SE463514B - Foerfarande foer framstaellning av penemderivat - Google Patents
Foerfarande foer framstaellning av penemderivatInfo
- Publication number
- SE463514B SE463514B SE8404004A SE8404004A SE463514B SE 463514 B SE463514 B SE 463514B SE 8404004 A SE8404004 A SE 8404004A SE 8404004 A SE8404004 A SE 8404004A SE 463514 B SE463514 B SE 463514B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- groups
- hydroxy
- process according
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical class S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 title description 3
- -1 formyloxy group Chemical group 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000008096 xylene Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 5
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 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 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- MYMJFVNSFNDTKW-UHFFFAOYSA-N 2-[tert-butyl(diphenyl)silyl]oxyethanethioic s-acid Chemical compound C=1C=CC=CC=1[Si](OCC(S)=O)(C(C)(C)C)C1=CC=CC=C1 MYMJFVNSFNDTKW-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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 3
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
- RLUBBPGXLKAPFW-PWVDTXNTSA-N (4-nitrophenyl)methyl (5R,6S)-3-(acetyloxymethyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound O[C@H](C)[C@@H]1[C@@H]2N(C(=C(S2)COC(C)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O RLUBBPGXLKAPFW-PWVDTXNTSA-N 0.000 description 2
- DKHFTSFWDSOEKQ-SULUZNBOSA-N (4-nitrophenyl)methyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound O[C@H](C)[C@@H]1[C@@H]2N(C(=C(S2)CSC2=NN=NN2C)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O DKHFTSFWDSOEKQ-SULUZNBOSA-N 0.000 description 2
- GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical class [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- CSJNGHADKXVTSR-UGOXQWAPSA-N (5R)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C[C@H](C1[C@@H]2N(C1=O)C(=CS2)C(=O)O)O[Si](C)(C)C(C)(C)C CSJNGHADKXVTSR-UGOXQWAPSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- JLKXXTALBTXNLY-UHFFFAOYSA-N 2-hydroxyethanethioic s-acid Chemical compound OCC(S)=O JLKXXTALBTXNLY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XOQWAKQRQLXZKR-KIXYHFEESA-N C(N)(=O)OC=1S[C@]2(N(C1C(=O)OCOC(C)=O)C([C@@H]2[C@@H](C)O)=O)C Chemical compound C(N)(=O)OC=1S[C@]2(N(C1C(=O)OCOC(C)=O)C([C@@H]2[C@@H](C)O)=O)C XOQWAKQRQLXZKR-KIXYHFEESA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- ARVZTBPSQOZCFA-ASUYLVSUSA-N C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)CO)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])O[Si](C)(C)C(C)(C)C Chemical compound C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)CO)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])O[Si](C)(C)C(C)(C)C ARVZTBPSQOZCFA-ASUYLVSUSA-N 0.000 description 1
- ILSMYXHRXPRTCI-YFYZNPQRSA-N C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)COC(=O)C)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])O[Si](C)(C)C(C)(C)C Chemical compound C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)COC(=O)C)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])O[Si](C)(C)C(C)(C)C ILSMYXHRXPRTCI-YFYZNPQRSA-N 0.000 description 1
- JIGIRBYRCMATON-ASUYLVSUSA-N C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)COC(=O)N)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])O[Si](C)(C)C(C)(C)C Chemical compound C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)COC(=O)N)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])O[Si](C)(C)C(C)(C)C JIGIRBYRCMATON-ASUYLVSUSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 101100422316 Schizosaccharomyces pombe (strain 972 / ATCC 24843) srw1 gene Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- FZKGLCPKPZBGLX-ROXVQFJHSA-N acetyloxymethyl (5r,6s)-3-(carbamoyloxymethyl)-6-[(1r)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound S1C(COC(N)=O)=C(C(=O)OCOC(C)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 FZKGLCPKPZBGLX-ROXVQFJHSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- DOBMPNYZJYQDGZ-UHFFFAOYSA-N dicoumarol Chemical compound C1=CC=CC2=C1OC(=O)C(CC=1C(OC3=CC=CC=C3C=1O)=O)=C2O DOBMPNYZJYQDGZ-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000005949 ozonolysis reaction Methods 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
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002217 penem group Chemical group 0.000 description 1
- 150000002961 penems Chemical class 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- FPLQVCOCYJJHBC-HIQLJADVSA-M sodium;(5r,6s)-3-(carbamoyloxymethyl)-6-[(1r)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].S1C(COC(N)=O)=C(C([O-])=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 FPLQVCOCYJJHBC-HIQLJADVSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005039 triarylmethyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/04—Preparation
- C07D499/06—Preparation by forming the ring or condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D205/09—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 sulfur atom directly attached in position 4
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838321677A GB8321677D0 (en) | 1983-08-11 | 1983-08-11 | Preparation of penems |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8404004D0 SE8404004D0 (sv) | 1984-08-07 |
| SE8404004L SE8404004L (sv) | 1985-02-12 |
| SE463514B true SE463514B (sv) | 1990-12-03 |
Family
ID=10547172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8404004A SE463514B (sv) | 1983-08-11 | 1984-08-07 | Foerfarande foer framstaellning av penemderivat |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4631150A (es) |
| JP (1) | JPS6058988A (es) |
| KR (1) | KR910002098B1 (es) |
| AT (1) | AT383808B (es) |
| BE (1) | BE900316A (es) |
| CA (1) | CA1279640C (es) |
| CH (1) | CH663024A5 (es) |
| DE (1) | DE3429102A1 (es) |
| DK (1) | DK167926B1 (es) |
| ES (1) | ES534892A0 (es) |
| FI (1) | FI83521C (es) |
| FR (1) | FR2550533B1 (es) |
| GB (2) | GB8321677D0 (es) |
| GR (1) | GR80102B (es) |
| HU (1) | HU192415B (es) |
| IL (1) | IL72612A (es) |
| IT (1) | IT1209578B (es) |
| NL (1) | NL8402478A (es) |
| PT (1) | PT79065B (es) |
| SE (1) | SE463514B (es) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8416651D0 (en) * | 1984-06-29 | 1984-08-01 | Erba Farmitalia | Penem derivatives |
| DE3688960D1 (de) * | 1985-09-11 | 1993-10-07 | Ciba Geigy | Synthese von Beta-Lactamverbindungen. |
| US5215997A (en) * | 1985-09-11 | 1993-06-01 | Ciba-Geigy Corporation | Synthesis of beta-lactam compounds |
| DE3752124T2 (de) * | 1986-01-17 | 1998-03-26 | Beecham Group Plc | Verfahren zur Herstellung von Penem Derivaten und Zwischenprodukte zu dieser Herstellung |
| EP0233155A1 (de) * | 1986-02-14 | 1987-08-19 | Ciba-Geigy Ag | Aminoacyloxymethyl-Verbindungen |
| US5215891A (en) * | 1986-10-15 | 1993-06-01 | Farmitalia Carlo Erba | Process for preparing penems |
| US5312914A (en) * | 1987-02-17 | 1994-05-17 | Ciba-Geigy Corp | Process for the manufacture of 4-acetoxy-3-hydroxyethyl-azetidinone |
| EP0279781A3 (de) * | 1987-02-17 | 1989-07-26 | Ciba-Geigy Ag | Verfahren zur Herstellung von 4-Acetoxy-3-hydroxyethyl-azetidinon |
| GB8713515D0 (en) * | 1987-06-10 | 1987-07-15 | Erba Farmitalia | Methoxymethyl compounds |
| GB2206578B (en) * | 1987-07-07 | 1991-07-03 | Erba Carlo Spa | Process for the preparation of penems |
| US5364768A (en) * | 1987-07-07 | 1994-11-15 | Farmitalia Carlo Erba S.R.L. | Process for the preparation of penems |
| US5191075A (en) * | 1988-10-19 | 1993-03-02 | Pfizer Inc | Process for the preparation of penems |
| US4992543A (en) * | 1988-10-19 | 1991-02-12 | Pfizer Inc. | Penem derivatives |
| US5273973A (en) * | 1988-10-24 | 1993-12-28 | Norwich Eaton Pharmaceuticals, Inc. | Antimicrobial quinolonyl esters |
| US5491139A (en) * | 1988-10-24 | 1996-02-13 | The Procter & Gamble Company | Antimicrobial quinolonyl lactams |
| CA2001203C (en) * | 1988-10-24 | 2001-02-13 | Thomas P. Demuth, Jr. | Novel antimicrobial dithiocarbamoyl quinolones |
| US5180719A (en) * | 1988-10-24 | 1993-01-19 | Norwich Eaton Pharmaceuticals, Inc. | Antimicrobial quinolonyl lactam esters |
| US5328908A (en) * | 1988-10-24 | 1994-07-12 | Procter & Gamble Pharmaceuticals, Inc. | Antimicrobial quinolone thioureas |
| EP0366189A3 (en) * | 1988-10-24 | 1992-01-02 | Norwich Eaton Pharmaceuticals, Inc. | Novel antimicrobial lactam-quinolones |
| US5198544A (en) * | 1989-04-29 | 1993-03-30 | Hoechst Aktiengesellschaft | Process for the preparation of penem compounds |
| EP0399228A1 (de) * | 1989-04-29 | 1990-11-28 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Penemverbindungen |
| CA2078444A1 (en) | 1990-04-18 | 1991-10-19 | Thomas P. Demuth, Jr. | Antimicrobial quinolonyl lactams |
| US5399679A (en) * | 1992-06-16 | 1995-03-21 | Farmitalia Carlo Erba S.R.L. | (1'R,3S,4R)4-acylthio azetidinones |
| EP0597401A3 (en) * | 1992-11-11 | 1995-07-26 | Takeda Chemical Industries Ltd | Preparation of penemes. |
| IT1286558B1 (it) * | 1996-02-27 | 1998-07-15 | Menarini Farma Ind | Processo per la preparazione di 2-alogenometil-penems e loro uso per la preparazione di penems antibatterici |
| CN100417654C (zh) * | 2004-01-09 | 2008-09-10 | 中国医学科学院医药生物技术研究所 | 2-苯羧酸酯青霉烯类化合物及其制备方法和应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4500457A (en) * | 1977-05-09 | 1985-02-19 | Ciba-Geigy Corporation | Process for preparing thia-aza compounds with a beta-lactam ring |
| US4168314A (en) * | 1977-11-17 | 1979-09-18 | Merck & Co., Inc. | 6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid |
| EP0042026B1 (de) * | 1978-02-02 | 1986-01-08 | Ciba-Geigy Ag | 3,4-Disubstituierte Azetidin-2-onverbindungen und Verfahren zu ihrer Herstellung |
| EP0013067A1 (en) * | 1978-12-22 | 1980-07-09 | Beecham Group Plc | Bicyclic beta-lactam antibacterial agents, their use in pharmaceutical compositions, processes for their preparation and intermediates for use in such processes |
| FI75163C (fi) * | 1979-02-24 | 1988-05-09 | Erba Farmitalia | Foerfarande foer framstaellning av nya penemkarboxylsyror eller -estrar. |
| US4269771A (en) * | 1979-04-06 | 1981-05-26 | Farmitalia Carlo Erba | Total synthesis of 7-oxo-4-thia-1-azabicyclo-[3,2,0]-heptane-2-carboxyl derivatives useful as β-lactamase inhibitors and antibacterial agents |
| ES502828A0 (es) * | 1980-06-06 | 1982-11-01 | Sankyo Co | Un procedimiento para la preparacion de derivados del acido penen-3-carboxilico. |
| GB2079744A (en) * | 1980-07-04 | 1982-01-27 | Erba Farmitalia | 6-Alkyl-2-functionalized penems |
| US4347183A (en) * | 1981-02-02 | 1982-08-31 | Schering Corporation | Process for the synthesis of penems and carbapenems |
| JPS588084A (ja) * | 1981-07-08 | 1983-01-18 | Takeda Chem Ind Ltd | （６ｒ）−置換−（５ｒ）−ペネム−３−カルボン酸誘導体およびその製造法 |
| US4411906A (en) * | 1981-11-25 | 1983-10-25 | Schering Corporation | (5R,6S,8R)-6-(1-Hydroxyethyl)-2-(2-fluoroethylthio)-penem-3-carboxylates |
| AT379399B (de) * | 1981-12-11 | 1985-12-27 | Erba Farmitalia | Verfahren zur herstellung von optisch aktiven penemen |
| US4443373A (en) * | 1982-03-30 | 1984-04-17 | Schering Corporation | Process for the production of antibiotic penems |
| US4584133A (en) * | 1983-11-07 | 1986-04-22 | Schering Corporation | Process for the production of penems |
-
1983
- 1983-08-11 GB GB838321677A patent/GB8321677D0/en active Pending
-
1984
- 1984-08-03 ES ES534892A patent/ES534892A0/es active Granted
- 1984-08-06 IT IT8422234A patent/IT1209578B/it active
- 1984-08-06 US US06/637,878 patent/US4631150A/en not_active Expired - Lifetime
- 1984-08-07 IL IL72612A patent/IL72612A/xx not_active IP Right Cessation
- 1984-08-07 DE DE19843429102 patent/DE3429102A1/de not_active Ceased
- 1984-08-07 SE SE8404004A patent/SE463514B/sv not_active IP Right Cessation
- 1984-08-07 FR FR8412466A patent/FR2550533B1/fr not_active Expired
- 1984-08-07 AT AT0255884A patent/AT383808B/de not_active IP Right Cessation
- 1984-08-08 DK DK382084A patent/DK167926B1/da not_active IP Right Cessation
- 1984-08-08 BE BE0/213460A patent/BE900316A/fr not_active IP Right Cessation
- 1984-08-08 FI FI843111A patent/FI83521C/fi not_active IP Right Cessation
- 1984-08-08 JP JP59165031A patent/JPS6058988A/ja active Granted
- 1984-08-09 GB GB08420236A patent/GB2144743B/en not_active Expired
- 1984-08-10 PT PT79065A patent/PT79065B/pt not_active IP Right Cessation
- 1984-08-10 GR GR80102A patent/GR80102B/el unknown
- 1984-08-10 KR KR1019840004797A patent/KR910002098B1/ko not_active IP Right Cessation
- 1984-08-10 CH CH3855/84A patent/CH663024A5/de not_active IP Right Cessation
- 1984-08-10 HU HU843056A patent/HU192415B/hu not_active IP Right Cessation
- 1984-08-10 NL NL8402478A patent/NL8402478A/xx not_active Application Discontinuation
- 1984-08-10 CA CA000460795A patent/CA1279640C/en not_active Expired - Fee Related
Also Published As
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