CA2133079A1 - Oxazolidinone antimicrobials containing substituted diazine moieties - Google Patents

Oxazolidinone antimicrobials containing substituted diazine moieties

Info

Publication number
CA2133079A1
CA2133079A1 CA002133079A CA2133079A CA2133079A1 CA 2133079 A1 CA2133079 A1 CA 2133079A1 CA 002133079 A CA002133079 A CA 002133079A CA 2133079 A CA2133079 A CA 2133079A CA 2133079 A1 CA2133079 A1 CA 2133079A1
Authority
CA
Canada
Prior art keywords
alkyl
hydrogen
substituted
cycloalkyl
independently
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
CA002133079A
Other languages
French (fr)
Other versions
CA2133079C (en
Inventor
Douglas K. Hutchinson
Steven Joseph Brickner
Michael Robert Barbachyn
Ronald B. Gammill
Mahesh V. Patel
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
Douglas K. Hutchinson
Steven Joseph Brickner
Michael Robert Barbachyn
Ronald B. Gammill
Mahesh V. Patel
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 Douglas K. Hutchinson, Steven Joseph Brickner, Michael Robert Barbachyn, Ronald B. Gammill, Mahesh V. Patel, Upjohn Company (The), Pharmacia & Upjohn Company, The Upjohn Company filed Critical Douglas K. Hutchinson
Publication of CA2133079A1 publication Critical patent/CA2133079A1/en
Application granted granted Critical
Publication of CA2133079C publication Critical patent/CA2133079C/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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • 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
    • 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
    • C07D413/10—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
    • 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

Abstract

A compound of structural formula (I) or pharmaceutically acceptable salts thereof wherein: Y is chosen from a-n as defined herein; wherein each occurrence of said C1-6 alkyl may be substituted with one or more F, Cl, Br, I, OR1, CO2R1, CN, SR1, or R1 (where R1 is a hydrogen or C1-4 alkyl); X and Z are independently C1-6 alkyl, C3-12 cycloalkyl or hydrogen, or X
and Z form a C0-3 bridging group, preferably X and Z are hydrogen; U, V and W
are independently C1-6 alkyl, F, Cl, Br, hydrogen or a C1-6 alkyl substituted with one or more of F, Cl, Br or I, preferably U and V are F and W is hydrogen; R is hydrogen, C1-12 alkyl, C3-12 cycloalkyl, C1-6 alkoxy, C1-6 alkyl substituted with one or more F, Cl, Br, I or OH; and d is 0 to 4 inclusive. Oxazolidinone derivatives possessing a substituted diazine moiety bonded to the N-aryl ring are useful antimic-robial agents, effective against a number of human and veterinary pathogens, including multiply-resistant staphylococci and streptococci, as well as anaerobic organisms such as bacteroides and clostridia species, and acid-fast organisms such as Mycobac-terium tuberculosis and Mycobaeterium avium.
CA002133079A 1992-05-08 1993-04-21 Oxazolidinone antimicrobials containing substituted diazine moieties Expired - Fee Related CA2133079C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US88043292A 1992-05-08 1992-05-08
US880,432 1992-05-08
PCT/US1993/003570 WO1993023384A1 (en) 1992-05-08 1993-04-21 Oxazolidinones containing a substituted diazine moiety and their use as antimicrobials

Publications (2)

Publication Number Publication Date
CA2133079A1 true CA2133079A1 (en) 1993-11-25
CA2133079C CA2133079C (en) 2004-08-03

Family

ID=25376270

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002133079A Expired - Fee Related CA2133079C (en) 1992-05-08 1993-04-21 Oxazolidinone antimicrobials containing substituted diazine moieties

Country Status (26)

Country Link
US (2) US5547950A (en)
EP (1) EP0640077B1 (en)
JP (1) JP3255920B2 (en)
KR (1) KR100281775B1 (en)
CN (1) CN1044236C (en)
AT (1) ATE219770T1 (en)
AU (1) AU668733B2 (en)
CA (1) CA2133079C (en)
CZ (1) CZ281884B6 (en)
DE (1) DE69332061T2 (en)
DK (1) DK0640077T3 (en)
ES (1) ES2180545T3 (en)
FI (1) FI945246A (en)
HU (2) HUT72296A (en)
IL (1) IL105555A (en)
LV (1) LV13075B (en)
MX (1) MX9302665A (en)
MY (1) MY117338A (en)
NO (1) NO306112B1 (en)
PL (2) PL174850B1 (en)
PT (1) PT640077E (en)
RU (1) RU2105003C1 (en)
SK (1) SK283420B6 (en)
TW (1) TW274549B (en)
WO (1) WO1993023384A1 (en)
ZA (1) ZA932855B (en)

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