DD262429A1 - Verfahren zur herstellung von isosilybinfreiem silibinin - Google Patents
Verfahren zur herstellung von isosilybinfreiem silibinin Download PDFInfo
- Publication number
- DD262429A1 DD262429A1 DD30516385A DD30516385A DD262429A1 DD 262429 A1 DD262429 A1 DD 262429A1 DD 30516385 A DD30516385 A DD 30516385A DD 30516385 A DD30516385 A DD 30516385A DD 262429 A1 DD262429 A1 DD 262429A1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- weight
- ethyl acetate
- parts
- hours
- silibinin
- 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 68
- 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 64
- 235000014899 silybin Nutrition 0.000 claims abstract description 55
- 229950000628 silibinin Drugs 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000000843 powder Substances 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 244000272459 Silybum marianum Species 0.000 claims abstract description 6
- 235000010841 Silybum marianum Nutrition 0.000 claims abstract description 5
- 235000011869 dried fruits Nutrition 0.000 claims abstract description 3
- 239000011877 solvent mixture Substances 0.000 claims abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 235000017700 silymarin Nutrition 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 9
- 229960004245 silymarin Drugs 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 5
- 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
- 239000012141 concentrate Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 235000013399 edible fruits Nutrition 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 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
- 239000000706 filtrate 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
- 239000000725 suspension Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 230000009172 bursting Effects 0.000 claims 1
- 238000004090 dissolution 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 description 12
- 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
- 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 description 7
- 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 description 7
- 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 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
- VLGROHBNWZUINI-UHFFFAOYSA-N Silybin Natural products COc1cc(ccc1O)C2OC3C=C(C=CC3OC2CO)C4Oc5cc(O)cc(O)c5C(=O)C4O VLGROHBNWZUINI-UHFFFAOYSA-N 0.000 description 5
- 231100000234 hepatic damage Toxicity 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
- 229940043175 silybin Drugs 0.000 description 5
- 231100000566 intoxication Toxicity 0.000 description 4
- 230000035987 intoxication Effects 0.000 description 4
- 210000004185 liver Anatomy 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
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 208000019423 liver disease Diseases 0.000 description 3
- 231100000572 poisoning Toxicity 0.000 description 3
- 230000000607 poisoning effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000126 substance Substances 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
- 230000002440 hepatic effect Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 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
- MBBZMMPHUWSWHV-UHFFFAOYSA-N 6-(methylamino)hexane-1,2,3,4,5-pentol Chemical class CNCC(O)C(O)C(O)C(O)CO MBBZMMPHUWSWHV-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
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000001929 anti-hepatotoxic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 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
- 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
- 230000001684 chronic effect Effects 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
- 230000000694 effects Effects 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
- 239000012535 impurity Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000013067 intermediate product Substances 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
- 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
- 238000003756 stirring Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000009827 uniform distribution 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 |
|---|---|
| DD262429A1 true DD262429A1 (de) | 1988-11-30 |
Family
ID=6250904
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD30516385A DD262429A1 (de) | 1984-11-22 | 1985-11-20 | Verfahren zur herstellung von isosilybinfreiem silibinin |
| DD28304385A DD258231A1 (de) | 1984-11-22 | 1985-11-20 | Verfahren zur herstellung von isosilybinfreiem silibinin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD28304385A DD258231A1 (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) | DD262429A1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA858935B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2761656C (en) * | 2009-05-14 | 2017-02-07 | Lucio Claudio Rovati | Amorphous silibinin for the treatment of viral hepatitis |
-
1985
- 1985-11-20 DD DD30516385A patent/DD262429A1/de not_active IP Right Cessation
- 1985-11-20 DD DD28304385A patent/DD258231A1/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 |
|---|---|
| JPS61197579A (ja) | 1986-09-01 |
| DD258231A1 (de) | 1988-07-13 |
| ZA858935B (en) | 1986-08-27 |
| JPH0339506B2 (enrdf_load_stackoverflow) | 1991-06-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3940094C2 (enrdf_load_stackoverflow) | ||
| DE3537656C2 (enrdf_load_stackoverflow) | ||
| EP2192911B1 (de) | Pflanzenextrakt aus thc-armen cannabis zur behandlung von erkrankungen | |
| DE10128266A1 (de) | Verfahren zur Herstellung eines Extrakts mit starker Antiinflammations-Antiblutplättchenaggregations- und Antifungi-Aktivität aus Zingiber officinale und pharmazeutische Zusammensetzungen, die diesen Extrakt enthalten | |
| DE4013696A1 (de) | Salze des azelastins mit verbesserter loeslichkeit | |
| DE3511609C2 (enrdf_load_stackoverflow) | ||
| EP1051170A1 (de) | Verwendung von substituierten aminomethyl-chromanen zur verhinderung der neuronalen degeneration und zur förderung der neuronalen regeneration | |
| CH642085A5 (de) | Verfahren zur gewinnung der polaren fraktion mit antipsoriatischer wirksamkeit eines extraktes aus farnpflanzen sowie ein gemaess diesem verfahren hergestelltes praeparat. | |
| EP0505519B1 (de) | Kawa-kawa-extrakt, verfahren zu seiner herstellung und seine verwendung | |
| DE2451933C2 (enrdf_load_stackoverflow) | ||
| DE2112430C3 (de) | Verfahren zur Herstellung eines Arzneimittels enthaltend Wirkstoffe und coronardilatorischen und periphervasodilatorischen Eigenschaften aus Pflanzenextrakten | |
| DE19603788B4 (de) | Wirkstoffextrakt aus Teufelskrallenwurzel, diesen enthaltendes human- oder veterinärmedizinisches Präparat, Verfahren zur Herstellung eines hochkonzentrierten Extraktes aus Radix Harpagophyti oder Herba und Radix Scrophularia sowie dessen Verwendung | |
| DD262429A1 (de) | Verfahren zur herstellung von isosilybinfreiem silibinin | |
| DE2625053C3 (de) | Arzneimittel zur Kontrolle von Leberkrankheiten | |
| EP0557876B1 (de) | Verwendung von Xanthinderivaten zur Behandlung von Muskelschädigungen nach vollständiger Unterbrechung der Blutzirkulation | |
| EP0422618B1 (de) | Polysaccharide mit antiphlogistischer Wirkung, Verfahren zu ihrer Gewinnung und sie enthaltende Arzneimittel | |
| DE4021428A1 (de) | Verfahren zur herstellung eines anthelminthikums | |
| DE60133138T2 (de) | (-)-olivil als antioxidationsmittel | |
| EP1326588B1 (de) | Orale zubereitungsformen von extrakten aus boswellia | |
| DE2135492C3 (de) | Gewinnung eines Anacardhim occidentale L-Rindenextraktes mit antihypertensiver Wirkung | |
| DE69922398T2 (de) | Phenantrenderivate mit medizinischer anwendung sowie dessen herstellungsverfahren | |
| DE2930039A1 (de) | Entzuendungshemmendes mittel | |
| DE2147263C3 (enrdf_load_stackoverflow) | ||
| DE2753466A1 (de) | Verwendung von extrakten von pflanzen der art prunus | |
| DE2131946A1 (de) | Salze der Orotsaeure mit Aminoalkoholen sowie Verfahren zu deren Herstellung und Anwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |