NO318020B1 - Cefemderivater, fremgangsmater for fremstilling derav, anvendelse derav for fremstilling av cefalosporiner samt fremgangsmate for fremstilling av 3-substituert-7-acylamino-cefalosporin. - Google Patents
Cefemderivater, fremgangsmater for fremstilling derav, anvendelse derav for fremstilling av cefalosporiner samt fremgangsmate for fremstilling av 3-substituert-7-acylamino-cefalosporin. Download PDFInfo
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- NO318020B1 NO318020B1 NO19964493A NO964493A NO318020B1 NO 318020 B1 NO318020 B1 NO 318020B1 NO 19964493 A NO19964493 A NO 19964493A NO 964493 A NO964493 A NO 964493A NO 318020 B1 NO318020 B1 NO 318020B1
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- compound
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- amino
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- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 18
- 150000001780 cephalosporins Chemical class 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 45
- 238000002360 preparation method Methods 0.000 title claims description 25
- 229930186147 Cephalosporin Natural products 0.000 title abstract description 9
- 150000001782 cephems Chemical class 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 56
- 239000001257 hydrogen Substances 0.000 claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 150000003839 salts Chemical group 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 163
- -1 salt anion Chemical class 0.000 claims description 71
- 238000006243 chemical reaction Methods 0.000 claims description 53
- TWAHQTDAFGRKLL-HWZXHQHMSA-N (6r)-7-amino-3-formyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class S1CC(C=O)=C(C(O)=O)N2C(=O)C(N)[C@H]21 TWAHQTDAFGRKLL-HWZXHQHMSA-N 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 150000001299 aldehydes Chemical class 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Chemical group 0.000 claims description 20
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 238000003776 cleavage reaction Methods 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 10
- 230000007017 scission Effects 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 238000005828 desilylation reaction Methods 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 14
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract description 12
- 239000000543 intermediate Substances 0.000 abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 44
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 229910001868 water Inorganic materials 0.000 description 30
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 26
- 238000003756 stirring Methods 0.000 description 25
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 19
- 239000000843 powder Substances 0.000 description 19
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- 150000003952 β-lactams Chemical class 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- 238000005949 ozonolysis reaction Methods 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 239000012296 anti-solvent Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000003242 anti bacterial agent Substances 0.000 description 7
- 229940088710 antibiotic agent Drugs 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000002955 isolation Methods 0.000 description 7
- 239000011877 solvent mixture Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- 238000002211 ultraviolet spectrum Methods 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 102000010029 Homer Scaffolding Proteins Human genes 0.000 description 5
- 108010077223 Homer Scaffolding Proteins Proteins 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- MAUHLWUADQYTDD-XCGJVMPOSA-N (6r)-4-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(C=C)S[C@@H]2CC(=O)N12 MAUHLWUADQYTDD-XCGJVMPOSA-N 0.000 description 4
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000007239 Wittig reaction Methods 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
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- 125000006239 protecting group Chemical group 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
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- 150000003462 sulfoxides Chemical class 0.000 description 4
- NOSORVMYVRSPRB-WPZCJLIBSA-N (6r)-3-formyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SCC(=C(N2C1=O)C(=O)O)C=O)NC(=O)CC1=CC=CC=C1 NOSORVMYVRSPRB-WPZCJLIBSA-N 0.000 description 3
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 208000035823 Non-specific autoimmune cerebellar ataxia without characteristic antibodies Diseases 0.000 description 3
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 3
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
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- 125000003172 aldehyde group Chemical group 0.000 description 2
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- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 2
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- KBFIHWHARFHELG-GWQXNCQPSA-N (4-methoxyphenyl)methyl (6R)-3-formyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound COc1ccc(COC(=O)C2=C(CS[C@@H]3C(NC(=O)Cc4ccccc4)C(=O)N23)C=O)cc1 KBFIHWHARFHELG-GWQXNCQPSA-N 0.000 description 1
- MLQMFCIUZGPETK-UHFFFAOYSA-N (4-sulfanyl-1,3-benzothiazol-2-yl) 2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound N=1C2=C(S)C=CC=C2SC=1OC(=O)C(=NOC)C1=CSC(N)=N1 MLQMFCIUZGPETK-UHFFFAOYSA-N 0.000 description 1
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- TVALAOPNRKCPQH-YLMDVALBSA-N (6R)-7-amino-3-[(E)-(1-methyl-2-oxopyrrolidin-3-ylidene)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O=C1N(C)CC\C1=C/C(CS1)=C(C(O)=O)N2[C@H]1C(N)C2=O TVALAOPNRKCPQH-YLMDVALBSA-N 0.000 description 1
- PZWYGIPMWLNWAK-HWZXHQHMSA-N (6R)-7-amino-3-[(carbamoylhydrazinylidene)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC1[C@H]2SCC(C=NNC(N)=O)=C(N2C1=O)C(O)=O PZWYGIPMWLNWAK-HWZXHQHMSA-N 0.000 description 1
- PHMGTTNVLQRNBB-CQSZACIVSA-N (6R)-7-benzylidene-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class C(C1=CC=CC=C1)=C1[C@@H]2N(C(=C(CS2)CO)C(=O)O)C1=O PHMGTTNVLQRNBB-CQSZACIVSA-N 0.000 description 1
- GQLGFBRMCCVQLU-XCGJVMPOSA-N (6r)-7-amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C=C)=C(C(O)=O)N2C(=O)C(N)[C@H]21 GQLGFBRMCCVQLU-XCGJVMPOSA-N 0.000 description 1
- VULFABRXVZOASE-JLOHTSLTSA-N (6r)-7-amino-8-oxo-3-(phenyliminomethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1C=NC1=CC=CC=C1 VULFABRXVZOASE-JLOHTSLTSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 1
- AFUMJKIGTDITJU-UHFFFAOYSA-N 2h-thiazine;hydrochloride Chemical compound Cl.N1SC=CC=C1 AFUMJKIGTDITJU-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- ULPAFXWDUMLWIV-UHFFFAOYSA-N C=1C=CC=CC=1P(C=1C=CC=CC=1)(CC(=O)OCC)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(CC(=O)OCC)C1=CC=CC=C1 ULPAFXWDUMLWIV-UHFFFAOYSA-N 0.000 description 1
- XVTBEXYPVIPZKC-XAZLJPHMSA-N CC(=O)NC1C(=C(N2[C@H](S1)C(C2=O)C3=CC=CS3)C(=O)OC(C4=CC=CC=C4)C5=CC=CC=C5)C=O Chemical compound CC(=O)NC1C(=C(N2[C@H](S1)C(C2=O)C3=CC=CS3)C(=O)OC(C4=CC=CC=C4)C5=CC=CC=C5)C=O XVTBEXYPVIPZKC-XAZLJPHMSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000350052 Daniellia ogea Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229910014299 N-Si Inorganic materials 0.000 description 1
- UWNPMOCBVPOGSN-VVKLYLLISA-N NC1[C@@H]2N(C(=C(CS2)/C=C\2/C(N(CC/2)CC(F)(F)F)=O)C(=O)O)C1=O Chemical compound NC1[C@@H]2N(C(=C(CS2)/C=C\2/C(N(CC/2)CC(F)(F)F)=O)C(=O)O)C1=O UWNPMOCBVPOGSN-VVKLYLLISA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ZWZUFQPXYVYAFO-UHFFFAOYSA-N Tert-butyl (triphenylphosphoranylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC(C)(C)C)C1=CC=CC=C1 ZWZUFQPXYVYAFO-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- WXJFKAOOMXIHNH-UHFFFAOYSA-M [2-oxo-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]-triphenylphosphanium;bromide Chemical compound [Br-].O=C1N(CC(F)(F)F)CCC1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WXJFKAOOMXIHNH-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- NSYKFYWYCHCFDR-HKEIOJSRSA-N benzhydryl (6R)-4-acetamido-3-(hydroxymethyl)-8-oxo-7-phenyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)OC(=O)C1=C(C(S[C@H]2N1C(C2C1=CC=CC=C1)=O)NC(C)=O)CO NSYKFYWYCHCFDR-HKEIOJSRSA-N 0.000 description 1
- WLBRAOUZRDZACO-LFHRXCRSSA-N benzhydryl (6r)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@@H]12)CC=C(C(=O)OC(C=3C=CC=CC=3)C=3C=CC=CC=3)N1C(=O)C2NC(=O)CC1=CC=CC=C1 WLBRAOUZRDZACO-LFHRXCRSSA-N 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- RTXOFQZKPXMALH-GHXIOONMSA-N cefdinir Chemical compound S1C(N)=NC(C(=N\O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 RTXOFQZKPXMALH-GHXIOONMSA-N 0.000 description 1
- 229960003719 cefdinir Drugs 0.000 description 1
- OKBVVJOGVLARMR-QSWIMTSFSA-N cefixime Chemical compound S1C(N)=NC(C(=N\OCC(O)=O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 OKBVVJOGVLARMR-QSWIMTSFSA-N 0.000 description 1
- 229960002129 cefixime Drugs 0.000 description 1
- XAKKNLNAJBNLPC-MAYKBZFQSA-N cefluprenam Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)/C=C/C[N+](C)(CC)CC(N)=O)C([O-])=O)C(=O)C(=N/OCF)\C1=NSC(N)=N1 XAKKNLNAJBNLPC-MAYKBZFQSA-N 0.000 description 1
- UNJFKXSSGBWRBZ-BJCIPQKHSA-N ceftibuten Chemical compound S1C(N)=NC(C(=C\CC(O)=O)\C(=O)N[C@@H]2C(N3C(=CCS[C@@H]32)C(O)=O)=O)=C1 UNJFKXSSGBWRBZ-BJCIPQKHSA-N 0.000 description 1
- 229960004086 ceftibuten Drugs 0.000 description 1
- HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000006324 decarbonylation Effects 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- BVMSMICCSFHCOO-UHFFFAOYSA-N ethyl 2-[chloro(triphenyl)-lambda5-phosphanyl]acetate Chemical compound CCOC(=O)CP(Cl)(c1ccccc1)(c1ccccc1)c1ccccc1 BVMSMICCSFHCOO-UHFFFAOYSA-N 0.000 description 1
- ULLRAXAATZPHIK-UHFFFAOYSA-N ethyl 4-(triphenyl-$l^{5}-phosphanylidene)butanoate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CCCC(=O)OCC)C1=CC=CC=C1 ULLRAXAATZPHIK-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XPYGGHVSFMUHLH-UUSULHAXSA-N falecalcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(O)(C(F)(F)F)C(F)(F)F)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C XPYGGHVSFMUHLH-UUSULHAXSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 1
- LULXBAGMGMJJRW-UHFFFAOYSA-N n,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)CC(=O)N[Si](C)(C)C LULXBAGMGMJJRW-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- 125000006250 trifluoro ethyl amino group Chemical group [H]N(*)C([H])([H])C(F)(F)F 0.000 description 1
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 1
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
- PBGYCOHYTZRVSN-JLOHTSLTSA-N trimethylsilyl (6R)-3-formyl-8-oxo-7-(trimethylsilylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C[Si](C)(C)NC1[C@H]2SCC(C=O)=C(N2C1=O)C(=O)O[Si](C)(C)C PBGYCOHYTZRVSN-JLOHTSLTSA-N 0.000 description 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0085894A AT402072B (de) | 1994-04-25 | 1994-04-25 | Cephemderivate und verfahren zu ihrer herstellung |
| AT85794A AT402927B (de) | 1994-04-25 | 1994-04-25 | Neue cefalosporinderivate, verfahren zu ihrer herstellung und ihre verwendung |
| AT0106694A AT402929B (de) | 1994-05-25 | 1994-05-25 | Neue cephalosporinderivate, verfahren zu ihrer herstellung und ihre verwendung |
| PCT/EP1995/001538 WO1995029182A1 (en) | 1994-04-25 | 1995-04-24 | Cephalosporin synthesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO964493D0 NO964493D0 (no) | 1996-10-23 |
| NO964493L NO964493L (no) | 1996-10-23 |
| NO318020B1 true NO318020B1 (no) | 2005-01-24 |
Family
ID=27146806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19964493A NO318020B1 (no) | 1994-04-25 | 1996-10-23 | Cefemderivater, fremgangsmater for fremstilling derav, anvendelse derav for fremstilling av cefalosporiner samt fremgangsmate for fremstilling av 3-substituert-7-acylamino-cefalosporin. |
Country Status (26)
| Country | Link |
|---|---|
| US (4) | US5856474A (xx) |
| EP (2) | EP0757691B1 (xx) |
| JP (1) | JP3302369B2 (xx) |
| KR (1) | KR100487833B1 (xx) |
| CN (3) | CN1092662C (xx) |
| AT (2) | ATE498627T1 (xx) |
| AU (1) | AU686380B2 (xx) |
| BR (1) | BR9507512A (xx) |
| CA (2) | CA2533837A1 (xx) |
| CY (1) | CY2494B1 (xx) |
| CZ (1) | CZ297565B6 (xx) |
| DE (2) | DE69536140D1 (xx) |
| DK (1) | DK0757691T3 (xx) |
| ES (1) | ES2202362T3 (xx) |
| FI (1) | FI963761A0 (xx) |
| HU (3) | HU0102725D0 (xx) |
| MX (1) | MX9604353A (xx) |
| NO (1) | NO318020B1 (xx) |
| NZ (2) | NZ285084A (xx) |
| PL (2) | PL184773B1 (xx) |
| PT (1) | PT757691E (xx) |
| RU (2) | RU2225411C2 (xx) |
| SI (1) | SI0757691T1 (xx) |
| SK (1) | SK285948B6 (xx) |
| TW (1) | TW427992B (xx) |
| WO (1) | WO1995029182A1 (xx) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6248881B1 (en) * | 1991-03-08 | 2001-06-19 | Biochemie Gmbh | Intermediates and process for the production of 3-vinyl cephalosporins |
| US5856474A (en) * | 1994-04-25 | 1999-01-05 | Biochemie Gesellschaft, M.B.H. | Cephalosporin synthesis |
| US6384214B1 (en) | 1999-07-05 | 2002-05-07 | Basilea Pharmaceutica Ag | Process for producing cephalosporin derivatives |
| US6544555B2 (en) | 2000-02-24 | 2003-04-08 | Advancis Pharmaceutical Corp. | Antibiotic product, use and formulation thereof |
| AU2001267011B2 (en) | 2000-06-21 | 2006-02-02 | Cubist Pharmaceuticals, Inc. | Compositions and methods to improve the oral absorption of antimicrobial agents |
| US7527807B2 (en) * | 2000-06-21 | 2009-05-05 | Cubist Pharmaceuticals, Inc. | Compositions and methods for increasing the oral absorption of antimicrobials |
| US20020068078A1 (en) | 2000-10-13 | 2002-06-06 | Rudnic Edward M. | Antifungal product, use and formulation thereof |
| AU2004258944B2 (en) | 2003-07-21 | 2011-02-10 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
| AU2004258953B2 (en) | 2003-07-21 | 2011-02-10 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
| AU2004258949B2 (en) | 2003-07-21 | 2011-02-10 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
| AU2004264939A1 (en) | 2003-08-11 | 2005-02-24 | Middlebrook Pharmaceuticals, Inc. | Robust pellet |
| CA2535398C (en) | 2003-08-12 | 2013-11-12 | Advancis Pharmaceuticals Corporation | Antibiotic product, use and formulation thereof |
| CA2535780A1 (en) | 2003-08-29 | 2005-03-17 | Advancis Pharmaceuticals Corporation | Antibiotic product, use and formulation thereof |
| AU2004273830B2 (en) | 2003-09-15 | 2011-03-24 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
| EP1771158A4 (en) | 2004-07-02 | 2008-03-12 | Advancis Pharmaceutical Corp | TABLET FOR PULSED DELIVERY |
| EP1877041A2 (en) * | 2005-04-29 | 2008-01-16 | Cubist Pharmaceuticals, Inc. | Therapeutic compositions |
| US8778924B2 (en) | 2006-12-04 | 2014-07-15 | Shionogi Inc. | Modified release amoxicillin products |
| US8357394B2 (en) | 2005-12-08 | 2013-01-22 | Shionogi Inc. | Compositions and methods for improved efficacy of penicillin-type antibiotics |
| US8299052B2 (en) | 2006-05-05 | 2012-10-30 | Shionogi Inc. | Pharmaceutical compositions and methods for improved bacterial eradication |
| CN102448966A (zh) * | 2009-05-25 | 2012-05-09 | 桑多斯股份公司 | 生产头孢托罗酯的方法 |
| ITMI20131820A1 (it) * | 2013-11-04 | 2015-05-05 | Laboratorio Chimico Int Spa | Procedimento per la preparazione di olopatadina |
| CN109180704B (zh) * | 2018-11-19 | 2020-06-05 | 齐鲁安替制药有限公司 | 一种头孢妥仑匹酯的合成方法 |
| TW202126664A (zh) | 2019-09-06 | 2021-07-16 | 奧地利商納畢瓦治療有限責任公司 | 鐵載體頭孢菌素共軛物及其用途 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351596A (en) * | 1966-09-21 | 1967-11-07 | Lilly Co Eli | 3-formyl cephalosporins |
| CH546794A (de) * | 1970-06-18 | 1974-03-15 | Ciba Geigy Ag | Verfahren zur herstellung von cephalosporansaeurederivaten. |
| CH556876A (de) * | 1971-05-19 | 1974-12-13 | Ciba Geigy Ag | Verfahren zur herstellung von cephalosporansaeurederivaten. |
| US3674784A (en) * | 1970-07-27 | 1972-07-04 | Lilly Co Eli | 3-formyl cephalosporin sulfoxides |
| GB1368231A (en) * | 1970-07-31 | 1974-09-25 | Glaxo Lab Ltd | Thio-substituted azetidinones and thiazolino azetidinones |
| US3880851A (en) * | 1971-12-24 | 1975-04-29 | Lilly Co Eli | Antibiotic method |
| CA1109860A (en) * | 1972-12-08 | 1981-09-29 | Shinji Terao | Process for producing lactol-type cephalosporins |
| JPS49109391A (xx) * | 1973-02-28 | 1974-10-17 | ||
| JPS5093989A (xx) * | 1973-10-25 | 1975-07-26 | ||
| JPS5071691A (xx) * | 1973-11-02 | 1975-06-13 | ||
| JPS5129492A (en) * | 1974-09-04 | 1976-03-12 | Sankyo Co | Sefuarosuhorinjudotai no seiho |
| GB1447959A (en) * | 1975-02-27 | 1976-09-02 | Shionogi & Co | Process for preparing cephem aldehyde derivatives |
| US4101658A (en) * | 1975-06-04 | 1978-07-18 | Shionogi & Co., Ltd. | Antibacterial hydrazono cephalosporins |
| GB8821797D0 (en) * | 1988-09-16 | 1988-10-19 | Beecham Group Plc | Novel compounds |
| US5081116A (en) | 1989-04-12 | 1992-01-14 | Yamanouchi Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
| JP2895900B2 (ja) * | 1990-03-08 | 1999-05-24 | 大塚化学株式会社 | ３―ホルミルセフエム誘導体の製造法 |
| DE69231815T2 (de) * | 1991-03-08 | 2001-09-27 | Biochemie Ges.M.B.H., Kundl | Verfahren zur Herstellung von Cephalosporinen und Zwischenprodukte in diesem Verfahren |
| AT400436B (de) * | 1992-11-10 | 1995-12-27 | Biochemie Gmbh | Neues verfahren zur herstellung von 3-vinylcephalosporinverbindungen |
| PT620225E (pt) | 1993-04-16 | 2003-03-31 | Basilea Pharmaceutica Ag | Derivados de cefalosporina |
| US5856474A (en) * | 1994-04-25 | 1999-01-05 | Biochemie Gesellschaft, M.B.H. | Cephalosporin synthesis |
-
1994
- 1994-04-24 US US08/732,501 patent/US5856474A/en not_active Expired - Lifetime
-
1995
- 1995-04-24 DE DE69536140T patent/DE69536140D1/de not_active Expired - Lifetime
- 1995-04-24 CN CN95192741A patent/CN1092662C/zh not_active Expired - Fee Related
- 1995-04-24 NZ NZ285084A patent/NZ285084A/en unknown
- 1995-04-24 SI SI9530680T patent/SI0757691T1/xx unknown
- 1995-04-24 WO PCT/EP1995/001538 patent/WO1995029182A1/en not_active Application Discontinuation
- 1995-04-24 JP JP52736095A patent/JP3302369B2/ja not_active Expired - Fee Related
- 1995-04-24 CZ CZ0310696A patent/CZ297565B6/cs not_active IP Right Cessation
- 1995-04-24 ES ES95917948T patent/ES2202362T3/es not_active Expired - Lifetime
- 1995-04-24 RU RU99124184/04A patent/RU2225411C2/ru not_active IP Right Cessation
- 1995-04-24 EP EP95917948A patent/EP0757691B1/en not_active Expired - Lifetime
- 1995-04-24 PL PL95345367A patent/PL184773B1/pl not_active IP Right Cessation
- 1995-04-24 CA CA002533837A patent/CA2533837A1/en not_active Abandoned
- 1995-04-24 MX MX9604353A patent/MX9604353A/es not_active IP Right Cessation
- 1995-04-24 PL PL95316661A patent/PL182864B1/pl not_active IP Right Cessation
- 1995-04-24 KR KR1019960705992A patent/KR100487833B1/ko not_active IP Right Cessation
- 1995-04-24 DE DE69531203T patent/DE69531203T2/de not_active Expired - Lifetime
- 1995-04-24 HU HU0102725A patent/HU0102725D0/hu unknown
- 1995-04-24 AT AT03012877T patent/ATE498627T1/de not_active IP Right Cessation
- 1995-04-24 AU AU24072/95A patent/AU686380B2/en not_active Ceased
- 1995-04-24 SK SK1357-96A patent/SK285948B6/sk unknown
- 1995-04-24 HU HU0102726A patent/HU0102726D0/hu unknown
- 1995-04-24 AT AT95917948T patent/ATE244247T1/de not_active IP Right Cessation
- 1995-04-24 NZ NZ329984A patent/NZ329984A/en unknown
- 1995-04-24 PT PT95917948T patent/PT757691E/pt unknown
- 1995-04-24 DK DK95917948T patent/DK0757691T3/da active
- 1995-04-24 EP EP03012877A patent/EP1340762B1/en not_active Expired - Lifetime
- 1995-04-24 RU RU96122784/04A patent/RU2150471C1/ru not_active IP Right Cessation
- 1995-04-24 HU HU9602940A patent/HUT75229A/hu unknown
- 1995-04-24 CN CNB011207469A patent/CN1145628C/zh not_active Expired - Fee Related
- 1995-04-24 CN CNB011207523A patent/CN1145629C/zh not_active Expired - Fee Related
- 1995-04-24 CA CA002180829A patent/CA2180829C/en not_active Expired - Fee Related
- 1995-04-24 BR BR9507512-7A patent/BR9507512A/pt not_active IP Right Cessation
- 1995-05-10 TW TW084104620A patent/TW427992B/zh not_active IP Right Cessation
-
1996
- 1996-09-20 FI FI963761A patent/FI963761A0/fi not_active Application Discontinuation
- 1996-10-23 NO NO19964493A patent/NO318020B1/no not_active IP Right Cessation
-
1998
- 1998-09-30 US US09/164,055 patent/US6063917A/en not_active Expired - Fee Related
- 1998-09-30 US US09/163,942 patent/US6034237A/en not_active Expired - Fee Related
- 1998-09-30 US US09/163,660 patent/US6093813A/en not_active Expired - Fee Related
-
2004
- 2004-11-24 CY CY0400084A patent/CY2494B1/xx unknown
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Legal Events
| Date | Code | Title | Description |
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| MM1K | Lapsed by not paying the annual fees |