CY1895A - Clavulanic acid preparation via certain polyamines - Google Patents
Clavulanic acid preparation via certain polyamines Download PDFInfo
- Publication number
- CY1895A CY1895A CY189596A CY189596A CY1895A CY 1895 A CY1895 A CY 1895A CY 189596 A CY189596 A CY 189596A CY 189596 A CY189596 A CY 189596A CY 1895 A CY1895 A CY 1895A
- Authority
- CY
- Cyprus
- Prior art keywords
- amino
- clavuianic
- alkyl
- acid
- salt
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 30
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 title description 13
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 title description 11
- 229960003324 clavulanic acid Drugs 0.000 title description 2
- 229920000768 polyamine Polymers 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 217
- 150000003839 salts Chemical class 0.000 claims description 151
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 137
- 150000001412 amines Chemical class 0.000 claims description 86
- 238000000034 method Methods 0.000 claims description 86
- 239000000243 solution Substances 0.000 claims description 80
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 125000003277 amino group Chemical group 0.000 claims description 66
- -1 alkali metal salt Chemical class 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 59
- 239000003960 organic solvent Substances 0.000 claims description 49
- 150000002148 esters Chemical class 0.000 claims description 44
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 36
- 239000007864 aqueous solution Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000000746 purification Methods 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- 238000000855 fermentation Methods 0.000 claims description 13
- 230000004151 fermentation Effects 0.000 claims description 13
- 150000002576 ketones Chemical class 0.000 claims 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 claims description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 8
- 239000003792 electrolyte Substances 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 244000005700 microbiome Species 0.000 claims description 6
- 238000002955 isolation Methods 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000003957 anion exchange resin Substances 0.000 claims description 4
- 239000003729 cation exchange resin Substances 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 238000004094 preconcentration Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims 2
- 238000010828 elution Methods 0.000 claims 2
- 239000004210 ether based solvent Substances 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- 229910003002 lithium salt Inorganic materials 0.000 claims 2
- 159000000002 lithium salts Chemical class 0.000 claims 2
- 239000003480 eluent Substances 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 10
- 239000012453 solvate Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 229940090805 clavulanate Drugs 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- ABVRVIZBZKUTMK-JSYANWSFSA-M potassium clavulanate Chemical compound [K+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 ABVRVIZBZKUTMK-JSYANWSFSA-M 0.000 description 5
- 239000011550 stock solution Substances 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 4
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 4
- AZUFHGGGPUUXKI-FLFDDASRSA-N benzyl (2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound O=C([C@@H]1N2C(=O)C[C@H]2O\C1=C/CO)OCC1=CC=CC=C1 AZUFHGGGPUUXKI-FLFDDASRSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 235000019371 penicillin G benzathine Nutrition 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000187433 Streptomyces clavuligerus Species 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000011033 desalting Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical class CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- JMRXTGCDVQLAFM-JSYANWSFSA-M lithium;(2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [Li+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 JMRXTGCDVQLAFM-JSYANWSFSA-M 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- KGSVNOLLROCJQM-UHFFFAOYSA-N 2-(benzylamino)acetic acid Chemical compound OC(=O)CNCC1=CC=CC=C1 KGSVNOLLROCJQM-UHFFFAOYSA-N 0.000 description 2
- DSFGXPJYDCSWTA-UHFFFAOYSA-N 7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CC(O)CN(CCO)C DSFGXPJYDCSWTA-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- SBBWEQLNKVHYCX-JTQLQIEISA-N ethyl L-tyrosinate Chemical compound CCOC(=O)[C@@H](N)CC1=CC=C(O)C=C1 SBBWEQLNKVHYCX-JTQLQIEISA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 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 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229940118318 xanthinol Drugs 0.000 description 2
- HYSOPXHRAHXSFM-UHFFFAOYSA-N (1-methylcyclohexa-2,4-dien-1-yl)methanamine Chemical compound NCC1(C)CC=CC=C1 HYSOPXHRAHXSFM-UHFFFAOYSA-N 0.000 description 1
- MHRYZUJLGUVINC-LURJTMIESA-N (2s)-2-(butylamino)-3-hydroxypropanoic acid Chemical compound CCCCN[C@@H](CO)C(O)=O MHRYZUJLGUVINC-LURJTMIESA-N 0.000 description 1
- GCIINHHRNRLMAT-VIFPVBQESA-N (2s)-3-hydroxy-2-[(4-nitrophenyl)methylamino]propanoic acid Chemical compound OC[C@@H](C(O)=O)NCC1=CC=C([N+]([O-])=O)C=C1 GCIINHHRNRLMAT-VIFPVBQESA-N 0.000 description 1
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
- IWSWFVNUXDVDLT-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-aminoacetate Chemical compound NCC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 IWSWFVNUXDVDLT-UHFFFAOYSA-N 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical compound CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 1
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 1
- VOGRCOIGNHZDSI-UHFFFAOYSA-N 2-(benzylamino)-2-(4-methoxyphenyl)acetic acid Chemical compound C1=CC(OC)=CC=C1C(C(O)=O)NCC1=CC=CC=C1 VOGRCOIGNHZDSI-UHFFFAOYSA-N 0.000 description 1
- LCRCODPYSHSWAR-UHFFFAOYSA-N 2-(benzylazaniumyl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)O)NCC1=CC=CC=C1 LCRCODPYSHSWAR-UHFFFAOYSA-N 0.000 description 1
- HHBSIIRCNFRFSW-UHFFFAOYSA-N 2-(butylamino)-2-phenylacetic acid Chemical compound CCCCNC(C(O)=O)C1=CC=CC=C1 HHBSIIRCNFRFSW-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- OIALIKXMLIAOSN-UHFFFAOYSA-N 2-Propylpyridine Chemical compound CCCC1=CC=CC=N1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 description 1
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- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
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- JNSUUJLFWBSBME-UHFFFAOYSA-N 3-(2-methylpiperidin-1-yl)propan-1-ol Chemical compound CC1CCCCN1CCCO JNSUUJLFWBSBME-UHFFFAOYSA-N 0.000 description 1
- NFQAIWOMJQWGSS-UHFFFAOYSA-N 3-amino-3-methylbutanoic acid Chemical compound CC(C)(N)CC(O)=O NFQAIWOMJQWGSS-UHFFFAOYSA-N 0.000 description 1
- RZJPBQGRCNJYBU-UHFFFAOYSA-N 3-chloropyridin-2-amine Chemical compound NC1=NC=CC=C1Cl RZJPBQGRCNJYBU-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
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- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
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- 239000004475 Arginine Substances 0.000 description 1
- JXYACYYPACQCDM-UHFFFAOYSA-N Benzyl glycinate Chemical compound NCC(=O)OCC1=CC=CC=C1 JXYACYYPACQCDM-UHFFFAOYSA-N 0.000 description 1
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- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
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- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
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- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 1
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- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
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- 241000187747 Streptomyces Species 0.000 description 1
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- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 229960005274 benzocaine Drugs 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
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- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
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- 238000005119 centrifugation Methods 0.000 description 1
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- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- SRMHHEPXZLWKOK-UHFFFAOYSA-N heptan-3-amine Chemical compound CCCCC(N)CC SRMHHEPXZLWKOK-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- HQLZFBUAULNEGP-UHFFFAOYSA-N hexan-3-amine Chemical compound CCCC(N)CC HQLZFBUAULNEGP-UHFFFAOYSA-N 0.000 description 1
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- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
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- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
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- ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- ZKONTOQLRAPWED-UHFFFAOYSA-N n-ethylmorpholin-4-amine Chemical compound CCNN1CCOCC1 ZKONTOQLRAPWED-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005750 substituted cyclic group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- NHBKWZCTSMCKDS-UHFFFAOYSA-N undecan-2-amine Chemical compound CCCCCCCCCC(C)N NHBKWZCTSMCKDS-UHFFFAOYSA-N 0.000 description 1
- PBUBUUWVOLTZGM-UHFFFAOYSA-N undecan-3-amine Chemical compound CCCCCCCCC(N)CC PBUBUUWVOLTZGM-UHFFFAOYSA-N 0.000 description 1
- QPXKYHCFSQPEFS-UHFFFAOYSA-N undecan-4-amine Chemical compound CCCCCCCC(N)CCC QPXKYHCFSQPEFS-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C27/00—Non-skid devices temporarily attachable to resilient tyres or resiliently-tyred wheels
- B60C27/006—Non-skid devices temporarily attachable to resilient tyres or resiliently-tyred wheels provided with protective parts, e.g. rubber elements to protect the rim portion
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C27/00—Non-skid devices temporarily attachable to resilient tyres or resiliently-tyred wheels
- B60C27/06—Non-skid devices temporarily attachable to resilient tyres or resiliently-tyred wheels extending over the complete circumference of the tread, e.g. made of chains or cables
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Mechanical Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929212379A GB9212379D0 (en) | 1992-06-11 | 1992-06-11 | Novel process |
| GB929222841A GB9222841D0 (en) | 1992-10-31 | 1992-10-31 | Novel process |
| GB929226061A GB9226061D0 (en) | 1992-12-14 | 1992-12-14 | Novel process |
| GB929226282A GB9226282D0 (en) | 1992-12-17 | 1992-12-17 | Novel process |
| GB9424595A GB2282810B (en) | 1992-06-11 | 1993-06-07 | Preparation or purification of clavulanic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1895A true CY1895A (en) | 1996-09-27 |
Family
ID=27450891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY189596A CY1895A (en) | 1992-06-11 | 1996-09-27 | Clavulanic acid preparation via certain polyamines |
