NO311298B1 - Spirosykliske og bisykliske diazinyl- og karbazinyloksazolidinoner - Google Patents
Spirosykliske og bisykliske diazinyl- og karbazinyloksazolidinoner Download PDFInfo
- Publication number
- NO311298B1 NO311298B1 NO19975158A NO975158A NO311298B1 NO 311298 B1 NO311298 B1 NO 311298B1 NO 19975158 A NO19975158 A NO 19975158A NO 975158 A NO975158 A NO 975158A NO 311298 B1 NO311298 B1 NO 311298B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- phenyl
- oxo
- diazabicyclo
- acetamide
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- -1 indolylcarbonyl Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000004480 active ingredient Substances 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- LEVJKELDHDXAAR-VWPQPMDRSA-N benzyl (3ar,6as)-2-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C[C@H]2CN(C(=O)OCC=3C=CC=CC=3)C[C@H]2C1 LEVJKELDHDXAAR-VWPQPMDRSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- FPRGFKZYMBMYFG-DJPFJPOOSA-N [2-[(4as,7as)-6-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b]pyridin-1-yl]-2-oxoethyl] acetate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C[C@H]2N(C(=O)COC(C)=O)CCC[C@H]2C1 FPRGFKZYMBMYFG-DJPFJPOOSA-N 0.000 claims 2
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- SALYPFUUKANBSJ-URLQWDBASA-N n-[[(5s)-3-[4-[(4as,7as)-1-(2-hydroxyacetyl)-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b]pyridin-6-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C[C@H]2N(C(=O)CO)CCC[C@H]2C1 SALYPFUUKANBSJ-URLQWDBASA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 5
- 208000015181 infectious disease Diseases 0.000 abstract description 3
- 230000000813 microbial effect Effects 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 238000000034 method Methods 0.000 description 25
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- 239000011541 reaction mixture Substances 0.000 description 23
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- 238000006243 chemical reaction Methods 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
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- 230000004048 modification Effects 0.000 description 8
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- 238000002360 preparation method Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
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- 235000011152 sodium sulphate Nutrition 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
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- 239000007858 starting material Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical compound C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 6
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- 239000003242 anti bacterial agent Substances 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
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- 239000000463 material Substances 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 description 3
- QISAUDWTBBNJIR-UHFFFAOYSA-N 2-phenylmethoxyacetyl chloride Chemical compound ClC(=O)COCC1=CC=CC=C1 QISAUDWTBBNJIR-UHFFFAOYSA-N 0.000 description 3
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
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- 241001148470 aerobic bacillus Species 0.000 description 1
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- YEXWLSXGXSMDNZ-QMHWCDLVSA-N benzyl (1r,5s)-3-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C[C@H]2N(C(=O)OCC=3C=CC=CC=3)C[C@H]2C1 YEXWLSXGXSMDNZ-QMHWCDLVSA-N 0.000 description 1
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- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
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- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
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- 239000000284 extract Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
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- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- 150000002513 isocyanates Chemical class 0.000 description 1
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- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
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- 239000001095 magnesium carbonate Substances 0.000 description 1
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- OVHCKYINCXWNAR-HACGYAERSA-N methyl (1r,5s)-3-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)OC)N1C(C(=C1)F)=CC=C1N1C[C@H](CNC(C)=O)OC1=O OVHCKYINCXWNAR-HACGYAERSA-N 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- CSZLOCRIBUMEIS-DJZRFWRSSA-N n-[[(5s)-3-[3-fluoro-4-(1-formyl-1,7-diazaspiro[4.4]nonan-7-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC2(N(CCC2)C=O)CC1 CSZLOCRIBUMEIS-DJZRFWRSSA-N 0.000 description 1
- MAJJDDQOFQAFSJ-DJZRFWRSSA-N n-[[(5s)-3-[3-fluoro-4-(7-formyl-2,7-diazaspiro[4.4]nonan-2-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC2(CN(CC2)C=O)CC1 MAJJDDQOFQAFSJ-DJZRFWRSSA-N 0.000 description 1
- OLTYMPALGKIHQC-HACGYAERSA-N n-[[(5s)-3-[3-fluoro-4-[(1r,5s)-6-(2-hydroxyacetyl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C[C@H]2N(C(=O)CO)C[C@H]2C1 OLTYMPALGKIHQC-HACGYAERSA-N 0.000 description 1
- SSZKCYDGEBSGHS-HACGYAERSA-N n-[[(5s)-3-[3-fluoro-4-[(1r,5s)-6-formyl-3,6-diazabicyclo[3.2.0]heptan-3-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C[C@H]2N(C=O)C[C@H]2C1 SSZKCYDGEBSGHS-HACGYAERSA-N 0.000 description 1
- ZVISVOGQCGHHSI-HACGYAERSA-N n-[[(5s)-3-[3-fluoro-4-[(1s,5s)-3-formyl-3,6-diazabicyclo[3.2.0]heptan-6-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1[C@@H]2CN(C=O)C[C@@H]2C1 ZVISVOGQCGHHSI-HACGYAERSA-N 0.000 description 1
- BRXOEOLONMQHEE-BJQOMGFOSA-N n-[[(5s)-3-[3-fluoro-4-[1-(2-hydroxyacetyl)-1,7-diazaspiro[4.4]nonan-7-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC2(N(CCC2)C(=O)CO)CC1 BRXOEOLONMQHEE-BJQOMGFOSA-N 0.000 description 1
- HWCNNQYFLPFJCB-ZVDOUQERSA-N n-[[(5s)-3-[4-[(3ar,6as)-5-(1h-indole-2-carbonyl)-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C[C@H]2CN(C(=O)C=3NC4=CC=CC=C4C=3)C[C@H]2C1 HWCNNQYFLPFJCB-ZVDOUQERSA-N 0.000 description 1
- SQNFUJWDYVBXQU-XJUOHMSHSA-N n-[[(5s)-3-[4-[(3ar,6as)-5-(2-phenylmethoxyacetyl)-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C[C@H]2CN(C(=O)COCC=3C=CC=CC=3)C[C@H]2C1 SQNFUJWDYVBXQU-XJUOHMSHSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000006772 olefination reaction Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical class CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- 150000003672 ureas Chemical class 0.000 description 1
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- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/54—Spiro-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (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 |
|---|---|---|---|
| US43870595A | 1995-05-11 | 1995-05-11 | |
| PCT/US1996/005202 WO1996035691A1 (en) | 1995-05-11 | 1996-04-18 | Spirocyclic and bicyclic diazinyl and carbazinyl oxazolidinones |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO975158D0 NO975158D0 (no) | 1997-11-10 |
| NO975158L NO975158L (no) | 1998-01-09 |
| NO311298B1 true NO311298B1 (no) | 2001-11-12 |
Family
ID=23741700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19975158A NO311298B1 (no) | 1995-05-11 | 1997-11-10 | Spirosykliske og bisykliske diazinyl- og karbazinyloksazolidinoner |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6090820A (ko) |
| EP (1) | EP0828741B1 (ko) |
| JP (1) | JPH11506430A (ko) |
| KR (1) | KR100463771B1 (ko) |
| CN (2) | CN1068328C (ko) |
| AT (1) | ATE204874T1 (ko) |
| AU (1) | AU702752B2 (ko) |
| CA (1) | CA2218088A1 (ko) |
| DE (1) | DE69614847T2 (ko) |
| DK (1) | DK0828741T3 (ko) |
| ES (1) | ES2162047T3 (ko) |
| FI (1) | FI974180A0 (ko) |
| HK (2) | HK1009449A1 (ko) |
| MX (1) | MX9708627A (ko) |
| NO (1) | NO311298B1 (ko) |
| NZ (1) | NZ306310A (ko) |
| PT (1) | PT828741E (ko) |
| WO (1) | WO1996035691A1 (ko) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11512429A (ja) * | 1995-09-15 | 1999-10-26 | ファルマシア・アンド・アップジョン・カンパニー | アミノアリールオキサゾリジノン ｎ−オキシド |
| GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| GB9702213D0 (en) | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
| CZ298060B6 (cs) * | 1996-04-11 | 2007-06-06 | Pharmacia & Upjohn Company | Zpusob prípravy oxazolidinonu |
| GB9609919D0 (en) * | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| GB9717807D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| KR100467309B1 (ko) * | 1997-09-04 | 2005-07-18 | 씨제이 주식회사 | 옥사졸리디논유도체및그의제조방법및항균제조성물 |
| KR100463111B1 (ko) * | 1997-10-30 | 2005-06-13 | 씨제이 주식회사 | 신규한옥사졸리디논유도체및제조방법및그를함유하는항균제조성물 |
| GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
| TR200003595T2 (tr) | 1998-06-05 | 2001-07-23 | Astrazeneca Ab | Kimyasal bileşikler |
| US6297242B1 (en) | 1999-08-12 | 2001-10-02 | Ortho-Mcneil Pharmaceutical, Inc. | N-substituted amidine and guanidine oxazolidinone antibacterials and methods of use thereof |
| US6413981B1 (en) * | 1999-08-12 | 2002-07-02 | Ortho-Mcneil Pharamceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
| US6608081B2 (en) | 1999-08-12 | 2003-08-19 | Ortho-Mcneil Pharmaceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| US6518285B2 (en) | 1999-12-21 | 2003-02-11 | Ortho Mcneil Pharmaceutical, Inc. | Piperidinyloxy and pyrrolidinyloxy oxazolidinone antibacterials |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| ITVA20000023A1 (it) * | 2000-07-19 | 2002-01-19 | Lamberti Spa | Composizioni di pvc stabili al calore. |
| SE0100326D0 (sv) | 2001-02-02 | 2001-02-02 | Astrazeneca Ab | New compounds |
| CA2440803A1 (en) | 2001-03-07 | 2002-09-12 | Pfizer Products Inc. | Modulators of chemokine receptor activity |
| WO2003048136A1 (en) * | 2001-11-29 | 2003-06-12 | Merck & Co., Inc. | Cyclopropyl hexane containing oxazolidinone antibiotics and derivatives thereof |
| US7141588B2 (en) | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| AR038536A1 (es) | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| EP1539745B1 (en) | 2002-08-12 | 2006-03-29 | Pharmacia & Upjohn Company LLC | N-aryl-2-oxazolidinones and their derivatives |
| KR100454099B1 (ko) * | 2002-08-22 | 2004-10-26 | 한국화학연구원 | 제초활성을 갖는9-(5-이속사졸린메톡시페닐)이미노-8-치아-1,6-디아자비시클로[4.3.0]노난-7-온 유도체 |
| BR0316483A (pt) | 2002-11-21 | 2005-10-11 | Upjohn Co | Derivados de n-(4-(piperazin-1-il)-fenil-2-oxazolidinona-5-carboxami da e compostos relacionados como agentes antibacterianos |
| KR20060113625A (ko) | 2003-07-02 | 2006-11-02 | 머크 앤드 캄파니 인코포레이티드 | 시클로프로필기 치환된 옥사졸리디논 항생제 및 그의유도체 |
| US7304050B2 (en) | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
| WO2006056848A1 (en) * | 2004-11-24 | 2006-06-01 | Pfizer Limited | Octahydropyrrolo[3,4-c]pyrrole derivatives |
| EP1671972A1 (en) * | 2004-11-24 | 2006-06-21 | Pfizer Limited | Octahydropyrrolo[3,4-c]pyrrole derivatives |
| KR100729344B1 (ko) * | 2006-02-16 | 2007-06-15 | 스마텍(주) | 차량용 사방 감지 카메라의 보호 및 작동 구조 |
| US7728031B2 (en) | 2006-02-24 | 2010-06-01 | Abbott Laboratories | Octahydro-pyrrolo[3,4-b]pyrrole derivatives |
| CN101809021B (zh) | 2007-09-11 | 2013-04-24 | 雅培制药有限公司 | 八氢-吡咯并[3,4-b]吡咯n-氧化物 |
| US8841306B2 (en) | 2008-11-20 | 2014-09-23 | Panacea Biotec Ltd. | Antimicrobials |
| AU2010264027B9 (en) | 2009-06-26 | 2013-06-13 | Panacea Biotec Ltd. | Novel azabicyclohexanes |
| 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 |
| KR101271224B1 (ko) | 2011-07-05 | 2013-06-10 | 한국과학기술연구원 | 항균활성을 갖는 신규 이중고리를 포함하는 옥사졸리디논 유도체 및 이의 제조방법 |
| EP2762480A4 (en) * | 2011-09-30 | 2015-03-18 | Xuanzhu Pharma Co Ltd | OXAZOLIDINONIBIOTICS WITH CONDENSED RINGS |
| 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 |
| RS63201B1 (sr) | 2015-07-02 | 2022-06-30 | Janssen Sciences Ireland Unlimited Co | Antibakterijska jedinjenja |
| EA037643B1 (ru) * | 2015-07-17 | 2021-04-26 | Зе Глобал Эллайенс Фо Тб Драг Девелопмент, Инк. | Замещенные фенилоксазолидиноны для антимикробной терапии |
| CN107400126A (zh) * | 2016-05-19 | 2017-11-28 | 陕西合成药业股份有限公司 | 新型噁唑烷酮类化合物及其制备方法和在医学上的应用 |
| MA45377A (fr) * | 2016-06-16 | 2019-04-24 | Janssen Sciences Ireland Unlimited Co | Composés hétérocycliques en tant qu'agents antibacteriens |
| BR112019017901A2 (pt) | 2017-03-01 | 2020-05-12 | Janssen Sciences Ireland Unlimited Company | Terapia de combinação |
| CN108727406B (zh) | 2017-03-28 | 2021-12-07 | 北京协和制药二厂 | 含氮杂环取代的苯并噁嗪噁唑烷酮类化合物及其制备方法和用途 |
| WO2020234636A1 (en) | 2019-05-17 | 2020-11-26 | Cadila Healthcare Limited | Novel compounds for the treatment of mammalian infections |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4921869A (en) * | 1987-10-09 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4801600A (en) * | 1987-10-09 | 1989-01-31 | 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 |
| ATE95176T1 (de) * | 1987-10-21 | 1993-10-15 | Du Pont Merck Pharma | Aminomethyl-oxo-oxazolidinyl-ethenylbenzenderivate, nuetzlich als antibakterielles mittel. |
| US4948801A (en) * | 1988-07-29 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| DE68929303T2 (de) * | 1988-09-15 | 2002-05-02 | Pharmacia & Upjohn Co., Kalamazoo | 3-(Stickstoff substituierte)phenyl-5-beta-amidomethyloxazoliden-2-one |
| CA2119556C (en) * | 1991-11-01 | 2004-07-06 | Michael Robert Barbachyn | Substituted aryl- and heteroaryl-phenyloxazolidinones |
| SK283420B6 (sk) * | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
| MY115155A (en) * | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| JPH0873455A (ja) * | 1994-03-15 | 1996-03-19 | Upjohn Co:The | オキサゾリジノン誘導体及びこれを有効成分とする医薬組成物 |
-
1996
- 1996-04-18 ES ES96911768T patent/ES2162047T3/es not_active Expired - Lifetime
- 1996-04-18 MX MX9708627A patent/MX9708627A/es not_active IP Right Cessation
- 1996-04-18 US US09/202,195 patent/US6090820A/en not_active Expired - Fee Related
- 1996-04-18 AU AU54849/96A patent/AU702752B2/en not_active Ceased
- 1996-04-18 JP JP8534070A patent/JPH11506430A/ja not_active Withdrawn
- 1996-04-18 WO PCT/US1996/005202 patent/WO1996035691A1/en active IP Right Grant
- 1996-04-18 CN CN96193861A patent/CN1068328C/zh not_active Expired - Fee Related
- 1996-04-18 EP EP96911768A patent/EP0828741B1/en not_active Expired - Lifetime
- 1996-04-18 DK DK96911768T patent/DK0828741T3/da active
- 1996-04-18 NZ NZ306310A patent/NZ306310A/en unknown
- 1996-04-18 KR KR1019970707926A patent/KR100463771B1/ko not_active IP Right Cessation
- 1996-04-18 CA CA002218088A patent/CA2218088A1/en not_active Abandoned
- 1996-04-18 PT PT96911768T patent/PT828741E/pt unknown
- 1996-04-18 AT AT96911768T patent/ATE204874T1/de not_active IP Right Cessation
- 1996-04-18 DE DE69614847T patent/DE69614847T2/de not_active Expired - Fee Related
-
1997
- 1997-11-10 NO NO19975158A patent/NO311298B1/no unknown
- 1997-11-10 FI FI974180A patent/FI974180A0/fi unknown
-
1998
- 1998-09-04 HK HK98110441A patent/HK1009449A1/xx not_active IP Right Cessation
-
2000
- 2000-10-31 CN CN00132826A patent/CN1336375A/zh active Pending
-
2002
- 2002-05-31 HK HK02104105.2A patent/HK1042093A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX9708627A (es) | 1998-02-28 |
| ATE204874T1 (de) | 2001-09-15 |
| NO975158L (no) | 1998-01-09 |
| KR19990008399A (ko) | 1999-01-25 |
| DE69614847T2 (de) | 2002-04-04 |
| FI974180A (fi) | 1997-11-10 |
| WO1996035691A1 (en) | 1996-11-14 |
| AU5484996A (en) | 1996-11-29 |
| NO975158D0 (no) | 1997-11-10 |
| EP0828741B1 (en) | 2001-08-29 |
| HK1009449A1 (en) | 1999-09-10 |
| DK0828741T3 (da) | 2001-11-26 |
| CN1184481A (zh) | 1998-06-10 |
| DE69614847D1 (de) | 2001-10-04 |
| PT828741E (pt) | 2002-02-28 |
| ES2162047T3 (es) | 2001-12-16 |
| NZ306310A (en) | 2001-05-25 |
| CN1336375A (zh) | 2002-02-20 |
| AU702752B2 (en) | 1999-03-04 |
| US6090820A (en) | 2000-07-18 |
| CA2218088A1 (en) | 1996-11-14 |
| JPH11506430A (ja) | 1999-06-08 |
| EP0828741A1 (en) | 1998-03-18 |
| FI974180A0 (fi) | 1997-11-10 |
| CN1068328C (zh) | 2001-07-11 |
| HK1042093A1 (zh) | 2002-08-02 |
| KR100463771B1 (ko) | 2005-05-16 |
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