DE1301433B - Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus Valerianaceae - Google Patents
Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus ValerianaceaeInfo
- Publication number
- DE1301433B DE1301433B DEP1717101.6-4A DEK0055025A DE1301433B DE 1301433 B DE1301433 B DE 1301433B DE K0055025 A DEK0055025 A DE K0055025A DE 1301433 B DE1301433 B DE 1301433B
- Authority
- DE
- Germany
- Prior art keywords
- isovaleric acid
- ester
- acid ester
- group
- solvents
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 5
- 241000792902 Valerianaceae Species 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 title 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical class CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 16
- -1 isovaleric acid ester Chemical class 0.000 claims description 14
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 6
- 238000010828 elution Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 239000010696 ester oil Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 2
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 244000126014 Valeriana officinalis Species 0.000 description 2
- 235000013832 Valeriana officinalis Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000016788 valerian Nutrition 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 241000606265 Valeriana jatamansi Species 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/84—Valerianaceae (Valerian family), e.g. valerian
-
- 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
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Alternative & Traditional Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP1717101.6-4A DE1301433B (de) | 1965-01-15 | 1965-01-15 | Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus Valerianaceae |
| GB46666A GB1091695A (en) | 1965-01-15 | 1966-01-05 | Therapeutically active compounds obtainable from valerianaceae |
| IL2493866A IL24938A (en) | 1965-01-15 | 1966-01-07 | Cyclopentano(c)-dihydropyran derivatives obtainable from valerianaceae |
| FI10166A FI44003B (xx) | 1965-01-15 | 1966-01-14 | |
| SE51966A SE349940B (xx) | 1965-01-15 | 1966-01-14 | |
| BE675165D BE675165A (xx) | 1965-01-15 | 1966-01-14 | |
| NL6600501A NL141186B (nl) | 1965-01-15 | 1966-01-14 | Werkwijze voor het winnen van therapeutisch werkzame isovaleriaanzuurersters en voor het bereiden van een of beide esters bevattende farmaceutische preparaten, alsmede aldus verkregen gevormde preparaten. |
| NO16124866A NO116435B (xx) | 1965-01-15 | 1966-01-14 | |
| DK21166A DK115347B (da) | 1965-01-15 | 1966-01-14 | Fremgangsmåde til udvinding af terapeutisk aktive isovalerianesyreestere. |
| BR17641566A BR6676415D0 (pt) | 1965-01-15 | 1966-01-14 | Processo para a obtencao de esteres isovalerianicos terapeuticamente eficazes de valerianaceas |
| FR46027A FR5640M (xx) | 1965-01-15 | 1966-01-15 | |
| CH58466A CH530979A (de) | 1965-01-15 | 1966-01-17 | Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus Valerianaceae |
| NO16973967A NO117492B (xx) | 1965-01-15 | 1967-09-14 | |
| SE731/68A SE343211B (xx) | 1965-01-15 | 1968-01-19 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP1717101.6-4A DE1301433B (de) | 1965-01-15 | 1965-01-15 | Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus Valerianaceae |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1301433B true DE1301433B (de) | 1969-08-21 |
Family
ID=7227325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP1717101.6-4A Pending DE1301433B (de) | 1965-01-15 | 1965-01-15 | Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus Valerianaceae |
Country Status (12)
| Country | Link |
|---|---|
| BE (1) | BE675165A (xx) |
| BR (1) | BR6676415D0 (xx) |
| CH (1) | CH530979A (xx) |
| DE (1) | DE1301433B (xx) |
| DK (1) | DK115347B (xx) |
| FI (1) | FI44003B (xx) |
| FR (1) | FR5640M (xx) |
| GB (1) | GB1091695A (xx) |
| IL (1) | IL24938A (xx) |
| NL (1) | NL141186B (xx) |
| NO (2) | NO116435B (xx) |
| SE (2) | SE349940B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5211948A (en) * | 1988-10-12 | 1993-05-18 | Nestec S.A. | Process for the preparation of a powdered extract of valerian roots |
| IE61919B1 (en) * | 1988-10-12 | 1994-11-30 | Nestle Sa | "Process for the preparation of a powdered extract of valerian roots" |
-
1965
- 1965-01-15 DE DEP1717101.6-4A patent/DE1301433B/de active Pending
-
1966
- 1966-01-05 GB GB46666A patent/GB1091695A/en not_active Expired
- 1966-01-07 IL IL2493866A patent/IL24938A/xx unknown
- 1966-01-14 BE BE675165D patent/BE675165A/xx not_active IP Right Cessation
- 1966-01-14 FI FI10166A patent/FI44003B/fi active
- 1966-01-14 NL NL6600501A patent/NL141186B/xx not_active IP Right Cessation
- 1966-01-14 NO NO16124866A patent/NO116435B/no unknown
- 1966-01-14 SE SE51966A patent/SE349940B/xx unknown
- 1966-01-14 DK DK21166A patent/DK115347B/da unknown
- 1966-01-14 BR BR17641566A patent/BR6676415D0/pt unknown
- 1966-01-15 FR FR46027A patent/FR5640M/fr not_active Expired
- 1966-01-17 CH CH58466A patent/CH530979A/de not_active IP Right Cessation
-
1967
- 1967-09-14 NO NO16973967A patent/NO117492B/no unknown
-
1968
- 1968-01-19 SE SE731/68A patent/SE343211B/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| NO116435B (xx) | 1969-03-24 |
| NO117492B (xx) | 1969-08-18 |
| SE349940B (xx) | 1972-10-16 |
| SE343211B (xx) | 1972-03-06 |
| FR5640M (xx) | 1967-12-26 |
| BR6676415D0 (pt) | 1973-09-06 |
| DK115347B (da) | 1969-09-29 |
| GB1091695A (en) | 1967-11-22 |
| CH530979A (de) | 1972-11-30 |
| BE675165A (xx) | 1966-05-03 |
| NL6600501A (xx) | 1966-07-18 |
| FI44003B (xx) | 1971-04-30 |
| IL24938A (en) | 1969-11-30 |
| NL141186B (nl) | 1974-02-15 |
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