CH623055A5 - Process for the preparation of novel cephalosporins - Google Patents

Process for the preparation of novel cephalosporins Download PDF

Info

Publication number: CH623055A5
Authority: CH; Switzerland
Prior art keywords: methyl; conh; formula; oxo; ceph
Prior art date: 1975-10-28

Application number

CH1345376A

Other languages

German (de)

English (en)

Inventor

Hans-Bodo Dr Koenig

Karl Georg Dr Metzger

Wilfried Dr Schroeck

Original Assignee

Bayer Ag

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.)

1975-10-28

Filing date

1976-10-25

Publication date

1981-05-15

1976-10-25 Application filed by Bayer Ag filed Critical Bayer Ag

1981-05-15 Publication of CH623055A5 publication Critical patent/CH623055A5/de

Links

229930186147 Cephalosporin Natural products 0.000 title claims description 22
229940124587 cephalosporin Drugs 0.000 title claims description 22
150000001780 cephalosporins Chemical class 0.000 title claims description 20
238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 11
-1 2-oxo-3-mesyl-imidazolidin-l- yl Chemical group 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 22
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125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
231100000252 nontoxic Toxicity 0.000 claims description 8
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150000007513 acids Chemical class 0.000 claims description 5
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
JTPZTKBRUCILQD-UHFFFAOYSA-N 1-methylimidazolidin-2-one Chemical compound CN1CCNC1=O JTPZTKBRUCILQD-UHFFFAOYSA-N 0.000 claims 1
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241000606834 [Haemophilus] ducreyi Species 0.000 description 1
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VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
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239000008272 agar Substances 0.000 description 1
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235000010443 alginic acid Nutrition 0.000 description 1
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XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
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LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000002647 aminoglycoside antibiotic agent Substances 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
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125000003118 aryl group Chemical group 0.000 description 1
229940065181 bacillus anthracis Drugs 0.000 description 1
239000002585 base 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
229960002903 benzyl benzoate Drugs 0.000 description 1
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206010006451 bronchitis Diseases 0.000 description 1
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239000000872 buffer Substances 0.000 description 1
235000019437 butane-1,3-diol Nutrition 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000000378 calcium silicate Substances 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 description 1
229960000603 cefalotin Drugs 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229940106164 cephalexin Drugs 0.000 description 1
AVGYWQBCYZHHPN-CYJZLJNKSA-N cephalexin monohydrate Chemical compound O.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 AVGYWQBCYZHHPN-CYJZLJNKSA-N 0.000 description 1
VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
229940079593 drug Drugs 0.000 description 1
208000019258 ear infection Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
206010014665 endocarditis Diseases 0.000 description 1
229940092559 enterobacter aerogenes Drugs 0.000 description 1
JJTJZFLRKYYGGS-UHFFFAOYSA-N ethoxyethane;methylsulfinylmethane Chemical compound CS(C)=O.CCOCC JJTJZFLRKYYGGS-UHFFFAOYSA-N 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
239000010642 eucalyptus oil Substances 0.000 description 1
229940044949 eucalyptus oil Drugs 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000835 fiber Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229960002518 gentamicin Drugs 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
239000003906 humectant Substances 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229930182823 kanamycin A Natural products 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000003973 paint Substances 0.000 description 1
239000000123 paper Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
206010034674 peritonitis Diseases 0.000 description 1
239000012071 phase Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 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
238000004321 preservation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229940007046 shigella dysenteriae Drugs 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229960005456 sisomicin Drugs 0.000 description 1
URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
229960000707 tobramycin Drugs 0.000 description 1
NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
229940118696 vibrio cholerae Drugs 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Fodder In General (AREA)

CH1345376A 1975-10-28 1976-10-25 Process for the preparation of novel cephalosporins CH623055A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19752548248 DE2548248A1 (de)	1975-10-28	1975-10-28	Cephalosporine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
CH623055A5 true CH623055A5 (en)	1981-05-15

Family

ID=5960288

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1345376A CH623055A5 (en)	1975-10-28	1976-10-25	Process for the preparation of novel cephalosporins

Country Status (19)

Country	Link
JP (1)	JPS5253892A (sv)
AT (1)	AT349632B (sv)
AU (1)	AU502403B2 (sv)
BE (1)	BE847730A (sv)
CA (1)	CA1084906A (sv)
CH (1)	CH623055A5 (sv)
DD (1)	DD127948A5 (sv)
DE (1)	DE2548248A1 (sv)
DK (1)	DK485576A (sv)
ES (1)	ES452778A1 (sv)
FI (1)	FI763046A (sv)
FR (1)	FR2329285A1 (sv)
GB (1)	GB1568385A (sv)
GR (1)	GR61164B (sv)
IE (1)	IE44028B1 (sv)
IL (1)	IL50760A (sv)
LU (1)	LU76072A1 (sv)
NL (1)	NL7611854A (sv)
SE (1)	SE7611926L (sv)

1975
- 1975-10-28 DE DE19752548248 patent/DE2548248A1/de not_active Withdrawn
1976
- 1976-10-25 CH CH1345376A patent/CH623055A5/de not_active IP Right Cessation
- 1976-10-25 IL IL50760A patent/IL50760A/xx unknown
- 1976-10-26 DD DD7600195462A patent/DD127948A5/xx unknown
- 1976-10-26 JP JP51127902A patent/JPS5253892A/ja active Pending
- 1976-10-26 LU LU76072A patent/LU76072A1/xx unknown
- 1976-10-26 CA CA264,210A patent/CA1084906A/en not_active Expired
- 1976-10-26 GR GR52018A patent/GR61164B/el unknown
- 1976-10-26 FI FI763046A patent/FI763046A/fi not_active Application Discontinuation
- 1976-10-26 NL NL7611854A patent/NL7611854A/xx not_active Application Discontinuation
- 1976-10-26 GB GB44420/76A patent/GB1568385A/en not_active Expired
- 1976-10-27 ES ES452778A patent/ES452778A1/es not_active Expired
- 1976-10-27 DK DK485576A patent/DK485576A/da unknown
- 1976-10-27 SE SE7611926A patent/SE7611926L/sv unknown
- 1976-10-27 IE IE2374/76A patent/IE44028B1/en unknown
- 1976-10-28 AT AT802176A patent/AT349632B/de not_active IP Right Cessation
- 1976-10-28 BE BE171864A patent/BE847730A/xx unknown
- 1976-10-28 AU AU19102/76A patent/AU502403B2/en not_active Expired
- 1976-10-28 FR FR7632617A patent/FR2329285A1/fr active Granted

Also Published As

Publication number	Publication date
GB1568385A (en)	1980-05-29
DE2548248A1 (de)	1977-05-05
DK485576A (da)	1977-04-29
LU76072A1 (sv)	1977-05-31
AT349632B (de)	1979-04-10
NL7611854A (nl)	1977-05-02
AU502403B2 (en)	1979-07-26
JPS5253892A (en)	1977-04-30
IE44028B1 (en)	1981-07-29
FR2329285B1 (sv)	1980-03-28
DD127948A5 (de)	1977-10-19
IE44028L (en)	1977-04-28
CA1084906A (en)	1980-09-02
FR2329285A1 (fr)	1977-05-27
GR61164B (en)	1978-10-03
IL50760A (en)	1979-11-30
AU1910276A (en)	1978-05-04
SE7611926L (sv)	1977-04-29
ATA802176A (de)	1978-09-15
BE847730A (fr)	1977-04-28
IL50760A0 (en)	1976-12-31
FI763046A (sv)	1977-04-29
ES452778A1 (es)	1978-01-16

Publication	Publication Date	Title
DE2736471C2 (sv)	1988-09-22
EP0004956B1 (de)	1981-10-14	Beta-Lactamantibiotika, Verfahren zu ihrer Herstellung, Futterzusatzmittel, Arzneimittel sowie Verfahren zu deren Herstellung
DE2407715C2 (de)	1982-12-02	Cephalosporine, Verfahren zu ihrer Herstellung sowie Arzneimittel
EP0000392B1 (de)	1982-04-28	Cephalosporin und Penicillin-derivate, Verfahren zu deren Herstellung, und deren pharmazeutische Präparate
CH623326A5 (sv)	1981-05-29
EP0092722B1 (de)	1986-09-10	Beta-Lactam-Antibiotika, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
DE2354219A1 (de)	1975-05-07	Beta-lactam-antibiotica, ein verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE3734004A1 (de)	1988-12-15	Substituierte vinylcephalosporine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE2633317A1 (de)	1978-01-26	Beta-lactamantibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2720579A1 (de)	1978-11-09	Beta-lactam-verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
CH633802A5 (de)	1982-12-31	Verfahren zur herstellung neuer beta-lactam-antibiotica.
DE2440268A1 (de)	1976-03-04	Beta-lactamantibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
EP0075169A1 (de)	1983-03-30	Beta-Lactam Antibiotica, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
DE2810083A1 (de)	1979-09-20	Beta-lactam-verbindungen
EP0035161B1 (de)	1983-11-23	Cephalosporine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0098433B1 (de)	1987-12-02	Beta-Lactamantibiotika, Verfahren zu deren Herstellung sowie sie enthaltende Mittel
DE2456307A1 (de)	1976-08-12	Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
CH623055A5 (en)	1981-05-15	Process for the preparation of novel cephalosporins
CH623056A5 (en)	1981-05-15	Process for the preparation of novel cephalosporins
DE2528079A1 (de)	1977-01-20	Penicilline, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2720580A1 (de)	1978-11-09	Beta-lactam-verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2658905A1 (de)	1978-10-19	Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2658718A1 (de)	1978-06-29	Methoxy-beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
CH628056A5 (en)	1982-02-15	Process for the preparation of beta-lactam antibiotics
DE2727586A1 (de)	1979-01-04	Methoxy-beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung

Legal Events

Date	Code	Title	Description
1983-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased