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AR058406A1 - Antagonistas del receptor de proquineticina 1 - Google Patents

Antagonistas del receptor de proquineticina 1

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Publication number
AR058406A1
AR058406A1 ARP060105853A ARP060105853A AR058406A1 AR 058406 A1 AR058406 A1 AR 058406A1 AR P060105853 A ARP060105853 A AR P060105853A AR P060105853 A ARP060105853 A AR P060105853A AR 058406 A1 AR058406 A1 AR 058406A1
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Argentina
Prior art keywords
alkyl
phenyl
amino
pyridin
alkoxy
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ARP060105853A
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Janssen Pharmaceutica Nv
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Publication of AR058406A1 publication Critical patent/AR058406A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
    • 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
    • A61P1/12—Antidiarrhoeals
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other 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
    • C07D401/06—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 carbon chain containing only aliphatic 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
    • C07D401/12—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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

Antagonistas del receptor de proquineticina 1, y métodos para preparar estos compuestos, composiciones, intermediarios y derivados de los mismos y para el tratamiento de trastornos producidos por los receptores de proquineticina 1 o de proquinetina 1. Reivindicacion 1: Un compuesto de formula (1), donde, A1 es CF3, alcoxi C1-4, arilo, ariloxi, heterociclilo benzofusionado, o heteroarilo; donde arilo, ariloxi, y heteroarilo están opcionalmente sustituidos con pirazol-1-ilo [1,2,3]tiadiazol-4- ilo; o arilo, ariloxi, la porcion benzo del heterociclilo benzofusionado, y heteroarilo están opcionalmente sustituidos con uno a tres sustituyentes independientemente seleccionados del grupo formado por alquilo C1-6, hidroxialquilo C1-6, alcoxi C1- 6, halogeno, nitro, alquilo C1-6 halogenado, alcoxi C1-6 halogenado, alquiltio C1-6, alcoxi C1-6carbonilo, amino, alquil C1-6amino, di(alquil C1-6)amino, ciano, hidroxi, aminocarbonilo, alquil C1-6aminocarbonilo, di(alquil C1-6)aminocarbonilo, alcoxi C1-6carbonilamino, alquil C1-6carbonilo, alquiltio C1-6carbonilo, formilo, alquil C1-6sulfonilo, alquil C1-6sulfonilamino, aminosulfonilo, alquil C1-6aminosulfonilo, y di(alquil C1-6)aminosulfonilo; siempre y cuando A1 no sea 3,5-di-t-butil- fenilo; L1 es -(CH2)r-, -CH2-alquenil C2-4-, o -CH2CH2X(CH2)s-, donde L1 está opcionalmente sustituido con uno a dos sustituyentes independientemente seleccionados del grupo formado por alquilo C1-6, alquenilo C2-6, alquinilo C2-6, y halogeno; y, r es un numero entero de 1 a 5; de tal modo que r es mayor que o igual a 4 cuando A1 es alcoxi C1-4; s es un numero entero de 1 a 3; X es O o S; D es -P-A2; donde P es -(CH2)1-2- o -CH2CH=CH- cuando A2 es fenilo, heterociclilo benzofusionado, heteroarilo, o cicloalquilo C3-8; alternativamente, P es -(CH2)3-6- cuando A2 es hidrogeno, alcoxi C1-4, o alcoxi C1-4carbonilo; y donde P está opcionalmente sustituido con uno a dos sustituyentes independientemente seleccionados del grupo formado por alquilo C1-6, alquenilo C2-6, alquinilo C2-6, y halogeno; A2 es hidrogeno, alcoxi C1-4, alcoxi(C1-4)carbonilo, fenilo, heterociclilo benzofusionado, heteroarilo, tetrahidro-piranilo, piperidinilo, o cicloalquilo C3-8; donde fenilo, heteroarilo, la porcion benzo del heterociclilo benzofusionado, y cicloalquilo C3-8 están opcionalmente sustituidos con uno a tres sustituyentes independientemente seleccionados del grupo formado por alquilo C1-6, alcoxi C1-6, halogeno, alquilo C1-6 halogenado, alcoxi C1-6 halogenado, arilalcoxi C1-6, fenilo, N-isoindol-1,3-diona, alquiltio C1-6, alquil C1-6sulfonilo, alcoxi C1-6carbonilo, amino, alquil C1-6amino, di(alquil C1-6)amino, ciano, hidroxi, nitro, alquil C1-6carbonilo, alquiltio C1-6carbonilo, aminocarbonilo, alquil C1-6aminocarbonilo, di(alquil C1-6)aminocarbonilo, alquil C1-6carbonilamino, y un cicloalquiloxi C3-6 no fusionado; de tal modo que no más de dos sustituyentes en A2 son arilalcoxi C1-6, fenilo, N-isoindol-1,3-diona, o un cicloalquiloxi C3-6 no fusionado; siempre y cuando A2 no sea 3,5-di-t-butil-fenilo; W es N o C(Rw); donde Rw es H o alquilo C1-2; Q se selecciona del grupo formado por (a) a (g), donde (a) es -NH(CH2)Ar1 donde Ar1 es piridinilo opcionalmente sustituido con uno a tres sustituyentes alquilo C1-4 o un sustituyente seleccionado del grupo formado por alcoxi C1-4 y amino; siempre que cuando Ar1 es piridin-3-ilo no sustituido o piridin-4-ilo no sustituido, y A2 es 4-metoxi-fenilo, A1 no sea fenilo no sustituido o 3,4-dicloro-fenilo; (b) es -NHCH(Rz)-Ar2 donde Rz es H o alquilo C1-3; Ar2 es piridinilo, pirimidinilo, pirazinilo, la estructura de formula (2), 1,2,3,4-tetrahidro-[1,8]naftiridinilo, imidazo[1,2-a]piridinilo, o quinolinilo; de tal modo que el punto de union al 1,2,3,4-tetrahidro-[1,8]naftiridinilo está en la posicion 6 o 7, y el punto de union al quinolinilo está en la posicion 2, 3 o 4; y donde Ar2 está opcionalmente sustituido con uno a tres sustituyentes independientemente seleccionados del grupo formado por alquilo C1-4, trifluorometilo, hidroxil-alquilo C1-4, aminoalquilo C1-4, (alquil C1-4)amino-alquilo C1-4, di(alquil C1-4)amino-alquilo C1-4, alcoxi C1-4, cicloalquil C3-8amino, amino, (alquil C1- 6)amino, y di(alquil C1-4)amino; o Ar2 está opcionalmente sustituido con un grupo amino y tres sustituyentes independientemente seleccionados del grupo formado por alquilo C1-4 y alcoxi C1-4, donde el grupo alquilo C1-6 de alquil C1-6amino y di(alquil C1-6)amino está opcionalmente sustituido con amino, alquil C1-4amino, di(alquil C1-4)amino, cicloalquil C3-8amino, alcoxi C1-4, alquiltio C1-4, hidroxi, un heteroarilo de 5 a 6 miembros, o un heterociclilo de 5 a 6 miembros; donde un átomo de nitrogeno del heterociclilo de 5 a 6 miembros está opcionalmente sustituido con un sustituyente alquilo C1-4; y donde piridin-2-ilo y piridin-3-ilo están además opcionalmente sustituidos con N-pirrolidinilo, N-piperazinilo, N-piperidinilo, N- morfolinilo, N-tiomorfolinilo, -CH2-O-CH2-PH, y fenilo; donde el sustituyente fenilo de piridin-2-ilo y piridin-3-ilo está opcionalmente sustituido con uno a tres sustituyentes independientemente seleccionados del grupo formado por alquilo C1-4, alcoxi C1-4, y halogeno; siempre que cuando Q es -NHCH2(2-amino-piridin-3-il), y A1 es piridin-4-ilo, 4-alquil C1-6-fenilo, 3,4-dicloro-fenilo, o 4-metansulfonil-fenilo, A2 no sea 4-metoxi-fenilo; siempre que cuando Q es -NHCH2(2-amino-piridin-3- il), L1 es -(CH2)2- o .(CH2)5-, y A1 es metoxi, A2 no sea 4-difluorometoxi-fenilo o 4-metoxi-fenilo; siempre que cuando Q es -NHCH2(2-amino-piridin-3-il), y A1 es benzotriazol1-ilo, A2 no sea 4-difluorometoxi-fenilo; siempre que cuando Q es -NHCH2(2- amino-piridin-3-il), L1 es -(CH2)3-, y A1 es pirrol-1-ilo, A2 no sea 4-metoxi-fenilo; siempre que cuando Q es -NHCH2(2-amino-piridin-3-il), L1 es -(CH2)2-, y A1 es 4-nitro-fenilo o etoxi, A2 no sea 4-metoxi-fenilo; siempre que cuando Q es -NHCH2(2- amino-piridin-3-il), y A1 es 4-fluoro-fenilo, A2 no sea 4fluoro-fenilo; siempre que cuando Q es -NHCH2(6-amino-piridin-2-il), y A1 es 4-fluoro-fenilo, A2 no sea 4-trifluorometoxi-fenilo; siempre que cuando Q es .NHCH2(6-metil-piridin-2-il), y A1 es 4-metoxi-fenilo, A2 no sea 4-metoxi-fenilo; siempre que cuando Q es -NHCH2(imidazo[1,2-a]piridinil), y A1 es 4-fluoro-fenilo, A2 no sea 4-metoxi-fenilo; siempre que cuando Q es -NHCH2(piridin-4-il), y A1 es fenilo no sustituido o 3,4-dicloro-fenilo, A2 no sea 4-metoxi-fenilo; siempre que cuando Q es -NHCH2(4,6-dimetil-piridin-3-il), y A1 es 4-metoxi- fenilo, -P-A2 no sea -(CH2)5-metoxi; siempre que cuando Q es -NHCH2(4,6-dimetil-piridin-3-il), L1 es -(CH2)2-, y A1 es pirazol-1-ilo, A2 no sea 4- difluorometoxi-fenilo; siempre que cuando Q es -NHCH2(4,6-dimetil-piridin-3-il) y A1 es 4-metoxi-fenilo, A2 no sea 2-etil-fenilo, 4-etil-fenilo, 3-metoxi-fenilo, 3-ciano-fenilo, 3-nitro-fenilo, y 3-trifluorometil-4-nitro-fenilo; siempre que cuando Q es -NHCH2(4,6-dimetil-piridin-3-il) y A1 es quinolin-8-ilo, benzotriazol-1-ilo, 3,5-dimetil-pirazolilo, 2-fluoro-fenilo, 2-cloro-fenilo, 2-nitro-fenilo, 2-trifluorometil-fenilo, 2-difluorometoxi-fenilo, 3-difluorometoxi-fenilo, 2-trifluorometoxi- fenilo, 2,4-difluoro-fenilo, 2,6-difluoro-fenilo, 2,6-dicloro-fenilo, 2-cloro-4-fluoro-fenilo, 2,6-difluoro-4-metoxi-fenilo, o 4-trifluorometoxi-fenilo, A2 no sea 4-difluorometoxi-fenilo; y, siempre que cuando Q es -NHCH2(4,6-dimetil-piridin-3-il) y A1 es 3-nitro-4-metoxi-fenilo, 2,6-difluoro-4-metoxi-fenilo, o 3,4-dicloro-fenilo, A2 no sea 4-metoxi-fenilo; (c) es -CH2NHCH2-Ar3, donde W es N o CH, y Ar3 es piridinilo, pirimidinilo, 1,2,3,4-tetrahidro[1,8]naftiridinilo, imidazo[1,2-a]piridinilo, o quinolinilo; de tal modo que el punto de union al 1,2,3,4-tetrahidro-[1,8]naftiridinilo está en la posicion 6 o 7, y que el punto de union al quinolinilo está en la posicion 2, 3 o 4; donde Ar3 está opcionalmente sustituido con uno a tres sustituyentes independientemente seleccionados del grupo formado por alquilo C1-4, aminoalquilo C1-4, (alquil C1-4amino-alquilo C1-4, di(alquil C1-4)amino-alquilo C1-4, alcoxi C1-4, amino, (alquil C1-6)amino, y di(alquil C1-6)amino; y donde el grupo alquilo C1-6 de (alquil C1-6)amino y di(alquil C1-6)amino está opcionalmente sustituido con amino, (alquil C1-4)amino, di(alquil C1-4)amino, cicloalquil C3-8amino, alcoxi C1-4, o hidroxi; (d) es -(CH2)2-Ar4, donde Ar4 es piridinilo, pirimidinilo, 1,2,3,4-tetrahidro-[1,8]naftiridinilo, imidazo[1,2-a]piridinilo, o quinolinilo; de tal modo que el punto de union a 1,2,3,4-tetrahidro-[1,8]naftiridinilo está en la posicion 6 o 7, y el punto de union al quinolinilo está en la posicion 2, 3 o 4; donde Ar4 está opcionalmente sustituido con uno a tres sustituyentes independientemente seleccionados del grupo formado por alquilo C1-4, aminoalquilo C1-4, (alquil C1-4)amino-alquilo C1-4, di(alquil C1-4)amino-alquilo C1-4, alcoxi C1-4, amino, (alquil C1-6)amino, di(alquil C1-6)amino, halogeno, y aminocarbonilo; y donde el grupo alquilo C1-6 de (alquil C1-6)amino y di(alquil C1-6)amino está opcionalmente sustituido con amino, (alquil C1-4)amino, di(alquil C1-4)amino, cicloalquil C3- 8amino, alcoxi C1-4, o hidroxi; (e) es -CH=CH-Ar5 donde Ar5 es piridinilo, pirimidinilo, 1,2,3,4-tetrahidro-[1,8]naftiridinilo, imidazo[1,2-a]piridinilo, o quinolinilo; de tal modo que el punto de union al 1,2,3,4-tetrahidro-[1,8]naftiridinilo está en la posicion 6 o 7, y el punto de union al quinolinilo está en la posicion 2, 3 o 4; donde Ar5 está opcionalmente sustituido con uno a tres sustituyentes independientemente seleccionados del grupo formado por alquilo C1-4, aminoalquilo C1-4, (alquil C1-4)amino-alquilo C1-4, di(alquil C1-4)amino-alquilo C1-4, alcoxi C1-4, amino, (alquil C1-6)amino, di(alquil C1-6)amino, halogeno, y aminocarbonilo; y donde el grupo alquilo C1-6 de (alquil C1-6)amino y di(alquil C1-6)amino está opcionalmente sustituido con amino, (alquil C1-4)amino, di(alquil C1-4)amino, cicloalquil C3-8amino, alcoxi C1-4, o hidroxi
ARP060105853A 2005-12-29 2006-12-28 Antagonistas del receptor de proquineticina 1 AR058406A1 (es)

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US (2) US7902358B2 (es)
EP (2) EP2385042B1 (es)
JP (1) JP5452934B2 (es)
CN (2) CN101495464B (es)
AR (1) AR058406A1 (es)
CA (1) CA2635842C (es)
CL (1) CL2006003736A1 (es)
DK (1) DK1973886T3 (es)
IL (1) IL192424A0 (es)
WO (1) WO2007079163A2 (es)

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Publication number Priority date Publication date Assignee Title
US7968710B2 (en) * 2005-03-24 2011-06-28 Janssen Pharmaceutica Nv Prokineticin 1 receptor antagonists
CN101495464B (zh) * 2005-12-29 2014-03-05 詹森药业有限公司 激肽原1受体拮抗剂
SG174016A1 (en) * 2006-07-24 2011-09-29 Korea Res Inst Chem Tech Hiv reverse transcriptase inhibitors
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