DE1768200C - 3,4-Methylenedioxybenzyl-biguanide and their pharmacologically non-toxic salts - Google Patents
3,4-Methylenedioxybenzyl-biguanide and their pharmacologically non-toxic saltsInfo
- Publication number
- DE1768200C DE1768200C DE1768200C DE 1768200 C DE1768200 C DE 1768200C DE 1768200 C DE1768200 C DE 1768200C
- Authority
- DE
- Germany
- Prior art keywords
- biguanide
- methylenedioxybenzyl
- acid
- hydrochloride
- toxic salts
- 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
- 150000003839 salts Chemical class 0.000 title claims description 5
- 239000011780 sodium chloride Substances 0.000 title claims description 5
- 230000003000 nontoxic Effects 0.000 title claims description 4
- 231100000252 nontoxic Toxicity 0.000 title claims description 4
- RFFRCCSXOSTBAI-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NCC1=CC=C2OCOC2=C1 RFFRCCSXOSTBAI-UHFFFAOYSA-N 0.000 title claims 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- -1 3,4-methylenedioxybenzyl Chemical group 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 description 4
- 241000700198 Cavia Species 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- QGBSISYHAICWAH-UHFFFAOYSA-N cyanoguanidine Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000036740 Metabolism Effects 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000004283 biguanides Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000002641 glycemic Effects 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 230000004060 metabolic process Effects 0.000 description 2
- 230000035786 metabolism Effects 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KBQQSMNMBJRWCS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-N-methylmethanamine;hydrochloride Chemical compound Cl.CNCC1=CC=C2OCOC2=C1 KBQQSMNMBJRWCS-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 210000004369 Blood Anatomy 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010012601 Diabetes mellitus Diseases 0.000 description 1
- 229960002598 Fumaric acid Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N Malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 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
- 241000700159 Rattus Species 0.000 description 1
- 229960005137 Succinic Acid Drugs 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003178 anti-diabetic Effects 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229940058933 biguanide antimalarials Drugs 0.000 description 1
- 229940090145 biguanide blood glucose lower drugs Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N diguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 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
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 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
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Description
Die Erfindung betrifft 3,4-Methylendioxybenzylbiguanidö der allgemeinen FormelThe invention relates to 3,4-methylenedioxybenzyl biguanido the general formula
Ii iiIi ii
R1 NH NHR 1 NH NH
in der R1 und R2 ein Wasserstoffatom oder eine Methylgruppe bedeuten, und deren pharmakologisch nicht giftige Salze.in which R 1 and R 2 represent a hydrogen atom or a methyl group, and their pharmacologically non-toxic salts.
Diese Verbindungen besitzen eine hypoglykämische Wirkung und verringern wirksam den Glukosegehalt im Blut von Säugetieren. Es ist zwar bekannt, daß bestimmte Biguanidverbindungen, wie die aus »Archiv für Experimentelle Pathologie und Pharmacologie«, 142 (1929), S. 290, und aus der britischen Patentschrift 852.584 bekannten Stoffe antidiabetische Eigenschaften besitzen, jedoch weisen die neuen Verbindungen eine stärkere hypuglykämische Wirksamkeit auf als die bekannten Biguanidverbindungen, und außerdem besitzen sie eine Regulierungswirkung Für den Lipoidstoffwechsel. These compounds have a hypoglycemic effect and are effective in reducing glucose levels in the blood of mammals. It is known that certain biguanide compounds, such as those from 'Archiv für Experimental Pathologie und Pharmacologie ', 142 (1929), p. 290, and from the British patent 852,584 known substances have antidiabetic properties, but the new compounds exhibit a stronger hypuglycemic activity than the known biguanide compounds, and moreover they have a regulating effect for the lipoid metabolism.
In Verglcichsversuchen wurde die glykämische Wirksamkeit einiger der neuen Stoffe gegenüber demIn comparison tests, the glycemic Effectiveness of some of the new substances against the
bekannten, gut wirksamen 1,1 - Dimethyl - biguanidchlorhydrat mit gleicher Wirkungsrichtung geprüft. Die Versuche wurden in der Weise durchgeführt, daß die zu untersuchenden Verbindungen Meerschweinchen subkutan verabreicht und dann die Glykämie bestimmt wurde. Die glykämischen Dosen wurden auf dem Autoanalysator »Technikon« in der entsprechend angewandten Technik von Hoffmann bestimmt. Der Ausdruck DA5q stellt hierbei die mittlere aktive Dosis dar, d.h. diejenige Dosis in mg/Pro-well-known, effective 1,1-dimethyl-biguanide chlorohydrate tested with the same direction of action. The experiments were carried out in such a way that the compounds to be examined were administered subcutaneously to guinea pigs and then the glycemia was determined. The glycemic doses were determined on the »Technikon« autoanalyzer using the technique used by Hoffmann. The expression DA 5q here represents the mean active dose, ie that dose in mg / per
dukt pro kg/Tier, welche eine 50%ige Verminderung der Glykämie hervorruft. Die akute Toxizität wurde bei der Maus durch intraperitoneale Verabreichung bestimmt. Der therapeutische Index stellt das Verhältnis von mittlerer toxischer Dosis zu mittlerer aktiver Dosis dar.product per kg / animal, which causes a 50% reduction in glycaemia. The acute toxicity was determined in the mouse by intraperitoneal administration. The therapeutic index represents the relationship from medium toxic dose to medium active dose.
In der nachstehenden Tabelle sind die hierbei erhaltenen Ergebnisse zusammengestellt.The results obtained in this way are compiled in the table below.
Geprüfte VerbindungTested connection
Toxizität DL50
mg/kg Maus, i. p.Toxicity DL 50
mg / kg mouse, ip
Wirksame Dosis DA50 Effective dose DA 50
mg/kg Meerschweinchen, s. c.mg / kg guinea pigs, s. c.
Therapeutischer IndexTherapeutic index
DL50
DA50 DL 50
DA 50
Beispiel 1 (Hydrochlorid) Example 1 (hydrochloride)
Beispiel 2 (Hydrochlorid) Example 2 (hydrochloride)
Beispiel 3 (Hydrochlorid) Example 3 (hydrochloride)
1,1-Dimethylbiguanidchlorhydrat (bekannt) 1,1-dimethylbiguanide chlorohydrate (known)
Aus den gefundenen Werten ist ersichtlich, daß die geprüften, neuen Verbindungen der Beispiele 1 bis 3 eine bedeutend bessere Wirksamkeit besitzen.From the values found it can be seen that the tested, new compounds of Examples 1 to 3 have a significantly better effectiveness.
Ferner wurde bei Versuchen an Meerschweinchen auf Glykämie nach subkutaner und oraler Verabreichung festgestellt, daß die aktive Mindestdosis der neuen Verbindungen zwischen 10 und 20 mg/kg bei subkutaner Verabreichung und zwischen 25 und 40 mg/kg bei oraler Verabreichung schwankt. Die Dosis, die eine 50%ige Verringerung der Glykämie hervorruft, beträgt 30 bis 40 mg/kg subkutan und 60 bis 80 mg/kg peroral. Weiterhin ist die Wirkungsdauer der neuen Verbindungen besonders lang, und die Erniedrigung der Glykämie erreicht ihr Maximum 5 bis 6 Stunden nach der peroralen Verabreichung und behält diese 8 bis 10 Stunden lang bei. Außerdem wurde eine interessante Wirksamkeit der neuen Verbindungen auf den Lipoidstoffwechsel beobachtet. Bei Verabreichung einer Dosis von 50 bis 100 mg/kg pro Tag während 10 Tagen bei der Ratte wurde eine Verhinderung der Gewichtsaufnahme bis zu 50% in bezug auf die nicht behandelten Vergleichstiere hervorgerufen. Gleichzeitig konnte eine Signifikante Verringerung des Epididymisfettes bei den behandelten Tieren um 25 bis 33% festgestellt werden, was die Wirksamkeit der neuen Verbindungen auf die Reservelipoide zeigt.Tests on guinea pigs also examined glycaemia after subcutaneous and oral administration found that the minimum active dose of the new compounds was between 10 and 20 mg / kg subcutaneous administration and between 25 and 40 mg / kg for oral administration. the Dose that produces a 50% reduction in glycemia is 30 to 40 mg / kg subcutaneously and 60 up to 80 mg / kg orally. Furthermore, the duration of action of the new compounds is particularly long, and the reduction glycemia reaches its maximum 5 to 6 hours after oral administration and persists this for 8 to 10 hours. In addition, there was an interesting effectiveness of the new compounds observed on lipoid metabolism. When administered at a dose of 50 to 100 mg / kg per On the 10th day for 10 days in the rat, prevention of weight absorption up to 50% was related on the non-treated comparison animals. At the same time there was a significant decrease of the epididymal fat can be found in the treated animals by 25 to 33%, which is the Shows effectiveness of new compounds on reserve lipids.
Die Verbindungen der oben angegebenen allgemeinen Formel können zur Diabetesbehandlung beim Menschen, vorzugsweise durch bukale Verabreichung verwendet werden. Sie können zusammen mit geeigneten pharmazeutischen Trägern verwendet werden.The compounds of the general formula given above can be used in the treatment of diabetes Humans, preferably by buccal administration. You can get along with suitable pharmaceutical carriers.
Die 3,4-Methylendioxybenzyl-biguanide der oben
angegebenen allgemeinen Formel und deren pharma-200
140
150
450The 3,4-methylenedioxybenzyl biguanides of the general formula given above and their pharma-200
140
150
450
165165
6,66
2,80
3,75
2,726.66
2.80
3.75
2.72
kologisch nicht giftige Salze werden nach an sich bekannten Methoden hergestellt. Beispielsweise wird das Hydrochlorid eines Amins der allgemeinen Formel Ecologically non-toxic salts are produced according to methods known per se. For example, will the hydrochloride of an amine of the general formula
CH2 — N — H
R1 CH 2 -N-H
R 1
in der R1 die obige Bedeutung besitzt, mit einem Dicyandiamid der allgemeinen Formelin which R 1 has the above meaning, with a dicyandiamide of the general formula
N = C- NH-C — NHR2 N = C-NH-C-NHR 2
IlIl
NHNH
in der R2 die oben angegebene Bedeutung besitzt, kondensiert und aus der Reaktiönsmischung das betreffende Biguanidhydrochlorid erhalten.in which R 2 has the meaning given above, is condensed and the biguanide hydrochloride in question is obtained from the reaction mixture.
