NO753285L - - Google Patents
Info
- Publication number
- NO753285L NO753285L NO753285A NO753285A NO753285L NO 753285 L NO753285 L NO 753285L NO 753285 A NO753285 A NO 753285A NO 753285 A NO753285 A NO 753285A NO 753285 L NO753285 L NO 753285L
- Authority
- NO
- Norway
- Prior art keywords
- acid
- group
- formula
- dihydro
- amino
- Prior art date
Links
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- 239000002253 acid Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 33
- 150000003839 salts Chemical class 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000003277 amino group Chemical group 0.000 description 17
- 238000001914 filtration Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 239000003610 charcoal Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 229930186147 Cephalosporin Natural products 0.000 description 10
- 229940124587 cephalosporin Drugs 0.000 description 10
- 150000001780 cephalosporins Chemical class 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 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 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- -1 nitrogenous organic base Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- 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 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- NLIJGBOIMJSYJQ-UHFFFAOYSA-N ethyl 2-hydroxyimino-3-oxo-4-(2-sulfanylethylsulfanyl)butanoate Chemical compound CCOC(=O)C(=NO)C(=O)CSCCS NLIJGBOIMJSYJQ-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229940056360 penicillin g Drugs 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 3
- PSORZDDANGBQTD-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-dithiin-5-yl)acetic acid Chemical compound OC(=O)CC1=CSCCS1 PSORZDDANGBQTD-UHFFFAOYSA-N 0.000 description 2
- ULGJWNIHLSLQPZ-UHFFFAOYSA-N 7-[(6,8-dichloro-1,2,3,4-tetrahydroacridin-9-yl)amino]-n-[2-(1h-indol-3-yl)ethyl]heptanamide Chemical compound C1CCCC2=NC3=CC(Cl)=CC(Cl)=C3C(NCCCCCCC(=O)NCCC=3C4=CC=CC=C4NC=3)=C21 ULGJWNIHLSLQPZ-UHFFFAOYSA-N 0.000 description 2
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 2
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 108010003977 aminoacylase I Proteins 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000006196 deacetylation Effects 0.000 description 2
- 238000003381 deacetylation reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- AQRVXLBLIWFXAZ-UHFFFAOYSA-N ethyl 4-(2-hydroxyethylsulfanyl)-2-hydroxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(=NO)C(=O)CSCCO AQRVXLBLIWFXAZ-UHFFFAOYSA-N 0.000 description 2
- WZFWZOMDWASODS-UHFFFAOYSA-N ethyl 4-chloro-2-hydroxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(=NO)C(=O)CCl WZFWZOMDWASODS-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 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
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 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
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- LGUHADBEXWHGIZ-UHFFFAOYSA-N butyl n-diazocarbamate Chemical compound CCCCOC(=O)N=[N+]=[N-] LGUHADBEXWHGIZ-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000011863 silicon-based powder Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Materials Engineering (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7432701A FR2285889A1 (fr) | 1974-09-27 | 1974-09-27 | Nouveaux derives de la cephalosporine, leur preparation et les compositions qui les contiennent |
| FR7522682A FR2318639A2 (fr) | 1975-07-21 | 1975-07-21 | Nouveaux derives de la cephalosporine, leur preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO753285L true NO753285L (bg) | 1976-03-30 |
Family
ID=26218535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO753285A NO753285L (bg) | 1974-09-27 | 1975-09-26 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4029781A (bg) |
| JP (1) | JPS5163190A (bg) |
| AT (1) | AT340050B (bg) |
| AU (1) | AU497268B2 (bg) |
| CA (1) | CA1038374A (bg) |
| CH (1) | CH609988A5 (bg) |
| DE (1) | DE2543000A1 (bg) |
| DK (1) | DK435375A (bg) |
| ES (1) | ES441300A1 (bg) |
| FI (1) | FI752694A (bg) |
| GB (1) | GB1481779A (bg) |
| HU (1) | HU169920B (bg) |
| IE (1) | IE41697B1 (bg) |
| IL (1) | IL48183A (bg) |
| LU (1) | LU73469A1 (bg) |
| NL (1) | NL7511086A (bg) |
| NO (1) | NO753285L (bg) |
| SE (1) | SE7510833L (bg) |
| SU (1) | SU562200A3 (bg) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| GB1600724A (en) * | 1977-06-09 | 1981-10-21 | Rhone Poulenc Ind | A-amino-(1,3-dithiin-5-yl)acetic acid and derivatives thereof |
| FR2421172A1 (fr) * | 1978-03-29 | 1979-10-26 | Rhone Poulenc Ind | Nouvel acide dithiinnoacetique et sa preparation |
| JPS6150973A (ja) * | 1983-11-16 | 1986-03-13 | Fujisawa Pharmaceut Co Ltd | 置換イミノ酢酸誘導体およびその塩類 |
| JPS60155167A (ja) * | 1984-07-31 | 1985-08-15 | Fujisawa Pharmaceut Co Ltd | 置換イミノ酢酸誘導体およびその塩類 |
| US4959495A (en) * | 1986-07-28 | 1990-09-25 | American Cyanamid Company | Process for the preparation of intermediates used to produce aminothiazoloximino cephalosporins |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH557381A (de) * | 1967-04-15 | 1974-12-31 | Fujisawa Pharmaceutical Co | Verfahren zur herstellung von (delta)3-cephemverbindungen. |
| US3692779A (en) * | 1970-08-12 | 1972-09-19 | Bristol Myers Co | 7-{8 n-(substituted-imidoyl)aminoacetamide{9 cephalosporanic acids and derivatives thereof |
| US3891629A (en) * | 1973-02-16 | 1975-06-24 | Squibb & Sons Inc | Process for the preparation of 6-{8 d-2-amino-2(1,4-cyclo-hexadienyl)acetamido{9 {0 penicillanic acid |
| US3886151A (en) * | 1974-03-18 | 1975-05-27 | American Home Prod | 7-{8 2-(Heteroazinylthio)acetamido{9 {0 cephalosporanic acid derivatives |
-
1975
- 1975-09-12 IE IE1998/75A patent/IE41697B1/en unknown
- 1975-09-16 AU AU84883/75A patent/AU497268B2/en not_active Expired
- 1975-09-19 NL NL7511086A patent/NL7511086A/xx not_active Application Discontinuation
- 1975-09-24 CA CA236,280A patent/CA1038374A/fr not_active Expired
- 1975-09-25 IL IL48183A patent/IL48183A/xx unknown
- 1975-09-25 HU HURO861A patent/HU169920B/hu unknown
- 1975-09-26 DK DK435375A patent/DK435375A/da unknown
- 1975-09-26 GB GB39589/75A patent/GB1481779A/en not_active Expired
- 1975-09-26 JP JP50116293A patent/JPS5163190A/ja active Pending
- 1975-09-26 DE DE19752543000 patent/DE2543000A1/de not_active Withdrawn
- 1975-09-26 SU SU2175260A patent/SU562200A3/ru active
- 1975-09-26 AT AT736975A patent/AT340050B/de not_active IP Right Cessation
- 1975-09-26 NO NO753285A patent/NO753285L/no unknown
- 1975-09-26 CH CH1251475A patent/CH609988A5/xx not_active IP Right Cessation
- 1975-09-26 ES ES441300A patent/ES441300A1/es not_active Expired
- 1975-09-26 FI FI752694A patent/FI752694A/fi not_active Application Discontinuation
- 1975-09-26 LU LU73469A patent/LU73469A1/xx unknown
- 1975-09-26 SE SE7510833A patent/SE7510833L/xx unknown
- 1975-09-26 US US05/617,066 patent/US4029781A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FI752694A (bg) | 1976-03-28 |
| JPS5163190A (bg) | 1976-06-01 |
| US4029781A (en) | 1977-06-14 |
| IE41697B1 (en) | 1980-02-27 |
| SU562200A3 (ru) | 1977-06-15 |
| AU8488375A (en) | 1977-03-24 |
| HU169920B (bg) | 1977-02-28 |
| GB1481779A (en) | 1977-08-03 |
| IL48183A (en) | 1979-03-12 |
| CA1038374A (fr) | 1978-09-12 |
| DK435375A (da) | 1976-03-28 |
| NL7511086A (nl) | 1976-03-30 |
| ES441300A1 (es) | 1977-03-16 |
| IE41697L (en) | 1976-03-27 |
| AU497268B2 (en) | 1978-12-07 |
| DE2543000A1 (de) | 1976-04-08 |
| IL48183A0 (en) | 1975-11-25 |
| ATA736975A (de) | 1977-03-15 |
| AT340050B (de) | 1977-11-25 |
| LU73469A1 (bg) | 1976-08-19 |
| CH609988A5 (bg) | 1979-03-30 |
| SE7510833L (sv) | 1976-03-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL96668B1 (pl) | Sposob wytwarzania estru ftalidylowego kwasu 6-/d/-/alfa-aminofenyloacetamido/-penicylanowego | |
| DK150201B (da) | Alfa-azido-n-acyl-6-aminopenicillansyreester til anvendelse ved fremstilling af den tilsvarende alfa-aminoforbindelse | |
| Doyle et al. | 272. Derivatives of 6-aminopenicillanic acid. Part I. α-Aminobenzylpenicillin and some related compounds | |
| US4138397A (en) | 6-(2,3-Dihydro-5-benzofuranyl)acetamido penicillin derivatives | |
| NO753285L (bg) | ||
| NO802686L (no) | Fremgangsmaate for fremstilling av en ester av et klavulansyreamin | |
| JP2008509105A (ja) | キヌレニン−アミノトランスフェラーゼ阻害剤として有用な４−スルホニル−置換ベンゾイルアラニン誘導体 | |
| US3714156A (en) | Lactam process | |
| US4071531A (en) | Oxathiino- and dithiino-aminoacetic acids | |
| US3270009A (en) | Carbocyclic-substituted aliphatic cephalosporins | |
| JPS6033397B2 (ja) | ペナム−１，１−ジオキシド | |
| JPH01319486A (ja) | セフアロスポリン化合物、その製法及びこれを含有する抗菌剤組成物 | |
| US4183943A (en) | Organic compounds | |
| US4193918A (en) | Process for the preparation of hydroxy-alpha-amino-benzyl penicillin | |
| PL94240B1 (en) | Substituted cephene-4-carboxylates and their method of preparation[us3962223a] | |
| PL142255B1 (en) | Process for preparing novel derivatives of ortho-condensed pyrrole | |
| SU566525A3 (ru) | Способ получени производных цефалоспорина или их солей с металлами или азотсодержащими основани ми | |
| US3720664A (en) | Alpha-ureidocyclohexadienylalkylene-penicillins | |
| JPS61126082A (ja) | アミノピロリジン誘導体、そのエステルおよびその塩 | |
| US3809700A (en) | Certain 5,6-dioxopyrrolo(2,1-b)thiazoles | |
| JPS60184077A (ja) | 抗炎症性オキシム前駆薬 | |
| US3639422A (en) | 4-phenylindole-1 (and 7)-acetic acids | |
| NO841441L (no) | Benzotienylglycylcefalosporinderivater og fremgangsmaate for deres fremstilling | |
| US3682981A (en) | 2-amino-2-(1,4-cyclohexadienyl) acetic acid | |
| JPS59199693A (ja) | インドリルグリシルセフアロスポリン誘導体 |