CH641810A5 - Acetamidocephalosporanic acid derivatives, process for their preparation and pharmaceutical forms which contain them - Google Patents

Acetamidocephalosporanic acid derivatives, process for their preparation and pharmaceutical forms which contain them Download PDF

Info

Publication number: CH641810A5
Authority: CH; Switzerland
Prior art keywords: group; formula; hydrogen; acid; compounds
Prior art date: 1979-02-16

Application number

CH154579A

Other languages

German (de)

English (en)

Inventor

Helmut Dr Hamberger

Hans Dr Fliri

Original Assignee

Sandoz 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.)

1979-02-16

Filing date

1979-02-16

Publication date

1984-03-15

1979-02-16 Application filed by Sandoz Ag filed Critical Sandoz Ag

1979-02-16 Priority to CH154579A priority Critical patent/CH641810A5/de

1980-02-07 Priority to SE8000982A priority patent/SE8000982L/xx

1980-02-07 Priority to DK53780A priority patent/DK53780A/da

1980-02-07 Priority to FI800381A priority patent/FI800381A7/fi

1980-02-11 Priority to BE1/9716A priority patent/BE881641A/fr

1980-02-11 Priority to DE19803005012 priority patent/DE3005012A1/de

1980-02-12 Priority to GB8004696A priority patent/GB2046734B/en

1980-02-13 Priority to FR8003143A priority patent/FR2449093A1/fr

1980-02-13 Priority to NL8000894A priority patent/NL8000894A/nl

1980-02-14 Priority to AT0078780A priority patent/AT374806B/de

1980-02-14 Priority to NZ192873A priority patent/NZ192873A/en

1980-02-14 Priority to AU55535/80A priority patent/AU541011B2/en

1980-02-14 Priority to IL59391A priority patent/IL59391A/xx

1980-02-14 Priority to CA000345659A priority patent/CA1161032A/fr

1980-02-14 Priority to PT70834A priority patent/PT70834A/pt

1980-02-14 Priority to IE284/80A priority patent/IE49395B1/en

1980-02-14 Priority to IE1624/84A priority patent/IE49396B1/en

1980-02-14 Priority to YU00402/80A priority patent/YU40280A/xx

1980-02-15 Priority to IT8047922A priority patent/IT8047922A0/it

1980-02-15 Priority to ES488651A priority patent/ES488651A0/es

1980-02-15 Priority to PH23650A priority patent/PH17926A/en

1980-02-15 Priority to JP1844280A priority patent/JPS55113794A/ja

1980-02-15 Priority to ZA00800885A priority patent/ZA80885B/xx

1980-11-20 Priority to ES497002A priority patent/ES497002A0/es

1982-06-21 Priority to US06/390,323 priority patent/US4477448A/en

1983-04-11 Priority to GB08309730A priority patent/GB2117774B/en

1984-03-15 Publication of CH641810A5 publication Critical patent/CH641810A5/de

1985-02-08 Priority to SE8500589A priority patent/SE8500589D0/xx

1985-12-30 Priority to MY128/85A priority patent/MY8500128A/xx

Links

239000002253 acid Substances 0.000 title claims description 15
238000000034 method Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 44
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
239000001257 hydrogen Substances 0.000 claims abstract description 31
125000000217 alkyl group Chemical group 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 19
-1 carbamoyloxy Chemical group 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
125000004185 ester group Chemical group 0.000 claims abstract description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 5
125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
239000000725 suspension Substances 0.000 claims description 4
230000000844 anti-bacterial effect Effects 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 2
150000001540 azides Chemical class 0.000 claims description 2
230000003115 biocidal effect Effects 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
150000002989 phenols Chemical class 0.000 claims description 2
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 2
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
239000003242 anti bacterial agent Substances 0.000 abstract description 2
230000000845 anti-microbial effect Effects 0.000 abstract description 2
229940088710 antibiotic agent Drugs 0.000 abstract description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
125000003277 amino group Chemical group 0.000 abstract 1
125000003884 phenylalkyl group Chemical group 0.000 abstract 1
239000000243 solution Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
DOOVDXPRGGINTD-UHFFFAOYSA-N methyl 2-methoxyiminoacetate Chemical compound CON=CC(=O)OC DOOVDXPRGGINTD-UHFFFAOYSA-N 0.000 description 6
MIHIJWOEDDPOLG-UHFFFAOYSA-N 2-methoxyiminoacetic acid Chemical compound CON=CC(O)=O MIHIJWOEDDPOLG-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-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
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
LULXBAGMGMJJRW-UHFFFAOYSA-N n,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)CC(=O)N[Si](C)(C)C LULXBAGMGMJJRW-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005277 alkyl imino group Chemical group 0.000 description 1
BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000036765 blood level Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000005521 carbonamide group Chemical group 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 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
239000012074 organic phase Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom

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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)

CH154579A 1979-02-16 1979-02-16 Acetamidocephalosporanic acid derivatives, process for their preparation and pharmaceutical forms which contain them CH641810A5 (en)

Priority Applications (28)

