AR066078A1 - Derivados de tetrahidroindol y tetrahidroindazol. procesos de obtencion, composiciones farmaceuticos y usos. - Google Patents

Derivados de tetrahidroindol y tetrahidroindazol. procesos de obtencion, composiciones farmaceuticos y usos.

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Publication number
AR066078A1
AR066078A1 ARP080101564A ARP080101564A AR066078A1 AR 066078 A1 AR066078 A1 AR 066078A1 AR P080101564 A ARP080101564 A AR P080101564A AR P080101564 A ARP080101564 A AR P080101564A AR 066078 A1 AR066078 A1 AR 066078A1
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AR
Argentina
Prior art keywords
alkyl
heteroaryl
cycloalkyl
alkoxy
aryl
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ARP080101564A
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English (en)
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Serenex Inc
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Publication of AR066078A1 publication Critical patent/AR066078A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • 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
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory 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
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Immunology (AREA)
  • Communicable Diseases (AREA)
  • Hematology (AREA)
  • Neurology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Vascular Medicine (AREA)
  • Virology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Obesity (AREA)
  • Diabetes (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biomedical Technology (AREA)
  • Transplantation (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Procesos de obtencion y usos de los mismos para tratar y/o prevenir enfermedades y/o trastornos aliviados por la inhibicion de la Proteína de Choque Térmico 90. La presente además proporciona composiciones farmacéuticas que comprenden dichoscompuestos. Reivindicacion 1: Un compuesto de la formula (1) o una sal farmacéuticamente aceptable del mismo, caracterizado porque: R1 y R2 son independientemente -H o alquilo C1-8, R3 está ausente o es -H, -F, -OCH3; R4 y R5 son independientemente-H, -F, -OCH3; R6 es alquenilo C2-14, alquilo C1-14, alquinilo C2-14, arilo, arilo alquilo C1-8, cicloalquenilo C3-8, cicloalquenilo C3-8-alquilo C1-8, cicloalquilo C3-8, cicloalquilo C3-8-alquilo C1-8, heteroarilo, heteroarilo alquilo C1-8,heteroarilo alquiltio C1-8-alquilo C1-8, heteroariltio alquilo C1-8, heterociclilo, heterociclo alquilo C1-8, o hidroxi alquilo C1-8, en donde el grupo R6 se sustituye opcionalmente con 1, 2, 3, 4, o 5 grupos los cuales son alquenilo C2-8, alcoxi C1-8, alcoxi C1-8-alquilo C1--8, alcoxicarbonilo C1-8, alquilo C1-8, alquilcarbonilo C1-8, alquilcarboniloxi C1-8, alquilsulfinilo C1-8, alquilsulfonilo C1-8, alquiltio C1-8, alquinilo C2-8, carboxi, carboxi alquilo C1-8, ciano, ciano alquilo C1-8,cicloalquilo C3-8, cicloalquilo C3-8-alquilo C1-8, formilo, halo alcoxi C1-8, halo alquilo C1-8, halogeno, hidroxi, hidroxi alcoxi C1-8, hidroxi alcoxi C1-8-alcoxi C1-8, hidroxi alquilo C1-8, mercapto, nitro, -NR11R12, (NR11R12) alquilo C1-8,carbonilo (NR11R12), oxo, HOCH2CH(NH2)C(O)O-, NH2(CH2)mC(O)O-, CH3NH(CH2)mC(O)O-, (CH3)2N(CH2)mC(O)O-, NH2(CH2)tC(O)NH(CH2)mC(O)O-, R12CH(NH2)C(O)O-, NH2(CH2)mC(R12)2(CH2)mC(O)O-, NH2CH2CH2C(O)O-, R11ON=CH(CH2)nO-, o HONHC(O)(CH2)nO-; o R5 y R6tomados junto con el átomo de nitrogeno al cual están unidos forman un heteroarilo, en donde el heteroarilo es imidazolilo, oxazolilo, pirazolilo, piridazinilo, piridinilo, pirazinilo, pirrolilo, o tiazolilo, en donde el heteroarilo se sustituyeopcionalmente con alcoxi C1-8, alcoxicarbonilo C1-8, alquilo C1-8, alquilcarbonilo C1-8, alquilcarboniloxi C1-8, arilo, arilo alquilo C1-8, ciano, ciano alquilo C1-8, cicloalquilo C3-8, cicloalquilo C3-8-alquilo C1-8, halo alcoxi C1-8, halo alquiloC1-8, halogeno, heteroarilo, heteroarilo alquilo C1-8, heterociclilo, heterociclo alquilo C1-8, hidroxi, hidroxi alquilo C1-8, mercapto, nitro, -NR11R12, (NR11R12) alquilo C1-8, o carbonilo (NR11R12); R7 es -H o alquilo C1-8; R8 es alquenilo C2-8,alquilo C1-8, alquinilo C2-8, cicloalquenilo C3-8, cicloalquenilo C3-8 alquilo C1-8, cicloalquilo C3-8, cicloalquilo C3-8 alquilo C1-8, arilo, arilo alquilo C1-8, halo alquilo C1-8, heteroarilo, heteroarilo alquilo C1-8, heterociclilo, heterocicloalquilo C1-8, o hidroxi alquilo C1-8; R9 y R10 son independientemente -H o alquilo C1-8; o R9 y R10 tomados junto con el átomo de carbono al cual están unidos forman cicloalquilo C3-8; R11 y R12 son independientemente -H, alquenilo C2-8, alquilo C1-8, alquilcarbonilo C1-8, alquinilo C2-8, arilo, arilo alquilo C1-8, cicloalquilo C3-8, cicloalquilo C3-8 alquilo C1-8, formilo, heteroarilo, heteroarilo alquilo C1-8, heterociclilo, o heterociclo alquilo C1-8; o dos grupos R12 junto con el carbonoal cual están unidos forman un grupo cicloalquilo C3-8; n es 1, 2, 3, 4, 5, o 6; cada m es independientemente 1, 2, 3, o 4; cada t es independientemente 1, 2, 3, o 4; X es H o CR13, Y es C o N; y R13 es -H o alquilo C1-8.
ARP080101564A 2007-04-16 2008-04-16 Derivados de tetrahidroindol y tetrahidroindazol. procesos de obtencion, composiciones farmaceuticos y usos. AR066078A1 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US91208307P 2007-04-16 2007-04-16
US1746907P 2007-12-28 2007-12-28
US1973208P 2008-01-08 2008-01-08

Publications (1)

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AR066078A1 true AR066078A1 (es) 2009-07-22

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ID=39769290

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ARP080101564A AR066078A1 (es) 2007-04-16 2008-04-16 Derivados de tetrahidroindol y tetrahidroindazol. procesos de obtencion, composiciones farmaceuticos y usos.

Country Status (9)

Country Link
US (1) US20080269193A1 (es)
EP (1) EP2146967A2 (es)
JP (1) JP2010524950A (es)
AR (1) AR066078A1 (es)
CA (1) CA2684240A1 (es)
CL (1) CL2008001069A1 (es)
TW (1) TW200906394A (es)
UY (1) UY31027A1 (es)
WO (1) WO2008130879A2 (es)

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TWI382015B (zh) * 2005-02-25 2013-01-11 Serenex Inc 苯、吡啶及噠嗪衍生物
US7678803B2 (en) * 2006-08-24 2010-03-16 Serenex, Inc. Quinazoline derivatives for the treatment of cancer
AR077405A1 (es) 2009-07-10 2011-08-24 Sanofi Aventis Derivados del indol inhibidores de hsp90, composiciones que los contienen y utilizacion de los mismos para el tratamiento del cancer
FR2949467B1 (fr) 2009-09-03 2011-11-25 Sanofi Aventis Nouveaux derives de 5,6,7,8-tetrahydroindolizine inhibiteurs d'hsp90, compositions les contenant et utilisation
CN101955461B (zh) * 2010-10-08 2012-11-21 广州暨南生物医药研究开发基地有限公司 一种Hsp90抑制剂Xbj-B11及其制备方法与应用
CN101967125B (zh) * 2010-10-08 2012-07-04 广州暨南生物医药研究开发基地有限公司 一种Hsp90抑制剂Xbj-B16-1及其制备方法与应用
CN103380117A (zh) * 2011-01-21 2013-10-30 Abbvie公司 激酶的吡啶酰胺抑制剂
AR088082A1 (es) * 2011-10-13 2014-05-07 Lilly Co Eli Moduladores selectivos del receptor androgeno
EP2879675B1 (en) 2012-08-06 2019-11-13 Duke University Compounds and methods for targeting hsp90
MX355943B (es) * 2013-06-26 2018-05-07 Abbvie Inc Carboxamidas primarias como inhibidores de btk.
CN103467356B (zh) * 2013-08-12 2015-04-01 绍兴文理学院 一种四氢吲哚化合物及其制备方法与应用
CN107428740A (zh) * 2014-09-11 2017-12-01 埃萨内克斯股份有限公司 吲唑基‑和吲哚基‑苯甲酰胺衍生物
US20160143884A1 (en) 2014-11-26 2016-05-26 Esanex, Inc. Use of tetrahydroindazolylbenzamide and tetrahydroindolylbenzamide derivatives for the treatment of human immunodeficiency virus (hiv) and acquired immune deficiency syndrome (aids)
WO2017059434A1 (en) 2015-10-02 2017-04-06 Esanex, Inc. Use of tetrahydroindazolylbenzamide and tetrahydroindolylbenzamide derivatives for the treatment of cancer
WO2017184956A1 (en) 2016-04-22 2017-10-26 Duke University Compounds and methods for targeting hsp90
JOP20190080A1 (ar) * 2016-10-14 2019-04-11 Bayer Pharma AG مركبات مشتقة من 6-(1h-بيرازول-1-يل) بيريميدين-4- أمين مستبدل واستخداماتها
US10975030B2 (en) 2016-10-31 2021-04-13 University Of Kansas Grp94 selective inhibitors and uses thereof
CN109796409A (zh) * 2019-01-31 2019-05-24 广州暨南生物医药研究开发基地有限公司 一种合成四氢吲唑化合物的方法

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US7208630B2 (en) * 2004-10-27 2007-04-24 University Of Kansas Heat shock protein 90 inhibitors
TWI382015B (zh) * 2005-02-25 2013-01-11 Serenex Inc 苯、吡啶及噠嗪衍生物
WO2006133634A1 (fr) * 2005-06-14 2006-12-21 Beijing Gylongly Biodemtech Co., Ltd Dérivés tétrahydroindole et dérivés tétrahydroindazole et leur utilisation
US20070185184A1 (en) * 2005-09-16 2007-08-09 Serenex, Inc. Carbazole derivatives
WO2007101156A1 (en) * 2006-02-27 2007-09-07 Serenex, Inc. Cyclohexylamino, benzene, pyridine, and pyridazine derivatives
US20080070933A1 (en) * 2006-08-24 2008-03-20 Huang Kenneth H Purine, Pyrimidine, and Azaindole Derivatives
WO2008024963A1 (en) * 2006-08-24 2008-02-28 Serenex, Inc. Benzene, pyridine, and pyridazine derivatives
US20080076813A1 (en) * 2006-08-24 2008-03-27 Huang Kenneth H Benzene, Pyridine, and Pyridazine Derivatives
WO2008024978A2 (en) * 2006-08-24 2008-02-28 Serenex, Inc. Tetrahydroindolone and tetrahydroindazolone derivatives
US7678803B2 (en) * 2006-08-24 2010-03-16 Serenex, Inc. Quinazoline derivatives for the treatment of cancer
WO2008024980A2 (en) * 2006-08-24 2008-02-28 Serenex, Inc. Pyrrole, thiophene, furan, imidazole, oxazole, and thiazole derivatives
WO2008024974A1 (en) * 2006-08-24 2008-02-28 Serenex, Inc. Pyrimidine and pyrazine derivatives
WO2008024961A1 (en) * 2006-08-24 2008-02-28 Serenex, Inc. Dihydropyridazine, tetrahydropyridine, chromanone, and dihydronaphthalenone derivatives as heat-shock protein 90 inhibitors

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WO2008130879A3 (en) 2008-12-18
UY31027A1 (es) 2008-11-28
TW200906394A (en) 2009-02-16
JP2010524950A (ja) 2010-07-22
CA2684240A1 (en) 2008-10-30
US20080269193A1 (en) 2008-10-30
EP2146967A2 (en) 2010-01-27
CL2008001069A1 (es) 2008-08-08
WO2008130879A2 (en) 2008-10-30

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