DE1792811C2 - "Drugs with a coronary vasodilator effect" - Google Patents
"Drugs with a coronary vasodilator effect"Info
- Publication number
- DE1792811C2 DE1792811C2 DE19661792811 DE1792811A DE1792811C2 DE 1792811 C2 DE1792811 C2 DE 1792811C2 DE 19661792811 DE19661792811 DE 19661792811 DE 1792811 A DE1792811 A DE 1792811A DE 1792811 C2 DE1792811 C2 DE 1792811C2
- Authority
- DE
- Germany
- Prior art keywords
- trapymin
- drugs
- coronary vasodilator
- vasodilator effect
- effect
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
Description
C2H5 C 2 H 5
CH3 CH 3
Der Wirkstoff ist unter dem Freinahmen Trapymin bekannt.The active ingredient is known under the brand name Trapymin.
Trapymin ist ein wertvoller Arzneistoff, der im Tierversuch eine in dieser Verbindungsklasse noch nicht beschriebene und bekannten Verbindungen gleicher Wirkungsrichtung überlegene koronargefäßerweiternde Wirkung zeigt. Er kann in der Humanmedizin zur Behandlung von Patienten mit Anginapectoris Syndrom eingesetzt werden.Trapymin is a valuable drug that has not yet been found in this class of compounds in animal experiments described and known compounds with the same direction of action are superior coronary vasodilators Shows effect. It can be used in human medicine to treat patients with angina pectoris syndrome can be used.
Es ist bekannt, diese Verbindung nach H. Kano, Y. Makisumi, Chem. Pharmac. Bull. (Tokyo), Bd. 6 (1958), S. 583 bis 586, aus 5-Methyl-7-chlor-s-triazolo(l,5-a)pyrimidin und Diäthylamin in 96 bis lOOprozentiger alkoholischer Lösung herzustellen.It is known that this compound according to H. Kano, Y. Makisumi, Chem. Pharmac. Bull. (Tokyo), Vol. 6 (1958), pp. 583 to 586, from 5-methyl-7-chloro-s-triazolo (1,5-a) pyrimidine and to prepare diethylamine in 96 to 100 percent alcoholic solution.
Das 5-Methyl-7-diäthylamino-s-triazol-(1 ,5-a)pyrimidin bewirkt eine langanhaltende Erschlaffung der glatten Gefäßmuskulatur und führt zu einer spezifischen Mehrdurchblutung der Koronargefäße des Herzens. Daneben zeigt die Verbindung an isolierten Sinusknqten- und Papillarmuskelpräparaten positiv chronotrope und inotrope Effekte. Klinische Untersuchungen haben ergeben, daß die Verbindung weniger eine Verbesserung der Kontraktionsform bewirkt, sondern sich als ein typischer Koronardilatator erweist.The 5-methyl-7-diethylamino-s-triazol- (1, 5-a) pyrimidine causes a long-lasting relaxation of the smooth vascular muscles and leads to a specific increased blood flow to the coronary vessels of the heart. In addition, the compound shows positive chronotropic effects on isolated sinus knot and papillary muscle specimens and inotropic effects. Clinical studies have shown that the compound is less of an improvement the form of contraction causes, rather than a typical coronary dilator proves.
Das Arzneimittel kann in üblichen Darreichungsformen vorliegen und oral oder parenteral, vorzugsweise intravenös gegeben werden.The medicament can be present in the usual dosage forms and orally or parenterally, preferably given intravenously.
Im pharmakologischen Versuch am isolierten Langendorff-Herzen erwies sich Trapymin wirksamer als Theophillin-Äthylendiamin.In the pharmacological experiment on the isolated Langendorff heart, Trapymin proved to be more effective than Theophillin-ethylenediamine.
K. Oguro et al., Arzneimittelforschung, Bd. 24 (1974), S. 911, untersuchten die hämodynamische Wirkung vonK. Oguro et al., Arzneimittelforschung, 24: 911 (1974) examined the hemodynamic effect of
Trapymin im Vergleich zu Papaverin und Theophillin-Ä:hyleiidiamin. Unter anderen wurde der dosisabhängige Effekt von Trapymin auf die Koronardurchblutung und die Durchblutung von Nieren und Femoralis im Vergleich zu Theophyllin-Äthylendiamin untersucht Die vasodilatierende Wirkung von Trapymin war etwa lOmal stärker als die von Theophillin-Äthylendiamin.Trapymine compared to papaverine and theophilline-Ä: hyleiidiamin. Among other things, the dose-dependent effect of trapymin on coronary blood flow was investigated and examined kidney and femoral blood flow in comparison to theophylline-ethylenediamine The vasodilating effect of trapymin was about ten times stronger than that of theophillin-ethylenediamine.
Im Rahmen von klinischen Untersuchungen bei Angina pectoris-Patienten (n=5\) wurde Trapymin gegenüber Prenylamin und Dipyridamol von der Mehrzahl der Patienten als subjektiv besser wirksam bezeichnet; vgl. P. Dittrich et aL, Das deutsche Gesundheitsweser., Bd. 36/1971.In the course of clinical studies in angina pectoris patients (n = 5 \) Trapymin was described by the majority of patients as being subjectively more effective than prenylamine and dipyridamole; see P. Dittrich et al, Das deutsche Gesundheitsweser., Vol. 36/1971.
Neben der koronardurchblutungsfördernden Wirkung wies bereits F. Hackel, Medicamentum, Berlin, Bd. 12 (1971), S. 228, auf den günstigen Effekt von Trapymin auf die periphere Hämodynamik hin. Mit Trapymin konnte bei Gefäßverschlüssen im Becken und Oberschenkelbereich eine signifikante und stärkere Erhöhung der Extremitätendurchblutung distal von Verschlüssen und Stenosen erzielt werden als mit Dipyridamol.In addition to the coronary blood flow-promoting effect already pointed out F. Hackel, Medicamentum, Berlin, vol. 12 (1971), p. 228, on the beneficial effect of trapymin on peripheral hemodynamics. With trapymin was able to show a significant and greater increase in vascular occlusions in the pelvis and thigh area blood flow to the extremities can be achieved distal from occlusions and stenoses than with Dipyridamole.
Die in der folgenden Tabelle zusammengestellten oralen LD5O-Werte zeigen für Trapymin eine geringere akute Toxizität als Theophillin-Äthylendiamin. Jedoch ist die akute Toxizität von Trapymin stärker als die von Dipyridamol, das jedoch nur als möglicherweise wirksam klassifiziert wird; vgl. Physicians Desk Reference, 1979, S. 671.The results summarized in the following table oral LD 5 O values show for Trapymin a lower acute toxicity than theophylline-ethylenediamine. However, the acute toxicity of trapymin is greater than that of dipyridamole, which, however, is only classified as possibly effective; See Physicians Desk Reference, 1979, p. 671.
Akute Toxizitätacute toxicity
TrapyminTrapymin
DipyridamolDipyridamole
80% Theophyllin + 20% Äthylcndiamin80% theophylline + 20% ethyl cndiamine
LD50 oral Maus,
Ratte
710-750 mg/kgLD 50 oral mouse,
rat
710-750 mg / kg
LD50 oral Maus,
Ratte
235-380 mg/kgLD 50 oral mouse,
rat
235-380 mg / kg
Ratte MausRat mouse
8 400 mg/kg (2) 447,6 mg/kg8,400 mg / kg (2) 447.6 mg / kg
8,4 g 5-Methyl-7-chlor-s-triazolo(l,5-a)pyrimidin werden in 30 ml Wasser suspendiert umi mit 7,3 g Diäthylamin versetzt. Nach 2stündigem Erwärmen unter Rühren wird alkalisch gemacht, das Amin in Chloroform aufgenommen und unter vermindertem Druck eingeengt. Der Rückstand wird aus n-Hcptan umkristallisiert. Man erhält 8,1 g des 5-Methyl-7-diäthylämino-s-triazolo(l,5-a)pyrimidins vom F. 103 bis 1040C. Das in üblicher Weise hergestellte Hydrochlorid hat einen F. von 212° C.8.4 g of 5-methyl-7-chloro-s-triazolo (l, 5-a) pyrimidine are suspended in 30 ml of water and 7.3 g of diethylamine are added. After 2 hours of heating with stirring, the mixture is made alkaline, the amine is taken up in chloroform and concentrated under reduced pressure. The residue is recrystallized from n-Hcptane. This gives 8.1 g of 5-methyl-7-diäthylämino-s-triazolo (l, 5-a) pyrimidine to 104 0 C. The hydrochloride produced in the conventional manner has a melting 103 F. of 212 ° C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19661792811 DE1792811C2 (en) | 1966-10-03 | 1966-10-03 | "Drugs with a coronary vasodilator effect" |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19661792811 DE1792811C2 (en) | 1966-10-03 | 1966-10-03 | "Drugs with a coronary vasodilator effect" |
| DEV0032057 | 1966-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1792811C2 true DE1792811C2 (en) | 1982-12-30 |
Family
ID=25756042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661792811 Expired DE1792811C2 (en) | 1966-10-03 | 1966-10-03 | "Drugs with a coronary vasodilator effect" |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1792811C2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0500136A1 (en) * | 1991-02-22 | 1992-08-26 | Egis Gyogyszergyar | 1,2,4-Triazolo[1,5-a]pyrimidine derivatives, a process for preparing them as well as medicaments containing them and the use of them |
-
1966
- 1966-10-03 DE DE19661792811 patent/DE1792811C2/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0500136A1 (en) * | 1991-02-22 | 1992-08-26 | Egis Gyogyszergyar | 1,2,4-Triazolo[1,5-a]pyrimidine derivatives, a process for preparing them as well as medicaments containing them and the use of them |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| 8110 | Request for examination paragraph 44 | ||
| 8136 | Disposal/non-payment of the fee for publication/grant | ||
| AC | Divided out of |
Ref country code: DE Ref document number: 1620694 Format of ref document f/p: P |
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| D2 | Grant after examination |