CA1055925A - N-formylcephalosporine a et c et procede de production - Google Patents

N-formylcephalosporine a et c et procede de production

Info

Publication number: CA1055925A
Authority: CA; Canada
Prior art keywords: formylcephalosporin; imino; cephalosporin; agent; group
Prior art date: 1974-09-30
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

CA236,028A

Other languages

English (en)

Inventor

Shigeo Seki

Masao Hirayama

Kenji Kawamura

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.)

Meiji Seika Kaisha Ltd

Original Assignee

Meiji Seika Kaisha 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.)

1974-09-30

Filing date

1975-09-22

Publication date

1979-06-05

1974-09-30 Priority claimed from JP11163474A external-priority patent/JPS5139690A/ja

1975-03-11 Priority claimed from JP2859575A external-priority patent/JPS51105089A/ja

1975-09-22 Application filed by Meiji Seika Kaisha Ltd filed Critical Meiji Seika Kaisha Ltd

1979-06-05 Application granted granted Critical

1979-06-05 Publication of CA1055925A publication Critical patent/CA1055925A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title description 6
HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 claims abstract description 41
239000003795 chemical substances by application Substances 0.000 claims abstract description 31
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims abstract description 24
125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 3
150000001768 cations Chemical class 0.000 claims abstract 3
238000000034 method Methods 0.000 claims description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
239000003463 adsorbent Substances 0.000 claims description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
238000006170 formylation reaction Methods 0.000 claims description 11
239000011541 reaction mixture Substances 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
230000022244 formylation Effects 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 7
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 6
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 6
150000007530 organic bases Chemical class 0.000 claims description 6
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
239000003957 anion exchange resin Substances 0.000 claims description 4
229920001429 chelating resin Polymers 0.000 claims description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 claims description 2
WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 claims description 2
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
238000007710 freezing Methods 0.000 claims description 2
230000008014 freezing Effects 0.000 claims description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
229910000077 silane Inorganic materials 0.000 claims description 2
MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 claims 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
239000005977 Ethylene Substances 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
238000005658 halogenation reaction Methods 0.000 claims 1
229960004592 isopropanol Drugs 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 13
HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 description 33
239000000243 solution Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
239000000203 mixture Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 18
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000011347 resin Substances 0.000 description 9
229920005989 resin Polymers 0.000 description 9
239000000047 product Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000002904 solvent Substances 0.000 description 7
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 6
-1 alkali metal salt Chemical class 0.000 description 6
150000001780 cephalosporins Chemical group 0.000 description 6
238000001816 cooling Methods 0.000 description 6
235000019253 formic acid Nutrition 0.000 description 6
125000003277 amino group Chemical group 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000002253 acid Substances 0.000 description 4
239000003513 alkali Substances 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000012531 culture fluid Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
229930186147 Cephalosporin Natural products 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229940124587 cephalosporin Drugs 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000010828 elution Methods 0.000 description 3
239000012535 impurity Substances 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000001099 ammonium carbonate Substances 0.000 description 2
235000012501 ammonium carbonate Nutrition 0.000 description 2
239000002585 base Substances 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
244000005700 microbiome Species 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
238000005375 photometry Methods 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
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 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000007547 defect Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000004224 protection Effects 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
JJPVWQWOOQYHCB-UHFFFAOYSA-N triethyl(phenyl)azanium Chemical class CC[N+](CC)(CC)C1=CC=CC=C1 JJPVWQWOOQYHCB-UHFFFAOYSA-N 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
238000002211 ultraviolet spectrum 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
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
- 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
- C07D501/02—Preparation
- C07D501/12—Separation; Purification

Landscapes

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

CA236,028A 1974-09-30 1975-09-22 N-formylcephalosporine a et c et procede de production Expired CA1055925A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP11163474A JPS5139690A (en)	1974-09-30	1974-09-30	nn horumirusefuarosuhorinc no seizoho
JP2859575A JPS51105089A (en)	1975-03-11	1975-03-11	77 aminosefuarosuhoransannoseiho

Publications (1)

Publication Number	Publication Date
CA1055925A true CA1055925A (fr)	1979-06-05

Family

ID=26366736

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA236,028A Expired CA1055925A (fr)	1974-09-30	1975-09-22	N-formylcephalosporine a et c et procede de production

Country Status (4)

Country	Link
CA (1)	CA1055925A (fr)
DE (1)	DE2543680A1 (fr)
FR (1)	FR2286142A1 (fr)
GB (1)	GB1491364A (fr)

1975
- 1975-09-17 GB GB3815375A patent/GB1491364A/en not_active Expired
- 1975-09-22 CA CA236,028A patent/CA1055925A/fr not_active Expired
- 1975-09-30 FR FR7529917A patent/FR2286142A1/fr not_active Withdrawn
- 1975-09-30 DE DE19752543680 patent/DE2543680A1/de active Pending

Also Published As

Publication number	Publication date
DE2543680A1 (de)	1976-04-22
FR2286142A1 (fr)	1976-04-23
GB1491364A (en)	1977-11-09

Publication	Publication Date	Title
JPS5946954B2 (ja)	1984-11-15	抗生物質の製法
SE453507B (sv)	1988-02-08	7-amino-3-(1-karboxi-(legre alkyl)-tetrazol-5-yltiometyl)-3-cefem-4-karboxylsyror till anvendning som mellanprodukter for framstellning av motsvarande 7-acylamido-cefalosporiner
US3957773A (en)	1976-05-18	Process for preparing cephalosporin compounds from 7-adca
US4003896A (en)	1977-01-18	Method of preparing a sparingly soluble complex of cephalexin
CA1055925A (fr)	1979-06-05	N-formylcephalosporine a et c et procede de production
US4387232A (en)	1983-06-07	Process for preparing N-acylcarnosine
US4036833A (en)	1977-07-19	7-[(5'-N-methylthioacetamido)-adipoamido] cephalosporin derivatives
US3931161A (en)	1976-01-06	Cephalosporin derivatives
US4076745A (en)	1978-02-28	Process for calcium salts α-ketocarboxylic acids
IL26135A (en)	1970-06-17	Esters of 7-aminocephalosporanic acid and their preparation
CA1069120A (fr)	1980-01-01	Preparation de derives de l'acide 7-aminocephalosporanique
US4204058A (en)	1980-05-20	Process for obtaining cephalosporin C and the salts and derivatives thereof from culture filtrates or culture solutions
US3983109A (en)	1976-09-28	Process for recovering cephalosporin C from A fermentation broth as the N-(p-nitrobenzoyl) derivative
KR830001969B1 (ko)	1983-09-29	6―｛D―(―) α-(4―에틸-2. 3-디옥소-1 피페라지노카보닐아미노) 페닐(또는 하이드록시페닐)아세트아미도 페니실란산 및 그 염의 제조방법
EP0166580A2 (fr)	1986-01-02	Préparation de ceftazidine
EP0108545B1 (fr)	1986-12-17	Procédé et intermédiaires pour la préparation de l'ester 1,1-dioxopénicillanoylméthylique de l'acide 6-bêta-aminopénicillanique
CA1071189A (fr)	1980-02-05	Procede pour la production de nouveaux produits chimiques et procede pour la production de composes de 6-(p-hydroxyphenylglycilamido)-penam ou de 7-(p-hydroxyphenylglycilamido)-cephem
US4091217A (en)	1978-05-23	7-((5'-N-Methylthioacetamido)-adipoamido)cephalosporin derivatives
JPS58126891A (ja)	1983-07-28	セフアロスポリン化合物
KR820000153B1 (ko)	1982-02-23	6-[D-(-)-α-[4'-알킬-2', 3'-디옥소피페라지노 카보닐)-아미노페닐(또는 하이드록시페닐)아세토아미도]-페니실란산 유도체의 제조방법
JPS63500721A (ja)	1988-03-17	化学化合物の新規製法
KR930007816B1 (ko)	1993-08-20	세펨 화합물의 새로운 제조방법
KR870000724B1 (ko)	1987-04-09	세팔로스포린 유도체의 제조방법
US3819619A (en)	1974-06-25	N-isobornyloxycarbonylcephalosporin c
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