CA2174107A1 - Esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones - Google Patents

Esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones

Info

Publication number
CA2174107A1
CA2174107A1 CA002174107A CA2174107A CA2174107A1 CA 2174107 A1 CA2174107 A1 CA 2174107A1 CA 002174107 A CA002174107 A CA 002174107A CA 2174107 A CA2174107 A CA 2174107A CA 2174107 A1 CA2174107 A1 CA 2174107A1
Authority
CA
Canada
Prior art keywords
alkyl
esters
substituted
och3
phenyl
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
CA002174107A
Other languages
French (fr)
Other versions
CA2174107C (en
Inventor
Steven J. Brickner
Michael R. Barbachyn
Douglas K. Hutchinson
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
Steven J. Brickner
Michael R. Barbachyn
Douglas K. Hutchinson
Upjohn Company (The)
Pharmacia & Upjohn Company
The 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 Steven J. Brickner, Michael R. Barbachyn, Douglas K. Hutchinson, Upjohn Company (The), Pharmacia & Upjohn Company, The Upjohn Company filed Critical Steven J. Brickner
Publication of CA2174107A1 publication Critical patent/CA2174107A1/en
Application granted granted Critical
Publication of CA2174107C publication Critical patent/CA2174107C/en
Anticipated expiration legal-status Critical
Expired - Fee Related 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
    • C07D413/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • 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 System
    • 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

Abstract

A compound of structural Formula (1) or pharmaceutically acceptable salts thereof wherein: R is -C(O)-R1, -PO3= or -P(O)(OH)2;
R1 is C1-6 alkyl, -N(R4)2, C1-6 alkyl-N(R4)2, -phenyl-N(R4)2, -phenyl-NHC(O)CH2NH2,-C2H4-morpholinyl, pyridinyl, C1-6 alkyl-OH, C1-6 alkyl-OCH3, C1-6 alkyl C(O)CH3, -O-C1-6 alkyl-OCH3, C0-3 alkyl-piperazinyl (optionally substituted with C1-3 alkyl), imidazolyl, C1-6 alkyl-COOH, -C(CH2OH)2CH3; R2 and R3 are independently selected from hydrogen or F except at least one of R2 or R3 is F; R4 are independently selected from hydrogen or C1-6 alkyl. The compounds are water soluble and are useful antimicrobial agents, effective against a number of human and veterinary pathogens, including multiply-resistant staphylococci, enterococci and streptococci, as well as anaerobic organisms such as bacteriodes and clostridia species, and acid-fast organisms such as Mycobacterium tuberculosis.
CA002174107A 1993-11-22 1994-09-27 Esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones Expired - Fee Related CA2174107C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US15598893A 1993-11-22 1993-11-22
US155,988 1993-11-22
PCT/US1994/010582 WO1995014684A1 (en) 1993-11-22 1994-09-27 Esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones

Publications (2)

Publication Number Publication Date
CA2174107A1 true CA2174107A1 (en) 1995-06-01
CA2174107C CA2174107C (en) 2005-04-12

Family

ID=22557606

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002174107A Expired - Fee Related CA2174107C (en) 1993-11-22 1994-09-27 Esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones

Country Status (20)

Country Link
US (1) US5652238A (en)
EP (1) EP0730591B1 (en)
JP (1) JP3698724B2 (en)
KR (1) KR100312903B1 (en)
CN (1) CN1046276C (en)
AT (1) ATE182142T1 (en)
AU (1) AU698699B2 (en)
CA (1) CA2174107C (en)
CO (1) CO4290433A1 (en)
DE (1) DE69419523T2 (en)
DK (1) DK0730591T3 (en)
ES (1) ES2133588T3 (en)
GR (1) GR3031420T3 (en)
IL (1) IL111215A0 (en)
LV (1) LV12538B (en)
NZ (1) NZ274966A (en)
PE (1) PE22896A1 (en)
TW (1) TW427987B (en)
WO (1) WO1995014684A1 (en)
ZA (1) ZA947885B (en)

