DE936446C - Process for the preparation of new amides of pyridine-3, 5-dicarboxylic acid - Google Patents
Process for the preparation of new amides of pyridine-3, 5-dicarboxylic acidInfo
- Publication number
- DE936446C DE936446C DEC4161A DEC0004161A DE936446C DE 936446 C DE936446 C DE 936446C DE C4161 A DEC4161 A DE C4161A DE C0004161 A DEC0004161 A DE C0004161A DE 936446 C DE936446 C DE 936446C
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- Prior art keywords
- pyridine
- carboxylic acid
- formula
- acid
- dicarboxylic acid
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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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
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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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
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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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung neuer Amide der Pyridin-3, 5-dicarbonsäure Gegenstand der Erfindung ist ein Verfahren zur Herstellung neuer Amide der Pyridin-3, 5-dicarborisäure von der allgemeinen Formel worin R1 und R2 Alkylreste bedeuten oder worin R1 und R2 zusammen einen Alkylenrest bedeuten, der mit beiden verfügbaren Wertigkeiten an das Amidstickstoffatom gebunden ist und durch ein Sauerstoff-oder Schwefelatom oder durch eine N-Alkylgruppe unterbrochen sein kann. Es wurde gefunden, daB Verbindungen dieser Formel überraschende pharmakologische Eigenschaften entwickeln.Process for the preparation of new amides of pyridine-3,5-dicarboxylic acid The invention relates to a process for the preparation of new amides of pyridine-3,5-dicarboric acid of the general formula in which R1 and R2 denote alkyl radicals or in which R1 and R2 together denote an alkylene radical which is bonded to the amide nitrogen atom with both valencies and can be interrupted by an oxygen or sulfur atom or by an N-alkyl group. It has been found that compounds of this formula develop surprising pharmacological properties.
Stoffe mit ähnlicher Konstitution sind teilweise schon bekanntgeworden. So beschreibt z. B. R. Graf (J. f. pr. Ch., N. F. Bd. 138, S. 25gff. [1g33]) die Herstellung von Pyridin-3, 5-dicarbonsäure-bis-dialkylamiden, welche in 2,6-Stellung noch methyliert sein können. Diese Verbindungen haben aber keine Wirkungssteigerung'im Vergleich zu dem bekannten Nicotinsäurediäthylamid gebracht, wurden sie doch, schon seit 1g33 bekannt, nicht in die Praxis eingeführt.Substances with a similar constitution have already become known in some cases. So describes z. B. R. Graf (J. f. Pr. Ch., N. F. Vol. 138, p. 25gff. [1g33]) the Production of pyridine-3, 5-dicarboxylic acid-bis-dialkylamides, which are in the 2,6-position can still be methylated. However, these compounds do not increase their effectiveness When compared to the well-known nicotinic acid diethylamide, they were, yes known since 1g33, not put into practice.
Durch die französische Patentschrift 798 639 sind verschiedene Pyridin-2, 3- und -3, 4.-dicarbonsäure-bisdialkylamide und durch Chemisches - Zentralblatt 193411, S.3255, Pyridin-2, 5-dicarbonsäure-bis-dialkylamide bekanntgeworden. Auch diese Verbindungen besitzen, wie eigene Versuche bestätigten, keinerlei Vorzüge gegenüber dem einfachen Nicotinsäurediäthylamid. Sperber und Mitarbeiter (Journ. Am. Soc., Bd. 72, S. 20I2ff. [195o]) versuchten, die Wirksamkeit und Löslichkeit des Nicotinsäure-(dibutyl-hexyl)-amids durch Einführung einer Carboxyl-bzw. Carbomethoxygruppe zu steigern. Sie fanden, daß durch diese Maßnahme die Wirksamkeit aber stark abnimmt, ja sogar verschwindet.Through the French patent 798 639 , various pyridine-2, 3- and -3, 4.-dicarboxylic acid-bisdialkylamides and through Chemisches - Zentralblatt 193411, p.3255, pyridine-2,5-dicarboxylic acid-bis-dialkylamides have become known. As our own experiments have confirmed, these compounds also have no advantages over the simple nicotinic acid diethylamide. Sperber et al. (Journ. Am. Soc., Vol. 72, pp. 20I2ff. [195o]) tried to improve the effectiveness and solubility of nicotinic acid (dibutylhexyl) amide by introducing a carboxyl or. Increase carbomethoxy group. They found that with this measure, however, the effectiveness strongly decreases, even disappears.
Um so überraschender war es nun zu finden, daß Verbindungen der eingangs erwähnten Formel wertvolle pharmakologische Eigenschaften entwickeln. So sind z. B. die Pyridin-3, 5-dicarbonsäure-3-amide-5-dialkylamide bzw. -5-morpholide, -piperidide wirksame Analeptica, ohne die bekannten und sehr unangenehmen Nebenwirkungen des Nicotinsäurediäthylamids zu zeigen. Ihre Toxizität liegt bedeutend tiefer als die der letzterwähnten Verbindung, wodurch den erfindungsgemäßen Stoffen eine größere therapeutische Breite zugesprochen werden kann.It was all the more surprising to find that connections of the initially mentioned formula develop valuable pharmacological properties. So are z. B. the pyridine-3, 5-dicarboxylic acid-3-amide-5-dialkylamides or -5-morpholide, -piperidide effective analeptics without the well-known and very unpleasant side effects of the To show nicotinic acid diethylamide. Their toxicity is significantly lower than that the last-mentioned compound, which gives the substances according to the invention a greater therapeutic breadth can be assigned.
Die in Frage stehenden Verbindungen werden hergestellt durch Umsetzung a) eines funktionellen Derivats der Pyridin-3-(bzw. -5-) carbonsäureamid-5- (bzw. -3-) carbonsäure der Formel mit einem Amin der Formel in welcher R1 und R2 die bereits erwähnte Bedeutung zukommt, b) der genannten Säure (I) oder eines ihrer Salze mit einem Carbaminsäurehalogenid der Formel worin R1 und R2 die obige Bedeutung haben und Hal ein Halogenatom darstellt, c) eines funktionellen Derivates einer Pyridin-5-(bzw. -3-) carbonsäureamid-3- (bzw. -5-) carbonsäure der Formel worin R1 und R2 die bereits erwähnte Bedeutung zukommt, mit Ammoniak, oder d) der genannten Säure. (IV) oder eines Salzes derselben mit einem ursubstituierten Carbaminsäurehalogenid.The compounds in question are prepared by reacting a) a functional derivative of pyridine-3- (or -5-) carboxamide-5- (or -3-) carboxylic acid of the formula with an amine of the formula in which R1 and R2 have the meaning already mentioned, b) the acid (I) mentioned or one of its salts with a carbamic acid halide of the formula where R1 and R2 have the above meaning and Hal represents a halogen atom, c) a functional derivative of a pyridine-5- (or. -3-) carboxamide-3- (or -5-) carboxylic acid of the formula where R1 and R2 have the meaning already mentioned, with ammonia, or d) the acid mentioned. (IV) or a salt thereof with an unsubstituted carbamic acid halide.
Beispiele I. 70 g Py-ridin-3-carbonsäuremethylester-5-carbonsäure-diäthylamid werden in 5oo ccm konzentriertes wäßriges Ammoniak eingetragen, und das Gemisch wird 36 Stunden bei 2o° stehengelassen. Anschließend dampft man bei 2o° einen Teil des überschüssigen Ammoniaks weg und saugt das Kristallisat ab. Das Filtrat wird zur Trockne verdampft, der Rückstand aus Essigester umkristallisiert und, mit dem ersten Kristallisat vereinigt, nochmals aus Dioxan umkristallisiert. Man erhält so 43 bis 45 g Pyridin-3 - carbonsäureamid - 5 -carbonsäure - diäthylarnid als farblose Kristalle, die-bei 139 bis I41° schmelzen. Leicht löslich in kaltem Wasser, Äthanol, Eisessig, wenig löslich in Äther, Benzol und Petroläther. Umkristallisierbar aus Dioxan und Essigester.EXAMPLES I. 70 g of methyl pyridine-3-carboxylate-5-carboxylic acid diethylamide are introduced into 500 cc of concentrated aqueous ammonia, and the mixture is left to stand for 36 hours at 20 °. Part of the excess ammonia is then evaporated at 20 ° and the crystals are filtered off with suction. The filtrate is evaporated to dryness, the residue is recrystallized from ethyl acetate and, combined with the first crystals, recrystallized again from dioxane. This gives 43 to 45 g of pyridine-3-carboxamide-5-carboxylic acid diethyl amide as colorless crystals which melt at 139 ° to 141 °. Easily soluble in cold water, ethanol, glacial acetic acid, slightly soluble in ether, benzene and petroleum ether. Recrystallizable from dioxane and ethyl acetate.
2. 33 g Pyridin-3, 5-dicarbonsäure-monoamid, erhalten aus Pyridin-3, 5-dicarbonsäure-mono-methylester und Ammoniak, werden in Ioo ccm gn-Natronlauge gelöst, die Lösung wird bei möglichst tiefer Temperatur verdampft und im Vakuum getrocknet. Zu dem Kolbenrückstand gibt man 28 g N, N-Diäthyl-carbaminsäurechlorid, gelöst in 150 ccm abs. Dioxan. Man kocht 8 Stunden am Rückfiußkühler und saugt dann noch heiß das gebildete Natriumchlorid ab. Beim Kühlen des Filtrats kristallisiert das Pyridin-3-carbonsäureamid-5-carbonsäure-diäthylamid in farblosen, bei 139 bis I41° schmelzenden Nadeln aus. Dieses kann nötigenfalls durch Umkristallisieren aus Essigester gereinigt werden.2. 33 g of pyridine-3,5-dicarboxylic acid monoamide, obtained from pyridine-3,5-dicarboxylic acid monomethyl ester and ammonia, are dissolved in 100 cc of gn sodium hydroxide solution, the solution is evaporated at the lowest possible temperature and in vacuo dried. 28 g of N, N-diethylcarbamic acid chloride, dissolved in 150 ccm of abs, are added to the flask residue. Dioxane. The mixture is boiled for 8 hours on the reflux condenser and the sodium chloride formed is then filtered off with suction while it is still hot. On cooling the filtrate, the pyridine-3-carboxamide-5-carboxy-acid diethylamide crystallizes out in colorless needles melting at 139 ° to 141 °. If necessary, this can be purified by recrystallization from ethyl acetate.
3. Aus dem Pyridin-3-carbonsäureäthylester-5-carbonsäuremorpholid und Ammoniak stellt man das Pyridin-3-carbonsäureamid-5-carbonsäuremorpholld her, Schmelzpunkt 169 bis I71°, leicht löslich in Chloroform, Äthanol, Wasser, Aceton, mäßig in Essigester.3. From the pyridine-3-carboxylic acid ethyl ester-5-carboxylic acid morpholide and ammonia one produces the pyridine-3-carboxamide-5-carboxylic acid morphold, Melting point 169 to 171 °, easily soluble in chloroform, ethanol, water, acetone, moderately in ethyl acetate.
4. Aus dem Pyridin-3-carbonsäureäthylester-5-carbonsäurepiperidid stellt man in äthanolisch-wäßriger Ammoniaklösung durch Sättigen mit Ammoniak bei o° das Pyridin-3-carbonsäureamid-5-carbonsäurepiperidid her, Schmelzpunkt 112 bis 1I3°, leicht löslich in Chloroform, Äthanol, Wasser, Aceton, mäßig löslich in Essigester.4. From the pyridine-3-carboxylic acid ethyl ester-5-carboxylic acid piperidide is provided in ethanolic aqueous ammonia solution by saturation with ammonia o ° the pyridine-3-carboxamide-5-carboxylic acid piperidide, melting point 112 bis 11.3 °, easily soluble in chloroform, ethanol, water, acetone, moderately soluble in ethyl acetate.
5. Das aus 6o g Pyridin-3, 5-dicarbonsäure-monoäthylester und 300 ccm Thionylchlorid durch 1/2stündiges Kochen erhaltene Esterchlorid wird nach dem Reinigen in 250 ccm Benzol gelöst und mit 34 g 2-Methylpiperidin und 24 g Pyridin in 250 ccm Benzol versetzt. Nach 2 Stunden saugt man das Pyridinhydrochloridab, wäscht mit Benzol nachundverdampft das Filtrat zur Trockne. Den Rückstand, bestehend aus Pyridin-3-carbonsäureäthylester-5-carbonsäure-(2'-methylpiperidid), übergießt man mit 5oo ccm wäßriger Ammoniaklösung, schüttelt 24 Stunden bei ,2o°, dampft ein und kocht den Rückstand mit Essigester aus. Die Extraktlösung wird durch eine Kohlesäule filtriert, auf die Hälfte verdampft, warm mit Äther bis zur Trübung versetzt und auf o° gekühlt. Man erhält 35 bis 37 g Pyridin-3-carbonsäureamid-5-carbonsäure-(2'-methylpiperidid). Schmelzpunkt 126,5 bis r28°; leicht löslich in heißem Wasser, Methanol, Äthanol und 2 n-Salzsäure, wenig löslich in Aceton, Benzol, Toluol und Äther.5. The ester chloride obtained from 60 g of pyridine-3,5-dicarboxylic acid monoethyl ester and 300 cc of thionyl chloride by boiling for 1/2 hour is dissolved in 250 cc of benzene after cleaning and with 34 g of 2-methylpiperidine and 24 g of pyridine in 250 cc of benzene offset. After 2 hours, the pyridine hydrochloride is filtered off with suction, washed with benzene and the filtrate is evaporated to dryness. The residue, consisting of pyridine-3-carboxylic acid ethyl ester-5-carboxylic acid (2'-methylpiperidide), is poured over with 500 ccm of aqueous ammonia solution, shaken for 24 hours at .20 °, evaporated and the residue is boiled with ethyl acetate. The extract solution is filtered through a charcoal column, evaporated to half, warm ether is added until it becomes cloudy and the mixture is cooled to 0 °. 35 to 37 g of pyridine-3-carboxamide-5-carboxylic acid (2'-methylpiperidide) are obtained. Melting point 126.5 to r28 °; Easily soluble in hot water, methanol, ethanol and 2N hydrochloric acid, slightly soluble in acetone, benzene, toluene and ether.
6. Aus dem Pyridin-3-carbonsäureäthylester-5-carbonsäure-(N'-isopropyl-piperazid) und Ammoniak stellt man das Pyridin-3-carbonsäureamid-5-carbonsäure-(N'-isopropyl-piperazid) her, farblose Kristalle, leicht löslich in Chloroform und Wasser. Das Monohydrochlorid erhält man in farblosen Nädelchen aus äthanolischer Salzsäure, leicht löslich in Wasser.6. From the pyridine-3-carboxylic acid ethyl ester-5-carboxylic acid (N'-isopropyl-piperazide) and ammonia, the pyridine-3-carboxamide-5-carboxylic acid (N'-isopropyl-piperazide) is produced forth, colorless crystals, easily soluble in chloroform and water. The monohydrochloride is obtained in colorless needles made from ethanolic hydrochloric acid, easily soluble in Water.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH936446X | 1950-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE936446C true DE936446C (en) | 1955-12-15 |
Family
ID=4549152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC4161A Expired DE936446C (en) | 1950-05-12 | 1951-05-08 | Process for the preparation of new amides of pyridine-3, 5-dicarboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE936446C (en) |
-
1951
- 1951-05-08 DE DEC4161A patent/DE936446C/en not_active Expired
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