NL7907414A - Werkwijze voor bereiding van semi-synthetische penicil- line antibiotica. - Google Patents

Werkwijze voor bereiding van semi-synthetische penicil- line antibiotica. Download PDF

Info

Publication number: NL7907414A
Authority: NL; Netherlands
Prior art keywords: carbon atoms; apa; alkyl radical; urea; process according
Prior art date: 1978-10-06

Application number

NL7907414A

Other languages

English (en)

Dutch (nl)

Original Assignee

Glaxo 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.)

1978-10-06

Filing date

1979-10-05

Publication date

1980-04-09

1979-10-05 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1980-04-09 Publication of NL7907414A publication Critical patent/NL7907414A/nl

Links

238000000034 method Methods 0.000 title claims description 57
238000002360 preparation method Methods 0.000 title claims description 39
239000003242 anti bacterial agent Substances 0.000 title claims description 14
229940088710 antibiotic agent Drugs 0.000 title description 9
IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 title 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 claims description 82
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 81
239000004202 carbamide Substances 0.000 claims description 65
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 49
125000004432 carbon atom Chemical group C* 0.000 claims description 47
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 34
-1 trialkylsilyl urea Chemical compound 0.000 claims description 28
229960003311 ampicillin trihydrate Drugs 0.000 claims description 26
238000006884 silylation reaction Methods 0.000 claims description 26
238000005917 acylation reaction Methods 0.000 claims description 22
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 18
239000005051 trimethylchlorosilane Substances 0.000 claims description 17
150000001263 acyl chlorides Chemical class 0.000 claims description 15
229930182555 Penicillin Natural products 0.000 claims description 14
230000010933 acylation Effects 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 13
239000012433 hydrogen halide Substances 0.000 claims description 13
229910000039 hydrogen halide Inorganic materials 0.000 claims description 13
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 11
229940049954 penicillin Drugs 0.000 claims description 11
159000000000 sodium salts Chemical class 0.000 claims description 10
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin 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=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims description 9
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 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
230000003115 biocidal effect Effects 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
150000004682 monohydrates Chemical class 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
238000011065 in-situ storage Methods 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
229960003326 cloxacillin Drugs 0.000 claims description 4
LQOLIRLGBULYKD-JKIFEVAISA-N cloxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl LQOLIRLGBULYKD-JKIFEVAISA-N 0.000 claims description 4
229960001585 dicloxacillin Drugs 0.000 claims description 4
GVVFCAFBYHYGEE-UHFFFAOYSA-N 2-amino-2-phenylacetyl chloride;hydron;chloride Chemical compound Cl.ClC(=O)C(N)C1=CC=CC=C1 GVVFCAFBYHYGEE-UHFFFAOYSA-N 0.000 claims description 3
YFAGHNZHGGCZAX-JKIFEVAISA-N dicloxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl YFAGHNZHGGCZAX-JKIFEVAISA-N 0.000 claims description 3
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
235000013877 carbamide Nutrition 0.000 description 55
239000000047 product Substances 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
239000000725 suspension Substances 0.000 description 28
RXDALBZNGVATNY-CWLIKTDRSA-N ampicillin trihydrate Chemical compound O.O.O.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 RXDALBZNGVATNY-CWLIKTDRSA-N 0.000 description 26
238000003756 stirring Methods 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 12
150000004684 trihydrates Chemical class 0.000 description 11
238000004458 analytical method Methods 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
238000002798 spectrophotometry method Methods 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
150000001266 acyl halides Chemical class 0.000 description 8
229960000723 ampicillin Drugs 0.000 description 7
238000001035 drying Methods 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 6
MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
125000005270 trialkylamine group Chemical group 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 3
229960003669 carbenicillin Drugs 0.000 description 3
KCUWTKOTPIUBRI-VICXVTCVSA-M cloxacillin sodium monohydrate Chemical compound O.[Na+].N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C([O-])=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl KCUWTKOTPIUBRI-VICXVTCVSA-M 0.000 description 3
SIGZQNJITOWQEF-VICXVTCVSA-M dicloxacillin sodium monohydrate Chemical compound O.[Na+].N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C([O-])=O)=O)C(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl SIGZQNJITOWQEF-VICXVTCVSA-M 0.000 description 3
238000012543 microbiological analysis Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229960003022 amoxicillin Drugs 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
229960004273 floxacillin Drugs 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 2
150000002960 penicillins Chemical class 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
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
AATYKEFFPLPLST-UHFFFAOYSA-N trimethylsilylurea Chemical compound C[Si](C)(C)NC(N)=O AATYKEFFPLPLST-UHFFFAOYSA-N 0.000 description 2
AVKUERGKIZMTKX-ZIOCXDFPSA-N (5R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N[C@@H](C(=O)NC1[C@@H]2N(C(C(S2)(C)C)C(=O)O)C1=O)C1=CC=CC=C1 AVKUERGKIZMTKX-ZIOCXDFPSA-N 0.000 description 1
MEAZEHJUPLREOQ-UHFFFAOYSA-N 2-amino-2-phenylacetyl chloride Chemical compound ClC(=O)C(N)C1=CC=CC=C1 MEAZEHJUPLREOQ-UHFFFAOYSA-N 0.000 description 1
DVMQNHACVBLYQH-UHFFFAOYSA-N 2-anilinoacetyl chloride;hydrochloride Chemical compound Cl.ClC(=O)CNC1=CC=CC=C1 DVMQNHACVBLYQH-UHFFFAOYSA-N 0.000 description 1
JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 1
RRDZILFFDGLJKE-UHFFFAOYSA-N 4-chloro-3-(2-chlorophenyl)-5-methyl-1,2-oxazole Chemical compound ClC1=C(C)ON=C1C1=CC=CC=C1Cl RRDZILFFDGLJKE-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
239000005046 Chlorosilane Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000005553 drilling Methods 0.000 description 1
230000012010 growth Effects 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229960003085 meticillin Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
229960001019 oxacillin Drugs 0.000 description 1
UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 description 1
238000000711 polarimetry Methods 0.000 description 1
231100000683 possible toxicity Toxicity 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
230000004580 weight loss Effects 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
- 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
- C07D499/04—Preparation
- C07D499/10—Modification of an amino radical directly attached in position 6
- C07D499/12—Acylation

Landscapes

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

NL7907414A 1978-10-06 1979-10-05 Werkwijze voor bereiding van semi-synthetische penicil- line antibiotica. NL7907414A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7839599		1978-10-06
GB7839599		1978-10-06

Publications (1)

Publication Number	Publication Date
NL7907414A true NL7907414A (nl)	1980-04-09

Family

ID=10500170

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7907414A NL7907414A (nl)	1978-10-06	1979-10-05	Werkwijze voor bereiding van semi-synthetische penicil- line antibiotica.

Country Status (16)

Country	Link
US (1)	US4272438A (fr)
JP (1)	JPS5551090A (fr)
KR (1)	KR830001290A (fr)
AT (1)	AT364848B (fr)
AU (1)	AU526766B2 (fr)
BE (1)	BE879221A (fr)
CH (1)	CH646435A5 (fr)
DE (1)	DE2940489A1 (fr)
DK (1)	DK417979A (fr)
ES (1)	ES484763A1 (fr)
FR (1)	FR2438049A1 (fr)
IT (1)	IT1162681B (fr)
NL (1)	NL7907414A (fr)
SE (1)	SE7908285L (fr)
YU (1)	YU242379A (fr)
ZA (1)	ZA795330B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5073844A (en) *	1991-01-11	1991-12-17	The Annlouise Partnership	Lighted baggage piece
CN102702227A (zh) *	2012-06-12	2012-10-03	河北华日药业有限公司	一种氟氯西林钠的制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4182709A (en) *	1976-01-15	1980-01-08	Glaxo Group Limited	Manufacture of semi-synthetic penicillin antibiotics
US4181656A (en) *	1976-01-15	1980-01-01	Glaxo Group Limited	Manufacture of semi-synthetic penicillin antibiotics

1979
- 1979-09-28 US US06/079,939 patent/US4272438A/en not_active Expired - Lifetime
- 1979-10-04 YU YU02423/79A patent/YU242379A/xx unknown
- 1979-10-04 KR KR1019790003421A patent/KR830001290A/ko not_active Ceased
- 1979-10-05 JP JP12807179A patent/JPS5551090A/ja active Pending
- 1979-10-05 CH CH900379A patent/CH646435A5/de not_active IP Right Cessation
- 1979-10-05 DE DE19792940489 patent/DE2940489A1/de not_active Withdrawn
- 1979-10-05 FR FR7924825A patent/FR2438049A1/fr active Granted
- 1979-10-05 ZA ZA00795330A patent/ZA795330B/xx unknown
- 1979-10-05 SE SE7908285A patent/SE7908285L/xx not_active Application Discontinuation
- 1979-10-05 DK DK417979A patent/DK417979A/da not_active Application Discontinuation
- 1979-10-05 BE BE197487A patent/BE879221A/fr unknown
- 1979-10-05 ES ES484763A patent/ES484763A1/es not_active Expired
- 1979-10-05 IT IT50468/79A patent/IT1162681B/it active
- 1979-10-05 AU AU51508/79A patent/AU526766B2/en not_active Ceased
- 1979-10-05 NL NL7907414A patent/NL7907414A/nl not_active Application Discontinuation
- 1979-10-05 AT AT0653079A patent/AT364848B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA795330B (en)	1980-11-26
DK417979A (da)	1980-04-07
ES484763A1 (es)	1980-06-16
SE7908285L (sv)	1980-05-22
AT364848B (de)	1981-11-25
KR830001290A (ko)	1983-04-30
YU242379A (en)	1982-10-31
AU526766B2 (en)	1983-01-27
JPS5551090A (en)	1980-04-14
CH646435A5 (de)	1984-11-30
AU5150879A (en)	1980-04-17
FR2438049B1 (fr)	1982-10-22
BE879221A (fr)	1980-04-08
FR2438049A1 (fr)	1980-04-30
IT1162681B (it)	1987-04-01
IT7950468A0 (it)	1979-10-05
ATA653079A (de)	1981-04-15
US4272438A (en)	1981-06-09
DE2940489A1 (de)	1980-04-24

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1986-12-01	BV	The patent application has lapsed

Publication	Publication Date	Title
KR100590342B1 (ko)	2006-06-15	아제티딘온 중간체 화합물의 에난티오-선택적 합성법
US4007168A (en)	1977-02-08	Process for preparing penicillins derivatives
US4254029A (en)	1981-03-03	Process for preparing β-lactam antibiotics
IL30703A (en)	1972-10-29	Preparation of alpha-aminopenicillins and their trimethylsilyl derivatives
US4272438A (en)	1981-06-09	Manufacture of semi-synthetic penicillin antibiotics
GB2034695A (en)	1980-06-11	Acylation of 6-APA via silyl intermediates
US3965098A (en)	1976-06-22	Intermediates for preparing cephalosporins and methods of production
GB2179348A (en)	1987-03-04	Process for the preparation of 6-D-( alpha )-(4-ethyl-2,3-dioxo-1 1-piperazinylcarbonylamin)- alpha -phenylacetamido- penicillanic acid
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