JP4917432B2 - インビボ効力が改良された抗菌活性を有する置換ピペリジノフェニルオキサゾリジノン化合物 - Google Patents
インビボ効力が改良された抗菌活性を有する置換ピペリジノフェニルオキサゾリジノン化合物 Download PDFInfo
- Publication number
- JP4917432B2 JP4917432B2 JP2006526008A JP2006526008A JP4917432B2 JP 4917432 B2 JP4917432 B2 JP 4917432B2 JP 2006526008 A JP2006526008 A JP 2006526008A JP 2006526008 A JP2006526008 A JP 2006526008A JP 4917432 B2 JP4917432 B2 JP 4917432B2
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- oxazolidine
- ylmethyl
- fluorophenyl
- acetamide
- 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.)
- Expired - Fee Related
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- DNRCUMDULWDBQC-UHFFFAOYSA-N 3-phenyl-4-piperidin-1-yl-1,3-oxazolidin-2-one Chemical class O=C1OCC(N2CCCCC2)N1C1=CC=CC=C1 DNRCUMDULWDBQC-UHFFFAOYSA-N 0.000 title claims description 8
- 238000001727 in vivo Methods 0.000 title description 11
- 230000000845 anti-microbial effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 354
- -1 methanesulfonyloxy, methoxy, ethoxy Chemical group 0.000 claims description 340
- 239000000203 mixture Substances 0.000 claims description 115
- 238000000034 method Methods 0.000 claims description 112
- 239000002904 solvent Substances 0.000 claims description 79
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 63
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 47
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 42
- 238000002360 preparation method Methods 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 37
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 30
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 20
- 235000019270 ammonium chloride Nutrition 0.000 claims description 20
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 18
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- ISDJNKMBJSFUNC-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-hydroxy-4-(methoxymethyl)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(COC)(O)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F ISDJNKMBJSFUNC-HNNXBMFYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- XMYQWUYFRFPERD-UHFFFAOYSA-N 4-(1-oxa-6-azaspiro[2.5]octan-6-yl)-3-phenyl-1,3-oxazolidin-2-one Chemical compound O=C1OCC(N2CCC3(OC3)CC2)N1C1=CC=CC=C1 XMYQWUYFRFPERD-UHFFFAOYSA-N 0.000 claims description 5
- 208000035143 Bacterial infection Diseases 0.000 claims description 5
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 5
- PBMWVGVUXXCUAY-AWEZNQCLSA-N n-[[(5s)-3-[4-[4-(azidomethyl)-4-hydroxypiperidin-1-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=C1N1CCC(O)(CN=[N+]=[N-])CC1 PBMWVGVUXXCUAY-AWEZNQCLSA-N 0.000 claims description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 4
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- KTKSQNNJFDDDKX-ZDUSSCGKSA-N n-[[(5s)-3-[4-[4-(azidomethyl)-4-hydroxypiperidin-1-yl]-3,5-difluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC(F)=C1N1CCC(O)(CN=[N+]=[N-])CC1 KTKSQNNJFDDDKX-ZDUSSCGKSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 172
- 230000008018 melting Effects 0.000 description 172
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
- 238000010898 silica gel chromatography Methods 0.000 description 68
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 54
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
- 239000000741 silica gel Substances 0.000 description 34
- 229910002027 silica gel Inorganic materials 0.000 description 34
- NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 125000000623 heterocyclic group Chemical group 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- 239000011541 reaction mixture Substances 0.000 description 29
- 150000003857 carboxamides Chemical class 0.000 description 28
- 238000000746 purification Methods 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 125000001072 heteroaryl group Chemical group 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 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 18
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 17
- 208000015181 infectious disease Diseases 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 16
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 description 14
- 229960003907 linezolid Drugs 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- UWAHVVNOMMENRW-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(4-oxopiperidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(=O)CC1 UWAHVVNOMMENRW-AWEZNQCLSA-N 0.000 description 13
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 13
- 150000003536 tetrazoles Chemical class 0.000 description 13
- 230000003197 catalytic effect Effects 0.000 description 12
- 125000003386 piperidinyl group Chemical group 0.000 description 12
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- 150000003852 triazoles Chemical class 0.000 description 12
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 238000011097 chromatography purification Methods 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- 230000000844 anti-bacterial effect Effects 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 229910052717 sulfur Chemical group 0.000 description 10
- 239000003826 tablet Substances 0.000 description 10
- ZZKYLYNQMDSFKZ-UHFFFAOYSA-N 4-(4-oxopiperidin-1-yl)-3-phenyl-1,3-oxazolidin-2-one Chemical compound O=C1OCC(N2CCC(=O)CC2)N1C1=CC=CC=C1 ZZKYLYNQMDSFKZ-UHFFFAOYSA-N 0.000 description 9
- 229910015900 BF3 Inorganic materials 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 9
- 239000000969 carrier Substances 0.000 description 9
- 239000002552 dosage form Substances 0.000 description 9
- 125000005241 heteroarylamino group Chemical group 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000651 prodrug Substances 0.000 description 8
- 229940002612 prodrug Drugs 0.000 description 8
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
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- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 238000013375 chromatographic separation Methods 0.000 description 7
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- 229940079593 drug Drugs 0.000 description 7
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- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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- 125000004391 aryl sulfonyl group Chemical group 0.000 description 6
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 description 6
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 6
- UBNOGFKMNUEPIW-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxa-6-azaspiro[2.5]octan-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=C1N1CCC2(OC2)CC1 UBNOGFKMNUEPIW-AWEZNQCLSA-N 0.000 description 6
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- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 description 6
- 238000011200 topical administration Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- SHLSSLVZXJBVHE-UHFFFAOYSA-N 3-sulfanylpropan-1-ol Chemical compound OCCCS SHLSSLVZXJBVHE-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 0 BC(*)(CN(CC1)c(c(C)c2)c(C)cc2N(C[C@](C*)O2)C2=O)C1=O Chemical compound BC(*)(CN(CC1)c(c(C)c2)c(C)cc2N(C[C@](C*)O2)C2=O)C1=O 0.000 description 5
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- AZSRSNUQCUDCGG-UHFFFAOYSA-N propan-2-yl 2-[4-[2-(dimethylamino)ethyl-methylamino]-2-methoxy-5-(prop-2-enoylamino)anilino]-4-(1-methylindol-3-yl)pyrimidine-5-carboxylate Chemical compound C(C=C)(=O)NC=1C(=CC(=C(C=1)NC1=NC=C(C(=N1)C1=CN(C2=CC=CC=C12)C)C(=O)OC(C)C)OC)N(C)CCN(C)C AZSRSNUQCUDCGG-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- FIKPXCOQUIZNHB-WDEREUQCSA-N repotrectinib Chemical compound C[C@H]1CNC(=O)C2=C3N=C(N[C@H](C)C4=C(O1)C=CC(F)=C4)C=CN3N=C2 FIKPXCOQUIZNHB-WDEREUQCSA-N 0.000 description 1
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- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 239000003762 serotonin receptor affecting agent Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- ZIQRIAYNHAKDDU-UHFFFAOYSA-N sodium;hydroiodide Chemical compound [Na].I ZIQRIAYNHAKDDU-UHFFFAOYSA-N 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
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- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
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- 239000007940 sugar coated tablet Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
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- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-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
-
- 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
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN924MU2003 | 2003-09-08 | ||
| IN924/MUM/2003 | 2003-09-08 | ||
| PCT/IN2004/000276 WO2005054234A2 (en) | 2003-09-08 | 2004-09-08 | Substituted piperidino phenyloxazolidinones having antimicriobial activity with improved in vivo efficacy |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007505102A JP2007505102A (ja) | 2007-03-08 |
| JP2007505102A5 JP2007505102A5 (enExample) | 2007-11-01 |
| JP4917432B2 true JP4917432B2 (ja) | 2012-04-18 |
Family
ID=34640331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006526008A Expired - Fee Related JP4917432B2 (ja) | 2003-09-08 | 2004-09-08 | インビボ効力が改良された抗菌活性を有する置換ピペリジノフェニルオキサゾリジノン化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7687627B2 (enExample) |
| EP (1) | EP1664038A2 (enExample) |
| JP (1) | JP4917432B2 (enExample) |
| AU (1) | AU2004295208A1 (enExample) |
| BR (1) | BRPI0413413A (enExample) |
| CA (1) | CA2537559C (enExample) |
| EA (1) | EA200600374A1 (enExample) |
| WO (1) | WO2005054234A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7687627B2 (en) * | 2003-09-08 | 2010-03-30 | Wockhardt Limited | Substituted piperidino phenyloxazolidinones having antimicrobial activity with improved in vivo efficacy |
| WO2007004049A1 (en) * | 2005-07-06 | 2007-01-11 | Pharmacia & Upjohn Company Llc | Oxazolidinones containing azetidine as antibacterial agents |
| JP5313126B2 (ja) * | 2006-05-09 | 2013-10-09 | ウォックハート リミテッド | 置換ピペリジノフェニルオキサゾリジノン |
| CN101616588B (zh) * | 2006-09-25 | 2013-09-25 | 沃克哈特研究中心 | 取代的哌啶子基苯基噁唑烷酮 |
| WO2009037542A2 (en) * | 2007-09-20 | 2009-03-26 | Glenmark Pharmaceuticals, S.A. | Spirocyclic compounds as stearoyl coa desaturase inhibitors |
| EP2072513A1 (en) * | 2007-12-17 | 2009-06-24 | Ferrer Internacional, S.A. | A cyano piperidinyl-phenil-oxazolidinone and use thereof |
| EP2254892B1 (en) | 2008-03-26 | 2014-04-23 | Global Alliance For Tb Drug Development | Bicyclic nitroimidazoles covalently linked to substituted phenyl oxazolidinones |
| EP2141161A1 (en) * | 2008-07-01 | 2010-01-06 | Ferrer Internacional, S.A. | 3-cyanopyrrolidinyl-phenyl-oxazolidinones as antibacterial agents |
| EP2410854B1 (en) * | 2009-03-27 | 2016-06-29 | Council of Scientific & Industrial Research | Substituted 1, 4-dioxa-8-azaspiro ý4,5¨decanes useful as fungicides and a process for the preparation thereof |
| CA2816515A1 (en) * | 2010-11-03 | 2012-05-10 | Wockhardt Limited | Process for the preparation of phosphoric acid mono-(1-{4-[(s)-5-(acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2,6-difluorophenyl}-4-methoxymethylpiperidin-4-yl) ester |
| US9359344B2 (en) | 2011-09-29 | 2016-06-07 | Xuanzhu Pharma Co., Ltd. | Biaryl heterocycle substituted oxazolidinone antibacterial agents |
| WO2015066413A1 (en) * | 2013-11-01 | 2015-05-07 | Novartis Ag | Oxazolidinone hydroxamic acid compounds for the treatment of bacterial infections |
| WO2016079757A2 (en) * | 2014-11-19 | 2016-05-26 | Symed Labs Limited | Novel processes for preparing 5-hydroxymethyl-oxazolidin-2-one derivatives |
| WO2019081210A1 (en) * | 2017-10-27 | 2019-05-02 | Huntsman International Llc | CATALYSTS FOR MANUFACTURING OXAZOLIDINONE MATERIALS |
| CN112543756A (zh) * | 2018-07-25 | 2021-03-23 | 卡迪拉保健有限公司 | 用于治疗哺乳动物感染的经取代噁唑烷酮类 |
| WO2020234636A1 (en) | 2019-05-17 | 2020-11-26 | Cadila Healthcare Limited | Novel compounds for the treatment of mammalian infections |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3344145A (en) * | 1963-10-21 | 1967-09-26 | Geschickter Fund Med Res | N-substituted phenoxyalkyl or phenylthioalkyl-mono azaspiroalkanes |
| 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. |
| US5489689A (en) * | 1993-09-30 | 1996-02-06 | Mallinckrodt Chemical, Inc. | Preparation of piperidine derivatives |
| US5668286A (en) * | 1994-03-15 | 1997-09-16 | Pharmacia & Upjohn Company | Oxazolidinone derivatives and pharmaceutical compositions containing them |
| 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 |
| SI0788498T1 (en) * | 1994-10-26 | 2001-12-31 | Upjohn Co | Phenyloxazolidinone antimicrobials |
| ES2214546T3 (es) * | 1995-09-15 | 2004-09-16 | PHARMACIA & UPJOHN COMPANY | N-oxidos de aminoariloxazolidinona. |
| GB9702213D0 (en) * | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
| GB9609919D0 (en) * | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| RU2208613C2 (ru) * | 1997-05-30 | 2003-07-20 | Фармация Энд Апджон Компани | Оксазолидиноновые антибактериальные агенты, содержащие тиокарбонильную функциональную группу |
| CA2333332A1 (en) * | 1998-06-05 | 1999-12-16 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| GB9821938D0 (en) * | 1998-10-09 | 1998-12-02 | Zeneca Ltd | Chemical compounds |
| JP2000204084A (ja) * | 1998-11-11 | 2000-07-25 | Hokuriku Seiyaku Co Ltd | チオカルバミド酸誘導体 |
| JP3270834B2 (ja) * | 1999-01-27 | 2002-04-02 | ファイザー・プロダクツ・インク | 抗がん剤として有用なヘテロ芳香族二環式誘導体 |
| CA2374383A1 (en) * | 1999-07-28 | 2001-02-08 | Pharmacia & Upjohn Company | Oxazolidinones and their use as antiinfectives |
| US6608081B2 (en) * | 1999-08-12 | 2003-08-19 | Ortho-Mcneil Pharmaceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
| GB2356389B (en) * | 1999-09-02 | 2003-07-16 | Bruce Stanley Gunton | Loading bay dock control |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| WO2002046156A2 (en) * | 2000-12-06 | 2002-06-13 | Sepracor, Inc. | 4,4-disubstituted piperidines for use as dopamine, serotonin and norepinephrine ligands |
| JP2005503435A (ja) * | 2001-04-17 | 2005-02-03 | メルク アンド カンパニー インコーポレーテッド | ビシクロ[3.1.0]ヘキサン含有オキサゾリジノン抗生物質及びその誘導体 |
| DE10129725A1 (de) * | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
| CA2492194A1 (en) * | 2002-07-11 | 2004-01-22 | Wockhardt Limited | Antibacterial cyano-(substituted)-methylenepiperidinophenyl oxazolidinones targeting multiple ribonucleoproteins sites |
| US7405228B2 (en) * | 2002-07-11 | 2008-07-29 | Wockhardt Limited | Antibacterial cyano-(substituted)-methylenepiperidinophenyl oxazolidinones targeting multiple ribonucleoprotein sites |
| AU2003274676A1 (en) * | 2002-07-11 | 2004-02-02 | Yati Chugh | Antimicrobial oxazolidinones, process of their preparation, and pharmaceutical compositions containing them |
| KR100490643B1 (ko) * | 2002-10-29 | 2005-05-19 | 한국과학기술연구원 | 새로운 메틸리덴 피페리딘일 옥사졸리딘온 유도체 및이들의 제조방법 |
| US7687627B2 (en) * | 2003-09-08 | 2010-03-30 | Wockhardt Limited | Substituted piperidino phenyloxazolidinones having antimicrobial activity with improved in vivo efficacy |
| JP5313126B2 (ja) * | 2006-05-09 | 2013-10-09 | ウォックハート リミテッド | 置換ピペリジノフェニルオキサゾリジノン |
-
2004
- 2004-09-07 US US10/935,708 patent/US7687627B2/en not_active Expired - Fee Related
- 2004-09-08 WO PCT/IN2004/000276 patent/WO2005054234A2/en not_active Ceased
- 2004-09-08 AU AU2004295208A patent/AU2004295208A1/en not_active Abandoned
- 2004-09-08 JP JP2006526008A patent/JP4917432B2/ja not_active Expired - Fee Related
- 2004-09-08 CA CA2537559A patent/CA2537559C/en not_active Expired - Fee Related
- 2004-09-08 BR BRPI0413413-3A patent/BRPI0413413A/pt not_active IP Right Cessation
- 2004-09-08 EA EA200600374A patent/EA200600374A1/ru unknown
- 2004-09-08 EP EP04817639A patent/EP1664038A2/en not_active Withdrawn
-
2010
- 2010-02-12 US US12/705,258 patent/US8729269B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005054234A3 (en) | 2005-09-29 |
| CA2537559A1 (en) | 2005-06-16 |
| US20050143421A1 (en) | 2005-06-30 |
| US7687627B2 (en) | 2010-03-30 |
| AU2004295208A1 (en) | 2005-06-16 |
| JP2007505102A (ja) | 2007-03-08 |
| WO2005054234A2 (en) | 2005-06-16 |
| US8729269B2 (en) | 2014-05-20 |
| EA200600374A1 (ru) | 2006-08-25 |
| EP1664038A2 (en) | 2006-06-07 |
| BRPI0413413A (pt) | 2007-01-09 |
| CA2537559C (en) | 2012-11-20 |
| WO2005054234A8 (en) | 2006-11-23 |
| US20100144735A1 (en) | 2010-06-10 |
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