CA2637158A1 - Oxazolidinones containing oxindoles as antibacterial agents - Google Patents
Oxazolidinones containing oxindoles as antibacterial agents Download PDFInfo
- Publication number
- CA2637158A1 CA2637158A1 CA002637158A CA2637158A CA2637158A1 CA 2637158 A1 CA2637158 A1 CA 2637158A1 CA 002637158 A CA002637158 A CA 002637158A CA 2637158 A CA2637158 A CA 2637158A CA 2637158 A1 CA2637158 A1 CA 2637158A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- acid
- bacteria
- infections
- methyl
- 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.)
- Abandoned
Links
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 6
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 11
- 150000005623 oxindoles Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 31
- 208000015181 infectious disease Diseases 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 241000894006 Bacteria Species 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- GAHYZNZNHVIRIO-AWEZNQCLSA-N (5r)-3-(2-oxo-1-propan-2-yl-3h-indol-5-yl)-5-(triazol-1-ylmethyl)-1,3-oxazolidin-2-one Chemical compound C([C@H]1CN(C(O1)=O)C=1C=C2CC(=O)N(C2=CC=1)C(C)C)N1C=CN=N1 GAHYZNZNHVIRIO-AWEZNQCLSA-N 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- WAVOOALFKPEBMT-ZDUSSCGKSA-N (5r)-3-(1-ethyl-2-oxo-3h-indol-5-yl)-5-(triazol-1-ylmethyl)-1,3-oxazolidin-2-one Chemical compound C([C@H]1CN(C(O1)=O)C=1C=C2CC(=O)N(C2=CC=1)CC)N1C=CN=N1 WAVOOALFKPEBMT-ZDUSSCGKSA-N 0.000 claims description 3
- 241000192125 Firmicutes Species 0.000 claims description 3
- 241000606790 Haemophilus Species 0.000 claims description 3
- 241000588621 Moraxella Species 0.000 claims description 3
- 241000295644 Staphylococcaceae Species 0.000 claims description 3
- AACLABFVHBPSQH-LBPRGKRZSA-N (5r)-3-(1-methyl-2-oxo-3h-indol-5-yl)-5-(triazol-1-ylmethyl)-1,3-oxazolidin-2-one Chemical compound C([C@H]1CN(C(O1)=O)C=1C=C2CC(=O)N(C2=CC=1)C)N1C=CN=N1 AACLABFVHBPSQH-LBPRGKRZSA-N 0.000 claims description 2
- 241000606125 Bacteroides Species 0.000 claims description 2
- 241000606161 Chlamydia Species 0.000 claims description 2
- 241001112696 Clostridia Species 0.000 claims description 2
- 208000008960 Diabetic foot Diseases 0.000 claims description 2
- 206010014666 Endocarditis bacterial Diseases 0.000 claims description 2
- 208000001860 Eye Infections Diseases 0.000 claims description 2
- 241000606768 Haemophilus influenzae Species 0.000 claims description 2
- 241000588655 Moraxella catarrhalis Species 0.000 claims description 2
- 241000186367 Mycobacterium avium Species 0.000 claims description 2
- 206010031252 Osteomyelitis Diseases 0.000 claims description 2
- 208000005141 Otitis Diseases 0.000 claims description 2
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 2
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 2
- 241000193996 Streptococcus pyogenes Species 0.000 claims description 2
- 208000009361 bacterial endocarditis Diseases 0.000 claims description 2
- 208000019258 ear infection Diseases 0.000 claims description 2
- 206010014665 endocarditis Diseases 0.000 claims description 2
- 208000011323 eye infectious disease Diseases 0.000 claims description 2
- 201000007119 infective endocarditis Diseases 0.000 claims description 2
- 208000020029 respiratory tract infectious disease Diseases 0.000 claims description 2
- 201000008827 tuberculosis Diseases 0.000 claims description 2
- 241000194032 Enterococcus faecalis Species 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- -1 aluminum ion Chemical class 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 22
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 239000007832 Na2SO4 Substances 0.000 description 11
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- 239000002585 base Substances 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 230000000844 anti-bacterial effect Effects 0.000 description 10
- 238000010828 elution Methods 0.000 description 10
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- 230000014759 maintenance of location Effects 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
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- 239000002253 acid Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 5
- 238000007911 parenteral administration Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
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- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 150000003254 radicals Chemical class 0.000 description 4
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- 150000003852 triazoles Chemical class 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
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- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
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- 239000008117 stearic acid Chemical group 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- NNFOIPBIWGIGFZ-OAHLLOKOSA-N tert-butyl n-[(2r)-2-hydroxy-3-[(2-oxo-1-propan-2-yl-3h-indol-5-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CNC1=CC=C2N(C(C)C)C(=O)CC2=C1 NNFOIPBIWGIGFZ-OAHLLOKOSA-N 0.000 description 1
- BCERVHZUVNOSNR-ZCFIWIBFSA-N tert-butyl n-[(2s)-3-chloro-2-hydroxypropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CCl BCERVHZUVNOSNR-ZCFIWIBFSA-N 0.000 description 1
- ZBBGKXNNTNBRBH-LURJTMIESA-N tert-butyl n-[[(2s)-oxiran-2-yl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H]1CO1 ZBBGKXNNTNBRBH-LURJTMIESA-N 0.000 description 1
- GMKVRDXWWINYQJ-HNNXBMFYSA-N tert-butyl n-[[(5s)-2-oxo-3-(2-oxo-1-propan-2-yl-3h-indol-5-yl)-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound C=1C=C2N(C(C)C)C(=O)CC2=CC=1N1C[C@H](CNC(=O)OC(C)(C)C)OC1=O GMKVRDXWWINYQJ-HNNXBMFYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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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
- C07D413/14—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77157006P | 2006-02-08 | 2006-02-08 | |
| US60/771,570 | 2006-02-08 | ||
| PCT/IB2007/000284 WO2007091147A1 (en) | 2006-02-08 | 2007-02-06 | Oxazolidinones containing oxindoles as antibacterial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2637158A1 true CA2637158A1 (en) | 2007-08-16 |
Family
ID=38137316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002637158A Abandoned CA2637158A1 (en) | 2006-02-08 | 2007-02-06 | Oxazolidinones containing oxindoles as antibacterial agents |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20090149520A1 (enExample) |
| EP (1) | EP2004640A1 (enExample) |
| JP (1) | JP2009526036A (enExample) |
| CA (1) | CA2637158A1 (enExample) |
| WO (1) | WO2007091147A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2550437B (en) * | 2016-05-20 | 2021-06-23 | Bugworks Res Inc | Heterocyclic compounds useful as anti-bacterial agents and method for production |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| US7012088B2 (en) * | 2003-02-24 | 2006-03-14 | Pharmacia & Upjohn Company | Indolone oxazolidinones and derivatives thereof |
-
2007
- 2007-02-06 US US12/278,587 patent/US20090149520A1/en not_active Abandoned
- 2007-02-06 WO PCT/IB2007/000284 patent/WO2007091147A1/en not_active Ceased
- 2007-02-06 CA CA002637158A patent/CA2637158A1/en not_active Abandoned
- 2007-02-06 JP JP2008553844A patent/JP2009526036A/ja not_active Withdrawn
- 2007-02-06 EP EP07713021A patent/EP2004640A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007091147A1 (en) | 2007-08-16 |
| EP2004640A1 (en) | 2008-12-24 |
| JP2009526036A (ja) | 2009-07-16 |
| US20090149520A1 (en) | 2009-06-11 |
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