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NZ773022B2 - Substituted phenyloxazolidinones for antimicrobial therapy - Google Patents
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NZ773022B2 - Substituted phenyloxazolidinones for antimicrobial therapy - Google Patents

Substituted phenyloxazolidinones for antimicrobial therapy

Info

Publication number
NZ773022B2
NZ773022B2 NZ773022A NZ77302216A NZ773022B2 NZ 773022 B2 NZ773022 B2 NZ 773022B2 NZ 773022 A NZ773022 A NZ 773022A NZ 77302216 A NZ77302216 A NZ 77302216A NZ 773022 B2 NZ773022 B2 NZ 773022B2
Authority
NZ
New Zealand
Prior art keywords
independently
cycloalkyl
alkyl
compound
heteroaryl
Prior art date
Application number
NZ773022A
Other versions
NZ773022A (en
Inventor
Christopher B Cooper
Nader Fotouhi
Haihong Huang
Takushi Kaneko
Doongfeng Zhang
Original Assignee
The Global Alliance For Tb Drug Development Inc
Filing date
Publication date
Application filed by The Global Alliance For Tb Drug Development Inc filed Critical The Global Alliance For Tb Drug Development Inc
Publication of NZ773022A publication Critical patent/NZ773022A/en
Publication of NZ773022B2 publication Critical patent/NZ773022B2/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
    • 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
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5386—1,4-Oxazines, e.g. morpholine spiro-condensed or forming part of bridged ring systems
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P31/06—Antibacterial agents for tuberculosis
    • 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
    • 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
    • C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
    • 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
    • C07D413/06—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 only aliphatic carbon atoms
    • 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
    • C07D417/10—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 carbon chain containing aromatic rings
    • 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
    • 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
    • C07D417/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/08—Bridged systems

Abstract

The present invention relates to novel oxazolidinones (Formula I) or a pharmaceutically acceptable salt having ring A characterized by N-containing monocyclic, bicyclic or spirocyclic substituents, to their preparation, and to their use as drugs for treating Mycobacterium tuberculosis and other microbial infections, either alone or in combination with other anti-infective treatments.

Claims (9)

WHAT IS CLAIMED IS:
1. A compound of Formula I, or a pharmaceutically acceptable salt, e, or e thereof: R' O A N N wherein: R is independently OR1, OC(O)R2, OC(O)NHR2, R2, NHS(O)2R2, NR3R4, NHC(O)R5; R’ and R’’ are independently H, F, Cl or OMe; each R1 is independently C1-C6 alkyl, C3-C8 cycloalkyl, n said alkyl, cycloalkyl are optionally substituted with 1 to 4 groups selected from halo, hydroxy, C1-C6 alkyl, C1-C6 alkyloxy; each R2 is independently C3-C8 cycloalkyl, heterocyclyl, heteroaryl or aryl, n said cycloalkyl, heterocyclyl, heteroaryl, or aryl are optionally substituted with 1 to 4 groups selected from halo, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 acyloxy, CF3, NO2, CN and NH2; each R3 and R4 is ndently H, C1-C6 alkyl, C3-C8 cycloalkyl, heterocyclyl, heteroaryl, aryl, wherein R3 and R4 are not both H; or R3 and R4 taken together with the nitrogen to which they are attached, form a 4- to 8-membered heterocyclyl or heteroaryl with 1 to 3 onal heteroatoms selected from O, S, or N, wherein said alkyl, cycloalkyl, heterocyclyl, heteroaryl, or aryl are optionally substituted with 1 to 4 groups selected from halo, C1-C6 alkyl, C1-C6 alkoxy, CF3, NO2, CN; each R5 is independently C3-C8 cycloalkyl, heteroaryl, aryl, wherein said cycloalkyl, heterocyclyl, heteroaryl, or aryl are optionally substituted with 1 to 4 groups selected from halo, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 acyloxy, CF3, NO2, CN and Ring A is selected from: (CH2)m R7 , wherein, each R6 and R7 is independently H, F, CH3, CH2CH3, CF3, phenyl; X = O, S, SO, SO2; m is 1, or 2, and wherein R is not triazole.
2. A compound of Formula II, or a ceutically acceptable salt, hydrate, or solvate thereof: R' O X O N N R is independently OR1, OC(O)R2, NR3R4, NHS(O)2R2, NHC(O)R5; R’ and R’’ are independently H, or F; R1 is independently C1-C6 alkyl, C3-C6 cycloalkyl; R2 is independently C1-C6 alkyl, C3-C6 cycloalkyl; R3 and R4 is independently H, C1-C6 alkyl, C3-C6 cycloalkyl, , wherein R3 and R4 are not both H; or R3 and R4 taken together with the nitrogen to which they are attached to form line, thiamorpholine or piperazine; R5 is independently C3-C6 cycloalkyl, 5- or 6-membered heteroaryl or phenyl; R6 and R7 is independently H, F, CH3, CH2CH3, CF3; and X = O, S, SO, SO2.
3. A compound of Formula III, or a pharmaceutically acceptable salt, hydrate, or solvate thereof: R6 R' O X N N R7 R'' wherein, R is independently OR1, OC(O)R2, NR3R4, NHS(O)2R2, NHC(O)R5; R’ and R’’ are ndently H, or F; R1 is independently C1-C6 alkyl, C3-C6 cycloalkyl; R2 is independently C1-C6 alkyl, C3-C6 cycloalkyl; R3 and R4 is independently H, C1-C6 alkyl, C3-C6 cycloalkyl, or , wherein R3 and R4 are not both H; or R3 and R4 taken together with the nitrogen to which they are attached to form morpholine, rpholine, piperazine or triazole; R5 is independently C3-C6 cycloalkyl, C1-C6 alkoxy, 5- or 6-membered heteroaryl or phenyl; R6 and R7 is independently H, F, CH3, CH2CH3, CF3; and X = O, S, SO, SO2.
4. The compound of claim 2, wherein the compound is ented by Formula IIa or X O N N F O X O N N wherein, R is independently OCH3, OCH2CH3, OC(O)CH3, NHCH3, NHC6H5, NHS(O)2R2, R2 is independently C1-C6 alkyl; R5 is independently C3-C6 cycloalkyl, furan, thiophene or phenyl; R6 and R7 is ndently H, F, CH3, CH2CH3, CF3; and X = O, S, SO, SO2.
5. The compound of claim 3, wherein the compound is represented by Formula IIIa or IIIb: R6 O X N N R7 F R6 F O X N N R7 F R is independently OCH3, OCH2CH3, OC(O)CH3, NHCH3, NHC6H5, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, NHS(O)2R2, NHC(O)R5; R2 is independently C1-C6 alkyl; R5 is independently C3-C6 cycloalkyl, C1-C6 alkoxy, furan, thiophene or phenyl; R6 and R7 is independently H, F, CH3, CH2CH3, CF3; and X = O, S, SO, SO2.
6. A pharmaceutical composition comprising at least one compound of any one of claims 1 to 5, or a pharmaceutically acceptable salt, hydrate, or solvate thereof, and one or more ceutically acceptable carriers and/or additives.
7. The pharmaceutical ition of claim 6, further comprising one or more additional nfective treatments.
8. Use of the compound of any one of claims 1 to 5, or the pharmaceutical composition of claim 6 or claim 7, in the manufacture of a medicament for ting and treating a microbial infection in humans.
9. The use of claim 8, wherein the microbial infection is caused by Mycobacterium tuberculosis.
NZ773022A 2016-07-15 Substituted phenyloxazolidinones for antimicrobial therapy NZ773022B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201562193963P 2015-07-17 2015-07-17
NZ738702A NZ738702B2 (en) 2016-07-15 Substituted phenyloxazolidinones for antimicrobial therapy

Publications (2)

Publication Number Publication Date
NZ773022A NZ773022A (en) 2024-04-26
NZ773022B2 true NZ773022B2 (en) 2024-07-30

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