MXPA04007564A - Compuestos que modulan la actividad de ppar. - Google Patents

Info

Publication number

MXPA04007564A

MXPA04007564A MXPA04007564A MXPA04007564A MXPA04007564A MX PA04007564 A MXPA04007564 A MX PA04007564A MX PA04007564 A MXPA04007564 A MX PA04007564A MX PA04007564 A MXPA04007564 A MX PA04007564A MX PA04007564 A MXPA04007564 A MX PA04007564A

Authority

MX

Mexico

Prior art keywords

methyl

compound

acid

thiazol

hydrogen

Prior art date

2002-03-07

Links

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• Global Dossier
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• 230000000694 effects Effects 0.000 title abstract description 14
• 101150014691 PPARA gene Proteins 0.000 title description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title description 2
• 150000007978 oxazole derivatives Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 528
• 238000000034 method Methods 0.000 claims abstract description 34
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 16
• 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 13
• 241000124008 Mammalia Species 0.000 claims abstract description 12
• 238000002360 preparation method Methods 0.000 claims description 164
• 239000002253 acid Substances 0.000 claims description 131
• -1 methoxy, ethoxy, isopropoxy Chemical group 0.000 claims description 112
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 110
• 239000001257 hydrogen Substances 0.000 claims description 95
• 229910052739 hydrogen Inorganic materials 0.000 claims description 95
• 125000000217 alkyl group Chemical group 0.000 claims description 76
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 60
• 150000002431 hydrogen Chemical class 0.000 claims description 50
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
• 125000003342 alkenyl group Chemical group 0.000 claims description 24
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 125000000304 alkynyl group Chemical group 0.000 claims description 24
• 125000003118 aryl group Chemical group 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• 230000002265 prevention Effects 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000001188 haloalkyl group Chemical group 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 201000001320 Atherosclerosis Diseases 0.000 claims description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 101100082497 Oryza sativa subsp. japonica PCF3 gene Proteins 0.000 claims description 6
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 3
• OYDWHPGDTLGSKX-UHFFFAOYSA-N 1-[4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenyl]cyclopentane-1-carboxylic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC(C=C1)=CC=C1C1(C(O)=O)CCCC1 OYDWHPGDTLGSKX-UHFFFAOYSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 2
• DDIWEYHLKGCWLH-UHFFFAOYSA-N 1-[4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC(C=C1)=CC=C1C1(C(O)=O)CC1 DDIWEYHLKGCWLH-UHFFFAOYSA-N 0.000 claims 1
• HQUHMUAHNKEKBE-UHFFFAOYSA-N 2-[2,5-dimethyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC1=CC(C)=C(OCC(O)=O)C=C1C HQUHMUAHNKEKBE-UHFFFAOYSA-N 0.000 claims 1
• SMLLFAYWFOGLIE-UHFFFAOYSA-N 2-[2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-phenylacetic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC(C=C1C)=CC=C1OC(C(O)=O)C1=CC=CC=C1 SMLLFAYWFOGLIE-UHFFFAOYSA-N 0.000 claims 1
• URHSUAIFIXFSFV-UHFFFAOYSA-N 2-[4-[4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenyl]cyclohexyl]acetic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC(C=C1)=CC=C1C1CCC(CC(O)=O)CC1 URHSUAIFIXFSFV-UHFFFAOYSA-N 0.000 claims 1
• JYBJPICHZOJTAF-UHFFFAOYSA-N 2-[5-chloro-2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC1=CC(C)=C(OCC(O)=O)C=C1Cl JYBJPICHZOJTAF-UHFFFAOYSA-N 0.000 claims 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 58
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 abstract description 14
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 abstract description 14
• 239000003814 drug Substances 0.000 abstract description 5
• 229940124597 therapeutic agent Drugs 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 125
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 109
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 101
• 235000019439 ethyl acetate Nutrition 0.000 description 56
• 238000005481 NMR spectroscopy Methods 0.000 description 53
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 48
• 239000000047 product Substances 0.000 description 45
• 239000000243 solution Substances 0.000 description 43
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
• 230000015572 biosynthetic process Effects 0.000 description 39
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
• 238000003786 synthesis reaction Methods 0.000 description 38
• 239000007787 solid Substances 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 27
• 238000005160 1H NMR spectroscopy Methods 0.000 description 23
• 239000003921 oil Substances 0.000 description 23
• 235000019198 oils Nutrition 0.000 description 23
• 238000000746 purification Methods 0.000 description 23
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
• 238000004440 column chromatography Methods 0.000 description 22
• 150000004702 methyl esters Chemical class 0.000 description 21
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• 239000012267 brine Substances 0.000 description 20
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
• 239000002904 solvent Substances 0.000 description 20
• JQVJAQPUFIIRJP-UHFFFAOYSA-N 5-(chloromethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound S1C(CCl)=C(C)N=C1C1=CC=C(C(F)(F)F)C=C1 JQVJAQPUFIIRJP-UHFFFAOYSA-N 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 239000012071 phase Substances 0.000 description 18
• 238000004587 chromatography analysis Methods 0.000 description 17
• 239000012043 crude product Substances 0.000 description 17
• 150000002148 esters Chemical class 0.000 description 17
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
• 239000010409 thin film Substances 0.000 description 16
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 239000012074 organic phase Substances 0.000 description 15
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical class 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 14
• 238000010828 elution Methods 0.000 description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
• 229960000583 acetic acid Drugs 0.000 description 12
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 12
• 229910000024 caesium carbonate Inorganic materials 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 12
• KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 12
• 238000001953 recrystallisation Methods 0.000 description 12
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
• 235000019341 magnesium sulphate Nutrition 0.000 description 11
• 238000010992 reflux Methods 0.000 description 11
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
• 239000008346 aqueous phase Substances 0.000 description 10
• 210000004027 cell Anatomy 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 10
• 229910052938 sodium sulfate Inorganic materials 0.000 description 10
• 235000011152 sodium sulphate Nutrition 0.000 description 10
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
• 101150041968 CDC13 gene Proteins 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
• 229910052794 bromium Inorganic materials 0.000 description 9
• 229940125797 compound 12 Drugs 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• 239000000284 extract Substances 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• 108010010234 HDL Lipoproteins Proteins 0.000 description 7
• 102000015779 HDL Lipoproteins Human genes 0.000 description 7
• 238000001816 cooling Methods 0.000 description 7
• 125000004494 ethyl ester group Chemical group 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• 208000008589 Obesity Diseases 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 6
• 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 6
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 6
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 6
• 235000020824 obesity Nutrition 0.000 description 6
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 6
• 125000001424 substituent group Chemical group 0.000 description 6
• BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 6
• 125000005309 thioalkoxy group Chemical group 0.000 description 6
• 239000003981 vehicle Substances 0.000 description 6
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 5
• IFNDEOYXGHGERA-UHFFFAOYSA-N 2-methoxy-5-methylphenol Chemical compound COC1=CC=C(C)C=C1O IFNDEOYXGHGERA-UHFFFAOYSA-N 0.000 description 5
• 239000004215 Carbon black (E152) Substances 0.000 description 5
• 108020004414 DNA Proteins 0.000 description 5
• 108010007622 LDL Lipoproteins Proteins 0.000 description 5
• 102000007330 LDL Lipoproteins Human genes 0.000 description 5
• 108060001084 Luciferase Proteins 0.000 description 5
• 239000005089 Luciferase Substances 0.000 description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
• 125000002947 alkylene group Chemical group 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 229940125904 compound 1 Drugs 0.000 description 5
• 229940125810 compound 20 Drugs 0.000 description 5
• VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 5
• 235000019441 ethanol Nutrition 0.000 description 5
• JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• 150000002430 hydrocarbons Chemical class 0.000 description 5
• 201000001421 hyperglycemia Diseases 0.000 description 5
• 208000006575 hypertriglyceridemia Diseases 0.000 description 5
• 239000004615 ingredient Substances 0.000 description 5
• WHPRHZGDPJAHHX-UHFFFAOYSA-N methyl 2-(2-methyl-5-propan-2-yl-4-thiocyanatophenoxy)acetate Chemical compound COC(=O)COC1=CC(C(C)C)=C(SC#N)C=C1C WHPRHZGDPJAHHX-UHFFFAOYSA-N 0.000 description 5
• ROEOIGUDYLCRLA-UHFFFAOYSA-N methyl 2-(4-sulfanylphenyl)cyclopropane-1-carboxylate Chemical compound COC(=O)C1CC1C1=CC=C(S)C=C1 ROEOIGUDYLCRLA-UHFFFAOYSA-N 0.000 description 5
• YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 5
• BQRFZWGTJXCXSR-UHFFFAOYSA-N methyl 2-phenylcyclopropane-1-carboxylate Chemical compound COC(=O)C1CC1C1=CC=CC=C1 BQRFZWGTJXCXSR-UHFFFAOYSA-N 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 229920001223 polyethylene glycol Polymers 0.000 description 5
• 239000011591 potassium Substances 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
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