DE1595903B1 - 1-Substituted 2,6-dimethyl-4-phenylpiperazines - Google Patents
1-Substituted 2,6-dimethyl-4-phenylpiperazinesInfo
- Publication number
- DE1595903B1 DE1595903B1 DE19661595903 DE1595903A DE1595903B1 DE 1595903 B1 DE1595903 B1 DE 1595903B1 DE 19661595903 DE19661595903 DE 19661595903 DE 1595903 A DE1595903 A DE 1595903A DE 1595903 B1 DE1595903 B1 DE 1595903B1
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- substituted
- mixture
- phenyl
- solvent
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
N-QH5 (I)N-QH 5 (I)
CH-CH2 CH-CH 2
CH3 -CH 3 -
in der R ein Wasserstoffatom, eine niedere Alkyl-, eine mit Methoxygruppen substituierte Phenyläthyl-, eine Cinnamyl- oder eine Pyridyläthylgruppe bedeutet, und deren eis- und trans-Isomere.in which R is a hydrogen atom, a lower alkyl, a phenylethyl substituted with methoxy groups, means a cinnamyl or a pyridylethyl group, and their cis and trans isomers.
2. l-(3,4-Dimethoxyphenyläthyl)-2,6-dimethyl-4-phenylpiperazin und dessen eis- und trans-Isomere. 2. 1- (3,4-Dimethoxyphenylethyl) -2,6-dimethyl-4-phenylpiperazine and its cis and trans isomers.
3. Verfahren zur Herstellung der Verbindungen gemäß Anspruch 1, dadurch gekennzeichnet, daß man in an sich bekannter Weise ein 1-substituiertes 2,6 - Dimethyl - 4- phenyl- piperazinon - (3) der allgemeinen Formel II3. Process for the preparation of the compounds according to claim 1, characterized in that a 1-substituted 2,6 - dimethyl - 4 - phenyl piperazinone - (3) of the general formula II
ein 1 - substituiertes 2,6 - Dimethyl - 4 - phenyl - piperazinon-(3) der allgemeinen Formel IIa 1 - substituted 2,6 - dimethyl - 4 - phenyl - piperazinone- (3) of the general formula II
CH3 CH 3
CH — CH2 CH - CH 2
R-N N-C6H5 (II)RN NC 6 H 5 (II)
CH CCH C
IlIl
CH, OCH, O
in einem wasserfreien inerten organischen Lösungsmittel mit Lithiumaluminiumhydrid hydriert.hydrogenated in an anhydrous inert organic solvent with lithium aluminum hydride.
Die Ausgangsverbindungen, d. h. die 3-Piperazinone, können nach üblichen Methoden hergestellt werden. Eine vorteilhafte Synthese besteht z. B. aus den folgenden StufenThe starting compounds, i.e. H. the 3-piperazinones can be prepared by customary methods will. An advantageous synthesis consists, for. B. from the following stages
CH3
CH-CHCH 3
CH-CH
3030th
R —NR —N
N-QH5 (II)N-QH 5 (II)
CH-CH-
CH3 CH 3
-C O-C O
in einem wasserfreien inerten organischen Lösungsmittel mit Lithiumaluminiumhydrid hydriert.hydrogenated in an anhydrous inert organic solvent with lithium aluminum hydride.
4040
4545
Die vorliegende Erfindung betrifft 1-substituierte 2,6 - Dimethyl - 4 - phenylpiperazine der allgemeinen Formel IThe present invention relates to 1-substituted 2,6 - dimethyl - 4 - phenylpiperazines of the general kind Formula I.
CH3 CH 3
CH-CH2
R-N N-QH5 (I)CH-CH 2
RN N-QH 5 (I)
CH-CH2
CH,CH-CH 2
CH,
6060
in der R ein Wasserstoffaiom, eine niedere Alkyl-, eine mit Methoxygruppen substituierte Phenyläthyl-, eine Cinnamyl- oder eine Pyridyläthylgruppe bedeutet, und deren eis- und trans-Isomere.in which R is a hydrogen atom, a lower alkyl, a phenylethyl substituted with methoxy groups, means a cinnamyl or a pyridylethyl group, and their cis and trans isomers.
Diese Verbindungen werden erfindungsgemäß dadurch erhalten, daß man in an sich bekannter Weise CH3 — CH — COOC2H5 According to the invention, these compounds are obtained by adding CH 3 - CH - COOC 2 H 5
Br
-C2H5OHBr
-C 2 H 5 OH
(A)(A)
■+ CH, — CH — COOH■ + CH, - CH - COOH
BrBr
+ SOCl2 + SOCl 2
-»· CH3 — CH — COCl Br- »· CH 3 - CH - COCl Br
C6H5NH2 C 6 H 5 NH 2
NH, in ÄthanolNH, in ethanol
LiAlH4 LiAlH 4
+ A+ A
-> CH3-CH-CO-NH-QH5 Br-> CH 3 -CH-CO-NH-QH 5 Br
-»· CH3CH-CO-NHC6H5 NH2 - »· CH 3 CH-CO-NHC 6 H 5 NH 2
-» CH3 - CH - CH2 - NH - C6H5 NH2 - »CH 3 - CH - CH 2 - NH - C 6 H 5 NH 2
CH3 CH-CH2-NH-QH5 CH 3 CH-CH 2 -NH-QH 5
-* HN- * HN
260°260 °
CH-COOC2H5 CH-COOC 2 H 5
CH3 CH 3
CH3 CH 3
CH - CH2 CH - CH 2
-> HN N-C6H5 -> HN NC 6 H 5
CH-COCH-CO
CH,CH,
+ R — Halogen
oder H2CO/HCOOH + R - halogen
or H 2 CO / HCOOH
CH3 CH 3
CH - CH2 CH - CH 2
L-N N-L-N N-
CH-COCH-CO
CH,CH,
IOIO
Sowohl die Ausgangs- wie die Endverbindungen dieser Erfindung können wegen der beiden Methylgruppen in der cis-Form (äquatorial-äquatorial) und in der trans-Form (axial-äquatorial) auftreten. Die Trennung kann nach üblichen Methoden, z. B. durch fraktionierte Kristallisation oder Säulenchromatographie, durchgeführt werden. Je nach den Eigenschaften der Mischungen kann man zweckmäßig zuerst die 3-Piperazinone isolieren und die getrennten Isomeren hydrieren. Wahlweise kann die Trennung der cis-trans-Isomeren auch nach der Hydrierung, d. h. mit den Piperazinen erfolgen.Both the starting and the final compounds of this invention can because of the two methyl groups occur in the cis form (equatorial-equatorial) and in the trans-form (axial-equatorial). the Separation can be carried out by conventional methods, e.g. B. by fractional crystallization or column chromatography, be performed. Depending on the properties of the mixtures, one can expediently first isolate the 3-piperazinones and hydrogenate the separated isomers. Optionally, the separation of the cis-trans isomers even after the hydrogenation, d. H. done with the piperazines.
Die erfindungsgemäß erhältlichen Piperazine zeigen interessante pharmakologische Eigenschaften und insbesondere eine stark blutdrucksenkende Wirksamkeit.The piperazines obtainable according to the invention show interesting pharmacological properties and in particular a strong antihypertensive effect.
Die folgende Tabelle gibt die Dosen und die Werte der Blutdrucksenkung nach intravenöser Verabreichung einiger 2,6-Dimethyl-4-phenylpiperazine der allgemeinen Formel I bei anästhesierten Hunden im Vergleich zu Reserpin wieder.The following table gives the doses and values of lowering blood pressure after intravenous administration some 2,6-dimethyl-4-phenylpiperazines of the general formula I in anesthetized dogs in the Compared to reserpine again.
behandelten Tierenumber of
treated animals
mg/kgdose
mg / kg
des Aderdrucks
(mm Hg)Lowering
of the vein pressure
(mm Hg)
bei MäusenLD 50 Lp.
in mice
5555
Die folgenden Beispiele erläutern die Erfindung.The following examples illustrate the invention.
Beispiel 1
l,2,6-Trimethyl-4-phenylpiperazinexample 1
1,2,6-trimethyl-4-phenylpiperazine
a) Herstellung von 2,6-Dimethyl-4-phenylpiperazinon-(3) a) Preparation of 2,6-dimethyl-4-phenylpiperazinone- (3)
Eine Mischung von 375 g a-Brompropionsäure mit einem Überschuß Thionylchlorid (350 ecm) wird 3 Stunden am Rückfluß erhitzt. Dann wird durch fraktionierte Destillation das bei 129 bis 1330C übergehende Acylchlorid gewonnen.A mixture of 375 g of α-bromopropionic acid with an excess of thionyl chloride (350 ecm) is refluxed for 3 hours. The acyl chloride which passes over at 129 to 133 ° C. is then obtained by fractional distillation.
Das Acylchlorid wird mit Anilin und Triäthylamin in Diäthyläther umgesetzt, wobei die Mischung unter Rühren 1 Stunde erhitzt wird. Nach dem Abkühlen wird wäßrige l%ige Essigsäure zugesetzt, die Diäthylätherschicht über Natriumsulfat getrocknet und das Lösungsmittel abdestilliert. Der Rückstand ist a-Brompropionanilid; Ausbeute 450 g (82%). Das Anilid wird mit 8 1 29%igem Ammoniak und 21 Äthylalkohol (95%ig) umgesetzt. Nach einigen Tagen wird die Mischung im Vakuum konzentriert, der Rückstand gekühlt, mit Natriumhydroxid (50%ig) behandelt und mit Diäthyläther extrahiert. Die Ätherlösung wird zweimal mit Natriumchloridlösung gewaschen, über Natriumsulfat getrocknet und filtriert. Das Lösungsmittel wird abdestilliert, wobei a-Aminopropionanilid (289 g = 90%) als Rückstand erhalten wird. Dieses Anilid wird dann mit 130 g Lithiumaluminiumhydrid in 4,5 1 Diäthyläther zu a-Aminopropylanilin reduziert. Die Mischung wird 4 Stunden erhitzt und dann gekühlt. Das überschüssige Lithiumaluminiumhydrid wird mit wenig Wasser zerstört, die Mischung filtriert und über Natriumsulfat getrocknet. The acyl chloride is reacted with aniline and triethylamine in diethyl ether, the mixture is heated with stirring for 1 hour. After cooling, aqueous 1% acetic acid is added, the diethyl ether layer dried over sodium sulfate and the solvent was distilled off. The residue is α-bromopropionanilide; Yield 450g (82%). The anilide is with 8 1 29% ammonia and 21 Ethyl alcohol (95%) implemented. After a few days, the mixture is concentrated in vacuo, the Cooled residue, treated with sodium hydroxide (50%) and extracted with diethyl ether. The ethereal solution is washed twice with sodium chloride solution, dried over sodium sulfate and filtered. The solvent is distilled off, α-aminopropionanilide (289 g = 90%) being obtained as a residue will. This anilide is then mixed with 130 g of lithium aluminum hydride in 4.5 1 of diethyl ether to form α-aminopropylaniline reduced. The mixture is heated for 4 hours and then cooled. The excess lithium aluminum hydride is destroyed with a little water, the mixture is filtered and dried over sodium sulfate.
Das Lösungsmittel wird abdestilliert, wobei a-Aminopropylanilin erhalten wird (225 g = 85%). Das a-Aminopropylanilin wird mit etwa 300 g Äthyl-The solvent is distilled off, α-aminopropylaniline being obtained (225 g = 85%). The a-aminopropylaniline is mixed with about 300 g of ethyl
α-brompropionat in wasserfreiem Toluol (2,5 1) umgesetzt. Die Mischung wird 15 Stunden zum Rückfluß erhitzt, dann gekühlt und filtriert. Das Lösungsmittel wird abdestilliert und das rückständige öl mit verdünnter Salzsäure gewaschen. Anschließend wird Natriumkarbonatlösung zugesetzt, das Gemisch mit Diäthyläther extrahiert, über Natriumsulfat getrocknet, filtriert und das Lösungsmittel entfernt. Der erhaltene N - [1 - (2 - Phenylaminoisopropyl)]-alanin-äthylester (303 g = 80%) wird 4 Stunden bei 250 bis 265° C erhitzt, wobei sich Äthylalkohol bildet. Der Rückstand wird destilliert und die bei 140 bis 175° C (4 mm Hg) siedende Fraktion gesammelt; Ausbeute 180 g (60%) 2,6 - Dimethyl - 4 - phenylpiperazinon - (3); Siedepunkt 148 bis 15O0C/ 0,4 mm Hg.α-bromopropionate reacted in anhydrous toluene (2.5 1). The mixture is refluxed for 15 hours, then cooled and filtered. The solvent is distilled off and the residual oil is washed with dilute hydrochloric acid. Sodium carbonate solution is then added, the mixture is extracted with diethyl ether, dried over sodium sulfate, filtered and the solvent is removed. The obtained N - [1 - (2 - phenylaminoisopropyl)] - alanine ethyl ester (303 g = 80%) is heated for 4 hours at 250 to 265 ° C, whereby ethyl alcohol is formed. The residue is distilled and the fraction boiling at 140 to 175 ° C (4 mm Hg) is collected; Yield 180 g (60%) 2,6 - dimethyl - 4 - phenylpiperazinone - (3); Boiling point 148 to 15O 0 C / 0.4 mm Hg.
Die eis- und trans-Isomeren werden durch Säulenchromatographie auf Silicagel getrennt. Das Produkt wird in Chloroform/Methanol (99/1) gelöst. Aus 25 g Rohprodukt erhielt man 9 g des einen und 8 g des anderen Isomeren in reinem Zustande.The cis and trans isomers are determined by column chromatography separated on silica gel. The product is dissolved in chloroform / methanol (99/1). the end 25 g of crude product gave 9 g of one and 8 g of the other isomer in the pure state.
c) Herstellung von 1,2,6-Trimethyl-4-phenyl-piperazin c) Production of 1,2,6-trimethyl-4-phenyl-piperazine
2 g 1,2,6 - Trimethyl - 4 - phenyl - piperazinon - (3) werden mit 2 g Lithiumaluminiumhydrid in 60 ecm Diäthyläther 3 Stunden am Rückfluß erhitzt. Das Gemisch wird gekühlt, mit 5 ecm Wasser behandelt und filtriert. Das Filtrat wird über Natriumsulfat getrocknet und das Lösungsmittel abdestilliert. Ausbeute 1,6 g 1,2,6-Trimethyl-4-phenyl-piperazin (85%); Siedepunkt: 84 bis 860C bei 0,2 mm Hg.2 g of 1,2,6 - trimethyl - 4 - phenyl - piperazinone - (3) are refluxed with 2 g of lithium aluminum hydride in 60 ecm of diethyl ether for 3 hours. The mixture is cooled, treated with 5 ecm of water and filtered. The filtrate is dried over sodium sulfate and the solvent is distilled off. Yield 1.6 g of 1,2,6-trimethyl-4-phenyl-piperazine (85%); Boiling point: 84 to 86 0 C at 0.2 mm Hg.
Herstellung von 2,6-Dimethyl-4-phenyl-piperazin
5 g 2,6-Dimethyl-4-phenyl-piperazinon-(3) werden in 150 ecm Diäthyläther mit 2,5 g Lithiumaluminiumhydrid
versetzt. Die Mischung wird 3 Stunden erwärmt, dann gekühlt. 10 ecm Wasser werden
zugesetzt, die Diäthylätherschicht abgetrennt und das Lösungsmittel getrocknet. Ausbeute 4 g (80%)
2,6-Dimethyl-4-phenyl-piperazin; Siedepunkt: 87
bis 94°C bei 0,4 mm Hg.Production of 2,6-dimethyl-4-phenyl-piperazine
5 g of 2,6-dimethyl-4-phenyl-piperazinone- (3) are mixed with 2.5 g of lithium aluminum hydride in 150 ecm of diethyl ether. The mixture is heated for 3 hours then cooled. 10 ecm of water are added, the diethyl ether layer is separated off and the solvent is dried. Yield 4 g (80%) 2,6-dimethyl-4-phenyl-piperazine; Boiling point: 87 to 94 ° C at 0.4 mm Hg.
