NO812268L - Fremgangsmaate ved fremstilling av cefalosporiner. - Google Patents

Fremgangsmaate ved fremstilling av cefalosporiner.

Info

Publication number: NO812268L
Authority: NO; Norway
Prior art keywords: acid; amino; hydrogen; formula; thiazolyl
Prior art date: 1980-07-03

Application number

NO812268A

Other languages

English (en)

Norwegian (no)

Inventor

David Alan Berges

George Lawrence Dunn

Original Assignee

Smithkline Corp

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.)

1980-07-03

Filing date

1981-07-02

Publication date

1982-01-04

1981-07-02 Application filed by Smithkline Corp filed Critical Smithkline Corp

1982-01-04 Publication of NO812268L publication Critical patent/NO812268L/no

Links

238000000034 method Methods 0.000 title claims description 17
238000004519 manufacturing process Methods 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims description 21
-1 cephalosporin compound Chemical class 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
229930186147 Cephalosporin Natural products 0.000 claims description 10
229940124587 cephalosporin Drugs 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
229940126062 Compound A Drugs 0.000 description 5
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
150000001780 cephalosporins Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
OLVCFLKTBJRLHI-AXAPSJFSSA-N cefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-AXAPSJFSSA-N 0.000 description 3
229960003012 cefamandole Drugs 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
229940127557 pharmaceutical product Drugs 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
150000003573 thiols Chemical class 0.000 description 3
VIKZIPIQNIJTFL-ONNFQVAWSA-N (2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetamide Chemical compound CO\N=C(\C(N)=O)C1=CSC(N)=N1 VIKZIPIQNIJTFL-ONNFQVAWSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
239000002585 base Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
QITDACOZCQXYQY-BAFYGKSASA-N (6r)-7-amino-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC=CN2C(=O)C(N)[C@H]21 QITDACOZCQXYQY-BAFYGKSASA-N 0.000 description 1
NOXPGSDFQWSNSW-UHFFFAOYSA-N (sulfamoylamino)methane Chemical compound CNS(N)(=O)=O NOXPGSDFQWSNSW-UHFFFAOYSA-N 0.000 description 1
CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
HPVYMSBZIOPTKS-UHFFFAOYSA-N 1,2-dihydrotetrazole-5-thione;sodium Chemical compound [Na].[Na].S=C1N=NNN1 HPVYMSBZIOPTKS-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
241000894006 Bacteria Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
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 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000011358 absorbing material Substances 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
229960002989 glutamic acid Drugs 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
229960004275 glycolic acid Drugs 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229960000443 hydrochloric acid Drugs 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000003389 potentiating 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
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000004964 sulfoalkyl group Chemical group 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003536 tetrazoles Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

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

NO812268A 1980-07-03 1981-07-02 Fremgangsmaate ved fremstilling av cefalosporiner. NO812268L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/165,822 US4308267A (en)	1980-07-03	1980-07-03	7-[2-Alkoxyimino-2-(amino-thiazole)acetamido]-3-[1-(sulfaminoalkly)tetrazolthiomethyl]cephalosporins

Publications (1)

Publication Number	Publication Date
NO812268L true NO812268L (no)	1982-01-04

Family

ID=22600626

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO812268A NO812268L (no)	1980-07-03	1981-07-02	Fremgangsmaate ved fremstilling av cefalosporiner.

Country Status (23)

Country	Link
US (1)	US4308267A (de)
EP (1)	EP0043713B1 (de)
JP (1)	JPS5745189A (de)
KR (1)	KR840002046B1 (de)
AR (1)	AR228606A1 (de)
AT (1)	ATE9585T1 (de)
AU (1)	AU547942B2 (de)
CA (1)	CA1151150A (de)
DE (1)	DE3166321D1 (de)
DK (1)	DK286981A (de)
ES (1)	ES503622A0 (de)
FI (1)	FI66876C (de)
GR (1)	GR74363B (de)
HU (1)	HU185934B (de)
IE (1)	IE51365B1 (de)
IL (1)	IL63206A (de)
NO (1)	NO812268L (de)
NZ (1)	NZ197573A (de)
PH (1)	PH17670A (de)
PT (1)	PT73292B (de)
YU (1)	YU162481A (de)
ZA (1)	ZA814484B (de)
ZW (1)	ZW15181A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4526977A (en) *	1981-10-07	1985-07-02	American Home Products Corporation	2-(3-Amino-5-isoxazolyl)-2-oxyimino-acetic acids

