NL8003003A - Tussenprodukten te gebruiken bij de bereiding van cefalosporine antibiotica. - Google Patents
Tussenprodukten te gebruiken bij de bereiding van cefalosporine antibiotica. Download PDFInfo
- Publication number
- NL8003003A NL8003003A NL8003003A NL8003003A NL8003003A NL 8003003 A NL8003003 A NL 8003003A NL 8003003 A NL8003003 A NL 8003003A NL 8003003 A NL8003003 A NL 8003003A NL 8003003 A NL8003003 A NL 8003003A
- Authority
- NL
- Netherlands
- Prior art keywords
- ceph
- pyridiniummethyl
- amino
- compound
- formula
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 15
- 229930186147 Cephalosporin Natural products 0.000 title description 15
- 229940124587 cephalosporin Drugs 0.000 title description 15
- 150000001780 cephalosporins Chemical class 0.000 title description 10
- 239000003242 anti bacterial agent Substances 0.000 title description 9
- 229940088710 antibiotic agent Drugs 0.000 title description 9
- 239000000543 intermediate Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 79
- -1 halide ion Chemical class 0.000 claims description 62
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 40
- FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 27
- 125000006239 protecting group Chemical group 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 10
- 108090000790 Enzymes Proteins 0.000 claims description 9
- 102000004190 Enzymes Human genes 0.000 claims description 9
- 150000004683 dihydrates Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
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- 230000002255 enzymatic effect Effects 0.000 claims description 2
- 239000002609 medium Substances 0.000 claims description 2
- CLNBJHRIESVYLO-NHSZFOGYSA-N [(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl acetate Chemical compound NC1[C@@H]2N(C=C(CS2)COC(C)=O)C1=O CLNBJHRIESVYLO-NHSZFOGYSA-N 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 25
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
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- 239000007787 solid Substances 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 14
- 238000005917 acylation reaction Methods 0.000 description 13
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- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 229940088598 enzyme Drugs 0.000 description 8
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 6
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- 239000000706 filtrate Substances 0.000 description 6
- 125000002541 furyl group Chemical group 0.000 description 6
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- 238000003756 stirring Methods 0.000 description 6
- 239000000872 buffer Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical group NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 229960003866 cefaloridine Drugs 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 229940113088 dimethylacetamide Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 102000004092 Amidohydrolases Human genes 0.000 description 3
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- 239000004358 Butane-1, 3-diol Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 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 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- CKQQMPJQZXIYMJ-UHFFFAOYSA-N dihydrate;dihydrochloride Chemical compound O.O.Cl.Cl CKQQMPJQZXIYMJ-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005866 tritylation reaction Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7918428 | 1979-05-25 | ||
| GB7918428 | 1979-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8003003A true NL8003003A (nl) | 1980-11-27 |
Family
ID=10505477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8003003A NL8003003A (nl) | 1979-05-25 | 1980-05-23 | Tussenprodukten te gebruiken bij de bereiding van cefalosporine antibiotica. |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US4374983A (en, 2012) |
| JP (2) | JPS5612397A (en, 2012) |
| BE (1) | BE883453A (en, 2012) |
| CH (1) | CH654010A5 (en, 2012) |
| DE (1) | DE3019838A1 (en, 2012) |
| FR (1) | FR2457295A1 (en, 2012) |
| GB (1) | GB2052490B (en, 2012) |
| IT (1) | IT1145686B (en, 2012) |
| NL (1) | NL8003003A (en, 2012) |
| ZA (1) | ZA803093B (en, 2012) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE883453A (fr) * | 1979-05-25 | 1980-11-24 | Glaxo Group Ltd | Composes intermediaires pour la preparation de cephalosporines |
| SE449996B (sv) * | 1979-10-02 | 1987-06-01 | Glaxo Group Ltd | (6r,7r)-7-/(z)-2-(2-aminotiazol-4-yl)-2-(2-karboxiprop-2-oxiimino)acetamidol/-3-(1-pyridiniummetyl)cef-3-em-4-karboxylat i form av en kristallin bishydroklorid farmaceutisk komposition derav samt anvendning som mellanpr |
| AU557274B2 (en) * | 1981-07-17 | 1986-12-18 | Glaxo Group Limited | Cephalosporin antibiotics |
| JPS5859991A (ja) * | 1981-09-14 | 1983-04-09 | Fujisawa Pharmaceut Co Ltd | 新規セフェム化合物 |
| EP0113568B1 (en) * | 1982-12-27 | 1990-04-04 | Eli Lilly And Company | Intermediates for the preparation of ceftazidine, and process for their preparation |
| DE3248281A1 (de) * | 1982-12-28 | 1984-06-28 | Hoechst Ag, 6230 Frankfurt | Kristalisierte cephem-saeureadditionssalze und verfahren zu ihrer herstellung |
| US4540779A (en) * | 1983-06-20 | 1985-09-10 | Eli Lilly And Company | Crystalline 7-(R)-amino-3-(1'pyridiniummethyl)-ceph-3-em-4-carboxylate monohydrochloride monohydrate compound |
| DE3419014A1 (de) * | 1984-05-22 | 1985-11-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 7-amino-3-(3-formamidopyridinium)methyl-3-cephem-4-carboxylat und verwendung zur synthese von ss-lactamantibiotika |
| JPS6160296A (ja) * | 1984-08-30 | 1986-03-27 | Yoshitsuka Seiki:Kk | 全自動粉末成形プレス |
| EP0175544A3 (en) * | 1984-09-17 | 1987-06-03 | Eli Lilly And Company | An improved process for cephalosporin intermediates |
| JP2572382B2 (ja) * | 1984-11-23 | 1997-01-16 | ビオヘミ−・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | セフアロスポリン誘導体の新規製造方法 |
| JPH0649707B2 (ja) * | 1985-03-01 | 1994-06-29 | 第一製薬株式会社 | ３−ピリジニウムメチルセフエム誘導体 |
| US4703118A (en) * | 1985-04-08 | 1987-10-27 | Eli Lilly And Company | Synthesis of 3-iodomethyl cephalosporins |
| US4910301A (en) * | 1985-08-05 | 1990-03-20 | Bristol-Myers Company | Cefepime cephalosporin salts |
| US4714760A (en) * | 1985-08-20 | 1987-12-22 | Bristol-Myers Company | Cephalosporin intermediates |
| US4692518A (en) * | 1985-11-06 | 1987-09-08 | Eli Lilly And Company | Crystalline (7R)-7-amino-3-(1'-pyridiniummethyl)-3-cephem-4-carboxylate monohydrate compound |
| US4665168A (en) * | 1986-04-14 | 1987-05-12 | Eli Lilly And Company | Cephalosporin intermediate |
| CA2101571A1 (en) * | 1992-09-08 | 1994-03-09 | Elizabeth A. Garofalo | Crystalline dihydrate of a cephalosporin dihydrate salt and injectable compositions thereof |
| KR100342600B1 (ko) | 2000-03-06 | 2002-07-04 | 한미정밀화학주식회사 | 신규한 티아졸 화합물 및 그의 제조 방법 |
| KR100392409B1 (ko) | 2000-03-20 | 2003-07-22 | 한미정밀화학주식회사 | 신규한 티아졸 화합물을 이용한 세팔로스포린계항생물질의 제조 방법 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB953695A (en) | 1959-08-04 | 1964-03-25 | Nat Res Dev | Derivatives of cephalosporin c |
| BE638034A (en, 2012) * | 1962-10-03 | |||
| GB1028563A (en) | 1962-12-14 | 1966-05-04 | Glaxo Lab Ltd | Antibacterial derivative of 7-aminocephalosporanic acid |
| GB1052068A (en, 2012) * | 1963-11-04 | |||
| US3422099A (en) * | 1966-02-18 | 1969-01-14 | Bristol Myers Co | 7-(alpha-hydroxy-(2' or 3'-thienyl)-acetamido) cephalosporanic acids and related salts and derivatives |
| GB1522140A (en) * | 1974-12-20 | 1978-08-23 | Glaxo Lab Ltd | Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl cephalosporins methods for their preparation and compositions containing them |
| NL162387C (nl) * | 1977-09-06 | 1980-05-16 | Gist Brocades Nv | Werkwijze voor het bereiden van 6-(d-alpha-amino-p- -hydroxyfenylacetamido)penicillanzuur. |
| CY1168A (en) * | 1978-05-26 | 1983-06-10 | Glaxo Group Ltd | Cephalosporin antibiotics |
| AR229883A1 (es) * | 1978-05-26 | 1983-12-30 | Glaxo Group Ltd | Procedimiento para la preparacion de antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)-acetamido)-3-(1-piridinometil)-cef-3-em-4-carboxilato |
| BE883453A (fr) * | 1979-05-25 | 1980-11-24 | Glaxo Group Ltd | Composes intermediaires pour la preparation de cephalosporines |
| SE449996B (sv) * | 1979-10-02 | 1987-06-01 | Glaxo Group Ltd | (6r,7r)-7-/(z)-2-(2-aminotiazol-4-yl)-2-(2-karboxiprop-2-oxiimino)acetamidol/-3-(1-pyridiniummetyl)cef-3-em-4-karboxylat i form av en kristallin bishydroklorid farmaceutisk komposition derav samt anvendning som mellanpr |
-
1980
- 1980-05-23 BE BE0/200740A patent/BE883453A/fr not_active IP Right Cessation
- 1980-05-23 IT IT48772/80A patent/IT1145686B/it active
- 1980-05-23 NL NL8003003A patent/NL8003003A/nl not_active Application Discontinuation
- 1980-05-23 GB GB8017093A patent/GB2052490B/en not_active Expired
- 1980-05-23 CH CH4078/80A patent/CH654010A5/de not_active IP Right Cessation
- 1980-05-23 JP JP6797480A patent/JPS5612397A/ja active Granted
- 1980-05-23 ZA ZA00803093A patent/ZA803093B/xx unknown
- 1980-05-23 DE DE19803019838 patent/DE3019838A1/de not_active Withdrawn
- 1980-05-23 FR FR8011530A patent/FR2457295A1/fr active Granted
-
1981
- 1981-03-03 US US06/240,104 patent/US4374983A/en not_active Expired - Fee Related
- 1981-03-03 US US06/239,203 patent/US4369313A/en not_active Expired - Lifetime
-
1982
- 1982-09-30 US US06/429,134 patent/US4433141A/en not_active Expired - Lifetime
-
1989
- 1989-06-28 JP JP1164113A patent/JPH0242085A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0242085A (ja) | 1990-02-13 |
| FR2457295B1 (en, 2012) | 1983-11-10 |
| FR2457295A1 (fr) | 1980-12-19 |
| IT1145686B (it) | 1986-11-05 |
| US4374983A (en) | 1983-02-22 |
| JPS5612397A (en) | 1981-02-06 |
| GB2052490B (en) | 1983-09-07 |
| GB2052490A (en) | 1981-01-28 |
| BE883453A (fr) | 1980-11-24 |
| US4369313A (en) | 1983-01-18 |
| DE3019838A1 (de) | 1980-12-04 |
| IT8048772A0 (it) | 1980-05-23 |
| ZA803093B (en) | 1981-07-29 |
| US4433141A (en) | 1984-02-21 |
| JPH0250914B2 (en, 2012) | 1990-11-05 |
| CH654010A5 (de) | 1986-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BT | A notification was added to the application dossier and made available to the public | ||
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |