NO134913B - - Google Patents
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- Publication number
- NO134913B NO134913B NO2755/69A NO275569A NO134913B NO 134913 B NO134913 B NO 134913B NO 2755/69 A NO2755/69 A NO 2755/69A NO 275569 A NO275569 A NO 275569A NO 134913 B NO134913 B NO 134913B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- compound
- formula
- amino
- salt
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical group [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 11
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical group S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229930182555 Penicillin Natural products 0.000 claims description 5
- 229940124587 cephalosporin Drugs 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 229930186147 Cephalosporin Natural products 0.000 claims description 2
- 150000001780 cephalosporins Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002960 penicillins Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- -1 sodium or potassium Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 8
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 7
- 229940106164 cephalexin Drugs 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 3
- 229960002588 cefradine Drugs 0.000 description 3
- RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229940049954 penicillin Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JBJJTCGQCRGNOL-SSDOTTSWSA-N (2r)-2-amino-2-cyclohexa-1,4-dien-1-ylacetic acid Chemical compound OC(=O)[C@H](N)C1=CCC=CC1 JBJJTCGQCRGNOL-SSDOTTSWSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229960000723 ampicillin Drugs 0.000 description 2
- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- BDQWZLRWCGVHMG-SSDOTTSWSA-N (2r)-2-amino-2-cyclohexa-1,3-dien-1-ylacetic acid Chemical compound OC(=O)[C@H](N)C1=CC=CCC1 BDQWZLRWCGVHMG-SSDOTTSWSA-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-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
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000002768 Kirby-Bauer method Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 241000194022 Streptococcus sp. Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 description 1
- 150000004705 aldimines Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000002815 broth microdilution Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- RPBAFSBGYDKNRG-NJBDSQKTSA-N epicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CCC=CC1 RPBAFSBGYDKNRG-NJBDSQKTSA-N 0.000 description 1
- 229960002457 epicillin Drugs 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- ZXKKYROKHHMUIK-OGFXRTJISA-M sodium (2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetate Chemical compound [Na+].N[C@@H](C(=O)[O-])C1=CCC=CC1 ZXKKYROKHHMUIK-OGFXRTJISA-M 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-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
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74185268A | 1968-07-02 | 1968-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134913B true NO134913B (de) | 1976-09-27 |
| NO134913C NO134913C (de) | 1977-01-05 |
Family
ID=24982474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2755/69A NO134913C (de) | 1968-07-02 | 1969-07-01 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3485819A (de) |
| AT (1) | AT301020B (de) |
| BE (1) | BE735536A (de) |
| BG (2) | BG17331A3 (de) |
| BR (1) | BR6910296D0 (de) |
| CH (1) | CH518977A (de) |
| CS (1) | CS157672B2 (de) |
| DK (1) | DK131728C (de) |
| ES (1) | ES369005A1 (de) |
| FI (1) | FI52093C (de) |
| FR (1) | FR2012156B1 (de) |
| GB (1) | GB1276314A (de) |
| IE (1) | IE32888B1 (de) |
| IL (1) | IL32411A (de) |
| IT (1) | IT1052126B (de) |
| MY (1) | MY7300279A (de) |
| NL (1) | NL153545B (de) |
| NO (1) | NO134913C (de) |
| PL (1) | PL80099B1 (de) |
| SE (2) | SE397532B (de) |
| YU (2) | YU34901B (de) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3673183A (en) * | 1969-11-17 | 1972-06-27 | Squibb & Sons Inc | {60 -ureidocephalosporanic acid compounds |
| US3937699A (en) * | 1970-10-12 | 1976-02-10 | Takeda Chemical Industries, Ltd. | 6-(1'-cyclohexenylglycinamido)penicillanic acid and salts thereof |
| US3708479A (en) * | 1970-10-26 | 1973-01-02 | Squibb & Sons Inc | Acyloxymethyl esters of alpha-ureidocyclo-hexadie nylalkylene-cephalosporins |
| US3940483A (en) * | 1971-02-05 | 1976-02-24 | E. R. Squibb & Sons, Inc. | Antibiotic compositions and method |
| US3839329A (en) * | 1971-11-04 | 1974-10-01 | Squibb & Sons Inc | {60 -amidinothioacetamidocephalosporanic acid compounds |
| GB1382435A (en) * | 1971-11-22 | 1975-01-29 | Squibb & Sons Inc | Free flowing epicillin |
| US3905955A (en) * | 1972-05-26 | 1975-09-16 | Squibb & Sons Inc | Substituted amino acetamido penicillins |
| US3819620A (en) * | 1972-06-01 | 1974-06-25 | Squibb & Sons Inc | 7-(d-alpha-amino-1,4-cyclohexadien-1-ylacet-amido)desacetoxycephalosporanic acid dihydrate |
| US3846417A (en) * | 1972-06-23 | 1974-11-05 | Squibb & Sons Inc | 1,4-cyclohexadienyl imidazolidinyl cephalosporanic acids and derivatives thereof |
| US3912726A (en) * | 1973-02-16 | 1975-10-14 | Squibb & Sons Inc | Process for the preparation of 7-(D-2-amino-2-(1,4-cyclo-hexadienyl) acetamido) desacetoxycephalosporanic acid and 7-(D-2-amino-2-(1,4-cyclohexadienyl) acetamido) cephalosporanic acid |
| 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 |
| US3946000A (en) * | 1973-10-31 | 1976-03-23 | Bristol-Myers Company | 7-[α-(2-Aminomethyl-1-cyclohexenyl)-acetamido]-3-heterocyclic thiomethyl-3-cephem-4-carboxylic acids |
| US4063019A (en) | 1976-03-30 | 1977-12-13 | E. R. Squibb & Sons, Inc. | [[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]-acetylcephalosporin derivatives |
| US4206218A (en) * | 1978-08-31 | 1980-06-03 | E. R. Squibb & Sons, Inc. | Phthalidyl esters of the acetone adduct of epicillin |
| JPS56150049A (en) * | 1980-04-21 | 1981-11-20 | Nippon Kasei Kk | Production of d-2-amino-2- 1,4-cyclohexadienyl acetic acid |
| US4316905A (en) * | 1980-07-01 | 1982-02-23 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of various 4-substituted prolines |
| US4946838A (en) * | 1981-07-13 | 1990-08-07 | E. R. Squibb & Sons, Inc. | Crystalline anhydrous aztreonam |
| US4520022A (en) * | 1983-01-28 | 1985-05-28 | Bristol-Myers Company | Substituted vinyl cephalosporins |
| ZM884A1 (en) * | 1983-01-28 | 1984-10-22 | Bristol Myers Co | Substituted vinyl cephalosporins |
| DE3641822A1 (de) * | 1986-12-06 | 1988-06-16 | Goedecke Ag | Verwendung von dihydrophenylaminosaeurederivaten und diese enthaltende arzneimittel zur immunmodulation und cytostase |
| US5278157A (en) * | 1989-07-10 | 1994-01-11 | Gema, S.A. | Stable cephradine hydrate |
| LT1641933T (lt) * | 2003-07-03 | 2018-04-10 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Cefradino gamybos būdas |
| CN1320031C (zh) * | 2005-07-01 | 2007-06-06 | 清华大学 | 一种含有异山梨醇单元的聚酰胺及其制备方法 |
| CN101230014B (zh) * | 2008-02-01 | 2010-11-03 | 张超 | 一种d-二氢苯甘氨酸甲基邓钠盐生产中蒸氨冷量利用的方法 |
| CN101550089B (zh) * | 2008-11-21 | 2013-04-03 | 应忠芳 | 左旋双氢苯甘氨酸甲基邓钠盐的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2985648A (en) * | 1958-10-06 | 1961-05-23 | Doyle Frank Peter | Alpha-aminobenzylpenicillins |
| FR1520363A (fr) * | 1962-01-16 | 1968-04-12 | Merck & Co Inc | Nouveaux dérivés de l'acide 7-aminocéphalosporanique |
| US3117119A (en) * | 1962-11-13 | 1964-01-07 | Smith Kline French Lab | Cycloaliphatic penhicillin derivatives |
| GB1050422A (de) * | 1963-03-06 |
-
1968
- 1968-07-02 US US741852A patent/US3485819A/en not_active Expired - Lifetime
-
1969
- 1969-06-16 GB GB30325/69A patent/GB1276314A/en not_active Expired
- 1969-06-16 IE IE825/69A patent/IE32888B1/xx unknown
- 1969-06-17 IL IL32411A patent/IL32411A/xx unknown
- 1969-06-30 IT IT38337/69A patent/IT1052126B/it active
- 1969-06-30 BR BR210296/69A patent/BR6910296D0/pt unknown
- 1969-06-30 CH CH1000769A patent/CH518977A/fr not_active IP Right Cessation
- 1969-07-01 NO NO2755/69A patent/NO134913C/no unknown
- 1969-07-01 FR FR696922170A patent/FR2012156B1/fr not_active Expired
- 1969-07-01 BG BG012571A patent/BG17331A3/xx unknown
- 1969-07-01 ES ES369005A patent/ES369005A1/es not_active Expired
- 1969-07-01 PL PL1969134558A patent/PL80099B1/pl unknown
- 1969-07-01 DK DK355769A patent/DK131728C/da not_active IP Right Cessation
- 1969-07-02 YU YU169/69A patent/YU34901B/xx unknown
- 1969-07-02 SE SE7404448A patent/SE397532B/xx not_active IP Right Cessation
- 1969-07-02 NL NL696910123A patent/NL153545B/xx not_active IP Right Cessation
- 1969-07-02 BE BE735536D patent/BE735536A/xx not_active IP Right Cessation
- 1969-07-02 AT AT636769A patent/AT301020B/de not_active IP Right Cessation
- 1969-07-02 SE SE6909409A patent/SE383887B/xx unknown
- 1969-07-02 FI FI691969A patent/FI52093C/fi active
- 1969-07-02 CS CS469269A patent/CS157672B2/cs unknown
- 1969-07-11 BG BG016461A patent/BG17811A3/xx unknown
-
1973
- 1973-12-30 MY MY279/73A patent/MY7300279A/xx unknown
-
1979
- 1979-05-28 YU YU01243/79A patent/YU124379A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE397532B (sv) | 1977-11-07 |
| NO134913C (de) | 1977-01-05 |
| SE383887B (sv) | 1976-04-05 |
| IL32411A0 (en) | 1969-08-27 |
| DK131728B (da) | 1975-08-25 |
| IE32888B1 (en) | 1974-01-09 |
| DE1931722B2 (de) | 1976-09-23 |
| DE1931722A1 (de) | 1970-01-08 |
| FI52093B (de) | 1977-02-28 |
| FR2012156B1 (de) | 1973-01-12 |
| IL32411A (en) | 1974-01-14 |
| BR6910296D0 (pt) | 1973-02-08 |
| IE32888L (en) | 1970-01-02 |
| IT1052126B (it) | 1981-06-20 |
| YU124379A (en) | 1982-10-31 |
| YU34901B (en) | 1980-04-30 |
| BE735536A (de) | 1970-01-02 |
| DK131728C (da) | 1976-01-26 |
| DE1967020B2 (de) | 1977-01-13 |
| DE1967020A1 (de) | 1976-04-29 |
| ES369005A1 (es) | 1971-07-16 |
| GB1276314A (en) | 1972-06-01 |
| CS157672B2 (de) | 1974-09-16 |
| NL153545B (nl) | 1977-06-15 |
| FI52093C (fi) | 1977-06-10 |
| AT301020B (de) | 1972-08-25 |
| NL6910123A (de) | 1970-01-06 |
| CH518977A (fr) | 1972-02-15 |
| BG17811A3 (bg) | 1973-12-25 |
| YU169669A (en) | 1979-10-31 |
| BG17331A3 (bg) | 1973-07-25 |
| MY7300279A (en) | 1973-12-31 |
| US3485819A (en) | 1969-12-23 |
| FR2012156A1 (de) | 1970-03-13 |
| PL80099B1 (de) | 1975-08-30 |
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