AR075238A1 - Compuestos de piridazinona - Google Patents
Compuestos de piridazinonaInfo
- Publication number
- AR075238A1 AR075238A1 ARP100100304A ARP100100304A AR075238A1 AR 075238 A1 AR075238 A1 AR 075238A1 AR P100100304 A ARP100100304 A AR P100100304A AR P100100304 A ARP100100304 A AR P100100304A AR 075238 A1 AR075238 A1 AR 075238A1
- Authority
- AR
- Argentina
- Prior art keywords
- phenyl
- pyridazin
- trifluoromethyl
- pyrazol
- substituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 11
- 125000001424 substituent group Chemical group 0.000 abstract 8
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 7
- 125000005843 halogen group Chemical group 0.000 abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 3
- VHVUTJZQFZBIRR-UHFFFAOYSA-N 1h-pyridazin-4-one Chemical compound OC1=CC=NN=C1 VHVUTJZQFZBIRR-UHFFFAOYSA-N 0.000 abstract 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 2
- FKWWVSRLGIPKLD-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]pyrazol-3-yl]pyridazin-4-one Chemical compound ClC1=CC(C(F)(F)F)=CN=C1N1N=C(C=2C(C=CN(N=2)C=2C=CC(Cl)=CC=2)=O)C=C1 FKWWVSRLGIPKLD-UHFFFAOYSA-N 0.000 abstract 1
- HATADCJHNNRIJY-UHFFFAOYSA-N 1-(4-methoxyphenyl)pyrazole Chemical compound C1=CC(OC)=CC=C1N1N=CC=C1 HATADCJHNNRIJY-UHFFFAOYSA-N 0.000 abstract 1
- -1 3, 5-dimethyl-1H-pyrazol-1-yl Chemical group 0.000 abstract 1
- WLWVEKJXYGYSBO-UHFFFAOYSA-N 3-(1-phenylpyrazol-3-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4-one Chemical compound FC(F)(F)C1=CC=CC(N2N=C(C(=O)C=C2)C2=NN(C=C2)C=2C=CC=CC=2)=C1 WLWVEKJXYGYSBO-UHFFFAOYSA-N 0.000 abstract 1
- YGKPLXQSJLTMCO-UHFFFAOYSA-N 3-(2-phenylpyrazol-3-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4-one Chemical compound FC(F)(F)C1=CC=CC(N2N=C(C(=O)C=C2)C=2N(N=CC=2)C=2C=CC=CC=2)=C1 YGKPLXQSJLTMCO-UHFFFAOYSA-N 0.000 abstract 1
- DEHRBVPGHLIAFC-UHFFFAOYSA-N 3-(4-ethyl-5-sulfanylidene-1h-1,2,4-triazol-3-yl)-1-(4-methylphenyl)pyridazin-4-one Chemical compound N1C(=S)N(CC)C(C=2C(C=CN(N=2)C=2C=CC(C)=CC=2)=O)=N1 DEHRBVPGHLIAFC-UHFFFAOYSA-N 0.000 abstract 1
- CTVYAQZYCLMRQD-UHFFFAOYSA-N 3-[1-(2-fluorophenyl)pyrazol-3-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4-one Chemical compound FC1=CC=CC=C1N1N=C(C=2C(C=CN(N=2)C=2C=C(C=CC=2)C(F)(F)F)=O)C=C1 CTVYAQZYCLMRQD-UHFFFAOYSA-N 0.000 abstract 1
- ZRNONHUOKAABFD-UHFFFAOYSA-N 3-[1-(3-chlorophenyl)pyrazol-3-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4-one Chemical compound FC(F)(F)C1=CC=CC(N2N=C(C(=O)C=C2)C2=NN(C=C2)C=2C=C(Cl)C=CC=2)=C1 ZRNONHUOKAABFD-UHFFFAOYSA-N 0.000 abstract 1
- ITQNASUIPYPYPQ-UHFFFAOYSA-N 3-[1-(3-methoxyphenyl)pyrazol-3-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4-one Chemical compound COC1=CC=CC(N2N=C(C=C2)C=2C(C=CN(N=2)C=2C=C(C=CC=2)C(F)(F)F)=O)=C1 ITQNASUIPYPYPQ-UHFFFAOYSA-N 0.000 abstract 1
- JMRNUSBGEKLLTL-UHFFFAOYSA-N 3-[1-(3-nitrophenyl)pyrazol-3-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4-one Chemical compound [O-][N+](=O)C1=CC=CC(N2N=C(C=C2)C=2C(C=CN(N=2)C=2C=C(C=CC=2)C(F)(F)F)=O)=C1 JMRNUSBGEKLLTL-UHFFFAOYSA-N 0.000 abstract 1
- YUCJVWLNVSVTMS-UHFFFAOYSA-N 3-[1-(4-methylphenyl)pyrazol-3-yl]-1-phenylpyridazin-4-one Chemical compound C1=CC(C)=CC=C1N1N=C(C=2C(C=CN(N=2)C=2C=CC=CC=2)=O)C=C1 YUCJVWLNVSVTMS-UHFFFAOYSA-N 0.000 abstract 1
- LQYKXNQLFYWMLV-UHFFFAOYSA-N 3-[2-(1,1-dioxothiolan-3-yl)pyrazol-3-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4-one Chemical compound FC(F)(F)C1=CC=CC(N2N=C(C(=O)C=C2)C=2N(N=CC=2)C2CS(=O)(=O)CC2)=C1 LQYKXNQLFYWMLV-UHFFFAOYSA-N 0.000 abstract 1
- SABOFQQPIQQDHH-UHFFFAOYSA-N 3-[2-(2-fluorophenyl)pyrazol-3-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4-one Chemical compound FC1=CC=CC=C1N1C(C=2C(C=CN(N=2)C=2C=C(C=CC=2)C(F)(F)F)=O)=CC=N1 SABOFQQPIQQDHH-UHFFFAOYSA-N 0.000 abstract 1
- NVEGQMXGKYTTGE-UHFFFAOYSA-N 3-[2-(3-nitrophenyl)pyrazol-3-yl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4-one Chemical compound [O-][N+](=O)C1=CC=CC(N2C(=CC=N2)C=2C(C=CN(N=2)C=2C=C(C=CC=2)C(F)(F)F)=O)=C1 NVEGQMXGKYTTGE-UHFFFAOYSA-N 0.000 abstract 1
- SQSVPLPGOKIQIC-UHFFFAOYSA-N 3-[2-(4-methylphenyl)pyrazol-3-yl]-1-phenylpyridazin-4-one Chemical compound C1=CC(C)=CC=C1N1C(C=2C(C=CN(N=2)C=2C=CC=CC=2)=O)=CC=N1 SQSVPLPGOKIQIC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract 1
- 125000002015 acyclic group Chemical group 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 201000000980 schizophrenia Diseases 0.000 abstract 1
Classifications
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P25/32—Alcohol-abuse
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- 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
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- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
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- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
La presente provee un compuesto que tiene el efecto de inhibir la PDE, y que es util como un medicamento para prevenir o tratar la esquizofrenia o etc. Reivindicacion 1: Un compuesto de la formula (1) donde R1 representa un sustituyente, R2 representa un átomo de hidrogeno, o un sustituyente, R3 representa un átomo de hidrogeno, o un sustituyentes, el Anillo A representa un anillo aromático que puede estar sustituido, y el Anillo B representa un anillo aromático de 5 miembros que puede estar sustituido; con la condicion de que se excluyan los siguientes compuestos 1-(2-clorofenil)-6-metil-3-{5-tioxo-4-[3-(trifluorometil)fenil]-4,5-dihidro-1H-1,2,4-triazol-3-il}piridazin-4(1H)-ona, 1-(4-clorofenil)-3-[4-(2-fluorofenil)-5-tioxo-4,5-dihidro-1H-1,2,4-triazol-3-il]-6-metilpiridazin-4(1H)-ona, 1-(4-clorofenil)-6-metil-3-{5-tioxo-4-[3-(trifluorometil)fenil]-4,5-dihidro-1H-1,2,4-triazol-3-il}piridazin-4(1H)-ona, 1-(4-clorofenil)-3-[4-(2-fluorofenil)-5-(metilsulfanil)-4H-1,2,4-triazol-3-il]-6-metilpiridazin-4(1H)-ona, 1-(4-clorofenil)-6-metil-3-{5-(metilsulfanil)-4-[3-(trifluorometil)fenil]-4H-1,2,4-triazol-3-il)piridazin-4(1H)-ona, 1-(2-clorofenil)-6-metil-3-{5-(metilsulfanil)-4-[3-(trifluorometil)fenil]-4H-1,2,4-triazol-3-il}piridazin-4-(1H)-ona, 3-(3,5-dimetil-1H-pirazol-1-il)-1-fenilpiridazin-4(1H)-ona, 1-(4-clorofenil)-3-{1-[3-cloro-5-(trifluorometil)piridin-2-il]-1H-pirazol-5-il}piridazin-4(1H)-ona, 3-[1-(2-fluorofenil)-1H-pirazol-5-il]-1-[3-(trifluorometil)fenil]piridazin-4(1H)-ona, 3-[1-(3-clorofenil)-1H-pirazol-5-il]-1-[3-(trifluorometil)fenil]piridazin-4(1H)-ona, 3-[1-(4-metoxifenil)-1H-pirazol-5-il]-1-[3-trifluorometil)fenil]piridazin-4(1H)-ona, 3-(1-fenil-1H-pirazol-5-il)-1-[3-(trifluorometil)fenil]piridazin-4(1H)-ona, 3-[1-(3-nitrofenil)-1H-pirazol-5-il]-1-[3-(trifluorometil)fenil]piridazin-4(1H)-ona, 3-[1-(1,1-dioxidotetrahidrotiofen-3-il)-1H-pirazol-5-il]-1-[3-(trifluorometil)fenil]piridazin-4(1H)-ona, 3-[1-(4-metilfenil)-1H-pirazol-5-il]-1-fenilpiridazin-4(1H)-ona, 3-[1-(4-clorofenil)-1H-pirazol-5-il]-1-fenilpiridazin-4(1H)-ona, 3-(4-etil-5-tioxo-4,5-dihidro-1H-1,2,4-triazol-3-il)-1-(4-metilfenil)piridazin-4(1H)-ona, 1-(4-clorofenil)-3-{1-[3-cloro-5-(trifluorometil)piridin-2-il]-1H-pirazol-3-il}piridazin-4(1H)-ona, 3-[1-(2-fluorofenil)-1H-pirazol-3-il]-1-[3-(trifluorometil)fenil]piridazin-4(1H)-ona, 3-[1-(3-clorofenil)-1H-pirazol-3-il]-1-[3-(trifluorometil)fenil]piridazin-4(1H)-ona, 3-[1-(3-metoxifenil)-1H-pirazol-3-il]-1-[3-(trifluorometil) fenil] piridazin-4(1H)-ona, 3-(1-fenil-1H-pirazol-3-il)-1-[3-(trifluorometil)fenil]piridazin-4(1H)-ona, 3-[1-(3-nitrofenil)-1H-pirazol-3-il]-1-[3-(trifluorometil)fenil]piridazin-4(1H)-ona, 3-[1-(4-metilfenil)-1H-pirazol-3-il]-1-fenilpiridazin-4(1H)-ona, 3-[1-(4-clorofenil)-1H-pirazol-3-il]-1-fenilpiridazin-4(1H)-ona, un compuesto de formula (2) donde el Anillo A' es un anillo de benceno que puede estar sustituido con un sustituyente seleccionado de un átomo de halogeno, y un grupo alquilo, R1' es (i) un grupo etilo, o (ii) un grupo fenilo que puede estar sustituido con uno o más sustituyentes seleccionados de un átomo de fluor, y un grupo trifluorometilo, R3' es un átomo de hidrogeno, o un grupo metilo, y Ra es un átomo de hidrogeno, o un grupo hidrocarbonado acíclico C1-4 que puede estar sustituido, un compuesto de la formula (3) donde el Anillo A'' es un anillo de benceno que puede estar sustituido con halogeno, y R1'' es un grupo acilo; o una sal de los mismos. Reivindicacion 2: El compuesto de acuerdo con la reivindicacion 1, donde R2 representa un átomo de halogeno, un grupo hidroxi, un grupo alquilo C1-10 que pueda estar sustituido, o un grupo alcoxi C1-10 que puede estar sustituido. Reivindicacion 3: El compuesto de acuerdo con la reivindicacion 2, donde R2 representa un grupo alcoxi C1-10 que puede estar sustituido con uno o más sustituyentes seleccionados de un átomo de halogeno, un grupo alcoxi C1-10, y un grupo cicloalquilo C3-7. Reivindicacion 4: El compuesto de acuerdo con la reivindicacion 2, donde R2 representa un grupo alcoxi C1-10. Reivindicacion 5: El compuesto de acuerdo con la reivindicacion 2, donde R1 representa un grupo fenilo que puede estar sustituido con 1 a 5 sustituyentes seleccionados de un átomo de halogeno, un grupo alquilo C1-10 que puede estar sustituido, y un grupo alcoxi C1-10 que puede estar sustituido. Reivindicacion 6: El compuesto de acuerdo con la reivindicacion 2, donde R1 representa un grupo fenilo que puede estar sustituido con 1 a 5 sustituyentes seleccionados de un átomo de halogeno, un grupo alquilo C1-10, y un grupo alcoxi C1-10. Reivindicacion 7: El compuesto de acuerdo con la reivindicacion 2, donde R1 representa un grupo fenilo que puede estar sustituido con 1 a 5 átomos de halogeno. Reivindicacion 8: El compuesto de acuerdo con la reivindicacion 2, donde R3 representa un átomo de H, o un grupo alcoxi C1-10 que puede estar sustituido. Reivindicacion 9: El compuesto de acuerdo con la reivindicacion 2, donde R3 representa un átomo de hidrogeno, o un grupo alcoxi C1-10. Reivindicacion 10: El compuesto de acuerdo con la reivindicacion 2, donde R3 representa un átomo de hidrogeno.
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