KR20050106033A - 글루코스 대사 조절제로서의 페닐- 및피리딜피페리딘-유도체 - Google Patents
글루코스 대사 조절제로서의 페닐- 및피리딜피페리딘-유도체 Download PDFInfo
- Publication number
- KR20050106033A KR20050106033A KR1020057015582A KR20057015582A KR20050106033A KR 20050106033 A KR20050106033 A KR 20050106033A KR 1020057015582 A KR1020057015582 A KR 1020057015582A KR 20057015582 A KR20057015582 A KR 20057015582A KR 20050106033 A KR20050106033 A KR 20050106033A
- Authority
- KR
- South Korea
- Prior art keywords
- nitro
- alkyl
- phenyl
- compound
- phenoxy
- 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.)
- Ceased
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- 230000004153 glucose metabolism Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 389
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 110
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 35
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 230000002265 prevention Effects 0.000 claims abstract description 15
- -1 amino, carbonyl Chemical group 0.000 claims description 305
- 125000000217 alkyl group Chemical group 0.000 claims description 187
- 238000000034 method Methods 0.000 claims description 146
- 229910052736 halogen Inorganic materials 0.000 claims description 100
- 150000002367 halogens Chemical class 0.000 claims description 93
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 92
- 125000003545 alkoxy group Chemical group 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 229910052799 carbon Inorganic materials 0.000 claims description 69
- 125000002252 acyl group Chemical group 0.000 claims description 64
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 64
- 125000001424 substituent group Chemical group 0.000 claims description 64
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 63
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 62
- 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 description 56
- 239000008103 glucose Substances 0.000 claims description 55
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 54
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 45
- 125000004414 alkyl thio group Chemical group 0.000 claims description 45
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 45
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 44
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 39
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 241000282414 Homo sapiens Species 0.000 claims description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 32
- 125000004423 acyloxy group Chemical group 0.000 claims description 32
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 32
- 239000003814 drug Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 29
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 26
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 18
- 239000000556 agonist Substances 0.000 claims description 18
- 239000004202 carbamide Substances 0.000 claims description 18
- 241001465754 Metazoa Species 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
- 125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 15
- 125000004494 ethyl ester group Chemical group 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
- 239000005977 Ethylene Substances 0.000 claims description 11
- 206010022489 Insulin Resistance Diseases 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 201000001421 hyperglycemia Diseases 0.000 claims description 11
- 208000011580 syndromic disease Diseases 0.000 claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 9
- 235000012054 meals Nutrition 0.000 claims description 9
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 8
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 150000004677 hydrates Chemical class 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 6
- 208000015580 Increased body weight Diseases 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 229940125425 inverse agonist Drugs 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
- 230000007423 decrease Effects 0.000 claims description 4
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000004999 nitroaryl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- FABWZDHUYWQDKR-UHFFFAOYSA-N 1-[5-(4-ethenylphenoxy)-2-nitrophenyl]-4-propylpiperidine Chemical compound C1CC(CCC)CCN1C1=CC(OC=2C=CC(C=C)=CC=2)=CC=C1[N+]([O-])=O FABWZDHUYWQDKR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- YPXRIOYBDVXGIO-UHFFFAOYSA-N 1-[1-[6-(4-acetylphenoxy)-3-nitropyridin-2-yl]piperidin-4-yl]ethanone Chemical compound C1CC(C(=O)C)CCN1C1=NC(OC=2C=CC(=CC=2)C(C)=O)=CC=C1[N+]([O-])=O YPXRIOYBDVXGIO-UHFFFAOYSA-N 0.000 claims description 2
- UYZMRNXBHUIYIL-UHFFFAOYSA-N 1-[4-[3-[4-(methoxymethyl)piperidin-1-yl]-4-nitrophenoxy]phenyl]ethanone Chemical compound C1CC(COC)CCN1C1=CC(OC=2C=CC(=CC=2)C(C)=O)=CC=C1[N+]([O-])=O UYZMRNXBHUIYIL-UHFFFAOYSA-N 0.000 claims description 2
- DBULFMSJWWTZHT-UHFFFAOYSA-N 1-[4-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]phenyl]ethanone Chemical compound C1CC(CCC)CCN1C1=CC(OC=2C=CC(=CC=2)C(C)=O)=CC=C1[N+]([O-])=O DBULFMSJWWTZHT-UHFFFAOYSA-N 0.000 claims description 2
- PZJDKUSWONJXFN-UHFFFAOYSA-N 1-[4-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]phenyl]hexan-1-one Chemical compound C1=CC(C(=O)CCCCC)=CC=C1OC1=CC=C([N+]([O-])=O)C(N2CCC(CCC)CC2)=C1 PZJDKUSWONJXFN-UHFFFAOYSA-N 0.000 claims description 2
- UDUBLFGDNOWYFL-UHFFFAOYSA-N 1-[4-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]phenyl]pentan-1-one Chemical compound C1=CC(C(=O)CCCC)=CC=C1OC1=CC=C([N+]([O-])=O)C(N2CCC(CCC)CC2)=C1 UDUBLFGDNOWYFL-UHFFFAOYSA-N 0.000 claims description 2
- QGCMNWAITFFWRS-UHFFFAOYSA-N 1-[4-[4-nitro-3-(4-pyridin-2-ylsulfanylpiperidin-1-yl)phenoxy]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)SC=2N=CC=CC=2)=C1 QGCMNWAITFFWRS-UHFFFAOYSA-N 0.000 claims description 2
- BZQSVOJMQLADPO-UHFFFAOYSA-N 2-[1-[2-nitro-5-[4-(1,2,4-triazol-1-yl)phenoxy]phenyl]piperidin-4-yl]sulfanylpyridine Chemical compound C1=C(N2CCC(CC2)SC=2N=CC=CC=2)C([N+](=O)[O-])=CC=C1OC(C=C1)=CC=C1N1C=NC=N1 BZQSVOJMQLADPO-UHFFFAOYSA-N 0.000 claims description 2
- BNHXXPBMPCCDAX-UHFFFAOYSA-N 2-[1-[5-(4-methylsulfonylphenoxy)-2-nitrophenyl]piperidin-4-yl]sulfanylpyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)SC=2N=CC=CC=2)=C1 BNHXXPBMPCCDAX-UHFFFAOYSA-N 0.000 claims description 2
