FI80271C - Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 1-sulfo-2-azetidinoniderivat, och nya som mellanprodukt anvaendbara 2-azetidinonderivat. - Google Patents
Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 1-sulfo-2-azetidinoniderivat, och nya som mellanprodukt anvaendbara 2-azetidinonderivat. Download PDFInfo
- Publication number
- FI80271C FI80271C FI810352A FI810352A FI80271C FI 80271 C FI80271 C FI 80271C FI 810352 A FI810352 A FI 810352A FI 810352 A FI810352 A FI 810352A FI 80271 C FI80271 C FI 80271C
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- FI
- Finland
- Prior art keywords
- amino
- oxo
- acid
- solution
- added
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- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 cyano, nitro, amino, mercapto Chemical class 0.000 claims description 184
- 150000001875 compounds Chemical class 0.000 claims description 176
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 72
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- CDFGMYLBUSYTKQ-UHFFFAOYSA-N 2-oxoazetidine-1-sulfonic acid Chemical class OS(=O)(=O)N1CCC1=O CDFGMYLBUSYTKQ-UHFFFAOYSA-N 0.000 claims description 9
- 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 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 195
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 182
- 239000000243 solution Substances 0.000 description 174
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 165
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 149
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 129
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 101
- 239000000203 mixture Substances 0.000 description 91
- 239000002253 acid Substances 0.000 description 77
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 67
- 239000007787 solid Substances 0.000 description 66
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
- 238000003756 stirring Methods 0.000 description 58
- 239000002904 solvent Substances 0.000 description 45
- 229910052757 nitrogen Inorganic materials 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 40
- 239000000047 product Substances 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 35
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- 239000000706 filtrate Substances 0.000 description 31
- 239000002002 slurry Substances 0.000 description 31
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 30
- 238000007792 addition Methods 0.000 description 29
- 239000003921 oil Substances 0.000 description 29
- 241000588724 Escherichia coli Species 0.000 description 28
- 241000191967 Staphylococcus aureus Species 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 27
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 26
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 26
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 22
- 125000001841 imino group Chemical group [H]N=* 0.000 description 21
- LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 20
- 239000000284 extract Substances 0.000 description 19
- 239000010410 layer Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 17
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 17
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 17
- 239000012043 crude product Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 238000001914 filtration Methods 0.000 description 15
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 15
- 235000019796 monopotassium phosphate Nutrition 0.000 description 15
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 15
- 150000003952 β-lactams Chemical class 0.000 description 15
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 229910052786 argon Inorganic materials 0.000 description 13
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 13
- 239000003208 petroleum Substances 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 12
- 239000012298 atmosphere Substances 0.000 description 12
- 239000004202 carbamide Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- 238000001665 trituration Methods 0.000 description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- 238000010790 dilution Methods 0.000 description 11
- 239000012895 dilution Substances 0.000 description 11
- 235000019253 formic acid Nutrition 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 description 9
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 9
- 238000010828 elution Methods 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 8
- 229920001817 Agar Polymers 0.000 description 8
- 239000008272 agar Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000006277 sulfonation reaction Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 241000588919 Citrobacter freundii Species 0.000 description 7
- 241000588697 Enterobacter cloacae Species 0.000 description 7
- 241000194032 Enterococcus faecalis Species 0.000 description 7
- 241000588748 Klebsiella Species 0.000 description 7
- 241000588915 Klebsiella aerogenes Species 0.000 description 7
- 241000588747 Klebsiella pneumoniae Species 0.000 description 7
- 241000191938 Micrococcus luteus Species 0.000 description 7
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 7
- 241000588770 Proteus mirabilis Species 0.000 description 7
- 241000588767 Proteus vulgaris Species 0.000 description 7
- 241000588777 Providencia rettgeri Species 0.000 description 7
- 241000607142 Salmonella Species 0.000 description 7
- 241000607715 Serratia marcescens Species 0.000 description 7
- 241000607768 Shigella Species 0.000 description 7
- 241000193985 Streptococcus agalactiae Species 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 229940092559 enterobacter aerogenes Drugs 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 7
- 239000012452 mother liquor Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 229940007042 proteus vulgaris Drugs 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- GDMSQJFJWOAAIG-WNQIDUERSA-M (3S)-3-amino-2-oxoazetidine-1-sulfonate tetrabutylazanium Chemical compound N[C@H]1CN(C1=O)S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC GDMSQJFJWOAAIG-WNQIDUERSA-M 0.000 description 6
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 238000004108 freeze drying Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 150000003222 pyridines Chemical class 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- GCBWDZYSLVSRRI-UHFFFAOYSA-N 3-aminoazetidin-2-one Chemical class NC1CNC1=O GCBWDZYSLVSRRI-UHFFFAOYSA-N 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- KHUNFTAJVUPPCY-UHFFFAOYSA-N azetidine-1-sulfonic acid Chemical compound OS(=O)(=O)N1CCC1 KHUNFTAJVUPPCY-UHFFFAOYSA-N 0.000 description 5
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000008057 potassium phosphate buffer Substances 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 229930182555 Penicillin Natural products 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000000538 analytical sample Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 150000003951 lactams Chemical class 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 150000002960 penicillins Chemical class 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229940080818 propionamide Drugs 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- ISUIVWNWEDIHJD-GBXIJSLDSA-N (2r,3s)-3-azaniumyl-2-methyl-4-oxoazetidine-1-sulfonate Chemical compound C[C@@H]1[C@H](N)C(=O)N1S(O)(=O)=O ISUIVWNWEDIHJD-GBXIJSLDSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- BGPSVDWRELSFFK-UHFFFAOYSA-N 3-amino-2,2-dimethyl-4-oxoazetidine-1-sulfonic acid Chemical compound CC1(C)C(N)C(=O)N1S(O)(=O)=O BGPSVDWRELSFFK-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 208000022362 bacterial infectious disease Diseases 0.000 description 3
- PYZXYZOBPGPOFQ-SCZZXKLOSA-N benzyl n-[(2s,3r)-1-amino-3-hydroxy-1-oxobutan-2-yl]carbamate Chemical compound C[C@@H](O)[C@@H](C(N)=O)NC(=O)OCC1=CC=CC=C1 PYZXYZOBPGPOFQ-SCZZXKLOSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
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- 239000002808 molecular sieve Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 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
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- CAFBQUHTUHLBPZ-UHFFFAOYSA-M potassium 2-oxoazetidine-1-sulfonate Chemical compound [K+].O=C1N(CC1)S(=O)(=O)[O-] CAFBQUHTUHLBPZ-UHFFFAOYSA-M 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VSTSKETWEBYEHL-RITPCOANSA-N tert-butyl n-[(2r,3s)-2-methyl-4-oxoazetidin-3-yl]carbamate Chemical compound C[C@H]1NC(=O)[C@H]1NC(=O)OC(C)(C)C VSTSKETWEBYEHL-RITPCOANSA-N 0.000 description 1
- IYGVAKZKRMUMSN-RYUDHWBXSA-N tert-butyl n-[(2s,3s)-2-cyclohexyl-1-methoxy-4-oxoazetidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1C(=O)N(OC)[C@H]1C1CCCCC1 IYGVAKZKRMUMSN-RYUDHWBXSA-N 0.000 description 1
- XITYBUGKVAXFSS-AAEUAGOBSA-N tert-butyl n-[(2s,3s)-2-methyl-4-oxo-1-phenylmethoxyazetidin-3-yl]carbamate Chemical compound C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N1OCC1=CC=CC=C1 XITYBUGKVAXFSS-AAEUAGOBSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-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
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
- 150000003953 γ-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11927680A | 1980-02-07 | 1980-02-07 | |
| US11927680 | 1980-02-07 | ||
| US18889380A | 1980-09-29 | 1980-09-29 | |
| US18889380 | 1980-09-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI810352L FI810352L (fi) | 1981-08-08 |
| FI80271B FI80271B (fi) | 1990-01-31 |
| FI80271C true FI80271C (fi) | 1990-05-10 |
Family
ID=26817179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI810352A FI80271C (fi) | 1980-02-07 | 1981-02-06 | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 1-sulfo-2-azetidinoniderivat, och nya som mellanprodukt anvaendbara 2-azetidinonderivat. |
Country Status (29)
| Country | Link |
|---|---|
| JP (3) | JPS56125362A (de) |
| KR (1) | KR860001289B1 (de) |
| AR (1) | AR245932A1 (de) |
| AU (1) | AU569407B2 (de) |
| CA (1) | CA1338670C (de) |
| CH (2) | CH653993A5 (de) |
| DD (1) | DD156180A5 (de) |
| DE (1) | DE3104145C2 (de) |
| DK (1) | DK166280C (de) |
| ES (1) | ES8205397A1 (de) |
| FI (1) | FI80271C (de) |
| FR (1) | FR2509299B1 (de) |
| GB (2) | GB2071650B (de) |
| GR (1) | GR74151B (de) |
| HK (1) | HK57785A (de) |
| IE (2) | IE51392B1 (de) |
| IL (1) | IL62082A (de) |
| IT (1) | IT1135360B (de) |
| KE (1) | KE3539A (de) |
| LU (1) | LU83117A1 (de) |
| MY (1) | MY8600179A (de) |
| NL (1) | NL192924C (de) |
| NO (2) | NO161065C (de) |
| NZ (2) | NZ196202A (de) |
| PH (3) | PH24729A (de) |
| PT (1) | PT72465B (de) |
| SE (3) | SE457954B (de) |
| SG (1) | SG39185G (de) |
| YU (1) | YU44829B (de) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0050965A1 (de) * | 1980-10-23 | 1982-05-05 | Takeda Chemical Industries, Ltd. | Beta-Lactamase inhibierende Zusammensetzung |
| WO1982001873A1 (en) * | 1980-12-05 | 1982-06-10 | Takeda Chemical Industries Ltd | 1-sulfo-2-oxoazetidine derivatives and process for their preparation |
| US4673739A (en) * | 1980-12-05 | 1987-06-16 | Takeda Chemical Industries, Ltd. | 4-carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production |
| JPS57131758A (en) * | 1980-12-05 | 1982-08-14 | Takeda Chem Ind Ltd | 1-sulfo-2-oxoazetidine derivative, its preparation and use |
| WO1983000690A1 (en) * | 1981-08-25 | 1983-03-03 | Takeda Chemical Industries Ltd | Azetidine derivatives and process for their preparation |
| US4675397A (en) * | 1980-12-05 | 1987-06-23 | Takeda Chemical Industries, Ltd. | 1-sulfo-2-oxoazetidine derivatives and their production |
| MX7096E (es) * | 1980-12-05 | 1987-06-19 | Takeda Chemical Industries Ltd | Metodo para preparacion de derivados de 2-oxoazetidina |
| JPS58210061A (ja) * | 1982-05-31 | 1983-12-07 | Takeda Chem Ind Ltd | １−スルホ−２−オキソアゼチジン誘導体、その製造法および用途 |
| US4782147A (en) * | 1980-12-05 | 1988-11-01 | Takeda Chemical Industries, Ltd. | 1-sulfo-2-oxoazetidine derivatives and their production |
| US4572801A (en) * | 1981-04-30 | 1986-02-25 | Takeda Chemical Industries, Ltd. | 4-Carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production |
| CA1181075A (en) * | 1981-07-13 | 1985-01-15 | David M. Floyd | CRYSTALLINE ANHYDROUS FORM OF [3-S-[3.alpha.(Z),4 .beta.]]-3-[[(2-AMINO-4-THIAZOLYL) [(1-CARBOXY-1-METHYLETHOXY)IMINO]ACETYL] AMINO]-4-METHYL-2-OXO-1-AZETIDINESULFONIC ACID |
| FR2515182B1 (fr) * | 1981-10-23 | 1986-05-09 | Roussel Uclaf | Nouveaux produits derives de l'acide 3-amino 2-oxo azetidine 1-sulfamique, leur procede de preparation, leur application comme medicaments et les produits intermediaires necessaires a leur preparation |
| FR2538389B2 (fr) * | 1981-10-23 | 1986-05-16 | Roussel Uclaf | Nouveaux produits derives de l'acide 3-amino 2-oxo azetidine-1-sulfamique, nouveau procede de preparation de produits optiquement actifs, application des nouveaux produits comme medicaments et produits necessaires a leur preparation |
| IL67451A (en) * | 1981-12-25 | 1987-10-20 | Takeda Chemical Industries Ltd | 4-cyano-2-azetidinones and production thereof and process for the preparation of 4-carbamoyl-2-azetidinones using them |
| EP0088488B1 (de) * | 1982-01-22 | 1986-10-01 | Beecham Group Plc | Antibakteriell wirkende Mittel, ihre Herstellung und Verwendung |
| EP0086563A1 (de) * | 1982-01-22 | 1983-08-24 | Beecham Group Plc | Antibakteriel wirkende Mittel, ihre Herstellung und Verwendung |
| US4443374A (en) * | 1982-02-01 | 1984-04-17 | E. R. Squibb & Sons, Inc. | Process for preparing (3S)-3-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]-acetyl]amino]-2-oxo-1-azetidinesulfonic acid, and 4-substituted derivatives |
| WO1983002942A1 (en) * | 1982-02-19 | 1983-09-01 | Yoshioka, Kouichi | Process for preparing 2-azetidinone-1-sulfonic acids, and starting materials therefor |
| AU564150B2 (en) * | 1982-04-30 | 1987-08-06 | Takeda Chemical Industries Ltd. | 1-sulfo-2-azetidinone derivatives |
| EP0096296B1 (de) * | 1982-06-03 | 1987-07-29 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 1-Sulfo-2-oxoazetidinderivate |
| DE3377061D1 (en) * | 1982-06-03 | 1988-07-21 | Hoffmann La Roche | Process for the preparation of 1-sulfo-2-oxoazetidine derivatives |
| US4704457A (en) * | 1982-06-21 | 1987-11-03 | E. R. Squibb & Sons, Inc. | Process for the preparation of (3S)-3-[[[2-(protected amino)-4-thiazolyl]-oxoacetyl]amino]-2-oxo-1-azetidinesulfonic acid and 4-substituted derivatives thereof |
| US4939253A (en) * | 1982-08-04 | 1990-07-03 | E. R. Squibb & Sons, Inc. | 2-oxoazetidin-1-yloxy acetic acids and analogs |
| US4681937A (en) * | 1982-09-27 | 1987-07-21 | E. R. Squibb & Sons, Inc. | 3-acylamino-2-oxo-1-azetidinyl esters of phosphonic acids, phosphoric acid and phosphoric acid esters |
| US4551276A (en) * | 1982-10-06 | 1985-11-05 | E. R. Squibb & Sons, Inc. | 2-Oxoazetidin-1-yloxymethyl sulfonic acid and analogs |
| US4533495A (en) * | 1982-12-30 | 1985-08-06 | Takeda Chemical Industries, Ltd. | Method of producing 2-azetidinone-1-sulfonic acid compounds |
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| JPS601162A (ja) * | 1983-06-17 | 1985-01-07 | Dai Ichi Seiyaku Co Ltd | ３―アジド―２―オキソアゼチジン―１―スルホン酸誘導体の製造法 |
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| US4596777A (en) * | 1983-08-10 | 1986-06-24 | E. R. Squibb & Sons, Inc. | Process for preparing (3S)-3-[[[2-(protected or unprotected amino)-4-thiazolyl]acetyl]amino]-2-oxo-1-azetidinesulfonic acid and 4-substituted derivatives thereof |
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| JPS60112789A (ja) * | 1983-11-21 | 1985-06-19 | Otsuka Chem Co Ltd | ３−アシルアミノ−４−アルキル−２−アゼチジノン−１−スルホン酸誘導体、その製造方法および該誘導体を含有する薬剤 |
| JPS60226855A (ja) * | 1984-04-26 | 1985-11-12 | Nippon Kayaku Co Ltd | Ｎ−ベンジルオキシカルボニル−ｌ−スレオニンアミド・１／２水和物およびその製造法 |
| US4771135A (en) * | 1984-05-22 | 1988-09-13 | Eli Lilly And Company | Process for carbon-carbon bond formation at the C-4 position of 3-acylaminoazetidinones and products and starting materials therefor |
| US4918185A (en) * | 1984-05-22 | 1990-04-17 | Eli Lilly And Company | Process for carbon-carbon bond formation at the C-4 position of 3-acylaminoazetidinones and products and starting materials therefor |
| US4610824A (en) * | 1984-10-09 | 1986-09-09 | E. R. Squibb & Sons, Inc. | Hydrazide derivatives of monocyclic beta-lactam antibiotics |
| US4680409A (en) * | 1984-10-09 | 1987-07-14 | E. R. Squibb & Sons, Inc. | Hydrazide containing derivatives of 2-amino-4-thiazole-acetic acid |
| US4647660A (en) * | 1985-05-02 | 1987-03-03 | E. R. Squibb & Sons, Inc. | 3-acylamino-2-oxo-1-azetidinesulfonic acids |
| US4632985A (en) * | 1985-06-03 | 1986-12-30 | E. R. Squibb & Sons, Inc. | 3-acylamino-2-oxo-1-azetidinesulfonic acids |
| US4754041A (en) * | 1985-06-17 | 1988-06-28 | E. R. Squibb & Sons, Inc. | 3-acylamino-2-oxo-1-azetidinesulfonic acids |
| US4638062A (en) * | 1985-06-17 | 1987-01-20 | E. R. Squibb & Sons, Inc. | 3-acylamino-2-oxo-1-azetidinesulfonic acids |
| FR2588867B1 (fr) * | 1985-10-23 | 1988-12-09 | Roussel Uclaf | Nouveaux produits derives de la serie de la 3-amino 2-oxo azetidine, leur procede de preparation et leur application |
| MX2007000526A (es) * | 2005-05-09 | 2007-03-28 | Sicor Inc | Proceso para elaborar aztreonam. |
| JP5648250B2 (ja) * | 2007-11-21 | 2015-01-07 | 国立大学法人東京工業大学 | スルホン化含窒素複素環を有する高分子有機化合物および有機化合物、それらの製造方法、およびそれらを用いたイオン交換体、電解質膜、医薬品、触媒、膜電極接合体、燃料電池 |
| EP2804589A1 (de) | 2012-01-16 | 2014-11-26 | Mahmut Bilgic | Pharmazeutische formulierungen mit aztreonam |
| PL3122745T3 (pl) | 2014-03-24 | 2019-08-30 | Novartis Ag | Monobaktamowe związki organiczne do leczenia zakażeń bakteryjnych |
| DK3353175T3 (da) | 2015-09-23 | 2020-09-14 | Novartis Ag | Salte og faste former af et monobactam-antibiotikum |
| WO2019026004A2 (en) | 2017-08-02 | 2019-02-07 | Novartis Ag | CHEMICAL PROCESS FOR THE PREPARATION OF ANTIBIOTIC MONOBACTAM AND ITS INTERMEDIATES |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6046955B2 (ja) * | 1977-12-30 | 1985-10-18 | 武田薬品工業株式会社 | 抗生物質ｇ−６３０２ |
| JPS55164672A (en) * | 1979-06-08 | 1980-12-22 | Takeda Chem Ind Ltd | Azetidine derivative and its preparation |
| EP0021678B1 (de) * | 1979-06-08 | 1984-11-07 | Takeda Chemical Industries, Ltd. | 1-Sulfo-2-azetidinon-Derivate, ihre Herstellung und pharmazeutische Zusammensetzungen |
| WO1982001873A1 (en) * | 1980-12-05 | 1982-06-10 | Takeda Chemical Industries Ltd | 1-sulfo-2-oxoazetidine derivatives and process for their preparation |
| JPS57131758A (en) * | 1980-12-05 | 1982-08-14 | Takeda Chem Ind Ltd | 1-sulfo-2-oxoazetidine derivative, its preparation and use |
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1981
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- 1981-02-06 GB GB8103655A patent/GB2071650B/en not_active Expired
- 1981-02-06 CH CH5565/84A patent/CH653993A5/de not_active IP Right Cessation
- 1981-02-06 JP JP1737981A patent/JPS56125362A/ja active Pending
- 1981-02-06 IE IE230/81A patent/IE51392B1/en not_active IP Right Cessation
- 1981-02-06 PT PT72465A patent/PT72465B/pt unknown
- 1981-02-06 SE SE8100861A patent/SE457954B/sv not_active IP Right Cessation
- 1981-02-06 PH PH25195A patent/PH24729A/en unknown
- 1981-02-06 IT IT19587/81A patent/IT1135360B/it active Protection Beyond IP Right Term
- 1981-02-06 LU LU83117A patent/LU83117A1/fr unknown
- 1981-02-06 CH CH816/81A patent/CH651020A5/de not_active IP Right Cessation
- 1981-02-06 ES ES499171A patent/ES8205397A1/es not_active Expired
- 1981-02-06 NL NL8100571A patent/NL192924C/nl not_active IP Right Cessation
- 1981-02-06 NO NO810410A patent/NO161065C/no unknown
- 1981-02-06 FI FI810352A patent/FI80271C/fi not_active IP Right Cessation
- 1981-02-06 DE DE3104145A patent/DE3104145C2/de not_active Expired - Lifetime
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- 1981-02-06 IL IL62082A patent/IL62082A/xx not_active IP Right Cessation
- 1981-02-06 CA CA000370320A patent/CA1338670C/en not_active Expired - Fee Related
- 1981-02-06 YU YU319/81A patent/YU44829B/xx unknown
- 1981-02-06 KR KR1019810000379A patent/KR860001289B1/ko active
- 1981-02-06 IE IE2297/86A patent/IE51393B1/en not_active IP Right Cessation
- 1981-02-06 DD DD81227473A patent/DD156180A5/de not_active IP Right Cessation
- 1981-02-06 FR FR8102372A patent/FR2509299B1/fr not_active Expired
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1983
- 1983-12-13 GB GB08333191A patent/GB2139618B/en not_active Expired
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1984
- 1984-06-15 PH PH30820A patent/PH23317A/en unknown
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1985
- 1985-05-25 SG SG391/85A patent/SG39185G/en unknown
- 1985-05-29 KE KE3539A patent/KE3539A/xx unknown
- 1985-08-01 HK HK577/85A patent/HK57785A/xx not_active IP Right Cessation
- 1985-08-02 AU AU45748/85A patent/AU569407B2/en not_active Expired
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1986
- 1986-01-22 NO NO86860225A patent/NO170015C/no unknown
- 1986-05-14 SE SE8602194A patent/SE8602194D0/xx not_active Application Discontinuation
- 1986-05-14 SE SE8602193A patent/SE500216C2/sv unknown
- 1986-12-30 MY MY179/86A patent/MY8600179A/xx unknown
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1989
- 1989-11-22 JP JP1304538A patent/JPH0623188B2/ja not_active Expired - Lifetime
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1991
- 1991-05-27 JP JP3121251A patent/JPH0670006B2/ja not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
Owner name: E.R. SQUIBB & SONS, INC. |