Piperazine substituted 6-phenyldihydro-3(2H)-pyridazinones, and pharmaceutical preparations containing these

• US 4,954,501 A
• Filed: 09/21/1988
• Issued: 09/04/1990
• Est. Priority Date: 02/12/1988
• Status: Expired due to Fees

• Current Assignee: Heumann Pharma GmbH & Company
• Original Assignee: Heumann Pharma GmbH & Company
• Inventors: Engler, Heidrun, Herter, Rolf, Schickaneder, Helmut, Ahrens, Kurt-Henning, Morsdorf, Peter, Pfahlert, Volker
• Primary Examiner(s): Daus, Donald G.
• Application Number:
  US07/247,868
• Time in Patent Office: 713 Days
• Field of Search: 514/252, 514/247, 544/239, 544/238
• US Class Current: 514/252.02
• CPC Class Codes: A61P 9/04 Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
• CPC Class Codes: A61P 9/12 Antihypertensives
• CPC Class Codes: C07D 237/04 having less than three double bonds between ring members or between ring members and non-ring members
• CPC Class Codes: C07D 401/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links

Abstract

New 6-phenyldihydro-3(2H)-pyridazinones corresponding to the following general formula ##STR1## are described. These compounds are readily prepared in a form suitable for oral administration and are distinguished by a high positive inotropic action and have only a slight effect on blood pressure and cardiac frequency. A process for their preparation and pharmaceutical preparations containing these compounds are also described.

Claims

1. A 6-(4-piperazino)-phenyl-4,5-dihydro-3(2H)-pyridazinone, comprising ##STR55## wherein R¹ is nitro or cyano;

R² is selected from the group consisting of hydrogen, methyl and hydroxymethyl and R³ is selected from the group consisting of a C₁ -C₆ alkyl group, a C₁ -C₆ alkyl group substituted with amino or hydroxy, a phenyl group, a naphthyl group, a heteroaryl group wherein the hetero atom is selected from the group consisting of O, S and N, a substituted such aryl or heteroaryl group wherein the substituents are selected from the group consisting of halogen, C₁ -C₃ alkyl and C₁ -C₃ alkoxy, a cyano group, an acyl group with the proviso that, when said acyl group is aroyl, the aroyl ring may be substituted with substituents selected from the group consisting of halogen, C₁ -C₃ alkyl and C₁ -C₃ alkoxy, a carbonyl group and a C₁ -C₆ alkoxycarbonyl group, and a physiologically acceptable salt thereof.

2. A 6-Phenyldihydro-3(2H)-pyridazinone corresponding to the formula ##STR56## in which R¹ denotes a nitro or a cyano group, R² denotes a hydrogen atom or a methyl group and R³ stands for an ethoxycarbonyl or an acetyl group, and the physiologically acceptable salts thereof.

3. A 6-phenyldihydro-3(2H)-pyridazinone according to claim 2, consisting of 6-[4-(4-ethoxycarbonyl-piperazin-1-yl)-3-nitro-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone.

4. A 6-phenyldihydro-3(2H)-pyridazinone according to claim 2, consisting of 6-[4-(4-ethoxycarbonyl-piperazin-1-yl)-3-nitro-phenyl]-4,5-dihydro-3(2H)-pyridazinone.

5. A 6-phenyldihydro-3(2H)-pyridazinone according to claim 2, consisting of 6-[4-(4-acetyl-piperazin-1-yl)-3-nitro-phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone.

6. A 6-phenyldihydro-3(2H)-pyridazinone according to claim 2, consisting of 6-[3-cyano-4-(4-ethoxycarbonyl-piperazin-1-yl)phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone.

7. Pharmaceutical preparation, characterised in that it contains a compound according to claim 2 together with at least one inert, pharmaceutically acceptable carrier or diluent.