CH394236A - Process for the preparation of lysine hydrochloride - Google Patents
Process for the preparation of lysine hydrochlorideInfo
- Publication number
- CH394236A CH394236A CH884461A CH884461A CH394236A CH 394236 A CH394236 A CH 394236A CH 884461 A CH884461 A CH 884461A CH 884461 A CH884461 A CH 884461A CH 394236 A CH394236 A CH 394236A
- Authority
- CH
- Switzerland
- Prior art keywords
- lysine
- sub
- reaction
- solution
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims 2
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 title 1
- 229960005337 lysine hydrochloride Drugs 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 7
- 239000004472 Lysine Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 claims 1
- CPYVQXAASIFAMD-KNIFDHDWSA-N (2s)-2-aminobutanedioic acid;(2s)-2,6-diaminohexanoic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O.NCCCC[C@H](N)C(O)=O CPYVQXAASIFAMD-KNIFDHDWSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000001256 tonic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 231100000668 minimum lethal dose Toxicity 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 235000020075 ouzo Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005891 transamination reaction Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fodder In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Procédé de préparation de l'aspartate de lysine
La présente invention a pour r objet un procédé de préparation d'un nouveau composé : l'aspartate de lysine de formule brute : C10H21O6N3. H4O et de formule dÚveloppee :
EMI1.1
Ce com, posé s'est avéré prósenter d'intéressantes propriétés thérapeutiques ; il exerce une action toni- que et énergétique.
Son poids moléculaire est de 297, sa teneur en azote total est de 14, 14 /o et sa composition cor respond à :
-Acide aspartique 44,8 %
Lysine 49, 1 ouzo
-Eau 6, 10/o
Il présente les propriétés physiques suivantes : -Poudre cristalline blanche.
¯ Très soluble dans l'eau distillée (1 partie dans
3 parties à 200 C-1 partie dans 1 partie à
1000 C).
¯ Très peu soluble dans l'éthanol : 1 partie n'est
pas dissoute dans 240 parties d'méthanol à 950 à
la température de 20 C.
Il se décompose sans fondre de 3350 à 3400 C.
Le pH de la solution aqueuse à 10/e est de 6, 8-7, 2.
Le procédé de préparation de l'aspartate de lysine suivant l'invention est caractérisé en ce qu'il cob siste à faire réagir de l'acide aspartique sur de la lysine.
La réaction est avantageusement opérée en solu- tion aqueuse aux environs de la, température am- biante, les réactifs étant en proportions sensiblement équimoléculaires.
La réaction achevée, on ajoute avantageusement au milieu réaotionnel un solvant organique miscible à l'eau dans lequel l'aspartate de lysine est peu soluble, afin de faciliter sa précipitation. L'Úthanol est un solvant particulièrement approprié pour cet usage.
On donnera ci-dessous un exemple de mise en oeuvre du procédé de préparation de l'aspantate de lysine.
Dans un cristallisoir de 2000 ml, peser :
Solution de lysine base à 50 % 292, 0 g
Chauffer au baimnarie jusqu'à la température de 450 C.
Ajouter : -Acide aspartique 133, 1 g
L'addition doit se faire par petites quantités en agitant chaque fois jusqu'à dissolution complète.
Continuer l'agitation pendant soixante minutes environ. Laisser refroidir jusqu'à la température de 200 C.
A ce moment, ajouter un germe d'aspartate de lysine et agiter vigoureusement.
Laisser en repos pendant douze heures à 200 C.
Ajouter : -Ethanol à 950 600 ml par petites quantités en agitant à chaque addition longuement de façon à incorporer ce solvant à la masse cristalline. Continuer à agiter fréquemment pendant deux heures.
Lorsque cette opération est terminée, obturer le cristallisoir et laisser en repos pendant quarante-huit heures en brassant à différentes reprises de façon à assurer l'homogénéité de la masse et éviter une prise en grumeaux.
La. masse bien homogène ou rendue homogène si nécessaire par broyage, est filtrée, essorée, lavée avec 300ml d'éthanol à 95o.
Après essorage, elle est séchée sous vide à la température de 40O C.
Rendement obtenu : 270-275 g (93, 5 /o).
Le produit ainsi obtenu doit répondre aux nor- mes chimiques indiquées (solubilité, point de fusion, pH, caractères d'identité).
D'autre part, il doit être également conforme aux déterminations quantitatives indiquées ci-après.
Les caractères d'identité de l'aspartate de lysine peuvent être détetrminés suf une solution à 10"/o, sur laquelle on efteftue les réactions suivantes : (a) A 2 ml de cette solution, ajouter 10 gouttes de
solution de ninhydrine à 1' /o. Porter au bain
marie.
Il se produit une coloration violette.
(b) Prélever 2 ml de cette solution. Ajouter 2 ml de
solution aqueuse d'acide picrique saturée. Au
bout de quinze minutes il commence à se produire
quelques cristaux. Ceux-ci envahissent la masse
complètement au bout de vingt-cinq minutes à
trente minutes.
(c) Prélever 2 ml de cette solution, ajouter 2 ml
d'acide chlorhydrique dilué (R) et 2 ml de solu-
tion d'acide phosphotungstique.
Il se produit un abondant précipité blanc, très
dense.
(d) A 2 ml de cette solution, ajouter 2 ml de réactif
préparé suivant la formule : -paradiméthylaminobenzaldéhyde 5 g -acide sulfurique 10 g -eau q. s. 100 g
Il se produit un abondant précipité blanc.
Porter au bain-marie ; au bout de deux minutes
ce précipité se dissout, tandis qu'il se produit une
coloration bleue qui, par refroidissement devient
bleu vert.
II se forme un léger précipité.
(e) A 2 ml de cette solution ajouter 2 ml d'acide
chlorhydrique dilué (R) et 2 ml de réactif
d'Erhlich, pracdemment dafini. Il se produit une
coloration jaune vert.
Les déterminations quantitatives suivantes per- mettent de vérifier la pureté de l'aspartatc de lysine : (a) Titrage de l'azote total par la méthode décrite au
Codex, page 1068.
Le titre ne doit pas être inférieur à 13, 5 ni supé
rieur à 14, 5 /o.
(b) Titrage de l'azote aminé par la méthode poten
tiométrique décrite par Monsieur Vigneron dans
sa communication à l'Académie de Pharmacie, le
3 février 1960 (Ann. Pharm. Franc. 1960-sous
presse).
L'aspartate de lysine rigoureusement déshydraté par un séjour à l'étuve pendant deux heures a 350 C, réagit vis-à-vis de l'acide perchlorique, en milieu acé- tique anhydre, comme un composé contenant trois atomes d'azote basique. 1 ml d'acide perchlorique N/10 correspond à 0, 0099 g dSaspalrtate de lysine.
L'étude pharmacologique de l'aspartate de lysine met en évidence les résultats suivants : A-toxicité
Par voie veineuse, chez la souris, la dose léthale est de 8, 7 g/kg.
La dose léthale minima, par voie péritonéale, chez la souris, est inférieure à 10 g/kg.
Par voie orale, chez la souris, la dose minima léthale est inférieure à 20 g/kg.
B-Effets physiologiqates
Aux doses de 10, 20, 40 mg/kg, chez le rat, il n'a pas été noté de modifications sensibles de la pression artérielle, de la respiration, mais il a été décelé une augmentation de la diurèse et une activité tonique se traduisant par une augmentation du temps de nage, dans les conditions décrites par Labrit.
Les indications thérapeutiques de l'aspartate de lysine sont à rattacher à son rôle de plaque tournante du métabolisme intermédiaire, et singulièrement, de la transamination.
Ce produit agit sur la synthèse protéique en con tribuant à rendre positif le bilan azoté, et comme facteur de croissance.
L'aspartate de lysine est de ce fait utilisable en thérapeutique pour ses propriétés toniques et éner- gétiques.
Dans ces conditions, il est administré avantage- sement sous forme de comprimés, dont la formule est, par exemple, la suivante : -Aspartate de lysine 0, 400 g -Amidon 0, 085 g -Fécule 0, 043 g ¯ Talc.... 0, 064 g ¯ Stéarate de magnésie 0, 008 g
pour un comprimé terminé à 0, 60 g
L'aspartate de lysine peut être administré sous cette forme à des doses variant entre 0, 40 g et 3, 20 g par jour.
Le produit peut être également administré sous forme de solution injectable contenant une solution aqueuse à 10"/o, ainsi que sous forme de suppositoires avec les excipients propres à cette formulation.
Process for preparing lysine aspartate
The present invention relates to a process for preparing a new compound: lysine aspartate of the crude formula: C10H21O6N3. H4O and of structural formula:
EMI1.1
This compound has been found to have interesting therapeutic properties; it exerts a tonic and energetic action.
Its molecular weight is 297, its total nitrogen content is 14.14 / o and its composition corresponds to:
-Aspartic acid 44.8%
Lysine 49, 1 ouzo
-Water 6, 10 / o
It has the following physical properties: -White crystalline powder.
¯ Very soluble in distilled water (1 part in
3 parts at 200 C-1 part in 1 part at
1000 C).
¯ Very slightly soluble in ethanol: 1 part is not
not dissolved in 240 parts of methanol at 950 to
the temperature of 20 C.
It decomposes without melting from 3350 to 3400 C.
The pH of the 10 / e aqueous solution is 6.8-7.2.
The process for preparing lysine aspartate according to the invention is characterized in that it cob sists in reacting aspartic acid with lysine.
The reaction is advantageously carried out in aqueous solution at around room temperature, the reactants being in substantially equimolecular proportions.
When the reaction is complete, a water-miscible organic solvent in which lysine aspartate is sparingly soluble is advantageously added to the reaction medium, in order to facilitate its precipitation. Ethanol is a particularly suitable solvent for this use.
An example of implementation of the process for preparing lysine aspantate will be given below.
In a 2000 ml crystallizer, weigh:
50% lysine base solution 292.0 g
Heat in a baimnarie to a temperature of 450 C.
Add: -Aspartic acid 133, 1 g
The addition should be made in small quantities, stirring each time until complete dissolution.
Continue stirring for about sixty minutes. Leave to cool to a temperature of 200 C.
At this point, add a seed of lysine aspartate and shake vigorously.
Let stand for twelve hours at 200 C.
Add: -Ethanol to 950 600 ml in small quantities, stirring at each addition for a long time so as to incorporate this solvent into the crystalline mass. Continue to agitate frequently for two hours.
When this operation is completed, close the crystallizer and leave to stand for forty-eight hours, stirring several times so as to ensure the homogeneity of the mass and to avoid setting in lumps.
The very homogeneous mass, or made homogeneous if necessary by grinding, is filtered, drained and washed with 300 ml of 95 ° ethanol.
After spinning, it is dried under vacuum at a temperature of 40O C.
Yield obtained: 270-275 g (93.5 / o).
The product thus obtained must meet the chemical standards indicated (solubility, melting point, pH, identity characteristics).
On the other hand, it must also comply with the quantitative determinations indicated below.
The identity characteristics of lysine aspartate can be determined in a 10 "/ o solution, on which the following reactions are carried out: (a) To 2 ml of this solution, add 10 drops of
ninhydrin solution at 1%. Wear to bath
married.
A purple coloration occurs.
(b) Take 2 ml of this solution. Add 2 ml of
saturated aqueous picric acid solution. At
after fifteen minutes it starts to happen
some crystals. These invade the masses
completely after twenty-five minutes at
thirty minutes.
(c) Take 2 ml of this solution, add 2 ml
dilute hydrochloric acid (R) and 2 ml of solution
tion of phosphotungstic acid.
There is an abundant white precipitate, very
dense.
(d) To 2 ml of this solution, add 2 ml of reagent
prepared according to the formula: -paradimethylaminobenzaldehyde 5 g -sulfuric acid 10 g -water q. s. 100 g
An abundant white precipitate occurs.
Bring to a bain-marie; after two minutes
this precipitate dissolves, while a
blue coloration which, on cooling becomes
Blue green.
A slight precipitate forms.
(e) To 2 ml of this solution add 2 ml of acid
dilute hydrochloric acid (R) and 2 ml of reagent
of Erhlich, previously defined. There is a
green yellow coloring.
The following quantitative determinations make it possible to verify the purity of the lysine aspartate: (a) Titration of total nitrogen by the method described in
Codex, page 1068.
The title must not be less than 13.5 or greater
laughing at 14, 5 / o.
(b) Titration of amino nitrogen by the poten method
tiometric described by Monsieur Vigneron in
its communication to the Academy of Pharmacy, the
February 3, 1960 (Ann. Pharm. Franc. 1960-under
hurry).
Lysine aspartate, rigorously dehydrated by a stay in an oven for two hours at 350 C, reacts with perchloric acid, in anhydrous acetic medium, like a compound containing three basic nitrogen atoms. . 1 ml of N / 10 perchloric acid corresponds to 0.0099 g of lysine saspalrtate.
The pharmacological study of lysine aspartate shows the following results: A-toxicity
By the venous route, in mice, the lethal dose is 8.7 g / kg.
The minimum lethal dose, peritoneally, in mice is less than 10 g / kg.
Orally, in mice, the minimum lethal dose is less than 20 g / kg.
B-Physiological effects
At doses of 10, 20, 40 mg / kg, in rats, no significant changes in blood pressure or respiration were noted, but increased diuresis and tonic activity were detected. resulting in an increase in swimming time, under the conditions described by Labrit.
The therapeutic indications of lysine aspartate should be linked to its role as a hub of intermediate metabolism, and particularly of transamination.
This product acts on protein synthesis by helping to make the nitrogen balance positive, and as a growth factor.
Lysine aspartate is therefore usable in therapy for its tonic and energy properties.
Under these conditions, it is advantageously administered in the form of tablets, the formula of which is, for example, the following: -Lysine aspartate 0, 400 g -Starch 0, 085 g -French 0, 043 g ¯ Talc .. .. 0, 064 g ¯ Magnesia stearate 0, 008 g
for a tablet finished at 0.60 g
Lysine aspartate can be administered in this form at doses varying between 0.40 g and 3.20 g per day.
The product can also be administered in the form of an injection solution containing an aqueous solution at 10 "/ o, as well as in the form of suppositories with the excipients specific to this formulation.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR834521A FR86M (en) | 1960-07-29 | 1960-07-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH394236A true CH394236A (en) | 1965-06-30 |
Family
ID=8736587
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH884461A CH394236A (en) | 1960-07-29 | 1961-07-27 | Process for the preparation of lysine hydrochloride |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE606637A (en) |
CH (1) | CH394236A (en) |
ES (1) | ES269441A1 (en) |
FR (1) | FR86M (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE637448A (en) * | 1962-09-17 | 1900-01-01 | ||
BE789856A (en) * | 1971-10-13 | 1973-02-01 | Tixier Georges | MEDICINAL PRODUCT BASED ON LYSINE DERIVATIVES, WHICH MAY STIMULATE DIFFERENT METABOLISMS, IN PARTICULAR LEUKOCYTE GENESIS |
FR2495608A1 (en) * | 1980-12-04 | 1982-06-11 | Morelle Jean | NEW ASPARTIC ACID DERIVATIVES AND THEIR USES |
-
1960
- 1960-07-29 FR FR834521A patent/FR86M/fr active Active
-
1961
- 1961-07-27 BE BE606637A patent/BE606637A/en unknown
- 1961-07-27 CH CH884461A patent/CH394236A/en unknown
- 1961-07-28 ES ES0269441A patent/ES269441A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
ES269441A1 (en) | 1962-01-01 |
BE606637A (en) | 1961-11-16 |
FR86M (en) | 1961-01-09 |
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