DE1172663B - Process for the production of bismuth tri- (p-phenylcinnamate) - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Boarding school Class: C 07 c

German class: 12 ο-21

Number: 1172 663

File number: M 50745IV b / 12 ο

Filing date: October 31, 1961

Opening day: June 25, 1964

The invention relates to a process for the production of bismuth tri- (p-phenylcinnamate) or bismuth tri - (/? - [diphenyl] acrylate) by reacting p-phenylcinnamic acid with bismuth nitrate by adding p-phenylcinnamic acid (= Diphenylacrylic acid, 0.7 to 0.8 mol), which is in a mixture of dimethylaminoethanol (0.7 to 0.8 mol) and boiling water (100 to 150 mol) is slurried and the one gradually about three times the amount of water the original amount of water is added, the solution is filtered, the filtrate diluted with a large amount (1000 to 1500 moles) of boiling distilled water and diluted this Solution a concentrated aqueous bismuth nitrate solution (0.23 to 0.27 mol with 5 mol of water), which contains mannitol (0.24 to 0.28 mol) as a solubilizer, is added.

The resulting precipitate is filtered off after the mixture has been heated and cooled.

The compound that can be produced by the process corresponds to the following formula:

Process for the production of bismuth tri- (p-phenylcinnamate)

Applicant:

Maggioni & C. S. p. A., Milan (Italy)

Representative:

Dipl.-Ing. Dipl. Oec. publ. D. Lewinsky,

Patent attorney,

Munich-Pasing, Agnes ^ Bernauer-Str. 202

Claimed priority:

Italy of April 28, 1961 (7932)

-CH = CH-COO Bi

Bismuth tri- (p-phenylcinnamate) is used to treat ear, nose and throat diseases.

While it is known that bismuth salts have good anti-inflammatory effects in treatment normal sore throats, angina after P 1 a u t —V i η c e η t, tonsillitis and its side effects, inflammation of the oral mucosa (stomatitis) and catarrh of the throat show, but it is also known to have been used in the treatment of ear, nose and throat diseases used bismuth salts and bismuth compounds per se are not anti-inflammatory Have an effect, so that the unpleasant local symptoms of inflammation often even after they have been killed the pathogen persists.

It has now been found that bismuth tri- (p-phenylcinnamate) both an excellent therapeutic and a very formidable anti-inflammatory Has an effect. Furthermore, the pharmacological and clinical trials carried out show that the bismuth compound produced by the method of the invention of certain Mucous membranes, especially the rectal lining, is better absorbed than the bismuth compounds previously used for this purpose. This property is of great importance since the bismuth compounds are preferably used in the form of suppositories. at the treatment of the aforementioned diseases with bismuth tri- (p-phenylcinnamate) unpleasant side effects have never been observed, not even in children aged 4 to 5 years. The bismuth tri- (p-phenylcinnamate) can, however, also in tablet form (preferably 0.005 g of the Connection per tablet). The clinical results with oral administration were as good as the rectal administration of the suppositories. The new remedy also has at numerous patients developed its good properties after tonsil operations, whereby it was found that the wounds healed faster than usual and that there were no unpleasant side effects occurred. In general, there is at least 12 to 20 days for wound scarring after surgery necessary, while in patients treated with bismuth tri- (p-phenylcinnamate) were treated, occurred after 10 to 12 days. Below are some Pharmacological and clinical findings on the use of bismuth tri-p- (phenylcinnamate) were reported.

Pharmacological tests to determine the uptake of bismuth compounds by the

animal tissues

Several groups of rats, approximately 14 per group, were treated with suppositories containing 7.86 mg of bismuth camphor carbonate and sacrificed 14 hours after the suppository was inserted. The total bismuth uptake by the liver, spleen and kidneys of the animals was on average 23.9 ° / _0, while in a similar experiment bismuth tri- (p-phenylcinnamate) after the administration as a suppository, the

409 627/39 +

each contained 7.11 mg of this compound, on average 39.6% was recorded.

Clinical trials

Thirty-five people suffering from various forms of acute, erythemic tonsillitis, Catarrh of the throat, tonsillitis, follicular tonsillitis, pseudomembrane-like sore throat, Angina according to Plaut-Vincent and acute pharyngitis were affected treated with two to three suppositories, each containing 150 mg, per day. As far as temperature increase occurred was present, lowering of the fever, and the local signs of inflammation subsided much faster than in the treatment with the bismuth preparations previously used for this purpose.

A group of ten people was given suppositories and tablets after tonsil surgery each containing 150 mg bismuth tri- (p-phenylcinnamate), treated. The scarring of the wounds was after finished about 10 days.

example

170 g (0.76 mol) of p-phenylcinnamic acid are slurried in a boiling solution of 67.5 g (0.76 mol) of dimethylaminoethanol in about 21 water (110 mol). The mixture is then gradually diluted with a total of 6 liters (330 mol) of water, the liquid being kept at boiling temperature. The insoluble portion of the mixture is filtered off and the warm filtrate is poured into 201 (1100 moles) of boiling distilled water. A concentrated aqueous solution of 121.2 g (0.25 mol) of bismuth nitrate-5H ₂ O and 47.5 g (0.26 mol) of mannitol in 500 cm ³ (28 mol) of water is then added, and the resulting precipitate is added boiled for a few minutes and filtered off after the solution has cooled.

The yield is 190 g, corresponding to 85% of theory.

(C ₁₅ H ₁₁ Oa) ₃ Bi; Molecular weight 878.7;

found ... 23.03% Bi;
calculated ... 23.78% Bi.

Claims (1)

Claim: Process for the production of bismuth tri- (p - phenylcinnamate), characterized in that that one p-phenylcinnamic acid (0.7 to 0.8 mol) in a mixture of dimethylaminoethanol (0.7 to 0.8 moles) and boiling water (100 to 150 moles) and then gradually slurried add about three times the amount of the original amount of water, filter the mixture, dilute the filtrate with a large amount (1000 to 1500 moles) of boiling distilled water and this solution a concentrated aqueous bismuth nitrate solution (0.23 to 0.27 mol with 5 mol of water), which contains mannitol (0.24 to 0.28 mol) as a solubilizer, is added. 409 627/39 * 6.64 © Bundesdruckerei Berlin