SE452620B - Forfarande for framstellning av derivat av beta-laktamantibiotika - Google Patents

Forfarande for framstellning av derivat av beta-laktamantibiotika

Info

Publication number: SE452620B
Authority: SE; Sweden
Prior art keywords: group; compound; formula; acid; ylthio
Prior art date: 1981-02-23

Application number

SE8201087A

Other languages

English (en)

Swedish (sv)

Other versions

SE8201087L (sv

Inventor

J Nakazawa

M Kaneko

T Miyaoka

Original Assignee

Sankyo Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-02-23

Filing date

1982-02-22

Publication date

1987-12-07

1981-02-23 Priority claimed from JP56025059A external-priority patent/JPS57139077A/ja

1981-03-27 Priority claimed from JP4485481A external-priority patent/JPS57159789A/ja

1982-02-22 Application filed by Sankyo Co filed Critical Sankyo Co

1982-08-24 Publication of SE8201087L publication Critical patent/SE8201087L/

1987-12-07 Publication of SE452620B publication Critical patent/SE452620B/sv

Links

238000000034 method Methods 0.000 title claims description 31
238000002360 preparation method Methods 0.000 title claims description 6
239000003242 anti bacterial agent Substances 0.000 title 1
229940088710 antibiotic agent Drugs 0.000 title 1
-1 monobromoacetyl Chemical group 0.000 claims description 52
150000001875 compounds Chemical class 0.000 claims description 49
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 29
230000008569 process Effects 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
150000007522 mineralic acids Chemical class 0.000 claims description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
229910052725 zinc Inorganic materials 0.000 claims description 8
239000011701 zinc Substances 0.000 claims description 8
KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229940098779 methanesulfonic acid Drugs 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 3
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
150000003460 sulfonic acids Chemical class 0.000 claims description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
238000009938 salting Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
239000000243 solution Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
239000000047 product Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 6
239000007858 starting material Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
239000013078 crystal Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
150000001266 acyl halides Chemical class 0.000 description 4
239000012467 final product Substances 0.000 description 4
125000004468 heterocyclylthio group Chemical group 0.000 description 4
239000012535 impurity Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000004811 liquid chromatography Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
UCKZMPLVLCKKMO-LHLIQPBNSA-N cephamycin Chemical class S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](C)[C@]21OC UCKZMPLVLCKKMO-LHLIQPBNSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000005924 transacylation reaction Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical class S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 description 1
XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 1
YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
FKJSFKCZZIXQIP-UHFFFAOYSA-N 2-bromo-1-(4-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=C(Br)C=C1 FKJSFKCZZIXQIP-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
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 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000238366 Cephalopoda Species 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
LXWBXEWUSAABOA-UHFFFAOYSA-N Cephamycin-C Natural products S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)C(OC)(NC(=O)CCCC(N)C(O)=O)C21 LXWBXEWUSAABOA-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
101150046432 Tril gene Proteins 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000003782 beta lactam antibiotic agent Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
LXWBXEWUSAABOA-VXSYNFHWSA-N cephamycin C Chemical group S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)[C@@](OC)(NC(=O)CCC[C@@H](N)C(O)=O)[C@H]21 LXWBXEWUSAABOA-VXSYNFHWSA-N 0.000 description 1
150000001782 cephems Chemical class 0.000 description 1
230000008859 change Effects 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
238000012258 culturing Methods 0.000 description 1
PAFZNILMFXTMIY-UHFFFAOYSA-O cyclohexylammonium Chemical compound [NH3+]C1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-O 0.000 description 1
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
FEZFGJCSBWYLCC-UHFFFAOYSA-N dicyclohexylazanium;bromide Chemical compound Br.C1CCCCC1NC1CCCCC1 FEZFGJCSBWYLCC-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000009413 insulation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
244000005700 microbiome Species 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000001012 protector Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
230000035899 viability Effects 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1
150000003952 β-lactams Chemical class 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
- C07D501/36—Methylene radicals, substituted by sulfur atoms
- 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
- C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines
- 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)
Cephalosporin Compounds (AREA)

SE8201087A 1981-02-23 1982-02-22 Forfarande for framstellning av derivat av beta-laktamantibiotika SE452620B (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP56025059A JPS57139077A (en)	1981-02-23	1981-02-23	Eliminating method of protecting group from carboxy group
JP4485481A JPS57159789A (en)	1981-03-27	1981-03-27	Preparation of cephamycin derivative

Publications (2)

Publication Number	Publication Date
SE8201087L SE8201087L (sv)	1982-08-24
SE452620B true SE452620B (sv)	1987-12-07

Family

ID=26362653

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8201087A SE452620B (sv)	1981-02-23	1982-02-22	Forfarande for framstellning av derivat av beta-laktamantibiotika

Country Status (8)

Country	Link
CA (1)	CA1194470A (it)
CH (1)	CH646977A5 (it)
DK (1)	DK162603C (it)
ES (1)	ES8305362A1 (it)
FI (1)	FI72521C (it)
IT (1)	IT1157951B (it)
NL (1)	NL8200708A (it)
SE (1)	SE452620B (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101302226B (zh) *	2008-06-12	2011-01-12	齐鲁安替制药有限公司	头霉素中间体化合物的制备方法
CN113512046B (zh) *	2021-03-31	2023-04-25	西南大学	C-7位卤代酰基头孢化合物、制备方法和应用

1982
- 1982-02-22 DK DK075582A patent/DK162603C/da not_active IP Right Cessation
- 1982-02-22 CH CH108282A patent/CH646977A5/de not_active IP Right Cessation
- 1982-02-22 SE SE8201087A patent/SE452620B/sv unknown
- 1982-02-23 NL NL8200708A patent/NL8200708A/nl not_active Application Discontinuation
- 1982-02-23 IT IT67194/82A patent/IT1157951B/it active
- 1982-02-23 FI FI820582A patent/FI72521C/fi not_active IP Right Cessation
- 1982-02-23 ES ES509837A patent/ES8305362A1/es not_active Expired
- 1982-02-23 CA CA000396796A patent/CA1194470A/en not_active Expired

Also Published As

Publication number	Publication date
IT1157951B (it)	1987-02-18
ES509837A0 (es)	1983-04-01
CA1194470A (en)	1985-10-01
FI72521C (fi)	1987-06-08
NL8200708A (nl)	1982-09-16
CH646977A5 (en)	1984-12-28
ES8305362A1 (es)	1983-04-01
DK162603C (da)	1992-04-06
DK162603B (da)	1991-11-18
IT8267194A0 (it)	1982-02-23
FI72521B (fi)	1987-02-27
SE8201087L (sv)	1982-08-24
DK75582A (da)	1982-08-24
FI820582L (fi)	1982-08-24

Legal Events

Date

Code

Title

Description

1995-01-31

NAL

Patent in force

Ref document number: 8201087-7

Format of ref document f/p: F

Publication	Publication Date	Title
WO2007105253A2 (en)	2007-09-20	PREPARATION OF (1-OXA- OR l-THIA-)3- CEPHEM DERIVATIVES
JPH09512259A (ja)	1997-12-09	セファロスポリン合成
CA1276929C (en)	1990-11-27	Cephalosporin antibacterial agents
US4482710A (en)	1984-11-13	Process for preparing 3-alkoxymethylcephalosporin derivatives
CH642662A5 (de)	1984-04-30	Cephalosporine und verfahren zu deren herstellung.
FI63586B (fi)	1983-03-31	Foerfarande foer framstaellning av 7-beta-(2-oxiimino-2-arylacetamido)-3-(sulfoalkyltetrazol-5-yltiometyl)-3-cefem-4-karboxylsyror med antibakteriell verkan
JP3713282B2 (ja)	2005-11-09	３−（２−置換−ビニル）−セファロスポリンのｚ異性体の選択的製造方法
FI84268B (fi)	1991-07-31	7 -amino-3-propenylcefalosporansyra och dess estrar och ett foerfarande foer framstaellning av dessa.
JP2939129B2 (ja)	1999-08-25	セファロスポリンの合成における中間体
SE452620B (sv)	1987-12-07	Forfarande for framstellning av derivat av beta-laktamantibiotika
AU690482B2 (en)	1998-04-23	Process for producing cephalosporin antibiotics
SE409713B (sv)	1979-09-03	Forfarande for separering av cefalosporin c-emnen fran polysackarid- och proteinhaltiga fororeningar
US4281117A (en)	1981-07-28	Process for 3-chloro cephalosporin nucleus
US5109132A (en)	1992-04-28	Process for the preparation of 3-exomethylene cepham derivatives
US4959495A (en)	1990-09-25	Process for the preparation of intermediates used to produce aminothiazoloximino cephalosporins
JPH0521912B2 (it)	1993-03-25
US5665888A (en)	1997-09-09	Protected aminothiazolylacetic acid derivatives
JP2549494B2 (ja)	1996-10-30	ピリドンイソオキサゾールセフェム化合物及びその製造方法
CA1155835A (en)	1983-10-25	Process for preparing cephalosporin derivatives
EP0045717B1 (en)	1985-09-25	New cephalosporin derivatives, their production and their use
US4237280A (en)	1980-12-02	Intermediate for cephalosporin type compound
US5066799A (en)	1991-11-19	Intermediates for the preparation of aminothiazoloximino cephalosporins
EP0160564A2 (en)	1985-11-06	Process for preparing cephalosporin compounds
JPH0310626B2 (it)	1991-02-14
JPH01308285A (ja)	1989-12-12	β−ラクタム誘導体