DE2028330C3 - Thiophosphorimide-isoquinoline adducts and agents containing them - Google Patents
Thiophosphorimide-isoquinoline adducts and agents containing themInfo
- Publication number
- DE2028330C3 DE2028330C3 DE19702028330 DE2028330A DE2028330C3 DE 2028330 C3 DE2028330 C3 DE 2028330C3 DE 19702028330 DE19702028330 DE 19702028330 DE 2028330 A DE2028330 A DE 2028330A DE 2028330 C3 DE2028330 C3 DE 2028330C3
- Authority
- DE
- Germany
- Prior art keywords
- adducts
- thiophosphoric acid
- isoquinoline
- thiophosphorimide
- agents containing
- 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
- RYYWUUFWQRZTIU-UHFFFAOYSA-N thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 12
- INVGWHRKADIJHF-UHFFFAOYSA-N Sanguinarin Chemical compound C1=C2OCOC2=CC2=C3[N+](C)=CC4=C(OCO5)C5=CC=C4C3=CC=C21 INVGWHRKADIJHF-UHFFFAOYSA-N 0.000 claims description 8
- YBHILYKTIRIUTE-UHFFFAOYSA-N Berberine Chemical compound C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 YBHILYKTIRIUTE-UHFFFAOYSA-N 0.000 claims description 6
- 229940093265 Berberine Drugs 0.000 claims description 6
- 229930015400 berberine Natural products 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 241001233914 Chelidonium majus Species 0.000 claims description 4
- 229940084560 sanguinarine Drugs 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 5
- 229930013930 alkaloids Natural products 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- CKTNHGVJKUQEBM-UHFFFAOYSA-N ethylazanide Chemical compound CC[NH-] CKTNHGVJKUQEBM-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WDFZWSZNOFELJY-UHFFFAOYSA-N Arene oxide Chemical compound C1=CC=CC2OC21 WDFZWSZNOFELJY-UHFFFAOYSA-N 0.000 description 1
- 210000004369 Blood Anatomy 0.000 description 1
- 210000000481 Breast Anatomy 0.000 description 1
- 210000003679 Cervix Uteri Anatomy 0.000 description 1
- 210000003238 Esophagus Anatomy 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 210000002149 Gonads Anatomy 0.000 description 1
- 229940068560 Greater Celandine Drugs 0.000 description 1
- 210000000867 Larynx Anatomy 0.000 description 1
- 230000036740 Metabolism Effects 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N Nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 210000002307 Prostate Anatomy 0.000 description 1
- 210000003932 Urinary Bladder Anatomy 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 201000009030 carcinoma Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000003807 isoquinoline alkaloid derivatives Chemical class 0.000 description 1
- 229930013397 isoquinoline alkaloids Natural products 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000035786 metabolism Effects 0.000 description 1
- 238000001668 nucleic acid synthesis Methods 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000241 respiratory Effects 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- -1 thiophosphoric acid ethylene imide Chemical class 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 229940048102 triphosphoric acid Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
Die Erfindung betrifft den in den Ansprüchen definierten Gegenstand. Bei dieser Umsetzung ist es zweckmäßig, als organische Lösungsmittel Benzol, Chloroform oder Dioxan zu verwenden.The invention relates to the subject matter defined in the claims. In this implementation it is expedient to use benzene, chloroform or dioxane as the organic solvent.
Die wirksamsten Substanzen sind Thiophosphorsäure-di-(äthylenimido)-N-berberin-äthylamid, Thiophosphorsäure-tri-(N-sanguinarin)-äthylamid und Thiophosphorsäuretriäthylenimid-derivate von Alkaloiden der Isochinolinreihe des großen Schöllkrautes.The most effective substances are thiophosphoric acid-di- (ethyleneimido) -N-berberine-ethylamide, Thiophosphoric acid tri- (N-sanguinarine) ethylamide and thiophosphoric acid triethyleneimide derivatives of alkaloids the isoquinoline series of the greater celandine.
Die erfindungsgemäßen Addukte werden hergestellt, indem Thiophosphorsäure-tri(äthylenimid) in einem organischen Lösungsmittel bei erhöhter Temperatur, insbesondere der Siedetemperatur des Lösungsmittels, mit Sanguinarin, Berberin oder einem Isochinolinalkaloid des Schöllkrauts umgesetzt wird.The adducts according to the invention are prepared by thiophosphoric acid tri (ethyleneimide) in an organic solvent at an elevated temperature, in particular the boiling point of the solvent, with sanguinarine, berberine or an isoquinoline alkaloid from celandine.
Die erhaltenen Addukte weiden dann durch Entfernen des Lösungsmittels aus dem Reaktionsgemisch, Auswaschen der nicht umgesetzten Ausgangsprodukte und Umkristallisation isoliert.The adducts obtained then graze by removing the solvent from the reaction mixture, Washing out of the unreacted starting materials and recrystallization isolated.
Die Verbindungen finden Anwendung zur Behandlung der Geschwülste von Mamma, weiblicher Keimdrüse, Gebärmutterhals, Harnblase, Prostata, Kehlkopf, Speiseröhre und anderer Lokalisationen. Ihr Wirkungsmechanismus besteht in der Einwirkung auf die Mechanismen des Zellmetabolismus, welche zur Störung der Nukleinsäuresynthese und zur Erhöhung der Intensität der aeroben Atmungsphase führen.The compounds are used for the treatment of tumors of the breast, female gonad, Cervix, urinary bladder, prostate, larynx, esophagus and other locations. Her Mechanism of action consists in the action on the mechanisms of cell metabolism, which lead to Disturbance of nucleic acid synthesis and lead to an increase in the intensity of the aerobic respiratory phase.
Erfindungsgemäß enthalten die Arzneimittel den Wirkstoff in einem üblichen pharmazeutischen Träger, insbesondere in Lösung oder in einer üblichen Salben- oder Suppositoriengrundlage. Vorzugsweise wird ein Lösungsmittel folgender Zusammensetzung in Gewichtsteilen verwendet: Wasser — 1,5; PoIyäthylenglykol mit einem Molekulargewicht von 400—1,5; Dimethylsulfoxid— 2. Es ist zweckmäßig, die Lösung mit einem Gehalt an Wirkstoff von 0,3—0,5 Gew.-% zu verwenden.According to the invention, the medicaments contain the active ingredient in a conventional pharmaceutical carrier, especially in solution or in a conventional ointment or suppository base. Preferably a solvent of the following composition is used in parts by weight: water - 1.5; Polyethylene glycol with a molecular weight of 400-1.5; Dimethyl sulfoxide - 2. It is advisable to to use the solution with an active ingredient content of 0.3-0.5% by weight.
Die erfindungsgemäßen Arzneimittel zeigen eine wesentlich stärkere Hemmung des Wachstums verschiedener Karzinome, als die zur Herstellung der Addukte verwendeten Alkaloide.The medicaments according to the invention show a much stronger inhibition of the growth of various Carcinomas, as the alkaloids used to make the adducts.
Darüber hinaus hemmen sie sogar in den maximal verträglichen Dosen die Blutbildung nicht. Außerdem sind sie weniger toxisch als die Ausgangsmaterialien.In addition, they do not inhibit blood formation even in the maximum tolerated doses. Besides that they are less toxic than the starting materials.
7,5 Mmol Sanguinarin (F. 267° C) und 14,27 Mmol Thiophosphorsäuretriäthylenimid werden in 700 ml Benzol gelöst, und das Gemisch wird in einem Kolben mit Rückflußkühler während 2 Stunden gekocht. Das erhaltene Gemisch wird mit der Aktivkohle entfärbt7.5 mmoles of sanguinarine (m.p. 267 ° C) and 14.27 mmoles Thiophosphorsäuretriethylenimid are dissolved in 700 ml of benzene, and the mixture is in a flask boiled with reflux condenser for 2 hours. The mixture obtained is decolorized with the activated charcoal
»5 und das Lösungsmittel verdampft. Der trockene Rückstand wird sorgfältig mit Äther gewaschen, um nicht umgesetzte Ausgangsstoffe zu entfernen. Man erhält 1,5 g Thiophosphorsäurc-tri-(N-sangiiinarin)-äthylamid als gelblichen kristallinen Stoff, der in Benzol, Chloroform, Dimethylformamid, Dichloräthan gut, in Wasser schwer, in KKuiger Salzsäure beim Erwärmen löslich, in Methanol und Äther unlöslich ist. Die Ausbeute beträgt 50,8 Gew.-"/« der Theorie. »5 and the solvent evaporates. The dry residue is carefully washed with ether in order to remove unreacted starting materials. 1.5 g of thiophosphoric acid tri- (N-sangiiinarine) ethylamide are obtained as a yellowish crystalline substance which is good in benzene, chloroform, dimethylformamide, dichloroethane, difficult in water, soluble in KKuiger hydrochloric acid when heated, and insoluble in methanol and ether . The yield is 50.8% by weight of theory.
F. 189—191° C (aus einem Gemisch von Chloroform und Methanol). Das Absorptionsmaximum: 238, 338, 398 und 407 nm. C00H17NnO1-PS. Verhältnis von Sanguinarin zu Triphosphorsäuretriäthylenimid = 3:1.189-191 ° C (from a mixture of chloroform and methanol). The absorption maximum: 238, 338, 398 and 407 nm. C 00 H 17 N n O 1 -PS. Ratio of sanguinarine to triphosphoric acid triethylenimide = 3: 1.
Analyse:Analysis:
Berechnet: S 2,59, N 6,79, P 2,50,-C 64,07,Calculated: S 2.59, N 6.79, P 2.50, -C 64.07,
H 4,64%;
gefunden: S 2,70, 2,71, N 6,82, 6,90, P 2,45,H 4.64%;
found: S 2.70, 2.71, N 6.82, 6.90, P 2.45,
2,62, C 63,90, 63,87, H 4,60, 4,7 M/o.2.62, C 63.90, 63.87, H 4.60, 4.7 M / o.
8,86 Mmol Berberin und 13,5 Mmol Thiophosphorsäurelriäthylenimid werden in 600 ml wasserfreiem Dioxan in einem Kolben mit Rückflußkühler während 2 Stunden gekocht. Das erhaltene Gemisch wird mit Aktivkohle entfärbt und das Lösungsmittel unter Vakuum von 10 Torr verdampft. Man wäscht den trockenen Rückstand mit Äther und Chloroform und erhält 3,3 g Thiophosphorsäure-di-(äthylenimido)-N-berberinäthylamid, einen dunkelgelben kristallinen Stoff, der beim Erwärmen in der Salzsäure gut, in gewöhnlichen organischen Lösungsmitteln schwer löslich ist. Die Ausbeute beträgt 97 Gew.-% der Theorie.8.86 mmoles of berberine and 13.5 mmoles of thiophosphoric acid triethylenimide are boiled in 600 ml of anhydrous dioxane in a flask with a reflux condenser for 2 hours. The resulting mixture is decolorized with activated charcoal and the solvent evaporated under vacuum of 10 Torr. One washes the dry residue with ether and chloroform and receives 3.3 g of thiophosphoric acid-di- (ethyleneimido) -N-berberinäthylamid, a dark yellow crystalline substance which, when heated, works well in hydrochloric acid, in common organic solvents is difficult to dissolve. The yield is 97% by weight of theory.
F. 135° C (aus dem Gemisch von Benzol und Dimethylsulfoxid). Mp 135 ° C (from the mixture of benzene and dimethyl sulfoxide).
C H N O PSC H N O PS
Verhältnis von Berberin zu Thiophosphorsäuretriäthylenimid = 1:1.Ratio of berberine to thiophosphoric acid triethylenimide = 1: 1.
Analyse:Analysis:
Berechnet: S 5,91, N 10,37, P 10,33, C 57,55,Calculated: S 5.91, N 10.37, P 10.33, C 57.55,
H 5,76 ·/„;H 5.76 · / ";
gefunden: S 5,90, 5,79, N 10,52, 10,54, P 10,41, 10,39, C 57,40, H 5,84 »/0.found: S 5.90, 5.79, N 10.52, 10.54, P 10.41, 10.39, C 57.40, H 5.84 »/ 0.
Das Absorptionsmaximum: 231, 282, 373 nm.The absorption maximum: 231, 282, 373 nm.
-Beispiel *3.-Example * 3.
3,5 g der aus dem wäßrigen Extrakt von Chelidonium majus L. isolierten Alkaloide (Durchschnittsmolekulargewicht331) und 3,8 g (20,1 Mmol) Thiophosphorsäureäthylenimid löst man in 60 ml Chloroform und kocht in einem Kolben mit RückflußküHler während .2 Stunden. Das erhaltene Produkt wird mit Aktivkohle entfärbt und das Lösungsmittel verdampft. Der trockene Rückstand wird sorgfältig mit Äther gewaschen, um nicht umgesetzte Ausgangsstoffe zu entfernen. Man erhält 1,45 g Endprodukt von hellbrauner Farbe, das in Chloroform, Dimethylsulfoxid, Dimethylformamid gut, in Dichloräthan, Dioxan und Methanol schwer löslich und in Wasser und Äther unlöslich ist. Die Ausbeute beträft ^4 53.5 g of the alkaloids (average molecular weight 331) isolated from the aqueous extract of Chelidonium majus L. and 3.8 g (20.1 mmol) of thiophosphoric acid ethylene imide is dissolved in 60 ml of chloroform and boiled in a flask with a reflux condenser for .2 hours. The product obtained is decolorized with activated charcoal and the solvent is evaporated. The dry residue is carefully washed with ether to remove any unreacted starting materials to remove. 1.45 g of end product of light brown color are obtained, which is dissolved in chloroform, dimethyl sulfoxide, Dimethylformamide good, sparingly soluble in dichloroethane, dioxane and methanol and in water and ether is insoluble. The yield is ^ 4 5
Gew.-'Vii. Für das Durchschnittsmolekularucwicht von etwa 1120:Wt .- 'Vii. For the average molecular weight of around 1120:
Analyst:Analyst:
Berechnet: S 2,85, N 7,50",O;
gefunden: S 2,82, N 7,60"/.,.Calculated: S 2.85, N 7.50 ", O;
found: S 2.82, N 7.60 "/.,.
Das Absorptionsmaximum: 284 nm. Verhältnis Alkaloide zu Thiophosphorsäuretriäthylenimid = 3:1.The absorption maximum: 284 nm. Ratio of alkaloids to thiophosphoric acid triethyleneimide = 3: 1.
Die Reaktion wird analog Beispiel 3 durchgeführt; als organisches Lösungsmittel wird Benzol verwendet.The reaction is carried out analogously to Example 3; benzene is used as the organic solvent.
Die Ausbeute an Endprodukt beträgt 35 Gew.-0/». Für das Durchschnittsmolekulargewicht von etwa 1180:The yield of the final product is 35 weight 0 /. " For the average molecular weight of around 1180:
Berechnet: S 2,72, N 7,12%;Calculated: S 2.72, N 7.12%;
gefunden: S 2,64, 2,62, N 7,30, 7,251Vn.found: S 2.64, 2.62, N 7.30, 7.25, 1 Vn.
Das Absoiptionsmaximum: 271, 375 nm.
Verhältnis Alkaloide zu Thiophosphorsäuretriüthylenimid -— 3:1.The absorption maximum: 271, 375 nm.
Ratio of alkaloids to thiophosphoric acid trietylenimide - 3: 1.
0,03 Mmol Berberin (Schmelzpunkt ungefähr 1400C) und 0,03 Mmol Thiophosphorsäuretriäthylenimid werden 15 Stunden in 400 ml Methanol gekocht. Das erhaltene Gemisch wird mit Aktivkohle entfärbt und das Lösungsmittel verdampft. Der Rückstand wird mit Äther gewaschen und 9,0 g Thiophosphorsäurstri-(N-beiberinäthylamid) als braunes Produkt erhalten. F. 186 bis 188° C unter Zersetzung. Verhältnis von Berberin zu Thiophosphorsäuretriäthylenimid = 3:1.0.03 mmol berberine (melting point about 140 0 C) and 0.03 mmol Thiophosphorsäuretriäthylenimid are boiled for 15 hours in the 400 ml of methanol. The mixture obtained is decolorized with activated charcoal and the solvent is evaporated. The residue is washed with ether and 9.0 g of thiophosphoric acid tri- (N-beiberinäthylamid) are obtained as a brown product. F. 186 to 188 ° C with decomposition. Ratio of berberine to thiophosphoric acid triethylenimide = 3: 1.
C0nH(JJiN11O15PS, Absorptionsmaximum 228, 260, 341 nm.C 0n H (JJiN 11 O 15 PS, absorption maximum 228, 260, 341 nm.
Berechnet: S 257, N6,73°/o;
gefunden: S 2,52, N 6,50%.Calculated: S 257, N 6.73%;
found: S 2.52, N 6.50%.
Claims (2)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1330542 | 1969-06-16 | ||
| SU1330542A SU368254A1 (en) | 1969-06-16 | 1969-06-16 | Method of producing compounds of thiophosphamide with alkaloids of a large cleaner |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2028330A1 DE2028330A1 (en) | 1971-05-27 |
| DE2028330B2 DE2028330B2 (en) | 1977-02-03 |
| DE2028330C3 true DE2028330C3 (en) | 1977-09-15 |
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