BE441861A - - Google Patents

Info

Publication number

BE441861A

BE441861A BE441861DA BE441861A BE 441861 A BE441861 A BE 441861A BE 441861D A BE441861D A BE 441861DA BE 441861 A BE441861 A BE 441861A

Authority

BE

Belgium

Prior art keywords

pantothenic acid

quinine

salt

salts

cinchonidine

Prior art date

Links

• Espacenet
• Global Dossier
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• LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 18
• 239000011780 sodium chloride Substances 0.000 claims description 18
• KMPWYEUPVWOPIM-KODHJQJWSA-N Cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 claims description 16
• FAPWYRCQGJNNSJ-UBKPKTQASA-L calcium D-pantothenic acid Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UBKPKTQASA-L 0.000 claims description 15
• 229960002079 calcium pantothenate Drugs 0.000 claims description 15
• 239000011713 pantothenic acid Substances 0.000 claims description 15
• 235000019161 pantothenic acid Nutrition 0.000 claims description 11
• GHOKWGTUZJEAQD-ZETCQYMHSA-N pantothenic acid Natural products OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims description 9
• 235000001258 Cinchona calisaya Nutrition 0.000 claims description 8
• 241000434299 Cinchona officinalis Species 0.000 claims description 8
• 229940055726 Pantothenic Acid Drugs 0.000 claims description 8
• 229960000948 Quinine Drugs 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 8
• GHOKWGTUZJEAQD-UHFFFAOYSA-N Pantothenic acid Chemical compound OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 3
• 150000007513 acids Chemical class 0.000 claims description 2
• 238000001640 fractional crystallisation Methods 0.000 claims description 2
• 238000000034 method Methods 0.000 claims description 2
• 239000000126 substance Substances 0.000 claims description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
• 239000000243 solution Substances 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
• TZCXTZWJZNENPQ-UHFFFAOYSA-L Barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 5
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
• 229910052601 baryte Inorganic materials 0.000 description 4
• 239000010428 baryte Substances 0.000 description 4
• 239000000203 mixture Substances 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• 229910052788 barium Inorganic materials 0.000 description 3
• DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 150000002948 pantothenic acids Chemical class 0.000 description 3
• 239000006188 syrup Substances 0.000 description 3
• 235000020357 syrup Nutrition 0.000 description 3
• 239000001576 FEMA 2977 Substances 0.000 description 2
• 229960003110 Quinine Sulfate Drugs 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 159000000009 barium salts Chemical class 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000005712 crystallization Effects 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 230000001264 neutralization Effects 0.000 description 2
• 229940014662 pantothenate Drugs 0.000 description 2
• -1 pantothenate ion Chemical class 0.000 description 2
• RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 230000002194 synthesizing Effects 0.000 description 2
• WBBHOISPYYYBTC-FNGHZUEVSA-N (R)-[(2S,5S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C([C@H]([C@H]3N4CCC([C@@H](C4)C=C)C3)O)=CC=NC2=C1.C1=CC=C2C([C@H]([C@H]3N4CCC([C@@H](C4)C=C)C3)O)=CC=NC2=C1 WBBHOISPYYYBTC-FNGHZUEVSA-N 0.000 description 1
• RRKTZKIUPZVBMF-IBTVXLQLSA-N Brucine Chemical class O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
• 206010016256 Fatigue Diseases 0.000 description 1
• KJFMBFZCATUALV-UHFFFAOYSA-N Phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
• 230000001476 alcoholic Effects 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 150000003797 alkaloid derivatives Chemical class 0.000 description 1
• 229930013930 alkaloids Natural products 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 235000019658 bitter taste Nutrition 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 125000004432 carbon atoms Chemical group C* 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 230000005591 charge neutralization Effects 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• 239000000727 fraction Substances 0.000 description 1
• 150000002596 lactones Chemical class 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 230000003287 optical Effects 0.000 description 1
• GHOKWGTUZJEAQD-UHFFFAOYSA-M pantothenate Chemical compound OCC(C)(C)C(O)C(=O)NCCC([O-])=O GHOKWGTUZJEAQD-UHFFFAOYSA-M 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
• 235000011121 sodium hydroxide Nutrition 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 235000019156 vitamin B Nutrition 0.000 description 1
• 239000011720 vitamin B Substances 0.000 description 1