JP2007500719A5 - - Google Patents
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- JP2007500719A5 JP2007500719A5 JP2006522095A JP2006522095A JP2007500719A5 JP 2007500719 A5 JP2007500719 A5 JP 2007500719A5 JP 2006522095 A JP2006522095 A JP 2006522095A JP 2006522095 A JP2006522095 A JP 2006522095A JP 2007500719 A5 JP2007500719 A5 JP 2007500719A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- group
- independently selected
- cycloalkyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 80
- VGYSWOQZWCAVQZ-UHFFFAOYSA-N 5-bromo-n-(2-cyclopropylethyl)-6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridine-3-sulfonamide Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCN(CC2)C=2C(=CC(=CN=2)S(=O)(=O)NCCC2CC2)Br)=C1 VGYSWOQZWCAVQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 119
- 239000001257 hydrogen Substances 0.000 claims 119
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 77
- 125000000753 cycloalkyl group Chemical group 0.000 claims 73
- 125000000217 alkyl group Chemical group 0.000 claims 71
- 125000003710 aryl alkyl group Chemical group 0.000 claims 71
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 68
- 125000000623 heterocyclic group Chemical group 0.000 claims 68
- 125000001072 heteroaryl group Chemical group 0.000 claims 65
- 125000003118 aryl group Chemical group 0.000 claims 59
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 50
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 47
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 43
- 150000002431 hydrogen Chemical class 0.000 claims 42
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 36
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims 36
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 30
- -1 bromo, fluoro, chloro, methyl Chemical group 0.000 claims 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims 24
- 125000005843 halogen group Chemical group 0.000 claims 20
- 125000001424 substituent group Chemical group 0.000 claims 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 16
- 125000003367 polycyclic group Chemical group 0.000 claims 15
- 108010087894 Fatty acid desaturases Proteins 0.000 claims 14
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 claims 14
- 239000003814 drug Substances 0.000 claims 14
- 229940079593 drug Drugs 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 201000010099 disease Diseases 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 13
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 239000003795 chemical substances by application Substances 0.000 claims 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 8
- 241000124008 Mammalia Species 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 6
- 239000000651 prodrug Substances 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 230000005856 abnormality Effects 0.000 claims 5
- 230000001404 mediated effect Effects 0.000 claims 5
- 125000001246 bromo group Chemical group Br* 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 208000004930 Fatty Liver Diseases 0.000 claims 2
- 206010019708 Hepatic steatosis Diseases 0.000 claims 2
- 101000631826 Homo sapiens Stearoyl-CoA desaturase Proteins 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 2
- 208000010706 fatty liver disease Diseases 0.000 claims 2
- 102000055981 human SCD1 Human genes 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 2
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- BWHQNZKTIFGBIY-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]urea Chemical compound C1=CC(F)=CC=C1CNC(=O)NC1=CC=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=C1 BWHQNZKTIFGBIY-UHFFFAOYSA-N 0.000 claims 1
- SHIBQVFGKOYTOZ-UHFFFAOYSA-N 1-[6-[4-(cyclohexanecarbonyl)piperazin-1-yl]pyridin-3-yl]-3-pentylurea Chemical compound N1=CC(NC(=O)NCCCCC)=CC=C1N1CCN(C(=O)C2CCCCC2)CC1 SHIBQVFGKOYTOZ-UHFFFAOYSA-N 0.000 claims 1
- VJXYOPYNLAFVLT-UHFFFAOYSA-N 1-[6-[4-(cyclopentanecarbonyl)piperazin-1-yl]pyridin-3-yl]-3-pentylurea Chemical compound N1=CC(NC(=O)NCCCCC)=CC=C1N1CCN(C(=O)C2CCCC2)CC1 VJXYOPYNLAFVLT-UHFFFAOYSA-N 0.000 claims 1
- MSAJNTURICXWMG-UHFFFAOYSA-N 1-benzyl-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=CC(NC(=O)NCC=3C=CC=CC=3)=CC=2)CC1 MSAJNTURICXWMG-UHFFFAOYSA-N 0.000 claims 1
- SETHYFAYGJYELK-UHFFFAOYSA-N 1-butyl-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]urea Chemical compound N1=CC(NC(=O)NCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 SETHYFAYGJYELK-UHFFFAOYSA-N 0.000 claims 1
- OWQDTUMYACMNPZ-UHFFFAOYSA-N 1-pentyl-3-[6-[4-(pyridine-2-carbonyl)piperazin-1-yl]pyridin-3-yl]urea Chemical compound N1=CC(NC(=O)NCCCCC)=CC=C1N1CCN(C(=O)C=2N=CC=CC=2)CC1 OWQDTUMYACMNPZ-UHFFFAOYSA-N 0.000 claims 1
- NFJJLEVUQMOBTC-UHFFFAOYSA-N 1-pentyl-3-[6-[4-(pyridine-4-carbonyl)piperazin-1-yl]pyridin-3-yl]urea Chemical compound N1=CC(NC(=O)NCCCCC)=CC=C1N1CCN(C(=O)C=2C=CN=CC=2)CC1 NFJJLEVUQMOBTC-UHFFFAOYSA-N 0.000 claims 1
- UTUFVPXFZZZFGN-UHFFFAOYSA-N 1-pentyl-3-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]urea Chemical compound N1=CC(NC(=O)NCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 UTUFVPXFZZZFGN-UHFFFAOYSA-N 0.000 claims 1
- DYGCSVJUSRRMNV-UHFFFAOYSA-N 3-phenyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]propanamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=CC(NC(=O)CCC=3C=CC=CC=3)=CC=2)CC1 DYGCSVJUSRRMNV-UHFFFAOYSA-N 0.000 claims 1
- PMPRNHCEJRGQER-UHFFFAOYSA-N 3-phenyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]propane-1-sulfonamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=CC(NS(=O)(=O)CCCC=3C=CC=CC=3)=CC=2)CC1 PMPRNHCEJRGQER-UHFFFAOYSA-N 0.000 claims 1
- DWLBJBPXPZTHRL-UHFFFAOYSA-N 4-methyl-n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]pentanamide Chemical compound N1=CC(NC(=O)CCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 DWLBJBPXPZTHRL-UHFFFAOYSA-N 0.000 claims 1
- MRZOEVPTAGFNBJ-UHFFFAOYSA-N CC(C1=CC=CC=C1)NC(NC1=CC=C(N(CC2)CCN2C(C2=C(C(F)(F)F)C=CC=C2)=O)N=C1)=O Chemical compound CC(C1=CC=CC=C1)NC(NC1=CC=C(N(CC2)CCN2C(C2=C(C(F)(F)F)C=CC=C2)=O)N=C1)=O MRZOEVPTAGFNBJ-UHFFFAOYSA-N 0.000 claims 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- XCXZTLXCCYWIHM-UHFFFAOYSA-N n-(2-cyclopropylethyl)-6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridine-3-sulfonamide Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCN(CC2)C=2N=CC(=CC=2)S(=O)(=O)NCCC2CC2)=C1 XCXZTLXCCYWIHM-UHFFFAOYSA-N 0.000 claims 1
- LYUAIDPXQPEPAN-UHFFFAOYSA-N n-[6-[2-oxo-4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]-4-phenylbutanamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CC(=O)N(C=2N=CC(NC(=O)CCCC=3C=CC=CC=3)=CC=2)CC1 LYUAIDPXQPEPAN-UHFFFAOYSA-N 0.000 claims 1
- LWZBMBILYPQPLU-UHFFFAOYSA-N n-[6-[4-(2,5-dichlorobenzoyl)piperazin-1-yl]pyridin-3-yl]heptanamide Chemical compound N1=CC(NC(=O)CCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=C(Cl)C=2)Cl)CC1 LWZBMBILYPQPLU-UHFFFAOYSA-N 0.000 claims 1
- YSRJBLAQQFNIFF-UHFFFAOYSA-N n-[6-[4-(2,5-dichlorobenzoyl)piperazin-1-yl]pyridin-3-yl]hexane-1-sulfonamide Chemical compound N1=CC(NS(=O)(=O)CCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=C(Cl)C=2)Cl)CC1 YSRJBLAQQFNIFF-UHFFFAOYSA-N 0.000 claims 1
- OTLZKWOIKPHLAG-UHFFFAOYSA-N n-[6-[4-(2,5-dichlorobenzoyl)piperazin-1-yl]pyridin-3-yl]pentane-1-sulfonamide Chemical compound N1=CC(NS(=O)(=O)CCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=C(Cl)C=2)Cl)CC1 OTLZKWOIKPHLAG-UHFFFAOYSA-N 0.000 claims 1
- GTDXQDLDSBIWGE-UHFFFAOYSA-N n-[6-[4-(2-bromobenzoyl)piperazin-1-yl]pyridin-3-yl]pentane-1-sulfonamide Chemical compound N1=CC(NS(=O)(=O)CCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)Br)CC1 GTDXQDLDSBIWGE-UHFFFAOYSA-N 0.000 claims 1
- KDXJVMPAIXDGML-UHFFFAOYSA-N n-[6-[4-(cyclohexanecarbonyl)piperazin-1-yl]pyridin-3-yl]cyclohexanecarboxamide Chemical compound C1CCCCC1C(=O)NC(C=N1)=CC=C1N(CC1)CCN1C(=O)C1CCCCC1 KDXJVMPAIXDGML-UHFFFAOYSA-N 0.000 claims 1
- YHZAMSOVDNMGLC-UHFFFAOYSA-N n-[6-[4-(naphthalene-1-carbonyl)piperazin-1-yl]pyridin-3-yl]hexane-1-sulfonamide Chemical compound N1=CC(NS(=O)(=O)CCCCCC)=CC=C1N1CCN(C(=O)C=2C3=CC=CC=C3C=CC=2)CC1 YHZAMSOVDNMGLC-UHFFFAOYSA-N 0.000 claims 1
- YTTGWVXQNYROBJ-UHFFFAOYSA-N n-[6-[4-(naphthalene-1-carbonyl)piperazin-1-yl]pyridin-3-yl]pentane-1-sulfonamide Chemical compound N1=CC(NS(=O)(=O)CCCCC)=CC=C1N1CCN(C(=O)C=2C3=CC=CC=C3C=CC=2)CC1 YTTGWVXQNYROBJ-UHFFFAOYSA-N 0.000 claims 1
- SKVZSPBXGPHGKS-UHFFFAOYSA-N n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]butane-1-sulfonamide Chemical compound N1=CC(NS(=O)(=O)CCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 SKVZSPBXGPHGKS-UHFFFAOYSA-N 0.000 claims 1
- ANKMEDVQGBWVNU-UHFFFAOYSA-N n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]heptanamide Chemical compound N1=CC(NC(=O)CCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 ANKMEDVQGBWVNU-UHFFFAOYSA-N 0.000 claims 1
- XXUQOIASRQOUAG-UHFFFAOYSA-N n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]hexanamide Chemical compound N1=CC(NC(=O)CCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 XXUQOIASRQOUAG-UHFFFAOYSA-N 0.000 claims 1
- CEUVRTXEJIZJNR-UHFFFAOYSA-N n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]hexane-1-sulfonamide Chemical compound N1=CC(NS(=O)(=O)CCCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 CEUVRTXEJIZJNR-UHFFFAOYSA-N 0.000 claims 1
- NIESZWJHNKBXSD-UHFFFAOYSA-N n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridin-3-yl]pentane-1-sulfonamide Chemical compound N1=CC(NS(=O)(=O)CCCCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 NIESZWJHNKBXSD-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- MONRWRVYLOHUFA-UHFFFAOYSA-N pentylurea Chemical compound CCCCCNC(N)=O MONRWRVYLOHUFA-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000012267 brine Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZOGZOXRETBBBJI-UHFFFAOYSA-N 2-cyclopropylethanamine Chemical compound NCCC1CC1 ZOGZOXRETBBBJI-UHFFFAOYSA-N 0.000 description 1
- WOJIIXQKYCQUIZ-UHFFFAOYSA-N 5-bromo-6-chloro-n-(2-cyclopropylethyl)pyridine-3-sulfonamide Chemical compound C1=C(Br)C(Cl)=NC=C1S(=O)(=O)NCCC1CC1 WOJIIXQKYCQUIZ-UHFFFAOYSA-N 0.000 description 1
- TURGMVYIESHZBE-UHFFFAOYSA-N 5-bromo-6-chloropyridine-3-sulfonyl chloride Chemical compound ClC1=NC=C(S(Cl)(=O)=O)C=C1Br TURGMVYIESHZBE-UHFFFAOYSA-N 0.000 description 1
- ZKHVSNDPPPJHTM-UHFFFAOYSA-N [5-fluoro-2-(trifluoromethyl)phenyl]-piperazin-1-ylmethanone Chemical compound FC1=CC=C(C(F)(F)F)C(C(=O)N2CCNCC2)=C1 ZKHVSNDPPPJHTM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49111803P | 2003-07-30 | 2003-07-30 | |
| US49111603P | 2003-07-30 | 2003-07-30 | |
| US49134003P | 2003-07-30 | 2003-07-30 | |
| US60/491,340 | 2003-07-30 | ||
| US60/491,116 | 2003-07-30 | ||
| US60/491,118 | 2003-07-30 | ||
| PCT/US2004/024657 WO2005011656A2 (en) | 2003-07-30 | 2004-07-29 | Pyridyl derivatives and their use as therapeutic agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007500719A JP2007500719A (ja) | 2007-01-18 |
| JP2007500719A5 true JP2007500719A5 (https=) | 2007-09-13 |
| JP4782008B2 JP4782008B2 (ja) | 2011-09-28 |
Family
ID=34119804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006522095A Expired - Fee Related JP4782008B2 (ja) | 2003-07-30 | 2004-07-29 | ピリジル誘導体および治療剤としてのその用途 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7605161B2 (https=) |
| EP (2) | EP2316825A1 (https=) |
| JP (1) | JP4782008B2 (https=) |
| KR (1) | KR20060036106A (https=) |
| AU (2) | AU2004261267B9 (https=) |
| BR (1) | BRPI0412352A (https=) |
| CA (1) | CA2533900A1 (https=) |
| EC (1) | ECSP066312A (https=) |
| ES (1) | ES2397389T3 (https=) |
| IL (1) | IL173398A0 (https=) |
| MA (1) | MA28008A1 (https=) |
| NO (1) | NO20060972L (https=) |
| SG (1) | SG145700A1 (https=) |
| TN (1) | TNSN06036A1 (https=) |
| WO (1) | WO2005011656A2 (https=) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7517884B2 (en) | 1998-03-30 | 2009-04-14 | Kalypsys Inc. | Sulfonyl-substituted bicyclic compounds as modulators of PPAR |
| MXPA06001202A (es) * | 2003-07-29 | 2006-08-31 | Xenon Pharmaceuticals Inc | Derivados piridilo y su uso como agentes terapeuticos. |
| WO2006004200A1 (ja) * | 2004-07-02 | 2006-01-12 | Sankyo Company, Limited | ウレア誘導体 |
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-
2004
- 2004-07-29 KR KR1020067002002A patent/KR20060036106A/ko not_active Ceased
- 2004-07-29 AU AU2004261267A patent/AU2004261267B9/en not_active Ceased
- 2004-07-29 JP JP2006522095A patent/JP4782008B2/ja not_active Expired - Fee Related
- 2004-07-29 CA CA002533900A patent/CA2533900A1/en not_active Abandoned
- 2004-07-29 EP EP10184703A patent/EP2316825A1/en not_active Withdrawn
- 2004-07-29 SG SG200805679-8A patent/SG145700A1/en unknown
- 2004-07-29 BR BRPI0412352-2A patent/BRPI0412352A/pt not_active IP Right Cessation
- 2004-07-29 US US10/566,193 patent/US7605161B2/en not_active Expired - Fee Related
- 2004-07-29 WO PCT/US2004/024657 patent/WO2005011656A2/en not_active Ceased
- 2004-07-29 ES ES04779655T patent/ES2397389T3/es not_active Expired - Lifetime
- 2004-07-29 EP EP04779655A patent/EP1651606B1/en not_active Expired - Lifetime
-
2006
- 2006-01-25 EC EC2006006312A patent/ECSP066312A/es unknown
- 2006-01-26 IL IL173398A patent/IL173398A0/en unknown
- 2006-01-27 TN TNP2006000036A patent/TNSN06036A1/en unknown
- 2006-02-27 MA MA28836A patent/MA28008A1/fr unknown
- 2006-02-28 NO NO20060972A patent/NO20060972L/no not_active Application Discontinuation
-
2009
- 2009-05-11 AU AU2009201861A patent/AU2009201861A1/en not_active Abandoned
- 2009-09-02 US US12/552,868 patent/US8153636B2/en not_active Expired - Fee Related
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