NO135344B - - Google Patents
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- NO135344B NO135344B NO2993/72A NO299372A NO135344B NO 135344 B NO135344 B NO 135344B NO 2993/72 A NO2993/72 A NO 2993/72A NO 299372 A NO299372 A NO 299372A NO 135344 B NO135344 B NO 135344B
- Authority
- NO
- Norway
- Prior art keywords
- extraction
- dopa
- growth
- plant
- water
- Prior art date
Links
- 238000000605 extraction Methods 0.000 claims description 39
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 25
- 241000196324 Embryophyta Species 0.000 claims description 22
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 22
- 230000012010 growth Effects 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 240000006677 Vicia faba Species 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 235000002096 Vicia faba var. equina Nutrition 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 230000009105 vegetative growth Effects 0.000 claims description 4
- 235000010749 Vicia faba Nutrition 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 159000000014 iron salts Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006872 enzymatic polymerization reaction Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 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)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/28—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (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)
- Extraction Or Liquid Replacement (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Plant Substances (AREA)
Description
Foreliggende oppfinnelse angår en fremgangsmåte for ekstrahering av 3- (3,4-dihydroksyfenyl)-L-alanin (L-dopa) fra heste-bønner (Vicia faba). L-dopa er en kjemisk forbindelse som er relativt vanlig forekommende i dyrevev og vekster. Den er terapeutisk virksom mot Parkinsons sykdom og anvendes for behandling av denne. L-dopa er tidligere ekstrahert fra malte frø av hes.tebønnen i fortynnet svovelsyrling eller fortynnede vannoppløsninger av organiske syrer, hvorefter den er separert fra den erholdte ekstrakt. The present invention relates to a method for extracting 3-(3,4-dihydroxyphenyl)-L-alanine (L-dopa) from horse beans (Vicia faba). L-dopa is a chemical compound that is relatively common in animal tissues and plants. It is therapeutically effective against Parkinson's disease and is used to treat it. L-dopa has previously been extracted from ground seeds of the horse tea bean in dilute sulfuric acid or dilute aqueous solutions of organic acids, after which it is separated from the extract obtained.
Formålet med oppfinnelsen er å tilveiebringe en fremgangsmåte for ekstrahering av L-dopa fra hestbønnen, hvilken metode mul-iggjør fremstilling av L-dopa på en økonomisk fordelaktigere måte en tidligere. The purpose of the invention is to provide a method for extracting L-dopa from the horse bean, which method enables the production of L-dopa in a more economically advantageous way than before.
I henhold til oppfinnelsen tilveiebringes en fremgangsmåte According to the invention, a method is provided
til ekstrahering av 3-(3,4-dihydroksyfenyl)-L-alanin (L-dopa) fra hestebønne (Vicia faba), med vann som inneholder svovelsyrling som antioksydasjonsmiddel. Fremgangsmåten karakteriseres ved at hele vekstens vegetative vekstmasse ekstraheres i form av fersk hakkelse ved en kontinuerlig motstrømsekstraksjon under anvendelse av 1 - 2 liter vann pr. kg veksthakkelse og ved en temperatur på 70 - 80°C, for the extraction of 3-(3,4-dihydroxyphenyl)-L-alanine (L-dopa) from horse bean (Vicia faba), with water containing sulfuric acid as an antioxidant. The method is characterized by the fact that the entire plant's vegetative growth mass is extracted in the form of fresh chopping by a continuous countercurrent extraction using 1 - 2 liters of water per kg crop chop and at a temperature of 70 - 80°C,
idet ekstraksjonsvannet inneholder et egnet stoff, så som et salt av etylendiamintetraeddiksyre som kompleksdanner for eventuelt tilstedeværende jern, den ekstraherte vekstmasse sammenpresses, og den erholdte væske returneres til ekstraksjonsprosessen. as the extraction water contains a suitable substance, such as a salt of ethylenediaminetetraacetic acid which forms a complex for any iron present, the extracted growth mass is compressed, and the liquid obtained is returned to the extraction process.
For å forhindre oksydasjon av L-dopaen er det vesentlig at det til det for ekstraksjonen anvendte vann settes svovelsyrling, To prevent oxidation of the L-dopa, it is essential that sulfuric acid is added to the water used for the extraction,
samt et stoff, f.eks. et salt av etylendiamintetraeddiksyre, som danner et kompleks med eventuelt jern i ekstraksjonsoppløsningen. Jernsalter fremmer nemlig oksydasjon og polymerisasjon av L-dopa. as well as a substance, e.g. a salt of ethylenediaminetetraacetic acid, which forms a complex with any iron in the extraction solution. Namely, iron salts promote oxidation and polymerization of L-dopa.
Det er ikke tidligere gjort noen forsøk på å anvende hele No attempt has previously been made to apply the whole
den vegetative vekstmasse som utgangsmateriale for utvinning av L- the vegetative growth mass as starting material for the extraction of L-
dopa, åpenbart av den årsak at de store mengder fersk vekstmasse som er nødvendig, er vanskelige å håndtere. Hvis man ikke har en metode for rask innsamling og bearbeidning av vekstmaterialet, dopa, obviously for the reason that the large quantities of fresh growth mass required are difficult to handle. If one does not have a method for rapid collection and processing of the growing material,
blir Utbyttet dessuten dårlig, eftersom dopa raskt nedbrytes ved enzymatiske reaksjoner, polymerisasjon samt innvirkning av luftens oksygen. Hvis veksten tørkes, ødelegges tilstedeværende dopa nesten helt (Naturwissenschaften £0:57, 1953). The yield is also poor, since the dopa is quickly broken down by enzymatic reactions, polymerization and the influence of the oxygen in the air. If the growth is dried, the dopa present is almost completely destroyed (Naturwissenschaften £0:57, 1953).
Det er konstatert at hestebønnens L-dopa-innhold kan være helt opptil 0,50% av den ferske plantes vekt, eller ca. 4% av hele plantens tørrstoff. Når man som råmateriale anvender hele den vegetative vekstmasse, blir den L-dopa som utvinnes fra veksten, betraktelig billigere enn den man får med bare frøene som råstoff. It has been established that the horse bean's L-dopa content can be up to 0.50% of the weight of the fresh plant, or approx. 4% of the whole plant's dry matter. When the entire vegetative growth mass is used as raw material, the L-dopa that is extracted from the growth is considerably cheaper than that obtained with only the seeds as raw material.
Da en stor del av den L-dopa som inngår i vekstmassen, desuuten er oppløst i vekstsaften, ekstraheres den lett og nesten kvantitativt fra vekstmassen, og ekstraktens volum er bare 2-2,5 ganger større enn den opprinnelige vekstmasses volum, hvilket letter etter-behandlingen. En betraktelig økonomisk fordel ligger også deri at man til ekstraksjonsoppløsningen, dvs. vannet, i tillegg til de ovennevnte tilsetningsstoffer ikke behøver å sette noen organisk syre. Since a large part of the L-dopa that is included in the growth mass is also dissolved in the growth sap, it is easily and almost quantitatively extracted from the growth mass, and the volume of the extract is only 2-2.5 times larger than the volume of the original growth mass, which facilitates -the treatment. A considerable economic advantage also lies in the fact that, in addition to the above-mentioned additives, no organic acid needs to be added to the extraction solution, i.e. the water.
Det vekstmateriale som anvendes i henhold til fremgangsmåten, kan høstes og berges fra åkeren f.eks. med kombinert slå-/hakkelse-maskin, som skjærer ned veksten og blåser den med en luftstrøm inn i en beholder eller transportvogn hvorifra den tømmes i en transport-beholder for transport til fabrikken. The growing material used according to the method can be harvested and salvaged from the field, e.g. with a combined mowing/chopping machine, which cuts down the growth and blows it with a stream of air into a container or transport cart from which it is emptied into a transport container for transport to the factory.
Hestebønnen kan ekstraheres i et ekstraksjonsanlegg som er utviklet av De danske Sukkerfabrikker A/S for ekstraksjon av sukker fra sukkerroer skåret i skriver. Ved bearbeidning av sukkerroer er anleggets kapasitet 60 tonn/time, det er 22 m langt og har et vol- The horse bean can be extracted in an extraction plant developed by De danske Sukkerfabrikker A/S for the extraction of sugar from sugar beet cut in a press. When processing sugar beet, the plant's capacity is 60 tonnes/hour, it is 22 m long and has a vol-
um på 180 m 3 . Anlegget be"ståo r av et svakt skråonende, horisontalt trau forsynt med dobbeltspiraler, der spiralene fører vekstmassen over mens ekstraksjonsvæsken på grunn av sin egen tyngde renner ned-over gjennom massen. I den nedre ende ledes ekstraksjonsvæsken ut gjennom en silbunn. En løfteanordning overfører massen fra ekstraksjonsanleggets øvre ende til en transportanordning som fører den videre til en skruepresse med dobbeltspiral, utviklet av det norske firma Stord Barts Industri A/S. Den pressede saften føres tilbake area of 180 m 3 . The plant consists of a slightly inclined, horizontal trough equipped with double spirals, where the spirals carry the growth mass over while the extraction liquid, due to its own weight, flows downwards through the mass. At the lower end, the extraction liquid is led out through a sieve bottom. A lifting device transfers the pulp from the upper end of the extraction plant to a transport device that takes it on to a screw press with a double helix, developed by the Norwegian company Stord Barts Industri A/S. The pressed juice is fed back
til ekstraksjonsanleggets øvre ende. Temperaturen i ekstraksjonsanlegget kan forhøyes og bibeholdes.ved hjelp av termostatregulert to the upper end of the extraction plant. The temperature in the extraction system can be raised and maintained using a thermostat
damp som ledes inn i mantelen. steam that is directed into the mantle.
Vekstmassen ekstraheres i motstrøm, med så lite ekstrak-sjonsoppløsning, dvs. vann, som mulig. I alminnelighet får man en nesten kvantitativ ekstraksjon av L-dopa fra hestebønne, hvis den anvendte vannmengde i forhold til vekstmassen er 1,5 : 1. The growth mass is extracted in countercurrent, with as little extraction solution, i.e. water, as possible. In general, an almost quantitative extraction of L-dopa from horse bean is obtained if the amount of water used in relation to the growth mass is 1.5:1.
Til ekstraksjonsvannet settes svoveldioksyd for å forhindre oksydasjon av L-dopaen. Svoveldioksydet tjener samtidig som konserveringsmiddel, hvilket behøves, eftersom vekstsaft er et bra næringsmiddel for mikrober, og mikrobedannelse i ekstrakten fører til en rask nedgang i L-dopa-innholdet. Svoveldioksydet doseres ved hjelp av en pH-regulator hvis elektroder er plassert på pass-ende steder i ekstraksjonsanlegget. Sulfur dioxide is added to the extraction water to prevent oxidation of the L-dopa. The sulfur dioxide also serves as a preservative, which is needed, since plant sap is a good food source for microbes, and microbe formation in the extract leads to a rapid decrease in the L-dopa content. The sulfur dioxide is dosed using a pH regulator whose electrodes are placed in suitable places in the extraction plant.
Til ekstraks jonsvannet kan man også sette en natiriumsalt-oppløsning av etylendiamintetraeddiksyre for å. binde i et EDTA-kompleks det jern som eventuelt er tilstede i vekstmaterialet eller frigjøres fra ekstraksjonsanlegget, og derved unngå jernsaltenes katalyserende effekt på L-dopaens oksydasjon og polymerisasjon. A sodium salt solution of ethylenediaminetetraacetic acid can also be added to the extract ion water to bind in an EDTA complex the iron that may be present in the growth material or released from the extraction plant, thereby avoiding the catalytic effect of the iron salts on L-dopa's oxidation and polymerisation.
Den våte rest av vekstmassen som har passert gjennom ekstraks jonsanlegget , presses så tørr som mulig i en skruepresse eller på annen måte, og den derved erholdte væske føres tilbake til ekstraks jonsanlegget som oppløsningsmiddel. Resten av vekstmassen kan tørkes i varm luft og eventuelt anvendes som kreaturfor. The wet residue of the growth mass that has passed through the extraction plant is pressed as dry as possible in a screw press or in another way, and the resulting liquid is returned to the extraction plant as a solvent. The rest of the growing mass can be dried in hot air and possibly used as animal feed.
EKSEMPEL EXAMPLE
En hestebønne-vekstmengde på 30 000 kg pr. åkerhektar, som inneholdt 16,2% tørrstoff og 0,24% L-dopa, ble høstet og skåret med en hakkelsesmaskin i 15 mm lange biter som umiddelbart ble trans-portert med lastebil til ekstraksjonsanlegget slik at det gikk høyst 4 5 minutter fra vekstene ble høstet til hakkelsen ble ekstrahert. Ekstraksjonen ble utført som en kontinuerlig motstrømsekstraksjon A horse bean growth quantity of 30,000 kg per hectare, which contained 16.2% dry matter and 0.24% L-dopa, was harvested and cut with a chipper into 15 mm long pieces which were immediately transported by truck to the extraction plant so that it took no more than 4 5 minutes from the crops was harvested until the chips were extracted. The extraction was carried out as a continuous countercurrent extraction
i et anlegg som er utviklet av De danske Sukkerfabrikker A/S og som opprinnelig var tenkt for ekstraksjon av sukker fra sukkerroeskiver. Den finhakkede vekstmassen ble innmatet i ekstraksjonsanlegget via in a plant developed by De danske Sukkerfabrikker A/S and which was originally intended for the extraction of sugar from sugar beet slices. The finely chopped growth mass was fed into the extraction plant via
et transportbånd med en middelshastighet av 30,5 tonn i timen. Samtidig ble det tilført ekstraksjonsvann i en middelmengde på 34 tonn i timen. Til ekstraksjonsvannet ble satt svoveldioksyd og natrium-salt av etylendiamintetraeddiksyre. Svoveldioksydet ble dosert ved hjelp av en pH-stat slik at ekstraksjonsoppløsningens pH var 3,0. Na-EDTA, 0,056% av den anvendte vannmengde, ble satt i fast form di-rekte til ekstraksjonsanlegget ved hjelp av en vibrasjonsmater. a conveyor belt with an average speed of 30.5 tonnes per hour. At the same time, extraction water was added in an average amount of 34 tonnes per hour. Sulfur dioxide and sodium salt of ethylenediaminetetraacetic acid were added to the extraction water. The sulfur dioxide was dosed using a pH meter so that the pH of the extraction solution was 3.0. Na-EDTA, 0.056% of the amount of water used, was added in solid form directly to the extraction plant by means of a vibrating feeder.
Temperaturen i ekstraksjonsanlegget var maksimalt 75°C, og den ut-strømmende ekstraksjonsvæskens middeltemperatur var 47°C. Resten av vekstmassen som hadde passert gjennom ekstraksjonsanlegget, The temperature in the extraction plant was a maximum of 75°C, and the average temperature of the exiting extraction liquid was 47°C. The rest of the growth mass that had passed through the extraction plant,
ble presset i en skruepresse, og den derved erholdte væske ble matet pånytt sammen med friskt vann til ekstraksjonsanlegget. was pressed in a screw press, and the resulting liquid was fed again together with fresh water to the extraction plant.
Av 305 tonn finhakkede hestebønneplanter fikk man på denne måte 450 tonn ekstrakt hvis L-dopa-innhold var' 0,18%. L-dopa kan derefter isoleres fra ekstrakten f.eks. som be-skrevet i dansk patent 129.907. From 305 tonnes of finely chopped horse bean plants, 450 tonnes of extract were obtained in this way, whose L-dopa content was 0.18%. L-dopa can then be isolated from the extract, e.g. as described in Danish patent 129,907.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI712421A FI47629C (en) | 1971-08-30 | 1971-08-30 | Process for extracting 3- (3,4-dihydroxyphenyl) -L-alanine from pea plants. |
Publications (2)
Publication Number | Publication Date |
---|---|
NO135344B true NO135344B (en) | 1976-12-20 |
NO135344C NO135344C (en) | 1977-03-30 |
Family
ID=8507076
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO2993/72A NO135344C (en) | 1971-08-30 | 1972-08-21 | PROCEDURES FOR EXTRACTING 3- (3,4-DIHYDROXYPHENYL) -L-ALANINE FROM HORSEBREED. |
Country Status (13)
Country | Link |
---|---|
JP (1) | JPS4835019A (en) |
AT (1) | AT318135B (en) |
BE (1) | BE788178A (en) |
CA (1) | CA979007A (en) |
DE (1) | DE2241390A1 (en) |
DK (1) | DK130452B (en) |
ES (1) | ES405706A1 (en) |
FI (1) | FI47629C (en) |
FR (1) | FR2151898A5 (en) |
GB (1) | GB1377675A (en) |
NL (1) | NL7211294A (en) |
NO (1) | NO135344C (en) |
SE (1) | SE393600B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50147042A (en) * | 1974-05-16 | 1975-11-26 | ||
ES2548804B1 (en) * | 2014-03-20 | 2016-09-06 | Consejo Superior De Investigaciones Científicas (Csic) | PROCEDURE FOR OBTAINING AMINO ACIDS FREE OF INTEREST FROM LEGUMINOUS FLOURS |
-
0
- BE BE788178D patent/BE788178A/en unknown
-
1971
- 1971-08-30 FI FI712421A patent/FI47629C/en active
-
1972
- 1972-07-19 GB GB3375472A patent/GB1377675A/en not_active Expired
- 1972-07-26 AT AT643972A patent/AT318135B/en not_active IP Right Cessation
- 1972-07-28 ES ES405706A patent/ES405706A1/en not_active Expired
- 1972-08-15 DK DK402872AA patent/DK130452B/en unknown
- 1972-08-18 NL NL7211294A patent/NL7211294A/xx not_active Application Discontinuation
- 1972-08-21 NO NO2993/72A patent/NO135344C/en unknown
- 1972-08-23 DE DE2241390A patent/DE2241390A1/en active Pending
- 1972-08-23 JP JP7283839A patent/JPS4835019A/ja active Pending
- 1972-08-24 FR FR7230119A patent/FR2151898A5/fr not_active Expired
- 1972-08-29 CA CA150,438A patent/CA979007A/en not_active Expired
- 1972-08-29 SE SE7211157A patent/SE393600B/en unknown
Also Published As
Publication number | Publication date |
---|---|
SE393600B (en) | 1977-05-16 |
ES405706A1 (en) | 1975-09-01 |
FI47629B (en) | 1973-10-31 |
GB1377675A (en) | 1974-12-18 |
DE2241390A1 (en) | 1973-03-08 |
FR2151898A5 (en) | 1973-04-20 |
NL7211294A (en) | 1973-03-02 |
CA979007A (en) | 1975-12-02 |
NO135344C (en) | 1977-03-30 |
DK130452B (en) | 1975-02-24 |
BE788178A (en) | 1973-02-28 |
JPS4835019A (en) | 1973-05-23 |
DK130452C (en) | 1975-08-18 |
AT318135B (en) | 1974-09-25 |
FI47629C (en) | 1974-02-11 |
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