CA2147753A1 - Tropone-substituted phenyloxazolidinone antibacterial agents - Google Patents

Tropone-substituted phenyloxazolidinone antibacterial agents

Info

Publication number
CA2147753A1
CA2147753A1 CA002147753A CA2147753A CA2147753A1 CA 2147753 A1 CA2147753 A1 CA 2147753A1 CA 002147753 A CA002147753 A CA 002147753A CA 2147753 A CA2147753 A CA 2147753A CA 2147753 A1 CA2147753 A1 CA 2147753A1
Authority
CA
Canada
Prior art keywords
antibacterial agents
tropone
substituted
group
same
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
CA002147753A
Other languages
French (fr)
Other versions
CA2147753C (en
Inventor
Michael Robert Barbachyn
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.)
Pharmacia and Upjohn Co
Original Assignee
Michael Robert Barbachyn
The Upjohn Company
Pharmacia & Upjohn Company
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 Michael Robert Barbachyn, The Upjohn Company, Pharmacia & Upjohn Company filed Critical Michael Robert Barbachyn
Publication of CA2147753A1 publication Critical patent/CA2147753A1/en
Application granted granted Critical
Publication of CA2147753C publication Critical patent/CA2147753C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • 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

Abstract

A novel class of phenyloxazolidinone antibacterial agents which have, as their salient structural feature, an appended substituted tropone moiety, are described. Intermediates and processes for the preparation of these antibiotics are also disclosed. These compounds are useful antibacterial agents to eradicate or control suceptible organisms.
In formula (I), R1, R2 and R3 are the same as in claim 1 and R4 is selected from the group consisting of (a), (b), (c) and (d), wherein R
and R a are the same or different and are selected from the group consisting of (C1-C8) alkyl optionally substituted with chloro, fluoro, hydroxy, (C1-C8) alkoxy, amino, (C1-C8) alkylamino, (C1-C8) dialkylamino. (see formula I)
CA002147753A 1992-12-08 1993-10-14 Tropone-substituted phenyloxazolidinone antibacterial agents Expired - Fee Related CA2147753C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US98858992A 1992-12-08 1992-12-08
US988,589 1992-12-08
US377893A 1993-01-13 1993-01-13
US003,778 1993-01-13
US6635693A 1993-05-21 1993-05-21
US066,356 1993-05-21
PCT/US1993/009589 WO1994013649A1 (en) 1992-12-08 1993-10-14 Tropone-substituted phenyloxazolidinone antibacterial agents

Publications (2)

Publication Number Publication Date
CA2147753A1 true CA2147753A1 (en) 1994-06-23
CA2147753C CA2147753C (en) 2004-08-03

Family

ID=27357482

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002147753A Expired - Fee Related CA2147753C (en) 1992-12-08 1993-10-14 Tropone-substituted phenyloxazolidinone antibacterial agents

Country Status (20)

Country Link
US (1) US5523403A (en)
EP (1) EP0673370B1 (en)
JP (1) JP3558088B2 (en)
KR (1) KR100276382B1 (en)
AT (1) ATE161833T1 (en)
AU (1) AU670842B2 (en)
CA (1) CA2147753C (en)
CZ (1) CZ288788B6 (en)
DE (1) DE69316240T2 (en)
DK (1) DK0673370T3 (en)
ES (1) ES2111188T3 (en)
FI (1) FI952798A0 (en)
GR (1) GR3026228T3 (en)
HU (1) HUT74099A (en)
NO (1) NO952253L (en)
NZ (1) NZ257031A (en)
PL (1) PL175782B1 (en)
RU (1) RU2119484C1 (en)
SK (1) SK282453B6 (en)
WO (1) WO1994013649A1 (en)

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GB9609919D0 (en) * 1996-05-11 1996-07-17 Zeneca Ltd Chemical compounds
WO1998007708A1 (en) * 1996-08-21 1998-02-26 Pharmacia & Upjohn Company Isoxazoline derivatives useful as antimicrobials
US5998414A (en) * 1996-08-22 1999-12-07 Hoechst Marion Roussel, Inc. Troponyl piperazines as dopamine D4 receptor ligands
GB9717807D0 (en) * 1997-08-22 1997-10-29 Zeneca Ltd Chemical compounds
GB9717804D0 (en) 1997-08-22 1997-10-29 Zeneca Ltd Chemical compounds
DK1028940T3 (en) * 1997-11-07 2007-07-30 Pharmacia & Upjohn Co Llc Process for the preparation of oxazolidinones
GB9725244D0 (en) 1997-11-29 1998-01-28 Zeneca Ltd Chemical compounds
US6083967A (en) * 1997-12-05 2000-07-04 Pharmacia & Upjohn Company S-oxide and S,S-dioxide tetrahydrothiopyran phenyloxazolidinones
KR20010015910A (en) * 1998-01-23 2001-02-26 로렌스 티. 마이젠헬더 Oxazolidinone Combinatorial Libraries, Compositions and Methods of Preparation
HUP0103082A3 (en) 1998-06-05 2002-12-28 Astrazeneca Ab Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them
US6420349B1 (en) 1998-08-24 2002-07-16 Bristol-Myers Squibb Company Isoxazolinone antibacterial agents
TW572757B (en) * 1998-08-24 2004-01-21 Bristol Myers Squibb Co Novel isoxazolinone antibacterial agents
JP2002535680A (en) 1999-01-27 2002-10-22 ファルマシア・アンド・アップジョン・カンパニー Assay method for elongation factor p activity modulator
GB9928568D0 (en) 1999-12-03 2000-02-02 Zeneca Ltd Chemical compounds
GB0009803D0 (en) * 2000-04-25 2000-06-07 Astrazeneca Ab Chemical compounds
US6465456B2 (en) 2000-06-29 2002-10-15 Bristol-Myers Squibb Company Isoxazolinone antibacterial agents
US6689769B2 (en) 2000-12-21 2004-02-10 Pharmacia & Upjohn Company Antimicrobial quinolone derivatives and use of the same to treat bacterial infections
AU2002360238B2 (en) * 2001-04-17 2007-11-15 Kyorin Pharmaceutical Co., Ltd. Bicyclo[3,1,0]hexane containing oxazolidinone antibiotic and derivatives thereof
TW200302095A (en) * 2002-01-25 2003-08-01 Upjohn Co Oxazolidinone cotherapy
MXPA04007468A (en) 2002-02-05 2004-11-10 Upjohn Co Antimicrobial thiadiazinone derivatives useful in treatment of bacterial infections.
US7141588B2 (en) * 2002-02-25 2006-11-28 Pfizer, Inc. N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
AR038536A1 (en) * 2002-02-25 2005-01-19 Upjohn Co N-ARIL-2-OXAZOLIDINONA-5- CARBOXAMIDS AND ITS DERIVATIVES
EP1490059A1 (en) * 2002-03-29 2004-12-29 Pharmacia & Upjohn Company LLC Parenteral, intravenous, and oral administration of oxazolidinones for treating diabetic foot infections
WO2004014897A1 (en) * 2002-08-12 2004-02-19 Pharmacia & Upjohn Company Llc N-aryl-2-oxazolidinones and their derivatives
JP2006509035A (en) * 2002-11-21 2006-03-16 ファルマシア・アンド・アップジョン・カンパニー・エルエルシー N- (4- (piperazin-1-yl) -phenyl-2-oxazolidinone-5-carboxamide derivatives and related compounds as antibacterial agents
US7474742B2 (en) * 2003-01-31 2009-01-06 Qwest Communications International Inc. Environmentally-controlled network interface device and methods
US8050281B2 (en) * 2003-01-31 2011-11-01 Qwest Communications International Inc. Alert gateway, systems and methods
US8813142B2 (en) * 2003-01-31 2014-08-19 Qwest Communications International Inc. Methods, systems and apparatus for providing video transmissions over multiple media
BRPI0407252A (en) * 2003-02-07 2006-01-31 Warner Lambert Co Antibacterial agents.
US20040204463A1 (en) * 2003-04-01 2004-10-14 Harris Christina Renee N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
WO2005019211A2 (en) 2003-06-03 2005-03-03 Rib-X Pharmaceuticals, Inc. Biaryl heterocyclic compounds and methods of making and using the same
US8324398B2 (en) 2003-06-03 2012-12-04 Rib-X Pharmaceuticals, Inc. Process for the synthesis of biaryl oxazolidinones
JP2007521283A (en) * 2003-07-02 2007-08-02 メルク アンド カンパニー インコーポレーテッド Oxazolidinone antibiotics and derivatives thereof substituted with cyclopropyl groups
US20070293493A1 (en) * 2003-07-02 2007-12-20 Milton Hammond Oxazolidinone antibiotics and derivatives thereof
EP1656357A1 (en) * 2003-07-02 2006-05-17 Merck & Co., Inc. Oxazolidinone antibiotics and derivatives thereof
EP1646629B1 (en) 2003-07-02 2010-06-23 Merck Sharp & Dohme Corp. Cyclopropyl group substituted oxazolidinone antibiotics and derivatives thereof
WO2005019214A1 (en) * 2003-08-25 2005-03-03 Warner-Lambert Company Llc Novel antimicrobial aryloxazolidinone compounds
US7304050B2 (en) * 2003-09-16 2007-12-04 Pfizer Inc. Antibacterial agents
US7129259B2 (en) * 2003-12-17 2006-10-31 Rib-X Pharmaceuticals, Inc. Halogenated biaryl heterocyclic compounds and methods of making and using the same
KR100854211B1 (en) 2003-12-18 2008-08-26 동아제약주식회사 Novel oxazolidinone derivatives, a process for the preparation thereof and pharmaceutical composition comprising the same for antibiotics
JP5534497B2 (en) 2005-06-08 2014-07-02 メリンタ セラピューティクス，インコーポレイテッド Method for synthesizing triazoles
CN103497173A (en) * 2006-03-31 2014-01-08 财团法人乙卯研究所 Novel compound having heterocyclic ring
JPWO2007116960A1 (en) * 2006-04-06 2009-08-20 財団法人乙卯研究所 Oxazolidinone derivatives having carbocyclic rings
US8530646B2 (en) * 2007-10-02 2013-09-10 Research Foundation Itsuu Laboratory Oxazolidinone derivative having 7-membered hetero ring
US8604209B2 (en) * 2008-10-10 2013-12-10 Trius Therapeutics, Inc. Methods for preparing oxazolidinones and compositions containing them
KR101739923B1 (en) 2009-02-03 2017-05-25 머크 샤프 앤드 돔 코포레이션 Crystalline form of R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate
US8580767B2 (en) * 2009-05-28 2013-11-12 Trius Therapeutics, Inc. Oxazolidinone containing dimer compounds, compositions and methods to make and use

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US4801600A (en) * 1987-10-09 1989-01-31 E. I. Du Pont De Nemours And Company Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents
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US4977173A (en) * 1987-10-21 1990-12-11 E. I. Du Pont De Nemours And Company Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents
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Also Published As

Publication number Publication date
EP0673370B1 (en) 1998-01-07
US5523403A (en) 1996-06-04
PL175782B1 (en) 1999-02-26
SK74695A3 (en) 1995-10-11
NZ257031A (en) 1996-07-26
DE69316240T2 (en) 1998-05-20
ES2111188T3 (en) 1998-03-01
NO952253L (en) 1995-08-08
KR100276382B1 (en) 2000-12-15
HU9501670D0 (en) 1995-08-28
NO952253D0 (en) 1995-06-07
JP3558088B2 (en) 2004-08-25
JPH08504205A (en) 1996-05-07
ATE161833T1 (en) 1998-01-15
WO1994013649A1 (en) 1994-06-23
CA2147753C (en) 2004-08-03
AU5323994A (en) 1994-07-04
CZ136695A3 (en) 1995-10-18
CZ288788B6 (en) 2001-09-12
HUT74099A (en) 1996-11-28
RU2119484C1 (en) 1998-09-27
DK0673370T3 (en) 1998-09-07
AU670842B2 (en) 1996-08-01
PL309283A1 (en) 1995-10-02
GR3026228T3 (en) 1998-05-29
SK282453B6 (en) 2002-02-05
DE69316240D1 (en) 1998-02-12
FI952798A (en) 1995-06-07
RU95114378A (en) 1997-06-10
FI952798A0 (en) 1995-06-07
EP0673370A1 (en) 1995-09-27

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