CA1155835A - Procede de preparation de la cephalosporine - Google Patents

Procede de preparation de la cephalosporine

Info

Publication number: CA1155835A
Authority: CA; Canada
Prior art keywords: group; formula; compound; iii; epoxy
Prior art date: 1980-10-24
Legal status (The legal status 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 status listed.): Expired

Application number

CA000388592A

Other languages

English (en)

Inventor

Junichi Nakazawa

Masanao Kaneko

Takeo Miyaoka

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sankyo Co Ltd

Original Assignee

Sankyo Co Ltd

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.)

1980-10-24

Filing date

1981-10-23

Publication date

1983-10-25

1981-10-23 Application filed by Sankyo Co Ltd filed Critical Sankyo Co Ltd

1983-10-25 Application granted granted Critical

1983-10-25 Publication of CA1155835A publication Critical patent/CA1155835A/fr

Status Expired legal-status Critical Current

Links

229930186147 Cephalosporin Natural products 0.000 title claims abstract description 8
229940124587 cephalosporin Drugs 0.000 title claims abstract description 8
150000001780 cephalosporins Chemical class 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title claims abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 48
-1 1H-tetrazol-5-yl group Chemical group 0.000 claims abstract description 38
239000002253 acid Substances 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
125000004849 alkoxymethyl group Chemical group 0.000 claims abstract description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 10
239000002904 solvent Substances 0.000 claims abstract description 10
125000002252 acyl group Chemical group 0.000 claims abstract description 9
150000008282 halocarbons Chemical class 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims abstract description 3
125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 3
125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 25
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 8
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
KSLSZOOZWRMSAP-UHFFFAOYSA-N 2-[(4-chlorophenoxy)methyl]oxirane Chemical compound C1=CC(Cl)=CC=C1OCC1OC1 KSLSZOOZWRMSAP-UHFFFAOYSA-N 0.000 claims description 2
CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 claims description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 2
238000005924 transacylation reaction Methods 0.000 abstract description 11
150000002148 esters Chemical class 0.000 abstract description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 14
239000000243 solution Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
150000002118 epoxides Chemical class 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
238000003756 stirring Methods 0.000 description 5
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 4
239000007864 aqueous solution Substances 0.000 description 4
LXWBXEWUSAABOA-VXSYNFHWSA-N cephamycin C Chemical compound 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 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
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
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
239000011230 binding agent 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
238000003379 elimination reaction Methods 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000006884 silylation reaction Methods 0.000 description 2
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 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
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
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 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
GLYOPNLBKCBTMI-UHFFFAOYSA-N [2-chloro-2-(1-chloro-2-phenylethoxy)ethyl]benzene Chemical compound C=1C=CC=CC=1CC(Cl)OC(Cl)CC1=CC=CC=C1 GLYOPNLBKCBTMI-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
NGXUUAFYUCOICP-UHFFFAOYSA-N aminometradine Chemical group CCN1C(=O)C=C(N)N(CC=C)C1=O NGXUUAFYUCOICP-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001782 cephems Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
229940061627 chloromethyl methyl ether Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
PAFZNILMFXTMIY-UHFFFAOYSA-O cyclohexylammonium Chemical compound [NH3+]C1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-O 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 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
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007689 inspection Methods 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical compound CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- C07D501/57—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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)

CA000388592A 1980-10-24 1981-10-23 Procede de preparation de la cephalosporine Expired CA1155835A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP149112/80		1980-10-24
JP55149112A JPS5772986A (en)	1980-10-24	1980-10-24	Production of cephalosporin derviative

Publications (1)

Publication Number	Publication Date
CA1155835A true CA1155835A (fr)	1983-10-25

Family

ID=15467965

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000388592A Expired CA1155835A (fr)	1980-10-24	1981-10-23	Procede de preparation de la cephalosporine

Country Status (7)

Country	Link
JP (1)	JPS5772986A (fr)
CA (1)	CA1155835A (fr)
CH (1)	CH649088A5 (fr)
ES (1)	ES8303430A1 (fr)
FI (1)	FI72122C (fr)
IT (1)	IT1144849B (fr)
NL (1)	NL8104831A (fr)

1980
- 1980-10-24 JP JP55149112A patent/JPS5772986A/ja active Granted
1981
- 1981-10-23 IT IT68386/81A patent/IT1144849B/it active
- 1981-10-23 CH CH6792/81A patent/CH649088A5/de not_active IP Right Cessation
- 1981-10-23 CA CA000388592A patent/CA1155835A/fr not_active Expired
- 1981-10-23 ES ES506532A patent/ES8303430A1/es not_active Expired
- 1981-10-23 FI FI813320A patent/FI72122C/fi not_active IP Right Cessation
- 1981-10-26 NL NL8104831A patent/NL8104831A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
FI72122C (fi)	1987-04-13
IT8168386A0 (it)	1981-10-23
IT1144849B (it)	1986-10-29
ES506532A0 (es)	1983-02-01
FI72122B (fi)	1986-12-31
JPH0157116B2 (fr)	1989-12-04
CH649088A5 (en)	1985-04-30
FI813320L (fi)	1982-04-25
ES8303430A1 (es)	1983-02-01
JPS5772986A (en)	1982-05-07
NL8104831A (nl)	1982-05-17

Legal Events

Date	Code	Title	Description
2000-10-25	MKEX	Expiry

Publication	Publication Date	Title
US4298529A (en)	1981-11-03	Alkoxyimino dioxy butyric acid derivatives
US5183929A (en)	1993-02-02	Method for production of T-butyl 3-oxobutyrates and their use
US4012382A (en)	1977-03-15	α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives
GB1599722A (en)	1981-10-07	Cephalosporin derivatives
US4482710A (en)	1984-11-13	Process for preparing 3-alkoxymethylcephalosporin derivatives
KR870001986B1 (ko)	1987-10-24	세팔로스포린 유도체의 제조방법
EP0043546B1 (fr)	1986-01-29	7-Oxo-céphalosporines et 6-oxo-pénicillines, leurs homologues et procédé pour leur préparation
US4245088A (en)	1981-01-13	Novel 3-acyloxymethyl-cephem compounds useful as intermediates for preparing cephalosporin antibiotics
US4695639A (en)	1987-09-22	Thiazole derivatives
DK163584B (da)	1992-03-16	7-amino-3-propenylcephalosporinsyrederivater samt fremgangsmaade til fremstilling deraf
CA1050531A (fr)	1979-03-13	Methode pour la preparation de derives de la cephalosporine
AU690482B2 (en)	1998-04-23	Process for producing cephalosporin antibiotics
US4564676A (en)	1986-01-14	Process for preparing cephalosporin derivatives
CA1155835A (fr)	1983-10-25	Procede de preparation de la cephalosporine
US4118563A (en)	1978-10-03	Production of 7-(2-aminomethylphenylacetamido-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid
EP0045717B1 (fr)	1985-09-25	Dérivés de céphalosporine, leur préparation et leur application
US4959495A (en)	1990-09-25	Process for the preparation of intermediates used to produce aminothiazoloximino cephalosporins
EP0029202A1 (fr)	1981-05-27	Esters de tétrazol-5-thiol et procédé de préparation de céphamandole les utilisant
FI72521C (fi)	1987-06-08	Foerfarande foer framstaellning av cefalosporinderivat.
KR910005230B1 (ko)	1991-07-24	아제티디논의 제조방법
US3998816A (en)	1976-12-21	7-[5-N-(n-Butoxyethoxy carbonyl and 2-chloroethoxy carbonyl)-amino] cephalosporins C
CA1174233A (fr)	1984-09-11	Cetohydroxyiminocephalosporines
EP0397212A1 (fr)	1990-11-14	Procédé de préparation de céphalosporines
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