JPS6067491A - 純粋なヘレブリンの製造法 - Google Patents

純粋なヘレブリンの製造法

Info

Publication number: JPS6067491A
Authority: JP; Japan
Prior art keywords: mixture; water; alkanol; ethanol; acetone
Prior art date: 1982-05-11
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.): Granted

Application number

JP58172367A

Other languages

English (en)

Japanese (ja)

Other versions

JPS64400B2 (2

Inventor

ゲルハルト・エーペン

カール‐ハインツ・マンガルツ

ノルベルト・ザイフリート

ユルゲン・エンゲル

オツトー・イザーク

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Evonik Operations GmbH

Original Assignee

Degussa GmbH

Deutsche Gold und Silber Scheideanstalt

Priority date (The priority date 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 date listed.)

1982-05-11

Filing date

1983-09-20

Publication date

1985-04-17

1983-09-20 Application filed by Degussa GmbH, Deutsche Gold und Silber Scheideanstalt filed Critical Degussa GmbH

1985-04-17 Publication of JPS6067491A publication Critical patent/JPS6067491A/ja

1989-01-06 Publication of JPS64400B2 publication Critical patent/JPS64400B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
DCSLTSSPIJWEJN-UHFFFAOYSA-N (3beta,5beta)-3-[(6-deoxy-4-O-beta-D-glucopyranosyl-alpha-L-mannopyranosyl)oxy]-5,14-dihydroxy-19-oxo-bufa-20,22-dienolide Natural products OC1C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(C)OC1OC(CC1(O)CCC2C3(O)CC4)CCC1(C=O)C2CCC3(C)C4C=1C=CC(=O)OC=1 DCSLTSSPIJWEJN-UHFFFAOYSA-N 0.000 title description 8
DCSLTSSPIJWEJN-YRFFWODSSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-3-[(2r,3r,4s,5r,6s)-3,4-dihydroxy-6-methyl-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[ Chemical compound C=1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C=O)CC[C@@H](C[C@@]5(O)CC[C@H]4[C@@]3(O)CC2)O[C@@H]2O[C@H]([C@@H]([C@@H](O)[C@H]2O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C)C=CC(=O)OC=1 DCSLTSSPIJWEJN-YRFFWODSSA-N 0.000 title description 8
FUTYDOSGHYCQGU-UHFFFAOYSA-N Hellebrin Natural products CC1OC(OC2CCC3(C=O)C4CCC5(C)C(CCC5(O)C4CCC3(O)C2)C6=COC(=O)C=C6)C(OC7OC(CO)C(O)C(O)C7O)C(O)C1O FUTYDOSGHYCQGU-UHFFFAOYSA-N 0.000 title description 8
239000000203 mixture Substances 0.000 claims description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
239000000284 extract Substances 0.000 claims description 27
238000000605 extraction Methods 0.000 claims description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 21
229960001701 chloroform Drugs 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
150000008282 halocarbons Chemical class 0.000 claims description 9
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 7
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 7
229950005499 carbon tetrachloride Drugs 0.000 claims description 6
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 5
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims description 4
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
239000012676 herbal extract Substances 0.000 claims description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 2
239000012071 phase Substances 0.000 description 59
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000003860 storage Methods 0.000 description 7
229940079593 drug Drugs 0.000 description 6
239000003814 drug Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000000926 separation method Methods 0.000 description 5
241000206389 Helleborus Species 0.000 description 4
239000000499 gel Substances 0.000 description 4
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 4
235000012239 silicon dioxide Nutrition 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000011282 treatment Methods 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 3
239000003245 coal Substances 0.000 description 3
239000000469 ethanolic extract Substances 0.000 description 3
229930182470 glycoside Natural products 0.000 description 3
150000002338 glycosides Chemical class 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000002245 particle Substances 0.000 description 3
239000004033 plastic Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
239000004809 Teflon Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000005238 degreasing Methods 0.000 description 2
238000010586 diagram Methods 0.000 description 2
241000411851 herbal medicine Species 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
239000011148 porous material Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
-1 zolonosonol Chemical compound 0.000 description 2
YGLMVCVJLXREAK-MTVMDMGHSA-N 1,1-dimethyl-3-[(1S,2R,6R,7S,8R)-8-tricyclo[5.2.1.02,6]decanyl]urea Chemical compound C([C@H]12)CC[C@@H]1[C@@H]1C[C@@H](NC(=O)N(C)C)[C@H]2C1 YGLMVCVJLXREAK-MTVMDMGHSA-N 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
240000001879 Digitalis lutea Species 0.000 description 1
244000094788 Dombeya wallichii Species 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
240000000249 Morus alba Species 0.000 description 1
235000008708 Morus alba Nutrition 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000002156 adsorbate Substances 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
229940097217 cardiac glycoside Drugs 0.000 description 1
239000002368 cardiac glycoside Substances 0.000 description 1
QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012632 extractable Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
230000005484 gravity Effects 0.000 description 1
210000003128 head Anatomy 0.000 description 1
238000000622 liquid--liquid extraction Methods 0.000 description 1
238000011068 loading method Methods 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
241000894007 species Species 0.000 description 1
230000003068 static effect Effects 0.000 description 1
229930002534 steroid glycoside Natural products 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
- C07J19/005—Glycosides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Saccharide Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP58172367A 1982-05-11 1983-09-20 純粋なヘレブリンの製造法 Granted JPS6067491A (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/377,251 US4435563A (en)	1982-05-11	1982-05-11	Process for the recovery of pure hellebrin

Publications (2)

Publication Number	Publication Date
JPS6067491A true JPS6067491A (ja)	1985-04-17
JPS64400B2 JPS64400B2 (2)	1989-01-06

Family

ID=23488362

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58172367A Granted JPS6067491A (ja)	1982-05-11	1983-09-20	純粋なヘレブリンの製造法

Country Status (4)

Country	Link
US (1)	US4435563A (2)
JP (1)	JPS6067491A (2)
AT (1)	AT382878B (2)
CA (1)	CA1202298A (2)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4590264A (en) *	1983-02-18	1986-05-20	Wofor Ag	Lipoglycosides and process of extracting same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE605073C (de)	1933-06-25	1934-11-03	Hoffmanni La Roche & Co Akt Ge	Verfahren zur Darstellung eines hochwirksamen Glucosides aus Helleborus niger, L.
FR2100367A5 (2)	1970-07-31	1972-03-17	Degussa
FR2137397B1 (2)	1971-05-12	1973-05-25	Degussa

1982
- 1982-05-11 US US06/377,251 patent/US4435563A/en not_active Expired - Fee Related
1983
- 1983-09-06 AT AT0317883A patent/AT382878B/de active
- 1983-09-20 JP JP58172367A patent/JPS6067491A/ja active Granted
- 1983-09-30 CA CA000438051A patent/CA1202298A/en not_active Expired

Also Published As

Publication number	Publication date
US4435563A (en)	1984-03-06
CA1202298A (en)	1986-03-25
ATA317883A (de)	1986-09-15
JPS64400B2 (2)	1989-01-06
AT382878B (de)	1987-04-27

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