NL8601842A - Ceph-3-em-carbonzuurderivaten, werkwijze ter bereiding daarvan, dergelijke verbindingen bevattende farmaceutische preparaten, werkwijze voor de bereiding van deze laatste, alsmede werkwijze voor de behandeling van patienten, die lijden aan bacteriele ziekten. - Google Patents

Ceph-3-em-carbonzuurderivaten, werkwijze ter bereiding daarvan, dergelijke verbindingen bevattende farmaceutische preparaten, werkwijze voor de bereiding van deze laatste, alsmede werkwijze voor de behandeling van patienten, die lijden aan bacteriele ziekten. Download PDF

Info

Publication number: NL8601842A
Authority: NL; Netherlands
Prior art keywords: formula; ceph; methyl; tetrazol; chloro
Prior art date: 1985-07-16

Application number

NL8601842A

Other languages

English (en)

Dutch (nl)

Original Assignee

Biogal Gyogyszergyar

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.)

1985-07-16

Filing date

1986-07-15

Publication date

1987-02-16

1986-07-15 Application filed by Biogal Gyogyszergyar filed Critical Biogal Gyogyszergyar

1987-02-16 Publication of NL8601842A publication Critical patent/NL8601842A/nl

Links

238000000034 method Methods 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title claims description 15
239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims description 39
-1 3-chloro-isoxazol-5-yl Chemical group 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 5
208000035143 Bacterial infection Diseases 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
URYHLKSQDVSSAP-UHFFFAOYSA-N 2-(3-chloro-2H-1,2-oxazol-3-yl)acetic acid Chemical compound ClC1(NOC=C1)CC(=O)O URYHLKSQDVSSAP-UHFFFAOYSA-N 0.000 claims description 2
ORXXIFVDJYHWJS-UHFFFAOYSA-N acetic acid 3-chloro-1,2-oxazole Chemical compound C(C)(=O)O.ClC1=NOC=C1 ORXXIFVDJYHWJS-UHFFFAOYSA-N 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
230000037396 body weight Effects 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
241000699670 Mus sp. Species 0.000 description 9
159000000000 sodium salts Chemical class 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
244000005700 microbiome Species 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000007912 intraperitoneal administration Methods 0.000 description 5
241000588724 Escherichia coli Species 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000036765 blood level Effects 0.000 description 4
239000003814 drug Substances 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
238000003756 stirring Methods 0.000 description 4
229930186147 Cephalosporin Chemical class 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical group 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 description 3
241000191940 Staphylococcus Species 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
230000000845 anti-microbial effect Effects 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
229960002682 cefoxitin Drugs 0.000 description 3
229940124587 cephalosporin Drugs 0.000 description 3
150000001780 cephalosporins Chemical class 0.000 description 3
229940079593 drug Drugs 0.000 description 3
229940049954 penicillin Drugs 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 2
244000063299 Bacillus subtilis Species 0.000 description 2
235000014469 Bacillus subtilis Nutrition 0.000 description 2
102000004506 Blood Proteins Human genes 0.000 description 2
108010017384 Blood Proteins Proteins 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000000973 chemotherapeutic effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000000842 isoxazolyl group Chemical group 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
FZDRVLJSDYQRPO-HWZXHQHMSA-N (6r)-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(C)S[C@@H]2CC(=O)N21 FZDRVLJSDYQRPO-HWZXHQHMSA-N 0.000 description 1
LQUMUKHHUVGAQC-UHFFFAOYSA-N 2-(3-chloro-1,2-oxazol-5-yl)acetic acid Chemical compound OC(=O)CC1=CC(Cl)=NO1 LQUMUKHHUVGAQC-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
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241000588779 Bordetella bronchiseptica Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
GNWUOVJNSFPWDD-XMZRARIVSA-M Cefoxitin sodium Chemical compound [Na+].N([C@]1(OC)C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)CC1=CC=CS1 GNWUOVJNSFPWDD-XMZRARIVSA-M 0.000 description 1
241000194032 Enterococcus faecalis Species 0.000 description 1
241000588722 Escherichia Species 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-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
241000588748 Klebsiella Species 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
241001467018 Typhis Species 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000000676 alkoxyimino group Chemical group 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
230000023555 blood coagulation Effects 0.000 description 1
OLVCFLKTBJRLHI-AXAPSJFSSA-N cefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-AXAPSJFSSA-N 0.000 description 1
229960003012 cefamandole Drugs 0.000 description 1
229960004261 cefotaxime Drugs 0.000 description 1
AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 description 1
JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 description 1
229960001668 cefuroxime Drugs 0.000 description 1
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound 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 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 1
229940106164 cephalexin Drugs 0.000 description 1
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
150000002545 isoxazoles Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
150000003952 β-lactams Chemical class 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
- 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
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings

Landscapes

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

NL8601842A 1985-07-16 1986-07-15 Ceph-3-em-carbonzuurderivaten, werkwijze ter bereiding daarvan, dergelijke verbindingen bevattende farmaceutische preparaten, werkwijze voor de bereiding van deze laatste, alsmede werkwijze voor de behandeling van patienten, die lijden aan bacteriele ziekten. NL8601842A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU852725A HU203243B (en)	1985-07-16	1985-07-16	Process for producing cefalosporin derivative
HU272585		1985-07-16

Publications (1)

Publication Number	Publication Date
NL8601842A true NL8601842A (nl)	1987-02-16

Family

ID=10960853

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8601842A NL8601842A (nl)	1985-07-16	1986-07-15	Ceph-3-em-carbonzuurderivaten, werkwijze ter bereiding daarvan, dergelijke verbindingen bevattende farmaceutische preparaten, werkwijze voor de bereiding van deze laatste, alsmede werkwijze voor de behandeling van patienten, die lijden aan bacteriele ziekten.

Country Status (14)

Country	Link
JP (1)	JPS6222787A (de)
KR (1)	KR930007263B1 (de)
CN (1)	CN1012614B (de)
AT (1)	AT389877B (de)
BE (1)	BE905113A (de)
DE (1)	DE3623900A1 (de)
FI (1)	FI83877C (de)
FR (1)	FR2591598B1 (de)
GB (1)	GB2177696B (de)
GR (1)	GR861855B (de)
HU (1)	HU203243B (de)
IL (1)	IL79410A0 (de)
IT (1)	IT1196494B (de)
NL (1)	NL8601842A (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2012729C (en)	1989-04-07	1997-05-20	Takashi Kuroda	Dulled stretched molding and process for producing the same
JP2893286B2 (ja) *	1990-05-17	1999-05-17	グンゼ株式会社	熱収縮性発泡複合フィルム及びその製法
JP2515295Y2 (ja) *	1993-06-30	1996-10-30	株式会社川崎製作所	管継手
KR100408343B1 (ko) *	2001-11-01	2003-12-06	주식회사 이앤티	자돈의 항상성(Homeostasis)을 유지시킬 수 있는 사료 및그 제조방법

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7402778A (de) *	1973-03-02	1974-09-04
JPS539787A (en) *	1976-07-16	1978-01-28	Yamanouchi Pharmaceut Co Ltd	Novel cephalosporin derivatives and their preparation

1985
- 1985-07-16 HU HU852725A patent/HU203243B/hu unknown
1986
- 1986-07-15 IT IT21135/86A patent/IT1196494B/it active
- 1986-07-15 KR KR1019860005723A patent/KR930007263B1/ko not_active Expired - Fee Related
- 1986-07-15 JP JP61166540A patent/JPS6222787A/ja active Pending
- 1986-07-15 DE DE3623900A patent/DE3623900A1/de not_active Ceased
- 1986-07-15 FR FR868610264A patent/FR2591598B1/fr not_active Expired - Lifetime
- 1986-07-15 NL NL8601842A patent/NL8601842A/nl not_active Application Discontinuation
- 1986-07-15 GB GB08617181A patent/GB2177696B/en not_active Expired
- 1986-07-15 AT AT0192686A patent/AT389877B/de active
- 1986-07-15 IL IL79410A patent/IL79410A0/xx not_active IP Right Cessation
- 1986-07-15 BE BE0/216927A patent/BE905113A/fr not_active IP Right Cessation
- 1986-07-16 FI FI862965A patent/FI83877C/fi not_active IP Right Cessation
- 1986-07-16 GR GR861855A patent/GR861855B/el unknown
- 1986-07-16 CN CN86104805A patent/CN1012614B/zh not_active Expired

Also Published As

Publication number	Publication date
IT8621135A0 (it)	1986-07-15
CN1012614B (zh)	1991-05-15
GB2177696A (en)	1987-01-28
IL79410A0 (en)	1986-10-31
GB8617181D0 (en)	1986-08-20
FI83877C (fi)	1991-09-10
DE3623900A1 (de)	1987-01-29
KR870001219A (ko)	1987-03-12
BE905113A (fr)	1986-11-03
JPS6222787A (ja)	1987-01-30
GR861855B (en)	1986-11-18
ATA192686A (de)	1989-07-15
IT1196494B (it)	1988-11-16
FI862965A7 (fi)	1987-01-17
AT389877B (de)	1990-02-12
FR2591598B1 (fr)	1990-01-26
KR930007263B1 (ko)	1993-08-04
GB2177696B (en)	1989-01-05
HUT48890A (en)	1989-07-28
FR2591598A1 (fr)	1987-06-19
HU203243B (en)	1991-06-28
CN86104805A (zh)	1987-02-18
FI862965A0 (fi)	1986-07-16
FI83877B (fi)	1991-05-31

Legal Events

Date	Code	Title	Description
1993-09-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US4201782A (en)	1980-05-06	Thiadiazolyl cephalosporin analogs
KR100455544B1 (ko)	2005-01-15	세팔로스포린항생제
GB2099418A (en)	1982-12-08	Cephalosporin derivatives
JP2635078B2 (ja)	1997-07-30	結晶化したセフェム−酸付加塩およびそれらの製法
US3719673A (en)	1973-03-06	Derivatives of 7-aminocephalosporanic acid
US4103008A (en)	1978-07-25	7[2(2,3 Dioxopiperazin-1-yl-carbonylamino)substituted 2 phenylacetamido]-3-2'-thiadiazolyl cephalosporanic acid derivatives
FI83877C (fi)	1991-09-10	Foerfarande foer framstaellning av en ny terapeutiskt anvaendbar 7-(3-klorisoxazol-5-yl)-acetamido-3- (1-metyl-1h-1,2,3,4-tetrazol-5-yl)-tiometyl-cef-3-em-4-karboxylsyra
US3814755A (en)	1974-06-04	7-(omikron-aminomethylphenylacetamido)-3-(tetrazolo(4,5-b)pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid
KR830001130B1 (ko)	1983-06-14	세팔로스포린 항생제의 제조방법
US4311842A (en)	1982-01-19	Cephalosporin compounds
US4810702A (en)	1989-03-07	Antibacterial agent for mammal use comprising cephalosporin derivatives as an effective ingredient
US4629726A (en)	1986-12-16	Penem carboxylic acids
KR870000827B1 (ko)	1987-04-23	세팔로스포린 유도체의 제조방법
US4160829A (en)	1979-07-10	Antibacterial 1,2,4-oxadiazolylacetamido cephalosporins
US4034088A (en)	1977-07-05	Cephalosporin derivatives, and compositions containing them
DE2736071C2 (de)	1985-12-05	&alpha;-Methoxy-cephalosporinderivate, Verfahren zu ihrer Herstellung sowie diese als Wirkstoffe enthaltende pharmazeutische Zubereitungen
US4046904A (en)	1977-09-06	Novel penicillin, and its preparation and use
FR2696179A1 (fr)	1994-04-01	Dérivés de thioalkylthiocarbacéphalosporine, procédé pour leurs préparations et formulation pharmaceutique les contenant pour le traitement ou la prophylaxie des infections bactériennes.
EP0883621A1 (de)	1998-12-16	Cephalosporinderivate und verfahren zu ihrer herstellung
US4088761A (en)	1978-05-09	3-[(1,3-Dithiin-5-yl)-acetamido]-cephalosporins and antibacterial compositions containing them
US3944580A (en)	1976-03-16	7-[2-(Dithiocarboxylamino)alkanamido]-cephalosporanic acid derivatives
US3646023A (en)	1972-02-29	Derivatives of 7-aminocephalosporanic acid
KR830001592B1 (ko)	1983-08-16	세팔로스포린 항생제의 제조방법
US4283398A (en)	1981-08-11	Cephalosporins
GB2091263A (en)	1982-07-28	7-((carboxy-methoximino)-lh-pyrazol-3-yl-acetyl))-amino-3-desacetoxy-3-(l-methyl-lh-tetrazol-5-yl-thio)cepha 10-sporanic acid