NZ196202A - Beta-lactam antibiotics (of azetidine-sulphonic acid type) - Google Patents
Beta-lactam antibiotics (of azetidine-sulphonic acid type)Info
- Publication number
- NZ196202A NZ196202A NZ196202A NZ19620281A NZ196202A NZ 196202 A NZ196202 A NZ 196202A NZ 196202 A NZ196202 A NZ 196202A NZ 19620281 A NZ19620281 A NZ 19620281A NZ 196202 A NZ196202 A NZ 196202A
- Authority
- NZ
- New Zealand
- Prior art keywords
- amino
- oxo
- acid
- salt
- hydrogen
- Prior art date
Links
- KHUNFTAJVUPPCY-UHFFFAOYSA-N azetidine-1-sulfonic acid Chemical compound OS(=O)(=O)N1CCC1 KHUNFTAJVUPPCY-UHFFFAOYSA-N 0.000 title description 11
- 239000003782 beta lactam antibiotic agent Substances 0.000 title description 5
- 239000002132 β-lactam antibiotic Substances 0.000 title 1
- 229940124586 β-lactam antibiotics Drugs 0.000 title 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 344
- -1 2-phenylethenyl Chemical group 0.000 claims description 323
- 150000001875 compounds Chemical class 0.000 claims description 256
- 239000002253 acid Substances 0.000 claims description 227
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 119
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 114
- 239000001257 hydrogen Substances 0.000 claims description 100
- 229910052739 hydrogen Inorganic materials 0.000 claims description 100
- 238000000034 method Methods 0.000 claims description 100
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 82
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 80
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 74
- 150000003839 salts Chemical group 0.000 claims description 71
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000000284 extract Substances 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 244000005700 microbiome Species 0.000 claims description 21
- 150000001768 cations Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 17
- 238000006277 sulfonation reaction Methods 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 11
- 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 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000001301 oxygen Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000008103 glucose Substances 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 229920001817 Agar Polymers 0.000 claims description 6
- 239000008272 agar Substances 0.000 claims description 6
- 229940041514 candida albicans extract Drugs 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 239000012138 yeast extract Substances 0.000 claims description 6
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 125000005276 alkyl hydrazino group Chemical group 0.000 claims description 5
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 3
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 235000015278 beef Nutrition 0.000 claims description 2
- 229910001414 potassium ion Inorganic materials 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 7
- 101100059652 Mus musculus Cetn1 gene Proteins 0.000 claims 5
- 101100059655 Mus musculus Cetn2 gene Proteins 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 241000588724 Escherichia coli Species 0.000 claims 4
- 241000191967 Staphylococcus aureus Species 0.000 claims 4
- 241000588915 Klebsiella aerogenes Species 0.000 claims 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 241000588624 Acinetobacter calcoaceticus Species 0.000 claims 1
- 241000588919 Citrobacter freundii Species 0.000 claims 1
- 241000588697 Enterobacter cloacae Species 0.000 claims 1
- 241000194032 Enterococcus faecalis Species 0.000 claims 1
- 241000588747 Klebsiella pneumoniae Species 0.000 claims 1
- 241000191938 Micrococcus luteus Species 0.000 claims 1
- 101001034845 Mus musculus Interferon-induced transmembrane protein 3 Proteins 0.000 claims 1
- 241000588770 Proteus mirabilis Species 0.000 claims 1
- 241000588767 Proteus vulgaris Species 0.000 claims 1
- 241000588777 Providencia rettgeri Species 0.000 claims 1
- 241000607142 Salmonella Species 0.000 claims 1
- 241000607715 Serratia marcescens Species 0.000 claims 1
- 241000607760 Shigella sonnei Species 0.000 claims 1
- 241000193985 Streptococcus agalactiae Species 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 229940092559 enterobacter aerogenes Drugs 0.000 claims 1
- 230000005021 gait Effects 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 229940007042 proteus vulgaris Drugs 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229940115939 shigella sonnei Drugs 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 408
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 342
- 239000000243 solution Substances 0.000 description 248
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 246
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 207
- 229910001868 water Inorganic materials 0.000 description 200
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 192
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 189
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 185
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 181
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 174
- 238000002844 melting Methods 0.000 description 160
- 230000008018 melting Effects 0.000 description 160
- 239000000203 mixture Substances 0.000 description 124
- 239000000047 product Substances 0.000 description 87
- 239000002904 solvent Substances 0.000 description 84
- 238000003756 stirring Methods 0.000 description 75
- 239000007787 solid Substances 0.000 description 60
- 239000003921 oil Substances 0.000 description 58
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 58
- 238000007792 addition Methods 0.000 description 55
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 47
- 239000000706 filtrate Substances 0.000 description 45
- 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 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 42
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 41
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 35
- 229960003424 phenylacetic acid Drugs 0.000 description 34
- 239000002002 slurry Substances 0.000 description 32
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 238000004587 chromatography analysis Methods 0.000 description 29
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 29
- 239000002244 precipitate Substances 0.000 description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 238000010828 elution Methods 0.000 description 27
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 27
- 235000019796 monopotassium phosphate Nutrition 0.000 description 27
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 27
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 26
- 239000012043 crude product Substances 0.000 description 26
- 239000000741 silica gel Substances 0.000 description 26
- 229910002027 silica gel Inorganic materials 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
- 239000000463 material Substances 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 238000001914 filtration Methods 0.000 description 23
- 239000010410 layer Substances 0.000 description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 20
- 239000003480 eluent Substances 0.000 description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 20
- 238000000746 purification Methods 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 19
- 229910052938 sodium sulfate Inorganic materials 0.000 description 19
- 235000011152 sodium sulphate Nutrition 0.000 description 19
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 18
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 18
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 239000012298 atmosphere Substances 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 238000001665 trituration Methods 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- NSRVGDULUQOEBX-REOHCLBHSA-N (3s)-3-amino-2-oxoazetidine-1-sulfonic acid Chemical compound N[C@H]1CN(S(O)(=O)=O)C1=O NSRVGDULUQOEBX-REOHCLBHSA-N 0.000 description 14
- 239000004202 carbamide Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
- 239000012452 mother liquor Substances 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 13
- 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 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 13
- DAKDZRFZKWOQEG-DKWTVANSSA-M potassium (3S)-3-amino-2-oxoazetidine-1-sulfonate Chemical compound N[C@@H]1C(N(C1)S(=O)(=O)[O-])=O.[K+] DAKDZRFZKWOQEG-DKWTVANSSA-M 0.000 description 13
- 239000008057 potassium phosphate buffer Substances 0.000 description 13
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- 238000004108 freeze drying Methods 0.000 description 12
- 239000002609 medium Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 235000011181 potassium carbonates Nutrition 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 241000588879 Chromobacterium violaceum Species 0.000 description 11
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
- 150000003222 pyridines Chemical class 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 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 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 241000589236 Gluconobacter Species 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- NONZZMVLNASYPE-UHFFFAOYSA-N 3-amino-3-methoxy-2-oxoazetidine-1-sulfonic acid Chemical compound COC1(N)CN(S(O)(=O)=O)C1=O NONZZMVLNASYPE-UHFFFAOYSA-N 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000003115 biocidal effect Effects 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 8
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 239000007868 Raney catalyst Substances 0.000 description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
- 229910000564 Raney nickel Inorganic materials 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- 229910021538 borax Inorganic materials 0.000 description 7
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- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- LXWBXEWUSAABOA-VXSYNFHWSA-N cephamycin C Chemical compound S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)[C@@](OC)(NC(=O)CCC[C@@H](N)C(O)=O)[C@H]21 LXWBXEWUSAABOA-VXSYNFHWSA-N 0.000 description 1
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 1
- 229960000228 cetalkonium chloride Drugs 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- XHCADAYNFIFUHF-TVKJYDDYSA-N esculin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=C1)O)=CC2=C1OC(=O)C=C2 XHCADAYNFIFUHF-TVKJYDDYSA-N 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- TUHMQDODLHWPCC-UHFFFAOYSA-N formyl cyanide Chemical compound O=CC#N TUHMQDODLHWPCC-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- SPUACDWLOLSOQO-UHFFFAOYSA-M methoxyazanium;chloride Chemical compound [Cl-].CO[NH3+] SPUACDWLOLSOQO-UHFFFAOYSA-M 0.000 description 1
- TVHCXXXXQNWQLP-DMTCNVIQSA-N methyl (2s,3r)-2-amino-3-hydroxybutanoate Chemical compound COC(=O)[C@@H](N)[C@@H](C)O TVHCXXXXQNWQLP-DMTCNVIQSA-N 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000011176 pooling Methods 0.000 description 1
- XWBUIICLDIDCQV-FVGYRXGTSA-M potassium (3S)-2-oxo-3-(phenylmethoxycarbonylamino)azetidine-1-sulfonate Chemical compound C(C1=CC=CC=C1)OC(=O)N[C@@H]1C(N(C1)S(=O)(=O)[O-])=O.[K+] XWBUIICLDIDCQV-FVGYRXGTSA-M 0.000 description 1
- VDZHXBLLTKHLJR-UHFFFAOYSA-M potassium 3-butoxy-2-oxo-3-[(2-phenylacetyl)amino]azetidine-1-sulfonate Chemical compound C(CCC)OC1(C(N(C1)S(=O)(=O)[O-])=O)NC(CC1=CC=CC=C1)=O.[K+] VDZHXBLLTKHLJR-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LJCNRYVRMXRIQR-UHFFFAOYSA-L potassium sodium tartrate Chemical compound [Na+].[K+].[O-]C(=O)C(O)C(O)C([O-])=O LJCNRYVRMXRIQR-UHFFFAOYSA-L 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- TYWSZFDSUNIVSG-UHFFFAOYSA-N potassium tetrabutylazanium Chemical compound [K+].CCCC[N+](CCCC)(CCCC)CCCC TYWSZFDSUNIVSG-UHFFFAOYSA-N 0.000 description 1
- URMALJRLBMFBEQ-UHFFFAOYSA-N potassium;pyridine Chemical compound [K].C1=CC=NC=C1 URMALJRLBMFBEQ-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 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
- 239000012475 sodium chloride buffer Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 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
- XSYFPNDNVLNEMI-BQBZGAKWSA-N tert-butyl n-[(2s,3s)-2-ethyl-4-oxoazetidin-3-yl]carbamate Chemical compound CC[C@@H]1NC(=O)[C@H]1NC(=O)OC(C)(C)C XSYFPNDNVLNEMI-BQBZGAKWSA-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
- VSTSKETWEBYEHL-WDSKDSINSA-N tert-butyl n-[(2s,3s)-2-methyl-4-oxoazetidin-3-yl]carbamate Chemical compound C[C@@H]1NC(=O)[C@H]1NC(=O)OC(C)(C)C VSTSKETWEBYEHL-WDSKDSINSA-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
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-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
- 239000006150 trypticase soy agar Substances 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- 208000019206 urinary tract infection Diseases 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 (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11927680A | 1980-02-07 | 1980-02-07 | |
US18889380A | 1980-09-29 | 1980-09-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
NZ196202A true NZ196202A (en) | 1984-07-31 |
Family
ID=26817179
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NZ196202A NZ196202A (en) | 1980-02-07 | 1981-02-05 | Beta-lactam antibiotics (of azetidine-sulphonic acid type) |
NZ205240A NZ205240A (en) | 1980-02-07 | 1981-02-05 | Sulphonamide derivatives,being starting materials for producing beta-lactams |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NZ205240A NZ205240A (en) | 1980-02-07 | 1981-02-05 | Sulphonamide derivatives,being starting materials for producing beta-lactams |
Country Status (29)
Country | Link |
---|---|
JP (3) | JPS56125362A (da) |
KR (1) | KR860001289B1 (da) |
AR (1) | AR245932A1 (da) |
AU (1) | AU569407B2 (da) |
CA (1) | CA1338670C (da) |
CH (2) | CH651020A5 (da) |
DD (1) | DD156180A5 (da) |
DE (1) | DE3104145C2 (da) |
DK (1) | DK166280C (da) |
ES (1) | ES499171A0 (da) |
FI (1) | FI80271C (da) |
FR (1) | FR2509299B1 (da) |
GB (2) | GB2071650B (da) |
GR (1) | GR74151B (da) |
HK (1) | HK57785A (da) |
IE (2) | IE51393B1 (da) |
IL (1) | IL62082A (da) |
IT (1) | IT1135360B (da) |
KE (1) | KE3539A (da) |
LU (1) | LU83117A1 (da) |
MY (1) | MY8600179A (da) |
NL (1) | NL192924C (da) |
NO (2) | NO161065C (da) |
NZ (2) | NZ196202A (da) |
PH (3) | PH24729A (da) |
PT (1) | PT72465B (da) |
SE (3) | SE457954B (da) |
SG (1) | SG39185G (da) |
YU (1) | YU44829B (da) |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0050965A1 (en) * | 1980-10-23 | 1982-05-05 | Takeda Chemical Industries, Ltd. | Beta-lactamase inhibitory composition |
WO1982001873A1 (en) * | 1980-12-05 | 1982-06-10 | Takeda Chemical Industries Ltd | 1-sulfo-2-oxoazetidine derivatives and process for their preparation |
WO1983000690A1 (en) * | 1981-08-25 | 1983-03-03 | Takeda Chemical Industries Ltd | Azetidine 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 |
US4673739A (en) * | 1980-12-05 | 1987-06-16 | Takeda Chemical Industries, Ltd. | 4-carbamoyloxymethyl-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 |
US4675397A (en) * | 1980-12-05 | 1987-06-23 | Takeda Chemical Industries, Ltd. | 1-sulfo-2-oxoazetidine derivatives and their production |
US4782147A (en) * | 1980-12-05 | 1988-11-01 | Takeda Chemical Industries, Ltd. | 1-sulfo-2-oxoazetidine derivatives and their production |
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 |
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 (en) * | 1982-01-22 | 1986-10-01 | Beecham Group Plc | Antibacterial agents, their preparation and use |
EP0086563A1 (en) * | 1982-01-22 | 1983-08-24 | Beecham Group Plc | Antibacterial agents, their preparation and use |
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 |
EP0096297B1 (de) * | 1982-06-03 | 1988-06-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Verfahren zur Herstellung von 1-Sulfo-2-oxoazetidinderivaten |
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 |
US4548747A (en) * | 1983-05-02 | 1985-10-22 | E. R. Squibb & Sons, Inc. | 3-Acylamino-1-sulfonylaminocarbonylmethoxy-2-azetidinones |
US4670554A (en) * | 1983-05-31 | 1987-06-02 | E. R. Squibb & Sons, Inc. | ((3-Acylamino-2-oxo-1-azetidinyl)oxy)methyl)phosphinic acids |
