CH451156A - Process for the preparation of the new N- (2-chloro-ethyl) -N '- (5-nitro-thiazolyl-2) -urea - Google Patents
Process for the preparation of the new N- (2-chloro-ethyl) -N '- (5-nitro-thiazolyl-2) -ureaInfo
- Publication number
- CH451156A CH451156A CH1103062A CH1103062A CH451156A CH 451156 A CH451156 A CH 451156A CH 1103062 A CH1103062 A CH 1103062A CH 1103062 A CH1103062 A CH 1103062A CH 451156 A CH451156 A CH 451156A
- Authority
- CH
- Switzerland
- Prior art keywords
- urea
- thiazolyl
- new
- salts
- nitro
- Prior art date
Links
- 239000004202 carbamide Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 8
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KQMBDBQMFJVWAX-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(1,3-thiazol-2-yl)urea Chemical compound ClCCNC(=O)NC1=NC=CS1 KQMBDBQMFJVWAX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000223932 Eimeria tenella Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- -1 alkaline earth metal salts Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 230000000384 rearing effect Effects 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- 206010001986 Amoebic dysentery Diseases 0.000 description 1
- 208000003495 Coccidiosis Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000948220 Histomonas meleagridis Species 0.000 description 1
- 206010023076 Isosporiasis Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- 241000242678 Schistosoma Species 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 201000004409 schistosomiasis Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/58—Nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung des neuen N- äthyl)-N' (5-nitro thiazolyl-2)-harnstoffes
Gegenstand der Erfindung ist ein Verfahren zur Herstellung des neuen N- (2-Chlor-äthyl)-N'- (5-nitro thiazolyl-2)-harnstoffes oder seiner Salze.
Salze der neuen Verbindung sind z. B. Metallsalze, insbesondere Alkali-und Erdalkalimetallsalze, wie Natrum-, Kalium-oder Kalziumsalze, Ammoniumsalze oder Salze von organischen Aminen.
Der neue Harnstoff und seine Salze besitzen antiparasitäre Eigenschaften, insbesondere gegenüber Pro tozoen, wie Entamöba, Flagellaten, wie Trichomonaden, und Eimeria tenella, sowie gegen Schistosomen.
Sie können entsprechende pharmakologische Anwendung am Tier finden. Die neue Verbindung eignet sich aber insbesondere zur Behandlung der durch die genannten Parasiten verursachten Erkrankungen, z. B. der Schistosomiasis, der Amöbenruhr oder der Amöbenhepatitis beim Menschen oder z. B. dem durch Histomonas meleagridis oder durch Eimeria tenella verursachten Infekt bei Tieren, z. B. zur Behandlung von blackhead oder der Coccidiose bei Geflügel oder Kaninchen. Die genannten Verbindungen können auch als Zwischenprodukte für die Herstellung anderer wertvoller Stoffe dienen.
Das erfindungsgemässe Verfahren zur Herstellung des neuen Harnstoffes besteht darin, dass man N- (2-chloräthyl)-N'-thiazolyl- (2)-harnstoff in 5-Stellung des Thiazolrestes nitriert.
Die genannte Reaktion kann in üblicher Weise, in An-oder Abwesenheit von Verdünnungsmitteln, Kon densationsmitteln und/oder Katalysatoren, bei ernied- rigter, gewöhnlicher oder erhöhter Temperatur, bei normalem oder erhöhtem Druck und/oder unter einer Inertgasatmosphäre durchgeführt werden.
Der verwendete Ausgangsstoff kann in an sich be kannter Weise hergestellt werden.
Je nach der Arbeitsweise erhält man die neue Verbindung in freier Form oder in Form ihrer Salze. Letztere lassen sich in üblicher Weise, z. B. durch Ansäuern einer diese enthaltenden Lösung, in die freie Verbindung überführen. Diese wiederum lässt sich nach bekannten Methoden, beispielsweise durch Reaktion mit basischen Mitteln, z. B. Metallhydroxyden oder basischen Salzen, speziell Alkali-oder Erdalkalimetallhydroxyden, wie Natrium-, Kalium-oder Kalziumhydroxyd, Alkalimeta7l. carbonaten, wie Natriumoder Kaliumcarbonat, Ammoniak oder organischen Aminen, in die entsprechenden Salze überführen.
Der neue Harnstoff und seine Salze können als Heilmittel, z. B. in Form pharmazeutischer Präparate, verwendet werden, welche diese Verbindung zusammen mit pharmazeutischen, organischen oder anorgani- schen, festen oder flüssigen Trägerstoffen, die für ente rale, z. B. orale, oder parenterale Gabe geeignet sind, enthalten.
Die eingangs genannte Verbindung kann aber auch zusammen mit gebräuchlichen Futter-bzw. Trägerstof- fen in der Veterinärmedizin in Form von Präparaten oder als Futter-bzw. Futterzusatzmittel bei der Aufzucht von Tieren Verwendung finden. Vorzugsweise soll sie als Zusätze von Tierfuttermitteln, insbesondere für die Aufzucht und Haltung von Geflügel oder Kaninchen, Verwendung finden.
Im folgenden Beispiel sind die Temperaturen in Celsiusgraden angegeben.
Beispiel
Zu einer Lösung von 10 g N- (2-Chlor-äthyl)- N'- (2-thiazolyl)-harnstoff in 100 cms Eisessig tropft man bei 15 eine Mischung von 7cm3 konzentrierter Salpetersäure in 15 cm3 Eisessig. Nach 2 Stunden Rühren bei 15 gibt man 100 cm3 Wasser zu und de kantiert von dem ausgefallenen öl ab. Dieses wird mit wenig Alkohol versetzt ; hierauf gibt man Isopropyl- äther zu und lässt bei 40 stehen. Nach einiger Zeit kristallisiert der N- (2-Chlor-äthyl)-N- (5-nitro-thiazolyl)- (2)-harnstoff der Formel
EMI2.1
in Kristallen von f. 137-142¯ aus.
Der als Ausgangsmaterial verwendete N- (2-Chlor äthyl)-N'- (2-thiazolyl)-hamstoff wird hergestellt durch Kochen von 15 g 2-Amino-thiazol und 16 g ¯-ChlorÏth ylisocyanat in 200 cm3 Äther. Der Harnstoff fällt in weissen Kristallen vom F. 130-132 aus.
Process for the preparation of the new N-ethyl) -N '(5-nitro thiazolyl-2) urea
The invention relates to a process for the preparation of the new N- (2-chloro-ethyl) -N'- (5-nitro thiazolyl-2) urea or its salts.
Salts of the new compound are e.g. B. metal salts, in particular alkali and alkaline earth metal salts, such as sodium, potassium or calcium salts, ammonium salts or salts of organic amines.
The new urea and its salts have anti-parasitic properties, in particular against Pro tozoen such as Entamöba, flagellates such as Trichomonaden, and Eimeria tenella, and against Schistosomes.
You can find appropriate pharmacological application on animals. The new compound is particularly suitable for treating the diseases caused by the parasites mentioned, e.g. B. schistosomiasis, amoebic dysentery or amoebic hepatitis in humans or z. B. the infection caused by Histomonas meleagridis or by Eimeria tenella in animals, e.g. B. for the treatment of blackhead or coccidiosis in poultry or rabbits. The compounds mentioned can also serve as intermediates for the production of other valuable substances.
The process according to the invention for the preparation of the new urea consists in nitrating N- (2-chloroethyl) -N'-thiazolyl- (2) -urea in the 5-position of the thiazole radical.
The reaction mentioned can be carried out in the customary manner, in the presence or absence of diluents, condensing agents and / or catalysts, at lower, ordinary or elevated temperature, at normal or elevated pressure and / or under an inert gas atmosphere.
The starting material used can be prepared in a manner known per se.
Depending on the mode of operation, the new compound is obtained in free form or in the form of its salts. The latter can be used in the usual way, for. B. by acidifying a solution containing them, converted into the free compound. This in turn can be determined by known methods, for example by reacting with basic agents, e.g. B. metal hydroxides or basic salts, especially alkali or alkaline earth metal hydroxides, such as sodium, potassium or calcium hydroxide, alkali metal. carbonates, such as sodium or potassium carbonate, ammonia or organic amines, are converted into the corresponding salts.
The new urea and its salts can be used as remedies, e.g. B. in the form of pharmaceutical preparations can be used, which this compound together with pharmaceutical, organic or inorganic, solid or liquid excipients, which are for ente rale, z. B. oral or parenteral administration are suitable.
The connection mentioned at the beginning can, however, also be used together with conventional feed or. Carriers in veterinary medicine in the form of preparations or as feed or. Find feed additives in the rearing of animals use. It should preferably be used as additives to animal feed, in particular for the rearing and keeping of poultry or rabbits.
In the following example the temperatures are given in degrees Celsius.
example
A mixture of 7 cm3 of concentrated nitric acid in 15 cm3 of glacial acetic acid is added dropwise at 15 cm to a solution of 10 g of N- (2-chloro-ethyl) -N'- (2-thiazolyl) -urea in 100 cms of glacial acetic acid. After stirring for 2 hours at 15, 100 cm3 of water are added and the precipitated oil is decanted off. A little alcohol is added to this; then isopropyl ether is added and allowed to stand at 40. After some time, the N- (2-chloro-ethyl) -N- (5-nitro-thiazolyl) - (2) -urea of the formula crystallizes
EMI2.1
in crystals of f. 137-142¯ from.
The N- (2-chloroethyl) -N'- (2-thiazolyl) -urea used as starting material is prepared by boiling 15 g of 2-amino-thiazole and 16 g of ¯-chloroethyl isocyanate in 200 cm3 of ether. The urea precipitates in white crystals from F. 130-132.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1103062A CH451156A (en) | 1962-09-18 | 1962-09-18 | Process for the preparation of the new N- (2-chloro-ethyl) -N '- (5-nitro-thiazolyl-2) -urea |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1103062A CH451156A (en) | 1962-09-18 | 1962-09-18 | Process for the preparation of the new N- (2-chloro-ethyl) -N '- (5-nitro-thiazolyl-2) -urea |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH451156A true CH451156A (en) | 1968-05-15 |
Family
ID=4369330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1103062A CH451156A (en) | 1962-09-18 | 1962-09-18 | Process for the preparation of the new N- (2-chloro-ethyl) -N '- (5-nitro-thiazolyl-2) -urea |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH451156A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000026203A1 (en) * | 1998-10-30 | 2000-05-11 | Pharmacia & Upjohn S.P.A. | 2-ureido-thiazole derivatives, process for their preparation, and their use as antitumor agents |
| US7125888B2 (en) | 2002-05-02 | 2006-10-24 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| US7265134B2 (en) | 2001-08-17 | 2007-09-04 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
-
1962
- 1962-09-18 CH CH1103062A patent/CH451156A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000026203A1 (en) * | 1998-10-30 | 2000-05-11 | Pharmacia & Upjohn S.P.A. | 2-ureido-thiazole derivatives, process for their preparation, and their use as antitumor agents |
| US7265134B2 (en) | 2001-08-17 | 2007-09-04 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| US7125888B2 (en) | 2002-05-02 | 2006-10-24 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
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