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WO1999015527A1 - PROCEDE D'OBTENTION DU 2-[4-[4-(m- ETHYLSULFONAMIDOPHENYL) PIPERAZINE-1-YL] BUTYL]-1,3- DIOXOPERHYDROPYRROLO [1,2-c]IMIDAZOL - Google Patents

PROCEDE D'OBTENTION DU 2-[4-[4-(m- ETHYLSULFONAMIDOPHENYL) PIPERAZINE-1-YL] BUTYL]-1,3- DIOXOPERHYDROPYRROLO [1,2-c]IMIDAZOL Download PDF

Info

Publication number
WO1999015527A1
WO1999015527A1 PCT/ES1998/000250 ES9800250W WO9915527A1 WO 1999015527 A1 WO1999015527 A1 WO 1999015527A1 ES 9800250 W ES9800250 W ES 9800250W WO 9915527 A1 WO9915527 A1 WO 9915527A1
Authority
WO
WIPO (PCT)
Prior art keywords
dioxoperhydropyrrolo
imidazole
butyl
piperazin
obtaining
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.)
Ceased
Application number
PCT/ES1998/000250
Other languages
English (en)
Spanish (es)
Inventor
Maria Luz Lopez Rodriguez
Maria Jose Morcillo Ortega
Esther Fernandez Velando
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Universidad Complutense de Madrid
Original Assignee
Universidad Complutense de Madrid
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Universidad Complutense de Madrid filed Critical Universidad Complutense de Madrid
Priority to AU90730/98A priority Critical patent/AU9073098A/en
Publication of WO1999015527A1 publication Critical patent/WO1999015527A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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

Definitions

  • a subject of the present invention is a new process for obtaining 2- [4- [4- (m-ethyl sulfonamidophenyl) piperazin-1-yljbutyl] -1,3-dioxoperhydropyrrolo [1,2-c] imidazole (1, EF- 7412), a synthetic compound with therapeutic interest due to its antagonistic character of the 5-HT 1A receptor.
  • Selective serotonin reuptake inhibitors constitute a group of antidepressant drugs (WF Boyer and JP Feighner, Selective Serotonin Re-Uptake Inhibitors; JP Feighner and WF Boyer, Eds .; Wiley, 1991; pp 89-108) , which exert their action by increasing serotonergic transmission in the brain. These agents have a latency period of three to six weeks (Y. Lecrubier, New Pharmacological Approaches to the Therapy or / Depressive Disorders. Int. Acad Biomed Drugs Res.; J. Mendlewics et al., Eds .; Karger: Basel, 1993; Vol. 5, pp 83-91).
  • a subject of the present invention is a new process for obtaining 2- [4- [4- (m-ethyl sulfonamidophenyl) piperazin-l-yl] butyl] -l, 3-dioxoperhydropyrrolo [1, 2-c] imidazole (1, EF-7412), a synthetic compound with therapeutic interest due to its antagonistic character of the 5-HT IA receptor.
  • Reagents (a) HNa, DMF; (b) Et 3 N, l- (-ethylsulfonamidophenyl) piperazine (4).
  • Reagents (a) KaCC ⁇ , diglyme / ⁇ ; (b) HNa / DMF; (c) EtjN, acetonitrile / ⁇ ; (d) H 2> Pd (C) / MeOH; (e) EtSO ⁇ Cl, pyridine acetone.
  • reaction mixture is diluted in water, the solvents are removed under reduced pressure and the solid residue is purified by silica gel column chromatography (ethyl acetate / ethanol 9: 1), isolating 17.1 g (82%) of 1 as a solid that is transformed into the hydrochloride and crystallized from methanol / ethyl ether: mp 187-190 ° C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne un nouveau procédé d'obtention du 2-[4-[4-( m-éthylsulfonamidophényl) pipérazine-1-yl] butyl]-1,3- dioxoperhydropyrrolo [1,2-c]imidazol (1, EF-7412), composé de synthèse présentant un intérêt thérapeutique lié à son caractère antagoniste du récepteur 5-HT1A. Ce nouveau procédé permet de surmonter les difficultés rencontrées auparavant lors de la préparation, car ce procédé permet d'obtenir le produit souhaité en une séquence synthétique de plus grande simplicité et avec des rendements supérieurs.
PCT/ES1998/000250 1997-09-23 1998-09-15 PROCEDE D'OBTENTION DU 2-[4-[4-(m- ETHYLSULFONAMIDOPHENYL) PIPERAZINE-1-YL] BUTYL]-1,3- DIOXOPERHYDROPYRROLO [1,2-c]IMIDAZOL Ceased WO1999015527A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU90730/98A AU9073098A (en) 1997-09-23 1998-09-15 Process for obtaining 2-(4-(4-(m- ethylsulfonamido-phenyl) piperazine-1-yl) butyl)-1,3- dioxoperhydroyrrolo (1,2-c)imidazol

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES9701987A ES2129370B1 (es) 1997-09-23 1997-09-23 Procedimiento para la obtencion del 2-(4-(4-(m-etilsulfonamidofenil)p iperazin-1-il(butil)-1,3-dioxoperhidropirrolo)1,2-c(imidazol
ESP9701987 1997-09-23

Publications (1)

Publication Number Publication Date
WO1999015527A1 true WO1999015527A1 (fr) 1999-04-01

Family

ID=8300663

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/ES1998/000250 Ceased WO1999015527A1 (fr) 1997-09-23 1998-09-15 PROCEDE D'OBTENTION DU 2-[4-[4-(m- ETHYLSULFONAMIDOPHENYL) PIPERAZINE-1-YL] BUTYL]-1,3- DIOXOPERHYDROPYRROLO [1,2-c]IMIDAZOL

Country Status (3)

Country Link
AU (1) AU9073098A (fr)
ES (1) ES2129370B1 (fr)
WO (1) WO1999015527A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7351732B2 (en) 2002-07-31 2008-04-01 Schwarz Pharma S.L. Cycloalkanedione derivatives, method for the production thereof and their pharmacological applications

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996006846A1 (fr) * 1994-09-01 1996-03-07 Universidad Complutense De Madrid Nouveaux derives d'aryle piperazines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996006846A1 (fr) * 1994-09-01 1996-03-07 Universidad Complutense De Madrid Nouveaux derives d'aryle piperazines

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
JOURNAL MEDICINAL CHEMISTRY, Vol. 32, 1989, G.E. MARTIN et al., "Activity of Aromatic Substituted Phenylpiperazines Lacking Affinity for Dopamine Binding Sites in a Preclinical Test of Antipsychotic Efficacy", pp. 1052-1056. *
JOURNAL MEDICINAL CHEMISTRY, Vol. 39, 1996, M.L. LOPEZ-RODRIGUEZ et al., "Synthesis and Structure-Activity Relationships of a New Model of Arylpiperazines", pp. 4439-4450. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7351732B2 (en) 2002-07-31 2008-04-01 Schwarz Pharma S.L. Cycloalkanedione derivatives, method for the production thereof and their pharmacological applications

Also Published As

Publication number Publication date
AU9073098A (en) 1999-04-12
ES2129370A1 (es) 1999-06-01
ES2129370B1 (es) 2000-03-01

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