- YVCMBGPPTCBEDP-UHFFFAOYSA-N 2-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]-5-(trifluoromethyl)pyridine Chemical compound C1CC(CCC)CCN1C1=CC(OC=2N=CC(=CC=2)C(F)(F)F)=CC=C1[N+]([O-])=O YVCMBGPPTCBEDP-UHFFFAOYSA-N 0.000 claims description 2
- MFCHYWIMSNKJMB-UHFFFAOYSA-N 2-methyl-5-[4-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]phenyl]-1,3,4-oxadiazole Chemical compound C1CC(CCC)CCN1C1=CC(OC=2C=CC(=CC=2)C=2OC(C)=NN=2)=CC=C1[N+]([O-])=O MFCHYWIMSNKJMB-UHFFFAOYSA-N 0.000 claims description 2
- DPLLVROAWZVABY-UHFFFAOYSA-N 3-[4-[3-(4-ethoxycarbonylpiperidin-1-yl)-4-nitrophenoxy]phenyl]-2-oxopropanoic acid Chemical compound C1CC(C(=O)OCC)CCN1C1=CC(OC=2C=CC(CC(=O)C(O)=O)=CC=2)=CC=C1[N+]([O-])=O DPLLVROAWZVABY-UHFFFAOYSA-N 0.000 claims description 2
- GFWQTXLDRGKEFG-UHFFFAOYSA-N 3-[4-[3-(4-ethoxycarbonylpiperidin-1-yl)-4-nitrophenoxy]phenyl]propanoic acid Chemical compound C1CC(C(=O)OCC)CCN1C1=CC(OC=2C=CC(CCC(O)=O)=CC=2)=CC=C1[N+]([O-])=O GFWQTXLDRGKEFG-UHFFFAOYSA-N 0.000 claims description 2
- WWNKXJCYOXVTGI-UHFFFAOYSA-N 3-[4-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]phenyl]-2-oxopropanoic acid Chemical compound C1CC(CCC)CCN1C1=CC(OC=2C=CC(CC(=O)C(O)=O)=CC=2)=CC=C1[N+]([O-])=O WWNKXJCYOXVTGI-UHFFFAOYSA-N 0.000 claims description 2
- CEQVJPOYQDBGNE-UHFFFAOYSA-N 3-[4-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]phenyl]propanoic acid Chemical compound C1CC(CCC)CCN1C1=CC(OC=2C=CC(CCC(O)=O)=CC=2)=CC=C1[N+]([O-])=O CEQVJPOYQDBGNE-UHFFFAOYSA-N 0.000 claims description 2
- VFVIASZDGVBAEW-UHFFFAOYSA-N 3-methyl-5-[3-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]phenyl]-1,2,4-oxadiazole Chemical compound C1CC(CCC)CCN1C1=CC(OC=2C=C(C=CC=2)C=2ON=C(C)N=2)=CC=C1[N+]([O-])=O VFVIASZDGVBAEW-UHFFFAOYSA-N 0.000 claims description 2
- QTVLQPAOZWHNFH-UHFFFAOYSA-N 4-[4-[2-nitro-5-(4-propylpiperidin-1-yl)phenoxy]phenyl]butan-2-one Chemical compound C1CC(CCC)CCN1C1=CC=C([N+]([O-])=O)C(OC=2C=CC(CCC(C)=O)=CC=2)=C1 QTVLQPAOZWHNFH-UHFFFAOYSA-N 0.000 claims description 2
- SSZRMWSKPKWIIG-UHFFFAOYSA-N 4-[4-[3-[4-(3-methyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-4-nitrophenoxy]phenyl]butan-2-one Chemical compound C1=CC(CCC(=O)C)=CC=C1OC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)C=2ON=C(C)N=2)=C1 SSZRMWSKPKWIIG-UHFFFAOYSA-N 0.000 claims description 2
- HIBOMQBOJFSMRJ-UHFFFAOYSA-N 4-[4-[3-[4-(methoxymethyl)piperidin-1-yl]-4-nitrophenoxy]phenyl]butan-2-one Chemical compound C1CC(COC)CCN1C1=CC(OC=2C=CC(CCC(C)=O)=CC=2)=CC=C1[N+]([O-])=O HIBOMQBOJFSMRJ-UHFFFAOYSA-N 0.000 claims description 2
- QAQHPPBTEWEEJM-UHFFFAOYSA-N 4-[4-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]phenyl]butan-2-one Chemical compound C1CC(CCC)CCN1C1=CC(OC=2C=CC(CCC(C)=O)=CC=2)=CC=C1[N+]([O-])=O QAQHPPBTEWEEJM-UHFFFAOYSA-N 0.000 claims description 2
- JFIDBMRSEIBNAE-UHFFFAOYSA-N 4-[4-[4-nitro-3-(4-pyridin-2-ylsulfanylpiperidin-1-yl)phenoxy]phenyl]butan-2-one Chemical compound C1=CC(CCC(=O)C)=CC=C1OC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)SC=2N=CC=CC=2)=C1 JFIDBMRSEIBNAE-UHFFFAOYSA-N 0.000 claims description 2
- SOMGOTJVNWMMAF-UHFFFAOYSA-N 4-[4-[5-nitro-6-(4-propylpiperidin-1-yl)pyridin-2-yl]oxyphenyl]butan-2-one Chemical compound C1CC(CCC)CCN1C1=NC(OC=2C=CC(CCC(C)=O)=CC=2)=CC=C1[N+]([O-])=O SOMGOTJVNWMMAF-UHFFFAOYSA-N 0.000 claims description 2
- YWCCANLUHWZFLR-UHFFFAOYSA-N 4-[4-[5-nitro-6-(4-pyridin-2-ylsulfanylpiperidin-1-yl)pyridin-2-yl]oxyphenyl]butan-2-one Chemical compound C1=CC(CCC(=O)C)=CC=C1OC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)SC=2N=CC=CC=2)=N1 YWCCANLUHWZFLR-UHFFFAOYSA-N 0.000 claims description 2
- AUZWGLPRXPPHDO-UHFFFAOYSA-N 5-bromo-1-[4-nitro-3-(4-propylpiperidin-1-yl)phenyl]pyridin-2-one Chemical compound C1CC(CCC)CCN1C1=CC(N2C(C=CC(Br)=C2)=O)=CC=C1[N+]([O-])=O AUZWGLPRXPPHDO-UHFFFAOYSA-N 0.000 claims description 2
- BMNJJEMCZIRGBX-UHFFFAOYSA-N 5-bromo-2-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]pyridine Chemical compound C1CC(CCC)CCN1C1=CC(OC=2N=CC(Br)=CC=2)=CC=C1[N+]([O-])=O BMNJJEMCZIRGBX-UHFFFAOYSA-N 0.000 claims description 2
- HZOHXUIECWRSJH-UHFFFAOYSA-N 5-ethylsulfonyl-2-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]aniline Chemical compound C1CC(CCC)CCN1C1=CC(OC=2C(=CC(=CC=2)S(=O)(=O)CC)N)=CC=C1[N+]([O-])=O HZOHXUIECWRSJH-UHFFFAOYSA-N 0.000 claims description 2
- LDARMEAYYFGMCX-UHFFFAOYSA-N C1CC(CCC)CCN1C1=CC(OC=2C=CC(=CC=2)C2=NN(C)C(O)=C2)=CC=C1[N+]([O-])=O Chemical compound C1CC(CCC)CCN1C1=CC(OC=2C=CC(=CC=2)C2=NN(C)C(O)=C2)=CC=C1[N+]([O-])=O LDARMEAYYFGMCX-UHFFFAOYSA-N 0.000 claims description 2
- VAEPOXPGUPMLJK-UHFFFAOYSA-N [4-[2-nitro-5-(4-propylpiperidin-1-yl)phenoxy]phenyl]-phenylmethanone Chemical compound C1CC(CCC)CCN1C1=CC=C([N+]([O-])=O)C(OC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=C1 VAEPOXPGUPMLJK-UHFFFAOYSA-N 0.000 claims description 2
- GACZXTJOCSDCMT-UHFFFAOYSA-N [4-[3-[4-(methoxymethyl)piperidin-1-yl]-4-nitrophenoxy]phenyl]-phenylmethanone Chemical compound C1CC(COC)CCN1C1=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=CC=C1[N+]([O-])=O GACZXTJOCSDCMT-UHFFFAOYSA-N 0.000 claims description 2
- WVUDQXPBMXVYBW-UHFFFAOYSA-N [4-[4-nitro-3-(4-propylpiperidin-1-yl)anilino]phenyl]-phenylmethanone Chemical compound C1CC(CCC)CCN1C1=CC(NC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=CC=C1[N+]([O-])=O WVUDQXPBMXVYBW-UHFFFAOYSA-N 0.000 claims description 2
- ICWUHNPSRKLUBV-UHFFFAOYSA-N [4-[4-nitro-3-(4-propylpiperidin-1-yl)phenoxy]phenyl]-phenylmethanone Chemical compound C1CC(CCC)CCN1C1=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=CC=C1[N+]([O-])=O ICWUHNPSRKLUBV-UHFFFAOYSA-N 0.000 claims description 2
- DRIFBFDYGLBJJR-UHFFFAOYSA-N [4-[[5-nitro-6-(4-pyridin-2-ylsulfanylpiperidin-1-yl)pyridin-2-yl]amino]phenyl]-phenylmethanone Chemical compound N1=C(N2CCC(CC2)SC=2N=CC=CC=2)C([N+](=O)[O-])=CC=C1NC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 DRIFBFDYGLBJJR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- JFDVGACPVMKGDT-UHFFFAOYSA-N ethyl 1-[2-nitro-5-[4-(3-oxobutyl)phenoxy]phenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC(OC=2C=CC(CCC(C)=O)=CC=2)=CC=C1[N+]([O-])=O JFDVGACPVMKGDT-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D401/02—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 containing two hetero rings
- C07D401/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
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- C—CHEMISTRY; METALLURGY
- 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
- C07D401/02—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 containing two hetero rings
- C07D401/10—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 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D401/02—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 containing two hetero rings
- C07D401/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D401/14—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 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44978803P | 2003-02-24 | 2003-02-24 | |
| US60/449,788 | 2003-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050106033A true KR20050106033A (ko) | 2005-11-08 |
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-
2004
- 2004-02-23 WO PCT/US2004/005555 patent/WO2004076413A2/en not_active Ceased
- 2004-02-23 JP JP2006503856A patent/JP2006518763A/ja active Pending
- 2004-02-23 MX MXPA05007614A patent/MXPA05007614A/es active IP Right Grant
- 2004-02-23 EP EP04713803A patent/EP1606282B1/en not_active Expired - Lifetime
- 2004-02-23 BR BRPI0407620-6A patent/BRPI0407620A/pt not_active IP Right Cessation
- 2004-02-23 AT AT04713803T patent/ATE414076T1/de active
- 2004-02-23 DK DK04713803T patent/DK1606282T3/da active
- 2004-02-23 ES ES04713803T patent/ES2316964T3/es not_active Expired - Lifetime
- 2004-02-23 CA CA002515963A patent/CA2515963A1/en not_active Withdrawn
- 2004-02-23 PL PL378295A patent/PL378295A1/pl not_active Application Discontinuation
- 2004-02-23 EA EA200501348A patent/EA200501348A1/ru unknown
- 2004-02-23 AU AU2004215344A patent/AU2004215344B2/en not_active Ceased
- 2004-02-23 CN CNA2004800044127A patent/CN1751038A/zh active Pending
- 2004-02-23 DE DE602004017703T patent/DE602004017703D1/de not_active Expired - Lifetime
- 2004-02-23 SI SI200431030T patent/SI1606282T1/sl unknown
- 2004-02-23 PT PT04713803T patent/PT1606282E/pt unknown
- 2004-02-23 KR KR1020057015582A patent/KR20050106033A/ko not_active Ceased
- 2004-02-23 US US10/546,665 patent/US20070066590A1/en not_active Abandoned
-
2009
- 2009-01-29 CY CY20091100109T patent/CY1108736T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006518763A (ja) | 2006-08-17 |
| HK1077305A1 (en) | 2006-02-10 |
| CY1108736T1 (el) | 2014-04-09 |
| ATE414076T1 (de) | 2008-11-15 |
| US20070066590A1 (en) | 2007-03-22 |
| WO2004076413A3 (en) | 2004-12-02 |
| EA200501348A1 (ru) | 2006-02-24 |
| CN1751038A (zh) | 2006-03-22 |
| EP1606282B1 (en) | 2008-11-12 |
| AU2004215344A1 (en) | 2004-09-10 |
| PL378295A1 (pl) | 2006-03-20 |
| SI1606282T1 (sl) | 2009-04-30 |
| CA2515963A1 (en) | 2004-09-10 |
| DE602004017703D1 (de) | 2008-12-24 |
| BRPI0407620A (pt) | 2006-02-21 |
| DK1606282T3 (da) | 2009-03-16 |
| WO2004076413A2 (en) | 2004-09-10 |
| AU2004215344B2 (en) | 2010-06-24 |
| EP1606282A2 (en) | 2005-12-21 |
| MXPA05007614A (es) | 2006-05-25 |
| PT1606282E (pt) | 2009-02-10 |
| ES2316964T3 (es) | 2009-04-16 |
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