DE3037101A1 - Cephalosporinantibiotika - Google Patents

Cephalosporinantibiotika

Info

Publication number: DE3037101A1
Authority: DE; Germany
Prior art keywords: group; formula; compound; acid; compounds
Prior art date: 1979-10-02
Legal status (The legal status 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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE19803037101

Other languages

German (de)

English (en)

Inventor

David George Hubert Princes Risborough Buckinghamshire Livermore

Christopher Earle Ealing London Newall

Cynthia Hilda Gerrards Cross O'Callaghan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Group Ltd

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.)

1979-10-02

Filing date

1980-10-01

Publication date

1981-04-16

1980-10-01 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1981-04-16 Publication of DE3037101A1 publication Critical patent/DE3037101A1/de

Status Withdrawn legal-status Critical Current

Links

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231100000252 nontoxic Toxicity 0.000 claims description 22
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238000000034 method Methods 0.000 claims description 17
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
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241000191967 Staphylococcus aureus Species 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
RRNJROHIFSLGRA-JEDNCBNOSA-N acetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(O)=O.NCCCC[C@H](N)C(O)=O RRNJROHIFSLGRA-JEDNCBNOSA-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
230000002378 acidificating effect Effects 0.000 description 1
125000005041 acyloxyalkyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
238000005804 alkylation reaction Methods 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
150000001412 amines Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000013011 aqueous formulation Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical group [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
125000005518 carboxamido group Chemical group 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
QHTOIDKCEPKVCM-ZCFIWIBFSA-N cepham Chemical compound S1CCCN2C(=O)C[C@H]21 QHTOIDKCEPKVCM-ZCFIWIBFSA-N 0.000 description 1
150000001782 cephems Chemical class 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229920006026 co-polymeric resin Polymers 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
IEMGWBMVQLVHEY-UHFFFAOYSA-N ethyl 2-(3-amino-6,7-dihydro-5h-cyclopenta[b]pyridin-7-yl)acetate Chemical compound NC1=CN=C2C(CC(=O)OCC)CCC2=C1 IEMGWBMVQLVHEY-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
229940013688 formic acid Drugs 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
229940047650 haemophilus influenzae Drugs 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
229940006461 iodide ion Drugs 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
229960005357 lysine acetate Drugs 0.000 description 1
239000002609 medium Substances 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 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
125000002560 nitrile group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
244000052769 pathogen Species 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 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
KIDBBTHHMJOMAU-UHFFFAOYSA-N propan-1-ol;hydrate Chemical compound O.CCCO KIDBBTHHMJOMAU-UHFFFAOYSA-N 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
230000005588 protonation Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010791 quenching Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940115939 shigella sonnei Drugs 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
AAMCVENDCXWDPJ-UHFFFAOYSA-N sulfanyl acetate Chemical class CC(=O)OS AAMCVENDCXWDPJ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000005866 tritylation reaction Methods 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
- 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)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (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)

DE19803037101 1979-10-02 1980-10-01 Cephalosporinantibiotika Withdrawn DE3037101A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7934069		1979-10-02

Publications (1)

Publication Number	Publication Date
DE3037101A1 true DE3037101A1 (de)	1981-04-16

Family

ID=10508218

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19803037101 Withdrawn DE3037101A1 (de)	1979-10-02	1980-10-01	Cephalosporinantibiotika

Country Status (10)

Country	Link
JP (1)	JPS5657790A (it)
AU (1)	AU538653B2 (it)
BE (1)	BE885487A (it)
CH (1)	CH645906A5 (it)
DE (1)	DE3037101A1 (it)
FR (1)	FR2466468A1 (it)
GB (1)	GB2062624B (it)
IT (1)	IT1143007B (it)
NL (1)	NL8005440A (it)
ZA (1)	ZA806084B (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58210093A (ja) *	1982-05-20	1983-12-07	グラクソ・グル−プ・リミテツド	セフアロスポリン抗生物質

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1522140A (en) *	1974-12-20	1978-08-23	Glaxo Lab Ltd	Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl cephalosporins methods for their preparation and compositions containing them
PH17188A (en) *	1977-03-14	1984-06-14	Fujisawa Pharmaceutical Co	New cephem and cepham compounds and their pharmaceutical compositions and method of use
SE439312B (sv) *	1977-03-25	1985-06-10	Roussel Uclaf	Sett att framstella nya oximderivat av 3-acetoximetyl-7-aminotiazolylacetamido cefalosporansyra
DE2758001A1 (de) *	1977-12-24	1979-07-12	Hoechst Ag	Cephalosporinderivate und verfahren zu ihrer herstellung
AR228726A1 (es) *	1978-05-26	1983-04-15	Glaxo Group Ltd	Procedimiento para la preparacion del antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)acetamido)-3-(1-piridiniometil)cef-3-em-4-carboxilato

1980
- 1980-10-01 IT IT49784/80A patent/IT1143007B/it active
- 1980-10-01 AU AU62881/80A patent/AU538653B2/en not_active Ceased
- 1980-10-01 FR FR8021035A patent/FR2466468A1/fr active Granted
- 1980-10-01 BE BE0/202299A patent/BE885487A/fr not_active IP Right Cessation
- 1980-10-01 NL NL8005440A patent/NL8005440A/nl not_active Application Discontinuation
- 1980-10-01 DE DE19803037101 patent/DE3037101A1/de not_active Withdrawn
- 1980-10-01 JP JP13822380A patent/JPS5657790A/ja active Pending
- 1980-10-01 GB GB8031704A patent/GB2062624B/en not_active Expired
- 1980-10-01 ZA ZA00806084A patent/ZA806084B/xx unknown
- 1980-10-01 CH CH734280A patent/CH645906A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1143007B (it)	1986-10-22
GB2062624A (en)	1981-05-28
FR2466468B1 (it)	1984-02-10
BE885487A (fr)	1981-04-01
IT8049784A0 (it)	1980-10-01
AU538653B2 (en)	1984-08-23
JPS5657790A (en)	1981-05-20
CH645906A5 (de)	1984-10-31
FR2466468A1 (fr)	1981-04-10
ZA806084B (en)	1982-05-26
AU6288180A (en)	1981-04-09
GB2062624B (en)	1983-09-07
NL8005440A (nl)	1981-04-06

Legal Events

Date	Code	Title	Description
1986-10-09	8139	Disposal/non-payment of the annual fee

Publication	Publication Date	Title
AT370420B (de)	1983-03-25	Verfahren zur herstellung von neuen cephalosporin-antibiotika
AT369749B (de)	1983-01-25	Verfahren zur herstellung von neuen cephalosporinantibiotika
DE2439880A1 (de)	1975-04-03	Antibiotika und verfahren zu ihrer herstellung
NO793688L (no)	1980-05-19	Fremgangsmaate ved fremstilling av cephalosporinderivater
DE69028342T2 (de)	1997-02-13	Cephalosporinverbindungen und Verfahren zu ihrer Herstellung
DE2943427A1 (de)	1980-05-08	Cephalosporinverbindungen
CH649557A5 (de)	1985-05-31	Cephalosporinantibiotika.
DE3011038A1 (de)	1980-11-27	Cephalosporinantibiotika
DE69030502T2 (de)	1997-07-24	Cephalosporinverbindungen und deren herstellung
DE3006777A1 (de)	1980-09-04	Cephalosporin-antibiotika
KR830001130B1 (ko)	1983-06-14	세팔로스포린 항생제의 제조방법
CH637139A5 (de)	1983-07-15	Verfahren zur herstellung von cephalosporinverbindungen.
DE2943437A1 (de)	1980-05-08	Cephalosporinverbindungen
AT391319B (de)	1990-09-25	Verfahren zur herstellung von neuen cephalosporinverbindungen
DE3037101A1 (de)	1981-04-16	Cephalosporinantibiotika
AT375663B (de)	1984-08-27	Verfahren zur herstellung von neuen cephalosporinantibiotika
DE3323462A1 (de)	1984-01-12	Cephalosporin-antibiotika
DE3342317A1 (de)	1984-05-24	Cephalosporin-antibiotika
AT375662B (de)	1984-08-27	Verfahren zur herstellung von neuen cephalosporinantibiotika
DE3323450A1 (de)	1984-01-12	Cephalosporin-antibiotika
AT371125B (de)	1983-06-10	Verfahren zur herstellung von neuen cephalosporinantibiotika
AT371474B (de)	1983-06-27	Verfahren zur herstellung von neuen cephalosporinantibiotika
DE2921344A1 (de)	1979-12-06	Cephalosporinantibiotika
AT371126B (de)	1983-06-10	Verfahren zur herstellung von neuen cephalosporin-antibiotika
AT371476B (de)	1983-06-27	Verfahren zur herstellung von neuen cephalosporinantibiotika