DE1062245B - Process for the preparation of 2-amino-4-pyridyl- (2 ') -thiazole and its salts - Google Patents
Process for the preparation of 2-amino-4-pyridyl- (2 ') -thiazole and its saltsInfo
- Publication number
- DE1062245B DE1062245B DEC15641A DEC0015641A DE1062245B DE 1062245 B DE1062245 B DE 1062245B DE C15641 A DEC15641 A DE C15641A DE C0015641 A DEC0015641 A DE C0015641A DE 1062245 B DE1062245 B DE 1062245B
- Authority
- DE
- Germany
- Prior art keywords
- salts
- thiourea
- thiazole
- amino
- pyridyl
- 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 11
- 150000003839 salts Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- NFBWZBZROWRCPY-UHFFFAOYSA-N 2-chloro-1-pyridin-2-ylethanone Chemical compound ClCC(=O)C1=CC=CC=N1 NFBWZBZROWRCPY-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- HTXQOROHFFYFMC-UHFFFAOYSA-N 5-methyl-4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1C HTXQOROHFFYFMC-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstellung von 2-Amino-4-pyridyl-(2')-thiazol und seinen Salzen Gegenstand der Erfindung sind Verfahren zur Herstellung von 2-Amino-4-pyridyl-(2')-thiazol der Formel \N / N'\NH 2 und seinen Salzen.Process for the preparation of 2-amino-4-pyridyl- (2 ') -thiazole and its salts The invention relates to processes for the preparation of 2-amino-4-pyridyl- (2') -thiazole of the formula \ N / N ' \ NH 2 and its salts.
Die neue Verbindung und ihre Salze besitzen gute analgetische Eigenschaften und sind antipyretisch wirksam. Sie können dementsprechend als Arzneimittel verwendet werden. Die Prüfung der Analgesie an der Maus, gemessen an der Verlängerung der Reaktionszeit bei Einwirkung eines thermischen Reizes an der Schwanzspitze, ergibt für das aus »Helvetica Chimica Acta,, Bd. 38 [19551, S. 1289 bis 1291, bekannte 2,4-Bis-(a-pyridyl)-thiazol bei einer Dosis von 500 mg/kg peroral keine Wirkung, während 2-Amino-4-pvridyl-(2')-thiazol bei niedriger Toxizität schon bei einer Dosis von 250 mg/kg peroral eine Verlängerung der Reaktionszeit um 63 % zeigt.The new compound and its salts have good analgesic properties and are antipyretic. Accordingly, they can be used as a medicine. Testing the analgesia in the mouse, measured by the extension of the reaction time when exposed to a thermal stimulus at the tip of the tail, results in the 2,4- known from Helvetica Chimica Acta, Vol. 38 [19551, pp. 1289 to 1291, Bis- (a-pyridyl) -thiazole at a dose of 500 mg / kg orally has no effect, while 2-amino-4-pvridyl- (2 ') -thiazole with low toxicity already has an effect at a dose of 250 mg / kg orally Showing 63 % increase in response time.
Das ebenfalls bekannte 2-Amino-4-phenyl-5-methylthiazol weist auf Grund der Angaben in »Bulletin de la societe chimique de France", 5. serie, Bd. 17 [1950], S. 582, keine analgetische Wirkung auf und ist für Mäuse sehr toxisch.The also known 2-amino-4-phenyl-5-methylthiazole has no analgesic effect on the basis of the information in "Bulletin de la societe chimique de France", 5th series, Vol. 17 [ 1950], p. 582 and is very toxic to mice.
Die neue Verbindung wird in an sich bekannter Weise erhalten. Ein Verfahren besteht z. B. darin, daß man 2-Acetylpyridin, das im Acetylrest einen reaktionsfähigen Substituenten, z. B. die Diazogruppe, oder eine reaktionsfähige veresterte Oxygruppe trägt, vorzugsweise 2-Halogenacetylpyridin mit Thioharnstoff umsetzt. So kann man beispielsweise 2-Chloracetylpyridin mit Thioharnstoff umsetzen.The new compound is obtained in a manner known per se. A Procedure consists e.g. B. in that you have 2-acetylpyridine, the one in the acetyl radical reactive substituents, e.g. B. the diazo group, or a reactive one esterified oxy group, preferably 2-haloacetylpyridine with thiourea implements. For example, 2-chloroacetylpyridine can be reacted with thiourea.
