CA2725749A1

CA2725749A1 - Novel compounds, pharmaceutical compositions containing same, and methods of use for same

Novel compounds, pharmaceutical compositions containing same, and methods of use for same Download PDF

Info

Publication number: CA2725749A1
Authority: CA; Canada
Prior art keywords: group; compound; comprised; alkyl; substituted
Prior art date: 2008-06-02
Legal status : Abandoned

Application number

CA2725749A

Other languages

English (en)

French (fr)

Inventor

Craig A. Townsend

Rajaa El Meskini

Kandasamy Subburaj

Susan Medghaichi

Jill Marie Sturdivant

Current Assignee

FASgen Inc

Original Assignee

Johns Hopkins University

FASgen Inc

Priority date

2008-06-02

Filing date

2009-06-02

Publication date

2009-12-10

2009-06-02 Application filed by Johns Hopkins University, FASgen Inc filed Critical Johns Hopkins University

2009-12-10 Publication of CA2725749A1 publication Critical patent/CA2725749A1/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 166
238000000034 method Methods 0.000 title claims description 72
239000008194 pharmaceutical composition Substances 0.000 title claims description 21
125000003118 aryl group Chemical group 0.000 claims abstract description 52
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 40
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 32
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
125000004429 atom Chemical group 0.000 claims abstract description 20
238000006467 substitution reaction Methods 0.000 claims abstract description 20
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 19
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 19
229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 16
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 8
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
108010039731 Fatty Acid Synthases Proteins 0.000 claims description 82
230000004580 weight loss Effects 0.000 claims description 33
229910052739 hydrogen Inorganic materials 0.000 claims description 26
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 25
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
125000005843 halogen group Chemical group 0.000 claims description 23
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 19
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 18
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 14
-1 N-substituted piperazine Chemical class 0.000 claims description 13
230000000694 effects Effects 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
229910006074 SO2NH2 Inorganic materials 0.000 claims description 10
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
241001465754 Metazoa Species 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
206010028980 Neoplasm Diseases 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 4
230000000813 microbial effect Effects 0.000 claims description 4
239000008024 pharmaceutical diluent Substances 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 3
230000012010 growth Effects 0.000 claims description 3
125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 8
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 8
102000015303 Fatty Acid Synthases Human genes 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
230000001939 inductive effect Effects 0.000 claims 1
102100022089 Acyl-[acyl-carrier-protein] hydrolase Human genes 0.000 description 81
101150041968 CDC13 gene Proteins 0.000 description 63
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 63
239000000243 solution Substances 0.000 description 61
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
JACYMBNQPPWQML-UHFFFAOYSA-N sodium;4-methoxy-5-[3-(2-methoxy-4-nitro-5-sulfophenyl)-5-(phenylcarbamoyl)tetrazol-3-ium-2-yl]-2-nitrobenzenesulfonate Chemical compound [Na+].COC1=CC([N+]([O-])=O)=C(S([O-])(=O)=O)C=C1N1[N+](C=2C(=CC(=C(C=2)S(O)(=O)=O)[N+]([O-])=O)OC)=NC(C(=O)NC=2C=CC=CC=2)=N1 JACYMBNQPPWQML-UHFFFAOYSA-N 0.000 description 52
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
238000005160 1H NMR spectroscopy Methods 0.000 description 36
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
239000007787 solid Substances 0.000 description 28
239000003112 inhibitor Substances 0.000 description 27
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 26
210000004027 cell Anatomy 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
102100039239 Amidophosphoribosyltransferase Human genes 0.000 description 25
108010039224 Amidophosphoribosyltransferase Proteins 0.000 description 25
239000000203 mixture Substances 0.000 description 25
229910001868 water Inorganic materials 0.000 description 24
229910052943 magnesium sulfate Inorganic materials 0.000 description 23
102000004190 Enzymes Human genes 0.000 description 21
108090000790 Enzymes Proteins 0.000 description 21
235000019341 magnesium sulphate Nutrition 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
235000019439 ethyl acetate Nutrition 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 17
239000000047 product Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 16
238000005481 NMR spectroscopy Methods 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000012043 crude product Substances 0.000 description 14
235000014113 dietary fatty acids Nutrition 0.000 description 14
239000000194 fatty acid Substances 0.000 description 14
229930195729 fatty acid Natural products 0.000 description 14
230000005764 inhibitory process Effects 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
GVEZIHKRYBHEFX-NQQPLRFYSA-N cerulenin Chemical compound C\C=C\C\C=C\CCC(=O)[C@H]1O[C@H]1C(N)=O GVEZIHKRYBHEFX-NQQPLRFYSA-N 0.000 description 12
150000004665 fatty acids Chemical class 0.000 description 12
238000003818 flash chromatography Methods 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
LTYOQGRJFJAKNA-KKIMTKSISA-N Malonyl CoA Natural products S(C(=O)CC(=O)O)CCNC(=O)CCNC(=O)[C@@H](O)C(CO[P@](=O)(O[P@](=O)(OC[C@H]1[C@@H](OP(=O)(O)O)[C@@H](O)[C@@H](n2c3ncnc(N)c3nc2)O1)O)O)(C)C LTYOQGRJFJAKNA-KKIMTKSISA-N 0.000 description 11
125000000217 alkyl group Chemical group 0.000 description 11
230000004136 fatty acid synthesis Effects 0.000 description 11
LTYOQGRJFJAKNA-DVVLENMVSA-N malonyl-CoA 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)NCCSC(=O)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 LTYOQGRJFJAKNA-DVVLENMVSA-N 0.000 description 11
239000000843 powder Substances 0.000 description 11
XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 10
230000003647 oxidation Effects 0.000 description 10
238000007254 oxidation reaction Methods 0.000 description 10
GVEZIHKRYBHEFX-MNOVXSKESA-N 13C-Cerulenin Natural products CC=CCC=CCCC(=O)[C@H]1O[C@@H]1C(N)=O GVEZIHKRYBHEFX-MNOVXSKESA-N 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
GVEZIHKRYBHEFX-UHFFFAOYSA-N caerulein A Natural products CC=CCC=CCCC(=O)C1OC1C(N)=O GVEZIHKRYBHEFX-UHFFFAOYSA-N 0.000 description 9
229950005984 cerulenin Drugs 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000003814 drug Substances 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
238000012417 linear regression Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000003981 vehicle Substances 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
235000019270 ammonium chloride Nutrition 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
239000012267 brine Substances 0.000 description 8
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
238000011534 incubation Methods 0.000 description 8
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
230000037361 pathway Effects 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
208000008589 Obesity Diseases 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
230000002255 enzymatic effect Effects 0.000 description 7
230000000670 limiting effect Effects 0.000 description 7
235000020824 obesity Nutrition 0.000 description 7
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 6
101150064015 FAS gene Proteins 0.000 description 6
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
238000003556 assay Methods 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
230000001419 dependent effect Effects 0.000 description 6
239000010410 layer Substances 0.000 description 6
244000005700 microbiome Species 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
239000008279 sol Substances 0.000 description 6
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
206010006187 Breast cancer Diseases 0.000 description 5
208000026310 Breast neoplasm Diseases 0.000 description 5
102000005870 Coenzyme A Ligases Human genes 0.000 description 5
108010011449 Long-chain-fatty-acid-CoA ligase Proteins 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
239000013641 positive control Substances 0.000 description 5
239000011343 solid material Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
NKTGCVUIESDXPU-YLEPRARLSA-N triacsin C Chemical compound CCC\C=C\C\C=C\C=C\C=N\NN=O NKTGCVUIESDXPU-YLEPRARLSA-N 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
101710104378 Putative malate oxidoreductase [NAD] Proteins 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-HQMMCQRPSA-N acetic acid Chemical compound C[14C](O)=O QTBSBXVTEAMEQO-HQMMCQRPSA-N 0.000 description 4
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
239000012346 acetyl chloride Substances 0.000 description 4
229910000024 caesium carbonate Inorganic materials 0.000 description 4
238000001816 cooling Methods 0.000 description 4
150000002085 enols Chemical class 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000012530 fluid Substances 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
238000010348 incorporation Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
APYUCYRDBYSFAB-UHFFFAOYSA-N octyl trifluoromethanesulfonate Chemical compound CCCCCCCCOS(=O)(=O)C(F)(F)F APYUCYRDBYSFAB-UHFFFAOYSA-N 0.000 description 4
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 4
230000008569 process Effects 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
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 4
239000006228 supernatant Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
YSTUPBOIUOUMHG-UHFFFAOYSA-N 2-bromo-n-(4-chlorophenyl)acetamide Chemical compound ClC1=CC=C(NC(=O)CBr)C=C1 YSTUPBOIUOUMHG-UHFFFAOYSA-N 0.000 description 3
KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 3
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 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
102100027943 Carnitine O-palmitoyltransferase 1, liver isoform Human genes 0.000 description 3
101710120614 Carnitine O-palmitoyltransferase 1, liver isoform Proteins 0.000 description 3
101710108984 Carnitine O-palmitoyltransferase 1, muscle isoform Proteins 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241000195626 Hanusia phi Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000000872 buffer Substances 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
239000008367 deionised water Substances 0.000 description 3
229910021641 deionized water Inorganic materials 0.000 description 3
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 3
229910000396 dipotassium phosphate Inorganic materials 0.000 description 3
235000019797 dipotassium phosphate Nutrition 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000011049 filling Methods 0.000 description 3
125000004438 haloalkoxy group Chemical group 0.000 description 3
IPCSVZSSVZVIGE-VPMSBSONSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCC[14C](O)=O IPCSVZSSVZVIGE-VPMSBSONSA-N 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
239000012139 lysis buffer Substances 0.000 description 3
229910001629 magnesium chloride Inorganic materials 0.000 description 3
239000000463 material Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
239000002609 medium Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
DGCISTIHJIZQDX-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(2-methyl-2-octyl-5-oxothiophen-3-yl)oxyacetamide Chemical compound CCCCCCCCC1(C)SC(=O)C=C1OCC(=O)NC1=CC=C(Cl)C=C1 DGCISTIHJIZQDX-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000002243 precursor Substances 0.000 description 3
238000010926 purge Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
150000003222 pyridines Chemical class 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
238000012360 testing method Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DJQYYYCQOZMCRC-UHFFFAOYSA-N 2-aminopropane-1,3-dithiol Chemical compound SCC(N)CS DJQYYYCQOZMCRC-UHFFFAOYSA-N 0.000 description 2
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
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