BE558480A - - Google Patents

Info

Publication number

BE558480A

BE558480A BE558480DA BE558480A BE 558480 A BE558480 A BE 558480A BE 558480D A BE558480D A BE 558480DA BE 558480 A BE558480 A BE 558480A

Authority

BE

Belgium

Prior art keywords

compounds

oxo

dehydro

hydroxy

residue

Prior art date

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 claims description 25
• 150000002148 esters Chemical class 0.000 claims description 14
• JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 12
• 238000000034 method Methods 0.000 claims description 8
• 108090000790 Enzymes Proteins 0.000 claims description 7
• 102000004190 Enzymes Human genes 0.000 claims description 7
• 125000004432 carbon atoms Chemical group C* 0.000 claims description 7
• 241000233866 Fungi Species 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 238000005658 halogenation reaction Methods 0.000 claims description 5
• 229910052744 lithium Inorganic materials 0.000 claims description 5
• 230000000694 effects Effects 0.000 claims description 4
• BUGBHKTXTAQXES-UHFFFAOYSA-N selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 4
• 150000003343 selenium compounds Chemical class 0.000 claims description 4
• 229940065287 selenium compounds Drugs 0.000 claims description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 3
• 125000005466 alkylenyl group Chemical group 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 150000004820 halides Chemical class 0.000 claims description 3
• -1 isoprop6nyl Chemical group 0.000 claims description 3
• 150000007530 organic bases Chemical group 0.000 claims description 3
• 230000001131 transforming Effects 0.000 claims description 3
• 239000000460 chlorine Substances 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 150000002081 enamines Chemical class 0.000 claims description 2
• 229910052751 metal Inorganic materials 0.000 claims description 2
• 239000002184 metal Substances 0.000 claims description 2
• 150000002739 metals Chemical class 0.000 claims description 2
• 230000000737 periodic Effects 0.000 claims description 2
• 239000000843 powder Substances 0.000 claims description 2
• 229910052711 selenium Inorganic materials 0.000 claims description 2
• 239000011669 selenium Substances 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
• 241000223600 Alternaria Species 0.000 claims 1
• 241000228438 Bipolaris maydis Species 0.000 claims 1
• 241000555695 Didymella Species 0.000 claims 1
• 241000190509 Ophiobolus Species 0.000 claims 1
• 230000001476 alcoholic Effects 0.000 claims 1
• 150000001336 alkenes Chemical group 0.000 claims 1
• 238000005695 dehalogenation reaction Methods 0.000 claims 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
• 238000004362 fungal culture Methods 0.000 claims 1
• 229910052736 halogen Inorganic materials 0.000 claims 1
• 150000002367 halogens Chemical group 0.000 claims 1
• 125000005394 methallyl group Chemical group 0.000 claims 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
• 239000000243 solution Substances 0.000 description 31
• XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 238000003756 stirring Methods 0.000 description 11
• 229960000583 Acetic Acid Drugs 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
• 238000009835 boiling Methods 0.000 description 9
• 239000012362 glacial acetic acid Substances 0.000 description 9
• 239000000203 mixture Substances 0.000 description 9
• PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• 229910052938 sodium sulfate Inorganic materials 0.000 description 7
• 235000011152 sodium sulphate Nutrition 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• MSXVEPNJUHWQHW-UHFFFAOYSA-N Tert-Amyl alcohol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 235000019441 ethanol Nutrition 0.000 description 6
• 238000001704 evaporation Methods 0.000 description 6
• 238000002844 melting Methods 0.000 description 6
• 238000001953 recrystallisation Methods 0.000 description 6
• 238000000926 separation method Methods 0.000 description 6
• 239000000284 extract Substances 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 238000002425 crystallisation Methods 0.000 description 4
• 230000005712 crystallization Effects 0.000 description 4
• 239000012452 mother liquor Substances 0.000 description 4
• 229910052757 nitrogen Inorganic materials 0.000 description 4
• OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
• 239000007795 chemical reaction product Substances 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
• 230000000875 corresponding Effects 0.000 description 3
• 239000001257 hydrogen Substances 0.000 description 3
• 229910052739 hydrogen Inorganic materials 0.000 description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
• 229910052753 mercury Inorganic materials 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• 150000002902 organometallic compounds Chemical class 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• 239000012047 saturated solution Substances 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• 239000002904 solvent Substances 0.000 description 3
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
• 101710008973 CAP01 Proteins 0.000 description 2
• WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
• 241000201940 Oena Species 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• 101710006037 SRV2 Proteins 0.000 description 2
• VWDWKYIASSYTQR-UHFFFAOYSA-N Sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• 238000007792 addition Methods 0.000 description 2
• XHODMTAOVMFHQJ-UHFFFAOYSA-N aluminum;propan-2-ol Chemical compound [Al].CC(C)O XHODMTAOVMFHQJ-UHFFFAOYSA-N 0.000 description 2
• 230000001195 anabolic Effects 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
• 239000012141 concentrate Substances 0.000 description 2
• 238000000354 decomposition reaction Methods 0.000 description 2
• 238000006356 dehydrogenation reaction Methods 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 238000003379 elimination reaction Methods 0.000 description 2
• 239000008103 glucose Substances 0.000 description 2
• 238000005984 hydrogenation reaction Methods 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• 239000000155 melt Substances 0.000 description 2
• 230000001264 neutralization Effects 0.000 description 2
• 235000015097 nutrients Nutrition 0.000 description 2
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• 230000001568 sexual Effects 0.000 description 2
• 239000001187 sodium carbonate Substances 0.000 description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 description 2
• DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N testosterone group Chemical group [C@@H]12CC[C@H](O)[C@@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
• QRRSHRVKVLSFQS-UHFFFAOYSA-N 1-ethylcyclohexane-1-carboxylic acid Chemical compound CCC1(C(O)=O)CCCCC1 QRRSHRVKVLSFQS-UHFFFAOYSA-N 0.000 description 1
• OVXJWSYBABKZMD-UHFFFAOYSA-N 2-chloro-1,1-diethoxyethane Chemical class CCOC(CCl)OCC OVXJWSYBABKZMD-UHFFFAOYSA-N 0.000 description 1
• 241000198597 Alternaria passiflorae Species 0.000 description 1
• UYJXRRSPUVSSMN-UHFFFAOYSA-P Ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
• 206010003549 Asthenia Diseases 0.000 description 1
• 241001273385 Boeremia lycopersici Species 0.000 description 1
• RSIHSRDYCUFFLA-DYKIIFRCSA-N Boldenone Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 RSIHSRDYCUFFLA-DYKIIFRCSA-N 0.000 description 1
• LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
• 241000577959 Calonectria Species 0.000 description 1
• 229940041514 Candida albicans extract Drugs 0.000 description 1
• JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
• FXHOOIRPVKKKFG-UHFFFAOYSA-N DMA Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
• 241001268392 Dalla Species 0.000 description 1
• FGPGANCDNDLUST-CEGNMAFCSA-N Ethyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](CC)(O)[C@@]1(C)CC2 FGPGANCDNDLUST-CEGNMAFCSA-N 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
• 240000007842 Glycine max Species 0.000 description 1
• 235000010469 Glycine max Nutrition 0.000 description 1
• 229940093915 Gynecological Organic acids Drugs 0.000 description 1
• GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 description 1
• 229940061634 Magnesium sulfate heptahydrate Drugs 0.000 description 1
• 239000001888 Peptone Substances 0.000 description 1
• 108010080698 Peptones Proteins 0.000 description 1
• 229940066779 Peptones Drugs 0.000 description 1
• 229940107700 Pyruvic Acid Drugs 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• 210000003371 Toes Anatomy 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• ADTNAQKEGWXKCL-UHFFFAOYSA-O acetohydrazide;pyridin-1-ium Chemical compound CC(=O)NN.C1=CC=[NH+]C=C1 ADTNAQKEGWXKCL-UHFFFAOYSA-O 0.000 description 1
• 150000001339 alkali metal compounds Chemical class 0.000 description 1
• 239000006286 aqueous extract Substances 0.000 description 1
• 229910052786 argon Inorganic materials 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 125000004429 atoms Chemical group 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 238000005893 bromination reaction Methods 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 239000003610 charcoal Substances 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
• 229910052804 chromium Inorganic materials 0.000 description 1
• 239000011651 chromium Substances 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 235000005824 corn Nutrition 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 201000010099 disease Diseases 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 150000004674 formic acids Chemical class 0.000 description 1
• 230000004927 fusion Effects 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 150000002430 hydrocarbons Chemical group 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
• VXNJNMSEJLGMFP-UHFFFAOYSA-N isopropenyllithium Chemical compound [Li]C(C)=C VXNJNMSEJLGMFP-UHFFFAOYSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 229910001641 magnesium iodide Inorganic materials 0.000 description 1
• WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
• FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
• YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
• 230000002503 metabolic Effects 0.000 description 1
• 230000002906 microbiologic Effects 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
• 229940113083 morpholine Drugs 0.000 description 1
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
• 239000003921 oil Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
• 235000019319 peptone Nutrition 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 229910003446 platinum oxide Inorganic materials 0.000 description 1
• 230000002980 postoperative Effects 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 235000011056 potassium acetate Nutrition 0.000 description 1
• 239000001103 potassium chloride Substances 0.000 description 1
• 235000011164 potassium chloride Nutrition 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 230000035935 pregnancy Effects 0.000 description 1
• 239000003380 propellant Substances 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 239000004317 sodium nitrate Substances 0.000 description 1
• 235000010344 sodium nitrate Nutrition 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 230000002522 swelling Effects 0.000 description 1
• 239000003760 tallow Substances 0.000 description 1
• 230000001225 therapeutic Effects 0.000 description 1
• 101710040762 topB Proteins 0.000 description 1
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
• GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000012138 yeast extract Substances 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1