CH401063A - Verfahren zur Herstellung von Penicillinen aus 6-Aminopenlicillansäure - Google Patents

Verfahren zur Herstellung von Penicillinen aus 6-Aminopenlicillansäure

Info

Publication number: CH401063A
Authority: CH; Switzerland
Prior art keywords: acid; acetoxy; amino; chloride; benzylpenicillin
Prior art date: 1961-07-04

Application number

CH766862A

Other languages

German (de)

English (en)

Inventor

Peter Doyle Frank

Charles Nayler John Herbert

Original Assignee

Beecham Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1961-07-04

Filing date

1962-06-26

Publication date

1965-10-31

1961-07-04 Priority claimed from GB2405661A external-priority patent/GB989882A/en

1962-06-26 Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd

1965-10-31 Publication of CH401063A publication Critical patent/CH401063A/de

Links

238000000034 method Methods 0.000 title claims description 29
239000002253 acid Substances 0.000 title claims description 21
229930182555 Penicillin Natural products 0.000 title claims description 9
150000002960 penicillins Chemical class 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title description 4
229940056360 penicillin g Drugs 0.000 claims description 27
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Natural products 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 26
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 24
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 23
150000003839 salts Chemical class 0.000 claims description 20
235000019371 penicillin G benzathine Nutrition 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 10
239000007864 aqueous solution Substances 0.000 claims description 9
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 8
239000003795 chemical substances by application Substances 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
230000007935 neutral effect Effects 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
BERNQQVIUAZUHY-UHFFFAOYSA-N (2-chloro-2-oxo-1-phenylethyl) acetate Chemical compound CC(=O)OC(C(Cl)=O)C1=CC=CC=C1 BERNQQVIUAZUHY-UHFFFAOYSA-N 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
159000000000 sodium salts Chemical class 0.000 description 13
239000000126 substance Substances 0.000 description 13
-1 aralkoxy Chemical group 0.000 description 10
239000000047 product Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000007787 solid Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
239000008346 aqueous phase Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
230000003115 biocidal effect Effects 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
KZORFVFMSKYMGX-UHFFFAOYSA-N ClC(C(=O)C(C(=O)O)(O)C1=CC=CC=C1)Cl Chemical compound ClC(C(=O)C(C(=O)O)(O)C1=CC=CC=C1)Cl KZORFVFMSKYMGX-UHFFFAOYSA-N 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
150000008065 acid anhydrides Chemical class 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 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
229960004919 procaine Drugs 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
MTKGSFRVYUVPOD-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-hydroxy-3-oxobutanoyl chloride Chemical compound C(C)(=O)C(C(=O)Cl)(O)C1=CC=C(C=C1)Cl MTKGSFRVYUVPOD-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
108010087702 Penicillinase Proteins 0.000 description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
239000006286 aqueous extract Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000007705 chemical test Methods 0.000 description 2
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
229950009506 penicillinase Drugs 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
BWSFWXSSALIZAU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=C(Cl)C=C1 BWSFWXSSALIZAU-UHFFFAOYSA-N 0.000 description 1
MZDRYFWFWMRYJB-UHFFFAOYSA-N 2-hydroxy-3-oxo-2-phenylbutanoyl chloride Chemical compound CC(=O)C(O)(C(Cl)=O)C1=CC=CC=C1 MZDRYFWFWMRYJB-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-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 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
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
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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
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
239000012345 acetylating agent Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002021 butanolic extract Substances 0.000 description 1
239000011575 calcium Substances 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
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229940012017 ethylenediamine Drugs 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
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
208000004396 mastitis Diseases 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 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
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
229910052763 palladium Inorganic materials 0.000 description 1
229940056367 penicillin v Drugs 0.000 description 1
239000003208 petroleum Substances 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
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
244000144977 poultry Species 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
239000012064 sodium phosphate buffer Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
238000005303 weighing Methods 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- 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)

CH766862A 1961-07-04 1962-06-26 Verfahren zur Herstellung von Penicillinen aus 6-Aminopenlicillansäure CH401063A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB2405661A GB989882A (en)	1961-07-04	1961-07-04	Penicillins
GB3547361		1961-10-02

Publications (1)

Publication Number	Publication Date
CH401063A true CH401063A (de)	1965-10-31

Family

ID=26256875

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH766862A CH401063A (de)	1961-07-04	1962-06-26	Verfahren zur Herstellung von Penicillinen aus 6-Aminopenlicillansäure

Country Status (6)

Country	Link
AT (1)	AT243985B (fr)
BE (1)	BE619628R (fr)
BR (1)	BR6240478D0 (fr)
CH (1)	CH401063A (fr)
ES (1)	ES278857A1 (fr)
FR (1)	FR37F (fr)

1962
- 1962-06-25 FR FR901822A patent/FR37F/fr not_active Expired
- 1962-06-26 CH CH766862A patent/CH401063A/de unknown
- 1962-06-29 AT AT524262A patent/AT243985B/de active
- 1962-06-29 BR BR14047862A patent/BR6240478D0/pt unknown
- 1962-07-02 ES ES278857A patent/ES278857A1/es not_active Expired
- 1962-07-02 BE BE619628A patent/BE619628R/fr active

Also Published As

Publication number	Publication date
BE619628R (fr)	1962-11-05
ES278857A1 (es)	1962-11-01
BR6240478D0 (pt)	1973-05-24
AT243985B (de)	1965-12-10
FR37F (fr)	1963-10-04

Publication	Publication Date	Title
CH457440A (de)	1968-06-15	Verfahren zur Herstellung von a-Aminobenzylpenicillin-arylsulfonaten
CH401063A (de)	1965-10-31	Verfahren zur Herstellung von Penicillinen aus 6-Aminopenlicillansäure
CH394206A (de)	1965-06-30	Verfahren zur Herstellung von Abkömmlingen der 6-Amino-penicillansäure
DE1205103B (de)	1965-11-18	Verfahren zur Herstellung eines 3-Dichlorphenyl-5-methylisoxazolyl-(4)-penicillins
CH495377A (de)	1970-08-31	Verfahren zur Herstellung von Penicillinen
DE1143817B (de)	1963-02-21	Verfahren zur Herstellung von 6-Phenoxyacylamidopenicillansaeure-derivaten und von nicht giftigen Salzen derselben
CH396003A (de)	1965-07-31	Verfahren zur Herstellung von Penicillinderivaten
DE1146061C2 (de)	1977-09-01	Verfahren zur herstellung von derivaten der 6-aminopenicillansaeure
DE1670382C3 (de)	1974-12-05	Derivate der 6-Aminopenicillansäure und Verfahren zu ihrer Herstellung
AT239440B (de)	1965-04-12	Verfahren zur Herstellung von neuen Derivaten der 6-Amino-Penicillansäure
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