IE43338B1 - Pharmaceutical compositions - Google Patents
Pharmaceutical compositionsInfo
- Publication number
- IE43338B1 IE43338B1 IE1930/75A IE193075A IE43338B1 IE 43338 B1 IE43338 B1 IE 43338B1 IE 1930/75 A IE1930/75 A IE 1930/75A IE 193075 A IE193075 A IE 193075A IE 43338 B1 IE43338 B1 IE 43338B1
- Authority
- IE
- Ireland
- Prior art keywords
- compositions
- methyl
- prop
- piperazine
- bis
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1521052 Pharmaceutical compositions BOEHRINGER INGELHEIM GmbH 2 Sept 1975 [3 Sept 1974] 03218/78 Divided out of 1521051 Heading A5B Pharmaceutical compositions in the form of dosage units useful in reducing the blood lipid level and the blood cholesterol level comprise as active ingredient N-[1-(3', 4'- methylenedioxyphenyl) - prop - 2 - yl] - N' - (2- chloro-phenyl)-piperazine or a physiologically compatible acid addition salt thereof in association with a pharmaceutical carrier or excipient, each dosage unit containing greater than 40 mg, but no greater than 60 mg of active ingredient. The compositions may further contain a coronary dilator such as 2, 6- bis-(diethanolamino)-4, 8-dipiperidino pyrimido [5, 4-d] pyrimidine, 3-(#-diethylamino ethyl)- 4-methyl-7-carbethoxymethoxy-2-oxo-2H - chromen, 3, 3'-(N, N'-dimethylethylenediamino)- bis-(propyl 3, 4, 5-trimethoxy benzoate, N-3'- phenylpropyl-(2')-1, 1-diphenyl-(3)-amine, α- isopropyl-α-[N-(methyl-N-homoveratryl)- y - aminopropyl]-3, 4-dimethoxy phenyl-acetonitrile or L-#-(#-hydroxy-α-methyl-phenylethylamino)-3-methoxypropiophenone. The compositions may be administered orally, parenterally or rectally in the form of granules, tablets, coated tablets, capsules, pills, syrups, emulsions, suspensions, powders, drops, suppositories or injection solutions.
Description
The present invention relates to pharmaceutical compositions comprising N-jj-(3l,4'-methylenedioxyphenyl)-prop-2-ylj-N'(2-chlorophenyl)-piperazine and acid addition salts thereof.
It is know from out Patent Specification No. 31348 that compounds of general formula CH. j (wherein Ar represents a fused bicyclic aromatic group in which the ring remote from the remainder of the molecule may, if desired, be a carbo- or heterocyclically saturated or aromatic ring; and and R2, which may be the same or different, each represents a hydrogen or halogen atom or a trifluoromethyl group or an alkyl or alkoxy group with 1 to 4 carbon atoms) and acid addition salts thereof, possess a depressant activity on the central nervous system and, therefore, appear to be suitable for use as sedatives, neuroleptics or major tranquilizers.
The present invention is based upon the discovery that a compound, i.e. N-[l-(31,4'-methylenedioxyphenyl)-prop-2-ylJ-N‘- (2-chlorophenyl)piperazine and the physiologically compatible acid addition salts thereof, possess the property of decreasing the level of lipids and the cholesterol level in the blood.
In particular tests which have been conducted show that N-0 - (3' ,4' -methyl enedi oxyphenyl) -prop-2-ylJ-N' - (2-chl orophenyl) piperazine and its physiologically compatible acid addition salts are even superior to the compounds disclosed in our Patent Specification No. 36586. Furthermore, the toxicity of the compounds of the present invention is low, so that these compounds are suitable for therepeutic use.
Thus according to one feature of the present invention there are provided pharmaceutical compositions comprising as active ingredient N-[j-(3' ,4'-methyl enedi oxyphenyl )-prop-2-ylJ-N'- (2-chl orophenyl )piperazine or a physiologically compatible acid addition salt thereof and a coronary dilator, together with a pharmaceutical carrier or excipient.
The coronary dilator to be employed in the pharmaceutical compositions of the present invention may, for example, include any of the following: 3-(B-diethyl ami noethyl)-4-methyl-7-carbethoxymethoxy-2-oxo-2H-chromen; 3,3'-(N,Ν'-dimethylethylenediamino)-bis-(propyl-3,4,5-trimethoxybenzoate); N-3'-phenyl propyl-(21)-1,1-diphenyl-(3)-amine; a-isopropyl-a-[n-(methyl-N-homoveratryl)-γ-aminopropyl ]-3,4dimethoxyphenyl-acetoni trile and ί-ω(g-hydroxy-a-methyl-phenyl ethylamino)-3-methoxy-propiophenone, but is preferably 'dipyridamol'. Thus, for example, for the prophylactic treatment of coronary thromboses, compositions, according to the invention contain N-[_l-(3‘ ,4'-methylenedioxyphenyl)-prop-2-yl] -N‘-(2-chlorophenyl)-piperazine or a physiologically compatible acid addition salt thereof and a coronary dilator such as 'dipyridamol' [i.e. 2,6-bis-(diethanol-amino)- 4,8-dipiperidino pyrimido[[5,4-djpyrimidinej .
The pharmaceutical compositions of the present invention are preferably in dosage unit form, each dosage unit preferably containing from 5 to 75 mg, especially from 40 to 60 mg, of n£-(3' ,4'-methylenedioxyphenyl)- prop-2-yl[]-N‘-(2-chlorophenyl)piperazine or a physiologically compatible acid addition salt thereof. Each dosage unit also preferably contains from 10 to 150 mg of the coronary dilator.
Pharmaceutical compositions in the form of dosage units comprising as active ingredient N-[l-(3',4'-methylenedioxy-phqnyl)prop-2-yl]-Ν'-(2-chlorophenyl)-piperazine or a physiologically compatible acid addition salt thereof in association with a pharmaceutical carrier or excipient, each dosage unit containing greater than 40 mg., but no greater than 60 mg of active ingredient are described and claimed in our Patent Specification No. 1840/80 the subject matter of which was divided out of the present specification.
N-(j -(3',4'-methylenedi oxyphenyl)-prop-2-ylJ -N'25 (2-chlorophenyl)-piperazine or a physiologically compatible acid addition salt thereof is conveniently administered in a daily dosage of from 25 to 75, preferably 40 to 60 mg., the compound being administered for example, 1 to 5 times daily. The coronary dilator is preferably administered in a daily dosage of 50 to 150 mg.
N-[l-(31,4'-methylenedioxyphenyl)-prop-2-ylJ-N'~ (2-chlorophenyl)-piperazine contains an asymmetric carbon atom and thus exists notonly in racemic form but also in the form of optically active isomers. It will be appreciated that pharmaceutical compositions containing any or all such forms of this compound (and physiologically compatible acid addition salts thereof) are within the scope of the present invention.
N-[l -(3' ,4'-methylenedioxyphenyl)-prop-2-ylJ-N'-(2-chlorophenyl) -piperazine, in either racemic or optically active form, and its physiologically compatible acid addition salts thereof may, for example, be prepared as described in our Patent Specification No. 31348.
The pharmaceutical compositions may be presented, for example, in a form suitable for oral, parenteral or rectal administration.
Thus the compositions may, for example, be presented in the conventional pharmacological forms of administration such as, for example, granules, tablets, coated tablets, pills, suspensions, drops, emulsions, powders, capsules or in a form suitable for obtaining sustained release. These compositions may, for example, be producted by the use of conventional pharmaceutical excipients employing the conventional methods of preparation.
Tablets may be produced, for example, by mixing the active ingredients with known excipients, such as inert diluents e.g. calcium carbonate, calcium phosphate or lactose, disintegrants such as corn starch or alginic acid, binders such as starch or gelatin, lubricants such as magnesium stearate or talcum and/or agents for obtaining a sustained release such as carboxypolymethylene, carboxy-methyl cellulose, cellulose acetatephthalate or polyvinyl acetate. The tablets may, if desired, also consist of several layers.
Coated tablets e.g. sugar-coated tablets may be produced in a similar manner by coatihg cores, produced in a similar manner to the tablets, with agents generally used for tablet coatings, such as polyvinylpyrrolidone, shellac, gum arabic, talcum, titanium dioxide or sugar. In order to obtain sustained release effects or in order to avoid incompatibilities, the core may consist of several layers. The tablet coat may also consist of several layers in order to obtain a sustained release, in which case the excipients mentioned above for tablets may be used.
Syrups of the active ingredient or active ingredient combinations according to the invention may, if desired, additionally contain a sweetener, such as saccharin, cyclamate, glycerin or sugar, and/or a taste improving agent such as flavourings, e.g. vanillin or orange extract.
They may also contain suspension agents or thickeners such as !5 sodium carboxymethylcellulose, wetting agents such as condensation products of fatty alcohols with ethylene oxide, or preservatives such as j>-hydroxy-benzoates.
Capsules containing an active ingredient or active ingredient combination may, for example, be produced by mixing the active ingredients with inert carriers, such as lactose or solbitol, and filling the mixture into gelatine capsules.
Suitable suppositories may be produced, for example, by mixing the active ingredient or active ingredient combinations with the conventional carriers envisaged for this purpose such as neutral fats or polyethylene glycol or derivatives thereof.
For parenteral administration, the carrier may be a sterile, parenterally compatible liquid such as sterile water, or a parenterally compatible oil e.g. arachis oil, in the form of injection solutions contained in ampoules.
The cholesterol decreasing action of N-^l-(3',4'methylenedioxyphenyl)-prop-2-ylJ-N'-(2-chlorophenyl)-piperazine and the physiologically compatible acid addition salts thereof was examined in a trial lasting 18 days and involving rats of the FU 49 strain. The compound was administered perorally, once daily by stomack-probe, in emulsion form together with the solubilizer Tween 80 (the word Tween is a trade mark). The controls received physiological, common salt solution together with Tween 80.
The serum-cholesterol was determined according to the methods of Levine, and J. and B. Zak in Clin. Chem. Acta 10, pages 381-384 (1964). The doses of Clofibrate, a preparation at present on the market, were 6 times higher than the doses of the other substances. The results are presented in the following table: Compound_Day 0 Day 4 Day 8 Day 18 rnnparison Compounds lofibrate 93.3 72.8 (-22%) 65.6 (-30%) 78.1 (-16%) -Cl-(3',4'-Methylenedioxyphenyl) irop-2-yli-N’-phenylpiperazine. HCl 89.9 70.8 (-21%) 55.7 (-38%) 51.3 (-43%) pound employed in the position of the present ention 1-(31,4'-Methylenedioxyphenyl) ip-2-ylJ-N'-(2-chlorbphenyi) irazine. HCl 75.0 33.7 (-55%) 20.4 (-73%) 5.9 (-92%) The total cholesterol content (average over 10 animals) in mg per 100 ml of serum and the percentage decrease over the course of the examination is stated in each case together with the final value for each group (D 0 = 100%).
The following non-limiting Examples serve to illustrate the invention. In each case the compositions were packed together with printed directions for the use of the compositions in reducing the blood lipid level and the blood cholesterol level. 433 38 Example 1 (Coated Tablets) N-[l- (31,4'-methylenedi oxyphenyl)prop-2-y1_j-N'-(2-chlorophenyl )piperazine. HCl 40 mg 5 2,6-bis-(diethanolaminp)-4,8-dipiperidinopyrimido [5,4-dl pyrimidine J 70 mg corn starch 60 mg sec. calcium phosphate 50 mg 10 magnesium stearate 3 mg water soluble starch 3 mg colloidal silicic acid 4 mg 280 mg Production The active ingredients are mixed with part of the excipients, thoroughly kneaded with an aqueous solution of the soluble starch and then granulated in the conventional manner. The granulate is mixed with the remaining excipients and pressed into tablet cores each weighing 380 mg of weight. The cores are coated with the aid of talcum, sugar and gum arabic in the conventional way. 3 3 3 8 Example 2 (Coated Tablets) core contains: N-3'-Phenylpropyl(2')-1, 1-diphenyl (3)-amine lactate 45.0 mg Lactose Potato starch Polyvi nylpyrrolidone Magnesium stearate .0 mg .0 mg 16.0 mg 3.0 mg 1.0 mg 110.0 mg Preparation: The mixture of the active substances lactose and potato starch is moistened with a 25% (by weight) ethanolic solution of polyvinylpyrrolidone, granulated through a sieve with a 1.5 mm. mesh 15 and dried at 45°C. The dried granulate is again granulated through a sieve of 1 mm. mesh and mixed with the magnesium stearate.
The cores thus obtained are coated in conventional manner with a coat which consists substantially of sugar and talc. The coated tablets thus obtained are polished with beeswax.
Final weight = 150 mg.
Example 3 (Suppositories) Suppository contains: 3-( @-Di ethyl ami noethyl)-4-methyl-7-carbethoxymethoxy2-oxo-2jl-chromen hydrochloride 125.0 mg N-Q-(3',4'-methyl enedi oxy)prop-2-yl]-N'piperazine 75.0 mg * Suppository base e.g. Witepsol H 12 1600.0 mg 1800.0 mg (*Witepsol is a trade mark) The finely divided active substance is stirred into the melted suppository base at 40°C. The mixture is homogenised and poured at about 35°C into slightly pre-cooled moulds.
Suppository weight: 1.7 g.
Example 4 (Coated Tablets) core contains:N-[l-(3' ,4'-methyl enedi oxyphenyl )-prop-2-ylJ- N'-(2-chlorophenyl)-piperazine HCl 40 mg α-isopropyl-a -Tn-(methyl-N-homoveratryl)a-aminopropylj-3,4-dimethoxyphenylacetonitrile 70 mg corn starch 60 mg lactose 50 mg sec. calcium phosphate 50 mg magnesium stearate 3 mg water soluble starch 3 mg collodal silicic acid 4 mg Production: As described in Example 1 280 mg 13338 Example 5 (Coated Tablets) core contains:N- [1 - (3 ‘ -4'-methylenedi oxyphenyl)-prop-2-ylJ -N'-(2-chlorophenyl)-pi perazi ne HCl 40 mg 5 L-in~( p-hydroxy-a-methyl -phenyl ethyl ami no) - 3-methoxy-propiophenone 70 mg lactose 50 mg corn starch 60 mg sec. calcium phosphate 50 mg 10 magnesium stearate 3 mg water soluble starch 3 mg colloidal silicic acid 4 mg 280 mg Production: As described in Example 1 No claim is made herein to pharmaceutical compositions in dosage unit form, wherein each dosage unit contains a coronary dilator, a pharmaceutical carrier or excipient and greater than 40 mg. but no greater than 60 mg. of N-Ql-(3',4'-methylenedioxyphenyl)-prop2-yl.]-N'-(2-chlorophenyl)-piperazine or a physiologically compatible acid addition salt thereof.
Claims (10)
1. Pharmaceutical compositions comprising as active ingredient N-|j -(3'»4methylenedi oxyphenyl)-prop-2-ylJ-N'-(2-chlorophenyl)piperazine or a physiologically compatible acid addition salt thereof 5 and a coronary dilator together with a pharmaceutical carrier or excipient.
2. Compositions as claimed in claim 1 wherein the coronary dilator comprises 2,6-bis-(diethanolamino)-4,8-dipiperidino pyr i mi do [5,4-dj pyr imi dine. 10
3. Compositions as claimed in claim 1 wherein the coronary dilator comprises 3-(β-d i ethyl ami noethyl)-4-methyl-7-carbethoxymethoxy2-oxo-2H-chromen; 3, 3'-(N,N'-dimethylethy1enediamino)-bis(propyl-3,4,5-trimethoxy-benzoate); N-3 1 -phenyl propyl-(2')-1. 1-di phenyl-(3)-ami ne; α-i sopropyl-α-pl-methyl-N-homoveratryl)-γ15 aminopropylj-3,4-dimethoxyphenyl-acetonitrile or Lω-(β-hydroxy-a-methyl-phenyl ethyl ami no)-3-methoxy-propi ophenone.
4. Compositions as claimed in any of the preceding claims in the form of dosage units.
5. Compositions as claimed in claim 4 wherein each dosage unit 20 contains from 5 to 75 mg of N-jj-(3‘ ,4'-methyl enedi oxyphenyl )-prop -2-yl]-N'-(2-chlorophenyl)-piperazine or a physiologically compatible acid addition salt thereof.
6. Compositions as claimed in claim 4 or claim 5 wherein each dosage unit contains from 10 to 150 mg of a coronary dilator.
7. Compositions as claimed in any of the preceding claims in the form of granules, tablets, coated tablets, capsules, pills, syrups, emulsions, suspensions, powders, drops, suppositories or injection solutions. 5
8. Compositions as claimed in claim 1 substantially as herein described.
9. Compositions as claimed in claim 1 substantially as herein described in Example 1.
10. Compositions as claimed in claim 1 substantially as herein lo described in any one of Examples 2 to 5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE1840/80A IE43339B1 (en) | 1974-09-03 | 1975-09-03 | Pharmaceutical compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2442158A DE2442158C3 (en) | 1974-09-03 | 1974-09-03 | New substituted N- [1 (3,4-methylenedioxyphenyl) propyl (2)] -N'-subst phenylpiperazines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43338L IE43338L (en) | 1976-03-03 |
| IE43338B1 true IE43338B1 (en) | 1981-02-11 |
Family
ID=5924765
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1930/75A IE43338B1 (en) | 1974-09-03 | 1975-09-03 | Pharmaceutical compositions |
| IE1929/75A IE41667B1 (en) | 1974-09-03 | 1975-09-03 | Substituted phenylpiperazine compounds and pharmaceutical uses thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1929/75A IE41667B1 (en) | 1974-09-03 | 1975-09-03 | Substituted phenylpiperazine compounds and pharmaceutical uses thereof |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS52287A (en) |
| AT (1) | AT344699B (en) |
| BE (2) | BE833003A (en) |
| BG (1) | BG26381A3 (en) |
| CA (2) | CA1063027A (en) |
| CH (1) | CH615174A5 (en) |
| CS (1) | CS192521B2 (en) |
| DD (1) | DD124118A5 (en) |
| DE (1) | DE2442158C3 (en) |
| DK (1) | DK137387C (en) |
| ES (5) | ES440630A1 (en) |
| FI (1) | FI60006C (en) |
| FR (1) | FR2283682A1 (en) |
| GB (3) | GB1521051A (en) |
| HU (1) | HU176754B (en) |
| IE (2) | IE43338B1 (en) |
| IL (2) | IL48033A (en) |
| LU (2) | LU73317A1 (en) |
| NL (1) | NL7510319A (en) |
| NO (1) | NO142911C (en) |
| NZ (1) | NZ178566A (en) |
| PH (1) | PH13631A (en) |
| PL (1) | PL95233B1 (en) |
| RO (1) | RO68380B (en) |
| SE (1) | SE419084B (en) |
| YU (1) | YU37164B (en) |
| ZA (2) | ZA755602B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54109307U (en) * | 1978-01-19 | 1979-08-01 | ||
| US4647606A (en) * | 1982-12-27 | 1987-03-03 | Owens-Corning Fiberglas Corporation | Blend of rapid set asphaltic emulsion with slow set asphalt emulsion |
| HU187229B (en) * | 1983-04-14 | 1985-11-28 | Koezponti Valto Hitelbank | Method for producing fodder increasing yield or additional fodder composition |
| AUPN359095A0 (en) * | 1995-06-19 | 1995-07-13 | Mount Shamrock Pty Ltd | Saw system |
-
1974
- 1974-09-03 DE DE2442158A patent/DE2442158C3/en not_active Expired
-
1975
- 1975-08-13 FI FI752288A patent/FI60006C/en not_active IP Right Cessation
- 1975-08-25 AT AT653875A patent/AT344699B/en not_active IP Right Cessation
- 1975-08-28 RO RO83281A patent/RO68380B/en unknown
- 1975-09-01 DD DD188118A patent/DD124118A5/xx unknown
- 1975-09-01 CS CS755930A patent/CS192521B2/en unknown
- 1975-09-01 BG BG030900A patent/BG26381A3/en unknown
- 1975-09-02 JP JP50106441A patent/JPS52287A/en active Pending
- 1975-09-02 IL IL48033A patent/IL48033A/en unknown
- 1975-09-02 PL PL1975183066A patent/PL95233B1/pl unknown
- 1975-09-02 GB GB36147/75A patent/GB1521051A/en not_active Expired
- 1975-09-02 DK DK393775A patent/DK137387C/en active
- 1975-09-02 NO NO753020A patent/NO142911C/en unknown
- 1975-09-02 IL IL48036A patent/IL48036A/en unknown
- 1975-09-02 GB GB36152/75A patent/GB1514546A/en not_active Expired
- 1975-09-02 GB GB3218/78A patent/GB1521052A/en not_active Expired
- 1975-09-02 HU HU75BO1570A patent/HU176754B/en unknown
- 1975-09-02 ES ES440630A patent/ES440630A1/en not_active Expired
- 1975-09-02 YU YU2219/75A patent/YU37164B/en unknown
- 1975-09-02 BE BE159687A patent/BE833003A/en not_active IP Right Cessation
- 1975-09-02 NL NL7510319A patent/NL7510319A/en not_active Application Discontinuation
- 1975-09-02 SE SE7509746A patent/SE419084B/en unknown
- 1975-09-02 BE BE159686A patent/BE833002A/en not_active IP Right Cessation
- 1975-09-03 ZA ZA755602A patent/ZA755602B/en unknown
- 1975-09-03 LU LU73317A patent/LU73317A1/xx unknown
- 1975-09-03 FR FR7527056A patent/FR2283682A1/en active Granted
- 1975-09-03 CA CA234,708A patent/CA1063027A/en not_active Expired
- 1975-09-03 NZ NZ178566A patent/NZ178566A/en unknown
- 1975-09-03 ZA ZA755601A patent/ZA755601B/en unknown
- 1975-09-03 IE IE1930/75A patent/IE43338B1/en unknown
- 1975-09-03 PH PH17540A patent/PH13631A/en unknown
- 1975-09-03 IE IE1929/75A patent/IE41667B1/en unknown
- 1975-09-03 LU LU73316A patent/LU73316A1/xx unknown
- 1975-09-03 CA CA234,707A patent/CA1061343A/en not_active Expired
-
1976
- 1976-12-03 ES ES453935A patent/ES453935A1/en not_active Expired
- 1976-12-03 ES ES453934A patent/ES453934A1/en not_active Expired
- 1976-12-03 ES ES453932A patent/ES453932A1/en not_active Expired
- 1976-12-03 ES ES453933A patent/ES453933A1/en not_active Expired
-
1979
- 1979-05-07 CH CH425779A patent/CH615174A5/en not_active IP Right Cessation
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