KR20050106461A - 타입 2 당뇨병과 죽상동맥경화증 치료에 ｐｐａｒ 조절제로사용되는 3-(2-페닐-옥사졸-4-일 메톡시)사이클로헥실메톡시 아세트산 유도체 및 이와 관련된화합물 - Google Patents

Info

Publication number

KR20050106461A

KR20050106461A KR1020057015995A KR20057015995A KR20050106461A KR 20050106461 A KR20050106461 A KR 20050106461A KR 1020057015995 A KR1020057015995 A KR 1020057015995A KR 20057015995 A KR20057015995 A KR 20057015995A KR 20050106461 A KR20050106461 A KR 20050106461A

Authority

KR

South Korea

Prior art keywords

alkyl

methyl

cis

tert

phenyl

Prior art date

2003-02-27

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 203
• 208000001072 type 2 diabetes mellitus Diseases 0.000 title claims abstract description 9
• 201000001320 Atherosclerosis Diseases 0.000 title description 6
• CQWYYUYAROQPOK-UHFFFAOYSA-N 2-[[3-[(2-phenyl-1,3-oxazol-4-yl)methoxy]cyclohexyl]methoxy]acetic acid Chemical class C1(=CC=CC=C1)C=1OC=C(N1)COC1CC(CCC1)COCC(=O)O CQWYYUYAROQPOK-UHFFFAOYSA-N 0.000 title 1
• 101150014691 PPARA gene Proteins 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 35
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
• 150000003839 salts Chemical class 0.000 claims abstract description 15
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 5
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 5
• 239000008103 glucose Substances 0.000 claims abstract description 5
• 239000000203 mixture Substances 0.000 claims description 133
• -1 (C5-C11) -heteroaryl Chemical group 0.000 claims description 125
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 64
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 17
• 238000011282 treatment Methods 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• 230000002265 prevention Effects 0.000 claims description 12
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
• 150000002632 lipids Chemical class 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 208000030159 metabolic disease Diseases 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 229940125708 antidiabetic agent Drugs 0.000 claims description 4
• 239000003472 antidiabetic agent Substances 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
• 230000009286 beneficial effect Effects 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 150000001242 acetic acid derivatives Chemical class 0.000 abstract description 2
• 230000004129 fatty acid metabolism Effects 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 255
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 137
• 239000000243 solution Substances 0.000 description 123
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 120
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 108
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 95
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 67
• 239000012074 organic phase Substances 0.000 description 58
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
• 210000004027 cell Anatomy 0.000 description 41
• 230000015572 biosynthetic process Effects 0.000 description 40
• 239000003921 oil Substances 0.000 description 40
• 239000002904 solvent Substances 0.000 description 40
• 238000003786 synthesis reaction Methods 0.000 description 40
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 39
• 239000012071 phase Substances 0.000 description 39
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 38
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 34
• 239000000741 silica gel Substances 0.000 description 31
• 229910002027 silica gel Inorganic materials 0.000 description 31
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 239000008346 aqueous phase Substances 0.000 description 29
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 28
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 28
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 27
• BNCNAQNTIYCMGB-UHFFFAOYSA-N 4-(iodomethyl)-2-(4-methylphenyl)-5-phenyl-1,3-oxazole Chemical compound C1=CC(C)=CC=C1C1=NC(CI)=C(C=2C=CC=CC=2)O1 BNCNAQNTIYCMGB-UHFFFAOYSA-N 0.000 description 25
• 102000023984 PPAR alpha Human genes 0.000 description 25
• 239000004480 active ingredient Substances 0.000 description 25
• 239000000556 agonist Substances 0.000 description 25
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• 239000013612 plasmid Substances 0.000 description 24
• 239000000725 suspension Substances 0.000 description 24
• 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 21
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000011541 reaction mixture Substances 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• 108060001084 Luciferase Proteins 0.000 description 20
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
• 102000000536 PPAR gamma Human genes 0.000 description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
• 229920006395 saturated elastomer Polymers 0.000 description 19
• 108010016731 PPAR gamma Proteins 0.000 description 18
• 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 18
• 239000000047 product Substances 0.000 description 18
• 238000003756 stirring Methods 0.000 description 18
• YMKJZUSBDODQIC-NWDGAFQWSA-N tert-butyl 2-[[(1s,3r)-3-hydroxycyclohexyl]methoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC[C@H]1CCC[C@@H](O)C1 YMKJZUSBDODQIC-NWDGAFQWSA-N 0.000 description 18
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 17
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
• 239000005089 Luciferase Substances 0.000 description 15
• FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 description 15
• 238000003556 assay Methods 0.000 description 14
• 239000012043 crude product Substances 0.000 description 14
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 13
• 229960000583 acetic acid Drugs 0.000 description 13
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 13
• 239000012230 colorless oil Substances 0.000 description 12
• CPGISPNRQJPVBR-OLZOCXBDSA-N tert-butyl 2-[[(1s,3r)-3-(hydroxymethyl)cyclohexyl]methoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC[C@H]1CCC[C@@H](CO)C1 CPGISPNRQJPVBR-OLZOCXBDSA-N 0.000 description 12
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 239000001257 hydrogen Substances 0.000 description 11
• 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 11
• NHGZEJHJHUHZDI-UHFFFAOYSA-N methyl 2-sulfanylbutanoate Chemical compound CCC(S)C(=O)OC NHGZEJHJHUHZDI-UHFFFAOYSA-N 0.000 description 11
• 229910000104 sodium hydride Inorganic materials 0.000 description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
• SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 10
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
• JWQLIAZJZXIDGS-WBVHZDCISA-N 4-[[(1s,3r)-3-(iodomethyl)cyclohexyl]oxymethyl]-5-methyl-2-(4-methylphenyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(C)=CC=2)=NC=1CO[C@H]1CCC[C@@H](CI)C1 JWQLIAZJZXIDGS-WBVHZDCISA-N 0.000 description 9
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 9
• 102100039556 Galectin-4 Human genes 0.000 description 9
• 101000608765 Homo sapiens Galectin-4 Proteins 0.000 description 9
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 238000006243 chemical reaction Methods 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 238000004128 high performance liquid chromatography Methods 0.000 description 9
• 239000002609 medium Substances 0.000 description 9
• 239000008194 pharmaceutical composition Substances 0.000 description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
• MISUXMWJCDKLQC-QWHCGFSZSA-N tert-butyl 2-[[(1s,3r)-3-(methoxymethoxy)cyclohexyl]methoxy]acetate Chemical compound COCO[C@@H]1CCC[C@H](COCC(=O)OC(C)(C)C)C1 MISUXMWJCDKLQC-QWHCGFSZSA-N 0.000 description 9
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 8
• 239000012280 lithium aluminium hydride Substances 0.000 description 8
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
• 235000019260 propionic acid Nutrition 0.000 description 8
• 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 8
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
• 102000004877 Insulin Human genes 0.000 description 7
• 108090001061 Insulin Proteins 0.000 description 7
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 235000011089 carbon dioxide Nutrition 0.000 description 7
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• 108020001507 fusion proteins Proteins 0.000 description 7
• 102000037865 fusion proteins Human genes 0.000 description 7
• 239000003446 ligand Substances 0.000 description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
• 239000012312 sodium hydride Substances 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
• 206010028980 Neoplasm Diseases 0.000 description 6
• 150000001351 alkyl iodides Chemical class 0.000 description 6
• 239000005557 antagonist Substances 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 208000035475 disorder Diseases 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 238000011534 incubation Methods 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 238000004809 thin layer chromatography Methods 0.000 description 6
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
• DQFNFCZJCTWYGP-UHFFFAOYSA-N 4-(iodomethyl)-2-(4-methylphenyl)-5-propan-2-yl-1,3-oxazole Chemical compound ICC1=C(C(C)C)OC(C=2C=CC(C)=CC=2)=N1 DQFNFCZJCTWYGP-UHFFFAOYSA-N 0.000 description 5
• AONKVWHDUVHQSZ-UHFFFAOYSA-N 4-(iodomethyl)-5-methyl-2-(4-methylphenyl)-1,3-oxazole Chemical compound ICC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 AONKVWHDUVHQSZ-UHFFFAOYSA-N 0.000 description 5
• 206010020649 Hyperkeratosis Diseases 0.000 description 5
• 208000001126 Keratosis Diseases 0.000 description 5
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 5
• 229930182816 L-glutamine Natural products 0.000 description 5
• 229940100389 Sulfonylurea Drugs 0.000 description 5
• 102000040945 Transcription factor Human genes 0.000 description 5
• 108091023040 Transcription factor Proteins 0.000 description 5
• 150000001413 amino acids Chemical class 0.000 description 5
• 239000012298 atmosphere Substances 0.000 description 5
• 230000027455 binding Effects 0.000 description 5
• 229910002091 carbon monoxide Inorganic materials 0.000 description 5
• 239000013613 expression plasmid Substances 0.000 description 5
• 239000003112 inhibitor Substances 0.000 description 5
• 229940125396 insulin Drugs 0.000 description 5
• 230000037356 lipid metabolism Effects 0.000 description 5
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 238000002156 mixing Methods 0.000 description 5
• 238000002953 preparative HPLC Methods 0.000 description 5
• 108090000623 proteins and genes Proteins 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 238000011160 research Methods 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• RCINKPHVMAXNBC-PWWKTKHKSA-N tert-butyl (2s)-3-methyl-2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methylamino]butanoate Chemical compound C1[C@@H](CN[C@@H](C(C)C)C(=O)OC(C)(C)C)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 RCINKPHVMAXNBC-PWWKTKHKSA-N 0.000 description 5
• BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 5
• YQLIHTHYPPKZSY-RBBKRZOGSA-N tert-butyl 2-methyl-2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxy]propanoate Chemical compound CC=1OC(C=2C=CC(C)=CC=2)=NC=1CO[C@@H]1CCC[C@H](COC(C)(C)C(=O)OC(C)(C)C)C1 YQLIHTHYPPKZSY-RBBKRZOGSA-N 0.000 description 5
• UAAIEWSIARLHPR-JWQCQUIFSA-N tert-butyl 4-[(1r,3r)-3-[tert-butyl(diphenyl)silyl]oxycyclohexyl]butanoate Chemical compound C1[C@@H](CCCC(=O)OC(C)(C)C)CCC[C@H]1O[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 UAAIEWSIARLHPR-JWQCQUIFSA-N 0.000 description 5
• OPWMLWHXIUSITO-BDAKNGLRSA-N (1s,3s)-3-prop-2-enylcyclohexan-1-ol Chemical compound O[C@H]1CCC[C@@H](CC=C)C1 OPWMLWHXIUSITO-BDAKNGLRSA-N 0.000 description 4
• XJKVVHCZKAADFP-UHFFFAOYSA-N 4-(iodomethyl)-2-(3-methoxyphenyl)-5-methyl-1,3-oxazole Chemical compound COC1=CC=CC(C=2OC(C)=C(CI)N=2)=C1 XJKVVHCZKAADFP-UHFFFAOYSA-N 0.000 description 4
• YHFHYYAOKIABPW-UHFFFAOYSA-N 5-methyl-2-(4-methylphenyl)-1,3-oxazole-4-carbaldehyde Chemical compound O=CC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 YHFHYYAOKIABPW-UHFFFAOYSA-N 0.000 description 4
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 241000254064 Photinus pyralis Species 0.000 description 4
• 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 4
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
• TXKAQZRUJUNDHI-UHFFFAOYSA-K bismuth tribromide Chemical compound Br[Bi](Br)Br TXKAQZRUJUNDHI-UHFFFAOYSA-K 0.000 description 4
• 210000004369 blood Anatomy 0.000 description 4
• 239000008280 blood Substances 0.000 description 4
• 238000009835 boiling Methods 0.000 description 4
• 230000001413 cellular effect Effects 0.000 description 4
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• 238000010367 cloning Methods 0.000 description 4
• 239000002299 complementary DNA Substances 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 238000010790 dilution Methods 0.000 description 4
• 239000012895 dilution Substances 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• STXQYTGSIQCKFA-UHFFFAOYSA-N ethyl 2-amino-4-methyl-3-oxopentanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(N)C(=O)C(C)C STXQYTGSIQCKFA-UHFFFAOYSA-N 0.000 description 4
• 238000003818 flash chromatography Methods 0.000 description 4
• 230000006870 function Effects 0.000 description 4
• MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
• 239000004615 ingredient Substances 0.000 description 4
• 239000011630 iodine Substances 0.000 description 4
• 229910052740 iodine Inorganic materials 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 229910000489 osmium tetroxide Inorganic materials 0.000 description 4
• 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 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 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 4
• 230000001105 regulatory effect Effects 0.000 description 4
• 238000004007 reversed phase HPLC Methods 0.000 description 4
• 238000012163 sequencing technique Methods 0.000 description 4
• VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• ZVFOQKURZQGOHX-ZWKOTPCHSA-N tert-butyl 2-[[(1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclohexyl]methoxy]-2-methylpropanoate Chemical compound [Si](C)(C)(C(C)(C)C)OC[C@H]1C[C@H](CCC1)COC(C(=O)OC(C)(C)C)(C)C ZVFOQKURZQGOHX-ZWKOTPCHSA-N 0.000 description 4
• VWGUIVBXDKOASG-UONOGXRCSA-N tert-butyl 2-[[(1s,3r)-3-(methoxymethoxymethyl)cyclohexyl]methoxy]acetate Chemical compound COCOC[C@@H]1CCC[C@H](COCC(=O)OC(C)(C)C)C1 VWGUIVBXDKOASG-UONOGXRCSA-N 0.000 description 4
• KSLFVKVWRDORNW-CHWSQXEVSA-N tert-butyl 4-[(1r,3r)-3-hydroxycyclohexyl]-2,2-dimethylbutanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)CC[C@H]1CCC[C@@H](O)C1 KSLFVKVWRDORNW-CHWSQXEVSA-N 0.000 description 4
• MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 4
• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 4
• 238000011144 upstream manufacturing Methods 0.000 description 4
• ZVJBPHMCBRHVEV-GQCTYLIASA-N (2e)-2-hydroxyiminopentan-3-one Chemical compound CCC(=O)C(\C)=N\O ZVJBPHMCBRHVEV-GQCTYLIASA-N 0.000 description 3
• KQQKCVRSVVMFBH-FJIJXJHWSA-N (2s)-2-[acetyl-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methyl]amino]-3-methylbutanoic acid Chemical compound C1[C@@H](CN([C@@H](C(C)C)C(O)=O)C(C)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 KQQKCVRSVVMFBH-FJIJXJHWSA-N 0.000 description 3
• ZCDVTJKHKVSYSS-PZJWPPBQSA-N 1-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxy]cyclopentane-1-carboxylic acid Chemical compound C([C@H]1CCC[C@H](C1)OCC=1N=C(OC=1C)C=1C=CC(C)=CC=1)OC1(C(O)=O)CCCC1 ZCDVTJKHKVSYSS-PZJWPPBQSA-N 0.000 description 3
• NSDMRCKMFYOVAJ-UYAOXDASSA-N 2,2-dimethyl-4-[(1r,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]butanoic acid Chemical compound CC=1OC(C=2C=CC(C)=CC=2)=NC=1CO[C@@H]1CCC[C@H](CCC(C)(C)C(O)=O)C1 NSDMRCKMFYOVAJ-UYAOXDASSA-N 0.000 description 3
• JDHCASIRZZQYSO-CRAIPNDOSA-N 2-[(1s,3r)-3-[[2-(3-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]cyclohexyl]acetaldehyde Chemical compound COC1=CC=CC(C=2OC(C)=C(CO[C@H]3C[C@@H](CC=O)CCC3)N=2)=C1 JDHCASIRZZQYSO-CRAIPNDOSA-N 0.000 description 3
• XYUQYPADKQJWAJ-SJLPKXTDSA-N 2-[(1s,3r)-3-[[5-methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]acetaldehyde Chemical compound CC=1OC(C=2C=C(C)C=CC=2)=NC=1CO[C@@H]1CCC[C@H](CC=O)C1 XYUQYPADKQJWAJ-SJLPKXTDSA-N 0.000 description 3
• HNJQIGJPLYPMPU-NHCUHLMSSA-N 2-[(1s,3r)-3-[tert-butyl(diphenyl)silyl]oxycyclohexyl]acetaldehyde Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)O[C@@H]1CCC[C@H](CC=O)C1 HNJQIGJPLYPMPU-NHCUHLMSSA-N 0.000 description 3
• FGLZRBPXMFFJJW-OPMJYIBYSA-N 2-[2-[(1r,3r)-3-[tert-butyl(diphenyl)silyl]oxycyclohexyl]ethyl]-3-methylbutanoic acid Chemical compound C1[C@@H](CCC(C(C)C)C(O)=O)CCC[C@H]1O[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 FGLZRBPXMFFJJW-OPMJYIBYSA-N 0.000 description 3
• GKQXOXZABLMFEM-MOPGFXCFSA-N 2-methyl-2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxymethyl]cyclohexyl]methoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC(C)=CC=2)=NC=1COC[C@@H]1CCC[C@H](COC(C)(C)C(O)=O)C1 GKQXOXZABLMFEM-MOPGFXCFSA-N 0.000 description 3
• WEWPHAAWLKAJKC-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-5-phenyl-1,3-oxazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=C(C=2C=CC=CC=2)O1 WEWPHAAWLKAJKC-UHFFFAOYSA-N 0.000 description 3
• BRZRJPLCEKTSKE-VQIMIIECSA-N 4-[(1r,3r)-3-[[2-(3-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]cyclohexyl]butanoic acid Chemical compound COC1=CC=CC(C=2OC(C)=C(CO[C@H]3C[C@@H](CCCC(O)=O)CCC3)N=2)=C1 BRZRJPLCEKTSKE-VQIMIIECSA-N 0.000 description 3
• NIVGNNIVMXYXFG-UHFFFAOYSA-N 4-methyl-2-(4-methylphenyl)-3-oxido-5-phenyl-1,3-oxazol-3-ium Chemical compound [O-][N+]=1C(C)=C(C=2C=CC=CC=2)OC=1C1=CC=C(C)C=C1 NIVGNNIVMXYXFG-UHFFFAOYSA-N 0.000 description 3
• XOTZYEUWGPYLID-WPLVIQRKSA-N 4-methyl-2-[2-[(1r,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethyl]pentanoic acid Chemical compound C1[C@@H](CCC(CC(C)C)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 XOTZYEUWGPYLID-WPLVIQRKSA-N 0.000 description 3
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
• 201000004624 Dermatitis Diseases 0.000 description 3
• 108090000331 Firefly luciferases Proteins 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• 206010020772 Hypertension Diseases 0.000 description 3
• 229910010084 LiAlH4 Inorganic materials 0.000 description 3
• 241000713333 Mouse mammary tumor virus Species 0.000 description 3
• 238000005481 NMR spectroscopy Methods 0.000 description 3
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
• 108010028924 PPAR alpha Proteins 0.000 description 3
• 102000004257 Potassium Channel Human genes 0.000 description 3
• 108010052090 Renilla Luciferases Proteins 0.000 description 3
• 108010084455 Zeocin Proteins 0.000 description 3
• QJHAWRGKDNXWIY-UHFFFAOYSA-N [2-(4-methylphenyl)-5-propan-2-yl-1,3-oxazol-4-yl]methanol Chemical compound OCC1=C(C(C)C)OC(C=2C=CC(C)=CC=2)=N1 QJHAWRGKDNXWIY-UHFFFAOYSA-N 0.000 description 3
• 150000001299 aldehydes Chemical class 0.000 description 3
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
• 229910052786 argon Inorganic materials 0.000 description 3
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 235000009508 confectionery Nutrition 0.000 description 3
• 235000014113 dietary fatty acids Nutrition 0.000 description 3
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
• 201000010099 disease Diseases 0.000 description 3
• XWKOSAYDZJXYQO-UHFFFAOYSA-N ethyl 2-(4-methylphenyl)-5-propan-2-yl-1,3-oxazole-4-carboxylate Chemical compound O1C(C(C)C)=C(C(=O)OCC)N=C1C1=CC=C(C)C=C1 XWKOSAYDZJXYQO-UHFFFAOYSA-N 0.000 description 3
• SMAOVIHJZYGLNT-UHFFFAOYSA-N ethyl 2-hydroxyimino-4-methyl-3-oxopentanoate Chemical compound CCOC(=O)C(=NO)C(=O)C(C)C SMAOVIHJZYGLNT-UHFFFAOYSA-N 0.000 description 3
• OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical group CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 3
• BZXOHHBDFGNCMW-WIYYLYMNSA-N ethyl 4-[(1r,3r)-3-[[2-(3-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]cyclohexyl]butanoate Chemical compound C1[C@@H](CCCC(=O)OCC)CCC[C@H]1OCC1=C(C)OC(C=2C=C(OC)C=CC=2)=N1 BZXOHHBDFGNCMW-WIYYLYMNSA-N 0.000 description 3
• HDTDHYKMFULBIB-UHFFFAOYSA-N ethyl 4-methyl-2-[(4-methylbenzoyl)amino]-3-oxopentanoate Chemical compound CCOC(=O)C(C(=O)C(C)C)NC(=O)C1=CC=C(C)C=C1 HDTDHYKMFULBIB-UHFFFAOYSA-N 0.000 description 3
• 229930195729 fatty acid Natural products 0.000 description 3
• 239000000194 fatty acid Substances 0.000 description 3
• 150000004665 fatty acids Chemical class 0.000 description 3
• BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Natural products O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 3
• 239000012362 glacial acetic acid Substances 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 239000000122 growth hormone Substances 0.000 description 3
• 230000036541 health Effects 0.000 description 3
• 108020001756 ligand binding domains Proteins 0.000 description 3
• 210000004185 liver Anatomy 0.000 description 3
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 3
• 229960003105 metformin Drugs 0.000 description 3
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
• BJNZGZRMUOLENY-DTWKUNHWSA-N methyl (1s,3r)-3-(methoxymethoxy)cyclohexane-1-carboxylate Chemical compound COCO[C@@H]1CCC[C@H](C(=O)OC)C1 BJNZGZRMUOLENY-DTWKUNHWSA-N 0.000 description 3
• 238000010369 molecular cloning Methods 0.000 description 3
• 238000000465 moulding Methods 0.000 description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
• CWCMIVBLVUHDHK-ZSNHEYEWSA-N phleomycin D1 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC[C@@H](N=1)C=1SC=C(N=1)C(=O)NCCCCNC(N)=N)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C CWCMIVBLVUHDHK-ZSNHEYEWSA-N 0.000 description 3
• 108020001213 potassium channel Proteins 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 239000000651 prodrug Substances 0.000 description 3
• 229940002612 prodrug Drugs 0.000 description 3
• FZQJEKQLFOKGGV-PZJWPPBQSA-N propan-2-yl 2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methylamino]acetate Chemical compound C1[C@@H](CNCC(=O)OC(C)C)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 FZQJEKQLFOKGGV-PZJWPPBQSA-N 0.000 description 3
• 102000005962 receptors Human genes 0.000 description 3
• 108020003175 receptors Proteins 0.000 description 3
• 208000017520 skin disease Diseases 0.000 description 3
• 239000000758 substrate Substances 0.000 description 3
• QIBSHQJGUKYFLG-LADGPHEKSA-N tert-butyl 1-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxy]cyclopentane-1-carboxylate Chemical compound C([C@H]1CCC[C@H](C1)OCC=1N=C(OC=1C)C=1C=CC(C)=CC=1)OC1(C(=O)OC(C)(C)C)CCCC1 QIBSHQJGUKYFLG-LADGPHEKSA-N 0.000 description 3
• RMKKETWVIMJZMG-FYYLOGMGSA-N tert-butyl 2,2-dimethyl-4-[(1r,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]butanoate Chemical compound CC=1OC(C=2C=CC(C)=CC=2)=NC=1CO[C@@H]1CCC[C@H](CCC(C)(C)C(=O)OC(C)(C)C)C1 RMKKETWVIMJZMG-FYYLOGMGSA-N 0.000 description 3
• FXUFOSJIJOVDAQ-DLBZAZTESA-N tert-butyl 2-[[(1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclohexyl]methoxy]acetate Chemical compound [Si](C)(C)(C(C)(C)C)OC[C@H]1C[C@H](CCC1)COCC(=O)OC(C)(C)C FXUFOSJIJOVDAQ-DLBZAZTESA-N 0.000 description 3
• RBGBOLPYSZLBQB-LOSJGSFVSA-N tert-butyl 2-[[(1s,3r)-3-[tert-butyl(diphenyl)silyl]oxycyclohexyl]methoxy]-2-methylpropanoate Chemical compound C1[C@@H](COC(C)(C)C(=O)OC(C)(C)C)CCC[C@H]1O[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 RBGBOLPYSZLBQB-LOSJGSFVSA-N 0.000 description 3
• SHUBURLJVUAJRU-WLDKUNSKSA-N tert-butyl 2-[[(1s,3r)-3-hydroxycyclohexyl]methoxy]pentanoate Chemical compound CC(C)(C)OC(=O)C(CCC)OC[C@H]1CCC[C@@H](O)C1 SHUBURLJVUAJRU-WLDKUNSKSA-N 0.000 description 3
• PHLUQNYTOQEUAB-UHFFFAOYSA-N tert-butyl 2-diethoxyphosphoryl-3-methylbutanoate Chemical compound CCOP(=O)(OCC)C(C(C)C)C(=O)OC(C)(C)C PHLUQNYTOQEUAB-UHFFFAOYSA-N 0.000 description 3
• XBMDTKNKTAJHTJ-CLJLJLNGSA-N tert-butyl 4-[(1r,3r)-3-[tert-butyl(diphenyl)silyl]oxycyclohexyl]-2,2-dimethylbutanoate Chemical compound C1[C@@H](CCC(C)(C)C(=O)OC(C)(C)C)CCC[C@H]1O[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 XBMDTKNKTAJHTJ-CLJLJLNGSA-N 0.000 description 3
• 238000001890 transfection Methods 0.000 description 3
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
• 229940005605 valeric acid Drugs 0.000 description 3
• DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 2
• 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 2
• YPINLRNGSGGJJT-JXMROGBWSA-N (2e)-2-hydroxyimino-1-phenylpropan-1-one Chemical compound O\N=C(/C)C(=O)C1=CC=CC=C1 YPINLRNGSGGJJT-JXMROGBWSA-N 0.000 description 2
• FJRBPVOMNOILIY-MLWJCNIFSA-N (2s)-2-[(4-methoxyphenoxy)carbonyl-[2-[(1r,3r)-3-[[5-methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethyl]amino]-3-methylbutanoic acid Chemical compound C1=CC(OC)=CC=C1OC(=O)N([C@@H](C(C)C)C(O)=O)CC[C@@H]1C[C@H](OCC2=C(OC(=N2)C=2C=C(C)C=CC=2)C)CCC1 FJRBPVOMNOILIY-MLWJCNIFSA-N 0.000 description 2
• OJFUQZUNNXWSAP-DWLFOUALSA-N (2s)-3-methyl-2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methylamino]butanoic acid Chemical compound C1[C@@H](CN[C@@H](C(C)C)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 OJFUQZUNNXWSAP-DWLFOUALSA-N 0.000 description 2
• HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 2
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical group C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 2
• BKZHSJNLPPAJKB-UHFFFAOYSA-N 1-(2-methyl-1,3-benzoxazol-6-yl)-3-(1,5-naphthyridin-4-yl)urea;hydrochloride Chemical compound Cl.C1=CN=C2C(NC(=O)NC3=CC=C4N=C(OC4=C3)C)=CC=NC2=C1 BKZHSJNLPPAJKB-UHFFFAOYSA-N 0.000 description 2
• MTHCACYGISCLOU-IFMALSPDSA-N 1-[2-[(1r,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethyl]cyclopentane-1-carboxylic acid Chemical compound C([C@H]1CCC[C@H](C1)OCC=1N=C(OC=1C)C=1C=CC(C)=CC=1)CC1(C(O)=O)CCCC1 MTHCACYGISCLOU-IFMALSPDSA-N 0.000 description 2
• GIYZJSLQVOWCAR-UHFFFAOYSA-N 1-cyclohexyl-2-hydroxyiminopropan-1-one Chemical compound ON=C(C)C(=O)C1CCCCC1 GIYZJSLQVOWCAR-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
• 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 2
• PBYRGXGELHNSCQ-NFBKMPQASA-N 2-[2-[(1r,3r)-3-[[5-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethyl]-2-propylpentanoic acid Chemical compound C1[C@@H](CCC(CCC)(CCC)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=C(C=CC=2)C(F)(F)F)=N1 PBYRGXGELHNSCQ-NFBKMPQASA-N 0.000 description 2
• JGSULQKZJFJJMO-MAUKXSAKSA-N 2-[[(1s,3r)-3-[[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxy]-2-methylpropanoic acid Chemical compound CC=1OC(C=2C=CC(F)=CC=2)=NC=1CO[C@@H]1CCC[C@H](COC(C)(C)C(O)=O)C1 JGSULQKZJFJJMO-MAUKXSAKSA-N 0.000 description 2
• OPOAGZUTQZNVSN-MOPGFXCFSA-N 2-[[(1s,3r)-3-[[5-ethyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxymethyl]cyclohexyl]methoxy]-2-methylpropanoic acid Chemical compound CCC=1OC(C=2C=CC(C)=CC=2)=NC=1COC[C@@H]1CCC[C@H](COC(C)(C)C(O)=O)C1 OPOAGZUTQZNVSN-MOPGFXCFSA-N 0.000 description 2
• IXPFOYOVQPMELU-RUYIAYPLSA-N 2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxy]pentanoic acid Chemical compound C1[C@@H](COC(CCC)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 IXPFOYOVQPMELU-RUYIAYPLSA-N 0.000 description 2
• ITFLYMSQFDOPIU-GWKQTIPISA-N 2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methylsulfanyl]heptanoic acid Chemical compound C1[C@@H](CSC(CCCCC)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 ITFLYMSQFDOPIU-GWKQTIPISA-N 0.000 description 2
• OVDQTQKZVZDVSA-RUYIAYPLSA-N 2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methylsulfanyl]pentanoic acid Chemical compound C1[C@@H](CSC(CCC)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 OVDQTQKZVZDVSA-RUYIAYPLSA-N 0.000 description 2
• LPSCRDHPMNPMNL-UKILVPOCSA-N 2-[benzyl-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methyl]amino]acetic acid Chemical compound C([C@H]1CCC[C@H](C1)OCC=1N=C(OC=1C)C=1C=CC(C)=CC=1)N(CC(O)=O)CC1=CC=CC=C1 LPSCRDHPMNPMNL-UKILVPOCSA-N 0.000 description 2
• ROUHMQVDQKMCSR-UVAYFRITSA-N 2-benzyl-4-[(1r,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]butanoic acid Chemical compound C([C@H]1CCC[C@H](C1)OCC=1N=C(OC=1C)C=1C=CC(C)=CC=1)CC(C(O)=O)CC1=CC=CC=C1 ROUHMQVDQKMCSR-UVAYFRITSA-N 0.000 description 2
• ZVJBPHMCBRHVEV-UHFFFAOYSA-N 2-hydroxyiminopentan-3-one Chemical compound CCC(=O)C(C)=NO ZVJBPHMCBRHVEV-UHFFFAOYSA-N 0.000 description 2
• PEJVOHQLVWWLMB-PKOBYXMFSA-N 2-methyl-2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC(C)=CC=2)=NC=1CO[C@@H]1CCC[C@H](COC(C)(C)C(O)=O)C1 PEJVOHQLVWWLMB-PKOBYXMFSA-N 0.000 description 2
• WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
• RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 description 2
• UIHFJWGNNPLCBT-ZJBPFHOOSA-N 3-methyl-2-[2-[(1r,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethyl]butanoic acid Chemical compound C1[C@@H](CCC(C(C)C)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 UIHFJWGNNPLCBT-ZJBPFHOOSA-N 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
• KKVBULDFFNFYHJ-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]octan-7-one Chemical compound C1C2C(=O)OC1CCC2 KKVBULDFFNFYHJ-UHFFFAOYSA-N 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• 206010059313 Anogenital warts Diseases 0.000 description 2
• 206010003210 Arteriosclerosis Diseases 0.000 description 2
• 229940123208 Biguanide Drugs 0.000 description 2
• 240000008886 Ceratonia siliqua Species 0.000 description 2
• 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
• XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
• 208000002330 Congenital Heart Defects Diseases 0.000 description 2
• 241000701022 Cytomegalovirus Species 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
• 230000004568 DNA-binding Effects 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
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 description 2
• 241000701806 Human papillomavirus Species 0.000 description 2
• 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 2
• 208000002260 Keloid Diseases 0.000 description 2
• 206010023330 Keloid scar Diseases 0.000 description 2
• 239000005909 Kieselgur Substances 0.000 description 2
• 238000008214 LDL Cholesterol Methods 0.000 description 2
• 241000254158 Lampyridae Species 0.000 description 2
• 102000016267 Leptin Human genes 0.000 description 2
• 108010092277 Leptin Proteins 0.000 description 2
• 229940086609 Lipase inhibitor Drugs 0.000 description 2
• 206010024612 Lipoma Diseases 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• 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 2
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
• 208000008589 Obesity Diseases 0.000 description 2
• 239000005662 Paraffin oil Substances 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 108700008625 Reporter Genes Proteins 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• 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 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 229940123464 Thiazolidinedione Drugs 0.000 description 2
• 102000006601 Thymidine Kinase Human genes 0.000 description 2
• 108020004440 Thymidine kinase 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
• 108090000631 Trypsin Proteins 0.000 description 2
• 102000004142 Trypsin Human genes 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• 102000005630 Urocortins Human genes 0.000 description 2
• 108010059705 Urocortins Proteins 0.000 description 2
• BBBVDPWVHDYQGB-DTWKUNHWSA-N [(1s,3r)-3-(methoxymethoxy)cyclohexyl]methanol Chemical compound COCO[C@@H]1CCC[C@H](CO)C1 BBBVDPWVHDYQGB-DTWKUNHWSA-N 0.000 description 2
• UEMRNPFSYNBVMH-VHSXEESVSA-N [(1s,3r)-3-(methoxymethoxymethyl)cyclohexyl]methanol Chemical compound COCOC[C@@H]1CCC[C@H](CO)C1 UEMRNPFSYNBVMH-VHSXEESVSA-N 0.000 description 2
• VDDBRZJNFWSEGV-UHFFFAOYSA-N [5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methanol Chemical compound OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 VDDBRZJNFWSEGV-UHFFFAOYSA-N 0.000 description 2
• 235000010489 acacia gum Nutrition 0.000 description 2
• 229960002632 acarbose Drugs 0.000 description 2
• 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 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 239000000654 additive Substances 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 229940025084 amphetamine Drugs 0.000 description 2
• 150000001450 anions Chemical class 0.000 description 2
• 239000003242 anti bacterial agent Substances 0.000 description 2
• 230000003110 anti-inflammatory effect Effects 0.000 description 2
• 239000000883 anti-obesity agent Substances 0.000 description 2
• 229940088710 antibiotic agent Drugs 0.000 description 2
• 229940125710 antiobesity agent Drugs 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 208000011775 arteriosclerosis disease Diseases 0.000 description 2
• 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 2
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 239000003613 bile acid Substances 0.000 description 2
• 230000033228 biological regulation Effects 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 230000023852 carbohydrate metabolic process Effects 0.000 description 2
• 235000021256 carbohydrate metabolism Nutrition 0.000 description 2
• 230000024245 cell differentiation Effects 0.000 description 2
• 239000006285 cell suspension Substances 0.000 description 2
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 238000010276 construction Methods 0.000 description 2
• 208000029078 coronary artery disease Diseases 0.000 description 2
• 230000001419 dependent effect Effects 0.000 description 2
• 238000010511 deprotection reaction Methods 0.000 description 2
• 229960004597 dexfenfluramine Drugs 0.000 description 2
• 235000013325 dietary fiber Nutrition 0.000 description 2
• 230000001079 digestive effect Effects 0.000 description 2
• 208000016097 disease of metabolism Diseases 0.000 description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
• DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
• DRHPVHQCDZJCNG-UHFFFAOYSA-N ethyl 3-methyl-2-sulfanylbutanoate Chemical compound CCOC(=O)C(S)C(C)C DRHPVHQCDZJCNG-UHFFFAOYSA-N 0.000 description 2
• 238000011156 evaluation Methods 0.000 description 2
• 229940125753 fibrate Drugs 0.000 description 2
• 239000002657 fibrous material Substances 0.000 description 2
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 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 2
• 239000003316 glycosidase inhibitor Substances 0.000 description 2
• 230000005831 heart abnormality Effects 0.000 description 2
• 229940088597 hormone Drugs 0.000 description 2
• 239000005556 hormone Substances 0.000 description 2
• 102000054223 human PPARA Human genes 0.000 description 2
• 208000015181 infectious disease Diseases 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000004026 insulin derivative Substances 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
• 210000003734 kidney Anatomy 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 229940060975 lantus 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
• 229910052744 lithium Inorganic materials 0.000 description 2
• 229960004844 lovastatin Drugs 0.000 description 2
• 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 2
• 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 2
• 238000003670 luciferase enzyme activity assay Methods 0.000 description 2
• 238000005259 measurement Methods 0.000 description 2
• 230000001404 mediated effect Effects 0.000 description 2
• 229950004994 meglitinide Drugs 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
• WKBHZYNYZZQHAN-NWDGAFQWSA-N methyl (1s,3r)-3-[tert-butyl(dimethyl)silyl]oxycyclohexane-1-carboxylate Chemical compound COC(=O)[C@H]1CCC[C@@H](O[Si](C)(C)C(C)(C)C)C1 WKBHZYNYZZQHAN-NWDGAFQWSA-N 0.000 description 2
• DAOFJPZFGBKAMZ-NSHDSACASA-N methyl (2s)-2-amino-2-methyl-3-phenylpropanoate Chemical compound COC(=O)[C@@](C)(N)CC1=CC=CC=C1 DAOFJPZFGBKAMZ-NSHDSACASA-N 0.000 description 2
• VLNNACMZTDZCFH-UHFFFAOYSA-N methyl 1-aminocyclopentane-1-carboxylate Chemical compound COC(=O)C1(N)CCCC1 VLNNACMZTDZCFH-UHFFFAOYSA-N 0.000 description 2
• 150000004702 methyl esters Chemical class 0.000 description 2
• 208000010125 myocardial infarction Diseases 0.000 description 2
• 235000001968 nicotinic acid Nutrition 0.000 description 2
• 229960003512 nicotinic acid Drugs 0.000 description 2
• 239000011664 nicotinic acid Substances 0.000 description 2
• 235000020824 obesity Nutrition 0.000 description 2
• 239000012285 osmium tetroxide Substances 0.000 description 2
• 229910052763 palladium Inorganic materials 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• 230000035790 physiological processes and functions Effects 0.000 description 2
• 229960005095 pioglitazone Drugs 0.000 description 2
• 239000004033 plastic Substances 0.000 description 2
• 229920003023 plastic Polymers 0.000 description 2
• 201000010065 polycystic ovary syndrome Diseases 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
• 230000003389 potentiating effect Effects 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 230000008569 process Effects 0.000 description 2
• 230000022532 regulation of transcription, DNA-dependent Effects 0.000 description 2
• 229960004586 rosiglitazone Drugs 0.000 description 2
• 201000010153 skin papilloma Diseases 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 235000009518 sodium iodide Nutrition 0.000 description 2
• 239000004317 sodium nitrate Substances 0.000 description 2
• 235000010344 sodium nitrate Nutrition 0.000 description 2
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
• 239000011550 stock solution Substances 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
• 239000005720 sucrose Substances 0.000 description 2
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
• 208000011580 syndromic disease Diseases 0.000 description 2
• GARZSWFTPUBBCZ-FLIPHLSNSA-N tert-butyl (2s)-2-[(4-methoxyphenoxy)carbonyl-[2-[(1r,3r)-3-[[5-methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethyl]amino]-3-methylbutanoate Chemical compound C1=CC(OC)=CC=C1OC(=O)N([C@@H](C(C)C)C(=O)OC(C)(C)C)CC[C@@H]1C[C@H](OCC2=C(OC(=N2)C=2C=C(C)C=CC=2)C)CCC1 GARZSWFTPUBBCZ-FLIPHLSNSA-N 0.000 description 2
• JRSRIAAIVJXGLR-GHTZIAJQSA-N tert-butyl 2-[[(1s,3r)-3-[[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxy]-2-methylpropanoate Chemical compound CC=1OC(C=2C=CC(F)=CC=2)=NC=1CO[C@@H]1CCC[C@H](COC(C)(C)C(=O)OC(C)(C)C)C1 JRSRIAAIVJXGLR-GHTZIAJQSA-N 0.000 description 2
• GDQNVKDJIGLBOL-UHFFFAOYSA-N tert-butyl 2-diethoxyphosphoryl-3-phenylpropanoate Chemical compound CCOP(=O)(OCC)C(C(=O)OC(C)(C)C)CC1=CC=CC=C1 GDQNVKDJIGLBOL-UHFFFAOYSA-N 0.000 description 2
• NFEGNISFSSLEGU-UHFFFAOYSA-N tert-butyl 2-diethoxyphosphorylacetate Chemical compound CCOP(=O)(OCC)CC(=O)OC(C)(C)C NFEGNISFSSLEGU-UHFFFAOYSA-N 0.000 description 2
• CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 description 2
• DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
• 229960005371 tolbutamide Drugs 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
• 238000012546 transfer Methods 0.000 description 2
• 239000012588 trypsin Substances 0.000 description 2
• 239000000777 urocortin Substances 0.000 description 2
• 230000002792 vascular Effects 0.000 description 2
• 239000013598 vector Substances 0.000 description 2
• MBMQEIFVQACCCH-QBODLPLBSA-N zearalenone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-QBODLPLBSA-N 0.000 description 2
• DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical group CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical class NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
• FAUXGBNDWXZEIB-AQHOXQCLSA-N (2s)-2-[benzoyl-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methyl]amino]-3-methylbutanoic acid Chemical compound O([C@@H]1CCC[C@@H](C1)CN([C@@H](C(C)C)C(O)=O)C(=O)C=1C=CC=CC=1)CC(=C(O1)C)N=C1C1=CC=C(C)C=C1 FAUXGBNDWXZEIB-AQHOXQCLSA-N 0.000 description 1
• NKMXRQPSPLOMQI-JAHCWSGRSA-N (2s)-3-methyl-2-[methyl-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methyl]amino]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@@H](CN(C)[C@@H](C(C)C)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 NKMXRQPSPLOMQI-JAHCWSGRSA-N 0.000 description 1
• ALSCEGDXFJIYES-YFKPBYRVSA-N (2s)-pyrrolidine-2-carbonitrile Chemical compound N#C[C@@H]1CCCN1 ALSCEGDXFJIYES-YFKPBYRVSA-N 0.000 description 1
• ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
• HBZBAMXERPYTFS-SECBINFHSA-N (4S)-2-(6,7-dihydro-5H-pyrrolo[3,2-f][1,3]benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)[C@H]1CSC(=N1)c1nc2cc3CCNc3cc2s1 HBZBAMXERPYTFS-SECBINFHSA-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
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• OMXRTIUYSHDUTH-UHFFFAOYSA-N 1-(3-ethyl-1-benzofuran-7-yl)piperazine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC=C2C(CC)=COC2=C1N1CCNCC1 OMXRTIUYSHDUTH-UHFFFAOYSA-N 0.000 description 1
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
• QTFJFAZLKXSFSA-GGXMVOPNSA-N 1-[2-[(1r,3r)-3-[[5-methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethyl-phenylmethoxycarbonylamino]cyclopentane-1-carboxylic acid Chemical compound C([C@H]1CCC[C@H](C1)OCC=1N=C(OC=1C)C=1C=C(C)C=CC=1)CN(C1(CCCC1)C(O)=O)C(=O)OCC1=CC=CC=C1 QTFJFAZLKXSFSA-GGXMVOPNSA-N 0.000 description 1
• BYUKMGPIDIWLAC-UHFFFAOYSA-N 1-[4-chloro-3-(methylsulfonylmethyl)phenyl]-2-[2-[(2,3-dimethyl-1h-indol-6-yl)oxy]ethylamino]ethanol;hydrochloride Chemical compound Cl.C=1C=C2C(C)=C(C)NC2=CC=1OCCNCC(O)C1=CC=C(Cl)C(CS(C)(=O)=O)=C1 BYUKMGPIDIWLAC-UHFFFAOYSA-N 0.000 description 1
• MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
• OMLOASXVBUNPTN-UHFFFAOYSA-N 2,4-dimethylcyclohexane-1-carbaldehyde Chemical compound CC1CCC(C=O)C(C)C1 OMLOASXVBUNPTN-UHFFFAOYSA-N 0.000 description 1
• WKNRGTXARYMYLR-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4-(iodomethyl)-5-methyl-1,3-oxazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(CI)=C(C)O1 WKNRGTXARYMYLR-UHFFFAOYSA-N 0.000 description 1
• UEJHHKGNCWUBHD-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-(iodomethyl)-5-methyl-1,3-oxazole Chemical compound ICC1=C(C)OC(C=2C=CC(F)=CC=2)=N1 UEJHHKGNCWUBHD-UHFFFAOYSA-N 0.000 description 1
• VWSKNCOVQCPWRL-GHMZBOCLSA-N 2-[(1s,3r)-3-(methoxymethoxymethyl)cyclohexyl]ethanol Chemical compound COCOC[C@@H]1CCC[C@H](CCO)C1 VWSKNCOVQCPWRL-GHMZBOCLSA-N 0.000 description 1
• FXZNMFWKXGNSSD-ZEQKJWHPSA-N 2-[2-[(1r,3r)-3-[[5-methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethyl-phenylmethoxycarbonylamino]acetic acid Chemical compound C([C@H]1CCC[C@H](C1)OCC=1N=C(OC=1C)C=1C=C(C)C=CC=1)CN(CC(O)=O)C(=O)OCC1=CC=CC=C1 FXZNMFWKXGNSSD-ZEQKJWHPSA-N 0.000 description 1
• UJGBTZUTZSMGCO-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-5,7-dimethylindol-1-yl]acetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(C)C=C(C)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC UJGBTZUTZSMGCO-UHFFFAOYSA-N 0.000 description 1
• NEXPOGHHMJHJPG-UXHICEINSA-N 2-[[(1s,3r)-3-[(5-ethyl-2-naphthalen-2-yl-1,3-oxazol-4-yl)methoxymethyl]cyclohexyl]methoxy]-2-methylpropanoic acid Chemical compound CCC=1OC(C=2C=C3C=CC=CC3=CC=2)=NC=1COC[C@@H]1CCC[C@H](COC(C)(C)C(O)=O)C1 NEXPOGHHMJHJPG-UXHICEINSA-N 0.000 description 1
• SETFJYMSNFDHPA-UDGGGLCFSA-N 2-[[(1s,3r)-3-[[2-(3-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxy]propanoic acid Chemical compound COC1=CC=CC(C=2OC(C)=C(CO[C@H]3C[C@@H](COC(C)C(O)=O)CCC3)N=2)=C1 SETFJYMSNFDHPA-UDGGGLCFSA-N 0.000 description 1
• VFABFUUZBZQNGK-MSOLQXFVSA-N 2-[[(1s,3r)-3-[[5-ethyl-2-(3-methoxyphenyl)-1,3-oxazol-4-yl]methoxymethyl]cyclohexyl]methoxy]-2-methylpropanoic acid Chemical compound CCC=1OC(C=2C=C(OC)C=CC=2)=NC=1COC[C@@H]1CCC[C@H](COC(C)(C)C(O)=O)C1 VFABFUUZBZQNGK-MSOLQXFVSA-N 0.000 description 1
• OQHBOFIUEPQSPT-WFTITGEASA-N 2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxy]propanoic acid Chemical compound C1[C@@H](COC(C)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 OQHBOFIUEPQSPT-WFTITGEASA-N 0.000 description 1
• FHAMLNBBCXHHBH-FOHCZPNYSA-N 2-[[(1s,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methylsulfanyl]butanoic acid Chemical compound C1[C@@H](CSC(CC)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 FHAMLNBBCXHHBH-FOHCZPNYSA-N 0.000 description 1
• IMTDARJUFJZNLE-JAIYHHTPSA-N 2-[[(1s,3r)-3-[[5-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]cyclohexyl]methoxy]propanoic acid Chemical compound C1[C@@H](COC(C)C(O)=O)CCC[C@H]1CC1=C(C)OC(C=2C=C(C=CC=2)C(F)(F)F)=N1 IMTDARJUFJZNLE-JAIYHHTPSA-N 0.000 description 1
• MTOMZRXGNOCENL-IIAQOEISSA-N 2-ethyl-4-[(1r,3r)-3-[[2-(3-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]cyclohexyl]butanoic acid Chemical compound C1[C@@H](CCC(CC)C(O)=O)CCC[C@H]1OCC1=C(C)OC(C=2C=C(OC)C=CC=2)=N1 MTOMZRXGNOCENL-IIAQOEISSA-N 0.000 description 1
• PEJVOHQLVWWLMB-MJGOQNOKSA-N 2-methyl-2-[[(1r,3s)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC(C)=CC=2)=NC=1CO[C@H]1CCC[C@@H](COC(C)(C)C(O)=O)C1 PEJVOHQLVWWLMB-MJGOQNOKSA-N 0.000 description 1
• AAGBEPQFKGTGAL-MSOLQXFVSA-N 2-methyl-2-[[(1s,3r)-3-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxymethyl]cyclohexyl]methoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1COC[C@@H]1CCC[C@H](COC(C)(C)C(O)=O)C1 AAGBEPQFKGTGAL-MSOLQXFVSA-N 0.000 description 1
• PULUCJCWYVQZMW-IMFNMPFLSA-N 2-methyl-2-[[(1s,3r)-3-[(5-methylnaphthalen-2-yl)-(1,3-oxazol-4-ylmethoxy)methyl]cyclohexyl]methoxy]propanoic acid Chemical compound C=1C=C2C(C)=CC=CC2=CC=1C([C@H]1C[C@@H](COC(C)(C)C(O)=O)CCC1)OCC1=COC=N1 PULUCJCWYVQZMW-IMFNMPFLSA-N 0.000 description 1
• YCOXJFAUNLRWPU-UHFFFAOYSA-N 2-methyl-n,n-dipropyl-9-(2,4,6-trimethylphenyl)pyrimido[4,5-b]indol-4-amine Chemical compound C12=CC=CC=C2C=2C(N(CCC)CCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C YCOXJFAUNLRWPU-UHFFFAOYSA-N 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
• PWSXRGRLZKVHLW-UHFFFAOYSA-N 2-phosphonobutanoic acid Chemical compound CCC(C(O)=O)P(O)(O)=O PWSXRGRLZKVHLW-UHFFFAOYSA-N 0.000 description 1
• 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 1
• RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 description 1
• USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
• SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
• UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
• WQIAQJQZRFUYEG-UHFFFAOYSA-N 4-(1-iodoethyl)-2-(4-methylphenyl)-1,3-oxazole Chemical compound CC(I)C1=COC(C=2C=CC(C)=CC=2)=N1 WQIAQJQZRFUYEG-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
• XQXAMDSDBOCMHF-UHFFFAOYSA-N 4-(chloromethoxymethyl)-5-ethyl-2-(4-methylphenyl)-1,3-oxazole Chemical compound ClCOCC1=C(CC)OC(C=2C=CC(C)=CC=2)=N1 XQXAMDSDBOCMHF-UHFFFAOYSA-N 0.000 description 1
• MVUPNMYSPWFTJE-UHFFFAOYSA-N 4-(iodomethyl)-2-(3-methoxyphenyl)-5-(trifluoromethyl)-1,3-oxazole Chemical compound COC1=CC=CC(C=2OC(=C(CI)N=2)C(F)(F)F)=C1 MVUPNMYSPWFTJE-UHFFFAOYSA-N 0.000 description 1
• OKHGLMQXLUEZMI-UHFFFAOYSA-N 4-(iodomethyl)-2-(3-methoxyphenyl)-5-phenyl-1,3-oxazole Chemical compound COC1=CC=CC(C=2OC(=C(CI)N=2)C=2C=CC=CC=2)=C1 OKHGLMQXLUEZMI-UHFFFAOYSA-N 0.000 description 1
• CUPROPFTDOKVRM-UHFFFAOYSA-N 4-(iodomethyl)-2-(4-methoxyphenyl)-5-methyl-1,3-oxazole Chemical compound C1=CC(OC)=CC=C1C1=NC(CI)=C(C)O1 CUPROPFTDOKVRM-UHFFFAOYSA-N 0.000 description 1
• AUZKRBKDXZUWMZ-UHFFFAOYSA-N 4-(iodomethyl)-2-(4-methylphenyl)-5-(trifluoromethyl)-1,3-oxazole 4-methylbenzoyl chloride Chemical compound ICC=1N=C(OC1C(F)(F)F)C1=CC=C(C=C1)C.CC1=CC=C(C(=O)Cl)C=C1 AUZKRBKDXZUWMZ-UHFFFAOYSA-N 0.000 description 1
• QKSYAXASYDZMFY-UHFFFAOYSA-N 4-(iodomethyl)-5-(trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]-1,3-oxazole Chemical compound ICC1=C(C(F)(F)F)OC(C=2C=C(C=CC=2)C(F)(F)F)=N1 QKSYAXASYDZMFY-UHFFFAOYSA-N 0.000 description 1
• LAKXJTRDJPBSAS-UHFFFAOYSA-N 4-(iodomethyl)-5-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-oxazole Chemical compound ICC1=C(C)OC(C=2C=C(C=CC=2)C(F)(F)F)=N1 LAKXJTRDJPBSAS-UHFFFAOYSA-N 0.000 description 1
• SLYIGTWFTNDINH-UHFFFAOYSA-N 4-(iodomethyl)-5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazole Chemical compound ICC1=C(C)OC(C=2C=CC(=CC=2)C(F)(F)F)=N1 SLYIGTWFTNDINH-UHFFFAOYSA-N 0.000 description 1
• DMHMTFWZDRZMNU-LQRGHNGLSA-N 4-[(1r,3r)-3-[[2-(3-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]cyclohexyl]-2-methylbutanoic acid Chemical compound COC1=CC=CC(C=2OC(C)=C(CO[C@H]3C[C@@H](CCC(C)C(O)=O)CCC3)N=2)=C1 DMHMTFWZDRZMNU-LQRGHNGLSA-N 0.000 description 1
• IXVNJZOBYTWMPZ-UHFFFAOYSA-N 4-[[chloro-(5-methylnaphthalen-2-yl)methoxy]methyl]-1,3-oxazole Chemical compound C=1C=C2C(C)=CC=CC2=CC=1C(Cl)OCC1=COC=N1 IXVNJZOBYTWMPZ-UHFFFAOYSA-N 0.000 description 1
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
• UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
• 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 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
• NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
• ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 1
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
• WZOMSQRBEXCMRP-UHFFFAOYSA-N 5-ethyl-4-(iodomethyl)-2-(3-methoxyphenyl)-1,3-oxazole Chemical compound ICC1=C(CC)OC(C=2C=C(OC)C=CC=2)=N1 WZOMSQRBEXCMRP-UHFFFAOYSA-N 0.000 description 1
• IBKTYZFDQOEJIP-UHFFFAOYSA-N 5-ethyl-4-(iodomethyl)-2-[3-(trifluoromethyl)phenyl]-1,3-oxazole;3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1.ICC1=C(CC)OC(C=2C=C(C=CC=2)C(F)(F)F)=N1 IBKTYZFDQOEJIP-UHFFFAOYSA-N 0.000 description 1
• NCIZGFYECCPUKS-UHFFFAOYSA-N 5-methyl-2-(4-methylphenyl)-1,3-oxazole Chemical compound O1C(C)=CN=C1C1=CC=C(C)C=C1 NCIZGFYECCPUKS-UHFFFAOYSA-N 0.000 description 1
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
• 239000005541 ACE inhibitor Substances 0.000 description 1
• 102000004146 ATP citrate synthases Human genes 0.000 description 1
• 108090000662 ATP citrate synthases Proteins 0.000 description 1
• 208000004611 Abdominal Obesity Diseases 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• 208000002874 Acne Vulgaris Diseases 0.000 description 1
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
• 206010002383 Angina Pectoris Diseases 0.000 description 1
• 208000019901 Anxiety disease Diseases 0.000 description 1
• 102000018619 Apolipoproteins A Human genes 0.000 description 1
• 108010027004 Apolipoproteins A Proteins 0.000 description 1
• 102000018616 Apolipoproteins B Human genes 0.000 description 1
• 108010027006 Apolipoproteins B Proteins 0.000 description 1
• 206010003211 Arteriosclerosis coronary artery Diseases 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
• XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
• 210000002237 B-cell of pancreatic islet Anatomy 0.000 description 1
• 208000005440 Basal Cell Neoplasms Diseases 0.000 description 1
• 206010004146 Basal cell carcinoma Diseases 0.000 description 1
• 239000005711 Benzoic acid Substances 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
