DE594849C - Process for the preparation of ketones of the pyridine and quinoline series - Google Patents
Process for the preparation of ketones of the pyridine and quinoline seriesInfo
- Publication number
- DE594849C DE594849C DEB137478D DEB0137478D DE594849C DE 594849 C DE594849 C DE 594849C DE B137478 D DEB137478 D DE B137478D DE B0137478 D DEB0137478 D DE B0137478D DE 594849 C DE594849 C DE 594849C
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- Prior art keywords
- pyridine
- ketones
- preparation
- melting point
- water
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Darstellung von Ketonen der Pyridin- und Chinolinreihe Es wurde gefunden, daß man die bisher auf synthetischem Wege nicht hergestellten Ketone der Pyridin- und Chinolinreihe vom Typus des 2-Phenacylpyridins C,H,N # CH, CO # C6H5 in guter Ausbeute erhalten kann, wenn man im 2-Methylpyridin oder in dessen Derivaten, wie z. B. 2, 6-Dimethylpyridin (a, a'-Lutidin) oder 2-Methylchinolin (Clünaldin), die in 2-Stellung haftenden Methylgruppen ganz oder teilweise durch Phenacylreste (Phenacyl = - C H2 . C O # C6 H5) ersetzt.Process for the preparation of ketones of the pyridine and quinoline series It has been found that those previously not produced synthetically Ketones of the pyridine and quinoline series of the 2-phenacylpyridine type C, H, N # CH, CO # C6H5 can be obtained in good yield if one is in 2-methylpyridine or in its Derivatives such as B. 2,6-dimethylpyridine (a, a'-lutidine) or 2-methylquinoline (Clünaldin), all or part of the methyl groups adhering in the 2-position Phenacyl residues (Phenacyl = - C H2. C O # C6 H5) replaced.
In Ausübung des Verfahrens kann man z. B. 2-Methylpyridin oder Derivate desselben in üblicher Weise durch Kondensation mit Benzaldehyd in Verbindungen vom Typus des 2-Styrylpyridins überführen, diese durch Behandeln mit Halogen in die betreffenden symmetrischen Phenylpyridyldihalogenäthane überführen, aus welchen man durch einmalige oder auch stufenweise Halog enwass erstoffabspaltung glatt zu Pyridylphenylacetylen oder dessen Derivaten gelangt. Durch Wasseranlagerung an die .genannten Acetylenderivate, z. B. durch Behandeln mit 6o bis 70%iger Schwefelsäure, gelangt man überraschenderweise mit vorzüglicher Ausbeute zu den gewünschten Ketonen, deren einfachster Vertreter das i-Pyridyl-2-phenyläth:an-2-on darstellt.In exercising the method you can, for. B. 2-methylpyridine or derivatives same in the usual way by condensation with benzaldehyde in compounds from Convert type of 2-styrylpyridine, this by treatment with halogen in the relevant symmetrical Phenylpyridyldihalogenäthane convert from which can be achieved smoothly by splitting off halogen water once or in stages Pyridylphenylacetylene or its derivatives arrives. By accumulation of water on the . mentioned acetylene derivatives, z. B. by treatment with 6o to 70% sulfuric acid, surprisingly, the desired ketones are obtained in excellent yield, whose simplest representative is i-pyridyl-2-phenyleth: an-2-one.
War schon nicht zu erwarten, daß die Halogenwasserstoffabspaltung der Phenylpyridyldihalogenäthane gut vor sich gehen würde, so ist noch um so überraschender, daß die Wasseranlagerung an die Acetylenderivate vom Typus- des Pyridylphenylacetylens ausschließlich zu Phenacylderivaten führt, wo doch bekannt ist, daß z. B. bei aliphatischen unsynunetrischen Derivaten des Acetylens die Wasseranlagerung in zwei Richtungen hin erfolgt. Beispiel i Durch Erhitzen von 2-Methylpyridin mit Benzaldehyd bei Gegenwart von Chlorzink erhält man 2-Styrylpyridin. 181 g dieses z-Styrylpyridins werden in 11 siedendem Tetrachlorkohlenstoff gelöst. In die siedende Lösung läßt man im Verlauf von etwa i Stunde 165 g Brom, gelöst in 200 ccm Tetrachlorkohlenstoff, .eintropfen. Nach dem Erkalten saugt man vom auskristallisierten Dibrornid ab und wäscht mit Tetrachlorkohlenstoff nach. Ausbeute 32q.9= 95 % der Theorie an Dibromid vom Schmelzpunkt i75°. Die noch fehlenden 5 % können durch Einengen der Mutterlauge gewonnen werden.Was not to be expected that the elimination of hydrogen halide the Phenylpyridyldihalogenäthane would go well, it is all the more surprising, that the water attachment to the acetylene derivatives of the pyridylphenylacetylene type leads exclusively to phenacyl derivatives, where it is known that z. B. with aliphatic Unsymmetrical derivatives of acetylene cause water to accumulate in two directions is done. Example i By heating 2-methylpyridine with benzaldehyde in the presence 2-styrylpyridine is obtained from zinc chloride. 181 g of this z-styrylpyridine are used in 11 boiling carbon tetrachloride dissolved. In the boiling solution one leaves in the course drop 165 g of bromine dissolved in 200 cc of carbon tetrachloride for about one hour. After cooling, the dibrornide which has crystallized out is suctioned off and washed with it Carbon tetrachloride. Yield 32q.9 = 95% of theory of dibromide from the melting point i75 °. The remaining 5% can be obtained by concentrating the mother liquor.
341 g dieses 2-Styrylpyridindibromids werden mit 1,351 einer alkoholischen 2,25 n-Kalilauge i Stunde lang am Rückflußkühler gekocht; nach Absaugen des ausgeschiedenen Kaliiunbromids und Abdestillieren des Alkohols wird der Rückstand mit Wasser versetzt, das Acetylenderivat in Äther aufgenommen und nach Abdestillieren des Äthers durch Destillation im Vakuum gereinigt. Kpl 152'; Ausbeute 165 g = 92 °'o der Theorie.341 g of this 2-styrylpyridinedibromide are refluxed for 1 hour with 1.351 of an alcoholic 2.25 N potassium hydroxide solution; After the precipitated potassium bromide has been filtered off with suction and the alcohol has been distilled off, the residue is mixed with water, the acetylene derivative is taken up in ether and, after the ether has been distilled off, purified by distillation in vacuo. Kpl 152 '; Yield 1,65 g = 92 ° o of theory.
1799 symmetrisches Py-ridinphenylacetylen werden mit r,51 65%iger Schwefelsäure 5 Minuten ;gekocht. Nach dem Erkalten vcrsetzt man mit Wasser und macht mit Ammoniak alkalisch. Das ausfallende Öl, welches nach kurzer Zeit erstarrt, wird abgesaugt oder in Äther aufgenommen und nach Abdestillieren des letzteren im Vakuum destilliert. Ausbeute 93 % der Theorie. Das 2-Pheiiacylpyridin kristallisiert aus Benzin in derben Prismen vom F. 59° und siedet unter i mm Druck bei 159'. 1799 symmetrical pyridine phenylacetylene are boiled with r.51 65% sulfuric acid for 5 minutes. After cooling, the mixture is reacted with water and made alkaline with ammonia. The precipitated oil, which solidifies after a short time, is suctioned off or taken up in ether and, after the latter has been distilled off, distilled in vacuo. Yield 93% of theory. The 2-Pheiiacylpyridin crystallizes from gasoline in coarse prisms with a melting point of 59 ° and boils under 1 mm pressure at 159 °.
Das Oxim des 2-Phenacylpyridins kristallisiert aus Alkohol in Form zarter Prismen und schmilzt bei i 2o'. Beispiele 141,59 2, 6-Distyrylpyridin werden in i 1 kochendem Tetrachlorkohlenstof gelöst und mit Zoo g Brom i Stunde lang unter Rückfluß gekocht. Nach dem Erkalten saugt man von dem auskristallisierten Tetrabromid ab. Ausbeute 9¢ % der Theorie. Schmelzpunkt des Tetrabromids i 8o'.The oxime of 2-phenacylpyridine crystallizes from alcohol in the form delicate prisms and melts at i 2o '. Examples 141,59 2,6-distyrylpyridine dissolved in 1 boiling carbon tetrachloride and mixed with zoo g bromine for 1 hour Refluxed. After cooling, the crystallized tetrabromide is sucked off away. Yield 9% of theory. Melting point of the tetrabromide i 8o '.
i 5o,8 g Tetrabroin-2, 6-distyrylpyridin werden in o,81 kochendem Benzol gelöst und mit 50%igem überschuß von alkoholischer Isaliümhydroxydlösung einige Minuten lang gekocht, wobei das entstellende Kaliumbromid fast quantitativ ausfällt. Nach Absaugen von Kaliumbr omid wird das Filtrat auf etwa o,51 eingeengt. Beim Erkalten kristallisieren 56g eines in langen filzigen Nadeln kristallisierenden, bei 137° schmelzenden Körpers aus. Wenn man diesen Körper in methylalkoliolischer Lösung bzw. Suspension in Gegenwart von Palladium mit Wasserstoff behandelt, so werden mit außerordentlich großer Geschwindigkeit 2 M01 Wasserstoff aufgenommen, wobei die Hydrierungsgeschwindigkeit sich sehr verlangsamt. Bricht man nach Aufnahme der 2 M01 Wasserstoff die Hy drieriulg ab, so erhält man fast quantitativ 2, 6-Distyrylpyridin vom Schmelzpunkt 16.f°, wodurch bewiesen ist, daß der durch Bromwasserstoffabspaltung erhaltene Körper vom Schmelzpunkt 137° das Diacetylenderivat des 2, 6-Di-((3-phenyläthinyl)-pyridili darstellt.I 50.8 g of tetrabroin-2,6-distyrylpyridine are dissolved in o.81 boiling benzene and boiled for a few minutes with a 50% excess of alcoholic Isaliümhydroxydlösung, the disfiguring potassium bromide precipitates almost quantitatively. After suctioning off potassium bromide, the filtrate is concentrated to about 0.51. On cooling, 56g of a body crystallizing in long felted needles and melting at 137 ° crystallizes out. If this body is treated with hydrogen in a methyl alcoholic solution or suspension in the presence of palladium, 2 M01 hydrogen are absorbed at an extraordinarily high rate, the rate of hydrogenation being very slow. If the hydrogenation is interrupted after the 2 M01 hydrogen has been absorbed, 2,6-distyrylpyridine with a melting point of 16.f ° is obtained almost quantitatively, which proves that the body obtained by splitting off hydrogen bromide with a melting point of 137 ° is the diacetylene derivative of 2.6 -Di - ((3-phenyläthinyl) -pyridili represents.
35g 2, 6-Di("3-phenyläthinyl)-pyridin werden mit einem Gemisch von 200 ccm konzentrierter Schwefelsäure und 200 ccm Wasser i o Minuten lang gekocht. Auf Zusatz von Alkali fällt das 2, 6-Diphenacylpyridin als Öl aus, das alsbald kristallinisch erstarrt. Ausbeute 8o bis 9o % der Theorie. Das 2, 6-Diphenacylpyridin kristallisiert aus Alkohol in derben Nadeln vom Schmelzpunkt 87'. Der .:Schmelzpunkt des Oxims dieser Verbindung, welches aus Alkohol in dünnen Prismen erhalten wird, liegt bei r88°.35 g of 2,6-di ("3-phenylethinyl) pyridine are boiled for 10 minutes with a mixture of 200 cc of concentrated sulfuric acid and 200 cc of water. Upon addition of alkali, the 2,6-diphenacylpyridine precipitates as an oil, which immediately crystallizes Solidified. Yield 80 to 90% of theory. The 2,6-diphenacylpyridine crystallizes from alcohol in coarse needles with a melting point of 87 °. The melting point of the oxime of this compound, which is obtained from alcohol in thin prisms, is about 88 °.
Beispiel 3 , 3,b - Dibromid des 2-Styrylchinolins, h; rgestellt -nach Berichte 16 (i883# S. 20o8), werden mit alkoholischer Kalilauge erwärmt. Man saust vom ausfallenden Kaliumbromid ab, versetzt das Filtrat mit etwa 11 Nasser und äthert aus. Der Ätherrückstand kristallisiert aus Methanol in kleinen Täfelchen vom Schmelzpunkt i o i'; Ausbeute i o, 5 g.Example 3 , 3, b - Dibromide des 2-styrylquinoline, h; Established - according to reports 16 (i883 # p. 20o8), are heated with alcoholic potassium hydroxide solution. One rushes from the precipitated potassium bromide, the filtrate is mixed with about 1 1 Wet and extracted with ether from. The ether residue crystallizes from methanol in small tablets with a melting point of io i '; Yield 10.5 g.
Zog dieses bei ioi° schmelzenden Acetylderivates werden mit 300- 66o'oiger Schwefelsäure gekocht und nach dem Erkalten mit etwa i l Wasser versetzt. Das ausfallende Sulfat wird abgesaugt, in Methanol gelöst und zwecks Fällung der Base mit wäßrigem Ammoniak versetzt. Das 2-Phenacylchinolin kristallisiert aus Alkohol in kleinen Prismen vom Schmelzpunkt i 16°. Beispiel 3o- 2-Styrylchinoliri-q.-carbonsäure, hergestellt in üblicher Weise durch Kondensation von 2-Metliylchinolin-:i-carbonsäure und Benzaldehyd, werden in i l Chloroform mit i 9 g Brom i Stunde lang unter Rückfluß gekocht. Nach dem Erkalten der Chloroformlösung kann man 41 g des entstandenen Dibr omids absaugen und durch Einengen der Mutterlauge noch weitere 3 g gewinnen. (Das Dibromidkristallisiert aus Chloroform in dünnen gelben Platten vom Schmelzpunkt 267°.) 29g des erhaltenen Dibromids werden mit alkoholischer Kalilauge (log Kaliumhydroxyd in Zoo ccm absolutem Alkohol) 1l/2 Stunden lang gekocht. Nach dem Erkalten neutralisiert man mit verdünnter Salzsäure und versetzt mit etwa 30o ccm Wasser, wobei das entstandene Acetylenderivat praktisch quantitativ ausfällt. Ausbeute i 6, 5 g. (Aus Alkohol gelbliche dünne Prismen vom Schmelzpunkt 288°.) 2o g des bei 288° schmelzenden Acetylenderivates werden mit einem Gemisch von 35o ccm konzentrierter Schwefelsäure und Zoo ccm ZVasser 5 Minuten lang gekocht. Man kühlt ab, versetzt mit etwa 1,51 Wasser und gibt so viel Ammoniak zu, daß eben noch deutlich kongosaure Reaktion vorhanden ist. Die 2-Pheiiacylcbinolil1-:l-carbonsäure wird abgesaugt, mit Wasser gewaschen und aus Alkohol umkristallisiert. Gelbe Nädelchen vom Schmelzpunkt Die nach dem vorliegenden Verfahren erhältlichen neuen Verbindungen sollen als Zwischenprodukte zur Herstellung therapeutisch wertvoller Verbindungen, die natürlich vorkommenden Alkaloiden nahestehen, Verwendung finden.Pulled this melting at ioi ° acetyl derivative cooked with sulfuric acid and 300 66o'oiger added after cooling to about il water. The precipitated sulfate is filtered off with suction, dissolved in methanol and aqueous ammonia is added to precipitate the base. The 2-phenacylquinoline crystallizes from alcohol in small prisms with a melting point of 16 °. Example 3o-2-styrylquinoline-q.-carboxylic acid, prepared in the customary manner by condensation of 2-methylquinoline-: i-carboxylic acid and benzaldehyde, are refluxed for 1 hour in chloroform with 9 g of bromine. After the chloroform solution has cooled down, 41 g of the dibromide formed can be suctioned off and a further 3 g can be obtained by concentrating the mother liquor. (The dibromide crystallizes from chloroform in thin yellow plates with a melting point of 267 °.) 29 g of the dibromide obtained are boiled with alcoholic potassium hydroxide solution (log potassium hydroxide in zoo cc of absolute alcohol) for 1 1/2 hours. After cooling, it is neutralized with dilute hydrochloric acid and mixed with about 30o ccm of water, the acetylene derivative formed precipitating practically quantitatively. Yield i 6.5 g. (From alcohol, yellowish thin prisms with a melting point of 288 °.) 20 g of the acetylene derivative, which melts at 288 °, are boiled for 5 minutes with a mixture of 35 ° cc of concentrated sulfuric acid and zoo cc of water. The mixture is cooled, mixed with about 1.51 of water and ammonia is so much to that just yet clearly congo acid reaction is present. The 2-Pheiiacylcbinolil1-: l-carboxylic acid is filtered off with suction, washed with water and recrystallized from alcohol. Yellow needles with melting point The new compounds obtainable by the present process are intended to be used as intermediates for the preparation of therapeutically valuable compounds that are close to naturally occurring alkaloids.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB137478D DE594849C (en) | 1928-05-11 | 1928-05-11 | Process for the preparation of ketones of the pyridine and quinoline series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB137478D DE594849C (en) | 1928-05-11 | 1928-05-11 | Process for the preparation of ketones of the pyridine and quinoline series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE594849C true DE594849C (en) | 1934-03-22 |
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ID=6999208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB137478D Expired DE594849C (en) | 1928-05-11 | 1928-05-11 | Process for the preparation of ketones of the pyridine and quinoline series |
Country Status (1)
| Country | Link |
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| DE (1) | DE594849C (en) |
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1928
- 1928-05-11 DE DEB137478D patent/DE594849C/en not_active Expired
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