CH530979A - Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus Valerianaceae - Google Patents
Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus ValerianaceaeInfo
- Publication number
- CH530979A CH530979A CH58466A CH58466A CH530979A CH 530979 A CH530979 A CH 530979A CH 58466 A CH58466 A CH 58466A CH 58466 A CH58466 A CH 58466A CH 530979 A CH530979 A CH 530979A
- Authority
- CH
- Switzerland
- Prior art keywords
- isovaleric acid
- ester
- isovaleric
- acid esters
- lipophilic solvents
- Prior art date
Links
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical class CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 241000792902 Valerianaceae Species 0.000 title claims description 6
- 239000000284 extract Substances 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 4
- -1 isovaleryloxy group Chemical group 0.000 claims description 26
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 239000003929 acidic solution Substances 0.000 claims description 5
- 241000196324 Embryophyta Species 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical class [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 claims description 2
- 239000000341 volatile oil Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims 2
- 239000002253 acid Substances 0.000 abstract description 2
- 238000004587 chromatography analysis Methods 0.000 abstract description 2
- 230000001624 sedative effect Effects 0.000 abstract description 2
- 241000792914 Valeriana Species 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 235000014593 oils and fats Nutrition 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 235000017468 valeriana Nutrition 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 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
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal 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
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000016788 valerian Nutrition 0.000 description 2
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- 101000884271 Homo sapiens Signal transducer CD24 Proteins 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 102100038081 Signal transducer CD24 Human genes 0.000 description 1
- 241000606265 Valeriana jatamansi Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000002955 isolation Methods 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 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)
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 |
|---|---|
| CH530979A true CH530979A (de) | 1972-11-30 |
Family
ID=7227325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH58466A CH530979A (de) | 1965-01-15 | 1966-01-17 | Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus Valerianaceae |
Country Status (12)
| Country | Link |
|---|---|
| BE (1) | BE675165A (en)van) |
| BR (1) | BR6676415D0 (en)van) |
| CH (1) | CH530979A (en)van) |
| DE (1) | DE1301433B (en)van) |
| DK (1) | DK115347B (en)van) |
| FI (1) | FI44003B (en)van) |
| FR (1) | FR5640M (en)van) |
| GB (1) | GB1091695A (en)van) |
| IL (1) | IL24938A (en)van) |
| NL (1) | NL141186B (en)van) |
| NO (2) | NO116435B (en)van) |
| SE (2) | SE349940B (en)van) |
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 DK DK21166A patent/DK115347B/da unknown
- 1966-01-14 BR BR17641566A patent/BR6676415D0/pt unknown
- 1966-01-14 BE BE675165D patent/BE675165A/xx not_active IP Right Cessation
- 1966-01-14 NO NO16124866A patent/NO116435B/no unknown
- 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 SE SE51966A patent/SE349940B/xx 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
Also Published As
| Publication number | Publication date |
|---|---|
| BR6676415D0 (pt) | 1973-09-06 |
| BE675165A (en)van) | 1966-05-03 |
| DE1301433B (de) | 1969-08-21 |
| NL141186B (nl) | 1974-02-15 |
| NO116435B (en)van) | 1969-03-24 |
| NL6600501A (en)van) | 1966-07-18 |
| NO117492B (en)van) | 1969-08-18 |
| SE349940B (en)van) | 1972-10-16 |
| GB1091695A (en) | 1967-11-22 |
| FI44003B (en)van) | 1971-04-30 |
| SE343211B (en)van) | 1972-03-06 |
| DK115347B (da) | 1969-09-29 |
| FR5640M (en)van) | 1967-12-26 |
| IL24938A (en) | 1969-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2760006C2 (de) | Optisch aktive Norpinanone und Verfahren zu ihrer Herstellung | |
| DE2532000A1 (de) | Aliphatische carbonsaeureester von vitamin e und verfahren zu ihrer herstellung | |
| DE2356655C3 (de) | Substituierte Phenoxy-α-methylpropionsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE1191515B (de) | Verfahren zur Gewinnung von sedativ und spasmolytisch wirksamen Estern aus Radix valerianae | |
| CH530979A (de) | Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus Valerianaceae | |
| DE2456082B2 (de) | Substituierte Phenoxyäthanolester, Verfahren zu deren Herstellung und Schädlingsbekämpfungsmittel | |
| AT261109B (de) | Verfahren zur Gewinnung von therapeutisch wirksamen Verbindungen aus Valerianaceae | |
| DE2129507B2 (de) | Verfahren zur Herstellung von 8-AIkoxy-3halogenmethyl-4-acetoxy- 10-methylen-2,9dioxatricyclo(43,l,03-7 )decanen | |
| DE2046904A1 (de) | Indohzinessigsauren und Verfahren zu ihrer Herstellung | |
| DE1005956B (de) | Verfahren zur Herstellung von Vitamin A bzw. dessen Estern | |
| DE2019835B2 (de) | Verfahren zur Gewinnung von Solanesol | |
| DE1793478A1 (de) | Alisol-Verbindungen | |
| DE2700341A1 (de) | Oxo-c-ring-benzopyrane | |
| CH653334A5 (de) | Verfahren zur herstellung von vinkaminsaeureestern. | |
| DE724268C (de) | Verfahren zur Herstellung eines reinen ª‡-Tokopherolesters bzw. von reinem ª‡-Tokopherol | |
| DE705312C (de) | Verfahren zur Herstellung des Wirkstoffes aus hydriertem Tachysterin | |
| DE825686C (de) | Verfahren zur UEberfuehrung von í¸-20-Cyanpregnenen mit einer oder mehreren kerngebundenen Hydroxylgruppen in 17 alpha-Oxy-20-ketopregnane | |
| DE611390C (de) | Verfahren zum Herstellen einer photographischen Gelatinehalogensilberemulsion | |
| DE873700C (de) | Verfahren zur Darstellung von Androstenol-(17)-onen-(3) bzw. deren Derivaten | |
| DE1936695C3 (de) | 2-n-PropyI-5-thiazolcarbonsäure, ihre Salze und Ester, Verfahren zu deren Herstellung sowie therapeutische Zusammensetzungen | |
| DE1618728C (de) | Verfahren zur Gewinnung von Isoprenylalkoholen mit 9,11 und 12 Isopreneinheiten | |
| DE806036C (de) | Verfahren zur Herstellung von Penicillinsalzen | |
| DE752752C (de) | Verfahren zur Herstellung von im Ring A aromatisierten Steroidverbindungen | |
| DE1002337C2 (de) | Verfahren zur Herstellung von Hydrophenanthrylcarbonsaeuren | |
| AT253677B (de) | Verfahren zur Isolierung eines zentral sedativ wirkenden Isovaleriansäureesters aus nicht wässerigen Baldrianextrakten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |