GB2078218A - A Process for the Production of 5-Arylidene Hydantoins - Google Patents
A Process for the Production of 5-Arylidene Hydantoins Download PDFInfo
- Publication number
- GB2078218A GB2078218A GB8116684A GB8116684A GB2078218A GB 2078218 A GB2078218 A GB 2078218A GB 8116684 A GB8116684 A GB 8116684A GB 8116684 A GB8116684 A GB 8116684A GB 2078218 A GB2078218 A GB 2078218A
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- Prior art keywords
- hydantoin
- arylidene
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- imine
- hydantoins
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
5-Arylidene hydantoins are obtained by condensing from 10 to 100 mole percent of an arylidene imine and from 90 to 0 mole percent of the aromatic aldehyde on which the arylidene imine is based with unsubstituted hydantoin or with hydantoin substituted in the 1-, 3-position or in the 1- and 3-positions. The arylidene imine may either be used in pure form or may be produced in situ from the aromatic aldehyde and 0.1 to 1.0 times the molar quantity of ammonia or of a primary amine.
Description
SPECIFICATION
A Process for the Production of 5-Arylidene
Hydantoins
This invention relates to'a process for the production of 5-arylidene hydantoins. 5-arylidene hydantoins are important intermediate products for the production of phenyl alanine and phenyl alanines substituted in the aromatic nucleus.
It is already known that 5-arylidene hydantoins can be produced by condensing benzaldehyde or substituted aromatic aldehydes with hydantoin in the presence of piperidine or diethylamine and in the absence of a solvent or in pyridine as solvent (Biochem. J. 29, pages 542 to 545 (1935)). Apart from the fact that the yields differ greatly from aldehyde to aldehyde, acceptable yields always require an undesirably long reaction time.
It is also known that condensation of the aldehyde with the hydantoin may becarried out in the presence of acetic acid and anhydrous sodium acetate (J. Amer. Chem, Soc. 45, pages 368 to 383 (191 1)). In the reaction of benzaldehyde, the yields amount for example to between 70 and 80%, based on the hydantoin used. To obtain these yields, however, it is necessary to use relatively large amounts of anhydrous sodium acetate. If the amount of sodium acetate is reduced, the yield falls drastically,
The present invention provides a process for the production of 5-arylidene hydantoins, which comprises reacting from 10 to 100 mole percent of an arylidene imine and from 90 toO mole percent of the aromatic aldehyde on which the arylidene imine is based with unsubstituted hydantoin or with hydantoin substituted in the 1-, 3- or in the 1- and 3-position.
Where 100 mole percent of an arylidene imine is used, the reaction on which the process according to the invention is based takes place in the absence of any additional catalysts. If, by contrast, a mixture of at least 10 mole percent of an arylidene imine and at most 90 mole percent of the corresponding aromatic aldehyde is used, the arylidene imine apparently acts as a catalyst to the condensation of the aromatic aldehyde with the hydantion. In both cases, the reaction leads relatively quickly to substantially quantitative yields of the required 5-arylidene hydantoins which, in addition, accumulate in highly pure form.
The most important representative of the arylidene imines (=Schiff's bases) used in the process according to the invention is benzylidene imine. However, virtually any arylidene imines substituted in the aromatic nucleus may also be used with equal effect. The arylidene imines may be produced in known manner from the corresponding aromatic aldehyde and ammonia or primary amines. Although they may be used in pure form, it is of particular advantage to produce them in situ from the corresponding aromatic aldehyde and 0.1 to 1.0 times the molar quantity of ammonia or a primary amine and to react the crude reaction product obtained with the hydantoin.
The most simple representative of the hydantoins used in the process according to the invention is hydantoin itself. However, virtually any hydantoins substituted in the 1-position, in the 3-position or in the 1- and 3-positions may also be used with equal effect.
The process according to the invention is particularly suitable for the production of 5arylidene hydantoins corresponding to the following general formula
in which R1,R2 and R3 which may be the same or different, each represent hydrogen, halogen, a hydroxyl group, a nitro group, an amino group an unbranched or branched alkyl or alkenyl group, a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an alkaryl group, an alkoxy group, an alkylthio group, an acyloxy group, an acylthio group, a mono- or dialkylamino group or an acylamino group.The alkyl groups preferably contain from 1 to 6 carbon atoms and more particularly from 1 to 3 carbon atoms, the alkenyl groups preferably contain from 2 to 6 carbon atoms and more particularly from 2 to 3 carbon atoms and the cycloalkyl and cycloalkenyl groups preferably contain from 3 to 8 and, more particularly from 3 to 6 carbon atoms.
In the cycloalkyl and cycloalkenyl groups, - OH2- may even be replaced one or more times by -0-, -S- or -NH- or -CH= may even be replaced one or more times by -N=, so that corresponding heterocyclic rings containing from 3 to 8 and, more particularly, from 3 to 6 ring members are present. The aralkyl and alkaryl groups preferably contain from 1 to 6 and more particularly from 1 to 3 carbon atoms in the alkylene or alkyl group. The alkoxy, alkylthio, acyloxy, acylthio, mono- or di-alkyl amino and acylamino groups preferably contain from 1 to 6 and, more particularly, from 1 to 3 carbon atoms in the alkyl or acyl groups.Two of the radicals R to R3 together may even form an alkylene or alkenylene group containing from 2 to 6 and more particularly from 2 to 4 carbon atoms. In this case, too, -OH2- may be replaced one or more times by -0-, -S-or -NH- or -OH may be replaced one or more times by -N=. R4 and
R5 may also be the same or different and each represent hydrogen, an unbranched or branched alkyl or alkenyl group, a cycloalkyl group, a cycloalkenyl group, an aryl group or an acyloxy group.In the radicals R4 and R5, the alkyl and acyloxy groups again preferably contain from 1 to 6 and more particularly from 1 to 3 carbon atoms, the alkenyl groups contains from 2 to 6 and more particularly from 2 to 3 carbon atoms and the cycloalkyl or cycloalkenyl groups contain from 3 to 8 and more particularly from 3 to 6 carbon atoms.
Accordingly, it is possible to use arylidene imines corresponding to the following general formula
in which R1, R2 and R3 are as defined above and R6 represents hydrogen, an unbranched or branched alkyl or alkenyl group, a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group or an alkaryl group. The alkyl groups preferably contain from 1 to 12 and more particularly from 1 to 6 carbon atoms, the alkenyl groups preferably contain from 2 to 1 2 and more particularly from 2 to 6 carbon atoms and the cycloalkyl and cycloalkenyl groups preferably contain from 3 to 8 and more particularly from 3 to 6 carbon atoms.
In the alkyl, alkenyl, cycloalkyl or cycloalkenyl groups, -OH2- may even be replaced one or more times by-0-,-S-, > C=O or-NH- or --CH= may be replaced one or more times by --N= or H may be replaced one or more times by -NH2,-SH, -OH or by halogen. The aralkyl and alkaryl groups preferably contain from 1 to 6 and more particularly from 1 to 3 carbon atoms in the aikylene or alkyl group.
Example of arylidene mines or Schiff's bases of the type in quention are benzylidene mine, Nbenzylidene ethylamine, N-benzylidene tert.butylamine, N-benzylidene-n-propylamine, Nbenzylidene ethanolamine, N-(4-isopropylbenzylidene)-ethylamine, N-(4hydroxybenzylidene)-benzylamine, N-(3,4,5trimethoxybenzylidene)-n-butylamine, N-(3bromo-4-methoxy-benzylidene)-cyclohexylamine, benzaldehydeanil, N-(3,4-methylenedioxybenzylidene)-methylamine, N-(4dimethylaminobenzylidene)-dodecylamine or N (3,5-dichloro-4-hydroxy-benzylidene)cyclopropylamine.
Accordingly, it is also possible to use aromatic aldehydes corresponidng to the following general formula
in which R1, R2 and R3 are as defined above.
Aldehydes such as these are, for example, benzaldehyde, 4-isopropylbenzaldehyde, 4hydroxybenzaldehyde, 3,4,5trimethoxybenzaldehyde, 3-bromo-4methoxybenzaldehyde, 3,4methylenedioxybenzaldehyde, 4dimethylaminobenzaldehyde and 3,5-dichloro-4hydroxybenzaldehyde.
Finally, it is possible to use hydantoins corresponding to the following general formula
in which R4 and R5 are as defined above. Suitable hydantoins are, for example, hydantoin itself, 1methyl hydantoin, 1-ethyl hydantoin, 1-propyl hydantoin, 1-acetyl hydantoin, 1,3-dimethyl hydantoin, 1,3-diphenyl hydantoin or 1- phenyl-3acetyl hydantoin.
It can be of advantage to carry out the reaction in a solvent. Suitable solvents are water, aliphatic or aromatic alcohols, aliphatic or aromatic hydrocarbons, halogenated aliphatic or aromatic hydrocarbons or mixtures thereof. For example, ethanol, n-butanol, toluene, xylene, benzylalcohol or chlorobenzene may be used as the solvent.
The reaction is generally carried out at a temperature of from about 20 to 2000C and, more particularly, at a temperature from 700C to the boiling temperature of the mixture. The pressure may be selected largely as required. In other words, the reaction may be carried out at normal pressure and also at relatively low or relatively high pressure. Although it is generally of advantage to work at approximately normal pressure, elevated pressure may be necessary on account of the volatility of the substances. The quantitative ratio between the aldehyde present in the arylidene imine and the optionally free aromatic aldehyde may be both stoichiometric and also sub-stoichiometric or overstoichiometric. In general, it is of advantage to use one mole of (total) aldehyde per mole of hydantoin.
The reaction mixture should best contain at least 0.1 mole, preferably at least 0.2 mole and, more particularly at least 0.4 mole of arylidene imine per mole of hydantoin.
Example 1
133 g (1 mole) of N-benzylidene ethylamine were added over a period of 30 minutes at 800C to a solution of 100 g (1 mole) of hydantoin in 400 ml of water. The mixture was stirred for 4 hours at 80 to 900C. 5-benzylidene hydantoin separated out on cooling to room temperature.
The yield amounted to 184 g, corresponding to 98% of the theoretical, based on hydantoin. The product had a melting point of 219 to 2200C and was found by thin-layer chromatography to be pure.
Example 2
195 g (1 mole) of N-benzylidene benzylamine,
128 g (1 mole) of 1,3-dimethyl hydantoin and
500 ml of water were heated for 3 hours to reflux temperature, 5-benzylidene-1 ,3-dimethyl hydantoin separated out on cooling to room temperature. The yield amounted to 205 g, corresponding to 95% of the theoretical, based on 1,3-dimethyl hydantoin. The product had a melting point of 265 to 2670C and was found to be pure by thin-layer chromatography.
Example 3
A mixture of 149 g (1 mole) of N-benzylidene ethanolamine, 100 g (1 mole) of hydantoin and 300 ml of water was stirred for 4 hours at temperatures between 70 and 800C. 178 g of 5benzylidene hydantoin were obtained after cooling to room temperature, corresponding to a yield of 95% of the theoretical, based on hydantoin.
Example 4
A mixture of 177 g (1 mole) of N-(3,4 methylenedioxybenzylidene)-ethylamine, 1 00 g (1 mole) of hydantoin and 350 ml of water was stirred for 3 hours at 1 0000. After cooling to room temperature, 220 g of 5-(3',4'-methylenedioxybenzylidene)-hydantoin were obtained which corresponds to a yield of 95% of the theoretical, based on hydantoin. The product had a melting point of 244 to 2450C and was found by thin-layer chromatography to be pure.
Example 5
A mixture of 161 g (1 mole) of N-benzylidenen-propyl amine, 141 g (1 mole) of 1-acetyl hydantoin and 400 ml of n-butanol was heated for 5 hours to reflux temperature. 223 g of 5 benzylidene-1-acetyl hydantoin were obtained after cooling to room temperature, corresponding to a yield of 97% of the theoretical, based on hydantoin. The product had a melting point of 205 to 2080C and was found by thin-layer chromatography to be pure.
Example 6
A mixture of 84.8 g (0.8 mole) of benzaldehyde, 26.6 g (0.2 mole) of N-benzylidene ethylamine and 500 ml of water was stirred for 3 hours at 800C following the addition of 100 g (1.0 mole) of hydantoin. 5-benzylidene hydantoin separated out on cooling to room temperature.
The yield amounted to 180.5 g corresponding to 96% of the theoretical, based on hydantoin. The product had a melting point of 219 to 2200C and was found by thin-layer chromatography to be pure.
Example 7
30.5 g (0.5 mole) of ethanolamine were added dropwise with stirring at 25 to 300C to a mixture of 106 g (1.0 mole) of benzaldehyde and 400 ml of water. The mixture was then stirred for another 30 minutes at 25 to 300C and subsequently heated to 75 to 800C. 100 g (1.0 mole) of hydantoin were added at that temperature. The mixture was stirred for 3 hours at 800C. 5- benzylidene hydantoin separated out after cooling to room temperature. The yield amounted to 184.2 g, corresponding to 98% of the theoretical, based on hydantoin. The product was identical with the product obtained in accordance with
Example 6.
Example 8
The procedure was as in Example 6, except that 90 g (0.6 mole) of 3,4-methylene dioxybenzaldehyde and 70.8 g (0.4 mole) of N (3,4-methylene-dioxybenzylidene)-ethylamif were used, 213 g of 5-(3'-4'-methylenedioxybenzylidene)-hydantoin were obtained which corresponds to a yield of 92% of the theoretical. The product had a melting point of 244 to 2460C and was found by thin-layer chromatography to be pure.
Example 9
The procedure was as in Example 7 except that 106 g (1.0 mole) of benzaldehyde, 47.3 g (0.8 mole) of n-propylamine and 141 g (1.0 mole) of 1-acetyl hydantoin were used. The yield of 5 benzylidene-1-acetyl hydantoin amounted to 21 8.4 g, corresponding to 95% of the theoretical, based on 1-acetyl hydantoin. The product had a melting point of 206 to 2080C and was found by thin-layer chromatography to be pure.
Example 10
The procedure was as described in Example 7, except that 1 22 g (1.0 mole) of 4-hydroxy benzaldehyde, 32.1 g (0.3 mole) of benzylamine and 100 g (1.0 mole) of hydantoin in 300 ml of nbutanol were used. The yield of 5-(4'hydroxybenzylidene)-hydantoin amounted to 1 86 g, corresponding to 91% of the theoretical, based on hydantoin.
Example 11
The procedure was as described in Example 6, except that 75.5 g (0.5 mole) of 4nitrobenzaldehyde, 103 g (0.5 mole) of N-(4nitrobenzylidene)n-butylamine and 128 g (1.0 mole) of 1,3-dimethyl hydantoin were used. The yield of 5-(4'-nitrobenzylidene)-1 ,3-dimethyl hydantoin amounted to 240.1 g, corresponding to 92% of the theoretical, based on 1,3-dimethyl hydantoin. The product had a melting point of 258 to 2600C and was found by thin-layer chromatography to be pure.
Claims (5)
1. A process for the production of 5-arylidene hydantoins, which comprises reacting from 10 to 100 mole percent of an arylidene imine and from 90 to 0 mole percent of the aromatic aldehyde on which the arylidene imine is based with unsubstituted hydantoin or with hydantoin substituted in the 1-, 3- or in the 1- and 3position.
2. A process as claimed in Claim 1, wherein the arylidene imine is used in pure form.
3. A process as claimed in Claim 1, wherein the arylidene imine is produced in situ from the aromatic aldehyde and 0.1 to 1.0 times the molar quantity of ammonia or of a primary amine and the crude reaction product obtained is reacted with the hydantoin.
4. A process for the production of 5-arylidene hydantoins substantially as described with particular reference to any of the Examples.