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GB9614238D0 (en) * 1996-07-06 1996-09-04 Zeneca Ltd Chemical compounds
GB9717804D0 (en) 1997-08-22 1997-10-29 Zeneca Ltd Chemical compounds
GB9717807D0 (en) 1997-08-22 1997-10-29 Zeneca Ltd Chemical compounds
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ES2193592T3 (en) * 1997-11-18 2003-11-01 Upjohn Co USE OF OXAZOLIDINONE DERIVATIVES FOR THE TREATMENT OF ARTHRITIS.
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KR20010079530A (en) * 1998-07-14 2001-08-22 로렌스 티. 마이젠헬더 Oxazolidinones to Treat Eye Infections
AR020660A1 (en) * 1998-09-30 2002-05-22 Alcon Lab Inc ANTIBIOTIC COMPOSITIONS FOR THE TREATMENT OF EYES, EARS AND NOSE
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
PE20010851A1 (en) * 1999-12-14 2001-08-17 Upjohn Co BENZOIC ACID ESTERS OF OXAZOLIDINONES HAVING A HYDROXYACETILPIPERAZINE SUBSTITUENT
US6642238B2 (en) 2000-02-10 2003-11-04 Pharmacia And Upjohn Company Oxazolidinone thioamides with piperazine amide substituents
GB0009803D0 (en) * 2000-04-25 2000-06-07 Astrazeneca Ab Chemical compounds
AU5889701A (en) * 2000-06-05 2001-12-17 Dong A Pharm Co Ltd Novel oxazolidinone derivatives and a process for the preparation thereof
WO2003008389A1 (en) * 2001-07-16 2003-01-30 Ranbaxy Laboratories Limited Oxazolidinone derivatives as potential antimicrobials
JP2004504321A (en) * 2000-07-17 2004-02-12 ランバクシー　ラボラトリーズ　リミテッド Oxazolidinone derivatives as antimicrobial agents
PE20020300A1 (en) * 2000-08-22 2002-05-10 Pharmacia Corp COMPOSITION OF SOLUTION OF AN ANTIBIOTIC DRUG BASED ON OXAZOLIDINONE WITH IMPROVEMENT OF DRUG LOAD
PE20020578A1 (en) 2000-10-10 2002-08-14 Upjohn Co A TOPICAL ANTIBIOTIC COMPOSITION FOR THE TREATMENT OF EYE INFECTIONS
US6861433B2 (en) * 2000-12-15 2005-03-01 Pharmacia & Upjohn Company Oxazolidinone photoaffinity probes
US6956040B2 (en) 2001-07-16 2005-10-18 Ranbaxy Laboratories Limited Oxazolidinone piperazinyl derivatives as potential antimicrobials
TW200302095A (en) * 2002-01-25 2003-08-01 Upjohn Co Oxazolidinone cotherapy
MXPA04008173A (en) * 2002-02-22 2004-11-26 Pharmacia Corp Ophthalmic antibiotic drug formulations containing a cyclodextrin compound and cetyl pyridinium chloride.
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
RU2354372C2 (en) * 2002-03-29 2009-05-10 Фармация Энд Апджон Компани Ллс Parenteral intravenous and peroral introduction of oxazolidinones for treatment of infectious foot lesions in diabetes
EP1539745B1 (en) * 2002-08-12 2006-03-29 Pharmacia & Upjohn Company LLC N-aryl-2-oxazolidinones and their derivatives
EP1578734A1 (en) * 2002-08-22 2005-09-28 Orchid Chemicals and Pharmaceuticals Ltd Novel antibacterial agents
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AU2003280143A1 (en) * 2002-11-21 2004-06-15 Pharmacia & Upjohn Company Llc N-(4-(piperazin-1-yl)-phenyl-2-oxazolidinone-5-carboxamide derivates and related compounds as antibacterial agents
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Also Published As

Publication number Publication date
EP0730591A1 (en) 1996-09-11
WO1995014684A1 (en) 1995-06-01
TW427987B (en) 2001-04-01
ES2133588T3 (en) 1999-09-16
NZ274966A (en) 1998-01-26
JPH09505582A (en) 1997-06-03
US5652238A (en) 1997-07-29
PE22896A1 (en) 1996-06-07
CO4290433A1 (en) 1996-04-17
GR3031420T3 (en) 2000-01-31
DE69419523D1 (en) 1999-08-19
EP0730591B1 (en) 1999-07-14
ZA947885B (en) 1996-04-09
JP3698724B2 (en) 2005-09-21
IL111215A0 (en) 1994-12-29
AU8010394A (en) 1995-06-13
ATE182142T1 (en) 1999-07-15
CN1046276C (en) 1999-11-10
KR100312903B1 (en) 2002-02-28
CA2174107C (en) 2005-04-12
LV12538B (en) 2000-12-20
AU698699B2 (en) 1998-11-05
CN1135752A (en) 1996-11-13
DE69419523T2 (en) 1999-11-25
DK0730591T3 (en) 2000-01-31
LV12538A (en) 2000-10-20
KR960705818A (en) 1996-11-08

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