CH645906A5 - Cephalosporinantibiotika. - Google Patents

Cephalosporinantibiotika. Download PDF

Info

Publication number: CH645906A5
Authority: CH; Switzerland
Prior art keywords: group; carboxyl; formula; compound; salt
Prior art date: 1979-10-02

Application number

CH734280A

Other languages

German (de)

English (en)

Inventor

Cynthia Hilda O'callaghan

David George Hubert Livermore

Christopher Earle 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.)

1979-10-02

Filing date

1980-10-01

Publication date

1984-10-31

1980-10-01 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1984-10-31 Publication of CH645906A5 publication Critical patent/CH645906A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 111
-1 2-aminothiazol-4-yl Chemical group 0.000 claims description 77
150000003839 salts Chemical class 0.000 claims description 55
239000002253 acid Substances 0.000 claims description 38
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
231100000252 nontoxic Toxicity 0.000 claims description 26
230000003000 nontoxic effect Effects 0.000 claims description 26
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
229940124587 cephalosporin Drugs 0.000 claims description 21
238000000034 method Methods 0.000 claims description 21
229930186147 Cephalosporin Natural products 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 18
239000003242 anti bacterial agent Substances 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 17
150000001780 cephalosporins Chemical class 0.000 claims description 16
229940088710 antibiotic agent Drugs 0.000 claims description 14
230000003115 biocidal effect Effects 0.000 claims description 14
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 7
150000001450 anions Chemical class 0.000 claims description 5
239000012038 nucleophile Substances 0.000 claims description 5
241000282414 Homo sapiens Species 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
239000012453 solvate Substances 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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238000006243 chemical reaction Methods 0.000 description 25
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
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239000000463 material Substances 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 5
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
235000011007 phosphoric acid Nutrition 0.000 description 4
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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 4
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
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241000588772 Morganella morganii Species 0.000 description 1
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241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
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241000191940 Staphylococcus Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
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ZIQPQYFSSSHQBP-UHFFFAOYSA-N acetyl 2,3-dihydroxypropanoate Chemical compound CC(=O)OC(=O)C(O)CO ZIQPQYFSSSHQBP-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
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125000005907 alkyl ester group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000013011 aqueous formulation Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
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239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
150000001782 cephems Chemical class 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
101150102678 clu1 gene Proteins 0.000 description 1
229920006026 co-polymeric resin Polymers 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
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150000002170 ethers Chemical class 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
229940013688 formic acid Drugs 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
229940047650 haemophilus influenzae Drugs 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 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
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
229940006461 iodide ion Drugs 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 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
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
229960005357 lysine acetate Drugs 0.000 description 1
239000002609 medium Substances 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 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
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
125000002560 nitrile group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
244000052769 pathogen Species 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 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
229920002223 polystyrene Polymers 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
KIDBBTHHMJOMAU-UHFFFAOYSA-N propan-1-ol;hydrate Chemical compound O.CCCO KIDBBTHHMJOMAU-UHFFFAOYSA-N 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
230000005588 protonation Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
229940115939 shigella sonnei Drugs 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017550 sodium carbonate 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
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000012258 stirred mixture 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
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
125000003375 sulfoxide group Chemical group 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
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 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
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003568 thioethers Chemical class 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
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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 1
238000005866 tritylation reaction Methods 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
150000003952 β-lactams Chemical class 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH734280A 1979-10-02 1980-10-01 Cephalosporinantibiotika. CH645906A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7934069		1979-10-02

Publications (1)

Publication Number	Publication Date
CH645906A5 true CH645906A5 (de)	1984-10-31

Family

ID=10508218

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH734280A CH645906A5 (de)	1979-10-02	1980-10-01	Cephalosporinantibiotika.

Country Status (10)

Country	Link
JP (1)	JPS5657790A (it)
AU (1)	AU538653B2 (it)
BE (1)	BE885487A (it)
CH (1)	CH645906A5 (it)
DE (1)	DE3037101A1 (it)
FR (1)	FR2466468A1 (it)
GB (1)	GB2062624B (it)
IT (1)	IT1143007B (it)
NL (1)	NL8005440A (it)
ZA (1)	ZA806084B (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58210093A (ja) *	1982-05-20	1983-12-07	グラクソ・グル−プ・リミテツド	セフアロスポリン抗生物質

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1522140A (en) *	1974-12-20	1978-08-23	Glaxo Lab Ltd	Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl cephalosporins methods for their preparation and compositions containing them
PH17188A (en) *	1977-03-14	1984-06-14	Fujisawa Pharmaceutical Co	New cephem and cepham compounds and their pharmaceutical compositions and method of use
SE439312B (sv) *	1977-03-25	1985-06-10	Roussel Uclaf	Sett att framstella nya oximderivat av 3-acetoximetyl-7-aminotiazolylacetamido cefalosporansyra
DE2758001A1 (de) *	1977-12-24	1979-07-12	Hoechst Ag	Cephalosporinderivate 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

1980
- 1980-10-01 IT IT49784/80A patent/IT1143007B/it active
- 1980-10-01 AU AU62881/80A patent/AU538653B2/en not_active Ceased
- 1980-10-01 FR FR8021035A patent/FR2466468A1/fr active Granted
- 1980-10-01 BE BE0/202299A patent/BE885487A/fr not_active IP Right Cessation
- 1980-10-01 NL NL8005440A patent/NL8005440A/nl not_active Application Discontinuation
- 1980-10-01 DE DE19803037101 patent/DE3037101A1/de not_active Withdrawn
- 1980-10-01 JP JP13822380A patent/JPS5657790A/ja active Pending
- 1980-10-01 GB GB8031704A patent/GB2062624B/en not_active Expired
- 1980-10-01 ZA ZA00806084A patent/ZA806084B/xx unknown
- 1980-10-01 CH CH734280A patent/CH645906A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1143007B (it)	1986-10-22
GB2062624A (en)	1981-05-28
FR2466468B1 (it)	1984-02-10
BE885487A (fr)	1981-04-01
IT8049784A0 (it)	1980-10-01
AU538653B2 (en)	1984-08-23
JPS5657790A (en)	1981-05-20
DE3037101A1 (de)	1981-04-16
FR2466468A1 (fr)	1981-04-10
ZA806084B (en)	1982-05-26
AU6288180A (en)	1981-04-09
GB2062624B (en)	1983-09-07
NL8005440A (nl)	1981-04-06

Legal Events

Date	Code	Title	Description
1986-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
AT370420B (de)	1983-03-25	Verfahren zur herstellung von neuen cephalosporin-antibiotika
AT369749B (de)	1983-01-25	Verfahren zur herstellung von neuen cephalosporinantibiotika
DE2834097A1 (de)	1979-02-22	Eckige klammer auf 2-(syn)-carbamoyloximinoacetamido eckige klammer zu -cephalosporine, verfahren zu deren herstellung sowie diese enthaltende therapeutische mittel fuer die behandlung von bakteriellen infektionen
US4464368A (en)	1984-08-07	Cephalosporin antibiotics
DE2943427A1 (de)	1980-05-08	Cephalosporinverbindungen
CH649557A5 (de)	1985-05-31	Cephalosporinantibiotika.
US4315005A (en)	1982-02-09	Cephalosporin antibiotics
CH649298A5 (de)	1985-05-15	Cephalosporin-antibiotika.
CH637139A5 (de)	1983-07-15	Verfahren zur herstellung von cephalosporinverbindungen.
DE2943437A1 (de)	1980-05-08	Cephalosporinverbindungen
KR830001130B1 (ko)	1983-06-14	세팔로스포린 항생제의 제조방법
CH645906A5 (de)	1984-10-31	Cephalosporinantibiotika.
AT375663B (de)	1984-08-27	Verfahren zur herstellung von neuen cephalosporinantibiotika
GB2037281A (en)	1980-07-09	7-( alpha -(2-amino.4-thiazolyl)- alpha - hydroximino-acetamido)- cephalosporins
DE3323462A1 (de)	1984-01-12	Cephalosporin-antibiotika
AT371474B (de)	1983-06-27	Verfahren zur herstellung von neuen cephalosporinantibiotika
DE3342317A1 (de)	1984-05-24	Cephalosporin-antibiotika
CH649297A5 (en)	1985-05-15	Cephalosporin compounds, their preparation and pharmaceutical compositions containing them
AT371126B (de)	1983-06-10	Verfahren zur herstellung von neuen cephalosporin-antibiotika
AT375662B (de)	1984-08-27	Verfahren zur herstellung von neuen cephalosporinantibiotika
AT371125B (de)	1983-06-10	Verfahren zur herstellung von neuen cephalosporinantibiotika
DE2760488C2 (de)	1994-04-07	Cephalosporinderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
AT371476B (de)	1983-06-27	Verfahren zur herstellung von neuen cephalosporinantibiotika
CH646704A5 (en)	1984-12-14	Cephalosporin antibiotics, their preparation, and pharmaceutical compositions containing them
CH646705A5 (en)	1984-12-14	Cephalosporin antibiotics, their preparation, and a pharmaceutical composition containing them