Application Number	Priority Date	Filing Date	Title
CH154579A CH641810A5 (en)	1979-02-16	1979-02-16	Acetamidocephalosporanic acid derivatives, process for their preparation and pharmaceutical forms which contain them
SE8000982A SE8000982L (sv)	1979-02-16	1980-02-07	Nya cefalosporinderivat, deras framstellning och anvendning som antimikrobiella medel
DK53780A DK53780A (da)	1979-02-16	1980-02-07	Fremgangsmaade til fremstilling af cephalosporinderivater
FI800381A FI800381A7 (fi)	1979-02-16	1980-02-07	Uusia kefalosporiini johdannaisia, niiden valmistus ja käyttö mikrobin vastaisina aineina.
BE1/9716A BE881641A (fr)	1979-02-16	1980-02-11	Nouveaux derives de la cephalosporine, leur preparation et leur application comme medicaments
DE19803005012 DE3005012A1 (de)	1979-02-16	1980-02-11	Neue cephalosporinderivate, verfahren zu ihrer herstellung und ihre verwendung
GB8004696A GB2046734B (en)	1979-02-16	1980-02-12	7-(-oximino-pyrazolyl(-acetamido)-cephen derivatives
FR8003143A FR2449093A1 (fr)	1979-02-16	1980-02-13	Nouveaux derives de la cephalosporine, leur preparation et leur application comme medicaments
NL8000894A NL8000894A (nl)	1979-02-16	1980-02-13	Nieuwe cefalosporinederivaten en werkwijzen voor het bereiden en toepassen van deze derivaten.
CA000345659A CA1161032A (fr)	1979-02-16	1980-02-14	Derives de la cephalosporine, production et utilisation comme agents antimicrobiens
NZ192873A NZ192873A (en)	1979-02-16	1980-02-14	Cephalosporin derivatives:preparation and pharmaceutical compositions
AU55535/80A AU541011B2 (en)	1979-02-16	1980-02-14	Cephalosporins
IL59391A IL59391A (en)	1979-02-16	1980-02-14	7-pyrazolyl-oximinoacetylamino-cephalosporanic acid derivatives,their production and chemotherapeutical compositions containing them
AT0078780A AT374806B (de)	1979-02-16	1980-02-14	Verfahren zur herstellung neuer cephalosporinderivate
PT70834A PT70834A (en)	1979-02-16	1980-02-14	Process for the production of new cephalosporin derivatives having pharmaceutical properties
IE284/80A IE49395B1 (en)	1979-02-16	1980-02-14	New cephalosporin derivatives,their production and use as antimicrobial agents
IE1624/84A IE49396B1 (en)	1979-02-16	1980-02-14	Oximinoacetic acid derivatives
YU00402/80A YU40280A (en)	1979-02-16	1980-02-14	Process for preparing new cephalosporin derivatives
IT8047922A IT8047922A0 (it)	1979-02-16	1980-02-15	Derivati della cefalosporina loro preparazione e loro impiego come antibiotici
ES488651A ES488651A0 (es)	1979-02-16	1980-02-15	Procedimiento para preparar derivados de acido acetico
PH23650A PH17926A (en)	1979-02-16	1980-02-15	New cephalosporin derivatives,and pharmaceutical compositions containing same
JP1844280A JPS55113794A (en)	1979-02-16	1980-02-15	Novel cephalosporin derivative*its manufacture and use as antibacterial
ZA00800885A ZA80885B (en)	1979-02-16	1980-02-15	New cephalosporin derivatives, their production and use as antimicrobial agents
ES497002A ES497002A0 (es)	1979-02-16	1980-11-20	Procedimiento para preparar derivados de acido acetico
US06/390,323 US4477448A (en)	1979-02-16	1982-06-21	Cephalosporin derivatives and use as antimicrobial agents
GB08309730A GB2117774B (en)	1979-02-16	1983-04-11	Oximinoacetic acid derivatives
SE8500589A SE8500589D0 (sv)	1979-02-16	1985-02-08	Oximinoettiksyraderivat
MY128/85A MY8500128A (en)	1979-02-16	1985-12-30	New cephalosporin derivatives, their production and use as antimicrobial agents

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH154579A CH641810A5 (en)	1979-02-16	1979-02-16	Acetamidocephalosporanic acid derivatives, process for their preparation and pharmaceutical forms which contain them

Publications (1)

Publication Number	Publication Date
CH641810A5 true CH641810A5 (en)	1984-03-15

Family

ID=4212918

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH154579A CH641810A5 (en)	1979-02-16	1979-02-16	Acetamidocephalosporanic acid derivatives, process for their preparation and pharmaceutical forms which contain them

Country Status (4)

Country	Link
JP (1)	JPS55113794A (fr)
BE (1)	BE881641A (fr)
CH (1)	CH641810A5 (fr)
ZA (1)	ZA80885B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH648038A5 (de) *	1981-01-19	1985-02-28	Sandoz Ag	7-((carboxymethoxyimino)-1h-pyrazol-3-yl-acetyl)amino-3-desacetoxy-3-(1-methyl-1h-tetrazol-5-yl-thio)cephalosporansaeure und salze, verfahren zur herstellung und verwendung.

1979
- 1979-02-16 CH CH154579A patent/CH641810A5/de not_active IP Right Cessation
1980
- 1980-02-11 BE BE1/9716A patent/BE881641A/fr not_active IP Right Cessation
- 1980-02-15 ZA ZA00800885A patent/ZA80885B/xx unknown
- 1980-02-15 JP JP1844280A patent/JPS55113794A/ja active Pending

Also Published As

Publication number	Publication date
ZA80885B (en)	1981-09-30
JPS55113794A (en)	1980-09-02
BE881641A (fr)	1980-08-11

Legal Events

Date	Code	Title	Description
1986-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

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