GB2140005A - A benzidamine salt - Google Patents
A benzidamine salt Download PDFInfo
- Publication number
- GB2140005A GB2140005A GB08405869A GB8405869A GB2140005A GB 2140005 A GB2140005 A GB 2140005A GB 08405869 A GB08405869 A GB 08405869A GB 8405869 A GB8405869 A GB 8405869A GB 2140005 A GB2140005 A GB 2140005A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzidamine
- salt
- acid
- fluphenamic
- fluphenamate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Benzidamine fluphenamate has strong antiflammatory activity and can be prepared by reacting fluphenamic acid with benzidamide.
Description
SPECIFICATION
A benzidamine salt
The present invention relates to a benzidamine salt. Benzidamine is an amine, the complete name of which is N,N-dimethyl-3-[(1-phenylmethyl)-1 H-imidazole-3-yl)-oxy]-1-propanamine and which can produce salts of addition with strong acids such as the chlorhydrate which is commercially available.
The present invention provides the fluphenamic acid of benzidamine.
Fluphenamic acid is 2-[(3-[trifuoromethyl]phenyl)]-amino]benzoic acid which is also commercially available.
The salt has the following structural formula:
The derivative of this invention is advantageous with respect to otherfluphenamic acid or benzidamine salts since it combines in the same chemical structure the anti-inflammatory properties of both components, which is not the case with other fluphenamic acid and benzidamine derivatives.
The local tolerance has been studied in rats by topical application of the derivative and it has been observed that the product is well tolerated.
It was confirmed that the novel product has an experimental anti-inflammatory effect after inflammation was caused in rats' ears by means of ricinus oil.
The attached Figure shows a curve representing the effect, in a test, expressed as a percentage of the inhibition of the inflammation on the ordinate, as a function of the dose expressed as a percentage of benzidamine fluphenamate on the abcissae.
For therapeutic use benzidamine fluphenamate can be administered without restriction topically, orally, rectally or parenterally.
The active ingredient, benzidamine fluphenamate, is found in each composition in an effective quantity and in dependence upon the amounts of fluphenamic and benzidamine required.
The present invention also provides a preparative method which is characterized in that fluphenamic acid, either as itself in the form of an acid or in the form of a soluble salt with an alkali metal or ammonium, is reacted with benzidamine typically as the chlorhydrate or basic benzidamine, in approximately equal quantities in a solvent, which can be water or an alcohol having a low molecular weight (say less than 100), at a temperature which may be as high as the boiling temperature of the solvent.
When the reaction medium is an alcohol the alkali metal or ammonium salt which is formed can be separated by filtration and the salt obtained by evaporating the alcohol.
When the medium is aqueous, extraction can repeatedly carried out by means of a chlorinated solvent, which may be carbon tetrachloride, chloroform, methylene chloride and once the combined extracts have been dried they can be evaporated so as to obtain the salt.
The salt is then obtained in the form of a caramel-coloured resin.
Some examples for performing the method are described hereinafter by way of non-limiting illustration.
Example 7 281.24 g of fluphenamic acid are added to a solution of 40 g of sodium hydroxide in two litres of water.
When dissolution is complete a previously prepared solution of 345.9 g of benzidamine chlorhydrate in 1 litre of water is slowly added with stirring.
The resultant solution is repeatedly extracted by means of chloroform. The extracts are collected and dried over sodium sulphate. The chloroform is eliminated by distillation and 502.0 g of a caramel-coloured resin are obtained.
U.V. (methanol): max. 215 and 295 nm l.R.film on KBr: 2400-3200 2960(m), 1600 (s), 1570 1500 (s), 1450(m), 1380(s), (s),1330 (s), . . . cm-1.
Elementary analysis
Calculated for C33H33F3N403: % C 67.11; % H 5.63; % N 9.48; % F 9.65 Obtained:%C66.9%H5.8-%N9.8-%F9.9.
Example 2
A solution of 345.9 g benzidamine chlorhydrate and 281.42 g offluphenamicacid in 1.51 of methanol is refluxed for two hours. When it is cold methanolic sodium hydroxide is added until a pH of 8.8 is reached, and a sodium chloride precipitate forms which is eliminated by filtration. The methanol is evaporated in a rotary evaporator and finally in a vacuum dryer. 324.8 g of resin similar to that in the first example are obtained.
Claims (2)
1. Benzidaminefluphenamate.
2. A process for obtaining a novel derivative offluphenamic acid and benzidamine having the formula:
characterized in thatfluphenamic acid is reacted with benzidamine in a polar solvent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES520391A ES8403876A1 (en) | 1983-03-08 | 1983-03-08 | A benzidamine salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8405869D0 GB8405869D0 (en) | 1984-04-11 |
| GB2140005A true GB2140005A (en) | 1984-11-21 |
Family
ID=8485419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08405869A Withdrawn GB2140005A (en) | 1983-03-08 | 1984-03-06 | A benzidamine salt |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES8403876A1 (en) |
| GB (1) | GB2140005A (en) |
-
1983
- 1983-03-08 ES ES520391A patent/ES8403876A1/en not_active Expired
-
1984
- 1984-03-06 GB GB08405869A patent/GB2140005A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB8405869D0 (en) | 1984-04-11 |
| ES520391A0 (en) | 1984-04-16 |
| ES8403876A1 (en) | 1984-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4190671A (en) | Chalcone derivatives | |
| US4008323A (en) | Method of reducing cholesterol using certain aromatic keto acids | |
| US4287190A (en) | Complexes of bivalent copper | |
| US4080380A (en) | 2-Naphthyl-lower-alkylamines | |
| GB2140005A (en) | A benzidamine salt | |
| CA1151183A (en) | N-acylcarnosine aluminum salt, its preparation, and a digestive ulcer remedy containing such salt | |
| US3278600A (en) | alpha-amine-p-methoxyisobutyrophenone and salts thereof | |
| GB2098989A (en) | Lysine salts | |
| CA1041541A (en) | Process for preparing 4-cyclopropyl-methyleneoxy-3-chlorophenylacetic acid and salts thereof | |
| DE2039426C3 (en) | 1-Benzylidene-indenyl- (3) -acetic acids, their non-toxic, pharmacologically acceptable salts, processes for their production and pharmaceuticals containing them | |
| FI59087C (en) | FOERFARANDE FOER FRAMSTAELLNING AV 2,5-DISUBSTITUERADE BENSAMIDER | |
| US4118504A (en) | Isoindoline derivatives for treating pain | |
| US4233304A (en) | Pyridoxine derivatives | |
| US4886908A (en) | Method of preparing (R)-4-amino-3-hydroxybutyric acid | |
| EP1476446A1 (en) | Method for producing n-ethyl-n- 3-(3-cyanopyrazolo 1,5a]pyrimidine-7-yl)phenyl acetamide | |
| US4189607A (en) | Anilionotropone derivatives | |
| FR2478094A1 (en) | AMMONIO SUBSTITUTED CINNAMYLMORANOLINE DERIVATIVES WITH INHIBITION ACTIVITY OF SUGAR LEVEL IN BLOOD | |
| US4855443A (en) | Chromoglycic acid derivative | |
| DE2559928C2 (en) | N-aroyl-L-phenylalanyl-L-tyrosine, process for their preparation and pharmaceuticals containing these compounds | |
| US4028369A (en) | Preparation of glycol (2-(p-chlorophenoxy)-2-methylpropionate)-2-nicotinate | |
| JP2541723B2 (en) | Novel salicylic acid-maltol complex | |
| US2868804A (en) | Betaine ascorbate | |
| US5750775A (en) | Sodium orthohydroxymandelate/phenol/water complex, preparation process and use for isolation of sodium orthohydroxymandelate | |
| FI64153C (en) | MELLAN PRODUCTS FOR FRAMSTATING AV PHARMACEUTICAL ACTIVE 7-ACYL ACID 3-ACETOXIMETYL-CEFALOSPORINER | |
| FI73669B (en) | FORMULATION OF FRAMSTAELLNING AV 5-ALKYL-2-CARBOXY PYRAZINE. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |