NO301371B1 - Et pyrrolidyltiokarbapenemderivat - Google Patents
Et pyrrolidyltiokarbapenemderivat Download PDFInfo
- Publication number
- NO301371B1 NO301371B1 NO923256A NO923256A NO301371B1 NO 301371 B1 NO301371 B1 NO 301371B1 NO 923256 A NO923256 A NO 923256A NO 923256 A NO923256 A NO 923256A NO 301371 B1 NO301371 B1 NO 301371B1
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- Norway
- Prior art keywords
- mixture
- group
- mmol
- hydrogen
- solution
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- XLJMOHKQRRPBDS-IENPIDJESA-N (5S)-4-pyrrolidin-1-ylsulfanyl-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical class N1(CCCC1)SC1C=CN2[C@H]1CC2=O XLJMOHKQRRPBDS-IENPIDJESA-N 0.000 title claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- 125000006239 protecting group Chemical group 0.000 claims abstract description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 19
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 9
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 7
- -1 t-butyloxycarbonyl Chemical group 0.000 claims description 166
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims description 26
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 13
- 241000894006 Bacteria Species 0.000 claims description 11
- 239000003242 anti bacterial agent Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 abstract description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 5
- 239000011593 sulfur Substances 0.000 abstract description 5
- 125000004429 atom Chemical group 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 239000001301 oxygen Substances 0.000 abstract description 4
- 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 273
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 216
- 239000000203 mixture Substances 0.000 description 174
- 239000000243 solution Substances 0.000 description 139
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 136
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 114
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 112
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 112
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 109
- 238000002360 preparation method Methods 0.000 description 104
- 239000011541 reaction mixture Substances 0.000 description 101
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 69
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 56
- 235000019341 magnesium sulphate Nutrition 0.000 description 56
- 238000001816 cooling Methods 0.000 description 55
- 150000001875 compounds Chemical class 0.000 description 50
- 238000010898 silica gel chromatography Methods 0.000 description 49
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 38
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
- 239000012044 organic layer Substances 0.000 description 30
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
- 239000012267 brine Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 25
- 239000005457 ice water Substances 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 20
- 239000013078 crystal Substances 0.000 description 20
- 239000010410 layer Substances 0.000 description 20
- 239000012299 nitrogen atmosphere Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 18
- 238000010511 deprotection reaction Methods 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 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 16
- BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical class OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 229960002260 meropenem Drugs 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 description 12
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 12
- 230000000717 retained effect Effects 0.000 description 12
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 11
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 11
- 229960002182 imipenem Drugs 0.000 description 11
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 10
- WPCQASPMIALUEE-UHFFFAOYSA-N tert-butyl n-sulfamoylcarbamate Chemical compound CC(C)(C)OC(=O)NS(N)(=O)=O WPCQASPMIALUEE-UHFFFAOYSA-N 0.000 description 10
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 9
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- 229920006026 co-polymeric resin Polymers 0.000 description 9
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 9
- 239000001632 sodium acetate Substances 0.000 description 9
- 235000017281 sodium acetate Nutrition 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- 210000002700 urine Anatomy 0.000 description 9
- JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 8
- PMMYEEVYMWASQN-UHFFFAOYSA-N 4-hydroxyproline Chemical compound OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 7
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000005051 trimethylchlorosilane Substances 0.000 description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 6
- 230000000845 anti-microbial effect Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 241000192125 Firmicutes Species 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- JZDPDTVMCHRLNV-SMCANUKXSA-N (4-methoxyphenyl)methyl (2s,4s)-2-(aminomethyl)-4-tritylsulfanylpyrrolidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)N1[C@H](CN)C[C@H](SC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 JZDPDTVMCHRLNV-SMCANUKXSA-N 0.000 description 4
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 239000003708 ampul Substances 0.000 description 4
- 230000036765 blood level Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229910001961 silver nitrate Inorganic materials 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 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 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- BENKAPCDIOILGV-RQJHMYQMSA-N (2s,4r)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(O)=O BENKAPCDIOILGV-RQJHMYQMSA-N 0.000 description 3
- ZZJIPKOIYIJJMP-ZWKOTPCHSA-N (4-methoxyphenyl)methyl (2S,4R)-4-hydroxy-2-[(4-methylphenyl)sulfonyloxymethyl]pyrrolidine-1-carboxylate Chemical compound C1(=CC=C(C=C1)S(=O)(=O)OC[C@H]1N(C[C@@H](C1)O)C(=O)OCC1=CC=C(C=C1)OC)C ZZJIPKOIYIJJMP-ZWKOTPCHSA-N 0.000 description 3
- HOOXHKLDUCPVQW-SMCANUKXSA-N (4-methoxyphenyl)methyl (2s,4s)-2-(hydroxymethyl)-4-tritylsulfanylpyrrolidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)N1[C@H](CO)C[C@H](SC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 HOOXHKLDUCPVQW-SMCANUKXSA-N 0.000 description 3
- ADUZAUSNGVEOSG-CDZUIXILSA-N (4-methoxyphenyl)methyl (2s,4s)-2-(methylsulfonyloxymethyl)-4-tritylsulfanylpyrrolidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)N1[C@H](COS(C)(=O)=O)C[C@H](SC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 ADUZAUSNGVEOSG-CDZUIXILSA-N 0.000 description 3
- PZMYDYXHARHYBE-VQIIKMDRSA-N (4-methoxyphenyl)methyl (2s,4s)-2-[[(4-methoxyphenyl)methoxycarbonylsulfamoylamino]methyl]-4-tritylsulfanylpyrrolidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)NS(=O)(=O)NC[C@H]1N(C(=O)OCC=2C=CC(OC)=CC=2)C[C@@H](SC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 PZMYDYXHARHYBE-VQIIKMDRSA-N 0.000 description 3
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 3
- MZMNEDXVUJLQAF-HTQZYQBOSA-N 1-o-tert-butyl 2-o-methyl (2r,4r)-4-hydroxypyrrolidine-1,2-dicarboxylate Chemical compound COC(=O)[C@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C MZMNEDXVUJLQAF-HTQZYQBOSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- JQXFEQZHDMPMJE-GHMZBOCLSA-N tert-butyl (2r,4r)-2-[[(2-methylpropan-2-yl)oxycarbonyl-sulfamoylamino]methyl]-4-sulfanylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N(S(N)(=O)=O)C[C@H]1C[C@@H](S)CN1C(=O)OC(C)(C)C JQXFEQZHDMPMJE-GHMZBOCLSA-N 0.000 description 1
- JQXFEQZHDMPMJE-MNOVXSKESA-N tert-butyl (2r,4s)-2-[[(2-methylpropan-2-yl)oxycarbonyl-sulfamoylamino]methyl]-4-sulfanylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N(S(N)(=O)=O)C[C@H]1C[C@H](S)CN1C(=O)OC(C)(C)C JQXFEQZHDMPMJE-MNOVXSKESA-N 0.000 description 1
- CZIBLNJSWPMUGC-ZJUUUORDSA-N tert-butyl (2r,4s)-4-acetylsulfanyl-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(=O)S[C@H]1C[C@H](CO)N(C(=O)OC(C)(C)C)C1 CZIBLNJSWPMUGC-ZJUUUORDSA-N 0.000 description 1
- KNRUKLCMHGCYRP-OLZOCXBDSA-N tert-butyl (2r,4s)-4-acetylsulfanyl-2-[[(2-methylpropan-2-yl)oxycarbonyl-sulfamoylamino]methyl]pyrrolidine-1-carboxylate Chemical compound CC(=O)S[C@H]1C[C@H](CN(C(=O)OC(C)(C)C)S(N)(=O)=O)N(C(=O)OC(C)(C)C)C1 KNRUKLCMHGCYRP-OLZOCXBDSA-N 0.000 description 1
- GBUOWVDRNWNHOE-IUCAKERBSA-N tert-butyl (2s,4s)-2-(hydroxymethyl)-4-methylsulfonyloxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@@H](OS(C)(=O)=O)C[C@H]1CO GBUOWVDRNWNHOE-IUCAKERBSA-N 0.000 description 1
- BOJKNONDFMODRQ-YUMQZZPRSA-N tert-butyl (2s,4s)-2-[(sulfamoylamino)methyl]-4-sulfanylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@@H](S)C[C@H]1CNS(N)(=O)=O BOJKNONDFMODRQ-YUMQZZPRSA-N 0.000 description 1
- HYHGOLISXHJSAX-UHFFFAOYSA-N tert-butyl 2-(aminomethyl)-2-sulfamoyl-4-sulfanylpyrrolidine-1-carboxylate Chemical compound S(N)(=O)(=O)C1(N(CC(C1)S)C(=O)OC(C)(C)C)CN HYHGOLISXHJSAX-UHFFFAOYSA-N 0.000 description 1
- JQXFEQZHDMPMJE-UHFFFAOYSA-N tert-butyl 2-[[(2-methylpropan-2-yl)oxycarbonyl-sulfamoylamino]methyl]-4-sulfanylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N(S(N)(=O)=O)CC1CC(S)CN1C(=O)OC(C)(C)C JQXFEQZHDMPMJE-UHFFFAOYSA-N 0.000 description 1
- KAJZZLBZXOBEMD-UHFFFAOYSA-N tert-butyl n-chlorosulfonylcarbamate Chemical compound CC(C)(C)OC(=O)NS(Cl)(=O)=O KAJZZLBZXOBEMD-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- WORJEOGGNQDSOE-ASTXPPQBSA-N trichloro(deuterio)methane;trideuterio(deuteriooxy)methane Chemical compound [2H]C(Cl)(Cl)Cl.[2H]OC([2H])([2H])[2H] WORJEOGGNQDSOE-ASTXPPQBSA-N 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/04—Diamides of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/02—Preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/14—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms 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 3
- C07D477/20—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20797291 | 1991-08-20 | ||
JP3536692 | 1992-02-21 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO923256D0 NO923256D0 (no) | 1992-08-19 |
NO923256L NO923256L (no) | 1993-02-22 |
NO301371B1 true NO301371B1 (no) | 1997-10-20 |
Family
ID=26374345
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO923256A NO301371B1 (no) | 1991-08-20 | 1992-08-19 | Et pyrrolidyltiokarbapenemderivat |
Country Status (18)
Country | Link |
---|---|
US (2) | US5317016A (zh) |
EP (1) | EP0528678B1 (zh) |
JP (1) | JP2542773B2 (zh) |
KR (1) | KR100245671B1 (zh) |
CN (2) | CN1032257C (zh) |
AT (1) | ATE201413T1 (zh) |
AU (1) | AU652273B2 (zh) |
CA (2) | CA2076430C (zh) |
DE (2) | DE122009000002I1 (zh) |
DK (1) | DK0528678T3 (zh) |
ES (1) | ES2159277T3 (zh) |
GR (1) | GR3036434T3 (zh) |
LU (1) | LU91519I2 (zh) |
MX (1) | MX9204805A (zh) |
NL (1) | NL300374I2 (zh) |
NO (1) | NO301371B1 (zh) |
PT (1) | PT528678E (zh) |
TW (1) | TW325475B (zh) |
Families Citing this family (44)
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PT611115E (pt) * | 1993-02-10 | 2001-07-31 | Shionogi & Co | Preparacao de compostos beta-lactamicos e seus intermediarios |
US5563264A (en) * | 1993-02-10 | 1996-10-08 | Shionogi & Co., Ltd. | Preparation of βlactam compounds |
WO1995029913A1 (fr) * | 1994-05-02 | 1995-11-09 | Shionogi & Co., Ltd. | Cristal de derive de pyrrolidylthiocarbapeneme, preparation lyophilisee le contenant et son procede de production |
TW445265B (en) | 1996-11-25 | 2001-07-11 | Meiji Seika Kaisha | Carbapenem derivatives and antimicrobial agents |
TW577875B (en) * | 1997-01-31 | 2004-03-01 | Shionogi & Co | Pyrrolidine derivatives with inhibitory activity for phospholipase A2 |
US6750344B1 (en) * | 1997-09-05 | 2004-06-15 | Isis Pharmaceuticals, Inc. | Amine compounds and combinatorial libraries comprising same |
EP1270575B1 (en) * | 2000-03-31 | 2005-09-07 | Shionogi & Co., Ltd. | Novel crystal form of pyrrolidylthiocarbapenem derivative |
CA2415681C (en) | 2000-07-19 | 2008-05-20 | F. Hoffmann-La Roche Ag | Pyrrolidine derivatives |
JP3983663B2 (ja) * | 2000-07-19 | 2007-09-26 | エフ.ホフマン−ラ ロシュ アーゲー | メタロプロテアーゼインヒビターとしてのピロリジン誘導体 |
JP5328170B2 (ja) * | 2001-05-10 | 2013-10-30 | 塩野義製薬株式会社 | アセチルチオピロリジン誘導体の製法 |
JP5004355B2 (ja) * | 2001-05-10 | 2012-08-22 | 塩野義製薬株式会社 | アセチルチオピロリジン誘導体の製法 |
KR100473398B1 (ko) * | 2002-08-31 | 2005-03-10 | 주식회사 하원제약 | 옥심기를 포함하는 피롤리딘 치환체를 가지는1-베타메틸카바페넴 유도체 및 그 제조방법 |
JP4404316B2 (ja) * | 2003-02-14 | 2010-01-27 | 塩野義製薬株式会社 | カルバペネム合成中間体の結晶 |
US20050065141A1 (en) * | 2003-07-31 | 2005-03-24 | Odink Debra A. | Carbapenems useful in treating and preventing pulmonary infections, pharmaceutical compositions thereof and modes of administration thereof |
EP1797879A4 (en) * | 2004-10-08 | 2009-05-06 | Dainippon Sumitomo Pharma Co | NEW ANTIMICROBIAL MEDICAMENT |
JP2008044847A (ja) * | 2004-11-01 | 2008-02-28 | Shionogi & Co Ltd | カルバペネム合成体およびその製造法 |
US7932381B2 (en) * | 2005-02-15 | 2011-04-26 | Shionogi & Co., Ltd. | Process for producing carbapenem derivative and intermediate crystal therefor |
TWI393721B (zh) * | 2005-02-15 | 2013-04-21 | Shionogi & Co | 碳配念衍生物之製法及其中間體結晶 |
WO2006117763A2 (en) * | 2005-05-03 | 2006-11-09 | Ranbaxy Laboratories Limited | A process for the preparation of doripenem |
TWI353855B (en) | 2005-05-26 | 2011-12-11 | Shionogi & Co | Method for preparing an aqueous solution of doripe |
WO2007004028A2 (en) * | 2005-06-30 | 2007-01-11 | Ranbaxy Laboratories Limited | Processes for the preparation of penems and its intermediate |
CN100460389C (zh) * | 2005-07-15 | 2009-02-11 | 成都地奥九泓制药厂 | 吡咯烷衍生物中间体及其制备方法和用途 |
JP2008303143A (ja) * | 2005-08-19 | 2008-12-18 | Shionogi & Co Ltd | 連続化反応によるカルバぺネム誘導体の製法 |
WO2007029084A2 (en) | 2005-09-05 | 2007-03-15 | Ranbaxy Laboratories Limited | A process for the preparation of carbapenem compounds |
CN100582106C (zh) * | 2006-01-27 | 2010-01-20 | 上海医药工业研究院 | 一种吡咯烷硫基碳青霉烯衍生物的制备方法及其中间体 |
CN101479279B (zh) * | 2006-06-28 | 2011-08-17 | 辉瑞产品公司 | 培南前药 |
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US10695322B2 (en) | 2016-01-29 | 2020-06-30 | The Johns Hopkins University | Inhibitors of bacterial growth |
US11180504B2 (en) | 2016-03-16 | 2021-11-23 | Orchid Pharma Ltd. | Substituted carbapenems for the treatment of bacterial infections |
JP7446424B2 (ja) * | 2019-11-22 | 2024-03-08 | スージョウ アーイェ ファーマシューティカル カンパニー リミテッド | スルホニル尿素環置換単環式β-ラクタム系抗生物質 |
CN111960984B (zh) * | 2020-09-11 | 2023-04-28 | 江西如益科技发展有限公司 | 一种合成多尼培南侧链中间体的制备方法 |
Family Cites Families (11)
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US4260543A (en) * | 1978-07-03 | 1981-04-07 | Merck & Co., Inc. | Crystalline N-formimidoyl thienamycin |
DK153486C (da) * | 1978-07-03 | 1988-11-28 | Merck & Co Inc | Analogifremgangsmaade til fremstilling af krystallinsk n-formimidoyl-thienamycin-monohydrat |
JPS60233076A (ja) * | 1984-05-03 | 1985-11-19 | Sumitomo Chem Co Ltd | 新規なβ−ラクタム化合物およびその製造法 |
JPS62155279A (ja) * | 1984-11-08 | 1987-07-10 | Sumitomo Pharmaceut Co Ltd | 新規なβ−ラクタム化合物 |
CA1281720C (en) * | 1984-11-08 | 1991-03-19 | Makoto Sunagawa | Carbapenem compounds and production thereof |
KR880006244A (ko) * | 1986-11-24 | 1988-07-22 | 후지사와 도모 기찌 로 | 3-피롤리디닐티오-1-아자바이스클로[3.2.0]햅트2-엔-2-카르복실산 화합물 및 이의 제조방법 |
HU209817B (en) * | 1989-03-28 | 1994-11-28 | Pfizer | Process for the production of antibacterial 2-carbapenem derivatives |
US5157125A (en) * | 1989-09-25 | 1992-10-20 | Pfizer Inc. | Optically active 2-alkyl-2,5-diazabicyclo[2.2.1]heptanes |
FI96311C (fi) * | 1989-12-04 | 1996-06-10 | Squibb Bristol Myers Co | Menetelmä farmaseuttisesti käyttökelpoisten 6-(1-hydroksietyyli)-3-(substituoitu tio)-7-okso-1-atsabisyklo/3.2.0/hept-2-eeni-2-karboksyylihappojohdannaisten valmistamiseksi |
IL99513A0 (en) * | 1990-09-20 | 1992-08-18 | Hoechst Ag | Process for the preparation of carbapenem compounds |
TW209220B (zh) * | 1991-11-27 | 1993-07-11 | Manyu Seiyaku Kk |
-
1992
- 1992-08-14 US US07/929,961 patent/US5317016A/en not_active Expired - Lifetime
- 1992-08-18 DE DE122009000002C patent/DE122009000002I1/de active Pending
- 1992-08-18 PT PT92307547T patent/PT528678E/pt unknown
- 1992-08-18 ES ES92307547T patent/ES2159277T3/es not_active Expired - Lifetime
- 1992-08-18 DK DK92307547T patent/DK0528678T3/da active
- 1992-08-18 AT AT92307547T patent/ATE201413T1/de active
- 1992-08-18 EP EP92307547A patent/EP0528678B1/en not_active Expired - Lifetime
- 1992-08-18 DE DE69231834T patent/DE69231834T2/de not_active Expired - Lifetime
- 1992-08-18 AU AU21090/92A patent/AU652273B2/en not_active Ceased
- 1992-08-19 CA CA002076430A patent/CA2076430C/en not_active Expired - Lifetime
- 1992-08-19 CA CA002203942A patent/CA2203942C/en not_active Expired - Lifetime
- 1992-08-19 NO NO923256A patent/NO301371B1/no not_active IP Right Cessation
- 1992-08-19 TW TW081106573A patent/TW325475B/zh not_active IP Right Cessation
- 1992-08-20 MX MX9204805A patent/MX9204805A/es unknown
- 1992-08-20 JP JP4221767A patent/JP2542773B2/ja not_active Expired - Lifetime
- 1992-08-20 KR KR1019920014970A patent/KR100245671B1/ko not_active IP Right Cessation
- 1992-08-20 CN CN92111069A patent/CN1032257C/zh not_active Expired - Lifetime
-
1995
- 1995-04-21 CN CN95104834A patent/CN1034571C/zh not_active Expired - Lifetime
- 1995-12-19 US US08/574,863 patent/US5703243A/en not_active Expired - Lifetime
-
2001
- 2001-08-22 GR GR20010401285T patent/GR3036434T3/el unknown
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2009
- 2009-01-23 LU LU91519C patent/LU91519I2/fr unknown
- 2009-01-23 NL NL300374C patent/NL300374I2/nl unknown
Also Published As
Publication number | Publication date |
---|---|
TW325475B (en) | 1998-01-21 |
CN1034571C (zh) | 1997-04-16 |
DE69231834T2 (de) | 2002-03-28 |
ATE201413T1 (de) | 2001-06-15 |
MX9204805A (es) | 1993-05-01 |
KR930004306A (ko) | 1993-03-22 |
NO923256D0 (no) | 1992-08-19 |
DE69231834D1 (de) | 2001-06-28 |
NL300374I1 (nl) | 2009-04-01 |
EP0528678B1 (en) | 2001-05-23 |
EP0528678A1 (en) | 1993-02-24 |
CN1071428A (zh) | 1993-04-28 |
DE122009000002I1 (de) | 2009-05-20 |
DK0528678T3 (da) | 2001-07-30 |
JP2542773B2 (ja) | 1996-10-09 |
AU652273B2 (en) | 1994-08-18 |
US5703243A (en) | 1997-12-30 |
KR100245671B1 (ko) | 2000-05-01 |
AU2109092A (en) | 1993-02-25 |
LU91519I2 (fr) | 2009-03-23 |
JPH05294970A (ja) | 1993-11-09 |
CA2076430C (en) | 1997-12-23 |
ES2159277T3 (es) | 2001-10-01 |
CA2203942C (en) | 2001-02-13 |
GR3036434T3 (en) | 2001-11-30 |
NL300374I2 (nl) | 2009-06-02 |
NO923256L (no) | 1993-02-22 |
PT528678E (pt) | 2001-08-30 |
CA2203942A1 (en) | 1993-02-21 |
CN1032257C (zh) | 1996-07-10 |
CA2076430A1 (en) | 1993-02-21 |
US5317016A (en) | 1994-05-31 |
CN1113233A (zh) | 1995-12-13 |
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