CH592102A5 - 3-Pyridyl amino ergoline derivs - for treatment of galactorrhoea, breast cancer, oedema, hypertension, parkinsons disease etc. - Google Patents
3-Pyridyl amino ergoline derivs - for treatment of galactorrhoea, breast cancer, oedema, hypertension, parkinsons disease etc.Info
- Publication number
- CH592102A5 CH592102A5 CH523474A CH523474A CH592102A5 CH 592102 A5 CH592102 A5 CH 592102A5 CH 523474 A CH523474 A CH 523474A CH 523474 A CH523474 A CH 523474A CH 592102 A5 CH592102 A5 CH 592102A5
- Authority
- CH
- Switzerland
- Prior art keywords
- treatment
- formula
- oedema
- hypertension
- breast cancer
- Prior art date
Links
- -1 3-Pyridyl amino Chemical group 0.000 title abstract description 9
- 238000011282 treatment Methods 0.000 title abstract description 5
- 206010006187 Breast cancer Diseases 0.000 title abstract 2
- 208000026310 Breast neoplasm Diseases 0.000 title abstract 2
- 206010017600 Galactorrhoea Diseases 0.000 title abstract 2
- 206010020772 Hypertension Diseases 0.000 title abstract 2
- 206010030113 Oedema Diseases 0.000 title abstract 2
- 208000018737 Parkinson disease Diseases 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical compound O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 abstract 1
- 208000001287 Galactorrhea Diseases 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 208000019695 Migraine disease Diseases 0.000 abstract 1
- 206010036618 Premenstrual syndrome Diseases 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000033228 biological regulation Effects 0.000 abstract 1
- 230000001684 chronic effect Effects 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 230000006651 lactation Effects 0.000 abstract 1
- 206010027599 migraine Diseases 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 241000699800 Cricetinae Species 0.000 description 2
- 241001502500 Trichomonadida Species 0.000 description 2
- 230000003569 amebicidal effect Effects 0.000 description 2
- 230000001857 anti-mycotic effect Effects 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 208000004881 Amebiasis Diseases 0.000 description 1
- 206010001980 Amoebiasis Diseases 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000224421 Heterolobosea Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000005448 Trichomonas Infections Diseases 0.000 description 1
- 206010044620 Trichomoniasis Diseases 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 210000003001 amoeba Anatomy 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000002963 trichomonacidal effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Ergoline derivs. of formula (I) and their salts: (where R = 3-pyridyl, opt. subst. by one or more of the following: halogen, hydroxy, phenoxy, lower alkyl, alkoxy and alkylthio, and -N-R1R2, R1 and R2 = H or lower alkyl) are useful as prophylaxis and for the treatment of physiological lactation, galactorrhea, and breast cancer, treatment of chronic renal nephropathia and inflammation, the regulation of electrolytic and hydric balance, treatment of oedema, hypertension, migraine attacks, pre-menstrual syndrome, and Parkinson's disease.
Description
Die Erfindung betrifft ein Verfahren zur Herstellung neuer heterocyclischer Verbindungen der Formel I
EMI1.1
worin X und B unabhängig voneinander für Sauerstoff, Schwefel oder eine N-R-Gruppe, worin R niederes Alkyl bedeutet, Y und A unabhängig voneinander für Stickstoff oder die CH-Gruppe und n für 1 oder 0 stehen.
Erfindungsgemäss gelangt man zu den Verbindungen der Formel I, indem man eine Verbindung der Formel II,
EMI1.2
worin X, Y und n obige Bedeutung besitzen, mit einer Verbindung der Formel III
EMI1.3
worin A und B obige Bedeutung besitzen und Z für Halogen oder einen Rest der Formel IV,
EMI1.4
worin A und B obige Bedeutung besitzen, steht, umsetzt.
Das erfindungsgemässe Verfahren kann beispielsweise in einem unter den Reaktionsbedingungen inerten Lösungsmittel, z. B. in einem aromatischen Kohlenwasserstoff wie Benzol, vorzugsweise bei Zimmertemperatur ausgeführt werden.
Das Reaktionsprodukt kann aus dem Reaktionsgemisch nach an sich bekannten Methoden isoliert und gegebenenfalls gereinigt werden.
Die durch R dargestellten niederen Alkylgruppen besitzen vorzugsweise 1-4 Kohlenstoffatome und bedeuten insbesondere die Methyl- oder Äthylgruppe.
Die als Ausgangsprodukte benötigten Verbindungen der Formel II können erhalten werden, indem man eine Verbindung der Formel V,
EMI1.5
worin X, Y und n obige Bedeutung besitzen und R1 für niederes Alkyl mit 1H Kohlenstoffatomen steht, mit Hydroxylamin reagieren lässt. Die Reaktion lässt sich unter Verwendung eines unter den Reaktionsbedingungen inerten Lösungsmittels, z. B. eines niederen Alkohols wie Äthanol oder Methanol, ausführen.
Die Verbindungen der Formel III und V sind bekannt oder nach an sich bekannten Verfahren bzw. analog zu den hier beschriebenen oder analog zu an sich bekannten Verfahren herstellbar.
Die Verbindungen der Formel I können auch in ihrer tautomeren Form der Formel Ia
EMI1.6
die Verbindungen der Formel II auch in ihrer tautomeren Form der Formel IIa
EMI1.7
vorliegen, worin X, Y, A, B und n obige Bedeutung besitzen.
Die Verbindungen der Formel I besitzen bei geringer Toxizität interessante pharmakodynamische Eigenschaften und können daher als Heilmittel verwendet werden. Sie entfalten eine Hemmwirkung gegen Bakterien, wie sich durch Untersuchungen in vitro mit dem Agarplattentest unter Verwendung verschiedener Bakterienstämme zeigen lässt. Diese Hemmwirkung wurde ab einer Konzentration von cal. 0,4 bis 50 ,ug/ml festgestellt. Daher können die erfindungsgemässen Verbindungen als Hemmstoffe des Bakterienwachstums verwendet werden.
Als Heilmittel können die Verbindungen der Formel I allein oder in geeigneten Arzneiformen gemeinsam mit anorganischen oder organischen, pharmakologisch indifferenten Hilfsstoffen verabreicht werden. Beispielsweise werden sie als Bestandteil von Kapseln oder Tabletten eingesetzt, wobei die Konzentration in der zubereiteten Form ca. 50 bis 500 mg Wirkstoff pro Einheit der Dosisform betragen kann.
Weiter zeigen die erfindungsgemässen Substanzen auch eine antimykotische Wirksamkeit, wie sich durch Untersuchungen in vitro unter Verwendung von Myceten (z. B.
Trichophyton quinckeaneum, Aspergillus fumigatus u. a. m.) zeigen lässt. Diese Wirksamkeit wurde ab einer Hemmkonzentration von ca. 10 bis 100 pg/ml festgestellt. Daher können die erfindungsgemässen Verbindungen als Antimykotika verwendet werden.
Als Heilmittel können die neuen Verbindungen der Formel I allein oder in geeigneten Arzneiformen gemeinsam mit anorganischen oder organischen, pharmakologisch indifferenten Hilfsstoffen verabreicht werden. Beispielsweise werden sie als Bestandteil einer Salbe eingesetzt, wobei die Konzentration in der Salbe ca. 5 bis 50 mg Wirkstoff pro g Salbe betragen kann.
Ausserdem entfalten die Verbindungen der Formel I auch eine abtötende Wirkung gegen Trichomonaden und Amöben, wie sich durch in vitro Untersuchungen mit dem Reihenverdünnungstest wie auch in vivo Versuchen in der Maus und im Hamster zeigen lässt.
Die im CACH-Medium [Müller et al., Angew. Parasit.
11, 170-176 (1970)1 geprüfte Trichomonadenwirksamkeit beginnt bei ca. 3 ,ug/ml. Im TTY-SB-Medium [Diamond L. S., J. Parasitol. 54, 715-719 (1968)1 erwiesen sich die Substanzen im Konzentrationsbereich ab ca. 12 ug/ml amöbizid. Die trichomonazide Wirksamkeit wurde in der Maus und die amöbizide Wirkung in Ratte und Hamster geprüft.
