Phenylpiperazines which are useful in the treatment of schistosomiasis

• US 4,515,793 A
• Filed: 07/27/1983
• Issued: 05/07/1985
• Est. Priority Date: 07/27/1983
• Status: Expired due to Fees

• Current Assignee: The Edna McConnell Clark Foundation
• Original Assignee: The Edna McConnell Clark Foundation
• Inventors: Werbel, Leslie M., Worth, Donald F., Colbry, Norman, Turner, William
• Primary Examiner(s): Hollrah, Glennon H.
• Assistant Examiner(s): TURNIPSEED, JAMES
• Application Number:
  US06/517,883
• Time in Patent Office: 650 Days
• Field of Search: 544/392, 544/394, 544/364, 544/375, 544/379, 424/250
• US Class Current: 514/254.11
• CPC Class Codes: C07C 45/63 by introduction of halogen; by substitution of halogen atoms by other halogen atoms
• CPC Class Codes: C07C 49/80 containing halogen
• CPC Class Codes: C07D 213/50 Ketonic radicals
• CPC Class Codes: C07D 295/092 with aromatic radicals attached to the chain
• CPC Class Codes: C07D 295/108 to an acyclic saturated chain
• CPC Class Codes: C07D 307/52 Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 307/81 Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 333/22 Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
• CPC Class Codes: C07D 333/28 Halogen atoms
• CPC Class Codes: C07D 333/76 Dibenzothiophenes
• CPC Class Codes: C07D 339/08 Six-membered rings

Abstract

A compound of the formula ##STR1## in which A is ##STR2## n is 1, 2 or 3, and R is phenyl optionally substituted with halogen, alkyl, phenyl, cyano, hydroxy, alkoxy, mercapto, sulfinyl, sulfonyl, amino, nitro, trifluoromethyl and/or naphthyl radicals; or a furan, thiophene, pyridine, benzofuran, dibenzothiophene or thianthrene radical,

or a pharmacologically acceptable salt thereof, for treating schistosomiasis.

Claims

1. 2(4-(3-Chloro-4-hydroxymethylphenyl)-1-piperazinyl)-1-(2,3,4-trichloro-phenyl)-ethanone of the formula ##STR35## or a pharmacologically acceptable salt thereof.

2. 2-(4-(3-Chloro-4-hydroxymethylphenyl)-1-piperazinyl)-1-(2-benzofuranyl)-ethanone of the formula ##STR36## or a pharmacologically acceptable salt thereof.

3. A method of combating a schistosomal infection in a patient which comprises administering to such patient an antischistosomal effective amount of a compound of the formula ##STR37## in which A is ##STR38## n is 1, 2 or 3, and R is phenyl optionally substituted with halogen, alkyl, phenyl, cyano, hydroxy, alkoxy, mercapto, sulfinyl, sulfonyl, amino, nitro, trifluoromethyl and/or naphthyl radicals;

or a furan, thiophene, pyridine, benzofuran, dibenzothiophene or thianthrene radical optionally substituted by halogen and/or alkyl of up to 4 carbon atoms,

or a pharmaceutically acceptable salt thereof.

4. The method according to claim 3 wherein such compound is

2(4-(3-chloro-4-hydroxymethylphenyl)-1-piperazinyl)-1-(2,3,4-trichlorophenyl)-ethanone,

2-(4-(3-chloro-4-hydroxymethylphenyl)-1-piperazinyl)-1-(4-chlorphenyl)-propanone or

2-(4-(3-chloro-4-hydroxymethylphenyl)-1-piperazinyl-1-(2-benzofuryl)-ethanone,

or a pharmacologically acceptable salt thereof.