CN1314813A - 新的异噁唑啉酮抗菌剂 - Google Patents
新的异噁唑啉酮抗菌剂 Download PDFInfo
- Publication number
- CN1314813A CN1314813A CN99809894A CN99809894A CN1314813A CN 1314813 A CN1314813 A CN 1314813A CN 99809894 A CN99809894 A CN 99809894A CN 99809894 A CN99809894 A CN 99809894A CN 1314813 A CN1314813 A CN 1314813A
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- CN
- China
- Prior art keywords
- alkyl
- optional
- phenyl
- alkoxyl
- replaces
- Prior art date
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- JGRCHNVLXORPNM-UHFFFAOYSA-N 1,2-oxazol-4-one Chemical compound O=C1CON=C1 JGRCHNVLXORPNM-UHFFFAOYSA-N 0.000 title abstract description 13
- 239000003242 anti bacterial agent Substances 0.000 title description 3
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 134
- 150000001875 compounds Chemical class 0.000 claims description 84
- 229910052757 nitrogen Inorganic materials 0.000 claims description 82
- -1 pyrimidine radicals Chemical class 0.000 claims description 77
- 229910052717 sulfur Inorganic materials 0.000 claims description 74
- 125000005843 halogen group Chemical group 0.000 claims description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 229910052799 carbon Inorganic materials 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 229910052760 oxygen Inorganic materials 0.000 claims description 50
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 47
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 32
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 32
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
- 125000004429 atom Chemical group 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- 150000001721 carbon Chemical group 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 13
- 125000004423 acyloxy group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical class 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 5
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 3
- 150000002790 naphthalenes Chemical class 0.000 claims description 3
- 229910001415 sodium ion Inorganic materials 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- 239000000203 mixture Substances 0.000 description 81
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 79
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
- 239000007787 solid Substances 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000002585 base Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 238000005481 NMR spectroscopy Methods 0.000 description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
- 239000000376 reactant Substances 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 235000019439 ethyl acetate Nutrition 0.000 description 24
- 239000012141 concentrate Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- 238000005406 washing Methods 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000000227 grinding Methods 0.000 description 10
- 125000004193 piperazinyl group Chemical group 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 7
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 7
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000001154 acute effect Effects 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 6
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
- 239000004519 grease Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 4
- 150000000177 1,2,3-triazoles Chemical class 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000194032 Enterococcus faecalis Species 0.000 description 3
- 241000192125 Firmicutes Species 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 241000194017 Streptococcus Species 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 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
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940032049 enterococcus faecalis Drugs 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 2
- QPMULSBLPCPFPS-UHFFFAOYSA-N 5-amino-3-phenyl-1,2-oxazol-4-one Chemical compound O=C1C(N)ON=C1C1=CC=CC=C1 QPMULSBLPCPFPS-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- TWIASPXZARVBBY-UHFFFAOYSA-N tributyl(2,3-dihydro-1,4-dioxin-5-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=COCCO1 TWIASPXZARVBBY-UHFFFAOYSA-N 0.000 description 1
- SANWDQJIWZEKOD-UHFFFAOYSA-N tributyl(furan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CO1 SANWDQJIWZEKOD-UHFFFAOYSA-N 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/12—Oxygen atoms
-
- 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US9757498P | 1998-08-24 | 1998-08-24 | |
US60/097574 | 1998-08-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1314813A true CN1314813A (zh) | 2001-09-26 |
Family
ID=22264103
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN99809894A Pending CN1314813A (zh) | 1998-08-24 | 1999-08-23 | 新的异噁唑啉酮抗菌剂 |
Country Status (22)
Country | Link |
---|---|
EP (1) | EP1107756A4 (xx) |
JP (1) | JP2002523369A (xx) |
KR (1) | KR20010072945A (xx) |
CN (1) | CN1314813A (xx) |
AR (1) | AR020250A1 (xx) |
AU (1) | AU748750B2 (xx) |
BR (1) | BR9913225A (xx) |
CA (1) | CA2341271A1 (xx) |
CO (1) | CO5160266A1 (xx) |
CZ (1) | CZ2001669A3 (xx) |
HU (1) | HUP0103433A3 (xx) |
ID (1) | ID27690A (xx) |
IL (1) | IL141542A0 (xx) |
NO (1) | NO20010916L (xx) |
NZ (1) | NZ509867A (xx) |
PE (1) | PE20001063A1 (xx) |
PL (1) | PL346267A1 (xx) |
TR (1) | TR200100672T2 (xx) |
TW (1) | TW572757B (xx) |
UY (1) | UY25677A1 (xx) |
WO (1) | WO2000010566A1 (xx) |
ZA (1) | ZA200101505B (xx) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110423610A (zh) * | 2019-08-29 | 2019-11-08 | 浙江理工大学 | 一种检测双光子汞离子荧光探针及其制备方法与使用方法 |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6465456B2 (en) * | 2000-06-29 | 2002-10-15 | Bristol-Myers Squibb Company | Isoxazolinone antibacterial agents |
JP2002020366A (ja) * | 2000-07-05 | 2002-01-23 | Sumitomo Seika Chem Co Ltd | アルキルチオフェニル酢酸類の製造方法 |
PE20030044A1 (es) | 2000-11-17 | 2003-02-09 | Upjohn Co | Isoxazolinonas biciclicas de formula i |
PE20020689A1 (es) | 2000-11-17 | 2002-08-03 | Upjohn Co | Oxazolidinonas con un heterociclo de 6 o 7 miembros unidos con enlace anular al benceno |
US6861433B2 (en) | 2000-12-15 | 2005-03-01 | Pharmacia & Upjohn Company | Oxazolidinone photoaffinity probes |
CA2424402A1 (en) | 2000-12-21 | 2002-08-01 | Pharmacia & Upjohn Company | Antimicrobial quinolone derivatives and use of the same to treat bacterial infections |
ES2180456B1 (es) * | 2001-07-20 | 2004-05-01 | Laboratorios S.A.L.V.A.T., S.A. | Isoxazoles sustituidos y su utilizacion como antibioticos. |
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 |
JP2005512975A (ja) | 2001-10-25 | 2005-05-12 | アストラゼネカ アクチボラグ | 抗菌薬として有用なイソキサゾリン誘導体 |
US6875784B2 (en) | 2002-10-09 | 2005-04-05 | Pharmacia & Upjohn Company | Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives |
MXPA05003774A (es) * | 2002-10-10 | 2005-06-08 | Pharmacia & Upjohn Co Llc | Compuestos de 1-aril-dihidropiridona con actividad antimicrobiana. |
WO2004069832A2 (en) * | 2003-02-07 | 2004-08-19 | Warner-Lambert Company Llc | Antibacterial agents |
RU2351335C2 (ru) | 2003-04-30 | 2009-04-10 | Морфохем Акциенгезельшафт Фюр Комбинаторише Хеми | Применение оксазолидинон-хинолиновых гибридных антибиотиков для лечения сибирской язвы и других инфекций |
AR045690A1 (es) | 2003-06-03 | 2005-11-09 | Rib X Pharmaceuticals Inc | Compuestos biaril heterociclicos y metodos para preparar y utilizar los mismos |
WO2005070904A2 (en) * | 2003-06-03 | 2005-08-04 | Rib-X Pharmaceutical, Inc. | Sulfonamide compounds and methods of making and using the same |
US8324398B2 (en) | 2003-06-03 | 2012-12-04 | Rib-X Pharmaceuticals, Inc. | Process for the synthesis of biaryl oxazolidinones |
WO2005012270A2 (en) * | 2003-07-29 | 2005-02-10 | Rib-X Pharmaceuticals, Inc. | Biaryl heterocyclic amines, amides, and sulfur-containing compounds and methods of making and using the same |
DE10340485B4 (de) * | 2003-09-03 | 2015-05-13 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Verfahren zur Herstellung von Oxazolidinon-Chinolon Hybriden |
US7304050B2 (en) * | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
JP2007514782A (ja) | 2003-12-17 | 2007-06-07 | リブ−エックス ファーマシューティカルズ,インコーポレイテッド | ハロゲン化ビアリール複素環式化合物ならびにその作製方法および使用方法 |
ES2310299T5 (es) | 2003-12-18 | 2014-02-10 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Antibióticos híbridos a base de oxazolidinona-quinolona |
US8158797B2 (en) | 2003-12-18 | 2012-04-17 | Morphochem Aktiengesellschaft Fur Kombinatorische Chemie | Oxazolidinone-quinolone hybrid antibiotics |
WO2005082900A2 (en) * | 2004-01-28 | 2005-09-09 | Pharmacia & Upjohn Company Llc | Oxazolidinone amidoximes as antibacterial agents |
WO2006133397A2 (en) | 2005-06-08 | 2006-12-14 | Rib-X Pharmaceuticals, Inc. | Process for the synthesis of triazoles |
AT503354B1 (de) * | 2006-02-22 | 2008-07-15 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von 3,4-disubstituierten phenylessigsäuren, sowie neue zwischenverbindungen |
JP4518066B2 (ja) * | 2006-10-25 | 2010-08-04 | 宇部興産株式会社 | ジアルコキシニトリル誘導体及びその製法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2045049A1 (de) * | 1970-09-11 | 1972-03-23 | Dr Karl Thomae GmbH, 7950 Biberach | Neue Nitrofurandenvate und Ver fahren zu ihrer Herstellung |
US4000155A (en) * | 1975-12-11 | 1976-12-28 | Eli Lilly And Company | Herbicidal 2-methyl-4-phenyl-5-pyrazolinones[and isoxazolinones] |
ATE161833T1 (de) * | 1992-12-08 | 1998-01-15 | Upjohn Co | Durch eine tropon gruppe substituierte phenyloxazolidinone-derivate als antibakterielles mittel |
US5708169A (en) * | 1995-09-15 | 1998-01-13 | Pharmacia & Upjohn Company | 5-amidomethyl α,β-saturated and -unsaturated 3-aryl butyrolactone antibacterial agents |
GB9521508D0 (en) * | 1995-10-20 | 1995-12-20 | Zeneca Ltd | Chemical compounds |
PT920421E (pt) * | 1996-08-21 | 2003-03-31 | Upjohn Co | Derivados de isoxazolina uteis como agentes antimicrobianos |
-
1999
- 1999-08-19 TW TW88114208A patent/TW572757B/zh active
- 1999-08-23 KR KR1020017002377A patent/KR20010072945A/ko not_active Application Discontinuation
- 1999-08-23 NZ NZ509867A patent/NZ509867A/en unknown
- 1999-08-23 HU HU0103433A patent/HUP0103433A3/hu unknown
- 1999-08-23 ID IDW20010439A patent/ID27690A/id unknown
- 1999-08-23 CN CN99809894A patent/CN1314813A/zh active Pending
- 1999-08-23 WO PCT/US1999/019265 patent/WO2000010566A1/en not_active Application Discontinuation
- 1999-08-23 PL PL99346267A patent/PL346267A1/xx not_active Application Discontinuation
- 1999-08-23 BR BR9913225-7A patent/BR9913225A/pt not_active IP Right Cessation
- 1999-08-23 TR TR2001/00672T patent/TR200100672T2/xx unknown
- 1999-08-23 AU AU57833/99A patent/AU748750B2/en not_active Ceased
- 1999-08-23 EP EP99945157A patent/EP1107756A4/en not_active Withdrawn
- 1999-08-23 CZ CZ2001669A patent/CZ2001669A3/cs unknown
- 1999-08-23 IL IL14154299A patent/IL141542A0/xx unknown
- 1999-08-23 CO CO99053191A patent/CO5160266A1/es unknown
- 1999-08-23 JP JP2000565887A patent/JP2002523369A/ja active Pending
- 1999-08-23 CA CA002341271A patent/CA2341271A1/en not_active Abandoned
- 1999-08-24 PE PE1999000853A patent/PE20001063A1/es not_active Application Discontinuation
- 1999-08-24 AR ARP990104229A patent/AR020250A1/es not_active Application Discontinuation
- 1999-08-24 UY UY25677A patent/UY25677A1/es unknown
-
2001
- 2001-02-22 ZA ZA200101505A patent/ZA200101505B/en unknown
- 2001-02-23 NO NO20010916A patent/NO20010916L/no not_active Application Discontinuation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110423610A (zh) * | 2019-08-29 | 2019-11-08 | 浙江理工大学 | 一种检测双光子汞离子荧光探针及其制备方法与使用方法 |
CN110423610B (zh) * | 2019-08-29 | 2023-05-12 | 浙江理工大学 | 一种检测双光子汞离子荧光探针及其制备方法与使用方法 |
Also Published As
Publication number | Publication date |
---|---|
CO5160266A1 (es) | 2002-05-30 |
AU748750B2 (en) | 2002-06-13 |
CZ2001669A3 (cs) | 2001-08-15 |
KR20010072945A (ko) | 2001-07-31 |
EP1107756A4 (en) | 2003-02-26 |
AU5783399A (en) | 2000-03-14 |
NO20010916D0 (no) | 2001-02-23 |
NZ509867A (en) | 2003-08-29 |
BR9913225A (pt) | 2001-05-22 |
JP2002523369A (ja) | 2002-07-30 |
HUP0103433A2 (hu) | 2002-01-28 |
WO2000010566A1 (en) | 2000-03-02 |
ZA200101505B (en) | 2002-02-22 |
PL346267A1 (en) | 2002-01-28 |
UY25677A1 (es) | 2001-08-27 |
CA2341271A1 (en) | 2000-03-02 |
EP1107756A1 (en) | 2001-06-20 |
AR020250A1 (es) | 2002-05-02 |
HUP0103433A3 (en) | 2002-08-28 |
TR200100672T2 (tr) | 2001-07-23 |
IL141542A0 (en) | 2002-03-10 |
ID27690A (id) | 2001-04-19 |
TW572757B (en) | 2004-01-21 |
NO20010916L (no) | 2001-04-10 |
PE20001063A1 (es) | 2000-12-24 |
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