Die Substanzen erscheinen zur chemotherapeutischen Behandlung der verschiedenen Formen der Trichomoniasis und Amöbiasis geeignet, wobei ihre systemische Wirkung von besonderem Vorteil angesehen wird.
Als Heilmittel können die Verbindungen der Formel I allein oder in geeigneten Arzneiformen gemeinsam mit anorganischen oder organischen, pharmakologisch indifferenten Hilfsstoffen verabreicht werden. Beispielsweise werden sie als Bestandteil von Kapseln, Tabletten oder einer Injektionslösung eingesetzt, wobei die Kapseln oder Tabletten z. B. 10 bis 500 mg Wirkstoff pro Kapsel oder Tablette enthalten können.
In den nachfolgenden Beispielen, die die Erfindung näher erläutern, ihren Umfang aber in keiner Weise einschränken sollen, erfolgen alle Temperaturangaben in Celsiusgraden.
Beispiel 1
5-Nitro-2-thienyl-O-(5-nitro-2-thienylacryloyl) -oxamidin
3 g 5-Nitro-2-thienylacrylsäurechlorid und 2,58 g 5 Nitro-2-thienyloxamidin werden in 100 ml Benzol gelöst und 24 Stunden bei Zimmertemperatur gerührt. Das dabei entstehende gelbe Kristallisat wird abgesaugt, mit Benzol gewaschen und dann aus Äthanol/Wasser umkristallisiert.
Fp. 198-2000.
Analog wie in Beispiel 1 beschrieben, können auch folgende Verbindungen der Formel I erhalten werden (Beispiel 2 bis 4):
Beispiel 2
5-Nitro-2-thiazolyl-O-(5 -nitro-2-furylacryloyl)-oxamidin
Fp. 199-2010.
Beispiel 3
5-Nitro-2-furyl-O-(5-nitro-2-furylacryloyl)-oxamidin
Fp. 205-2060.
Beispiel 4
5-Nitro-2-furylacryl-O-(5-nitro-2-furylacryloyl)-oxamidin
Fp. 209-2100.
The invention relates to a process for the preparation of new heterocyclic compounds of the formula I.
EMI1.1
in which X and B independently of one another represent oxygen, sulfur or an N-R group, in which R is lower alkyl, Y and A independently of one another represent nitrogen or the CH group and n represents 1 or 0.
According to the invention, the compounds of the formula I are obtained by adding a compound of the formula II,
EMI1.2
wherein X, Y and n have the above meanings, with a compound of the formula III
EMI1.3
wherein A and B have the above meaning and Z is halogen or a radical of the formula IV,
EMI1.4
where A and B have the above meaning, is, is converted.
The inventive method can, for example, in a solvent inert under the reaction conditions, eg. B. in an aromatic hydrocarbon such as benzene, preferably at room temperature.
The reaction product can be isolated from the reaction mixture by methods known per se and, if necessary, purified.
The lower alkyl groups represented by R preferably have 1-4 carbon atoms and are in particular the methyl or ethyl group.
The compounds of the formula II required as starting materials can be obtained by adding a compound of the formula V,
EMI1.5
where X, Y and n have the above meaning and R1 is lower alkyl with 1H carbon atoms, can react with hydroxylamine. The reaction can be carried out using a solvent which is inert under the reaction conditions, e.g. B. a lower alcohol such as ethanol or methanol, run.
The compounds of the formulas III and V are known or can be prepared by processes known per se or analogously to those described here or analogously to processes known per se.
The compounds of the formula I can also be used in their tautomeric form of the formula Ia
EMI1.6
the compounds of the formula II also in their tautomeric form of the formula IIa
EMI1.7
are present, in which X, Y, A, B and n have the above meanings.
The compounds of the formula I have interesting pharmacodynamic properties with low toxicity and can therefore be used as medicaments. They develop an inhibitory effect against bacteria, as can be shown by studies in vitro with the agar plate test using different bacterial strains. This inhibitory effect was determined from a concentration of cal. 0.4 to 50 μg / ml. Therefore, the compounds of the present invention can be used as bacterial growth inhibitors.
As medicaments, the compounds of the formula I can be administered alone or in suitable pharmaceutical forms together with inorganic or organic, pharmacologically indifferent auxiliaries. For example, they are used as a component of capsules or tablets, the concentration in the prepared form being approximately 50 to 500 mg of active ingredient per unit of the dosage form.
Furthermore, the substances according to the invention also show an antimycotic activity, as shown by in vitro studies using mycetes (e.g.
Trichophyton quinckeaneum, Aspergillus fumigatus u. a. m.) shows. This effectiveness was determined from an inhibitory concentration of approx. 10 to 100 pg / ml. Therefore, the compounds according to the invention can be used as antimycotics.
As medicaments, the new compounds of the formula I can be administered alone or in suitable pharmaceutical forms together with inorganic or organic, pharmacologically indifferent auxiliary substances. For example, they are used as a constituent of an ointment, the concentration in the ointment being about 5 to 50 mg of active ingredient per g of ointment.
In addition, the compounds of the formula I also develop a killing effect against trichomonads and amoebas, as can be shown by in vitro studies with the serial dilution test and in vivo tests in mice and hamsters.
The in the CACH medium [Müller et al., Angew. Parasite.
11, 170-176 (1970) 1 tested trichomonads effectiveness begins at about 3. ug / ml. In TTY-SB medium [Diamond L.S., J. Parasitol. 54, 715-719 (1968) 1, the substances proved to be amoebicidal in the concentration range from about 12 μg / ml. The trichomonacidal activity was tested in the mouse and the amoebicidal activity in the rat and hamster.
The substances appear to be suitable for the chemotherapeutic treatment of the various forms of trichomoniasis and amebiasis, their systemic action being considered to be particularly advantageous.
As medicaments, the compounds of the formula I can be administered alone or in suitable pharmaceutical forms together with inorganic or organic, pharmacologically indifferent auxiliaries. For example, they are used as a component of capsules, tablets or an injection solution, the capsules or tablets z. B. may contain 10 to 500 mg of active ingredient per capsule or tablet.
In the following examples, which explain the invention in greater detail but are not intended to limit its scope in any way, all temperatures are given in degrees Celsius.
example 1
5-nitro-2-thienyl-O- (5-nitro-2-thienylacryloyl) oxamidine
3 g of 5-nitro-2-thienyl acrylic acid chloride and 2.58 g of 5-nitro-2-thienyloxamidine are dissolved in 100 ml of benzene and stirred for 24 hours at room temperature. The resulting yellow crystals are filtered off with suction, washed with benzene and then recrystallized from ethanol / water.
M.p. 198-2000.
Analogously to that described in Example 1, the following compounds of the formula I can also be obtained (Examples 2 to 4):
Example 2
5-nitro-2-thiazolyl-O- (5-nitro-2-furylacryloyl) oxamidine
M.p. 199-2010.
Example 3
5-nitro-2-furyl-O- (5-nitro-2-furylacryloyl) oxamidine
M.p. 205-2060.
Example 4
5-nitro-2-furylacryloyl-O- (5-nitro-2-furylacryloyl) oxamidine
Mp 209-2100.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH523474A CH592102A5 (en) | 1974-04-16 | 1974-04-16 | 3-Pyridyl amino ergoline derivs - for treatment of galactorrhoea, breast cancer, oedema, hypertension, parkinsons disease etc. |
| US05/566,355 US4004011A (en) | 1974-04-16 | 1975-04-09 | 3-Pyridylamine substituted ergolines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH523474A CH592102A5 (en) | 1974-04-16 | 1974-04-16 | 3-Pyridyl amino ergoline derivs - for treatment of galactorrhoea, breast cancer, oedema, hypertension, parkinsons disease etc. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH592102A5 true CH592102A5 (en) | 1977-10-14 |
Family
ID=4290185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH523474A CH592102A5 (en) | 1974-04-16 | 1974-04-16 | 3-Pyridyl amino ergoline derivs - for treatment of galactorrhoea, breast cancer, oedema, hypertension, parkinsons disease etc. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH592102A5 (en) |
-
1974
- 1974-04-16 CH CH523474A patent/CH592102A5/en not_active IP Right Cessation
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|---|---|---|---|
| PL | Patent ceased | ||
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