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
• JVEGCGQXRCOAFN-UHFFFAOYSA-N C(C(C)C)[AlH]CC(C)C.[Li] Chemical compound C(C(C)C)[AlH]CC(C)C.[Li] JVEGCGQXRCOAFN-UHFFFAOYSA-N 0.000 description 1
• OJHPFKUAMDQEGI-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)O.OCC(C)(C)NCC(=O)N1C(CCC1)C#N Chemical compound C1(=CC=CC=C1)S(=O)(=O)O.OCC(C)(C)NCC(=O)N1C(CCC1)C#N OJHPFKUAMDQEGI-UHFFFAOYSA-N 0.000 description 1
• FIJAUVJVWTWVBB-UHFFFAOYSA-N CC1=C(N=C(O1)C1=CC=C(C=C1)C)COC1CC(CCC1)COC(C(=O)O)CC.CC1=C(N=C(O1)C1=CC=C(C=C1)C)CI Chemical compound CC1=C(N=C(O1)C1=CC=C(C=C1)C)COC1CC(CCC1)COC(C(=O)O)CC.CC1=C(N=C(O1)C1=CC=C(C=C1)C)CI FIJAUVJVWTWVBB-UHFFFAOYSA-N 0.000 description 1
• FYSPQUCYAHVEBR-TYMOSBPTSA-N CC1=C(N=C(O1)C1=CC=C(C=C1)C)COC[C@H]1C[C@H](CCC1)COC(C(=O)O)C(C)C.CC1=C(N=C(O1)C1=CC=C(C=C1)C)C=O Chemical compound CC1=C(N=C(O1)C1=CC=C(C=C1)C)COC[C@H]1C[C@H](CCC1)COC(C(=O)O)C(C)C.CC1=C(N=C(O1)C1=CC=C(C=C1)C)C=O FYSPQUCYAHVEBR-TYMOSBPTSA-N 0.000 description 1
• VLYXAYUZZIJCCY-SPKIJCNCSA-N CC1=C(N=C(O1)C1=CC=C(C=C1)C)CO[C@H]1C[C@H](CCC1)COC(C(=O)O)CC1=CC=CC=C1.CC1=C(N=C(O1)C1=CC=C(C=C1)C)CI Chemical compound CC1=C(N=C(O1)C1=CC=C(C=C1)C)CO[C@H]1C[C@H](CCC1)COC(C(=O)O)CC1=CC=CC=C1.CC1=C(N=C(O1)C1=CC=C(C=C1)C)CI VLYXAYUZZIJCCY-SPKIJCNCSA-N 0.000 description 1
• FVTKSNMBKDHYIN-JUOYHRLASA-N CC1=C(N=C(O1)C1=CC=C(C=C1)C)CO[C@H]1C[C@H](CCC1)CSC(C(=O)O)(C)C.SC(C(=O)OCC)(C)C Chemical compound CC1=C(N=C(O1)C1=CC=C(C=C1)C)CO[C@H]1C[C@H](CCC1)CSC(C(=O)O)(C)C.SC(C(=O)OCC)(C)C FVTKSNMBKDHYIN-JUOYHRLASA-N 0.000 description 1
• ABVSWZBOEQLDRF-VDBVIFAESA-N CC1=C(N=C(O1)C=1C=C(C=CC1)C)CO[C@H]1C[C@H](CCC1)COC(C(=O)O)C.CC1=C(N=C(O1)C=1C=C(C=CC1)C)CI Chemical compound CC1=C(N=C(O1)C=1C=C(C=CC1)C)CO[C@H]1C[C@H](CCC1)COC(C(=O)O)C.CC1=C(N=C(O1)C=1C=C(C=CC1)C)CI ABVSWZBOEQLDRF-VDBVIFAESA-N 0.000 description 1
• WALNECANBDYCNN-JAHCWSGRSA-N COC(=O)N([C@H](C(=O)O)C(C)C)C[C@@H]1C[C@@H](CCC1)OCC=1N=C(OC1C)C1=CC=C(C=C1)C.COC(=O)Cl Chemical compound COC(=O)N([C@H](C(=O)O)C(C)C)C[C@@H]1C[C@@H](CCC1)OCC=1N=C(OC1C)C1=CC=C(C=C1)C.COC(=O)Cl WALNECANBDYCNN-JAHCWSGRSA-N 0.000 description 1
• KGVIWKFTSVJKEJ-PPMCDXLLSA-N COC=1C=C(C=CC1)C=1OC(=C(N1)CO[C@H]1C[C@H](CCC1)CCC(C(=O)O)C(C)C)C.[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)O[C@H]1C[C@H](CCC1)CCC(C(=O)O)C(C)C Chemical compound COC=1C=C(C=CC1)C=1OC(=C(N1)CO[C@H]1C[C@H](CCC1)CCC(C(=O)O)C(C)C)C.[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)O[C@H]1C[C@H](CCC1)CCC(C(=O)O)C(C)C KGVIWKFTSVJKEJ-PPMCDXLLSA-N 0.000 description 1
• XULADKKSNBHZAT-YQERHDSCSA-N COC=1C=C(C=CC1)C=1OC(=C(N1)CO[C@H]1C[C@H](CCC1)CCC(C(=O)O)CCC)C.P(=O)(O)(O)C(C(=O)O)CCC Chemical compound COC=1C=C(C=CC1)C=1OC(=C(N1)CO[C@H]1C[C@H](CCC1)CCC(C(=O)O)CCC)C.P(=O)(O)(O)C(C(=O)O)CCC XULADKKSNBHZAT-YQERHDSCSA-N 0.000 description 1
• GMYVDZNLNFWXET-DLJMHQLKSA-N CS(=O)(=O)CS(=O)(=O)N([C@H](C(=O)O)C(C)C)C[C@@H]1C[C@@H](CCC1)OCC=1N=C(OC1C)C1=CC=C(C=C1)C.C(C)N(CC)CC Chemical compound CS(=O)(=O)CS(=O)(=O)N([C@H](C(=O)O)C(C)C)C[C@@H]1C[C@@H](CCC1)OCC=1N=C(OC1C)C1=CC=C(C=C1)C.C(C)N(CC)CC GMYVDZNLNFWXET-DLJMHQLKSA-N 0.000 description 1
• 206010006895 Cachexia Diseases 0.000 description 1
• 229940127291 Calcium channel antagonist Drugs 0.000 description 1
• 208000031229 Cardiomyopathies Diseases 0.000 description 1
• 241000218645 Cedrus Species 0.000 description 1
• 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
• 206010065941 Central obesity Diseases 0.000 description 1
• 229940122502 Cholesterol absorption inhibitor Drugs 0.000 description 1
• 229920001268 Cholestyramine Polymers 0.000 description 1
• 108020004635 Complementary DNA Proteins 0.000 description 1
• 208000011231 Crohn disease Diseases 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
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 description 1
• 208000001976 Endocrine Gland Neoplasms Diseases 0.000 description 1
• 208000032541 Epidermal naevus Diseases 0.000 description 1
• 206010015150 Erythema Diseases 0.000 description 1
• LXXNWCFBZHKFPT-UHFFFAOYSA-N Ethyl 2-mercaptopropionate Chemical compound CCOC(=O)C(C)S LXXNWCFBZHKFPT-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• MXTHCJIHNDNOBK-ULXOMSGMSA-N FC(C(=O)O)(F)F.S1C(=CC=C1)CN(CC(=O)O)C[C@@H]1C[C@@H](CCC1)OCC=1N=C(OC1C)C1=CC=C(C=C1)C.S1C(=CC=C1)C=O Chemical compound FC(C(=O)O)(F)F.S1C(=CC=C1)CN(CC(=O)O)C[C@@H]1C[C@@H](CCC1)OCC=1N=C(OC1C)C1=CC=C(C=C1)C.S1C(=CC=C1)C=O MXTHCJIHNDNOBK-ULXOMSGMSA-N 0.000 description 1
• 208000001034 Frostbite Diseases 0.000 description 1
• 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 1
• 102000019432 Galanin Human genes 0.000 description 1
• 101800002068 Galanin Proteins 0.000 description 1
• 108010010803 Gelatin Proteins 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
• 102400000321 Glucagon Human genes 0.000 description 1
• 108060003199 Glucagon Proteins 0.000 description 1
• 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 1
• 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 1
• 108090000079 Glucocorticoid Receptors Proteins 0.000 description 1
• 102100033417 Glucocorticoid receptor Human genes 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• 102000007390 Glycogen Phosphorylase Human genes 0.000 description 1
• 108010046163 Glycogen Phosphorylase Proteins 0.000 description 1
• 229940122069 Glycosidase inhibitor Drugs 0.000 description 1
• 201000005569 Gout Diseases 0.000 description 1
• 102000018997 Growth Hormone Human genes 0.000 description 1
• 108010051696 Growth Hormone Proteins 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 239000007821 HATU Substances 0.000 description 1
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
• 229910004373 HOAc Inorganic materials 0.000 description 1
• 101000998969 Homo sapiens Inositol-3-phosphate synthase 1 Proteins 0.000 description 1
• 101000741790 Homo sapiens Peroxisome proliferator-activated receptor gamma Proteins 0.000 description 1
• 101000684208 Homo sapiens Prolyl endopeptidase FAP Proteins 0.000 description 1
• 208000035150 Hypercholesterolemia Diseases 0.000 description 1
• 206010020608 Hypercoagulation Diseases 0.000 description 1
• 208000031226 Hyperlipidaemia Diseases 0.000 description 1
• JPCBKGFLVJBYRV-UHFFFAOYSA-N ICC=1N=C(OC1C)C=1OC(=CC1)C.CC1=CC=C(O1)C=O Chemical compound ICC=1N=C(OC1C)C=1OC(=CC1)C.CC1=CC=C(O1)C=O JPCBKGFLVJBYRV-UHFFFAOYSA-N 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 102100036881 Inositol-3-phosphate synthase 1 Human genes 0.000 description 1
• 108010057186 Insulin Glargine Proteins 0.000 description 1
• COCFEDIXXNGUNL-RFKWWTKHSA-N Insulin glargine 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)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(=O)NCC(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 COCFEDIXXNGUNL-RFKWWTKHSA-N 0.000 description 1
• 229940122355 Insulin sensitizer Drugs 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• 102000000853 LDL receptors Human genes 0.000 description 1
• 108010001831 LDL receptors Proteins 0.000 description 1
• 239000004166 Lanolin Substances 0.000 description 1
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• 102000004882 Lipase Human genes 0.000 description 1
• 108090001060 Lipase Proteins 0.000 description 1
• 239000004367 Lipase Substances 0.000 description 1
• 108010013563 Lipoprotein Lipase Proteins 0.000 description 1
• 102100022119 Lipoprotein lipase Human genes 0.000 description 1
• 108090001030 Lipoproteins Proteins 0.000 description 1
• 102000004895 Lipoproteins Human genes 0.000 description 1
• 229940122014 Lyase inhibitor Drugs 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 241000124008 Mammalia Species 0.000 description 1
• UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
• RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
• 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 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
• IRLWJILLXJGJTD-UHFFFAOYSA-N Muraglitazar Chemical compound C1=CC(OC)=CC=C1OC(=O)N(CC(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 IRLWJILLXJGJTD-UHFFFAOYSA-N 0.000 description 1
• 101000964477 Mus musculus Zinc finger and BTB domain-containing protein 17 Proteins 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 201000007224 Myeloproliferative neoplasm Diseases 0.000 description 1
• 208000021908 Myocardial disease Diseases 0.000 description 1
• 201000009053 Neurodermatitis Diseases 0.000 description 1
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
• 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
• 102000002512 Orexin Human genes 0.000 description 1
• 206010033307 Overweight Diseases 0.000 description 1
• 229940126033 PPAR agonist Drugs 0.000 description 1
• 108010015181 PPAR delta Proteins 0.000 description 1
• 229940124754 PPAR-alpha/gamma agonist Drugs 0.000 description 1
• 108091008768 PPARγ1 Proteins 0.000 description 1
• 108091008767 PPARγ2 Proteins 0.000 description 1
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
• 206010033645 Pancreatitis Diseases 0.000 description 1
• 208000018737 Parkinson disease Diseases 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
• 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
• 102100040918 Pro-glucagon Human genes 0.000 description 1
• 206010036774 Proctitis Diseases 0.000 description 1
• 206010036783 Proctitis ulcerative Diseases 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• 102000009572 RNA Polymerase II Human genes 0.000 description 1
• 108010009460 RNA Polymerase II Proteins 0.000 description 1
• 208000017442 Retinal disease Diseases 0.000 description 1
• 206010038923 Retinopathy Diseases 0.000 description 1
• 208000025747 Rheumatic disease Diseases 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
• 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
• 208000000453 Skin Neoplasms Diseases 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 229940123495 Squalene synthetase inhibitor Drugs 0.000 description 1
• 208000006011 Stroke Diseases 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
• 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 1
• ZWZUFQPXYVYAFO-UHFFFAOYSA-N Tert-butyl (triphenylphosphoranylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC(C)(C)C)C1=CC=CC=C1 ZWZUFQPXYVYAFO-UHFFFAOYSA-N 0.000 description 1
• 102100031241 Thioredoxin reductase 2, mitochondrial Human genes 0.000 description 1
• 208000007536 Thrombosis Diseases 0.000 description 1
• 108010071769 Thyroid Hormone Receptors beta Proteins 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 206010047115 Vasculitis Diseases 0.000 description 1
• 238000007239 Wittig reaction Methods 0.000 description 1
• FOXXUKXSEOICIT-VQTJNVASSA-N [(1s,3r)-3-[tert-butyl(diphenyl)silyl]oxycyclohexyl]methanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)O[C@@H]1CCC[C@H](CO)C1 FOXXUKXSEOICIT-VQTJNVASSA-N 0.000 description 1
• 239000002250 absorbent Substances 0.000 description 1
• 230000002745 absorbent Effects 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• 239000001785 acacia senegal l. willd gum Substances 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 206010000496 acne Diseases 0.000 description 1
• 208000009621 actinic keratosis Diseases 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 150000001263 acyl chlorides Chemical class 0.000 description 1
• 239000000853 adhesive Substances 0.000 description 1
• 230000001070 adhesive effect Effects 0.000 description 1
• 210000001789 adipocyte Anatomy 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 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
• KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 239000003392 amylase inhibitor Substances 0.000 description 1
• 230000033115 angiogenesis Effects 0.000 description 1
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
• 229920006318 anionic polymer Polymers 0.000 description 1
• 230000003178 anti-diabetic effect Effects 0.000 description 1
• 230000002785 anti-thrombosis Effects 0.000 description 1
• 239000003146 anticoagulant agent Substances 0.000 description 1
• 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 230000003078 antioxidant effect Effects 0.000 description 1
• 230000036506 anxiety Effects 0.000 description 1
• 229940112930 apidra Drugs 0.000 description 1
• RCHHVVGSTHAVPF-ZPHPLDECSA-N apidra 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=3N=CNC=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](CCC(O)=O)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](CCCCN)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CNC=N1 RCHHVVGSTHAVPF-ZPHPLDECSA-N 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 238000003491 array Methods 0.000 description 1
• 210000001367 artery Anatomy 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• 229960005370 atorvastatin Drugs 0.000 description 1
• OIHKDDSBGJVHFZ-UHFFFAOYSA-N benzaldehyde 4-(chloromethyl)-5-methyl-2-phenyl-1,3-oxazole Chemical compound C(C1=CC=CC=C1)=O.ClCC=1N=C(OC1C)C1=CC=CC=C1 OIHKDDSBGJVHFZ-UHFFFAOYSA-N 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 229960004365 benzoic acid Drugs 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
• PNPBGYBHLCEVMK-UHFFFAOYSA-N benzylidene(dichloro)ruthenium;tricyclohexylphosphanium Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-N 0.000 description 1
• 229940125388 beta agonist Drugs 0.000 description 1
• 239000002876 beta blocker Substances 0.000 description 1
• 229940097320 beta blocking agent Drugs 0.000 description 1
• GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
• 229960000516 bezafibrate Drugs 0.000 description 1
• IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 1
• 125000002619 bicyclic group Chemical group 0.000 description 1
• 150000004283 biguanides Chemical class 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• DNDCVAGJPBKION-DOPDSADYSA-N bombesin 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=1NC2=CC=CC=C2C=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=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 description 1
• SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 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
• 244000309464 bull Species 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• GTXRYQGMNAPQDP-UHFFFAOYSA-N butyl-chloro-diphenylsilane Chemical group C=1C=CC=CC=1[Si](Cl)(CCCC)C1=CC=CC=C1 GTXRYQGMNAPQDP-UHFFFAOYSA-N 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 244000309466 calf Species 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 150000001720 carbohydrates Chemical class 0.000 description 1
• 235000014633 carbohydrates Nutrition 0.000 description 1
• 150000001721 carbon Chemical group 0.000 description 1
• HNYBJHSDNWSBDU-UHFFFAOYSA-N carbonic acid;cyclopentane Chemical compound OC(O)=O.C1CCCC1 HNYBJHSDNWSBDU-UHFFFAOYSA-N 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 210000003855 cell nucleus Anatomy 0.000 description 1
• 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
• 208000026106 cerebrovascular disease Diseases 0.000 description 1
• 238000000451 chemical ionisation Methods 0.000 description 1
• 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 description 1
• 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 229960004106 citric acid Drugs 0.000 description 1
• 229960001214 clofibrate Drugs 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
• 239000008199 coating composition Substances 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 239000013066 combination product Substances 0.000 description 1
• 229940127555 combination product Drugs 0.000 description 1
• 239000007891 compressed tablet Substances 0.000 description 1
• 208000026758 coronary atherosclerosis Diseases 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 230000009089 cytolysis Effects 0.000 description 1
• 231100000433 cytotoxic Toxicity 0.000 description 1
• 230000001472 cytotoxic effect Effects 0.000 description 1
• DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
• FSEUPUDHEBLWJY-UHFFFAOYSA-N diacetylmonoxime Chemical compound CC(=O)C(C)=NO FSEUPUDHEBLWJY-UHFFFAOYSA-N 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 229940043279 diisopropylamine Drugs 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 230000002526 effect on cardiovascular system Effects 0.000 description 1
• 238000001962 electrophoresis Methods 0.000 description 1
• 238000000132 electrospray ionisation Methods 0.000 description 1
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 201000011523 endocrine gland cancer Diseases 0.000 description 1
• 239000002158 endotoxin Substances 0.000 description 1
• 230000037149 energy metabolism Effects 0.000 description 1
• 239000002532 enzyme inhibitor Substances 0.000 description 1
• 210000002615 epidermis Anatomy 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• UTVNSHXHFRIXMM-UHFFFAOYSA-N ethyl 1-bromocyclobutane-1-carboxylate Chemical compound CCOC(=O)C1(Br)CCC1 UTVNSHXHFRIXMM-UHFFFAOYSA-N 0.000 description 1
• KSYHPKMYSPQQNU-UHFFFAOYSA-N ethyl 1-sulfanylcyclobutane-1-carboxylate Chemical compound CCOC(=O)C1(S)CCC1 KSYHPKMYSPQQNU-UHFFFAOYSA-N 0.000 description 1
• IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
• BKTKLDMYHTUESO-UHFFFAOYSA-N ethyl 2-bromo-2-phenylacetate Chemical compound CCOC(=O)C(Br)C1=CC=CC=C1 BKTKLDMYHTUESO-UHFFFAOYSA-N 0.000 description 1
• WNFUWONOILPKNX-UHFFFAOYSA-N ethyl 2-bromo-3-methylbutanoate Chemical compound CCOC(=O)C(Br)C(C)C WNFUWONOILPKNX-UHFFFAOYSA-N 0.000 description 1
• GNCLPIAYAPQPOU-UHFFFAOYSA-N ethyl 2-bromoheptanoate Chemical compound CCCCCC(Br)C(=O)OCC GNCLPIAYAPQPOU-UHFFFAOYSA-N 0.000 description 1
• ORSIRXYHFPHWTN-UHFFFAOYSA-N ethyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC ORSIRXYHFPHWTN-UHFFFAOYSA-N 0.000 description 1
• CSQHGJFWJSLRGL-UHFFFAOYSA-N ethyl 2-cyclohexyl-2-sulfanylacetate Chemical compound CCOC(=O)C(S)C1CCCCC1 CSQHGJFWJSLRGL-UHFFFAOYSA-N 0.000 description 1
• BJYGHGCEEJDHDR-UHFFFAOYSA-N ethyl 2-methyl-2-sulfanylpropanoate Chemical compound CCOC(=O)C(C)(C)S BJYGHGCEEJDHDR-UHFFFAOYSA-N 0.000 description 1
• SKZPUJNZLGMHDG-UHFFFAOYSA-N ethyl 2-phenyl-2-sulfanylacetate Chemical compound CCOC(=O)C(S)C1=CC=CC=C1 SKZPUJNZLGMHDG-UHFFFAOYSA-N 0.000 description 1
• SQQQKDHNXXPLKS-UHFFFAOYSA-N ethyl 2-sulfanylheptanoate Chemical compound CCCCCC(S)C(=O)OCC SQQQKDHNXXPLKS-UHFFFAOYSA-N 0.000 description 1
• FUTTXUAGQMGQBR-UHFFFAOYSA-N ethyl 2-sulfanylpentanoate Chemical compound CCCC(S)C(=O)OCC FUTTXUAGQMGQBR-UHFFFAOYSA-N 0.000 description 1
• XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 1
• SXCMSTGPRZRAMW-UHFFFAOYSA-N ethyl 5-methyl-2-(4-methylphenyl)-1,3-oxazole-4-carboxylate Chemical compound O1C(C)=C(C(=O)OCC)N=C1C1=CC=C(C)C=C1 SXCMSTGPRZRAMW-UHFFFAOYSA-N 0.000 description 1
• UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 1
• 229960000815 ezetimibe Drugs 0.000 description 1
• 229960001582 fenfluramine Drugs 0.000 description 1
• 229960002297 fenofibrate Drugs 0.000 description 1
• YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
• 239000012894 fetal calf serum Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 229960003765 fluvastatin Drugs 0.000 description 1
• 235000013305 food Nutrition 0.000 description 1
• 235000012041 food component Nutrition 0.000 description 1
• 239000005417 food ingredient Substances 0.000 description 1
• 230000037406 food intake Effects 0.000 description 1
• 235000012631 food intake Nutrition 0.000 description 1
• 235000019256 formaldehyde Nutrition 0.000 description 1
• 229960004279 formaldehyde Drugs 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 238000004108 freeze drying Methods 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 230000004927 fusion Effects 0.000 description 1
• 230000030136 gastric emptying Effects 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 229960003627 gemfibrozil Drugs 0.000 description 1
• 230000002068 genetic effect Effects 0.000 description 1
• 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 1
• 229960001381 glipizide Drugs 0.000 description 1
• 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 1
• 229960004666 glucagon Drugs 0.000 description 1
• 239000000174 gluconic acid Substances 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 230000009229 glucose formation Effects 0.000 description 1
• 230000004153 glucose metabolism Effects 0.000 description 1
• 230000004190 glucose uptake Effects 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 230000004116 glycogenolysis Effects 0.000 description 1
• 210000002149 gonad Anatomy 0.000 description 1
• 239000011984 grubbs catalyst Substances 0.000 description 1
• 210000003780 hair follicle Anatomy 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 230000002440 hepatic effect Effects 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
• 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
• 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
• 230000003027 hypercoagulation Effects 0.000 description 1
• 201000001421 hyperglycemia Diseases 0.000 description 1
• 208000015210 hypertensive heart disease Diseases 0.000 description 1
• 230000002218 hypoglycaemic effect Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 239000000411 inducer Substances 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 230000002458 infectious effect Effects 0.000 description 1
• 230000004968 inflammatory condition Effects 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 230000028709 inflammatory response Effects 0.000 description 1
• 239000003978 infusion fluid Substances 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 239000003999 initiator Substances 0.000 description 1
• 239000007972 injectable composition Substances 0.000 description 1
• 108700039926 insulin glulisine Proteins 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 208000028867 ischemia Diseases 0.000 description 1
• 229940045996 isethionic acid Drugs 0.000 description 1
• 239000012948 isocyanate Substances 0.000 description 1
• 150000002513 isocyanates Chemical class 0.000 description 1
• FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
• 150000002540 isothiocyanates Chemical class 0.000 description 1
• 210000001117 keloid Anatomy 0.000 description 1
• 206010023332 keratitis Diseases 0.000 description 1
• 210000003292 kidney cell Anatomy 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229940099563 lactobionic acid Drugs 0.000 description 1
• 229940039717 lanolin Drugs 0.000 description 1
• 235000019388 lanolin Nutrition 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• 201000011486 lichen planus Diseases 0.000 description 1
• 235000019421 lipase Nutrition 0.000 description 1
• 230000008604 lipoprotein metabolism Effects 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 206010025135 lupus erythematosus Diseases 0.000 description 1
• 239000002697 lyase inhibitor Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000011777 magnesium Substances 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
• 210000001161 mammalian embryo Anatomy 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 201000001441 melanoma Diseases 0.000 description 1
• 108020004999 messenger RNA Proteins 0.000 description 1
• 230000006371 metabolic abnormality Effects 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• JNCPTEDQFZOIHX-SFYZADRCSA-N methyl (1s,3r)-3-(hydroxymethyl)cyclohexane-1-carboxylate Chemical compound COC(=O)[C@H]1CCC[C@@H](CO)C1 JNCPTEDQFZOIHX-SFYZADRCSA-N 0.000 description 1
• RPTZTBUZVQPCRN-UHFFFAOYSA-N methyl 2-acetylsulfanylbutanoate Chemical compound CC(=O)SC(CC)C(=O)OC RPTZTBUZVQPCRN-UHFFFAOYSA-N 0.000 description 1
• FVRCRECNPNQSKL-UHFFFAOYSA-N methyl 2-bromo-2-cyclohexylacetate Chemical compound COC(=O)C(Br)C1CCCCC1 FVRCRECNPNQSKL-UHFFFAOYSA-N 0.000 description 1
• UFQQDNMQADCHGH-UHFFFAOYSA-N methyl 2-bromobutanoate Chemical compound CCC(Br)C(=O)OC UFQQDNMQADCHGH-UHFFFAOYSA-N 0.000 description 1
• RXVSKTQXIVIUFE-UHFFFAOYSA-N methyl 2-cyclohexyl-2-sulfanylacetate Chemical compound COC(=O)C(S)C1CCCCC1 RXVSKTQXIVIUFE-UHFFFAOYSA-N 0.000 description 1
• 229940017219 methyl propionate Drugs 0.000 description 1
• 229960001110 miglitol Drugs 0.000 description 1
• 239000007932 molded tablet Substances 0.000 description 1
• 239000002808 molecular sieve Substances 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
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
• LXEDKSZTPGCEPU-UHFFFAOYSA-N n-[2-(3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl)-1-(4-chlorophenyl)-2-oxoethyl]-1-amino-1,2,3,4-tetrahydronaphthalene-2-carboxamide Chemical compound O=C1N(C)N=C2CCN(C(=O)C(NC(=O)C3C(C4=CC=CC=C4CC3)N)C=3C=CC(Cl)=CC=3)CC21CC1=CC=CC=C1 LXEDKSZTPGCEPU-UHFFFAOYSA-N 0.000 description 1
• DIQDKUNCSVFGHH-UHFFFAOYSA-N n-[[4-[[(4-aminoquinazolin-2-yl)amino]methyl]cyclohexyl]methyl]naphthalene-1-sulfonamide;hydrochloride Chemical compound Cl.C1=CC=C2C(N)=NC(NCC3CCC(CNS(=O)(=O)C=4C5=CC=CC=C5C=CC=4)CC3)=NC2=C1 DIQDKUNCSVFGHH-UHFFFAOYSA-N 0.000 description 1
• PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• 239000002660 neuropeptide Y receptor antagonist Substances 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• 230000035764 nutrition Effects 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 108060005714 orexin Proteins 0.000 description 1
• 125000001181 organosilyl group Chemical group [SiH3]* 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
• 201000008482 osteoarthritis Diseases 0.000 description 1
• YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical compound O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
• 150000002923 oximes Chemical class 0.000 description 1
• FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
• 201000002528 pancreatic cancer Diseases 0.000 description 1
• 208000003154 papilloma Diseases 0.000 description 1
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 235000010603 pastilles Nutrition 0.000 description 1
• 230000007310 pathophysiology Effects 0.000 description 1
• 229940049954 penicillin Drugs 0.000 description 1
• 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 239000002831 pharmacologic agent Substances 0.000 description 1
• 238000005191 phase separation Methods 0.000 description 1
• 208000017983 photosensitivity disease Diseases 0.000 description 1
• 230000001766 physiological effect Effects 0.000 description 1
• 229960002797 pitavastatin Drugs 0.000 description 1
• VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
• 238000013492 plasmid preparation Methods 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 238000006116 polymerization reaction Methods 0.000 description 1
• 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
• 230000000291 postprandial effect Effects 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 159000000001 potassium salts Chemical class 0.000 description 1
• 229960002965 pravastatin Drugs 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
• 230000001737 promoting effect Effects 0.000 description 1
• UBKCIXXGQRZHRO-UHFFFAOYSA-N propan-2-yl 2-aminoacetate;hydrochloride Chemical compound Cl.CC(C)OC(=O)CN UBKCIXXGQRZHRO-UHFFFAOYSA-N 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
• 208000023958 prostate neoplasm Diseases 0.000 description 1
• 102000004169 proteins and genes Human genes 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
• 229960002354 repaglinide Drugs 0.000 description 1
• 230000010410 reperfusion Effects 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• 108091008146 restriction endonucleases Proteins 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 229960000672 rosuvastatin Drugs 0.000 description 1
• BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
• 208000008742 seborrheic dermatitis Diseases 0.000 description 1
• 230000003248 secreting effect Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 230000000862 serotonergic effect Effects 0.000 description 1
• 239000000952 serotonin receptor agonist Substances 0.000 description 1
• 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 238000007493 shaping process Methods 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
• 229960002855 simvastatin Drugs 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
• 210000003491 skin Anatomy 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 239000004059 squalene synthase inhibitor Substances 0.000 description 1
• 229960005322 streptomycin Drugs 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 230000002459 sustained effect Effects 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• RJBVJBGFJIHJSZ-ZETCQYMHSA-N tert-butyl (2s)-2-amino-3-methylbutanoate Chemical compound CC(C)[C@H](N)C(=O)OC(C)(C)C RJBVJBGFJIHJSZ-ZETCQYMHSA-N 0.000 description 1
• YCOBSJVCYBFZKU-NOOIUNMQSA-N tert-butyl (2s)-3-methyl-2-[2-[(1r,3r)-3-[[5-methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethylamino]butanoate Chemical compound C1[C@@H](CCN[C@@H](C(C)C)C(=O)OC(C)(C)C)CCC[C@H]1OCC1=C(C)OC(C=2C=C(C)C=CC=2)=N1 YCOBSJVCYBFZKU-NOOIUNMQSA-N 0.000 description 1
• NGGSNNRGSVLCHU-JKSUJKDBSA-N tert-butyl 1-[[(1s,3r)-3-(methoxymethoxy)cyclohexyl]methoxy]cyclopentane-1-carboxylate Chemical compound C1[C@H](OCOC)CCC[C@@H]1COC1(C(=O)OC(C)(C)C)CCCC1 NGGSNNRGSVLCHU-JKSUJKDBSA-N 0.000 description 1
• OHXVSPGBLXLRSQ-NEPJUHHUSA-N tert-butyl 2-[[(1s,3r)-3-(hydroxymethyl)cyclohexyl]methoxy]acetate Chemical compound CC(C)(C)OC(=O)COC[C@H]1CCC[C@@H](CO)C1 OHXVSPGBLXLRSQ-NEPJUHHUSA-N 0.000 description 1
• PABDFXJIUIZVNT-UVAYFRITSA-N tert-butyl 4-methyl-2-[2-[(1r,3r)-3-[[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethyl]pent-4-enoate Chemical compound C1[C@@H](CCC(CC(=C)C)C(=O)OC(C)(C)C)CCC[C@H]1OCC1=C(C)OC(C=2C=CC(C)=CC=2)=N1 PABDFXJIUIZVNT-UVAYFRITSA-N 0.000 description 1
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 229950004704 tesaglitazar Drugs 0.000 description 1
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 230000001732 thrombotic effect Effects 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 239000012096 transfection reagent Substances 0.000 description 1
• 238000003146 transient transfection Methods 0.000 description 1
• 150000003626 triacylglycerols Chemical class 0.000 description 1
• GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 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 1
• 229960001641 troglitazone Drugs 0.000 description 1
• 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 1
• 210000001635 urinary tract Anatomy 0.000 description 1
• 210000003462 vein Anatomy 0.000 description 1
• SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1