CH200247A - Process for the preparation of the 3-carboxamide of N-ribosido-dihydropyridine. - Google Patents
Process for the preparation of the 3-carboxamide of N-ribosido-dihydropyridine.Info
- Publication number
- CH200247A CH200247A CH200247DA CH200247A CH 200247 A CH200247 A CH 200247A CH 200247D A CH200247D A CH 200247DA CH 200247 A CH200247 A CH 200247A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- carboxamide
- preparation
- dihydropyridine
- ribosido
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001603 reducing effect Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 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)
- Pyridine Compounds (AREA)
Description
Verfahren zur Darstellung des 3-Carbonsäureamids des N-Ribosido-dihydropyridins.
EMI0001.0003
Es <SEP> wurde <SEP> gefunden, <SEP> dass <SEP> sich <SEP> aus <SEP> dem
<tb> zum <SEP> Beispiel <SEP> durch <SEP> Einwirkung <SEP> von <SEP> Aceto halogenribose <SEP> und <SEP> '.ikotinsäureamid <SEP> in <SEP> einem
<tb> indifferenten <SEP> Lösungsmittel <SEP> erhältlichen <SEP> 3 Canbonsäureamiden <SEP> Ader <SEP> N-Triaoetylribosido pyridiniumhalogenide <SEP> durch <SEP> Behandlung <SEP> mit
<tb> Reduktionsmitteln <SEP> in <SEP> alkalischer <SEP> Lösung <SEP> das
<tb> 3-Carbo#ns,äureamid <SEP> des <SEP> N-Triacetylribosido dihydropyri:
dins <SEP> gewinnen <SEP> lässt <SEP> , <SEP> olhne <SEP> da.ss <SEP> da bei <SEP> der <SEP> acylierte <SEP> Zuckerrest <SEP> irgendwie <SEP> ver ändert <SEP> wird. <SEP> Die <SEP> entstehende <SEP> gut <SEP> kristalli sieTende <SEP> Dihyd@rov <SEP> erbindung <SEP> besitzt <SEP> vermut lich <SEP> folgende <SEP> Konstitution:
EMI0001.0004
Aus dem so erhaltenen 3-Carbons,äureamid des N-Triacetylribosidodihydropyridins wird erfindungsgemäss durch Abspaltung der Acetylreste das 3--Carbonsäureamid des N- Ribosidodihydro@pyridins hergestellt.
. Die neue Verbindung ist in MTas@ser und Alkohol sehr leicht löslich und wirkt stark reduzierend. Sie soll alst Ausgangsstoff für die Herstellung von Arzneimitteln dienen. Beispiel:
2 Teile der Verbindung aus Acetobrom- ribose und Nikotinsäureamid werden in 100 Teilen Wasser, in welchem 8 Teile Natrium bicarbonat gelöst sind, aufgenommen. In die Flüssigkeit werden, allmählich 3,6 Teile Natrium#hydrosulfit eingetragen.
Nach etwa 14stündigem Stehen wird das Reaktions- gemisch mit insgesamt 40.0 Teilen Chloro form ausgeschüttelt; die Chloroformauszüge werden über Calciumehlorid getrocknet.
Beim Abdampfen des Chloroforms hinterbleibt das 3-Carbonsäureamid -des N-Triacetylribosido- dihydropyridins in Form eines Sirups, der sich durch Lösen in wenig abso lutem Alkohol und Äther in ein gelbliches Pulver verwandelt. Zur Abspaltung der Aoetyl,gruppen wird die Verbindung mit alkoholischem Ammoniak bei 0 behandelt.
Der Alkohol wird abgedampft und der Rück stand zur Entfernung des entstehenden Acet- amids mit heissem Essigester ausgezogen und hierauf mit Äther nachgewaschen. Es bleibt das 3-Carbonsäureaniiddes N-R.ibosido- dihydropy ridins als Pulver zurück, das aus hochprozentigem Alkohol umkristallisiert werden kann.
Process for the preparation of the 3-carboxamide of N-ribosido-dihydropyridine.
EMI0001.0003
<SEP> was found <SEP>, <SEP> that <SEP> is <SEP> from <SEP> the
<tb> for <SEP> example <SEP> by <SEP> action <SEP> of <SEP> aceto halogenribose <SEP> and <SEP> '.icotinamide <SEP> in <SEP> one
<tb> indifferent <SEP> solvent <SEP> available <SEP> 3 canboxamides <SEP> core <SEP> N-Triaoetylribosido pyridiniumhalogenide <SEP> by <SEP> treatment <SEP> with
<tb> reducing agents <SEP> in <SEP> alkaline <SEP> solution <SEP> das
<tb> 3-Carbo # ns, acid amide <SEP> of <SEP> N-Triacetylribosido dihydropyri:
win dins <SEP> <SEP> allows <SEP>, <SEP> without <SEP> da.ss <SEP> because with <SEP> the <SEP> acylated <SEP> sugar residue <SEP> somehow changes <SEP> < SEP> will. <SEP> The <SEP> resulting <SEP> well <SEP> crystallizing <SEP> Dihyd @ rov <SEP> compound <SEP> has <SEP> presumably <SEP> the following <SEP> constitution:
EMI0001.0004
According to the invention, the 3-carboxamide of N-ribosidodihydropyridine is prepared from the 3-carboxamide of N-triacetylribosidodihydropyridine obtained by splitting off the acetyl radicals.
. The new compound is very easily soluble in MTas @ ser and alcohol and has a strong reducing effect. It is intended to serve as the starting material for the manufacture of pharmaceuticals. Example:
2 parts of the compound of acetobromoribose and nicotinic acid amide are taken up in 100 parts of water in which 8 parts of sodium bicarbonate are dissolved. 3.6 parts of sodium hydrosulfite are gradually added to the liquid.
After standing for about 14 hours, the reaction mixture is shaken out with a total of 40.0 parts of chloroform; the chloroform extracts are dried over calcium chloride.
When the chloroform evaporates, the 3-carboxamide -des N-triacetylribosido- dihydropyridine remains in the form of a syrup, which turns into a yellowish powder when dissolved in a little absolute alcohol and ether. To split off the aoetyl groups, the compound is treated with alcoholic ammonia at 0.
The alcohol is evaporated and the residue is extracted with hot ethyl acetate to remove the acetamide that is formed and then washed with ether. The 3-carboxylic acid aniide of N-R.ibosidodihydropyridine remains as a powder, which can be recrystallized from high-percentage alcohol.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH200247T | 1936-12-08 | ||
| CH195950T | 1936-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200247A true CH200247A (en) | 1938-09-30 |
Family
ID=25722817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200247D CH200247A (en) | 1936-12-08 | 1936-12-08 | Process for the preparation of the 3-carboxamide of N-ribosido-dihydropyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH200247A (en) |
-
1936
- 1936-12-08 CH CH200247D patent/CH200247A/en unknown
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