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AR066146A1 - Antagonistas de trpvi y usos de los mismos - Google Patents

Antagonistas de trpvi y usos de los mismos

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Publication number
AR066146A1
AR066146A1 ARP080101756A ARP080101756A AR066146A1 AR 066146 A1 AR066146 A1 AR 066146A1 AR P080101756 A ARP080101756 A AR P080101756A AR P080101756 A ARP080101756 A AR P080101756A AR 066146 A1 AR066146 A1 AR 066146A1
Authority
AR
Argentina
Prior art keywords
halo
alkyl
independently
phenyl
alkenyl
Prior art date
Application number
ARP080101756A
Other languages
English (en)
Inventor
Tafesse Laykea
Noriyuki Kurose
Original Assignee
Shionogi & Co
Purdue Pharma Lp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shionogi & Co, Purdue Pharma Lp filed Critical Shionogi & Co
Publication of AR066146A1 publication Critical patent/AR066146A1/es

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • 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
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • 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
    • C07D417/12—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 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
    • C07D417/14—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 three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Anesthesiology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Composiciones que comprenden una cantidad efectiva de. un compuesto de Formula 1 o un derivado farmacéuticamente aceptable del mismo, y métodos para tratar o prevenir una condicion como el dolor, UI, ulcera, IBD e IBS. Reivindicacion 1: Un compuesto de formula (1) o un derivado farmacéuticamente aceptable del mismo, caracterizado porque X es O, S, N-CN, N-OH, o N-OR10; W es N o C; la línea punteada denota la presencia o ausencia de un enlace, y cuando la línea punteada denota la presencia de un enlace o W es N, luego R4 está ausente, de lo contrario R4 es -OH, -OCF3, -halo, -alquil C1-6, -CH2OH, -CH2CI, -CH2Br, -CH2I, -CH2F, -CH(halo)2, -CF3, -OR10, -SR10, -COOH, -COOR10, -C(O)R10, -C(O)H, -OC(O)R10, -OC(O)NHR10, -NHC(O)R13, CON(R13)2, -S(O)2R10,o -NO2; R10 es -alquil C1-4; cada R13 es independientemente -H, -alquil C1-4, -alquenil C1-4, -alquinil C1-4, o -fenil; Ar1 es seleccionado del grupo de formulas (2); Ar2 un compuesto del grupo de formulas (3); c es el entero 0, 1 o 2; Y1, Y2, Y3 son independientemente C, N, u O; donde no más que uno de Y1, Y2, o Y3 puede ser O, y para cada Y1, Y2 e Y3 que sea N, el N está enlazado a un grupo R21 y para cada Y1, Y2, e Y3 que sea C, el C está enlazado a dos grupos R20, siempre que no haya más que un total de dos grupos alquil C1-6 sustituidos en todos los Y1, Y2, e Y3; R12a y R12b son independientemente -H o -alquil C1-6; E es =O, =S, =CH-alquil C1-5, =CH-alquenil C1-5, -NH-alquil C1-6, o =N-OR20; R1 es -H, -halo, -alquil C1-4, -NO2, -CN, -OH, -OCH3, -NH2, -C(halo)3, -CH(halo)2, -CH2(halo), -OC(halo)3, -OCH(halo)2, o -OCH2(halo); cada R2 es independientemente: (a) -halo, -OH, -O-alquil C1-4, -CN, -NO2, -NH2, alquil C1-10, alquenil C2-10, -alquinil C2-10, -fenil, o (b) un grupo de formula Q; donde Q es un compuesto del grupo de formulas (4); Z1 es H, OR7, SR7, -CH2-OR7, -CH2-SR7, -CH2-N(R20)2, o halo; Z2 es -H, -alquil C1-6, alquenil C2-6, -alquinil C2-6, -CH2-OR7, fenil, o -halo; cada Z3 es independientemente -H, -alquil C1-6, -alquenil C2-6, (C2-6)alquinil C2-6, o -fenil; Z4 es -H, -OH, -OR20, -alquil C1-6, o -N(R20)2; J es -OR20, -SR20, -N(R20)2, o -CN; siempre y cuando al menos un grupo R2 sea un grupo de Formula Q, y siempre que, cuando Z1 es -OR7 o -SR7, luego Z2 no es -halo; cada R3 es independientemente: (a) -H, alquil C1-6, o CH2OR7 o (b) dos grupos R3 juntos forman un puente , que está no sustituido o sustituido con 1, 2 o 3 grupos R8 independientemente seleccionados, y cuyo puente contiene opcionalmente -HC=CH- dentro del puente ; o (c) dos grupos R3 juntos forman un puente -CH2-N(Ra)-CH2-, un puente -CH2-N(C(:O)Rb)-CH2- o un puente -CH2-N(SO2)Rb)-CH2- Ra se selecciona de -H, -alquil C1-6, -cicloalquil C3-8, -CH2-C(O)-Rc, -(CH2)-C(O)-ORc, -(CH2)-C(O)-N(Rc)2, -(CH2)2-O-Rc, -(CH2)2-S(O)2-N(Rc)2, o -(CH2)2- N(RcS(O)2-Rc; Rb se selecciona de: (a) -H, -alquil C1-6, -cicloalquil C3-8, -heterociclo de 3 a 7 miembros, -N(Rc)2, -N(Rc)-cicloalquil C3-8, o -N(Rc)-heterociclo de 3 a 7 miembros; o (b) -fenil, -heteroaril de 5 o 6 miembros, -N(Rc)-fenil, o -N(Rc)-heteroaril de 5 a 10 miembros, cada uno de los cuales esta no sustituido o sustituido con 1, 2 o 3 grupos R7 independientemente seleccionados; cada Rc se selecciona independientemente de -H o -alquil C1-4; cada R7 es independientemente -H, -alquil C1-6, -alquenil C2-6, -alquinil C2-6, -cicloalquil C3-8, -cicloalquenil C5-8, -fenil, -haloalquil C1-6, -hidroxialquil C1-6, -alcoxi C1-6alquil C1-6, -alquil C1-6-N(R20)2, o -CON(R20)2 cada R8 y R9 es independientemente: (a) -alquil C1-6, -alquenil C2-6, -alquinil C2-6, -cicloalquil C3-8, -cicloalquenil C5-8 o -fenil, cada uno de los cuales esta no sustituido o sustituido con 1 o 2 grupos -OH; o (b) -H, -CH2C(halo)3, -C(halo)3, -CH(halo)2, -CH2(halo), -OC(halo)3, -OCH(halo)2, -OCH2(halo), -SC(halo)3, -SCH(halo)2, -SCH2(halo), -CN, -O-CN, -OH, -halo, -N3, -NO2, -CH=NR7, -N(R7)2, -NR7OH, -OR7, -C(O)R7, -C(O)OR7, -OC(O)R7, -OC(O)OR7, -SR7, -S(O)R7, o -S(O)2R7; cada R11 es independientemente -CN, -OH, -alquil C1-6, -alquenil C2-6, -halo, -N3, -NO2, -N(R7)2, -CH=NR7, -NR7OH, -OR7, -C(O)R7, -C(O)OR7, -OC(O)R7, o -OC(O)OR7; cada R14 es independientemente -H, -alquil C1-6, -alquenil C2-6, -alquinil C2-6, -cicloalquil C3-8, -cicloalquenil C5-8, -alcoxi C1-6alquil C1-6, -fenil, -C(halo)3, -CH(halo)2, -CH2(halo), -heterociclo de 3 a 7 miembros, -haloalquil C1-6, -haloalquenil C2-6, -haloalquinil C2-6, -hidroxialquenil C2-6, -hidroxialquinil C2-6, -alcoxi C1-6alquil C2-6, -alcoxi C1-6alquenil C2-6, alcoxi C1-6alquinil C2-6, -alcoxi C1-6cicloalquil C3-8, -CN, -OH, -halo, -OC(halo)3, -N3, -NO2, -CH=NR7, -N(R7)2, -NR7OH, -OR7,, -SR7, -O(CH2)bOR7, -O(CH2)bSR7, - O(CH2)bN(R7)2, -N(R7)(CH2)bOR7, -N(R7)(CH2)bSR7, -N(R7)(CH2)bN(R7)2, -N(R7)COR7, -C(O)R7, -C(O)OR7, -OC(O)R7, -OC(O)OR7, -S(O)R7, o -S(O)2R7, -S(O)2N(R7)2, -SO2C(halo)3, -SO2-heterociclo de 3 a 7 miembros, -CON(R7)2, -alquil C1-5-C=NOR7, -alquil C1-5-C(O)-N(R7)2, -alquil C1-6-NHSO2N(R7)2, o -alquil C1-6-C(=NH)-N(R7)2 cada R20 es independientemente -H, -alquil C1-6, o -cicloalquil C3-8; cada R21 es independientemente -H, -alquil C1-6, y los radicales del grupo de formulas (5); cada halo es independientemente -F, -Cl, -Br, o, -I; n es el entero 1, 2 o 3; p es el entero 1 o 2; cada b es independientemente 1 o 2; q es el entero 0, 1, 2, 3 o 4; r es el entero 0, 1, 2, 3, 4, 5 o 6; s es el entero 0, 1, 2, 3, 4 o 5; t es el entero 0, 1, 2 o 3; y m es el entero 0, 1 o 2.
ARP080101756A 2007-04-27 2008-04-25 Antagonistas de trpvi y usos de los mismos AR066146A1 (es)

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US92666107P 2007-04-27 2007-04-27
US93003607P 2007-05-11 2007-05-11
US93700307P 2007-06-21 2007-06-21
US96240907P 2007-07-27 2007-07-27

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EP (3) EP2604599A1 (es)
JP (2) JP5462784B2 (es)
KR (2) KR20100005725A (es)
CN (1) CN101932570B (es)
AR (1) AR066146A1 (es)
AU (1) AU2008243874B2 (es)
BR (1) BRPI0809795A2 (es)
CA (3) CA2756791C (es)
CO (1) CO6241153A2 (es)
CY (1) CY1115262T1 (es)
DK (1) DK2142529T3 (es)
ES (2) ES2571533T3 (es)
HR (1) HRP20140279T1 (es)
IL (2) IL201688A (es)
ME (1) ME02123B (es)
MX (1) MX2009011600A (es)
MY (1) MY148657A (es)
NZ (1) NZ580266A (es)
PE (2) PE20090422A1 (es)
PH (1) PH12013500848B1 (es)
PL (1) PL2142529T3 (es)
PT (1) PT2142529E (es)
RS (1) RS53212B (es)
TW (1) TWI362930B (es)
UY (1) UY31050A1 (es)
WO (1) WO2008132600A2 (es)

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Publication number Priority date Publication date Assignee Title
WO2002060446A1 (fr) 2001-01-29 2002-08-08 Shionogi & Co., Ltd. Preparation medicamenteuse contenant du 5-methyle-1-phenyle-2-(1h)-pyridone en tant que principe actif
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AU2008243874B2 (en) 2012-01-19
US20180208575A1 (en) 2018-07-26
JP5462784B2 (ja) 2014-04-02
US9365563B2 (en) 2016-06-14
IL225521A0 (en) 2013-06-27
CN101932570B (zh) 2014-11-26
US20160355499A1 (en) 2016-12-08
EP2604598B1 (en) 2016-04-06
CA2833209A1 (en) 2013-11-13
ES2571533T3 (es) 2016-05-25
US8889690B2 (en) 2014-11-18
PL2142529T3 (pl) 2014-06-30
CY1115262T1 (el) 2017-01-04
PH12013500848A1 (en) 2015-05-18
US8476277B2 (en) 2013-07-02
PT2142529E (pt) 2014-03-20
PE20130325A1 (es) 2013-03-18
HK1139949A1 (en) 2010-09-30
AU2008243874A1 (en) 2008-11-06
US8575199B2 (en) 2013-11-05
US20120177570A1 (en) 2012-07-12
CO6241153A2 (es) 2011-01-20
MX2009011600A (es) 2010-11-26
MY148657A (en) 2013-05-15
US20150018366A1 (en) 2015-01-15
PE20090422A1 (es) 2009-04-18
CA2756791C (en) 2016-09-13
JP2014015465A (ja) 2014-01-30
CA2685266A1 (en) 2008-11-06
IL201688A (en) 2017-01-31
EP2604599A1 (en) 2013-06-19
TW200911249A (en) 2009-03-16
US10584110B2 (en) 2020-03-10
UY31050A1 (es) 2008-07-03
US20090170868A1 (en) 2009-07-02
JP2010525048A (ja) 2010-07-22
ES2453947T3 (es) 2014-04-09
CA2756791A1 (en) 2008-11-06
BRPI0809795A2 (pt) 2014-10-07
EP2142529B1 (en) 2013-12-25
IL201688A0 (en) 2010-05-31
US20090176796A1 (en) 2009-07-09
WO2008132600A2 (en) 2008-11-06
EP2142529A2 (en) 2010-01-13
KR20130004524A (ko) 2013-01-10
HK1184152A1 (en) 2014-01-17
DK2142529T3 (da) 2014-02-10
RS53212B (sr) 2014-08-29
NZ580266A (en) 2012-03-30
ME02123B (me) 2014-08-29
WO2008132600A3 (en) 2009-03-12
CN101932570A (zh) 2010-12-29
TWI362930B (en) 2012-05-01
US20090170867A1 (en) 2009-07-02
EP2604598A1 (en) 2013-06-19
HRP20140279T1 (hr) 2014-04-25
CA2833209C (en) 2016-06-28
CA2685266C (en) 2014-01-28
PH12013500848B1 (en) 2015-05-18

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