DE1470357C - 1 (3 Dimethylammopropyl) 4 myristoyl amidopiperidine, its acid addition salts and process for their preparation - Google Patents
1 (3 Dimethylammopropyl) 4 myristoyl amidopiperidine, its acid addition salts and process for their preparationInfo
- Publication number
- DE1470357C DE1470357C DE1470357C DE 1470357 C DE1470357 C DE 1470357C DE 1470357 C DE1470357 C DE 1470357C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- acid addition
- addition salts
- preparation
- amidopiperidine
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims description 11
- 150000003839 salts Chemical class 0.000 title claims description 6
- 239000011780 sodium chloride Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 title 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 235000021360 Myristic acid Nutrition 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PGBHMTALBVVCIT-VCIWKGPPSA-N Neomycin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 description 4
- 229940053050 Neomycin Sulfate Drugs 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000001580 bacterial Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UCSJYZPVAKXKNQ-HZYVHMACSA-N 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229940064005 Antibiotic throat preparations Drugs 0.000 description 2
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 2
- 229940042052 Antibiotics for systemic use Drugs 0.000 description 2
- 229940042786 Antitubercular Antibiotics Drugs 0.000 description 2
- 241001480043 Arthrodermataceae Species 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L Barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 229940093922 Gynecological Antibiotics Drugs 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000845 anti-microbial Effects 0.000 description 2
- 230000003115 biocidal Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000037304 dermatophytes Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229940079866 intestinal antibiotics Drugs 0.000 description 2
- 229960004927 neomycin Drugs 0.000 description 2
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- -1 1- (3'-dimethylaminopropyl) -piperidin-4-amine Chemical compound 0.000 description 1
- DTFAJAKTSMLKAT-JDCCYXBGSA-N 2-deoxystreptamine Chemical compound N[C@H]1C[C@@H](N)[C@H](O)[C@@H](O)[C@@H]1O DTFAJAKTSMLKAT-JDCCYXBGSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L Barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 229960005322 Streptomycin Drugs 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000000172 allergic Effects 0.000 description 1
- 201000005794 allergic hypersensitivity disease Diseases 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000009114 investigational therapy Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001235 sensitizing Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LKWYTUHHMNCZEQ-UHFFFAOYSA-M tetradecanoic acid;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC(O)=O LKWYTUHHMNCZEQ-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 238000005429 turbidity Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Die Erfindung betrifft l-(3'-Dimethylaminopropyl)-4-myristoylamidopiperidin der Formel IThe invention relates to 1- (3'-dimethylaminopropyl) -4-myristoylamidopiperidine of the formula I.
CHCH
N — CH, — CH, — CH, — NN - CH, - CH, - CH, - N
NH — C — (CH2J12 — CH3 NH - C - (CH 2 J 12 - CH 3
dessen Säureadditionssalze und Verfahren zu ihrer Herstellung.its acid addition salts and process for their preparation.
Erfindungsgemäß wird die neue Verbindung durch Umsetzung von l-(3'-Dimethylaminopropyl)-piperidin-4-amin der Formel IIAccording to the invention, the new compound is made by reacting 1- (3'-dimethylaminopropyl) -piperidin-4-amine of formula II
3\ 3 \
) N — CH2 — CH2 — CH2 — N CH/) N - CH 2 - CH 2 - CH 2 - N CH /
NH,NH,
mit einem Säurehalogenid der Myristinsäure, gegebenenfalls in Gegenwart eines säurebindenden Mittels, in an sich bekannter Weise erhalten.with an acid halide of myristic acid, optionally in the presence of an acid-binding agent, obtained in a manner known per se.
Die Umsetzung erfolgt zweckmäßig bei Raumtemperatur entweder in einem organischen Lösungsmittel, wie Benzol, Tetrahydrofuran oder Chloroform, oder nach Schotten — Baumann in wäßriger Lösung in Gegenwart einer anorganischen Base. Bei der Umsetzung in einem organischen Lösungsmittel können als säurebindende Mittel anorganische oder tertiäre organische Basen, beispielsweise Pyridin, verwendet werden, letztere können dann auch gleichzeitig als Lösungsmittel dienen. '. The reaction is expediently carried out at room temperature either in an organic solvent, such as benzene, tetrahydrofuran or chloroform, or, according to Schotten-Baumann, in an aqueous solution in the presence of an inorganic base. In the case of the reaction in an organic solvent, inorganic or tertiary organic bases, for example pyridine, can be used as acid-binding agents; the latter can then also serve as solvents at the same time. '.
Die erhaltene Base kann gewünschtenfalls nachträglich nach üblichen Methoden mit einer anorganischen oder organischen Säure, beispielsweise mit Salzsäure, Schwefelsäure, Phosphorsäure, Weinsäure, Bernsteinsäure, Zitronensäure, Maleinsäure oder Adipinsäure, in ihre Säureadditionssalze übergeführt werden.The base obtained can, if desired, subsequently by customary methods with an inorganic or organic acid, for example with hydrochloric acid, sulfuric acid, phosphoric acid, tartaric acid, Succinic acid, citric acid, maleic acid or adipic acid, converted into their acid addition salts will.
Das als Ausgangsstoff verwendete l-(3'-Dimethylaminopropyi)-piperidin-4-amin der Formel II ist ebenfalls neu; es läßt sich beispielsweise nach den von P. Brook s und Mitarbeiter im J. Chem. Soc, 1957, S. 3165, beschriebenen Verfahren durch Reduktion des entsprechenden Oxims mittels Natrium in Äthanol oder mittels katalytischer Hydrierung darstellen. Die Substanz hat einen Siedepunkt von 99 bis 1000C/ 0,2 mm Hg; sie wurde in 68%iger Ausbeute erhalten.The l- (3'-Dimethylaminopropyi) -piperidin-4-amine of the formula II used as starting material is also new; it can be prepared, for example, by the method described by P. Brooks and coworkers in J. Chem. Soc, 1957, p. 3165, by reducing the corresponding oxime by means of sodium in ethanol or by means of catalytic hydrogenation. The substance has a boiling point of 99 to 100 0 C / 0.2 mm Hg; it was obtained in 68% yield.
Das 1 - (3' - Dimethylaminopropyl) - 4 - myristoylamidopiperidin = A weist wertvolle therapeutische Eigenschaften auf, insbesondere wirkt es antimikrobiell und verhindert das Wachstum von Dermatophyten und Schimmelpilzen. Es wurde vergleichend mit Neomycinsulfat == B im Hinblick auf die antimikrobielle Wirkung bei Streptococcus Aronson untersucht. The 1 - (3 '- dimethylaminopropyl) - 4 - myristoylamidopiperidine = A has valuable therapeutic properties, in particular it has an antimicrobial effect and prevents the growth of dermatophytes and molds. It became comparative with neomycin sulfate == B in terms of antimicrobial Effect on Streptococcus Aronson investigated.
Diese Untersuchung wurde mit Hilfe des Reihentestes durchgeführt. Es wurde eine Bakteriensuspension· hergestellt, die mit Hilfe eines Photometers so eingestellt wurde, daß sie die Trübung einer Bariumsulfataufschlämmung zeigte, die durch Versetzen von 97,0 ml einer 1 %igen Schwefelsäure mit 3,0 ml einer l°/oigen Bariumchloridlösung zustande kommt. Es wurde ein Tropfen einer so eingestellten Bakteriensuspension in eine Nährbouillon eingetragen, die die Wirksubstanz in bestimmten Konzentrationen enthielt. Diese Kultur wurde 17 Stunden lang bei 37"C bebrütet. Hernach wurde festgestellt, ob ein Bakterienwachstum stattfand oder nicht. Es wurde dabei gefunden, daß die Substanz A vorliegender Erfindung eine Wachstumshemmung bis zu einer Konzentration von 2 y/ml erzielt, Wachstum von SC. Aronson trat erst bei einer Konzentration unterhalb von 2y/ml ein; Neomycinsulfat verhinderte dagegen das Wachstum erst ab einer Konzentration von lOy/ml, unterhalb von lOy/ml trat Wachstum ein. This investigation was carried out with the aid of the row test. A bacterial suspension was created which was adjusted with the aid of a photometer so that it was the turbidity of a barium sulfate slurry showed that by adding 97.0 ml of a 1% sulfuric acid with 3.0 ml of a 10% barium chloride solution comes about. It became a drop of a bacterial suspension adjusted in this way entered into a nutrient broth that contained the active ingredient in certain concentrations. This culture was incubated for 17 hours at 37 ° C. It was then determined whether there was any bacterial growth took place or not. It was found that the substance A of the present invention achieved growth inhibition up to a concentration of 2 μg / ml, growth of SC. Aronson stepped only at a concentration below 2y / ml; Neomycin sulfate, on the other hand, prevented growth Growth only started at a concentration of 10y / ml and below 10y / ml.
