WO2010015703A3 - 6 - o - substituted 15 -membered 8a- and 9a - lactams - Google Patents

6 - o - substituted 15 -membered 8a- and 9a - lactams Download PDF

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Publication number
WO2010015703A3
WO2010015703A3 PCT/EP2009/060273 EP2009060273W WO2010015703A3 WO 2010015703 A3 WO2010015703 A3 WO 2010015703A3 EP 2009060273 W EP2009060273 W EP 2009060273W WO 2010015703 A3 WO2010015703 A3 WO 2010015703A3
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
piperazin
membered
decladinosyl
homoerythromycin
Prior art date
Application number
PCT/EP2009/060273
Other languages
French (fr)
Other versions
WO2010015703A2 (en
Inventor
Stjepan Mutak
Drazen Pavlovic
Original Assignee
Glaxosmithkline Istrazivacki Centar Zagreb D.O.O.
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 Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. filed Critical Glaxosmithkline Istrazivacki Centar Zagreb D.O.O.
Publication of WO2010015703A2 publication Critical patent/WO2010015703A2/en
Publication of WO2010015703A3 publication Critical patent/WO2010015703A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Communicable Diseases (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to novel anti-bacterial 15-membered 6-O-substituted-8a-aza-8a- homoerythromycin A and 6-O-substituted-9a-aza-9a-homoerythromycin A, their 6-O- substituted-3-O-decladinosyl-3-oxy and 6-O-substituted-3-O-decladinosyl-3-oxo compound of the general formula (I), wherein A represents NH; and B simultaneously represents -C(O)-, or A represents -C(O)- and B simultaneously represents NH; R4 represents: a straight or branched chain C3-C7 alkyl group containing a moiety selected from piperazin-1,4-yl, 2-methyl-piperazin-1,4-yl, 2-methyl-piperazin-1,4-yl-S(O)2, NH and N(CH3), or containing two NH moieties; wherein the second alkyl carbon atom is substituted by a hydroxy substituent, and the terminal carbon atom or heteroatom is substituted by phenyl (itself optionally substituted); or prop-2-enyl (i.e. allyl) optionally substituted by naphthyl or quinolinyl; or CH2-oxiranyl group; and R5 represents (a) dimethylamino [-N(CH3)2] or (b) dimethylamino-N-oxide [-N(O)(CH3)2] group.
PCT/EP2009/060273 2008-08-07 2009-08-07 Novel 6-o-substituted 15-membered 8a- and 9a-lactams WO2010015703A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US8689308P 2008-08-07 2008-08-07
US61/086,893 2008-08-07

Publications (2)

Publication Number Publication Date
WO2010015703A2 WO2010015703A2 (en) 2010-02-11
WO2010015703A3 true WO2010015703A3 (en) 2012-06-28

Family

ID=41664023

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2009/060273 WO2010015703A2 (en) 2008-08-07 2009-08-07 Novel 6-o-substituted 15-membered 8a- and 9a-lactams

Country Status (1)

Country Link
WO (1) WO2010015703A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2908575C (en) 2013-04-04 2021-11-16 President And Fellows Of Harvard College Macrolides and methods of their preparation and use
CN106998685A (en) 2014-10-08 2017-08-01 哈佛大学的校长及成员们 14 yuan of ketone lactones and its preparation and application
JP2018509452A (en) 2015-03-25 2018-04-05 プレジデント アンド フェローズ オブ ハーバード カレッジ Macrolides with modified desosamine sugars and uses thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002032917A1 (en) * 2000-10-19 2002-04-25 Glaxo Group Limited Macrolides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002032917A1 (en) * 2000-10-19 2002-04-25 Glaxo Group Limited Macrolides

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ALIHODZIC S ET AL: "Synthesis and antibacterial activity of isomeric 15-membered azalides", ABSTRACTS OF THE INTERSCIENCE CONFERENCE ON ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, vol. 41, 2001, & 41ST ANNUAL MEETING OF THE INTERSCIENCE CONFERENCE ON ANTIMICROBIAL AGENTS AND CHEMOTHERAPY; CHICAGO, ILLINOIS, USA; SEPTEMBER 22-25, 2001, pages 236, XP002674954 *
HENNINGER TODD C ET AL: "Synthesis and antibacterial activity of C-6 carbamate ketolides, a novel series of orally active ketolide antibiotics", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 17, 6 September 2004 (2004-09-06), pages 4495 - 4499, XP002674956, ISSN: 0960-894X *
KEYES ROBERT F ET AL: "Synthesis and antibacterial activity of 6-O-arylbutynyl ketolides with improved activity against some key erythromycin-resistant pathogens.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 46, no. 10, 8 May 2003 (2003-05-08), pages 1795 - 1798, XP002674955, ISSN: 0022-2623 *
MA Z ET AL: "Novel erythromycin derivatives with aryl groups tethered to the C-6 position are potent protein synthesis inhibitors and active against multidrug-resistant respiratory pathogens", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 44, 1 January 2001 (2001-01-01), pages 4137 - 4156, XP002215521, ISSN: 0022-2623, DOI: 10.1021/JM0102349 *

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WO2010015703A2 (en) 2010-02-11

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WO2010015703A3 (en) 6 - o - substituted 15 -membered 8a- and 9a - lactams

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