KR830000606B1 - 세팔로스포린 항생제의 제조방법 - Google Patents

세팔로스포린 항생제의 제조방법 Download PDF

Info

Publication number: KR830000606B1
Authority: KR; South Korea
Prior art keywords: acid; compound; group; compounds; formula
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

Application number

KR7901689A

Other languages

English (en)

Korean (ko)

Inventor

오칼라간 신티아힐다

죠지 허버트 리버모어 데비드

뉴얼 크리스토퍼얼

Original Assignee

헤롤드 월터 마틴

글락소 그룹 리미티드

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

1979-05-25

Publication date

1983-03-17

1979-05-25 Application filed by 헤롤드 월터 마틴, 글락소 그룹 리미티드 filed Critical 헤롤드 월터 마틴

1983-01-25 Priority to KR1019830000281A priority Critical patent/KR830000835B1/ko

1983-03-17 Application granted granted Critical

1983-03-17 Publication of KR830000606B1 publication Critical patent/KR830000606B1/ko

Status Expired legal-status Critical Current

Links

229940124587 cephalosporin Drugs 0.000 title claims description 27
229930186147 Cephalosporin Natural products 0.000 title claims description 26
150000001780 cephalosporins Chemical class 0.000 title claims description 21
239000003242 anti bacterial agent Substances 0.000 title description 19
229940088710 antibiotic agent Drugs 0.000 title description 18
238000004519 manufacturing process Methods 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 118
-1 compound anion Chemical class 0.000 claims description 79
239000002253 acid Substances 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 34
150000002148 esters Chemical class 0.000 claims description 24
231100000252 nontoxic Toxicity 0.000 claims description 23
230000003000 nontoxic effect Effects 0.000 claims description 23
230000003115 biocidal effect Effects 0.000 claims description 21
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
238000005917 acylation reaction Methods 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
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125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
239000000203 mixture Substances 0.000 description 39
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
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239000000243 solution Substances 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
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238000002360 preparation method Methods 0.000 description 24
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238000006243 chemical reaction Methods 0.000 description 15
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
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238000003756 stirring Methods 0.000 description 10
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239000003795 chemical substances by application Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
238000007796 conventional method Methods 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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239000007858 starting material Substances 0.000 description 7
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
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150000007513 acids Chemical class 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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229940126575 aminoglycoside Drugs 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
230000000845 anti-microbial effect Effects 0.000 description 5
238000001816 cooling Methods 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000012071 phase Substances 0.000 description 5
235000011007 phosphoric acid Nutrition 0.000 description 5
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 5
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 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
102000006635 beta-lactamase Human genes 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
229940113088 dimethylacetamide Drugs 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
125000005646 oximino group Chemical group 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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241000589516 Pseudomonas Species 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
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
239000012267 brine Substances 0.000 description 3
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125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
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NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
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
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
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HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
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
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 2
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 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
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241000699670 Mus sp. Species 0.000 description 2
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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
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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
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SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 2
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IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
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IACSYDRIOYGJNH-ALCCZGGFSA-N ethyl (2z)-2-hydroxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(=N/O)\C(C)=O IACSYDRIOYGJNH-ALCCZGGFSA-N 0.000 description 2
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 2
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SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
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235000017550 sodium carbonate Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
BRKPVWIIOFNEBA-UHFFFAOYSA-N tert-butyl 1-bromocyclobutane-1-carboxylate Chemical compound CC(C)(C)OC(=O)C1(Br)CCC1 BRKPVWIIOFNEBA-UHFFFAOYSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
238000012360 testing method Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000008215 water for injection Substances 0.000 description 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
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241000588748 Klebsiella Species 0.000 description 1
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241000588772 Morganella morganii Species 0.000 description 1
101100022451 Mus musculus Mbnl3 gene Proteins 0.000 description 1
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GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
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241000283984 Rodentia Species 0.000 description 1
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QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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239000013543 active substance Substances 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
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150000001450 anions Chemical class 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000013011 aqueous formulation Substances 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
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239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
125000005518 carboxamido group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
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239000003054 catalyst Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
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238000006297 dehydration reaction Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
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239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
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239000002024 ethyl acetate extract Substances 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
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239000012467 final product Substances 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
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238000007710 freezing Methods 0.000 description 1
229960002518 gentamicin Drugs 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
229940047650 haemophilus influenzae Drugs 0.000 description 1
125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
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238000011065 in-situ storage Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000004407 iron oxides and hydroxides Substances 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
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 1
HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
231100001095 no nephrotoxicity Toxicity 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
150000002924 oxiranes Chemical class 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
239000008194 pharmaceutical composition Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate 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
239000004584 polyacrylic acid Substances 0.000 description 1
229920005990 polystyrene resin 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
230000008569 process Effects 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000013139 quantization Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000007789 sealing Methods 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
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 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
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
230000008023 solidification Effects 0.000 description 1
238000007711 solidification Methods 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000758 substrate 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
150000003462 sulfoxides Chemical class 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
CTNNHJMKRCKQBI-UHFFFAOYSA-N tert-butyl 1-aminooxycyclopropane-1-carboxylate Chemical compound CC(C)(C)OC(=O)C1(ON)CC1 CTNNHJMKRCKQBI-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
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 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
231100000331 toxic Toxicity 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
230000002588 toxic effect Effects 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
210000003708 urethra Anatomy 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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)

KR7901689A 1978-05-26 1979-05-25 세팔로스포린 항생제의 제조방법 Expired KR830000606B1 (ko)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
KR1019830000281A KR830000835B1 (ko)	1978-05-26	1983-01-25	세팔로스포린 항생제의 제조방법

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB22911/78		1978-05-26
GB2291178		1978-05-26

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1019830000281A Division KR830000835B1 (ko)	1978-05-26	1983-01-25	세팔로스포린 항생제의 제조방법

Publications (1)

Publication Number	Publication Date
KR830000606B1 true KR830000606B1 (ko)	1983-03-17

Family

ID=10187065

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
KR7901689A Expired KR830000606B1 (ko)	1978-05-26	1979-05-25	세팔로스포린 항생제의 제조방법
KR1019830000281A Expired KR830000835B1 (ko)	1978-05-26	1983-01-25	세팔로스포린 항생제의 제조방법

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
KR1019830000281A Expired KR830000835B1 (ko)	1978-05-26	1983-01-25	세팔로스포린 항생제의 제조방법

Country Status (10)

Country	Link
JP (6)	JPS54154786A (pt)
KR (2)	KR830000606B1 (pt)
AT (2)	AT369380B (pt)
BE (1)	BE876538A (pt)
CA (1)	CA1132538A (pt)
CY (1)	CY1168A (pt)
GB (2)	GB2058791B (pt)
HU (1)	HU184631B (pt)
IT (1)	IT1210588B (pt)
ZA (2)	ZA807323B (pt)

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
GB8413152D0 (en) *	1983-06-03	1984-06-27	Ici Pharma	Cephalosporin derivatives
US4855420A (en) *	1983-06-03	1989-08-08	Ici Pharma	Cephalosporin derivatives
GB8406218D0 (en) *	1984-03-09	1984-04-11	Glaxo Group Ltd	Process
GB8410992D0 (en) *	1984-04-30	1984-06-06	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
FI851934A7 (fi) *	1984-05-30	1985-12-01	Ici Plc	Kefalosporiinijohdannaisia.
DE3775798D1 (de)	1986-03-19	1992-02-20	Banyu Pharma Co Ltd	Cephalosporinverbindungen, verfahren zu ihrer herstellung und antibakterielle mittel.
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 GB GB7918488A patent/GB2058791B/en not_active Expired
- 1979-05-25 GB GB7918488A patent/GB2025398B/en not_active Expired
- 1979-05-25 ZA ZA807323A patent/ZA807323B/xx unknown
- 1979-05-25 CY CY1168A patent/CY1168A/en unknown
- 1979-05-25 KR KR7901689A patent/KR830000606B1/ko not_active Expired
- 1979-05-25 BE BE0/195381A patent/BE876538A/xx not_active IP Right Cessation
- 1979-05-25 ZA ZA792581A patent/ZA792581B/xx unknown
- 1979-05-25 HU HU79GA1287A patent/HU184631B/hu unknown
- 1979-05-25 JP JP6669579A patent/JPS54154786A/ja active Granted
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 Expired
1985
- 1985-03-27 JP JP6315785A patent/JPS6127921A/ja active Granted
- 1985-03-27 JP JP6315885A patent/JPS6127989A/ja active Granted
- 1985-03-27 JP JP6315985A patent/JPS6127990A/ja active Granted
1987
- 1987-06-09 JP JP62142418A patent/JPS6322093A/ja active Granted

Also Published As

Publication number	Publication date
CA1132538A (en)	1982-09-28
GB2025398B (en)	1982-08-11
GB2025398A (en)	1980-01-23
JPH0257073B2 (pt)	1990-12-03
JPH0257069B2 (pt)	1990-12-03
GB2058791A (en)	1981-04-15
ZA792581B (en)	1981-01-28
IT1210588B (it)	1989-09-14
HU184631B (en)	1984-09-28
JPS6127990A (ja)	1986-02-07
IT8149648A0 (it)	1981-11-06
ZA807323B (en)	1981-02-25
CY1168A (en)	1983-06-10
JPS6127921A (ja)	1986-02-07
BE876538A (fr)	1979-11-26
ATA173881A (de)	1982-05-15
JPH0257554B2 (pt)	1990-12-05
KR830000835B1 (ko)	1983-04-20
GB2058791B (en)	1982-11-24
JPS6354689B2 (pt)	1988-10-28
JPS6322093A (ja)	1988-01-29
AT369380B (de)	1982-12-27
JPS625916B2 (pt)	1987-02-07
JPS54154786A (en)	1979-12-06
JPS6127989A (ja)	1986-02-07
ATA173981A (de)	1982-05-15
AT369381B (de)	1982-12-27
JPS55149289A (en)	1980-11-20

Publication	Publication Date	Title
KR830000606B1 (ko)	1983-03-17	세팔로스포린 항생제의 제조방법
FI67555C (fi)	1985-04-10	Foerfarande foer framstaellning av terapeutiskt anvaendbart (6 7r)-7-((z)-2-(2-aminotiazol-4-yl)-2-(2-karboxiprop-2-oxi imno)-acetamido)-3-(1-pyridiniummetyl)-cef-3-em-4-karboxyla t
FI67384B (fi)	1984-11-30	Foerfarande foer framstaellning av farmaceutiskt anvaendbara 7-(2-(2-imino-4-tiazolin-4-yl)-2-hydroxiiminoacetamido)-3-cefem-4-karboxylsyraderivat
US4621081A (en)	1986-11-04	Cephalosporin antibiotics
US4464368A (en)	1984-08-07	Cephalosporin antibiotics
CA1130280A (en)	1982-08-24	Cephalosporin compounds
US4315005A (en)	1982-02-09	Cephalosporin antibiotics
CA1144156A (en)	1983-04-05	Cephalosporin antibiotics
KR830001130B1 (ko)	1983-06-14	세팔로스포린 항생제의 제조방법
KR830001891B1 (ko)	1983-09-17	세팔로스포린 항생물질의 제조방법
US4560683A (en)	1985-12-24	Cephalosporin antibiotics
US4200746A (en)	1980-04-29	Cephalosporins
KR830001593B1 (ko)	1983-08-16	세팔로스포린 항생제의 제조방법
SE438859B (sv)	1985-05-13	7-acylamido-3-karbamoyloximetyl-3-cefem-4-karboxylsyraderivat och forfarande for framstellning derav
CA1129408A (en)	1982-08-10	Cephalosporin antibiotics
CA1122973A (en)	1982-05-04	Cephalosporin antibiotics
EP0095329A2 (en)	1983-11-30	Cephalosporin antibiotics
GB2183630A (en)	1987-06-10	Cephalosporin antibiotics
GB2183629A (en)	1987-06-10	Cephalosporin antibiotics

Legal Events

Date	Code	Title	Description
1979-05-25	PA0109	Patent application	Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19790525
1982-06-01	PE0902	Notice of grounds for rejection	Comment text: Notification of reason for refusal Patent event date: 19820601 Patent event code: PE09021S01D
1983-01-26	E902	Notification of reason for refusal
1983-01-26	PE0902	Notice of grounds for rejection	Comment text: Notification of reason for refusal Patent event date: 19830126 Patent event code: PE09021S01D
1983-02-18	G160	Decision to publish patent application
1983-03-17	PG1605	Publication of application before grant of patent	Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19830218
1983-11-25	O132	Decision on opposition [patent]
1983-11-25	PO1301	Decision on opposition	Comment text: Decision on Opposition Patent event date: 19831125 Patent event code: PO13011S01D
1983-12-21	GRNT	Written decision to grant
1983-12-21	PR0701	Registration of establishment	Comment text: Registration of Establishment Patent event date: 19831221 Patent event code: PR07011E01D
1983-12-21	PR1002	Payment of registration fee	Payment date: 19831221 End annual number: 3 Start annual number: 1
1986-03-12	PR1001	Payment of annual fee	Payment date: 19860312 Start annual number: 4 End annual number: 4
1987-02-28	PR1001	Payment of annual fee	Payment date: 19870228 Start annual number: 5 End annual number: 5
1988-03-08	PR1001	Payment of annual fee	Payment date: 19880308 Start annual number: 6 End annual number: 6
1989-03-09	PR1001	Payment of annual fee	Payment date: 19890309 Start annual number: 7 End annual number: 7
1990-03-12	PR1001	Payment of annual fee	Payment date: 19900312 Start annual number: 8 End annual number: 8
1991-03-05	PR1001	Payment of annual fee	Payment date: 19910305 Start annual number: 9 End annual number: 9
1992-03-06	PR1001	Payment of annual fee	Payment date: 19920306 Start annual number: 10 End annual number: 10
1993-03-08	PR1001	Payment of annual fee	Payment date: 19930308 Start annual number: 11 End annual number: 11
1994-01-17	J206	Request for trial to confirm the scope of a patent right
1994-01-17	PJ0206	Trial to confirm the scope of a patent	Patent event code: PJ02062R01D Patent event date: 19940117 Comment text: Request for Trial Patent event code: PJ02061E01I Patent event date: 19831221 Comment text: Registration of Establishment Decision date: 19940225 Request date: 19940117 Appeal identifier: 1994100000062 Appeal kind category: Confirmation of the scope of right_defensive
1994-02-25	J121	Written withdrawal of request for trial
1994-02-25	PJ1201	Withdrawal of trial	Patent event code: PJ12011R01D Patent event date: 19940225 Comment text: Written Withdrawal of Request for Trial Appeal identifier: 1994100000062 Request date: 19940117 Appeal kind category: Confirmation of the scope of right_defensive Decision date: 19940225
1994-03-17	FPAY	Annual fee payment	Payment date: 19940317 Year of fee payment: 12
1994-03-17	PR1001	Payment of annual fee	Payment date: 19940317 Start annual number: 12 End annual number: 12
1994-05-26	EXPY	Expiration of term
1994-05-26	PC1801	Expiration of term	Termination date: 19951120 Termination category: Others