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4171362A (en) *	1975-10-30	1979-10-16	Smithkline Corporation	7-Acylamino-3-(sulfaminoalkyl substituted tetrazolylthiomethyl)cephalosporins antibacterial compositions containing them and methods of treating bacterial infections with them
DE2760123C2 (de) *	1976-01-23	1986-04-30	Roussel-Uclaf, Paris	7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
JPS52125188A (en)	1976-04-14	1977-10-20	Takeda Chem Ind Ltd	Cephalosporin derivatives and their preparation
US4066762A (en) *	1976-07-12	1978-01-03	Smithkline Corporation	Derivatives of 7-(2-substituted-2-hydroxyiminoacetamido)-3-(1-substituted tetrazol-5-ylthiomethyl-3-cephem-4-carboxylic acid
DE2714880A1 (de) *	1977-04-02	1978-10-26	Hoechst Ag	Cephemderivate und verfahren zu ihrer herstellung
MC1259A1 (fr)	1978-05-30	1980-01-14	Hoffmann La Roche	Derives acyles
US4220761A (en) *	1978-09-12	1980-09-02	Fujisawa Pharmaceutical Co., Ltd.	7-[Substituted oximinoacetamido]-3-[hydroxy alkyltetrazolo]cephalosporin derivatives

1980
- 1980-07-03 US US06/165,822 patent/US4308267A/en not_active Expired - Lifetime
1981
- 1981-06-29 DK DK286981A patent/DK286981A/da not_active Application Discontinuation
- 1981-06-29 CA CA000380845A patent/CA1151150A/en not_active Expired
- 1981-06-29 IL IL63206A patent/IL63206A/xx unknown
- 1981-06-29 JP JP56102168A patent/JPS5745189A/ja active Pending
- 1981-06-29 AU AU72343/81A patent/AU547942B2/en not_active Ceased
- 1981-06-30 YU YU01624/81A patent/YU162481A/xx unknown
- 1981-06-30 GR GR65386A patent/GR74363B/el unknown
- 1981-06-30 FI FI812046A patent/FI66876C/fi not_active IP Right Cessation
- 1981-06-30 NZ NZ197573A patent/NZ197573A/en unknown
- 1981-06-30 PH PH25836A patent/PH17670A/en unknown
- 1981-06-30 PT PT73292A patent/PT73292B/pt unknown
- 1981-07-01 ZW ZW151/81A patent/ZW15181A1/xx unknown
- 1981-07-02 ZA ZA814484A patent/ZA814484B/xx unknown
- 1981-07-02 IE IE1481/81A patent/IE51365B1/en unknown
- 1981-07-02 KR KR1019810002403A patent/KR840002046B1/ko not_active Expired
- 1981-07-02 HU HU811934A patent/HU185934B/hu unknown
- 1981-07-02 NO NO812268A patent/NO812268L/no unknown
- 1981-07-02 ES ES503622A patent/ES503622A0/es active Granted
- 1981-07-03 AT AT81303044T patent/ATE9585T1/de not_active IP Right Cessation
- 1981-07-03 EP EP81303044A patent/EP0043713B1/de not_active Expired
- 1981-07-03 DE DE8181303044T patent/DE3166321D1/de not_active Expired
- 1981-07-03 AR AR285975A patent/AR228606A1/es active

Also Published As

Publication number	Publication date
PH17670A (en)	1984-11-02
DE3166321D1 (en)	1984-10-31
JPS5745189A (en)	1982-03-13
HU185934B (en)	1985-04-28
KR840002046B1 (ko)	1984-11-06
ES8203908A1 (es)	1982-04-01
AU547942B2 (en)	1985-11-14
AU7234381A (en)	1982-01-07
IL63206A0 (en)	1981-09-13
ES503622A0 (es)	1982-04-01
US4308267A (en)	1981-12-29
IL63206A (en)	1986-09-30
EP0043713B1 (de)	1984-09-26
ZW15181A1 (en)	1981-09-29
PT73292B (en)	1982-07-22
DK286981A (da)	1982-01-04
NZ197573A (en)	1984-09-28
FI66876B (fi)	1984-08-31
IE51365B1 (en)	1986-12-10
CA1151150A (en)	1983-08-02
KR830006310A (ko)	1983-09-20
IE811481L (en)	1982-01-03
GR74363B (de)	1984-06-28
ZA814484B (en)	1982-07-28
FI812046L (fi)	1982-01-04
AR228606A1 (es)	1983-03-30
YU162481A (en)	1983-06-30
ATE9585T1 (de)	1984-10-15
FI66876C (fi)	1984-12-10
PT73292A (en)	1981-07-01
EP0043713A1 (de)	1982-01-13

Publication	Publication Date	Title
DE3750443T2 (de)	1995-04-20	Cephalosporinverbindungen, Verfahren zu ihrer Herstellung und antibakterielle Mittel.
US5095012A (en)	1992-03-10	Antibiotic c-7 catechol-substituted cephalosporin compounds, compositions, and method of use thereof
JPH0749432B2 (ja)	1995-05-31	セファロスポリンハロゲン化水素酸塩のアルカリ金属塩への変換
CS264257B2 (en)	1989-06-13	Process for preparing new derivatives of cephalosporine
JPS63146863A (ja)	1988-06-18	カルボン酸類
US5234920A (en)	1993-08-10	Antibiotic C-7 catechol-substituted cephalosporin compounds, compositions, and method of use thereof
BE897864A (fr)	1984-03-29	Procede de production de composes de 3-vinyl-3-cephem 7-substitues et nouveaux produits ainsi obtenus
US4866055A (en)	1989-09-12	Cephalosporin derivatives and their crystalline derivatives
US5389627A (en)	1995-02-14	Cephem compounds
US4880798A (en)	1989-11-14	Cephalosporin derivatives
US4609654A (en)	1986-09-02	Derivatives of cephalosporins substituted in 3 position by a thiomethyl heterocycle group; and pharmaceutical compositions containing them
US3222362A (en)	1965-12-07	Arylaminoalkyl cephalosporins
EP0553792B1 (de)	1999-05-26	Verfahren zur Herstellung von Ceftriaxon-dinatriumsalzhemiheptahydrat
EP0043713B1 (de)	1984-09-26	Antibakterielle Cephalosporinverbindungen
US3222363A (en)	1965-12-07	Carbocycloxyalkyl cephalosporins
US3647789A (en)	1972-03-07	Cephalosporanic acids
JPH0288582A (ja)	1990-03-28	新規セフェム化合物およびその製造法
JPS62167784A (ja)	1987-07-24	新規セフアロスポリン誘導体、その製法およびそれらを有効成分とする抗菌剤
JP3041309B2 (ja)	2000-05-15	３―置換ビニルセファロスポリン誘導体
WO1992022556A1 (en)	1992-12-23	Novel 3-fused pyridiniummethyl cephalosporins
JP2002514650A (ja)	2002-05-21	新規なセファロスポリン化合物、その製造方法およびそれを含有する抗菌性組成物
JPH0491088A (ja)	1992-03-24	ピラノン化合物
JPH03232891A (ja)	1991-10-16	新規な３―イソオキサゾリジニルセファロスポリン誘導体
JPS61115087A (ja)	1986-06-02	７−チアジアゾリルアセトアミド−３−セフエム誘導体
JPH03128382A (ja)	1991-05-31	チアゾリルアセトアミドセフェム系化合物