TWI441823B - Ｎ１／ｎ２－內醯胺乙醯輔酶ａ羧酶抑制劑類 - Google Patents

Info

Publication number

TWI441823B

TWI441823B TW100138909A TW100138909A TWI441823B TW I441823 B TWI441823 B TW I441823B TW 100138909 A TW100138909 A TW 100138909A TW 100138909 A TW100138909 A TW 100138909A TW I441823 B TWI441823 B TW I441823B

Authority

TW

Taiwan

Prior art keywords

mmol

reaction

carboxylic acid

etoac

nmr

Prior art date

2010-10-29

Links

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• 229940121373 acetyl-coa carboxylase inhibitor Drugs 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims description 233
• 150000003839 salts Chemical class 0.000 claims description 47
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 10
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 524
• 235000019439 ethyl acetate Nutrition 0.000 description 219
• 238000006243 chemical reaction Methods 0.000 description 203
• 239000000203 mixture Substances 0.000 description 158
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 157
• 238000005481 NMR spectroscopy Methods 0.000 description 147
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
• 239000000243 solution Substances 0.000 description 116
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 110
• 239000000543 intermediate Substances 0.000 description 107
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 99
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 90
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
• 238000000034 method Methods 0.000 description 77
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 73
• -1 pyrazolopyridyl Chemical group 0.000 description 72
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 51
• 239000003112 inhibitor Substances 0.000 description 50
• 239000002904 solvent Substances 0.000 description 50
• 239000010410 layer Substances 0.000 description 49
• 238000002360 preparation method Methods 0.000 description 40
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
• 238000003818 flash chromatography Methods 0.000 description 36
• 239000007787 solid Substances 0.000 description 35
• 238000003756 stirring Methods 0.000 description 35
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 34
• 229910052938 sodium sulfate Inorganic materials 0.000 description 34
• 235000011152 sodium sulphate Nutrition 0.000 description 34
• 239000011541 reaction mixture Substances 0.000 description 30
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
• 239000012267 brine Substances 0.000 description 28
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
• 239000007864 aqueous solution Substances 0.000 description 25
• 241001465754 Metazoa Species 0.000 description 24
• 239000002585 base Substances 0.000 description 24
• 239000012044 organic layer Substances 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
• 230000015572 biosynthetic process Effects 0.000 description 21
• 201000010099 disease Diseases 0.000 description 21
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 21
• JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1h-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical class C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 description 20
• 101000677540 Homo sapiens Acetyl-CoA carboxylase 2 Proteins 0.000 description 20
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 20
• 238000010992 reflux Methods 0.000 description 19
• 102100021641 Acetyl-CoA carboxylase 2 Human genes 0.000 description 18
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
• 239000005516 coenzyme A Substances 0.000 description 18
• 229940093530 coenzyme a Drugs 0.000 description 18
• 230000002829 reductive effect Effects 0.000 description 18
• 229920006395 saturated elastomer Polymers 0.000 description 18
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
• 239000000556 agonist Substances 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 17
• 239000002244 precipitate Substances 0.000 description 17
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• 208000008589 Obesity Diseases 0.000 description 16
• 238000004128 high performance liquid chromatography Methods 0.000 description 16
• 235000020824 obesity Nutrition 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 238000003786 synthesis reaction Methods 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 15
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
• 238000000746 purification Methods 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 101000894929 Homo sapiens Bcl-2-related protein A1 Proteins 0.000 description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 230000005764 inhibitory process Effects 0.000 description 14
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
• 235000019341 magnesium sulphate Nutrition 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
• 102000004190 Enzymes Human genes 0.000 description 13
• 108090000790 Enzymes Proteins 0.000 description 13
• 229940088598 enzyme Drugs 0.000 description 13
• 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 13
• 239000012071 phase Substances 0.000 description 13
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 102100039164 Acetyl-CoA carboxylase 1 Human genes 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical compound N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 description 11
• 206010022489 Insulin Resistance Diseases 0.000 description 11
• 239000002253 acid Substances 0.000 description 11
• 238000004458 analytical method Methods 0.000 description 11
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 11
• QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 11
• 125000001072 heteroaryl group Chemical group 0.000 description 11
• 101710190443 Acetyl-CoA carboxylase 1 Proteins 0.000 description 10
• RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 10
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
• 239000005557 antagonist Substances 0.000 description 10
• 239000003472 antidiabetic agent Substances 0.000 description 10
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 10
• 150000001733 carboxylic acid esters Chemical class 0.000 description 10
• RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 10
• 230000008878 coupling Effects 0.000 description 10
• 238000010168 coupling process Methods 0.000 description 10
• 238000005859 coupling reaction Methods 0.000 description 10
• KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 10
• 125000005843 halogen group Chemical group 0.000 description 10
• 210000004185 liver Anatomy 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• 235000017557 sodium bicarbonate Nutrition 0.000 description 10
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
• 238000010561 standard procedure Methods 0.000 description 10
• 125000001424 substituent group Chemical group 0.000 description 10
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 9
• 238000010511 deprotection reaction Methods 0.000 description 9
• 206010012601 diabetes mellitus Diseases 0.000 description 9
• 239000003814 drug Substances 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 239000000284 extract Substances 0.000 description 9
• 230000002440 hepatic effect Effects 0.000 description 9
• 239000012948 isocyanate Substances 0.000 description 9
• 229910052757 nitrogen Inorganic materials 0.000 description 9
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• 229960000583 acetic acid Drugs 0.000 description 8
• 229940125708 antidiabetic agent Drugs 0.000 description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• 239000001257 hydrogen Substances 0.000 description 8
• 229910052739 hydrogen Inorganic materials 0.000 description 8
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
• 125000001624 naphthyl group Chemical group 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• 210000001519 tissue Anatomy 0.000 description 8
• 239000003643 water by type Substances 0.000 description 8
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
• 125000000217 alkyl group Chemical group 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 235000014113 dietary fatty acids Nutrition 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 239000000194 fatty acid Substances 0.000 description 7
• 229930195729 fatty acid Natural products 0.000 description 7
• 150000004665 fatty acids Chemical class 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 7
• 230000014759 maintenance of location Effects 0.000 description 7
• 238000007254 oxidation reaction Methods 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 239000000523 sample Substances 0.000 description 7
• 239000012453 solvate Substances 0.000 description 7
• 241000894007 species Species 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 6
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• 101000963424 Homo sapiens Acetyl-CoA carboxylase 1 Proteins 0.000 description 6
• 241000124008 Mammalia Species 0.000 description 6
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• 239000012190 activator Substances 0.000 description 6
• 235000019270 ammonium chloride Nutrition 0.000 description 6
• 239000012491 analyte Substances 0.000 description 6
• 239000000010 aprotic solvent Substances 0.000 description 6
• 229910002091 carbon monoxide Inorganic materials 0.000 description 6
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 6
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 6
• 208000035475 disorder Diseases 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 239000012458 free base Substances 0.000 description 6
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• 238000004519 manufacturing process Methods 0.000 description 6
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• 229960005489 paracetamol Drugs 0.000 description 6
• 108090000765 processed proteins & peptides Proteins 0.000 description 6
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 6
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
• 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 6
• 239000003039 volatile agent Substances 0.000 description 6
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 5
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
• 239000007821 HATU Substances 0.000 description 5
• 208000001145 Metabolic Syndrome Diseases 0.000 description 5
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 5
• 102000001708 Protein Isoforms Human genes 0.000 description 5
• 108010029485 Protein Isoforms Proteins 0.000 description 5
• 239000007983 Tris buffer Substances 0.000 description 5
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 5
• 239000000908 ammonium hydroxide Substances 0.000 description 5
• 239000000883 anti-obesity agent Substances 0.000 description 5
• 229940125710 antiobesity agent Drugs 0.000 description 5
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 5
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
• 229910000024 caesium carbonate Inorganic materials 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 239000012141 concentrate Substances 0.000 description 5
• 235000008504 concentrate Nutrition 0.000 description 5
• 239000013078 crystal Substances 0.000 description 5
• 238000010828 elution Methods 0.000 description 5
• 238000010438 heat treatment Methods 0.000 description 5
• 102000047784 human ACACB Human genes 0.000 description 5
• 238000005984 hydrogenation reaction Methods 0.000 description 5
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