 236
• -1 R 1 Chemical group 0.000 claims description 213
• 238000002360 preparation method Methods 0.000 claims description 151
• 239000000203 mixture Substances 0.000 claims description 124
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
• 125000000217 alkyl group Chemical group 0.000 claims description 73
• 125000000623 heterocyclic group Chemical group 0.000 claims description 50
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 229910052717 sulfur Inorganic materials 0.000 claims description 42
• 229910052760 oxygen Inorganic materials 0.000 claims description 40
• 125000005842 heteroatom Chemical group 0.000 claims description 37
• 125000005843 halogen group Chemical group 0.000 claims description 34
• 150000002148 esters Chemical class 0.000 claims description 29
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 23
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
• UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 21
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 21
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 20
• 125000001475 halogen functional group Chemical group 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 208000035475 disorder Diseases 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 108010014502 beta-3 Adrenergic Receptors Proteins 0.000 claims description 12
• 206010012601 diabetes mellitus Diseases 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000004434 sulfur atom Chemical group 0.000 claims description 8
• 230000002485 urinary effect Effects 0.000 claims description 8
• 239000005711 Benzoic acid Substances 0.000 claims description 7
• 235000010233 benzoic acid Nutrition 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 230000001404 mediated effect Effects 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 6
• 208000008589 Obesity Diseases 0.000 claims description 6
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 235000020824 obesity Nutrition 0.000 claims description 6
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 6
• PXPVVHPMXVMBOP-DGPALRBDSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-(2-phenylethyl)benzoic acid Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C(C=1)=CC=C(C(O)=O)C=1CCC1=CC=CC=C1 PXPVVHPMXVMBOP-DGPALRBDSA-N 0.000 claims description 5
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 5
• 102000015779 HDL Lipoproteins Human genes 0.000 claims description 5
• 108010010234 HDL Lipoproteins Proteins 0.000 claims description 5
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
• 125000006383 alkylpyridyl group Chemical group 0.000 claims description 5
• 102000016959 beta-3 Adrenergic Receptors Human genes 0.000 claims description 5
• 201000010099 disease Diseases 0.000 claims description 5
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 5
• YZJGAHHGBFDEFY-GGAORHGYSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C1=CC=C(O[C@@H](CNC[C@H](O)C=2C=NC=CC=2)CC2)C2=C1 YZJGAHHGBFDEFY-GGAORHGYSA-N 0.000 claims description 4
• 206010021639 Incontinence Diseases 0.000 claims description 4
• 206010036018 Pollakiuria Diseases 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000003003 spiro group Chemical group 0.000 claims description 4
• GLHIAFUUFYHCIJ-RTWAWAEBSA-N (1r)-1-(6-aminopyridin-3-yl)-2-[[(2r)-6-[4-(2h-tetrazol-5-yl)phenyl]-3,4-dihydro-2h-chromen-2-yl]methylamino]ethanol Chemical compound C1=NC(N)=CC=C1[C@@H](O)CNC[C@@H]1OC2=CC=C(C=3C=CC(=CC=3)C=3NN=NN=3)C=C2CC1 GLHIAFUUFYHCIJ-RTWAWAEBSA-N 0.000 claims description 3
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
• XSESTUCLKNZCGJ-UHSQPCAPSA-N 1-(4-chloro-2-methylphenyl)-3-[4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]phenyl]sulfonylurea Chemical compound CC1=CC(Cl)=CC=C1NC(=O)NS(=O)(=O)C1=CC=C(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)C=C1 XSESTUCLKNZCGJ-UHSQPCAPSA-N 0.000 claims description 3
• SVDQIHLVRZJJMJ-PXJZQJOASA-N 1-[4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]phenyl]sulfonyl-3-(4-methylphenyl)urea Chemical compound C1=CC(C)=CC=C1NC(=O)NS(=O)(=O)C1=CC=C(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)C=C1 SVDQIHLVRZJJMJ-PXJZQJOASA-N 0.000 claims description 3
• LLSWMDSPHVOGKD-IAPPQJPRSA-N 1-[4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]phenyl]sulfonyl-3-phenylurea Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C(C=C1)=CC=C1S(=O)(=O)NC(=O)NC1=CC=CC=C1 LLSWMDSPHVOGKD-IAPPQJPRSA-N 0.000 claims description 3
• YWMCHQQXZXIIPB-SJORKVTESA-N 1-[[(2r)-2-[[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]methyl]-3,4-dihydro-2h-chromene-6-carbonyl]amino]cyclopropane-1-carboxylic acid Chemical compound C1=NC(N)=CC=C1[C@@H](O)CNC[C@@H]1OC2=CC=C(C(=O)NC3(CC3)C(O)=O)C=C2CC1 YWMCHQQXZXIIPB-SJORKVTESA-N 0.000 claims description 3
• NEQHVHSNHJQCBF-VPUSJEBWSA-N 2-(4-chlorophenoxy)-4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]benzoic acid Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C(C=1)=CC=C(C(O)=O)C=1OC1=CC=C(Cl)C=C1 NEQHVHSNHJQCBF-VPUSJEBWSA-N 0.000 claims description 3
• BXAZPLFDHGKKOL-PXJZQJOASA-N 2-(4-ethoxycarbonylphenoxy)-4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]benzoic acid Chemical compound C1=CC(C(=O)OCC)=CC=C1OC1=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=CC=C1C(O)=O BXAZPLFDHGKKOL-PXJZQJOASA-N 0.000 claims description 3
• KRNPEOPMLMYQRD-GGAORHGYSA-N 2-ethoxy-4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(OCC)=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 KRNPEOPMLMYQRD-GGAORHGYSA-N 0.000 claims description 3
• XWXXYSJWYMIXNI-KNQAVFIVSA-N 2-fluoro-4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]benzoic acid Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C1=CC=C(C(O)=O)C(F)=C1 XWXXYSJWYMIXNI-KNQAVFIVSA-N 0.000 claims description 3
• LDSCAVNMYGABES-KNQAVFIVSA-N 2-hydroxy-4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]benzoic acid Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C1=CC=C(C(O)=O)C(O)=C1 LDSCAVNMYGABES-KNQAVFIVSA-N 0.000 claims description 3
• UPGQXSWXIJXLSK-NOZRDPDXSA-N 3-(cyclopropylmethoxy)-4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]benzoic acid Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C1=CC=C(C(O)=O)C=C1OCC1CC1 UPGQXSWXIJXLSK-NOZRDPDXSA-N 0.000 claims description 3
• GXGREEWZHKZXMH-IZLXSDGUSA-N 3-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-n-(2-methylphenyl)sulfonylbenzamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)C1=CC=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 GXGREEWZHKZXMH-IZLXSDGUSA-N 0.000 claims description 3
• CANAPWMKNAYZFT-PXJZQJOASA-N 3-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-n-(4-methoxyphenyl)sulfonylbenzamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 CANAPWMKNAYZFT-PXJZQJOASA-N 0.000 claims description 3
• XHKPZFLKONEDLG-RPBOFIJWSA-N 3-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-n-propylsulfonylbenzamide Chemical compound CCCS(=O)(=O)NC(=O)C1=CC=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 XHKPZFLKONEDLG-RPBOFIJWSA-N 0.000 claims description 3
• AQRSGCAKTMHAGY-SDJMYADNSA-N 3-[(e)-hex-1-enyl]-4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]benzoic acid Chemical compound CCCC\C=C\C1=CC(C(O)=O)=CC=C1C1=CC=C(O[C@@H](CNC[C@H](O)C=2C=NC=CC=2)CC2)C2=C1 AQRSGCAKTMHAGY-SDJMYADNSA-N 0.000 claims description 3
• HBGBOHHJDZDJGB-RPWUZVMVSA-N 3-[2-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]ethyl]benzoic acid Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2CCC1=CC=CC(C(O)=O)=C1 HBGBOHHJDZDJGB-RPWUZVMVSA-N 0.000 claims description 3
• XCALYEBMDSVIQA-KNQAVFIVSA-N 3-chloro-4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]benzoic acid Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C1=CC=C(C(O)=O)C=C1Cl XCALYEBMDSVIQA-KNQAVFIVSA-N 0.000 claims description 3
