BRPI0612996A2 - ativadores de urÉia glucocinase - Google Patents

Info

Publication number

BRPI0612996A2

BRPI0612996A2 BRPI0612996-0A BRPI0612996A BRPI0612996A2 BR PI0612996 A2 BRPI0612996 A2 BR PI0612996A2 BR PI0612996 A BRPI0612996 A BR PI0612996A BR PI0612996 A2 BRPI0612996 A2 BR PI0612996A2

Authority

BR

Brazil

Prior art keywords

alkyl

cycloalkyl

independently selected

aryl

compound according

Prior art date

2005-07-14

Links

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• 102000030595 Glucokinase Human genes 0.000 title abstract description 37
• 108010021582 Glucokinase Proteins 0.000 title abstract description 37
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title abstract description 8
• 239000012190 activator Substances 0.000 title abstract description 8
• 239000004202 carbamide Substances 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 278
• -1 cyano, hydroxy Chemical group 0.000 claims description 667
• 125000000217 alkyl group Chemical group 0.000 claims description 289
• 125000001424 substituent group Chemical group 0.000 claims description 155
• 239000002253 acid Substances 0.000 claims description 118
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 90
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 79
• 125000003545 alkoxy group Chemical group 0.000 claims description 69
• 125000003118 aryl group Chemical group 0.000 claims description 67
• 125000001072 heteroaryl group Chemical group 0.000 claims description 61
• 239000000203 mixture Substances 0.000 claims description 54
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 44
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 41
• 125000000623 heterocyclic group Chemical group 0.000 claims description 41
• 150000002367 halogens Chemical class 0.000 claims description 39
• 229910052757 nitrogen Inorganic materials 0.000 claims description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 28
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 26
• 239000000460 chlorine Substances 0.000 claims description 25
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
• 229910052794 bromium Inorganic materials 0.000 claims description 21
• 229910052801 chlorine Inorganic materials 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 19
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 229910052717 sulfur Chemical group 0.000 claims description 14
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 13
• 125000005108 alkenylthio group Chemical group 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
• 239000001301 oxygen Chemical group 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• 239000011593 sulfur Chemical group 0.000 claims description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 10
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
• 125000004043 oxo group Chemical group O=* 0.000 claims description 8
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 5
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 5
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004344 phenylpropyl group Chemical group 0.000 claims description 5
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 5
• 229930192474 thiophene Natural products 0.000 claims description 5
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
• 125000004710 2-methylpropylthio group Chemical group CC(CS*)C 0.000 claims description 4
• KBSDLBVPAHQCRY-UHFFFAOYSA-N 307496-19-1 Chemical group C1CC=CCC1CC[Si](O1)(O2)O[Si](O3)(C4CCCC4)O[Si](O4)(C5CCCC5)O[Si]1(C1CCCC1)O[Si](O1)(C5CCCC5)O[Si]2(C2CCCC2)O[Si]3(C2CCCC2)O[Si]41C1CCCC1 KBSDLBVPAHQCRY-UHFFFAOYSA-N 0.000 claims description 4
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
• 125000005110 aryl thio group Chemical group 0.000 claims description 4
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 4
• 230000003287 optical effect Effects 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 3
• 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 3
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 229910052744 lithium Inorganic materials 0.000 claims description 3
• 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 3
• 125000006655 (C3-C8) heteroaryl group Chemical group 0.000 claims description 2
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
• 229910052799 carbon Inorganic materials 0.000 claims 2
• 125000002877 alkyl aryl group Chemical group 0.000 claims 1
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims 1
• 125000005241 heteroarylamino group Chemical group 0.000 claims 1
• 125000004468 heterocyclylthio group Chemical group 0.000 claims 1
• 238000011282 treatment Methods 0.000 abstract description 68
• 238000002360 preparation method Methods 0.000 abstract description 44
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 26
• 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract description 25
• 201000010099 disease Diseases 0.000 abstract description 17
• 239000003814 drug Substances 0.000 abstract description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 262
• 229960000583 acetic acid Drugs 0.000 description 237
• 230000015572 biosynthetic process Effects 0.000 description 134
• 238000003786 synthesis reaction Methods 0.000 description 130
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 124
• 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 description 97
• 238000005160 1H NMR spectroscopy Methods 0.000 description 96
• 238000000034 method Methods 0.000 description 81
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 66
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 58
• 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 description 47
• 239000008103 glucose Substances 0.000 description 47
• 108090001061 Insulin Proteins 0.000 description 45
• 102000004877 Insulin Human genes 0.000 description 45
• QRIYTBYTQBRMNL-UHFFFAOYSA-N ethyl 2-[(2-amino-1,3-thiazol-5-yl)sulfanyl]acetate Chemical compound CCOC(=O)CSC1=CN=C(N)S1 QRIYTBYTQBRMNL-UHFFFAOYSA-N 0.000 description 45
• 229940125396 insulin Drugs 0.000 description 45
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• GDKRHCIXCFSWKN-UHFFFAOYSA-N 2-[[2-[[cyclohexyl(2-phenylethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C1CCCCC1)CCC1=CC=CC=C1 GDKRHCIXCFSWKN-UHFFFAOYSA-N 0.000 description 42
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
• YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 40
• 239000008194 pharmaceutical composition Substances 0.000 description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• 125000004494 ethyl ester group Chemical group 0.000 description 33
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
• 238000006243 chemical reaction Methods 0.000 description 31
• 239000011541 reaction mixture Substances 0.000 description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 26
• 239000002904 solvent Substances 0.000 description 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 24
• 210000004369 blood Anatomy 0.000 description 23
• 239000008280 blood Substances 0.000 description 23
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• 206010012601 diabetes mellitus Diseases 0.000 description 21
• 150000003254 radicals Chemical class 0.000 description 21
• 206010020772 Hypertension Diseases 0.000 description 20
• 239000000243 solution Substances 0.000 description 20
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 19
• KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 19
• PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 19
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
• 208000013016 Hypoglycemia Diseases 0.000 description 18
• 150000001412 amines Chemical class 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 17
• PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 description 17
• 230000002473 insulinotropic effect Effects 0.000 description 17
• 208000008589 Obesity Diseases 0.000 description 16
• 229940100389 Sulfonylurea Drugs 0.000 description 16
• 230000002218 hypoglycaemic effect Effects 0.000 description 16
• 235000020824 obesity Nutrition 0.000 description 16
• 239000012074 organic phase Substances 0.000 description 16
• 230000002829 reductive effect Effects 0.000 description 16
• 238000003556 assay Methods 0.000 description 15
• 230000001965 increasing effect Effects 0.000 description 15
• 238000010606 normalization Methods 0.000 description 15
• 101000976075 Homo sapiens Insulin Proteins 0.000 description 14
• 239000000556 agonist Substances 0.000 description 14
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