BE625212A

BE625212A -

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Publication number: BE625212A
Authority: BE; Belgium
Prior art keywords: solution; water; acid; radical; added
Prior art date

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English (en)

French (fr)

Publication of BE625212A publication Critical patent/BE625212A/fr

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239000000243 solution Substances 0.000 description 84
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
239000002253 acid Substances 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate 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
239000000203 mixture Substances 0.000 description 22
150000001875 compounds Chemical class 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000007864 aqueous solution Substances 0.000 description 16
DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 15
238000000034 method Methods 0.000 description 13
235000011121 sodium hydroxide Nutrition 0.000 description 13
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 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
239000011734 sodium Substances 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
229930003451 Vitamin B1 Natural products 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
229960003495 thiamine Drugs 0.000 description 9
239000011691 vitamin B1 Substances 0.000 description 9
235000010374 vitamin B1 Nutrition 0.000 description 9
238000001816 cooling Methods 0.000 description 8
239000003921 oil Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
-1 ethane-sulfonyl-thio Chemical group 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical group [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
239000011707 mineral Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
150000003573 thiols Chemical class 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
229910052783 alkali metal Inorganic materials 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
GTQXMAIXVFLYKF-UHFFFAOYSA-N thiochrome Chemical compound CC1=NC=C2CN3C(C)=C(CCO)SC3=NC2=N1 GTQXMAIXVFLYKF-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
239000000470 constituent Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
230000001376 precipitating effect Effects 0.000 description 3
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
235000019345 sodium thiosulphate Nutrition 0.000 description 3
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
229940088594 vitamin Drugs 0.000 description 3
229930003231 vitamin Natural products 0.000 description 3
235000013343 vitamin Nutrition 0.000 description 3
239000011782 vitamin Substances 0.000 description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
JGHZJRVDZXSNKQ-UHFFFAOYSA-N methyl octanoate Chemical compound CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
239000003760 tallow Substances 0.000 description 2
150000003722 vitamin derivatives Chemical class 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
KGSSUZBQZIYTSL-UHFFFAOYSA-N CCC(CCCCC(OC)=[S+]I)C(C)=O Chemical compound CCC(CCCCC(OC)=[S+]I)C(C)=O KGSSUZBQZIYTSL-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
239000005641 Methyl octanoate Substances 0.000 description 1
101100014660 Rattus norvegicus Gimap8 gene Proteins 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
229930003270 Vitamin B Natural products 0.000 description 1
YXIVSUKSBCFYFO-UHFFFAOYSA-N [K].II Chemical compound [K].II YXIVSUKSBCFYFO-UHFFFAOYSA-N 0.000 description 1
YGXVNFMRNNRJJE-UHFFFAOYSA-N [Na].CCCCCCC Chemical compound [Na].CCCCCCC YGXVNFMRNNRJJE-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000004347 all-trans-retinol derivatives Chemical class 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
210000000601 blood cell Anatomy 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003518 caustics Substances 0.000 description 1
229950001485 cocarboxylase Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002195 fatty ethers Chemical class 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
101150043924 metXA gene Proteins 0.000 description 1
UVRXKLLZNMROGK-UHFFFAOYSA-N methyl 6-acetylsulfanyloctanoate Chemical compound CC(=O)SC(CC)CCCCC(=O)OC UVRXKLLZNMROGK-UHFFFAOYSA-N 0.000 description 1
231100000957 no side effect Toxicity 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229940005657 pyrophosphoric acid Drugs 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
YXVCLPJQTZXJLH-UHFFFAOYSA-N thiamine(1+) diphosphate chloride Chemical compound [Cl-].CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N YXVCLPJQTZXJLH-UHFFFAOYSA-N 0.000 description 1
125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1
235000019156 vitamin B Nutrition 0.000 description 1
239000011720 vitamin B Substances 0.000 description 1