JP4960355B2 - ウレア型グルコキナーゼ活性化剤 - Google Patents

Info

Publication number

JP4960355B2

JP4960355B2 JP2008520892A JP2008520892A JP4960355B2 JP 4960355 B2 JP4960355 B2 JP 4960355B2 JP 2008520892 A JP2008520892 A JP 2008520892A JP 2008520892 A JP2008520892 A JP 2008520892A JP 4960355 B2 JP4960355 B2 JP 4960355B2

Authority

JP

Japan

Prior art keywords

methyl

ylsulfanyl

thiazol

ureido

cyclohexyl

Prior art date

2005-07-14

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.)

Expired - Fee Related

Links

• Espacenet
• Global Dossier
• Discuss

• 229940124828 glucokinase activator Drugs 0.000 title description 3
• -1 methoxy, methylthio, ethoxy, cyclopropyl-methoxy Chemical group 0.000 claims description 631
• 150000001875 compounds Chemical class 0.000 claims description 280
• 125000001424 substituent group Chemical group 0.000 claims description 101
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 67
• 150000003839 salts Chemical class 0.000 claims description 28
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 229910052794 bromium Inorganic materials 0.000 claims description 17
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 229910052731 fluorine Inorganic materials 0.000 claims description 16
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• 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 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
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000004710 2-methylpropylthio group Chemical group CC(CS*)C 0.000 claims description 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 337
• 229960000583 acetic acid Drugs 0.000 description 276
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 206
• 230000015572 biosynthetic process Effects 0.000 description 196
• 238000003786 synthesis reaction Methods 0.000 description 194
• 238000005481 NMR spectroscopy Methods 0.000 description 123
• 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 98
• 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 96
• 238000011282 treatment Methods 0.000 description 88
• 238000000034 method Methods 0.000 description 87
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
• 239000000203 mixture Substances 0.000 description 69
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
• KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 62
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 60
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• 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 52
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 51
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
• 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 48
• 239000008103 glucose Substances 0.000 description 48
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
• 229940125396 insulin Drugs 0.000 description 45
• 238000002360 preparation method Methods 0.000 description 44
• 108090001061 Insulin Proteins 0.000 description 43
• 102000004877 Insulin Human genes 0.000 description 43
• YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• 125000003118 aryl group Chemical group 0.000 description 42
• 239000011541 reaction mixture Substances 0.000 description 42
• SECHCLWZVJEJOT-UHFFFAOYSA-N 2-[2-[[cyclopentylmethyl-(4-methylsulfonylphenyl)carbamoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N(C(=O)NC=1SC=C(CC(O)=O)N=1)CC1CCCC1 SECHCLWZVJEJOT-UHFFFAOYSA-N 0.000 description 40
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 39
• 102000030595 Glucokinase Human genes 0.000 description 37
• 108010021582 Glucokinase Proteins 0.000 description 37
• 239000008194 pharmaceutical composition Substances 0.000 description 36
• 238000005160 1H NMR spectroscopy Methods 0.000 description 35
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• 125000001072 heteroaryl group Chemical group 0.000 description 31
• 238000006243 chemical reaction Methods 0.000 description 30
• 239000012074 organic phase Substances 0.000 description 30
• 239000002904 solvent Substances 0.000 description 30
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 26
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 25
• 239000002253 acid Substances 0.000 description 25
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 24
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
• 125000000217 alkyl group Chemical group 0.000 description 23
• VMLUPVHSIYWRJB-UHFFFAOYSA-N ethyl 2-[(2-amino-1,3-thiazol-5-yl)sulfanyl]propanoate Chemical compound CCOC(=O)C(C)SC1=CN=C(N)S1 VMLUPVHSIYWRJB-UHFFFAOYSA-N 0.000 description 23
• 229910052757 nitrogen Inorganic materials 0.000 description 23
• 239000000243 solution Substances 0.000 description 23
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• 210000004369 blood Anatomy 0.000 description 21
• 239000008280 blood Substances 0.000 description 21
• 201000010099 disease Diseases 0.000 description 21
• 235000019439 ethyl acetate Nutrition 0.000 description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
• 239000000460 chlorine Substances 0.000 description 20
• 229910052736 halogen Inorganic materials 0.000 description 20
• 150000002367 halogens Chemical class 0.000 description 20
• 206010020772 Hypertension Diseases 0.000 description 19
• 238000007630 basic procedure Methods 0.000 description 19
• 239000003814 drug Substances 0.000 description 19
• 208000013016 Hypoglycemia Diseases 0.000 description 18
• 239000013078 crystal Substances 0.000 description 18
• 206010012601 diabetes mellitus Diseases 0.000 description 18
• AJZKVNWXZNAORH-UHFFFAOYSA-N 2-[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NC(=O)N(CC2CCCC2)C=2C=C(F)C(F)=CC=2)=N1 AJZKVNWXZNAORH-UHFFFAOYSA-N 0.000 description 17
• 101000976075 Homo sapiens Insulin Proteins 0.000 description 17
• 239000000556 agonist Substances 0.000 description 17
• 230000002218 hypoglycaemic effect Effects 0.000 description 17
• MKCGLXWQSUNOCI-UHFFFAOYSA-N tert-butyl n-(3-hydroxypropyl)-n-(4-methylcyclohexyl)carbamate Chemical compound CC1CCC(N(CCCO)C(=O)OC(C)(C)C)CC1 MKCGLXWQSUNOCI-UHFFFAOYSA-N 0.000 description 17
• 208000008589 Obesity Diseases 0.000 description 16
• 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 16
• 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 16
• 235000020824 obesity Nutrition 0.000 description 16
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 15
• 229940100389 Sulfonylurea Drugs 0.000 description 15
• 238000003556 assay Methods 0.000 description 15
• 150000002148 esters Chemical class 0.000 description 15
• 230000002829 reductive effect Effects 0.000 description 15
• 125000004429 atom Chemical group 0.000 description 14
• 125000000753 cycloalkyl group Chemical group 0.000 description 14
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 14
• 229960003105 metformin Drugs 0.000 description 14
• 238000010606 normalization Methods 0.000 description 14
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
• 239000008346 aqueous phase Substances 0.000 description 13
• 239000002585 base Substances 0.000 description 13
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 12
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 12
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 12
• 239000012043 crude product Substances 0.000 description 12
• 230000000694 effects Effects 0.000 description 12
• 238000009472 formulation Methods 0.000 description 12
• 125000000623 heterocyclic group Chemical group 0.000 description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 11
• 208000002705 Glucose Intolerance Diseases 0.000 description 11
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• 230000007062 hydrolysis Effects 0.000 description 11
• 238000006460 hydrolysis reaction Methods 0.000 description 11
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
• 239000000546 pharmaceutical excipient Substances 0.000 description 11
• 201000009104 prediabetes syndrome Diseases 0.000 description 11
• 239000003826 tablet Substances 0.000 description 11
• 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 description 10
• 239000004480 active ingredient Substances 0.000 description 10
• 125000000539 amino acid group Chemical group 0.000 description 10
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
• 230000034994 death Effects 0.000 description 10
• PSKHNOASLUSHEP-UHFFFAOYSA-N ethyl 2-[(2-amino-1,3-thiazol-5-yl)sulfanyl]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)SC1=CN=C(N)S1 PSKHNOASLUSHEP-UHFFFAOYSA-N 0.000 description 10
• UKVFVQPAANCXIL-FJVFSOETSA-N glp-1 (1-37) amide Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 UKVFVQPAANCXIL-FJVFSOETSA-N 0.000 description 10
• 229910052739 hydrogen Inorganic materials 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 9
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 9
• 229940079593 drug Drugs 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 125000005842 heteroatom Chemical group 0.000 description 9
• 239000001257 hydrogen Substances 0.000 description 9
• 229910052760 oxygen Inorganic materials 0.000 description 9
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• 238000006467 substitution reaction Methods 0.000 description 9
• 229910052717 sulfur Inorganic materials 0.000 description 9
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 8
• 101000840558 Homo sapiens Hexokinase-4 Proteins 0.000 description 8
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
• 150000001408 amides Chemical class 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
• 239000003937 drug carrier Substances 0.000 description 8
• 230000006870 function Effects 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• 210000004185 liver Anatomy 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
• 239000001301 oxygen Substances 0.000 description 8
• 102220183188 rs75549650 Human genes 0.000 description 8
• 229910000104 sodium hydride Inorganic materials 0.000 description 8
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 8
• 238000001356 surgical procedure Methods 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 7
• 201000001320 Atherosclerosis Diseases 0.000 description 7
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 7
• 208000031226 Hyperlipidaemia Diseases 0.000 description 7
• 229940122199 Insulin secretagogue Drugs 0.000 description 7
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 239000005557 antagonist Substances 0.000 description 7
• 239000000883 anti-obesity agent Substances 0.000 description 7
• 229940125710 antiobesity agent Drugs 0.000 description 7
• 239000000872 buffer Substances 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 7
• 230000008878 coupling Effects 0.000 description 7
• 235000014113 dietary fatty acids Nutrition 0.000 description 7
• 239000003085 diluting agent Substances 0.000 description 7
• 239000000194 fatty acid Substances 0.000 description 7
• 229930195729 fatty acid Natural products 0.000 description 7
• 210000003494 hepatocyte Anatomy 0.000 description 7
• 150000002431 hydrogen Chemical class 0.000 description 7
• 201000001421 hyperglycemia Diseases 0.000 description 7
• 239000003112 inhibitor Substances 0.000 description 7
• 239000004026 insulin derivative Substances 0.000 description 7
• SFRRZMCARPGPAC-UHFFFAOYSA-N n-(cyclopentylmethyl)-4-methylsulfonylaniline Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NCC1CCCC1 SFRRZMCARPGPAC-UHFFFAOYSA-N 0.000 description 7
• 125000004076 pyridyl group Chemical group 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• 208000024891 symptom Diseases 0.000 description 7
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 241001465754 Metazoa Species 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 239000003524 antilipemic agent Substances 0.000 description 6
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• WRINLEMDTGKJHQ-UHFFFAOYSA-N ethyl 3-[(2-amino-1,3-thiazol-5-yl)sulfanyl]propanoate Chemical compound CCOC(=O)CCSC1=CN=C(N)S1 WRINLEMDTGKJHQ-UHFFFAOYSA-N 0.000 description 6
• 150000004665 fatty acids Chemical class 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 238000003818 flash chromatography Methods 0.000 description 6
• 230000036541 health Effects 0.000 description 6
• 238000001727 in vivo Methods 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
• 235000019341 magnesium sulphate Nutrition 0.000 description 6
• 239000002609 medium Substances 0.000 description 6
• HVVIHDSQOSMIGQ-LURJTMIESA-N methyl (2s)-1-[(2-amino-1,3-thiazol-5-yl)sulfonyl]pyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1CCCN1S(=O)(=O)C1=CN=C(N)S1 HVVIHDSQOSMIGQ-LURJTMIESA-N 0.000 description 6
• PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• 239000011593 sulfur Substances 0.000 description 6
• 208000011580 syndromic disease Diseases 0.000 description 6
• 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 description 5
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
• AXNUZKSSQHTNPZ-UHFFFAOYSA-N 3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1 AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 5
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
• 102000004190 Enzymes Human genes 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• 241000588724 Escherichia coli Species 0.000 description 5
• 229920002527 Glycogen Polymers 0.000 description 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
• 229960002632 acarbose Drugs 0.000 description 5
• XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 5
• 230000009471 action Effects 0.000 description 5
• 239000013543 active substance Substances 0.000 description 5
• 150000001299 aldehydes Chemical class 0.000 description 5
• 235000019789 appetite Nutrition 0.000 description 5
• 230000036528 appetite Effects 0.000 description 5
• 125000004104 aryloxy group Chemical group 0.000 description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
• 230000037396 body weight Effects 0.000 description 5
• 230000001276 controlling effect Effects 0.000 description 5
• 238000010168 coupling process Methods 0.000 description 5
• 238000005859 coupling reaction Methods 0.000 description 5
• 208000035475 disorder Diseases 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 229940088598 enzyme Drugs 0.000 description 5
• 230000037406 food intake Effects 0.000 description 5
• 235000012631 food intake Nutrition 0.000 description 5
• 239000012634 fragment Substances 0.000 description 5
• 230000004153 glucose metabolism Effects 0.000 description 5
• 229940096919 glycogen Drugs 0.000 description 5
• 230000002473 insulinotropic effect Effects 0.000 description 5
• 150000002632 lipids Chemical class 0.000 description 5
• 229950001413 metamfepramone Drugs 0.000 description 5
• OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 5
• 229960000698 nateglinide Drugs 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 150000003141 primary amines Chemical class 0.000 description 5
• 229940002612 prodrug Drugs 0.000 description 5
• 239000000651 prodrug Substances 0.000 description 5
• 238000006268 reductive amination reaction Methods 0.000 description 5
• 150000003335 secondary amines Chemical class 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000003765 sweetening agent Substances 0.000 description 5
• 230000001225 therapeutic effect Effects 0.000 description 5
• GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 5
• 229960001641 troglitazone Drugs 0.000 description 5
• GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 4
• DZSQDBSSALZIQK-UHFFFAOYSA-N 2-[[2-[[3-methylbutyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonylamino]acetic acid Chemical compound N=1C=C(S(=O)(=O)NCC(O)=O)SC=1NC(=O)N(CCC(C)C)C1CCC(C)CC1 DZSQDBSSALZIQK-UHFFFAOYSA-N 0.000 description 4
• IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 4
• 125000006228 2-isobutoxyethyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
• CHYRXHBVBVPCLF-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-methyl-4-oxobutanoic acid Chemical compound OC(=O)C(C)CC(=O)C1=CC=CC(F)=C1 CHYRXHBVBVPCLF-UHFFFAOYSA-N 0.000 description 4
• ARHCLXWELPFVFQ-UHFFFAOYSA-N 5-bromo-1,3-thiazol-2-amine Chemical compound NC1=NC=C(Br)S1 ARHCLXWELPFVFQ-UHFFFAOYSA-N 0.000 description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
• 208000002249 Diabetes Complications Diseases 0.000 description 4
• 206010012655 Diabetic complications Diseases 0.000 description 4
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
• 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 4
• 102400000322 Glucagon-like peptide 1 Human genes 0.000 description 4
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
• 235000019483 Peanut oil Nutrition 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• 229910004298 SiO 2 Inorganic materials 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
• 230000004913 activation Effects 0.000 description 4
• 125000000304 alkynyl group Chemical group 0.000 description 4
• 239000003472 antidiabetic agent Substances 0.000 description 4
• 239000002220 antihypertensive agent Substances 0.000 description 4
• 239000007900 aqueous suspension Substances 0.000 description 4
• 230000008901 benefit Effects 0.000 description 4
• 238000004440 column chromatography Methods 0.000 description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 description 4
• 235000005911 diet Nutrition 0.000 description 4
• 230000037213 diet Effects 0.000 description 4
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
• DXBJOELSXQRATR-UHFFFAOYSA-N ethyl 2-[(2-amino-1,3-thiazol-5-yl)sulfonylamino]acetate Chemical compound CCOC(=O)CNS(=O)(=O)C1=CN=C(N)S1 DXBJOELSXQRATR-UHFFFAOYSA-N 0.000 description 4
• DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 4
• 230000004634 feeding behavior Effects 0.000 description 4
• 239000000796 flavoring agent Substances 0.000 description 4
• 235000003599 food sweetener Nutrition 0.000 description 4
• 239000007903 gelatin capsule Substances 0.000 description 4
• 229960004580 glibenclamide Drugs 0.000 description 4
• 230000009229 glucose formation Effects 0.000 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 description 4
• 239000008187 granular material Substances 0.000 description 4
• 125000005553 heteroaryloxy group Chemical group 0.000 description 4
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
• 238000004128 high performance liquid chromatography Methods 0.000 description 4
• 150000002430 hydrocarbons Chemical group 0.000 description 4
• 239000005457 ice water Substances 0.000 description 4
• 230000003914 insulin secretion Effects 0.000 description 4
• BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
• 239000002480 mineral oil Substances 0.000 description 4
• 235000010446 mineral oil Nutrition 0.000 description 4
• 150000007522 mineralic acids Chemical class 0.000 description 4
• 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 4
• 208000010125 myocardial infarction Diseases 0.000 description 4
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 235000019198 oils Nutrition 0.000 description 4
• 239000004006 olive oil Substances 0.000 description 4
• 235000008390 olive oil Nutrition 0.000 description 4
• 150000002923 oximes Chemical class 0.000 description 4
• 125000004043 oxo group Chemical group O=* 0.000 description 4
• 239000000312 peanut oil Substances 0.000 description 4
• 239000012071 phase Substances 0.000 description 4
• DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• 238000001556 precipitation Methods 0.000 description 4
• 238000002953 preparative HPLC Methods 0.000 description 4
• 230000002265 prevention Effects 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 230000009467 reduction Effects 0.000 description 4
• 238000006722 reduction reaction Methods 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 230000035945 sensitivity Effects 0.000 description 4
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
• 239000000741 silica gel Substances 0.000 description 4
• 229910002027 silica gel Inorganic materials 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• 239000012453 solvate Substances 0.000 description 4
• 239000000758 substrate Substances 0.000 description 4
• 239000000375 suspending agent Substances 0.000 description 4
• 239000006188 syrup Substances 0.000 description 4
• 235000020357 syrup Nutrition 0.000 description 4
• 125000003396 thiol group Chemical group [H]S* 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
• 239000000080 wetting agent Substances 0.000 description 4
• HUMARXMRTXDPPK-UHFFFAOYSA-N (2-amino-1,3-thiazol-5-yl) thiocyanate Chemical compound NC1=NC=C(SC#N)S1 HUMARXMRTXDPPK-UHFFFAOYSA-N 0.000 description 3
• GIRKJSRZELQHDX-UHFFFAOYSA-N (4-methylcyclohexyl)azanium;chloride Chemical compound Cl.CC1CCC(N)CC1 GIRKJSRZELQHDX-UHFFFAOYSA-N 0.000 description 3
• 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 description 3
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
• YLHCMDNAKVPTIO-UHFFFAOYSA-N 2-(4-hydroxycyclohexyl)isoindole-1,3-dione Chemical compound C1CC(O)CCC1N1C(=O)C2=CC=CC=C2C1=O YLHCMDNAKVPTIO-UHFFFAOYSA-N 0.000 description 3
• KNUPPKPEHRHTSY-UHFFFAOYSA-N 2-[[2-[[(3,4-difluorophenyl)-[(4-methylcyclohexyl)methyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1CC(C)CCC1CN(C=1C=C(F)C(F)=CC=1)C(=O)NC1=NC=C(SCC(O)=O)S1 KNUPPKPEHRHTSY-UHFFFAOYSA-N 0.000 description 3
• TVLULZPORLSLHT-UHFFFAOYSA-N 2-[[2-[[[4-(methoxymethyl)cyclohexyl]-(3-methylbutyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1CC(COC)CCC1N(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 TVLULZPORLSLHT-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 3
• JMVZTKQBQNSZLT-UHFFFAOYSA-N 3-[[2-[[cyclohexyl(2-phenylethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound S1C(SCCC(=O)O)=CN=C1NC(=O)N(C1CCCCC1)CCC1=CC=CC=C1 JMVZTKQBQNSZLT-UHFFFAOYSA-N 0.000 description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
• 125000005330 8 membered heterocyclic group Chemical group 0.000 description 3
• 239000004475 Arginine Substances 0.000 description 3
• 210000002237 B-cell of pancreatic islet Anatomy 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• 208000035484 Cellulite Diseases 0.000 description 3
• PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 3
• 208000032928 Dyslipidaemia Diseases 0.000 description 3
• 208000007530 Essential hypertension Diseases 0.000 description 3
• 239000007995 HEPES buffer Substances 0.000 description 3
• 206010019280 Heart failures Diseases 0.000 description 3
• 102000005548 Hexokinase Human genes 0.000 description 3
• 108700040460 Hexokinases Proteins 0.000 description 3
• 208000017170 Lipid metabolism disease Diseases 0.000 description 3
• 241000124008 Mammalia Species 0.000 description 3
• 208000001145 Metabolic Syndrome Diseases 0.000 description 3
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 3
• 206010028980 Neoplasm Diseases 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 206010049752 Peau d'orange Diseases 0.000 description 3
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 3
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 3
• BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 3
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• 102000034527 Retinoid X Receptors Human genes 0.000 description 3
• 108010038912 Retinoid X Receptors Proteins 0.000 description 3
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
• 206010041277 Sodium retention Diseases 0.000 description 3
• 235000021355 Stearic acid Nutrition 0.000 description 3
• 229930006000 Sucrose Natural products 0.000 description 3
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 230000005856 abnormality Effects 0.000 description 3
• 239000012190 activator Substances 0.000 description 3
• 239000008186 active pharmaceutical agent Substances 0.000 description 3
• 235000001014 amino acid Nutrition 0.000 description 3
• 229940024606 amino acid Drugs 0.000 description 3
• 229940030600 antihypertensive agent Drugs 0.000 description 3
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 3
• 235000010323 ascorbic acid Nutrition 0.000 description 3
• 239000011668 ascorbic acid Substances 0.000 description 3
• 229960005070 ascorbic acid Drugs 0.000 description 3
• 125000005605 benzo group Chemical group 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 230000004071 biological effect Effects 0.000 description 3
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
• 239000012267 brine Substances 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 230000036232 cellulite Effects 0.000 description 3
• 210000003710 cerebral cortex Anatomy 0.000 description 3
• 235000012000 cholesterol Nutrition 0.000 description 3
• 239000003086 colorant Substances 0.000 description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
• 230000007812 deficiency Effects 0.000 description 3
• 230000001419 dependent effect Effects 0.000 description 3
• 239000002270 dispersing agent Substances 0.000 description 3
• 229940088679 drug related substance Drugs 0.000 description 3
• 125000000524 functional group Chemical group 0.000 description 3
• 125000002541 furyl group Chemical group 0.000 description 3
• 210000001035 gastrointestinal tract Anatomy 0.000 description 3
• 208000019622 heart disease Diseases 0.000 description 3
• 150000003840 hydrochlorides Chemical class 0.000 description 3
• 210000003016 hypothalamus Anatomy 0.000 description 3
• 125000001041 indolyl group Chemical group 0.000 description 3
• 238000007918 intramuscular administration Methods 0.000 description 3
• 238000001990 intravenous administration Methods 0.000 description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
• 125000000842 isoxazolyl group Chemical group 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• 229940057995 liquid paraffin Drugs 0.000 description 3
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 3
• 229960004844 lovastatin Drugs 0.000 description 3
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 3
• 235000019359 magnesium stearate Nutrition 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 230000001404 mediated effect Effects 0.000 description 3
• 229910052751 metal Inorganic materials 0.000 description 3
• 239000002184 metal Substances 0.000 description 3
• GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 3
• 239000002808 molecular sieve Substances 0.000 description 3
• HYESTPIIALLAAO-UHFFFAOYSA-N n-(2-phenylethyl)cyclohexanamine Chemical compound C1CCCCC1NCCC1=CC=CC=C1 HYESTPIIALLAAO-UHFFFAOYSA-N 0.000 description 3
• XBAZZGBTSBJEQX-UHFFFAOYSA-N n-(cyclohexylmethyl)-3,4-difluoroaniline Chemical compound C1=C(F)C(F)=CC=C1NCC1CCCCC1 XBAZZGBTSBJEQX-UHFFFAOYSA-N 0.000 description 3
• 230000007935 neutral effect Effects 0.000 description 3
• 239000012299 nitrogen atmosphere Substances 0.000 description 3
• 231100000252 nontoxic Toxicity 0.000 description 3
• 230000003000 nontoxic effect Effects 0.000 description 3
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
• 150000007524 organic acids Chemical class 0.000 description 3
• 238000007911 parenteral administration Methods 0.000 description 3
• 230000036961 partial effect Effects 0.000 description 3
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
• 125000004344 phenylpropyl group Chemical group 0.000 description 3
• 150000003904 phospholipids Chemical class 0.000 description 3
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
• 239000003755 preservative agent Substances 0.000 description 3
• 230000001737 promoting effect Effects 0.000 description 3
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
• 235000019260 propionic acid Nutrition 0.000 description 3
• 230000036186 satiety Effects 0.000 description 3
• 230000028327 secretion Effects 0.000 description 3
• 239000001632 sodium acetate Substances 0.000 description 3
• 235000017281 sodium acetate Nutrition 0.000 description 3
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
• 239000008117 stearic acid Substances 0.000 description 3
• 230000000638 stimulation Effects 0.000 description 3
• 238000007920 subcutaneous administration Methods 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• 239000005720 sucrose Substances 0.000 description 3
• 230000002459 sustained effect Effects 0.000 description 3
• 238000002560 therapeutic procedure Methods 0.000 description 3
• 125000000335 thiazolyl group Chemical group 0.000 description 3
• 229930192474 thiophene Natural products 0.000 description 3
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
• 210000001519 tissue Anatomy 0.000 description 3
• 230000004580 weight loss Effects 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• JKYMEMFIFMJTTM-KRWDZBQOSA-N (2s)-1-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1S(=O)(=O)C(S1)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 JKYMEMFIFMJTTM-KRWDZBQOSA-N 0.000 description 2
• ZQSSUOZHKGFJOM-SFHVURJKSA-N (2s)-1-[[2-[[cyclopentylmethyl-(4-methylsulfonylphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]pyrrolidine-2-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)N1[C@@H](CCC1)C(O)=O)CC1CCCC1 ZQSSUOZHKGFJOM-SFHVURJKSA-N 0.000 description 2
• NGJOFQZEYQGZMB-KTKZVXAJSA-N (4S)-5-[[2-[[(2S,3R)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[2-[[(1S)-4-carbamimidamido-1-carboxybutyl]amino]-2-oxoethyl]amino]-1-oxohexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-2-oxoethyl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-4-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]propanoyl]amino]-5-oxopentanoic acid Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 NGJOFQZEYQGZMB-KTKZVXAJSA-N 0.000 description 2
• FFEKJBVVAJTQST-WLHGVMLRSA-N (e)-but-2-enedioic acid;1,1-dimethyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound OC(=O)\C=C\C(O)=O.CN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 FFEKJBVVAJTQST-WLHGVMLRSA-N 0.000 description 2
• ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
• FQSYHBGUTMPDPX-UHFFFAOYSA-N 1,3-dithiole-4,5-diol Chemical compound OC1=C(O)SCS1 FQSYHBGUTMPDPX-UHFFFAOYSA-N 0.000 description 2
• YXNMORHRGMYQKF-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-ylmethanol Chemical compound C1CC(CO)CCC21OCCO2 YXNMORHRGMYQKF-UHFFFAOYSA-N 0.000 description 2
• MYYYZNVAUZVXBO-UHFFFAOYSA-N 1-(bromomethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(CBr)=C1 MYYYZNVAUZVXBO-UHFFFAOYSA-N 0.000 description 2
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 2
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
• 125000005976 1-phenylethyloxy group Chemical group 0.000 description 2
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
• 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• MMWHNMTUULZDAB-UHFFFAOYSA-N 2-[(2-amino-1,3-thiazol-5-yl)sulfonyl-methylamino]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CN(C)S(=O)(=O)C1=CN=C(N)S1 MMWHNMTUULZDAB-UHFFFAOYSA-N 0.000 description 2
• BVXFKEGFIVGMSV-UHFFFAOYSA-N 2-[[2-[[(3,4-difluorophenyl)-[[4-(trifluoromethyl)cyclohexyl]methyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCC(C(F)(F)F)CC1 BVXFKEGFIVGMSV-UHFFFAOYSA-N 0.000 description 2
• XREKJHMMCPJFJP-UHFFFAOYSA-N 2-[[2-[[(3-acetamidophenyl)-(3,3-dimethylbutyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC(=O)NC1=CC=CC(N(CCC(C)(C)C)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 XREKJHMMCPJFJP-UHFFFAOYSA-N 0.000 description 2
• ZCAFINCURUPLCX-UHFFFAOYSA-N 2-[[2-[[(3-acetamidophenyl)-(3-methylbutyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C=1C=CC(NC(C)=O)=CC=1N(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 ZCAFINCURUPLCX-UHFFFAOYSA-N 0.000 description 2
• WLZFYGAURPTVSH-UHFFFAOYSA-N 2-[[2-[[(3-acetamidophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC(=O)NC1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 WLZFYGAURPTVSH-UHFFFAOYSA-N 0.000 description 2
• ZEGDVJSDTSZKBN-UHFFFAOYSA-N 2-[[2-[[(3-acetamidophenyl)-(cyclopropylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC(=O)NC1=CC=CC(N(CC2CC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 ZEGDVJSDTSZKBN-UHFFFAOYSA-N 0.000 description 2
• PULYKDYZSXNCJN-UHFFFAOYSA-N 2-[[2-[[(3-acetamidophenyl)-benzylcarbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC(=O)NC1=CC=CC(N(CC=2C=CC=CC=2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 PULYKDYZSXNCJN-UHFFFAOYSA-N 0.000 description 2
• SMGKZAMONGYSNB-UHFFFAOYSA-N 2-[[2-[[(3-acetamidophenyl)-hexylcarbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C=1C=CC(NC(C)=O)=CC=1N(CCCCCC)C(=O)NC1=NC=C(SCC(O)=O)S1 SMGKZAMONGYSNB-UHFFFAOYSA-N 0.000 description 2
• LDINXDBARKTZAN-UHFFFAOYSA-N 2-[[2-[[(3-acetamidophenyl)-pentylcarbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C=1C=CC(NC(C)=O)=CC=1N(CCCCC)C(=O)NC1=NC=C(SCC(O)=O)S1 LDINXDBARKTZAN-UHFFFAOYSA-N 0.000 description 2
• ITZSPQUAFZAQRB-UHFFFAOYSA-N 2-[[2-[[(3-carbamoylphenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound NC(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 ITZSPQUAFZAQRB-UHFFFAOYSA-N 0.000 description 2
• SJHXKFNBTVBNAU-UHFFFAOYSA-N 2-[[2-[[(3-chloro-4-fluorophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(Cl)C(F)=CC=1)CC1CCCC1 SJHXKFNBTVBNAU-UHFFFAOYSA-N 0.000 description 2
• TXZUHQQNXASEKF-UHFFFAOYSA-N 2-[[2-[[(4-methylcyclohexyl)-(3-phenylpropyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CCCC1=CC=CC=C1 TXZUHQQNXASEKF-UHFFFAOYSA-N 0.000 description 2
• SQICZXGTZAZEHW-UHFFFAOYSA-N 2-[[2-[[(4-tert-butylcyclohexyl)methyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1CC(C(C)(C)C)CCC1CN(C=1C=C(F)C(F)=CC=1)C(=O)NC1=NC=C(SCC(O)=O)S1 SQICZXGTZAZEHW-UHFFFAOYSA-N 0.000 description 2
• YMBNCBTXOAIEQG-UHFFFAOYSA-N 2-[[2-[[(6-acetamidopyridin-3-yl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=NC(NC(=O)C)=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 YMBNCBTXOAIEQG-UHFFFAOYSA-N 0.000 description 2
• VFBHZXCJZMYLRA-UHFFFAOYSA-N 2-[[2-[[1,3-benzodioxol-5-yl(cyclohexylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C2OCOC2=CC=1)CC1CCCCC1 VFBHZXCJZMYLRA-UHFFFAOYSA-N 0.000 description 2
• QJNHTPFGVPKLFQ-UHFFFAOYSA-N 2-[[2-[[1,3-benzodioxol-5-yl(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C2OCOC2=CC=1)CC1CCCC1 QJNHTPFGVPKLFQ-UHFFFAOYSA-N 0.000 description 2
• YRMXMGPZYUTBCK-UHFFFAOYSA-N 2-[[2-[[2-(3-fluoro-4-methoxyphenyl)ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]-2-methylpropanoic acid Chemical compound C1=C(F)C(OC)=CC=C1CCN(C(=O)NC=1SC(=CN=1)S(=O)(=O)C(C)(C)C(O)=O)C1CCC(C)CC1 YRMXMGPZYUTBCK-UHFFFAOYSA-N 0.000 description 2
• HFCXDZBQDULLRB-UHFFFAOYSA-N 2-[[2-[[2-(cyclohexen-1-yl)ethyl-cyclohexylcarbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C1CCCCC1)CCC1=CCCCC1 HFCXDZBQDULLRB-UHFFFAOYSA-N 0.000 description 2
• MDCYYQYIMVJNAV-UHFFFAOYSA-N 2-[[2-[[3-bicyclo[2.2.1]heptanylmethyl(cyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C1CCCCC1)CC1C(C2)CCC2C1 MDCYYQYIMVJNAV-UHFFFAOYSA-N 0.000 description 2
• JWFAXBWINSRLDN-UHFFFAOYSA-N 2-[[2-[[3-methylbutyl-(4-propoxycyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1CC(OCCC)CCC1N(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 JWFAXBWINSRLDN-UHFFFAOYSA-N 0.000 description 2
• BQUGBBPBFHBMIW-UHFFFAOYSA-N 2-[[2-[[5-bicyclo[2.2.1]hept-2-enylmethyl(cyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C1CCCCC1)CC1C(C=C2)CC2C1 BQUGBBPBFHBMIW-UHFFFAOYSA-N 0.000 description 2
• QQLXINXLYFPBOC-UHFFFAOYSA-N 2-[[2-[[[3-(azetidine-1-carbonyl)phenyl]-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(C=CC=1)C(=O)N1CCC1)CC1CCCC1 QQLXINXLYFPBOC-UHFFFAOYSA-N 0.000 description 2
• QDTMKTYSIVVQHP-UHFFFAOYSA-N 2-[[2-[[butyl(3-methylbutyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CCCCN(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 QDTMKTYSIVVQHP-UHFFFAOYSA-N 0.000 description 2
• HYGVNDPQZVRKPR-UHFFFAOYSA-N 2-[[2-[[cyclobutylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCC1 HYGVNDPQZVRKPR-UHFFFAOYSA-N 0.000 description 2
• STYRQWFDCDLGHB-UHFFFAOYSA-N 2-[[2-[[cyclohexyl(2-cyclohexylethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C1CCCCC1)CCC1CCCCC1 STYRQWFDCDLGHB-UHFFFAOYSA-N 0.000 description 2
