CH481938A - Process for the preparation of new nitrothiazole compounds - Google Patents
Process for the preparation of new nitrothiazole compoundsInfo
- Publication number
- CH481938A CH481938A CH1726966A CH1726966A CH481938A CH 481938 A CH481938 A CH 481938A CH 1726966 A CH1726966 A CH 1726966A CH 1726966 A CH1726966 A CH 1726966A CH 481938 A CH481938 A CH 481938A
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- formula
- new
- preparation
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 5
- ALNUOSXDMYFQNQ-UHFFFAOYSA-N 2-nitro-1,3-thiazole Chemical class [O-][N+](=O)C1=NC=CS1 ALNUOSXDMYFQNQ-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims 3
- VVVCJCRUFSIVHI-UHFFFAOYSA-N 5-nitro-1,3-thiazole Chemical class [O-][N+](=O)C1=CN=CS1 VVVCJCRUFSIVHI-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 230000002141 anti-parasite Effects 0.000 description 4
- 239000003096 antiparasitic agent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000224489 Amoeba Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000224483 Coccidia Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000242678 Schistosoma Species 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- 241001467018 Typhis Species 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000000645 desinfectant 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
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000002700 urine Anatomy 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Description
Verfahren zur Herstellung neuer Nitrothiazolverbindungen
Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung neuer 5-Nitrohiazolverbindungen der Formel
EMI1.1
worin Rt und R2 Wasserstoff oder niedere Alkylreste bedeuten und R für eine gegebenenfalls substituierte Aminogruppe steht, und ihrer Salze.
Diese Verbindungen besitzen insbesondere antiparasitäre und antibakterielle Eigenschaften.
Es wurde nun gefunden, dass die Verbindungen der Formel
EMI1.2
worin R' und R" unabhängig voneinander Wasserstoffatome oder Methylgruppen bedeuten, besonders wertvolle antiparasitäre und antibakterielle Eigenschaften aufweisen.
Die vorliegende Erfindung betrifft daher ein Verfahren zur Herstellung von Verbindungen der Formel II.
Die neuen Verbindungen besitzen wertvolle pharmakologische, insbesondere antiparasitäre und antibakterielle Eigenschaften. Sie zeigen vor allem eine Wirkung gegen Protozoen und Würmer und sind, z. B. am infizierten Tier, beispielsweise an Mäusen, gegen grampositive und besonders gegen gram-negative Bakterien, z. B. Salmolnella typhi oder Coli-Bazillen, wie Esch. coli, wirksam. Insbesondere wirken die neuen Verbindungen, wie sich z. B. bei Versuchen an Hamstern zeigt, gegen Trichomonaden und Amoeben, vor allem auch gegen Amoeben in der Leber, sowie, z. B. an Mäusen und Schafen, gegen Schistosomen. Ferner besitzen sie eine Wirkung gegen Coccidien und gegen den Erreger von Enterohepatitis (Blackhead). Die neuen Verbindungen sind entsprechend als antiparasitäre und antibakterielle Mittel nützlich.
Sie können auch als Harndesinfizientien verwendet werden. Insbesondere eignen sie sich zur Behandlung der durch die genannten Erreger verursachten Erkrankungen. Die neuen Verbindungen sind aber auch wertvolle Zwischenprodukte für die Herstellung anderer nützlicher Stoffe.
Das erfindungsgemässe Verfahren zur Herstellung der neuen Verbindungen ist dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.3
mit einer Verbindung der Formel
EMI1.4
umsetzt, worin R' und R" die eingangs angegebenen Bedeutungen besitzen und einer der Reste X und Y für Wasserstoff und der andere für den Rest der Formel
EMI1.5
worin X' eine freie oder vorzugsweise eine reaktionsfähig abgewandelte Oxygruppe, wie eine reaktionsfähig veresterte oder verätherte Oxygruppe, vor allem ein Halogenatom, insbesondere ein Chlor- oder Bromatom bedeutet, steht.
Die erfindungsgemässe Umsetzung kann in üblicher Weise erfolgen, vorzugsweise in Anwesenheit von Lösungs- und/oder Verdünnungsmitteln, gegebenenfalls in Anwesenheit von Kondensationsmitteln, wie basischen Kondensationsmitteln, bei tiefer, gewöhnlicher oder erhöhter Temperatur im offenen oder im geschlossenen Gefäss unter Druck.
Die Ausgangsstoffe sind bekannt oder können nach an sich bekannten Methoden gewonnen werden.
Die als Ausgangsstoffe verwendeten Verbindungen der Formel
EMI2.1
worin X' die angegebene Bedeutung hat, können z. B. erhalten werden, wenn man eine Verbindung der Formel
EMI2.2
mit einer Verbindung der Formel
EMI2.3
worin X' die angegebene Bedeutung hat und X" eine reaktionsfähig abgewandelte, wie eine reaktionsfähig veresterte oder verätherte Oxygruppe, vor allem ein Halogenatom, insbesondere ein Chlor- oder Bromatom, bedeutet, umsetzt. Die Umsetzung erfolgt in üblicher Weise. Der oben genannte Ausgangsstoff der Formel V braucht dabei nicht isoliert zu werden, sondern man kann diesen direkt ohne Isolierung nach dem erfindungsgemässen Verfahren in das Oxamid überführen.
Die neuen Verbindungen können z. B. in Form pharmazeutischer Präparate, Verwendung finden, welche sie in Mischung mit einem für die enterale, parenterale oder topische Applikation geeigneten pharmazeutischen organischen oder anorganischen, festen oder flüssigen Trägermaterial enthalten.
Die neuen Verbindungen können auch in der Tiermedizin, z. B. in einer der oben genannten Formen oder in Form von Futtermitteln oder von Zusatzmitteln für Tierfutter verwendet werden.
In den folgenden Beispielen sind die Temperaturen in Celsiusgraden angegeben.
Beispiel 1
Zu einer Lösung von 12, 7 g Oxalylchlorid in 300 ml absolutem Tetrahydrofuran werden bei einer Temperatur von 20-22 14, 5 g 5-Nitro-2-aminothiazol, gelöst in 200 ml absolutem Tetrahydrofuran, eingetropft. Man rührt während einer halben Stunde bei Raumtemperatur weiter. Hierauf leitet man bei einer Temperatur von 15-25 Ammoniakgas ein, bis die Suspension einen pH-Wert von ungefähr 6 aufweist.
Dann erwärmt man allmählich innert einer Stunde bis zum Sieden und filtriert dann das ausgefallene Nebenprodukt heiss ab. Das Filtrat wird durch Einengen im Vakuum auf ein Volumen von ungefähr 70 ml zum Kristallisieren gebracht. Das auskristallisierte Produkt wird abgenutscht, mit Wasser ausgewaschen und sehr viel Äthanol umkristallisiert. Man erhält so das N2-(5-Nitro-2-thiazolyl)-oxamid der Formel
EMI2.4
in blassgelben Kristallen vom F. 270 (Zers.).
Beispiel 2
Zu einer Lösung von 12, 7 g Oxalylchlorid in 200 ml absolutem Tetrahydrofuran werden bei einer Temperatur von 15-17 14, 5 g 5-Nitro-2-aminothiazol, gelöst in 200ml absolutem Tetrahydrofuran, eingetropft. Man rührt eine halbe Stunde bei der gleichen Temperatur weiter und tropft dann bei Raumtemperatur eine Lösung von 13,5 g Dimethylamin in 100ml absolutem Tetrahydrofuran dazu. Anschliessend wird während einer halben Stunde bei Raumtemperatur weitergerührt und hierauf langsam auf Siedetemperatur erwärmt und während einer halben Stunde weiter zum Sieden erhitzt. Nach dem Erkalten wird das ausgefallene Produkt abgenutscht, mit Wasser ausgewaschen und aus viel i Äthanol umkristallisiert.
Man erhält so das N1, Nt-Di-methyl-N2- (5-nitro-2-thiazolyl)-oxamid der Formel
EMI2.5
in blassgelben Kristallen vom F. 222-224".
Beispiel 3
Zu einer Lösung von 12,7 g Oxalylchlorid in 200 ml absolutem Tetrahydrofuran werden bei einer Temperatur von 15-17 14, 5 g 5-Nitro-2-aminothiazol, gelöst in 200 ml absolutem Tetrahydrofuran, eingetropft. Man rührt eine halbe Stunde bei der gleichen Temperatur weiter und tropft dann bei Raumtemperatur eine Lösung von 9,3 g Methylamin in 100 ml absolutem Tetrahydrofuran dazu. Anschliessend wird während einer halben Stunde bei Raumtemperatur weitergerührt und hierauf langsam auf Siedetemperatur erwärmt und während einer halben Stunde weiter zum Sieden erhitzt. Nach dem Abkühlen wird der ausgefallene Niederschlag abgenutscht und mit Wasser ausgewaschen. Das erhaltene Produkt wird getrocknet und mit 500 ml siedendem Äthanol ausgerührt.
Man erhält so das Nl-Methyl-N2-(5-nitro-2-thiazolyl)-oxamid der Formel
EMI2.6
in gelben Kristallen vom F. 2750 (Zers.).
Process for the preparation of new nitrothiazole compounds
The main patent relates to a process for the preparation of new 5-nitrohiazole compounds of the formula
EMI1.1
where Rt and R2 are hydrogen or lower alkyl radicals and R is an optionally substituted amino group, and their salts.
In particular, these compounds have antiparasitic and antibacterial properties.
It has now been found that the compounds of the formula
EMI1.2
where R 'and R "are independently hydrogen atoms or methyl groups, have particularly valuable anti-parasitic and antibacterial properties.
The present invention therefore relates to a process for the preparation of compounds of the formula II.
The new compounds have valuable pharmacological, in particular anti-parasitic and antibacterial properties. Above all, they show an effect against protozoa and worms and are, for. B. on the infected animal, for example on mice, against gram-positive and especially against gram-negative bacteria, e.g. B. Salmolnella typhi or Coli bacilli such as Esch. coli, effective. In particular, the new compounds act as z. B. in experiments on hamsters shows against trichomonads and amoeba, especially against amoeba in the liver, and, for. B. on mice and sheep, against schistosomes. Furthermore, they have an effect against coccidia and against the pathogen of enterohepatitis (blackhead). The new compounds are accordingly useful as antiparasitic and antibacterial agents.
They can also be used as urine disinfectants. In particular, they are suitable for treating the diseases caused by the pathogens mentioned. The new compounds are also valuable intermediates for the production of other useful substances.
The process according to the invention for preparing the new compounds is characterized in that a compound of the formula
EMI1.3
with a compound of the formula
EMI1.4
reacted, in which R 'and R "have the meanings given at the beginning and one of the radicals X and Y is hydrogen and the other is the radical of the formula
EMI1.5
where X 'is a free or preferably a reactively modified oxy group, such as a reactively esterified or etherified oxy group, especially a halogen atom, in particular a chlorine or bromine atom.
The reaction according to the invention can be carried out in the customary manner, preferably in the presence of solvents and / or diluents, optionally in the presence of condensing agents such as basic condensing agents, at low, normal or elevated temperatures in an open or in a closed vessel under pressure.
The starting materials are known or can be obtained by methods known per se.
The compounds of the formula used as starting materials
EMI2.1
wherein X 'has the meaning given, can, for. B. obtained when using a compound of the formula
EMI2.2
with a compound of the formula
EMI2.3
where X 'has the meaning given and X "is a reactive modified, such as a reactive esterified or etherified oxy group, especially a halogen atom, in particular a chlorine or bromine atom, is converted. The reaction is carried out in the usual manner Formula V does not need to be isolated, but can be converted directly into the oxamide by the process according to the invention without isolation.
The new connections can e.g. B. in the form of pharmaceutical preparations, which contain them mixed with a pharmaceutical, organic or inorganic, solid or liquid carrier material suitable for enteral, parenteral or topical application.
The new compounds can also be used in veterinary medicine, e.g. B. in one of the forms mentioned above or in the form of feed or additives for animal feed.
In the following examples the temperatures are given in degrees Celsius.
example 1
14.5 g of 5-nitro-2-aminothiazole, dissolved in 200 ml of absolute tetrahydrofuran, are added dropwise to a solution of 12.7 g of oxalyl chloride in 300 ml of absolute tetrahydrofuran at a temperature of 20-22. Stirring is continued for half an hour at room temperature. Ammonia gas is then passed in at a temperature of 15-25 until the suspension has a pH of approximately 6.
The mixture is then gradually heated to boiling over the course of one hour and the precipitated by-product is then filtered off while hot. The filtrate is crystallized by concentration in vacuo to a volume of approximately 70 ml. The product that has crystallized out is filtered off with suction, washed out with water and a great deal of ethanol is recrystallized. This gives the N2- (5-nitro-2-thiazolyl) oxamide of the formula
EMI2.4
in pale yellow crystals from F. 270 (dec.).
Example 2
14.5 g of 5-nitro-2-aminothiazole, dissolved in 200 ml of absolute tetrahydrofuran, are added dropwise to a solution of 12.7 g of oxalyl chloride in 200 ml of absolute tetrahydrofuran at a temperature of 15-17. The mixture is stirred for a further half an hour at the same temperature and then a solution of 13.5 g of dimethylamine in 100 ml of absolute tetrahydrofuran is added dropwise at room temperature. The mixture is then stirred for a further half an hour at room temperature and then slowly heated to the boiling temperature and heated to the boil for a further half an hour. After cooling, the precipitated product is filtered off with suction, washed out with water and recrystallized from a large amount of ethanol.
This gives the N1, Nt-dimethyl-N2- (5-nitro-2-thiazolyl) oxamide of the formula
EMI2.5
in pale yellow crystals from F. 222-224 ".
Example 3
To a solution of 12.7 g of oxalyl chloride in 200 ml of absolute tetrahydrofuran, 5 g of 5-nitro-2-aminothiazole, dissolved in 200 ml of absolute tetrahydrofuran, are added dropwise at a temperature of 15-17 14. The mixture is stirred for a further half an hour at the same temperature and then a solution of 9.3 g of methylamine in 100 ml of absolute tetrahydrofuran is added dropwise at room temperature. The mixture is then stirred for a further half an hour at room temperature and then slowly heated to the boiling temperature and heated to the boil for a further half an hour. After cooling, the deposited precipitate is filtered off with suction and washed out with water. The product obtained is dried and stirred with 500 ml of boiling ethanol.
The Nl-methyl-N2- (5-nitro-2-thiazolyl) oxamide of the formula is obtained in this way
EMI2.6
in yellow crystals from F. 2750 (dec.).
Claims (1)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308865A CH459214A (en) | 1965-03-05 | 1965-03-05 | Process for the preparation of new nitrothiazole compounds |
| IL25238A IL25238A (en) | 1965-03-05 | 1966-02-23 | Nitrothiazole compounds and process for their manufacture |
| DE19661670335 DE1670335A1 (en) | 1965-03-05 | 1966-02-26 | New nitrothiazole compounds and processes for their preparation |
| GB8926/66A GB1099104A (en) | 1965-03-05 | 1966-03-01 | New nitrothiazole compounds and process for their manufacture |
| NL6602878A NL6602878A (en) | 1965-03-05 | 1966-03-04 | |
| BE677381D BE677381A (en) | 1965-03-05 | 1966-03-04 | |
| BR177555/66A BR6677555D0 (en) | 1965-03-05 | 1966-03-04 | PROCESS FOR THE MANUFACTURE OF NEW NITROTIAZOLIC COMPOUNDS |
| FR52028A FR1470665A (en) | 1965-03-05 | 1966-03-04 | Novel nitrothiazoles and process for their preparation |
| FR63840A FR5515M (en) | 1965-03-05 | 1966-06-02 | |
| FR63839A FR5514M (en) | 1965-03-05 | 1966-06-02 | |
| CH909669A CH486481A (en) | 1965-03-05 | 1966-12-02 | Process for the preparation of new nitrothiazole compounds |
| CH909769A CH486482A (en) | 1965-03-05 | 1966-12-02 | Process for the preparation of new nitrothiazole compounds |
| US684617A US3538089A (en) | 1965-03-05 | 1967-11-21 | 5-nitro-2-thiazolyl-oxamides |
| ES347819A ES347819A1 (en) | 1965-03-05 | 1967-11-30 | 5-nitro-2-thiazolyl-oxamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA952910 | 1966-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH481938A true CH481938A (en) | 1969-11-30 |
Family
ID=4142456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1726966A CH481938A (en) | 1965-03-05 | 1966-12-02 | Process for the preparation of new nitrothiazole compounds |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH481938A (en) |
| ES (1) | ES337051A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5925622A (en) * | 1998-07-13 | 1999-07-20 | Romark Laboratories, L.C. | Synthesis of aryl glucuronide of 2-hydroxy-N- (5-nitro-2-thiazolyl) benzamide, and pharmaceutical compositions comprising same |
-
1966
- 1966-12-02 CH CH1726966A patent/CH481938A/en unknown
-
1967
- 1967-02-20 ES ES337051A patent/ES337051A1/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5925622A (en) * | 1998-07-13 | 1999-07-20 | Romark Laboratories, L.C. | Synthesis of aryl glucuronide of 2-hydroxy-N- (5-nitro-2-thiazolyl) benzamide, and pharmaceutical compositions comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| ES337051A1 (en) | 1968-01-16 |
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