WO2004099199A1 - Dérivés d'oxazolidinone utiles comme agents antimicrobiens - Google Patents

Dérivés d'oxazolidinone utiles comme agents antimicrobiens Download PDF

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Publication number
WO2004099199A1
WO2004099199A1 PCT/IB2003/001754 IB0301754W WO2004099199A1 WO 2004099199 A1 WO2004099199 A1 WO 2004099199A1 IB 0301754 W IB0301754 W IB 0301754W WO 2004099199 A1 WO2004099199 A1 WO 2004099199A1
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Prior art keywords
alkyl
cycloalkyl
substituted
formula
alkoxy
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PCT/IB2003/001754
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English (en)
Inventor
Anita Mehta
Ajjarapu Venkata Subrahmanya Raja Rao
Ashok Rattan
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Ranbaxy Laboratories Limited
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Publication date
Application filed by Ranbaxy Laboratories Limited filed Critical Ranbaxy Laboratories Limited
Priority to AU2003223034A priority Critical patent/AU2003223034A1/en
Priority to EP03719003A priority patent/EP1625124A1/fr
Priority to PCT/IB2003/001754 priority patent/WO2004099199A1/fr
Publication of WO2004099199A1 publication Critical patent/WO2004099199A1/fr

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    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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

Definitions

  • the present invention relates to certain substituted phenyl oxazolidinones and to the processes for the synthesis of the same.
  • This invention also relates to pharmaceutical compositions containing the compounds of the present invention as antimicrobials.
  • the compounds are useful antimicrobial agents, effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria such as multiply-resistant staphylococci, streptococci and enterococci as well as anaerobic organisms such as Bacterioides spp. and Clostridia spp. species, and acid fast organisms such as Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp.
  • Vancomycin which inspite of its various drawbacks, has become the drug of choice for MRS A infections. Streptococcus pneumoniae is a major pathogen causing pneumonia, sinusitis and meningitis. Until very recently it was highly susceptible to penicillin. Recently though, different PBP 2' strains with different susceptibility to penicillin have been reported from across the globe.
  • Oxazolidinones are a new class of synthetic antimicrobial agents which kill gram positive pathogens by inhibiting a very early stage of protein synthesis. Oxazolidinones inhibit the formation of ribosomal initiation complex involving 30S and 50S ribosomes leading to prevention of initiation complex formation. Due to their novel mechanism of action, these compounds are active against pathogens resistant to other clinically useful antibiotics.
  • the invention involves the synthesis; identification and profiling of oxazolidinone molecules which have good activity against multiply resistant gram positive pathogens like MRSA, VRE and PRSP. Some of these molecules have activity against MDR-TB and MAI strains, while others have significant activity against important anaerobic bacteria.
  • the present invention provides processes for the syntheses of phenyloxazolidinone derivatives which can exhibit significant antibacterial activity against multiply resistant gram positive pathogens like MRSA, VRE and PRSP against MDR-TB and MAI strains, in order to provide safe and effective treatment of bacterial infections.
  • T is a five to seven membered heterocyclic ring, substituted heterocyclic ring, aryl, substituted aryl, bound to the ring C with a linker W, for example, particular forms of T are selected from aryl and five membered heteroaryl which are further substituted by a group represented by R, wherein R is H, C 1-6 alkyl, F, Cl, Br, I, - CN, COR 5 , COOR 5 , N ⁇ R?), NHCOC(R 8 , R 9 , R 10 ), CON (Rs, R 7 ), CH 2 NO 2 ,
  • R 4 is hydrogen, C 2 alkyl, C 3 12 cycloalkyl, C 1 6 alkoxy, aryl, heteroaryl, C 1-6 alkoxycarbonyl or C 1 6 alkyl substituted with one or more of F, Cl, Br, I or OH;
  • R 5 is H, C 1-12 alkyl, C 3-12 cycloalkyl, C 1-6 alkoxy, C ⁇ -6 alkyl substituted with one or more of F, Cl, Br, I or OH, aryl or heteroaryl;
  • R 6 and R 7 are independently H, optionally substituted - 12 alkyl, C 3-12 cycloalkyl
  • n is an integer in the range from 0 to 3;
  • X is CH, CH-S, CH-O, N or CHNR ⁇ , wherein R ⁇ is hydrogen, optionally substituted C ⁇ 2 alkyl, C 3 12 cycloalkyl, C 1 6 alkoxy, C 1 6 alkyl, C 1-6 alkylcarbonyl, C 1-6 alkylcarboxy, aryl or heteroaryl;
  • E is hydrogen, hydroxy or lower alkyl (C ⁇ -C 4 );
  • Y and Z are independently hydrogen, C 1 6 alkyl, C 3 12 cycloalkyl or a C Q _ 3 bridging group;
  • U and V are independently hydrogen, optionally substituted C j _ 6 alkyl, F, Cl, Br, I, C j _ 12 alkyl substituted with one or more of F, Cl, Br, I;
  • Particular compounds of Formula I have as acetamide, halogen, ether linked heteroaryl or amino-heteroaryl, substituted acetamide and the most preferred compounds in this series would be prepared as the optically pure enantiomers having the (S)- configuration according to the Cahn-Ingold-Prelog notation at C 5 of the oxazolidinone ring.
  • R are independently hydrogen, C 2 alkyl, C 3 _ 12 cycloalkyl, C 1 6 alkoxy, aryl, heteroaryl,
  • U and V are independently hydrogen, optionally substituted C 1-6 alkyl, F, Cl, Br, C 1-1 alkyl substituted with one or more of F, Cl, Br, I;
  • Y and Z are independently hydrogen, C 1-6 alkyl, C 3-12 cycloalkyl, C 0- bridging group;
  • X is CH, CH-S, CH-O, N or CHNR ⁇ , wherein R ⁇ is hydrogen, optionally substituted . 12 alkyl, C 3-12 cycloalkyl, C 1-6 alkoxy, C 1-6 alkyl carbonyl, C 1-6 alkylcarboxy, aryl or heteroaryl;
  • E is hydrogen, hydroxy or lower alkyl (Ci-C 4 );
  • R ⁇ is hydrogen, optionally substituted C 1-12 alkyl, C 3-12 cycloalkyl, C 1-6 alkoxy, C 1-6 alkyl carbonyl, C 1-6 alkylcarboxy, aryl or heteroaryl;
  • Qi is O, S or NR ⁇ , wherein R ⁇ is as defined above;
  • R 6 and R 7 are independently H, optionally substituted C 1-12 alkyl, C 3-12 cycloalkyl, C 1-6 alkoxy;
  • R 8 and R 9 are independently H, C 1-6 alkyl, F, Cl, Br, I, C 1-12 alkyl substituted with one or more of F, Cl, Br, I, OR 5 , SR 4 , N(R 6 ,R 7 );
  • R 10 H, optionally substituted C 1-12 alkyl, C -1 cycloalkyl, C 1-6 alkoxy, C 1-6 alkyl, aryl or heteroaryl;
  • n is an integer in the range from 0 to 3.
  • ring C may be 6-8 membered in size and the ring may have either two or three carbon atoms between each nitrogen atom, for example:
  • the ring C may be bridged to form a bicyclic system as shown below:
  • ring C is optionally substituted at positions Y and Z
  • alkyl groups, cycloalkyl groups, fluoro group, carboxylic and corresponding esters, amides, substituted alkyls or bridging alkyl groups are as shown below:
  • ring C also includes the following structures:
  • n is as defined earlier.
  • U and V are independently hydrogen, optionally substituted C 1-6 alkyl, F, Cl, Br, C ⁇ -12 alkyl substituted with one or more of F, Cl, Br, I;
  • Y and Z are independently hydrogen, C 1-6 alkyl, C -1 cycloalkyl, or a C 0-3 bridging group;
  • X is CH, CH-S, CH-O, N or CHNR ⁇ , wherein R ⁇ is hydrogen, optionally substituted Q. 12 alkyl, C 3-12 cycloalkyl, C 1-6 alkoxy, C 1-6 alkyl carbonyl, C 1-6 alkylcarboxy, aryl or heteroaryl;
  • E is hydrogen, hydroxy or lower alkyl (C1-C4)
  • n' is an integer in the range from 0 to 3;
  • R ⁇ is hydrogen, optionally substituted C 1-12 alkyl, C 3-12 cycloalkyl, C 1-6 alkoxy, C 1-6 alkyl carbonyl, C 1-6 alkylcarboxy, aryl or heteroaryl;
  • G, J, L are independently H, C 1-6 alkyl, F, Cl, Br, I, -CN, COR 5 ,COOR 5 , N(R 6 ,R 7 ),
  • n is an integer in the range from 0 to 3.
  • Particular G, J and L substitutions can include nitro, aldehydes and halides.
  • U and V are independently hydrogen, optionally substituted C 1-6 alkyl, F, Cl, Br, C 1-12 alkyl substituted with one or more of F, Cl, Br, I;
  • Y and Z are independently hydrogen, C 1-6 alkyl, C -12 cycloalkyl, C 0-3 bridging group;
  • X is CH, CH-S, CH-O, N or CHNR ⁇ , wherein R ⁇ is hydrogen, optionally substituted .
  • E is hydrogen, hydroxy or lower alkyl (CrC 4 );
  • R ⁇ is hydrogen, optionally substituted C 1-12 alkyl, C 3-12 cycloalkyl, C 1-6 alkoxy, C 1-6 alkyl carbonyl, Ci- ⁇ alkylcarboxy, aryl or heteroaryl;
  • Qi is O, S or NR ⁇ , wherein R ⁇ is as defined earlier;
  • n is an integer in the range from 0 to 3.
  • a particular compound of Formula TV is
  • Compounds of the, present invention can be useful antimicrobial agents, effective against a number of human and veterinary pathogens, particularly aerobic Gram-positive bacteria, including multiply-antibiotic resistant staphylococci and streptococci as well as anaerobic organisms such as Mycobacterium tuberculosis and other mycobacterium species.
  • inert, pharmaceutically acceptable carriers can be either solid or liquid.
  • Solid form preparations include powders, tablets, dispersible granules, capsules, cachets, suppositories and ointments.
  • a solid carrier can be one or more substances which may also act as diluents, flavouring agents, solubilizers, lubricants, suspending agents, binders or tablets disintegrating agents; it can also be as finely divided solid which is in admixture with the finely divided active compound.
  • the active compound is mixed with carrier having the necessary binding properties in suitable proportions and compacted in the shape and size desired.
  • the powders and tablets preferably contain from about 5 to about 70 percent of the active ingredient.
  • suitable solid carriers are lactose, pectin, dextrin, starch, gelatin, tragacanth, low melting wax, cocoa butter, and the like.
  • preparation is intended to include the formulation of the active compound with encapsulating material as carrier providing a capsule in which the active component (with or without other carriers) is surrounded by carrier, which is thus in association with it.
  • capsules can be used as solid dosage forms suitable for oral administration.
  • Liquid form preparations include solutions, suspensions and emulsions. As an example may be mentioned water or water-propylene glycol solutions for parenteral injection. Such solutions are prepared so as to be acceptable to biological systems
  • Liquid preparations can also be formulated in solution in aqueous polyethylene glycol solution.
  • Aqueous solutions suitable for oral use can be prepared by dissolving the active component in water and adding suitable colorants, flavours, stabilizing and thickening agents as desired.
  • Aqueous suspension suitable for oral use can be made by dispersing the finely divided active component in water with viscous material, i.e. natural or synthetic gums, resins, methyl cellulose, sodium carboxymethyl cellulose and other well-known suspending agents.
  • Ointment preparations contain heavy metal salts of a compound of Formula I with a physiologically acceptable carrier.
  • the carrier is desirably a conventional water- dispersible hydrophilic or oil-in-water carrier, particularly a conventional semi-soft or cream-like water-dispersible or water soluble, oil-in-water emulsion infected surface with a minimum of discomfort.
  • Suitable compositions may be prepared by merely incorporating or homogeneously admixing finely divided compounds with the hydrophilic carrier or base or ointment.
  • the pharmaceutical preparations can be in unit dosage form.
  • the preparation is subdivided into unit doses containing appropriate quantities of the active component.
  • the unit dosage form can be a packaged preparation, the package containing discrete capsules, powders in vials or ampoules, and ointments capsule, cachet, tablet, gel, or cream itself or it can be the appropriate number of any of these packaged forms.
  • the quantity of active compound in a unit dose of preparation may be varied or adjusted from less than 1 mg to several grams according to the particular application and the potency of the active ingredient.
  • the compounds utilized in the pharmaceutical method of this invention are administered at the initial dosage of about 3 mg to about 40 mg per kilogram daily.
  • the dosages may be varied depending upon the requirements of the patient and the compound being employed. Determination of the proper dosage for a particular situation is within the smaller dosages which are less than the optimum dose. Small increments until the optimum effect under the daily dosage may be divided and administered in portions during the day if desired.
  • the invention provides process for the syntheses of compounds of Formulae I, II, III and IV.
  • Pharmaceutically acceptable non-toxic acid addition salts of the compounds of the present invention of Formulae I, II, III and IV may be formed with inorganic or organic acids, by methods well known in the art.
  • the present invention also includes within its scope prodrugs of the compounds of
  • prodrugs will be functional derivatives of these compounds which readily get converted in vivo into defined compounds.
  • Conventional procedures for the selection and preparation of suitable prodrugs are known to the artisan of ordinary skill in the art.
  • the invention also includes pharmaceutically acceptable salts, the enantiomers, diastereomers, N-oxides, metabolites in combination with pharmaceutically acceptable carrier and optionally included excipients.
  • the compounds of the present invention may be prepared by following the reaction sequences as depicted in the schemes defined below.
  • CH 2 C1, CHC1 2 , CC1 3 ; and R 3 , R_ ⁇ can be heteroaryl rings such as isoxazolyl, thiazolyl,or pyridyl;
  • E is hydrogen, hydroxy or lower alkyl (d-C 4 );
  • Y and Z are independently hydrogen, C 1 6 alkyl, C 3 _ 12 cycloalkyl or C 0 _ 3 bridging groups;
  • U and V are independently hydrogen, optionally substituted C 1 6 alkyl, F, Cl, Br, I, C 1 12 alkyl substituted with one or more of F, Cl, Br, I,
  • R 5 is H, C 1-12 alkyl, C 3-12 cycloalkyl, C 1-6 alkoxy, C 1-6 alkyl substituted with one or more of F, Cl, Br, I or OH, aryl or heteroaryl;
  • R 6 and R 7 are independently selected from H, optionally substituted C 1-1 alkyl, C 3- ⁇ 2 cycloalkyl, C ⁇ -6 alkoxy;
  • R 8 and R 9 are independently H, C 1-6 alkyl, F, Cl, Br, I, C 1-12 alkyl substituted with one or more of F, Cl,
  • R ⁇ o H, optionally substituted C ⁇ - ⁇ 2 alkyl, C - ⁇ 2 cycloalkyl, C ⁇ -6 alkoxy, C ⁇ -6 alkyl, aryl or heteroaryl;
  • W is (CH 2 )o.
  • C O, CH 2 NH, NHCH 2 , CH 2 NHCH 2 , CH 2 N(R ⁇ )CH 2 , CH 2 N(R ⁇ ),
  • n' is an integer in the range from 0 to 3;
  • R ⁇ is hydrogen, optionally substituted C ⁇ _ ⁇ 2 alkyl, C 3- ⁇ 2 cycloalkyl, C ⁇ -6 alkoxy, C ⁇ -6 alkyl carbonyl, C ⁇ -6 alkylcarboxy, aryl or heteroaryl;
  • R ⁇ 2 is a suitable leaving group well l ⁇ iown to one of ordinary skill in the art such as fluoro, chloro, bromo, SCH 3 , -SO 2 CH 3 , -SO 2 CF 3 , Tos, OC 6 H 5 , -COOH or-CHO-.
  • the corresponding aldehyde can be used through a process of reductive animation and is attached to the amine of Formula V.
  • the corresponding acid can be used and the amine of Formula V can be acylated through activated esters in the presence of condensing agents, for example, 1,3- dicyclohexylcarbodiimide (DCC) and l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC).
  • condensing agents for example, 1,3- dicyclohexylcarbodiimide (DCC) and l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC).
  • DCC 1,3- dicyclohexylcarbodiimide
  • EDC l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
  • Other methods of acylation can also be employed.
  • E is hydrogen, hydroxy or lower alkyl (C ⁇ -C 4 ); Y and Z are independently hydrogen, C 1 6 alkyl, C 3 12 cycloalkyl or C Q 3 bridging groups;
  • U and V are independently hydrogen, optionally substituted C 1 6 alkyl, F, Cl, Br, I, C ⁇ alkyl substituted with one or more of F, Cl, Br, I,
  • R ⁇ 2 is a suitable leaving group such as fluoro, chloro, bromo, SCH 3 , -SO 2 CH 3 , -SO CF 3 ,
  • Qi is O, S or NRn, wherein R ⁇ is hydrogen, optionally substituted C 1-1 alkyl, C 3-12 cycloalkyl, C 1-6 alkoxy, C 1-6 alkyl carbonyl, C 1-6 alkylcarboxy, aryl or heteroaryl;
  • G, J, L are independently H, C 1-6 alkyl, F, Cl, Br, I, -CN, COR 5 ,COOR 5 , N(R 6 ,R 7 ),
  • n is an integer in the range from 0 to 3.
  • the reaction can be carried out in a suitable solvent, for example, dimethylformamide, dimethylacetamide, ethanol or ethylene glycol at a suitable temperature in the range of about -70°C to about 180°C to afford compounds of Formula II.
  • a suitable base such as triethylamine, diisopropylamine, potassium carbonate, sodium bicarbonate is useful in some cases to improve the yield of the reaction.
  • the compounds having carbonyl link can also be made by reacting heteroaromatic compound of the Formula VI, such as N-methyl pyrrole with the intermediate amine of Formula V, in the presence of triphosgene or phosgene.
  • the carbonyl linkers may also be introduced between heteroaromatic compound, such as 3- bromothiophene and the amine of Formula V with carbon monoxide in the presence of a catalyst, such as Pd (PPh 3 ) 2 Cl 2 .
  • the extended chain pyrroles having dicarbonyl linkers can also be obtained from treatment with oxalyl chloride and the amine of the Formula V.
  • the key intermediate amines of Formula V for the analogue preparation were prepared from commercially available reagents, wherein Mi is NH, NHR 13 , -CH 2 NHR ⁇ 3 , wherein R ⁇ 3 is H, ethyl, methyl, isopropyl, acetyl, cyclopropyl, alkoxy and R U, V, Y, Z and E are as defined earlier.
  • optically pure amines of Formula V could be obtained either by one of a number of assymetric syntheses or alternatively by resolution from a racemic mixture by selective crystallization of a salt prepared, with an appropriate optically active acid, such as dibenzoyl tartrate or 10-camphorsulfonic acid, followed by treatment with base to afford the optically pure amine.
  • an appropriate optically active acid such as dibenzoyl tartrate or 10-camphorsulfonic acid
  • the compounds of the invention display antibacterial activity when tested by the agar incorporation method.
  • the following minimum inhibitory concentrations ( ⁇ g/ml) were obtained for representative compounds of the invention which are given below in the following Table 1.
  • MRSA 15187 Metal Resistant Staphylococcus aureus

