DD126705B1 - Verfahren zur herstellung pharmazeutisch verwendbare dehydrocholsaure - Google Patents

Info

Publication number

DD126705B1

DD126705B1 DD19360076A DD19360076A DD126705B1 DD 126705 B1 DD126705 B1 DD 126705B1 DD 19360076 A DD19360076 A DD 19360076A DD 19360076 A DD19360076 A DD 19360076A DD 126705 B1 DD126705 B1 DD 126705B1

Authority

DD

German Democratic Republic

Prior art keywords

acid

item

carried out

pharmaceutically acceptable

dehydrogenation

Prior art date

1976-06-28

Links

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• Global Dossier
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• OHXPGWPVLFPUSM-KLRNGDHRSA-N 3,7,12-trioxo-5beta-cholanic acid Chemical compound C1CC(=O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)C(=O)C[C@@H]3[C@]21C OHXPGWPVLFPUSM-KLRNGDHRSA-N 0.000 title description 15
• 229960002997 dehydrocholic acid Drugs 0.000 title description 15
• 238000004519 manufacturing process Methods 0.000 title description 3
• KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 31
• BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 17
• 239000004380 Cholic acid Substances 0.000 claims description 17
• 229960002471 cholic acid Drugs 0.000 claims description 17
• 235000019416 cholic acid Nutrition 0.000 claims description 17
• BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims description 16
• KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 14
• 229960003964 deoxycholic acid Drugs 0.000 claims description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
• 238000000034 method Methods 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 9
• 239000000243 solution Substances 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 238000006356 dehydrogenation reaction Methods 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 239000000460 chlorine Substances 0.000 claims description 5
• 239000000203 mixture Substances 0.000 claims description 5
• 230000018044 dehydration Effects 0.000 claims description 4
• 238000006297 dehydration reaction Methods 0.000 claims description 4
• 239000007800 oxidant agent Substances 0.000 claims description 4
• 238000006243 chemical reaction Methods 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• 239000002904 solvent Substances 0.000 claims description 3
• -1 aliphatic fatty acids Chemical class 0.000 claims description 2
• 239000007864 aqueous solution Substances 0.000 claims description 2
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
• 229930195729 fatty acid Natural products 0.000 claims description 2
• 239000000194 fatty acid Substances 0.000 claims description 2
• 238000000926 separation method Methods 0.000 description 6
• 238000003756 stirring Methods 0.000 description 4
• 150000001875 compounds Chemical class 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
• 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
• 239000003613 bile acid Substances 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• 241000490229 Eucephalus Species 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 210000000941 bile Anatomy 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 125000003716 cholic acid group Chemical group 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 238000011403 purification operation Methods 0.000 description 1
• 238000004064 recycling Methods 0.000 description 1
• 238000001226 reprecipitation Methods 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1