• QPZQQYVMIQBVDZ-RTWAWAEBSA-N 4-[(2r)-2-[[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]benzoic acid Chemical compound C1=NC(N)=CC=C1[C@@H](O)CNC[C@@H]1OC2=CC=C(C=3C=CC(=CC=3)C(O)=O)C=C2CC1 QPZQQYVMIQBVDZ-RTWAWAEBSA-N 0.000 claims description 3
• OWTKRFQGTFKXNQ-PKTZIBPZSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2,6-dimethylbenzoic acid Chemical compound CC1=C(C(O)=O)C(C)=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 OWTKRFQGTFKXNQ-PKTZIBPZSA-N 0.000 claims description 3
• ALJJBOKUOINEBD-VWNXMTODSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-(2-methoxyethoxy)benzoic acid Chemical compound C1=C(C(O)=O)C(OCCOC)=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 ALJJBOKUOINEBD-VWNXMTODSA-N 0.000 claims description 3
• ZLBKXPBEZWIACX-RSXGOPAZSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-(2-methylpropyl)benzoic acid Chemical compound C1=C(C(O)=O)C(CC(C)C)=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 ZLBKXPBEZWIACX-RSXGOPAZSA-N 0.000 claims description 3
• WWQOMERSUMBCRS-IAPPQJPRSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-(4-methoxyphenoxy)benzoic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=CC=C1C(O)=O WWQOMERSUMBCRS-IAPPQJPRSA-N 0.000 claims description 3
• ZCNDKNHXAYNDQT-IAPPQJPRSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-(4-methylphenoxy)benzoic acid Chemical compound C1=CC(C)=CC=C1OC1=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=CC=C1C(O)=O ZCNDKNHXAYNDQT-IAPPQJPRSA-N 0.000 claims description 3
• QYSINFPZMCNIDU-UHSQPCAPSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-(4-methylphenyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=CC=C1C(O)=O QYSINFPZMCNIDU-UHSQPCAPSA-N 0.000 claims description 3
• OAJXNPVLACUJPN-GGAORHGYSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-methylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 OAJXNPVLACUJPN-GGAORHGYSA-N 0.000 claims description 3
• PHQMOLCASOFUNR-VPUSJEBWSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-phenoxybenzoic acid Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C(C=1)=CC=C(C(O)=O)C=1OC1=CC=CC=C1 PHQMOLCASOFUNR-VPUSJEBWSA-N 0.000 claims description 3
• ZDGWNVNZRSOUOW-VWNXMTODSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-propoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 ZDGWNVNZRSOUOW-VWNXMTODSA-N 0.000 claims description 3
• YTVROTUURLAKHG-IRLDBZIGSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1C1=CC=C(O[C@@H](CNC[C@H](O)C=2C=NC=CC=2)CC2)C2=C1 YTVROTUURLAKHG-IRLDBZIGSA-N 0.000 claims description 3
• ASYYJYASZWFNSY-NAKRPHOHSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-n-(4-methoxyphenyl)sulfonylpyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(=O)C1=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=CC=N1 ASYYJYASZWFNSY-NAKRPHOHSA-N 0.000 claims description 3
• LRFBGWSTPPWWDW-RPBOFIJWSA-N 4-[4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]phenyl]thiophene-2-carboxylic acid Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C(C=C1)=CC=C1C1=CSC(C(O)=O)=C1 LRFBGWSTPPWWDW-RPBOFIJWSA-N 0.000 claims description 3
• JSPZGQIBLFFWEM-RPWUZVMVSA-N 5-[4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]phenyl]thiophene-2-carboxylic acid Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C(C=C1)=CC=C1C1=CC=C(C(O)=O)S1 JSPZGQIBLFFWEM-RPWUZVMVSA-N 0.000 claims description 3
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
• 206010056997 Impaired fasting glucose Diseases 0.000 claims description 3
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 3
• 230000003143 atherosclerotic effect Effects 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
• NGCUTHMQSLSFJS-IRLDBZIGSA-N n-[6-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]pyridin-3-yl]methanesulfonamide Chemical compound N1=CC(NS(=O)(=O)C)=CC=C1C1=CC=C(O[C@@H](CNC[C@H](O)C=2C=NC=CC=2)CC2)C2=C1 NGCUTHMQSLSFJS-IRLDBZIGSA-N 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
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