NL7909081A - PROCESS FOR THE PREPARATION OF L-LYSINE CARBAMATE - Google Patents
PROCESS FOR THE PREPARATION OF L-LYSINE CARBAMATE Download PDFInfo
- Publication number
- NL7909081A NL7909081A NL7909081A NL7909081A NL7909081A NL 7909081 A NL7909081 A NL 7909081A NL 7909081 A NL7909081 A NL 7909081A NL 7909081 A NL7909081 A NL 7909081A NL 7909081 A NL7909081 A NL 7909081A
- Authority
- NL
- Netherlands
- Prior art keywords
- lysine
- carbamate
- carbon dioxide
- filtrate
- filtered
- 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
- 238000002360 preparation method Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 20
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 16
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 9
- 235000019766 L-Lysine Nutrition 0.000 claims description 8
- 239000004472 Lysine Substances 0.000 claims description 8
- 239000001569 carbon dioxide Substances 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229940072033 potash Drugs 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 238000004042 decolorization Methods 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000002156 mixing Methods 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000007938 effervescent tablet 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
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-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
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000004480 active ingredient 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
- 230000003139 buffering effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- MHJAJDCZWVHCPF-UHFFFAOYSA-L dimagnesium phosphate Chemical compound [Mg+2].OP([O-])([O-])=O MHJAJDCZWVHCPF-UHFFFAOYSA-L 0.000 description 1
- 229910000395 dimagnesium phosphate Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940068517 fruit extracts Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 235000014659 low sodium diet Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 210000002784 stomach Anatomy 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
• ” .• ”.
' '' ' ' "^s ·'· >'' '' '"^ s ·' ·>
Br/O/lh/1Br / O / lh / 1
Werkwijze voor de bereiding van L-lysinecarbamaat.Process for the preparation of L-lysine carbamate.
De uitvinding heeft betrekking op een goedkopere werkwijze voor de bereiding van. L-lysinecarbamaat.The invention relates to a cheaper method for the preparation of. L-lysine carbamate.
L-lysinecarbamaat wordt gebruikt als bestanddeel van bruis-preparaten voor brulzende dranken en bruizen-5 de geneesmiddelen, bijvoorbeeld in zakjes of in dê vorm van tabletten, enz. Zulk een preparaat wordt vooral gebruikt voor geneesmiddelen met geen of weinig alkali-ionen, waardoor bij gebruik van het geneesmiddel een ongewenste accumulatie van alkali-ionen in organisme niet optreedt, zodat 10 daarmee patiënten met een natrium-arm dieet kunnen worden behandeld.L-lysine carbamate is used as a constituent of effervescent preparations for sparkling drinks and effervescent medicines, for example in sachets or in the form of tablets, etc. Such a preparation is mainly used for medicines with little or no alkali ions, so that when using the drug, an undesired accumulation of alkali ions in the organism does not occur, so that patients with a low sodium diet can thus be treated.
Andere voordelen van het gebruik van L-lysinecarbamaat bestaan hieruit, dat de maag het goed verdraagt ·* dankzij een bufferend milieu en dat het nagenoeg onmiddel-15 lijk door' het bloed wordt opgenomen.Other advantages of using L-lysine carbamate are that the stomach tolerates it well, * thanks to a buffering environment, and is absorbed almost immediately by the blood.
De uitvinding verschaft een nieuwe werkwijze voor de bereiding van L-lysinecarbamaat, waarbij van het monochloorhydraat van betrekkelijk goedkoop .L-lysine van diervoeder-kwaliteit kan worden uitgegaan. .The invention provides a new process for the preparation of L-lysine carbamate, in which the monochlorohydrate of relatively cheap feed grade L-lysine can be started from. .
20 Een oplossing van het monochloorhydraat wordt eerst met actieve koolstof behandeld, waarna het mengsel wordt gefiltreerd’ en het filtraat met een base, bijvoorbeeld kalium- of natriumcarbonaat, wordt behandeld en het gevormde zout, bijvoorbeeld kalium of natriumchloriöe, op bekende 25 wijze wordt verwijderd (bijvoorbeeld door filtreren) na toevoeging van bij voorkeur methanol. In of aan de verkregen' L-lysine-oplossing wordt dan koolzuur geleid of vast koolzuur toegevoegd, waarna het gevormde neerslag, alszijnde het gewenste produkt, wordt afgefiltreerd.A solution of the monochlorohydrate is first treated with activated carbon, then the mixture is filtered and the filtrate is treated with a base, for example potassium or sodium carbonate, and the salt formed, for example potassium or sodium chlorine, is removed in a known manner. (e.g. by filtration) after addition of preferably methanol. Carbon dioxide or solid carbon dioxide is then introduced into or into the L-lysine solution obtained, after which the precipitate formed, being the desired product, is filtered off.
