SE438507B - Nya cefalosporinantibiotika samt forfarande for framstellning derav - Google Patents

Nya cefalosporinantibiotika samt forfarande for framstellning derav

Info

Publication number: SE438507B
Authority: SE; Sweden
Prior art keywords: compound; formula; acid; group; compounds
Prior art date: 1978-05-26

Application number

SE7904576A

Other languages

English (en)

Swedish (sv)

Other versions

SE7904576L (sv

Inventor

C H O'callaghan

D G H Livermore

C E Newall

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

1979-05-25

Publication date

1985-04-22

1979-05-25 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1980-02-11 Publication of SE7904576L publication Critical patent/SE7904576L/xx

1985-04-22 Publication of SE438507B publication Critical patent/SE438507B/sv

Links

238000000034 method Methods 0.000 title claims description 18
239000003242 anti bacterial agent Substances 0.000 title claims description 16
229940124587 cephalosporin Drugs 0.000 title description 19
229930186147 Cephalosporin Natural products 0.000 title description 18
150000001780 cephalosporins Chemical class 0.000 title description 16
229940088710 antibiotic agent Drugs 0.000 title description 14
150000001875 compounds Chemical class 0.000 claims description 126
-1 2-aminothiazol-4-yl Chemical group 0.000 claims description 84
239000002253 acid Substances 0.000 claims description 46
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 30
238000006243 chemical reaction Methods 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
150000002148 esters Chemical class 0.000 claims description 20
230000003115 biocidal effect Effects 0.000 claims description 19
231100000252 nontoxic Toxicity 0.000 claims description 19
230000003000 nontoxic effect Effects 0.000 claims description 19
150000007513 acids Chemical class 0.000 claims description 16
230000000903 blocking effect Effects 0.000 claims description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 11
238000001727 in vivo Methods 0.000 claims description 11
230000008569 process Effects 0.000 claims description 9
230000009467 reduction Effects 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000012038 nucleophile Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
239000000203 mixture Substances 0.000 description 43
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 41
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 18
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000007858 starting material Substances 0.000 description 12
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 11
238000005917 acylation reaction Methods 0.000 description 11
239000002585 base Substances 0.000 description 11
230000000694 effects Effects 0.000 description 11
235000019253 formic acid Nutrition 0.000 description 11
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238000001914 filtration Methods 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
238000003756 stirring Methods 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
230000010933 acylation Effects 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
239000000725 suspension Substances 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
241000589516 Pseudomonas Species 0.000 description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 5
229940126575 aminoglycoside Drugs 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
239000010410 layer Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
230000000269 nucleophilic effect Effects 0.000 description 5
235000011007 phosphoric acid Nutrition 0.000 description 5
239000002904 solvent Substances 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
238000005406 washing Methods 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
238000006266 etherification reaction Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000006260 foam Substances 0.000 description 4
239000011521 glass Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 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
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241000588769 Proteus <enterobacteria> Species 0.000 description 3
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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
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HJJDBAOLQAWBMH-YCRCPZNHSA-N cefmenoxime Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NN=NN1C HJJDBAOLQAWBMH-YCRCPZNHSA-N 0.000 description 3
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229960001760 dimethyl sulfoxide Drugs 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
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238000012360 testing method Methods 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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241000894006 Bacteria Species 0.000 description 2
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241000588914 Enterobacter Species 0.000 description 2
241000588697 Enterobacter cloacae Species 0.000 description 2
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241000588749 Klebsiella oxytoca Species 0.000 description 2
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239000004472 Lysine Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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241000288906 Primates Species 0.000 description 2
241000588770 Proteus mirabilis Species 0.000 description 2
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150000001408 amides Chemical class 0.000 description 2
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238000002425 crystallisation Methods 0.000 description 2
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238000000354 decomposition reaction Methods 0.000 description 2
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
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
239000007789 gas Substances 0.000 description 2
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
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Classifications

- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)

SE7904576A 1978-05-26 1979-05-25 Nya cefalosporinantibiotika samt forfarande for framstellning derav SE438507B (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB2291178		1978-05-26
GB2291378		1978-05-26

Publications (2)

Publication Number	Publication Date
SE7904576L SE7904576L (sv)	1980-02-11
SE438507B true SE438507B (sv)	1985-04-22

Family

ID=26256190

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SE7904576A SE438507B (sv)	1978-05-26	1979-05-25	Nya cefalosporinantibiotika samt forfarande for framstellning derav
SE8402887A SE8402887L (sv)	1978-05-26	1984-05-28	Cefalosporinantibiotika

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SE8402887A SE8402887L (sv)	1978-05-26	1984-05-28	Cefalosporinantibiotika

Country Status (27)

Country	Link
US (2)	US4258041A (fr)
AR (2)	AR228726A1 (fr)
AT (1)	AT370420B (fr)
AU (1)	AU524671B2 (fr)
CA (1)	CA1127633A (fr)
CH (2)	CH649556A5 (fr)
DE (1)	DE2921316C2 (fr)
DK (1)	DK157685C (fr)
ES (2)	ES480915A1 (fr)
FI (2)	FI67555C (fr)
FR (2)	FR2426695A1 (fr)
HK (1)	HK40183A (fr)
IE (2)	IE49172B1 (fr)
IL (3)	IL57400A (fr)
IT (1)	IT1116198B (fr)
KE (1)	KE3252A (fr)
LU (1)	LU81319A1 (fr)
MY (1)	MY8400017A (fr)
NL (2)	NL176855C (fr)
NO (2)	NO155347C (fr)
NZ (2)	NZ190558A (fr)
PH (1)	PH16961A (fr)
PT (2)	PT69669A (fr)
SE (2)	SE438507B (fr)
SG (1)	SG58382G (fr)
SI (2)	SI7911231A8 (fr)
YU (2)	YU41635B (fr)

Families Citing this family (112)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4963542A (en) *	1976-09-08	1990-10-16	Takeda Chemical Industries, Ltd.	Cephalosporin derivatives
DE2714880A1 (de) *	1977-04-02	1978-10-26	Hoechst Ag	Cephemderivate und verfahren zu ihrer herstellung
AR228726A1 (es) *	1978-05-26	1983-04-15	Glaxo Group Ltd	Procedimiento para la preparacion del antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)acetamido)-3-(1-piridiniometil)cef-3-em-4-carboxilato
US4237128A (en) *	1979-04-12	1980-12-02	E. R. Squibb & Sons, Inc.	7-[2-(2-Amino-4-thiazolyl)-2-[(1-carboxy-1,1-dialkyl)alkoxyimino]acetamido]cephem sulfoxides
DE3019838A1 (de) *	1979-05-25	1980-12-04	Glaxo Group Ltd	Zwischenprodukte zur verwendung bei der herstellung von cephalosporin-antibiotika
AU540382B2 (en) *	1979-10-02	1984-11-15	Glaxo Group Limited	7(2-(2-aminothiazol-4-yl)-2-(2-carboxy prop-2-oxyimino) acetamido)-3-(1-pyridiniummethyl) ceph-3-em-4-carboxylate
US4329453A (en) *	1979-10-02	1982-05-11	Glaxo Group Limited	Cephalosporin antibiotic
AU538653B2 (en) *	1979-10-02	1984-08-23	Glaxo Group Limited	7-(2-(2-amino thiazol-4-yl)-2-(carboxymethoxyimino) acetamioo)-3-(1-pyridiniammethyl)-ceph-3-em-4-carboxylate
US4332800A (en) *	1979-10-12	1982-06-01	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds
US4338313A (en) *	1979-10-12	1982-07-06	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds
DE3006888A1 (de) *	1980-02-23	1981-09-10	Hoechst Ag, 6000 Frankfurt	Cephalosporinderivate und verfahren zu ihrer herstellung
FR2476647A2 (fr) *	1980-02-26	1981-08-28	Roussel Uclaf	Procede de preparation de derives de l'acide 2-(2-amino protege 4-thiazolyl) 2-alkoxyimino acetique isomere syn
US4252802A (en) *	1980-03-13	1981-02-24	E. R. Squibb & Sons, Inc.	Hydroxamic acid derivatives of 7-[(2-amino-4-thiazolyl)-oximino] cephalosporins
GR75706B (fr) *	1980-06-30	1984-08-02	Sanofi Sa
US4443444A (en) *	1980-08-11	1984-04-17	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds
EP0156118A1 (fr) *	1980-08-29	1985-10-02	Fujisawa Pharmaceutical Co., Ltd.	Produits de départ pour la préparation de composés céphem et procédés pour leur préparation
NZ198350A (en) *	1980-09-25	1985-02-28	Toyama Chemical Co Ltd	Cephalosporins and intermediates;pharmaceutical compositions
FR2494276A2 (fr) *	1980-11-20	1982-05-21	Rhone Poulenc Ind	Nouvelles vinyl-3 cephalosporines, et leur preparation
US4427677A (en)	1980-12-31	1984-01-24	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds
JPS57144291A (en) *	1981-03-02	1982-09-06	Ajinomoto Co Inc	Preparation of imidazoledicarboxylic acid derivative
US4336253A (en) *	1981-03-11	1982-06-22	Eli Lilly And Company	Cephalosporin antibiotics
JPS6011917B2 (ja) *	1981-04-09	1985-03-28	山之内製薬株式会社	新規なセファロスポリン化合物