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  • Organic Chemistry (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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Abstract

L'invention concerne certaines phényl-oxazolidinones substituées de formules I ou II et les méthodes de synthèse de celles-ci, ainsi que des compositions pharmaceutiques qui contiennent les composés décrits comme agents antimicrobiens. Ces composés constituent des agents antimicrobiens utiles et efficaces contre nombre d'agents pathogènes humains et vétérinaires, y compris des bactéries aérobies gram positif telles que des staphylocoques, streptocoques et entérocoques polyrésistants ainsi que des organismes anaérobies tels que les espèces Bacterioides spp et Clostridia spp, et des organismes résistants aux acides tels que le Mycobacterium tuberculosis, le Mycobacterium avium et le Mycobacterium spp.
PCT/IB2003/001754 2003-05-06 2003-05-06 Dérivés d'oxazolidinone utiles comme agents antimicrobiens WO2004099199A1 (fr)

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AU2003223034A AU2003223034A1 (en) 2003-05-06 2003-05-06 Oxazolidinone derivatives as antimicrobials
EP03719003A EP1625124A1 (fr) 2003-05-06 2003-05-06 Derives d'oxazolidinone utiles comme agents antimicrobiens
PCT/IB2003/001754 WO2004099199A1 (fr) 2003-05-06 2003-05-06 Dérivés d'oxazolidinone utiles comme agents antimicrobiens

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7462633B2 (en) 2003-07-02 2008-12-09 Merck & Co., Inc. Cyclopropyl group substituted oxazolidinone antibiotics and derivatives thereof
US7858644B2 (en) 2003-01-29 2010-12-28 Asterand Uk Limited EP4 receptor antagonists
US8829041B2 (en) 2006-06-23 2014-09-09 Abbvie Inc. Cyclopropyl amine derivatives
US8853390B2 (en) 2010-09-16 2014-10-07 Abbvie Inc. Processes for preparing 1,2-substituted cyclopropyl derivatives
US9108948B2 (en) 2006-06-23 2015-08-18 Abbvie Inc. Cyclopropyl amine derivatives
US9186353B2 (en) 2009-04-27 2015-11-17 Abbvie Inc. Treatment of osteoarthritis pain
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof
US11555033B2 (en) 2020-06-18 2023-01-17 Akagera Medicines, Inc. Oxazolidinone compounds, liposome compositions comprising oxazolidinone compounds and method of use thereof

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WO1997009328A1 (fr) * 1995-09-01 1997-03-13 Pharmacia & Upjohn Company Pheniloxazolidinones presentant une liaison c-c avec des structures heterocycliques a 4-8 elements
WO1997030995A1 (fr) * 1996-02-24 1997-08-28 Zeneca Limited Derives antibiotiques d'oxazolidinone
WO1999010342A1 (fr) * 1997-08-22 1999-03-04 Zeneca Limited Derives d'oxazolidinone antibiotiques
WO1999064417A2 (fr) * 1998-06-05 1999-12-16 Astrazeneca Ab Composes chimiques
WO2000021960A1 (fr) * 1998-10-09 2000-04-20 Astrazeneca Ab Heterocyclyl amino methyloxa zolidinones comme agents antibacteriens
WO2002096916A1 (fr) * 2001-06-01 2002-12-05 Astrazeneca Ab Processus de phosphorylation
WO2003027083A1 (fr) * 2001-04-17 2003-04-03 Merck & Co., Inc. Antibiotiques oxazolidinone contenant du bicyclo[3.1.0] hexane et derives de ces derniers
WO2003072575A1 (fr) * 2002-02-28 2003-09-04 Astrazeneca Ab Composes chimiques

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997009328A1 (fr) * 1995-09-01 1997-03-13 Pharmacia & Upjohn Company Pheniloxazolidinones presentant une liaison c-c avec des structures heterocycliques a 4-8 elements
WO1997030995A1 (fr) * 1996-02-24 1997-08-28 Zeneca Limited Derives antibiotiques d'oxazolidinone
WO1999010342A1 (fr) * 1997-08-22 1999-03-04 Zeneca Limited Derives d'oxazolidinone antibiotiques
WO1999064417A2 (fr) * 1998-06-05 1999-12-16 Astrazeneca Ab Composes chimiques
WO2000021960A1 (fr) * 1998-10-09 2000-04-20 Astrazeneca Ab Heterocyclyl amino methyloxa zolidinones comme agents antibacteriens
WO2003027083A1 (fr) * 2001-04-17 2003-04-03 Merck & Co., Inc. Antibiotiques oxazolidinone contenant du bicyclo[3.1.0] hexane et derives de ces derniers
WO2002096916A1 (fr) * 2001-06-01 2002-12-05 Astrazeneca Ab Processus de phosphorylation
WO2003072575A1 (fr) * 2002-02-28 2003-09-04 Astrazeneca Ab Composes chimiques

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7858644B2 (en) 2003-01-29 2010-12-28 Asterand Uk Limited EP4 receptor antagonists
US7462633B2 (en) 2003-07-02 2008-12-09 Merck & Co., Inc. Cyclopropyl group substituted oxazolidinone antibiotics and derivatives thereof
US7582659B2 (en) 2003-07-02 2009-09-01 Merck & Co., Inc. Cyclopropyl group substituted oxazolidinone antibiotics and derivatives thereof
US8829041B2 (en) 2006-06-23 2014-09-09 Abbvie Inc. Cyclopropyl amine derivatives
US9108948B2 (en) 2006-06-23 2015-08-18 Abbvie Inc. Cyclopropyl amine derivatives
US9186353B2 (en) 2009-04-27 2015-11-17 Abbvie Inc. Treatment of osteoarthritis pain
US8853390B2 (en) 2010-09-16 2014-10-07 Abbvie Inc. Processes for preparing 1,2-substituted cyclopropyl derivatives
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof
US11555033B2 (en) 2020-06-18 2023-01-17 Akagera Medicines, Inc. Oxazolidinone compounds, liposome compositions comprising oxazolidinone compounds and method of use thereof
US11566023B2 (en) 2020-06-18 2023-01-31 Akagera Medicines, Inc. Oxazolidinone compounds, liposome compositions comprising oxazolidinone compounds and method of use thereof

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AU2003223034A1 (en) 2004-11-26

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