NL7906029A - PROCESS FOR PREPARING DERIVATIVES OF PYRAZOLIDINE-DIONE AND PREPARING A MEDICAMENT - Google Patents
PROCESS FOR PREPARING DERIVATIVES OF PYRAZOLIDINE-DIONE AND PREPARING A MEDICAMENT Download PDFInfo
- Publication number
- NL7906029A NL7906029A NL7906029A NL7906029A NL7906029A NL 7906029 A NL7906029 A NL 7906029A NL 7906029 A NL7906029 A NL 7906029A NL 7906029 A NL7906029 A NL 7906029A NL 7906029 A NL7906029 A NL 7906029A
- Authority
- NL
- Netherlands
- Prior art keywords
- preparing
- dione
- pyrazolidine
- derivatives
- medicament
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
- C07D231/36—Oxygen atoms with hydrocarbon radicals, substituted by hetero atoms, attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
W' -1- 20860/JD/tj \W '-1- 20860 / JD / tj \
Aanvrager: Synthélabo, Parijs-Cedex, Frankrijk.Applicant: Synthélabo, Paris-Cedex, France.
Korte aanduiding: Werkwijze voor het bereiden van derivaten van pyrazo-lidine-dione en het bereiden van een medicament.Short designation: Process for the preparation of derivatives of pyrazo-lidin-dione and the preparation of a medicament.
5 De onderhavige uitvinding, heeft betrekking op een werkwijze voor het bereiden van derivaten van pyrazolidine-dione; en ook betrekking op een werkwijze voor het bereiden van een medicament.The present invention relates to a process for preparing derivatives of pyrazolidine-dione; and also relates to a method of preparing a medicament.
De derivaten, bereid volgens de werkwijze van de onderhavige uitvinding, beantwoorden aan de formule I van het-formuleblad, waarbij en 10 Rg e^> onafhankelijk van elkaar, een waterstofatoom, een alkylgroep met 1-6 koolstofatomen vertegenwoordigen, of waarbij NR^R^ samen een heterocyclische verbinding vormen, of een andere heteroatoom bevatten die zelf een substituent kan dragen.The derivatives prepared according to the method of the present invention correspond to the formula I of the formula sheet, wherein and 10 Rg and independently represent a hydrogen atom, an alkyl group with 1-6 carbon atoms, or wherein NR ^ R ^ together form a heterocyclic compound, or contain another heteroatom which may itself carry a substituent.
De heterocyclische groepen kunnen morfolinegroepen zijn, piperazine, 15 piperadine en in het bijzonder methyl-4-piperazine-1 groep zijn.The heterocyclic groups can be morpholine groups, piperazine, piperadine and in particular methyl-4-piperazine-1 group.
Volgens de onderhavige uitvinding bereidt men de derivaten door de reactie van pyrazolidine-dione met de algemene formule II van het formuleblad, met formaldehyde of een trimeer en een amine met algemene formule III van het formuleblad.According to the present invention, the derivatives are prepared by the reaction of pyrazolidine-dione of the general formula II of the formula sheet, with formaldehyde or a trimer and an amine of general formula III of the formula sheet.
20 Het voorbeeld dat nu volgt illustreert de uitvinding.The example that follows illustrates the invention.
De analyses en IR en NMR spectra bevestigen de structuur van de verbinding.The analyzes and IR and NMR spectra confirm the structure of the compound.
' Voorbeeld."Example.
Bereiding van difenyl-1 ,2(fenyl-sulfinyl-2-ethyl)-4[pethyl-4-pipera-25 zine)-methy^J-4-pyrazolidine-dione-3,5.Preparation of diphenyl-1,2 (phenyl-sulfinyl-2-ethyl) -4 [pethyl-4-piperazin-2-yl) -methyl-4-pyrazolidine-dione-3,5.
Men roert een oplossing van 4,044 g (0,01 mol) difenyl-1,2(fenyl- 3 3 sulfinyl-2-ethy1)-4-pyrazolidine-dione-3,5, 10 cm isopropanol, 1,048 cm formaldehyde en 1,23 cm (0,0111 mol) N-methyl-piperazine. De temperatuur stijgt naar 29°C. Men verwarmt op de refluxtemperatuur gedurende 2\ uur.A solution of 4.044 g (0.01 mol) of diphenyl-1,2 (phenyl-3-sulphinyl-2-ethyl-4-pyrazolidine-dione-3,5, 10 cm isopropanol, 1.048 cm formaldehyde and 1 ml) is stirred. 23 cm (0.0111 mol) N-methyl-piperazine. The temperature will rise to 29 ° C. The reflux temperature is heated for 2 hours.
30 Men verdampt het oplosmiddel en neemt chloroform welke op MgSO^ gedroogd wordt.The solvent is evaporated and chloroform is taken, which is dried over MgSO4.
Men verdampt de chloroform en lost het verdampingsresidu op in ether door re-fluctie.Men scheidt het onoplosbare produkt af en verdampt de ether. Men verkrijgt een wit produkt. F = 139°C.The chloroform is evaporated and the evaporation residue is dissolved in ether by reflux. The insoluble product is separated and the ether is evaporated. A white product is obtained. F = 139 ° C.
De farmacologische proeven die uitgevoerd zijn op de derivaten, 35 bereid volgens de onderhavige uitvinding en tonen aan dat ze actief zijn als 7906029 -2- 2.0860/JD/tj anti-plaatjesaggregaten.The pharmacological tests performed on the derivatives prepared according to the present invention demonstrate that they are active as 7906029-2-2.0860 / JD / tj anti-platelet aggregates.
De inhibitie van plaatjesaggregatie is gemeten voor konijneplaatjes, in vitro, volgens de test van Born en Cross, J. Physiol. 1963, 168-178; waarbij ADP en collageen als aggregaatmiddelen gebruikt worden.Platelet aggregation inhibition has been measured for rabbit platelets, in vitro, according to the test of Born and Cross, J. Physiol. 1963, 168-178; using ADP and collagen as aggregate agents.
5 In aanwezigheid van ADP ligt CA 50, uitgedrukt in jug/ml, in de buurt van 400 voor het derivaat,bereid volgens het voorbeeld. In aanwezigheid van collageen ligt CA 50 in de buurt van 135 ^ug/ml. De derivaten bereid volgens de werkwijze volgens de onderhavige uitvinding kunnen gebruikt worden voor het behandelen van plaatjesaggregatie. De uitvinding omvat alle farmaceu-10 tologische verbindingen met de algemene formule I, welke in principe actief zijn, in associatie met alle excipienten geschikt voor het "’toedienen, in het bijzonder oraal, maar ook endorectaai of parenteraal.In the presence of ADP, CA 50, expressed in jug / ml, is close to 400 for the derivative prepared according to the example. In the presence of collagen, CA 50 is close to 135 µg / ml. The derivatives prepared according to the method of the present invention can be used to treat platelet aggregation. The invention encompasses all pharmaceutical compounds of the general formula I, which are in principle active, in association with all excipients suitable for administration, in particular orally, but also endorectally or parenterally.
-CONCLUSIES- f t 7906029- CONCLUSIONS - f t 7906029
Claims (4)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7823438 | 1978-08-09 | ||
| FR7823438A FR2433020A1 (en) | 1978-08-09 | 1978-08-09 | PYRAZOLIDINE-DIONE DERIVATIVES AND THEIR THERAPEUTIC APPLICATION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL7906029A true NL7906029A (en) | 1980-02-12 |
Family
ID=9211717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7906029A NL7906029A (en) | 1978-08-09 | 1979-08-07 | PROCESS FOR PREPARING DERIVATIVES OF PYRAZOLIDINE-DIONE AND PREPARING A MEDICAMENT |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5524200A (en) |
| AT (1) | AT369735B (en) |
| BE (1) | BE878158A (en) |
| DE (1) | DE2932054A1 (en) |
| ES (1) | ES483236A1 (en) |
| FR (1) | FR2433020A1 (en) |
| GB (1) | GB2028324A (en) |
| IT (1) | IT1122740B (en) |
| LU (1) | LU81582A1 (en) |
| NL (1) | NL7906029A (en) |
| PT (1) | PT70042A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1191034B (en) * | 1982-10-15 | 1988-02-24 | Edmondo Pharma Srl | COMPOUND WITH VASODILATOR, ANTI-AGGREGATING AND HYPO-COLESTEROLEMIZING ACTIVITY, PROCEDURE FOR ITS PREPARATION AND RELATIVE PHARMACEUTICAL COMPOSITION |
-
1978
- 1978-08-09 FR FR7823438A patent/FR2433020A1/en active Granted
-
1979
- 1979-08-07 DE DE19792932054 patent/DE2932054A1/en not_active Withdrawn
- 1979-08-07 NL NL7906029A patent/NL7906029A/en not_active Application Discontinuation
- 1979-08-07 AT AT0539279A patent/AT369735B/en not_active IP Right Cessation
- 1979-08-07 GB GB7927472A patent/GB2028324A/en not_active Withdrawn
- 1979-08-08 LU LU81582A patent/LU81582A1/en unknown
- 1979-08-08 IT IT24997/79A patent/IT1122740B/en active
- 1979-08-08 PT PT70042A patent/PT70042A/en unknown
- 1979-08-08 JP JP10178979A patent/JPS5524200A/en active Pending
- 1979-08-08 ES ES483236A patent/ES483236A1/en not_active Expired
- 1979-08-09 BE BE0/196660A patent/BE878158A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5524200A (en) | 1980-02-21 |
| ATA539279A (en) | 1982-06-15 |
| BE878158A (en) | 1980-02-11 |
| PT70042A (en) | 1979-09-01 |
| FR2433020A1 (en) | 1980-03-07 |
| FR2433020B1 (en) | 1980-12-05 |
| IT1122740B (en) | 1986-04-23 |
| GB2028324A (en) | 1980-03-05 |
| AT369735B (en) | 1983-01-25 |
| LU81582A1 (en) | 1981-03-24 |
| DE2932054A1 (en) | 1980-02-21 |
| ES483236A1 (en) | 1980-05-16 |
| IT7924997A0 (en) | 1979-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |