CA1108463A - Process to obstruct the attack by viruses - Google Patents

Process to obstruct the attack by viruses

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Publication number
CA1108463A
CA1108463A CA320,356A CA320356A CA1108463A CA 1108463 A CA1108463 A CA 1108463A CA 320356 A CA320356 A CA 320356A CA 1108463 A CA1108463 A CA 1108463A
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Canada
Prior art keywords
terpene
micro
organisms
foodstuffs
oil
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.)
Expired
Application number
CA320,356A
Other languages
French (fr)
Inventor
Erich Wolf
Andreas Lembke
Rolf Deininger
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Chimicasa GmbH
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Chimicasa GmbH
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Publication date
Application filed by Chimicasa GmbH filed Critical Chimicasa GmbH
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Publication of CA1108463A publication Critical patent/CA1108463A/en
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    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N7/00Viruses; Bacteriophages; Compositions thereof; Preparation or purification thereof
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23CDAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00Milk preparations; Milk powder or milk powder preparations
    • A23C9/12Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/123Fermented milk preparations; Treatment using microorganisms or enzymes using only microorganisms of the genus lactobacteriaceae; Yoghurt
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23CDAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00Milk preparations; Milk powder or milk powder preparations
    • A23C9/12Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/11Aldehydes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/12Ketones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/21Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/185Magnoliopsida (dicotyledons)
    • A61K36/23Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/185Magnoliopsida (dicotyledons)
    • A61K36/54Lauraceae (Laurel family), e.g. cinnamon or sassafras
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/185Magnoliopsida (dicotyledons)
    • A61K36/67Piperaceae (Pepper family), e.g. Jamaican pepper or kava
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/88Liliopsida (monocotyledons)
    • A61K36/899Poaceae or Gramineae (Grass family), e.g. bamboo, corn or sugar cane
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/88Liliopsida (monocotyledons)
    • A61K36/906Zingiberaceae (Ginger family)
    • A61K36/9064Amomum, e.g. round cardamom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/38Chemical stimulation of growth or activity by addition of chemical compounds which are not essential growth factors; Stimulation of growth by removal of a chemical compound
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2710/00MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA dsDNA viruses
    • C12N2710/00011Details
    • C12N2710/10011Adenoviridae
    • C12N2710/10311Mastadenovirus, e.g. human or simian adenoviruses
    • C12N2710/10361Methods of inactivation or attenuation
    • C12N2710/10363Methods of inactivation or attenuation by chemical treatment

Abstract

ABSTRACT OF THE DISCLOSURE
The invention relates to a method and a preparation for combatting theviruses and bacteriphages to which micro-organisms, such as bacteria, fungi, yeasts and algae, used in the preparation of foodstuffs by fermentation, caseation, and the like, are subject. This is achieved by the addition of terpenes preferably obtained in their natural form from spice plants. The following terpenes are mentioned as being particularly suitable: black-pepper oil, cinnamon-flower oil, cardamum oil, linalyl acetate, sinnamic aldehyde safrol carvone and cis/trans citral.

Description

34~3 . .
The invention relates to a method for preparing foodstuffs ~mder the action of micro-or~ani.sms in which a viable culture of micro-organisms~
capable of prop~gating, is inoeulated into the foodstuff to be prepared and suitable living conditions for the said micro-organisms are provided and maintained, for ~he duration of the effect sought, by the addition of nutrients~ and/or by adjusting the temperature, the humidity and/or the pH value, and to a preparation for protecting the said micro-organisms against attack by bacteriophages~
The industrial preparation of foodstuffs, by attenuation~ ease-ation, and fermentation, for example, is carried out wi~h the co-operation of micro-organisms, namely bacteria, yeasts, fungi or algaeO In the cul-tures where they are kept in readiness, and also while they are acting upon the foodstuf.fs, these micro-organisms are subject to attack by bacter-iophages and viruses, which may interfere with the reaction processes which the micro-organisms produce.
It is the purpose of ~he present invention to eliminate this interference~
The invention is characteri~ed in that the micro-organisms are protected against attack by bacteriophages and viruses by the addition, intermi~ing, and reaction of terpene obtainable from spice plants the amount of terpelle uscd being between 1 and 1000 mg of terpene to 10 kg of food-stuff.
The terpenes have a virucidal action (i.e. a virus-destroying action) in a concentration which is lower by one or more powers of ten than the concentratioll at which they have a to.~ic effect upon living cells~ This ~j , .

- ' ~ ~ , ' :. ' ' , - ~

'. . : ~ ', : ~'' : '' wide gap provides a useful dosage range within which the desired virucidal action may be obtained without any danger of simultaneously harming the . micro-organismsO
Since these terpenes may be obtained from spice plants which have been used in human and animal foods for many years, and have proven harmless in the amounts thus used~ this ensures that the amounts of terpene to be used according to the invention will have no harmful effects when consumed with the foodstuffs treated therewith.
- Since the virucidal action sought is obtainable with a relatively small addition of terpenes, there is also no question of the said terpenes impairing the taste of the foodstuffs After inoculation, the micro-organisms increase in number and the amount of terpene needed to protect the total volume of micro-organisms may be added to the foodstuff all at once. However, the terpene may also be added to chronologically consecutive batches as the micro-organism pop--; ulation increases.
The following terpenes~ or mixtures of terpenes9 have been found to be partic~larly satisfactory: black-pepper oil, cinnamon~flower oil cardamum oil, linalyl acetate, cinnamic aldehyde, safrol~ carvone and cis/
trans citral and these may be used separately or mixed together.
The terpenes used may be obtained as follows from spice plants by steam distillation:
black-pepper oil: from ~he pips of the piper nigrum;
cinnamon-flower oil- from the blossoms of the cinnamonum cassia;
cardamum oil: from the seeds of th~ elettaria cardamomum;

.

. "''' ' ' -. '' ' ' : -, ' -' ' ~' ' ' ~ ~ ' " , " ' linalyl acetate: from the blossoms of the lavender:
cinnamic aldehyde: from the bark of the cinnamonum ceylanicum;
safrol: from the root of the sassafras;
carvone: from the fruit of the carl~ carvi, and cis/trans citral: from the leaves of the cymbopogon citratus.
It is also possible to use, instead of these natural terpenes, syn~hetic terpenes identical therewith~ iE they are avai]able. ~owever~
natural terpenes obtained from spice plants are to be preferredO
The resuLts obtainable with the invention are determined by com-parison tests as follows:
; Gell cultures were grown in various vessels, under optimal con-ditions, from permanent strains such as "Girardi Heart" ~GH)~ "Flow'l12000 (FL) "Intestine 407" ~IN) and "Vero Kidney" (V~) forming on the bottom of each vessel a mat of cell culture containing abouk 0025 mg of cell substance.
A suspension of Virus Adeno Type 6 was also used.
For the total of eight terpenes shown in Table 1 twenty cultures were prepared from each type of cellO The said twenty cultures from each type of cell were treated with different amounts of the relevant terpene~
as shown below:
The first two cell cultures received 10~ mg of terpene per 10 kg of cell substanceO The next ~wo cell cultures received 104 mg of terpene per 10 kg of cell substance. The ne~t two cell cultures received 103 mg of terpene per 10 kg of cell substance~ and so on to the last two of these twenty cell cultures which received 0.1 mg of terpene per 10 kg of cell substance. Thus two similar cell cultures were always treated with the - .
..
:, :
.
:, ~ - .. , : .
, same amo~mt of the same terpene. One of these two similar cell cultures was left as it was and was used as a control~ while the second was also inoculated, while still in the form of a virus suspension3 with 5 x 10 virus particles per 0025 mg of cell substances. The other cell cultures and terpenes were dealt with accordingly.
The cell cultures thus treated were allowed to stand and~ after four and six days, the~ were examined microscopically ~or cell damage~
` the damage observed being grouped into four stages as follows7 stage O signifying no damage ` 10 stage 1 signifying loosened growth of cell bonds stage 2 signifying that the cells had formed balls had become detached from the bottom of the vessel stage 3 signifying that the cell structures had been largely or completely destroyed.
It was fo~md that inoculated cell structures which had been pro-tected with a very small amouIlt of terpene had reached stage 3 or 2, since `~ the viruses had damaged the cells. Inoculated cell cultures containing a very large amount of terpene had also reached stage 3 or 2g since the cells had been damaged by an excess of terpene. ~lowever~ cell cultures containing only a moderate amount of terpene were at stage 0~ i.e. they showed no signs of damage. Thus the moderate amount of terpene did enough ~ damage to the viruses to protect the cells from attack~ but without damag-:
ing the cells themselves. Terpene concentrations at which the inoculated cell cultures after four and six days, were at stage 0, with a few at stage 1~ i.e. in which the viruses had been damaged without damaging the cells, are given in Table 1.
The first colwnn in Table 1 indicates the terpene used~ colu~

~ . .6 .~

; -4-- , . : .................................... :

:, , ,
2 gives the cell strains treated-abbreviated as indicated hereinbefore, while column 3 gives the amount of terpene used, in mg/10 kg of treated cell substance, for the concentration range within which no substantial cell damage was observed (i.e. stage 0). This is the treatment range, which in each case extends over several powers of ten. Thus in the case of all of the terpenes given in Table 1, the virucidal action sought occurs at a concentration which is lower~ by several powers of ten~ than the lowest concentration at which cell damage was observed, i.e. at which damage to the micro-organisms to be protected could occur.
Table I

Terpene Cell Substance Virucidal concentration ; treated range o~er which no cell damage was observed, ex~
pressed in mg of terpene per 10 kg of treated cell substance Black-pepper oil GH ~10 to 0.1 " FL 100 to 0~1 IN 100 to 1 " VE 100 to 0.1 Cinnamon-Flower oil GH lO~ to 0.1 Fl 103 to 0.1 " IN 100 to Oo1 l, VE 100 to 0.1 Cardamum oil GH 100 to 1 FL 100 to 1 " IN 100 to 1 VE 100 to 10 ': . . : ~ : ., : : , '' . : ' ~ ' : : '' - ~ .
` `: ~ : ` ` :: : ': `, .

Table 1 continuecl __ Terpene Cell Substance Virucidal concentration treated range over which no cell damage was observed, ex-pressed in mg of terpene per 10 kg of treated cell substance Linalyl Acetate GH 100 to O.1 " FL 100 to 1 " IN 100 to 1 1' VE 100 to 1 Cinnamic aldehyde GH 100 to 1 ~' FL lOO to 1 IN 100 to 1 " Y~ 100 to 1 Safrol GH 100 to 1 FL 100 to 1 IN 100 to 10 VE 100 to 1 ;
i Carvone GH 100 to 1 1t ` FL 100 to 1 " IN 100 to 1 ~ VE 100 to 1 Cis/trans citral &H 10 to 1 ~,' FL 10 to 1 " IN 100 to 1 VE 100 to 1 :

. : `, ' ' ' ` . . i " ~MPLE 1 For the production of yoghurt 100 l of cow~s milk are sterilized and ~hen adjusted to 40C. 500 mg of black-pepper oil are then added to the milk, stirring being used to ensure thorough mixing, after which the milk is inoculated with a pure culture of lactic-acid bacteria-lactobacillus bulgaricus. The mixture is allowed to stand at 40~ for 12 hours~ protected from external influences~ ~til the yoghurt has formedO
"'~ l~XAMPLE ~
100 l of finished, filtered beer wort are adjusted to 10C~ 500 mg of black-pepper oil are mixed thereinto, after which it is inoculated with a culture of pure yeast obtained from saccharomyces cerevisae and allowed to stand at 10 C for 8 to 10 days~ protected from external influ ences. The finished beer is now removed from the yeast, which has in the meanwhile settled, and is filled into barrels.

;~ 100 1 of finished, filtered beer wort are adjusted to 10 C. 500 mg of black-pepper oil are mixed thereinto. 1 mg of black-pepper oil is mixed with 100 g of a pure yeast culture derived from saccharomyces cere-~-visiae, and the mixture is aIlowed to stand for 15 minutes. The 100 1 of beer wort are then inoculated with this yeast and are allowed to stand at 10 C for 8 to 10 days~ protected from external influences. D~uring this period, batches of black-pepper oil~ each containing 2480 mg, are added to the fermenting beer wort at 5, 10, 12 and 14 hours after the inoculation.
After the final batch has been added, the beer is allowed to remain quiet so that fermentation is completed~ the yeast settles, and the finished beer - ~ .~
~B~

can be removed therefrom and filled into barrels. The total amount of terpene added was 10~000 mgO
In these examples~ the addition of terpene pre~ented damage by viruses and bacteriophages, but because of the small amount of terpene no taste or other problems had to be taken into account.
The examples given may be modified by replacing the black-pepper oil with the same amount of another terpene from Table 1~ or with a mixture of several of these terpenes. The amount of terpene used may also be var-ied~ within the range given in ~he claimsO In all of these cases~ a viru-cidal action is obtained, without any taste or other problems.

Black_pepper oil is obtained from black pepper by steam distil-lationO The black-pepper oil is dissol~ed in 1~27dihydroxypropane in a ; weight ratio of 1:50. The solution is sterilized for 50 minutes at 121 C
in an autoclave. The preparation thus obtained is added to the foodstuff, to be treated with the micro-organisms in a weight ratio of between 50 mg and 5.0 g of the preparation to 10 kg of the foodstuff~ corresponding to between 1 and 100 mg of terpene to 10 kg of foodstuff.
Example 4 may be modified by replacing the black-pepper oil with ~0 the same amount of another terpene in Table 1~ or with a mixture of several terpenes. It is also possible in this example to vary the terpene: 1~2 dihydroxypropane in the range between 1:10 and 1:1000. In this case~ the amount of the preparation added to the foodstuff must be altered to maintain ; the concentration of between 1 and 100 mg of terpene to 10 kg of foodstuff.
The preparation according to Example 4~ or modified as indicated~

- . . , ~ , . ~ . ' ' :

is used to add the terpene to foodstuffs, and it may also be used in con-j~mtion with Examples 1~ 2 and 3.
The aforementioned micro-organisms are accessible to the public as follows:
1. Girardi lleart under CCL27 at ATCC(American Type Culture Collection) 2. Flow 12,000 under 02-150 at Flow Laboratories GmbH ~Dietzstr. 10, 5300 Bonn 3, Fed. Rep. of Germany
3. Intestine 407 under CCL 6 at ATCC
4. Vero Kidney under 01-000 at Flow Laboratories GmbH
5. Lactobacillus bulgaricus under 20080 and 20081 at DSM ~Deutsche Sammlung von Mikroorganismen, Gesellschaft fur biotechnologische Forschung mbH, Griesebachstr. 8, 3400 Gottingen, Fed. Rep~ of Germany)
6~ Saccoromyces cerevisiae under 1133, 1134 and 70449 at DSM.

~' i:
!

~ ~,' _ g _

Claims (5)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method for preparing foodstuffs under the action of micro-organisms, in which a viable culture of the micro-organisms, capable of propagating, is inoculated into the foodstuff to be prepared and suitable living conditions for said micro-organisms are provided and maintained, for the duration of the action sought, by the addition of nutrients and/or by adjusting the temperature, humidity, and/or the pH value characterized in that the micro-organisms are protected against attack by bacteriophages and viruses by the addition, intermixing and reaction of at least one terpene selected from the group consisting of black-pepper oil, cinnamon-flower oil, cardamum oil, linalyl acetate, cinnamic aldehyde, safrol, carvone and cis/trans citral, all of which may be obtained in a natural form from spice plants, the amount of terpene used being between 1 and 1000 mg to 10 kg of foodstuffs.
2. A method according to claim 1, characterized in that a said terpene is added to the foodstuff to be prepared as soon as the micro-organisms begin to act.
3. A method according to claim 1, characterized in that part of a said terpene is added to the culture of micro-organisms before the foodstuffs are inoculated therewith, the remainder of the terpene being added, to and mixed with, the foodstuffs inoculated with the said micro-organisms in chronoligically consecutive batches, through-out the period of activity of the said micro-organisms.
4. A method according to claim 1 characterized in that in the preparation of milk products using lactic-acid streptococcus, said terpene are used to protect said lactic-acid streptococcus.
5. A method according to claim 1 characterized in that in fermenting beer wort by the use of a yeast derived from saccharo-myces cerevisiae, this is protected by the use of said terpene.
CA320,356A 1978-01-27 1979-01-26 Process to obstruct the attack by viruses Expired CA1108463A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LU78955A LU78955A1 (en) 1978-01-27 1978-01-27 METHOD FOR INACTIVATING VIRUSES
LU78955 1978-01-27

Publications (1)

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CA1108463A true CA1108463A (en) 1981-09-08

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AT (1) AT374345B (en)
AU (2) AU4361879A (en)
BE (1) BE873695A (en)
CA (2) CA1103165A (en)
CH (1) CH640138A5 (en)
DD (1) DD143924A5 (en)
DE (1) DE2901829A1 (en)
ES (1) ES477197A1 (en)
GB (1) GB2013086B (en)
IE (2) IE47787B1 (en)
LU (1) LU78955A1 (en)
MX (1) MX5421E (en)
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ZA (2) ZA79335B (en)

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GB508407A (en) * 1938-03-08 1939-06-30 Thomas Lewis Shepherd A new and improved disinfectant insecticidal, fungicidal, vermin destroying and therapeutic substance and method of making the same
GB1060447A (en) * 1963-05-14 1967-03-01 Maple Leaf Trust Compositions for the preservation of foodstuffs, for the sterilization and hygiene ofair in confined spaces and for cosmetic and pharmaceutical purposes
US3595975A (en) * 1969-07-29 1971-07-27 Holliston Lab Inc Disinfecting compositions
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IE790156L (en) 1979-07-27
US4592910A (en) 1986-06-03
US4595593A (en) 1986-06-17
GB2013086B (en) 1982-12-22
ZA79334B (en) 1980-02-27
IE790155L (en) 1979-07-27
LU78955A1 (en) 1979-09-06
SE7900728L (en) 1979-07-28
AT374345B (en) 1984-04-10
IE47909B1 (en) 1984-07-25
SE452948B (en) 1988-01-04
JPS54110310A (en) 1979-08-29
BE873695A (en) 1979-05-16
JPH024579B2 (en) 1990-01-29
CH640138A5 (en) 1983-12-30
IE47787B1 (en) 1984-06-13
MX5421E (en) 1983-08-01
DE2901829C2 (en) 1990-08-09
AU4361879A (en) 1979-08-02
AU4361779A (en) 1979-08-02
GB2013086A (en) 1979-08-08
ZA79335B (en) 1980-02-27
US4402950A (en) 1983-09-06
JPS54113449A (en) 1979-09-05
DE2901829A1 (en) 1979-08-02
ES477197A1 (en) 1979-10-16
DD143924A5 (en) 1980-09-17
ATA60079A (en) 1983-09-15
CA1103165A (en) 1981-06-16

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