Country Status (35)
| Country | Link |
|---|---|
| EP (7) | EP0806426A1 (cs) |
| JP (3) | JPH07507324A (cs) |
| KR (1) | KR0162264B1 (cs) |
| CN (3) | CN1037967C (cs) |
| AP (3) | AP474A (cs) |
| AT (3) | ATE157981T1 (cs) |
| AU (3) | AU4342793A (cs) |
| BG (3) | BG60999B1 (cs) |
| CA (2) | CA2160768A1 (cs) |
| CS (1) | CS202194A3 (cs) |
| CY (1) | CY1895A (cs) |
| CZ (5) | CZ54495A3 (cs) |
| DE (6) | DE4345286A1 (cs) |
| DK (5) | DK0672669T3 (cs) |
| ES (3) | ES2095059T3 (cs) |
| FI (7) | FI980631L (cs) |
| GB (2) | GB2287026B (cs) |
| GR (4) | GR950300070T1 (cs) |
| HK (2) | HK1003222A1 (cs) |
| HU (3) | HU9501214D0 (cs) |
| IL (1) | IL105966A (cs) |
| LU (1) | LU88567A1 (cs) |
| MA (1) | MA22907A1 (cs) |
| MX (1) | MX9303441A (cs) |
| MY (1) | MY131501A (cs) |
| NL (1) | NL9320037A (cs) |
| NO (3) | NO943093L (cs) |
| PT (2) | PT101711A (cs) |
| RO (3) | RO111193B1 (cs) |
| RU (1) | RU2081121C1 (cs) |
| SE (5) | SE9404290L (cs) |
| SI (1) | SI9300296B (cs) |
| SK (3) | SK278561B6 (cs) |
| UY (1) | UY24154A1 (cs) |
| WO (1) | WO1993025557A1 (cs) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT400033B (de) | 1992-03-10 | 1995-09-25 | Biochemie Gmbh | Neues verfahren zur isolierung und reinigung von clavulansäure und zur herstellung von pharmakologisch verträglichen salzen derselben |
| AT399155B (de) * | 1992-03-26 | 1995-03-27 | Lek Tovarna Farmacevtskih | Neue alkylendiammonium-diclavulanat-derivate, verfahren zu deren herstellung sowie deren verwendung |
| SI9300296B (sl) | 1992-06-11 | 1998-06-30 | Smithkline Beecham P.L.C. | Postopek in intermedianti za pripravo klavulanske kisline |
| KR100200239B1 (ko) * | 1992-10-21 | 1999-06-15 | 김충환 | 클라불란산 칼륨염의 제조방법 |
| RU2135502C1 (ru) | 1993-03-26 | 1999-08-27 | Гист-Брокейдс Н.В. | Диаминовые соли клавулановой кислоты, способ их получения (варианты), способ получения клавулановой кислоты или ее фармацевтически приемлемой соли, способ очистки клавулановой кислоты или ее соли |
| EP0719778A1 (en) * | 1993-03-26 | 1996-07-03 | Gist-Brocades N.V. | Diamine salts of clavulanic acid |
| US5741903A (en) * | 1993-03-26 | 1998-04-21 | Gist-Brocades N.V. | Diamine salts for purification of clavulanic acid |
| US5821364A (en) * | 1993-03-26 | 1998-10-13 | Gist-Brocades N.V. | Diamine salts of clavulanic acid |
| US5760218A (en) * | 1993-03-26 | 1998-06-02 | Gist-Brocades N.V. | Diamine salts of clavulanic acid |
| ATE198892T1 (de) | 1993-11-17 | 2001-02-15 | Biochemie Gmbh | Trennung von cephalosporinisomeren |
| SI9400107A (en) | 1994-03-02 | 1995-10-31 | Lek Tovarna Farmacevtskih | New process of the isolation of clavulanic acid and its pharmaceutical salts from fermented broth of streptomyces sp.p 6621 ferm p 2804. |
| GB9426261D0 (en) * | 1994-12-24 | 1995-02-22 | Spurcourt Ltd | Clavulanic acid salts |
| JPH11501023A (ja) * | 1995-02-25 | 1999-01-26 | スパーコート リミテッド | クラブラン酸塩 |
| SI9500134B (sl) * | 1995-04-20 | 2004-04-30 | Lek, | Postopek za pripravo čistih alkalijskih soli klavulanske kisline |
| GB9515809D0 (en) * | 1995-08-02 | 1995-10-04 | Smithkline Beecham Plc | Process |
| SI9500265A1 (en) | 1995-08-28 | 1997-02-28 | Lek Tovarna Farmacevtskih | Process for purification of the aqueous fermented broth filtrate of streptomyces sp. p 6621 ferm p 2804 by ultrafiltration |
| AT403375B (de) * | 1995-11-15 | 1998-01-26 | Biochemie Gmbh | Verfahren zur fällung von alkalisalzen der clavulansäure |
| ZA975198B (en) | 1996-06-13 | 1997-12-15 | Smithkline Beecham Corp | Improved process for preparing potassium clavulanate. |
| EP0937084A1 (en) * | 1996-11-11 | 1999-08-25 | Gist-Brocades B.V. | Process for the preparation of salts and esters of clavulanic acid |
| AT404728B (de) * | 1996-11-27 | 1999-02-25 | Biochemie Gmbh | Verfahren zur herstellung von clavulansäure-aminsalzen |
| DZ2456A1 (fr) * | 1997-04-04 | 2003-01-18 | Smithkline Beecham Plc | Procédé de préparation de sels de l'acide clavulanique. |
| EP1095046A1 (en) * | 1998-07-16 | 2001-05-02 | Dsm N.V. | Improved process for the preparation of salts and esters of clavulanic acid |
| US6440708B1 (en) * | 1998-09-29 | 2002-08-27 | Dsm N.V. | Fermentation of clavulanic acid at a controlled level of ammonia |
| DE19917428A1 (de) * | 1999-04-19 | 2000-10-26 | Clariant Gmbh | Flammwidrige phosphormodifizierte Epoxidharze |
| GB0003305D0 (en) | 2000-02-15 | 2000-04-05 | Zeneca Ltd | Pyrimidine derivatives |
| DK1284978T4 (da) | 2000-05-13 | 2009-01-05 | Smithkline Beecham Plc | Fremgangsmåde til oprensning af et salt af clavulansyre |
| ITMI20011764A1 (it) | 2001-08-10 | 2003-02-10 | Dinamite Dipharma Spa | Metodo per l'ottenimento del pemirolast ad elevata purezza |
| GB201010439D0 (en) * | 2010-06-21 | 2010-08-04 | Arch Timber Protection Ltd | A method |
| CN103304583B (zh) * | 2013-07-09 | 2016-01-20 | 山东新时代药业有限公司 | 一种从克拉维酸胺盐结晶母液中回收克拉维酸的方法 |
| CN105384758B (zh) * | 2015-12-01 | 2018-05-01 | 国药集团威奇达药业有限公司 | 克拉维酸胺盐的制备方法 |
| EP3613866B1 (en) | 2017-04-19 | 2022-12-14 | Nippon Light Metal Company, Ltd. | Al-si-fe aluminum alloy casting material and production method therefor |
| CN109305978A (zh) * | 2017-07-26 | 2019-02-05 | 山东睿鹰先锋制药有限公司 | 一种制备克拉维酸盐的新方法 |
| CN116283498B (zh) * | 2023-03-07 | 2025-02-28 | 国药集团威奇达药业有限公司 | 从克拉维酸钾生产废液中回收有机溶剂的方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1508977A (en) * | 1974-04-20 | 1978-04-26 | Beecham Group Ltd | Beta-lactam antibiotic from streptomyces clavuligerus |
| GB1507978A (en) | 1974-03-28 | 1978-04-19 | Dunlop Ltd | Pneumatic tyre and wheel rim assemblies |
| GB1543563A (en) | 1975-02-07 | 1979-04-04 | Glaxo Lab Ltd | Beta-lactam antibiotic in purified form |
| GB1508978A (en) | 1975-04-11 | 1978-04-26 | Beecham Group Ltd | Esters of clavulanic acid |
| GB1578739A (en) | 1976-07-23 | 1980-11-05 | Beecham Group Ltd | Amine salts of clavulanic acid methods for their preparation and compositions containing them |
| EP0002312B1 (en) * | 1977-11-26 | 1982-02-03 | Beecham Group Plc | Derivatives of clavulanic acid and pharmaceutical compositions containing them |
| BE862211A (fr) * | 1977-12-22 | 1978-06-22 | Beecham Group Ltd | Agents antibacteriens |
| JPS5562993A (en) | 1978-11-07 | 1980-05-12 | Idemitsu Petrochem Co Ltd | Operation of olefin manufacturing equipment |
| JPS55162993A (en) * | 1979-06-07 | 1980-12-18 | Sanraku Inc | Preparation of culavulanic acid |
| EP0026044B1 (en) | 1979-08-24 | 1983-06-08 | Beecham Group Plc | Amine salt of clavulanic acid, its preparation and use |
| NZ213963A (en) * | 1984-10-27 | 1989-01-06 | Antibioticos Sa | Production of clavulanic acid |
| ES2010143A6 (es) * | 1989-03-01 | 1989-10-16 | Pharma Mar S A Pharmar | Un nuevo procedimiento de obtencion del acido z(2r,5r)-3-(2-hiadroxietiliden)-7- oxo-4-oxa-1-azabiciclo(3,2,0) -heptano-2-carboxilico y de sales estares farmaceutiacamente aceptables del mismo,a partir de caldos de fermentacion de streptomyces, sp. |
| FR2644543A1 (cs) | 1989-03-17 | 1990-09-21 | Renault | |
| PT94908B (pt) | 1990-08-03 | 1998-05-29 | Portela & Ca Lda | Processo para a preparacao de derivados carboxilicos beta-lactamicos altamente purificados estaveis e hipoalergenicos |
| AT400033B (de) * | 1992-03-10 | 1995-09-25 | Biochemie Gmbh | Neues verfahren zur isolierung und reinigung von clavulansäure und zur herstellung von pharmakologisch verträglichen salzen derselben |
| AT399155B (de) * | 1992-03-26 | 1995-03-27 | Lek Tovarna Farmacevtskih | Neue alkylendiammonium-diclavulanat-derivate, verfahren zu deren herstellung sowie deren verwendung |
| SI9300296B (sl) | 1992-06-11 | 1998-06-30 | Smithkline Beecham P.L.C. | Postopek in intermedianti za pripravo klavulanske kisline |
| KR100200239B1 (ko) * | 1992-10-21 | 1999-06-15 | 김충환 | 클라불란산 칼륨염의 제조방법 |
| GB9305565D0 (en) * | 1993-03-18 | 1993-05-05 | Smithkline Beecham Plc | Novel compounds and processes |
| EP0719778A1 (en) * | 1993-03-26 | 1996-07-03 | Gist-Brocades N.V. | Diamine salts of clavulanic acid |
| EP0887178A1 (de) | 1997-06-27 | 1998-12-30 | Pamag Ag | Verfahren zum Bündeln von Seitenfaltbeuteln und Vorrichtung zur Durchführung des Verfahrens |
-
1993
- 1993-06-03 SI SI9300296A patent/SI9300296B/sl unknown
- 1993-06-07 EP EP97201887A patent/EP0806426A1/en not_active Withdrawn
- 1993-06-07 DE DE4345286A patent/DE4345286A1/de not_active Ceased
- 1993-06-07 EP EP95117448A patent/EP0699682A1/en not_active Withdrawn
- 1993-06-07 ES ES93913311T patent/ES2095059T3/es not_active Expired - Lifetime
- 1993-06-07 FI FI980631A patent/FI980631L/fi not_active Application Discontinuation
- 1993-06-07 NL NL9320037A patent/NL9320037A/nl not_active Application Discontinuation
- 1993-06-07 SK SK994-94A patent/SK278561B6/sk unknown
- 1993-06-07 CZ CZ95544A patent/CZ54495A3/cs unknown
- 1993-06-07 PT PT101711A patent/PT101711A/pt not_active Application Discontinuation
- 1993-06-07 EP EP95201084A patent/EP0672669B1/en not_active Expired - Lifetime
- 1993-06-07 CZ CZ942676A patent/CZ267694A3/cs unknown
- 1993-06-07 GB GB9508497A patent/GB2287026B/en not_active Expired - Fee Related
- 1993-06-07 JP JP6501253A patent/JPH07507324A/ja active Pending
- 1993-06-07 FI FI944031A patent/FI944031A7/fi not_active Application Discontinuation
- 1993-06-07 EP EP96202593A patent/EP0747383A3/en not_active Withdrawn
- 1993-06-07 RO RO95-00880A patent/RO111193B1/ro unknown
- 1993-06-07 HK HK98101976A patent/HK1003222A1/en not_active IP Right Cessation
- 1993-06-07 EP EP95201085A patent/EP0672670B1/en not_active Revoked
- 1993-06-07 AT AT95201084T patent/ATE157981T1/de not_active IP Right Cessation
- 1993-06-07 HU HU9501214A patent/HU9501214D0/hu not_active Application Discontinuation
- 1993-06-07 EP EP97201652A patent/EP0801069A1/en not_active Withdrawn
- 1993-06-07 EP EP93913311A patent/EP0644887B1/en not_active Expired - Lifetime
- 1993-06-07 DE DE69306574T patent/DE69306574T2/de not_active Expired - Fee Related
- 1993-06-07 SK SK1533-94A patent/SK278367B6/sk unknown
- 1993-06-07 CA CA002160768A patent/CA2160768A1/en not_active Abandoned
- 1993-06-07 RU RU9595112522A patent/RU2081121C1/ru active
- 1993-06-07 DK DK95201084.1T patent/DK0672669T3/da active
- 1993-06-07 CZ CZ942675A patent/CZ267594A3/cs unknown
- 1993-06-07 WO PCT/GB1993/001206 patent/WO1993025557A1/en not_active Application Discontinuation
- 1993-06-07 DK DK95201085.8T patent/DK0672670T3/da active
- 1993-06-07 HU HU9500610A patent/HU212583B/hu not_active IP Right Cessation
- 1993-06-07 KR KR1019940703225A patent/KR0162264B1/ko not_active Expired - Fee Related
- 1993-06-07 AT AT93913311T patent/ATE146180T1/de not_active IP Right Cessation
- 1993-06-07 ES ES95201085T patent/ES2080710T3/es not_active Expired - Lifetime
- 1993-06-07 ES ES95201084T patent/ES2106615T3/es not_active Expired - Lifetime
- 1993-06-07 AU AU43427/93A patent/AU4342793A/en not_active Abandoned
- 1993-06-07 CZ CZ951254A patent/CZ281102B6/cs not_active IP Right Cessation
- 1993-06-07 GB GB9508496A patent/GB2287025B/en not_active Expired - Fee Related
- 1993-06-07 CA CA002117538A patent/CA2117538A1/en not_active Abandoned
- 1993-06-07 DK DK93913311.2T patent/DK0644887T3/da active
- 1993-06-07 AT AT95201085T patent/ATE134192T1/de not_active IP Right Cessation
- 1993-06-07 RO RO94-01806A patent/RO111191B1/ro unknown
- 1993-06-07 CZ CZ96193A patent/CZ19396A3/cs unknown
- 1993-06-07 DE DE4392664T patent/DE4392664T1/de not_active Withdrawn
- 1993-06-07 PT PT101710A patent/PT101710A/pt not_active IP Right Cessation
- 1993-06-07 HU HU9402405A patent/HUT69374A/hu unknown
- 1993-06-07 FI FI982790A patent/FI982790A7/fi unknown
- 1993-06-07 SK SK1532-94A patent/SK278520B6/sk unknown
- 1993-06-07 CS CZ942021A patent/CS202194A3/cs unknown
- 1993-06-07 FI FI980630A patent/FI980630A0/fi not_active Application Discontinuation
- 1993-06-07 DE DE4345311A patent/DE4345311C1/de not_active Expired - Lifetime
- 1993-06-07 RO RO95-00659A patent/RO111192B1/ro unknown
- 1993-06-07 DE DE69301571T patent/DE69301571T2/de not_active Expired - Fee Related
- 1993-06-07 DE DE69313869T patent/DE69313869T2/de not_active Expired - Fee Related
- 1993-06-08 MY MYPI93001142A patent/MY131501A/en unknown
- 1993-06-09 MX MX9303441A patent/MX9303441A/es not_active IP Right Cessation
- 1993-06-09 IL IL105966A patent/IL105966A/xx not_active IP Right Cessation
- 1993-06-09 MA MA23206A patent/MA22907A1/fr unknown
- 1993-06-10 CN CN93106612A patent/CN1037967C/zh not_active Expired - Fee Related
- 1993-06-10 AP APAP/P/1995/000738A patent/AP474A/en active
- 1993-06-10 AP APAP/P/1993/000537A patent/AP471A/en active
- 1993-06-10 AP APAP/P/1995/000737A patent/AP473A/en active
-
1994
- 1994-08-22 NO NO943093A patent/NO943093L/no unknown
- 1994-10-20 BG BG99131A patent/BG60999B1/bg unknown
- 1994-10-20 BG BG99639/95A patent/BG61306B1/bg unknown
- 1994-12-07 LU LU88567A patent/LU88567A1/fr unknown
- 1994-12-08 DK DK140694A patent/DK140694A/da not_active Application Discontinuation
- 1994-12-09 SE SE9404290A patent/SE9404290L/xx not_active Application Discontinuation
-
1995
- 1995-02-27 NO NO950758A patent/NO950758D0/no unknown
- 1995-02-27 SE SE9500718A patent/SE9500718L/xx not_active Application Discontinuation
- 1995-03-09 AU AU14737/95A patent/AU680099B2/en not_active Ceased
- 1995-03-24 FI FI951414A patent/FI103973B1/fi active
- 1995-03-31 JP JP7075492A patent/JPH08134072A/ja active Pending
- 1995-04-26 SE SE9501544A patent/SE503077C2/sv not_active IP Right Cessation
- 1995-04-28 CN CN95104832A patent/CN1041934C/zh not_active Expired - Fee Related
- 1995-05-03 NO NO951725A patent/NO178499C/no not_active IP Right Cessation
- 1995-05-15 CN CN95104675A patent/CN1036592C/zh not_active Expired - Fee Related
- 1995-05-16 BG BG99640A patent/BG61190B1/bg unknown
- 1995-05-19 JP JP7121206A patent/JPH08157480A/ja active Pending
- 1995-06-08 FI FI952820A patent/FI96952C/fi active
- 1995-06-15 DK DK068595A patent/DK170569B1/da not_active IP Right Cessation
-
1996
- 1996-01-11 HK HK6996A patent/HK6996A/xx not_active IP Right Cessation
- 1996-01-30 UY UY24154A patent/UY24154A1/es unknown
- 1996-01-31 GR GR950300070T patent/GR950300070T1/el unknown
- 1996-02-15 GR GR960400402T patent/GR3019006T3/el unknown
- 1996-02-29 SE SE9600797A patent/SE504220C2/sv not_active IP Right Cessation
- 1996-04-22 FI FI961739A patent/FI104488B/fi active
- 1996-09-27 CY CY189596A patent/CY1895A/en unknown
- 1996-12-12 GR GR960403146T patent/GR3022006T3/el unknown
-
1997
- 1997-02-14 AU AU14716/97A patent/AU681569B3/en not_active Revoked
- 1997-09-09 GR GR970402308T patent/GR3024666T3/el unknown
- 1997-11-19 SE SE9704244A patent/SE9704244D0/xx unknown
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