CH200245A - Process for the preparation of the 3-carboxamide of N-arabinosido-dihydropyridine. - Google Patents
Process for the preparation of the 3-carboxamide of N-arabinosido-dihydropyridine.Info
- Publication number
- CH200245A CH200245A CH200245DA CH200245A CH 200245 A CH200245 A CH 200245A CH 200245D A CH200245D A CH 200245DA CH 200245 A CH200245 A CH 200245A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxamide
- preparation
- arabinosido
- dihydropyridine
- sep
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 230000001603 reducing effect Effects 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012442 inert solvent 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
- 229910001961 silver nitrate Inorganic materials 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darsteltung des 3-Carbonsäureamids des N-Arabinosido-dihydropyridins. Es wurde gefunden, dass sich aus den zum Beispiel durch Einwirkung von 1-Aceto- halogenirabinose und Nikotins2#ureami@d in .einem indifferenten Lösungsmittel erhält lieh-en 3-Carbonsäureami:
den der N-Triacetyl- a.rabinos.dopyridiniumhalogenide durch Be handlung mit Reduktionsmitteln in aJka.- lischer Lösung das 3-Carbonsäureamid des N-Triacetylarabinosidodihydropyridins. ge winnen lässt, ohne ,dass .dabei der acylierte Zuckerrest irgendwie verändert wird.
Die entstehende gut kristallisierende Dihydrover- bindung b.e@itzt vermutlich folgende Konsti- tution
EMI0001.0029
Aus dem so erhaltenen @3-Carbonsäureamid des N-Triacetylarabinosidodihydropyridins wird,erfindungsb mäss durch Abspaltung der
EMI0001.0036
I@ <SEP> I <SEP> i <SEP> i'i <SEP> I <SEP> @I <SEP> I <SEP> @@I Acetyl@reste das - 3,
-Carbonsäureamid des, N- Arabinasidodihydropyridins hergestellt.
Die neue Verbindung zersetzt sich ober halb IM , wirkt reduzierend und zeigt in alkalischer Lösung ein Absorptionsmaximum bei 340,u,u. .Sie soll als Ausgangsstoff für die Herstellung von Arzneimitteln dienen.
<I>Beispiel:</I> Teile der Verbindung aus 1-Acetobrom- arabinose und Nikotinsä.ureamid werden in 50 Teilen Wasser gelöst und dazu je 5 Teile Natriumbicarbonat und 5 Teile Natrium- hydrosulfit gegeben. Dabei färbt sich die Lösung gelb.
Nach mehrstündigem Stehen extrahiert man die Flüssigkeit wiederholt mit Chloroform und dampft die Chloroform- egtrakte unter verminderbem Druck ein. Da bei bleibt das 3-Carbonsäureamid des N-Triacetylarabinosidodihydropyridins als amorphe -Masse zurück.
Die Verbindung reduziert Silbernitratlösung in der Wärme. Zur Abspaltung .der Acetylgruppe löst mann sie in konzentriertem alkoholischem Am moniak, lässt acht Stunden bei Zimmertempe- ratur stehen, verdampft hierauf das Ijö- sungsmittel im Vakuum und kristallisiert den Rückstand,
das 3-Carbonsäureamid des N-Arabinosidodihydropyridins aus etwa 90 % igem Alkohol um.
Process for the preparation of the 3-carboxamide of N-arabinosido-dihydropyridine. It has been found that the 3-carboxylic acid amides obtained, for example, by the action of 1-acetohalogenirabinose and nicotine2 # ureami @ d in an inert solvent:
that of the N-triacetyl a.rabinos.dopyridinium halide by treatment with reducing agents in aJka.- lischer solution the 3-carboxamide of N-triacetylarabinosidodihydropyridine. can be obtained without the acylated sugar residue being changed in any way.
The resulting dihydro compound, which crystallizes well, b.e@itzt presumably has the following constitution
EMI0001.0029
The resulting @ 3-carboxamide of N-triacetylarabinosidodihydropyridine is, according to the invention, by splitting off the
EMI0001.0036
I @ <SEP> I <SEP> i <SEP> i'i <SEP> I <SEP> @I <SEP> I <SEP> @@ I Acetyl @ reste das - 3,
-Carboxamide des, N-Arabinasidodihydropyridins produced.
The new compound decomposes above half IM, has a reducing effect and shows an absorption maximum at 340, u, u in alkaline solution. It is intended to serve as a raw material for the manufacture of drugs.
<I> Example: </I> parts of the compound from 1-acetobromoarabinose and nicotinic acid amide are dissolved in 50 parts of water and 5 parts of sodium bicarbonate and 5 parts of sodium hydrosulfite are added. The solution turns yellow.
After standing for several hours, the liquid is extracted repeatedly with chloroform and the chloroform extracts are evaporated under reduced pressure. The 3-carboxamide of N-triacetylarabinosidodihydropyridine remains as an amorphous mass.
The compound reduces silver nitrate solution in the heat. To split off the acetyl group, dissolve it in concentrated alcoholic ammonia, leave it to stand for eight hours at room temperature, then evaporate the solvent in vacuo and crystallize the residue.
the 3-carboxamide of N-arabinosidodihydropyridine from about 90% alcohol.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH195950T | 1936-12-08 | ||
| CH200245T | 1936-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200245A true CH200245A (en) | 1938-09-30 |
Family
ID=25722815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200245D CH200245A (en) | 1936-12-08 | 1936-12-08 | Process for the preparation of the 3-carboxamide of N-arabinosido-dihydropyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH200245A (en) |
-
1936
- 1936-12-08 CH CH200245D patent/CH200245A/en unknown
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