[go: up one dir, main page]

WO2005037810A2 - Derives de cyclopropylmethanones, leur preparation et leur utilisation en therapeutique - Google Patents

Derives de cyclopropylmethanones, leur preparation et leur utilisation en therapeutique Download PDF

Info

Publication number
WO2005037810A2
WO2005037810A2 PCT/FR2004/002637 FR2004002637W WO2005037810A2 WO 2005037810 A2 WO2005037810 A2 WO 2005037810A2 FR 2004002637 W FR2004002637 W FR 2004002637W WO 2005037810 A2 WO2005037810 A2 WO 2005037810A2
Authority
WO
WIPO (PCT)
Prior art keywords
phenyl
methanone
propoxy
frans
cyclopropyl
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/FR2004/002637
Other languages
English (en)
Other versions
WO2005037810A3 (fr
Inventor
Juan Antonio Diaz Martin
Beatriz Escribano Arenales
Ulpiano Martin Escudero Perez
Magali Romanach Ferrer
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.)
Sanofi Aventis France
Original Assignee
Sanofi Aventis France
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
Priority claimed from FR0312139A external-priority patent/FR2861072B1/fr
Priority claimed from FR0408807A external-priority patent/FR2874215B1/fr
Application filed by Sanofi Aventis France filed Critical Sanofi Aventis France
Publication of WO2005037810A2 publication Critical patent/WO2005037810A2/fr
Publication of WO2005037810A3 publication Critical patent/WO2005037810A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Composé répondant à la formule (I) dans laquelle n égal 1 à 6 ; A représente un aryle, tel qu'un phényle ou un naphthyle, ou un hétéroaryle monocyclique tel qu'un thiényle, furyle ou pyrrolyle ; l'aryle ou l'hétéroaryle étant éventuellement substitué; B représente NR1R2, R1 et R2 représentent, indépendamment l'un de l'autre, un groupe C1-6 alkyle ; ou R1 et R2 représentent ensemble un groupe C2-6 alkylidène, un groupe -C1-3 alkylidène-O-C1-3 alkylidène-, ou un groupe -C1-3 alkylidène-N(R3)­-C1-3 alkylidène- où R3 représente un atome d'hydrogène, un groupe C1-3 alkyle ou C1-6 alkylcarbonyle, ou un aminocycle tel qu'aziridine, azetidine, pyrrolidine, pipéridine, lié par un carbone de l'aminocyle au groupe -O-(C)n-; les groupes R1, R2, ainsi que l'aminocycle étant éventuellement et -O-(C)n- représente un groupe -O-C1-6 alkylidène, éventuellement substitué. Application en thérapeutique.

