DE1092933B - Process for the preparation of amoebicidally active esters of p-oxy-N-dichloroacet-N-alkyl-anilides - Google Patents
Process for the preparation of amoebicidally active esters of p-oxy-N-dichloroacet-N-alkyl-anilidesInfo
- Publication number
- DE1092933B DE1092933B DEB50245A DEB0050245A DE1092933B DE 1092933 B DE1092933 B DE 1092933B DE B50245 A DEB50245 A DE B50245A DE B0050245 A DEB0050245 A DE B0050245A DE 1092933 B DE1092933 B DE 1092933B
- Authority
- DE
- Germany
- Prior art keywords
- dichloroacet
- oxy
- amoebicidally
- preparation
- anilides
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title claims description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 9
- WYODKEXCSBRCDL-UHFFFAOYSA-N [4-(methylamino)phenyl] benzoate Chemical compound C1=CC(NC)=CC=C1OC(=O)C1=CC=CC=C1 WYODKEXCSBRCDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical group ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 230000003569 amebicidal effect Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 241000224489 Amoeba Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- -1 Acetanilide ester Chemical class 0.000 description 1
- 241000224432 Entamoeba histolytica Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 210000004534 cecum Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940007078 entamoeba histolytica Drugs 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000003812 trophozoite Anatomy 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung therapeutisch wertvoller amoebicid wirkender Acetanilidester der allgemeinen FormelThe present invention relates to a process for the production of therapeutically valuable amoebicidally active substances Acetanilide ester of the general formula
CLCHCONCLCHCON
worin R eine niedere Alkylgruppe bedeutet.wherein R represents a lower alkyl group.
Es ist zwar schon bekannt, daß N-acylierte m-Oxyanilin-Verbindungen amoebicide Wirkungen aufweisen. Hieraus konnte jedoch nicht gefolgert werden, daß auch die erfindungsgemäß hergestellten Verbindungen solche Wirkungen besitzen.It is already known that N-acylated m-oxyaniline compounds have amoebicidal effects. From this, however, it could not be concluded that either the compounds prepared according to the invention have such effects.
Verbindungen der allgemeinen Formel I werden in an sich bekannter Weise durch Reaktion von Verbindungen der allgemeinen FormelCompounds of the general formula I are produced in a manner known per se by reacting compounds the general formula
HN —<HN - <
wobei R die oben angegebene Bedeutung besitzt, mit einem Dichloracylierungsmittel hergestellt. Die Reaktion kann in Gegenwart eines säurebindenden Mittels ausgeführt werden.where R has the meaning given above, prepared with a dichloroacylating agent. The reaction can be carried out in the presence of an acid binding agent.
Die amoebicide Wirksamkeit der erfindungsgemäßen Verbindungen wurde bei Tieren in der folgenden Weise nachgewiesen. Die Technik ist im wesentlichen diejenige, wie sie von Jones (Annals of Tropical Medicine and Parasitology, 1946, 40, S. 130) beschrieben wurde, wobei soeben entwöhnte Ratten intracaecal mit Trophozoiten von Entamoeba histolytica geimpft werden. Beginnend mit dem Tage nach der Impfung, werden jedem Tier aus einer Gruppe von Ratten fünf Tagesdosen der zu prüfenden Droge mittels einer Magensonde verabfolgt; die Tiere werden 1 Tag nach Verabfolgung der letzten Dosis getötet. Der Blinddarm jeder Ratte wird sowohl mikroskopisch als auch makroskopisch untersucht, und bei jeder Ratte wird der Grad der Infektion nach einer willkürlich gewählten Skala bewertet. Für jede Gruppe wird dann der durchschnittliche Infektionsgrad berechnet, nachstehend als A. D. I. bezeichnet. Man sieht eine Verbindung als amoebenabtötend an, wenn der A. D. I. der behandelten Gruppe geringer ist als die Hälfte des A. D. I. der nicht behandelten Kontrollgruppe. Bei hochwirksamen Drogen werden die Ratten völlig von den Amoeben befreit, und der A. D. I. ist dann gleich Null. In der nachstehenden Tabelle ist das bei dem obigen Test mit der erfindungsgemäßen Verbindung 4-Benzoyloxy-N-dichloracet-N-methylanüid erhaltene Ergebnis verzeichnet. Es werden hierbei Einzelheiten über die Höhe der Tagesdosen der Testverbindung sowie der Wirksamkeit angegeben. Die »Wirksamkeit« wird hierbei definiert als dieThe amoebicidal activity of the compounds of the invention was determined in animals in the following manner proven. The technique is essentially that described by Jones (Annals of Tropical Medicine and Parasitology, 1946, 40, p. 130), with rats that have just been weaned intracaecally with trophozoites be vaccinated by Entamoeba histolytica. Starting the day after vaccination, each animal will be out administered five daily doses of the drug to be tested to a group of rats by means of a gastric tube; the animals are killed 1 day after the last dose was administered. The cecum of each rat is seen both microscopically as well as examined macroscopically, and in each rat the degree of infection after one becomes arbitrary selected scale. The average degree of infection is then calculated for each group, hereinafter referred to as A. D. I. One sees a connection as amoebic if the A. D. I. der treated group is less than half of the A.DI of the untreated control group. With highly effective With drugs, the rats are completely freed from the amoeba, and the ADI is then zero. In the following The table is that in the above test with the compound according to the invention 4-benzoyloxy-N-dichloroacet-N-methylanide result obtained. There are details about the amount of the daily dose the test compound as well as the effectiveness. The "effectiveness" is defined here as that
Verfahren zur HerstellungMethod of manufacture
amoebicid wirksamer Ester von p-Oxy-amoebicidally effective ester of p-oxy-
N-dichloracet-N-alkyl-anilidenN-dichloroacet-N-alkyl-aniliden
Anmelder:Applicant:
Boots Pure Drug Company Limited,
Nottingham (Großbritannien)Boots Pure Drug Company Limited,
Nottingham (Great Britain)
Vertreter: Dr. M. Eule, Patentanwalt,
München 13, Kurfürstenplatz 2Representative: Dr. M. Eule, patent attorney,
Munich 13, Kurfürstenplatz 2
Beanspruchte Priorität:
Großbritannien vom 3. November 1955Claimed priority:
Great Britain 3 November 1955
Peter Oxley, Gerald Woolfe,
Norman William Bris'tow, James Fräser,Peter Oxley, Gerald Woolfe,
Norman William Bris'tow, James Millers,
George Alfred Harrison Williams
und Eric Charles Wilmshurst, NottinghamGeorge Alfred Harrison Williams
and Eric Charles Wilmshurst, Nottingham
(Großbritannien),
sind als Erfinder genannt worden(Great Britain),
have been named as inventors
Zahl, welche man erhält, wenn man den bei der Kontrollgruppe erhaltenen A. D. I. dividiert durch den A. D. I. der behandelten Gruppe (wobei jede Zahl das Ergebnis eines Versuches darstellt). Eine auf diese Weise erhaltene Zahl, welche größer ist als 1, bedeutet also, daß die Testverbindung eine amoebicide Wirkung zeigt. Je größer diese Zahl ist, desto höher ist auch die Wirksamkeit. Im Falle einer vollständigen Austreibung der Amoeben durch die Testverbindung kann man daher die »Wirksamkeit« als unendlich groß bezeichnen.Number obtained by dividing the A.D.I. obtained in the control group by the A.D.I. the treated group (where each number represents the result of an experiment). One obtained in this way A number which is greater than 1 therefore means that the test compound shows an amoebicidal effect. The bigger that number is, the higher the effectiveness. In the case of a complete expulsion of the amoeba through the test connection one can therefore describe the "effectiveness" as infinitely great.
(mg/kg)Daily dose
(mg / kg)
acet-N-methylanilid ... J4-benzoyloxy-N-dichloro
acet-N-methylanilide ... J.
50200
50
unendlichinfinite
infinite
Die nachstehenden Beispiele dienen zur Erläuterung der vorliegenden Erfindung:The following examples serve to illustrate the present invention:
Bei der Herstellung von 4-Benzoyloxy-N-dichloracet-N-methylanilid wird eine Lösung von 3 g Dichloracetylchlorid in 4 cm3 Benzol langsam unter Rühren einemIn the preparation of 4-benzoyloxy-N-dichloroacet-N-methylanilide, a solution of 3 g of dichloroacetyl chloride in 4 cm 3 of benzene is slowly stirred into a
009 648/406009 648/406
Gemisch aus 4 g 4-Methylaminophenyl-benzoat, 25 cm3 Benzol, 25 cm3 Wasser und 4 g Natriumacetat hinzugesetzt. Nach vollendetem Zusatz wird das Reaktionsgemisch weitere 10 Minuten lang gerührt, worauf die Benzolschicht abgetrennt und mit 30 cm3 2n-Salzsäure, 30 cm3 einer 5%igen Natriumcarbonatlösung sowie 30 cm3 Wasser gewaschen wird. Die gewaschene Benzollösung wird über kristallwasserfreiem Magnesiumsulfat getrocknet und unter vermindertem Druck bis zur Trockne eingedampft. Man erhält auf diese Weise 4-Benzoyloxy-N-dichloracet-N-methylanilid in Formeines kristallinen festen Körpers mit einem Schmelzpunkt von 114bis 1170C. (DieAnalyseergab4,5%N; C16H13O3NCl2 erfordert 4,1 % H.)Mixture of 4 g of 4-methylaminophenyl benzoate, 25 cm 3 of benzene, 25 cm 3 of water and 4 g of sodium acetate were added. After the addition is complete, the reaction mixture is stirred for a further 10 minutes, after which the benzene layer is separated off and washed with 30 cm 3 of 2N hydrochloric acid, 30 cm 3 of a 5% sodium carbonate solution and 30 cm 3 of water. The washed benzene solution is dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. Is obtained in this manner, 4-benzoyloxy-N-dichloracet-N-methylanilide in the form of a crystalline solid substance having a melting point of 117 0 C. 114bis (DieAnalyseergab4,5% N; C 16 H 13 O 3 NCl 2 requires 4.1% H.)
Das bei dem obigen Vorgang als Ausgangsstoff verwendete 4-Methylaminophenyl-benzoat wird in der folgenden Weise hergestellt: Ein Gemisch aus 100 g p-MethylaminophenoI-sulfat, 200 cm3 Ameisensäure und 4 g Natriumformiat wird 1 Stunde lang am Rückfluß erhitzt und dann unter vermindertem Druck bis zur Trockne eingedampft. Der Rückstand wird mit Wasser verrieben. Der feste Körper wird abfiltriert, im Vakuum getrocknet und aus Benzol umkristallisiert. Man erhält auf diese Weise Formo-4-oxy-N-methylanilid in Form eines kristallinen festen Körpers mit einem Schmelzpunkt von 105 bis 1060C. (Die Analyse ergab 9,4% N; C8H9O2N erfordert 9,3% N.) Eine Lösung von 15,1g Formo-4-oxy-N-methylanilid in 75 cm3 einer 7%igen Natronlauge mit einem Gehalt von etwa 50 g Eis setzt man 13 cm3 Benzoylchlorid hinzu; das sich dabei ergebende Gemisch wird 20 Minuten lang geschüttelt. Der sich abscheidende Niederschlag wird abnitriert und zweimal aus Alkohol umkristallisiert. Man erhält auf diese Weise 4-(Formo-N-methylamido)-phenyl-benzoat in Form eines kristallinen festen Körpers mit einem Schmelzpunkt von 122 bis 123°C. (Die Analyse ergab 70,2 C, 5,4 H, 5,3 N; C15H13O3N erfordert 70,6 C, 5,1 H sowie 5,5% N.) Man erhitzt ein Gemisch aus 13,55 g 4-(Formo-N-methylamido)-phenyl-benzoat und 100 cm3 η-Salzsäure am Rückfluß, bis man eine klare Lösung erhält. Diese Lösung wird gekühlt und einer im Überschuß vorhandenen 5n-Natronlauge hinzugesetzt. Der dabei ausgefällte Niederschlag wird abfiltriert, mit 25 cm3 n-Natronlauge sowie 50 cm3 Wasser gewaschen, im Vakuum getrocknet und aus Alkohol umkristallisiert. Man erhält auf diese Weise 4-Methylaminophenyl-benzoat in Form eines kristallinen festen Körpers mit einem Schmelzpunkt von 125 bis 126° C. (Die Analyse ergab 73,5 % C, 5,7 % H und 6,4% N; C14H13O2N erfordert 74,0% C, 5,7% H sowie 6,2% N.)The 4-methylaminophenyl benzoate used as starting material in the above process is prepared in the following manner: A mixture of 100 g of p-methylaminophenol sulfate, 200 cm 3 of formic acid and 4 g of sodium formate is refluxed for 1 hour and then under reduced pressure Pressure evaporated to dryness. The residue is triturated with water. The solid is filtered off, dried in vacuo and recrystallized from benzene. In this way, formo-4-oxy-N-methylanilide is obtained in the form of a crystalline solid body with a melting point of 105 to 106 ° C. (The analysis showed 9.4% N; C 8 H 9 O 2 N requires 9, 3% N.) A solution of 15.1 g of formo-4-oxy-N-methylanilide in 75 cm 3 of 7% sodium hydroxide solution containing about 50 g of ice is added to 13 cm 3 of benzoyl chloride; the resulting mixture is shaken for 20 minutes. The precipitate which separates out is filtered off and recrystallized twice from alcohol. 4- (Formo-N-methylamido) -phenyl-benzoate is obtained in this way in the form of a crystalline solid body with a melting point of 122 to 123.degree. (The analysis showed 70.2 C, 5.4 H, 5.3 N; C 15 H 13 O 3 N requires 70.6 C, 5.1 H and 5.5% N.) A mixture of 13 is heated , 55 g of 4- (Formo-N-methylamido) -phenyl-benzoate and 100 cm 3 of η-hydrochloric acid under reflux until a clear solution is obtained. This solution is cooled and added to an excess of 5N sodium hydroxide solution. The precipitate which precipitates out is filtered off, washed with 25 cm 3 of N sodium hydroxide solution and 50 cm 3 of water, dried in vacuo and recrystallized from alcohol. In this way, 4-methylaminophenyl benzoate is obtained in the form of a crystalline solid body with a melting point of 125 to 126 ° C. (The analysis showed 73.5% C, 5.7% H and 6.4% N; C 14 H 13 O 2 N requires 74.0% C, 5.7% H and 6.2% N.)
Bei der Herstellung von 4-Benzoyloxy-N-dichloracet-N-methylanilid wird ein Gemisch aus 4,54 g 4-Methylaminophenyl-benzoat, 3,5 g Dichloracetylchlorid und cm3 Benzol am Rückfluß erhitzt, bis die Entwicklung von Chlorwasserstoffgas aufhört.In the preparation of 4-benzoyloxy-N-dichloroacet-N-methylanilide, a mixture of 4.54 g of 4-methylaminophenyl benzoate, 3.5 g of dichloroacetyl chloride and cm 3 of benzene is refluxed until the evolution of hydrogen chloride gas ceases.
Die sich dabei ergebende Lösung wird mit 30 cm3 Wasser, 50 cm3 einer 5%igen Natriumcarbonatlösung und cm3 Wasser gewaschen, über kristallwasserfreiem Magnesiumsulfat getrocknet und unter vermindertem Druck bis zur Trockne eingedampft. Man erhält auf diese Weise 4-Benzoyloxy-N-dichloracet-N-methylanilid in Form eines kristallinen festen Körpers, welcher identisch ist mit dem Produkt des Beispiels 1.The resulting solution is washed with 30 cm 3 of water, 50 cm 3 of a 5% strength sodium carbonate solution and cm 3 of water, dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. In this way, 4-benzoyloxy-N-dichloroacet-N-methylanilide is obtained in the form of a crystalline solid which is identical to the product of Example 1.
Claims (4)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB356471X | 1955-11-03 | ||
| GB90356X | 1956-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1092933B true DE1092933B (en) | 1960-11-17 |
Family
ID=26242602
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB50246A Pending DE1095844B (en) | 1955-11-03 | 1956-10-27 | Process for the preparation of amoebicidally active esters of p-oxy-N-dichloroacet-N-alkyl-anilides and their salts |
| DEB50336A Pending DE1091575B (en) | 1955-11-03 | 1956-10-27 | Process for the preparation of amoebicidally active N-dichloroacet-p-oxy-anilide esters |
| DEB50245A Pending DE1092933B (en) | 1955-11-03 | 1956-10-27 | Process for the preparation of amoebicidally active esters of p-oxy-N-dichloroacet-N-alkyl-anilides |
| DEB42293A Pending DE1092932B (en) | 1955-11-03 | 1956-10-27 | Process for the preparation of amoebicidally active N-dichloroacet-oxy-anilide esters |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB50246A Pending DE1095844B (en) | 1955-11-03 | 1956-10-27 | Process for the preparation of amoebicidally active esters of p-oxy-N-dichloroacet-N-alkyl-anilides and their salts |
| DEB50336A Pending DE1091575B (en) | 1955-11-03 | 1956-10-27 | Process for the preparation of amoebicidally active N-dichloroacet-p-oxy-anilide esters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB42293A Pending DE1092932B (en) | 1955-11-03 | 1956-10-27 | Process for the preparation of amoebicidally active N-dichloroacet-oxy-anilide esters |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE552250A (en) |
| CH (1) | CH356471A (en) |
| DE (4) | DE1095844B (en) |
| GB (1) | GB794762A (en) |
| NL (2) | NL96977C (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB855556A (en) * | 1958-05-06 | 1960-12-07 | Boots Pure Drug Co Ltd | New acetanilide derivatives |
| CH1085667A4 (en) * | 1967-08-01 | 1969-03-14 | ||
| DE2714440C2 (en) * | 1977-03-31 | 1982-10-21 | Siemens AG, 1000 Berlin und 8000 München | Process for the production of titanate ceramic |
| FR2649977B1 (en) * | 1989-07-18 | 1991-10-04 | Cird | BI-AROMATIC ESTERS, THEIR PREPARATION PROCESS AND THEIR USE IN HUMAN OR VETERINARY MEDICINE AND IN COSMETICS |
-
0
- NL NL211890D patent/NL211890A/xx unknown
- NL NL96977D patent/NL96977C/xx active
- BE BE552250D patent/BE552250A/xx unknown
-
1955
- 1955-11-03 GB GB31482/55A patent/GB794762A/en not_active Expired
-
1956
- 1956-10-27 DE DEB50246A patent/DE1095844B/en active Pending
- 1956-10-27 DE DEB50336A patent/DE1091575B/en active Pending
- 1956-10-27 DE DEB50245A patent/DE1092933B/en active Pending
- 1956-10-27 DE DEB42293A patent/DE1092932B/en active Pending
- 1956-11-02 CH CH356471D patent/CH356471A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE552250A (en) | |
| DE1092932B (en) | 1960-11-17 |
| CH356471A (en) | 1961-08-31 |
| DE1095844B (en) | 1960-12-29 |
| GB794762A (en) | 1958-05-07 |
| NL96977C (en) | |
| DE1091575B (en) | 1960-10-27 |
| NL211890A (en) |
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