Eine andere Ausführungsform des Verfahrens besteht darin, daß man 2-Acetylpyridin mit Thioharnstoff und Oxydationsmitteln, z. B. Jod, reagieren läßt.Another embodiment of the method is that one 2-acetylpyridine with thiourea and oxidizing agents, e.g. B. iodine can react.
Je nach der Arbeitsweise erhält man die neue Verbindung in Form der freien Base oder ihrer Salze. Aus den Salzen kann in an sich bekannter Weise die freie Base gewonnen werden. Von letzteren lassen sich durch Umsetzung mit Säuren, die zur Bildung therapeutisch verwendbarer Salze geeignet sind, Salze gewinnen, z. B. die der Halogenwasserstoffsäuren,Schwefelsäure, Salpetersäure, Phosphorsäure, Rhodanwasserstoffsäure, Essigsäure, Propionsäure, Oxalsäure, Malonsäure, Bernsteinsäure, Äpfelsäure, Methansulfonsäure, Äthansulfonsäure, Oxyäthansulfonsäure, Benzol- oder Toluolsulfonsäure oder von an sich therapeutisch wirksamen Säuren.Depending on the working method, the new connection is obtained in the form of the free base or its salts. From the salts can in a manner known per se free base can be obtained. The latter can be converted into acids, which are suitable for the formation of therapeutically useful salts, extract salts, z. B. those of the hydrohalic acids, sulfuric acid, nitric acid, phosphoric acid, Rhodanic acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, Malic acid, methanesulphonic acid, ethanesulphonic acid, oxyethanesulphonic acid, benzene or Toluenesulfonic acid or of therapeutically effective acids per se.
Die neue Verbindung oder ihre Salze können in Mischung mit einem für die enterale, parenterale oder topicale Applikation geeigneten, pharmazeutischen, organischen oder anorganischen, festen oder flüssigen Trägermaterial als Arzneimittel Verwendung finden. Die verfahrensgemäß verwendeten Ausgangsstoffe sind bekannt oder können nach an sich bekannten Methoden gewonnen werden. Sie können auch unter den Reaktionsbedingungen erhalten werden.The new compound or its salts can be mixed with one for pharmaceutical, enteral, parenteral or topical application organic or inorganic, solid or liquid carrier material as a medicament Find use. The starting materials used according to the process are known or can be obtained by methods known per se. You can also use the Reaction conditions are obtained.
Die Erfindung wird in den folgenden Beispielen näher beschrieben.The invention is described in more detail in the following examples.
Beispiel 1 3 g rohes 2-Chloracetylpyridin in 50 cm3 absolutem Äthanol werden mit 5 g Thioharnstoff 10 Stunden unter Rückfluß gekocht. Darauf wird der Alkohol abdestilliert und der Rückstand noch 90 Minuten auf 150°C erwärmt. Das Reaktionsgemisch wird in 50 cm3 4 n-Salzsäure aufgenommen, dreimal mit je 50 cm3 Äther ausgeschüttelt, um Nebenprodukte zu entfernen, die wäßrige Phase mit gesättigter Natriumbicarbonatlösung alkalisch gemacht und dreimal mit je 100 cm3 Äther ausgeschüttelt. Der dunkelbraune, kristalline Ätherrückstand wird fünfmal mit je 40 cm3 heißem Ligroin extrahiert. Beim Erkalten des Ligroins scheiden sich farblose Kristalle aus, die noch zweimal aus Ligroin umkristallisiert werden. Man erhält so das 2-Amino-4-pyridyl-(2')-thiazol, F. 175 bis 176'C (Gelbfärbung).Example 1 3 g of crude 2-chloroacetylpyridine in 50 cm3 of absolute ethanol are refluxed with 5 g of thiourea for 10 hours. Then the Alcohol is distilled off and the residue is heated to 150 ° C. for a further 90 minutes. The reaction mixture is taken up in 50 cm3 of 4N hydrochloric acid, extracted three times with 50 cm3 of ether each time, to remove by-products, the aqueous phase with saturated sodium bicarbonate solution made alkaline and shaken out three times with 100 cm3 of ether each time. The dark brown one crystalline ether residue is extracted five times with 40 cm3 hot ligroin each time. When the ligroin cools down, colorless crystals separate out, which twice more be recrystallized from ligroin. The 2-amino-4-pyridyl- (2 ') -thiazole is obtained in this way, F. 175 to 176 ° C (yellow color).
Beispiel 2 10 g 2-Acetylpyridin, 19 g Jod und 12,8 g feinverriebener Thioharnstoff werden in 50 cm3 Tetrachlorkohlenstoff 16 Stunden auf dem Wasserbad erwärmt, wobei sich das Gemisch entfärbt. Anschließend wird der Tetrachlorkohlenstoff im Vakuum abgedampft. Das rohe Hydrojodid wird dreimal mit Zusatz von Tierkohle aus je 150 cm3 Wasser umkristallisiert. Anschließend wird in heißem Wasser gelöst, die Lösung mit konzentrierter Ammoniaklösung alkalisch gemacht, das ausgefallene freie Amin abfiltriert und nach dem Trocknen aus Ligroin umkristallisiert. Man erhält farblose Kristalle des 2 Amino-4-pyridyl-(2')-thiazols, die bei 172 bis 174°C schmelzen.Example 2 10 g of 2-acetylpyridine, 19 g of iodine and 12.8 g of finely ground Thiourea are in 50 cm3 carbon tetrachloride for 16 hours on a water bath heated, whereby the mixture discolored. Then the carbon tetrachloride evaporated in vacuo. The raw hydroiodide is made three times with the addition of animal charcoal from ever 150 cm3 of water recrystallized. Then in hot Dissolved water, made the solution alkaline with concentrated ammonia solution, that precipitated free amine is filtered off and recrystallized from ligroin after drying. Colorless crystals of 2-amino-4-pyridyl- (2 ') - thiazole are obtained, which at 172 to Melting at 174 ° C.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC15641A DE1062245B (en) | 1957-10-17 | 1957-10-17 | Process for the preparation of 2-amino-4-pyridyl- (2 ') -thiazole and its salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC15641A DE1062245B (en) | 1957-10-17 | 1957-10-17 | Process for the preparation of 2-amino-4-pyridyl- (2 ') -thiazole and its salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1062245B true DE1062245B (en) | 1959-07-30 |
Family
ID=7015882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC15641A Pending DE1062245B (en) | 1957-10-17 | 1957-10-17 | Process for the preparation of 2-amino-4-pyridyl- (2 ') -thiazole and its salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1062245B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2429787A1 (en) * | 1978-06-27 | 1980-01-25 | Boehringer Sohn Ingelheim | NOVEL DERIVATIVES OF THIAZOL-2-OXAMIC ACID SUBSTITUTED IN POSITION 4, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS |
| EP0149884A3 (en) * | 1983-09-09 | 1986-07-30 | Takeda Chemical Industries, Ltd. | 5-pyridyl-1,3-thiazole derivatives, their production and use |
| EP0234011A1 (en) * | 1985-12-02 | 1987-09-02 | Warner-Lambert Company | 4-(1,2,5,6-tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines and 4-(hexahydro-1-alkyl-3-pyridinyl)-2-thiazolamines |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2481674A (en) * | 1945-03-01 | 1949-09-13 | Eastman Kodak Co | 4-(2-pyrryl) thiazoles and 4-(2-pyrryl) selenazoles |
-
1957
- 1957-10-17 DE DEC15641A patent/DE1062245B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2481674A (en) * | 1945-03-01 | 1949-09-13 | Eastman Kodak Co | 4-(2-pyrryl) thiazoles and 4-(2-pyrryl) selenazoles |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2429787A1 (en) * | 1978-06-27 | 1980-01-25 | Boehringer Sohn Ingelheim | NOVEL DERIVATIVES OF THIAZOL-2-OXAMIC ACID SUBSTITUTED IN POSITION 4, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS |
| EP0149884A3 (en) * | 1983-09-09 | 1986-07-30 | Takeda Chemical Industries, Ltd. | 5-pyridyl-1,3-thiazole derivatives, their production and use |
| EP0234011A1 (en) * | 1985-12-02 | 1987-09-02 | Warner-Lambert Company | 4-(1,2,5,6-tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines and 4-(hexahydro-1-alkyl-3-pyridinyl)-2-thiazolamines |
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