DD258231A1 - Verfahren zur herstellung von isosilybinfreiem silibinin - Google Patents
Verfahren zur herstellung von isosilybinfreiem silibinin Download PDFInfo
- Publication number
- DD258231A1 DD258231A1 DD28304385A DD28304385A DD258231A1 DD 258231 A1 DD258231 A1 DD 258231A1 DD 28304385 A DD28304385 A DD 28304385A DD 28304385 A DD28304385 A DD 28304385A DD 258231 A1 DD258231 A1 DD 258231A1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- methanol
- ethyl acetate
- weight
- silibinin
- isosilybin
- Prior art date
Links
- SEBFKMXJBCUCAI-HKTJVKLFSA-N silibinin Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC=C(C=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-HKTJVKLFSA-N 0.000 title claims abstract description 71
- 238000004519 manufacturing process Methods 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 71
- SEBFKMXJBCUCAI-UHFFFAOYSA-N NSC 227190 Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC=C(C=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-UHFFFAOYSA-N 0.000 claims abstract description 66
- 235000014899 silybin Nutrition 0.000 claims abstract description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 229950000628 silibinin Drugs 0.000 claims abstract description 50
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000012141 concentrate Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000000843 powder Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 235000010841 Silybum marianum Nutrition 0.000 claims abstract description 7
- 244000272459 Silybum marianum Species 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000000725 suspension Substances 0.000 claims abstract description 4
- 235000011869 dried fruits Nutrition 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 12
- 235000017700 silymarin Nutrition 0.000 claims description 11
- 229960004245 silymarin Drugs 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 235000013399 edible fruits Nutrition 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000011877 solvent mixture Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 239000010685 fatty oil Substances 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000009827 uniform distribution Methods 0.000 claims 1
- FDQAOULAVFHKBX-UHFFFAOYSA-N Isosilybin A Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC(=CC=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-UHFFFAOYSA-N 0.000 abstract description 14
- FDQAOULAVFHKBX-KMRPREKFSA-N (+)-Isosilybin A Natural products C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC(=CC=C3O2)[C@@H]2[C@@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-KMRPREKFSA-N 0.000 abstract description 8
- FDQAOULAVFHKBX-HKTJVKLFSA-N (2r,3r)-3,5,7-trihydroxy-2-[(2r,3r)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC(=CC=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-HKTJVKLFSA-N 0.000 abstract description 8
- KDMGQPNVTKUNHV-UHFFFAOYSA-N Isosilybin Natural products C1=C(O)C(OC)=CC=C1C1C(CO)OC2=CC=C(C3C(C(=O)C4=C(O)C=C(O)C=C4O3)O)C=C2O1 KDMGQPNVTKUNHV-UHFFFAOYSA-N 0.000 abstract description 8
- VLGROHBNWZUINI-UHFFFAOYSA-N Silybin Natural products COc1cc(ccc1O)C2OC3C=C(C=CC3OC2CO)C4Oc5cc(O)cc(O)c5C(=O)C4O VLGROHBNWZUINI-UHFFFAOYSA-N 0.000 abstract description 6
- 229940043175 silybin Drugs 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 4
- 208000019423 liver disease Diseases 0.000 abstract description 4
- KPKZJLCSROULON-QKGLWVMZSA-N Phalloidin Chemical compound N1C(=O)[C@@H]([C@@H](O)C)NC(=O)[C@H](C)NC(=O)[C@H](C[C@@](C)(O)CO)NC(=O)[C@H](C2)NC(=O)[C@H](C)NC(=O)[C@@H]3C[C@H](O)CN3C(=O)[C@@H]1CSC1=C2C2=CC=CC=C2N1 KPKZJLCSROULON-QKGLWVMZSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 7
- 239000000902 placebo Substances 0.000 description 6
- 229940068196 placebo Drugs 0.000 description 6
- 206010067125 Liver injury Diseases 0.000 description 5
- 108010009711 Phalloidine Proteins 0.000 description 5
- 229910052777 Praseodymium Inorganic materials 0.000 description 5
- 231100000234 hepatic damage Toxicity 0.000 description 5
- 210000004185 liver Anatomy 0.000 description 5
- 230000008818 liver damage Effects 0.000 description 5
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 5
- 231100000566 intoxication Toxicity 0.000 description 4
- 230000035987 intoxication Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 208000019425 cirrhosis of liver Diseases 0.000 description 3
- 231100000572 poisoning Toxicity 0.000 description 3
- 230000000607 poisoning effect Effects 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 230000007882 cirrhosis Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- NXQJDVBMMRCKQG-UHFFFAOYSA-N 5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=CC=CC=C1 NXQJDVBMMRCKQG-UHFFFAOYSA-N 0.000 description 1
- 208000022309 Alcoholic Liver disease Diseases 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 102000015790 Asparaginase Human genes 0.000 description 1
- 108010024976 Asparaginase Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 241000320380 Silybum Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229960003272 asparaginase Drugs 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-M asparaginate Chemical compound [O-]C(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-M 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- BMLIIPOXVWESJG-LMBCONBSSA-N silychristin Chemical compound C1=C(O)C(OC)=CC([C@H]2[C@@H](C3=C(C(=CC(=C3)[C@@H]3[C@H](C(=O)C4=C(O)C=C(O)C=C4O3)O)O)O2)CO)=C1 BMLIIPOXVWESJG-LMBCONBSSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3442641 | 1984-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD258231A1 true DD258231A1 (de) | 1988-07-13 |
Family
ID=6250904
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD28304385A DD258231A1 (de) | 1984-11-22 | 1985-11-20 | Verfahren zur herstellung von isosilybinfreiem silibinin |
| DD30516385A DD262429A1 (de) | 1984-11-22 | 1985-11-20 | Verfahren zur herstellung von isosilybinfreiem silibinin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD30516385A DD262429A1 (de) | 1984-11-22 | 1985-11-20 | Verfahren zur herstellung von isosilybinfreiem silibinin |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS61197579A (enrdf_load_stackoverflow) |
| DD (2) | DD258231A1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA858935B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI529167B (zh) * | 2009-05-14 | 2016-04-11 | 歐羅梅德股份有限公司 | 用於治療病毒性肝炎之非晶型水飛薊賓 |
-
1985
- 1985-11-20 DD DD28304385A patent/DD258231A1/de not_active IP Right Cessation
- 1985-11-20 DD DD30516385A patent/DD262429A1/de not_active IP Right Cessation
- 1985-11-21 ZA ZA858935A patent/ZA858935B/xx unknown
- 1985-11-22 JP JP60261630A patent/JPS61197579A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DD262429A1 (de) | 1988-11-30 |
| JPS61197579A (ja) | 1986-09-01 |
| JPH0339506B2 (enrdf_load_stackoverflow) | 1991-06-14 |
| ZA858935B (en) | 1986-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RPV | Change in the person, the name or the address of the representative (searches according to art. 11 and 12 extension act) | ||
| ENJ | Ceased due to non-payment of renewal fee |