CH243025A - Process for the preparation of a soluble salt of 4,4'-di-amidino-a, γ-diphenoxy-propane. - Google Patents
Process for the preparation of a soluble salt of 4,4'-di-amidino-a, γ-diphenoxy-propane.Info
- Publication number
- CH243025A CH243025A CH243025DA CH243025A CH 243025 A CH243025 A CH 243025A CH 243025D A CH243025D A CH 243025DA CH 243025 A CH243025 A CH 243025A
- Authority
- CH
- Switzerland
- Prior art keywords
- amidino
- diphenoxy
- propane
- soluble salt
- preparation
- Prior art date
Links
- 239000001294 propane Substances 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001875 compounds Chemical group 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- -1 dichlorohydrate Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/263—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings the aromatic rings being non-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines löslichen Salzes des 4,4'-1)1-amidino-a, r-diphenogy-propans. Es hat sich gezeigt, dass 4,4'-Di-amidino- a,y-diphenoxy-propan von beträchtlichem therapeutischem Interesse ist, doch sind seine Salze, wie das Dichlorhydrat, gleich wie bei andern aromatischen Di-amidinen, in Wasser nicht sehr gut löslich. Es ist jedoch gerade in der Therapie von Vorteil, beständige, in Was ser leicht lösliche Salze zur Verfügung zu haben, und die vorliegende Erfindung befasst sich mit der Herstellung eines solchen Salzes.
In vielen Fällen ergaben, wie festgestellt wurde, therapeutisch wertvolle basische Ver bindungen mit Methansulfonaten äusserst lös liche Salze; im Falle des 4,4'-Di-amidino-a,y- diphenoxy-propans ist jedoch das Di-methan- sulfonat nur wenig mehr löslich als das Di- chlorhydrat.
Gemäss dem Verfahren des vorliegenden Patentes wird ein leicht lösliches Salz des 4,4' - Di - amidino - a,y-diphenoxy-propans, das als Di-isäthionat bezeichnet werden kann, da durch hergestellt, dass man 4,4'-Di-amidino- a,y-diphenoxy-propan mit ,ö-Oxyäthansulfon- säure umsetzt. <I>Beispiel:
</I> 8,2 g 4,4'-Di-amidino-a,y-diphenoxy-pro- pan wurden in einem geringen Überschuss an 4 n ss-Oxyäthansulfosäure gelöst, die Lösung war gerade iackmussauer. Sie wurde mit Kohle filtriert, die festen Anteile mit etwas Methanol gewaschen und das Di-isäthionat aus Filtrat und Waschflüssigkeit durch Zu gabe von Aceton gefällt. Die Ausbeute an 4,4'-Di-amidino-a,y-diphenoxy-propan betrug 5,29. Die Löslichkeit in Wasser war etwa 1 in 4 bei 20 C.
Process for the preparation of a soluble salt of 4,4'-1) 1-amidino-a, r-diphenogy-propane. 4,4'-Di-amidino-α, γ-diphenoxy-propane has been shown to be of considerable therapeutic interest, but its salts, like dichlorohydrate, like other aromatic di-amidines, are not very much in water easily soluble. However, it is precisely in therapy of advantage to have stable, readily soluble salts in what water available, and the present invention is concerned with the production of such a salt.
In many cases, it was found that therapeutically valuable basic compounds with methanesulfonates resulted in extremely soluble salts; in the case of 4,4'-di-amidino-α, γ-diphenoxy-propane, however, the di-methanesulfonate is only slightly more soluble than the dichlorohydrate.
According to the process of the present patent, a readily soluble salt of 4,4'-di-amidino-a, y-diphenoxy-propane, which can be referred to as di-isethionate, is produced by the fact that 4,4'-di -amidino- a, y-diphenoxy-propane with, ö-oxyethanesulfonic acid. <I> example:
8.2 g of 4,4'-di-amidino-a, γ-diphenoxy-propane were dissolved in a slight excess of 4 n ß-oxyethanesulfonic acid, the solution was just iackmussauer. It was filtered with charcoal, the solid components were washed with a little methanol and the di-isethionate was precipitated from the filtrate and washing liquid by adding acetone. The yield of 4,4'-di-amidino-a, γ-diphenoxy-propane was 5.29. The solubility in water was about 1 in 4 at 20 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB243025X | 1941-04-25 | ||
| CH236875T | 1945-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH243025A true CH243025A (en) | 1946-06-15 |
Family
ID=25728194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH243025D CH243025A (en) | 1941-04-25 | 1942-04-20 | Process for the preparation of a soluble salt of 4,4'-di-amidino-a, γ-diphenoxy-propane. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH243025A (en) |
-
1942
- 1942-04-20 CH CH243025D patent/CH243025A/en unknown
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