NO121939B - - Google Patents
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- Publication number
- NO121939B NO121939B NO15566664A NO15566664A NO121939B NO 121939 B NO121939 B NO 121939B NO 15566664 A NO15566664 A NO 15566664A NO 15566664 A NO15566664 A NO 15566664A NO 121939 B NO121939 B NO 121939B
- Authority
- NO
- Norway
- Prior art keywords
- triazine
- acid
- diethylamino
- bis
- salts
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 5
- MLGUQYVAVJHCGI-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetraethyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC=NC(N(CC)CC)=N1 MLGUQYVAVJHCGI-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 2
- IRQOBYXMACIFKD-UHFFFAOYSA-N meladrazine Chemical compound CCN(CC)C1=NC(=NN)N=C(N(CC)CC)N1 IRQOBYXMACIFKD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- -1 1,3,5-triazine compound Chemical class 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- QHXDTLYEHWXDSO-UHFFFAOYSA-N 6-chloro-2-n,2-n,4-n,4-n-tetraethyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(Cl)=NC(N(CC)CC)=N1 QHXDTLYEHWXDSO-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- LOZOGGLFSJGOHI-UHFFFAOYSA-N triazin-4-ylhydrazine Chemical compound NNC1=CC=NN=N1 LOZOGGLFSJGOHI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65B—MACHINES, APPARATUS OR DEVICES FOR, OR METHODS OF, PACKAGING ARTICLES OR MATERIALS; UNPACKING
- B65B25/00—Packaging other articles presenting special problems
- B65B25/06—Packaging slices or specially-shaped pieces of meat, cheese, or other plastic or tacky products
- B65B25/061—Packaging slices or specially-shaped pieces of meat, cheese, or other plastic or tacky products of fish
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Processing Of Meat And Fish (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Basic Packing Technique (AREA)
Description
Fremgangsmåte til fremstilling av 2-hydrazmo-4,6-bis-dietylamino -1,3,5 -triazin.
Gjenstanden for foreliggende oppfin-nelse er fremstilling av 2-hydrazino-4,6-bis-dietylamino-l,3,5-triazin med formelen
og dens salter.
Den nevnte forbindelser og dens salter oppviser verdifulle farmakologiske egen-skaper. Således har de en hemmende virk-ning på pirringsoverføringen i sentralner-vesystemet og kan derfor anvendes som legemiddel ved nevrologiske sykdommer.
Den nye 1,3,5-triazinforbindelse fåes når man i en 4,6-bis-dietylamino-l,3,5-tri-azin, som i 2-stilling har en rest som kan overføres til hydrazinogruppen, danner hydrazinogruppen. Således kan man omsette en 4,6-bisdietylamino-l,3,5-triazin, som i 2-stilling har en utbyttbar rest, f. eks. forestret oksygruppe, særlig et holo-genatom, med hydrazin. Hydrazin kan også anvendes i form av dets salter. Om-setningen foretas hensiktsmessig i nærvær av fortynningsmidler, i alle tilfelle også i nærvær av kondensasjonsmidler, idet man dessuten kan arbeide i nærvær av katal-ysatorer, slik som kobberpulver.
Såfremt de for gjennomføringen av nevnte reaksjoner nødvendige utgangsstof-
fer ikke er kjent, kan de fremstilles etter vanlige fremgangsmåter.
Alt etter arbeidsmåten får man det nye hydrazinotriazin i form av dets base eller dets salter. Fra basen kan det dannes terapeutisk anvendelige salter, slik som av halogenvannstoffsyrene, svovelsyre, salpe-tersyre, fosforsyre, eddiksyre, propionsyre, oksalsyre, eplesyre, sitronsyre metansulfonsyre, etansulfonsyre, oksyetansulfon-syre, bensoesyre, salisylsyre, p-aminosali-sylsyre eller toluolsulfonsyre. Erholdte salter kan på vanlig måte overføres til den fri base.
Den nye forbindelse eller dens salter kan anvendes som legemidler, f. eks. i form av farmasøytiske preparater, som inneholder dette eller deres salter i blan-ding med et for enteral, parenteral eller topikal anvendelse egnet farmasøytisk organisk eller anorganisk, fast eller fly-tende bærematerial.
Oppfinnelsen beskrives nærmere i de følgende eksempler. Temperaturene er an-gitt i Celsius-grader.