Es wurde des weiteren gefunden, daß die Substanz A gegen Dermatophyten sehr gut wirksam ist; Neomycinsulfat zeigte dagegen keine Wirkung.It has also been found that substance A is very effective against dermatophytes; Neomycin sulfate on the other hand showed no effect.
Die Substanz A verhinderte das Wachstum von Trichophyton mentagrophytes und von Trichophyton rubrum noch in einer Konzentration von lOy/ml.Substance A prevented the growth of Trichophyton mentagrophytes and Trichophyton rubrum still in a concentration of 10 y / ml.
Die Substanz A ist ebenfalls gut wirksam gegen Schimmelpilze, allerdings erst in höheren Konzentrationen. Da die Substanz A äußerliche Anwendung finden soll, wurde die akute Toxizität an Gruppen von je 10 Mäusen pro Dosis durch subcutane Applikation bestimmt. Es wurde für die Substanz A eine LDj0 von 125 mg/kg Maus gefunden; Neomycinsulfat besitzt eine LD50 von 180 mg/kg Maus, subcutan (vgl. auch G. E. W e b e r, Antibiotica Codex, Wiss. Verl. Ges.m.b.H., Stuttgart, 1963).Substance A is also very effective against mold, but only in higher concentrations. Since substance A is to be used externally, the acute toxicity was determined in groups of 10 mice per dose by subcutaneous application. An LDj 0 of 125 mg / kg mouse was found for substance A; Neomycin sulfate has an LD 50 of 180 mg / kg mouse, subcutaneously (cf. also GE Weber, Antibiotica Codex, Wiss. Verl. Ges.mbH, Stuttgart, 1963).
Von Neomycin ist bekannt, daß diese Substanz allergisch wirkt. Bei einzelnen Patienten besteht eine Gruppenallergie gegen antibakterielle Antibiotika, wie z. B. Neomycin, Bacithracin, und Streptomycin, wobei diese Antibiotika den gleichen Aminozucker Desoxystreptamin enthalten (vgl. Wolfgang Raab, »Diagnose von Arzneimittelallergien«, Verlag Urban, und Schwarzenberg, München, 1968, S. 24). Die Substanz A ist dagegen frei von solchen Sensibilisierungserscheinungen. Neomycin is known to have an allergic effect. There is one in individual patients Group allergy to antibacterial antibiotics such as B. neomycin, bacithracin, and streptomycin, where these antibiotics contain the same amino sugar deoxystreptamine (cf. Wolfgang Raab, »Diagnose von Arzneimittelallergien ", Verlag Urban, and Schwarzenberg, Munich, 1968, p. 24). the Substance A, on the other hand, is free from such sensitization symptoms.
Lösungen von 2,8 g l-(3'-Dimethylaminopropyl)-piperidin-4-amin und 3,7 g Myristinsäurechlorid in je 10 ml absolutem Benzol werden vermischt und das Gemisch 2 Stunden unter Rückfluß erhitzt oder über Nacht bei Raumtemperatur belassen. Nach dem Abkühlen wird mit 50 ml Wasser und 5 ml 2 n-Salzsäure versetzt. Die wäßrige Phase wird abgetrennt, einmal mit Äther ausgeschüttelt und dann mit 2 n-Natronlauge alkalisch gestellt. Das ausgefallene Produkt wird in Äther aufgenommen und die Lösung über Natriumsulfat getrocknet. Nach Abdestillieren des Lösungsmittels bleibt ein fester Rückstand, der aus Petroläther umkristallisiert wird. Man erhält so 3,6 g I -(3'-Dimethylaminopropyl)-4-myristoylamidopiperidin vom F. 88 bis 89" C.Solutions of 2.8 g of l- (3'-dimethylaminopropyl) piperidin-4-amine and 3.7 g of myristic acid chloride in 10 ml of absolute benzene each time are mixed and the mixture is heated under reflux for 2 hours or over Leave at room temperature overnight. After cooling, 50 ml of water and 5 ml of 2N hydrochloric acid are added offset. The aqueous phase is separated off, extracted once with ether and then with 2N sodium hydroxide solution made alkaline. The precipitated product is taken up in ether and the solution over Dried sodium sulfate. After the solvent has been distilled off, a solid residue remains Petroleum ether is recrystallized. 3.6 g of I - (3'-dimethylaminopropyl) -4-myristoylamidopiperidine are obtained in this way from F. 88 to 89 "C.
Claims (2)
Family
ID=
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