[go: up one dir, main page]

WO2013015661A3 - Novel prodrugs of 5-(2,4-dihydroxy-5-isopropylphenyl)-n-ethyl-4-(5-methyl1-1,2,4-oxadiazol-3-yl)isoxazole-3-carboxamide - Google Patents

Novel prodrugs of 5-(2,4-dihydroxy-5-isopropylphenyl)-n-ethyl-4-(5-methyl1-1,2,4-oxadiazol-3-yl)isoxazole-3-carboxamide Download PDF

Info

Publication number
WO2013015661A3
WO2013015661A3 PCT/KR2012/006043 KR2012006043W WO2013015661A3 WO 2013015661 A3 WO2013015661 A3 WO 2013015661A3 KR 2012006043 W KR2012006043 W KR 2012006043W WO 2013015661 A3 WO2013015661 A3 WO 2013015661A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
methyl1
isopropylphenyl
oxadiazol
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2012/006043
Other languages
French (fr)
Other versions
WO2013015661A2 (en
Inventor
Jae-Hoon Kang
Hong-Sub Lee
Jin-Sun Kwon
Joon-Tae Park
Jin-Ah Jeong
Sung-Wook Kwon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ildong Pharmaceutical Co Ltd
Original Assignee
Ildong Pharmaceutical Co Ltd
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 Ildong Pharmaceutical Co Ltd filed Critical Ildong Pharmaceutical Co Ltd
Priority claimed from KR1020120082521A external-priority patent/KR20130018548A/en
Publication of WO2013015661A2 publication Critical patent/WO2013015661A2/en
Publication of WO2013015661A3 publication Critical patent/WO2013015661A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The present invention relates to the novel compound of Formula I. The compound of Formula I are used as a prodrug of the parent compound, Formula II, and have valuable pharmacological properties. The compound of Formula I have improved solubility by 1,000~20,000 times or more, and increased bioavailability compared to those of the compound of Formula II. Furthermore, they can be absorbed into the body with increased concentration by improved value of AUC0-120min and Cmax, more by 3~5 times and 10~20 times respectively compared to the compound of Formula II. Thus, those improved pharmacokinetic properties can be used very effectively to treat various diseases by inhibition of HSP90 activity, especially for ovarian and gastric cancer.
PCT/KR2012/006043 2011-07-28 2012-07-27 Novel prodrugs of 5-(2,4-dihydroxy-5-isopropylphenyl)-n-ethyl-4-(5-methyl1-1,2,4-oxadiazol-3-yl)isoxazole-3-carboxamide Ceased WO2013015661A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20110074867 2011-07-28
KR10-2011-0074867 2011-07-28
KR10-2012-0082521 2012-07-27
KR1020120082521A KR20130018548A (en) 2011-07-28 2012-07-27 Novel prodrugs of 5-(2,4-dihydroxy-5-isopropylphenyl)-n-ethyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)isoxazole-3-carboxamide

Publications (2)

Publication Number Publication Date
WO2013015661A2 WO2013015661A2 (en) 2013-01-31
WO2013015661A3 true WO2013015661A3 (en) 2013-05-02

Family

ID=47601688

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2012/006043 Ceased WO2013015661A2 (en) 2011-07-28 2012-07-27 Novel prodrugs of 5-(2,4-dihydroxy-5-isopropylphenyl)-n-ethyl-4-(5-methyl1-1,2,4-oxadiazol-3-yl)isoxazole-3-carboxamide

Country Status (1)

Country Link
WO (1) WO2013015661A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9533002B2 (en) 2012-05-25 2017-01-03 Berg Llc Methods of treating a metabolic syndrome by modulating heat shock protein (HSP) 90-β
EP3152307A4 (en) 2014-06-06 2018-05-02 Berg LLC Methods of treating a metabolic syndrome by modulating heat shock protein (hsp) 90-beta
WO2019059344A1 (en) 2017-09-22 2019-03-28 大日本住友製薬株式会社 Chemically activated water-soluble prodrug

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004072051A1 (en) * 2003-02-11 2004-08-26 Vernalis (Cambridge) Limited Isoxazole compounds as inhibitors of heat shock proteins
WO2008104595A1 (en) * 2007-03-01 2008-09-04 Novartis Ag Acid addition salts, hydrates and polymorphs of 5-(2,4-dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide and formulations comprising these forms
WO2009036012A1 (en) * 2007-09-10 2009-03-19 Curis, Inc. Hsp90 inhibitors containing a zinc binding moiety
WO2011102660A2 (en) * 2010-02-17 2011-08-25 Ildong Pharm Co., Ltd. A novel 5-membered heterocycle derivatives and manufacturing process thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004072051A1 (en) * 2003-02-11 2004-08-26 Vernalis (Cambridge) Limited Isoxazole compounds as inhibitors of heat shock proteins
WO2008104595A1 (en) * 2007-03-01 2008-09-04 Novartis Ag Acid addition salts, hydrates and polymorphs of 5-(2,4-dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide and formulations comprising these forms
WO2009036012A1 (en) * 2007-09-10 2009-03-19 Curis, Inc. Hsp90 inhibitors containing a zinc binding moiety
WO2011102660A2 (en) * 2010-02-17 2011-08-25 Ildong Pharm Co., Ltd. A novel 5-membered heterocycle derivatives and manufacturing process thereof

Also Published As

Publication number Publication date
WO2013015661A2 (en) 2013-01-31

Similar Documents

Publication Publication Date Title
HK1215579A1 (en) Substituted 2,3-dihydrobenzofuranyl compounds and uses thereof
WO2011123946A8 (en) Kinase inhibitors and method of treating cancer with same
WO2013053983A8 (en) Protein kinase inhibitors
PH12015501037A1 (en) Pyridine derivative
MX2013011589A (en) Methods and compositions for treating parkinson's disease.
WO2010108074A3 (en) Inhibitors of pi3 kinase
BR112014002202A2 (en) macrocycles as factor xia inhibitors
WO2013040286A3 (en) Pharmaceutical compositions
PH12017501429A1 (en) Derivatives of betulin
MY164776A (en) Heterocyclic compound
WO2012099942A3 (en) Methods and compositions for treating metabolic syndrome
WO2009091898A3 (en) 6-and 7-amino isoquinoline compounds and methods for making and using the same
WO2014031872A3 (en) Small molecule inhibitors for treating parasitic infections
WO2012141796A3 (en) Prostate cancer therapy with hsp90 inhibitory compounds
EP2581372A4 (en) CYANOQUINOLINE DERIVATIVE
WO2012015681A3 (en) Drug-ligand conjugates, synthesis thereof, and intermediates thereto
WO2014197345A3 (en) Imidazole derivatives and methods of use thereof for improving the pharmacokinetics of a drug
WO2011156557A3 (en) Compounds active at the neurotensin receptor
CA2817362C (en) Lipoyl compounds and their use for treating ischemic injury
WO2014036502A8 (en) Tetracycline compounds
WO2012135615A3 (en) Enopeptins, uses thereof, and methods of synthesis thereto
WO2015042414A8 (en) Multicyclic compounds and methods of using same
WO2010132670A3 (en) Pentacycline compounds
WO2013015661A3 (en) Novel prodrugs of 5-(2,4-dihydroxy-5-isopropylphenyl)-n-ethyl-4-(5-methyl1-1,2,4-oxadiazol-3-yl)isoxazole-3-carboxamide
WO2012030170A3 (en) Novel compound acting as a cannabinoid receptor-1 inhibitor

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12816959

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12816959

Country of ref document: EP

Kind code of ref document: A2