RU2453546C2 - Производные 5-гидроксиметилоксазолидин-2-она - Google Patents
Производные 5-гидроксиметилоксазолидин-2-она Download PDFInfo
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- RU2453546C2 RU2453546C2 RU2009121812/04A RU2009121812A RU2453546C2 RU 2453546 C2 RU2453546 C2 RU 2453546C2 RU 2009121812/04 A RU2009121812/04 A RU 2009121812/04A RU 2009121812 A RU2009121812 A RU 2009121812A RU 2453546 C2 RU2453546 C2 RU 2453546C2
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- Prior art keywords
- fluoro
- formula
- compound
- oxo
- carboxylic acid
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- LSYOFPBORRARMF-UHFFFAOYSA-N 5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical class OCC1CNC(=O)O1 LSYOFPBORRARMF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 225
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011737 fluorine Substances 0.000 claims abstract description 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 9
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 9
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
- -1 (R) -5-hydroxymethyl-2-oxooxazolidin-3-yl Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- XWFCFMXQTBGXQW-GOSISDBHSA-N cadazolid Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1OCC1(O)CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1 XWFCFMXQTBGXQW-GOSISDBHSA-N 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- SWOGALKAENXHGV-LJQANCHMSA-N 1-cyclopropyl-6-fluoro-7-[4-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]piperidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1OCC1CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1 SWOGALKAENXHGV-LJQANCHMSA-N 0.000 claims description 4
- OIFJTJPMWBXTHP-JWRCQZCYSA-N 1-cyclopropyl-6-fluoro-7-[(3s)-3-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]-3-hydroxypyrrolidin-1-yl]-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@@]1(CCN(C1)C1=C(C2=C(C(C(C(O)=O)=CN2C2CC2)=O)C=C1F)OC)O)OC(C(=C1)F)=CC=C1N1C[C@H](CO)OC1=O OIFJTJPMWBXTHP-JWRCQZCYSA-N 0.000 claims description 3
- WICILBKKMJRQQS-QGZVFWFLSA-N 1-cyclopropyl-6-fluoro-7-[4-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]-4-hydroxypiperidin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1OCC1(O)CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3N=2)C2CC2)F)CC1 WICILBKKMJRQQS-QGZVFWFLSA-N 0.000 claims description 3
- QGKRIADGRBLWEU-OAHLLOKOSA-N 6-fluoro-7-[4-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]-4-hydroxypiperidin-1-yl]-4-oxo-1h-quinoline-3-carboxylic acid Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1OCC1(O)CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CNC=3C=2)F)CC1 QGKRIADGRBLWEU-OAHLLOKOSA-N 0.000 claims description 3
- XYMOZFBAOXAFFX-JYRCXFKTSA-N 1-cyclopropyl-6-fluoro-7-[(3r)-3-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]-3-hydroxypyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1OC[C@]1(O)CN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1 XYMOZFBAOXAFFX-JYRCXFKTSA-N 0.000 claims description 2
- VTIASVRAJJZFQX-CRAIPNDOSA-N 1-cyclopropyl-6-fluoro-7-[(3r)-3-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]pyrrolidin-1-yl]-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@@H]1CCN(C1)C1=C(C2=C(C(C(C(O)=O)=CN2C2CC2)=O)C=C1F)OC)OC(C(=C1)F)=CC=C1N1C[C@H](CO)OC1=O VTIASVRAJJZFQX-CRAIPNDOSA-N 0.000 claims description 2
- XYMOZFBAOXAFFX-UULLZXFKSA-N 1-cyclopropyl-6-fluoro-7-[(3s)-3-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]-3-hydroxypyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1OC[C@@]1(O)CN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1 XYMOZFBAOXAFFX-UULLZXFKSA-N 0.000 claims description 2
- FDBPYSDSEGUHHL-MAUKXSAKSA-N 1-cyclopropyl-6-fluoro-7-[(3s)-3-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]pyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1OC[C@@H]1CN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1 FDBPYSDSEGUHHL-MAUKXSAKSA-N 0.000 claims description 2
- VTIASVRAJJZFQX-MAUKXSAKSA-N 1-cyclopropyl-6-fluoro-7-[(3s)-3-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]pyrrolidin-1-yl]-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@H]1CCN(C1)C1=C(C2=C(C(C(C(O)=O)=CN2C2CC2)=O)C=C1F)OC)OC(C(=C1)F)=CC=C1N1C[C@H](CO)OC1=O VTIASVRAJJZFQX-MAUKXSAKSA-N 0.000 claims description 2
- CUEMRLSQSFRPHB-GOSISDBHSA-N 1-cyclopropyl-6-fluoro-7-[4-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]-4-phosphonooxypiperidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1OCC1(OP(O)(O)=O)CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1 CUEMRLSQSFRPHB-GOSISDBHSA-N 0.000 claims description 2
- FQTILHNGBOUBMB-GOSISDBHSA-N 1-ethyl-6-fluoro-7-[4-[[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]piperidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N(CC1)CCC1COC(C(=C1)F)=CC=C1N1C[C@H](CO)OC1=O FQTILHNGBOUBMB-GOSISDBHSA-N 0.000 claims description 2
- KZDINWHIBGGNGZ-FXAWDEMLSA-N 7-[4-[[4-[(5r)-5-[[(2s)-2-aminopropanoyl]oxymethyl]-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenoxy]methyl]-4-hydroxypiperidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound O=C1O[C@@H](COC(=O)[C@@H](N)C)CN1C(C=C1F)=CC=C1OCC1(O)CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1 KZDINWHIBGGNGZ-FXAWDEMLSA-N 0.000 claims description 2
- YEXQGCQBBNPKAP-LAUBAEHRSA-N 7-[4-[[4-[(5r)-5-[[(2s)-2-aminopropanoyl]oxymethyl]-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenoxy]methyl]piperidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound O=C1O[C@@H](COC(=O)[C@@H](N)C)CN1C(C=C1F)=CC=C1OCC1CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1 YEXQGCQBBNPKAP-LAUBAEHRSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 105
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- 239000000243 solution Substances 0.000 description 49
- 239000000543 intermediate Substances 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
- 125000006239 protecting group Chemical group 0.000 description 20
- 230000002829 reductive effect Effects 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 238000001914 filtration Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
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- 229910052763 palladium Inorganic materials 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 125000005103 alkyl silyl group Chemical group 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 7
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- 235000001014 amino acid Nutrition 0.000 description 7
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- 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 description 7
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
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Classifications
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic 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
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- 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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
-
- 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
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- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB2006054189 | 2006-11-10 | ||
| IBPCT/IB2006/054189 | 2006-11-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009121812A RU2009121812A (ru) | 2010-12-20 |
| RU2453546C2 true RU2453546C2 (ru) | 2012-06-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2009121812/04A RU2453546C2 (ru) | 2006-11-10 | 2007-11-09 | Производные 5-гидроксиметилоксазолидин-2-она |
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| JP (2) | JP4484965B2 (OSRAM) |
| KR (1) | KR101118402B1 (OSRAM) |
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| AR (1) | AR063788A1 (OSRAM) |
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| MY (1) | MY148847A (OSRAM) |
| NO (1) | NO344727B1 (OSRAM) |
| NZ (1) | NZ577538A (OSRAM) |
| PL (1) | PL2086968T3 (OSRAM) |
| PT (1) | PT2086968E (OSRAM) |
| RU (1) | RU2453546C2 (OSRAM) |
| SI (1) | SI2086968T1 (OSRAM) |
| TW (1) | TWI374138B (OSRAM) |
| WO (1) | WO2008056335A1 (OSRAM) |
| ZA (1) | ZA200904028B (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003031443A1 (en) | 2001-10-04 | 2003-04-17 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Dual actions antibiotics comprising a oxazoldinone and a quinolone or naphthyridinone moiety |
| ES2308171T3 (es) | 2003-04-30 | 2008-12-01 | Morphochem Aktiengesellschaft Fur Kombinatorische Chemie | Uso de antibioticos hibridos de oxazolidinona-quinolina para el tratamiento del antrax y de otras infecciones. |
| DE10340485B4 (de) | 2003-09-03 | 2015-05-13 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Verfahren zur Herstellung von Oxazolidinon-Chinolon Hybriden |
| US8158797B2 (en) | 2003-12-18 | 2012-04-17 | Morphochem Aktiengesellschaft Fur Kombinatorische Chemie | Oxazolidinone-quinolone hybrid antibiotics |
| CA2549675C (en) † | 2003-12-18 | 2012-11-20 | Morphochem Aktiengesellschaft Fur Kombinatorische Chemie | Oxazolidinone-quinolone hybrid antibiotics |
| US8124623B2 (en) | 2006-11-10 | 2012-02-28 | Actelion Pharmaceuticals Ltd. | 5-hydroxymethyl-oxazolidin-2-one-derivatives and their uses as antibacterials |
| RU2527769C2 (ru) * | 2008-05-09 | 2014-09-10 | Актелион Фармасьютиклз Лтд | Производные 5-гидроксиметилоксазолидин-2-она для лечения бактериальных кишечных заболеваний |
| JP6030146B2 (ja) * | 2011-11-08 | 2016-11-24 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | ２−オキソ−オキサゾリジン−３，５−ジイル抗生物質誘導体 |
| CN105246476B (zh) | 2013-05-28 | 2019-11-15 | 莫弗凯姆联合化学股份公司 | 含噁唑烷酮-喹诺酮的联合疗法在治疗细菌感染中的应用 |
| MX371037B (es) | 2013-05-28 | 2020-01-14 | Morphochem Aktiengesellschaft Fuer Komb Chemie | Antibacterianos híbridos de oxazolidinona-quinolona para el tratamiento parenteral o profilaxis de enfermedades bacterianas. |
| WO2016079757A2 (en) * | 2014-11-19 | 2016-05-26 | Symed Labs Limited | Novel processes for preparing 5-hydroxymethyl-oxazolidin-2-one derivatives |
| WO2017146246A1 (ja) | 2016-02-26 | 2017-08-31 | 大塚製薬株式会社 | ピペリジン誘導体 |
| US10087171B2 (en) | 2016-12-19 | 2018-10-02 | Actelion Pharmaceuticals Ltd | Crystalline forms of cadazolid |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4461773A (en) * | 1982-09-15 | 1984-07-24 | E. I. Dupont De Nemours And Company | P-Oxooxazolidinylbenzene compounds as antibacterial agents |
| WO2002059116A2 (en) * | 2000-12-21 | 2002-08-01 | Pharmacia & Upjohn Company | Antimicrobial quinolone derivatives and use of the same to treat bacterial infections |
| WO2003032962A2 (en) * | 2001-10-04 | 2003-04-24 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Dual action antibiotics |
| WO2004096221A1 (en) * | 2003-04-30 | 2004-11-11 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
| WO2005058886A1 (en) * | 2003-12-18 | 2005-06-30 | Dong-A Pharm.Co.,Ltd. | Novel oxazolidinone derivatives |
| WO2005058888A2 (en) * | 2003-12-18 | 2005-06-30 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Oxazolidinone-quinolone hybrid antibiotics |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1156597A3 (ru) * | 1982-04-28 | 1985-05-15 | Е.И.Дюпон Де Немур Энд Компани (Фирма) | Способ получени производных 3-( @ -алкилсульфонилфенил)оксазолидинона или их фармацевтически приемлемых кислотно-аддитивных солей |
| US6608081B2 (en) * | 1999-08-12 | 2003-08-19 | Ortho-Mcneil Pharmaceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
| US6413981B1 (en) * | 1999-08-12 | 2002-07-02 | Ortho-Mcneil Pharamceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
| US6951863B2 (en) * | 2001-02-07 | 2005-10-04 | Ortho-Mcneil Pharmaceutical, Inc. | Pyridoarylphenly oxazolidinone antibacterials, and related compositions and methods |
| ZA200509147B (en) * | 2003-04-30 | 2007-03-28 | Morphochem Ag | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
-
2007
- 2007-11-09 AT AT07827038T patent/ATE544764T1/de active
- 2007-11-09 CA CA2668280A patent/CA2668280C/en active Active
- 2007-11-09 BR BRPI0718862A patent/BRPI0718862B8/pt not_active IP Right Cessation
- 2007-11-09 NZ NZ577538A patent/NZ577538A/en not_active IP Right Cessation
- 2007-11-09 HR HRP20120385TT patent/HRP20120385T1/hr unknown
- 2007-11-09 PL PL07827038T patent/PL2086968T3/pl unknown
- 2007-11-09 EP EP07827038A patent/EP2086968B1/en active Active
- 2007-11-09 AU AU2007318901A patent/AU2007318901B2/en not_active Ceased
- 2007-11-09 CN CN2007800418985A patent/CN101535305B/zh not_active Expired - Fee Related
- 2007-11-09 DK DK07827038.6T patent/DK2086968T3/da active
- 2007-11-09 TW TW096142564A patent/TWI374138B/zh not_active IP Right Cessation
- 2007-11-09 RU RU2009121812/04A patent/RU2453546C2/ru active
- 2007-11-09 JP JP2009535864A patent/JP4484965B2/ja not_active Expired - Fee Related
- 2007-11-09 CL CL200703232A patent/CL2007003232A1/es unknown
- 2007-11-09 KR KR1020097010924A patent/KR101118402B1/ko not_active Expired - Fee Related
- 2007-11-09 WO PCT/IB2007/054557 patent/WO2008056335A1/en not_active Ceased
- 2007-11-09 ES ES07827038T patent/ES2380388T3/es active Active
- 2007-11-09 PT PT07827038T patent/PT2086968E/pt unknown
- 2007-11-09 MX MX2009004764A patent/MX2009004764A/es active IP Right Grant
- 2007-11-09 MY MYPI20091893A patent/MY148847A/en unknown
- 2007-11-09 SI SI200730902T patent/SI2086968T1/sl unknown
- 2007-11-12 AR ARP070105031A patent/AR063788A1/es active IP Right Grant
-
2009
- 2009-05-07 IL IL198645A patent/IL198645A/en active IP Right Grant
- 2009-06-01 MA MA31939A patent/MA30960B1/fr unknown
- 2009-06-09 ZA ZA200904028A patent/ZA200904028B/xx unknown
- 2009-06-09 NO NO20092209A patent/NO344727B1/no unknown
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2010
- 2010-01-27 JP JP2010016076A patent/JP5490553B2/ja not_active Expired - Fee Related
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2012
- 2012-04-24 CY CY20121100383T patent/CY1112696T1/el unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4461773A (en) * | 1982-09-15 | 1984-07-24 | E. I. Dupont De Nemours And Company | P-Oxooxazolidinylbenzene compounds as antibacterial agents |
| WO2002059116A2 (en) * | 2000-12-21 | 2002-08-01 | Pharmacia & Upjohn Company | Antimicrobial quinolone derivatives and use of the same to treat bacterial infections |
| WO2003032962A2 (en) * | 2001-10-04 | 2003-04-24 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Dual action antibiotics |
| WO2004096221A1 (en) * | 2003-04-30 | 2004-11-11 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
| WO2005058886A1 (en) * | 2003-12-18 | 2005-06-30 | Dong-A Pharm.Co.,Ltd. | Novel oxazolidinone derivatives |
| WO2005058888A2 (en) * | 2003-12-18 | 2005-06-30 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Oxazolidinone-quinolone hybrid antibiotics |
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| L.VERA-CABRERA et al.: "In vitro activities of DA-7157 and DA-7218 against mycobacterium tuberculosis and nocardia brasiliensis" Antimicrobial Agents and Chemotherapy, v.50, №9, September 2006, p.3170-3172. * |
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