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CA2282254A1 - Hydroxyazepanes as inhibitors of glycosidase and hiv protease - Google Patents

Hydroxyazepanes as inhibitors of glycosidase and hiv protease Download PDF

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Publication number
CA2282254A1
CA2282254A1 CA002282254A CA2282254A CA2282254A1 CA 2282254 A1 CA2282254 A1 CA 2282254A1 CA 002282254 A CA002282254 A CA 002282254A CA 2282254 A CA2282254 A CA 2282254A CA 2282254 A1 CA2282254 A1 CA 2282254A1
Authority
CA
Canada
Prior art keywords
hydroxyazepanes
glycosidase
hiv protease
inhibitors
respect
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.)
Granted
Application number
CA002282254A
Other languages
French (fr)
Other versions
CA2282254C (en
Inventor
Chi-Huey Wong
Francisco Moris-Varas
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.)
Scripps Research Institute
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2282254A1 publication Critical patent/CA2282254A1/en
Application granted granted Critical
Publication of CA2282254C publication Critical patent/CA2282254C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/001—Amines; Imines
    • 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
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
    • C07D223/08—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/26—Preparation of nitrogen-containing carbohydrates

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Virology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

Hydroxyazepanes display inhibitory activity with respect to glycosidase, with K i values from moderate to low micromolar range. Benzyl and 3,6-dibenzyl derivatives of hydroxyazepanes display inhibitory activity with respect to HIV protease. These compounds are synthesized either by chemoenzymatic or chemical methodologies. Methods are provided for producing a tetrahydroxyazepane with the formula:
(see formula I)
CA002282254A 1997-02-21 1997-02-21 Hydroxyazepanes as inhibitors of glycosidase and hiv protease Expired - Fee Related CA2282254C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1997/002927 WO1998037218A1 (en) 1997-02-21 1997-02-21 Hydroxyazepanes as inhibitors of glycosidase and hiv protease

Publications (2)

Publication Number Publication Date
CA2282254A1 true CA2282254A1 (en) 1998-08-27
CA2282254C CA2282254C (en) 2006-03-21

Family

ID=22260424

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002282254A Expired - Fee Related CA2282254C (en) 1997-02-21 1997-02-21 Hydroxyazepanes as inhibitors of glycosidase and hiv protease

Country Status (4)

Country Link
JP (1) JP2001515471A (en)
AU (1) AU2056397A (en)
CA (1) CA2282254C (en)
WO (1) WO1998037218A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6860891B2 (en) 2001-09-28 2005-03-01 Ethicen, Inc. Arrangement and method for vascular anastomosis
CN102993095B (en) * 2012-11-15 2015-04-29 中国科学院化学研究所 Seven-element-ring polyhydroxy nitrone and preparation method and application thereof
CN111018770A (en) * 2019-12-26 2020-04-17 北京鑫开元医药科技有限公司 Preparation method of bazedoxifene oxide

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3403778A1 (en) * 1984-02-03 1985-08-08 Degussa Ag, 6000 Frankfurt CYANOMETHYL- (2-CYANO-ETHYL) - (3-HYDROXY-PROPYL) -AMINE HIS USE FOR PRODUCING 1- (3-HYDROXY-PROPYL) -1,4-DIAZEPANE AND 1,4-BIS (3- (3rd , 4,5-TRIMETHOXYBENZOYLOXY) -PROPYL) -DIAZEPAN
AU686691B2 (en) * 1994-01-12 1998-02-12 F. Hoffmann-La Roche Ag Novel azepanes and homologs thereof

Also Published As

Publication number Publication date
AU2056397A (en) 1998-09-09
WO1998037218A1 (en) 1998-08-27
JP2001515471A (en) 2001-09-18
CA2282254C (en) 2006-03-21

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