US4652651A (en) * | 1983-05-31 | 1987-03-24 | Hoffmann-La Roche Inc. | Process for the manufacture of 1-sulpho-2-oxoazetidine carboxylic acid intermediates via catalytic ester cleavage |
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 |
US4501697A (en) * | 1983-06-17 | 1985-02-26 | E. R. Squibb & Sons, Inc. | 4-[[(Amidomethyl)oxy]methyl]-2-oxo-1-azetidinesulfonic acid salts |
US4587051A (en) * | 1983-07-18 | 1986-05-06 | E. R. Squibb & Sons, Inc. | Desulfonation process for preparing 2-azetidinones |
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 |
US4551277A (en) * | 1983-11-09 | 1985-11-05 | E. R. Squibb & Sons, Inc. | 4-(3-Acylamino-2-oxo-1-azetidinyl)-4-oxo-2-butenoic acid |
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 |
ES2321336T3 (es) * | 2005-05-09 | 2009-06-04 | Sicor Inc. | Procedimiento para la fabricacion de 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 (en) | 2012-01-16 | 2014-11-26 | Mahmut Bilgic | Pharmaceutical formulations comprising aztreonam |
PL3122745T3 (pl) | 2014-03-24 | 2019-08-30 | Novartis Ag | Monobaktamowe związki organiczne do leczenia zakażeń bakteryjnych |
JP6837480B2 (ja) | 2015-09-23 | 2021-03-03 | ノバルティス アーゲー | モノバクタム抗生物質の塩および固体形態 |
EP3661933B1 (en) | 2017-08-02 | 2022-03-23 | Novartis AG | Process for preparing 1-(((z)-(1-(2-aminothiazol-4-yl)-2-oxo-2-(((3s,4r)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)-1-sulfoazetidin-3- yl)amino)ethylidene)amino)oxy)cyclopropane carboxylic acid |
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 |
DE3069587D1 (en) * | 1979-06-08 | 1984-12-13 | Takeda Chemical Industries Ltd | 1-sulpho-2-oxoazetidine derivatives, their production and pharmaceutical compositions thereof |
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 |
-
1981
- 1981-02-05 NZ NZ196202A patent/NZ196202A/en unknown
- 1981-02-05 NZ NZ205240A patent/NZ205240A/en unknown
- 1981-02-06 PH PH25195A patent/PH24729A/en unknown
- 1981-02-06 GB GB8103655A patent/GB2071650B/en not_active Expired
- 1981-02-06 YU YU319/81A patent/YU44829B/xx unknown
- 1981-02-06 DD DD81227473A patent/DD156180A5/de not_active IP Right Cessation
- 1981-02-06 ES ES499171A patent/ES499171A0/es active Granted
- 1981-02-06 FR FR8102372A patent/FR2509299B1/fr not_active Expired
- 1981-02-06 LU LU83117A patent/LU83117A1/fr unknown
- 1981-02-06 NO NO810410A patent/NO161065C/no unknown
- 1981-02-06 CH CH816/81A patent/CH651020A5/de not_active IP Right Cessation
- 1981-02-06 NL NL8100571A patent/NL192924C/nl not_active IP Right Cessation
- 1981-02-06 CA CA000370320A patent/CA1338670C/en not_active Expired - Fee Related
- 1981-02-06 FI FI810352A patent/FI80271C/fi not_active IP Right Cessation
- 1981-02-06 IE IE2297/86A patent/IE51393B1/en not_active IP Right Cessation
- 1981-02-06 CH CH5565/84A patent/CH653993A5/de 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 GR GR64081A patent/GR74151B/el unknown
- 1981-02-06 IT IT19587/81A patent/IT1135360B/it active Protection Beyond IP Right Term
- 1981-02-06 DE DE3104145A patent/DE3104145C2/de not_active Expired - Lifetime
- 1981-02-06 IL IL62082A patent/IL62082A/xx 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 DK DK052381A patent/DK166280C/da active
- 1981-02-06 KR KR1019810000379A patent/KR860001289B1/ko active
- 1981-02-08 AR AR81284229A patent/AR245932A1/es active
-
1983
- 1983-12-13 GB GB08333191A patent/GB2139618B/en not_active Expired
-
1984
- 1984-06-15 PH PH30820A patent/PH23317A/en unknown
- 1984-06-15 PH PH30821A patent/PH23316A/en unknown
-
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
-
1986
- 1986-01-22 NO NO86860225A patent/NO170015C/no unknown
- 1986-05-14 SE SE8602194A patent/SE8602194L/xx not_active Application Discontinuation
- 1986-05-14 SE SE8602193A patent/SE500216C2/sv unknown
- 1986-12-30 MY MY179/86A patent/MY8600179A/xx unknown
-
1989
- 1989-11-22 JP JP1304538A patent/JPH0623188B2/ja not_active Expired - Lifetime
-
1991
- 1991-05-27 JP JP3121251A patent/JPH0670006B2/ja not_active Expired - Lifetime
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