SK1402003A3 - Oxazolidinone derivatives as antimicrobials - Google Patents
Oxazolidinone derivatives as antimicrobials Download PDFInfo
- Publication number
- SK1402003A3 SK1402003A3 SK140-2003A SK1402003A SK1402003A3 SK 1402003 A3 SK1402003 A3 SK 1402003A3 SK 1402003 A SK1402003 A SK 1402003A SK 1402003 A3 SK1402003 A3 SK 1402003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- acetamide
- oxo
- fluoro
- oxazolidinyl
- Prior art date
Links
- 239000004599 antimicrobial Substances 0.000 title abstract description 8
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 272
- 238000000034 method Methods 0.000 claims abstract description 123
- 230000008569 process Effects 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 593
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 441
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 292
- 125000004193 piperazinyl group Chemical group 0.000 claims description 163
- -1 2-furoyl Chemical group 0.000 claims description 144
- 229910052739 hydrogen Inorganic materials 0.000 claims description 81
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 239000000460 chlorine Substances 0.000 claims description 67
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 53
- 238000002360 preparation method Methods 0.000 claims description 50
- 229910052801 chlorine Inorganic materials 0.000 claims description 49
- 229910052731 fluorine Inorganic materials 0.000 claims description 47
- 229910052794 bromium Inorganic materials 0.000 claims description 45
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 150000001412 amines Chemical class 0.000 claims description 32
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 26
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 25
- 229910052740 iodine Inorganic materials 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 9
- 150000002390 heteroarenes Chemical class 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004989 dicarbonyl group Chemical group 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052720 vanadium Inorganic materials 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052770 Uranium Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000002207 metabolite Substances 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 3
- RRTQTOBOLIGMED-UHFFFAOYSA-N 2-(carboxyamino)-2-phenylacetic acid Chemical compound OC(=O)NC(C(O)=O)C1=CC=CC=C1 RRTQTOBOLIGMED-UHFFFAOYSA-N 0.000 claims description 3
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 3
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 claims description 3
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 229940043279 diisopropylamine Drugs 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
- 150000003233 pyrroles Chemical class 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- IJNDXPMFHMCYAD-UHFFFAOYSA-N acetamide 2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound C(C)(=O)N.C(CC(O)(C(=O)O)CC(=O)O)(=O)O IJNDXPMFHMCYAD-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 5
- 101100134922 Gallus gallus COR5 gene Chemical group 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000000813 microbial effect Effects 0.000 claims 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 101100439665 Arabidopsis thaliana SWI2 gene Proteins 0.000 claims 1
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims 1
- 101100240519 Caenorhabditis elegans nhr-13 gene Proteins 0.000 claims 1
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 claims 1
- 230000021736 acetylation Effects 0.000 claims 1
- 238000006640 acetylation reaction Methods 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 1
- NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 244000052769 pathogen Species 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 241000186359 Mycobacterium Species 0.000 abstract description 3
- 241000187479 Mycobacterium tuberculosis Species 0.000 abstract description 3
- 241000295644 Staphylococcaceae Species 0.000 abstract description 3
- 241001112696 Clostridia Species 0.000 abstract description 2
- 241000186367 Mycobacterium avium Species 0.000 abstract description 2
- 241001148470 aerobic bacillus Species 0.000 abstract description 2
- 230000000845 anti-microbial effect Effects 0.000 abstract description 2
- 241000894007 species Species 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 87
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 85
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 57
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- 239000000243 solution Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 26
- 239000002585 base Substances 0.000 description 25
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 23
- 239000011734 sodium Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
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- 239000002775 capsule Substances 0.000 description 7
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- DSRPYQXHWUDRBP-ZDUSSCGKSA-N n-[[(5s)-3-(3-fluoro-4-piperazin-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCNCC1 DSRPYQXHWUDRBP-ZDUSSCGKSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- PBTHJVDBCFJQGG-UHFFFAOYSA-N methyl azide Chemical compound CN=[N+]=[N-] PBTHJVDBCFJQGG-UHFFFAOYSA-N 0.000 description 5
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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
- C07D413/02—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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN654DE2000 | 2000-07-17 | ||
| PCT/IB2001/001262 WO2002006278A1 (en) | 2000-07-17 | 2001-07-16 | Oxazolidinone derivatives as antimicrobials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK1402003A3 true SK1402003A3 (en) | 2003-08-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK140-2003A SK1402003A3 (en) | 2000-07-17 | 2001-07-16 | Oxazolidinone derivatives as antimicrobials |
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|---|---|
| US (2) | US6734307B2 (cs) |
| EP (1) | EP1303511A1 (cs) |
| JP (1) | JP2004504321A (cs) |
| CN (1) | CN1447808A (cs) |
| AU (2) | AU2001269370B2 (cs) |
| BR (1) | BR0112826A (cs) |
| CA (1) | CA2415965A1 (cs) |
| CZ (1) | CZ2003228A3 (cs) |
| HU (1) | HUP0302918A2 (cs) |
| MX (1) | MXPA03000503A (cs) |
| NZ (1) | NZ523700A (cs) |
| PL (1) | PL363960A1 (cs) |
| RU (1) | RU2292345C9 (cs) |
| SK (1) | SK1402003A3 (cs) |
| WO (1) | WO2002006278A1 (cs) |
| ZA (1) | ZA200300471B (cs) |
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| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| CZ2003228A3 (cs) | 2000-07-17 | 2003-06-18 | Ranbaxy Laboratories Limited | Oxazolidinonové deriváty jako antimikrobiální látky |
| WO2003008389A1 (en) * | 2001-07-16 | 2003-01-30 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as potential antimicrobials |
| ES2248633T3 (es) | 2001-04-17 | 2006-03-16 | MERCK & CO., INC. | Antibioticos oxazolidinona que contienen biciclo (3,1,o)hexano y derivados de los mismos. |
| US6956040B2 (en) | 2001-07-16 | 2005-10-18 | Ranbaxy Laboratories Limited | Oxazolidinone piperazinyl derivatives as potential antimicrobials |
| FR2828488B1 (fr) * | 2001-08-08 | 2005-06-10 | Oreal | Composition pour la teinture de fibres keratiniques contenant une paraphenylenediamine substituee par un radical diazacycloheptane |
| WO2003082864A2 (en) * | 2002-04-01 | 2003-10-09 | Cadila Healthcare Limited | Antiinfectve compounds, process for their preparation and pharmaceutical compositions containing them |
| AU2003224345A1 (en) * | 2002-04-30 | 2003-11-17 | Orchid Chemicals & Pharmaceuticals | Antibacterial agents |
| CA2483600A1 (en) * | 2002-05-15 | 2003-11-27 | Ranbaxy Laboratories Limited | Polymorphic forms of phenyl oxazolidinone derivatives |
| WO2003097640A1 (en) * | 2002-05-22 | 2003-11-27 | Orchid Chemicals & Pharmaceuticals Ltd. | Oxazolidinone derivatives as antibacterial agents |
| MXPA05001199A (es) * | 2002-07-29 | 2005-05-16 | Ranbaxy Lab Ltd | Derivados de oxazolidinona como antimicrobianos. |
| WO2004018439A1 (en) * | 2002-08-22 | 2004-03-04 | Orchid Chemicals & Pharmaceuticals Ltd | Novel antibacterial agents |
| WO2004026848A1 (en) | 2002-09-20 | 2004-04-01 | Lupin Limited | Oxazolidinone derivatives, process for their preperation and their use as antimycobacterial agents |
| US6875784B2 (en) * | 2002-10-09 | 2005-04-05 | Pharmacia & Upjohn Company | Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives |
| GB0302094D0 (en) | 2003-01-29 | 2003-02-26 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| AU2003202753A1 (en) * | 2003-02-07 | 2004-08-30 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
| DE10306250A1 (de) * | 2003-02-14 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US7223788B2 (en) | 2003-02-14 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Substituted N-aryl heterocycles, process for their preparation and their use as medicaments |
| EP1620433A1 (en) * | 2003-04-07 | 2006-02-01 | Ranbaxy Laboratories, Ltd. | Oxazolidinone derivatives as antimicrobials |
| BRPI0409217A (pt) | 2003-04-09 | 2006-03-28 | Pharmacia & Upjohn Co Llc | derivados e análogos antimicrobianos da [3.1.0]bicicloexilfeniloxazolidinona |
| WO2005003087A2 (en) * | 2003-07-01 | 2005-01-13 | Orchid Chemicals And Pharmaceuticals Ltd. | Oxazole derivatives as antibacterial agents |
| KR20060113625A (ko) * | 2003-07-02 | 2006-11-02 | 머크 앤드 캄파니 인코포레이티드 | 시클로프로필기 치환된 옥사졸리디논 항생제 및 그의유도체 |
| US20060247286A1 (en) * | 2003-07-02 | 2006-11-02 | Milton Hammond | Oxazolidinone antibiotics and derivatives thereof |
| JP2007521283A (ja) * | 2003-07-02 | 2007-08-02 | メルク アンド カンパニー インコーポレーテッド | シクロプロピル基で置換されたオキサゾリジノン系抗生物質およびその誘導体 |
| JP2007521284A (ja) * | 2003-07-02 | 2007-08-02 | メルク アンド カンパニー インコーポレーテッド | オキサゾリジノン系抗生物質及びその誘導体 |
| GB0324269D0 (en) | 2003-10-16 | 2003-11-19 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| WO2005051933A1 (en) * | 2003-11-28 | 2005-06-09 | Ranbaxy Laboratories Limited | An improved process for the synthesis of 4-(4-benzyloxy-carbonylamino-2-fluorophenyl)-piperazine-1-carboxylic acid tert-butyl ester, a key intermediate for oxazolidinone antimicrobials and compounds prepared thereby |
| WO2005082899A1 (en) * | 2004-01-28 | 2005-09-09 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
| US20090247545A1 (en) * | 2004-10-11 | 2009-10-01 | Mukund Keshao Gurjar | Substituted oxazolidinone derivatives |
| WO2007000644A1 (en) | 2005-06-29 | 2007-01-04 | Pharmacia & Upjohn Company Llc | Homomorpholine oxazolidinones as antibacterial agents |
| FR2895735B1 (fr) | 2005-12-30 | 2008-04-18 | Ecopack France | Valve a poche amelioree |
| US7728031B2 (en) | 2006-02-24 | 2010-06-01 | Abbott Laboratories | Octahydro-pyrrolo[3,4-b]pyrrole derivatives |
| KR20080110877A (ko) | 2006-03-31 | 2008-12-19 | 재단법인 이쯔우 연구소 | 헤테로환을 갖는 신규 화합물 |
| WO2009036132A1 (en) | 2007-09-11 | 2009-03-19 | Abbott Laboratories | Octahydro-pyrrolo[3,4-b]pyrrole n-oxides |
| EP2233484A3 (en) | 2007-10-02 | 2012-04-04 | Research Foundation Itsuu Laboratory | Oxazolidinone derivatives having a 7-membered heterocyclic ring |
| WO2009132310A1 (en) * | 2008-04-25 | 2009-10-29 | Wisconsin Alumni Research Foundation | Inhibitors of udp-galactopyranose mutase thwart mycobacterial growth |
| US20130296569A1 (en) | 2010-11-03 | 2013-11-07 | Vijaykumar Jagdishwar Patil | Process for the preparation of phosphoric acid mono-(1--4-methoxymethyl-piperidin-4-yl) ester |
| UA112876C2 (uk) * | 2011-09-29 | 2016-11-10 | Сюаньчжу Фарма Ко., Лтд. | Біарилгетероциклзаміщені оксазолідинонові антибактеріальні засоби |
| WO2015173664A1 (en) | 2014-05-14 | 2015-11-19 | Wockhardt Limited | Process for the preparation of (5s)-n-{3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide |
| US10080757B2 (en) | 2016-03-11 | 2018-09-25 | Wisconsin Alumni Research Foundation | Inhibitors of UDP-galactopyranose mutase |
| CN109020873B (zh) * | 2018-07-16 | 2020-04-28 | 青岛农业大学 | 以靶标蛋白甾醇14α-脱甲基酶三维结构筛选的化合物及其在在制备杀菌剂中的应用 |
| WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| TWI846853B (zh) | 2019-04-03 | 2024-07-01 | 美商艾利格斯醫療公司 | 吡咯化合物 |
| AU2021292747A1 (en) | 2020-06-18 | 2023-02-23 | Akagera Medicines, Inc. | Oxazolidinone compounds, liposome compositions comprising oxazolidinone compounds and methods of use thereof |
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| CH611898A5 (cs) * | 1975-06-06 | 1979-06-29 | Hoffmann La Roche | |
| US4801600A (en) | 1987-10-09 | 1989-01-31 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4921869A (en) | 1987-10-09 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| CA1320730C (en) | 1987-10-16 | 1993-07-27 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents |
| US4948801A (en) | 1988-07-29 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
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| US5164402A (en) * | 1989-08-16 | 1992-11-17 | Pfizer Inc | Azabicyclo quinolone and naphthyridinone carboxylic acids |
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| SK283420B6 (sk) * | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
| KR100312903B1 (ko) * | 1993-11-22 | 2002-02-28 | 로렌스 티. 마이젠헬더 | 치환된-하이드록시아세틸피페라진페닐옥사졸리디논의에스테르 |
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| ATE257829T1 (de) * | 1995-09-15 | 2004-01-15 | Upjohn Co | Aminoaryl oxazolidinone n-oxide |
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| MY116093A (en) * | 1996-02-26 | 2003-11-28 | Upjohn Co | Azolyl piperazinyl phenyl oxazolidinone antimicrobials |
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-
2001
- 2001-07-16 CZ CZ2003228A patent/CZ2003228A3/cs unknown
- 2001-07-16 CA CA002415965A patent/CA2415965A1/en not_active Abandoned
- 2001-07-16 CN CN01814422A patent/CN1447808A/zh active Pending
- 2001-07-16 US US09/906,215 patent/US6734307B2/en not_active Expired - Fee Related
- 2001-07-16 JP JP2002512181A patent/JP2004504321A/ja active Pending
- 2001-07-16 AU AU2001269370A patent/AU2001269370B2/en not_active Ceased
- 2001-07-16 SK SK140-2003A patent/SK1402003A3/sk not_active Application Discontinuation
- 2001-07-16 BR BR0112826-4A patent/BR0112826A/pt not_active IP Right Cessation
- 2001-07-16 NZ NZ523700A patent/NZ523700A/en unknown
- 2001-07-16 HU HU0302918A patent/HUP0302918A2/hu unknown
- 2001-07-16 PL PL01363960A patent/PL363960A1/xx not_active Application Discontinuation
- 2001-07-16 AU AU6937001A patent/AU6937001A/xx active Pending
- 2001-07-16 WO PCT/IB2001/001262 patent/WO2002006278A1/en active IP Right Grant
- 2001-07-16 RU RU2003103767/04A patent/RU2292345C9/ru not_active IP Right Cessation
- 2001-07-16 EP EP01947730A patent/EP1303511A1/en not_active Withdrawn
- 2001-07-16 MX MXPA03000503A patent/MXPA03000503A/es unknown
-
2002
- 2002-01-21 US US10/483,905 patent/US20040242591A1/en not_active Abandoned
-
2003
- 2003-01-17 ZA ZA200300471A patent/ZA200300471B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0302918A2 (hu) | 2003-12-29 |
| CN1447808A (zh) | 2003-10-08 |
| US20040242591A1 (en) | 2004-12-02 |
| BR0112826A (pt) | 2003-06-24 |
| NZ523700A (en) | 2004-11-26 |
| CZ2003228A3 (cs) | 2003-06-18 |
| WO2002006278A1 (en) | 2002-01-24 |
| MXPA03000503A (es) | 2003-10-14 |
| AU2001269370B2 (en) | 2005-10-27 |
| ZA200300471B (en) | 2003-10-29 |
| CA2415965A1 (en) | 2002-01-24 |
| PL363960A1 (en) | 2004-11-29 |
| RU2292345C9 (ru) | 2007-05-10 |
| US6734307B2 (en) | 2004-05-11 |
| RU2292345C2 (ru) | 2007-01-27 |
| JP2004504321A (ja) | 2004-02-12 |
| EP1303511A1 (en) | 2003-04-23 |
| AU6937001A (en) | 2002-01-30 |
| US20020103186A1 (en) | 2002-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC9A | Refused patent application |