CH204759A - Process for the preparation of a new therapeutically effective amidine. - Google Patents
Process for the preparation of a new therapeutically effective amidine.Info
- Publication number
- CH204759A CH204759A CH204759DA CH204759A CH 204759 A CH204759 A CH 204759A CH 204759D A CH204759D A CH 204759DA CH 204759 A CH204759 A CH 204759A
- Authority
- CH
- Switzerland
- Prior art keywords
- quinoline
- ether
- therapeutically effective
- amidine
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000001409 amidines Chemical class 0.000 title claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- -1 quinoline - 8 - oxy - acetimido ethyl Chemical group 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen therapeutisch wirksamen Amidines. Es wurde gefunden, dass man zu einem neuen therapeutisch wirksamen Amdin ge langen kann, wenn man einen Chinolin-8- oxyacetimicloäther mit Piperidin umsetzt.
Das so gewonnene Chinolin-8-oxyätlienyl- piperidin-amidin der Formel
EMI0001.0016
bildet ein Dihydrochlorid vom F.2,08 bis 210, das sich, in Wasser leicht löst.
Die neue Verbindung soll therapeutische Verwendung finden.
Beispiel: 30 Teile Chinolin - 8 - oxyacetimidoäthyl- äther-hydrochlorid, aus dem sich während :der Umsetzung Chinolin - 8 - oxy - acetimido- äthyläther bildet, werden mit einer alkoholi- sehen Lösung von :
8,5 Teilen Piperidin in Gegenwart von Natriumalkoholat gezchüttelt. Sodann wird vom entstandenen Natrium- chlorid abgesaugt und :die Lösung mit alko holischer ':Salzsäure versetzt.
Man erhält so das Ghinolin- 8 -oxyätllenyl-piperidin-amidin- äihydrochlorid als farbloses Kristallpulver, aus dem sich mittels Alkalien die freie Base gewinnen lässt.
Das ,Natriumalkoholat kann auch. durch andere basische Mittel, wie z. B. Piperidin selbst, andere Alkoholorte oder tertiäre Basen ersetzt werden.
'Statt von Chinolin- 8 -oxyacetimidoätllyl- äther kann man ebensogut auch von einem andern Äther, wie .z. B. vom Methyl-, Pro- pyl- oder Butyläther, ausgehen.
An Stelle :des salzsauren Salzes,des Chino- lin-8-oxyaoetimidoätllyläthers kann auch ,die freie Base selbst oder ein anderes Salz wie z. B. :das Hydrobromid oder das s:chwefel- saure Salz Verwendung finden.
Process for the preparation of a new therapeutically effective amidine. It has been found that a new therapeutically effective amdin can be obtained by reacting a quinoline-8-oxyacetimicloether with piperidine.
The quinoline-8-oxyätlienyl-piperidin-amidine of the formula obtained in this way
EMI0001.0016
forms a dihydrochloride from F.2.08 to 210, which easily dissolves in water.
The new compound should find therapeutic use.
Example: 30 parts of quinoline - 8 - oxyacetimidoethyl ether hydrochloride, from which quinoline - 8 - oxy - acetimido ethyl ether is formed during: the reaction, are mixed with an alcoholic solution of:
8.5 parts of piperidine shaken in the presence of sodium alcoholate. The sodium chloride formed is then suctioned off and: alcoholic hydrochloric acid is added to the solution.
The ghinolin-8-oxyätllenyl-piperidin-amidin- Äihydrochlorid is obtained as a colorless crystal powder from which the free base can be obtained by means of alkalis.
That, sodium alcoholate can too. by other basic agents, such as. B. piperidine itself, other alcohol sites or tertiary bases are replaced.
'Instead of quinoline-8-oxyacetimidoethyl ether one can just as easily use another ether, such as e.g. B. from methyl, propyl or butyl ethers, start.
Instead of: the hydrochloric acid salt, the quinoline-8-oxyaoetimidoätllyläthers can also, the free base itself or another salt such. B.: the hydrobromide or the sulfuric acid salt can be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH204759T | 1935-06-21 | ||
| CH200478T | 1938-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH204759A true CH204759A (en) | 1939-05-15 |
Family
ID=25723516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH204759D CH204759A (en) | 1935-06-21 | 1935-06-21 | Process for the preparation of a new therapeutically effective amidine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH204759A (en) |
-
1935
- 1935-06-21 CH CH204759D patent/CH204759A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH204759A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204756A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204757A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204758A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204754A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204755A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204763A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH235951A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204753A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH234977A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204761A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204742A (en) | Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. | |
| DE933754C (en) | Process for the preparation of derivatives of tetrahydro-ª † -carboline | |
| CH229523A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204762A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH200478A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| DE644078C (en) | Process for the preparation of a salt of 4-oxy-3-acetylaminophenyl-1-arsic acid with the toxin of iso-octylhydrocupreine (vuzinotoxin) | |
| CH235953A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH204766A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| DE531363C (en) | Process for the preparation of basic esters of substituted quinoline-4-carboxylic acids | |
| DE1057133B (en) | Process for the production of new, pharmacologically active 1,1-diphenyl-2-aminoalkanols | |
| DE907295C (en) | Manufacture of alkyl mercury chloride | |
| CH204760A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH234982A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH234980A (en) | Process for the preparation of a new therapeutically effective amidine. |