DE3118732A1 (de) *	1981-05-12	1982-12-02	Hoechst Ag, 6000 Frankfurt	Cephalosporinderivate und verfahren zu ihrer herstellung
GR75487B (fr) *	1981-06-22	1984-07-23	Fujisawa Pharmaceutical Co
US4430499A (en)	1981-09-08	1984-02-07	Eli Lilly And Company	7-[2-(2-Aminooxazol-4-yl)-2-(oximino)acetamido]cephalosporin antibiotics
US4382932A (en) *	1981-09-08	1983-05-10	Eli Lilly And Company	Isoquinolinium substituted cephalosporins
US4382931A (en) *	1981-09-08	1983-05-10	Eli Lilly And Company	3'-Substituted quinolinium cephalosporins
US4577014A (en) *	1981-09-08	1986-03-18	Eli Lilly And Company	Thieno and furopyridinium-substituted cephalosporins
US4406898A (en) *	1981-09-08	1983-09-27	Eli Lilly And Company	Oxazole and oxadiazole cephalosporins
US4436912A (en)	1981-09-08	1984-03-13	Eli Lilly And Company	7-[2-(2-Aminooxazol-4-yl)-2-(oximino)acetamido cephalosporin antibiotics and intermediates therefor
JPS5859991A (ja) *	1981-09-14	1983-04-09	Fujisawa Pharmaceut Co Ltd	新規セフェム化合物
US4379787A (en) *	1981-10-02	1983-04-12	Eli Lilly And Company	Oximino-substituted cephalosporin compounds
US4388316A (en) *	1981-10-02	1983-06-14	Eli Lilly And Company	Amino-substituted oxazole, oxadiazole and isoxazole-substituted cephalosporins
US4401668A (en) *	1981-10-02	1983-08-30	Eli Lilly And Company	Pyrazinium substituted cephalosporins
US4450270A (en) *	1981-10-02	1984-05-22	Eli Lilly And Company	Dioximino cephalosporin antibiotics
US4402955A (en) *	1981-10-02	1983-09-06	Eli Lilly And Company	Dioximino cephalosporin antibiotics
US4406887A (en) *	1981-10-13	1983-09-27	Bristol-Myers Company	Method for treating resistant bacteria including anaerobes
ATE18219T1 (de) *	1981-11-13	1986-03-15	Glaxo Group Ltd	Thiazol-derivate und ihre verwendung bei der herstellung von beta-lactam-antibiotika.
US4497956A (en) *	1981-11-13	1985-02-05	Glaxo Group Limited	Manufacture of antibiotics
US4394503A (en) *	1981-12-07	1983-07-19	Bristol-Myers Company	Cephalosporin derivatives
US4474954A (en) *	1981-12-07	1984-10-02	Bristol-Myers Company	Intermediates for cephalosporin derivatives
US4501739A (en) *	1982-01-19	1985-02-26	Eli Lilly And Company	Thieno and furopyridinium-substituted cephalosporins
CA1213882A (fr) *	1982-03-04	1986-11-12	Jun Okumura	Cephalosporines
DE3207840A1 (de) *	1982-03-04	1983-09-15	Hoechst Ag, 6230 Frankfurt	"cephalosporinderivate und verfahren zu ihrer herstellung"
US4552696A (en) *	1982-04-09	1985-11-12	Bristol-Myers Company	Carbapenem antibiotics
DE3375013D1 (en) *	1982-04-29	1988-02-04	Glaxo Group Ltd	Thiazole derivative, process for its preparation and use in the preparation of beta-lactam antibiotics
DE3374410D1 (en)	1982-06-28	1987-12-17	Bristol Myers Co	Cephalosporin derivatives, a process for the manufacture thereof and pharmaceutical compositions containing said derivatives
IL69246A (en) *	1982-08-07	1986-07-31	Tanabe Seiyaku Co	7-((2-aminothiazolyl-2-pyrrolidonyl or(piperidonyl)-oxyimino)acetamido)cephem carboxylic acid derivatives,their preparation and pharmaceutical compositions containing them
ES8502863A1 (es) *	1982-09-10	1985-02-01	Glaxo Group Ltd	Un procedimiento para la produccion de un recipiente hermeticamente cerrado que contiene al menos un antibiotico de beta-lactama.
DE3381408D1 (de) *	1982-12-27	1990-05-10	Lilly Co Eli	Zwischenverbindungen fuer die herstellung von ceftazidin und verfahren zu ihrer herstellung.
EP0115770B2 (fr) *	1983-01-07	1996-06-19	Takeda Chemical Industries, Ltd.	Dérivés de thiazoles
US4486586A (en) *	1983-02-10	1984-12-04	Bristol-Myers Company	Cephalosporin derivatives
DE3313818A1 (de) *	1983-04-16	1984-10-18	Hoechst Ag, 6230 Frankfurt	Neue kristallmodifikation von ceftazidim
DE3313816A1 (de) *	1983-04-16	1984-10-18	Hoechst Ag, 6230 Frankfurt	Neue kristallmodifikation von ceftazidim
DE3316798A1 (de) *	1983-05-07	1984-11-08	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von cephemverbindungen
DE3316797A1 (de) *	1983-05-07	1984-11-08	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von cephemverbindungen
US4540779A (en) *	1983-06-20	1985-09-10	Eli Lilly And Company	Crystalline 7-(R)-amino-3-(1'pyridiniummethyl)-ceph-3-em-4-carboxylate monohydrochloride monohydrate compound
US4497811A (en) *	1983-07-01	1985-02-05	Seiji Shibahara	1-Oxadethiacephalosporin compound and antibacterial agent containing the _same
JPS6061528A (ja) *	1983-09-09	1985-04-09	ブリストル―マイヤーズ　スクイブ　カンパニー	嫌気性菌を包含する耐性バクテリアの処理法
AU566944B2 (en) *	1983-10-07	1987-11-05	Gist-Brocades N.V.	Preparation of 3-cephem derivatives
JPS60178891A (ja) *	1984-02-24	1985-09-12	Kureha Chem Ind Co Ltd	セファロスポリン誘導体及び該誘導体を含有する医薬
GB8406218D0 (en) *	1984-03-09	1984-04-11	Glaxo Group Ltd	Process
US4537959A (en) *	1984-03-26	1985-08-27	Eli Lilly And Company	Crystalline cephalosporin antibiotic salt
US4788185A (en) *	1984-04-23	1988-11-29	Takeda Chemical Industries, Ltd.	Cephalosporin compounds
PH22107A (en) *	1984-06-07	1988-06-01	Takeda Chemical Industries Ltd	3-pyrazolo(1,5-a)pyrdinium cephem compounds
CA1236089A (fr) *	1984-06-25	1988-05-03	Perry C. Heath	Ceftazidime
US4616080A (en) *	1984-07-02	1986-10-07	Eli Lilly And Company	Simplified process of forming crystalline ceftazidime pentahydrate
US4626534A (en) *	1984-07-23	1986-12-02	Eli Lilly And Company	Pharmaceutical formulation
EP0175544A3 (fr) *	1984-09-17	1987-06-03	Eli Lilly And Company	Procédé pour la préparation d'intermédiaires de céphalosporine
US4659813A (en) *	1984-11-08	1987-04-21	Eli Lilly And Company	Crystallization process for ceftazidime derivative
WO1988010263A1 (fr) *	1987-06-25	1988-12-29	Banyu Pharmaceutical Co., Ltd.	Composes cristallins de cephalosporine, procede de preparation et produits intermediaires pour la preparation de ces composes
GB8504072D0 (en) *	1985-02-18	1985-03-20	Fujisawa Pharmaceutical Co	Cephem compounds
ATE89826T1 (de) *	1985-03-01	1993-06-15	Takeda Chemical Industries Ltd	Antibakterielle verbindungen, ihre herstellung und verwendung.
US4703118A (en) *	1985-04-08	1987-10-27	Eli Lilly And Company	Synthesis of 3-iodomethyl cephalosporins
US4692518A (en) *	1985-11-06	1987-09-08	Eli Lilly And Company	Crystalline (7R)-7-amino-3-(1'-pyridiniummethyl)-3-cephem-4-carboxylate monohydrate compound
JPS62175489A (ja) *	1986-01-29	1987-08-01	Sanwa Kagaku Kenkyusho:Kk	新規なセフアロスポリン誘導体及びその塩、これらの製法並びに該化合物を有効成分とする感染症治療剤
US5359057A (en) *	1986-02-07	1994-10-25	Hoffmann-La Roche Inc.	Acylation of amines
JPS63107989A (ja) *	1986-06-04	1988-05-12	Tanabe Seiyaku Co Ltd	セファロスポリン化合物
AT387022B (de) *	1986-06-04	1988-11-25	Biochemie Gmbh	Verfahren zur herstellung einer neuen kristallinen form eines cefalosporinderivats
IL82738A0 (en) *	1986-06-16	1987-12-20	Tanabe Seiyaku Co	Cephalosporin compounds,their preparation and pharmaceutical compositions containing them
DE3778346D1 (de) *	1986-09-10	1992-05-21	Biochemie Gmbh	Stabile, kristalline form eines cefalosporin-zwischenproduktes.
US4954624A (en) *	1986-10-07	1990-09-04	Sandoz Ltd.	Process for the production of cephalosporin derivatives
US5021564A (en) *	1987-02-02	1991-06-04	Eli Lilly And Company	Process for preparing ceftazidime pentahydrate
EP0278656B1 (fr) *	1987-02-02	1992-06-03	Eli Lilly And Company	Procédé pour la préparation de pentahydrate de ceftazidime
GB8802622D0 (en) *	1988-02-05	1988-03-02	Glaxo Group Ltd	Chemical compound
KR0159760B1 (ko) *	1988-12-27	1998-12-01	리로이 휘테커	아실화 방법
US5194604A (en) *	1990-06-29	1993-03-16	E. R. Squibb & Sons, Inc.	Process and intermediates for beta-lactams having aminothiazole(iminooxyacetic acid)acetic acid sidechains
KR940000112B1 (ko) *	1990-07-05	1994-01-05	주식회사 대웅제약	신규의 3-치환 세펨화합물 및 그의 제조방법
US5281589A (en) *	1991-06-15	1994-01-25	Cheil Foods & Chemicals, Inc.	3-fused pyridiniummethyl cephalosporins
KR100194994B1 (ko) *	1993-06-05	1999-06-15	손경식	새로운 세펨 화합물
PL179415B1 (pl) *	1994-04-25	2000-09-29	Smithkline Beecham Plc	Preparat farmaceutyczny do leczenia zakazen bakteryjnych i sposób wytwarzania preparatu farmaceutycznego do leczenia zakazen bakteryjnych PL PL
US6472383B1 (en)	1994-04-25	2002-10-29	Smithkline Beecham P.L.C.	Pharmaceutical formulations
EP0760820A1 (fr) *	1994-05-23	1997-03-12	Korea Institute Of Science And Technology	Composes de cephalosporine et leurs procedes de preparation
US5831085A (en) *	1997-01-16	1998-11-03	Lupin Laboratories Limited	Process for manufacture of cephalosporin such as ceftazidime and intermediate thereof
IN189047B (fr)	1998-06-01	2002-12-14	Ranbaxy Lab Ltd
US6930983B2 (en) *	2000-03-15	2005-08-16	Texas Instruments Incorporated	Integrated circuits, systems, apparatus, packets and processes utilizing path diversity for media over packet applications
KR100342600B1 (ko)	2000-03-06	2002-07-04	한미정밀화학주식회사	신규한 티아졸 화합물 및 그의 제조 방법
KR100392409B1 (ko)	2000-03-20	2003-07-22	한미정밀화학주식회사	신규한 티아졸 화합물을 이용한 세팔로스포린계항생물질의 제조 방법
US6911441B2 (en) *	2002-12-16	2005-06-28	Akzo Nobel N.V.	Prolonged release pharmaceutical composition
CN1312158C (zh) *	2005-05-20	2007-04-25	天津市医药集团技术发展有限公司	一种头孢克肟的制备方法
EP2209474A4 (fr)	2007-10-09	2013-07-24	Sopharmia Inc	Inhibiteurs de bêta-lactamase à large spectre
CN101293891B (zh) *	2008-06-12	2011-01-12	齐鲁安替制药有限公司	头孢他啶中间体的制备方法
WO2013036783A2 (fr)	2011-09-09	2013-03-14	Cubist Pharmaceuticals, Inc.	Procédés de traitement d'infections intrapulmonaires
US8809314B1 (en)	2012-09-07	2014-08-19	Cubist Pharmacueticals, Inc.	Cephalosporin compound
US8476425B1 (en)	2012-09-27	2013-07-02	Cubist Pharmaceuticals, Inc.	Tazobactam arginine compositions
AU2014241481B9 (en)	2013-03-13	2018-02-15	Theravance Biopharma Antibiotics Ip, Llc	Hydrochloride salts of an antibiotic compound
US9872906B2 (en)	2013-03-15	2018-01-23	Merck Sharp & Dohme Corp.	Ceftolozane antibiotic compositions
US20140274997A1 (en)	2013-03-15	2014-09-18	Cubist Pharmaceuticals, Inc.	Cephalosporin pharmaceutical compositions
UA121298C2 (uk)	2013-03-15	2020-05-12	Мерк Шарп І Доум Корп.	Антибіотична композиція на основі цефтолозану і тазобактаму
EP3043797B1 (fr)	2013-09-09	2020-04-08	Merck Sharp & Dohme Corp.	Traitement d'infections au moyen de ceftolozane/tazobactam chez des sujets ayant une fonction rénale altérée
US8906898B1 (en)	2013-09-27	2014-12-09	Calixa Therapeutics, Inc.	Solid forms of ceftolozane
CN106336418B (zh) *	2016-08-19	2019-02-01	上海上药新亚药业有限公司	一种头孢他啶盐酸盐的固相合成法

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4017515A (en) *	1971-05-14	1977-04-12	Glaxo Laboratories Limited	α-(Etherified oximino) carboxylic acids and acid chlorides
US3971778A (en) *	1972-05-12	1976-07-27	Glaxo Laboratories Limited	Cephalosporins having (α-etherified oximino)acylamido groups at the 7-position
US4093803A (en) *	1971-05-14	1978-06-06	Glaxo Laboratories Limited	7β-[2-Etherified oximino-2-(thienyl-, furyl- or pyridylacetamido)] cephalosporins
US4064346A (en) *	1971-05-14	1977-12-20	Glaxo Laboratories Limited	3-Acetoxymethyl-7β-(2-carboxy-methoxyimino-2-arylacetamido)ceph-3-em-4-carboxylic acids and salts thereof
US4024137A (en) *	1971-05-14	1977-05-17	Glaxo Laboratories Limited	7β-[2-Etherified oximino-2-(phenyl- or naphthylacetamido)] cephalosporins
US4079178A (en) *	1971-05-14	1978-03-14	Glaxo Laboratories Limited	Cephalosporins having (α-etherified oximino) acylamido groups at the 7-position
US4091209A (en) *	1971-05-14	1978-05-23	Glaxo Laboratories Limited	7β-[2-Etherified oximino-2-(phenyl or naphthylacetamido)]cephalosporins having a 2-haloalkylcarbamoyloxymethyl group at the 3-position
US4033950A (en) *	1971-05-14	1977-07-05	Glaxo Laboratories Limited	3-Hydroxymethyl-7β-(2-alkoxy-or benzyloxyimino-2-arylacetamido)ceph-3-em-4-carboxylic acids and salts thereof
GB1399086A (en)	1971-05-14	1975-06-25	Glaxo Lab Ltd	Cephalosporin compounds
US4024133A (en) *	1971-05-14	1977-05-17	Glaxo Laboratories Limited	7β-[2-Etherified oximino-2-(thienyl-,furyl- or pyridylacetamido)]cephalosporins
GB1496757A (en)	1973-12-21	1978-01-05	Glaxo Lab Ltd	Cephalosporin derivatives
US4060686A (en) *	1973-12-21	1977-11-29	Janice Bradshaw	Cephalosporins having a 7-(carboxy substituted α-etherified oximinoarylacetamido) group
US4162360A (en) *	1973-12-21	1979-07-24	Glaxo Laboratories Limited	3-Carbamoyloxymethyl-7-substituted oximino acetamido cephalosporanic acid derivatives
US4144392A (en) *	1973-12-21	1979-03-13	Glaxo Laboratories Limited	Cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyimino-arylacetamido group and at position-3 the residue of a sulphur nucleophile
US4144393A (en) *	1973-12-21	1979-03-13	Glaxo Laboratories Limited	3-Acetoxymethyl cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyiminoarylacetamido group
US4032950A (en) *	1974-12-06	1977-06-28	Hughes Aircraft Company	Liquid phase epitaxial process for growing semi-insulating gaas layers
DK154939C (da) *	1974-12-19	1989-06-12	Takeda Chemical Industries Ltd	Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf
DE2760123C2 (de) *	1976-01-23	1986-04-30	Roussel-Uclaf, Paris	7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
US4165430A (en) *	1976-03-19	1979-08-21	Glaxo Laboratories Limited	Cephalosporins having a 7-carboxy substituted α-etherified oximinoarylacetamido) group
US4166115A (en) *	1976-04-12	1979-08-28	Fujisawa Pharmaceutical Co., Ltd.	Syn 7-oxoimino substituted derivatives of cephalosporanic acid
JPS52125188A (en)	1976-04-14	1977-10-20	Takeda Chem Ind Ltd	Cephalosporin derivatives and their preparation
AU520269B2 (en)	1977-03-14	1982-01-21	Fujisawa Pharmaceutical Co., Ltd.	Cephem and cepham compounds
FR2384782A1 (fr)	1977-03-25	1978-10-20	Roussel Uclaf	Nouvelles oximes derivees de l'acide 3-acetoxymethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
DE2714880A1 (de) *	1977-04-02	1978-10-26	Hoechst Ag	Cephemderivate und verfahren zu ihrer herstellung
DE2716677C2 (de)	1977-04-15	1985-10-10	Hoechst Ag, 6230 Frankfurt	Cephemderivate und Verfahren zu ihrer Herstellung
ZA781870B (en)	1977-04-02	1979-03-28	Hoechst Ag	Cephem derivatives and process for their manufacture
GB1602725A (en)	1977-04-27	1981-11-18	Glaxo Operations Ltd	7-(a-oxyiminoacetamido)-ceph-3-em-4-carboxylic acid derivatives
AR228726A1 (es) *	1978-05-26	1983-04-15	Glaxo Group Ltd	Procedimiento para la preparacion del antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)acetamido)-3-(1-piridiniometil)cef-3-em-4-carboxilato
US4237128A (en) *	1979-04-12	1980-12-02	E. R. Squibb & Sons, Inc.	7-[2-(2-Amino-4-thiazolyl)-2-[(1-carboxy-1,1-dialkyl)alkoxyimino]acetamido]cephem sulfoxides
US4394503A (en) *	1981-12-07	1983-07-19	Bristol-Myers Company	Cephalosporin derivatives

1979
- 1979-05-24 AR AR276665A patent/AR228726A1/es active
- 1979-05-24 AR AR276664A patent/AR229883A1/es active
- 1979-05-25 PT PT69669A patent/PT69669A/pt unknown
- 1979-05-25 CA CA328,413A patent/CA1127633A/fr not_active Expired
- 1979-05-25 CH CH1707/80A patent/CH649556A5/de not_active IP Right Cessation
- 1979-05-25 FI FI791678A patent/FI67555C/fi not_active IP Right Cessation
- 1979-05-25 CH CH491579A patent/CH646178A5/de not_active IP Right Cessation
- 1979-05-25 IT IT7949179A patent/IT1116198B/it active Protection Beyond IP Right Term
- 1979-05-25 DK DK216779A patent/DK157685C/da active
- 1979-05-25 US US06/042,594 patent/US4258041A/en not_active Expired - Lifetime
- 1979-05-25 ES ES480915A patent/ES480915A1/es not_active Expired
- 1979-05-25 SE SE7904576A patent/SE438507B/sv not_active IP Right Cessation
- 1979-05-25 YU YU1231/79A patent/YU41635B/xx unknown
- 1979-05-25 PH PH22562A patent/PH16961A/en unknown
- 1979-05-25 NL NLAANVRAGE7904122,A patent/NL176855C/xx not_active IP Right Cessation
- 1979-05-25 NZ NZ190558A patent/NZ190558A/xx unknown
- 1979-05-25 NO NO791731A patent/NO155347C/no unknown
- 1979-05-25 AU AU47422/79A patent/AU524671B2/en not_active Expired
- 1979-05-25 SI SI7911231A patent/SI7911231A8/sl unknown
- 1979-05-25 IL IL57400A patent/IL57400A/xx unknown
- 1979-05-25 IL IL59793A patent/IL59793A/xx unknown
- 1979-05-25 LU LU81319A patent/LU81319A1/fr unknown
- 1979-05-25 DE DE2921316A patent/DE2921316C2/de not_active Expired
- 1979-05-25 ES ES480914A patent/ES480914A1/es not_active Expired
- 1979-05-25 PT PT69670A patent/PT69670A/pt unknown
- 1979-05-28 FR FR7913531A patent/FR2426695A1/fr active Granted
- 1979-08-08 IE IE1025/79A patent/IE49172B1/en not_active IP Right Cessation
- 1979-08-08 IE IE2453/80A patent/IE49173B1/en unknown
1980
- 1980-03-06 NL NL8001348A patent/NL8001348A/nl not_active Application Discontinuation
- 1980-04-01 NZ NZ193326A patent/NZ193326A/xx unknown
- 1980-04-09 IL IL59793A patent/IL59793A0/xx unknown
- 1980-04-09 FR FR8007929A patent/FR2445835A1/fr active Granted
- 1980-05-19 FI FI801609A patent/FI67705C/fi not_active IP Right Cessation
1981
- 1981-05-27 AT AT0239281A patent/AT370420B/de not_active IP Right Cessation
1982
- 1982-09-13 US US06/417,656 patent/US4600772A/en not_active Expired - Lifetime
- 1982-10-05 YU YU2234/82A patent/YU43097B/xx unknown
- 1982-10-05 SI SI8212234A patent/SI8212234A8/sl unknown
- 1982-11-16 SG SG583/82A patent/SG58382G/en unknown
- 1982-11-26 KE KE3252A patent/KE3252A/xx unknown
1983
- 1983-10-13 HK HK401/83A patent/HK40183A/xx not_active IP Right Cessation
1984
- 1984-05-28 SE SE8402887A patent/SE8402887L/xx not_active Application Discontinuation
- 1984-12-30 MY MY17/84A patent/MY8400017A/xx unknown
1985
- 1985-01-14 NO NO850153A patent/NO850153L/no unknown

Also Published As

Publication number	Publication date
DE2921316C2 (de)	1982-09-16
DK157685B (da)	1990-02-05
AT370420B (de)	1983-03-25
AR228726A1 (es)	1983-04-15
FR2426695A1 (fr)	1979-12-21
KE3252A (en)	1983-01-28
US4258041A (en)	1981-03-24
FR2445835A1 (fr)	1980-08-01
SI8212234A8 (en)	1997-06-30
CH646178A5 (de)	1984-11-15
NO850153L (no)	1979-11-27
DE2921316A1 (de)	1979-12-06
FI801609A7 (fi)	1980-05-19
ES480915A1 (es)	1980-02-01
US4600772A (en)	1986-07-15
SE8402887D0 (sv)	1984-05-28
NO155347C (no)	1987-03-18
IE49172B1 (en)	1985-08-21
CH649556A5 (de)	1985-05-31
IE802453L (en)	1979-11-26
YU43097B (en)	1989-02-28
FI67705C (fi)	1985-05-10
IL59793A (en)	1982-08-31
YU41635B (en)	1987-12-31
FI791678A7 (fi)	1979-11-27
NL176855B (nl)	1985-01-16
ATA239281A (de)	1982-08-15
FI67555B (fi)	1984-12-31
IL57400A (en)	1982-08-31
YU123179A (en)	1983-01-21
IE49173B1 (en)	1985-08-21
NL7904122A (nl)	1979-11-28
IE791025L (en)	1979-11-26
IL59793A0 (en)	1980-06-30
SE7904576L (sv)	1980-02-11
SG58382G (en)	1983-09-02
AU524671B2 (en)	1982-09-30
DK216779A (da)	1979-11-27
SI7911231A8 (en)	1997-06-30
NO155347B (no)	1966-12-08
AU4742279A (en)	1979-11-29
NO791731L (no)	1979-11-27
DK157685C (da)	1990-07-09
NL8001348A (nl)	1980-06-30
FR2445835B1 (fr)	1983-06-03
HK40183A (en)	1983-10-21
MY8400017A (en)	1984-12-31
CA1127633A (fr)	1982-07-13
IL57400A0 (en)	1979-09-30
NZ190558A (en)	1982-05-31
FR2426695B1 (fr)	1982-06-11
NL176855C (nl)	1985-06-17
NZ193326A (en)	1982-05-31
PH16961A (en)	1984-04-27
PT69670A (en)	1979-06-01
AR229883A1 (es)	1983-12-30
IT1116198B (it)	1986-02-10
SE8402887L (sv)	1984-05-28
PT69669A (en)	1979-06-01
ES480914A1 (es)	1980-02-01
FI67555C (fi)	1985-04-10
LU81319A1 (fr)	1979-09-11
YU223482A (en)	1983-04-30
FI67705B (fi)	1985-01-31

Publication	Publication Date	Title
SE438507B (sv)	1985-04-22	Nya cefalosporinantibiotika samt forfarande for framstellning derav
KR830000606B1 (ko)	1983-03-17	세팔로스포린 항생제의 제조방법
DD202720A5 (de)	1983-09-28	Verfahren zur herstellung von cephalosporinderivaten
US4621081A (en)	1986-11-04	Cephalosporin antibiotics
US4464368A (en)	1984-08-07	Cephalosporin antibiotics
US4315005A (en)	1982-02-09	Cephalosporin antibiotics
US4427675A (en)	1984-01-24	Cephalosporin antibiotics
EP0181172B1 (fr)	1992-03-18	Antibiotiques à base de céphalosporine
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
NL7907881A (nl)	1980-04-29	Nieuwe cefalosporine-antibiotica, werkwijze voor de bereiding daarvan en farmaceutische preparaten die deze bevatten.
SE438508B (sv)	1985-04-22	Nya cefalosporinantibiotika samt forfarande for framstellning derav
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
GB2183630A (en)	1987-06-10	Cephalosporin antibiotics
EP0095329A2 (fr)	1983-11-30	Céphalosporines antibiotiques
GB2183629A (en)	1987-06-10	Cephalosporin antibiotics

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