CH400160A - Verfahren zur Herstellung von Hydroxypenicillinen - Google Patents

Verfahren zur Herstellung von Hydroxypenicillinen

Info

Publication number: CH400160A
Authority: CH; Switzerland
Prior art keywords: formula; ketopenicillin; salts; potassium; carried out
Prior art date: 1961-04-21

Application number

CH482562A

Other languages

German (de)

English (en)

Inventor

Gaston Perron Yvon

Bruce Jr Crast Leonard

Original Assignee

Bristol Myers Co

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.)

1961-04-21

Filing date

1962-04-19

Publication date

1965-10-15

1962-04-19 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1965-10-15 Publication of CH400160A publication Critical patent/CH400160A/de

Links

238000000034 method Methods 0.000 title claims description 23
238000004519 manufacturing process Methods 0.000 title description 13
-1 nitro, amino Chemical group 0.000 claims description 26
229910000033 sodium borohydride Inorganic materials 0.000 claims description 19
239000012279 sodium borohydride Substances 0.000 claims description 19
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 17
229910052700 potassium Inorganic materials 0.000 claims description 17
239000011591 potassium Substances 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000003513 alkali Substances 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000005336 allyloxy group Chemical group 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004799 bromophenyl group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000000068 chlorophenyl group Chemical group 0.000 claims description 3
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 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004344 phenylpropyl group Chemical group 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 7
239000000047 product Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000000203 mixture Substances 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
239000000126 substance Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 2
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 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000010575 fractional recrystallization Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
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 2
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000000391 smoking effect Effects 0.000 description 2
229940087562 sodium acetate trihydrate Drugs 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000003952 β-lactams Chemical group 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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 description 1
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 1
241000894006 Bacteria Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
125000005110 aryl thio group Chemical group 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 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
150000001768 cations Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000002655 kraft paper Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
239000000843 powder 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
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
230000000717 retained effect Effects 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
XWNXEWLCHSLQOI-UHFFFAOYSA-K trisodium;triacetate Chemical compound [Na+].[Na+].[Na+].CC([O-])=O.CC([O-])=O.CC([O-])=O XWNXEWLCHSLQOI-UHFFFAOYSA-K 0.000 description 1
238000005406 washing 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)

CH482562A 1961-04-21 1962-04-19 Verfahren zur Herstellung von Hydroxypenicillinen CH400160A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US10453161A	1961-04-21	1961-04-21

Publications (1)

Publication Number	Publication Date
CH400160A true CH400160A (de)	1965-10-15

Family

ID=22300982

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH482562A CH400160A (de)	1961-04-21	1962-04-19	Verfahren zur Herstellung von Hydroxypenicillinen

Country Status (3)

Country	Link
CH (1)	CH400160A (da)
DK (1)	DK117228B (da)
GB (1)	GB952293A (da)

1962
- 1962-04-17 DK DK175762A patent/DK117228B/da unknown
- 1962-04-18 GB GB1513762A patent/GB952293A/en not_active Expired
- 1962-04-19 CH CH482562A patent/CH400160A/de unknown

Also Published As

Publication number	Publication date
DK117228B (da)	1970-03-31
GB952293A (en)	1964-03-11

Publication	Publication Date	Title
DE1795763A1 (de)	1974-11-21	Verfahren zur herstellung von desacylierten vielkernigen indolverbindungen sowie deren estern
DE2228012B2 (de)	1979-05-23	-Aminophenylacetamido] -penicülansäure und Verfahren zu seiner Herstellung
AT349029B (de)	1979-03-12	Verfahren zur herstellung von neuen 1,2- dithiolderivaten
DE2822876C2 (da)	1988-01-07
DE1670222C3 (de)	1979-04-05	a-(Benzyloxycarbonyl)-thienyunethylpenicilline und deren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende antibakterielle Mittel
CH395967A (de)	1965-07-31	Verfahren zur Herstellung von racemischer und optisch aktiver 2,3-Dimercaptobernsteinsäure
DE2005959A1 (de)	1970-08-06	7-Nitro-8-hydroxychinolinester, ihre Verwendung und Verfahren zur Herstellung derselben
CH400160A (de)	1965-10-15	Verfahren zur Herstellung von Hydroxypenicillinen
DE1670163C3 (de)	1973-11-29	Cephaloglycindenvat und Verfahren zu seiner Herstellung
DE1929997C2 (de)	1983-12-08	Acylureidopenicilline, Verfahren zu ihrer Herstellung und antibakterielle Mittel, die diese Verbindungen enthalten
DE3002659A1 (de)	1980-07-31	Neue organische verbindungen, verfahren zu ihrer herstellung und ihre verwendung
AT230542B (de)	1963-12-10	Verfahren zur Herstellung von Hydroxypenicillinen
DE1289053B (de)	1969-02-13	ª‡-Hydroxy-2-thienylmethyl-penicilline und Verfahren zur ihrer Herstellung
AT375081B (de)	1984-06-25	Verfahren zur herstellung von 7-aminocephalosporansaeure und ihren estern
DE2033090C3 (de)	1981-01-29	deren Herstellung
DE2021073A1 (de)	1970-11-12	alpha-Amino-2,4,6-cycloheptatrienyl-methylcephalosporine und Verfahren zu ihrer Herstellung
DE1967320C2 (de)	1982-09-16	Verfahren zur Herstellung von wasserfreien 6-(1-Aminocycloalkylcarboxamido)-penicillansäuren
DE2221123C2 (de)	1983-04-28	Reserpsäurederivate, Verfahren zu deren Herstellung und Arzneimittel
DE2841363C2 (da)	1988-08-04
DE2258994A1 (de)	1973-06-20	Antibakterielle mittel und verfahren zu deren herstellung
DE2008272C3 (de)	1978-01-19	Verfahren zur Racemisierung und Auftrennung eines Salzes einer 2-(2-NaphthyO-propionsäure und einer stickstoffhaltigen Base
AT259132B (de)	1967-12-27	Verfahren zur Herstellung von neuen Penicillinderivaten
DE1470083C (de)	1972-08-24	Cinnamylpenicilline und Verfahren zu ihrer Herstellung
AT239440B (de)	1965-04-12	Verfahren zur Herstellung von neuen Derivaten der 6-Amino-Penicillansäure
AT234276B (de)	1964-06-25	Verfahren zur Herstellung der neuen Verbindung α-Azidobenzylpenicillin