DE1141986B - Process for the preparation of 3, 4, 5-trimethoxybenzoic acid amides having a tranquillose-dative action - Google Patents
Process for the preparation of 3, 4, 5-trimethoxybenzoic acid amides having a tranquillose-dative actionInfo
- Publication number
- DE1141986B DE1141986B DEV17061A DEV0017061A DE1141986B DE 1141986 B DE1141986 B DE 1141986B DE V17061 A DEV17061 A DE V17061A DE V0017061 A DEV0017061 A DE V0017061A DE 1141986 B DE1141986 B DE 1141986B
- Authority
- DE
- Germany
- Prior art keywords
- trimethoxybenzoic acid
- tranquillose
- acid amides
- preparation
- action
- 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
- GGNMTJKRHHLJHH-UHFFFAOYSA-N 3,4,5-trimethoxybenzamide Chemical class COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 230000001624 sedative effect Effects 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 5
- SBAJRGRUGUQKAF-UHFFFAOYSA-N 3-(2-cyanoethylamino)propanenitrile Chemical compound N#CCCNCCC#N SBAJRGRUGUQKAF-UHFFFAOYSA-N 0.000 description 5
- VMBFKKOESWAMII-UHFFFAOYSA-N n-butyl-3,4,5-trimethoxybenzamide Chemical compound CCCCNC(=O)C1=CC(OC)=C(OC)C(OC)=C1 VMBFKKOESWAMII-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000932 sedative agent Substances 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 3
- 230000000147 hypnotic effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000004899 motility Effects 0.000 description 3
- CEHVLIKQGJYEJA-UHFFFAOYSA-N 2-amino-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CN CEHVLIKQGJYEJA-UHFFFAOYSA-N 0.000 description 2
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 description 2
- -1 alkyl radical Chemical group 0.000 description 2
- 239000002249 anxiolytic agent Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- UWIGEOMJXLJZEG-SNAWJCMRSA-N (E)-N-carbamoylhex-2-enamide Chemical compound C(C)C/C=C/C(=O)NC(=O)N UWIGEOMJXLJZEG-SNAWJCMRSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- KGCVQLXXCMENQK-UHFFFAOYSA-N 3,4,5-trimethoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC(OC)=C(OC)C(OC)=C1 KGCVQLXXCMENQK-UHFFFAOYSA-N 0.000 description 1
- GWNOGPNGHZUGGO-UHFFFAOYSA-N 3-amino-1-(3,4,5-trimethoxyphenyl)propan-1-one Chemical compound COC1=CC(C(=O)CCN)=CC(OC)=C1OC GWNOGPNGHZUGGO-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- FOGDWPRYGZOGJK-UHFFFAOYSA-N COC=1C=C(C(=O)CCCN)C=C(C=1OC)OC Chemical compound COC=1C=C(C(=O)CCCN)C=C(C=1OC)OC FOGDWPRYGZOGJK-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 244000061121 Rauvolfia serpentina Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- OYQNWSQQNVEVPY-UHFFFAOYSA-N n-hexyl-3,4,5-trimethoxybenzamide Chemical compound CCCCCCNC(=O)C1=CC(OC)=C(OC)C(OC)=C1 OYQNWSQQNVEVPY-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- JVHNBFFHWQQPLL-WOXROFTLSA-N reserpic acid Chemical compound COC1=CC=C2C(CCN3C[C@H]4C[C@@H](O)[C@@H]([C@H]([C@H]4C[C@@H]33)C(O)=O)OC)=C3NC2=C1 JVHNBFFHWQQPLL-WOXROFTLSA-N 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von tranquillosedativ wirksamen 3,4, 5-Trimethoxybenzoesäureamiden Die Erfindung bezieht sich auf ein Verfahren zur Herstellung von tranquillosedativ wirksamen 3,4,5-Trimethoxybenzoesäureamiden der allgemeinen Formel in der R einen Alkylrest mit 2 bis 6 Kohlenstoff atomen bedeutet.Process for the preparation of 3,4,5-trimethoxybenzoic acid amides having a tranquillose effect. The invention relates to a process for the preparation of 3,4,5-trimethoxybenzoic acid amides having a tranquilose effect and having the general formula in which R is an alkyl radical having 2 to 6 carbon atoms.
Es ist bereits bekannt, das 3,4,5-Trimethoxybenzoesäuremethylamid herzustellen (vgl. Berichte der deutschen chemischen Gesellschaft, Bd.58, 1925, S. 1096 bis 1103). Pharmakologisch ist diese Verbindung bisher jedoch noch nicht untersucht worden. Es wurde nun gefunden, daß Verbindungen der oben angegebenen allgemeinen Formel gute tranquillosedative Eigenschaften besitzen. Bisher war lediglich bekannt, daß einige Carbonsäureamide, wie Bromdiäthylacetamid und Allyldiäthylacetamid, eine ausgesprochene sedative und hypnotische Wirkung auf das Zentralnervensystem ausüben.It is already known that 3,4,5-trimethoxybenzoic acid methylamide (see reports of the German Chemical Society, Vol. 58, 1925, Pp. 1096 to 1103). However, this compound is not yet pharmacological been investigated. It has now been found that compounds of the above general formula have good tranquillosedative properties. So far was only known that some carboxamides, such as Bromdiäthylacetamid and Allyldiäthylacetamid, a pronounced sedative and hypnotic effect on the central nervous system exercise.
Weiterhin hat die Konstitutionsaufklärung der Alkaloide aus Rauwolfia serpentina gezeigt, daß ihre sedative Wirkung auf dem Alkaloid Reserpin beruht, bei dessen hydrolytischer Spaltung Reserpsäure und 3,4,5-Trimethoxybenzoesäure erhalten werden. Da gerade diesem Alkaloid die sedative Wirkung zugeschrieben wird, war es nicht vorauszusehen, daß auch andere Derivate der 3,4,5-Trimethoxybenzoesäure tranquillosedative Eigenschaften besitzen.Furthermore, the constitution elucidation of the alkaloids from Rauwolfia serpentina has shown that its sedative effect is based on the alkaloid reserpine, in its hydrolytic cleavage, reserpic acid and 3,4,5-trimethoxybenzoic acid are obtained will. Since the sedative effect is ascribed to this alkaloid, it was not foreseen that other derivatives of 3,4,5-trimethoxybenzoic acid will also be tranquillosedative Possess properties.
Es wurde nun gefunden, daß man tranquillosedativ wirksame 3,4,5-Trimethoxybenzoesäureamide der allgemeinen Formel in der R einen Alkylrest mit 2 bis 6 Kohlenstoffatomen bedeutet, in guter Ausbeute erhält, wenn man 3,4,5-Trimethoxybenzoylchlorid in einem mit Wasser nicht mischbaren inerten organischen Lösungsmittel mit einem primären Alkylamin mit 2 bis 6 Kohlenstoffatomen in Wasser in an sich bekannter Weise umsetzt. Von den nach der Erfindung herstellbaren Verbindungen wurde das 3,4,5-Trimethoxybenzoesäurebutylamid (1) mit den im Handel befindlichen Verbindungen 3,4,5-Trimethoxybenzoesäureglycindiäthylamid (II) und Äthylcrotonylharnstoff (III) verglichen, welche bekanntlich ebenfalls tranquillosedative Eigenschaften besitzen.It has now been found that 3,4,5-trimethoxybenzoic acid amides of the general formula which have a tranquillose effect can be obtained in which R denotes an alkyl radical having 2 to 6 carbon atoms, is obtained in good yield if 3,4,5-trimethoxybenzoyl chloride is known per se in a water-immiscible inert organic solvent with a primary alkylamine having 2 to 6 carbon atoms in water Way. Of the compounds that can be prepared according to the invention, the 3,4,5-trimethoxybenzoic acid butylamide (1) was compared with the commercially available compounds 3,4,5-trimethoxybenzoic acid glycine diethylamide (II) and ethylcrotonylurea (III), which are known to also have tranquilising properties.
Die Untersuchungen wurden, soweit nicht anders angegeben, an der weißen Maus bei oraler Verabreichung (2%ige Gummiarabikumemulsion) durchgeführt. Die Bestimmungen der mittleren Wirkungsmenge erfolgten graphisch im Wahrscheinlichkeitsnetz. Die Bestimmung der mittleren Wirkungsmenge beruht auf der graphischen Darstellung der quantitativen Abhängigkeit einer Wirkung von der dazugehörigen Menge im Wahrscheinlichkeitsnetz. Hierbei werden die Einzelmengen auf der logarithmisch unterteilten Abszisse (1 bis 10 000), der Prozentsatz der jeweils reagierenden Tiere auf der nach dem Gaußschen Integral unterteilten Ordinate aufgetragen und durch die so definierten Punkte eine Gerade gelegt. Der Schnittpunkt dieser Geraden mit der Ordinate für 50% der reagierenden Tiere ergibt die entsprechende, auf der Abszisse abzulesende Wirkungsmenge. Bei größeren Streuungen der Einzelpunkte von dieser sogenannten Regressionsgeraden muß letztere berechnet werden (Literatur D. Y. Finney, Probit Analysis, Cambridge, 1952).Unless otherwise stated, the examinations were carried out on the white Mouse when administered orally (2% gum arabic emulsion). The regulations the mean amount of action were shown graphically in the probability grid. the Determination of the average amount of action is based on the graphic representation of the quantitative dependence of an effect on the associated quantity in the probability plot. The individual quantities are displayed on the logarithmically subdivided abscissa (1 to 10,000), the percentage of each reacting animal based on the Gaussian The ordinate is plotted integrally subdivided and a Just laid. The intersection of this straight line with the ordinate for 50% of the responding Animals gives the corresponding amount of action to be read on the abscissa. at larger scatter of the individual points of this so-called regression line the latter can be calculated (literature D. Y. Finney, Probit Analysis, Cambridge, 1952).
Die sedative Wirkung wurde durch Bestimmung der mittleren Wirkungsmenge für die Motilität (Bewegungsaktivität der Tiere) im »IDPN-Test« (Tiere zeigen nach Behandlung mit Iminodipropionsäurenitril eine irreversible Erhöhung der motorischen Aktivität, die durch Tranquillosedativa aufgehoben werden kann) und am Drehstab (Stab von 1 cm Durchmesser mit 15 Umdrehungen je Minute, auf den die . Tiere gesetzt werden, um ihr Haltevermögen zeitlich zu messen) ermittelt.The sedative effect was determined by determining the mean amount of effect for motility (Movement activity of the animals) in the »IDPN test« (Animals show an irreversible increase after treatment with iminodipropiononitrile motor activity that can be reversed by tranquillose edatives) and on the torsion bar (bar 1 cm in diameter at 15 revolutions per minute, on the the . Animals are placed to measure their holding ability over time).
Die qualitative Auswertung des »IDPN«-Testes und die Auswertung des Kampffischtestes (Beta splendens) lassen neben der rein sedativen Wirkung offenbar auch eine echte Beeinflussung psychischer Funktionen erkennen. Demzufolge ist die Verbindung als Tranquillosedativum zu bezeichnen.The qualitative evaluation of the »IDPN« test and the evaluation of the Fight fish tests (beta splendens) reveal the purely sedative effect also recognize a real influence on mental functions. As a result, the To designate compound as Tranquillose edativum.
Das besondere Kennzeichen der Tranquillosedativa ist ihre außerordentlich hohe Verträglichkeit bei fehlender hypnotischer Wirkung und ihr weiter sedativer Bereich, der bereits bei der Verabreichung von geringen Mengen beginnt. Der weite Abstand einerseits zwischen sedativer und hypnotischer Wirkung als auch zwischen sedativer und toxischer Wirkung bietet ein hohes Maß an therapeutischer Sicherheit.The special characteristic of the Tranquillose edativa is their extraordinary high tolerance in the absence of hypnotic effect and its further sedative Area that begins with the administration of small amounts. The wide one Distance on the one hand between sedative and hypnotic effects and between sedative and toxic effects offer a high level of therapeutic safety.
Aus der Tabelle ist ersichtlich, daß die Verbindung I gegenüber den
beiden zum Vergleich herangezogenen Verbindungen 11 und III doppelt so hoch
verträglich ist (LDso). Des weiteren zeichnet sie sich durch einen besonders großen
Abstand zwischen der LDSO und dem Eintritt der sedativen Wirkung (Motilität im IDPN-Test)
aus bei gleichzeitig eindeutiger Wirkung im Kampffischtest in außerordentlich geringer
Dosierung.
Die Mischung wird noch 30 Minuten gerührt und das ausgefallene Produkt abgesaugt, getrocknet und aus Tetrachlorkohlenstoff umkristallisiert. Man erhält 46 g (entsprechend 88% der Theorie) 3,4,5-Trimethoxybenzoyläthylamid; F. = 105- bis 106°C.The mixture is stirred for a further 30 minutes and the precipitated product suctioned off, dried and recrystallized from carbon tetrachloride. You get 46 g (corresponding to 88% of theory) 3,4,5-trimethoxybenzoylethylamide; F. = 105- up to 106 ° C.
Beispiel 2 38 g n-Propylamin werden in 100 ccm Wasser vorgelegt und analog zu Beispiel 1 mit 50 g 3,4,5-Trimethoxybenzoylchlorid, gelöst in 100 ccm Benzol, umgesetzt und in gleicher Weise aufgearbeitet. Man erhält 48 g (entsprechend 870% der Theorie) 3,4,5-Trimethoxybenzoylpropylamid; F. = 113 bis 114°C. Beispiel 3 65g Buty1arnin werden in 250 ccm Wasser vorgelegt und unter Rühren 30g 3,4,5-Trimethoxybenzoylchlorid, gelöst in 250 ccm Essigester, langsam zugetropft. Die Temperatur wird durch den Zulauf so geregelt, daß sie 40°C nicht überschreitet. Die Mischung wird noch 3 Stunden gerührt und die Essigesterschicht abgetrennt. Der Essigester wird abdestilliert und das 3,4,5-Trimethoxybenzoesäurebutylamid aus 70%igem Äthanol umkristallisiert; F. = 127°C. Die Ausbeuten liegen bei 80 bis 90% der Theorie.Example 2 38 g of n-propylamine are placed in 100 ccm of water and analogous to Example 1 with 50 g of 3,4,5-trimethoxybenzoyl chloride, dissolved in 100 ccm Benzene, reacted and worked up in the same way. 48 g are obtained (corresponding to 870% of theory) 3,4,5-trimethoxybenzoylpropylamide; M.p. = 113 to 114 ° C. example 3 65g of butylamine are placed in 250 ccm of water and 30g of 3,4,5-trimethoxybenzoyl chloride, dissolved in 250 cc of ethyl acetate, slowly added dropwise. The temperature is controlled by the Controlled feed so that it does not exceed 40 ° C. The mixture is another 3 hours stirred and the ethyl acetate layer separated. The ethyl acetate is distilled off and the 3,4,5-trimethoxybenzoic acid butylamide recrystallized from 70% ethanol; M.p. = 127 ° C. The yields are 80 to 90% of theory.
Beispiel 4 Zu 40 g n-Hexylamin, gelöst in 125 ccm Wasser, werden unter Rühren 11,5 g 3,4,5-Trimethoxybenzoylchlorid, gelöst in 125 ccm Essigester, gegeten, wobei leichte Erwärmung auftritt, die durch den Zulauf geregelt werden kann. Die Mischung wird noch 2 Stunden gerührt, die Esterschicht abgetrennt und der Essigester abdestilliert. Das 3,4,5-Trimethoxybenzoesäure-n-hexylamid wird aus 50%igem Äthanol umkristallisiert; F. = 109 bis 110°C. Die Ausbeuten liegen bei 70% der Theorie.Example 4 To 40 g of n-hexylamine, dissolved in 125 ccm of water, are added under Stirring 11.5 g of 3,4,5-trimethoxybenzoyl chloride, dissolved in 125 cc of ethyl acetate, poured, slight heating occurs, which can be regulated by the inlet. the The mixture is stirred for a further 2 hours, the ester layer is separated off and the ethyl acetate distilled off. The 3,4,5-trimethoxybenzoic acid-n-hexylamide is made from 50% ethanol recrystallized; F. = 109 to 110 ° C. The yields are 70% of theory.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV17061A DE1141986B (en) | 1959-08-12 | 1959-08-12 | Process for the preparation of 3, 4, 5-trimethoxybenzoic acid amides having a tranquillose-dative action |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV17061A DE1141986B (en) | 1959-08-12 | 1959-08-12 | Process for the preparation of 3, 4, 5-trimethoxybenzoic acid amides having a tranquillose-dative action |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1141986B true DE1141986B (en) | 1963-01-03 |
Family
ID=7576087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEV17061A Pending DE1141986B (en) | 1959-08-12 | 1959-08-12 | Process for the preparation of 3, 4, 5-trimethoxybenzoic acid amides having a tranquillose-dative action |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1141986B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0142241A1 (en) * | 1983-09-13 | 1985-05-22 | Kureha Kagaku Kogyo Kabushiki Kaisha | Dihydroxybenzamide derivatives having anti-inflammatory activity |
| US5140020A (en) * | 1983-09-13 | 1992-08-18 | Kureha Kagatu Kogyo Kabushiki Kaisha | Derivative of dihydroxybenzamide and a pharmaceutical composition thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1023029B (en) | 1955-04-23 | 1958-01-23 | Philips Nv | Process for the production of spasmolytically active, N-substituted salicylic acid amides and their acetic acid esters |
-
1959
- 1959-08-12 DE DEV17061A patent/DE1141986B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1023029B (en) | 1955-04-23 | 1958-01-23 | Philips Nv | Process for the production of spasmolytically active, N-substituted salicylic acid amides and their acetic acid esters |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0142241A1 (en) * | 1983-09-13 | 1985-05-22 | Kureha Kagaku Kogyo Kabushiki Kaisha | Dihydroxybenzamide derivatives having anti-inflammatory activity |
| US4725598A (en) * | 1983-09-13 | 1988-02-16 | Kureha Kagaku Kogyo Kabushiki Kaisha | Derivative of dihydroxybenzamide and a pharmaceutical composition having an anti-inflammatory activity |
| US5140020A (en) * | 1983-09-13 | 1992-08-18 | Kureha Kagatu Kogyo Kabushiki Kaisha | Derivative of dihydroxybenzamide and a pharmaceutical composition thereof |
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