AU616367B2 - Ginkgolide derivatives - Google Patents
Ginkgolide derivatives Download PDFInfo
- Publication number
- AU616367B2 AU616367B2 AU24644/88A AU2464488A AU616367B2 AU 616367 B2 AU616367 B2 AU 616367B2 AU 24644/88 A AU24644/88 A AU 24644/88A AU 2464488 A AU2464488 A AU 2464488A AU 616367 B2 AU616367 B2 AU 616367B2
- Authority
- AU
- Australia
- Prior art keywords
- ginkgolide
- alkoxy
- mixture
- ginkgolides
- diazoalkane
- 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.)
- Ceased
Links
- 229930184727 ginkgolide Natural products 0.000 title claims description 25
- 238000000034 method Methods 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical group C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000011369 resultant mixture Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 claims 1
- 235000009917 Crataegus X brevipes Nutrition 0.000 claims 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 claims 1
- 235000009685 Crataegus X maligna Nutrition 0.000 claims 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 claims 1
- 235000009486 Crataegus bullatus Nutrition 0.000 claims 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 claims 1
- 235000009682 Crataegus limnophila Nutrition 0.000 claims 1
- 235000004423 Crataegus monogyna Nutrition 0.000 claims 1
- 240000000171 Crataegus monogyna Species 0.000 claims 1
- 235000002313 Crataegus paludosa Nutrition 0.000 claims 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 210000002837 heart atrium Anatomy 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 206010006482 Bronchospasm Diseases 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- SQOJOAFXDQDRGF-WJHVHIKBSA-N ginkgolide B Natural products O=C1[C@@H](C)[C@@]2(O)[C@@H]([C@H](O)[C@]34[C@@H]5OC(=O)[C@]23O[C@H]2OC(=O)[C@H](O)[C@@]42[C@H](C(C)(C)C)C5)O1 SQOJOAFXDQDRGF-WJHVHIKBSA-N 0.000 description 5
- 230000007885 bronchoconstriction Effects 0.000 description 4
- 238000010253 intravenous injection Methods 0.000 description 4
- AMOGMTLMADGEOQ-FNZROXQESA-N Ginkgolide C Chemical compound O([C@H]1O2)C(=O)[C@H](O)C31[C@]14[C@@H](O)[C@@H]5OC(=O)[C@@H](C)[C@]5(O)[C@@]12C(=O)O[C@@H]4[C@@H](O)[C@H]3C(C)(C)C AMOGMTLMADGEOQ-FNZROXQESA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- FPUXKXIZEIDQKW-MFJLLLFKSA-N ginkgolide A Natural products O=C1[C@H](C)[C@@]2(O)[C@@H](O1)C[C@]13[C@@H]4OC(=O)[C@]21O[C@@H]1OC(=O)[C@H](O)[C@]31[C@@H](C(C)(C)C)C4 FPUXKXIZEIDQKW-MFJLLLFKSA-N 0.000 description 3
- AMOGMTLMADGEOQ-DPFZUGDXSA-N ginkgolide C Natural products O=C1[C@@H](C)[C@]2(O)[C@H]([C@H](O)[C@@]34[C@H]5[C@H](O)[C@@H](C(C)(C)C)[C@]63[C@H](O)C(=O)O[C@H]6O[C@@]24C(=O)O5)O1 AMOGMTLMADGEOQ-DPFZUGDXSA-N 0.000 description 3
- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000283977 Oryctolagus Species 0.000 description 2
- 108010003541 Platelet Activating Factor Proteins 0.000 description 2
- 208000009144 Pure autonomic failure Diseases 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- LMEHVEUFNRJAAV-HOSIAMDISA-N ginkgolide J Natural products O=C1[C@H](C)[C@@]2(O)[C@H](O1)C[C@@]13[C@H]4[C@@H](O)[C@@H](C(C)(C)C)[C@@]51[C@@H](O)C(=O)O[C@@H]5O[C@@]23C(=O)O4 LMEHVEUFNRJAAV-HOSIAMDISA-N 0.000 description 2
- SQOJOAFXDQDRGF-MMQTXUMRSA-N ginkgolide-b Chemical compound O[C@H]([C@]12[C@H](C(C)(C)C)C[C@H]3OC4=O)C(=O)O[C@H]2O[C@]24[C@@]13[C@@H](O)[C@@H]1OC(=O)[C@@H](C)[C@]21O SQOJOAFXDQDRGF-MMQTXUMRSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- -1 1-ethoxy Ginkgolide A Chemical compound 0.000 description 1
- 208000033399 Anaphylactic responses Diseases 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- YZXBAPSDXZZRGB-DOFZRALJSA-M Arachidonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O YZXBAPSDXZZRGB-DOFZRALJSA-M 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- CBAUUWCEZZNYTD-OOWJTCQTSA-N Ginkgolide M Natural products O=C1[C@@H](C)[C@@H]2[C@@H]([C@@H](O)[C@@]34[C@H]5[C@@H](O)[C@@H](CC(C)C)[C@@]63[C@@H](O)C(=O)O[C@@H]6O[C@@]24C(=O)O5)O1 CBAUUWCEZZNYTD-OOWJTCQTSA-N 0.000 description 1
- KDKROYXEHCYLJQ-DYXVGVPESA-N Ginkgolide M Chemical compound C[C@H]1[C@H]2[C@H]([C@@H](C34[C@]25C(=O)O[C@@H]3[C@@H]([C@H](C46[C@H](C(=O)O[C@H]6O5)O)C(C)(C)C)O)O)OC1=O KDKROYXEHCYLJQ-DYXVGVPESA-N 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 230000007503 antigenic stimulation Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229940114078 arachidonate Drugs 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- FPUXKXIZEIDQKW-VKMVSBOZSA-N ginkgolide-a Chemical compound O[C@H]([C@]12[C@H](C(C)(C)C)C[C@H]3OC4=O)C(=O)O[C@H]2O[C@]24[C@@]13C[C@@H]1OC(=O)[C@@H](C)[C@]21O FPUXKXIZEIDQKW-VKMVSBOZSA-N 0.000 description 1
- LMEHVEUFNRJAAV-UKWFQYJJSA-N ginkgolide-j Chemical compound O([C@H]1O2)C(=O)[C@H](O)[C@@]31[C@]14C[C@@H]5OC(=O)[C@@H](C)[C@]5(O)[C@@]12C(=O)O[C@@H]4[C@H](O)[C@H]3C(C)(C)C LMEHVEUFNRJAAV-UKWFQYJJSA-N 0.000 description 1
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 201000003144 pneumothorax Diseases 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- 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
- A61K31/365—Lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878725871A GB8725871D0 (en) | 1987-11-04 | 1987-11-04 | Ginkgolide derivatives |
| GB8725871 | 1987-11-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2464488A AU2464488A (en) | 1989-05-25 |
| AU616367B2 true AU616367B2 (en) | 1991-10-24 |
Family
ID=10626449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU24644/88A Ceased AU616367B2 (en) | 1987-11-04 | 1988-11-03 | Ginkgolide derivatives |
Country Status (28)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5895785A (en) * | 1987-10-20 | 1999-04-20 | Ruth Korth | Treatment and prevention of disorders mediated by LA-paf or endothelial cells |
| DE69132379T2 (de) * | 1990-06-06 | 2001-03-01 | Ruth-Maria Korth | Behandlung von Erkrankungen mit Paf-Antagonisten und Verfahren zur Bestimmung deren Wirksamkeit |
| ES2181665T3 (es) * | 1991-11-04 | 2003-03-01 | Ruth-Maria Korth | Tratamiento y prevencion de enfermedades mentales, acompañadas por unos elevados niveles de liso paf, con los antagonistas de paf. |
| GB9408044D0 (en) * | 1994-04-22 | 1994-06-15 | Sod Conseils Rech Applic | Conversion of ginkgolide c to ginkgolide b |
| FR2763592B1 (fr) * | 1997-05-20 | 1999-07-16 | Sod Conseils Rech Applic | Nouveaux derives glycosyles des ginkgolides, leur application en tant que medicaments et compositions pharmaceutiques les contenant |
| FR2771639B1 (fr) * | 1997-12-03 | 2000-05-05 | Sod Conseils Rech Applic | Utilisation d'extraits de ginkgo biloba pour preparer un medicament destine a faciliter le sevrage d'individus dependants de la consommation d'une substance engendrant une dependance et/ou une addiction |
| FR2777280B1 (fr) * | 1998-04-10 | 2001-04-20 | Centre Nat Rech Scient | Derives de ginkgolides, leur procede de preparation et compositions pharmaceutiques les contenant |
| CN106892930B (zh) * | 2015-12-18 | 2020-02-18 | 成都百裕金阁莱药业有限公司 | 银杏内酯b衍生物及其制备方法与应用 |
| CN108373474B (zh) * | 2017-12-25 | 2020-06-09 | 上海信谊百路达药业有限公司 | 一种从银杏叶中提取的银杏内酯化合物及其制备方法 |
| CN108383852B (zh) * | 2017-12-25 | 2019-11-22 | 上海信谊百路达药业有限公司 | 一种从银杏叶中提取的银杏内酯化合物及其制备 |
| CN117567480A (zh) | 2019-04-24 | 2024-02-20 | 复旦大学 | 银杏内酯b衍生物及其盐，及其制备方法和用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8418424D0 (en) * | 1984-07-19 | 1984-08-22 | Scras | Inhibition of platelets aggregation |
| DE3710921C2 (de) * | 1986-10-21 | 1996-09-26 | Korth Ruth | Verwendung der Gingkolide BN 52020, BN 52021 und BN 52063 zur Behandlung von Arteriosklerose |
| DE3735525C2 (de) * | 1987-10-20 | 1997-02-20 | Korth Ruth Maria | Verfahren zur Bestimmung der Wirksamkeit von paf-Acether-Rezeptor-Antagonisten |
-
1987
- 1987-11-04 GB GB878725871A patent/GB8725871D0/en active Pending
-
1988
- 1988-10-24 GB GB8824859A patent/GB2211841B/en not_active Expired - Lifetime
- 1988-10-26 GR GR880100726A patent/GR1000264B/el unknown
- 1988-10-26 NL NL8802635A patent/NL8802635A/nl not_active Application Discontinuation
- 1988-10-26 IN IN928DE1988 patent/IN173404B/en unknown
- 1988-10-27 NZ NZ226738A patent/NZ226738A/xx unknown
- 1988-10-28 MY MYPI88001236A patent/MY103446A/en unknown
- 1988-10-28 BE BE8801244A patent/BE1003455A3/fr not_active IP Right Cessation
- 1988-10-31 SE SE8803931A patent/SE8803931L/xx not_active Application Discontinuation
- 1988-11-01 MA MA21665A patent/MA21423A1/fr unknown
- 1988-11-01 ZA ZA888184A patent/ZA888184B/xx unknown
- 1988-11-02 FI FI885046A patent/FI90081C/fi not_active IP Right Cessation
- 1988-11-02 ES ES8803334A patent/ES2009364A6/es not_active Expired
- 1988-11-02 AT AT0269688A patent/AT397097B/de not_active IP Right Cessation
- 1988-11-03 TN TNTNSN88118A patent/TNSN88118A1/fr unknown
- 1988-11-03 AU AU24644/88A patent/AU616367B2/en not_active Ceased
- 1988-11-03 IE IE331588A patent/IE61541B1/en not_active IP Right Cessation
- 1988-11-03 KR KR1019880014439A patent/KR970005536B1/ko not_active Expired - Lifetime
- 1988-11-03 DK DK612788A patent/DK612788A/da not_active Application Discontinuation
- 1988-11-03 PT PT88924A patent/PT88924B/pt not_active IP Right Cessation
- 1988-11-03 NO NO884900A patent/NO167739C/no unknown
- 1988-11-03 CH CH4081/88A patent/CH675583A5/fr not_active IP Right Cessation
- 1988-11-03 CA CA000582165A patent/CA1303619C/en not_active Expired - Lifetime
- 1988-11-04 DE DE3837550A patent/DE3837550A1/de active Granted
- 1988-11-04 IT IT8822493A patent/IT1227456B/it active
- 1988-11-04 JP JP63277522A patent/JPH0686455B2/ja not_active Expired - Lifetime
- 1988-11-04 FR FR888814393A patent/FR2622448B1/fr not_active Expired - Lifetime
- 1988-11-04 FR FR888814392A patent/FR2622584B1/fr not_active Expired - Lifetime
-
1992
- 1992-04-29 SG SG48292A patent/SG48292G/en unknown
- 1992-07-23 HK HK539/92A patent/HK53992A/xx not_active IP Right Cessation
Also Published As
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