JP2004532227A5 - - Google Patents
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- JP2004532227A5 JP2004532227A5 JP2002583418A JP2002583418A JP2004532227A5 JP 2004532227 A5 JP2004532227 A5 JP 2004532227A5 JP 2002583418 A JP2002583418 A JP 2002583418A JP 2002583418 A JP2002583418 A JP 2002583418A JP 2004532227 A5 JP2004532227 A5 JP 2004532227A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- methyl
- dihydro
- pyridinyl
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 33
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 18
- 125000005842 heteroatom Chemical group 0.000 claims 16
- 229910052717 sulfur Inorganic materials 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000002148 esters Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 12
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 10
- 239000003937 drug carrier Substances 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- -1 perfluoro Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 7
- 239000005711 Benzoic acid Substances 0.000 claims 6
- 235000010233 benzoic acid Nutrition 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- NCOCDZBFSLWJJR-PKTZIBPZSA-N 4-[(2r)-2-[[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]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=C(Cl)C=CC=3)CC1=CC=2C1=CC=C(C(O)=O)C=C1 NCOCDZBFSLWJJR-PKTZIBPZSA-N 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
- 125000006383 alkylpyridyl group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 229960003512 nicotinic acid Drugs 0.000 claims 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- 239000011664 nicotinic acid Substances 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 230000002485 urinary effect Effects 0.000 claims 2
- 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 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 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 1
- FSUIRDZQAZKAMK-IAPPQJPRSA-N 1-(4-fluorophenyl)-3-[4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]phenyl]sulfonylurea 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=C(F)C=C1 FSUIRDZQAZKAMK-IAPPQJPRSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- YEYWVLQJCBVXLW-IAPPQJPRSA-N 1-cyclohexyl-3-[4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]phenyl]sulfonylurea 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)NC1CCCCC1 YEYWVLQJCBVXLW-IAPPQJPRSA-N 0.000 claims 1
- 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 1
- 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 1
- OQSUPHPIRVUPBF-VPUSJEBWSA-N 2-(4-fluorophenoxy)-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(F)C=C1 OQSUPHPIRVUPBF-VPUSJEBWSA-N 0.000 claims 1
- OQDHXELLTUCNHY-VGSWGCGISA-N 2-chloro-5-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(Cl)=C(C(O)=O)C=C1F OQDHXELLTUCNHY-VGSWGCGISA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- BZVVLCMMOOIDHV-NOZRDPDXSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-(2-methylpropoxy)benzoic acid Chemical compound C1=C(C(O)=O)C(OCC(C)C)=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 BZVVLCMMOOIDHV-NOZRDPDXSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- VHCFCXIWHWHQCV-NAKRPHOHSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-(4-methylsulfonylphenoxy)benzoic acid Chemical compound C1=CC(S(=O)(=O)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 VHCFCXIWHWHQCV-NAKRPHOHSA-N 0.000 claims 1
- MOVHPVPONWXHIR-IRLDBZIGSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 MOVHPVPONWXHIR-IRLDBZIGSA-N 0.000 claims 1
- 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 1
- 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 1
- VJMINWBZFFKARA-VWNXMTODSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-2-propan-2-yloxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=C3CC[C@H](CNC[C@H](O)C=4C=NC=CC=4)OC3=CC=2)=C1 VJMINWBZFFKARA-VWNXMTODSA-N 0.000 claims 1
- 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 1
- XYAOQLLLBPYHJY-NOZRDPDXSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-3-(2-methylpropoxy)benzoic acid Chemical compound CC(C)COC1=CC(C(O)=O)=CC=C1C1=CC=C(O[C@@H](CNC[C@H](O)C=2C=NC=CC=2)CC2)C2=C1 XYAOQLLLBPYHJY-NOZRDPDXSA-N 0.000 claims 1
- 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 1
- 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 1
- IRZPRVADTGJBFQ-VWNXMTODSA-N 4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]-3-propoxybenzoic acid Chemical compound CCCOC1=CC(C(O)=O)=CC=C1C1=CC=C(O[C@@H](CNC[C@H](O)C=2C=NC=CC=2)CC2)C2=C1 IRZPRVADTGJBFQ-VWNXMTODSA-N 0.000 claims 1
- 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 1
- KLBCDERROIKSHM-RPWUZVMVSA-N 4-[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=C(C(O)=O)C=C1 KLBCDERROIKSHM-RPWUZVMVSA-N 0.000 claims 1
- 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 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- HTSGECRKWVPTEB-RPWUZVMVSA-N 5-[4-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]phenyl]furan-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)O1 HTSGECRKWVPTEB-RPWUZVMVSA-N 0.000 claims 1
- 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 1
- 102000015779 HDL Lipoproteins Human genes 0.000 claims 1
- 108010010234 HDL Lipoproteins Proteins 0.000 claims 1
- 206010021639 Incontinence Diseases 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 230000027939 micturition Effects 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- UEDWDOWDNMRVKB-SQHAQQRYSA-N n-[6-[(2r)-2-[[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-6-yl]pyridin-3-yl]benzenesulfonamide Chemical compound C([C@@H](OC1=CC=2)CNC[C@H](O)C=3C=NC=CC=3)CC1=CC=2C(N=C1)=CC=C1NS(=O)(=O)C1=CC=CC=C1 UEDWDOWDNMRVKB-SQHAQQRYSA-N 0.000 claims 1
- 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 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
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| US28571901P | 2001-04-23 | 2001-04-23 | |
| US32451801P | 2001-09-26 | 2001-09-26 | |
| PCT/US2002/012940 WO2002085891A1 (en) | 2001-04-23 | 2002-04-22 | 2,6-substituted chroman derivatives useful as beta-3 adrenoreceptor agonists |
Publications (2)
| Publication Number | Publication Date |
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| JP2004532227A JP2004532227A (ja) | 2004-10-21 |
| JP2004532227A5 true JP2004532227A5 (https=) | 2005-12-22 |
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| Country | Link |
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| EP (1) | EP1389202B1 (https=) |
| JP (1) | JP2004532227A (https=) |
| AR (1) | AR035858A1 (https=) |
| DE (1) | DE60201437T2 (https=) |
| DO (1) | DOP2002000385A (https=) |
| ES (1) | ES2230487T3 (https=) |
| PE (1) | PE20021073A1 (https=) |
| WO (1) | WO2002085891A1 (https=) |
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| EP1831203A1 (en) | 2004-12-21 | 2007-09-12 | F. Hoffmann-Roche AG | Chroman derivatives and uses thereof in the treatment of cns disorders |
| MX2007007558A (es) * | 2004-12-21 | 2007-07-24 | Hoffmann La Roche | Derivados de tetralina y de indano y usos de los mismos. |
| CA2592001A1 (en) * | 2004-12-21 | 2006-06-29 | F. Hoffmann-La Roche Ag | Chroman derivatives and their use as 5-ht receptor ligands |
| ATE448216T1 (de) * | 2004-12-21 | 2009-11-15 | Hoffmann La Roche | Tetralin- und indanderivate und anwendungen davon |
| MX2007007482A (es) * | 2004-12-21 | 2007-07-20 | Hoffmann La Roche | Derivados de tetralina e indano y usos de los mismos como antagonistas de 5-ht. |
| EP1856126A2 (en) | 2005-02-17 | 2007-11-21 | Wyeth a Corporation of the State of Delaware | Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives |
| BRPI0618206A2 (pt) * | 2005-11-03 | 2011-08-23 | Hoffmann La Roche | arilsulfonil cromanos como inibidores de 5-ht6, bem como composição farmacêutica, uso e processo para produção dos mesmos |
| GB0526252D0 (en) * | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| EP2402320A1 (en) | 2006-03-31 | 2012-01-04 | Novartis AG | Anorectic agents |
| BRPI0713502A2 (pt) * | 2006-06-20 | 2012-03-13 | F. Hoffmann-La Roche Ag | derivados de tetralina de arilsulfonamidil e empregos destes |
| CA2654822A1 (en) * | 2006-06-20 | 2007-12-27 | F. Hoffmann-La Roche Ag | Arylsulfonyl naphthalene derivatives and uses thereof |
| CN101472884A (zh) * | 2006-06-20 | 2009-07-01 | 弗·哈夫曼-拉罗切有限公司 | 1,2,3,4-四氢化萘和茚满衍生物及其用途 |
| SI2750677T1 (sl) | 2011-08-30 | 2017-10-30 | Chdi Foundation, Inc. | Inhibitorji kinurenin-3-monooksigenaze, farmacevtski sestavki in postopki njihove uporabe |
| UA122520C2 (uk) | 2013-01-09 | 2020-11-25 | Басф Агро Б.В. | Кристалічна форма 2-[4-(4-хлорфенокси)-2-(трифторметил)феніл]-1-(1,2,4-триазол-1-іл)пропан-2-олу, агрохімічна композиція, застосування та спосіб боротьби зі шкідливими грибами |
| US9790231B2 (en) * | 2013-06-24 | 2017-10-17 | Lupin Limited | Chromane and chromene derivatives and their use as CRAC modulators |
| WO2015003908A1 (en) | 2013-07-08 | 2015-01-15 | Basf Se | Compositions comprising a triazole compound and a biopesticide |
| EA037646B1 (ru) * | 2013-12-12 | 2021-04-27 | Басф Агро Б.В. | Способ получения замещенных триазолов |
| EA201892682A1 (ru) | 2014-06-25 | 2019-04-30 | Басф Агро Б.В. | Пестицидные композиции |
| DK3166932T3 (en) | 2014-07-08 | 2018-10-01 | Basf Agro Bv | PROCEDURE FOR PREPARING SUBSTITUTED OXIRANES AND TRIAZOLES |
| CN106715421A (zh) | 2014-07-17 | 2017-05-24 | Chdi基金会股份有限公司 | 用于治疗hiv相关病症的方法和组合物 |
| PL3214937T3 (pl) | 2014-11-07 | 2024-10-14 | Basf Se | Mieszaniny szkodnikobójcze |
| DK3294700T3 (da) | 2015-05-08 | 2020-04-14 | Basf Agro Bv | Fremgangsmåde til fremstilling af limonen-4-ol |
| EP3294720B1 (en) | 2015-05-08 | 2020-12-02 | BASF Agro B.V. | A process for the preparation of terpinolene epoxide |
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| WO2017095722A1 (en) * | 2015-11-30 | 2017-06-08 | Merck Sharp & Dohme Corp. | Aryl acylsulfonamides as blt1 antagonists |
| WO2017157920A1 (en) | 2016-03-16 | 2017-09-21 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits |
| RU2754614C2 (ru) | 2016-03-16 | 2021-09-03 | Басф Се | Применение тетразолинонов для борьбы с устойчивыми фитопатогенными грибами на злаковых культурах |
| BR112018068705B1 (pt) | 2016-03-16 | 2022-09-06 | Basf Se | Método para controlar fungos fitopatogênicos |
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-
2002
- 2002-04-17 AR ARP020101393A patent/AR035858A1/es not_active Application Discontinuation
- 2002-04-22 DE DE60201437T patent/DE60201437T2/de not_active Expired - Fee Related
- 2002-04-22 JP JP2002583418A patent/JP2004532227A/ja not_active Withdrawn
- 2002-04-22 WO PCT/US2002/012940 patent/WO2002085891A1/en not_active Ceased
- 2002-04-22 US US10/131,448 patent/US6660752B2/en not_active Expired - Fee Related
- 2002-04-22 DO DO2002000385A patent/DOP2002000385A/es unknown
- 2002-04-22 ES ES02723958T patent/ES2230487T3/es not_active Expired - Lifetime
- 2002-04-22 EP EP02723958A patent/EP1389202B1/en not_active Expired - Lifetime
- 2002-04-23 PE PE2002000337A patent/PE20021073A1/es not_active Application Discontinuation
-
2003
- 2003-09-17 US US10/666,903 patent/US6919371B2/en not_active Expired - Fee Related
-
2005
- 2005-04-28 US US11/117,759 patent/US20050215594A1/en not_active Abandoned
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