CH639096A5 - Cephalosporin derivatives, process for their preparation and pharmaceutical preparations containing them - Google Patents

Cephalosporin derivatives, process for their preparation and pharmaceutical preparations containing them Download PDF

Info

Publication number: CH639096A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; fur; ceph; carboxylate
Prior art date: 1977-04-19

Application number

CH414678A

Other languages

German (de)

English (en)

Inventor

Michael Gregson

Original Assignee

Glaxo Lab 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.)

1977-04-19

Filing date

1978-04-18

Publication date

1983-10-31

1978-04-18 Application filed by Glaxo Lab Ltd filed Critical Glaxo Lab Ltd

1983-10-31 Publication of CH639096A5 publication Critical patent/CH639096A5/de

Links

238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 9
239000000825 pharmaceutical preparation Substances 0.000 title claims 2
229930186147 Cephalosporin Natural products 0.000 title description 4
229940124587 cephalosporin Drugs 0.000 title description 4
150000001780 cephalosporins Chemical class 0.000 title description 3
150000002148 esters Chemical class 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 27
JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 claims description 22
-1 methoxycarbonyloxymethyl (6R, 7R) -3-carbamoyloxy-methyl-7 - [(Z) -2- (fur-2-yl) -2-methoxyiminoacetamido] -ceph-3-em-4-carboxylate Chemical compound 0.000 claims description 22
229960001668 cefuroxime Drugs 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
JFPVXVDWJQMJEE-SWWZKJRFSA-N 55268-75-2 Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)/C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-SWWZKJRFSA-N 0.000 claims description 2
241000251730 Chondrichthyes Species 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
150000007942 carboxylates Chemical class 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
239000008177 pharmaceutical agent Substances 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
239000007787 solid Substances 0.000 description 15
239000000047 product Substances 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
238000010521 absorption reaction Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000284 extract Substances 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 7
235000010262 sodium metabisulphite Nutrition 0.000 description 7
238000001665 trituration Methods 0.000 description 7
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 6
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239000002585 base Substances 0.000 description 6
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230000032050 esterification Effects 0.000 description 6
238000005886 esterification reaction Methods 0.000 description 6
210000001035 gastrointestinal tract Anatomy 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
210000002966 serum Anatomy 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
239000012346 acetyl chloride Substances 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
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 4
230000015572 biosynthetic process Effects 0.000 description 4
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239000011734 sodium Substances 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000009518 sodium iodide Nutrition 0.000 description 4
229940001584 sodium metabisulfite Drugs 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
108090000371 Esterases Proteins 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000003782 beta lactam antibiotic agent Substances 0.000 description 3
239000006260 foam Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
GCAJKKPVKXKYGK-JTBFTWTJSA-M potassium;(6r,7r)-3-(carbamoyloxymethyl)-7-[[(2z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [K+].N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 GCAJKKPVKXKYGK-JTBFTWTJSA-M 0.000 description 3
239000004296 sodium metabisulphite Substances 0.000 description 3
239000002132 β-lactam antibiotic Substances 0.000 description 3
229940124586 β-lactam antibiotics Drugs 0.000 description 3
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
230000021235 carbamoylation Effects 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 2
244000005700 microbiome Species 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
229940056360 penicillin g Drugs 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000012453 solvate Substances 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
ZNQCEVIJOQZWLO-VURMDHGXSA-N (2z)-2-(furan-2-yl)-2-methoxyiminoacetic acid Chemical compound CO\N=C(/C(O)=O)C1=CC=CO1 ZNQCEVIJOQZWLO-VURMDHGXSA-N 0.000 description 1
JFPVXVDWJQMJEE-NCIZMAFVSA-N (6r)-3-(carbamoyloxymethyl)-7-[[(2z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]12)CC(COC(N)=O)=C(C(O)=O)N1C(=O)C2NC(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-NCIZMAFVSA-N 0.000 description 1
SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical class S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
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 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
108020004256 Beta-lactamase Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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DARWLDOSIAZDME-IUYQGCFVSA-N C[C@H]([C@H](C)Cl)OC(=O)O Chemical compound C[C@H]([C@H](C)Cl)OC(=O)O DARWLDOSIAZDME-IUYQGCFVSA-N 0.000 description 1
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FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
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VIOAGOMGEZTUHG-UHFFFAOYSA-L magnesium;2-hydroxyacetate;octadecanoate Chemical compound [Mg+2].OCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O VIOAGOMGEZTUHG-UHFFFAOYSA-L 0.000 description 1
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239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229940059096 powder for oral suspension Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
235000012751 sunset yellow FCF Nutrition 0.000 description 1
239000004173 sunset yellow FCF Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
- 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings

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)

CH414678A 1977-04-19 1978-04-18 Cephalosporin derivatives, process for their preparation and pharmaceutical preparations containing them CH639096A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB16202/77A GB1598568A (en)	1977-04-19	1977-04-19	Esters of(6r,7r)-3-carbamoyloxymethyl-7-((z)-2-(fur-2-yl)-2-methoxyiminoacetamido)-ceph-3-em-4-carboxylic acid

Publications (1)

Publication Number	Publication Date
CH639096A5 true CH639096A5 (en)	1983-10-31

Family

ID=10073017

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH414678A CH639096A5 (en)	1977-04-19	1978-04-18	Cephalosporin derivatives, process for their preparation and pharmaceutical preparations containing them

Country Status (20)

Country	Link
JP (1)	JPS53132592A (fr)
KR (1)	KR840000081B1 (fr)
AT (1)	AT363183B (fr)
AU (1)	AU521098B2 (fr)
BE (1)	BE866093A (fr)
CA (1)	CA1093068A (fr)
CH (1)	CH639096A5 (fr)
DE (1)	DE2816873A1 (fr)
DK (1)	DK147513C (fr)
ES (1)	ES468895A1 (fr)
FR (1)	FR2387988A1 (fr)
GB (1)	GB1598568A (fr)
IE (1)	IE46726B1 (fr)
IL (1)	IL54531A (fr)
IT (1)	IT1104842B (fr)
NL (1)	NL7804097A (fr)
NZ (1)	NZ186998A (fr)
SE (1)	SE433748B (fr)
YU (1)	YU90978A (fr)
ZA (1)	ZA782211B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2482587A1 (fr) *	1980-05-14	1981-11-20	Poudres & Explosifs Ste Nale	Procede de synthese de chloroformiates a-chlores et nouveaux chloroformiates a-chlores
GR76477B (fr) *	1981-03-23	1984-08-10	Kyoto Pharma Ind
FR2532933B1 (fr) *	1982-06-29	1987-11-13	Astra Laekemedel Ab	Perfectionnements apportes a la preparation d'antibiotiques
IT1190897B (it) *	1982-06-29	1988-02-24	Opos Biochimica Srl	Procedimento per la preparazione dell'estere 1-etossicarbonilossietilico dell'acido 6-(d(-)-alfa aminoalfa fenilacetamido)-penicillanico
IL68992A (en) *	1982-06-29	1991-06-10	Astra Laekemedel Ab	Alpha-bromo diethyl carbonate and process for the preparation of ethoxycarbonyloxy esters of penicillanic acids
GB2123821B (en) *	1982-06-29	1987-04-23	Astra Laekemedel Ab	At-halogeno diethyl carbonates and their use in the preparation of antibiotics
YU44680B (en) *	1982-07-30	1990-12-31	Glaxo Lab Ltd	Process for obtaining very pure amorphous form of cephuroxim axetile
US4606865A (en) *	1982-09-20	1986-08-19	Astra Lakemedel Aktiebolag	Methods for the preparation of α-bromodiethylcarbonate
IL67623A (en) *	1983-01-05	1984-09-30	Teva Pharma	1'-ethoxycarbonyloxyethyl ester of valproic acid,its preparation and pharmaceutical compositions containing it
GB8320521D0 (en) *	1983-07-29	1983-09-01	Glaxo Group Ltd	Chemical process
FR2551058B1 (fr) *	1983-08-26	1986-09-26	Poudres & Explosifs Ste Nale	Procede de preparation de chloroformiates a-chlores
GB8400024D0 (en) *	1984-01-03	1984-02-08	Glaxo Group Ltd	Cephalosporin antibiotics
US4612143A (en) *	1984-09-17	1986-09-16	Societe Nationale Des Poudres Et Explosifs	Process for the preparation of fluoroformates
US5202454A (en) *	1986-07-11	1993-04-13	Societe Nationale Des Poudres Et Explosifs	Process for the manufacture of 1-bromoalkyl hydrocarbyl carbonates
KR100342944B1 (ko)	1999-11-08	2002-07-02	민경윤	고순도 세프포독심 프록세틸의 제조방법
GB0301938D0 (en) *	2003-01-28	2003-02-26	Biochemie Gmbh	Organic compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1453049A (en) *	1973-08-21	1976-10-20	Glaxo Lab Ltd	Cephalosporing antibiotics
CA1094545A (fr) *	1976-02-16	1981-01-27	Michael Gregson	Traduction non-disponible
CA1093549A (fr) *	1976-02-16	1981-01-13	Michael Gregson	Traduction non-disponible

1977
- 1977-04-19 GB GB16202/77A patent/GB1598568A/en not_active Expired
1978
- 1978-04-03 CA CA300,315A patent/CA1093068A/fr not_active Expired
- 1978-04-18 CH CH414678A patent/CH639096A5/de not_active IP Right Cessation
- 1978-04-18 AU AU35187/78A patent/AU521098B2/en not_active Expired
- 1978-04-18 NL NL7804097A patent/NL7804097A/xx not_active Application Discontinuation
- 1978-04-18 ES ES468895A patent/ES468895A1/es not_active Expired
- 1978-04-18 BE BE186875A patent/BE866093A/fr not_active IP Right Cessation
- 1978-04-18 ZA ZA00782211A patent/ZA782211B/xx unknown
- 1978-04-18 JP JP4643178A patent/JPS53132592A/ja active Pending
- 1978-04-18 IT IT48941/78A patent/IT1104842B/it active
- 1978-04-18 KR KR7801139A patent/KR840000081B1/ko not_active Expired
- 1978-04-18 AT AT0274878A patent/AT363183B/de not_active IP Right Cessation
- 1978-04-18 DE DE19782816873 patent/DE2816873A1/de not_active Withdrawn
- 1978-04-18 DK DK168778A patent/DK147513C/da not_active IP Right Cessation
- 1978-04-18 YU YU00909/78A patent/YU90978A/xx unknown
- 1978-04-18 SE SE7804400A patent/SE433748B/sv unknown
- 1978-04-18 IL IL54531A patent/IL54531A/xx unknown
- 1978-04-18 NZ NZ186998A patent/NZ186998A/xx unknown
- 1978-04-18 IE IE760/78A patent/IE46726B1/en unknown
- 1978-04-19 FR FR7811514A patent/FR2387988A1/fr active Granted

Also Published As

Publication number	Publication date
FR2387988B1 (fr)	1982-06-11
SE7804400L (sv)	1978-10-20
SE433748B (sv)	1984-06-12
IL54531A0 (en)	1978-07-31
AT363183B (de)	1981-07-10
IT1104842B (it)	1985-10-28
NL7804097A (nl)	1978-10-23
YU90978A (en)	1983-01-21
ES468895A1 (es)	1978-12-01
JPS53132592A (en)	1978-11-18
AU521098B2 (en)	1982-03-18
IE780760L (en)	1978-10-19
KR840000081B1 (ko)	1984-02-08
BE866093A (fr)	1978-10-18
DK147513B (da)	1984-09-10
FR2387988A1 (fr)	1978-11-17
IT7848941A0 (it)	1978-04-18
IL54531A (en)	1981-07-31
DK147513C (da)	1985-03-18
KR830000246A (ko)	1983-03-30
GB1598568A (en)	1981-09-23
DK168778A (da)	1978-10-20
DE2816873A1 (de)	1978-11-02
ZA782211B (en)	1979-04-25
ATA274878A (de)	1980-12-15
CA1093068A (fr)	1981-01-06
NZ186998A (en)	1981-05-01
IE46726B1 (en)	1983-09-07
AU3518778A (en)	1979-10-25

Publication	Publication Date	Title
DE2706413C2 (de)	1986-08-28	Acyloxyethylester des Cefuroxims, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
CH639096A5 (en)	1983-10-31	Cephalosporin derivatives, process for their preparation and pharmaceutical preparations containing them
DE2228012B2 (de)	1979-05-23	-Aminophenylacetamido] -penicülansäure und Verfahren zu seiner Herstellung
DE2744135A1 (de)	1978-04-06	Cephalosporinderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel
DD210279A5 (de)	1984-06-06	Verfahren zur herstellung von cephalosporinverbindungen
AT392279B (de)	1991-02-25	Verfahren zur herstellung von neuen cephalosporin-antibiotika
DE2537070C2 (fr)	1987-06-25
DE3789720T2 (de)	1994-08-18	Cephalosporinverbindungen.
EP0030632B1 (fr)	1985-02-20	Dérivés de benzothiazole, compositions pharmaceutiques les contenant et procédé pour leur préparation
DE68915928T2 (de)	1994-09-22	Benzoheterozyklische Verbindungen.
DE2118635A1 (de)	1972-11-02	Acylaminocephalosporansäuren und Verfahren zu ihrer Herstellung
DE2706360A1 (de)	1977-08-18	Cephalosporinantibiotika, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen
DE1242619B (de)	1967-06-22	Verfahren zur Herstellung von neuen Nikotionsaeureestern
DE3020421A1 (de)	1981-12-10	Imidazoazolalkensaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln
DE2557397A1 (de)	1976-06-24	Cephalosporin-antibiotika
DE2043817C3 (de)	1981-09-03	1,4-Dihydro-3-carboxy-cyclopentano-(h)-chinolon-(4)-derivate, Verfahren zu deren Herstellung sowie deren Verwendung zur Bekämpfung antibakterieller Erkrankungen
DE2011885C3 (de)	1981-05-21	1,4-Dihydro-3-carboxy-cyclopentano (h)-chinolon-(4)-derivate, Verfahren zur Herstellung derselben und ihre Verwendung
AT322562B (de)	1975-05-26	Verfahren zur herstellung von neuen pyridopyridazinderivaten und deren pharmazeutisch vertraeglichen salzen
DE69422793T2 (de)	2000-06-21	Phosphonsäurediester-derivat
DE2605824B2 (de)	1980-07-24	N-Acylaniline, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen
AT335605B (de)	1977-03-25	Verfahren zur herstellung neuer acylderivate des antibiotikums ws-4545
AT361627B (de)	1981-03-25	Verfahren zur herstellung von neuen cephalos- porinantibiotika
DE69422495T2 (de)	2000-05-18	Chinolondisulfide als zwischenverbindungen
DE3200427A1 (de)	1983-03-03	Neue organische verbindung, verfahren zu ihrer herstellung und ihre verwendung
AT358174B (de)	1980-08-25	Verfahren zur herstellung von neuen 2-nied. alkyl-7-subst.-2- oder -3-cephem-4-carbonsaeure- verbindungen

Legal Events

Date	Code	Title	Description
1986-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased