CN101570545A - 作为内酰胺酶抑制剂的二环6-亚烷基-表霉烯 - Google Patents
作为内酰胺酶抑制剂的二环6-亚烷基-表霉烯 Download PDFInfo
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- CN101570545A CN101570545A CNA2009101331547A CN200910133154A CN101570545A CN 101570545 A CN101570545 A CN 101570545A CN A2009101331547 A CNA2009101331547 A CN A2009101331547A CN 200910133154 A CN200910133154 A CN 200910133154A CN 101570545 A CN101570545 A CN 101570545A
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- 239000003781 beta lactamase inhibitor Substances 0.000 title description 8
- 229940126813 beta-lactamase inhibitor Drugs 0.000 title description 8
- 125000002619 bicyclic group Chemical group 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 154
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
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- 239000000203 mixture Substances 0.000 claims description 215
- 229910052799 carbon Inorganic materials 0.000 claims description 198
- 229910052760 oxygen Inorganic materials 0.000 claims description 134
- -1 alkyl-aryloxy alkylamine Chemical class 0.000 claims description 131
- 235000019439 ethyl acetate Nutrition 0.000 claims description 115
- 229910052717 sulfur Inorganic materials 0.000 claims description 107
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 93
- 238000002360 preparation method Methods 0.000 claims description 86
- 159000000000 sodium salts Chemical class 0.000 claims description 86
- 150000003839 salts Chemical class 0.000 claims description 58
- 229910052757 nitrogen Inorganic materials 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000004494 ethyl ester group Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 25
- 150000001721 carbon Chemical group 0.000 claims description 24
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 24
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 239000002132 β-lactam antibiotic Substances 0.000 claims description 22
- 229940124586 β-lactam antibiotics Drugs 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 19
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 claims description 19
- HHXMXAQDOUCLDN-UHFFFAOYSA-N 4-thia-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical compound S1C=CN2C(=O)CC21 HHXMXAQDOUCLDN-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 229960002292 piperacillin Drugs 0.000 claims description 9
- WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 claims description 9
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 8
- 238000011049 filling Methods 0.000 claims description 8
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229930182555 Penicillin Natural products 0.000 claims description 5
- 125000005325 aryloxy aryl group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 229940049954 penicillin Drugs 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- 229960003022 amoxicillin Drugs 0.000 claims description 4
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 3
- JWCSIUVGFCSJCK-CAVRMKNVSA-N Disodium Moxalactam Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CO[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C1=CC=C(O)C=C1 JWCSIUVGFCSJCK-CAVRMKNVSA-N 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 3
- 229960000433 latamoxef Drugs 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 3
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 claims description 3
- 229960004659 ticarcillin Drugs 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- JETQIUPBHQNHNZ-NJBDSQKTSA-N (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-phenyl-2-sulfoacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H](C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)S(O)(=O)=O)=CC=CC=C1 JETQIUPBHQNHNZ-NJBDSQKTSA-N 0.000 claims description 2
- WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 claims description 2
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims description 2
- JFPVXVDWJQMJEE-QMTHXVAHSA-N Cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)C(=NOC)C1=CC=CO1 JFPVXVDWJQMJEE-QMTHXVAHSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 229960000723 ampicillin Drugs 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical compound O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 claims description 2
- 229960003644 aztreonam Drugs 0.000 claims description 2
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229940056360 penicillin g Drugs 0.000 claims description 2
- 229940081561 rocephin Drugs 0.000 claims description 2
- 229960004932 sulbenicillin Drugs 0.000 claims description 2
- KTAVBOYXMBQFGR-MAODNAKNSA-J tetrasodium;(6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-1-oxidoethylidene]amino]-3-[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C([O-])=NN1C.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C([O-])=NN1C KTAVBOYXMBQFGR-MAODNAKNSA-J 0.000 claims description 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
- SNAJDOSOLZFUIK-UHFFFAOYSA-N CC1(CCC(NC1)=O)C.[Na] Chemical compound CC1(CCC(NC1)=O)C.[Na] SNAJDOSOLZFUIK-UHFFFAOYSA-N 0.000 claims 1
- 229930186147 Cephalosporin Natural products 0.000 claims 1
- 229960001139 cefazolin Drugs 0.000 claims 1
- FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 claims 1
- 229940124587 cephalosporin Drugs 0.000 claims 1
- 150000001780 cephalosporins Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 abstract 2
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 310
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 297
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 249
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 233
- 239000011541 reaction mixture Substances 0.000 description 212
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 151
- 239000012141 concentrate Substances 0.000 description 133
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 129
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 111
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- 239000012044 organic layer Substances 0.000 description 102
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 100
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 99
- 238000005406 washing Methods 0.000 description 99
- 239000010410 layer Substances 0.000 description 86
- 238000003756 stirring Methods 0.000 description 84
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 74
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- 239000012299 nitrogen atmosphere Substances 0.000 description 66
- 238000010898 silica gel chromatography Methods 0.000 description 64
- 239000000047 product Substances 0.000 description 58
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 57
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- 238000005286 illumination Methods 0.000 description 56
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 50
- 229960003328 benzoyl peroxide Drugs 0.000 description 48
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 44
- 238000001035 drying Methods 0.000 description 43
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 42
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 39
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 24
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- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 22
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 19
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- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000005051 dihydropyrazinyl group Chemical group N1(CC=NC=C1)* 0.000 description 1
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 description 1
- 125000005058 dihydrotriazolyl group Chemical group N1(NNC=C1)* 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 244000000058 gram-negative pathogen Species 0.000 description 1
- 244000000059 gram-positive pathogen Species 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005367 heteroarylalkylthio group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000005235 imidazopyrazines Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Inorganic materials O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QMOLJWDHFVAQQX-UHFFFAOYSA-N methyl 3,4-dihydropyridine-2-carboxylate Chemical compound COC(=O)C1=NC=CCC1 QMOLJWDHFVAQQX-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 238000005142 microbroth dilution method Methods 0.000 description 1
- JUNOWSHJELIDQP-UHFFFAOYSA-N morpholin-4-ium-3-carboxylate Chemical compound OC(=O)C1COCCN1 JUNOWSHJELIDQP-UHFFFAOYSA-N 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- LSCYTCMNCWMCQE-UHFFFAOYSA-N n-methylpyridin-4-amine Chemical compound CNC1=CC=NC=C1 LSCYTCMNCWMCQE-UHFFFAOYSA-N 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000005789 organism growth Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- MTYYIWGKIVFIMX-UHFFFAOYSA-N oxazine-2-carboxylic acid Chemical compound OC(=O)N1OC=CC=C1 MTYYIWGKIVFIMX-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- NRTTUJLILQPENP-UHFFFAOYSA-N pyridine-2-carbaldehyde;hydrochloride Chemical compound Cl.O=CC1=CC=CC=N1 NRTTUJLILQPENP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- IJOUCDYZGQFHNL-UHFFFAOYSA-N thiazinane-4-carboxylic acid Chemical compound OC(=O)C1CCSNC1 IJOUCDYZGQFHNL-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-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
- 238000009834 vaporization Methods 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/881—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with a hydrogen atom or an unsubstituted hydrocarbon radical, attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/86—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with only atoms other than nitrogen atoms directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/861—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with only atoms other than nitrogen atoms directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with a hydrocarbon radical or a substituted hydrocarbon radical, directly attached in position 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37705202P | 2002-05-01 | 2002-05-01 | |
| US60/377052 | 2002-05-01 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN038097338A Division CN1649883B (zh) | 2002-05-01 | 2003-04-30 | 作为内酰胺酶抑制剂的二环6-亚烷基-表霉烯 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101570545A true CN101570545A (zh) | 2009-11-04 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN038097338A Expired - Fee Related CN1649883B (zh) | 2002-05-01 | 2003-04-30 | 作为内酰胺酶抑制剂的二环6-亚烷基-表霉烯 |
| CNA2009101331547A Pending CN101570545A (zh) | 2002-05-01 | 2003-04-30 | 作为内酰胺酶抑制剂的二环6-亚烷基-表霉烯 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN038097338A Expired - Fee Related CN1649883B (zh) | 2002-05-01 | 2003-04-30 | 作为内酰胺酶抑制剂的二环6-亚烷基-表霉烯 |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US7112582B2 (enExample) |
| EP (2) | EP1988093A1 (enExample) |
| JP (2) | JP4602759B2 (enExample) |
| KR (1) | KR20050007368A (enExample) |
| CN (2) | CN1649883B (enExample) |
| AR (1) | AR039774A1 (enExample) |
| AU (1) | AU2003231205A1 (enExample) |
| BR (1) | BR0309757A (enExample) |
| CA (1) | CA2483538A1 (enExample) |
| CR (3) | CR7508A (enExample) |
| EC (1) | ECSP045397A (enExample) |
| IL (1) | IL164899A0 (enExample) |
| MX (1) | MXPA04010663A (enExample) |
| NO (1) | NO20044549L (enExample) |
| NZ (1) | NZ536182A (enExample) |
| RU (1) | RU2339640C2 (enExample) |
| SG (1) | SG162614A1 (enExample) |
| TW (1) | TW200307687A (enExample) |
| UA (1) | UA79117C2 (enExample) |
| WO (1) | WO2003093279A1 (enExample) |
| ZA (1) | ZA200409686B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104119858A (zh) * | 2013-04-27 | 2014-10-29 | 海洋王照明科技股份有限公司 | 一种铱金属配合物有机电致磷光材料及其制备方法和有机电致发光器件 |
| CN104119857A (zh) * | 2013-04-27 | 2014-10-29 | 海洋王照明科技股份有限公司 | 一种铱金属配合物有机电致磷光材料及其制备方法和有机电致发光器件 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040132708A1 (en) * | 2002-05-01 | 2004-07-08 | Wyeth | Process for preparing 6-alkylidene penem derivatives |
| AR039475A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | 6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa |
| AR039476A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | Proceso para preparar derivados de 6-alquiliden penem |
| AR039774A1 (es) * | 2002-05-01 | 2005-03-02 | Wyeth Corp | 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas |
| EP1660506A4 (en) * | 2003-08-25 | 2009-02-25 | Revaax Pharmaceuticals Llc | ORAL NEUROTHERAPEUTIC CEFAZOLINE COMPOSITIONS |
| TW200716102A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Bicyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| TW200716104A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Tricyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| AU2006285308A1 (en) * | 2005-07-27 | 2007-03-08 | Wyeth | Tricyclic 6-alkylidene-penem beta-lactamase inhibitors and beta-lactam antibiotic combination: a broad spectrum antibiotic |
| RU2008102912A (ru) * | 2005-07-27 | 2009-09-10 | Вайет (Us) | Сочетание ингибиторов бетта-лактазмы бициклического 6-алкилиденпенема с бетта-лактанным антибиотиком: антибиотик широкого спектра |
| GT200600380A (es) * | 2005-08-24 | 2007-03-29 | Proceso para la preparacion de inhibidores de beta-lactamasa | |
| US20090018332A1 (en) * | 2007-06-28 | 2009-01-15 | Wyeth | Processes For Preparing Bicyclic Oxazine Carboxaldehyde and Beta-Lactamase Inhibitors |
| BR112018015191B1 (pt) | 2016-02-23 | 2023-10-17 | Pfizer Inc | Compostos de 6,7-di-hidro-5h-pirazolo[5,1-b][1,3]oxazina-2-carboxamida, seu uso e composição farmacêutica que os compreende |
| CN108473510B (zh) * | 2016-04-28 | 2021-10-29 | 豪夫迈·罗氏有限公司 | 制备2-吡唑并[1,5-a]吡嗪-2-基吡啶并[1,2-a]嘧啶-4-酮的方法 |
| RU2019107162A (ru) | 2016-08-15 | 2020-09-15 | Байер Кропсайенс Акциенгезельшафт | Конденсированные бициклические гетероциклические производные в качестве средств для борьбы с вредителями |
| CN114957258A (zh) * | 2021-02-25 | 2022-08-30 | 华东理工大学 | 基于碳青霉烯结构的广谱丝氨酸β-内酰胺酶抑制剂的合成及其在耐药细菌抑制中的应用 |
| BR112023023866A2 (pt) * | 2021-05-21 | 2024-02-06 | Chengdu Baiyu Pharmaceutical Co Ltd | Derivado de piperazina e seu uso na medicina |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2004A (en) * | 1841-03-12 | Improvement in the manner of constructing and propelling steam-vessels | ||
| US4206067A (en) * | 1978-10-02 | 1980-06-03 | Chevron Research Company | Thermally stabilized erosion-inhibited functional fluids containing perhalometal compounds and an organic base |
| DE3176517D1 (en) | 1980-04-24 | 1987-12-17 | Beecham Group Plc | Beta-lactam compounds, their preparation and use |
| EP0120613A1 (en) | 1983-03-02 | 1984-10-03 | Beecham Group Plc | Penem derivatives and precursors |
| GB8402086D0 (en) | 1984-01-26 | 1984-02-29 | Beecham Group Plc | Compounds |
| FI82471C (fi) | 1984-01-26 | 1991-03-11 | Beecham Group Plc | Foerfarande foer framstaellning av farmakologiskt aktiva 6-metylenpenemderivater. |
| EP0150984B1 (en) | 1984-01-30 | 1991-09-11 | Pfizer Inc. | 6-(substituted) methylenepenicillanic and 6-(substituted) hydroxymethylpenicillanic acids and derivatives thereof |
| EP0167050A1 (en) * | 1984-06-21 | 1986-01-08 | Beecham Group Plc | Clavulanate compounds, their preparation and use and intermediates thereof |
| GB8518416D0 (en) * | 1985-07-22 | 1985-08-29 | Beecham Group Plc | Compounds |
| GB8518422D0 (en) | 1985-07-22 | 1985-08-29 | Beecham Group Plc | Compounds |
| GB8518421D0 (en) | 1985-07-22 | 1985-08-29 | Beecham Group Plc | Compounds |
| ATE159021T1 (de) | 1986-01-17 | 1997-10-15 | Beecham Group Plc | Verfahren zur herstellung von penem derivaten und zwischenprodukte zu dieser herstellung |
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| DE3725375A1 (de) * | 1987-07-31 | 1989-02-09 | Bayer Ag | Stabile oxapenem-3-carbonsaeuren |
| GB8724566D0 (en) | 1987-10-20 | 1987-11-25 | Roussel Lab Ltd | Chemical compounds |
| GB8729614D0 (en) | 1987-12-18 | 1988-02-03 | Beecham Group Plc | Novel compounds |
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| NZ237202A (en) | 1990-02-23 | 1994-01-26 | Bristol Myers Squibb Co | Composition containing beta-lactam antibiotic and cationic oligopeptide |
| EP0447704A1 (en) | 1990-03-21 | 1991-09-25 | Smithkline Beecham Farmaceutici S.p.A. | N-Acylated azacyclic compounds, processes for their preparations and their use as medications |
| GB9116236D0 (en) | 1991-07-27 | 1991-09-11 | Smithkline Beecham Plc | Novel compounds |
| GB9222700D0 (en) * | 1992-10-29 | 1992-12-09 | Smithkline Beecham Plc | Chemical compounds |
| US5349045A (en) | 1993-01-26 | 1994-09-20 | United States Surgical Corporation | Polymer derived from cyclic amide and medical devices manufactured therefrom |
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| ES2206502T3 (es) | 1994-04-25 | 2004-05-16 | Smithkline Beecham Plc | Formulaciones farmaceuticas que contienen un penem inhibidor de beta-lactamasa en combinacion con un antibiotico de beta-lactama y su uso en el tratamiento de infecciones bacterianas. |
| US5629322A (en) | 1994-11-15 | 1997-05-13 | Merck & Co., Inc. | Cyclic amidine analogs as inhibitors of nitric oxide synthase |
| OA11666A (en) * | 1998-10-15 | 2004-12-08 | Sarawak Medichem Pharmaceuticals Inc | Method and composition for treating and preventingtuberculosis. |
| GB9928290D0 (en) * | 1999-12-01 | 2000-01-26 | Univ Belfast | Process for preparing ambient temperature ionic liquids |
| EP1199077A1 (en) * | 2000-10-19 | 2002-04-24 | Amura Limited | Stable compositions of oxapenem-3-carboxylic acids by Co-lyophilisation with pharmaceutical carriers |
| GB0106428D0 (en) * | 2001-03-15 | 2001-05-02 | Amura Ltd | Antibacterial composition |
| US20040132708A1 (en) * | 2002-05-01 | 2004-07-08 | Wyeth | Process for preparing 6-alkylidene penem derivatives |
| AR039774A1 (es) * | 2002-05-01 | 2005-03-02 | Wyeth Corp | 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas |
| AR039476A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | Proceso para preparar derivados de 6-alquiliden penem |
| AR039475A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | 6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa |
| AR046041A1 (es) * | 2003-10-03 | 2005-11-23 | Aventis Pharma Inc | Procedimiento para la preparacion de compuestos heterociclicos n-amino sustituidos |
| TW200716104A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Tricyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| TW200716102A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Bicyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| RU2008102912A (ru) * | 2005-07-27 | 2009-09-10 | Вайет (Us) | Сочетание ингибиторов бетта-лактазмы бициклического 6-алкилиденпенема с бетта-лактанным антибиотиком: антибиотик широкого спектра |
-
2003
- 2003-04-28 AR ARP030101471A patent/AR039774A1/es unknown
- 2003-04-29 TW TW092110033A patent/TW200307687A/zh unknown
- 2003-04-30 AU AU2003231205A patent/AU2003231205A1/en not_active Abandoned
- 2003-04-30 UA UA20041109833A patent/UA79117C2/uk unknown
- 2003-04-30 BR BR0309757-9A patent/BR0309757A/pt not_active IP Right Cessation
- 2003-04-30 CA CA002483538A patent/CA2483538A1/en not_active Abandoned
- 2003-04-30 RU RU2004135082/04A patent/RU2339640C2/ru not_active IP Right Cessation
- 2003-04-30 SG SG200607462-9A patent/SG162614A1/en unknown
- 2003-04-30 EP EP08004917A patent/EP1988093A1/en not_active Withdrawn
- 2003-04-30 CN CN038097338A patent/CN1649883B/zh not_active Expired - Fee Related
- 2003-04-30 NZ NZ536182A patent/NZ536182A/en not_active IP Right Cessation
- 2003-04-30 WO PCT/US2003/013428 patent/WO2003093279A1/en not_active Ceased
- 2003-04-30 KR KR10-2004-7017597A patent/KR20050007368A/ko not_active Ceased
- 2003-04-30 CN CNA2009101331547A patent/CN101570545A/zh active Pending
- 2003-04-30 MX MXPA04010663A patent/MXPA04010663A/es active IP Right Grant
- 2003-04-30 JP JP2004501418A patent/JP4602759B2/ja not_active Expired - Fee Related
- 2003-04-30 EP EP03724340A patent/EP1499621A1/en not_active Ceased
- 2003-05-01 US US10/427,380 patent/US7112582B2/en not_active Expired - Fee Related
-
2004
- 2004-10-06 CR CR7508A patent/CR7508A/es not_active Application Discontinuation
- 2004-10-22 NO NO20044549A patent/NO20044549L/no not_active Application Discontinuation
- 2004-10-28 IL IL16489904A patent/IL164899A0/xx unknown
- 2004-10-29 EC EC2004005397A patent/ECSP045397A/es unknown
- 2004-11-30 ZA ZA200409686A patent/ZA200409686B/xx unknown
-
2006
- 2006-06-06 US US11/447,814 patent/US20060217361A1/en not_active Abandoned
-
2008
- 2008-08-21 US US12/195,706 patent/US7812014B2/en not_active Expired - Fee Related
-
2009
- 2009-08-21 CR CR10986A patent/CR10986A/es not_active Application Discontinuation
- 2009-08-21 CR CR10983A patent/CR10983A/es not_active Application Discontinuation
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2010
- 2010-06-02 JP JP2010127126A patent/JP2010215652A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104119858A (zh) * | 2013-04-27 | 2014-10-29 | 海洋王照明科技股份有限公司 | 一种铱金属配合物有机电致磷光材料及其制备方法和有机电致发光器件 |
| CN104119857A (zh) * | 2013-04-27 | 2014-10-29 | 海洋王照明科技股份有限公司 | 一种铱金属配合物有机电致磷光材料及其制备方法和有机电致发光器件 |
Also Published As
| Publication number | Publication date |
|---|---|
| SG162614A1 (en) | 2010-07-29 |
| EP1499621A1 (en) | 2005-01-26 |
| CR10986A (es) | 2009-09-09 |
| US7112582B2 (en) | 2006-09-26 |
| NZ536182A (en) | 2006-10-27 |
| EP1988093A1 (en) | 2008-11-05 |
| JP4602759B2 (ja) | 2010-12-22 |
| AR039774A1 (es) | 2005-03-02 |
| US20060217361A1 (en) | 2006-09-28 |
| RU2004135082A (ru) | 2006-01-20 |
| KR20050007368A (ko) | 2005-01-17 |
| TW200307687A (en) | 2003-12-16 |
| NO20044549L (no) | 2005-01-25 |
| UA79117C2 (en) | 2007-05-25 |
| CR7508A (es) | 2005-01-05 |
| JP2010215652A (ja) | 2010-09-30 |
| RU2339640C2 (ru) | 2008-11-27 |
| CR10983A (es) | 2009-09-09 |
| US20040077622A1 (en) | 2004-04-22 |
| WO2003093279A1 (en) | 2003-11-13 |
| US7812014B2 (en) | 2010-10-12 |
| CN1649883A (zh) | 2005-08-03 |
| CA2483538A1 (en) | 2003-11-13 |
| AU2003231205A1 (en) | 2003-11-17 |
| JP2005533017A (ja) | 2005-11-04 |
| US20080312203A1 (en) | 2008-12-18 |
| BR0309757A (pt) | 2005-03-08 |
| ECSP045397A (es) | 2005-01-03 |
| ZA200409686B (en) | 2007-09-26 |
| CN1649883B (zh) | 2010-05-26 |
| MXPA04010663A (es) | 2005-04-20 |
| IL164899A0 (en) | 2005-12-18 |
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