DE3544457A1 - Arzneimittel zur behandlung von leberkrankheiten - Google Patents
Arzneimittel zur behandlung von leberkrankheitenInfo
- Publication number
- DE3544457A1 DE3544457A1 DE19853544457 DE3544457A DE3544457A1 DE 3544457 A1 DE3544457 A1 DE 3544457A1 DE 19853544457 DE19853544457 DE 19853544457 DE 3544457 A DE3544457 A DE 3544457A DE 3544457 A1 DE3544457 A1 DE 3544457A1
- Authority
- DE
- Germany
- Prior art keywords
- biflavanoids
- biflavanoid
- ethyl acetate
- nuts
- active ingredient
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000003814 drug Substances 0.000 title claims abstract description 21
- 208000019423 liver disease Diseases 0.000 title claims description 8
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- 229940079593 drug Drugs 0.000 claims description 11
- 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 description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 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 claims description 9
- 229950000628 silibinin Drugs 0.000 claims description 9
- 235000014899 silybin Nutrition 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000469 ethanolic extract Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002024 ethyl acetate extract Substances 0.000 claims 2
- 235000010205 Cola acuminata Nutrition 0.000 claims 1
- 244000228088 Cola acuminata Species 0.000 claims 1
- 235000015438 Cola nitida Nutrition 0.000 claims 1
- 241001207047 Garcinia afzelii Species 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 210000003494 hepatocyte Anatomy 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 6
- 230000006819 RNA synthesis Effects 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 238000001243 protein synthesis Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 230000014616 translation Effects 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241001207073 Garcinia kola Species 0.000 description 3
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 208000006454 hepatitis Diseases 0.000 description 2
- 231100000283 hepatitis Toxicity 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000007449 liver function test Methods 0.000 description 2
- 230000007257 malfunction Effects 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 208000030090 Acute Disease Diseases 0.000 description 1
- 241000546193 Clusiaceae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000320380 Silybum Species 0.000 description 1
- 235000010841 Silybum marianum Nutrition 0.000 description 1
- 229920004482 WACKER® Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000004251 balanced diet Nutrition 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 239000002021 butanolic extract Substances 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000007946 flavonol Chemical class 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853544457 DE3544457A1 (de) | 1985-12-16 | 1985-12-16 | Arzneimittel zur behandlung von leberkrankheiten |
| EP19870900127 EP0250508A1 (fr) | 1985-12-16 | 1986-12-16 | Medicament pour le traitement des maladies du foie |
| PCT/EP1986/000751 WO1987003590A1 (fr) | 1985-12-16 | 1986-12-16 | Medicament pour le traitement des maladies du foie |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853544457 DE3544457A1 (de) | 1985-12-16 | 1985-12-16 | Arzneimittel zur behandlung von leberkrankheiten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3544457A1 true DE3544457A1 (de) | 1987-06-19 |
Family
ID=6288568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853544457 Withdrawn DE3544457A1 (de) | 1985-12-16 | 1985-12-16 | Arzneimittel zur behandlung von leberkrankheiten |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0250508A1 (fr) |
| DE (1) | DE3544457A1 (fr) |
| WO (1) | WO1987003590A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5773462A (en) * | 1995-06-23 | 1998-06-30 | Medichem Research, Inc. | Biflavanoids and derivatives thereof as antiviral agents |
| US6399654B1 (en) | 1995-06-23 | 2002-06-04 | Advanced Life Sciences, Inc. | Biflavanoids and derivatives thereof as antiviral agents |
| US6677350B1 (en) | 1999-09-22 | 2004-01-13 | Advanced Life Sciences, Inc. | Beta-fluoroethyl thiourea compounds and use |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115894424B (zh) * | 2023-01-06 | 2023-05-12 | 中日友好医院(中日友好临床医学研究所) | 新型双黄酮类化合物及其制备方法、药物组合物和应用 |
-
1985
- 1985-12-16 DE DE19853544457 patent/DE3544457A1/de not_active Withdrawn
-
1986
- 1986-12-16 EP EP19870900127 patent/EP0250508A1/fr not_active Withdrawn
- 1986-12-16 WO PCT/EP1986/000751 patent/WO1987003590A1/fr not_active Ceased
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5773462A (en) * | 1995-06-23 | 1998-06-30 | Medichem Research, Inc. | Biflavanoids and derivatives thereof as antiviral agents |
| US5948918A (en) * | 1995-06-23 | 1999-09-07 | Medichem Research, Inc. | Biflavanoids and derivatives thereof as antiviral agents |
| US6399654B1 (en) | 1995-06-23 | 2002-06-04 | Advanced Life Sciences, Inc. | Biflavanoids and derivatives thereof as antiviral agents |
| US6677350B1 (en) | 1999-09-22 | 2004-01-13 | Advanced Life Sciences, Inc. | Beta-fluoroethyl thiourea compounds and use |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1987003590A1 (fr) | 1987-06-18 |
| EP0250508A1 (fr) | 1988-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |