DE106502C - - Google Patents
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- Publication number
- DE106502C DE106502C DENDAT106502D DE106502DA DE106502C DE 106502 C DE106502 C DE 106502C DE NDAT106502 D DENDAT106502 D DE NDAT106502D DE 106502D A DE106502D A DE 106502DA DE 106502 C DE106502 C DE 106502C
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- DE
- Germany
- Prior art keywords
- acid
- chloroacetyl
- methyl ester
- free base
- parts
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 4
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical class ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 150000004702 methyl esters Chemical class 0.000 description 16
- 239000012458 free base Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000001476 alcoholic Effects 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- -1 esters chloroacetyl chloride Chemical class 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 description 2
- 150000002832 nitroso derivatives Chemical class 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LQJARUQXWJSDFL-UHFFFAOYSA-N 2-amino-N-(4-ethoxyphenyl)acetamide Chemical compound CCOC1=CC=C(NC(=O)CN)C=C1 LQJARUQXWJSDFL-UHFFFAOYSA-N 0.000 description 1
- WVMBPWMAQDVZCM-UHFFFAOYSA-N N-methylanthranilic acid Chemical compound CNC1=CC=CC=C1C(O)=O WVMBPWMAQDVZCM-UHFFFAOYSA-N 0.000 description 1
- 241000394605 Viola striata Species 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000001754 anti-pyretic Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 229950010879 phenamine Drugs 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/12—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by hydrolysis, i.e. solvolysis in general
- C07K1/124—Hydrazinolysis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Lä'fst man auf Amido- oder Amidooxycarbonsäureester nach einander Chloracetylchlorid und dann Amine einwirken, so erhält man neue Verbindungen, denen die allgemeine FormelOne runs on amido or amidooxycarboxylic acid esters chloroacetyl chloride and then amines act one after the other, so one obtains new compounds that have the general formula
, . D , , /NH- C OCH„ — NX2
(aromat.Rad.)<COOAIkyl ,. D ,, / NH- C OCH " - NX 2
(aromatic rad.) < COOAIkyl
zukommt.comes to.
Diese neuen Verbindungen, die man als GIycocollamidocarbonsäureester bezeichnen kann, sind werthvolle Producte, da sie. die Eigenschaft besitzen, Anaesthesie zu erzeugen. Sie haben diese Eigenschaft gemeinsam mit den Amidocarbonsäureestern , deren Derivate sie sind, unterscheiden sich aber von diesen vortheilhaft durch ihre stark basische Natur, die sie befähigt, in Wasser mit neutraler Reaction lösliche Salze zu bilden.1 Sie sind deshalb auch für subcutane Injection vorzüglich geeignet. Aus aromatischen Aminen hat man schon Glycocollderivate, wie das Phenocoll dargestellt (vergl. Patentschrift 59121), die als Antipyretica therapeutischen Werth besitzen.These new compounds, which can be called glycocollamidocarboxylic acid esters, are valuable products because they are. have the property of producing anesthesia. They have this property in common with the amidocarboxylic acid esters, of which they are derivatives, but differ from these advantageously in their strongly basic nature, which enables them to form salts which are soluble in water with a neutral reaction. 1 They are therefore eminently suitable for subcutaneous injection. From aromatic amines one has already found glycocoll derivatives, such as the phenocoll shown (see patent specification 59121), which have therapeutic value as antipyretics.
Bemerkenswerth ist, dafs der Grad des Anaesthesirungsvermögens der Glycocollderivate der Amidocarbonsäureester keineswegs dem ihrer Muttersubstanzen entspricht, z. B. anaesthesirt das UCl-SaIz des Diäthylglycocollp - amido - m - oxy benzoe'säuremethylesters weit schwächer als der ihm zu Grunde liegende Amidooxyester.It is noteworthy that the degree of anesthesia of the glycocollic derivatives of the amidocarboxylic acid esters in no way corresponds to that of their parent substances, e.g. B. the UCl salt of diethyl glycocollipamido-m-oxy benzoic acid methyl ester anesthetizes far weaker than the amidooxyester on which it is based.
Zunächst sei kurz die Darstellung der Chloracetylderivate, die als Zwischenproducte dienen, erwähnt, z. B. des Chloracetylanthranilsäuremethylesters und des Chloracetyl-p-amidosalicylsäuremethylesters. Let us first briefly describe the chloroacetyl derivatives, which serve as intermediate products, mentioned, e.g. B. of chloroacetylanthranilic acid methyl ester and chloroacetyl-p-amidosalicylic acid methyl ester.
Zu einer Lösung von 12 Theilen Anthranilsäuremethylester in 100 Theilen Benzol giebt man 10 Theile Chloracetylchlorid und erhitzt so lange auf dem Wasserbade, bis die SaIzsäureentwickelung aufhört, was nach circa 2. Stunden der Fall ist. Dann destillirt man etwa 2/3 des Benzols ab und lä'fst erkälten, wobei sich der Chloracetylanthranilsäuremethylester ausscheidet, der aus absolutem Alkohol in feinen weifsen Nadeln vom Schmp. 920 krystallisirt.10 parts of chloroacetyl chloride are added to a solution of 12 parts of methyl anthranilic acid in 100 parts of benzene, and the mixture is heated on the water bath until the development of hydrochloric acid ceases, which is the case after about two hours. Then distilling about 2/3 of benzene, and a cold lä'fst, wherein the Chloracetylanthranilsäuremethylester excretes which crystallizes from absolute alcohol in whites fine needles of mp. 92 0th
Chloracetyl-p-arnidosalicylsä'uremethylester. Methyl chloroacetyl-p-arnidosalicylic acid.
34 Theile ρ -Amidosalicylsäuremethylester werden in 220 Theilen Benzol gelöst und mit 24 Theilen Chloracetylchlorid erwärmt, bis keine Salzsäure mehr entweicht. Schon während der Reaction und vollständig beim Erkalten scheidet sich der Chloracetyl-p-amidosalicylsäuremethylester als schwach violett gefärbte Krystallmasse ab, die man absaugt und mit Benzol auswäscht. Die Verbindung krystallisirt aus absolutem Alkohol in feinen flachen Prismen, Schmp. 158°.34 parts of ρ-amidosalicylic acid methyl ester are dissolved in 220 parts of benzene and mixed with Heat 24 parts of chloroacetyl chloride until no more hydrochloric acid escapes. Already during After the reaction and completely on cooling, the methyl chloroacetyl-p-amidosalicylate separates as a pale violet colored crystal mass, which is sucked off and washes out with benzene. The compound crystallizes from absolute alcohol in fine, flat forms Prisms, m.p. 158 °.
In entsprechender Weise erhält man auch die nachbenannten Chloracetylderivate:The chloroacetyl derivatives mentioned below are also obtained in a corresponding manner:
Nadeln, Schmp. 96 °,Needles, m.p. 96 °,
Chloracetyl-m-amidobenzoesäuremethylester,Methyl chloroacetyl-m-amidobenzoate,
-p-amidobenzoesäureäthylester, -o-amidosalicylsäuremethylester,-p-amidobenzoic acid ethyl ester, -o-amidosalicylic acid methyl ester,
-p-amidosalicylsäureäthylester,-p-amidosalicylic acid ethyl ester,
-p-amido-m-oxybenzoe'säuremethylester,-p-amido-m-oxybenzoic acid methyl ester,
-p-amidozimmtsäuremethylester, Blättchen, Schmp. 155 bis 1560,-p-amidozimmtsäuremethylester, leaflets, m.p. 155 to 156 0 ,
-m- - . Nadeln, Schmp. 1200.-m- -. Needles, m.p. 120 0 .
n6°,
io6°, .
- 158°,n6 °,
io6 °,.
- 158 °,
Nadeln, Schmp. 189'Needles, m.p. 189 '
Aus diesen Chloracetylderivaten der Amidocarbonsäureester erhält man durch Umsetzung mit Aminen die Glycocollderivate. Das Verfahren ist in folgenden Beispielen näher beschrieben. The amidocarboxylic acid esters are obtained from these chloroacetyl derivatives by reaction with amines the Glycocollderivate. The process is described in more detail in the following examples.
ι. Zu 4,1 Theilen einer mit Alkohol verdünnten 3 3 Va Proc· wässerigen Methylaminlösung giebt man unter Umschütteln eine alkoholische Lösung von 5 Theilen Chloracetylanthranilsäuremethylester und erwärmt unter Rückflufs oder besser im Druckgefäfs etwa 2 Stunden lang im Wasserbad, dann destillirt man den Alkohol ab, säuert den Rückstand mit verdünnter wässeriger Salzsäure an, filtrirt event, von ungelöster Substanz ab, sättigt das Filtrat mit kohlensaurem Kali und extrahirt mit Aether. Beim Verdunsten desselben hinterbleibt der Methylglycocollanthranilsäuremethylester als basisches OeI, welches mit alkoholischer Salzsäure ein salzsaures Salz bildet, das aus Alkohol und Aether in feinen Kryställchen erhalten wird, die bei 202° unter Zersetzung schmelzen.und mit salpetriger Säure eineNitrosoverbindung liefern.ι. An alcoholic solution of 5 parts methyl chloroacetylanthranilate is added to 4.1 parts of a 3 3 va P roco aqueous methylamine solution diluted with alcohol and heated under reflux or, better, in a pressure vessel for about 2 hours in a water bath, then the alcohol is distilled off. acidify the residue with dilute aqueous hydrochloric acid, filter off any undissolved substance, saturate the filtrate with carbonate of potash and extract with ether. When it evaporates, the methyl glycocollanthranilic acid methyl ester remains as a basic oil, which forms a hydrochloric acid salt with alcoholic hydrochloric acid, which is obtained from alcohol and ether in fine crystals, which melt at 202 ° with decomposition and produce a nitroso compound with nitrous acid.
2. Man fügt zu 6 Theilen einer mit Alkohol versetzten 33Y2 proc. wässerigen Aethylaminlösung unter Umschütteln eine alkoholische Lösung von 5 g Chloracetyl-p-Amidobenzoesäuremethylester und verfährt wie bei 1. Das hierbei gewonnene salzsaure Salz des Aethylglycoco 11-p-ami dob enzoe säure methylesters krystallisirt aus Wasser in weifsen Krystallen, Schmp. 2250 und giebt mit salpetriger Säure eine Nitrosoverbindung. Der freie Ester krystallisirt aus Sprit in Nadeln vom Schmp. 105 bis io6°.2. Add to 6 parts of a 33Y 2 per cent. aqueous Aethylaminlösung while shaking an alcoholic solution of 5 g chloroacetyl-p-Amidobenzoesäuremethylester and procedure as in 1. The hereby obtained hydrochloric acid salt gives the Aethylglycoco 11-p-ami dob enzoe acid methylesters crystallizes from water in whites crystals, mp. 225 0 and a nitroso compound with nitrous acid. The free ester crystallizes from fuel in needles of m.p. 105 to 10.6 °.
3. Man trägt 6 Theile Chloracetyl-m-amidop-oxybenzoesäuremethylester unter Eiskühlung in ca. 5 Theile Diäthylamin ein, rührt um und digerirt nach etwa 24 Stunden mit Wasser, säuert mit Salzsäure an, filtrirt vom Ungelösten ab und macht das Filtrat mit Soda alkalisch, wobei sich in guter Ausbeute der Diäthylglycocoll-m-amido-p-oxyb enzoe säuremethylester abscheidet, der aus Sprit in Blättchen vom Schmp. 175° krystallisirt.3. Six parts of methyl chloroacetyl-m-amidop-oxybenzoate are carried with ice cooling in about 5 parts of diethylamine, stirred and digested after about 24 hours with water, acidify with hydrochloric acid, filter off the undissolved material and make the filtrate alkaline with soda, with the diethylglycocoll-m-amido-p-oxyb enzoic acid methyl ester is deposited, which crystallizes from fuel in leaflets with a melting point of 175 °.
Das salzsaure Salz scheidet sich aus Aceton in weifsen Krystallen ab, seine wässerige Lösung giebt mit Eisenchlorid eine schwache rothviolette Farbenreaction.The hydrochloric acid salt separates out of acetone in white crystals; its aqueous solution with ferric chloride gives a pale red-violet Color reaction.
4. 45 Theile Chloracetyl-p-amidosalicylsäuremethylester und 28 Theile Diäthylamin werden in 100 Theilen Alkohol 2 Stunden unter Rückflufs gekocht. Hierauf verdunstet man den Alkohol, versetzt den Rückstand mit verdünnter Sodalösung, extrahirt mit Aether. Beim Abdestilliren des Lösungsmittels hinterbleibt der Diäthylglycocoll-p-amidosalicy Isäuremethylester als OeI; sein salzsaures Salz krystallisirt aus absolutem Alkohol in Prismen, Schmp. 1850, und giebt in wässeriger Lösung mit Eisenchlorid eine violette Farbenreaction.4. 45 parts of methyl chloroacetyl-p-amidosalicylate and 28 parts of diethylamine are refluxed in 100 parts of alcohol for 2 hours. The alcohol is then evaporated, the residue is mixed with dilute soda solution, and extracted with ether. When the solvent is distilled off, the diethylglycocoll-p-amidosalicy is acid methyl ester remains as an oil; its hydrochloric acid salt crystallizes from absolute alcohol in prisms, m.p. 185 0 , and gives a violet color reaction in aqueous solution with ferric chloride.
5. 5 g Chloracetyl - ρ - amidobenzoesäuremethylester werden mit 50 ecm concentrirtem methylalkoholischem Ammoniak 24 Stunden in der Druckflasche auf 60 bis 70 ° erwärmt, wobei alles bis auf einen kleinen Rückstand in Lösung geht, der nach dem Erkalten abfiltrirt wird. Das Filtrat wird auf dem Wasserbade eingedunstet, es hinterbleibt ein krystallinischer Rückstand, der bis auf einen kleinen Rest bei der Behandlung mit stark verdünnter Salzsäure in Lösung geht. Mit Soda fällt aus der, sauren Lösung die Hauptmasse des Glycocoll-pamidobenzoe'säuremethylesters aus; vollständig scheidet er sich erst beim Aussalzen mit Pottasche ab. Der Ester krystallisirt aus mit wenig Methylalkohol versetztem Wasser in kleinen Nadeln vom Schmp. 910.5. 5 g of methyl chloroacetyl-ρ-amidobenzoate are heated to 60 to 70 ° in a pressure bottle with 50 ecm of concentrated methyl alcoholic ammonia for 24 hours, all but a small residue going into solution, which is filtered off after cooling. The filtrate is evaporated on the water bath, leaving a crystalline residue which, apart from a small residue, dissolves on treatment with highly dilute hydrochloric acid. Most of the glycocollipamidobenzoic acid methyl ester precipitates from the acidic solution with soda; it only separates completely when it is salted out with potash. The ester crystallizes from methyl alcohol with little added water in small needles of mp. 91 0th
Weitere Beispiele von analog zu erhaltenden Verbindungen sind in folgender Tabelle zusammengestellt: . ...Further examples of connections to be obtained analogously are compiled in the following table: . ...
H Cl- Aethylglycocollanthranilsäuremethylester: weifse Krystalle, Schmp. 191 °; H Cl- ethylglycocollanthranilic acid methyl ester: white crystals, melting point 191 °;
freie Base OeI.
HJBr-Dirnethylglycocollanthranilsäuremethylester: weifse Krystalle, Schmp. 195°;free base OeI.
H JBr-dimethylglycocollanthranilic acid methyl ester: white crystals, melting point 195 °;
freie Base OeI. ■free base OeI. ■
if Br-Diäthylglycocollanthranilsäuremethylester: Nädelchen, Schmp. 1200; .··if Br-Diäthylglycocollanthranilsäuremethylester: needles, mp 120 0;. . ··
• freie Base OeL ,-■· .• free base OeL, - ■ ·.
HCl-Aethylglycocoll-m-amidobenzoe'sä'uremethylester: weifse Krystalle, Schmp. 2000; HCl Aethylglycocoll m amidobenzoe'sä'uremethylester: whiteness crystals, mp 200 0;.
freie Base Schmp. 59 bis 6o°. HCZ-Diathylglycocoll-m-amidobenzoe'sauremethylester: weifse Krystalle, Schmp. i8o°;free base m.p. 59 to 60 °. H CZ-diethylglycocoll-m-amidobenzoic acid methyl ester: white crystals, mp. 180 °;
freie Base OeI. i/CZ-Methylglycocoll-p-amidobenzoe'sauremethylester: weifse Krystalle, Schmp. 2130;free base OeI. i / CZ Methylglycocoll-p-amidobenzoe'sauremethylester: whiteness crystals, mp 213 0;.
freie Base Schmp. 96 bis 98 °. HBr-Diäthylglycocoll -p- amidobenzoe'säuremethylester: körnige Krystalle, Schmp. 1720;free base m.p. 96 to 98 °. HBr -diethylglycocoll -p- amidobenzoic acid methyl ester: granular crystals, m.p. 172 0 ;
freie Base Schmp. 60°. ii J-Dimethylglycocoll -p -amidobenzoesäureäthylester: Blättchen, Schmp. 850;free base m.p. 60 °. ii J-Dimethylglycocoll-p -amidobenzoic acid ethyl ester: leaflets, m.p. 85 0 ;
freie Base OeI. HCl-Diäthylglycocoll-o-amidosalicylsäuremethylester: Nadeln, Schmp. 80 bis 820;free base OeI. HCl- diethylglycocoll-o-amidosalicylic acid methyl ester: needles, m.p. 80 to 82 0 ;
freie Base Schmp. 40 bis 42 °. HCl- Aetbylglycocoll-p-amidosalicylsäuremethylester: weifse Krystalle, Schmp. 2300;free base m.p. 40 to 42 °. HCl- Aetbylglycocoll-p-amidosalicylsäuremethylester: white crystals, m.p. 230 0 ;
freie Base Schmp. 6o°. HCl-Dimethylglycocoll- p-amidosalicylsäuremethylester: Nadeln, Schmp. 2370;free base m.p. 60 °. HCl- dimethylglycocoll-p-amidosalicylic acid methyl ester: needles, melting point 237 0 ;
freie Base Schmp. 59 bis 60°. HCl-Diäthylglycocoll-ρ-amidosalicylsäureäthylester: weifse Krystalle, Schmp. 198,5°;free base m.p. 59 to 60 °. HCl diethylglycocoll-ρ-amidosalicylic acid ethyl ester: white crystals, melting point 198.5 °;
freie Base OeI. iiC7-Diäthylglycocoll-p-amido-m- oxybenzoe'säuremethylester: Nädelchen, Schmp. 99°;free base OeI. iiC7-diethylglycocoll-p-amido-m-oxybenzoic acid methyl ester: needles, melting point 99 °;
freie Base Schmp. 1580. üTCZ-Diäthylglycocoll-p-amidozimmtsäuremethylester: Nädelchen, Schmp. 198 bis 1990;free base m.p. 158 0 . üTCZ-diethylglycocoll-p-amidozimmtsäuremethylester: needles, mp. 198 to 199 0 ;
freie Base zähes OeI. /JCZ-Diäthylglycocoll-m-ämidozimmtsäuremethylester: Nädelchen, Schmp. 165°;free base tough oil. / JCZ-diethylglycocoll-m-ämidozimmtsäuremethylester: needles, mp. 165 °;
freie Base dickes OeI.free base thick oil.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE968561C (en) * | 1943-07-15 | 1958-03-06 | Astra Apotekarnes Kem Fab | Process for the preparation of monoaminoacylanilides substituted on the amino nitrogen |
| US3291824A (en) * | 1962-04-06 | 1966-12-13 | Hoffmann La Roche | Nu-(2-halo-lower alkanoyl) anthranilic acid derivatives |
| WO2003063858A2 (en) * | 2002-01-31 | 2003-08-07 | Kalil-Fihlo, Jorge, Elias | Compounds, particularly of urea derivatives or ester derivatives of haloacetamidobenzoic acid and use thereof for the treatment of parasitic diseases |
-
0
- DE DENDAT106502D patent/DE106502C/de active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE968561C (en) * | 1943-07-15 | 1958-03-06 | Astra Apotekarnes Kem Fab | Process for the preparation of monoaminoacylanilides substituted on the amino nitrogen |
| US3291824A (en) * | 1962-04-06 | 1966-12-13 | Hoffmann La Roche | Nu-(2-halo-lower alkanoyl) anthranilic acid derivatives |
| WO2003063858A2 (en) * | 2002-01-31 | 2003-08-07 | Kalil-Fihlo, Jorge, Elias | Compounds, particularly of urea derivatives or ester derivatives of haloacetamidobenzoic acid and use thereof for the treatment of parasitic diseases |
| WO2003063858A3 (en) * | 2002-01-31 | 2004-03-25 | Patrice Lepape | Compounds, particularly of urea derivatives or ester derivatives of haloacetamidobenzoic acid and use thereof for the treatment of parasitic diseases |
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