IE861925L - N-oxides of n,n-dimethyl ethylamine. - Google Patents
N-oxides of n,n-dimethyl ethylamine.Info
- Publication number
- IE861925L IE861925L IE861925A IE192586A IE861925L IE 861925 L IE861925 L IE 861925L IE 861925 A IE861925 A IE 861925A IE 192586 A IE192586 A IE 192586A IE 861925 L IE861925 L IE 861925L
- Authority
- IE
- Ireland
- Prior art keywords
- oxyde
- pharmaceutical compositions
- examples
- hereinbefore described
- dimethyl
- Prior art date
Links
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001204 N-oxides Chemical class 0.000 title 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000003981 vehicle Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
- 229960004046 apomorphine Drugs 0.000 description 3
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 231100001231 less toxic Toxicity 0.000 description 3
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 3
- 229960000317 yohimbine Drugs 0.000 description 3
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 230000003001 depressive effect Effects 0.000 description 2
- 230000002631 hypothermal effect Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- QNMGHBMGNRQPNL-UHFFFAOYSA-N medifoxamine Chemical compound C=1C=CC=CC=1OC(CN(C)C)OC1=CC=CC=C1 QNMGHBMGNRQPNL-UHFFFAOYSA-N 0.000 description 2
- 229960003123 medifoxamine Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 2
- 229960003147 reserpine Drugs 0.000 description 2
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- -1 capsulesc Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- KJOMYNHMBRNCNY-UHFFFAOYSA-N pentane-1,1-diamine Chemical class CCCCC(N)N KJOMYNHMBRNCNY-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1. 2,2-bis phenoxy NN-dimethylethylamine N-oxyde having the formula see diagramm : EP0216646,P5,F3
[EP0216646A2]
Description
58999 f This invention relates to a novel derivative of NN-dimethyl ethylamine and more particularly to an N-oxyde* ;This invention specifically provides the M-oxyde of 2 p 2-bis phenoxy MN-dimethyl ethyl ami Be having the formula ;This invention also relates to the salts of M-oxyde with a mineral or organic acid and more precisely with a strong acid as hydrochloric acide, hydrohromic acid or sulphuric acid. ;The N-oxyde of 2,, 2-bis phenoxy NN-dimethyl ethylamine is a 10 weak base and leads to acid addition salts only with non-reducing strong acids. ;The N«oxyde and. the salts thereof are prepared according to a process which consists to react 2,2-bis phenoxy NM-dimethyl ethylamine or a salt thereof with a mineral or organic 15 peroxyde in an inert solvent. Preferablyf the peroxyde is perhydrol. It may also be a hydroperoxide from an alkanol such as tert-butyl peroxyde; a hydroperoxyde from a ketone such as hexafluoro acetone peroxyde^ a peracid such as p.nitroperbenzoic acid or 4-chloroperbensoic acid. ;20 The solvent of the reaction medium is an inert solvent such as methanol, ethanol or an aromatic hydrocarbon such as toluene ;- 3 - ;or xylol or a NM-disubstituted lower alkylamide such as dimethyl formamide or dimethyl acetamide. ;2 £ 2-bis phenoxy MM-dime thy1ethy1amiBe M-oxyde and its salts show the characteristic properties of the conation anti-5 depressive agents on the classical pharmacological tests» They inhibit the hypothermizing effect of Reserpine and Apomorphine„ They increase the group toxicity induced by injection of yohimbin and they antagonize the dispair test in the mice. ;10 2,2-bis phenoxy OT-dimethylethylamine has already been disclosed in the literature as well as its salts (see French brevet special de Medicament 5498M). The salts of 2,2-bis phenoxy MM-dimethy1ethy1amine have been described as having anti-depressant activities. The testing performed by the 15 applicant has evidenced the fact that these compounds show a significative acute toxicity in the mice which allows to locate the mean lethal doses to 800mg/kg„ ;In contrast thereof the N-oxyde which is the subject matter of this application shows a very weak toxicity while keeping 20 about the same level of activity and consequently it has not been possible to determine at doses acceptable for the animals„ a mean lethal doses. ;Moreover j. the M~oxyde presents an antagonistic action in the test of apomorphine ? and a positive action against the group 25 toxicity with yohimbine clearly more marked than those shown by 2 £, 2-bis phenoxy KB -d ime thy 1 ethy 1 amine „ In other words, the M-oxyde is more active than the prior art compound from which it derives, while being clearly less toxic. ;The French patent 2,384,495 has been cited to show the 30 equivalency existing between a M-acylated pentane diamine and its M-oxyde. It may merely be stated that in a 'juite ;- 4 - ;different chemical family,, the two kinds of compounds behave in pharmacology in a similar fashion. In contrast thereof , in , the series of bis phenoxy ethylamine, the 2 e2-bis phenoxy NN- ;s dimethyl ethylamine and its K- oxyde possess very different ;I 5 pharmacological properties. It appears to be frequent in the literature to notice that a H-oxyde is less toxic or possess about the same level of toxicity that the tertiary amine, from which it derives,, but this decrease is also the result of a lowering of the pharmacological activity in the animals. In 10 the case of bis phenoxy MM-dimethyl ethylamine, not only the N-oxyde subject matter of this invention is much less toxic f but in addition e it is markedly more active than the starting tertiary amine. ;Due to their anti-depressive properties £, they found an use in 15 human or veterinary medicine in the treatment of depressive condition e of the involuting psychoses, of the maniaco-depressive states, of the depressions of reaction or behaviour. These molecules being very weakly toxic, their therapeutical margin is very extended and they may be given 20 without fear of side-effects (such as dryness of the mouthe extrapyramidal disturbances) which may occur with the antipressant drugs belonging to the tricyclic group. ;The production of these pharmaceutical compositions is carried out according to the known methods of pharmacotechnology, 25 namely to produce tablets, coated tablets f dragees, soft gelatine capsules, capsulesc, drops£, injectable or drinkable solutionsi preparations for percutaneous applications. ;The following examples are merely intended for illustrating ^ the invention. They do not limit it in any manner. ;\ ;.1 ;_ 5 - ;BX38JHPI.B 1 ;Preparation of the N-oxyde of 2 £, 2-bis phenoxy MM-dimethyl ethylamine. ;- In a three-neck flask of 100 ml fitted with a decantation 5 funnela thermometer,, a cooling devicee, 5,15 g (0t,02M) of M-dimethyl-2? 2-bis phenoxy ethylamine previously dissolved in 50 ml methanol are introduced to which 6 ml 30% - perhyd.ro 1 are dropwise added. After completion of the addition„ stirring at room temperature is kept for 30 ran then the mixture is heated 10 at about 35 0 for 12 hours. ;Finally methanol is distilled off and water is discarded by anisotropic distillation with ethanol. The residual oily residue is taken up in ether; a white solid matter appears. After filtration and drying 3.08g N-oxyde of MM-dimethyl which 15 melts at 104°C. The yield amounts to 56,5 % ;Rf = 0,14 (CHCI3/CH3OH 9x1) ;NMR: (CDCL3) 10H (m, 6,8-7,3) ;1H (t; 6,7) ;2H (d; 3,7) ;20 6H (s; 3,2) ;MMR: (CDCL3) of MEDIFOXAMINE 10H (m; 6,8-7,3) ;1H (t; 5,8) ;2H (dp 2,8) 25 6H (s; 2,32). ;EE&MjpjLE II ;Study of the pha:onaco 1 ogica3. characteristics of the M-cxyde of 2, 2 bis phenoxy SN-dimethyl ethylamine see Table I ;- 6 - ;EXAMPLE II ;Pharmacological study on 2,2-bis phenoxy NN-dimethyl ethylamine N-oxyde ;PRODUCT ;CHEMICAL STRUCTURE ;ACUTE ;TOXICITY HYPOTHERMIA ;HYPOTHERMIA TOXICITY TO ;ON MICE TO RESERPINE TO APOMORPHINE YOHIMBINE ;P.Oo ;100 P.O. 50 P.O. ;100 ;DESPAIR TEST ;p7T| \ too p.o.■■ | | ;«- ;i%T"J ;f\ ;MEDIFOXAMINE ;ch — on — ;-an ;*CHj 600 0/10 700 3/10 300 5/10 + 2°5 + ri + 0"S 5/tO 60% N-OXYDE CHj ch j 500 0/10 1000 1/10 + 2° + 0°7 + J°8 7/10 51% TABLE I 7
Claims (5)
1.CLAIMS
2. 5 2.
3. 10
4. 15 5. 6. 20 The N-oxyde of 2,2 -bis phenoxy NN-dimethyl ethylamine of the formula The acid addition salts of the N-oxyde of claim 1 with a mineral or organic acid. A process for producing the N-oxyde of claim 1 in which a 2,2-bis phenoxy NN~dimethyl ethylamine or an acid addition salt thereof is reacted with a mineral or organic peroxyde in an inert medium. The pharmaceutical compositions having as active ingredient a compound according to any of claims 1 or 2 in combination or admixture with an inert non-f.oxic pharmaceutically-acceptable carrier or vehicle. The pharmaceutical compositions according to claim 4 in which the carrier or the vehicle is one of those suitable for parenteral, oral, rectal or percutaneous ways of administration. The pharmaceutical compositions according to any of claims 4 or 5 in which the content of active ingredient ranges from 0.05 g to 0.5 g per unit dosage. A compound substantially as hereinbefore described with reference to the Examples. 3 - 8 - 8. A process substantially as hereinbefore described with reference to the Examples. 9. A composition substantially as hereinbefore described with reference to the Examples.
5. Dated this 21st day of July, 1986 CRUICKSHANK & CO. Agents for the Applicant 1 Holies Street Dublin 2 mm\a:rt5\821S.iiJl
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8511152 | 1985-07-22 | ||
| FR8515448A FR2588552B3 (en) | 1985-10-16 | 1985-10-16 | NOVEL OXIDE DERIVATIVE OF NN-DIMETHYL ETHYLAMINE, PROCESS FOR PREPARING THE SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE861925L true IE861925L (en) | 1987-01-22 |
| IE58999B1 IE58999B1 (en) | 1993-12-15 |
Family
ID=26224627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE192586A IE58999B1 (en) | 1985-07-22 | 1986-07-21 | Novel N-oxyde of NN-dimethyl ethylamine, a process for it's production and the pharmaceutical compositions containing it |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0216646B1 (en) |
| KR (1) | KR940011528B1 (en) |
| AU (1) | AU593562B2 (en) |
| DE (1) | DE3674873D1 (en) |
| IE (1) | IE58999B1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2583639B3 (en) * | 1985-06-24 | 1987-09-25 | Rolland Sa A | NOVEL PHARMACEUTICAL COMPOSITIONS IMPROVING PSYCHOMOTOR PERFORMANCE AND PROCESS FOR OBTAINING SAME |
| KR870001153A (en) * | 1985-07-22 | 1987-03-11 | 데. 롤랑 | Pharmaceutical composition containing diphenoxyethylamine derivative and its production method |
| FR2589357B3 (en) * | 1985-11-05 | 1988-01-29 | Rolland Sa A | NOVEL PHARMACEUTICAL COMPOSITIONS IMPROVING CEREBRAL OXYGENATION BASED ON DIPHENOXY DIMETHYLAMINOETHANE AND PROCESS FOR OBTAINING SAME |
| CA2014201A1 (en) * | 1989-04-26 | 1990-10-26 | Albemarle Corporation | Solid non-hygroscopic trialkylamine oxides |
| US5866718A (en) * | 1997-03-20 | 1999-02-02 | General Electric Company | Synthesis of tertiary amine oxides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR5498M (en) * | 1966-05-18 | 1967-10-30 | ||
| DE2749214A1 (en) * | 1976-11-30 | 1978-06-01 | Upjohn Co | N- (2-AMINOCYCLOPENTYL) -N-ALKANOYLANILIDE OR THE 2-N-OXIDES THEREOF, METHOD FOR THEIR PREPARATION AND USE OF THE SAME IN THE TREATMENT OF DEPRESSIVE CONDITIONS |
| KR870001153A (en) * | 1985-07-22 | 1987-03-11 | 데. 롤랑 | Pharmaceutical composition containing diphenoxyethylamine derivative and its production method |
-
1986
- 1986-07-21 AU AU60385/86A patent/AU593562B2/en not_active Ceased
- 1986-07-21 IE IE192586A patent/IE58999B1/en not_active IP Right Cessation
- 1986-07-22 KR KR1019860005928A patent/KR940011528B1/en not_active Expired - Fee Related
- 1986-07-22 DE DE8686401630T patent/DE3674873D1/en not_active Expired - Fee Related
- 1986-07-22 EP EP86401630A patent/EP0216646B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IE58999B1 (en) | 1993-12-15 |
| AU6038586A (en) | 1987-01-29 |
| KR940011528B1 (en) | 1994-12-20 |
| KR870001144A (en) | 1987-03-11 |
| AU593562B2 (en) | 1990-02-15 |
| DE3674873D1 (en) | 1990-11-15 |
| EP0216646A3 (en) | 1987-11-04 |
| EP0216646B1 (en) | 1990-10-10 |
| EP0216646A2 (en) | 1987-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |