CH199955A - Process for the preparation of the 3-carboxamide of N-triacetyl-arabinosido-pyridinium bromide. - Google Patents
Process for the preparation of the 3-carboxamide of N-triacetyl-arabinosido-pyridinium bromide.Info
- Publication number
- CH199955A CH199955A CH199955DA CH199955A CH 199955 A CH199955 A CH 199955A CH 199955D A CH199955D A CH 199955DA CH 199955 A CH199955 A CH 199955A
- Authority
- CH
- Switzerland
- Prior art keywords
- triacetyl
- pyridinium bromide
- arabinosido
- preparation
- carboxamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 235000005152 nicotinamide Nutrition 0.000 claims description 4
- 239000011570 nicotinamide Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CYAYKKUWALRRPA-RGDJUOJXSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O CYAYKKUWALRRPA-RGDJUOJXSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- -1 nicotinic acid imide Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/048—Pyridine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung des 3-Carbonsäureamids des N-Triacetyl- arabinosido-pyridiniumbromids. Bei der Einwirkung von Acetohalogen- zuckern, wie Acetobromglucose, Acetobrom- arabinose oder Acetobromribose auf Nikotin- säuretimid in indifferenten Lösungsmitteln, wie Dioxan, bilden sich Verbindungen, die den Formeln I und II
EMI0001.0013
entsprechen.
In ihnen können die Acetylreste durch Verseifung, zum Beispiel mit sehr ver dünnter Bromwasserstoffsäure, abgespalten werden. Eine 'Verbindung des Pyridins mit Acetobromglucose ist vor längerer Zeit von E. Fischer und g. Raske (Berichte der Deut schen Chemischen Gesellschaft 43 [1910] S. 1750) zufällig erhalten worden.
Daraus konnte aber natürlich nicht vorausgesehen werden, ob sich auch Derivate des Pyridins, insbesondere Nikotinsäureamid, mit Aceto- halogenzuckern verbinden lassen; dies umso weniger, als die genannten Forscher fanden, dass auch die Anlagerung von Acetobrom- glucose an Pyridin nur bei Gegenwart eines Katalysators, etwa Phenol, gelang.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung des 3-Carbon- säureamids des N-Triacetyl-arabinosido-pyri- diniumbromids, welches dadurch gekennzeich net ist, dass man 1-Acetobromarabinose auf Nikotinsäureamid in Gegenwart eines in differenten Lösungsmittels einwirken lässt.
Das 3-Carbonsäureamid des N-Triacetyl- arabinosido-pyridiniumbromids zeigt wenig Neigung zur Kristallisation. Es ist eehr leicht löslich in Wasser und in Alkohol, unlöslich in Äther und Benzin und soll als Ausgangs stoff für die Herstellung von Arzneimitteln dienen.
Beispiel: 12,1 Teile Nikotinsäureamid werden in Diogan gelöst und in die Lösung 33,9 Teile 1-Acetobromarabinose eingetragen. Die Lösung bleibt sodann 48 Stunden bei<B>37'</B> stehen. Das 3-Carbonsäureamid des N-Triacetyl-arabino- sido-pyridiniumbromids findet sich hauptsäch lich in der Dioganmutterlauge und zeigt wenig Neigung zur Kristallisation.
Process for the preparation of the 3-carboxamide of N-triacetyl-arabinosido-pyridinium bromide. When acetohalosugars, such as acetobromoglucose, acetobromarabinose or acetobromribose, act on nicotinic acid imide in inert solvents such as dioxane, compounds are formed which correspond to the formulas I and II
EMI0001.0013
correspond.
In them, the acetyl residues can be split off by saponification, for example with very dilute hydrobromic acid. A 'connection of pyridine with acetobromoglucose is a long time ago by E. Fischer and g. Raske (reports of the German Chemical Society 43 [1910] p. 1750) was received by chance.
From this, however, it could of course not be foreseen whether derivatives of pyridine, in particular nicotinic acid amide, could also be combined with aceto-halogen sugars; This is all the less so since the researchers mentioned found that the addition of acetobromoglucose to pyridine only succeeded in the presence of a catalyst such as phenol.
The subject of the present patent is a process for the preparation of the 3-carboxylic acid amide of N-triacetyl-arabinosido-pyridinium bromide, which is characterized in that 1-acetobromarabinose is allowed to act on nicotinic acid amide in the presence of a different solvent.
The 3-carboxamide of N-triacetyl-arabinosido-pyridinium bromide shows little tendency to crystallize. It is very easily soluble in water and alcohol, insoluble in ether and gasoline and is intended to serve as a starting material for the manufacture of medicines.
Example: 12.1 parts of nicotinic acid amide are dissolved in Diogan and 33.9 parts of 1-acetobromarabinose are added to the solution. The solution then remains at <B> 37 '</B> for 48 hours. The 3-carboxamide of N-triacetyl-arabinosido-pyridinium bromide is mainly found in the Diogan's mother liquor and shows little tendency to crystallize.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH199955T | 1936-12-08 | ||
| CH195322T | 1936-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199955A true CH199955A (en) | 1938-09-15 |
Family
ID=25722739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199955D CH199955A (en) | 1936-12-08 | 1936-12-08 | Process for the preparation of the 3-carboxamide of N-triacetyl-arabinosido-pyridinium bromide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199955A (en) |
-
1936
- 1936-12-08 CH CH199955D patent/CH199955A/en unknown
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