Claims

43Revendications :
1. Composé de formule (I)
Figure imgf000044_0001
I dans laquelle: n égal 1 à 6 ;
A représente • un aryle, tel qu'un phényle ou un naphthyle, ou
• un hétéroaryle monocyclique tel qu'un thiényle, furyle ou pyrrolyle ; l'aryle ou l'hétéroaryle étant éventuellement substitué par 1 à 4 substituants choisis parmi un atome d'halogène, un groupe hydroxy, nitro, cyano, amino, Cι_3 monoalkylamino, C2-6 dialkylamino, C1-3 alkyle, Cι-2 perhalogénoalkyle, C1-3 halogénoalkyle ou C1-3 alcoxy ;
B représente * NR1 R2, - R1 et R2 représentent, indépendamment l'un de l'autre, un groupe C-ι-6 alkyle; ou - R1 et R2 représentent ensemble un groupe C2-6 alkylidène, un groupe -C1-3 alkylidène-O- Cι-3 alkylidène-, ou un groupe -C1-3 alkylidène- N(R3)-Cι_3 alkylidène- où R3 représente un atome d'hydrogène, un groupe C1.3 alkyle ou C1.6 alkylcarbonyle, les groupes C1-3 alkyle et Cι-6 alkylcarbonyle pouvant être substitués par 1 à 2 substituants choisis parmi un atome d'halogène, un groupe hydroxyle, C-ι-3 alcoxy, nitro, cyano, amino, C-ι-3 monoalkylamino, C2-6 dialkylamino ou phényle, ou * un aminocycle tel qu'aziridine, azetidine, pyrrolidine, 44 piperidine, lié par un carbone au groupe -O-(C)n-; les groupes R1 , R2, ainsi que l'aminocycle étant éventuellement substitués par 1 à 4 substituants choisis parmi un atome d'halogène, un groupe hydroxy, nitro, cyano, amino, C1-3 monoalkylamino, C2.6 dialkylamino, Cι-3 alkyle ou d-3 alcoxy ; et
-O-(C)n- représente un groupe -O-C1-6 alkylidène, éventuellement substitué par 1 à 4 substituants choisis parmi un atome d'halogène, un groupe hydroxy, nitro, cyano, amino, C1.3 monoalkylamino, C2.6 dialkylamino ou C-ι-3 alcoxy; à l'état de base ou de sel d'addition à un acide, ainsi qu'à l'état d'hydrate ou de solvat.
2. Composé selon la revendication 1 caractérisé en ce que : n est égal à 2, 3 ou 4 ;
- A représente un phényle, un thiophène ou un furane ; A étant éventuellement substitué ; - le groupe -0-(C)n-B se trouve en position 4 sur le phényl ; et
- B représente * NR1 R2, - R1 et R2 représentant, indépendamment l'un de l'autre, un groupe C-M alkyle; ou - lorsque R1 et R2 représentent ensemble un groupe C-ι-6 alkylidène, X1-3 alkylidène-O- C1.3 alkylidène- ou -C-ι-3 alkylidène-N(R3)-Cι-3 alkylidène- , B représente un groupe :
Figure imgf000045_0001
* un aminocyle tel qu'une pyrrolidine ou piperidine, lié par un carbone de l'aminocyle au groupe -O-(C)n-; les groupes R1 , R2 et R3 ainsi que l'aminocycle étant éventuellement substitués ; à l'état de base ou de sel d'addition à un acide, ainsi qu'à l'état d'hydrate ou de solvat. 45
3. Composé de formule I selon la revendication 1 ou 2 caractérisé en ce qu'il consiste en le : frar7s-(+/-)-[4-(3-Diméthylamino-propoxy)phényl]-(2-phénylcyclopropyl)- méthanone; frans-(+/-)-[4-(3-Diéthylamino-propoxy)phényl]-(2-phénylcyclopropyl)- méthanone; frans-(+/-)-(2-PhénylcyclopropyI)-[4-(3-pyrrolidin-1-yl-propoxy)phényl]- méthanone; frans-(+/-)-(2-Phénylcyclopropyl)-[4-(3-pipéridin-1-yl-propoxy)phényl]- méthanone; frans-(+/-)-[4-(3-Morpholin-4-yl-propoxy)phényl]-(2~phénylcyclopropyl)- méthanone; f/ans-(+/-)-(2-Phénylcyclopropyl)-[4-(3-pipérazin-1-yl-propoxy)phényl]- méthanone; • fraπs-(+/-)-[2-(4-Bromo-phényl)cyclopropyl]-[4-(3-diméthylamino- propoxy)phényl]- méthanone; frans-(+/-)-[2-(4-Bromo-phényl)cyclopropyl]-[4-(3-diéthylamino- propoxy)phényl]- méthanone; fra/?s-(+/-)-[2-(4-Bromo-phényl)cyclopropyl]-[4-(3-pyrrolidin-1-yl- propoxy)phényl]- méthanone; frans-(+/-)-[2-(4-Bromo-phényl)cyclopropyl]-[4-(3-pipéridin-1-yl- propoxy)phényl]- méthanone; frans-(+/-)-[2-(4-Bromo-phényl)cyclopropyl]-[4-(3-pipérazin-1-yl- propoxy)phényl]- méthanone; • fraπs-(+/-)-[2-(3-Bromo-phényl)cyclopropyl]-[4-(3-diéthylamino- propoxy)phényl]- méthanone; frans-(+/-)-[4-(3-Diéthylamino-propoxy)phényl]-[2-(4-fluoro- phényl)cyclopropyl]-méthanone; ans-(+/-)-4-{2-[4-(3-Diéthylamino-propoxy)benzoyl]-cyclopropyl}- benzonitrile; frans-(+/-)-3-Amino-1-(4-{3-[4-(2-phénylcycIopropanecarbonyl)-phénoxy]- propyl}-piperazin-1 -yl)-propan-1 -one; 46 frans-(+/-)-4-Amino-1-(4-{3-[4-(2-phénylcyclopropanecarbonyl)-phénoxy]- propyl}-piperazin-1 -yl)-butan-1 -one; frans-(+/-)-{4-[2-(1-Méthyl-pyrrolidin-2-yl)-ethoxy]-phényl}-[2- phénylcyclopropyl)-méthanone; frans-(+/-)-[4-(3-Diéthylamino-propoxy)phényl]-(2-thiophen-2-yl- cyclopropyl)-méthanone; frans-(+/-)-[4-(3-Pirrolidin-1-yl-propoxy)phényl]-(2-thiophen-2-yl- cyclopropyl)-méthanone; frans-(+/-)-[4-(3-Pipéridin-1-yl-propoxy)phényl]-(2-thiophen-2-yl- cyclopropyl)-méthanone; fraπs-(+/-)-[4-(3-Diéthylamino-propoxy)phényl]-(2-thiophen-3-yl- cyclopropyl)-méthanone; frans-(+/-)-[4-(3-Diéthylamino-propoxy)phényl]-(2-furan-2-yl-cyclopropyl)- méthanone frans-(+/-)-3-Amino-1-[4-(3-{4-[2-(4-bromo-phenyl)-cyclopropanecarbonyl]- phénoxy}-propyl)-pipérazin-1 -yl]-propan-1 -one; fraπs-(+/-)-[2-(4-Triflurométhyl-phényl)cyclopropyl]-[4-(3-pipérazin-1-yl- propoxy)phényl]- méthanone frans-(+/-)-(2-Phénylcyclopropyl)-[4-(3-[1-4]diazépan-1-yl-propoxy)- phénylj-méthanone ; trans-(+/-)- 3-Amino-1-(4-{3-[4-(2-phénylcyclopropanecarbonyl)-phénoxy]- propyl}-[1 ,4]diazepan-1 -yl)-propan-1 -one; frans-(+/-)-(2-(4-Bromophényl)-cyclopropyl)-[4-(3-[1-4]diazépan-1-yl- propoxy)-phényl]-méthanone ; frans-(+/-)-3-Amino-1-[4-(3-{4-[2-(4-bromo-phényl)-cyclopropanecarbonyl]- phénoxy}-propyl)-[1 ,4]diazépan-1-yl]-propan-1-one ; frans-(+/-)-(2-(4-Trifluorométhylphényl)-cyclopropyl)-[4-(3-[1-4]diazépan-1- yl-propoxy)-phényl]-méthanone. ; frans-(+)-3-Amino-1-(4-{3-[4-(2-phényl-cyclopropanecarbonyl)-phénoxy]- propyl}-piperazin-1-yl)-propan-1-one; et frans-(-)-3-Amino-1-(4-{3-[4-(2-phényl-cyclopropanecarbonyl)-phénoxy]- propyl}-piperazin-1 -yl)-propan-1 -one, 47
• c/s-(+/-)-3-Amino-1-(4-{3-[4-(2-phényl-cyclopropanecarbonyl)-phénoxy]- propyl}-piperazin-1-yl)-propan-1-one ; à l'état de base ou de sel d'addition à un acide, ainsi qu'à l'état d'hydrate ou de solvat.
4. Composé de formule (II):
Figure imgf000048_0001
dans laquelle A est tel que défini dans la revendication 1 , à l'exclusion du : (3-hydroxy-phényl)-(2-phényl-cyclopropyl)-méthanone, (3-hydroxy-phényl)-[2-(2- hydroxyphényl))-cyclopropyl)-méthanone, (3-hydroxy-phényl)-[2-(4- hydroxyphényl))-cyclopropyl)-méthanone, (2-hydroxy-phényl)-[2-(2- hydroxyphényl))-cyclopropyl)-méthanone et (2-hydroxy-phényl)-(2-phényl- cyclopropyl)-méthanone.
5. Composé de formule (IX):
Figure imgf000048_0002
dans laquelle A et n sont tels que définis dans la revendication.
6. Procédé de préparation d'un composé de formule (I) selon l'une quelconque des revendications 1 à 4 caractérisé en ce que l'on fait réagir un composé de formule (II)
Figure imgf000048_0003
dans laquelle A est tel que défini dans la revendication 1 avec un composé de formule (III)
Figure imgf000048_0004
, dans laquelle Y, B et n sont tels que définis dans la revendication 1. 48
7. Composition pharmaceutique contenant un composé de formule (I) , selon l'une quelconque des revendications 1 à 4, ou son sel, solvat ou hydrate, et au moins un excipient pharmaceutique.
8. Utilisation d'un composé de formule (I) selon l'une quelconque des revendications 1 à 4, ou son sel, solvat ou hydrate, pour la préparation d'un médicament destiné à traiter l'obésité et le diabète.
9. Utilisation d'un composé de formule (I) selon l'une quelconque des revendications 1 à 4, ou son sel, solvat ou hydrate, pour la préparation d'un médicament destiné au traitement des maladies du système nerveux central telles que troubles de la vigilance et du sommeil, la narcolepsie, la maladie d'Alzheimer et autres démences, la maladie de Parkinson, les troubles de l'attention chez l'enfant hyperkinétique, les troubles de la mémoire et de l'apprentissage, l'épilepsie, la schizophrénie, les troubles cognitifs modérés, la dépression, l'anxiété, les dysfonctionnements sexuels, l'hypertension, les vertiges et le mal des voyages.
PCT/FR2004/002637 2003-10-17 2004-10-15 Derives de cyclopropylmethanones, leur preparation et leur utilisation en therapeutique Ceased WO2005037810A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0312139 2003-10-17
FR0312139A FR2861072B1 (fr) 2003-10-17 2003-10-17 Derives de cyclopropylmethanones, leur preparation et leur utilisation en therapeutique
FR0408807 2004-08-11
FR0408807A FR2874215B1 (fr) 2004-08-11 2004-08-11 Derives de cyclopropylmethanones, leur preparation et leur utilisation en therapeutique

Publications (2)

Publication Number Publication Date
WO2005037810A2 true WO2005037810A2 (fr) 2005-04-28
WO2005037810A3 WO2005037810A3 (fr) 2005-07-07

Family

ID=34466414

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2004/002637 Ceased WO2005037810A2 (fr) 2003-10-17 2004-10-15 Derives de cyclopropylmethanones, leur preparation et leur utilisation en therapeutique

Country Status (3)

Country Link
AR (1) AR046116A1 (fr)
TW (1) TW200524859A (fr)
WO (1) WO2005037810A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2004591A4 (fr) * 2006-03-10 2009-11-11 Univ New York State Res Found Cyclopropanes à activité de système nerveux central

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5523302A (en) * 1993-11-24 1996-06-04 The Du Pont Merck Pharmaceutical Company Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists
FR2833004B1 (fr) * 2001-12-05 2004-12-10 Aventis Pharma Sa Aryl-cycloalcaines substitues, compositions les contenant et utilisation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2004591A4 (fr) * 2006-03-10 2009-11-11 Univ New York State Res Found Cyclopropanes à activité de système nerveux central

Also Published As

Publication number Publication date
TW200524859A (en) 2005-08-01
WO2005037810A3 (fr) 2005-07-07
AR046116A1 (es) 2005-11-23

Similar Documents

Publication Publication Date Title
KR20060120715A (ko) 무스카린 수용체에 대해 활성을 갖는 화합물
JPH0224819B2 (fr)
CA2702933A1 (fr) Urees de n-phenyl-bipyrrolidine substituees et leur utilisation therapeutique
RU2004113207A (ru) Хинолиновые производные в качестве антагонистов нейропептида y
ATE283047T1 (de) Verwendung von ibudilast zur herstellung eines arzneimittels zur behandlung multiple sklerose
RU2669943C2 (ru) Производные 1,7-нафтиридин-3-карбоксамида, полезные в качестве нейрогенных агентов
US12343319B2 (en) Compositions and methods for treatment of diseases and disorders
RU95122587A (ru) 1-фенилалканоны новые лиганды рецепторов 5-ht*004
RU2005121908A (ru) Производные зн-хиназолин-4-она
WO2005037810A2 (fr) Derives de cyclopropylmethanones, leur preparation et leur utilisation en therapeutique
RU2003101396A (ru) Замещенные нитрированные катехолы, их применение в лечении некоторых расстройств центральной и периферической нервной системы и содержащие их фармацевтические композиции
JP2011506353A (ja) セロトニントランスポーター、セロトニン受容体およびノルアドレナリントランスポーターに親和性を有する化合物の治療的使用
WO2022204519A1 (fr) Utilisation de zt-1a et de ses analogues pour prévenir et/ou traiter des troubles neurodégénératifs et neurocognitifs
RU2169727C2 (ru) Замещенные 1,2,3,4-тетрагидро-2-нафталинамины, способ их получения и фармацевтическая композиция на их основе
Bajad et al. Discovery of pyrazoline analogs as multi-targeting cholinesterase, β-secretase and Aβ aggregation inhibitors through lead optimization strategy
US7514454B2 (en) Piperidin-2,6-dione pamoate salts and their use for the treatment of stress-related affective disorders
US6469064B2 (en) Materials and methods for the treatment of depression
US6403574B1 (en) Azetidinecarboxamide derivatives for treating CNS disorders
JPS6214545B2 (fr)
DE69210229T2 (de) Dihydrochinolin NMDA Antagonisten
WO1991018886A1 (fr) Composes destines au traitement de troubles de la memoire et d'autres troubles cognitifs dûs au vieillissement
FR2465733A1 (fr) Nouveaux derives imidazolylethoxymethyliques de 1,3-dioxoloquinoleines utiles notamment comme medicaments antibacteriens et antifongiques, leur procede de preparation et compositions therapeutiques et formes pharmaceutiques les contenant
US4042584A (en) Ethynylaryl phenyl cyclopropyl thiazines and morpholines
US3218232A (en) Method for relieving depression and composition therefor
EP4400494A1 (fr) Nouveau composé et son utilisation pour traiter des troubles du comportement émotionnel

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase