PT102295B - Processo para a preparacao do cloridrato de 7-amino-3-vinil-3-cefeme-4-carboxilato de difenilmetilo para utilizacao na preparacao de cefixima - Google Patents

Info

Publication number

PT102295B

PT102295B PT102295A PT10229599A PT102295B PT 102295 B PT102295 B PT 102295B PT 102295 A PT102295 A PT 102295A PT 10229599 A PT10229599 A PT 10229599A PT 102295 B PT102295 B PT 102295B

Authority

PT

Portugal

Prior art keywords

formula

process according

preparation

chlorine

compound

Prior art date

1999-01-29

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• 238000000034 method Methods 0.000 title claims abstract description 17
• 238000002360 preparation method Methods 0.000 title claims abstract description 13
• 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 title claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 12
• -1 aliphatic halogenated hydrocarbon Chemical class 0.000 claims abstract description 11
• JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 claims abstract description 11
• 150000007530 organic bases Chemical class 0.000 claims abstract description 10
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 6
• 150000001298 alcohols Chemical class 0.000 claims abstract description 6
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 6
• 238000006243 chemical reaction Methods 0.000 claims abstract description 6
• 239000000460 chlorine Substances 0.000 claims abstract description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
• 239000012535 impurity Substances 0.000 claims abstract description 5
• 230000003381 solubilizing effect Effects 0.000 claims abstract description 5
• 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 claims abstract description 5
• 229960002129 cefixime Drugs 0.000 claims abstract description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• JPLIYTCALCWKAS-UHFFFAOYSA-N triphenyl-$l^{3}-chlorane Chemical compound C1=CC=CC=C1Cl(C=1C=CC=CC=1)C1=CC=CC=C1 JPLIYTCALCWKAS-UHFFFAOYSA-N 0.000 claims description 5
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
• YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
• 229940035429 isobutyl alcohol Drugs 0.000 claims description 3
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
• PGRIZKHTKNBWQC-FBLFFUNLSA-N benzhydryl (6r)-7-amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@@H]1C(C(N11)=O)N)CC(C=C)=C1C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PGRIZKHTKNBWQC-FBLFFUNLSA-N 0.000 claims description 2
• 150000002009 diols Chemical class 0.000 claims description 2
• 238000009413 insulation Methods 0.000 claims description 2
• 150000003333 secondary alcohols Chemical class 0.000 claims description 2
• 150000003509 tertiary alcohols Chemical class 0.000 claims description 2
• 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 abstract description 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
• 150000001336 alkenes Chemical class 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 230000020176 deacylation Effects 0.000 description 1
• 238000005947 deacylation reaction Methods 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1