JP2009526832A - 抗菌剤としてのベンゾオキサジノンおよびベンゾオキサゼピノンオキサゾリジノン - Google Patents
抗菌剤としてのベンゾオキサジノンおよびベンゾオキサゼピノンオキサゾリジノン Download PDFInfo
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- JP2009526832A JP2009526832A JP2008554878A JP2008554878A JP2009526832A JP 2009526832 A JP2009526832 A JP 2009526832A JP 2008554878 A JP2008554878 A JP 2008554878A JP 2008554878 A JP2008554878 A JP 2008554878A JP 2009526832 A JP2009526832 A JP 2009526832A
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- Prior art keywords
- methyl
- oxo
- alkyl
- benzo
- oxazin
- 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.)
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- 239000003242 anti bacterial agent Substances 0.000 title abstract description 8
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 title description 3
- DLYJDTZXVPOWKM-UHFFFAOYSA-N O1C(NCC1)=O.O1NC(C=CC2=C1C=CC=C2)=O Chemical compound O1C(NCC1)=O.O1NC(C=CC2=C1C=CC=C2)=O DLYJDTZXVPOWKM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 132
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- -1 1,2,3-triazol-1-ylmethyl Chemical group 0.000 claims description 152
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 11
- 208000035143 Bacterial infection Diseases 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 208000015181 infectious disease Diseases 0.000 claims description 9
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- SEVVMFJXWHWBJX-LLVKDONJSA-N (5r)-n-methyl-3-(1-methyl-2-oxo-4h-3,1-benzoxazin-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C1=CC=C(N(C)C(=O)OC2)C2=C1 SEVVMFJXWHWBJX-LLVKDONJSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- JEJNBRKUZXERTF-ZDUSSCGKSA-N n-[[(5s)-3-(1-methyl-2-oxo-4,5-dihydro-3,1-benzoxazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1=C2CCOC(=O)N(C)C2=CC=C1N1C[C@H](CNC(C)=O)OC1=O JEJNBRKUZXERTF-ZDUSSCGKSA-N 0.000 claims description 6
- PWHQRHQZASRMQE-LBPRGKRZSA-N n-[[(5s)-3-(1-methyl-2-oxo-4h-3,1-benzoxazin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C=C2N(C)C(=O)OCC2=CC=1N1C[C@H](CNC(C)=O)OC1=O PWHQRHQZASRMQE-LBPRGKRZSA-N 0.000 claims description 6
- MJPNBDMITRCENY-LBPRGKRZSA-N 1-methyl-6-[(5r)-2-oxo-5-(triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]-4h-3,1-benzoxazin-2-one Chemical compound C([C@H]1CN(C(O1)=O)C=1C=C2COC(=O)N(C2=CC=1)C)N1C=CN=N1 MJPNBDMITRCENY-LBPRGKRZSA-N 0.000 claims description 5
- RFHPWKPYKDTZNH-QMMMGPOBSA-N n-[[(5s)-3-(5,8-difluoro-1-methyl-2-oxo-4h-3,1-benzoxazin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C(F)=C2N(C)C(=O)OCC2=C(F)C=1N1C[C@H](CNC(C)=O)OC1=O RFHPWKPYKDTZNH-QMMMGPOBSA-N 0.000 claims description 5
- 229910052757 nitrogen Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- WLICVOPNJBIGRE-SNVBAGLBSA-N (5r)-3-(1-methyl-2-oxo-4h-3,1-benzoxazin-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C=1C=C2N(C)C(=O)OCC2=CC=1N1C[C@H](C(N)=O)OC1=O WLICVOPNJBIGRE-SNVBAGLBSA-N 0.000 claims description 4
- 241000186367 Mycobacterium avium Species 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- NYXHSRNBKJIQQG-UHFFFAOYSA-N methyl n-methylcarbamate Chemical compound CNC(=O)OC NYXHSRNBKJIQQG-UHFFFAOYSA-N 0.000 claims description 4
- BHAJBNXXGVSKTM-NSHDSACASA-N n-[[(5s)-3-(8-fluoro-1-methyl-2-oxo-4h-3,1-benzoxazin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C(F)=C2N(C)C(=O)OCC2=CC=1N1C[C@H](CNC(C)=O)OC1=O BHAJBNXXGVSKTM-NSHDSACASA-N 0.000 claims description 4
- LVCYPXAIOVKHRW-LBPRGKRZSA-N n-[[(5s)-3-(9-fluoro-1-methyl-2-oxo-4,5-dihydro-3,1-benzoxazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1=C2CCOC(=O)N(C)C2=C(F)C=C1N1C[C@H](CNC(C)=O)OC1=O LVCYPXAIOVKHRW-LBPRGKRZSA-N 0.000 claims description 4
- UEWSCJGPMVIYJQ-LLVKDONJSA-N (5r)-3-(1-methyl-2-oxo-4,5-dihydro-3,1-benzoxazepin-7-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2CCOC(=O)N(C)C2=CC=C1N1C[C@H](C(N)=O)OC1=O UEWSCJGPMVIYJQ-LLVKDONJSA-N 0.000 claims description 3
- UXPJRMKAUHGOCE-SECBINFHSA-N (5r)-3-(8-fluoro-1-methyl-2-oxo-4h-3,1-benzoxazin-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C=1C(F)=C2N(C)C(=O)OCC2=CC=1N1C[C@H](C(N)=O)OC1=O UXPJRMKAUHGOCE-SECBINFHSA-N 0.000 claims description 3
- YKWCPZKKMHGBQK-SNVBAGLBSA-N (5r)-3-(8-fluoro-1-methyl-2-oxo-4h-3,1-benzoxazin-6-yl)-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C1=CC(F)=C(N(C)C(=O)OC2)C2=C1 YKWCPZKKMHGBQK-SNVBAGLBSA-N 0.000 claims description 3
- XIUMCEOEBCANMI-GFCCVEGCSA-N (5r)-n-methyl-3-(1-methyl-2-oxo-4,5-dihydro-3,1-benzoxazepin-7-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C1=CC=C(N(C)C(=O)OCC2)C2=C1 XIUMCEOEBCANMI-GFCCVEGCSA-N 0.000 claims description 3
- 208000001860 Eye Infections Diseases 0.000 claims description 3
- 241000192125 Firmicutes Species 0.000 claims description 3
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 208000011323 eye infectious disease Diseases 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- XVTYGXVIJSGQKE-ZDUSSCGKSA-N n-[[(5s)-3-(1-methyl-2-oxo-4,5-dihydro-3,1-benzoxazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C1=CC=C(N(C)C(=O)OCC2)C2=C1 XVTYGXVIJSGQKE-ZDUSSCGKSA-N 0.000 claims description 3
- CJUXGGKJFYBDDN-LBPRGKRZSA-N n-[[(5s)-3-(1-methyl-2-oxo-4h-3,1-benzoxazin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C1=CC=C(N(C)C(=O)OC2)C2=C1 CJUXGGKJFYBDDN-LBPRGKRZSA-N 0.000 claims description 3
- XQTFYTLXFLTPQF-NSHDSACASA-N n-[[(5s)-3-(8-fluoro-1-methyl-2-oxo-4h-3,1-benzoxazin-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C1=CC(F)=C(N(C)C(=O)OC2)C2=C1 XQTFYTLXFLTPQF-NSHDSACASA-N 0.000 claims description 3
- JYMXDJZYWJPLHH-LBPRGKRZSA-N n-[[(5s)-3-(9-fluoro-1-methyl-2-oxo-4,5-dihydro-3,1-benzoxazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C1=CC(F)=C(N(C)C(=O)OCC2)C2=C1 JYMXDJZYWJPLHH-LBPRGKRZSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 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
- 241000194032 Enterococcus faecalis Species 0.000 claims description 2
- 241000606768 Haemophilus influenzae Species 0.000 claims description 2
- 241000588621 Moraxella Species 0.000 claims description 2
- 241000588655 Moraxella catarrhalis 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
- 241000295644 Staphylococcaceae Species 0.000 claims description 2
- 241000193996 Streptococcus pyogenes Species 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 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
- 201000007119 infective endocarditis Diseases 0.000 claims description 2
- 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 2
- 241000894006 Bacteria Species 0.000 claims 4
- 241000606125 Bacteroides Species 0.000 claims 1
- 241000606790 Haemophilus Species 0.000 claims 1
- 241000191940 Staphylococcus Species 0.000 claims 1
- 241000194017 Streptococcus Species 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 166
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 87
- 238000002360 preparation method Methods 0.000 description 83
- 239000000203 mixture Substances 0.000 description 73
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 60
- 239000011734 sodium Substances 0.000 description 59
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- 239000000243 solution Substances 0.000 description 47
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 45
- 238000010828 elution Methods 0.000 description 45
- 230000014759 maintenance of location Effects 0.000 description 45
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 43
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 10
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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
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 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
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride 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
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Chemical group 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 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
- RALQKLVPOYSSFR-ZDUSSCGKSA-N tert-butyl n-[[(5s)-3-[3-fluoro-5-(2-hydroxyethyl)-4-(methylamino)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound C1=C(CCO)C(NC)=C(F)C=C1N1C(=O)O[C@@H](CNC(=O)OC(C)(C)C)C1 RALQKLVPOYSSFR-ZDUSSCGKSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-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
- 238000012360 testing method Methods 0.000 description 1
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 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
- 229960000281 trometamol Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- 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)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77307106P | 2006-02-14 | 2006-02-14 | |
| PCT/IB2007/000377 WO2007093904A1 (en) | 2006-02-14 | 2007-02-05 | Benzoxazinone and benzoxazepinone oxazolidinones as antibacterial agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009526832A true JP2009526832A (ja) | 2009-07-23 |
| JP2009526832A5 JP2009526832A5 (enExample) | 2011-04-07 |
Family
ID=38068038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008554878A Withdrawn JP2009526832A (ja) | 2006-02-14 | 2007-02-05 | 抗菌剤としてのベンゾオキサジノンおよびベンゾオキサゼピノンオキサゾリジノン |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20090318431A1 (enExample) |
| EP (1) | EP1987025B1 (enExample) |
| JP (1) | JP2009526832A (enExample) |
| AT (1) | ATE443061T1 (enExample) |
| CA (1) | CA2642406A1 (enExample) |
| DE (1) | DE602007002476D1 (enExample) |
| DK (1) | DK1987025T3 (enExample) |
| ES (1) | ES2331930T3 (enExample) |
| WO (1) | WO2007093904A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2411930T3 (es) * | 2008-02-20 | 2013-07-09 | Actelion Pharmaceuticals Ltd. | Compuestos antibióticos azatricíclicos |
| JP5404652B2 (ja) * | 2008-02-22 | 2014-02-05 | アクテリオン ファーマシューティカルズ リミテッド | オキサゾリジノン誘導体 |
| KR100980681B1 (ko) | 2008-09-16 | 2010-09-07 | 한국과학기술연구원 | 디플루오로페닐 유도체를 갖는 신규한 옥사졸리디논 유도체또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 하는 항생제 조성물 |
| EP2334636A2 (en) | 2008-09-19 | 2011-06-22 | Pfizer Inc. | Hydroxamic acid derivatives useful as antibacterial agents |
| MY158520A (en) | 2008-10-07 | 2016-10-14 | Actelion Pharmaceuticals Ltd | Tricyclic oxazolidinone antibiotic compounds |
| RU2522582C2 (ru) | 2008-11-20 | 2014-07-20 | Панацеа Биотек Лтд. | Новые противомикробные средства |
| US8906913B2 (en) | 2009-06-26 | 2014-12-09 | Panacea Biotec Limited | Azabicyclohexanes |
| PL2512474T3 (pl) | 2009-12-16 | 2015-03-31 | Pfizer | N-przyłączone pochodne kwasu hydroksamowego użyteczne jako środki przeciwbakteryjne |
| CN103717582B (zh) * | 2011-04-08 | 2015-09-30 | 辉瑞大药厂 | 用作抗菌剂的异*唑衍生物 |
| UA112897C2 (uk) | 2012-05-09 | 2016-11-10 | Байєр Фарма Акцієнгезелльшафт | Біциклічно заміщені урацили та їх застосування для лікування і/або профілактики захворювань |
| GB2550437B (en) * | 2016-05-20 | 2021-06-23 | Bugworks Res Inc | Heterocyclic compounds useful as anti-bacterial agents and method for production |
| CN113264949B (zh) * | 2021-05-31 | 2022-04-05 | 西南大学 | 一类螺苯并噁嗪哌啶α,β-不饱和酮类衍生物的设计合成与应用 |
| CN114133360A (zh) * | 2021-11-30 | 2022-03-04 | 南京工业大学 | 一种含氟苯并[d]-1,3-氧氮杂卓化合物及其合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19802239A1 (de) * | 1998-01-22 | 1999-07-29 | Bayer Ag | Neue mit Bicyclen substituierte Oxazolidinone |
| WO2000029409A1 (de) * | 1998-11-17 | 2000-05-25 | Bayer Aktiengesellschaft | Neue heterocyclyl-substituierte oxazolidon-derivate |
| WO2005082897A1 (en) * | 2004-01-28 | 2005-09-09 | Pharmacia & Upjohn Company Llc | Oxazolidinone antibacterial agents |
-
2007
- 2007-02-05 ES ES07705605T patent/ES2331930T3/es active Active
- 2007-02-05 DE DE602007002476T patent/DE602007002476D1/de active Active
- 2007-02-05 EP EP07705605A patent/EP1987025B1/en active Active
- 2007-02-05 US US12/279,120 patent/US20090318431A1/en not_active Abandoned
- 2007-02-05 JP JP2008554878A patent/JP2009526832A/ja not_active Withdrawn
- 2007-02-05 AT AT07705605T patent/ATE443061T1/de not_active IP Right Cessation
- 2007-02-05 CA CA002642406A patent/CA2642406A1/en not_active Abandoned
- 2007-02-05 DK DK07705605T patent/DK1987025T3/da active
- 2007-02-05 WO PCT/IB2007/000377 patent/WO2007093904A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ATE443061T1 (de) | 2009-10-15 |
| EP1987025B1 (en) | 2009-09-16 |
| WO2007093904A1 (en) | 2007-08-23 |
| EP1987025A1 (en) | 2008-11-05 |
| US20090318431A1 (en) | 2009-12-24 |
| DK1987025T3 (da) | 2009-12-07 |
| ES2331930T3 (es) | 2010-01-20 |
| DE602007002476D1 (de) | 2009-10-29 |
| CA2642406A1 (en) | 2007-08-23 |
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