CS199676B2 - Method of producing derivatives of 7-acylamino-pyrazinylthiomethyl-3-cephem-4-carboxylic acid - Google Patents

Method of producing derivatives of 7-acylamino-pyrazinylthiomethyl-3-cephem-4-carboxylic acid Download PDF

Info

Publication number: CS199676B2
Authority: CS; Czechoslovakia
Prior art keywords: cephem; alkyl; pyrazinylthiomethyl; carboxylic acid; image
Prior art date: 1976-05-21

Application number

CS773205A

Other languages

Czech (cs)

English (en)

Inventor

Giorgio Palamidossi

Franco Zarini

Giovanni Franceschi

Giovanna Schioppacassi

Federico Arcamone

Original Assignee

Farmaceutici Italia

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.)

1976-05-21

Filing date

1977-05-16

Publication date

1980-07-31

1977-05-16 Application filed by Farmaceutici Italia filed Critical Farmaceutici Italia

1980-07-31 Publication of CS199676B2 publication Critical patent/CS199676B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 10
-1 1,4-cyclohexadienyl Chemical group 0.000 claims abstract description 21
125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
HKAVADYDPYUPRD-UHFFFAOYSA-N 1h-pyrazine-2-thione Chemical compound SC1=CN=CC=N1 HKAVADYDPYUPRD-UHFFFAOYSA-N 0.000 claims description 10
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 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 abstract description 12
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 abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
229910052708 sodium Inorganic materials 0.000 abstract description 4
239000011734 sodium Substances 0.000 abstract description 4
229910052717 sulfur Inorganic materials 0.000 abstract description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 2
229910052760 oxygen Inorganic materials 0.000 abstract description 2
229910052700 potassium Inorganic materials 0.000 abstract description 2
239000011591 potassium Substances 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract 6
125000004432 carbon atom Chemical group C* 0.000 abstract 4
239000000460 chlorine Substances 0.000 abstract 4
125000003545 alkoxy group Chemical group 0.000 abstract 2
229910052794 bromium Inorganic materials 0.000 abstract 2
229910052801 chlorine Inorganic materials 0.000 abstract 2
239000001257 hydrogen Substances 0.000 abstract 2
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
125000001544 thienyl group Chemical group 0.000 abstract 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
229910052783 alkali metal Inorganic materials 0.000 abstract 1
150000001340 alkali metals Chemical group 0.000 abstract 1
229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
150000001342 alkaline earth metals Chemical class 0.000 abstract 1
125000003282 alkyl amino group Chemical group 0.000 abstract 1
125000004414 alkyl thio group Chemical group 0.000 abstract 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
125000005518 carboxamido group Chemical group 0.000 abstract 1
125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract 1
229910052731 fluorine Inorganic materials 0.000 abstract 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
125000006000 trichloroethyl group Chemical group 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
239000002253 acid Substances 0.000 description 19
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 16
150000001875 compounds Chemical class 0.000 description 16
229910052799 carbon Inorganic materials 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 9
150000004702 methyl esters Chemical class 0.000 description 9
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000000047 product Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
241000699670 Mus sp. Species 0.000 description 7
XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 6
229960001139 cefazolin Drugs 0.000 description 6
150000001780 cephalosporins Chemical class 0.000 description 6
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
229930186147 Cephalosporin Natural products 0.000 description 5
229960000603 cefalotin Drugs 0.000 description 5
229940124587 cephalosporin Drugs 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
229930192474 thiophene Natural products 0.000 description 4
241000894006 Bacteria Species 0.000 description 3
241000607142 Salmonella Species 0.000 description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007858 starting material Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000010534 nucleophilic substitution reaction Methods 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
HTHRNPWONOKUQU-JFUPDXTOSA-N (6R)-4-acetamido-3-[(6-methoxypyrazin-2-yl)sulfanylmethyl]-8-oxo-7-thiophen-2-yl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(=CC=C1)C1[C@@H]2N(C(=C(C(S2)NC(C)=O)CSC2=NC(=CN=C2)OC)C(=O)O)C1=O HTHRNPWONOKUQU-JFUPDXTOSA-N 0.000 description 1
SFFNPNOKEYHRGN-SNVBAGLBSA-N (6R)-8-oxo-3-(pyrazin-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N1=C(C=NC=C1)SCC=1CS[C@H]2N(C1C(=O)O)C(C2)=O SFFNPNOKEYHRGN-SNVBAGLBSA-N 0.000 description 1
NYNCOSPESPZROP-QHDYGNBISA-N (6r)-7-amino-8-oxo-3-(pyrazin-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC1=CN=CC=N1 NYNCOSPESPZROP-QHDYGNBISA-N 0.000 description 1
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 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
241000156724 Antirhea Species 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
125000006414 CCl Chemical group ClC* 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
VEXZGXHMUGYJMC-DYCDLGHISA-N Deuterium chloride Chemical compound [2H]Cl VEXZGXHMUGYJMC-DYCDLGHISA-N 0.000 description 1
241001522878 Escherichia coli B Species 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
241000219470 Mirabilis Species 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
235000014676 Phragmites communis Nutrition 0.000 description 1
241000295644 Staphylococcaceae Species 0.000 description 1
206010041925 Staphylococcal infections Diseases 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003573 thiols 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

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

CS773205A 1976-05-21 1977-05-16 Method of producing derivatives of 7-acylamino-pyrazinylthiomethyl-3-cephem-4-carboxylic acid CS199676B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB21032/76A GB1579532A (en)	1976-05-21	1976-05-21	Cephalosporins

Publications (1)

Publication Number	Publication Date
CS199676B2 true CS199676B2 (en)	1980-07-31

Family

ID=10156029

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS773205A CS199676B2 (en)	1976-05-21	1977-05-16	Method of producing derivatives of 7-acylamino-pyrazinylthiomethyl-3-cephem-4-carboxylic acid

Country Status (22)

Country	Link
US (1)	US4148996A (de)
JP (1)	JPS52142093A (de)
AT (1)	AT355719B (de)
AU (1)	AU509448B2 (de)
BE (1)	BE854845A (de)
CA (1)	CA1102790A (de)
CH (1)	CH639095A5 (de)
CS (1)	CS199676B2 (de)
DE (1)	DE2722666C2 (de)
DK (1)	DK216877A (de)
FR (1)	FR2424922A1 (de)
GB (1)	GB1579532A (de)
GR (1)	GR73013B (de)
HU (1)	HU174072B (de)
IL (1)	IL52123A (de)
NL (1)	NL7705262A (de)
NO (1)	NO771744L (de)
NZ (1)	NZ184110A (de)
SE (1)	SE433851B (de)
SU (1)	SU799669A3 (de)
YU (1)	YU123077A (de)
ZA (1)	ZA772859B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10533018B2 (en)	2015-06-29	2020-01-14	Duke University	Antimicrobial prochelators to target drug-resistant bacteria and methods of making and using the same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL38099A (en) *	1970-12-17	1976-01-30	Smith Kline French Lab	3-heterocyclyl thiomethylcephalosporins
US4007173A (en) *	1973-05-07	1977-02-08	Smithkline Corporation	α-amino-α-(ureidophenyl)acetamidocephalosporins
DE2359544A1 (de) *	1973-11-29	1975-10-30	Hoechst Ag	Cephemderivate und verfahren zu ihrer herstellung
US3960849A (en) *	1974-03-13	1976-06-01	E. R. Squibb & Sons, Inc.	Amino-1,2,4-oxadiazolyl-3-acetyl cephalosporins
DE2512284A1 (de) *	1974-03-28	1975-10-09	Fujisawa Pharmaceutical Co	Cephalosporansaeurederivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel

1976
- 1976-05-21 GB GB21032/76A patent/GB1579532A/en not_active Expired
1977
- 1977-05-11 AU AU25071/77A patent/AU509448B2/en not_active Expired
- 1977-05-12 NL NL7705262A patent/NL7705262A/xx not_active Application Discontinuation
- 1977-05-13 ZA ZA00772859A patent/ZA772859B/xx unknown
- 1977-05-16 CS CS773205A patent/CS199676B2/cs unknown
- 1977-05-16 US US05/797,606 patent/US4148996A/en not_active Expired - Lifetime
- 1977-05-16 NZ NZ184110A patent/NZ184110A/xx unknown
- 1977-05-16 AT AT348977A patent/AT355719B/de not_active IP Right Cessation
- 1977-05-17 YU YU01230/77A patent/YU123077A/xx unknown
- 1977-05-17 FR FR7715045A patent/FR2424922A1/fr active Granted
- 1977-05-18 SE SE7705934A patent/SE433851B/xx unknown
- 1977-05-18 NO NO771744A patent/NO771744L/no unknown
- 1977-05-18 DE DE2722666A patent/DE2722666C2/de not_active Expired
- 1977-05-18 DK DK216877A patent/DK216877A/da unknown
- 1977-05-19 IL IL52123A patent/IL52123A/xx unknown
- 1977-05-20 CH CH625577A patent/CH639095A5/de not_active IP Right Cessation
- 1977-05-20 HU HU77SO1190A patent/HU174072B/hu unknown
- 1977-05-20 SU SU772483403A patent/SU799669A3/ru active
- 1977-05-20 JP JP5862277A patent/JPS52142093A/ja active Pending
- 1977-05-20 CA CA278,851A patent/CA1102790A/en not_active Expired
- 1977-05-20 GR GR53525A patent/GR73013B/el unknown
- 1977-05-20 BE BE177745A patent/BE854845A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH639095A5 (de)	1983-10-31
JPS52142093A (en)	1977-11-26
BE854845A (fr)	1977-11-21
AT355719B (de)	1980-03-25
SE433851B (sv)	1984-06-18
DK216877A (da)	1977-11-22
GR73013B (de)	1984-01-25
GB1579532A (en)	1980-11-19
IL52123A (en)	1980-11-30
AU509448B2 (en)	1980-05-15
DE2722666C2 (de)	1982-04-15
YU123077A (en)	1982-10-31
AU2507177A (en)	1978-11-16
NL7705262A (nl)	1977-11-23
ATA348977A (de)	1979-08-15
FR2424922B1 (de)	1983-07-08
NO771744L (no)	1977-11-22
IL52123A0 (en)	1977-07-31
FR2424922A1 (fr)	1979-11-30
CA1102790A (en)	1981-06-09
HU174072B (hu)	1979-10-28
US4148996A (en)	1979-04-10
ZA772859B (en)	1978-04-26
SE7705934L (sv)	1977-11-22
DE2722666A1 (de)	1977-12-01
NZ184110A (en)	1979-08-31
SU799669A3 (ru)	1981-01-23

Publication	Publication Date	Title
FI56686C (fi)	1980-03-10	Foerfarande foer framstaellning av 7-aminocefalosporansyraderivat med antibiotisk verkan
GB2071654A (en)	1981-09-23	Hydroxamic acid derivatives of 7-(2-amino-4-thiazolyl)oximino cephalosporins
US4104469A (en)	1978-08-01	7-(Syn-α-alkoxy-iminofuryl)acetamido-3-(2-methyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
US4456755A (en)	1984-06-26	7-Oxygen analogs of cephalosporins
HU176287B (en)	1981-01-28	Process for producing 7-bracket-2-thienylacetamido-bracket closed-3-triasolylthiomethyl-3-cepheme-4-carboxylic acid derivative
US4604387A (en)	1986-08-05	1,2,4-triazinylthiomethyl-3-cephem sulfoxides, and a procedure for their preparation
US4145540A (en)	1979-03-20	7β-Phosphoramido-7α-methoxycephalosporanic acid derivatives
US4103085A (en)	1978-07-25	7-(Syn-α-alkoxy-iminofurylacetamido-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
US3956287A (en)	1976-05-11	7-[(2-Oxo-1-pyridinyl)acylamino]cephalosporin derivatives
CS199676B2 (en)	1980-07-31	Method of producing derivatives of 7-acylamino-pyrazinylthiomethyl-3-cephem-4-carboxylic acid
US4138554A (en)	1979-02-06	7-[D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-α-phenyl (and p-hydroxyphenyl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acids
US4210750A (en)	1980-07-01	Process for the preparation of 3-carbamoyl cephalosporins using isocyanates
US4005081A (en)	1977-01-25	3-Heterothiomethyl-7α-methoxy-7β-tetrazolylmethylthioacetamido-3-cephem derivatives
US3991051A (en)	1976-11-09	[(Oxyalkyl)thioacetyl]cephalosporin derivatives
US3971780A (en)	1976-07-27	Thio-β-lactam cephalosporins
US4178444A (en)	1979-12-11	Hydrazono derivatives of cephalosporins
US4179502A (en)	1979-12-18	7[2-Hydroxyiminoacetamido]cephalosporins
US4124762A (en)	1978-11-07	7-[(Pyridylthiomethyl)phenyl]acetamido-cephalosporin derivatives
US3928335A (en)	1975-12-23	{8 {8 (Alkylthioc arbonyl)oxy{9 acetyl{9 cephalosporins
US3993758A (en)	1976-11-23	Cephalosporin compounds
US4497811A (en)	1985-02-05	1-Oxadethiacephalosporin compound and antibacterial agent containing the _same
US3929778A (en)	1975-12-30	{8 (Acylcarbamoyl) thioacetyl{9 {0 cephalosporin derivatives
US3880845A (en)	1975-04-29	Thiocarbonylthioacetyl cephalosporins
US3879381A (en)	1975-04-22	7-(2-Carbamoy L-1-oxaspiro(2,x)alkane-carboxamido) penicillanic acids
US4124761A (en)	1978-11-07	7-[(substituted-thiomethyl)phenyl] acetamidocephalosporin derivatives