CH199956A - Process for the preparation of the 3-carboxamide of N-triacetyl-ribosido-pyridinium bromide. - Google Patents
Process for the preparation of the 3-carboxamide of N-triacetyl-ribosido-pyridinium bromide.Info
- Publication number
- CH199956A CH199956A CH199956DA CH199956A CH 199956 A CH199956 A CH 199956A CH 199956D A CH199956D A CH 199956DA CH 199956 A CH199956 A CH 199956A
- Authority
- CH
- Switzerland
- Prior art keywords
- triacetyl
- ribosido
- pyridinium bromide
- carboxamide
- acid amide
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 10
- 235000005152 nicotinamide Nutrition 0.000 claims description 5
- 239000011570 nicotinamide Substances 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- 239000007858 starting 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
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- -1 nicotinic acid amide bromohydrate Chemical compound 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup 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-ribosido- pyridiniumbromids. Bei der Einwirkung von Acetohalogen- zuckern, wie Acetobromglukose, Acetobrom- arabinose oder Acetobromribose auf Nikotin- säureamid in indifferenten Lösungsmitteln, wie Dioxan, bilden sich Verbindungen, die den Formeln I und II
EMI0001.0014
entsprechen.
In ihnen können die Acetyl- reste durch Verseifung, z. B. mit sehr ver dünnter Bromwasserstoffsäure, abgespalten werden. Eine Verbindung des Pyridins mit Acetobromglukose ist vor längerer Zeit von E. Fischer und K. 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- glukose an Pyridin nur bei Gegenwart eines Katalysators, etwas Phenol, gelang.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung des 3-Carbon- säureamids des N-Triacetyl-ribosido-pyridi- niumbromids, welches dadurch gekennzeich net ist, dass man a-Acetobromribose auf Nikotinsäureamid in einem indifferenten Lö sungsmittel einwirken lässt.
Das 3-Carbonsäureamid des N-Triacetyl- ribosido-pyridiniumbromids ist in Wasser und in Alkohol leicht löslich. Es soll als Ausgangsstoff für die Herstellung von Arznei mitteln dienen.
Beispiel: 0,93 Teile Nikotinsäureamid werden in der Hitze in 12 Teilen Diogan gelöst, die Flüssigkeit erkalten gelassen und hierauf mit 2,6 Teilen kristallisierter a-Acetobrom- ribose versetzt. Nach einigem Stehen hat sich ein kristalliner Niederschlag abgeschie den, der hauptsächlich aus Nikotinsäureamid- bromhydrat besteht. Das gebildete 3-Carbon- säureamid des N-Triacetyl-ribosido-pyridi- niumbromids findet sich in der Mutterlauge.
Nach dem Abfiltrieren des kristallinen Pro duktes wird die Dioganmutterlauge im Va kuum eingedampft und dabei ein Sirup er- halten, der im wesentlichen aus 3-Carbon- säureamid des N - Triacetyl - ribosido - pyridi- niumbromids besteht.
Process for the preparation of the 3-carboxamide of N-triacetyl-ribosidopyridinium bromide. When acetohalosugars, such as acetobromoglucose, acetobromarabinose or acetobromribose, act on nicotinic acid amide in inert solvents such as dioxane, compounds are formed which correspond to the formulas I and II
EMI0001.0014
correspond.
The acetyl residues in them can be saponified, e.g. B. be cleaved with very dilute hydrobromic acid ver. A compound of pyridine with acetobromoglucose was accidentally obtained a long time ago by E. Fischer and K. Raske (reports from the German Chemical Society 43 (1910) p. 1750).
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, a little phenol.
The subject of the present patent is a process for the preparation of the 3-carboxylic acid amide of N-triacetyl-ribosido-pyridinium bromide, which is characterized in that a-acetobromribose is allowed to act on nicotinic acid amide in an inert solvent.
The 3-carboxamide of N-triacetyl-ribosido-pyridinium bromide is easily soluble in water and alcohol. It is intended to serve as a raw material for the manufacture of pharmaceuticals.
Example: 0.93 parts of nicotinic acid amide are dissolved in 12 parts of Diogan in the heat, the liquid is allowed to cool and then 2.6 parts of crystallized α-acetobromoribose are added. After standing for a while, a crystalline precipitate has been deposited, which consists mainly of nicotinic acid amide bromohydrate. The 3-carboxylic acid amide of N-triacetyl-ribosido-pyridinium bromide formed is found in the mother liquor.
After the crystalline product has been filtered off, the Diogan mother liquor is evaporated in a vacuum and a syrup is obtained which essentially consists of 3-carboxylic acid amide of N-triacetyl-ribosido-pyridinium bromide.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH195322T | 1936-12-08 | ||
| CH199956T | 1936-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199956A true CH199956A (en) | 1938-09-15 |
Family
ID=25722740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199956D CH199956A (en) | 1936-12-08 | 1936-12-08 | Process for the preparation of the 3-carboxamide of N-triacetyl-ribosido-pyridinium bromide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199956A (en) |
-
1936
- 1936-12-08 CH CH199956D patent/CH199956A/en unknown
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