JPH0257554B2 - - Google Patents

Info

Publication number: JPH0257554B2
Authority: JP; Japan
Prior art keywords: formula; acid; group; compounds; compound
Prior art date: 1978-05-26
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 - Lifetime

Application number

JP62142418A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6322093A (ja

Inventor

Hiruda Okyarahan Shinshia

Jooji Hyuubaato Ribaamoa Deibitsudo

Aaru Nyuuooru Kurisutofuaa

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.)

Glaxo Group Ltd

Original Assignee

Glaxo Group 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.)

1978-05-26

Filing date

1987-06-09

Publication date

1990-12-05

1987-06-09 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1988-01-29 Publication of JPS6322093A publication Critical patent/JPS6322093A/ja

1990-12-05 Publication of JPH0257554B2 publication Critical patent/JPH0257554B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 160
-1 pyridine compound Chemical class 0.000 claims description 56
150000003839 salts Chemical class 0.000 claims description 34
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
231100000252 nontoxic Toxicity 0.000 claims description 19
230000003000 nontoxic effect Effects 0.000 claims description 19
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
125000003277 amino group Chemical group 0.000 claims description 6
125000000524 functional group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 3
239000012434 nucleophilic reagent Substances 0.000 claims description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 74
239000000203 mixture Substances 0.000 description 74
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 73
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
239000000243 solution Substances 0.000 description 64
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
239000000047 product Substances 0.000 description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
239000002253 acid Substances 0.000 description 40
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
239000007787 solid Substances 0.000 description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 28
229940124587 cephalosporin Drugs 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 27
229930186147 Cephalosporin Natural products 0.000 description 26
150000002148 esters Chemical class 0.000 description 25
150000001780 cephalosporins Chemical class 0.000 description 22
238000000034 method Methods 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
238000002360 preparation method Methods 0.000 description 19
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
244000005700 microbiome Species 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
238000004519 manufacturing process Methods 0.000 description 15
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 14
230000003115 biocidal effect Effects 0.000 description 14
235000019253 formic acid Nutrition 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
239000003242 anti bacterial agent Substances 0.000 description 13
229940088710 antibiotic agent Drugs 0.000 description 13
238000003756 stirring Methods 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
150000007513 acids Chemical class 0.000 description 12
230000000694 effects Effects 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
239000007858 starting material Substances 0.000 description 12
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
239000000872 buffer Substances 0.000 description 11
238000012360 testing method Methods 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
238000001914 filtration Methods 0.000 description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
239000002904 solvent Substances 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
239000000725 suspension Substances 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
230000000844 anti-bacterial effect Effects 0.000 description 8
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
239000006260 foam Substances 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
230000007935 neutral effect Effects 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
239000000843 powder Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 7
241000699670 Mus sp. Species 0.000 description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
238000005917 acylation reaction Methods 0.000 description 6
102000006635 beta-lactamase Human genes 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000000284 extract Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
230000008569 process Effects 0.000 description 6
229920005989 resin Polymers 0.000 description 6
239000011347 resin Substances 0.000 description 6
235000009518 sodium iodide Nutrition 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
238000005406 washing Methods 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000012267 brine Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
241000282412 Homo Species 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000010933 acylation Effects 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
230000000845 anti-microbial effect Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000006266 etherification reaction Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000011521 glass Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000010534 nucleophilic substitution reaction Methods 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
125000005646 oximino group Chemical group 0.000 description 4
235000011007 phosphoric acid Nutrition 0.000 description 4
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
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 4
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical group NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
108020004256 Beta-lactamase Proteins 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
108090000204 Dipeptidase 1 Proteins 0.000 description 3
241000588724 Escherichia coli Species 0.000 description 3
241000606768 Haemophilus influenzae Species 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000589516 Pseudomonas Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
RRNJROHIFSLGRA-JEDNCBNOSA-N acetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(O)=O.NCCCC[C@H](N)C(O)=O RRNJROHIFSLGRA-JEDNCBNOSA-N 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000005042 acyloxymethyl group Chemical group 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
229920001971 elastomer Polymers 0.000 description 3
229940047650 haemophilus influenzae Drugs 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
229960005357 lysine acetate Drugs 0.000 description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
230000009467 reduction Effects 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
150000003952 β-lactams Chemical class 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-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
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
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 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
241000288906 Primates Species 0.000 description 2
241000589517 Pseudomonas aeruginosa Species 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
229910021536 Zeolite Inorganic materials 0.000 description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
229940083916 aluminum distearate Drugs 0.000 description 2
RDIVANOKKPKCTO-UHFFFAOYSA-K aluminum;octadecanoate;hydroxide Chemical compound [OH-].[Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O RDIVANOKKPKCTO-UHFFFAOYSA-K 0.000 description 2
229960004821 amikacin Drugs 0.000 description 2
LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 2
229940126575 aminoglycoside Drugs 0.000 description 2
229950003476 aminothiazole Drugs 0.000 description 2
239000003708 ampul Substances 0.000 description 2
239000006286 aqueous extract Substances 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
244000052616 bacterial pathogen Species 0.000 description 2
PWLXILYCJRRXMU-VBORYMHYSA-N benzhydryl (6r,7r)-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound N1=CSC(\C=C/C=2CS[C@H]3N(C([C@H]3NC(=O)CC=3C=CC=CC=3)=O)C=2C(=O)OC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C PWLXILYCJRRXMU-VBORYMHYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
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239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100001095 no nephrotoxicity Toxicity 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000008363 phosphate buffer 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
239000002798 polar solvent Substances 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
230000005588 protonation Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
XVVXNXGBJNXJNU-UHFFFAOYSA-N pyridine-4-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.OC(=O)C1=CC=NC=C1 XVVXNXGBJNXJNU-UHFFFAOYSA-N 0.000 description 1
GWKKVWOEQGDUSY-UHFFFAOYSA-N pyridine;sodium Chemical compound [Na].C1=CC=NC=C1 GWKKVWOEQGDUSY-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
229940070891 pyridium Drugs 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
238000007789 sealing Methods 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
229940115939 shigella sonnei Drugs 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
239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
AAMCVENDCXWDPJ-UHFFFAOYSA-N sulfanyl acetate Chemical class CC(=O)OS AAMCVENDCXWDPJ-UHFFFAOYSA-N 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
UZKNZPUJLUKTDF-UHFFFAOYSA-N tert-butyl 1-(1,3-dioxoisoindol-4-yl)oxycyclopropane-1-carboxylate Chemical compound C=1C=CC=2C(=O)NC(=O)C=2C=1OC1(C(=O)OC(C)(C)C)CC1 UZKNZPUJLUKTDF-UHFFFAOYSA-N 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
IGVNJALYNQVQIT-UHFFFAOYSA-N tert-butyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)Br IGVNJALYNQVQIT-UHFFFAOYSA-N 0.000 description 1
UXFLTJLAEIHRCF-UHFFFAOYSA-N tert-butyl 2-bromocyclopentane-1-carboxylate Chemical compound CC(C)(C)OC(=O)C1CCCC1Br UXFLTJLAEIHRCF-UHFFFAOYSA-N 0.000 description 1
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000012085 test solution Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
238000005866 tritylation reaction Methods 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
239000012138 yeast extract 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
- C07D501/24—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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
- 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)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP62142418A 1978-05-26 1987-06-09 セフアロスポリン化合物の製法 Granted JPS6322093A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB2291178		1978-05-26
GB22911/1978		1978-05-26
GB22913/1978		1978-05-26

Publications (2)

Publication Number	Publication Date
JPS6322093A JPS6322093A (ja)	1988-01-29
JPH0257554B2 true JPH0257554B2 (hu)	1990-12-05

Family

ID=10187065

Family Applications (6)

Application Number	Title	Priority Date	Filing Date
JP6669579A Granted JPS54154786A (en)	1978-05-26	1979-05-25	Cephalosporin compound
JP3813280A Pending JPS55149289A (en)	1978-05-26	1980-03-24	Cephalosporin compound
JP6315985A Granted JPS6127990A (ja)	1978-05-26	1985-03-27	セフアロスポリン化合物
JP6315785A Granted JPS6127921A (ja)	1978-05-26	1985-03-27	セフアロスポリン化合物を有効成分とする薬学的組成物
JP6315885A Granted JPS6127989A (ja)	1978-05-26	1985-03-27	セフアロスポリン化合物の製法
JP62142418A Granted JPS6322093A (ja)	1978-05-26	1987-06-09	セフアロスポリン化合物の製法

Family Applications Before (5)

Application Number	Title	Priority Date	Filing Date
JP6669579A Granted JPS54154786A (en)	1978-05-26	1979-05-25	Cephalosporin compound
JP3813280A Pending JPS55149289A (en)	1978-05-26	1980-03-24	Cephalosporin compound
JP6315985A Granted JPS6127990A (ja)	1978-05-26	1985-03-27	セフアロスポリン化合物
JP6315785A Granted JPS6127921A (ja)	1978-05-26	1985-03-27	セフアロスポリン化合物を有効成分とする薬学的組成物
JP6315885A Granted JPS6127989A (ja)	1978-05-26	1985-03-27	セフアロスポリン化合物の製法

Country Status (10)

Country	Link
JP (6)	JPS54154786A (hu)
KR (2)	KR830000606B1 (hu)
AT (2)	AT369380B (hu)
BE (1)	BE876538A (hu)
CA (1)	CA1132538A (hu)
CY (1)	CY1168A (hu)
GB (2)	GB2025398B (hu)
HU (1)	HU184631B (hu)
IT (1)	IT1210588B (hu)
ZA (2)	ZA807323B (hu)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH654010A5 (de) *	1979-05-25	1986-01-31	Glaxo Group Ltd	Zwischenprodukte zur verwendung bei der herstellung von cephalosporin-antibiotika.
ZA806977B (en) *	1979-11-19	1981-10-28	Fujisawa Pharmaceutical Co	7-acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof
DE3006888A1 (de) *	1980-02-23	1981-09-10	Hoechst Ag, 6000 Frankfurt	Cephalosporinderivate und verfahren zu ihrer herstellung
JPS5756486A (en) *	1980-08-11	1982-04-05	Fujisawa Pharmaceut Co Ltd	Novel cephem compound or its salt, their preparation and prophylactic or remedy for microbism containing the same as active ingredient
US4336253A (en)	1981-03-11	1982-06-22	Eli Lilly And Company	Cephalosporin antibiotics
DE3207840A1 (de) *	1982-03-04	1983-09-15	Hoechst Ag, 6230 Frankfurt	"cephalosporinderivate und verfahren zu ihrer herstellung"
EP0097961B1 (en)	1982-06-28	1987-11-11	Bristol-Myers Company	Cephalosporin derivatives, a process for the manufacture thereof and pharmaceutical compositions containing said derivatives
DE3239365A1 (de) *	1982-10-23	1984-04-26	Bayer Ag, 5090 Leverkusen	Neue cephalosporine und verfahren zu ihrer herstellung
EP0113568B1 (en) *	1982-12-27	1990-04-04	Eli Lilly And Company	Intermediates for the preparation of ceftazidine, and process for their preparation
DE3313818A1 (de) *	1983-04-16	1984-10-18	Hoechst Ag, 6230 Frankfurt	Neue kristallmodifikation von ceftazidim
US4855420A (en) *	1983-06-03	1989-08-08	Ici Pharma	Cephalosporin derivatives
GB8413152D0 (en) *	1983-06-03	1984-06-27	Ici Pharma	Cephalosporin derivatives
GB8406218D0 (en) *	1984-03-09	1984-04-11	Glaxo Group Ltd	Process
GB8410991D0 (en) *	1984-04-30	1984-06-06	Glaxo Group Ltd	Process
GB8410993D0 (en) *	1984-04-30	1984-06-06	Glaxo Group Ltd	Process
GB8410992D0 (en) *	1984-04-30	1984-06-06	Glaxo Group Ltd	Process
FI851934L (fi) *	1984-05-30	1985-12-01	Ici Plc	Kefalosporinderivat.
EP0238060B1 (en)	1986-03-19	1992-01-08	Banyu Pharmaceutical Co., Ltd.	Cephalosporin derivatives, processes for their preparation and antibacterial agents
KR0164458B1 (ko) *	1995-04-04	1999-01-15	김은영	암모니오세팔로스포린 계열 항생제 및 그의 제조방법
US5872249A (en) *	1995-09-01	1999-02-16	Korea Institute Of Science And Technology	3-ammoniopropenyl cephalosporin compounds as antibacterial agents and process for preparing the same
JPH09110877A (ja)	1995-10-17	1997-04-28	Katayama Seiyakushiyo:Kk	セフェム化合物、その製造法及びそれを含有する抗菌剤

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS597717B2 (ja) *	1976-09-08	1984-02-20	武田薬品工業株式会社	セフアロスポリン誘導体およびその製造法

1979
- 1979-05-25 KR KR7901689A patent/KR830000606B1/ko not_active IP Right Cessation
- 1979-05-25 BE BE0/195381A patent/BE876538A/xx not_active IP Right Cessation
- 1979-05-25 CY CY1168A patent/CY1168A/xx unknown
- 1979-05-25 JP JP6669579A patent/JPS54154786A/ja active Granted
- 1979-05-25 GB GB7918488A patent/GB2025398B/en not_active Expired
- 1979-05-25 ZA ZA807323A patent/ZA807323B/xx unknown
- 1979-05-25 HU HU79GA1287A patent/HU184631B/hu unknown
- 1979-05-25 GB GB7918488A patent/GB2058791B/en not_active Expired
- 1979-05-25 ZA ZA792581A patent/ZA792581B/xx unknown
1980
- 1980-03-24 JP JP3813280A patent/JPS55149289A/ja active Pending
1981
- 1981-04-16 AT AT0173881A patent/AT369380B/de active
- 1981-04-16 AT AT0173981A patent/AT369381B/de not_active IP Right Cessation
- 1981-05-06 CA CA377,013A patent/CA1132538A/en not_active Expired
- 1981-11-06 IT IT8149648A patent/IT1210588B/it active
1983
- 1983-01-25 KR KR1019830000281A patent/KR830000835B1/ko not_active IP Right Cessation
1985
- 1985-03-27 JP JP6315985A patent/JPS6127990A/ja active Granted
- 1985-03-27 JP JP6315785A patent/JPS6127921A/ja active Granted
- 1985-03-27 JP JP6315885A patent/JPS6127989A/ja active Granted
1987
- 1987-06-09 JP JP62142418A patent/JPS6322093A/ja active Granted

Also Published As

Publication number	Publication date
JPH0257069B2 (hu)	1990-12-03
JPS6127989A (ja)	1986-02-07
KR830000606B1 (ko)	1983-03-17
JPS54154786A (en)	1979-12-06
GB2025398A (en)	1980-01-23
JPS6354689B2 (hu)	1988-10-28
GB2058791B (en)	1982-11-24
IT8149648A0 (it)	1981-11-06
CA1132538A (en)	1982-09-28
ZA807323B (en)	1981-02-25
JPS55149289A (en)	1980-11-20
JPS625916B2 (hu)	1987-02-07
GB2058791A (en)	1981-04-15
GB2025398B (en)	1982-08-11
AT369380B (de)	1982-12-27
IT1210588B (it)	1989-09-14
HU184631B (en)	1984-09-28
ATA173881A (de)	1982-05-15
KR830000835B1 (ko)	1983-04-20
JPH0257073B2 (hu)	1990-12-03
JPS6127921A (ja)	1986-02-07
ZA792581B (en)	1981-01-28
JPS6322093A (ja)	1988-01-29
ATA173981A (de)	1982-05-15
BE876538A (fr)	1979-11-26
CY1168A (en)	1983-06-10
JPS6127990A (ja)	1986-02-07
AT369381B (de)	1982-12-27

Publication	Publication Date	Title
US4258041A (en)	1981-03-24	(6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(1-pyridiniummethyl)-ceph-3-em-4-carboxylate and salts thereof
JPH0257554B2 (hu)	1990-12-05
US4264595A (en)	1981-04-28	7-[2-(2-Imino-4-thiazolin-4-yl)-2-(syn)-hydroxy-iminoacetamido]-cephalosporins
US4833134A (en)	1989-05-23	Cephem compounds
US4464368A (en)	1984-08-07	Cephalosporin antibiotics
FI74972B (fi)	1987-12-31	Foerfarande foer framstaellning av farmaceutiskt vaerdefull 7 -/(z)-2-(2-aminotiazol/-4-yl)-2-oxi- imino-acetamido/-3-cefem-4-karboxylsyra.
US4315005A (en)	1982-02-09	Cephalosporin antibiotics
US4427675A (en)	1984-01-24	Cephalosporin antibiotics
US4504477A (en)	1985-03-12	Cephalosporin antibiotics
KR830001891B1 (ko)	1983-09-17	세팔로스포린 항생물질의 제조방법
KR830001130B1 (ko)	1983-06-14	세팔로스포린 항생제의 제조방법
CA1074297A (en)	1980-03-25	Cephalosporins
US4560683A (en)	1985-12-24	Cephalosporin antibiotics
NL7907881A (nl)	1980-04-29	Nieuwe cefalosporine-antibiotica, werkwijze voor de bereiding daarvan en farmaceutische preparaten die deze bevatten.
GB2037281A (en)	1980-07-09	7-( alpha -(2-amino.4-thiazolyl)- alpha - hydroximino-acetamido)- cephalosporins
KR830001593B1 (ko)	1983-08-16	세팔로스포린 항생제의 제조방법
JPS58210093A (ja)	1983-12-07	セフアロスポリン抗生物質
JPH04338392A (ja)	1992-11-25	新規セフェム誘導体及びその製造方法
IE49171B1 (en)	1985-08-21	Cephalosporin antibiotics
JPS5913786A (ja)	1984-01-24	セフアロスポリン抗生物質
GB2183630A (en)	1987-06-10	Cephalosporin antibiotics
NL8005440A (nl)	1981-04-06	Cefalosporinen met antibiotische werking.