b) Herstellung von l,2,6-Trimethyl-4-phenylpiperazinon-(3) b) Preparation of 1,2,6-trimethyl-4-phenylpiperazinone- (3)
7 g 2,6-Dimethyl-4-phenyl-piperazinon-(3) werden 8 Stunden mit 14 g Formaldehyd (40%ig) und 16 g Ameisensäure (99%ig) am Rückfluß erhitzt. Das Gemisch wird gekühlt, mit Natronlauge (10%ig) behandelt und der Formaldehyd im Vakuum verdampft. Die Mischung wird mit Diäthyläther extrahiert, filtriert und das Lösungsmittel abdestilliert. Ausbeute 4 g l,2,6-Trimethyl-4-phenyl-piperazinon-(3).7 g of 2,6-dimethyl-4-phenyl-piperazinone- (3) are mixed with 14 g of formaldehyde (40%) and 16 g for 8 hours Formic acid (99%) heated to reflux. The mixture is cooled and treated with sodium hydroxide solution (10%) and the formaldehyde evaporates in vacuo. The mixture is extracted with diethyl ether, filtered and the solvent was distilled off. Yield 4 g of 1,2,6-trimethyl-4-phenyl-piperazinone- (3).
Beispiele 3 bis 5Examples 3 to 5
Nach dem in den vorigen Beispielen angegebenen Verfahren werden die folgenden Verbindungen der allgemeinen Formel I hergestellt:Following the procedure given in the previous examples, the following compounds are obtained general formula I produced:
4
53
4th
5
3,4-Dimethoxy-
phenyläthyl
4-PyridyläthylCinnamyl
3,4-dimethoxy
phenylethyl
4-pyridylethyl
72 bis 740C
99 bis 100°C210 to 222 ° C / 0.6mm
72 to 74 0 C
99 to 100 ° C
Claims (1)
CH-CHCH 3
CH-CH
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35441/65A GB1156498A (en) | 1965-08-18 | 1965-08-18 | Novel 2,6-Dimethyl-4-Phenyl-Piperazines and process for the manufacture thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1595903B1 true DE1595903B1 (en) | 1972-03-09 |
Family
ID=10377767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661595903 Pending DE1595903B1 (en) | 1965-08-18 | 1966-07-23 | 1-Substituted 2,6-dimethyl-4-phenylpiperazines |
Country Status (6)
| Country | Link |
|---|---|
| BR (1) | BR6681923D0 (en) |
| CH (1) | CH462823A (en) |
| DE (1) | DE1595903B1 (en) |
| FR (2) | FR1568736A (en) |
| GB (1) | GB1156498A (en) |
| NL (2) | NL6611479A (en) |
-
0
- NL NL132355D patent/NL132355C/xx active
-
1965
- 1965-08-18 GB GB35441/65A patent/GB1156498A/en not_active Expired
-
1966
- 1966-07-19 CH CH1043966A patent/CH462823A/en unknown
- 1966-07-23 DE DE19661595903 patent/DE1595903B1/en active Pending
- 1966-08-05 BR BR18192366A patent/BR6681923D0/en unknown
- 1966-08-16 NL NL6611479A patent/NL6611479A/xx unknown
- 1966-08-17 FR FR1568736D patent/FR1568736A/fr not_active Expired
- 1966-11-17 FR FR84018A patent/FR6128M/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR6128M (en) | 1968-06-24 |
| GB1156498A (en) | 1969-06-25 |
| FR1568736A (en) | 1969-05-30 |
| NL132355C (en) | |
| BR6681923D0 (en) | 1973-10-25 |
| CH462823A (en) | 1968-09-30 |
| NL6611479A (en) | 1967-02-20 |
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