GB2163744A - Preparation of 6-substituted-furo-(3,4-c)-pyridine derivatives - Google Patents
Preparation of 6-substituted-furo-(3,4-c)-pyridine derivatives Download PDFInfo
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- GB2163744A GB2163744A GB08520169A GB8520169A GB2163744A GB 2163744 A GB2163744 A GB 2163744A GB 08520169 A GB08520169 A GB 08520169A GB 8520169 A GB8520169 A GB 8520169A GB 2163744 A GB2163744 A GB 2163744A
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- hydroxy
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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Abstract
<IMAGE> The compounds I (A1, A2 independently = H, C1-C5hydrocarbon, heterocycle up to 6 ring atoms, carbomonocycle, phenylalkyl, phenylalkenyl; each (except H) unsubstituted or substituted by one or more of F, Cl, CF3, C1-C5alkyl, C1-C5alkoxy, C1-C5alkylthio, di(C1-C5alkyl)-amino, di(C1-C5alkyl)-amino- (C1-C5alkoxy), alpha - or beta -(C1-C5alkoxy)-N-pyrrolidinyl), which are known compounds of interest for their therapeutical activity, principally in the fields of diuresis, lowering of blood pressure, kidney protection and also as antihistaminic agents, are prepared by reacting the corresponding 6-formyl derivatives with 1- dimethylaminomethyl-vinylmagnesium bromide at the boil in a non-polar solvent such as tetrahydrofuran.
Description
SPECIFICATION
Preparation of 6-substituted-furo-(3,4c)-pyridine derivatives
The invention relates to the preparation of 1,3-dihydro-6-(1-hydroxy-2-dimethylaminomethyl-allyl)- 7-hydroxy-furo-(3,4-c)-pyridine derivatives of the general formula I
wherein each of A1 and A2 independently represents a hydrogen atom, a straight chain saturated or unsaturated hydrocarbon group having from 1 to 5 carbon atoms, a heterocyclic group having up to 6 ring atoms, a carbomonocyclic group, a phenylalkyl group or a phenylalkenyl group, each of the groups represented by At and A2 being unsubstituted or being substituted by one or more chlorine or fluorine atoms, trifluoromethyl groups, alkyl groups having from 1 to 5 carbon atoms, alkoxy groups having from 1 to 5 carbon atoms, alkylthio groups having from 1 to 5 carbon atoms, dialkylamino groups in which each alkyl group has from 1 to 5 carbon atoms, dialkylaminoalkoxy groups in which each of the two alkyl groups and the alkoxy group has from 1 to 5 carbon atoms or a or ss-alkoxy-N-pyrrolidinyl groups in which the alkoxy group has from 1 to 5 carbon atoms.
These compounds have been described and claimed in our British Patent Application No.
2153824. They are of interest for their therapeutical activity, principally in the fields of diuresis, lowering of the blood pressure, kidney protection and also as antihistaminic agents.
It has surprisingly been found that in the process described in our aforesaid Patent Application the protection of the hydroxy group in position 7 might be omitted and nevertheless the product might be prepared with a better yield.
Accordingly, the invention provides a process for the preparation of 1 ,3-dihydro-6-( 1 -hydroxy- 2-dimethylaminomethyl-allyl)-7-hydroxy-furo-(3,4-c)-pyridine derivatives of the general formula I as above defined, the process comprising a 6-formyl-7-hydroxy-furo-(3,4-c)-pyridine derivative of the general formula II
wherein A, and A2 are as above defined with a slight excess of 1 -dimethylaminomethyl-vinylmag- nesium bromide at the boil, in a non polar solvent such as tetrahydrofuran.
The 6-formyl-7-hydroxy-furo-(3,4-c)-pyridine derivatives II may be obtained frpm corresponding 6-methyl-7-hydroxy deriviatives of the general formula Ill
wherein A1 and A2 are as above defined by the following sequence of reactions:
The compounds Ill are disclosed in our British Patent Application No. 2137618.
The preparation of one only of the starting compounds, 1,3-dihydro-3-p-chlorophenyl-6-formyl- 7-hydroxy-furo-(3,4-c)-pyridine, is now described in detail, other starting materials being obtained by the same way.
a) Into a one litre reactor fitted with stirring, warming and cooling means, 22.3 g of 1,3 dihydro-3-p-chlorophenyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine were treated at 0 C, in the presence of 300 ml of methylene dichloride, with 18.2 g of m-peroxybenzoic acid, slowly added. After stirring overnight at room temperature, there were added 150 ml of 10% sodium sulphate solution. After stirring and decantation, the methylene dichloride phase was washed with the same amount of sodium sulphate solution, twice with 150 ml of sodium bicarbonate solution and three times with 100 ml of water than dried over anhydrous sodium sulphate. By evaporation to dryness, there was obtained a beige precipitate which was washed with petroleum ether, filtered and dried.Yield 22.9 g (96%) of 1,3-dihydro-3-pchlorophenyl-6-methyl-7- hydroxy -furo-(3,4-c)-pyridine-N-oxide.
b) In the same reactor as above, the 22.9 g of the compound obtained in the previous step were treated at 0-SOC, in the presence of 175 ml of methylene dichloride, with 4.3 ml of trifluoroacetic anhydride added dropwise under stirring. The mixture was stirred overnight at room temperature, and then cooled and treated dropwise with 95 ml of methanol. After evaporation to dryness, the residue was taken up in 300 ml of chloroform, washed twice with 75 ml of 10% sodium bicarbonate solution and three times with 100 ml of water and dried on anhydrous sodium sulphate. The chloroform was evaporated off and the residue was washed with diethyl ether and dried under reduced pressure. Yield 21.3 g (93 %) of 1,3-dihydro-3-p chlo roph enyl-6-hyd roxymethyl-7 -hyd roxy-fu ro-(3 ,4-c)-pyridine.
c) The 21.3 g of the compound obtained in the previous step were treated in a 2 litre reactor with 279 of manganese dioxide in the presence of 0.9 litre of chloroform at 28-30"C, under stirring for 3 hours. After separation, filtration, washing with chloroform and then with ethyl acetate, the solution was evaporated to dryness and the paste treated with isopropyl oxide then with pentane. There was thus obtained 20.1 g (95 %) of 1,3-dihydro-3-p-chlorophenyl-6-formyl- 7-hydroxy-furo-(3,4-c)-pyridine.
The following examples illustrate the invention.
Example 1 I, 9-dihsro-3-methyl-6-( I -hydroxy-2-dimethylaminomethyl-allyl)- 7-hydroxy-furo-(3, 4-c)-pyridine a) Preparation of the organomagnesium reagent
In a two litre reactor fitted with warming, cooling and stirring means were poured, under nitrogen circulation, 19.4 g (0.8 mol) of magnesium, and 100 ml of tetrahydrofuran, preferably distilled on lithium aluminium hydride. The mixture was refluxed.
There was then slowly added 132 g (0.8 mol) of 3-dimethylamino-2-bromo-1-propylene. No external heating was applied, the reflux being maintained and controlled by the addition of this compound. At the end of the addition, one litre of distilled tetrahydrofuran was added. The mixture was refluxed for two hours and then cooled to 10"C.
b) Reaction
To the reaction mixture from the previous step was slowly added, under stirring, 89 g (0.5 mol) of 1,3-dihydro-3-methyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. The temperature reached about 25"C at the end of the addition. Stirring was maintained overnight at room temperature.
The mixture was then cooled to 0 C and 250 ml of water saturated with ammonium chloride and 250 ml of diethyl ether were added to it. After stirring for 15 minutes at room temperature there was obtained a two-phase mixture with an oil supernatant.
The mixture was separated and the aqueous phase was extracted twice with 250 ml aliquots of diethyl ether. The extracts were added to the oily phase, which had been washed with water three times. The oily phase was then dried on magnesium sulphate, treated with carbon black, concentrated to dryness and extracted twice with 250ml of diisopropyl ether. The extracts were filtered, concentrated (reduction to 1/4 of initial volume) and cooled overnight, leading to a precipitate, which was separated and washed with diisopropyl ether. Yield 105 g (80%).
The preparation of the other compounds of the invention follows the same process except that, in step (b), the starting material is different; the following examples will, accordingly refer to example 1 and only mention the new starting material, the overall yield and the characteristics of the compound obtained.
Example 2
1, 3-dihydro-3-propyl-6-( 1 -hydroxy-2-dimethylaminomethyl-allyl)- 7-hydroxy-furo-(3, 4-c)-pyridine
The method of example 1 was repeated, but starting with 83 g (0.4 mol) of 1 ,3-dihydro-3- propyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 66% of a product melting at 187-194"C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula C16H24N203, 2HCI.
Example 3 1, 3-dihydro-3-cyclohexyl-6-( 1 -hydroxy-2-dime thylaminomethylallyl)- 7-hydroxy-furo- (3, 4-c)-pyridine The method of example 1 was repeated, but starting with 99 g (0.4 mol) of 1,3-dihydro-3cyclohexyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 59% of product melting at 180-184"C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula CtgH2BN203 2HCI.
Example 4 1,3-dihydro-3-phenyl-6-( 1-hydroxy-2-dimethylaminomethyl-allyl)-7-hydroxy-furo-(3,4-c)-pyridine The method of example 1 was repeated, but starting with 99 g of (0.4 mol) of 1,3-dihydro-3 phenyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 49% of a product melting at 210-215"C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula C19H22N203, 2HCI.
Example 5 7, 3-dihydro-3-p-chlorophenyl-6-( 1-hydroxy-2-dimethylaminomethylallyl)-7-hydroxy-furo-(3,4-c)-pyri- dine
The method of example 1 was repeated, but starting with 110 g (0.4 mol) of 1,3-dihydro-3-p chlorophenyl-6-formyl-7-hydroxy-furo-(3,4-c) -pyridine. Yield 57% of a product melting at 195-200"C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula ClgH21C1N203 2HCI.
Example 6 1,3-dihydro-3-(2,3-dichlorophenyl)-6-( i-hydroxy-2-dimethylaminomethyl-allyl)-7-hydroxy-furo-(3,4- c)-pyridine
The method of example 1 was repeated, but starting with 124 g (0.4 mol) of 1,3-dihydro-3 (2,3-dichloro-phenyl)-6-formyl-7-hydrnxy4uro-(3,4-c)-pyridine. Yield 62% of a product melting at 180-184"C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula C,9H20CI2N203. 2HCI.
Example 7 1,3-dEhydro-3-p-fluorophenyl-6-( l-hydroxy-2-dimethylaminomethylallyl)-7-hydroxy-furo-(3,4-c)-pyri- dine
The method of example 1 was repeated, but starting with 1049 (0.4 mol) of 1,3-dihydro-3- fluorophenyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 62% of a product melting at 198"C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula C19H21FN203.2HCI.
Example 8 1,3-dEhydro-3-p-toluyl-6-( 1-hydroxy-2-dimethylaminomerhylallyl)- 7-hydroxy-furo-(3,4-c)-pyridine
The method of example 1 was repeated, but starting with 103 g (0.4 mol) of 1,3-dihydro-3-p- toluyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 66% of a product melting at 203-207 C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula C20H24N203.2HCI.
Example 9
1,3-dihydro-3-p-methoxyphenyl-6-( 1-hydroxy-2-dimethylaminomethyl-allyl)-7-hydroxy-furo-(3,4-c) pyridine
The method of example 1 was repeated, but starting with 110 g of (0.4 mol) of 1,3-dihydro3-p-methoxyphenyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 63% of a product melting at 169-170"C (Tottoli), the analysis of which showed a good correspondence with the formula
C20H24N204. 2HCI.
Example 10
1,3-dshydro-3-m-trifluoromethylphenyl-6-(1-hydroxy-2-dimethylaminomethyl-allyq-7-hydroxy-furo- (3,4-c)-pyridine
The method of example 1 was repeated, but starting with 124 g (0.4 mol) of 1,3-dihydro-3 m-trifluoromethylphenyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 58% of a product melting at 217-223 C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula C20H21F3N203. 2HCI.
Example 11
1, 3-dihdro-3-p-(diethylaminoe thoxy-phenyl)-6-( 1-h ydroxy-2-dimethylaminomethylj-allyi)- 7-hydroxy- furo-3,4-c)-pyridine The method of example 1 was repeated, but starting with 142 g (0.4 mol) of 1,3-dihydro-3-p (diethylaminoethoxyphenyl)-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 51% of a product malting at 158-160"C (Tottoli), the analysis of which showed a good correspondence with the formula C25H3sN3Q. 2HCI.
Example 12 1,3-dihydro-3-p-(pyrrolidinylethoxy-phenyl)-6-( 1 -hydroxy-2-dimethylaminomethyl-allyq?77hydr
furo-(3, 4-c)-pyridine The method of example 1 was repeated, but starting with 142 g (0.4 mol) of 1,3-dihydro-3-p
(pyrrolidinylethoxyphenyl)-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 53% of a product melting at 173"C (Tottoli), the analysis of which showed a good correspondence with the formula C2sH33N304. 2HCI.
Example 13
1 ,3-dihydro-3-methyl-3-n-pentyl-6-( 1 -hydroxy-2-dimethylaminomethyl-allyl)-7-hydroxy-furo-(3,4-c)- pyridine
The method of example 1 was repeated, but starting with 99 g (0.4 mol) of 1,3-dihydro-3
methyl-3-n-pentyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 59% of a product melting at 187-191"C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula Cl > H30N203. 2HCI.
Example 14 1,3-dEhydro-3-methyl-3-phenyl-6-( 1-hydroxy-2-dimethyiammomethyl-aIlyl)-7-hydroxy-furo-(3,4-c)-py- ridine
The method of example 1 was repeated, but starting with 103 g (0,4 mol) of 1 ,3-dihydro-3- methyl-3-phenyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 69% of a product melting at 178-179"C (Tottoli), the analysis of which showed a good correspondence with the formula
C20H24N203. 2HCI.
Example 15 1, 3-dihydro-3-methyl-3-a-thienyl-6-( 1 -hydroxy-2-dimethylaminomethyl-allyl)- 7-hyoroxy-f'rn-(3, 4- c)pyridine
The method of example 1 was repeated, but starting with 103 g (0.4 mol) of 1,3-dihydro-3 methyl-3-a-thienyl-6-formyl-7-hydroxy4uro-(3,4-c)-pyridine. Yield 67% of a product melting at 169-175"C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula (C,8H22SN203. 2HCI.
Example 16 1, 3-dihydro-3-ethyl-3-m-trifluoromethylphenyl-6-( 1 -hydroxy-2-dimethylaminomethyl-allyl)- 7-hydroxyfuro-(3,4-c)-pyridine
The method of example 1 was repeated, but starting with 136 g (0.4 mol) of 1,3-dihydro-3 ethyl-3-m-trifluoromethylphenyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 72% of a product melting at 185"C (Tottoli), the analysis of which showed a good correspondence with the formula C22H25F3N203. 2HCI.
Example 17 1,3-dihydro-3-ethyl-3-a-furyl-6-( 1-hydroxy-2-dimethyiaminomethyl-allyl)-7-hydroxy-furo-(3,4-c)-pyri- dine
The method of example 1 was repeated, but starting with 104 g (0.4 mol) of 1,3-dihydro-3 ethyl-3-a-furyl-6-formyl-7-hydroxy-f uro(3 ,4-c)-pyridine. Yield 585o of a product melting at 164-169"C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula C19H24N204. 2HCI.
Example 18 1,3-dihydro-3-phenyl-3-p-ethoxyphenyl-6-( 1-hydroxy-2-dimethylaminomethyl-allyI)-7-hydroxy-furo- (3,4-c)-pyridine
The method of example 1 was repeated, but starting with 144 g (0.4 mol) of 1,3-dihydro-3 phenyl-3-p-ethoxyphenyl-6-formyl-7-hydroxy4uro-(3,4-c)pyridine. Yield 64% of a product melting at 148-149"C (Tottoli), the analysis of which showed a good correspondence with the formula
C27H30N204. 2HCI.
Example 19 1,3-dihydro-3, 3-di-p-fluorophenyl-6-( 1 -hydroxy-2-dimerhylaminomethyl-allyl)- 7-hydroxy-furo-(3, 4-c)- pyridine
The method of example 1 was repeated, but starting with 142 g (0,4 mol) of 1,3-dihydro-3,3di-p-fluorophenyl-6-formyl-7-hydroxy-furo-(3,4-c)-pyridine. Yield 70% of a product melting at 175"C (Tottoli), the analysis of which showed a good correspondence with the formula C2sH24F2N203. 2HCI.
Example 20
1,3-dihydro-3-a-furyl-3-p-thiomethylphenyl-6-( 1-hydroxy-2-dimethylaminomethyl-allyi)- 7-hydroxy furo-(3, 4-c)-pyridine The method of example 1 was repeated, but starting with 141 g (0.4 mol) of 1,3-dihydro-3-a furyl-3-pthiomethylphenyl-64ormyl-7-hydrnxy4urn-(3,4-c)-pyridine. Yield 48% of a product melting at 143-151"C (Tottoli), with decomposition, the analysis of which showed a good correspondence with the formula C24lI26SN204. 2HCI.
Claims (3)
1. A process for the preparation of a 1,3-dihydro-6-(1-hydroxy-2-dimethylaminomthyl-allyl)-7- hydroxy-furo-(3,4-c)-pyridine derivative having the general formula I as herein defined, the process comprising reacting a 6-formyl-7-hydroxy-furo-(3,4-c)-pyridine derivative having the general formula II as herein defined with a slight excess of 1-dimethylaminomethyl-vinylmagnesium bromide at the boil in a non polar solvent.
2. A process according to claim 1 in which the non-polar solvent is tetrahydrofuran.
3. A process for the preparation of a 1 ,3-dihydro-6-(1-hydroxy-2-dimethylaminomethyl-allyl)-7- hydroxy-furo-(3,4-c)-pyridine derivative having the general formula I as herein defined, the process being substantially as described herein with reference to any of the Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848422029A GB8422029D0 (en) | 1984-08-31 | 1984-08-31 | 6-substituted-furo-(3 4-c)-pyridine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8520169D0 GB8520169D0 (en) | 1985-09-18 |
| GB2163744A true GB2163744A (en) | 1986-03-05 |
| GB2163744B GB2163744B (en) | 1988-01-20 |
Family
ID=10566078
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB848422029A Pending GB8422029D0 (en) | 1984-08-31 | 1984-08-31 | 6-substituted-furo-(3 4-c)-pyridine derivatives |
| GB08520169A Expired GB2163744B (en) | 1984-08-31 | 1985-08-12 | Preparation of 6-substituted-furo-(3,4-c)-pyridine derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB848422029A Pending GB8422029D0 (en) | 1984-08-31 | 1984-08-31 | 6-substituted-furo-(3 4-c)-pyridine derivatives |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS6160688A (en) |
| AR (1) | AR241455A1 (en) |
| AT (1) | AT396590B (en) |
| BE (1) | BE903122A (en) |
| CA (1) | CA1300149C (en) |
| CH (1) | CH666688A5 (en) |
| DE (1) | DE3531004A1 (en) |
| DK (1) | DK157871C (en) |
| ES (1) | ES8604967A1 (en) |
| FI (1) | FI82468C (en) |
| FR (1) | FR2569698B1 (en) |
| GB (2) | GB8422029D0 (en) |
| HK (1) | HK6189A (en) |
| IE (1) | IE58522B1 (en) |
| IT (1) | IT1201459B (en) |
| LU (1) | LU86052A1 (en) |
| NL (1) | NL8502324A (en) |
| NO (1) | NO162071C (en) |
| OA (1) | OA08088A (en) |
| PT (1) | PT81054B (en) |
| SE (1) | SE462218B (en) |
| ZA (1) | ZA856088B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8427218D0 (en) * | 1984-10-27 | 1984-12-05 | Scras | Pyridine derivatives |
| GB8808001D0 (en) * | 1988-04-06 | 1988-05-05 | Scras | Stereospecific preparative process for furol(3,4-c)pyridine derivatives |
| DE10323602A1 (en) * | 2003-05-19 | 2004-12-16 | Südzucker AG Mannheim/Ochsenfurt | Hard caramel for human consumption, contains hard caramel base and supported food color inhomogeneously distributed within hard caramel base |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
| ZA842029B (en) * | 1983-04-05 | 1984-10-31 | Scras | Furo-(3,4-c)-pyridine derivatives preparation thereof and therapeutic compositions containing the same |
| GB2153824B (en) * | 1984-02-02 | 1987-04-01 | Scras | Furo-(3,4-c)-pyridine derivatives |
-
1984
- 1984-08-31 GB GB848422029A patent/GB8422029D0/en active Pending
-
1985
- 1985-08-12 ZA ZA856088A patent/ZA856088B/en unknown
- 1985-08-12 GB GB08520169A patent/GB2163744B/en not_active Expired
- 1985-08-19 SE SE8503869A patent/SE462218B/en not_active IP Right Cessation
- 1985-08-20 AR AR85301339A patent/AR241455A1/en active
- 1985-08-22 CA CA000489219A patent/CA1300149C/en not_active Expired - Fee Related
- 1985-08-22 LU LU86052A patent/LU86052A1/en unknown
- 1985-08-23 NL NL8502324A patent/NL8502324A/en not_active Application Discontinuation
- 1985-08-23 CH CH3653/85A patent/CH666688A5/en not_active IP Right Cessation
- 1985-08-26 BE BE0/215502A patent/BE903122A/en not_active IP Right Cessation
- 1985-08-28 FI FI853287A patent/FI82468C/en not_active IP Right Cessation
- 1985-08-29 AT AT0252985A patent/AT396590B/en not_active IP Right Cessation
- 1985-08-30 FR FR8512917A patent/FR2569698B1/en not_active Expired
- 1985-08-30 JP JP60190033A patent/JPS6160688A/en active Granted
- 1985-08-30 OA OA58669A patent/OA08088A/en unknown
- 1985-08-30 ES ES546590A patent/ES8604967A1/en not_active Expired
- 1985-08-30 IE IE214385A patent/IE58522B1/en not_active IP Right Cessation
- 1985-08-30 NO NO853418A patent/NO162071C/en unknown
- 1985-08-30 IT IT22035/85A patent/IT1201459B/en active
- 1985-08-30 DK DK396085A patent/DK157871C/en not_active IP Right Cessation
- 1985-08-30 DE DE19853531004 patent/DE3531004A1/en active Granted
- 1985-08-30 PT PT81054A patent/PT81054B/en not_active IP Right Cessation
-
1989
- 1989-01-19 HK HK61/89A patent/HK6189A/en not_active IP Right Cessation
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Effective date: 19980812 |