30 Het zo verkregen L-lysinecarbamaat is in de vorm van een wit kristallijn poeder, dat zeer goed in water oplosbaar is, doch fiiet in methanol, waarmee het-produkt dan ook uitgewassen kan worden.The L-lysine carbamate thus obtained is in the form of a white crystalline powder, which is very soluble in water, but is finite in methanol, with which the product can therefore be washed out.
Zonder de bedoeling·de uitvinding te beperken 35 wordt hier verondersteld, dat het L-lysinecarbamaat, alszijn- 7909081 ' -2- ·&*' de een reactieprodukt uit equimolaire hoeveelheden L-lysine en CO^/ door een tweede L-lysine-moleeuul wordt gestabiliseerd ter verschaffing van de volgende formule: 5 HOOC(NH2)CH - (CH2)4 - NH - CÖOH .... NH^CCE^ - CH(NH2)COQH, hetgeen door de resultaten van analyses is bevestigd.Without the intention of limiting the invention, it is here assumed that the L-lysine carbamate, as its 7909081 -2- & * ', is a reaction product from equimolar amounts of L-lysine and CO2 by a second L-lysine. molecule is stabilized to give the following formula: 5 HOOC (NH 2) CH - (CH 2) 4 - NH - COOH ... NH 2 CCE - CH (NH 2) COQH, which has been confirmed by the results of analyzes.
De uitvinding zal verder worden verduidelijkt aan de hand van de volgende niet beperkende voorbeelden.The invention will be further elucidated by the following non-limiting examples.
10 Voorbeeld IExample I
300 g monochloorhydraat van L-lysine (feed grade = diervoederkwaliteit; gehalte y 98%) wordt bij 50-60°C in 300 ml water opgelost, waarna aan de oplossing 6 g actieve koolstof wordt toegevoegd en 15 min bij 60°C geroerd. Het 15 mengsel wordt met papier gefiltreerd en aan de oplossing wordt bij -40°C onder roeren portiegewijs 110 g potas toege-voegd, waarna het geheel tot kamertemperatuur wordt afgekoeld en 1 uur wordt geroerd. Aan het mengsel wordt portiegewijs 1500 ml’ methanol- toegevoegd>—gevolgd doOr-^^—uur - ------ 20 roeren en het affiltreren van het gevormde kaliumchloride.300 g of monochlorohydrate of L-lysine (feed grade = feed grade; content y 98%) are dissolved in 300 ml of water at 50-60 ° C, after which 6 g of activated carbon are added to the solution and stirred at 60 ° C for 15 min. The mixture is filtered with paper and 110 g of potash are added portionwise to the solution at -40 ° C with stirring, after which it is cooled to room temperature and stirred for 1 hour. To the mixture is added portionwise 1500 ml of methanol- followed by stirring and stirring and filtering the potassium chloride formed.
In het filtraat wordt in circa 1 uur 60-80 g koolzuurgas geleid, waarna het reaktiemengsel 1 nacht aan zichzelf wordt overgelaten; Het gevormde neerslag wordt afgefiltreerd, met 95%tig methanol uitgewassen en bij 40°C 25 gedroogd ter verschaffing van 200 g van het beoogde produkt' met een smeltpunt van 249-250°C.60-80 g of carbon dioxide are introduced into the filtrate in about 1 hour, after which the reaction mixture is left to stand overnight; The precipitate formed is filtered off, washed with 95% methanol and dried at 40 ° C to give 200 g of the target product, mp 249-250 ° C.
Analyse : Cl3H28N4Og .Analysis: Cl3H28N4Og.
Berekend : q % 46,41; H % 8,39; N % 16,65? O % 28,54-Gevonden : C % 46,62; H % 8,37; N % 16,39; 0 % 28,33.Calculated: q% 46.41; H% 8.39; N% 16.65? O% 28.54-Found: C% 46.62; H% 8.37; N% 16.39; 0% 28.33.
30 Voorbeeld IIExample II
300 g monochloorhydraat van L-lysine (diervoederkwaliteit; gehalte > 98%) wordt bij 30°C in 450 ml water opgelost. Aan de oplossing wordt in 15 min bij 30°C onder roeren 6 g actieve koolstof toegevoegd, die dan wordt 55 afgefiltreerd. Aan het filtraat wordt bij 20°C portiegewijs 79 g soda toegevoegd, waarna het geheel tot kamertemperatuur wordt afgekoeld en 1 uur wordt geroerd. Daaraan wordt dan portiegewijs 2000 ml methanol toegevoegd, waarna het 79 0 9x081 _ ' __ ' i is* -3- geheel 3 uren wordt geroerd en het gevormde natriumchloride wordt afgefiltreerd.300 g of monochlorohydrate of L-lysine (feed quality; content> 98%) are dissolved in 450 ml of water at 30 ° C. 6 g of active carbon are added to the solution over 15 minutes at 30 ° C with stirring, which is then filtered off. 79 g of soda are added portionwise at 20 ° C to the filtrate, after which it is cooled to room temperature and stirred for 1 hour. Then, 2000 ml of methanol are added portionwise, after which it is stirred for 3 hours and the sodium chloride formed is filtered off.
In het filtraat wordt in circa l uur 60-80 g koolzuur geleid, waarna men het 1 uur laat staan- Het gevorm-5 de neerslag wordt afgefiltreerd, met 95%tig methanol uitgewassen en bij 40°C gedroogd ter verschaffing van 189 g van het gewenste produkt met een smeltpunt van 246-25G°C.60-80 g of carbonic acid are introduced into the filtrate in about 1 hour and then left for 1 hour. The precipitate formed is filtered off, washed with 95% methanol and dried at 40 ° C to give 189 g of the desired product with a melting point of 246-25 ° C.
AnalyseAnalysis
Berekend : C % 46,41; H % 8,39; N % 16,65; 0 % 28,54 10 Gevonden : C % 46,23; H % 8,43; N % 16,67; 0 % 28,29.Calculated: C% 46.41; H% 8.39; N% 16.65; 0% 28.54 Found: C% 46.23; H% 8.43; N% 16.67; 0% 28.29.
Voorbeeld IIIExample III
Voorbeeld X wordt herhaald, doch nu wordt in plaats van koolzuurgas in toenemende hoeveelheden vast koolzuur toegevoegd tot er geen wit neerslag meer wordt ge-15 vormd. Na weer op kamertemperatuur gekomen te zijn wordt het mengsel 3,5 uür geroerd, waarna het neerslag wordt afgefiltreerd en met 800 ml methanol uitgewassen ter verschaffing van 192 g van het beoogde produkt met een smeltpunt van 247-250°C.Example X is repeated, but now instead of carbon dioxide gas is added in increasing amounts of solid carbon dioxide until no more white precipitate is formed. After returning to room temperature, the mixture is stirred for 3.5 hours, then the precipitate is filtered off and washed with 800 ml of methanol to give 192 g of the target product, mp 247-250 ° C.
20 Voorbeeld IVExample IV
Bruis-tabletten met acetylsalicylzuur zonder alkali-ionen.Effervescent tablets with acetylsalicylic acid without alkali ions.
0,500 g acetylsalicylzuur, 1,6 g L-lysine-carbamaat en 0,4 g citroenzuur worden met elkaar vermengd ter verschaffing van een poeder voor een tablet met 0,5 g 25 actief ingredient.0.500 g of acetylsalicylic acid, 1.6 g of L-lysine carbamate and 0.4 g of citric acid are mixed together to provide a powder for a tablet with 0.5 g of active ingredient.
Voorbeeld VExample V
Een bruis-preparaat voor bruizende drank wordt verkregen door 17 g suiker, 1,4 g L-lysinecarbamaat en 2,7 g citroenzuur tot een poeder te vermengen, waaraan, voor het 30 verschaffen van een aroma, vruchtextracten worden toegevoegd.An effervescent preparation for an effervescent drink is obtained by mixing 17 g of sugar, 1.4 g of L-lysine carbamate and 2.7 g of citric acid into a powder, to which fruit extracts are added to provide an aroma.
Ook kan men. aan het poeder vitamine C toevoegen en een sinaas-appelsmaak geven.One can also. add vitamin C to the powder and give it an orange flavor.
Voorbeeld VIExample VI
Bruis-tabletten met 0,5 g fosfor.Effervescent tablets with 0.5 g of phosphorus.
35 Een poeder wordt verkregen door 1,4 g L-lysine carbamaat, 1,397 g glycocolfosfaat en 0,881 g watervrij magnesiurowaterstoffosfaat met elkaar te vermengen.A powder is obtained by mixing 1.4 g of L-lysine carbamate, 1.397 g of glycol phosphate and 0.881 g of anhydrous magnesium hydrogen phosphate.
De tabletten van de voorbeelden 4-6 worden op 79 0 9 0 8 ί -4- * .. 's ' bekende wijze verkregen· door de componenten afzonderlijk te drogen, zeven en vermengen, waarna het verkregen poeder wordt getabletteerd.The tablets of Examples 4-6 are obtained in a known manner in the known manner by drying, sieving and mixing the components separately, after which the powder obtained is tableted.
De therapeutische werkingen, doses en wijzen 5 van toediening van de preparaten' zijn eveneens' bekend.The therapeutic actions, doses and modes of administration of the compositions are "also" known.
7 9 0 9 0 8 f7 9 0 9 0 8 f
Claims (5)
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 |
|---|---|
| NL7909081A true NL7909081A (en) | 1980-06-24 |
Family
ID=9216407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7909081A NL7909081A (en) | 1978-12-21 | 1979-12-17 | 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 |
| LU82007A1 (en) | 1980-07-21 |
| IT7969447A0 (en) | 1979-12-20 |
| FR2444665B1 (en) | 1985-06-28 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU631543B2 (en) | Synthetic gtf chromium material and process therefor | |
| CA2467805C (en) | Novel chromium (iii) alpha amino acid complexes | |
| JPH09503002A (en) | Water-soluble nimesulide salt and its production, aqueous solution containing this salt, nimesulide-based formulation and their use | |
| Seifullina et al. | Design and synthesis of new homo-and heterometal coordination compounds of germanium (IV) for preparation of low toxic drugs with a wide therapeutic action | |
| CN105394351A (en) | Oligosaccharide chelated composite trace element mineral matter supplement and preparation method thereof | |
| CN101606715A (en) | A kind of preparation method who disturbs anionic food-grade amino acid ferrous chelate compound that do not contain | |
| KR0143232B1 (en) | Preparation for iron supply, preparation for vitamin supply and method for stabilizing a foam preparation | |
| MX2010014466A (en) | Composition of flavanolignan and amino acid with improved water solubility. | |
| CA2085523A1 (en) | Water soluble derivatives of biotin and related therapeutical compositions | |
| NL7909081A (en) | PROCESS FOR THE PREPARATION OF L-LYSINE CARBAMATE | |
| US3361769A (en) | Bi-metallic salts of gluconic, glucuronic, or galacturonic acid | |
| JPH05238940A (en) | Fast-acting medicine having high absorption rate in vivo and its production | |
| FI71314B (en) | PROCEDURE FOR THE FRAMEWORK OF PROPERTY THERAPEUTIC BETA- (4,5-DIPHENYLOXAZOL-2-YL) PROPIONSYRAKALCIUMSALT | |
| CN100542525C (en) | The method for preparing 3-hydroxy-3-methyl sodium butyrate solid preparation | |
| CN107207494B (en) | Highly soluble acetone-added pyrroloquinoline quinone salt | |
| JPH09263573A (en) | Production of theanine | |
| CN107438595A (en) | Crystal formation and preparation method thereof | |
| JPS58101660A (en) | Improving method for solubility of steviolbioside | |
| JP2986133B2 (en) | Mineral absorption enhancer | |
| Wisniak | Paul schützenberger | |
| JP2022500507A (en) | Zinc complex compound containing citric acid and arginine ligand | |
| Pujari | Cocrystals of nutraceuticals: Protocatechuic acid and quercetin | |
| JPH0680622A (en) | Production of 4,4'-diaminostilbene-2,2'-disulfonic acid or its salt | |
| JPS62148467A (en) | Dipeptide derivative, production and use thereof | |
| GB2168354A (en) | Hemin compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: BRU GEB. MAGNIEZ. NICOLE FRANCOISE - |
|
| BV | The patent application has lapsed |