5. 5-arylidene hydantoins when produced by a process as claimed in any of claims 1 to 4.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803023349 DE3023349A1 (en) | 1980-06-21 | 1980-06-21 | METHOD FOR PRODUCING 5-ARYLIDENE HYDANTOINES (C) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2078218A true GB2078218A (en) | 1982-01-06 |
| GB2078218B GB2078218B (en) | 1984-02-08 |
Family
ID=6105181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8116684A Expired GB2078218B (en) | 1980-06-21 | 1981-06-01 | A process for the production of 5-aryllidene hydantoins |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5731669A (en) |
| BE (1) | BE889319A (en) |
| CH (1) | CH650775A5 (en) |
| DE (1) | DE3023349A1 (en) |
| FR (1) | FR2485011A1 (en) |
| GB (1) | GB2078218B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5143928A (en) * | 1990-03-27 | 1992-09-01 | Warner-Lambert Company | 3,5-di-tertiarybutyl-4-hydroxyphenylmethylene derivatives of 2-substituted thiazolidinones, oxazolidinones, and imidazolidinones as antiinflammatory agents |
| US5464856A (en) * | 1988-05-25 | 1995-11-07 | Warner-Lambert Company | Arylmethylenyl derivatives of imidazolidinones useful as antiinflammatory agents |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0798808B2 (en) * | 1986-10-16 | 1995-10-25 | 味の素株式会社 | Novel dimethoxybenzal hydantoin derivative |
| JPH0798809B2 (en) * | 1986-10-16 | 1995-10-25 | 味の素株式会社 | New hydantoin derivative |
| IE62214B1 (en) * | 1988-05-25 | 1995-01-11 | Warner Lambert Co | Arylmethylenyl derivatives of thiazolidinones, imidazolidinones and oxazolidinones useful as antiallergy agents and antiinflammatory agents |
| US5143929A (en) * | 1991-05-09 | 1992-09-01 | Warner-Lambert Company | 2-substituted thiazolidinone, oxazolidinone, and imidazolidinone derivatives of fenamates as antiinflammatory agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2861079A (en) * | 1956-06-04 | 1958-11-18 | Dow Chemical Co | Process for making unsaturated hydantoins |
| GB1434074A (en) * | 1972-06-16 | 1976-04-28 | Canada Packers Ltd | Antiviral compositions comprising hydantoin derivatives |
-
1980
- 1980-06-21 DE DE19803023349 patent/DE3023349A1/en active Granted
-
1981
- 1981-04-09 FR FR8107112A patent/FR2485011A1/en active Granted
- 1981-06-01 GB GB8116684A patent/GB2078218B/en not_active Expired
- 1981-06-17 JP JP9239981A patent/JPS5731669A/en active Pending
- 1981-06-19 CH CH408981A patent/CH650775A5/en not_active IP Right Cessation
- 1981-06-19 BE BE6/47480A patent/BE889319A/en not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5464856A (en) * | 1988-05-25 | 1995-11-07 | Warner-Lambert Company | Arylmethylenyl derivatives of imidazolidinones useful as antiinflammatory agents |
| US5143928A (en) * | 1990-03-27 | 1992-09-01 | Warner-Lambert Company | 3,5-di-tertiarybutyl-4-hydroxyphenylmethylene derivatives of 2-substituted thiazolidinones, oxazolidinones, and imidazolidinones as antiinflammatory agents |
| US5290800A (en) * | 1990-03-27 | 1994-03-01 | Warner-Lambert Company | 3,5-di-tertiarybutyl-4-hydroxyphenylmethylene derivatives of 2-substituted thiazolidinones, oxazolidinones, and imidazolidinones as antiinflammatory agents |
| US5494927A (en) * | 1990-03-27 | 1996-02-27 | Warner-Lambert Company | 3,5-di-tertiarybutyl-4-hydroxyphenylmethylene derivatives of 2-substituted thiazolidinones, oxazolidinones, and imidazolidinones as antiinflammatory agents |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3023349A1 (en) | 1982-01-14 |
| BE889319A (en) | 1981-12-21 |
| DE3023349C2 (en) | 1988-02-18 |
| FR2485011B1 (en) | 1983-05-13 |
| JPS5731669A (en) | 1982-02-20 |
| CH650775A5 (en) | 1985-08-15 |
| GB2078218B (en) | 1984-02-08 |
| FR2485011A1 (en) | 1981-12-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |