CH403766A - Verfahren zur Herstellung von Penicillinen - Google Patents
Verfahren zur Herstellung von PenicillinenInfo
- Publication number
- CH403766A CH403766A CH1177761A CH1177761A CH403766A CH 403766 A CH403766 A CH 403766A CH 1177761 A CH1177761 A CH 1177761A CH 1177761 A CH1177761 A CH 1177761A CH 403766 A CH403766 A CH 403766A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- solution
- mol
- mcg
- isobutyl ketone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 229930182555 Penicillin Natural products 0.000 title claims description 12
- 150000002960 penicillins Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000002253 acid Substances 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 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 claims description 16
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [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 15
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 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 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims 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 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229940049954 penicillin Drugs 0.000 claims description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 74
- 239000000243 solution Substances 0.000 description 55
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 32
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000000284 extract Substances 0.000 description 28
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- 229910052938 sodium sulfate Inorganic materials 0.000 description 22
- 235000011152 sodium sulphate Nutrition 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000007864 aqueous solution Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 18
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical class [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- -1 alkyl radicals Chemical class 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 11
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 10
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 9
- 150000003952 β-lactams Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000035876 healing Effects 0.000 description 8
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 235000019371 penicillin G benzathine Nutrition 0.000 description 7
- 229940056360 penicillin g Drugs 0.000 description 7
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 5
- 239000011591 potassium Chemical class 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- IFCUOJRHUHPNRJ-UHFFFAOYSA-N 2-(furan-2-ylmethylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NCC1=CC=CO1 IFCUOJRHUHPNRJ-UHFFFAOYSA-N 0.000 description 4
- 101000599862 Homo sapiens Intercellular adhesion molecule 3 Proteins 0.000 description 4
- 102100037871 Intercellular adhesion molecule 3 Human genes 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical class COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 description 3
- KZRGQINXYBJMNB-UHFFFAOYSA-N 2-(benzylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NCC1=CC=CC=C1 KZRGQINXYBJMNB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108010087702 Penicillinase Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- HGWODTLOGZWZRF-UHFFFAOYSA-N 2-(propylcarbamoyl)benzoic acid Chemical compound CCCNC(=O)C1=CC=CC=C1C(O)=O HGWODTLOGZWZRF-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 125000003460 beta-lactamyl group Chemical group 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 2
- 229950009506 penicillinase Drugs 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- XVQUUVCOFZFTDA-UHFFFAOYSA-N 2-(2-phenylethylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NCCC1=CC=CC=C1 XVQUUVCOFZFTDA-UHFFFAOYSA-N 0.000 description 1
- JTRKMJYNFCVDEH-UHFFFAOYSA-N 2-(diethylcarbamoyl)benzoic acid Chemical compound CCN(CC)C(=O)C1=CC=CC=C1C(O)=O JTRKMJYNFCVDEH-UHFFFAOYSA-N 0.000 description 1
- MMJYFEBZBADSNQ-UHFFFAOYSA-N 2-(dimethylcarbamoyl)benzoic acid Chemical compound CN(C)C(=O)C1=CC=CC=C1C(O)=O MMJYFEBZBADSNQ-UHFFFAOYSA-N 0.000 description 1
- OTVDESMGXUUCQW-UHFFFAOYSA-N 2-(dodecylcarbamoyl)benzoic acid Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=CC=C1C(O)=O OTVDESMGXUUCQW-UHFFFAOYSA-N 0.000 description 1
- WYQIYQFQPHFODA-UHFFFAOYSA-N 2-(oxolan-2-ylmethylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NCC1OCCC1 WYQIYQFQPHFODA-UHFFFAOYSA-N 0.000 description 1
- XCLHANSFIVZGFC-UHFFFAOYSA-N 2-(tert-butylcarbamoyl)benzoic acid Chemical compound CC(C)(C)NC(=O)C1=CC=CC=C1C(O)=O XCLHANSFIVZGFC-UHFFFAOYSA-N 0.000 description 1
- PZSITMBIVNJHKF-UHFFFAOYSA-N 2-[di(propan-2-yl)carbamoyl]benzoic acid Chemical compound CC(C)N(C(C)C)C(=O)C1=CC=CC=C1C(O)=O PZSITMBIVNJHKF-UHFFFAOYSA-N 0.000 description 1
- CPUYOTLAVBXHSJ-UHFFFAOYSA-N 2-carbamoyl-3-propan-2-ylbenzoic acid Chemical compound CC(C)C1=CC=CC(C(O)=O)=C1C(N)=O CPUYOTLAVBXHSJ-UHFFFAOYSA-N 0.000 description 1
- QRAFJHXNLQTXQW-UHFFFAOYSA-N 2-methylpropyl hydrogen carbonate Chemical compound CC(C)COC(O)=O QRAFJHXNLQTXQW-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229930195708 Penicillin V Natural products 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010633 broth Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000007073 chemical hydrolysis Effects 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 208000004396 mastitis Diseases 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
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940056367 penicillin v Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6252660A | 1960-10-14 | 1960-10-14 | |
| US7448960A | 1960-12-08 | 1960-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH403766A true CH403766A (de) | 1965-12-15 |
Family
ID=26742379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1177761A CH403766A (de) | 1960-10-14 | 1961-10-11 | Verfahren zur Herstellung von Penicillinen |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH403766A (cs) |
| FR (1) | FR1454M (cs) |
| GB (1) | GB914419A (cs) |
| SE (1) | SE316476B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102099357B (zh) | 2008-04-23 | 2014-07-02 | 里格尔药品股份有限公司 | 用于治疗代谢障碍的甲酰胺化合物 |
-
1961
- 1961-09-26 SE SE9559/61A patent/SE316476B/xx unknown
- 1961-09-27 GB GB34562/61A patent/GB914419A/en not_active Expired
- 1961-10-10 FR FR875510A patent/FR1454M/fr active Active
- 1961-10-11 CH CH1177761A patent/CH403766A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB914419A (en) | 1963-01-02 |
| SE316476B (cs) | 1969-10-27 |
| FR1454M (fr) | 1962-08-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2324272A1 (de) | 3-methylencephalosporine | |
| CH403766A (de) | Verfahren zur Herstellung von Penicillinen | |
| DE1795861B1 (de) | alpha-(Alkoxycarbonyl)-thienylmethyl-penicilline und deren Salze,Verfahren zu deren Herstellung und diese Verbindungen enthaltende antibakterielle Mittel | |
| DE1205103B (de) | Verfahren zur Herstellung eines 3-Dichlorphenyl-5-methylisoxazolyl-(4)-penicillins | |
| DE1143817B (de) | Verfahren zur Herstellung von 6-Phenoxyacylamidopenicillansaeure-derivaten und von nicht giftigen Salzen derselben | |
| AT226366B (de) | Verfahren zur Herstellung von neuen Penicillinderivaten | |
| CH394206A (de) | Verfahren zur Herstellung von Abkömmlingen der 6-Amino-penicillansäure | |
| DE1670163B2 (de) | Cephaloglycinderivat und verfahren zu seiner herstellung | |
| AT259132B (de) | Verfahren zur Herstellung von neuen Penicillinderivaten | |
| AT228397B (de) | Verfahren zur Herstellung von Verbindungen mit antibakterieller Wirkung | |
| DE2033090C3 (de) | deren Herstellung | |
| CH400158A (de) | Verfahren zur Herstellung von Penicillinderivaten | |
| DE2025415B2 (de) | Verfahren zur Herstellung von cyclischen Acylureido-Penicillinen | |
| DE1670091C3 (de) | Derivate der 6-Aminopenicillansäure und Verfahren zu ihrer Herstellung | |
| DE3227284A1 (de) | 7ss-(2-(2'-(amino)-thiazol-4'-yl)-2-(hydrazono)-acetamido)-ceph-3-em-4-carbonsaeurederivate, verfahren zur herstellung derselben und diese enthaltende arzneimittel | |
| AT234276B (de) | Verfahren zur Herstellung der neuen Verbindung α-Azidobenzylpenicillin | |
| AT239440B (de) | Verfahren zur Herstellung von neuen Derivaten der 6-Amino-Penicillansäure | |
| AT255646B (de) | Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure | |
| AT231612B (de) | Verfahren zur Herstellung von neuen Penicillinderivaten | |
| CH396003A (de) | Verfahren zur Herstellung von Penicillinderivaten | |
| CH412902A (de) | Verfahren zur Herstellung von Penicillinderivaten | |
| AT229487B (de) | Verfahren zur Herstellung von neuen antibakteriellen Mitteln | |
| DE1670117A1 (de) | Cephalosporansaeurederivate und Verfahren zu ihrer Herstellung | |
| AT275036B (de) | Verfahren zur Herstellung von neuen Derivaten der 7-Aminocephalosporansäure | |
| DE1162374B (de) | Verfahren zur Herstellung von Penicillinen und deren nichttoxischen Salzen |