LU82007A1 - NEW PROCESS FOR THE PREPARATION OF L-LYSINE CARBAMATE - Google Patents
NEW PROCESS FOR THE PREPARATION OF L-LYSINE CARBAMATE Download PDFInfo
- Publication number
- LU82007A1 LU82007A1 LU82007A LU82007A LU82007A1 LU 82007 A1 LU82007 A1 LU 82007A1 LU 82007 A LU82007 A LU 82007A LU 82007 A LU82007 A LU 82007A LU 82007 A1 LU82007 A1 LU 82007A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- lysine
- filtrate
- preparation
- methanol
- carbamate
- Prior art date
Links
- XFQCPHGOMQULNH-JEDNCBNOSA-N carbamic acid;(2s)-2,6-diaminohexanoic acid Chemical compound NC(O)=O.NCCCC[C@H](N)C(O)=O XFQCPHGOMQULNH-JEDNCBNOSA-N 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 6
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 claims description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 238000004061 bleaching Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 235000011089 carbon dioxide Nutrition 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims description 2
- 229940072033 potash Drugs 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 230000005587 bubbling Effects 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 235000019766 L-Lysine Nutrition 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 239000007938 effervescent tablet Substances 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940068517 fruit extracts Drugs 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 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
- A61K31/60—Salicylic acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/40—Effervescence-generating compositions
-
- 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
- A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
-
- 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
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/618—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate
- A61K31/621—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate having the hydroxy group in position 2 esterified, e.g. benorylate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
- A61K9/0007—Effervescent
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
La présente invention concerne un nouveau procédé plus économique de préparation du carbamate de L-lysine.The present invention relates to a new, more economical process for the preparation of L-lysine carbamate.
On utilise notamment le carbamate de L-lysine comme ingrédient de mélanges effervescents, eux-mêmes utiles pour préparer notamment 5 des boissons pétillantes et des compositions pharmaceutiques effervescentes, par exemple cachets ou comprimés effervescents, etc. On citera en particulier comme application les compositions pharmaceutiques effervescentes ne contenant pas d'ions alcalins ou ne contenant qu'une faible quantité * d'ions alcalins. Gette classe de compositions pharmaceutiques évite en 10 effet l'accumulation indésirable d'ions alcalins dans l'organisme et permet le traitement de patients sous régime désodé.L-lysine carbamate is used in particular as an ingredient in effervescent mixtures, themselves useful for preparing in particular sparkling drinks and effervescent pharmaceutical compositions, for example effervescent cachets or tablets, etc. Mention will in particular be made, as application, of the effervescent pharmaceutical compositions which do not contain alkaline ions or which contain only a small quantity * of alkali ions. This class of pharmaceutical composition in fact avoids the undesirable accumulation of alkaline ions in the body and allows the treatment of patients on a low diet.
D'autres avantages de l'emploi du carbamate de L-lysine résident dans le fait que la tolérance gastrique est excellente grâce à un milieu tamponné, et dans le passage quasi immédiat dans le circuit 15 sanguin.Other advantages of using L-lysine carbamate reside in the fact that gastric tolerance is excellent thanks to a buffered medium, and in the almost immediate passage through the blood circuit.
La demanderesse a maintenant découvert selon l'invention un procédé nouveau de préparation du carbamate de L-lysine, qui autorise le choix comme produit de départ d'un monochlorhydrate de L-lysine de qualité alimentaire animale, donc relativement peu coûteux.The Applicant has now discovered according to the invention a new process for the preparation of L-lysine carbamate, which allows the choice as starting material of an L-lysine monohydrochloride of animal food quality, therefore relatively inexpensive.
20 Ce monochlorhydrate est, dans une première étape, traité en solution aqueuse par du noir décolorant qui est ensuite éliminé, par exemple par filtration.This monohydrochloride is, in a first step, treated in aqueous solution with bleaching black which is then removed, for example by filtration.
Une deuxième étape consiste à traiter le monochlorhydrate de L-lysine obtenu par une base, par exemple la potasse ou la soude, et à éli-25 miner le sel obtenu, par exemple le chlorure de potassium ou de sodium, par . une technique connue (par exemple essorage) après addition de méthanol comme solvant préféré.A second step consists in treating the L-lysine monohydrochloride obtained with a base, for example potash or soda, and in eliminating the salt obtained, for example potassium or sodium chloride, by. a known technique (for example wringing) after addition of methanol as preferred solvent.
La troisième étape du procédé selon l'invention consiste à traiter le filtrat obtenu à la seconde étape par du gaz carbonique (ou de 30 la carboglace) et à récupérer le précipité obtenu qui est le produit recherché .The third step of the process according to the invention consists in treating the filtrate obtained in the second step with carbon dioxide (or dry ice) and in recovering the precipitate obtained which is the desired product.
Le carbamate de L-lysine ainsi obtenu se présente sous la forme d'une poudre cristalline de couleur blanche ; ce produit est très soluble dans l'eau, mais est insoluble dans le méthanol, ce qui autorise 35 un lavage du précipité par ce produit.The L-lysine carbamate thus obtained is in the form of a white crystalline powder; this product is very soluble in water, but is insoluble in methanol, which allows the precipitate to be washed with this product.
Sans que la portée de l'invention soit limitée par l'hypothèse suivante, la demanderesse considère comme probable que le carbamate de L-lysine résultant de l'association d'une mole de L-lysine et d'une moleWithout the scope of the invention being limited by the following hypothesis, the applicant considers it probable that the L-lysine carbamate resulting from the association of a mole of L-lysine and a mole
XX
2 de C02 est stabilisé par une seconde molécule de L-lysine selon la formule suivante : hooc(nh2)ch - (ch2)4 - nh - cooh .... nh2(ch2)4 - ch(nh2)cooh ce qui est eonfirmé par les résultats des analyses effectuées.2 of C02 is stabilized by a second molecule of L-lysine according to the following formula: hooc (nh2) ch - (ch2) 4 - nh - cooh .... nh2 (ch2) 4 - ch (nh2) cooh which is confirmed by the results of the analyzes carried out.
5 Les exemples suivants illustrent l'invention sans toutefois en limiter la portée.The following examples illustrate the invention without, however, limiting its scope.
EXEMPLE 1 - On dissout entre 50 et 60°C 300 g de monochlorhydrate de > L-lysine "feed grade" (de qualité alimentaire animale) (titre >98 %) dans 3 300 cm .d'eau.EXAMPLE 1 300 g of> L-lysine monohydrochloride "feed grade" (animal feed quality) (titer> 98%) are dissolved between 50 and 60 ° C. in 3300 cm. Of water.
On laisse sous agitation durant 15 minutes à 60°C avec 6 g 10 de noir décolorant.The mixture is left stirring for 15 minutes at 60 ° C. with 6 g of bleaching black.
On filtre sur papier.We filter on paper.
On ajoute peu à peu vers 40°C, sous agitation, 110 g de potasse, on refroidit à température ambiante, on laisse sous agitation durant 3 une heure, on ajoute peu à peu 1500 cm de méthanol, on laisse sous agitais tion durant 2 heures 30 minutes et on essore le chlorure de potassium formé.110 g of potassium hydroxide are added little by little at 40 ° C., with stirring, the mixture is cooled to room temperature, the mixture is left stirring for 3 hours, gradually adding 1500 cm of methanol, the mixture is left stirring for 2 hours 30 minutes and the potassium chloride formed is drained.
On introduit peu à peu dans le filtrat, en 1 heure environ, 60 à 80 g de gaz carbonique. On laisse reposer une nuit, on filtre, on lave au méthanol à 95 % et on sèche vers 40°C. On obtient 200 g du produit recherché, F. 249-250°C.60 to 80 g of carbon dioxide are gradually introduced into the filtrate, over about 1 hour. It is left to stand overnight, filtered, washed with 95% methanol and dried at around 40 ° C. 200 g of the sought product are obtained, mp 249-250 ° C.
20 Analyse : C13H28N4°620 Analysis: C13H28N4 ° 6
Calculé: C % 46,41 H % 8,39 N % 16,65 0 % 28,54Calculated: C% 46.41 H% 8.39 N% 16.65 0% 28.54
Trouvé : C % 46,62 H % 8,37 N % 16,39 O % 28,33 EXEMPLE 2Found: C% 46.62 H% 8.37 N% 16.39 O% 28.33 EXAMPLE 2
On dissout à 30eC 300 g de monochlorhydrate de L-lysine 25 "feed grade" (titre V 98 %) dans 450 cm^ d'eau;300 g of L-lysine monohydrochloride 25 "feed grade" (titre V 98%) are dissolved at 30 ° C. in 450 cm 3 of water;
On laisse sous agitation durant 15 minutes à 30°C avec 6 g de noir décolorant.The mixture is left stirring for 15 minutes at 30 ° C. with 6 g of bleaching black.
On filtre sur papier.We filter on paper.
On ajoute peu à peu, vers 20°C, 79 g de soude, on refroidit 30 à température ambiante, on laisse sous agitation durant 1 heure, on ajoute 3 peu à peu 2000 cm de méthanol, on laisse sous agitation durant 3 h.et on essore le chlorure de sodium formé.79 g of sodium hydroxide are gradually added, at around 20 ° C., the mixture is cooled to ambient temperature, the mixture is left stirring for 1 hour, 2000 cm 3 of methanol is gradually added, the mixture is left stirring for 3 h. and the sodium chloride formed is drained.
On introduit peu à peu dans le filtrat, en 1 heure environ, 60 à 80 g de gaz carbonique, on laisse reposer une nuit, on filtre, on lave 35 au méthanol à 95 % et on sèche vers 40°C. On obtient 189 g du produit recherché. F. 246-250“C.60 to 80 g of carbon dioxide are gradually introduced into the filtrate, over about 1 hour, left to stand overnight, filtered, washed with 95% methanol and dried at around 40 ° C. 189 g of the sought product are obtained. F. 246-250 “C.
Analyse :Analysis:
Calculé : C % 46,41 H % 8,39 N % 16,65 0 % 28,54Calculated: C% 46.41 H% 8.39 N% 16.65 0% 28.54
Trouvé : C % 46,23 H % 8,43 N % 16,67 0 % 28,29 .Found: C% 46.23 H% 8.43 N% 16.67 0% 28.29.
^ * EXEMPLE 3 3^ * EXAMPLE 3 3
On reprend le mode opératoire de l'exemple 1, en remplaçant le CO2 par une introduction progressive de carboglace, jusqu'à ce qu'il ne se forme plus de précipité blanc. On laisse ensuite revenir à la tempéra- 5 ture ambiante, et on poursuit l'agitation pendant 3 heures 30 minutes. On 3 filtre avant de laver le produit ainsi obtenu par 800 cm de méthanol, ce = qui donne le produit recherché avec un rendement de 192 g. F. 247-250°C.The procedure of Example 1 is repeated, replacing the CO 2 by a gradual introduction of dry ice, until no more white precipitate is formed. It is then allowed to return to room temperature and the stirring is continued for 3 hours 30 minutes. 3 are filtered before washing the product thus obtained with 800 cm of methanol, which gives the desired product with a yield of 192 g. Mp 247-250 ° C.
EXEMPLE. 4EXAMPLE. 4
Comprimés effervescents contenant de l'acide acétylsalicylique, sans ions 10 alcalinsEffervescent tablets containing acetylsalicylic acid, without alkaline ions
On prépare un mélange effervescent dans les proportions suivantes : acide acétylsalicylique ....................... 0,500 g carbamate de L-lysine ......................... 1,6 g 15 acide citrique ................................0,4 g = Ces valeurs sont données pour un comprimé dosé de manière classique à 0,5 g d'acide acétylsalicylique.An effervescent mixture is prepared in the following proportions: acetylsalicylic acid ....................... 0.500 g L-lysine carbamate ........ ................. 1.6 g 15 citric acid .......................... ...... 0.4 g = These values are given for a tablet dosed in a conventional manner with 0.5 g of acetylsalicylic acid.
EXEMPLE 5EXAMPLE 5
On prépare une composition effervescente pour boisson pétillante 20 dans les proportions suivantes : sucre ......................................... 17 g carbamate de L-lysine ......................... 1,4 g acide citrique................................ 2,7 g que l'on peut aromatiser de manière connue par des extraits de fruits en 25 poudre. On peut également ajouter éventuellement de la vitamine C lorsque » l'on aromatise au goût d'orange, EXEMPLE 6An effervescent composition for a sparkling drink is prepared in the following proportions: sugar ................................... ...... 17 g L-lysine carbamate ......................... 1.4 g citric acid ...... .......................... 2.7 g which can be flavored in a known manner with powdered fruit extracts. You can also optionally add vitamin C when flavoring with orange flavor, EXAMPLE 6
Préparation de comprimés effervescents dosés à 0,5 g de phosphore On utilisera par exemple la formulation suivante : 30 carbamate de L-lysine ......................... 1,4 g phosphate de glycocclle ....................... 1,397 g phosphate monobasique de magnésium anhydre .... 0,881 g Les comprimés des exemples 4 et 6 sont préparés de manière connue de l'homme de l'art par desséchage séparé des composants, tamisage, 35 mélange et mise en comprimés.Preparation of effervescent tablets dosed with 0.5 g of phosphorus The following formulation will be used, for example: 30 L-lysine carbamate ........................ 1.4 g glycocclle phosphate ....................... 1.397 g monobasic anhydrous magnesium phosphate .... 0.881 g The tablets of Examples 4 and 6 are prepared in a manner known to those skilled in the art by separate drying of the components, sieving, mixing and tableting.
Les effets thérapeutiques, doses et voies d'administration de telles préparations sont également connus.The therapeutic effects, doses and routes of administration of such preparations are also known.
Claims (4)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7836011A FR2444665B1 (en) | 1978-12-21 | 1978-12-21 | NEW PROCESS FOR THE PREPARATION OF L-LYSINE CARBAMATE |
| FR7836011 | 1978-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82007A1 true LU82007A1 (en) | 1980-07-21 |
Family
ID=9216407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82007A LU82007A1 (en) | 1978-12-21 | 1979-12-18 | NEW PROCESS FOR THE PREPARATION OF L-LYSINE CARBAMATE |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5587753A (en) |
| BE (1) | BE880749A (en) |
| DE (1) | DE2951132A1 (en) |
| ES (1) | ES487158A1 (en) |
| FR (1) | FR2444665B1 (en) |
| GB (1) | GB2037760B (en) |
| IT (1) | IT1119633B (en) |
| LU (1) | LU82007A1 (en) |
| NL (1) | NL7909081A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4760138A (en) * | 1984-12-13 | 1988-07-26 | Nestec S. A. | Carbonating agents and their preparation |
| US4937083A (en) * | 1988-04-12 | 1990-06-26 | Mitsubishi Chemical Industries Limited | Feed additive for ruminants |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2215950A2 (en) * | 1973-02-01 | 1974-08-30 | Union Pharma Scient Appl | Carbonated lysine - as carbonate source in effervescent compositions |
-
1978
- 1978-12-21 FR FR7836011A patent/FR2444665B1/en not_active Expired
-
1979
- 1979-12-07 GB GB7942236A patent/GB2037760B/en not_active Expired
- 1979-12-17 JP JP16395479A patent/JPS5587753A/en active Granted
- 1979-12-17 NL NL7909081A patent/NL7909081A/en not_active Application Discontinuation
- 1979-12-18 LU LU82007A patent/LU82007A1/en unknown
- 1979-12-19 DE DE19792951132 patent/DE2951132A1/en active Granted
- 1979-12-20 ES ES487158A patent/ES487158A1/en not_active Expired
- 1979-12-20 IT IT69447/79A patent/IT1119633B/en active
- 1979-12-20 BE BE2/58288A patent/BE880749A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1119633B (en) | 1986-03-10 |
| ES487158A1 (en) | 1980-09-16 |
| DE2951132C2 (en) | 1988-12-22 |
| IT7969447A0 (en) | 1979-12-20 |
| FR2444665B1 (en) | 1985-06-28 |
| NL7909081A (en) | 1980-06-24 |
| FR2444665A1 (en) | 1980-07-18 |
| BE880749A (en) | 1980-06-20 |
| GB2037760A (en) | 1980-07-16 |
| DE2951132A1 (en) | 1980-07-10 |
| JPS5587753A (en) | 1980-07-02 |
| JPS6320220B2 (en) | 1988-04-26 |
| GB2037760B (en) | 1983-05-11 |
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