Eksempel 1:
983 g 2-klor-4,6-bis-dietylamino-l,3,5-triazin oppløses i 5000 ems 96 psfs alkohol og tilsettes 1000 cm» hydrazinhydrat. Etter 3 timers henstand ved romtemperatur opp-varmes blandingen ennu 2 timer på vann-bad. Oppløsningen inndampes fullstendig i vakuum, den oljeaktige rest oppløses i fortynnet saltsyre, innstilles alkalisk med natronlut og utrystes deretter flere ganger med eter. De forenede eteroppløsninger
rystes med fortynnet saltsyre, den vandige oppløsning innstilles på ny alkalisk med natronlut og rystes ut med eter, Den orga-niske fase tørkes og inndampes fullstendig. Man får således 2-hydrazino-4,6-bisdietyl-amino-l,3,5-triazin med følgende formel
Det er en fargeløs væske, som krystal-liserer etter lengere tids henstand og lar seg omsette med alkoholisk saltsyre og etertilsetning til dihydrokloridet med føl-gende formel :
Det smelter ved 198—200°.
Eksempel 2: 10 g 2-hydrazino-4,6-bis-dietylamino-1,3,5-trizin oppløses i 80 ems abs. eter og tilsettes langsomt 3,8 g metansulfonsyre, oppløst i 20 ems abs. eter. Det dannes straks et hvitt harpiks, som i løpet av to dager ved romtemperatur omdannes til en krystallisert forbindelse. Den hvite rest suges fra, vaskes med abs. eter og omkrys-talliseres fra eddikester/petroleter. Man får således 2-hydrazino-4,6-bis-dietylami-no-l,3,5-triazin-monometansulfonat med formelen :
som et hvitt krystallisert produkt, som smelter ved 97—99°. Fra eterfiltratet kan som biprodukt fåes noe 2-hydrazino-4,6-bis-dietylamino-1,3,5-triazin-dimetansulfonat med følgende formel
Det danner hvite krystaller, som smelter ved 175—176°.
Claims (2)
1. Fremgangsmåte til fremstilling av 2-hydrazino-4,6-bis-dietylamino-l,3,5-tria-zin, karakterisert ved at man i en 4,6-bis-dietylamino-l,3,5-triazin som i 2-stilling inneholder en utbyttbar substituent, f. eks. en forestret oksygruppe, danner hydrazin-gruppen ved omsetning med hydrazin og om ønskes overfører den eventuelt erholdte base til sine salter eller omdanner erholdte salter til den frie base.
2. Fremgangsmåte ifølge påstand 1, karakterisert ved at man omsetter et 2-halogen-4,6-bis-dietylamino-1,3,5-triazin med hydrazin.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB74343A DE1266204B (de) | 1963-11-20 | 1963-11-20 | Vorrichtung zum Verpacken von rohem Fischfilet in abgemessenen Mengen |
Publications (1)
Publication Number | Publication Date |
---|---|
NO121939B true NO121939B (no) | 1971-04-26 |
Family
ID=6978211
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO15566664A NO121939B (no) | 1963-11-20 | 1964-11-20 |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE1266204B (no) |
GB (1) | GB1058179A (no) |
NO (1) | NO121939B (no) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2758528B1 (fr) * | 1997-01-20 | 1999-03-05 | Neptune | Procede de dosage et/ou formage d'aliments, aliments obtenus par ledit procede, et conditionnement susceptible d'etre mis en oeuvre par ledit procede |
ES2350778B1 (es) * | 2008-09-05 | 2011-11-18 | Hermanos Rodriguez Gomez, S.A. - Hermasa | Maquina de compactacion y envasado de pescado. |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1450104A (en) * | 1921-02-08 | 1923-03-27 | Victor Kleinberg | Meat-packing machine |
US2334774A (en) * | 1941-04-03 | 1943-11-23 | Armour & Co | Method of packing comminuted meats |
US2575703A (en) * | 1946-08-08 | 1951-11-20 | Eben H Carruthers | Method for packing food products |
US2669378A (en) * | 1949-10-13 | 1954-02-16 | Eben H Carruthers | Machine for packing a predetermined weight of bulk product |
US2926095A (en) * | 1953-04-20 | 1960-02-23 | Keystone Packing Machine Corp | Method and apparatus for canning fish |
US2840121A (en) * | 1953-11-12 | 1958-06-24 | Eben H Carruthers | Machine for packing a predetermined weight of bulk products |
-
1963
- 1963-11-20 DE DEB74343A patent/DE1266204B/de active Pending
-
1964
- 1964-11-18 GB GB4701064A patent/GB1058179A/en not_active Expired
- 1964-11-20 NO NO15566664A patent/NO121939B/no unknown
Also Published As
Publication number | Publication date |
---|---|
GB1058179A (en) | 1967-02-08 |
DE1266204B (de) | 1968-04-11 |
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