WO2004078732B1 - Produits n-aryl-heteroaromatiques, compositions les contenant et utilisation - Google Patents

Produits n-aryl-heteroaromatiques, compositions les contenant et utilisation

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Publication number
WO2004078732B1
WO2004078732B1 PCT/FR2004/000168 FR2004000168W WO2004078732B1 WO 2004078732 B1 WO2004078732 B1 WO 2004078732B1 FR 2004000168 W FR2004000168 W FR 2004000168W WO 2004078732 B1 WO2004078732 B1 WO 2004078732B1
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Prior art keywords
phenyl
methyl
piperazin
pyrazol
methanone
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PCT/FR2004/000168
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English (en)
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WO2004078732A1 (fr
Inventor
Alain Le-Brun
Fabienne Thompson
Gilles Tiraboschi
Patrick Mailliet
Joseph M Salvino
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Aventis Pharma Sa
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Priority claimed from FR0300894A external-priority patent/FR2850379B1/fr
Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa
Priority to BR0407088-7A priority Critical patent/BRPI0407088A/pt
Priority to EP04705102A priority patent/EP1590329A1/fr
Priority to MXPA05008099A priority patent/MXPA05008099A/es
Priority to JP2006505660A priority patent/JP2006516656A/ja
Priority to AU2004218260A priority patent/AU2004218260A1/en
Priority to CA002512243A priority patent/CA2512243A1/fr
Publication of WO2004078732A1 publication Critical patent/WO2004078732A1/fr
Publication of WO2004078732B1 publication Critical patent/WO2004078732B1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P9/00—Drugs for disorders of the cardiovascular system
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    • 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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—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 two 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
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Produits N-aryl-hétéroaromatiques, compositions les contenant et utilisation. La présente invention concerne de nouveaux composés chimiques, particulièrement de nouveaux produits N-aryl-hétéroaromatiques, des compositions les contenant, et leur utilisation comme médicaments, en particulier en oncologie.

Claims

REVENDICATIONS MODIFIEES reçues par le Bureau international le 15 septembre 2004 (15.09.2004) revendications originales 4 et 9 sont supprimées; revendications originales 1-21 renumérotées en 1-19
1. Produit répondant à la formule (I) suivante :
Figure imgf000002_0001
dans laquelle
R1 est choisi parmi
- phényle,
- phényle substitué par au moins un radical choisi parmi halogène, (C1-C3)- alkyle, CON(R10)(R11), O-R10. S-R10, N(R10)(R11),
- pyridyle,
- pyridylθ substitué par au moins un radical choisi parmi halogène, (C1-C3)- alkyle, CON(R10)(R11), O-R10, S-R10, N(R10)(R11), dans lesquels R10, R11 sont indépendamment choisis parmi H, (C1-C3)-alkyle, (C1-C3 alkyle halogène ;
R2 est choisi parmi phényle, 3-pyridyle, phényle substitué par au moins un radical choisi parmi halogène, alkyle, O-R10, S-R10, N(R10)(R11), dans lequel R10, R11 sont indépendamment choisis parmi H, (C1-C3)alkyle, (C1-C3)alkyle halogène ; L est sélectionné dans le groupe constitué par C(R7)(R8), C≈O, C=S, C=N(R7); R3 est sélectionné dans le groupe constitué par H, halogène, CF3, alkyle, alkyle substitué, aikylène, aikylène substitué, alkynyle, alkynyie substitué, cycioalkyle, cycloalkylèπe, hétérocyclyle, hétérocyclyle substitué, CO-R7, C(R7)=N-0(R8), COOH, CONH-aryle, CONH-hétéroaryle, CONH-R7, CON(R7)(RS), CO-N(R7)- aryie, CO-N(R7)-hétéroaryle, C(OR7)=NH, C[N(R7)(R8)]=NH, NH2, NH-aryle, NH-hétéroaryle, NH(R7), N(R7)(R8), NH-CO-R7, N(R7)-CO-aryie, N(R7)-CO- hétéroaryle, NH-S02-R7, NH-S02-aryle. NH-S02-hétéroaryle, NH-CH2- C02(R7), NH-CH2-aryle, NH-CH2-hétéroaryle, NH-COO-(C1-C4)alkyle, NH-CH2- (C2-C3)alkylène, NH-CH2-(C2-C3)alkyny!e, N(R7)-N(R8)(R12), N-N-C(R7)(R8), CN, 0-R7, 0-CH2-arylβ, 0-CH2-hétéroary)e, S-R7, SO-R7, S02-R7, aryle, hétéroaryle, cycioalkyle substitué, aryle substitué, hétéroaryie substitué ; R4 est sélectionné dans le groupe constitué par constitué par H, (C1-C3alkyle) , cyclopropyle, (C2-C3)alkylène, (C2-C3)alkynyle, 0(C1-C3)alkyle, S-(C1- C3)alkyle, F, CI, Br ; X est N ou CH ;
188 R7, R8, R12 sont indépendamment sélectionnés dans le groupe constitué par H, (C1-C3)alkyle, (C1-C3)alkyle substitué, L-G-R1 est sélectionné dans le groupe constitué par
Figure imgf000003_0001
r S vθC !
- L, R1 tels que définis précédemment,
- R5 et R6 sont indépendamment sélectionnés dans le groupe constitué par H, (Cl-C3)alkyle, oxo, halogène ; et
- R9 ≈ (C1-C3)alkylθ; sous forme racémique, enrichie en un énantiomère, enrichie en un diastéréoisomère, ses tauîomères, ses prodrogues et ses sels pharmaceutiquement acceptables, sous réserve que le produit de formule (I) ne soit pas un des composés suivants :
Figure imgf000003_0002
[4-{3-méthoxy-phényl)-pipérazin-1-yl]-(2-phényI-2H-pyrazol-3-yl .méthanone,
[4-(6-méthyl-pyridiπ-2-yl)-pipérazin-1-yl]-(2-phényl-2H-pyrazol-3-yl)-méthaπone,
[4-(3-hydroxy-phényl)-pipérazin-1-yl]-(2-phényi-2H-pyrazol-3-yl>-méthanone,
[4-(3,5-diméthoxy-phéπyl)-pipérazin-1-ylH -(4-πitrophényl-5-trifluorométhyl-lH- pyrazol-4-yl)-méthanone,
2. Produit selon la revendication 1 , caractérisé en ce que X est N.
3. Produit selon la revendication 1 ou 2, caractérisé en ce que L-G-R1 est
dans lequel R5 et R6 sont chacun H.
189
4. Produit selon la revendication 3, caractérisé en ce que R1 est choisi parmi :
- phényle substitué par halogène, (C1-C3)-alkyle, (C1-C3)-alkoxy, ou carboxamide,
- 2-pyridyle ou 3-ρyridyle,
- 2-pyridyle ou 3-pyridyle substitué par halogène ou (C1 -C3)-aikyle.
5. Produit selon la revendication 4, caractérisé en ce que R1 est phényle substitué par :
- un radical chlore, ou
- un ou deux radicaux éthoxy, ou
- un radical carboxamide.
6. Produit selon l'une quelconque des revendications 4 à 5, caractérisé en ce que R1 est choisi parmi phényle-2.3-disubstitué, phényIe-2,5-disubstitué, phényle-3- substitué, phényle-3,5-disubstitué, phényle-3,4-disubstitué.
7. Produit selon la revendication 4, caractérisé en ce que R1 est choisi parmi 2-pyridyle-4-substitué, 2-pyridyle-6-substitué, 2-pyridyle-4,6-disubstitué, 3-pyridyle-2- substitué, et 3-pyridyle-5-substitué.
8. Produit selon la revendication 1, caractérisé en ce que R3 est choisi parmi H, (C1-C3)alkyle, CF3, hydroxyméthyle, amino, azétidino et pyrrolidino.
9. Produit selon la revendication 8, caractérisé en ce que R3 est choisi parmi méthyle, hydroxyméthyle, CF3 et amino.
10. Produit selon la revendication 1 , caractérisé en ce que R4 est H.
11. Produit selon la revendication 1 , caractérisé en ce qu'il est choisi parmi:
- (S.S-Dimethyl-l-pheπyl-IH-pyrazoM-y ^phenyl-piperazin-l-ylJ-methanone
- (3,5-Dimethyl-1-phenyl-1 H-pyrazol-4-yl)-[4-(2-methoxy-phenyl)-piperazin-1 -yl]- methanoπe
- (3,5-Dimethyl-1'pheπyl-1 H-pyrazol-4-yl)-[4-(3-trifluoromethyl-phenyl)"pipera2in-1 -yl]- methanone
- (S^-Dimethyl-l-phθnyl-lH yrazol^ylH ^^^01"0^^0^)-?!?6^^!^^^]- methanone
- 1 -{4-[4-(3,5-Dimethyl-1-phθnyl-l H-pyrazole-4-carbonyi)-piperazin-1 -yl]-phenyl}- ethanone
- [4-(2,4-Dimethyl-phenyl)-piperazin-1 -yl]-(3,5-dimeihyI-1 -phenyl-1 H-pyrazoi-4-yl)- methanone
190 - [4-(3,4-Dichloro-phenyl)-piperazin-1-yl]-(3,5-dlmethyl-1-phθnyl-1H-pyrazol-4-yl)- methanone
- [4 3,4-Dimethyl henyl)-piperazin-1 -yl]-(3,5-dimethyl-1 -phenyl-1 H-pyrazol-4-yl)- methanone - (3,5-Dimethyl-1-phenyl-1H-pyra∑oi-4-yl)-(4-o-tolyl-piperazin-1-yl)-methanone
- [4-(2,3-Dirπethy]-phenyl)-pipera∑in-1 -ylH3,5-dimethyl-1 -phenyl-1 H-pyrazol-4-yl)- rnθthanone
- (3,5-Dimθthyl-1 -phenyl-1 H-pyrazol-4-ylH4-(2-θthyl-phenyl)-piperazin-1 -yl]- mθthanone
- [4-(3-Ghloro-phenvl)-piperazin-1 -yi]-(3,5-dimethyl-1 -phenyl-1 H-pyrazol-4-yl)- methanone
- (3,5-Dtmβthyl-1 -phenyl-1 H-pyrazol-4-yl)-(4-m-tolyi-piperazin-1 -yl)-methanone
- (3,5-Dimethyl-l-phenyl-l H-pyrazol-4-yl)-[4-(4-mθthoxy-ρhenyl)-piperazin-1 -yl]- methanone
- [4-(2,4-Dimethoxy-phenyl)-piperazin-1 -ylHS.δ-dimethyl-l -phenyl-1 H-pyrazol-4-yl)- methaπone
- (3,5-Dimethyl-1 -phenyl-1 H-pyrazol-4-yl)-[4-(2-methylsulfanyl-phenyl)-piperazin-1 -yl]- ethanonθ
- [4-(4-Chloro-phenyl)-piperazin-1 -yl3-(3,5-dimethyl-1 -phenyl-1 H-pyrazol-4-yl)- methaπone
« (3τ5-Dimethyl-1-phenyl-1H-pyrazol-4-ylH4-πaphthalen-1-yl-piperazin-1-yl)- methanone
- [4-(5-Chioro-2-methyl-phenyi)-piperazin-1 -yl]-(3,5-dimethyl-l -phenyl-1 H-pyrazol-4- yl)-methanone
- (3,5-Dimethyl-1 -phenyl-1 H-pyrazoI-4-yl)-[4-(2-ethoxy-phenyl)-piperazin-1 -yl]- methanone
- [4-(2,3-Dichloro-phenyl)-piperazin-1-y]]-(3,5-dimethy[-1 -phenyl-1 H-ρyrazol-4-yl)- ethanone
- (3,5-Dimethyl-1 -phenyl-1 H-pyrazol-4«yl] [4-(4-trifluoromethyl-phenyl)-piperazin-1 -ylj- ethanone
- [4-(5-Chloro-2-methoxy-phenyl)-piperazin-1 -yi]-(3,5-dimethyl-1 -phenyl-1 H-pyrazol- 4-yl)-methanoπe
- [4-(4-Benzyloxy-phenyl piperazin-1 -yl]-(3,5-dimethyl-1 -phenyi-1 H-pyrazol-4-yl)- methanone
- (3,5-Dlmethyl-1-phenyl-1 H-pyrazol-4-ylH4-{2-trif]uoromθthyi-phenyi)-pipθrazin-1-yl3- methanone
- [4-(2,3-Dihydro-benzo[1 ,43dioxiπ-6-yl)-piperazin-1 -y!]-(3,5-dimethyl-1 -ρhenyl-1 H- pyrazol-4-yl)-methanone
191 - [2-(4-Methoxy-phenyl)-5-mθthyl-2H-pyrazol-3-yl]-(4-phenyl-ρiperazin-1-yl)- methanone - [2-(4-Methoxy-phenyI)-5-methyl-2H-pyrazol-3-yl]-[4-(2-mθthoxy-phenyl)-pipera∑in-1- yl]-methanone
- [2-(4-Methoχy-phenyl 5-methyl-2H-pyrazol-3-yl]-E4-(3-trifluoromethyl-phenyl)- pipera∑in-1 -yl]-mΘthanone
- [4-(4-Fluoro-phenyl)»pipera2in-1-yl]-[2-(4-meihoxy-phenyl)-5-methyl-2H-pyrazol-3- yl]-meîhanone
- 1^4-{4-I2-(4-Meîhoxyφheπy!)-5-mθthyl-2H-pyrazole-3^carbonyl]-pipera∑iπ-1-yl}- phenyl)-ethanoπθ
- E4-(2,4-Dimethyl-phenyl)-piperazin-1-yl]-[2-(4-methoxy-phenyl)-5-methyl-2H-pyrazol-
3-y!]-mθthanone
- [4-(3,4-Dichloro henyl)-pipera∑in-1-yl]-E2-(4-methoxy-phenyl)-5-methyl-2H-pyrazol-
3-yl]-methanone
- [4-(3,4-Dimethyl-phenyl)-piperazin-1-ylH2-(4-methoxy-phenyl>5-methyl-2H-pyrazol-
3-yl]-methanone
- [2-(4-Methoxy-phenyl)-5-mθthyl-2H-pyrazol-3-yi]-(4-o-tolyl-piperazin~1-yl)- methanone
- [4-(2,3-Dimethyl-phenyl)-piperaziπ-1-yll-[2-(4-methoxy-phenyl)-5-methy]-2H-ρyrazol-
3-yl]-methanone
- [4-{2-Ethyl-phenyl)-piperazin-1-yI]-[2-(4-methoxy-phenyl)-5-methyl-2H-pyrazol-3-yl]- methanone
- [4-(3-Chloro-phenyl)-piperaziπ-1-yl]-[2-(4-methoxy-phenyl)-5-methyl-2H-pyrazoI-3- yl]-methanone
- [2-(4-Mθthoxy-phθnyI)-5-methyI-2H-pyrazoI-3-yl]-(4-m-tolyl-piperazin-1-yl)- methanone
- [2-{4-Methoxy-phenyl)-5-methyl-2H-pyrazol-3-yl3-[4-(4-methoxy-pheπyl)-piperaziπ-1- yI]-methanone
- [4-{2I4-Dimethoxy-phenyl)-pipθrazin-1-ylH2-(4-mθthoxy-phenyl)-5-mθthyl-2H- pyrazol-3-yî]-methanone
- [2-(4-Methoxy-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(2-mθthylsulfaπyl-pheπyi)- piperazin-1 -yl]-methaπone
- [4-(4-Chloro-phenyl)-piperazin-1-yl]-[2-(4-mθthoxy-phenyl)-5-methyl-2H-pyrazol-3- ylj-methanoπe
• {2-(4-Methoxy-phenyl)-5-methyl-2H-pyrazol-3-yl]-(4-naphthalθn-l -yl-piperazin-1 -yl)- methaπoπe
- [4-{5'ChIoro-2-methyl-phenyl)-piperazin-1-yl]-[2-(4-methoxy-phenyl)-5-methyl-2H- pyrazol-3-yl]-methanone
192 - I4-(2-Ethoxy-phenyl)-piperazin-1-yl]-t2-(4-methθxy-phenyl)-5-methyl-2H-pyrazol-3- yl]-methanone - [4-(2,3-Dichloro-phθnyl)-piperazin-l-yl]-[2-(4-me-hoxy-phenyl)-5-methyl-2H-ρyrazol-
3-yl]-methanoπβ
- E2-(4- ethoxy-phenyl)-5-methyl-2H-pyrazol-3-yl]-î4-(4-trifluoromeîhyl-ρheπyI)- piperazin-1 -yl]-methanone - [4-(5-Chloro-2-methθ y-pheny])-pipera∑in'1-yl]-[2-{4-methoxy-phenyl)-5-methyl-2H- pyra∑oi-S-ylJ-meîhanona - [4-(4-Benzyloxy-phenyl)-piperaziπ-1-yl]-[2-(4-methoxy-phenyl)-5-methyl-2H-pyrazo]-
3-yl]-methanone - [2-(4-Methoxy-phenyl)-5-methyl-2H-pyrazol-3-ylH4-(2-trifluoromethyl-phΘnyl)- pipera∑in-1 -yO-mβihanoπe
- [4-(2,3-Dihydro-benzo[1 ,4]dioxin-6-yl)-piperazin-1 -yl}-[2-(4-methoxy-phenyl)-5- methyl-2H-pyrazol-3-yl]-methanone
- [2-(3-Methoxy-phenyl)-5-methyl-2H-pyrazol-3-yl]-(4-ρhenyl-piperazin-1-yl)^ methanone - [2-(3-Methoxy-phenyl 5-methyl-2H-pyrazol-3-ylH4-(2-methoxy-pheπyl)-piperazin-1- yl]-methaπone
- [2-(3- ethoxy-pheny))-5-methy]-2H-pyrazol-3-ylH4-(3-trifluoromethyl-phenyi)- piperazin-1-yl]-methanoπe
» [4-(4-Fiuoro-phenyi)-piperazin-1-yl]-[2-(3-methoxy-phenyl)-5-mθthyl-2H-pyrazol-3- yl]-methanone
- 1.( -{4-[2-{3- ethoxy-phenyl)-5-methyl-2H-ρyrazo]e-3-carbonyl]-piperazin-1-yl}- ρhenyl)-ethanone
- [4-(2,4-Dimethyt-phenyi)-piperazin-1-yl]-[2-(3-mθthoxy-phenyl)-5-methyl-2H-pyrazol-
3-yl]-methanone
- [4-(3,4-Dichioro-phenyl piperazin-1-ylM2-(3-mθthoxy-phenyl)-5-methyI-2H-pyrazol-
3-yl]-methanone
- [4-(3,4-Dimethyl-phenyl)-piperaziπ-1-yl]-[2-(3-methoxy-phenyl)-5-methyl-2H-pyrazol-
3-yl]-methanone
- [2-(3-Methoxy-phenyl)-5-methyI-2H-pyrazol-3-yl]-(4-o-tolyl-piperazin-1-yl)- ethanone
- [4-(2,3-Dimethy!-phenyl)-piperazin-1-yl]-[2-(3-methoxy-phenyl)-5-methyl-2H-pyra∑ol-
3-yl]-methanoπe
- [4-(2-Ethyl-phenyl)-piperazin-1-yl]-E2-(3-mθthoxy-phenyI)-5-methyl-2H-pyrazol-3-yl]- methanone
~ [4-(3-Chloro-phenyl)-pipθrazin-1-yl]-[2-(3-methoxy-phenyl)-5-mθthyl-2H-pyrazol-3- yl]-methanone
193 - [2-(3- ethoxy-phθnyl)-5-methyl-2H-pyra∑ol-3-yl]-(4-m-to[yl-piperazin-1-yl)- methaπone - [2-(3-Methoxy-phθny!)-5-methyl-2H-pyrazol-3-yl]-[4-(4-methoxy-phenyl)-piperazin-1- yi]-methanone
- [4-(2]4-Dimethoxy-phenyl)-pipθrazin-1-yl]-[2-(3-methoxy-phenyl)-5'-methy!-2H- pyra∑ol-3-yl]-methanonΘ
- [2-{3-Methoxy-phenyl 5-methyl-2H-pyra2ol-3-yl]-[4-(2-mθthylsulfanyl-phenyl pip@razin-1 -ylj-methanonθ
- [4-(4-Chloro-phenyl)-piperazin-1-yl]-l2-(3-methoxy-phenyl)-5-mθthyl-2H-pyrazol-3- yl]-methanone
- [2-(3-Methoxy-phenyl)-5-methyl-2H-pyra2θl-3-yl]-(4-naphthalen-1 -yl-piperazln-1 -yl)- ethanone
- [4-(5-Chloro-2-methyl-phenyl)-piperazin-1-yi]-[2-(3-methoxy-phenyl)-5-methyl-2H- pyrazoi-3-yl]-methanone
- [4-(2-Ethoxy-phenyl)-pipθrazin-1-yl]-[2-(3-methoxy-phenyl)-5-mθthyl-2H-pyrazol-3- yl]-methanone
- [4-(2,3-Dichloro-phenyl)-pipθrazin-1-yl]-[2-(3-methoxy-phenyl)-5-methyl-2H-pyrazoi- 3-yl]"methanone
- [2-{3-Methoxy-phenyl)-5-methyI-2H-pyrazol-3-yl]-[4-(4-irifluoromethyl-phenyl)- piperazin-1 -yl]-methanone
- [4-(5-Chloro-2-methoxy-phenyi)-piperazin-1-yl]-[2-(3-methoxy-phenyl)-5-methyl-2H- pyrazol-3-yl]-methanone
- [4-(4-Benzyloxy-phenyl)-piperazin-1-yl]-[2-(3-methoxy-phenyl)-5-methyl-2H-pyrazol- 3-yl]-methanone
- [2-(3-Methoxy-phenyl)-5-methyl-2H-pyrazol-3-yl3-[4-(2-trifluoromethyl-ρhenyl)- piperaziπ-1 -ylj-methanone
- [4-(2,3-Dihydro-benzo[1 ,4]dioxin-6-yl)-piperazin-1 -yl]-[2-(3-methoxy-ρhenyl)-5- methyI-2H-pyrazol-3-yl]-methanone
- (5-Meihyl-2-phenyl-2H-pyrazol-3-yl)-{4-phenyl-piperazln-1-yi)-methanone - [4-(2- ethoxy-phenyl)-piperazin-1-y]3-(5-methyl-2-phenyl-2H-pyrazol-3-yl)- methaπone
- (5-Methyl-2-phenyl-2H-pyrazol-3-yl)-[4-(3-trifiuoromethyl-ρhenyl)-piρerazin-1-yl]- methanone
- [4-(4-Fluoro-pheπyl)-piperazin-1-yl]-(5-mθthyl-2-phθnyl-2H-pyrazol-3-yl)-methanoπe - 1 -{4-[4-(5-Methyl-2-phenyl-2H-pyrazole-3-carbonyl)*piperazin"1 -yl]-phenyl}- ethanone
- [4-(2,4-Dimethyl-phenyl)-piperazin-1-yl3'(5"methyl-2-phenyl-2H-pyrazoi-3-yl)- rnethanone
194 - [4-(3,4-Dichloro-phenyl)-piρerazin-1-yl]-(5-mθthyl-2-ρhenyl-2H-pyrazol-3-yl)- methaπone
- (5-Methyl-2-pheπyl-2H-pyrazol-3-ylH4-o-tolyl-piperazin-1-yl)-methanone - [4-(2,3-Dimθthyl-phenyI)-piperazin-1-yl]-(5-methy[-2-phenyl-2H-pyra∑oi-3-yl)- methanone
- [4-(2-Eth l-phenyI)-pipera∑iπ-1-yl]-(5- efhyl-2-phenyl-2H-pyrazol-3-yl>methanone
- [4-(3-Chloro-phθnyl)-piperazin-1-yl]-(5-methyl-2-phenyl-2H-pyra∑ol-3-yl)-methanone
- [4-(3- etho^y-phenyl)-piρβrazîn-l-yl]-(5-methyl-2-phenyl-2H-pyrazol-3-yl)- methanone
- (5-Methyl-2-phenyl-2H-pyrazol-3-yl (4-m-tolyl-pipera∑in-1-yl)-mθthanone
- I4-(4-Methoxy-phenyl)-piperazin-1-yl]-(5-methyl-2-phenyl-2H-pyra∑ol-3-yl)- methanone
- [4-(2I4-Dimethoxy-phenyl)-piperazin-1-y!3-(5-methyl-2-phenyl-2H-pyrazol-3-yl)- methanone
- (5- ethyl-2-phenyl-2H-pyrazol-3-yl)-[4-(2»methyIsulfanyl-phenyl)-piperazin-1-yl]- methanone
- [4-(4-Chloro-phenyl piperazin-1-yl]-(5-methyl-2-phenyl-2H-pyrazol-3-yl)-methanone
- (5-Methyl-2-pheπyl-2H-pyrazol-3-yi)-(4-naphthalen-1 -yl-piperazin-1 -yl)-methanone - [4-(5-Chloro-2-methyl-phenyI)-piperazin-1-ylH5-mθthyl-2-phenyl-2H-pyrazol-3-yl)- methanone
- [4-(2-Ethoxy-phenyl)-piperazin-1-yl3-(5-methyl-2-phθnyl-2H-pyrazol-3-yl)-methanone - I4-(2J3-Dichloro-phθnyl)-pipθrazin-1-yl]-(5-methyl-2-phenyl-2H-pyrazol-3-yl)- methanone
- (5- ethyl-2-phθnyl-2H-pyrazol-3-yl)-[4-(4-trlfluoromethyl-phenyi)-piperazin-1-yl]- ethanone
- [4-(5-Chloro-2-methoxy-phenyl)-piρerazin-1 -yl3-(5-methyl-2-phenyl-2H-pyrazoi-3-yl )- methanone
- [4-(4-Benzyloxy-phenyl)-piperazin-1-yl]-(5-methyl-2-phenyl-2H"pyrazo["3"yl)- methanone
- [4-(2,3-Dihydro-benzo[l ,4]dioxin-6-yl)-piρerazin-1 -yl]-(5-methyl-2-phenyl-2H- pyrazol-3^yl)-methaπoπe
- N-{4-[4-(5-Methyl-2-phenyl-2Hl-pyrazole-3-carbonyl)-piperazin-1-yl]-phenyl}- methanesulfonamide
- [2-(2-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]-(4-phenyl-piperaziπ-1-yl)-methanone - [2-(2-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yi]-[4-(2-methoxy-phenyl)-piperazin-1- yl]-methanone
- [2-{2-FIuoro-phenyl)-5-methyl-2H-pyra∑ol-3-yl]-[4-(4-fluoro-phenyl)-piperazin-1-y!]- methanone
195 - 1 -{4-{4-[2-{2-Fluoro-phenyl)-5-methyl-2H-pyrazole-3-carbonyl]-piperazin-1 -yl}- phenyl ethanone
- [4-(2,4-Dimethyl-phenyl)-piperazin-1-yl]-[2-(2-fluoro-phθnyl)-5-methyl-2H-pyrazol-3- ylj-methanone
- [4-(3l4-Dichloro-phenyl)-pipera∑iπ-1-yl]-[2-(2-fluoro-phenyl)-5-methyl-2H-pyrazol-3- yl]-mβthanon©
- [4-(3,4-Dimethyl-phenyI pipera∑in-1-yl]-[2-(2-fluoro-phenyl)-5-methyl-2H-pyrazoi-3- yl]-methanoπ®
- [2-(2-Fluoro-phenyl)-5-methyl-2H-pyra∑oI-3-ylî-(4-o-tolyl-piperazin-1-yl)-methanone
- [4-(2,3-Dimethyl-phθnyl)-piperazin-1-yl]-[2-(2-fluoro-phenyl)-5-methyl-2H-pyra∑ol-3- yl]-methanone
- [4-(2-Ethyl-phenyl)-pipera∑in-1-yl]-[2-(2-fluoro-phenyl)-5-methy!-2H-pyra∑ol-3-yl]- methanone
- [4-(3-Chloro-phenyl)-piperazin-1-yl]-[2-(2-fluoro-phenyl)-5-methyl'2H-pyrazol-3-y!]- methanone
- [2-(2-Fluoro-phenyl)-S-methyi-2H-pyrazol-3-yl]-[4-(3-methoxy-phenyl)-piperazin-1- yl]-methanone
- [2-(2-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yi]-(4-m-tolyl-pipθrazin-1-yl)-mθthanone
- [2-(2-Fluoro-phenyl)-5-methyl-2H-pyrazoI-3-yl]-E4-(4-methoxy-phenyl)-piperazin-1- y]]-methanone
- E4-(2,4-Dimethoxy-phenyl)-piperazin-i-ylH2-(2-fluoro-phenyl '5-methyl-2H-pyrazol-
3-yl]-methanone
- [2-{2-Fluoro-phenyl)-5-methyl-2H-pyrazo]-3-yl]-E4-(2-methylsulfanyl-phenyl)- piperazin*1-yl]-methanone
- [4-(4-Chloro-pheπyl)-piperazin-1-yl]-[2-(2-fluoro-phenyl 5"methyl-2H-pyrazol-3-yl]- methanone
- [2-(2-Fluoro-phθnyl)-5-mθthyl-2H-pyrazol-3-yl]-{4-naphthalen-1 -yl-ρiperazln-1 -yf )- methanone
- [4-(5-Chloro-2-methyl-phenyl)-piperazin-1-yl]-[2-(2-fluoro-phenyl)-5-methyi-2H- pyrazol-3-yl]-methanone
- [4-(2-Ethoxy-phenyl)-piperazin-1-yl]-[2-(2-fluoro-phenyl)-5-methyl-2H-pyrazol-3-y]]- methanone
- [4-{2,3-Dichloro-phenyl)-ρiperazin-1-yl]-[2-(2-fluoro-phenyl)-5-methyl-2H-pyrazol-3- yl]-methanone
- (2-(2-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(4-trifIuoromethyl-phenyl)- pipera∑in-1 -y!]-methanone
- [4-(5-Chloro-2-methoxy-phenyl)-piperazin-1-yl]-[2-(2-fluoro-phenyl)-5-methyl-2H- pyra∑ol-3-yl]-methanone - P^-Fluoro-phenyiy-δ-methyl^H-pyrazot-S-yq-H^-trifluoromethyi-phenyl)- piperazin-1 -yl]-methanone
- [4-(2,3-Dihydro-benzo[1 ,4]dioxin-6-yl)-piperazin-1 -yl]-[2-(2-fluoro-phenyl)-5-methyl- 2H-pyrazol-3-yl]-methanone
. SM-(4- 4-[2-(2-Fluoro-phenyl)-5-methyl-2H-pyrazole-3-carbonyl]-piperazin-1-y!}- phenyl }-m©thanesulfonam ide
- [2-(3-Fluoro»phenyl>-5-methyl-2H-pyrazθl-3-yl3-(4-ρhenyl-piperazin-1-yl)-methanone
- [2'(3-Fluoro-phenyl>5-methyl-2H-pyra∑ol-3-yl3-E4-(2-methoxy-phenyl)-piperazin-1- yl]-methanone
- E2-(3-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl3-E4-(3-trifluoromethyl-phenyl)- piperazin-1-yl]-methanone - [2-(3-Fluoro-pheny!>5'methyl-2H-pyrazol-3»yl]-[4-(4-fluoro-phenyl)-pipera∑iπ-1-yl]- methanone
. 1 -(4-{4-[2-(3-Fluoro-phenyl)-5-methyl-2H-pyrazole-3-carbonyl]-piperazin-1 -yl}- phenyl)-ethanonθ - [4-{2,4-Dimethyl-phenyl)-pipθrazin-1-yl]-[2-(3-fluoro-phenyl)-5-methyl-2H-pyrazol-3- yl]-methanone - [4-(3,4-Dichloro-phenyl)-piperazin-1-yl]-[2-(3-fluoro-phenyl)-5-methyl-2H-pyrazol-3- yl]-methanoπe
- [4-<3,4-Dimethyl-phenyl)-piperazin-1 -yl]«[2-(3-fluoro-phθnyl)-5-methyl-2 H-pyrazol-3- ylj-methanone
- [2-(3-Fluoro-phenyl)-5-methyi-2H-pyrazol-3-yl]-(4-o-tθlyl-pipera∑in-1-yl)-methanone
- [4-(2,3-Dimethyl-ρhenyl)-piperazin-1-yl]-[2-(3-fluoro-phenyl)-5-methyl-2H-pyrazol-3- yl]-methanone
- [4-(2-Ethyl-phenyI)-piperazin-1-yl]-[2-(3-fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]- methanone
- [4-(3-Chloro-phenyl)-piperaziπ-1-yl]-[2-(3-fluoro-phenyi)-5-methyl-2H-pyrazol-3-yl]- methanone
- [2-(3-FI uoro-pheny!)-5-methyl-2H-pyrazol-3-yl]-[4-(3-methoxy-phenyl)-piperazin-1 - yl]-methanone
- [2-(3-Fluoro-phenyl '5-methyl-2H-ρyrazol-3-yl]-(4-m-tolyl-piperazin-1-yl)-mθthanonθ '• [2-(3-Fiuoro-phenyl 5-methy]-2H-pyrazol-3-yl]-[4-(4-methoxy-phenyl)-piperazin-1- yl]-methanone
- [4-(2,4-Dimethoxy-phenyi)-piperazin-1-yl]-[2-(3-fluoro-phenyl)-5-methyl-2H-pyrazol- 3-yl]-methanoπe
- [2-(3-Fluoro-phenyl 5-methyl-2H-ρyrazol-3-yl]-[4-(2-methylsulfanyl-phenyl)- piperazin-1 -yl]-methanone
197 - [4-{4-Chloro-phenyl)-piperazin-1-yl]-[2-(3-fluoro-phenyl)-5-methyl-2H-pyra∑of-3-yl3- methaπone - [2-(3-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-ylH4-naphthalen-1-yl-piperazin-1-yl)- methanone - [4-(5-Chloro-2-methyl-phenyl)-piperazin-1-yl]-[2-(3-fluoro-phenyl)-5-meihyl-2H- pyra∑ol-3-yl]-m@thanone - [4-(2-Ethoxy-phenyI)-piperaziπ-1-yl]-[2-(3-fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]- methanone
- [4-(2,3-Dichloro-pheπyl)-pipθrazin-1-yl]-[2-(3-fluoro-phenyl)-5-methyl-2H-pyrazûl-3- yl]-methanone
- [2-(3-Fluoro-ph0nyl)-5-methyI-2H-pyrazol-3-yi]-[4-(4-trifluoromethyl-phenyl)- piperazin~1 -ylï-methanone
- [4-(5-Chloro-2-methoxy-phenyl)-piperazin-l-yl]-[2-(3-fluoro-phenyl)-5-methyl-2H- pyrazoI-3-yl]-methanone
- [4-(4-Benzyloxy-phθnyl)-pipθrazin-1-yij-[2-(3-fluoro-phθnyl)-5-methyl-2H-pyrazoi-3- yl]-methanone
- [2-(3-Fluoro-phθπyl)-5-mθthyl-2H-pyrazol-3-yl]-[4-(2-trifluoromethyl-phenyl)- piperazin-1 -yl]»methanone
- [4-(2,3-Dihydro-benzo[1 ,4]dioχin-6-yl)-piperazin-1 -yl]-[2-(3-fluoro-phenyl)-5-methyl-
2H-pyrazol-3-yl]-methanone
- N-(4-{4-[2-(3-Fluoro-phenyl)-5-methyI-2H-pyrazole-3-carboπyl]-piperazin-1-yl}' phenyl)-methanesulfonamide
- [2-(4-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl3-(4-phenyl-piperazin-1-yl)-methanone
- [2-(4-Fiuoro-phεnyl)-5-meîhyl-2H-pyrazol-3-yl]-[4-(2-mθthoxy-pheπyl)-piperazin-1- yl]-methanonθ
- [2-(4-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(3-trifluoromethyl-pheπyI)- piperazin-1 -yl]-methanone
- [2-(4-Fluoro-phenyl)-5-methyi-2H-pyrazoi-3-yl]-[4-(4-fluoro-phenyl)-piperazin-1-yl]- methanone
- 1-(4-{4-t2-(4-Fluoro-phenyi)-5-methyl-2H-pyrazole-3-carbonyl]-piperazin-1-yl}- phenyl)-ethanone
- [4-(2,4-Dimethyl-pheπyl piperazin-1-yl]-[2-(4-fluoro-phenyl)-5-mθthyl-2H-pyrazol-3- yl]-methanone
- [4-(3,4-Dichloro-phenyl)-piperazin-1-ylH2-(4-fluoro-phenyl)-5-methyl-2H-pyrazol-3- yl]-methanone
- [4-(3,4-Dimethyl-phenyl)-piperazin-1-yl]-[2-(4-fluoro-phenyl)-5-methyl-2H-pyrazol-3- ylj-methaπone
- [2-(4-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl3-(4-o-tolyl-piρerazin-1-yl)-methanone
198 - [4-(2,3-Dimethyl-phenyl)-pipθrazin-1-yl]-[2-(4-fiuoro-pheny])-5-methyl-2H-pyrazol-3- yl]-methanoπe - t4-(2-Ethyl-phenyl)-pipθrazin-1-yl]-[2-(4-fluoro-pheny])-5-methyl-2H-pyrazoi-3-yi]- ethanone - I4-(3-Chloro-ρhenyl)-p!pera2in-1-yl]-[2-(4-fluoro-phenyl)-5-mθthyl-2H-pyrazol-3-yl]- eîhanone - [2-(4-Fluoro-phenyl)-5-mθthyl-2H-pyrazol-3-yl]-[4-(3-methoxy-phenyl)-pipθrazin-1- yl]-rneîhanone - [2-(4-Fluoro-ρhenyl)-5-methyl-2H-pyrazol-3-yl]-(4-m-tolyl-pipera∑in-1-yi)- ethanone
- [2-(4-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(4-methoxy-phenyl)-piperazin-1- yl]-methanone - [4^2,4-Dimethoxy-phenyl)-piperazin-1-yi]-[2-(4-fluoro-phenyl 5-methyl-2H-pyrazol-
3-yl3-methanone
- [2-{4-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(2-meihylsulfanyl-phenyl)- piperazin-1 *yl]-methanone
- [4-(4-Chloro-phenyl)-plpera∑in-1-yl]-[2-(4-fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]- methanone
- [2-(4-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]-(4-naphthalen-1-yl-piperazin-1-yl)- ethanone
- [4-(5-Chloro-2-methyl-phenyl)-piperaziπ-1-yl]-[2-(4-fluoro-phenyl)-5-methyl-2H- pyra∑ol-3-yl]-mθthanone
- [4-(2-Ethoxy-phenyl)-piperazin-1-yl]-[2-(4-fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]- methaπoπe
- [4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-[2-(4-fluoro-phθnyl)-5-methyI-2H-pyrazo]-3- ylj-methanone
- [2-(4-Fluoro-phenyi)-5-methyl-2H-pyra∑ol-3-yl]-[4-(4-trifluoromethyl-phenyl)- piperazin-1-yl]-methanone
- [4-(5-Chloro-2-methoxy-phenyl)-piperazin-1-yl]-[2-(4-fluoro-phθnyi)-5-mθthyl-2H- pyra∑ol-3-yl]-mθthaπone
- [4-(4-Benzyloxy-phenyl)-piperazin-1-yl]-[2-(4-fiuoro-phenyl)-5-methyl-2H-ρyrazol-3- yQ-methanone
- [2-(4-Fluoro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(2-trifluoromethyl-phenyl)- piperazin-1-yl]-methanone
- [4-(2,3-Dihydro-bθnzo[1,4]dioxin-6-yl)-piperazin-1-ylH2-(4~fluoro-phenyl)-5-methyl-
2H-pyrazol-3-yl3-methanone
~ [2-(4-Methanesu!fonyl-phenyl)-5-methyl-2H-pyra∑ol-3-yl]-{4-phenyl-piperazin-1-yl)- methanone
199 - [2-{4-Methanesulfonyl-phenyl)-5-methyl-2H-pyrazol-3-y]]-[4-(3-trifluoromethyl- phenyl )-piperazin-1 -yl]-methanone - 1-(4_{4-[2-(4-Mθthanesulfonyl-phenyl)-5-methyl-2H-pyrazole-3-carbonyl]-piperazin-
1 -yl}-phθnyl ethanone _ [4_(2I4-Dimethyl-phenyl)-piperazin-1-yl]-[2-(4-methanesulfonyl-phenyl)-5-methyI-2H- pyra∑ol-3-yl3-methanonΘ - [2-(4-iViethanesulfonyl-phenyl)-5-methyl-2H-pyra∑oI-3-yl]-(4-o-tolyl-pipθrazin-1-yl)- methanone - [4-(3-Chloro-ρhenyI)-pipera2in-1-yl3-E2-{4-methanesulfonyI-ρhenyl)-5-methyl-2H- pyrazol-3-yl]-methanone
- [2-(4-Methanesu]fonyl-phenyl)-5-methyl-2H-pyrazoI-3-yl]-[4-(3-methoxy-phθnyl)- piperazin-1 -y[]-methanone - [2-(4- θthanesulfonyl-phenyl)-5-methyl-2H-pyra∑oI-3-yl]-(4-m-toly!-piperazin-1-yi)- methanone
- [4-(2,4-Dlmethoxy-pheπyl)-pipθra2in-1-yl]-[2-(4-methanθsulfonyl-pheny])-5-methyl-
2H-pyrazol-3-yl]-methanone
- [2-(4-Methanesuifoπyl-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(2-methylsulfanyI- phenyl)-pipθrazin-1-yl]-methanone
- [4-(4-Chloro-phenyl)-piperazin-1-yl]-[2-(4-methanesulfonyl-phenyl)-5-methyl-2H- pyrazol-3-yl]-methanone
- [4-(5-ChIoro-2-methyl-phenyI)-pipθrazin-1-yl]-[2-(4-methaπesuifonyl-phθnyl)-5- methyl-2H-pyrazol-3-yi]-methanone
- [4-(2-Ethoxy-phenyl)-piperazin-1-yl]-[2-(4-methanesulfonyl-phenyl)-5-mθthyl-2H- pyrazol-3-yl]-methanone
- [4-(2,3-Dichloro-phθnyl)-piperazin-1-yl]-[2"(4-methaπesulfonyl-phenyl)-5-methyl-2H- pyra2θi-3-yl]-methanone
- [2-(4-Methanesulfonyl-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(4-trifluoromethyl- phenyl)-plperazin-1~yi]-methanone
- [4-(4-Benzyioxy-phenyl)-piperazin-1-yl]-[2-(4-methanesulfonyl-phθnyl)-5-methyl-2H- pyrazol-3-yl]-methanone
- [2-(4-Methanesulfonyl-phenyl)-5-methyl-2H-pyrazoI-3-yl]-[4-(2-trifiuoromθthyl- ρhenyl)-piperazin-1-yl]-methanone
- [4-(2,3-Dihydro-benzo[1 ,4]dioxin-6-yi)-piperazin-1 -yl]-[2-(4-methanesulfonyl-ρhenyl)-
5-methyl-2H-pyrazol-3-yl]-methanone
- [2-(3-Chloro-phenyl)-5»methyl-2H-pyrazol-3-yl]-{4-phenyl-piperazln-1-yl)-methanone
- [2-(3-Chloro-phenyl)-5-methyl-2H-pyrazoi-3-yl]-[4-(2-methoxy-phenyl>-piperazin-1- yl]-methanone
200 - [2-{3-Chloro-phenyl)-5-methyl-2H-pyrazol-3-y]]-[4-(3-trifluoromθthyI-phenyl)- piperazin-1-yl]-methanone
- [2-(3-Chloro-pheny])-5-meihyl-2H-pyrazol-3-yl]-I4-(2,4-dimθthyi-phenyl)-piperazin-1- yl]-methanoπe
- [2-(3-Chloro-phenyl)-5-methyl-2H-pyra2θl-3-yl3-[4-(3,4-dimethyl-ρhenyl)-ρipθrazin-1- ylj-methanone
- [2-(3-Chloro-phenyl S-methyI-2H-pyrazol-3-yl]-{4-o-tolyi-piperazin-1-yl)-methanone
-[2-(3-Ch]oro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-{2,3-dimethyl-phθnyl)-piperazin-1- yl]-methanone
- [2-(3-Chloro-phenyl)-5-methyl-2H-pyrazol-'3-yl]-[4-{3- ethoxy-phenyl)-piperazin-1- yl]-methanone
- [2-(3-Chloro-phenyl)-5-methyl-2H-pyra∑ol-3-yl3-(4-m-tolyl-piperazin-1-yl)-mθthanone
- [2-(3-Chloro-phenyi)-5-methyI-2H-pyrazof-3-yl]-[4-(2,4-dlmethoxy-phenyl)-piperazin-
1-yl]-methaπone
- [2-(3-Chloro-phenyi)-5-methyl-2H-pyrazol-3-yl]-[4-(2-methylsulfanyl-phenyl)- piperazin-1-yl]-methanone
- [2-(3-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(4-chloro-ρhenyl)-piperazin-1-yl]- methanone
- [2-(3-Chloro-phθnyl)-5-methyl-2H-pyrazol-3-yl]-(4-naphthalen-1 -yl-piperazin-1 -yl)- ethanone
- [2-(3-Chloro-phθnyl)-5-mθthyl-2H-pyrazol-3-yl]-[4-(2-ethoxy-phenyl)-piρerazin-1-yl]- methanone
- [2-(3-Chloro-phenyl)-5- ethyl-2H-pyrazol-3-yt]-(4-(2,3-dichloro-phenyl)-pipθrazin-1- yl]-methanone
- [2-(3-Chloro-phenyI)-5-methyl-2H-pyrazol-3-yl]-[4-(4-trifluoromethyl-phenyl)- plρerazin-1-y]J-methanone
- [4-(5-Ch]oro-2-methoxy-phenyl)-pipθrazîn-1-yl]-[2-(3-chloro-phenyl)-5-methyl-2H- pyrazoi-3-yl]-methanone
- [4-(4-Benzyloχy-phenyi)-pîpera2in-1-ylH2-(3-chloro-phenyl)-5-methyl-2H-pyrazol-3- yl]-methanone
- [2-(3-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(2-trifluoromethyl-ρhenyl)- piperazin-1 -yl]-methanone
- [2-(3-Chloro-phenyl)-5-meîhyl*2H-pyrazol-3-yl3-[4-(2,3-dihydro-benzo[1,4]dioxin-6- yl)-piperazin-l -yl]-methanone
- [2-(4-Chloro-phenyl)-5-methyl-2H-pyrazoi-3-yl]-(4-phenyl-piperazin-1-y])-methanone
- [2-(4-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(2-methoxy-phenyl)-piperazin-1- yl]-methanone
201 - [2-(4-Chloro-phenyl)-5-mθthyl-2H-pyrazol-3-yl]-[4-(3-trifluoromethyl-phenyl)- piperazin«1-yl]-methanone
- I2-(4-Chloro-phenyl)-5-mθthyl-2H-pyrazol-3-yl]-I4-(4-fluoro-phenyl)-piperazin-1-yl]- methanone
- 1-(4-{4-[2-(4-Chloro-phenyl)-5-meihyl-2H-pyrazole-3-carbonyl]-piperazin-1-yl}- phenyl ethanon@ - [2-(4-Chloro-phenyl)-5-methyl-2H-pyra∑ol-3-ylH4-(3,4-dichloro-phaπyl)-piperazin-1- yl3-methanone - [2-(4-Chloro-phenyl)-5-methyl-2H-pyra∑ol-3-yl]-î4-(3,4-dimethy[-phenyl)-piperazin-1- yl]-mθthanone
- I2-(4-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-(4-o-tolyl-piperazin-1-yl)-methanone
- [2-(4-Ch]oro-phenyl>5-methyl-2H-ρyrazol-3-yl]-[4-(2,3-dimethyl-phθnyl)-piρerazin-1- yl]-methanoπe - [2-(4-Chloro-phenyl)-5-methyl-2H-pyrazoi-3-yl]-[4-(2-ethyl-phenyl)-piperazin-1-yl3- methanone - [2-{4-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(3-chloro-phenyl)-pipθrazin-1-yl]- methanoπe
- [2-{4-ChIoro-pheny])-5-methyl-2H-pyrazol-3-yi]-(4-m-tolyl-piperazin-1-yl)-methanoπe
- [2> 4-Chloro-phenyl)-5-mθthyl-2H-pyrazol-3-yl]-[4-(4-methoxy-phenyl)-piperazin-1- yl]-methanone
- [2-(4-Chloro-phenyl)-5-methyl-2H-pyrazot-3-yl]-[4-(4-chloro-phenyl)-pipθrazin-1-yl]- methanone
- [2-(4-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-(4-naphthalθn-1-yl-piperazin-1-yl)- methanone
- [4-(5-ChIoro-2-methyI-phenyl piperazin-1-yl]-[2-(4-chloro-phθnyl)-5-mθthyl-2H- pyrazol-3-yl3-meihanoπe
- [2-(4-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yI]-[4-(2,3-dichloro-phenyl)-pipθrazin-1- yl]-methanone
- [4-(5-Chloro-2-methoxy-phenyl)-piperazin-1-yl]-E2-(4-ch!oro-phenyl)-5-methyl-2H- pyrazoi-3-yl]-methanone
- [4-(4-Benzyloxy-phenyl}*piperazin-1-yl]-[2-(4-chloro-phenyl)-5-mθthyl-2H-pyrazol-3- yl]-methanone
- [2-{4-Chloro-phenyl)-5-methyl-2H-pyrazol-3-ylH4-(2,3-dihydro-bθnzo[1,4]dioχin-6- yl)-piperazin-1 -yl]-methanone
- (5-Methyl-2-p-tolyl-2H-pyrazol-3-yl (4-phenyl-piperazin-1-yl)-mθthanonθ
- (5-Methyl-2-p-tolyl-2H-pyrazol-3-yl)-[4-{3-trifluoromethyl-phenyl)-piperazin-1-yl]- methanone
•> 1- 4-[4-(5-Methyl-2-p-toIyl-2H-pyra∑ole-3-carbonyl)-piperazin-1-yI]-phenyl}-ethanone
202 - [4-(3,4-Dichloro-phenyl)-piperazin-1-yl]-(5-mθthyl-2-p-tolyl-2H-pyrazol-3-yl)- methanone
- (5-Methyl-2-p-tolyl-2H-pyrazol-3-yl)-(4-o-tolyl-piperazin-1-yl)-methanone - [4-{2,3-Dlmethyl-phenyl)-piperazin-1'yl]-(5-methyl-2-p-tolyl-2H-pyrazol-3-yl)- ethaπone
- [4-(2-EthyI-ρhenyl)-pipera∑in-1-yl3-(5-methyl-2-p-tolyl-2H-pyrazol-3-yl)-methaπone
- ^-(S-Chloro-pheny -piperazin-l-ylJ^S-methyl^p-tolyl^H-pyrâzol-S-y -meîhanone
- [4-(3»Î 3ethθ5 y-phenyl)-piperazin-1'yl]-(5-meîhyl-2-p-tolyl-2H-pyrazol-3-y])- ethanone
- (5-Methyl-2-p-tolyl-2H-pyra∑ot-3-yIH4-m-tolyl-pipera∑in- 1 ~yl)-meîhanone - [4-(4-Methoxy-pheny])-piperazln-1-yl3-(5-methyl-2-p-toiyl-2H-pyrazol-'3-yl)- methanone
- [4-(2,4-Dimθthoxy-phenyl)-piperazin-1-yl]-(5-methyl-2-p-tolyl-2H-pyrazol-3-yl)- methanone
- [4-(2-Methylsulfanyl-phenyl)-pipera∑in-1-yl3-(5-methyl-2-p-tolyl-2H-pyrazol-3-yl)- methanoπe
- [4-(4-Chloro-phenyl)-piperazin-1-yl]-(5-methyl-2-p-tolyl-2H-pyrazol-3-yl)-methaπone
- (5-Methyl-2-p-tolyl-2H-pyrazoi-3-yl)-(4-naphthalen-1 -yl-ρiperazin-1 -yl)-methanone - [4-(5-Chloro-2-mθthyl-phenyl)-piperazin-1-yl]-(5-methyl-2-p-tolyl-2H-pyrazol-3-yl)- methanone
- [4-(2-Ethoxy-phθπyl)-piperazin-1-yri-(5-methy]-2-p-tolyl-2H-pyrazol-3-yl)-methanonθ
« [4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-(5-methyl-2-p-tolyl-2H-pyrazol-3-yl)- methanone
- (5-Methyl-2-p-tolyl-2H-pyrazol-3-yl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]- methanone
- [4-(5-Chloro-2-methoxy-phθny[)-pipera2in-1-yl]-(5-methyl-2-p-tolyl-2H-pyrazol-3Ni)- methaπone
- [ (4-Benzyloxy-phenyl)-piperazin-1-yl]-(5-methyl-2-p-toly|-2H-pyrazol-3-yl)- methaπone
- (5-Methyl-2-p-tolyl-2H-pyrazol-3-yl>[4-(2-trifluoromethyl-phenyi)-piperazin-1-yi]- methanone
- [4-(2,3-Dihydro-benzo[1 ,4]dioxin-6-yl)-piperazin-1 -yl]-(5-methy]-2-p-tolyi-2H-pyrazol- 3-yl)-methanone
- N-{4-[4-{5-Methyl-2-p-tolyI-2H-pyrazole-3-carbonyl)-piperazin-1-yl]-phenyl}- ethanesulfonamide
- (5- θthyl-2-m-tolyl-2H-pyrazol-3-yl)-(4-phenyl-pipθra∑in-1-yl methanone
[4-(2-Meîhoxy-phenyl)-pIperazin-1-yl]-(5-methyl-2-m-tolyl-2H-pyrazol-3-y])- meîhanone
203 - (5-Methyl-2-m-tolyl-2H-pyrazol-3-yl)-[4-(3-trifluoromethyl-phenyl)-piperazln-1-yl]- methanone
- [4-(4-Fluoro-phenyl)-pîperazin-1-yt]-(5-methyI-2-m-tolyl-2Hl-pyrazol-3-yl)-methanone
• H4-[4-(5- ethyl-2-m-tolyl-2H-pyrazole-3-carbonyl)-piperazin-1-yl3-phenyl}- βthanone
- [4-{2,4-Dimθthyl-phβn l)-pipera2in-1-y!3-(5-methyl-2-m-iolyl-2H-pyrazoI-3-yI)- mβîhanone
- [4-(3,4-Dichloro-ph@nyI)-plperazin-1-yl]-(5-rnethyI-2-m4olyl-2H-pyra∑ol-3-yl)- methanone
- [4-(3,4-Dîmethyl-phenyl)-piperazin-1-yl3-(5-methyl-2-m-îolyl-2H-pyrazol"3-yI)- methanone
- (5-Methyl-2-m-tolyl-2H-pyrazoI-3-yl)-(4-o-tolyl-pipera∑in-1-yl methanone
- [4-(2,3-Dimethyl-phenyl)-piperazin-1-yl]-(5-methyl-2-m-tolyl-2H-pyra∑ol-3-yl)- ethanone
- [4-(2-Ethyl-pheπyl)-piperazin-1-yl3-(5-methyi-2-m-tolyl-2H-pyrazol-3-yl)-methanone
- f4-(3-Chloro-phenyl)-piperazin-1-yl]-(5-mθthyl-2-m-toiyl-2H-pyrazol-3-yl)-methanone
- ^-(S-Methoxy-phenylJ-piperazin-l-ylJ-îδ-methyl^-m-tolyl^H-pyrazol-S-yl)- methanone
- (5-Methyl-2-m-to!y]-2H-pyrazoi-3-yl)-(4-m-tolyl-pipera∑in-1'yi)-methanone
- [4-(4-Methoxy-phenyl)-piperazin-1-y!]-(5-methyl-2-m-toIyl-2H-pyrazoI-3-yl)- methanone
- [4-(2,4-Dimethoxy-phenyl)-piperazln-1-yl]-(5-methyl-2-m-tolyI-2H-pyrazol-3-yl methanone
- [4«(2-Methylsulfanyl-phenyi)-piperazln-1-yl]-(5-methyl-2-m-tolyl-2H-pyrazoi-3-yf)- methanone
- [4-(4-Chloro-phenyl)-piperazin-1-yl]-(5-methyl-2-m-tolyl-2H-pyrazol-3-yî)-methanone
- (5-Mθthyl-2-m-tolyl-2H-pyrazol-3-yl)-{4-naphthalen-1-yI'piperazin-1-yl)-methanonθ
- [4-(δ-Chioro-2-methyl-phenyi)-piperazin-1-yl]-(5-methy|-2-m-tolyl-2H-pyrazo]-3-y[)- methanone
- [4-(2-Ethoxy-phenyl)-piperazin-1-yl]-(S-methyl-2-m-tolyl-2H-pyrazol-3-yl)-methanone
- [4-(2,3-Dichloro-phenyl)-pipθrazin-1-yl]-(δ-methyI-2-m-toly]-2H-pyrazol-3-y])- methaπone
- (δ-Methyl-2-m-tolyl-2H-pyrazol-3-yl)-[4-(4-trifiuoromethyl-pheny])-piperazin-1-yl]- methanone
- [4-(δ-Chloro-2-methoxy-phenyl)-pîρeraziπ-1-yl]-(δ-methyl-2-m-toly]-2H-ρyrazol-3-yl)- methanone
- [4-(4-Beπzyloxy-phenyl)-piperazin-1-yl]-(5-methy!-2-m-tolyl-2H-ρyrazoi-3-yl)- methanone
204 - (δ-Methyl-2-m-tolyl-2H-pyrazol-3-yl)-[4-(2-trifluoromethyl-phenyl)-piperazin-1-y]]- methanone
- [4-(2)3-Dihydro-benzoI1 ,4]dioxin-6-yl)-piperazin-1 -yi]-(δ-methyl-2-m-tolyl-2H- pyrazol-3-yl)-methanoπe
- H-{4-[4-(5-Methyl-2-m-tolyl-2H-pyra∑olθ-3-carbonyl)-piρerazin-1-yi]-phenyl}- me hanesulfonεimidΘ
- (2H-lndazûl-3-ylH4-phenyl-pipβra∑in-1 -yl)-methanone - (2H-lπda∑oi-3-yl)-[4"(â-meîhoxy-phenyl pipera∑in-1-yl]-mβthanone - (2H-lndazol-3-yl)-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone _ [4-(4.Fluorσ-phenyl)-pipθrazin-1-yl3-(2H-indazol-3-yi 'methanone
- 1 -{4-[4-(2H-lndazûle-3-carbonyl)-piperaziπ-1-yl3-phenyl}-ethanone - [4-(2!4-Dimethyl-phθnyl)-piperazin-1-yl3-(2H-indazoi-3-yl)-methanone - [4-(3,4-Dichloro-phenyl)-pipera∑in-1-yl]-(2H-iπda∑oi-3-yl)-mθthanonθ - [4-(3,4-Dimθthyl-phenyl piperazin-1-yl]-(2H-indazol-3-yl>-methanone
- (2H-lndazol-3-yl)-(4-o-tolyl-pipθrazin-1 -yl)-methanone - [4-(2,3-Dlmethyl-phenyl)-piperazin-1-yl]-(2H-indazol-3-yl)-methanone - [4-(2-EthyI-phenyl)-piperazin-1-yl]-(2H-indazoi-3-yl)-methanone - [4-(3-Chloro-phenyl)-piperazin-1-yi]-(2H-indazol-3-yl)-methanone - (2H-lndazol-3-yl)-[4-(3-methoxy-phenyl)-piperazin-1-yl]-methanone - (2H-lndazol-3-yl)-(4-m-toiyl-piperazin-1-yl)-methanone - (2H-lndazol-3-yI)-[4-(4-methoxy-phenyl)-piperazin-1-yl]-methanone - [4-(2,4-Dimethoxy-phenyl)-piperazin-l-yl]-(2H-indazol-3-yl)-methanonθ - (2H-lndazoI-3-yl)-[4-(2-methylsulfanyl-phenyl)-piperazin-1-yl]-methanone . [4-(4-Chloro-phenyl)-piperazin-1-yl]-(2H-indazol-3-yl)-mθthanone - (2H-lndazol-3-yi)-{4-naphthalen-1-yl-piperaziπ-1-yl)-methanone - [4-(5-Chloro-2-methyl-phenyl)-plperazin-l-yl]-(2H-indazol-3-yl)-methanoπe - [4-{2-Ethoxy-phenyi)-piperazin-1-yl]-(2H-indazoI-3-yl)-methanone - [4-(2,3-Dichloro-ρhenyl)-piρerazin-1-yl]-(2H-indazol-3-yl)-mθthanonθ - (2H-lπdazoI-3-yl)-[4-(4-trifluoromethyI-phenyl)-piperazin-1-yl]'methanone - [4-(5-Chloro-2-methoxy-phenyl)-piperazin-1-yl]-(2H-indazol-3-yl)-mθthanone - [4-(4-Bθnzyloxy-phθπyl)-piperazin-1-yl]-(2H-indazol-3-yI)-methanone - (2H-lndazol-3-yl [4-(2-trifluoromethyl-phenyl piperazin-1-yl]-methanone
- [4-(2,3-Dihydro-benzo[1 ,4]dioxln-6-yl)-piperazin-1 -yl]-(2H-indazol-3-yl)-methanone - N_{4-[4-(2H-lndazolθ-3-carboπyl)-piperazin-1-yl]-phenyl}-methanesulfonamidθ
- (2-MethyM -quino!in-2-yl-1 H-pyrrol-3-yl)-(4-phenyl-piperazin-1 -yl)-methanone - [4-(3,4-Dichloro-pheπyI)-piperazin-1-ylH2-methyl-1-qulnolin-2-yl-1 H-pyrrol-3-yl)- methanone
205 - [4-(2- ethoxy-phenyl)-plperazin-1 -yl]-(2-methyl-1 -quinolin-2-yl-1 H-pyrrol-3-yl}- methanoπe
- [4-{3,4-Dimethyl-phenyl)-ρiperazin-1 -yl]-(2-methyl-1 -quiπolin-2-yl-1 H-pyrrol-3-yl)- methanone
- [4-(3-Chloro-phenyl}-plperazin-1-yl]-(2-methyl-1 -quinolin-2-yl-1 H-pyrrol-3-yl)- methanone
. [4^3,4-DimΘthyl-phenyl)-pipera∑in-1 -yl]-(1 -isoquinolin-1 -yl-2-methyl-1 H-pyrrol-3-yl)- methanone
- [4-(3-Chloro-phenyl)-pipera∑in-1-ylHl-isoquinolin-1-yl-2-methyl-1H-pyrrol-3-yi)- methanone
- (3,5-Dimθthyl-1-phenyl«1H-pyrazol-4-yl)-[4-(3-methoxy-phenyl>pipera∑in-1-yl]- methanone
- N-{4-[4-(3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carbony])-piperazin-1-y]]-phenyl}- methanesulfoπamide
- [2-(4- ethoxy-ρhenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(3-methoxy-phenyl)-piperazin-1- yl]-methanone
- N-(4-{4-[2-(4-Methoxy-ρhenyl)-5-methyl-2H-pyrazo]e-3-carboπyl]-piperazin-1-yl}- phenyl)-methanesuIfonamide
- [2-(3-Methoxy-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(3-mθthoxy-phθnyi)-piperazin-1- ylj-methanone
- N-(4-{4-[2-{3-Methoxy-phenyl)-δ-methyl-2H-pyrazole-3-carboπyl]-pipθrazin-1-yl}- phenyl)-mθthanesulfonamidθ
- (5-Methyl'2-phenyl-2H-pyrazoi-3-yl)-[4-(2-trifluoromethyl-pheπyl)-pipera∑iπ-1-yl]- ethanone
- [4-(4-BenzyIoxy-phenyi)-piperazin-1-yI]-[2-(2-fluoro-phenyl)-δ-methyl-2H-pyrazol-3- yl]-methanone
- N-{4-{4-[2-(4-Fluoro-phenyl)-δ-methyl-2H-pyrazole-3-carboπyl]-piperaziπ-1-yl}- ρhenyl)-methanesulfonamide
- [2-(4-MethanesuIfonyl-phenyl)-δ-methyl-2H-pyrazol-3-yl]-[4-(2-methoxy-phenyl)- piperazin-1 -yl]-methanone
- [4-(4-Fluoro-phenyl)-pïperazin-1-yl3-[2-(4-methanesulfonyl-phenyl)-δ-methyl-2H- pyrazol-3-yl]-methanone
- [4-{3,4-Dichloro-phenyI)-piperaziπ-1-y!]-[2-(4-methanesulfonyl-phenyl)-δ-methyl-2H- pyra∑ol-3-y.]-methanone
- [4-(3,4-Dimethyi-phenyl)-pipθrazin-1-yl]-[2-(4-mθthanθsulfonyl-phenyl)-δ-methyl-2H- pyrazol-3-yl]-methanone
- [4-(2,3-Dimethyl-phenyl)-piperazin-1-yl]-[2-{4-meîhanesulfûnyl-phenyl)-5-methyl-2H- pyrazol-3-yl]-methanone
206 - [2-(4-Methanesulfoπyl-phenyl)-δ-methyI-2H-pyrazol-3-yl]-[4-(4-methoxy-phenyl)- piperazin-1 -yI]-methanone - E2-(4-MethanesuIfonyl-phenyl δ-methyl-2H-pyrazoI-3-yi]-(4-naphthaien-1-yi- piρerazin-1 -yl)-methanone
- [4-(5-Chlûro-2-methoxy-phenyl)-ρiperazin-1-yl]'[2-(4-methanesulfonyl-phenyl)-5- methyl-2H-pyra2θl-3-yl3-methanone
- M-(4_{4-[2-(4-iV.ethanΘSUlfûnyl-phenyl)-5-rnΘthyl-2H-pyra∑ole-3-carbonyl3-pipera∑in- 1 -yl}-phen i)-mθthanesulfonamidβ - [2-(3-Chloro-phenyI}-δ-methyl-2H»pyrazol-3-yt]-[4-(4-fluoro-phenyl)-pipera2in-1-yl]- methanone
- [2-(3-Chloro-phenyl)-5-methyl-2H-<pyra∑ol-3-ylH4-(3,4-dich[oro-pheπyl)-pîperazin-1- yl]-methanone - [2-{3-Chloro-pheπyl)-5-methyl~2H-pyrazol-3-yl]-[4-(2-ethyl-pheπyl)-piperazin-1-yl]- methanone
- [2-(3-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(3-chloro-ρheπyl)-pipθrazin-1-yi]- methanone
- [2-(3-Chloro-phenyl)-5-methyl-2H-pyra∑ol-3-yl]-[4-(4-methoxy-phenyl)-piperazin-1- y|]-methanone
- [ Cδ-Chloro^-methyl-pheny -piperazin-l-ylJ-^^S-chloro-pheny -δ-methyl^H- pyrazol-3-yl]-methanone
- N-(4-{4-[2-(3-Chloro-phenyl)-δ-methyl-2H-pyrazole-3-carbonyl]-piperazin-1-yl}« phenyl)-methanesuIfonamide
- [2-{4-Chloro-phenyl>-δ-methyl-2H-pyrazoI-3-yl]-[4-(2,4-dimethyl-ρhenyl)-piperazin-1- yl]»methanone
- [2-(4-Chloro-phenyl)-δ-methyl''2H-pyrazol-3-yl]-[4-(3-methoxy-phθnyl)-piperazin-1- yl]-methanone
- [2-(4-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-[4-(2l4-dimθthoxy-phθnyl)-piperazin-
1-yl]-methanone
- [2-{4-Chloro-phenyl δ-methyl-2H-pyrazol-3-yl]-[4-(2-methylsulfanyl-phenyi)- pipera∑in-1 -yl]-methanone
- [2-(4-Chloro-ρhenyl δ-methyl-2l-f-pyrazol-3-yl]-[4-(2-ethoxy-phenyl ρiperazin'1-yl]- ethanone
- [2-{4-Chloro-phenyl)-5-mθthyl-2H-pyrazol-3-yl]-[4-(4-trifluoromethyl-phenyl)- pipera2in-l -yi]-methanone
- [2-(4-Chloro-phenyl)-5-mθthy]-2H-pyrazol-3-yl3-[4-(2-trîfluoromethyl-phenyl)- piperazin-1 -yl]-methanone
- N-(4-{4-i;2-(4-Ch|oro-phenyl)-5-methyl-2H-pyrazole-3-carbonyl]-piperazin-1-yl}- phenyl)-methanesulfonamidθ - {4-{2-Methoxy-phenyl)-piperazin-1-yl]-(δ-methyl-2-p-tolyl-2H-pyrazol-3-yl)- methanone
. [4-(4-Fluoro-phθnyl)-piperaziπ-l-yl]-(5-methyl-2-p-tolyl-2H-pyrazol-3-yl)-methanone
. [4-(2,4-Dimethyl-phenyl piperazin-1-ylH5-methyI-2-p-toIyl-2H-pyrazol-3«yl)- methanone - [4-(3,4-Dim®thyl-phenyl)-ρipera∑in-1-yl3-(5-methyl-2-p-tolyl-2H-pyrazol-3-yi)- methanone
12. Produit selon la revendication 1, caractérisé en ce qu'il est choisi parmi : - [4-(3-Chloro-phéπyl)-pipérazin-1-yi]-(δ-méthyl-2-phényl-2H-pyrazol-3-yl)-méthanone (Exemple 1)
- [4-(3,4-Dîméfhyl-phényl)-piperazin-1-yl3-(5-méthyI-2-phényl-2H-pyrazol-3-yl)- méthanone (Exemple 2)
- [4-(3,5-Dichloro-phényl)-pipθrazin-1-yl]-(δ-méthy]-2-phényl-2H-pyrazûl-3-yl)- éthanone (Exemple E2)
- [4-(Quinoléin-4-y])-piperazin-1-yl]-(5-méthyl~2-phényI-2H-pyrazol-3-yl)-méthanone (Exemple 17)
- [4-(3-Chloro-phényl)-pipérazin-1-yl3-(δ-hydroxyméthyl-2-phényl-2H-pyrazoi-3-yl)- méthanone (Exemple E60)
- [4-(3,4-Méthyiènedioxy -phényl)-piperazin-1 -yl]-(δ-méthyi-2-phényl-2H-pyrazθl-3-yl)- méthanone (Exemple E30)
- [4-(3,δ-Diméthoxy-phényl)-piperazin-1-yl]-(δ-méthyl-2-phény]-2H-pyra∑ol-3-yl)- méthanone (Exemple E20)
- [4-(3,δ-Diméthyl-phényl)-piperazin~1-yl3-(δ-méthyl-2-phényl-2H-pyrazol-3-yl)- méthanone (Exemple E63)
- [4-(3-Dîfluorométhoxy-phényl)-piperazin-1-yl]-(5-méthyl-2-phényf-2H-pyrazol-3-yl)- méthanone (Exemple E74)
- [4-(3-Chloro-phényl)-piperazin-1-yl]-[δ-(2-méthyl-imidazoM-yl-méthyl)-2-phény]-2H- pyrazol-3-yl]-méthanone (Exemple E7δ)
- [4-(3,δ-Diméthoxy-phényl)-piperazin-1 -yi]-[5-(1 H-pyrrol-2-yl)-méthyl-2-phényi-2H- pyrazol-3-yl]-méthanone (Exemple E91)
- [4-(3,5-Diméthoχy-ρhényl)-ρlρerazin-1-yl]-i;5-(pyrrolidin"1-yl)-méthyl-2 hényl-2H- pyrazol-3-yl]-méthanoπe (Exemple E93)
- [4-(3-Carboxamido-phényl)"piperazin'1-y]]-(δ-trifIuorométhyl-2-phéπyl-2H-pyra∑o!-3- yl)-méthanone (Exemple E119)
- I5-(Azétidin-1-yl)-2-phényl-2H-pyrazo]-3-yl]-[4-(3,5-dimθthoxy-phényl)-piperazin-1- yl]-méthanone (Exemple E12Ô)
- [4-{3-Carboxamido-phényl)-piperazin-1-ylH2-phényl-2H-pyrazol-3-yl)-méthanone (Exemple E133)
208 - [4-(3-Carboxamido-phényl)-piperazin-1-yl]-(5-hydroxyméthy!-2-phényl-2H-pyrazol-3- yl)-méthanone (Exemple E134)
- [4-(3-Carboxamido-phényl)-piperazin-1-yl]-(5-méthyl-2-phényl-2H-pyrazol-3-yl)- méthanone (Exemple E23)
~ [4-(3,δ"Diméthoxy-phény])-piperazin-1-yl]-(5-hydroxyméthyl-2-phényl-2H-pyrazol-3- yl)-méthanone (Exemple E73)
- (5-Arnino-2-phéπyi-2H-pyrazol-3-yl>'ï4-(3,5-dimêthoxy-phényl)-pipera∑in-1-yl]- méthanon® (Exemple E99).
13. Produit selon la revendication 12, caractérisé en ce qu'il est choisi parmi ; - [4-(3-Carboxamido-phéπyl)-piperazin-1-yl]-(5-méthyl-2-phényl-2H-ρyra∑ol-3-yl)- méthanone (Exemple E23)
- [4-(3,5-Diméthoxy-phényl)-piperazin-1-yI]-(δ-hydroxyméthyl-2-phényl-2H~pyrazol-3- yi)-méthanone (Exemple E73)
- (δ-Amiπo-2-phény!-2H-ρyrazol-3-yi [4-(3,δ-diméthoxy-phényl)-piρerazin-1-yi]- méthanone (Exemple E99).
14. Composition pharmaceutique comprenant un produit selon l'une quelconque des revendications précédentes, en combinaison avec un excipient pharmaceutiquement acceptable.
15. Utilisation d'un produit selon l'une quelconque des revendications 1 à 13, comme agent inhibant la polymérisation de la tubuiine.
16. Utilisation d'un produit selon l'une quelconque des revendications 1 à 13, comme agent inhibant la prolifération de cellules tumorales.
17. Utilisation d'un produit selon l'une quelconque des revendications 1 à 13, pour favoriser la désagrégation d'amas de cellules provenant d'un tissu vasculaire.
18. Utilisation d'un produit selon l'une quelconque des revendications 1 à 13, pour la fabrication d'un médicament utile pour traiter un état pathologique.
19. Utilisation selon la revendication 18, dans laquelle l'état pathologique est le cancer.
209
PCT/FR2004/000168 2003-01-28 2004-01-26 Produits n-aryl-heteroaromatiques, compositions les contenant et utilisation WO2004078732A1 (fr)

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EP04705102A EP1590329A1 (fr) 2003-01-28 2004-01-26 Produits n-aryl-heteroaromatiques, compositions les contenant et utilisation
MXPA05008099A MXPA05008099A (es) 2003-01-28 2004-01-26 Productos n-aril-heteroaromaticos, composiciones que los contienen y su utilizacion.
JP2006505660A JP2006516656A (ja) 2003-01-28 2004-01-26 Ｎ−アリールヘテロ芳香族物質、それを含む組成物およびその用途
AU2004218260A AU2004218260A1 (en) 2003-01-28 2004-01-26 N-aryl heteroaromatic products, compositions containing same and use thereof
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TW200800946A (en) * 2005-08-15 2008-01-01 Astrazeneca Ab Substituted piperazines as metabotropic glutamate receptor antagonists
EP2009011A1 (fr) * 2006-04-14 2008-12-31 Takeda Pharmaceutical Company Limited Composé hétérocyclique azoté
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RU2501787C2 (ru) * 2007-11-02 2013-12-20 Метилджен Инк. Ингибиторы гистондеацетилазы
CN101597278B (zh) 2008-06-04 2013-04-17 中国中化股份有限公司 酰胺类化合物及其制备与应用
WO2010001258A2 (fr) * 2008-06-30 2010-01-07 Centre National De La Recherche Scientifique Inhibition de la croissance tumorale et de métastases
JP2012501344A (ja) * 2008-08-29 2012-01-19 トレヴェンティス コーポレイション アミロイド症を治療する組成物及び方法
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US9238643B2 (en) 2010-09-06 2016-01-19 Guangzhou Institutes Of Biomedicine And Health, Chinese Academy Of Sciences Amide compounds
PL2614052T3 (pl) * 2010-09-08 2015-06-30 Bristol Myers Squibb Co Nowe analogi piperazyny jako środki przeciw wirusowi grypy o szerokim spektrum
US9289365B2 (en) * 2011-10-24 2016-03-22 Avon Products, Inc. Compositions and methods for stimulating collagen synthesis in the skin
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