DE109259C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

In patents 90848, 91370, 93698 and 105666 as well as in the patent addendum to patent 91370 some new quinine preparations described, which can be understood as quinine carbonic acid derivatives. These are the chlorocarbonic acid ethers of quinine or the quinine carbonic acid chloride and the quinine carbonic acid alkyl and phenol ethers respectively. the corresponding compounds of other cinchona alkaloids, e.g. B. of cinchonidine. All of these bodies have one property in common, not at all or only to a very limited extent Most of the time they taste bitter, and in some cases they already have a prominent place secured in therapy.

We have now succeeded in producing further derivatives of quinine carbonic acid, which are not alone are tasteless, but in which the quinine carbonic acid is paired with bodies, which are also excellent medicinal

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Quinine carboxylic acid anilide dissolves. From the acidic solution it is called by alkalis white powder deposited, which in alcohol, ether, chloroform and benzene very easily, in Ligro'in and water is sparingly soluble. Of the

The analysis showed:

Calculated for CO (^ _T ^ ° C = 73.14 pO.,

H = 6.54 -.

Properties. These are preparations which are called derivatives of quinine carbonic acid amide can look at.

These new bodies can be replaced by the action of quinine on substituted isocyanates or obtained from substituted carbamic acid chlorides. For both methods are Examples given here.

Representation of quinine carbonic acid a ηi 1 i d (phenylcarbamic acid quinine ether).

^{Anhydrous quinine is briefly heated to 190 °} C. with a small excess of phenyl isocyanate, during which it dissolves into a brownish liquid which solidifies to an amorphous mass when it cools. The latter is finely ground with dilute acid, e.g. B. sulfuric acid, treated according to the equation

η _ _rn / OC ₂₀ H ₂₃ M ₂ O

The melting point is not sharp, at around 100 ^° C. the amorphous body is completely melted. The preparation is tasteless, but a somewhat bitter aftertaste is noticeable.

Found:

72.86 pct.,
6.69 -.

The preparation forms salts with acids, the salicylate is very easily soluble in ether.

Representation of Chini nk oh lens acid phenetidide (Paraethoxyphenylcarbamic acid

quinine ether).

To begin with, a benzene solution of paraethoxyphenylcarbamic acid chloride to obtain, one carries in a solution of 2 Moleculen phenetidine in benzene with good cooling ι Molecül Phpsgen a dissolved in benzene. According to the equation

2C ₆ H ₄ - (OC ₂ HJ -NH ₂ + CO Cl ₂ =

C ₆ Ht (OC ₂ HJNH-COCl + C ₆ H ₄ (OC ₂ HJNH ₂ -HCl

Paraethoxyphenylcarbamic acid chloride forms, which remains dissolved, while hydrochloric acid Phenetidine is deposited. This is filtered off and 2 molecules from the filtrate Quinine added, which go into solution with heating, after the equation

C ₆ H ₄ (OC ₂ HJ-NH-COCl + 2 C ₂₀ H _and N ₂ O ₂ =

OC ₂₀ H ₂₃ N ₂ O H

₂₃₂ - C ₆ H ₄ - OC ₂ H ₅

the desired body forms. The resulting hydrochloric acid quinine separates when it cools and is filtered off. The filtrate is first diluted with water, then with a Acid, e.g. B. sulfuric acid, shaken, which the latter absorbs the phenetidide. Ammonia can precipitate it from the acidic solution. It represents a white

The analysis showed:

Calculated for C 0 ( ⁰ ^ ^ -

C = 71.46 pct.,
H = 6.5 - -

The body forms salts with acids, of which the salicylate in ether is extraordinary is soluble.

The other cinchona bark alkaloids react like quinine. As an example the cinchonidine carbonic acid phenetidide listed here, which is made from cinchonidine in exactly same way as the quinine carbonic acid

The analysis showed:

C ₂₀ H ₂₄ N ₂ O ₂ -HCl

almost tasteless powder, which is very easily dissolved in alcohol, ether, chloroform and benzene, very difficult to dissolve in ligroin and water. It is quite resistant to acids, on the other hand, it can be completely converted into quinine and by heating with alcoholic sodium hydroxide solution Phenetidine are cleaved.

OC ₂ H ₅

Found:

71.74 pct.,
6.55 -.

phenetidid can be made from quinine. The cinchonidine carbonic acid phenetidide is a Crystalline white, tasteless powder, which forms salts and the composition

owns.

Calculated for C

C = 73.52 pCt,
H = 6, _7, 8 -.

^ NH- C ₆ H ₄ - OC ₂ H ₅ -NH-C ₆ H ₄ -OC ₂ H ₅

Found:
73.78 pct.,

The above-mentioned bodies respectively. their salts are said to be used in medicine. She, are not only tasteless, but also combine good properties of quinine and the antipyretic and antineuralgic effects of amidophenol derivatives, z. B. of paraphenetidine.

Claims (1)

Patent claim: Process for the production of substitution products of quinine alkaloids, consisting of quinine or a other china alkaloid phenyl isocyanate or phenylcarbamic acid chloride respectively. their substitution products has an effect.