Für die überführung der Basen der oben angegebenen allgemeinen Formel in Salze eignen sich z. B. Salzsäure, Bromwasserstoffsäure, Salpetersäure, Schwefelsäure und Phosphorsäure sowie Essigsäure, Malonsäure, Bernsteinsäure, Maleinsäure, Fumarsäure, Äpfelsäure, Weinsäure, Zitronsäure, Benzoesäure, Salicylsäure und Methansulfonsäure.For the conversion of the bases of the general formula given above in salts are, for. B. Hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid and phosphoric acid as well as acetic acid, Malonic acid, succinic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid, benzoic acid, Salicylic acid and methanesulfonic acid.
Beispiel la
N1 -(3,4-Methylendioxybenzyl)-biguanidhydrochloridExample la
N 1 - (3,4-methylenedioxybenzyl) biguanide hydrochloride
Eine Mischung aus 56 Gewichtsteilen Piperonylaminhydrochlcrid und 25 Gewichtsteilen Dicyandiamid wird in einem ölbad allmählich unter RührenA mixture of 56 parts by weight of piperonylamine hydrochloride and 25 parts by weight of dicyandiamide is gradually stirred in an oil bath
auf 150 bis 1600C erhitzt und etwa 1 Stunde auf dieser Temperatur gehalten und danach abkühlen gelassen. Das erhaltene Reaktionsgemisch wird dann mit 300 Teilen Isopropanol zum Sieden erhitzt und hierauf abkühlen gelassen. Das ausgefallene kristalline Produkt wird abfiltriert und aus Isopropanol umkristallisiert: Es werden 15 Gewichtsteile Nt-(3,4-Methylendioxybenzyl)-biguanidhydrochlorid vom F. 172 bis 173° C erhalten.heated to 150 to 160 0 C and held at this temperature for about 1 hour and then allowed to cool. The reaction mixture obtained is then heated to boiling with 300 parts of isopropanol and then allowed to cool. The precipitated crystalline product is filtered off and recrystallized from isopropanol: 15 parts by weight of N t - (3,4-methylenedioxybenzyl) biguanide hydrochloride with a melting point of 172 ° to 173 ° C. are obtained.
N^ß^Methylendioxybenzyty-biguanidN ^ ß ^ Methylenedioxybenzyty-biguanid
10 Teile des vorstehend erhaltenen Chlorhydrats10 parts of the hydrochloride obtained above
von N^ß^-Methylendioxybenzy'J-biguanid werdenbe of N ^ ß ^ -Methylenedioxybenzy'J-biguanid
in 175 Teilen Wasser gelöst. Die Lösung wird durchdissolved in 175 parts of water. The solution is through
Zugabe von 30 ml 2 η-Natronlauge alkalisch gestellt.Addition of 30 ml of 2 η sodium hydroxide solution made alkaline.
Hierbei schieden sich 7,3 Teile Nr(3,4-Methylen-7.3 parts of N r (3,4-methylene
dioxybenzyl)-biguanid vom F. 140° C (Wasser) aus.dioxybenzyl) biguanide from a temperature of 140 ° C (water).
Gemäß Beispiel 1 a wird, ausgehend von N-Methylpiperonylaminhydrochlorid und Dicyandiamid, das N1 - Methyl - N1 - (3,4 - methylendioxybenzyl) - biguanidhydrochlorid vom F. 199 bis 201° C (umkristallisiert aus Äthylalkohol) erhalten. Die Ausbeute beträgt 50% der Theorie.According to Example 1a, starting from N-methylpiperonylamine hydrochloride and dicyandiamide, N 1 - methyl - N 1 - (3,4 - methylenedioxybenzyl) biguanide hydrochloride with a melting point of 199 ° to 201 ° C. (recrystallized from ethyl alcohol) is obtained. The yield is 50% of theory.
B e i s ρ j e 1 3B e i s ρ j e 1 3
Gemäß Beispiel 1 a wird, ausgehend von Piperonylaminhydrochlorid und N-Methyl-dicyandiamid, das N1 - (3,4 - Methylendioxybenzyl) - N5 - methylbiguanidhydrochlorid vom F. 190 bis 195° C (umkristallisiert aus Äthylalkohol) erhalten. Die Ausbeute beträgt 10% der Theorie.According to Example 1a, starting from piperonylamine hydrochloride and N-methyl-dicyandiamide, N 1 - (3,4 - methylenedioxybenzyl) - N 5 - methylbiguanide hydrochloride with a melting point of 190 ° to 195 ° C. (recrystallized from ethyl alcohol) is obtained. The yield is 10% of theory.
Claims (1)
Family
ID=
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