JP2009538339A5

JP2009538339A5 -

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Publication number: JP2009538339A5
Authority: JP; Japan
Prior art keywords: alkyl; cycloalkyl; alkyloxy; group; optionally
Prior art date: 2007-05-22
Legal status : Granted

Application number

JP2009512269A

Other languages

English (en)

Japanese (ja)

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JP5230613B2 (ja

JP2009538339A (ja

Filing date

2007-05-22

Publication date

2010-07-08

2007-05-22 Application filed filed Critical

2007-05-22 Priority claimed from PCT/US2007/069487 external-priority patent/WO2007140191A2/en

2009-11-05 Publication of JP2009538339A publication Critical patent/JP2009538339A/ja

2010-07-08 Publication of JP2009538339A5 publication Critical patent/JP2009538339A5/ja

2013-07-10 Application granted granted Critical

2013-07-10 Publication of JP5230613B2 publication Critical patent/JP5230613B2/ja

Status Active legal-status Critical Current

2027-05-22 Anticipated expiration legal-status Critical

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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 description 529
125000000217 alkyl group Chemical group 0.000 claims description 386
-1 pyrrolidin-1-ylcarbonyl Chemical group 0.000 claims description 280
150000001875 compounds Chemical class 0.000 claims description 270
125000003545 alkoxy group Chemical group 0.000 claims description 160
125000000753 cycloalkyl group Chemical group 0.000 claims description 154
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 122
125000005843 halogen group Chemical group 0.000 claims description 111
125000001424 substituent group Chemical group 0.000 claims description 98
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 95
229910052739 hydrogen Inorganic materials 0.000 claims description 88
125000000000 cycloalkoxy group Chemical group 0.000 claims description 83
239000001257 hydrogen Substances 0.000 claims description 80
125000000392 cycloalkenyl group Chemical group 0.000 claims description 78
239000003814 drug Substances 0.000 claims description 78
229910052760 oxygen Inorganic materials 0.000 claims description 67
125000003342 alkenyl group Chemical group 0.000 claims description 66
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 63
229910052717 sulfur Inorganic materials 0.000 claims description 63
239000000203 mixture Substances 0.000 claims description 62
125000004093 cyano group Chemical group *C#N 0.000 claims description 61
150000002431 hydrogen Chemical class 0.000 claims description 59
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 55
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 52
125000000304 alkynyl group Chemical group 0.000 claims description 45
125000003118 aryl group Chemical group 0.000 claims description 44
125000001072 heteroaryl group Chemical group 0.000 claims description 43
229910002091 carbon monoxide Inorganic materials 0.000 claims description 42
239000000460 chlorine Substances 0.000 claims description 39
229940124597 therapeutic agent Drugs 0.000 claims description 37
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 36
229910052801 chlorine Inorganic materials 0.000 claims description 36
239000003795 chemical substances by application Substances 0.000 claims description 35
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 29
229940079593 drug Drugs 0.000 claims description 28
239000003112 inhibitor Substances 0.000 claims description 26
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 26
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 25
125000001153 fluoro group Chemical group F* 0.000 claims description 24
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 24
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
125000004104 aryloxy group Chemical group 0.000 claims description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
229910052731 fluorine Inorganic materials 0.000 claims description 22
239000011737 fluorine Substances 0.000 claims description 22
125000005553 heteroaryloxy group Chemical group 0.000 claims description 22
239000001301 oxygen Substances 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
239000003472 antidiabetic agent Substances 0.000 claims description 19
239000008194 pharmaceutical composition Substances 0.000 claims description 19
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 18
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
239000000556 agonist Substances 0.000 claims description 17
150000002632 lipids Chemical class 0.000 claims description 17
239000011593 sulfur Chemical group 0.000 claims description 17
208000002249 Diabetes Complications Diseases 0.000 claims description 16
206010012655 Diabetic complications Diseases 0.000 claims description 16
229940125708 antidiabetic agent Drugs 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
201000001320 Atherosclerosis Diseases 0.000 claims description 15
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
206010007558 Cardiac failure chronic Diseases 0.000 claims description 14
239000000883 anti-obesity agent Substances 0.000 claims description 14
229940125710 antiobesity agent Drugs 0.000 claims description 14
125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 14
125000005163 aryl sulfanyl group Chemical group 0.000 claims description 14
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 14
125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 14
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 14
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 14
125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
102000004877 Insulin Human genes 0.000 claims description 13
108090001061 Insulin Proteins 0.000 claims description 13
206010022489 Insulin Resistance Diseases 0.000 claims description 13
229940125396 insulin Drugs 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
229940123208 Biguanide Drugs 0.000 claims description 11
239000012190 activator Substances 0.000 claims description 11
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 11
239000002220 antihypertensive agent Substances 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 11
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 11
125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 11
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 11
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 10
229940030600 antihypertensive agent Drugs 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 10
201000001421 hyperglycemia Diseases 0.000 claims description 10
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 9
101150065749 Churc1 gene Proteins 0.000 claims description 9
102100038239 Protein Churchill Human genes 0.000 claims description 9
206010012601 diabetes mellitus Diseases 0.000 claims description 9
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 8
206010030113 Oedema Diseases 0.000 claims description 8
102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims description 8
229940100389 Sulfonylurea Drugs 0.000 claims description 8
108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims description 8
229960002797 pitavastatin Drugs 0.000 claims description 8
RHGYHLPFVJEAOC-FFNUKLMVSA-L pitavastatin calcium Chemical compound [Ca+2].[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1.[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 RHGYHLPFVJEAOC-FFNUKLMVSA-L 0.000 claims description 8
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 7
206010060378 Hyperinsulinaemia Diseases 0.000 claims description 7
206010020772 Hypertension Diseases 0.000 claims description 7
201000001431 Hyperuricemia Diseases 0.000 claims description 7
208000001145 Metabolic Syndrome Diseases 0.000 claims description 7
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 7
208000008589 Obesity Diseases 0.000 claims description 7
229940123464 Thiazolidinedione Drugs 0.000 claims description 7
201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 7
125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 7
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 7
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 7
230000003451 hyperinsulinaemic effect Effects 0.000 claims description 7
201000008980 hyperinsulinism Diseases 0.000 claims description 7
235000020824 obesity Nutrition 0.000 claims description 7
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 6
125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 6
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
108010078791 Carrier Proteins Proteins 0.000 claims description 6
102000014914 Carrier Proteins Human genes 0.000 claims description 6
208000032928 Dyslipidaemia Diseases 0.000 claims description 6
208000017170 Lipid metabolism disease Diseases 0.000 claims description 6
108010016731 PPAR gamma Proteins 0.000 claims description 6
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 6
125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 6
LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims description 6
PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 claims description 6
DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims description 6
HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 6
229940121649 protein inhibitor Drugs 0.000 claims description 6
239000012268 protein inhibitor Substances 0.000 claims description 6
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
108010041872 Islet Amyloid Polypeptide Proteins 0.000 claims description 5
102000036770 Islet Amyloid Polypeptide Human genes 0.000 claims description 5
102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims description 5
239000003741 agents affecting lipid metabolism Substances 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
239000003524 antilipemic agent Substances 0.000 claims description 5
210000004185 liver Anatomy 0.000 claims description 5
229940044601 receptor agonist Drugs 0.000 claims description 5
239000000018 receptor agonist Substances 0.000 claims description 5
229940044551 receptor antagonist Drugs 0.000 claims description 5
239000002464 receptor antagonist Substances 0.000 claims description 5
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 5
CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 claims description 5
SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 claims description 4
229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 4
239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 4
229960004580 glibenclamide Drugs 0.000 claims description 4
ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 claims description 4
229950004994 meglitinide Drugs 0.000 claims description 4
CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 claims description 4
229950004514 torcetrapib Drugs 0.000 claims description 4
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims description 3
XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims description 3
HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 3
ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims description 3
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 3
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 3
BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 claims description 3
VTAKZNRDSPNOAU-UHFFFAOYSA-M 2-(chloromethyl)oxirane;hydron;prop-2-en-1-amine;n-prop-2-enyldecan-1-amine;trimethyl-[6-(prop-2-enylamino)hexyl]azanium;dichloride Chemical compound Cl.[Cl-].NCC=C.ClCC1CO1.CCCCCCCCCCNCC=C.C[N+](C)(C)CCCCCCNCC=C VTAKZNRDSPNOAU-UHFFFAOYSA-M 0.000 claims description 3
ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims description 3
102000006902 5-HT2C Serotonin Receptor Human genes 0.000 claims description 3
108010072553 5-HT2C Serotonin Receptor Proteins 0.000 claims description 3
229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims description 3
DJQOOSBJCLSSEY-UHFFFAOYSA-N Acipimox Chemical compound CC1=CN=C(C(O)=O)C=[N+]1[O-] DJQOOSBJCLSSEY-UHFFFAOYSA-N 0.000 claims description 3
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 3
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 3
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 3
229940123158 Cannabinoid CB1 receptor antagonist Drugs 0.000 claims description 3
RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 claims description 3
229920001268 Cholestyramine Polymers 0.000 claims description 3
108010005939 Ciliary Neurotrophic Factor Proteins 0.000 claims description 3
102100031614 Ciliary neurotrophic factor Human genes 0.000 claims description 3
229920002905 Colesevelam Polymers 0.000 claims description 3
229920002911 Colestipol Polymers 0.000 claims description 3
URRAHSMDPCMOTH-LNLFQRSKSA-N Denagliptin Chemical compound C=1C=C(F)C=CC=1C([C@H](N)C(=O)N1[C@@H](C[C@H](F)C1)C#N)C1=CC=C(F)C=C1 URRAHSMDPCMOTH-LNLFQRSKSA-N 0.000 claims description 3
229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 claims description 3
102100030431 Fatty acid-binding protein, adipocyte Human genes 0.000 claims description 3
102000027487 Fructose-Bisphosphatase Human genes 0.000 claims description 3
108010017464 Fructose-Bisphosphatase Proteins 0.000 claims description 3
HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 claims description 3
229940122904 Glucagon receptor antagonist Drugs 0.000 claims description 3
229940121931 Gluconeogenesis inhibitor Drugs 0.000 claims description 3
102000003638 Glucose-6-Phosphatase Human genes 0.000 claims description 3
108010086800 Glucose-6-Phosphatase Proteins 0.000 claims description 3
229940123856 Glycogen synthase kinase 3 inhibitor Drugs 0.000 claims description 3
229940122199 Insulin secretagogue Drugs 0.000 claims description 3
XUIIKFGFIJCVMT-LBPRGKRZSA-N L-thyroxine Chemical compound IC1=CC(C[C@H]([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-LBPRGKRZSA-N 0.000 claims description 3
102000000853 LDL receptors Human genes 0.000 claims description 3
108010001831 LDL receptors Proteins 0.000 claims description 3
102000016267 Leptin Human genes 0.000 claims description 3
108010092277 Leptin Proteins 0.000 claims description 3
229940086609 Lipase inhibitor Drugs 0.000 claims description 3
102000004895 Lipoproteins Human genes 0.000 claims description 3
108090001030 Lipoproteins Proteins 0.000 claims description 3
239000000867 Lipoxygenase Inhibitor Substances 0.000 claims description 3
229940122142 Lipoxygenase inhibitor Drugs 0.000 claims description 3
102100030817 Liver carboxylesterase 1 Human genes 0.000 claims description 3
101710181187 Liver carboxylesterase 1 Proteins 0.000 claims description 3
ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 claims description 3
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JP2009512269A 2006-05-23 2007-05-22 グルコース輸送体阻害剤およびその使用方法 Active JP5230613B2 (ja)