WO2000029396A1 - Nouveaux derives de phenyloxazolidone substitues - Google Patents

Nouveaux derives de phenyloxazolidone substitues Download PDF

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Publication number
WO2000029396A1
WO2000029396A1 PCT/EP1999/008469 EP9908469W WO0029396A1 WO 2000029396 A1 WO2000029396 A1 WO 2000029396A1 EP 9908469 W EP9908469 W EP 9908469W WO 0029396 A1 WO0029396 A1 WO 0029396A1
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defined above
alkyl
hydrogen
group
formula
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PCT/EP1999/008469
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German (de)
English (en)
Inventor
Stephan Bartel
Siegfried Raddatz
Michael Härter
Ulrich Rosentreter
Hanno Wild
Rainer Endermann
Hein-Peter Kroll
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Bayer Aktiengesellschaft
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Priority to AU13799/00A priority Critical patent/AU1379900A/en
Publication of WO2000029396A1 publication Critical patent/WO2000029396A1/fr

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    • 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
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • Antibacterial oxazolidone derivatives which have a substituted phenyl group on the nitrogen of the oxazolidone skeleton are known in the prior art (cf. WO 96/23788, WO 93/09103, WO 93/23384, WO 95/14684, WO 94 / 13649, WO 95/07271, WO 97/09328, WO 97/21708, WO 97/30981, EP-A-0 127 902, EP-A-0 184 170, EP-A-0 316 594, EP-A- 0 311 090,
  • EP-A-0 352 781 and WO 97/30995 These substituted in the 3-position by substituted phenyl groups oxazolidones have in the 5-position z.
  • Carbonylaminomethyl substituents which can carry further substituents on the carbonyl carbon atom.
  • the inventors of the present invention set themselves the task of finding new phenyl-substituted oxazolidone derivatives with antibacterial activity, and they succeeded in finding new thiocarbonylaminomethyl-substituted oxazolidones with substituted phenyl radicals in the 3-position of the oxazolidone, which have an extraordinarily strong antibacterial Effectiveness.
  • the present invention therefore relates to compounds of the general formula (I) wo ⁇ n
  • R 1 -OR 4 wherein R 4 is (C, -C 8 ) alkyl or (C 3 -C 8 ) cycloalkyl, or
  • R 5 and R 6 are identical or different and are hydrogen, phenyl, pyridyl or (C, -C 8 ) alkyl, which is optionally substituted by N-linked morpholine,
  • R 2 is hydrogen, (C, -C 4 ) alkyl, hydroxy or halogen
  • R 3 is a saturated, unsaturated and / or aromatic, optionally condensed and / or substituted, carbomono-, bi- or tricyclic group or a saturated, unsaturated and / or aromatic, optionally condensed and / or substituted, heteromono-, heterobi- or heterotricyclic Group is, or
  • R 3 - C - R 7 in which R 7 is hydrogen, (C, -C 4 ) alkyl or (C 3 -C 8 ) cycloalkyl,
  • R 7 is as defined above, and R 8 -NR 7 R 9 , wherein R 7 'is independently as R 7 defined above and R 9 is hydrogen, (C, -C 4 ) alkyl or
  • R 7 and R are as defined above and R "is hydrogen or (C, -C 4 ) alkyl
  • R 9 is as defined above and R 12 and R 13 are independently hydrogen or (C 1 -C 4 ) alkyl or together form a (C 2 - C 3 ) alkanediyl group,
  • R 7 and R 9 are as defined above, and R 15 and R 16 are independently hydrogen, (C, -C 4 ) alkyl or (C 3 -C 8 ) cycloalkyl, or R 3 wherein R "is as defined above, R ' 7 and R 18 are independently hydrogen, (C, -C 4 ) alkyl, -NO 2 or -CN, or
  • n is an integer from 1 to 3
  • X is -CH 2 -, -O-, -S- or -NR ", wherein R 11 is as defined above, and
  • R 22 is hydrogen, (C, - C 4) alkyl, (C 2 -C 4) alkenyl, (C 3 -C 4) cycloalkyl, or -OR 21 is where
  • R 21 is as defined above, or
  • the compounds according to the invention can exist in stereoisomeric forms which either behave like image and mirror image (enantiomers) or do not behave like image and mirror image (diastereomers).
  • the invention relates to both the enantiomers or diastereomers or their respective mixtures.
  • the racemic forms can be separated into the stereoisomerically uniform constituents in a known manner.
  • the following formula shows the corresponding spellings for enantiomerically pure and racemic forms of the oxazolidone skeleton:
  • Physiologically acceptable salts of the compounds according to the invention can be salts of the substances according to the invention with mineral acids, carboxylic acids or sulfonic acids.
  • mineral acids carboxylic acids or sulfonic acids.
  • particular preference is given to Salts with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonic acid, ethanesulfonic acid, toluenesulfonic acid, benzenesulfonic acid, naphthalenedisulfonic acid, acetic acid,
  • Propionic acid lactic acid, tartaric acid, citric acid, fumaric acid, maleic acid or benzoic acid.
  • Salts which can furthermore be mentioned are salts with customary bases, such as, for example, alkali metal salts (e.g. sodium or potassium salts), alkaline earth metal salts (e.g.
  • Calcium or magnesium salts or ammonium salts derived from ammonia or organic amines such as diethylamine, triethylamine, ethyldiisopropylamine, procaine, dibenzylamine, N-methylmorpholine, dihydroabietylamine, 1-ephenamine or methyl-piperidine.
  • (C r C 8 ) -alkyl stands for straight-chain or branched alkyl having 1 to 8 carbon atoms, such as, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl and octyl and their branched-chain isomeric forms.
  • the corresponding alkyl groups with fewer carbon atoms, such as (C r C 4 ) alkyl are derived analogously from this definition. In general, (C r C 4 ) alkyl is preferred.
  • alkyl moiety in functionalized groups are derived from this definition, such as (C 2 -C 5 ) alkynyl (eg ethynyl, propynyl etc.), (C 2 -C 4 ) alkenyl (eg vinyl, propenyl etc.), (C r C 4 ) acyl (e.g. formyl, acetyl, propionyl, butyryl etc.), (C r C 4 ) alkoxy (such as methoxy,
  • Cycloalkyl stands for a cyclic hydrocarbon residue with 3 to 8
  • Carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • the cyclopropyl, cyclopentane and cyclohexane rings are preferred.
  • Aryl generally represents an aromatic radical having 6 to 10 carbon atoms.
  • Preferred aryl radicals are phenyl and naphthyl.
  • Halogen in the context of the invention represents fluorine, chlorine, bromine or iodine, with fluorine and chlorine being preferred.
  • a saturated, unsaturated and / or aromatic, optionally fused and / or substituted, carbomono-, bi- or tricyclic group for R 3 includes carbomono-, bi- or tricyclic groups, if these are bi- or tricyclic radicals which can be fused to one another, linked via a bond or linked via two bonds (spirocyclic compounds), and these cycles, if there are more than two in the remainder, can be independently saturated, unsaturated and / or aromatic .
  • This group can also be substituted or unsubstituted.
  • Such groups are known per se in the prior art and are described, for example, in the prior art described above.
  • heteromono-, heterobi- or heterotricyclic groups for R 3 include heteromono-, heterobi- or heterotricyclic groups which have at least one heteroatom, preferably 1 to 3 heteroatoms selected from S, N or
  • Contain O Contain O, a, where the cycles can be condensed, can be connected to one another by a bond or, as in the case of the spiro compounds, can be connected to one another by two bonds.
  • This definition also includes radicals R 3 in which carbocyclic and heterocyclic groups occur simultaneously. If there are more than two, the individual cycles can be independently saturated, unsaturated and / or aromatic and substituted. Such groups are also known per se from the prior art and are described, for example, by the prior art mentioned in the introduction. Specific examples of R 3 are shown in the following preferred embodiment of the compounds of the general formula
  • R 3 is selected from the groups of the formulas:
  • R is selected from the group of substituents which consists of:
  • n is an integer of 1 or 2
  • (n) is (C, -C 8 ) alkyl or (C 3 -C 8 ) cycloalkyl, which can optionally be substituted with one or more substituents, which come from the group of the abovementioned substituents
  • (q) is phenyl which may be optionally substituted with one or more substituents selected from the group of the above-mentioned substituents (a) to (n),
  • R 24 and R 24 are independently selected from:
  • phenyl which may be optionally substituted with one or more substituents selected from the group consisting of fluorine, chlorine, (C, -C 4 ) alkyl, hydroxy, (C, -C 4 ) -
  • R 26 is selected from the group of substituents consisting of:
  • R 25 is selected from the group of substituents, which consists of:
  • R 32 and R 33 are the same or 5 different and are hydrogen or (C, -C 4 ) alkyl or together form a (C 4 -C 6 ) alkanediyl group , or R 29 and R 30 together - (CH 2 ) 2 -O- (CH 2 ) 2 - or - (CH 2 ) 2 -N (R 31 ) - (CH 2 ) 2 -, wherein R 3 'as above is defined, form 10 (c) (C 2 -C 5 ) alkenyl,
  • R 35 is hydrogen, (C, -C 4 ) alkyl
  • Cycloalkyl, -OR 37 wherein R 37 is hydrogen or (C, -C 4 ) alkyl, or -NR 32 R 33 , wherein R 32 and R 33 are as defined above, -N 3 ,
  • R 38 is (C, -C 4 ) alkyl
  • R 37 is in each case as defined above, -NR 29 R 30 , in which R 29 and R 30 are as defined above, -S (O) 0 R 28 , where o and R 28 are as defined above, (C 3 -C 8 ) cycloalkyl,
  • R 29 is as defined above, or
  • H O is where P R29 is as defined above,
  • R 44 is R 29 or -NR 29 R 31 , wherein R 29 and
  • R 3 is a group of the formula:
  • R 45 -COR 46 wherein R 46 is (C, -C 6 ) alkyl that may be substituted with hydroxy, or -C (O) -OR 47 , wherein R 47 is (C, -C 6 ) alkyl , or
  • R 3 is a group of the formula
  • R 47 is as defined above, or
  • R 3 is a group of the formula:
  • Y is S or O, or
  • R 3 is a group of the formula:
  • R 48 is hydrogen, (C, -C 6 ) alkyl, that can optionally have one or more substituents selected from OH, CN or halogen, - (CH 2 ) r - (C 6 -C 10 ) aryl, wherein r is an integer from 1 to 4, or - (CH 2 ) r is -OR 49 , wherein r is as defined above, and R 49 is hydrogen, (C, -C 6 ) alkyl, - (CH 2 ) r - (C 6 -C 10 ) aryl, wherein r is as defined above, or is -C (O) R 50 , wherein R 50 is (C, C 6 ) alkyl, or
  • R 3 is a group of the formula:
  • R 3 is a group of the formula:
  • R 3 is a group of the formula:
  • R 55 and R 56 are independent of are each other hydrogen, (C, -C 4 ) alkyl, (C 3 -C 8 ) cycloalkyl or phenyl or together form a (C, -C 6 ) alkanediyl group, or
  • R 3 is a group of the formula:
  • R is as defined above
  • R 57 is selected from the group of substituents, which consists of:
  • R 29 is as defined above, or
  • I is II, Q , where R is as defined above, - N - C - R 29
  • R 29 , R 35 and R 41 are as defined above and R 44 is -R 29 or -NR 29 R 31 , wherein R 29 and R 31 are as defined above, 15 (v) (C, -C 8 ) alkyl, which may be optionally substituted with one or more substituents which are selected from the group consisting of: halogen; -OH, 20 - oxo that is not in the ⁇ position,
  • R 58 is hydrogen, halogen, OR 37 , wherein R 37 is as defined above, (C, -C 3 ) alkyl, or NO 2 , or when R 3
  • R 57 and R 58 together can form a six-membered carbocyclic ring.
  • R 1 is -OR 4 , in which R 4 is (C, -C 8 ) alkyl, or -NHR 5 , in which R 5 is hydrogen or (C, -C 8 ) alkyl,
  • R 2 is hydrogen or halogen
  • R 3 "CR , wherein R 7 is (C, -C 4 ) alkyl
  • R 7 is (C r C 4 ) alkyl and R 8 is -OR 7 ' , where R 7' is as defined above,
  • R 11 is as defined above
  • R 17 is hydrogen
  • R 18 is -CN or -NO 2 or R 17 -CN or -NO 2 and R ' 8 is hydrogen,
  • Pyridyl or is where Y is S or O.
  • Very particularly preferred compounds of the inventions are selected from the group consisting of:
  • the invention further relates to a process for the preparation of the compounds of formula (I) and their pharmaceutically acceptable salts, in which
  • R 2 and R 3 are as defined above, or their salts with compounds of the general formula (III)
  • R 4 is as defined above, or to obtain a salt thereof.
  • R 2 , R 3 , R 5 or R 6 are as defined above, or
  • A is halogen, preferably chlorine, reacted to obtain compounds of formula (I), or
  • the compounds of the invention find use as medicaments.
  • the invention therefore also relates to pharmaceuticals
  • compositions comprising at least one compound of the invention in admixture with at least one pharmaceutically acceptable carrier, and the use of the compounds of the invention in the manufacture of a medicament for the treatment of bacterial infections in humans or animals.
  • the compounds of the invention have a high antibacterial activity, which is superior to that of the prior art analog compounds, as shown by comparative examples 1 and 2, which is extremely surprising.
  • the MIC values were determined using the microdilution method in BH medium. Each test substance was dissolved in the nutrient medium. A series of concentrations of the test substances was created in the microtiter plate by serial dilution. Overnight cultures of the pathogens were used for inoculation, which were previously diluted 1: 250 in the nutrient medium. To 100 ⁇ l of the diluted active ingredient
  • Nutrient solutions were given 100 ⁇ l inoculation solution.
  • the microtiter plates were incubated at 37 ° C and read after about 20 hours or after 3 to 5 days.
  • the MIC value ( ⁇ g / ml) indicates the lowest active substance concentration at which no growth was discernible.
  • the compounds according to the invention have a broad antibacterial spectrum, especially against gram-positive germs and some gram-negative bacteria, as well as mycobacteria, corynebacteria, Haemophilus influenzae and anaerobic germs.
  • the compounds according to the invention are active against a broad spectrum of microorganisms. With their help, gram-positive germs, gram-negative bacteria and bacteria-like microorganisms such as mycoplasmas can be combated and the diseases caused by these pathogens can be prevented, improved and / or cured.
  • the compounds according to the invention are particularly effective against bacteria and bacteria-like microorganisms. They are therefore particularly well suited for the prophylaxis and chemotherapy of local and systemic infections in human and veterinary medicine that are caused by such pathogens.
  • the active ingredient (s) can optionally also be in microencapsulated form in one or more carriers.
  • the therapeutically active compounds should preferably be present in the pharmaceutical compositions listed above in a concentration of approximately 0.1 to 99.5, preferably approximately 0.5 to 95% by weight of the total mixture.
  • the pharmaceutical preparations listed above can also contain further active pharmaceutical ingredients.
  • the active compound (s) according to the invention in total amounts of about 0.5 to about 500, preferably 5 to 100 mg, kg body weight per 24 hours, optionally in the form of several Single doses to be administered to achieve the desired results.
  • a single dose contains the active ingredient (s) according to the invention preferably in amounts of about 1 to about 80, in particular 3 to 30 mg / kg, body weight.
  • the compounds of the invention can be used for the purpose of expanding the
  • Range of effects and in order to achieve an increase in effectiveness can also be combined with other antibiotics.

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract

L'invention concerne de nouveaux dérivés de phényloxazolidone substitués, leur procédé de production, des compositions pharmaceutiques les contenant et leur utilisation pour produire des médicaments, notamment des médicaments antibactériens destinés au traitement d'êtres humains et d'animaux.
PCT/EP1999/008469 1998-11-17 1999-11-05 Nouveaux derives de phenyloxazolidone substitues WO2000029396A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU13799/00A AU1379900A (en) 1998-11-17 1999-11-05 Novel substituted phenyloxazolidone derivatives

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DE19853001.3 1998-11-17
DE19853001 1998-11-17

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WO2000029396A1 true WO2000029396A1 (fr) 2000-05-25

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001009107A1 (fr) * 1999-07-28 2001-02-08 Pharmacia & Upjohn Company Oxazolidinones et leur utilisation comme anti-infectieux
WO2001042229A1 (fr) * 1999-08-12 2001-06-14 Ortho-Mcneil Pharmaceutical, Inc. Amidinomethyl- et guanidinomethyl-oxazolidinones antibacteriens
WO2004056819A1 (fr) * 2002-12-19 2004-07-08 Astrazeneca Ab Derives d'oxazolidinone utilises comme agents antibacteriens
WO2005061468A1 (fr) * 2003-12-17 2005-07-07 Rib-X Pharmaceuticals, Inc. Composes heterocycliques de biaryle halogenes et methodes de fabrication et d'utilisation
US7148219B2 (en) 2003-06-03 2006-12-12 Rib-X Pharmaceuticals, Inc. Biaryl heterocyclic compounds and methods of making and using the same
US7435751B2 (en) 2005-04-06 2008-10-14 Vara Prasad Venkata Nagendra Josyula 7-Fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents
US7592335B2 (en) 2005-04-15 2009-09-22 Ranbaxy Laboratories Limited Oxazolidinone derivatives as antimicrobials
EP2208729A1 (fr) * 2007-10-02 2010-07-21 Research Foundation Itsuu Laboratory Dérivé d'oxazolidinone avec hétérocycle à 7 chaînons
US8324398B2 (en) 2003-06-03 2012-12-04 Rib-X Pharmaceuticals, Inc. Process for the synthesis of biaryl oxazolidinones
US8399660B2 (en) 2005-06-08 2013-03-19 Rib-X Pharmaceuticals, Inc. Process for the synthesis of triazoles
US8785625B2 (en) 2006-03-31 2014-07-22 Research Foundation Itsuu Laboratory Compound having heterocyclic ring
US8841306B2 (en) 2008-11-20 2014-09-23 Panacea Biotec Ltd. Antimicrobials
JP2014530232A (ja) * 2011-10-11 2014-11-17 カウンシル オブ サイエンティフィク アンド インダストリアル リサーチ オキサゾリジノン誘導体のシラアナログ及びその合成
US8906913B2 (en) 2009-06-26 2014-12-09 Panacea Biotec Limited Azabicyclohexanes

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EP0312000A1 (fr) * 1987-10-16 1989-04-19 The Du Pont Merck Pharmaceutical Company Dérivés d'aminométhyl-oxo-oxazolidinyl-benzène comme agents antibactériens
EP0352781A2 (fr) * 1988-07-29 1990-01-31 The Du Pont Merck Pharmaceutical Company Dérivés d'aminométhyloxooxazolidinyl-arylbenzène comme agents antibactériens
WO1993009103A1 (fr) * 1991-11-01 1993-05-13 The Upjohn Company Aryl- et heteroarylphenyloxazolidinones substituees, utilisees comme agents antibacteriens
WO1995007271A1 (fr) * 1993-09-09 1995-03-16 The Upjohn Company Agents antimicrobiens oxazolidinone a substitution oxazine et thiazine
EP0789025A1 (fr) * 1996-02-06 1997-08-13 Bayer Ag Oxazolidinones substituées et leur utilisation comme médicaments antibactériens
WO1998054161A1 (fr) * 1997-05-30 1998-12-03 Pharmacia & Upjohn Company Agents antibacteriens oxazolidinone ayant une fonctionnalite thiocarbonyle
WO1999012914A1 (fr) * 1997-09-11 1999-03-18 Hokuriku Seiyaku Co., Ltd. Derives de thiouree

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0312000A1 (fr) * 1987-10-16 1989-04-19 The Du Pont Merck Pharmaceutical Company Dérivés d'aminométhyl-oxo-oxazolidinyl-benzène comme agents antibactériens
EP0352781A2 (fr) * 1988-07-29 1990-01-31 The Du Pont Merck Pharmaceutical Company Dérivés d'aminométhyloxooxazolidinyl-arylbenzène comme agents antibactériens
WO1993009103A1 (fr) * 1991-11-01 1993-05-13 The Upjohn Company Aryl- et heteroarylphenyloxazolidinones substituees, utilisees comme agents antibacteriens
WO1995007271A1 (fr) * 1993-09-09 1995-03-16 The Upjohn Company Agents antimicrobiens oxazolidinone a substitution oxazine et thiazine
EP0789025A1 (fr) * 1996-02-06 1997-08-13 Bayer Ag Oxazolidinones substituées et leur utilisation comme médicaments antibactériens
WO1998054161A1 (fr) * 1997-05-30 1998-12-03 Pharmacia & Upjohn Company Agents antibacteriens oxazolidinone ayant une fonctionnalite thiocarbonyle
WO1999012914A1 (fr) * 1997-09-11 1999-03-18 Hokuriku Seiyaku Co., Ltd. Derives de thiouree

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001009107A1 (fr) * 1999-07-28 2001-02-08 Pharmacia & Upjohn Company Oxazolidinones et leur utilisation comme anti-infectieux
US6441005B1 (en) 1999-07-28 2002-08-27 Pharmacia & Upjohn Company Oxazolidinone compounds and compositions, and methods of using the same
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