• VSGPRZCUZKORSL-UHFFFAOYSA-N 2-[[2-[[cyclohexyl(3-methylbutyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound N=1C=C(SCC(O)=O)SC=1NC(=O)N(CCC(C)C)C1CCCCC1 VSGPRZCUZKORSL-UHFFFAOYSA-N 0.000 description 2
• KMLMPHIOKWIONE-UHFFFAOYSA-N 2-[[2-[[cyclohexylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCCC1 KMLMPHIOKWIONE-UHFFFAOYSA-N 0.000 description 2
• QUPCWQPZAOUXFV-UHFFFAOYSA-N 2-[[2-[[cyclohexylmethyl-(6-methoxypyridin-3-yl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=NC(OC)=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCCC1 QUPCWQPZAOUXFV-UHFFFAOYSA-N 0.000 description 2
• PSJYQBFUIULADH-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(2,3,4-trifluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C(=C(F)C(F)=CC=1)F)CC1CCCC1 PSJYQBFUIULADH-UHFFFAOYSA-N 0.000 description 2
• JPLGTRVGSGBUHA-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(2,3-dichlorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C(=C(Cl)C=CC=1)Cl)CC1CCCC1 JPLGTRVGSGBUHA-UHFFFAOYSA-N 0.000 description 2
• ZUONRDVGYVRVBY-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(2,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C(=CC(F)=CC=1)F)CC1CCCC1 ZUONRDVGYVRVBY-UHFFFAOYSA-N 0.000 description 2
• ZZVYQSKDNSHLDB-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]-2-methylpropanoic acid Chemical compound S1C(SC(C)(C)C(O)=O)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 ZZVYQSKDNSHLDB-UHFFFAOYSA-N 0.000 description 2
• OLDGEXLWLBCMRS-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl-methylamino]-n,n-diethylacetamide Chemical compound S1C(S(=O)(=O)N(C)CC(=O)N(CC)CC)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 OLDGEXLWLBCMRS-UHFFFAOYSA-N 0.000 description 2
• SPHLMTUKCLONFV-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonylamino]acetic acid Chemical compound S1C(S(=O)(=O)NCC(=O)O)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 SPHLMTUKCLONFV-UHFFFAOYSA-N 0.000 description 2
• JTLNXWVTAXYYNR-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(3-fluoro-4-methoxyphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=C(F)C(OC)=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 JTLNXWVTAXYYNR-UHFFFAOYSA-N 0.000 description 2
• UOJHORWDVVIWEV-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(4-methylsulfonylphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]-2-methylpropanoic acid Chemical compound S1C(SC(C)(C)C(O)=O)=CN=C1NC(=O)N(C=1C=CC(=CC=1)S(C)(=O)=O)CC1CCCC1 UOJHORWDVVIWEV-UHFFFAOYSA-N 0.000 description 2
• MBLBAGHABIRUPO-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(4-methylsulfonylphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 MBLBAGHABIRUPO-UHFFFAOYSA-N 0.000 description 2
• XOUVMEILKKUOCV-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(4-methylsulfonylphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonylamino]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)NCC(O)=O)CC1CCCC1 XOUVMEILKKUOCV-UHFFFAOYSA-N 0.000 description 2
• BSLJIUXKJAUQPX-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(4-sulfamoylphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 BSLJIUXKJAUQPX-UHFFFAOYSA-N 0.000 description 2
• JOMNGQOASAFDFH-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(6-methoxypyridin-3-yl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=NC(OC)=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 JOMNGQOASAFDFH-UHFFFAOYSA-N 0.000 description 2
• YUVZBBJYAHQFEP-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[3-(dimethylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CN(C)C(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 YUVZBBJYAHQFEP-UHFFFAOYSA-N 0.000 description 2
• USUYYCYXFGWEOF-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[3-(ethylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CCNC(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 USUYYCYXFGWEOF-UHFFFAOYSA-N 0.000 description 2
• XTFKNJZGMPNLGU-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[3-(methylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CNC(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 XTFKNJZGMPNLGU-UHFFFAOYSA-N 0.000 description 2
• XWSVDYHGXZMXMD-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[3-(propan-2-ylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC(C)NC(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 XWSVDYHGXZMXMD-UHFFFAOYSA-N 0.000 description 2
• GAMRZGCKDHXDHT-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[3-(trifluoromethoxy)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(OC(F)(F)F)C=CC=1)CC1CCCC1 GAMRZGCKDHXDHT-UHFFFAOYSA-N 0.000 description 2
• SWCMGJLCHLFNOE-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[3-(trifluoromethyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(C=CC=1)C(F)(F)F)CC1CCCC1 SWCMGJLCHLFNOE-UHFFFAOYSA-N 0.000 description 2
• HVXAXVZCVRIFBI-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[4-(trifluoromethoxy)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=CC(OC(F)(F)F)=CC=1)CC1CCCC1 HVXAXVZCVRIFBI-UHFFFAOYSA-N 0.000 description 2
• XVQOANDDRRWDET-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[4-(trifluoromethyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=CC(=CC=1)C(F)(F)F)CC1CCCC1 XVQOANDDRRWDET-UHFFFAOYSA-N 0.000 description 2
• IXLPJYSBDFKXOK-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[4-fluoro-3-(trifluoromethyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(C(F)=CC=1)C(F)(F)F)CC1CCCC1 IXLPJYSBDFKXOK-UHFFFAOYSA-N 0.000 description 2
• KGLPUDLXEDKSHP-UHFFFAOYSA-N 2-[[2-[bis(3-methylbutyl)carbamoylamino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC(C)CCN(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 KGLPUDLXEDKSHP-UHFFFAOYSA-N 0.000 description 2
• VGYHEIFRKKUZTD-UHFFFAOYSA-N 2-amino-1,3-thiazole-5-sulfonamide Chemical class NC1=NC=C(S(N)(=O)=O)S1 VGYHEIFRKKUZTD-UHFFFAOYSA-N 0.000 description 2
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
• JRQAAYVLPPGEHT-UHFFFAOYSA-N 2-bromoethylcyclohexane Chemical compound BrCCC1CCCCC1 JRQAAYVLPPGEHT-UHFFFAOYSA-N 0.000 description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
• DQDHFZKPCQKGHC-UHFFFAOYSA-N 3-(cyclopentylmethylamino)-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(NCC2CCCC2)=C1 DQDHFZKPCQKGHC-UHFFFAOYSA-N 0.000 description 2
• YIUMJTAAICPZTH-UHFFFAOYSA-N 3-(cyclopentylmethylamino)benzamide Chemical compound NC(=O)C1=CC=CC(NCC2CCCC2)=C1 YIUMJTAAICPZTH-UHFFFAOYSA-N 0.000 description 2
• RLXJLTBOHJNDIH-UHFFFAOYSA-N 3-[[2-[[(3-acetamidophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound CC(=O)NC1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCCC(O)=O)=CN=2)=C1 RLXJLTBOHJNDIH-UHFFFAOYSA-N 0.000 description 2
• BEKQFUKPUYZHKW-UHFFFAOYSA-N 3-[[2-[[(3-carbamoylphenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound NC(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCCC(O)=O)=CN=2)=C1 BEKQFUKPUYZHKW-UHFFFAOYSA-N 0.000 description 2
• ADOPZAQKTSERMK-UHFFFAOYSA-N 3-[[2-[[2-(cyclohexen-1-yl)ethyl-cyclohexylcarbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound S1C(SCCC(=O)O)=CN=C1NC(=O)N(C1CCCCC1)CCC1=CCCCC1 ADOPZAQKTSERMK-UHFFFAOYSA-N 0.000 description 2
• CKRXSIJETDZCGC-UHFFFAOYSA-N 3-[[2-[[butyl(3-methylbutyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound CCCCN(CCC(C)C)C(=O)NC1=NC=C(SCCC(O)=O)S1 CKRXSIJETDZCGC-UHFFFAOYSA-N 0.000 description 2
• FVXWVVQBVGTFLV-UHFFFAOYSA-N 3-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound S1C(SCCC(=O)O)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 FVXWVVQBVGTFLV-UHFFFAOYSA-N 0.000 description 2
• ZGMFYSQDTGMUID-UHFFFAOYSA-N 3-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonylamino]propanoic acid Chemical compound S1C(S(=O)(=O)NCCC(=O)O)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 ZGMFYSQDTGMUID-UHFFFAOYSA-N 0.000 description 2
• FXTBFKAGDDJRJE-UHFFFAOYSA-N 3-[[2-[[cyclopentylmethyl-(4-methylsulfonylphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N(C(=O)NC=1SC(SCCC(O)=O)=CN=1)CC1CCCC1 FXTBFKAGDDJRJE-UHFFFAOYSA-N 0.000 description 2
• SYLJOQFRALHGGY-UHFFFAOYSA-N 3-[[2-[[cyclopentylmethyl-(4-methylsulfonylphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonylamino]propanoic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)NCCC(O)=O)CC1CCCC1 SYLJOQFRALHGGY-UHFFFAOYSA-N 0.000 description 2
• OAFIKBNXBCZONT-UHFFFAOYSA-N 3-[[2-[[cyclopentylmethyl-[3-(dimethylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound CN(C)C(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCCC(O)=O)=CN=2)=C1 OAFIKBNXBCZONT-UHFFFAOYSA-N 0.000 description 2
• OOUMFJWWCXFCTQ-UHFFFAOYSA-N 3-[[2-[[cyclopentylmethyl-[3-(methylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound CNC(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCCC(O)=O)=CN=2)=C1 OOUMFJWWCXFCTQ-UHFFFAOYSA-N 0.000 description 2
• IVQGZYJDKXVVQV-UHFFFAOYSA-N 3-[[2-[bis(3-methylbutyl)carbamoylamino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound CC(C)CCN(CCC(C)C)C(=O)NC1=NC=C(SCCC(O)=O)S1 IVQGZYJDKXVVQV-UHFFFAOYSA-N 0.000 description 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
• YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• KPQOQSYRJHFQHS-UHFFFAOYSA-N 4-(methoxymethyl)cyclohexan-1-one Chemical compound COCC1CCC(=O)CC1 KPQOQSYRJHFQHS-UHFFFAOYSA-N 0.000 description 2
• SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical class COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 2
• ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
• MZUBANKASMUHHF-UHFFFAOYSA-N 4-propoxycyclohexan-1-amine Chemical compound CCCOC1CCC(N)CC1 MZUBANKASMUHHF-UHFFFAOYSA-N 0.000 description 2
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 2
• KRNSYSYRLQDHDK-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[b]pyridine Chemical compound C1=CN=C2CCCC2=C1 KRNSYSYRLQDHDK-UHFFFAOYSA-N 0.000 description 2
• 244000215068 Acacia senegal Species 0.000 description 2
• 102000054930 Agouti-Related Human genes 0.000 description 2
• 101710127426 Agouti-related protein Proteins 0.000 description 2
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• 108010064733 Angiotensins Proteins 0.000 description 2
• 102000015427 Angiotensins Human genes 0.000 description 2
• 241000416162 Astragalus gummifer Species 0.000 description 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
• 239000005711 Benzoic acid Substances 0.000 description 2
• 229940123208 Biguanide Drugs 0.000 description 2
• FKHNBUQTXSVDEW-IYARVYRRSA-N C([C@H]1CC[C@@H](CC1)N(CCC(C)C)C(=O)NC=1SC(SCC(O)=O)=CN=1)OCC1CC1 Chemical compound C([C@H]1CC[C@@H](CC1)N(CCC(C)C)C(=O)NC=1SC(SCC(O)=O)=CN=1)OCC1CC1 FKHNBUQTXSVDEW-IYARVYRRSA-N 0.000 description 2
• RDISDDYBCOFHAW-JCNLHEQBSA-N C1C[C@@H](C)CC[C@@H]1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CCC1=CC=CC=C1 Chemical compound C1C[C@@H](C)CC[C@@H]1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CCC1=CC=CC=C1 RDISDDYBCOFHAW-JCNLHEQBSA-N 0.000 description 2
• JMJKSJLPFGUEJW-JCNLHEQBSA-N C1C[C@@H](C)CC[C@@H]1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CCC1=CCCCC1 Chemical compound C1C[C@@H](C)CC[C@@H]1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CCC1=CCCCC1 JMJKSJLPFGUEJW-JCNLHEQBSA-N 0.000 description 2
• HQIAEACKKUJZCR-SAABIXHNSA-N C1C[C@@H](C)CC[C@@H]1N(C(=O)NC=1SC(SCCC(O)=O)=CN=1)CCC1=CC=CC=C1 Chemical compound C1C[C@@H](C)CC[C@@H]1N(C(=O)NC=1SC(SCCC(O)=O)=CN=1)CCC1=CC=CC=C1 HQIAEACKKUJZCR-SAABIXHNSA-N 0.000 description 2
• SDPIMBOAUCWBAJ-HDJSIYSDSA-N C1C[C@@H](C)CC[C@@H]1N(CC=C(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 Chemical compound C1C[C@@H](C)CC[C@@H]1N(CC=C(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 SDPIMBOAUCWBAJ-HDJSIYSDSA-N 0.000 description 2
• VPGPZVHRICVPIH-SHTZXODSSA-N C1C[C@@H](C)CC[C@@H]1N(CC=C(C)C)C(=O)NC1=NC=C(SCCC(O)=O)S1 Chemical compound C1C[C@@H](C)CC[C@@H]1N(CC=C(C)C)C(=O)NC1=NC=C(SCCC(O)=O)S1 VPGPZVHRICVPIH-SHTZXODSSA-N 0.000 description 2
• OGYRGZFHJYNPNH-WKILWMFISA-N C1C[C@@H](COCC)CC[C@@H]1N(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 Chemical compound C1C[C@@H](COCC)CC[C@@H]1N(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 OGYRGZFHJYNPNH-WKILWMFISA-N 0.000 description 2
• JWFAXBWINSRLDN-WKILWMFISA-N C1C[C@@H](OCCC)CC[C@@H]1N(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 Chemical compound C1C[C@@H](OCCC)CC[C@@H]1N(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 JWFAXBWINSRLDN-WKILWMFISA-N 0.000 description 2
• KPOIIGXBBBTMCG-WKILWMFISA-N C1C[C@@H](OCCOC)CC[C@@H]1N(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 Chemical compound C1C[C@@H](OCCOC)CC[C@@H]1N(CCC(C)C)C(=O)NC1=NC=C(SCC(O)=O)S1 KPOIIGXBBBTMCG-WKILWMFISA-N 0.000 description 2
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 2
• 206010008111 Cerebral haemorrhage Diseases 0.000 description 2
• 102000008186 Collagen Human genes 0.000 description 2
• 108010035532 Collagen Proteins 0.000 description 2
• 102100021752 Corticoliberin Human genes 0.000 description 2
• 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 description 2
• 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 2
• 102100032165 Corticotropin-releasing factor-binding protein Human genes 0.000 description 2
• RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• 208000001380 Diabetic Ketoacidosis Diseases 0.000 description 2
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 description 2
• CJQWLNNCQIHKHP-UHFFFAOYSA-N Ethyl 3-mercaptopropanoic acid Chemical compound CCOC(=O)CCS CJQWLNNCQIHKHP-UHFFFAOYSA-N 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 102000001267 GSK3 Human genes 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 2
• 101150109586 Gk gene Proteins 0.000 description 2
• 102000051325 Glucagon Human genes 0.000 description 2
• 108060003199 Glucagon Proteins 0.000 description 2
• 101800004295 Glucagon-like peptide 1(7-36) Proteins 0.000 description 2
• 101800004266 Glucagon-like peptide 1(7-37) Proteins 0.000 description 2
• FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 2
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 description 2
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
• 229920000084 Gum arabic Polymers 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
• 206010060378 Hyperinsulinaemia Diseases 0.000 description 2
• 206010022489 Insulin Resistance Diseases 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
• XNSAINXGIQZQOO-UHFFFAOYSA-N L-pyroglutamyl-L-histidyl-L-proline amide Natural products NC(=O)C1CCCN1C(=O)C(NC(=O)C1NC(=O)CC1)CC1=CN=CN1 XNSAINXGIQZQOO-UHFFFAOYSA-N 0.000 description 2
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
• 102000016267 Leptin Human genes 0.000 description 2
• 108010092277 Leptin Proteins 0.000 description 2
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
• 240000007472 Leucaena leucocephala Species 0.000 description 2
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
• 239000004472 Lysine Substances 0.000 description 2
• 108010008364 Melanocortins Proteins 0.000 description 2
• 239000000637 Melanocyte-Stimulating Hormone Substances 0.000 description 2
• 108010007013 Melanocyte-Stimulating Hormones Proteins 0.000 description 2
• 101710151321 Melanostatin Proteins 0.000 description 2
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
• NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
• UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
• XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 2
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
• TUQMNGDEGMFPDC-SHTZXODSSA-N N=1C=C(S(=O)(=O)N(C)CC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 Chemical compound N=1C=C(S(=O)(=O)N(C)CC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 TUQMNGDEGMFPDC-SHTZXODSSA-N 0.000 description 2
• DBXXWVDKYKLXDO-ULQDDVLXSA-N N=1C=C(S(=O)(=O)N2[C@@H](CCC2)C(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 Chemical compound N=1C=C(S(=O)(=O)N2[C@@H](CCC2)C(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 DBXXWVDKYKLXDO-ULQDDVLXSA-N 0.000 description 2
• DZSQDBSSALZIQK-HDJSIYSDSA-N N=1C=C(S(=O)(=O)NCC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 Chemical compound N=1C=C(S(=O)(=O)NCC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 DZSQDBSSALZIQK-HDJSIYSDSA-N 0.000 description 2
• GOLXDXXTMDDQIW-SHTZXODSSA-N N=1C=C(S(=O)(=O)NCCC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 Chemical compound N=1C=C(S(=O)(=O)NCCC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 GOLXDXXTMDDQIW-SHTZXODSSA-N 0.000 description 2
• BMOYUMNYFGRTPE-HDJSIYSDSA-N N=1C=C(SCC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 Chemical compound N=1C=C(SCC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 BMOYUMNYFGRTPE-HDJSIYSDSA-N 0.000 description 2
• BTQMKVIUTZDOLX-WKILWMFISA-N N=1C=C(SCC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](OC(C)(C)C)CC1 Chemical compound N=1C=C(SCC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](OC(C)(C)C)CC1 BTQMKVIUTZDOLX-WKILWMFISA-N 0.000 description 2
• OQSVOPFXAWWQHF-JOCQHMNTSA-N N=1C=C(SCC(O)=O)SC=1NC(=O)N(CCCC)[C@H]1CC[C@H](C)CC1 Chemical compound N=1C=C(SCC(O)=O)SC=1NC(=O)N(CCCC)[C@H]1CC[C@H](C)CC1 OQSVOPFXAWWQHF-JOCQHMNTSA-N 0.000 description 2
• NUKDOIGHZFTPAU-SHTZXODSSA-N N=1C=C(SCCC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 Chemical compound N=1C=C(SCCC(O)=O)SC=1NC(=O)N(CCC(C)C)[C@H]1CC[C@H](C)CC1 NUKDOIGHZFTPAU-SHTZXODSSA-N 0.000 description 2
• AYDCXWSVCMGLCW-HDJSIYSDSA-N N=1C=C(SCCC(O)=O)SC=1NC(=O)N(CCCC)[C@H]1CC[C@H](C)CC1 Chemical compound N=1C=C(SCCC(O)=O)SC=1NC(=O)N(CCCC)[C@H]1CC[C@H](C)CC1 AYDCXWSVCMGLCW-HDJSIYSDSA-N 0.000 description 2
• 102400000064 Neuropeptide Y Human genes 0.000 description 2
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
• IDLMTZZKNGZHRN-MXVIHJGJSA-N O([C@H]1CC[C@@H](CC1)N(CCC(C)C)C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1=CC=CC=C1 Chemical compound O([C@H]1CC[C@@H](CC1)N(CCC(C)C)C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1=CC=CC=C1 IDLMTZZKNGZHRN-MXVIHJGJSA-N 0.000 description 2
• TVTAFKNHBUHDMT-QAQDUYKDSA-N O([C@H]1CC[C@@H](CC1)N(CCC(C)C)C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CC1 Chemical compound O([C@H]1CC[C@@H](CC1)N(CCC(C)C)C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CC1 TVTAFKNHBUHDMT-QAQDUYKDSA-N 0.000 description 2
• 235000021314 Palmitic acid Nutrition 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• 102000004257 Potassium Channel Human genes 0.000 description 2
• 229940127315 Potassium Channel Openers Drugs 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• 241000700159 Rattus Species 0.000 description 2
• 208000001647 Renal Insufficiency Diseases 0.000 description 2
• 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 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
• 229940123464 Thiazolidinedione Drugs 0.000 description 2
• 239000000627 Thyrotropin-Releasing Hormone Substances 0.000 description 2
• 102400000336 Thyrotropin-releasing hormone Human genes 0.000 description 2
• 101800004623 Thyrotropin-releasing hormone Proteins 0.000 description 2
• JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 2
• 229920001615 Tragacanth Polymers 0.000 description 2
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 description 2
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 2
• 235000010489 acacia gum Nutrition 0.000 description 2
• 239000000205 acacia gum Substances 0.000 description 2
• 238000009825 accumulation Methods 0.000 description 2
• PMZXXNPJQYDFJX-UHFFFAOYSA-N acetonitrile;2,2,2-trifluoroacetic acid Chemical compound CC#N.OC(=O)C(F)(F)F PMZXXNPJQYDFJX-UHFFFAOYSA-N 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 230000003213 activating effect Effects 0.000 description 2
• 210000000577 adipose tissue Anatomy 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 238000009098 adjuvant therapy Methods 0.000 description 2
• 230000001800 adrenalinergic effect Effects 0.000 description 2
• 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 2
• 125000003545 alkoxy group Chemical group 0.000 description 2
• 150000001350 alkyl halides Chemical class 0.000 description 2
• 125000004414 alkyl thio group Chemical group 0.000 description 2
• 125000002947 alkylene group Chemical group 0.000 description 2
• 239000003888 alpha glucosidase inhibitor Substances 0.000 description 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
• 150000001413 amino acids Chemical group 0.000 description 2
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
• 150000003863 ammonium salts Chemical class 0.000 description 2
• 229940025084 amphetamine Drugs 0.000 description 2
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
• 230000001315 anti-hyperlipaemic effect Effects 0.000 description 2
• 229940125708 antidiabetic agent Drugs 0.000 description 2
• 230000006907 apoptotic process Effects 0.000 description 2
• 125000004350 aryl cycloalkyl group Chemical group 0.000 description 2
• 125000005110 aryl thio group Chemical group 0.000 description 2
• 235000003704 aspartic acid Nutrition 0.000 description 2
• 239000007640 basal medium Substances 0.000 description 2
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
• 229940092714 benzenesulfonic acid Drugs 0.000 description 2
• 235000010233 benzoic acid Nutrition 0.000 description 2
• UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 2
• 239000002876 beta blocker Substances 0.000 description 2
• 229940097320 beta blocking agent Drugs 0.000 description 2
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
• 229910000085 borane Inorganic materials 0.000 description 2
• SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 2
• 239000001273 butane Substances 0.000 description 2
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
• 229910000019 calcium carbonate Inorganic materials 0.000 description 2
• 235000010216 calcium carbonate Nutrition 0.000 description 2
• 239000001506 calcium phosphate Substances 0.000 description 2
• 229910000389 calcium phosphate Inorganic materials 0.000 description 2
• 235000011010 calcium phosphates Nutrition 0.000 description 2
• 201000011510 cancer Diseases 0.000 description 2
• 125000002837 carbocyclic group Chemical group 0.000 description 2
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
• 230000000747 cardiac effect Effects 0.000 description 2
• 238000007675 cardiac surgery Methods 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 239000003153 chemical reaction reagent Substances 0.000 description 2
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
• 229960001231 choline Drugs 0.000 description 2
• 235000015165 citric acid Nutrition 0.000 description 2
• 239000011248 coating agent Substances 0.000 description 2
• 238000000576 coating method Methods 0.000 description 2
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
• 229920001436 collagen Polymers 0.000 description 2
• 238000002648 combination therapy Methods 0.000 description 2
• 238000013270 controlled release Methods 0.000 description 2
• 210000004351 coronary vessel Anatomy 0.000 description 2
• 108010083720 corticotropin releasing factor-binding protein Proteins 0.000 description 2
• 239000006071 cream Substances 0.000 description 2
• 125000005366 cycloalkylthio group Chemical group 0.000 description 2
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
• 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 description 2
• LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
• 230000007850 degeneration Effects 0.000 description 2
• 238000010511 deprotection reaction Methods 0.000 description 2
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 239000006185 dispersion Substances 0.000 description 2
• VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 2
• GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical group CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 2
• 229960003638 dopamine Drugs 0.000 description 2
• 239000003480 eluent Substances 0.000 description 2
• 238000010828 elution Methods 0.000 description 2
• SHQNGLYXRFCPGZ-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)acetate Chemical compound CCOC(=O)CC1=CSC(N)=N1 SHQNGLYXRFCPGZ-UHFFFAOYSA-N 0.000 description 2
• AFDZALFMHUZLIS-UHFFFAOYSA-N ethyl 2-[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NC(=O)N(CC2CCCC2)C=2C=C(F)C(F)=CC=2)=N1 AFDZALFMHUZLIS-UHFFFAOYSA-N 0.000 description 2
• IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 2
• PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 2
• QCTDKTISHYKODE-UHFFFAOYSA-N ethyl 3-[(2-amino-1,3-thiazol-5-yl)sulfanyl]-2,2-dimethylpropanoate Chemical compound CCOC(=O)C(C)(C)CSC1=CN=C(N)S1 QCTDKTISHYKODE-UHFFFAOYSA-N 0.000 description 2
• MKEKYOZQJSFNBB-UHFFFAOYSA-N ethyl 3-[(2-amino-1,3-thiazol-5-yl)sulfonylamino]propanoate Chemical compound CCOC(=O)CCNS(=O)(=O)C1=CN=C(N)S1 MKEKYOZQJSFNBB-UHFFFAOYSA-N 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 230000001747 exhibiting effect Effects 0.000 description 2
• 239000000284 extract Substances 0.000 description 2
• 239000011536 extraction buffer Substances 0.000 description 2
• 235000019197 fats Nutrition 0.000 description 2
• 230000004907 flux Effects 0.000 description 2
• 235000013355 food flavoring agent Nutrition 0.000 description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
• 239000012458 free base Substances 0.000 description 2
• 230000002496 gastric effect Effects 0.000 description 2
• 238000001502 gel electrophoresis Methods 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 238000002523 gelfiltration Methods 0.000 description 2
• 238000007429 general method Methods 0.000 description 2
• 230000002068 genetic effect Effects 0.000 description 2
• 208000004104 gestational diabetes Diseases 0.000 description 2
• 229960001381 glipizide Drugs 0.000 description 2
• ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 2
• MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 2
• 229960004666 glucagon Drugs 0.000 description 2
• 230000014101 glucose homeostasis Effects 0.000 description 2
• 229940074045 glyceryl distearate Drugs 0.000 description 2
• 229940075507 glyceryl monostearate Drugs 0.000 description 2
• 239000000122 growth hormone Substances 0.000 description 2
• 125000005843 halogen group Chemical group 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 230000002440 hepatic effect Effects 0.000 description 2
• 125000005349 heteroarylcycloalkyl group Chemical group 0.000 description 2
• 125000005368 heteroarylthio group Chemical group 0.000 description 2
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
• JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
• 229940088597 hormone Drugs 0.000 description 2
• 239000005556 hormone Substances 0.000 description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
• 230000003345 hyperglycaemic effect Effects 0.000 description 2
• 230000003451 hyperinsulinaemic effect Effects 0.000 description 2
• 201000008980 hyperinsulinism Diseases 0.000 description 2
• 229940126904 hypoglycaemic agent Drugs 0.000 description 2
• 230000002267 hypothalamic effect Effects 0.000 description 2
• 125000002883 imidazolyl group Chemical group 0.000 description 2
• 230000001976 improved effect Effects 0.000 description 2
• 239000012535 impurity Substances 0.000 description 2
• 229940102223 injectable solution Drugs 0.000 description 2
• 208000020658 intracerebral hemorrhage Diseases 0.000 description 2
• 238000007912 intraperitoneal administration Methods 0.000 description 2
• 238000007913 intrathecal administration Methods 0.000 description 2
• 208000002551 irritable bowel syndrome Diseases 0.000 description 2
• QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
• 125000001786 isothiazolyl group Chemical group 0.000 description 2
• 201000006370 kidney failure Diseases 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• 235000010445 lecithin Nutrition 0.000 description 2
• 239000000787 lecithin Substances 0.000 description 2
• 229940067606 lecithin Drugs 0.000 description 2
• NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 2
• 229940039781 leptin Drugs 0.000 description 2
• 230000003902 lesion Effects 0.000 description 2
• 239000002502 liposome Substances 0.000 description 2
• 239000006193 liquid solution Substances 0.000 description 2
• 239000006194 liquid suspension Substances 0.000 description 2
• 239000012280 lithium aluminium hydride Substances 0.000 description 2
• 230000003908 liver function Effects 0.000 description 2
• 230000007774 longterm Effects 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 230000014759 maintenance of location Effects 0.000 description 2
• 238000004949 mass spectrometry Methods 0.000 description 2
• 229950004994 meglitinide Drugs 0.000 description 2
• 239000002865 melanocortin Substances 0.000 description 2
• 208000030159 metabolic disease Diseases 0.000 description 2
• 229940098779 methanesulfonic acid Drugs 0.000 description 2
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• YXNVJAXCAQMTKL-UHFFFAOYSA-N n-(4-methylsulfonylphenyl)cyclopentanecarboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC(=O)C1CCCC1 YXNVJAXCAQMTKL-UHFFFAOYSA-N 0.000 description 2
• VNDFCLJKJLDQKX-UHFFFAOYSA-N n-(cyclopentylmethyl)-3,4-difluoroaniline Chemical compound C1=C(F)C(F)=CC=C1NCC1CCCC1 VNDFCLJKJLDQKX-UHFFFAOYSA-N 0.000 description 2
• WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 208000029140 neonatal diabetes Diseases 0.000 description 2
• 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 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• 239000000346 nonvolatile oil Substances 0.000 description 2
• URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 2
• QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
• 239000002674 ointment Substances 0.000 description 2
• 230000003287 optical effect Effects 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 description 2
• 125000002971 oxazolyl group Chemical group 0.000 description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
• NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
• 239000008188 pellet Substances 0.000 description 2
• 230000002093 peripheral effect Effects 0.000 description 2
• 239000008177 pharmaceutical agent Substances 0.000 description 2
• 239000000825 pharmaceutical preparation Substances 0.000 description 2
• 229940127557 pharmaceutical product Drugs 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• 229960005323 phenoxyethanol Drugs 0.000 description 2
• 229940100595 phenylacetaldehyde Drugs 0.000 description 2
• HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• 108020001213 potassium channel Proteins 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 230000008569 process Effects 0.000 description 2
• 108090000765 processed proteins & peptides Proteins 0.000 description 2
• AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
• XNSAINXGIQZQOO-SRVKXCTJSA-N protirelin Chemical compound NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H]1NC(=O)CC1)CC1=CN=CN1 XNSAINXGIQZQOO-SRVKXCTJSA-N 0.000 description 2
• 125000003373 pyrazinyl group Chemical group 0.000 description 2
• 125000003226 pyrazolyl group Chemical group 0.000 description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 description 2
• 125000000168 pyrrolyl group Chemical group 0.000 description 2
• 150000003254 radicals Chemical class 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 238000006578 reductive coupling reaction Methods 0.000 description 2
• 229960002354 repaglinide Drugs 0.000 description 2
• 238000011160 research Methods 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• 125000006413 ring segment Chemical group 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 229940076279 serotonin Drugs 0.000 description 2
• 239000003772 serotonin uptake inhibitor Substances 0.000 description 2
• 239000008159 sesame oil Substances 0.000 description 2
• 235000011803 sesame oil Nutrition 0.000 description 2
• 210000000329 smooth muscle myocyte Anatomy 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Inorganic materials [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
• VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 2
• 239000011877 solvent mixture Substances 0.000 description 2
• 235000011069 sorbitan monooleate Nutrition 0.000 description 2
• 239000001593 sorbitan monooleate Substances 0.000 description 2
• 229940035049 sorbitan monooleate Drugs 0.000 description 2
• 238000010561 standard procedure Methods 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 238000003860 storage Methods 0.000 description 2
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
• 235000000346 sugar Nutrition 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• 125000004434 sulfur atom Chemical group 0.000 description 2
• 239000006228 supernatant Substances 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 230000009885 systemic effect Effects 0.000 description 2
• 239000000454 talc Substances 0.000 description 2
• 235000012222 talc Nutrition 0.000 description 2
• 229910052623 talc Inorganic materials 0.000 description 2
• 235000002906 tartaric acid Nutrition 0.000 description 2
• 239000011975 tartaric acid Substances 0.000 description 2
• 125000003831 tetrazolyl group Chemical group 0.000 description 2
• 125000001113 thiadiazolyl group Chemical group 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• 238000004809 thin layer chromatography Methods 0.000 description 2
• 150000003573 thiols Chemical class 0.000 description 2
• 229940034199 thyrotropin-releasing hormone Drugs 0.000 description 2
• 229960005371 tolbutamide Drugs 0.000 description 2
• 230000000699 topical effect Effects 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 125000001425 triazolyl group Chemical group 0.000 description 2
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• 102000003390 tumor necrosis factor Human genes 0.000 description 2
• 239000002691 unilamellar liposome Substances 0.000 description 2
• 235000015112 vegetable and seed oil Nutrition 0.000 description 2
• 239000008158 vegetable oil Substances 0.000 description 2
• 239000003039 volatile agent Substances 0.000 description 2
• 239000003643 water by type Substances 0.000 description 2
• AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
• DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
• DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
• HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 description 1
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• QNDFBOXBUCDYNZ-NRFANRHFSA-N (2s)-2-ethoxy-3-[4-[2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(NC(=O)OC(C)(C)C)C=C1 QNDFBOXBUCDYNZ-NRFANRHFSA-N 0.000 description 1
• WMUIIGVAWPWQAW-DEOSSOPVSA-N (2s)-2-ethoxy-3-{4-[2-(10h-phenoxazin-10-yl)ethoxy]phenyl}propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2OC2=CC=CC=C21 WMUIIGVAWPWQAW-DEOSSOPVSA-N 0.000 description 1
• BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 description 1
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
• DMJWENQHWZZWDF-PKOBYXMFSA-N (6aS,13bR)-11-chloro-7-methyl-5,6,6a,8,9,13b-hexahydronaphtho[1,2-a][3]benzazepin-12-ol Chemical compound CN1CCC2=CC(Cl)=C(O)C=C2[C@H]2C3=CC=CC=C3CC[C@H]12 DMJWENQHWZZWDF-PKOBYXMFSA-N 0.000 description 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
• WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
• RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
• ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
• WTGVJERCTXWBLZ-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-hydroxybenzoic acid Chemical compound OC(=O)\C=C/C(O)=O.OC(=O)C1=CC=CC=C1O WTGVJERCTXWBLZ-BTJKTKAUSA-N 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
• 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
• 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 description 1
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
• 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 description 1
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
• LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical class OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
• IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
• YHXLWQGSQWIDIB-UHFFFAOYSA-N 1,3-thiazol-2-amine;urea Chemical class NC(N)=O.NC1=NC=CS1 YHXLWQGSQWIDIB-UHFFFAOYSA-N 0.000 description 1
• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 1
• YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
• 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
• RTWOAVKBRMACKZ-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)ethanol Chemical compound COC1=CC=C(C(C)O)C=C1OC RTWOAVKBRMACKZ-UHFFFAOYSA-N 0.000 description 1
• TXVVVEUSVBLDED-UHFFFAOYSA-N 1-(bromomethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1CBr TXVVVEUSVBLDED-UHFFFAOYSA-N 0.000 description 1
• ZSBCQBRVNBLWAW-UHFFFAOYSA-N 1-(bromomethyl)-2-(trifluoromethylsulfanyl)benzene Chemical compound FC(F)(F)SC1=CC=CC=C1CBr ZSBCQBRVNBLWAW-UHFFFAOYSA-N 0.000 description 1
• GAUUDQVOPUKGJD-UHFFFAOYSA-N 1-(bromomethyl)-2-chloro-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C(Cl)=C1 GAUUDQVOPUKGJD-UHFFFAOYSA-N 0.000 description 1
• PURSZYWBIQIANP-UHFFFAOYSA-N 1-(bromomethyl)-2-chlorobenzene Chemical compound ClC1=CC=CC=C1CBr PURSZYWBIQIANP-UHFFFAOYSA-N 0.000 description 1
• FFWQLZFIMNTUCZ-UHFFFAOYSA-N 1-(bromomethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CBr FFWQLZFIMNTUCZ-UHFFFAOYSA-N 0.000 description 1
• GYFDUIHVBNYYFE-UHFFFAOYSA-N 1-(bromomethyl)-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(CBr)=C1 GYFDUIHVBNYYFE-UHFFFAOYSA-N 0.000 description 1
• JDNPUJCKXLOHOW-UHFFFAOYSA-N 1-(bromomethyl)-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(CBr)C=C1 JDNPUJCKXLOHOW-UHFFFAOYSA-N 0.000 description 1
• IKSNDOVDVVPSMA-UHFFFAOYSA-N 1-(bromomethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(CBr)C=C1 IKSNDOVDVVPSMA-UHFFFAOYSA-N 0.000 description 1
• JMNOONULDANZRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluoro-2-(trifluoromethyl)benzene Chemical compound FC1=CC=C(CBr)C(C(F)(F)F)=C1 JMNOONULDANZRZ-UHFFFAOYSA-N 0.000 description 1
• NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 1
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical group C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 description 1
• CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• ZMXDDKWLCZADIW-WFVSFCRTSA-N 1-deuterio-n,n-dimethylformamide Chemical compound [2H]C(=O)N(C)C ZMXDDKWLCZADIW-WFVSFCRTSA-N 0.000 description 1
• 125000006039 1-hexenyl group Chemical group 0.000 description 1
• IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• 125000006023 1-pentenyl group Chemical group 0.000 description 1
• YHMRKVGUSQWDGZ-UHFFFAOYSA-N 1-phenylmethoxypropan-2-one Chemical compound CC(=O)COCC1=CC=CC=C1 YHMRKVGUSQWDGZ-UHFFFAOYSA-N 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
• ONOXJNUNOLWUEN-UHFFFAOYSA-N 2,2-dimethyl-3-[[2-[[(4-methylcyclohexyl)-(2-phenylethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(C)(C)C(O)=O)=CN=1)CCC1=CC=CC=C1 ONOXJNUNOLWUEN-UHFFFAOYSA-N 0.000 description 1
• YHWOSNKZLQBFSW-UHFFFAOYSA-N 2,2-dimethyl-3-[[2-[[(4-methylcyclohexyl)-(2-phenylmethoxyethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(C)(C)C(O)=O)=CN=1)CCOCC1=CC=CC=C1 YHWOSNKZLQBFSW-UHFFFAOYSA-N 0.000 description 1
• ABBJVZWZERUNJZ-UHFFFAOYSA-N 2,2-dimethyl-3-[[2-[[(4-methylcyclohexyl)-(3-phenoxypropyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(C)(C)C(O)=O)=CN=1)CCCOC1=CC=CC=C1 ABBJVZWZERUNJZ-UHFFFAOYSA-N 0.000 description 1
• OPVMUZQHHFBUSE-UHFFFAOYSA-N 2,2-dimethyl-3-[[2-[[(4-methylcyclohexyl)-(3-phenylsulfanylpropyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(C)(C)C(O)=O)=CN=1)CCCSC1=CC=CC=C1 OPVMUZQHHFBUSE-UHFFFAOYSA-N 0.000 description 1
• GZOWAMKNMXDBHV-UHFFFAOYSA-N 2,2-dimethyl-3-[[2-[[(4-methylcyclohexyl)-(3-phenylsulfanylpropyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(C)(C)C(O)=O)CCCSC1=CC=CC=C1 GZOWAMKNMXDBHV-UHFFFAOYSA-N 0.000 description 1
• WDZQROSDCVFJKO-UHFFFAOYSA-N 2,2-dimethyl-3-[[2-[[(4-methylcyclohexyl)-[2-[(2-methylphenyl)methoxy]ethyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(C)(C)C(O)=O)=CN=1)CCOCC1=CC=CC=C1C WDZQROSDCVFJKO-UHFFFAOYSA-N 0.000 description 1
• UWMKFZZKMJHOJI-UHFFFAOYSA-N 2,2-dimethyl-3-[[2-[[(4-methylcyclohexyl)-[2-[[2-(trifluoromethyl)phenyl]methoxy]ethyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(C)(C)C(O)=O)=CN=1)CCOCC1=CC=CC=C1C(F)(F)F UWMKFZZKMJHOJI-UHFFFAOYSA-N 0.000 description 1
• WVXMHZZTRIOGBE-UHFFFAOYSA-N 2,3-dichloro-n-(cyclopentylmethyl)aniline Chemical compound ClC1=CC=CC(NCC2CCCC2)=C1Cl WVXMHZZTRIOGBE-UHFFFAOYSA-N 0.000 description 1
• GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 1
• NVWVWEWVLBKPSM-UHFFFAOYSA-N 2,4-difluorophenol Chemical compound OC1=CC=C(F)C=C1F NVWVWEWVLBKPSM-UHFFFAOYSA-N 0.000 description 1
• SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
• JZAWBDIRCFFJBI-UHFFFAOYSA-N 2-(4-oxocyclohexyl)acetic acid Chemical compound OC(=O)CC1CCC(=O)CC1 JZAWBDIRCFFJBI-UHFFFAOYSA-N 0.000 description 1
• CNEQBJJJYWSQDJ-UHFFFAOYSA-N 2-(4-propoxycyclohexyl)isoindole-1,3-dione Chemical compound C1CC(OCCC)CCC1N1C(=O)C2=CC=CC=C2C1=O CNEQBJJJYWSQDJ-UHFFFAOYSA-N 0.000 description 1
• QGXNHCXKWFNKCG-UHFFFAOYSA-N 2-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=CC=C1C#N QGXNHCXKWFNKCG-UHFFFAOYSA-N 0.000 description 1
• IUDMXOOVKMKODN-UHFFFAOYSA-N 2-(cyclohexen-1-yl)ethanamine Chemical compound NCCC1=CCCCC1 IUDMXOOVKMKODN-UHFFFAOYSA-N 0.000 description 1
• DYORPHZZZAWZPI-UHFFFAOYSA-N 2-(cyclohexen-1-yl)ethanamine;hydrochloride Chemical compound Cl.NCCC1=CCCCC1 DYORPHZZZAWZPI-UHFFFAOYSA-N 0.000 description 1
• VAPVFLQNUDBCCN-UHFFFAOYSA-N 2-[(2-acetamido-1,3-thiazol-5-yl)sulfonyl-methylamino]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CN(C)S(=O)(=O)C1=CN=C(NC(C)=O)S1 VAPVFLQNUDBCCN-UHFFFAOYSA-N 0.000 description 1
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
• XAGQJDVCMCDHOP-UHFFFAOYSA-N 2-[[2-[[(1-acetyl-2,3-dihydroindol-6-yl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=C2N(C(=O)C)CCC2=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 XAGQJDVCMCDHOP-UHFFFAOYSA-N 0.000 description 1
• QERDZRUPUNEHQE-UHFFFAOYSA-N 2-[[2-[[(2-bromophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C(=CC=CC=1)Br)CC1CCCC1 QERDZRUPUNEHQE-UHFFFAOYSA-N 0.000 description 1
• QBXBVDZFHTXCQJ-UHFFFAOYSA-N 2-[[2-[[(2-chloro-3-fluorophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C(=C(F)C=CC=1)Cl)CC1CCCC1 QBXBVDZFHTXCQJ-UHFFFAOYSA-N 0.000 description 1
• GULDCOMIOMEXSM-UHFFFAOYSA-N 2-[[2-[[(3-acetamido-4-fluorophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=C(F)C(NC(=O)C)=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 GULDCOMIOMEXSM-UHFFFAOYSA-N 0.000 description 1
• BITZIOMMOKBJFE-UHFFFAOYSA-N 2-[[2-[[(3-acetamidophenyl)-(2-phenylethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC(=O)NC1=CC=CC(N(CCC=2C=CC=CC=2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 BITZIOMMOKBJFE-UHFFFAOYSA-N 0.000 description 1
• ZCUNZQVXKZOOOY-UHFFFAOYSA-N 2-[[2-[[(3-acetamidophenyl)-(cyclohexylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC(=O)NC1=CC=CC(N(CC2CCCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 ZCUNZQVXKZOOOY-UHFFFAOYSA-N 0.000 description 1
• VBZFWUYRQLMHQD-UHFFFAOYSA-N 2-[[2-[[(3-acetylphenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 VBZFWUYRQLMHQD-UHFFFAOYSA-N 0.000 description 1
• RXZPPCLNNKPXAL-UHFFFAOYSA-N 2-[[2-[[(3-bromophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(Br)C=CC=1)CC1CCCC1 RXZPPCLNNKPXAL-UHFFFAOYSA-N 0.000 description 1
• DBBCBOPYUBEQNO-UHFFFAOYSA-N 2-[[2-[[(3-chloro-2-fluorophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C(=C(Cl)C=CC=1)F)CC1CCCC1 DBBCBOPYUBEQNO-UHFFFAOYSA-N 0.000 description 1
• KZYOPUVJAZPOSI-UHFFFAOYSA-N 2-[[2-[[(3-chloro-2-methoxyphenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound COC1=C(Cl)C=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 KZYOPUVJAZPOSI-UHFFFAOYSA-N 0.000 description 1
• XVRSLNRAZSUMEM-UHFFFAOYSA-N 2-[[2-[[(3-chloro-2-methylphenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC1=C(Cl)C=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 XVRSLNRAZSUMEM-UHFFFAOYSA-N 0.000 description 1
• LZBASQCVJWZLGM-UHFFFAOYSA-N 2-[[2-[[(3-chloro-4-methoxyphenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 LZBASQCVJWZLGM-UHFFFAOYSA-N 0.000 description 1
• DUYUAQCMZZJCRN-UHFFFAOYSA-N 2-[[2-[[(4-bromo-2-fluorophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C(=CC(Br)=CC=1)F)CC1CCCC1 DUYUAQCMZZJCRN-UHFFFAOYSA-N 0.000 description 1
• DNFOWGMFTICIQC-UHFFFAOYSA-N 2-[[2-[[(4-methylcyclohexyl)-(2-phenylethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCC1=CC=CC=C1 DNFOWGMFTICIQC-UHFFFAOYSA-N 0.000 description 1
• JXVQDAOPBNLXQG-UHFFFAOYSA-N 2-[[2-[[(4-methylcyclohexyl)-(2-phenylmethoxyethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCOCC1=CC=CC=C1 JXVQDAOPBNLXQG-UHFFFAOYSA-N 0.000 description 1
• MZEGPXDBGLJFRH-UHFFFAOYSA-N 2-[[2-[[(4-methylcyclohexyl)-(3-phenoxypropyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCCOC1=CC=CC=C1 MZEGPXDBGLJFRH-UHFFFAOYSA-N 0.000 description 1
• GSAQUWYNHBDUQC-UHFFFAOYSA-N 2-[[2-[[(4-methylcyclohexyl)-(3-phenylsulfanylpropyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CCCSC1=CC=CC=C1 GSAQUWYNHBDUQC-UHFFFAOYSA-N 0.000 description 1
• ASAGUGALPMOYNP-UHFFFAOYSA-N 2-[[2-[[(4-methylcyclohexyl)-(3-phenylsulfanylpropyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCCSC1=CC=CC=C1 ASAGUGALPMOYNP-UHFFFAOYSA-N 0.000 description 1
• GQTPTEWMYBLWPU-UHFFFAOYSA-N 2-[[2-[[(4-methylcyclohexyl)-[2-[(2-methylphenyl)methoxy]ethyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCOCC1=CC=CC=C1C GQTPTEWMYBLWPU-UHFFFAOYSA-N 0.000 description 1
• KELXFXQYNONFLB-UHFFFAOYSA-N 2-[[2-[[(4-methylcyclohexyl)-[2-[[2-(trifluoromethyl)phenyl]methoxy]ethyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCOCC1=CC=CC=C1C(F)(F)F KELXFXQYNONFLB-UHFFFAOYSA-N 0.000 description 1
• XCLFKWLPPKKKBG-UHFFFAOYSA-N 2-[[2-[[2-(3-fluoro-4-methoxyphenyl)ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1=C(F)C(OC)=CC=C1CCN(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)C1CCC(C)CC1 XCLFKWLPPKKKBG-UHFFFAOYSA-N 0.000 description 1
• LDCSVBBSTWKJFY-UHFFFAOYSA-N 2-[[2-[[2-(4-ethoxyphenyl)ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1=CC(OCC)=CC=C1CCN(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)C1CCC(C)CC1 LDCSVBBSTWKJFY-UHFFFAOYSA-N 0.000 description 1
• GXFWFUJMVJBWBE-UHFFFAOYSA-N 2-[[2-[[2-(4-methoxyphenyl)ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1CCN(C(=O)NC=1SC(=CN=1)S(=O)(=O)C(C)(C)C(O)=O)C1CCC(C)CC1 GXFWFUJMVJBWBE-UHFFFAOYSA-N 0.000 description 1
• SVYARJPATSMITJ-UHFFFAOYSA-N 2-[[2-[[2-(4-methoxyphenyl)ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1=CC(OC)=CC=C1CCN(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)C1CCC(C)CC1 SVYARJPATSMITJ-UHFFFAOYSA-N 0.000 description 1
• AVVHHGSUMJGRGT-UHFFFAOYSA-N 2-[[2-[[2-[(2,4-difluorophenyl)methoxy]ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCOCC1=CC=C(F)C=C1F AVVHHGSUMJGRGT-UHFFFAOYSA-N 0.000 description 1
• PRGPJSHCFLSQSW-UHFFFAOYSA-N 2-[[2-[[2-[(2-chloro-4-fluorophenyl)methoxy]ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCOCC1=CC=C(F)C=C1Cl PRGPJSHCFLSQSW-UHFFFAOYSA-N 0.000 description 1
• LVHUVYWAZJLDQO-UHFFFAOYSA-N 2-[[2-[[2-[(2-chlorophenyl)methoxy]ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]-2-methylpropanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)C(C)(C)C(O)=O)CCOCC1=CC=CC=C1Cl LVHUVYWAZJLDQO-UHFFFAOYSA-N 0.000 description 1
• RXGJLBKXDRXUBI-UHFFFAOYSA-N 2-[[2-[[2-[(2-chlorophenyl)methoxy]ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCOCC1=CC=CC=C1Cl RXGJLBKXDRXUBI-UHFFFAOYSA-N 0.000 description 1
• YSGBXNQLGRIXNM-UHFFFAOYSA-N 2-[[2-[[2-[(2-fluorophenyl)methoxy]ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]-2-methylpropanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)C(C)(C)C(O)=O)CCOCC1=CC=CC=C1F YSGBXNQLGRIXNM-UHFFFAOYSA-N 0.000 description 1
• GCJLWXSDPLYGFA-UHFFFAOYSA-N 2-[[2-[[2-[(2-fluorophenyl)methoxy]ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCOCC1=CC=CC=C1F GCJLWXSDPLYGFA-UHFFFAOYSA-N 0.000 description 1
• DRHMKZLTHITKRP-UHFFFAOYSA-N 2-[[2-[[2-[[4-fluoro-2-(trifluoromethyl)phenyl]methoxy]ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]-2-methylpropanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)C(C)(C)C(O)=O)CCOCC1=CC=C(F)C=C1C(F)(F)F DRHMKZLTHITKRP-UHFFFAOYSA-N 0.000 description 1
• LCLPNFZQYQTXDJ-UHFFFAOYSA-N 2-[[2-[[2-[[4-fluoro-2-(trifluoromethyl)phenyl]methoxy]ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCOCC1=CC=C(F)C=C1C(F)(F)F LCLPNFZQYQTXDJ-UHFFFAOYSA-N 0.000 description 1
• MUYURUMWAYXHMR-UHFFFAOYSA-N 2-[[2-[[2-benzylsulfanylethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]-2-methylpropanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SC(C)(C)C(O)=O)=CN=1)CCSCC1=CC=CC=C1 MUYURUMWAYXHMR-UHFFFAOYSA-N 0.000 description 1
• FETHZKMAFIXZQX-UHFFFAOYSA-N 2-[[2-[[2-benzylsulfanylethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CCSCC1=CC=CC=C1 FETHZKMAFIXZQX-UHFFFAOYSA-N 0.000 description 1
• PTVWCUWDXAVKFG-UHFFFAOYSA-N 2-[[2-[[2-benzylsulfanylethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]-2-methylpropanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)C(C)(C)C(O)=O)CCSCC1=CC=CC=C1 PTVWCUWDXAVKFG-UHFFFAOYSA-N 0.000 description 1
• YVNNOIMLUBOBIG-UHFFFAOYSA-N 2-[[2-[[2-benzylsulfanylethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]acetic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(O)=O)CCSCC1=CC=CC=C1 YVNNOIMLUBOBIG-UHFFFAOYSA-N 0.000 description 1
• CIVODCYZAVGPIH-UHFFFAOYSA-N 2-[[2-[[2-cyclopentylethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CCC1CCCC1 CIVODCYZAVGPIH-UHFFFAOYSA-N 0.000 description 1
• WVFHLEQCVLLACA-UHFFFAOYSA-N 2-[[2-[[[3-(cyclopentanecarbonylamino)phenyl]-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(NC(=O)C2CCCC2)C=CC=1)CC1CCCC1 WVFHLEQCVLLACA-UHFFFAOYSA-N 0.000 description 1
• GNJKRCLZFCAEBJ-UHFFFAOYSA-N 2-[[2-[[butyl(cyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound N=1C=C(SCC(O)=O)SC=1NC(=O)N(CCCC)C1CCCCC1 GNJKRCLZFCAEBJ-UHFFFAOYSA-N 0.000 description 1
• TWYBXCSFUZFUKE-UHFFFAOYSA-N 2-[[2-[[cyclohexyl(2,2-dimethylpropyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound N=1C=C(SCC(O)=O)SC=1NC(=O)N(CC(C)(C)C)C1CCCCC1 TWYBXCSFUZFUKE-UHFFFAOYSA-N 0.000 description 1
• WCVRAISQEHSBBW-UHFFFAOYSA-N 2-[[2-[[cyclohexyl(3-methylbutyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]-2-methylpropanoic acid Chemical compound N=1C=C(SC(C)(C)C(O)=O)SC=1NC(=O)N(CCC(C)C)C1CCCCC1 WCVRAISQEHSBBW-UHFFFAOYSA-N 0.000 description 1
• BMXVAAJRBJSEHH-UHFFFAOYSA-N 2-[[2-[[cyclohexylmethyl-(2,3,4-trifluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C(=C(F)C(F)=CC=1)F)CC1CCCCC1 BMXVAAJRBJSEHH-UHFFFAOYSA-N 0.000 description 1
• PQELKXSMCXTEII-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(2,2-difluoro-1,3-benzodioxol-5-yl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C2OC(F)(F)OC2=CC=1)CC1CCCC1 PQELKXSMCXTEII-UHFFFAOYSA-N 0.000 description 1
• UBNXIBOMPQIIFE-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(2,3-difluoro-4-methoxyphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound FC1=C(F)C(OC)=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 UBNXIBOMPQIIFE-UHFFFAOYSA-N 0.000 description 1
• GRGJPZKHXZRUTM-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(2,3-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C(=C(F)C=CC=1)F)CC1CCCC1 GRGJPZKHXZRUTM-UHFFFAOYSA-N 0.000 description 1
• QFDZJPYVAXEZPF-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(2,4,6-trifluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C(=CC(F)=CC=1F)F)CC1CCCC1 QFDZJPYVAXEZPF-UHFFFAOYSA-N 0.000 description 1
• RNIFJMAOVUHFTK-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(2-fluoro-3-methylphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1F RNIFJMAOVUHFTK-UHFFFAOYSA-N 0.000 description 1
• DSCLETYBFOMHRR-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 DSCLETYBFOMHRR-UHFFFAOYSA-N 0.000 description 1
• GNUAELWFFZLYSR-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(3-fluoro-2-methylphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC1=C(F)C=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 GNUAELWFFZLYSR-UHFFFAOYSA-N 0.000 description 1
• FAUJJKXRYMECLR-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(3-sulfamoylphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound NS(=O)(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 FAUJJKXRYMECLR-UHFFFAOYSA-N 0.000 description 1
• QQAUOTOQIUWYLG-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=C(F)C(OC)=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 QQAUOTOQIUWYLG-UHFFFAOYSA-N 0.000 description 1
• QWSUIGJIDJDHQM-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(4-methoxyphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=CC(OC)=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 QWSUIGJIDJDHQM-UHFFFAOYSA-N 0.000 description 1
• MEXILGRQXHTUDO-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-(4-propan-2-yloxyphenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1=CC(OC(C)C)=CC=C1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)CC1CCCC1 MEXILGRQXHTUDO-UHFFFAOYSA-N 0.000 description 1
• MMNVKLCKSVZLOX-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[3-(2-methylpropanoylamino)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CC(C)C(=O)NC1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 MMNVKLCKSVZLOX-UHFFFAOYSA-N 0.000 description 1
• KXMJSSICGZQPMD-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[3-(propanoylamino)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound CCC(=O)NC1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 KXMJSSICGZQPMD-UHFFFAOYSA-N 0.000 description 1
• MRQRPEJVUDXEOY-UHFFFAOYSA-N 2-[[2-[[cyclopentylmethyl-[3-methoxy-5-(trifluoromethyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound FC(F)(F)C1=CC(OC)=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(O)=O)=CN=2)=C1 MRQRPEJVUDXEOY-UHFFFAOYSA-N 0.000 description 1
• FHEYFIGWYQJVDR-ACJLOTCBSA-N 2-[[3-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1h-indol-7-yl]oxy]acetic acid Chemical compound C1([C@@H](O)CN[C@@H](CC=2C3=CC=CC(OCC(O)=O)=C3NC=2)C)=CC=CC(Cl)=C1 FHEYFIGWYQJVDR-ACJLOTCBSA-N 0.000 description 1
• LUACLLSCZRRTIH-UPHRSURJSA-N 2-[[4-[(z)-4-[4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy]but-2-enoxy]phenyl]methyl]-1,2,4-oxadiazolidine-3,5-dione Chemical compound O1C(=O)NC(=O)N1CC(C=C1)=CC=C1OC\C=C/COC(C=C1)=CC=C1CN1C(=O)NC(=O)O1 LUACLLSCZRRTIH-UPHRSURJSA-N 0.000 description 1
• BJBCSGQLZQGGIQ-QGZVFWFLSA-N 2-acetamidoethyl (2r)-2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenoxy]acetate Chemical compound O([C@@H](C(=O)OCCNC(=O)C)C=1C=CC(Cl)=CC=1)C1=CC=CC(C(F)(F)F)=C1 BJBCSGQLZQGGIQ-QGZVFWFLSA-N 0.000 description 1
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
• JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 1
• FWOHDAGPWDEWIB-UHFFFAOYSA-N 2-bromoethoxymethylbenzene Chemical compound BrCCOCC1=CC=CC=C1 FWOHDAGPWDEWIB-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical compound CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 description 1
• ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
• DEDUBNVYPMOFDR-UHFFFAOYSA-N 2-ethoxypropan-1-ol Chemical compound CCOC(C)CO DEDUBNVYPMOFDR-UHFFFAOYSA-N 0.000 description 1
• HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000006040 2-hexenyl group Chemical group 0.000 description 1
• UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
• ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 1
• 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
• SADVMKJGVKCPHW-UHFFFAOYSA-N 2-methyl-2-[[2-[[(4-methylcyclohexyl)-(2-phenylethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)C(C)(C)C(O)=O)CCC1=CC=CC=C1 SADVMKJGVKCPHW-UHFFFAOYSA-N 0.000 description 1
• YEJZHIACVUIAKY-UHFFFAOYSA-N 2-methyl-2-[[2-[[(4-methylcyclohexyl)-(3-phenoxypropyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)C(C)(C)C(O)=O)CCCOC1=CC=CC=C1 YEJZHIACVUIAKY-UHFFFAOYSA-N 0.000 description 1
• OCVXXPPTRFAORO-UHFFFAOYSA-N 2-methyl-2-[[2-[[(4-methylcyclohexyl)-(3-phenylsulfanylpropyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)C(C)(C)C(O)=O)CCCSC1=CC=CC=C1 OCVXXPPTRFAORO-UHFFFAOYSA-N 0.000 description 1
• WKVKNIXBUDZIHM-UHFFFAOYSA-N 2-methyl-2-[[2-[[(4-methylcyclohexyl)-[2-[(2-methylphenyl)methoxy]ethyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]propanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)C(C)(C)C(O)=O)CCOCC1=CC=CC=C1C WKVKNIXBUDZIHM-UHFFFAOYSA-N 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000006024 2-pentenyl group Chemical group 0.000 description 1
• LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 1
• CUZKCNWZBXLAJX-UHFFFAOYSA-N 2-phenylmethoxyethanol Chemical compound OCCOCC1=CC=CC=C1 CUZKCNWZBXLAJX-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• LTNUSYNQZJZUSY-UHFFFAOYSA-N 3,3-dimethylbutanal Chemical compound CC(C)(C)CC=O LTNUSYNQZJZUSY-UHFFFAOYSA-N 0.000 description 1
• WNHPMKYMPWMAIT-UHFFFAOYSA-N 3,4,5,6-tetrahydro-2h-azepine Chemical compound C1CCC=NCC1 WNHPMKYMPWMAIT-UHFFFAOYSA-N 0.000 description 1
• 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 description 1
• BNPWVUJOPCGHIK-UHFFFAOYSA-N 3,4-difluorophenol Chemical compound OC1=CC=C(F)C(F)=C1 BNPWVUJOPCGHIK-UHFFFAOYSA-N 0.000 description 1
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
• JNBIJMYRSDRFLD-UHFFFAOYSA-N 3-(2-cyclopentylethylamino)-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC(NCCC2CCCC2)=C1 JNBIJMYRSDRFLD-UHFFFAOYSA-N 0.000 description 1
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
• UKYUMAVOUDTWNH-UHFFFAOYSA-N 3-(cyclopentylmethylamino)-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC(NCC2CCCC2)=C1 UKYUMAVOUDTWNH-UHFFFAOYSA-N 0.000 description 1
• ISNNULAJCDEYFS-UHFFFAOYSA-N 3-(cyclopentylmethylamino)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NCC2CCCC2)=C1 ISNNULAJCDEYFS-UHFFFAOYSA-N 0.000 description 1
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
• UWLJERQTLRORJN-UHFFFAOYSA-N 3-(trifluoromethoxy)phenol Chemical compound OC1=CC=CC(OC(F)(F)F)=C1 UWLJERQTLRORJN-UHFFFAOYSA-N 0.000 description 1
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
• SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
• KYKDWICOFXFDTR-UHFFFAOYSA-N 3-[[2-[[2-(3-fluoro-4-methoxyphenyl)ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]-2,2-dimethylpropanoic acid Chemical compound C1=C(F)C(OC)=CC=C1CCN(C(=O)NC=1SC(SCC(C)(C)C(O)=O)=CN=1)C1CCC(C)CC1 KYKDWICOFXFDTR-UHFFFAOYSA-N 0.000 description 1
• DHKINTHBAXWWHF-UHFFFAOYSA-N 3-[[2-[[2-[(2-chlorophenyl)methoxy]ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]-2,2-dimethylpropanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(C)(C)C(O)=O)=CN=1)CCOCC1=CC=CC=C1Cl DHKINTHBAXWWHF-UHFFFAOYSA-N 0.000 description 1
• YRJZNIPVQYVNRO-UHFFFAOYSA-N 3-[[2-[[2-[(2-fluorophenyl)methoxy]ethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]-2,2-dimethylpropanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(C)(C)C(O)=O)=CN=1)CCOCC1=CC=CC=C1F YRJZNIPVQYVNRO-UHFFFAOYSA-N 0.000 description 1
• NCDFQQPSLSPLAQ-UHFFFAOYSA-N 3-[[2-[[2-benzylsulfanylethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]-2,2-dimethylpropanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(SCC(C)(C)C(O)=O)=CN=1)CCSCC1=CC=CC=C1 NCDFQQPSLSPLAQ-UHFFFAOYSA-N 0.000 description 1
• QEYOVNXCUYKHQS-UHFFFAOYSA-N 3-[[2-[[2-benzylsulfanylethyl-(4-methylcyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]-2,2-dimethylpropanoic acid Chemical compound C1CC(C)CCC1N(C(=O)NC=1SC(=CN=1)S(=O)(=O)CC(C)(C)C(O)=O)CCSCC1=CC=CC=C1 QEYOVNXCUYKHQS-UHFFFAOYSA-N 0.000 description 1
• MTHONZLNGBYYSR-UHFFFAOYSA-N 3-[[2-[[butyl(cyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound N=1C=C(SCCC(O)=O)SC=1NC(=O)N(CCCC)C1CCCCC1 MTHONZLNGBYYSR-UHFFFAOYSA-N 0.000 description 1
• BGTDLUGJJRZEPU-UHFFFAOYSA-N 3-[[2-[[cyclohexyl(3-methylbutyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoic acid Chemical compound N=1C=C(SCCC(O)=O)SC=1NC(=O)N(CCC(C)C)C1CCCCC1 BGTDLUGJJRZEPU-UHFFFAOYSA-N 0.000 description 1
• FYHBVTYDATZUEE-UHFFFAOYSA-N 3-bromo-2,2-dimethylpropanoic acid Chemical compound BrCC(C)(C)C(O)=O FYHBVTYDATZUEE-UHFFFAOYSA-N 0.000 description 1
• PSUXTZLDBVEZTD-UHFFFAOYSA-N 3-bromopropoxymethylbenzene Chemical compound BrCCCOCC1=CC=CC=C1 PSUXTZLDBVEZTD-UHFFFAOYSA-N 0.000 description 1
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
• ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
• SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 description 1
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000006041 3-hexenyl group Chemical group 0.000 description 1
• HJBLUNHMOKFZQX-UHFFFAOYSA-N 3-hydroxy-1,2,3-benzotriazin-4-one Chemical group C1=CC=C2C(=O)N(O)N=NC2=C1 HJBLUNHMOKFZQX-UHFFFAOYSA-N 0.000 description 1
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 description 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
• JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• QXZBMSIDSOZZHK-DOPDSADYSA-N 31362-50-2 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CNC=N1 QXZBMSIDSOZZHK-DOPDSADYSA-N 0.000 description 1
• MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• ZTGWZABDCLVGEN-UHFFFAOYSA-N 4-(cyclopentylmethylamino)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NCC1CCCC1 ZTGWZABDCLVGEN-UHFFFAOYSA-N 0.000 description 1
• YMZGIMHHKLYBQZ-UHFFFAOYSA-N 4-(ethoxymethyl)cyclohexan-1-amine Chemical compound CCOCC1CCC(N)CC1 YMZGIMHHKLYBQZ-UHFFFAOYSA-N 0.000 description 1
• KVAVSBWXDWZOFL-UHFFFAOYSA-N 4-(methoxymethyl)cyclohexan-1-amine Chemical compound COCC1CCC(N)CC1 KVAVSBWXDWZOFL-UHFFFAOYSA-N 0.000 description 1
• WDRJNKMAZMEYOF-UHFFFAOYSA-N 4-(trifluoromethoxy)phenol Chemical compound OC1=CC=C(OC(F)(F)F)C=C1 WDRJNKMAZMEYOF-UHFFFAOYSA-N 0.000 description 1
• IJCTXLVZPMAIJS-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxy]cyclohexan-1-amine Chemical compound CC(C)(C)OC1CCC(N)CC1 IJCTXLVZPMAIJS-UHFFFAOYSA-N 0.000 description 1
• LGSOKZOQANLOEU-UHFFFAOYSA-N 4-[2-(2,4-dioxo-1,3-thiazolidin-5-yl)ethoxy]benzonitrile Chemical compound S1C(=O)NC(=O)C1CCOC1=CC=C(C#N)C=C1 LGSOKZOQANLOEU-UHFFFAOYSA-N 0.000 description 1
• YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
• QBQLYIISSRXYKL-UHFFFAOYSA-N 4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC1C(=O)NOC1=O QBQLYIISSRXYKL-UHFFFAOYSA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
• QBLISOIWPZSVIK-UHFFFAOYSA-N 4-bromobutoxybenzene Chemical compound BrCCCCOC1=CC=CC=C1 QBLISOIWPZSVIK-UHFFFAOYSA-N 0.000 description 1
• WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
• RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
• JKQSKKCOSUMZTE-UHFFFAOYSA-N 4-methyl-n-(3-methylbutyl)cyclohexan-1-amine Chemical compound CC(C)CCNC1CCC(C)CC1 JKQSKKCOSUMZTE-UHFFFAOYSA-N 0.000 description 1
• VOACDSSPEFGGPZ-UHFFFAOYSA-N 4-methyl-n-(3-phenylmethoxypropyl)cyclohexan-1-amine Chemical compound C1CC(C)CCC1NCCCOCC1=CC=CC=C1 VOACDSSPEFGGPZ-UHFFFAOYSA-N 0.000 description 1
• NMEAGYKSZYLEAS-UHFFFAOYSA-N 4-methylsulfonylaniline;hydrochloride Chemical compound Cl.CS(=O)(=O)C1=CC=C(N)C=C1 NMEAGYKSZYLEAS-UHFFFAOYSA-N 0.000 description 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
• QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
• SMSHIXOEBWOYJS-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinazoline Chemical compound C1=NC=C2CCCCC2=N1 SMSHIXOEBWOYJS-UHFFFAOYSA-N 0.000 description 1
• YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 description 1
• NFFXEUUOMTXWCX-UHFFFAOYSA-N 5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CC1SC(=O)NC1=O NFFXEUUOMTXWCX-UHFFFAOYSA-N 0.000 description 1
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
• MVDXXGIBARMXSA-PYUWXLGESA-N 5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-PYUWXLGESA-N 0.000 description 1
• LKKAMJRUPIIUTC-UHFFFAOYSA-N 5-[[4-[(6-methoxy-1-methylbenzimidazol-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;hydrochloride Chemical compound Cl.CN1C2=CC(OC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O LKKAMJRUPIIUTC-UHFFFAOYSA-N 0.000 description 1
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
• 125000006043 5-hexenyl group Chemical group 0.000 description 1
• RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 1
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
• LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 1
• ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical compound C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 1
• KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
• SLXTWXQUEZSSTJ-UHFFFAOYSA-N 6-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl]pyridine-3-carboxylic acid Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1(C=2N=CC(=CC=2)C(O)=O)CC1 SLXTWXQUEZSSTJ-UHFFFAOYSA-N 0.000 description 1
• 102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
• 108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 239000005541 ACE inhibitor Substances 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 229920001817 Agar Polymers 0.000 description 1
• PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
• PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
• 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
• 102100030988 Angiotensin-converting enzyme Human genes 0.000 description 1
• 235000003911 Arachis Nutrition 0.000 description 1
• 244000105624 Arachis hypogaea Species 0.000 description 1
• 208000031104 Arterial Occlusive disease Diseases 0.000 description 1
• 200000000007 Arterial disease Diseases 0.000 description 1
• XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 1
• XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
• 102000013585 Bombesin Human genes 0.000 description 1
• 108010051479 Bombesin Proteins 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• ZPBJIIXTXXUVDV-UHFFFAOYSA-N C(C)(=O)OCCSC1=CN=C(S1)N Chemical compound C(C)(=O)OCCSC1=CN=C(S1)N ZPBJIIXTXXUVDV-UHFFFAOYSA-N 0.000 description 1
• RBOJZYIJYALXID-HAQNSBGRSA-N C1C[C@@H](C)CC[C@@H]1CN(C=1C(=C(F)C(F)=CC=1)F)C(=O)NC1=NC=C(SCC(O)=O)S1 Chemical compound C1C[C@@H](C)CC[C@@H]1CN(C=1C(=C(F)C(F)=CC=1)F)C(=O)NC1=NC=C(SCC(O)=O)S1 RBOJZYIJYALXID-HAQNSBGRSA-N 0.000 description 1
• QEJZOTXVZFPSPN-JOCQHMNTSA-N C1C[C@@H](N)CC[C@@H]1OCC1=CC=CC=C1 Chemical compound C1C[C@@H](N)CC[C@@H]1OCC1=CC=CC=C1 QEJZOTXVZFPSPN-JOCQHMNTSA-N 0.000 description 1
• VQVVFYUZDFOHRA-MGCOHNPYSA-N C1C[C@@H](N)CC[C@@H]1OCC1CC1 Chemical compound C1C[C@@H](N)CC[C@@H]1OCC1CC1 VQVVFYUZDFOHRA-MGCOHNPYSA-N 0.000 description 1
• GTKQLQYRYIWAIY-XYPYZODXSA-N C1C[C@@H](NCOC)CC[C@@H]1C1CC1 Chemical compound C1C[C@@H](NCOC)CC[C@@H]1C1CC1 GTKQLQYRYIWAIY-XYPYZODXSA-N 0.000 description 1
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 1
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical class C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
• 229940127291 Calcium channel antagonist Drugs 0.000 description 1
• 206010007559 Cardiac failure congestive Diseases 0.000 description 1
• 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
• 208000006029 Cardiomegaly Diseases 0.000 description 1
• 208000024172 Cardiovascular disease Diseases 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
• 229920001268 Cholestyramine Polymers 0.000 description 1
• 102100021809 Chorionic somatomammotropin hormone 1 Human genes 0.000 description 1
• 108010005939 Ciliary Neurotrophic Factor Proteins 0.000 description 1
• 102100031614 Ciliary neurotrophic factor Human genes 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• BDNBGXGBMVAZBM-KMMPGQJCSA-N Cl.COC[C@H]1CC[C@H](N)CC1 Chemical compound Cl.COC[C@H]1CC[C@H](N)CC1 BDNBGXGBMVAZBM-KMMPGQJCSA-N 0.000 description 1
• 229920002911 Colestipol Polymers 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 208000014311 Cushing syndrome Diseases 0.000 description 1
• 229920000858 Cyclodextrin Polymers 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
• XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 1
• 101710088194 Dehydrogenase Proteins 0.000 description 1
• 102000016911 Deoxyribonucleases Human genes 0.000 description 1
• 108010053770 Deoxyribonucleases Proteins 0.000 description 1
• 102100034573 Desmoglein-4 Human genes 0.000 description 1
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 238000002965 ELISA Methods 0.000 description 1
• 102000016942 Elastin Human genes 0.000 description 1
• 108010014258 Elastin Proteins 0.000 description 1
• 108010061435 Enalapril Proteins 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• GGUVRMBIEPYOKL-WMVCGJOFSA-N GW 409544 Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 GGUVRMBIEPYOKL-WMVCGJOFSA-N 0.000 description 1
• 102400001370 Galanin Human genes 0.000 description 1
• 101800002068 Galanin Proteins 0.000 description 1
• 208000001762 Gastric Dilatation Diseases 0.000 description 1
• HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 1
• VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
• 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
• 235000010469 Glycine max Nutrition 0.000 description 1
• 244000068988 Glycine max Species 0.000 description 1
• 206010019663 Hepatic failure Diseases 0.000 description 1
• 206010020880 Hypertrophy Diseases 0.000 description 1
• 229940094910 Insulin receptor antagonist Drugs 0.000 description 1
• 229940122355 Insulin sensitizer Drugs 0.000 description 1
• 102000005755 Intercellular Signaling Peptides and Proteins Human genes 0.000 description 1
• 108010070716 Intercellular Signaling Peptides and Proteins Proteins 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• 229930182816 L-glutamine Natural products 0.000 description 1
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
• 108010028554 LDL Cholesterol Proteins 0.000 description 1
• 208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 1
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• 239000004367 Lipase Substances 0.000 description 1
• 108090001060 Lipase Proteins 0.000 description 1
• 102000004882 Lipase Human genes 0.000 description 1
• 229940086609 Lipase inhibitor Drugs 0.000 description 1
• 206010049287 Lipodystrophy acquired Diseases 0.000 description 1
• 108010007859 Lisinopril Proteins 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 206010067125 Liver injury Diseases 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
• 208000004221 Multiple Trauma Diseases 0.000 description 1
• 102000016943 Muramidase Human genes 0.000 description 1
• 108010014251 Muramidase Proteins 0.000 description 1
• 208000008238 Muscle Spasticity Diseases 0.000 description 1
• 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
• 150000001204 N-oxides Chemical group 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
• REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 102000002512 Orexin Human genes 0.000 description 1
• 102400000319 Oxyntomodulin Human genes 0.000 description 1
• 101800001388 Oxyntomodulin Proteins 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 229930182555 Penicillin Natural products 0.000 description 1
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
• MFOCDFTXLCYLKU-CMPLNLGQSA-N Phendimetrazine Chemical compound O1CCN(C)[C@@H](C)[C@@H]1C1=CC=CC=C1 MFOCDFTXLCYLKU-CMPLNLGQSA-N 0.000 description 1
• 108010003044 Placental Lactogen Proteins 0.000 description 1
• 239000000381 Placental Lactogen Substances 0.000 description 1
• 239000004793 Polystyrene Substances 0.000 description 1
• TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
• 102100024819 Prolactin Human genes 0.000 description 1
• 108010057464 Prolactin Proteins 0.000 description 1
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
• 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 description 1
• 102000016611 Proteoglycans Human genes 0.000 description 1
• 108010067787 Proteoglycans Proteins 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 208000004531 Renal Artery Obstruction Diseases 0.000 description 1
• 206010038378 Renal artery stenosis Diseases 0.000 description 1
• 108090000783 Renin Proteins 0.000 description 1
• 102100028255 Renin Human genes 0.000 description 1
• WIPXBTPAZQYJQF-WKILWMFISA-N S1C(S(=O)(=O)NCC(=O)OCC)=CN=C1NC(=O)N(CCC(C)C)[C@@H]1CC[C@@H](C)CC1 Chemical compound S1C(S(=O)(=O)NCC(=O)OCC)=CN=C1NC(=O)N(CCC(C)C)[C@@H]1CC[C@@H](C)CC1 WIPXBTPAZQYJQF-WKILWMFISA-N 0.000 description 1
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
• 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 description 1
• LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Chemical compound OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 1
• 244000000231 Sesamum indicum Species 0.000 description 1
• 206010040925 Skin striae Diseases 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 208000006011 Stroke Diseases 0.000 description 1
• 206010042434 Sudden death Diseases 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
• 239000012505 Superdex™ Substances 0.000 description 1
• 208000007536 Thrombosis Diseases 0.000 description 1
• KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 description 1
• GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
• 102000008219 Uncoupling Protein 2 Human genes 0.000 description 1
• 108010021111 Uncoupling Protein 2 Proteins 0.000 description 1
• ICMGLRUYEQNHPF-UHFFFAOYSA-N Uraprene Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2N(C(=O)N(C)C(=O)C=2)C)CC1 ICMGLRUYEQNHPF-UHFFFAOYSA-N 0.000 description 1
• 102000005630 Urocortins Human genes 0.000 description 1
• 108010059705 Urocortins Proteins 0.000 description 1
• KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
• 206010047139 Vasoconstriction Diseases 0.000 description 1
• FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 1
• LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
• WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
• XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• AUALQMFGWLZREY-UHFFFAOYSA-N acetonitrile;methanol Chemical compound OC.CC#N AUALQMFGWLZREY-UHFFFAOYSA-N 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 239000000048 adrenergic agonist Substances 0.000 description 1
• 230000002411 adverse Effects 0.000 description 1
• 238000001042 affinity chromatography Methods 0.000 description 1
• 239000008272 agar Substances 0.000 description 1
• 235000010419 agar Nutrition 0.000 description 1
• 230000002776 aggregation Effects 0.000 description 1
• 238000004220 aggregation Methods 0.000 description 1
• 235000004279 alanine Nutrition 0.000 description 1
• 229960002478 aldosterone Drugs 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 125000003302 alkenyloxy group Chemical group 0.000 description 1
• 125000005108 alkenylthio group Chemical group 0.000 description 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
• 125000003282 alkyl amino group Chemical group 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 150000005215 alkyl ethers Chemical class 0.000 description 1
• 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 1
• 125000004647 alkyl sulfenyl group Chemical group 0.000 description 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• 239000002160 alpha blocker Substances 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 229940124308 alpha-adrenoreceptor antagonist Drugs 0.000 description 1
• 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
• 235000008206 alpha-amino acids Nutrition 0.000 description 1
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 description 1
• 229960002213 alprenolol Drugs 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• VMWZRHGIAVCFNS-UHFFFAOYSA-J aluminum;lithium;tetrahydroxide Chemical compound [Li+].[OH-].[OH-].[OH-].[OH-].[Al+3] VMWZRHGIAVCFNS-UHFFFAOYSA-J 0.000 description 1
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 description 1
• 229960004050 aminobenzoic acid Drugs 0.000 description 1
• 229950003476 aminothiazole Drugs 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000003392 amylase inhibitor Substances 0.000 description 1
• 239000002269 analeptic agent Substances 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 230000003466 anti-cipated effect Effects 0.000 description 1
• 230000001773 anti-convulsant effect Effects 0.000 description 1
• 230000001430 anti-depressive effect Effects 0.000 description 1
• 239000001961 anticonvulsive agent Substances 0.000 description 1
• 239000000935 antidepressant agent Substances 0.000 description 1
• 229940005513 antidepressants Drugs 0.000 description 1
• 229960003965 antiepileptics Drugs 0.000 description 1
• 239000000739 antihistaminic agent Substances 0.000 description 1
• 229940127088 antihypertensive drug Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 230000003078 antioxidant effect Effects 0.000 description 1
• 235000006708 antioxidants Nutrition 0.000 description 1
• 210000000709 aorta Anatomy 0.000 description 1
• 230000001640 apoptogenic effect Effects 0.000 description 1
• 235000021407 appetite control Nutrition 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 1
• 125000005333 aroyloxy group Chemical group 0.000 description 1
• 208000021328 arterial occlusion Diseases 0.000 description 1
• 125000003710 aryl alkyl group Chemical group 0.000 description 1
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
• 229960002274 atenolol Drugs 0.000 description 1
• 230000003143 atherosclerotic effect Effects 0.000 description 1
• AXLOCHLTNQDFFS-BESJYZOMSA-N azastene Chemical compound C([C@H]1[C@@H]2CC[C@@]([C@]2(CC[C@@H]1[C@@]1(C)C2)C)(O)C)C=C1C(C)(C)C1=C2C=NO1 AXLOCHLTNQDFFS-BESJYZOMSA-N 0.000 description 1
• 238000010533 azeotropic distillation Methods 0.000 description 1
• 235000013871 bee wax Nutrition 0.000 description 1
• 239000012166 beeswax Substances 0.000 description 1
• 230000003542 behavioural effect Effects 0.000 description 1
• 229960004530 benazepril Drugs 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 150000004283 biguanides Chemical class 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• 210000004204 blood vessel Anatomy 0.000 description 1
• OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
• 229960002802 bromocriptine Drugs 0.000 description 1
• 239000000480 calcium channel blocker Substances 0.000 description 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
• 239000000920 calcium hydroxide Substances 0.000 description 1
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 235000019577 caloric intake Nutrition 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 229960000830 captopril Drugs 0.000 description 1
• FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 150000001720 carbohydrates Chemical class 0.000 description 1
• 235000014633 carbohydrates Nutrition 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 210000001715 carotid artery Anatomy 0.000 description 1
• 150000003943 catecholamines Chemical class 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 230000030833 cell death Effects 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 230000003833 cell viability Effects 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 230000030570 cellular localization Effects 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 210000001627 cerebral artery Anatomy 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• 239000013522 chelant Substances 0.000 description 1
• 229920001429 chelating resin Polymers 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 229960001761 chlorpropamide Drugs 0.000 description 1
• YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 description 1
• 229950009226 ciglitazone Drugs 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
• 229960001653 citalopram Drugs 0.000 description 1
• HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
• 229940018557 citraconic acid Drugs 0.000 description 1
• 229960004106 citric acid Drugs 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
• 229960001214 clofibrate Drugs 0.000 description 1
• 229960003920 cocaine Drugs 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 239000003240 coconut oil Substances 0.000 description 1
• 235000019864 coconut oil Nutrition 0.000 description 1
• GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 description 1
• 229960002604 colestipol Drugs 0.000 description 1
• 235000009508 confectionery Nutrition 0.000 description 1
• 230000008602 contraction Effects 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 208000029078 coronary artery disease Diseases 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
• ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
• 125000006622 cycloheptylmethyl group Chemical group 0.000 description 1
• MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 1
• UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 150000003946 cyclohexylamines Chemical class 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 0.000 description 1
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• QQKNSPHAFATFNQ-UHFFFAOYSA-N darglitazone Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCC(=O)C(C=C1)=CC=C1CC1SC(=O)NC1=O QQKNSPHAFATFNQ-UHFFFAOYSA-N 0.000 description 1
• 229950006689 darglitazone Drugs 0.000 description 1
• 238000003381 deacetylation reaction Methods 0.000 description 1
• 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000007547 defect Effects 0.000 description 1
• 230000002950 deficient Effects 0.000 description 1
• 230000008021 deposition Effects 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
• 229960003957 dexamethasone Drugs 0.000 description 1
• 229960004597 dexfenfluramine Drugs 0.000 description 1
• 229960001767 dextrothyroxine Drugs 0.000 description 1
• GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 229960004890 diethylpropion Drugs 0.000 description 1
• XXEPPPIWZFICOJ-UHFFFAOYSA-N diethylpropion Chemical compound CCN(CC)C(C)C(=O)C1=CC=CC=C1 XXEPPPIWZFICOJ-UHFFFAOYSA-N 0.000 description 1
• 229960004166 diltiazem Drugs 0.000 description 1
• HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
• 231100000676 disease causative agent Toxicity 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• FUZBPOHHSBDTJQ-CFOQQKEYSA-L disodium;5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound [Na+].[Na+].C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C([O-])=O)C([O-])=O)C)=CC=CC(Cl)=C1 FUZBPOHHSBDTJQ-CFOQQKEYSA-L 0.000 description 1
• 229960001389 doxazosin Drugs 0.000 description 1
• RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
• 239000008298 dragée Substances 0.000 description 1
• 238000002651 drug therapy Methods 0.000 description 1
• 230000020595 eating behavior Effects 0.000 description 1
• 229950009714 ecopipam Drugs 0.000 description 1
• 229920002549 elastin Polymers 0.000 description 1
• 229950000269 emiglitate Drugs 0.000 description 1
• 239000003974 emollient agent Substances 0.000 description 1
• 230000008451 emotion Effects 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
• 229960000873 enalapril Drugs 0.000 description 1
• 230000002124 endocrine Effects 0.000 description 1
• 229950002375 englitazone Drugs 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 230000002255 enzymatic effect Effects 0.000 description 1
• 125000004185 ester group Chemical group 0.000 description 1
• 238000010931 ester hydrolysis Methods 0.000 description 1
• AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
• VRHAQNTWKSVEEC-UHFFFAOYSA-N ethyl 1,3-dioxoisoindole-2-carboxylate Chemical compound C1=CC=C2C(=O)N(C(=O)OCC)C(=O)C2=C1 VRHAQNTWKSVEEC-UHFFFAOYSA-N 0.000 description 1
• RQXDEGRETPOTBZ-UHFFFAOYSA-N ethyl 2-[(2-acetamido-1,3-thiazol-5-yl)sulfonylamino]acetate Chemical compound CCOC(=O)CNS(=O)(=O)C1=CN=C(NC(C)=O)S1 RQXDEGRETPOTBZ-UHFFFAOYSA-N 0.000 description 1
• LFGHLGIPWMWNFI-UHFFFAOYSA-N ethyl 2-[2-[[cyclopentylmethyl-(4-methylsulfonylphenyl)carbamoyl]amino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NC(=O)N(CC2CCCC2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 LFGHLGIPWMWNFI-UHFFFAOYSA-N 0.000 description 1
• IORFXCJYMZAFGU-UHFFFAOYSA-N ethyl 2-[[2-[[(3,4-difluorophenyl)-[(4-methylcyclohexyl)methyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCC(C)CC1 IORFXCJYMZAFGU-UHFFFAOYSA-N 0.000 description 1
• HATHXJPFZNESKS-UHFFFAOYSA-N ethyl 2-[[2-[[(3-acetamidophenyl)-(3,3-dimethylbutyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(CCC(C)(C)C)C1=CC=CC(NC(C)=O)=C1 HATHXJPFZNESKS-UHFFFAOYSA-N 0.000 description 1
• LDKCMVHKRRXTJT-UHFFFAOYSA-N ethyl 2-[[2-[[(3-acetamidophenyl)-(3-methylbutyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(CCC(C)C)C1=CC=CC(NC(C)=O)=C1 LDKCMVHKRRXTJT-UHFFFAOYSA-N 0.000 description 1
• YUWJQBCLYVEWQM-UHFFFAOYSA-N ethyl 2-[[2-[[(3-acetamidophenyl)-(cyclohexylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(NC(C)=O)C=CC=1)CC1CCCCC1 YUWJQBCLYVEWQM-UHFFFAOYSA-N 0.000 description 1
• ROTISDHIDXKMPN-UHFFFAOYSA-N ethyl 2-[[2-[[(3-acetamidophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(NC(C)=O)C=CC=1)CC1CCCC1 ROTISDHIDXKMPN-UHFFFAOYSA-N 0.000 description 1
• LOIRFIHAAMQGPR-UHFFFAOYSA-N ethyl 2-[[2-[[(3-acetamidophenyl)-(cyclopropylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(NC(C)=O)C=CC=1)CC1CC1 LOIRFIHAAMQGPR-UHFFFAOYSA-N 0.000 description 1
• YENJNNHWQQWBCU-UHFFFAOYSA-N ethyl 2-[[2-[[(3-acetamidophenyl)-hexylcarbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound C=1C=CC(NC(C)=O)=CC=1N(CCCCCC)C(=O)NC1=NC=C(SCC(=O)OCC)S1 YENJNNHWQQWBCU-UHFFFAOYSA-N 0.000 description 1
• YQOKHNFSBMAJNJ-UHFFFAOYSA-N ethyl 2-[[2-[[(3-acetamidophenyl)-pentylcarbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound C=1C=CC(NC(C)=O)=CC=1N(CCCCC)C(=O)NC1=NC=C(SCC(=O)OCC)S1 YQOKHNFSBMAJNJ-UHFFFAOYSA-N 0.000 description 1
• ZNUYLIDJXQORKP-UHFFFAOYSA-N ethyl 2-[[2-[[(3-carbamoylphenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(C=CC=1)C(N)=O)CC1CCCC1 ZNUYLIDJXQORKP-UHFFFAOYSA-N 0.000 description 1
• LGEKFMGWWKVHPX-UHFFFAOYSA-N ethyl 2-[[2-[[cyclohexylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCCC1 LGEKFMGWWKVHPX-UHFFFAOYSA-N 0.000 description 1
• XWDSKJIKSQHMHF-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-(2,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C(=CC(F)=CC=1)F)CC1CCCC1 XWDSKJIKSQHMHF-UHFFFAOYSA-N 0.000 description 1
• MAYFJRNJJMOLNS-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonylamino]acetate Chemical compound S1C(S(=O)(=O)NCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 MAYFJRNJJMOLNS-UHFFFAOYSA-N 0.000 description 1
• FZZIGGRPHOZUHD-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-[3-(dimethylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(C=CC=1)C(=O)N(C)C)CC1CCCC1 FZZIGGRPHOZUHD-UHFFFAOYSA-N 0.000 description 1
• SZFWGONVSVUKLF-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-[3-(ethylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound CCNC(=O)C1=CC=CC(N(CC2CCCC2)C(=O)NC=2SC(SCC(=O)OCC)=CN=2)=C1 SZFWGONVSVUKLF-UHFFFAOYSA-N 0.000 description 1
• HHADZXHJPRLXNG-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-[3-(methylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(C=CC=1)C(=O)NC)CC1CCCC1 HHADZXHJPRLXNG-UHFFFAOYSA-N 0.000 description 1
• BHYANUNARZIYAF-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-[3-(methylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoate Chemical compound S1C(SC(C)C(=O)OCC)=CN=C1NC(=O)N(C=1C=C(C=CC=1)C(=O)NC)CC1CCCC1 BHYANUNARZIYAF-UHFFFAOYSA-N 0.000 description 1
• IZZIRVQNSLVLQF-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-[3-(propan-2-ylcarbamoyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(C=CC=1)C(=O)NC(C)C)CC1CCCC1 IZZIRVQNSLVLQF-UHFFFAOYSA-N 0.000 description 1
• ICQYNPISSHGPAJ-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-[3-(trifluoromethoxy)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(OC(F)(F)F)C=CC=1)CC1CCCC1 ICQYNPISSHGPAJ-UHFFFAOYSA-N 0.000 description 1
• XWTVNLCUPGMPTE-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-[3-(trifluoromethyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(C=CC=1)C(F)(F)F)CC1CCCC1 XWTVNLCUPGMPTE-UHFFFAOYSA-N 0.000 description 1
• DKDPBXFIVBXJMW-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-[4-(trifluoromethoxy)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=CC(OC(F)(F)F)=CC=1)CC1CCCC1 DKDPBXFIVBXJMW-UHFFFAOYSA-N 0.000 description 1
• HCXXJPGBHAERPJ-UHFFFAOYSA-N ethyl 2-[[2-[[cyclopentylmethyl-[4-(trifluoromethyl)phenyl]carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetate Chemical compound S1C(SCC(=O)OCC)=CN=C1NC(=O)N(C=1C=CC(=CC=1)C(F)(F)F)CC1CCCC1 HCXXJPGBHAERPJ-UHFFFAOYSA-N 0.000 description 1
• AGNVEUMRIIPPIJ-UHFFFAOYSA-N ethyl 3-[[2-[[(3-acetamidophenyl)-(cyclopentylmethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoate Chemical compound S1C(SCCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(NC(C)=O)C=CC=1)CC1CCCC1 AGNVEUMRIIPPIJ-UHFFFAOYSA-N 0.000 description 1
• FEWSLBQQHACWNV-UHFFFAOYSA-N ethyl 3-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]propanoate Chemical compound S1C(SCCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 FEWSLBQQHACWNV-UHFFFAOYSA-N 0.000 description 1
• HIBUMERWIBYTPL-UHFFFAOYSA-N ethyl 3-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonylamino]propanoate Chemical compound S1C(S(=O)(=O)NCCC(=O)OCC)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 HIBUMERWIBYTPL-UHFFFAOYSA-N 0.000 description 1
• NWWORXYTJRPSMC-QKPAOTATSA-N ethyl 4-[2-[(2r,3r,4r,5s)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]ethoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 NWWORXYTJRPSMC-QKPAOTATSA-N 0.000 description 1
• YVKRWIVXIPGKTL-UHFFFAOYSA-N ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate Chemical compound CCOC(=O)C1=NN=C(N)S1 YVKRWIVXIPGKTL-UHFFFAOYSA-N 0.000 description 1
• DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 230000007717 exclusion Effects 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• ZZCHHVUQYRMYLW-HKBQPEDESA-N farglitazar Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 ZZCHHVUQYRMYLW-HKBQPEDESA-N 0.000 description 1
• 150000002191 fatty alcohols Chemical class 0.000 description 1
• 229960003580 felodipine Drugs 0.000 description 1
• 229960001582 fenfluramine Drugs 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 239000007888 film coating Substances 0.000 description 1
• 238000009501 film coating Methods 0.000 description 1
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 125000001207 fluorophenyl group Chemical group 0.000 description 1
• 229960002464 fluoxetine Drugs 0.000 description 1
• 235000013373 food additive Nutrition 0.000 description 1
• 239000002778 food additive Substances 0.000 description 1
• 235000019138 food restriction Nutrition 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 229960002490 fosinopril Drugs 0.000 description 1
• 230000008014 freezing Effects 0.000 description 1
• 238000007710 freezing Methods 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• 208000020694 gallbladder disease Diseases 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 229960003627 gemfibrozil Drugs 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 210000004907 gland Anatomy 0.000 description 1
• 229960004346 glimepiride Drugs 0.000 description 1
• WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
• 108010063245 glucagon-like peptide 1 (7-36)amide Proteins 0.000 description 1
• 230000004110 gluconeogenesis Effects 0.000 description 1
• 239000000174 gluconic acid Substances 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 230000004190 glucose uptake Effects 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 229960002989 glutamic acid Drugs 0.000 description 1
• 230000004116 glycogenolysis Effects 0.000 description 1
• 229960004275 glycolic acid Drugs 0.000 description 1
• QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 239000007902 hard capsule Substances 0.000 description 1
• 230000008821 health effect Effects 0.000 description 1
• 210000005003 heart tissue Anatomy 0.000 description 1
• 231100000753 hepatic injury Toxicity 0.000 description 1
• OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
• 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
• FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000004800 hydroisoquinoline derivatives Chemical class 0.000 description 1
• 208000006575 hypertriglyceridemia Diseases 0.000 description 1
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
• 150000002462 imidazolines Chemical class 0.000 description 1
• 239000007943 implant Substances 0.000 description 1
• 238000000099 in vitro assay Methods 0.000 description 1
• 238000005462 in vivo assay Methods 0.000 description 1
• 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 description 1
• PEHSSTUGJUBZBI-UHFFFAOYSA-N indan-5-ol Chemical compound OC1=CC=C2CCCC2=C1 PEHSSTUGJUBZBI-UHFFFAOYSA-N 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 239000007972 injectable composition Substances 0.000 description 1
• 229940102213 injectable suspension Drugs 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 239000002198 insoluble material Substances 0.000 description 1
• 230000002452 interceptive effect Effects 0.000 description 1
• 230000003834 intracellular effect Effects 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• 208000028867 ischemia Diseases 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 229960004427 isradipine Drugs 0.000 description 1
• 235000015110 jellies Nutrition 0.000 description 1
• 230000000366 juvenile effect Effects 0.000 description 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 235000019421 lipase Nutrition 0.000 description 1
• 230000037356 lipid metabolism Effects 0.000 description 1
• 230000013190 lipid storage Effects 0.000 description 1
• 208000006132 lipodystrophy Diseases 0.000 description 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
• 239000008297 liquid dosage form Substances 0.000 description 1
• RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 1
• 229960002394 lisinopril Drugs 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 231100000835 liver failure Toxicity 0.000 description 1
• 208000007903 liver failure Diseases 0.000 description 1
• 230000004777 loss-of-function mutation Effects 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000004325 lysozyme Substances 0.000 description 1
• 235000010335 lysozyme Nutrition 0.000 description 1
• 229960000274 lysozyme Drugs 0.000 description 1
• 210000002540 macrophage Anatomy 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
• 239000000347 magnesium hydroxide Substances 0.000 description 1
• 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 238000007726 management method Methods 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 1
• 229960000299 mazindol Drugs 0.000 description 1
• 235000012054 meals Nutrition 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 229960003194 meglumine Drugs 0.000 description 1
• 210000002752 melanocyte Anatomy 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 1
• 229930182817 methionine Natural products 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• LMSHPFRVDKXULT-QMMMGPOBSA-N methyl (2s)-1-[(2-acetamido-1,3-thiazol-5-yl)sulfonyl]pyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1CCCN1S(=O)(=O)C1=CN=C(NC(C)=O)S1 LMSHPFRVDKXULT-QMMMGPOBSA-N 0.000 description 1
• DECTXQHUQYSCMT-SFHVURJKSA-N methyl (2s)-1-[[2-[[cyclopentylmethyl-(3,4-difluorophenyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfonyl]pyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1CCCN1S(=O)(=O)C(S1)=CN=C1NC(=O)N(C=1C=C(F)C(F)=CC=1)CC1CCCC1 DECTXQHUQYSCMT-SFHVURJKSA-N 0.000 description 1
• HQEIPVHJHZTMDP-JEDNCBNOSA-N methyl (2s)-pyrrolidine-2-carboxylate;hydrochloride Chemical compound Cl.COC(=O)[C@@H]1CCCN1 HQEIPVHJHZTMDP-JEDNCBNOSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
• 229960002237 metoprolol Drugs 0.000 description 1
• 206010062198 microangiopathy Diseases 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 229960001110 miglitol Drugs 0.000 description 1
• 239000012046 mixed solvent Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• SLZIZIJTGAYEKK-CIJSCKBQSA-N molport-023-220-247 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CN)[C@@H](C)O)C1=CNC=N1 SLZIZIJTGAYEKK-CIJSCKBQSA-N 0.000 description 1
• PXZWGQLGAKCNKD-DPNMSELWSA-N molport-023-276-326 Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 PXZWGQLGAKCNKD-DPNMSELWSA-N 0.000 description 1
• 229910052901 montmorillonite Inorganic materials 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 239000002324 mouth wash Substances 0.000 description 1
• 230000002107 myocardial effect Effects 0.000 description 1
• 208000037891 myocardial injury Diseases 0.000 description 1
• 208000031225 myocardial ischemia Diseases 0.000 description 1
• RHUYLAPWIXLSEF-UHFFFAOYSA-N n,n-diethyl-2-(methylamino)acetamide Chemical compound CCN(CC)C(=O)CNC RHUYLAPWIXLSEF-UHFFFAOYSA-N 0.000 description 1
• DHVASDVOMMPVBR-UHFFFAOYSA-N n-(4-ethylcyclohexylidene)hydroxylamine Chemical compound CCC1CCC(=NO)CC1 DHVASDVOMMPVBR-UHFFFAOYSA-N 0.000 description 1
• BKEYIBCKKVSKOZ-UHFFFAOYSA-N n-(cyclobutylmethyl)-3,4-difluoroaniline Chemical compound C1=C(F)C(F)=CC=C1NCC1CCC1 BKEYIBCKKVSKOZ-UHFFFAOYSA-N 0.000 description 1
• ZRTOLROLFSTEAO-UHFFFAOYSA-N n-(cyclohexylmethyl)-6-methoxypyridin-3-amine Chemical compound C1=NC(OC)=CC=C1NCC1CCCCC1 ZRTOLROLFSTEAO-UHFFFAOYSA-N 0.000 description 1
• IMTFTMQPGSCRDF-UHFFFAOYSA-N n-(cyclopentylmethyl)-2,4-difluoroaniline Chemical compound FC1=CC(F)=CC=C1NCC1CCCC1 IMTFTMQPGSCRDF-UHFFFAOYSA-N 0.000 description 1
• CJEIMTRABOWYPP-UHFFFAOYSA-N n-(cyclopentylmethyl)-3,4-difluoroaniline;3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1.C1=C(F)C(F)=CC=C1NCC1CCCC1 CJEIMTRABOWYPP-UHFFFAOYSA-N 0.000 description 1
• PETQZHVMSJIWTG-UHFFFAOYSA-N n-(cyclopentylmethyl)-3-(trifluoromethoxy)aniline Chemical compound FC(F)(F)OC1=CC=CC(NCC2CCCC2)=C1 PETQZHVMSJIWTG-UHFFFAOYSA-N 0.000 description 1
• WSHXLOCTHPZAOF-UHFFFAOYSA-N n-(cyclopentylmethyl)-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC=CC(NCC2CCCC2)=C1 WSHXLOCTHPZAOF-UHFFFAOYSA-N 0.000 description 1
• WISKJGHGZIMGIV-UHFFFAOYSA-N n-(cyclopentylmethyl)-4-(trifluoromethoxy)aniline Chemical compound C1=CC(OC(F)(F)F)=CC=C1NCC1CCCC1 WISKJGHGZIMGIV-UHFFFAOYSA-N 0.000 description 1
• AFSZUQWPTBSRMK-UHFFFAOYSA-N n-(cyclopentylmethyl)-4-(trifluoromethyl)aniline Chemical compound C1=CC(C(F)(F)F)=CC=C1NCC1CCCC1 AFSZUQWPTBSRMK-UHFFFAOYSA-N 0.000 description 1
• GZQAZNFBMKPALI-UHFFFAOYSA-N n-(cyclopentylmethyl)-6-methoxypyridin-3-amine Chemical compound C1=NC(OC)=CC=C1NCC1CCCC1 GZQAZNFBMKPALI-UHFFFAOYSA-N 0.000 description 1
• ZTGDAOSRFXNWKJ-UHFFFAOYSA-N n-[3-(benzylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(NCC=2C=CC=CC=2)=C1 ZTGDAOSRFXNWKJ-UHFFFAOYSA-N 0.000 description 1
• UDKIXUJNOBAIKV-UHFFFAOYSA-N n-[5-(cyclopentylmethylamino)pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1NCC1CCCC1 UDKIXUJNOBAIKV-UHFFFAOYSA-N 0.000 description 1
• WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
• AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• DQCKKXVULJGBQN-XFWGSAIBSA-N naltrexone Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=O)O)CC1)O)CC1CC1 DQCKKXVULJGBQN-XFWGSAIBSA-N 0.000 description 1
• 229960003086 naltrexone Drugs 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 230000001338 necrotic effect Effects 0.000 description 1
• 229960001783 nicardipine Drugs 0.000 description 1
• HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
• 229960001597 nifedipine Drugs 0.000 description 1
• 229960000715 nimodipine Drugs 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 description 1
• 125000005482 norpinyl group Chemical group 0.000 description 1
• 238000010899 nucleation Methods 0.000 description 1
• 230000035764 nutrition Effects 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
• 239000007764 o/w emulsion Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 239000003401 opiate antagonist Substances 0.000 description 1
• 239000003538 oral antidiabetic agent Substances 0.000 description 1
• 229940127209 oral hypoglycaemic agent Drugs 0.000 description 1
• 108060005714 orexin Proteins 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
• 229960001243 orlistat Drugs 0.000 description 1
• 230000003204 osmotic effect Effects 0.000 description 1
• YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 229940116315 oxalic acid Drugs 0.000 description 1
• LVSJDHGRKAEGLX-UHFFFAOYSA-N oxolane;2,2,2-trifluoroacetic acid Chemical compound C1CCOC1.OC(=O)C(F)(F)F LVSJDHGRKAEGLX-UHFFFAOYSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 229940055076 parasympathomimetics choline ester Drugs 0.000 description 1
• 230000001575 pathological effect Effects 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 235000010987 pectin Nutrition 0.000 description 1
• 239000001814 pectin Substances 0.000 description 1
• 229920001277 pectin Polymers 0.000 description 1
• 229940049954 penicillin Drugs 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 239000000813 peptide hormone Substances 0.000 description 1
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
• VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
• 230000010412 perfusion Effects 0.000 description 1
• 230000002085 persistent effect Effects 0.000 description 1
• 229960000436 phendimetrazine Drugs 0.000 description 1
• 229940117803 phenethylamine Drugs 0.000 description 1
• 208000028591 pheochromocytoma Diseases 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 150000008105 phosphatidylcholines Chemical class 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 1
• 229960002508 pindolol Drugs 0.000 description 1
• 229960005095 pioglitazone Drugs 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 239000004014 plasticizer Substances 0.000 description 1
• 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
• 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
• 229920000053 polysorbate 80 Polymers 0.000 description 1
• 229920002223 polystyrene Polymers 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 230000018656 positive regulation of gluconeogenesis Effects 0.000 description 1
• 230000029537 positive regulation of insulin secretion Effects 0.000 description 1
• 230000000291 postprandial effect Effects 0.000 description 1
• 239000003450 potassium channel blocker Substances 0.000 description 1
• CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
• TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
• 229960002965 pravastatin Drugs 0.000 description 1
• 229960001289 prazosin Drugs 0.000 description 1
• IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
• 230000002028 premature Effects 0.000 description 1
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• GCYXWQUSHADNBF-AAEALURTSA-N preproglucagon 78-108 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 GCYXWQUSHADNBF-AAEALURTSA-N 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
• FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
• 229960003912 probucol Drugs 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 230000000750 progressive effect Effects 0.000 description 1
• 229940097325 prolactin Drugs 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 229960003712 propranolol Drugs 0.000 description 1
• 235000013772 propylene glycol Nutrition 0.000 description 1
• 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
• 238000001243 protein synthesis Methods 0.000 description 1
• 108020000494 protein-tyrosine phosphatase Proteins 0.000 description 1
• 235000018102 proteins Nutrition 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
• 230000005180 public health Effects 0.000 description 1
• 230000002685 pulmonary effect Effects 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
• 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 1
• 229960001455 quinapril Drugs 0.000 description 1
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 150000003248 quinolines Chemical class 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
• 229960003401 ramipril Drugs 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000008085 renal dysfunction Effects 0.000 description 1
• 230000010410 reperfusion Effects 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• XMSXOLDPMGMWTH-UHFFFAOYSA-N rivoglitazone Chemical compound CN1C2=CC(OC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O XMSXOLDPMGMWTH-UHFFFAOYSA-N 0.000 description 1
• 229960004586 rosiglitazone Drugs 0.000 description 1
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
• 229940081974 saccharin Drugs 0.000 description 1
• 235000019204 saccharin Nutrition 0.000 description 1
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 0.000 description 1
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
• 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 229960004425 sibutramine Drugs 0.000 description 1
• UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
• 229960002855 simvastatin Drugs 0.000 description 1
• AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
• 235000010413 sodium alginate Nutrition 0.000 description 1
• 239000000661 sodium alginate Substances 0.000 description 1
• 229940005550 sodium alginate Drugs 0.000 description 1
• WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
• 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• 239000001488 sodium phosphate Substances 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 239000007901 soft capsule Substances 0.000 description 1
• 239000007909 solid dosage form Substances 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 229960005322 streptomycin Drugs 0.000 description 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
• XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical group S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
• 235000010269 sulphur dioxide Nutrition 0.000 description 1
• 230000008093 supporting effect Effects 0.000 description 1
• 230000004083 survival effect Effects 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
• 229960001693 terazosin Drugs 0.000 description 1
• IZCDSQRAXSGFMO-UHFFFAOYSA-N tert-butyl n-(4-methylcyclohexyl)-n-(3-phenylmethoxypropyl)carbamate Chemical compound C1CC(C)CCC1N(C(=O)OC(C)(C)C)CCCOCC1=CC=CC=C1 IZCDSQRAXSGFMO-UHFFFAOYSA-N 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 230000004797 therapeutic response Effects 0.000 description 1
• 125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
• 150000001467 thiazolidinediones Chemical class 0.000 description 1
• 230000008719 thickening Effects 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 229960004605 timolol Drugs 0.000 description 1
• 229960002277 tolazamide Drugs 0.000 description 1
• OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
• 229960004394 topiramate Drugs 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 230000009261 transgenic effect Effects 0.000 description 1
• 230000007704 transition Effects 0.000 description 1
• 230000014616 translation Effects 0.000 description 1
• 238000002054 transplantation Methods 0.000 description 1
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• 125000006168 tricyclic group Chemical group 0.000 description 1
• 229940086542 triethylamine Drugs 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• 229950002929 trinitrophenol Drugs 0.000 description 1
• RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
• 229960001130 urapidil Drugs 0.000 description 1
• 150000003672 ureas Chemical class 0.000 description 1
• 239000000777 urocortin Substances 0.000 description 1
• 239000004474 valine Substances 0.000 description 1
• 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 210000005167 vascular cell Anatomy 0.000 description 1
• 210000005166 vasculature Anatomy 0.000 description 1
• 230000025033 vasoconstriction Effects 0.000 description 1
• 239000005526 vasoconstrictor agent Substances 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 229960001722 verapamil Drugs 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 229960001729 voglibose Drugs 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000001993 wax Substances 0.000 description 1
• 230000004584 weight gain Effects 0.000 description 1
• 235000019786 weight gain Nutrition 0.000 description 1
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
• DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1