SE452621B - 7-amino cefalosporinderivat till anvendning som mellanprodukt for framstellning av motsvarande 7-substituerade cefalosporinderivat - Google Patents

7-amino cefalosporinderivat till anvendning som mellanprodukt for framstellning av motsvarande 7-substituerade cefalosporinderivat

Info

Publication number: SE452621B
Authority: SE; Sweden
Prior art keywords: formula; acid; carboxylic acid; amino; cephem
Prior art date: 1975-10-30

Application number

SE8006413A

Other languages

English (en)

Swedish (sv)

Other versions

SE8006413L (sv

Inventor

D A Berges

Original Assignee

Smithkline Beckman Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-10-30

Filing date

1976-09-28

Publication date

1987-12-07

1976-07-12 Priority claimed from US05/704,142 external-priority patent/US4118491A/en

1976-09-28 Application filed by Smithkline Beckman Corp filed Critical Smithkline Beckman Corp

1980-09-12 Publication of SE8006413L publication Critical patent/SE8006413L/sv

1987-12-07 Publication of SE452621B publication Critical patent/SE452621B/sv

Links

239000013067 intermediate product Substances 0.000 title claims 2
HOKIDJSKDBPKTQ-UHFFFAOYSA-N 3-(acetyloxymethyl)-7-[(5-amino-5-carboxypentanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 HOKIDJSKDBPKTQ-UHFFFAOYSA-N 0.000 title 2
-1 dihydrophenyl Chemical group 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 8
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000003831 tetrazolyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
NVRSPIKUPKOSIY-UHFFFAOYSA-N chembl1743348 Chemical group CC=1N=NOC=1O NVRSPIKUPKOSIY-UHFFFAOYSA-N 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
125000004185 ester group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 10
239000000243 solution Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
238000001914 filtration Methods 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
238000000034 method Methods 0.000 description 5
239000002585 base Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229930186147 Cephalosporin Natural products 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229940124587 cephalosporin Drugs 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000003456 ion exchange resin Substances 0.000 description 3
229920003303 ion-exchange polymer Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
239000012990 dithiocarbamate Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011734 sodium Substances 0.000 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 description 2
PUWQVDWJJCSTLK-SSDOTTSWSA-N (2R)-2-hydroxy-2-phenylacetyl chloride Chemical compound C([C@H](O)C1=CC=CC=C1)(=O)Cl PUWQVDWJJCSTLK-SSDOTTSWSA-N 0.000 description 1
HPVYMSBZIOPTKS-UHFFFAOYSA-N 1,2-dihydrotetrazole-5-thione;sodium Chemical compound [Na].[Na].S=C1N=NNN1 HPVYMSBZIOPTKS-UHFFFAOYSA-N 0.000 description 1
JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical compound SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 description 1
FIULQBJUTSDMEI-UHFFFAOYSA-N 2-(2,2,2-trifluoroethylsulfonyl)acetic acid Chemical compound OC(=O)CS(=O)(=O)CC(F)(F)F FIULQBJUTSDMEI-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000894006 Bacteria Species 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
241000588724 Escherichia coli Species 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
241000588772 Morganella morganii Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
QOTUIXXPANLHGV-UHFFFAOYSA-N N.[N-]=[N+]=[N-].[Na+] Chemical compound N.[N-]=[N+]=[N-].[Na+] QOTUIXXPANLHGV-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
PCWJEAMXBQHWEA-UHFFFAOYSA-N methyl n-(2-acetamidoethyl)carbamodithioate Chemical compound CSC(=S)NCCNC(C)=O PCWJEAMXBQHWEA-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical compound CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
IDOICNVNTGFRHG-UHFFFAOYSA-N n-[2-(5-sulfanylidene-2h-tetrazol-1-yl)ethyl]acetamide Chemical compound CC(=O)NCCN1N=NN=C1S IDOICNVNTGFRHG-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- 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
- 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
- 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

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)
Plural Heterocyclic Compounds (AREA)

SE8006413A 1975-10-30 1976-09-28 7-amino cefalosporinderivat till anvendning som mellanprodukt for framstellning av motsvarande 7-substituerade cefalosporinderivat SE452621B (sv)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US62716475A	1975-10-30	1975-10-30
US66583776A	1976-03-11	1976-03-11
US05/704,142 US4118491A (en)	1976-03-11	1976-07-12	7-Acyl-3-(sulfaminoalkyl substituted tetrazolylthiomethyl)cephalosporins, antibacterial compositions containing them and methods of treating bacterial infections with them

Publications (2)

Publication Number	Publication Date
SE8006413L SE8006413L (sv)	1980-09-12
SE452621B true SE452621B (sv)	1987-12-07

Family

ID=27417417

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
SE7610722A SE435291B (sv)	1975-10-30	1976-09-28	Forfarande for framstellning av 7-acylamino-3(1-(2-sulfaminoetyl)-tetrazol-5-yltiometyl)-3-cefem-4-karbonsyra
SE8006413A SE452621B (sv)	1975-10-30	1976-09-28	7-amino cefalosporinderivat till anvendning som mellanprodukt for framstellning av motsvarande 7-substituerade cefalosporinderivat
SE8006414A SE437025B (sv)	1975-10-30	1980-09-12	1-(2-sulfaminoetyl)-tetrazol-5-tiol till anvendning for framstellning av cefalosporinforeningar med antibakteriell aktivitet

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
SE7610722A SE435291B (sv)	1975-10-30	1976-09-28	Forfarande for framstellning av 7-acylamino-3(1-(2-sulfaminoetyl)-tetrazol-5-yltiometyl)-3-cefem-4-karbonsyra

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SE8006414A SE437025B (sv)	1975-10-30	1980-09-12	1-(2-sulfaminoetyl)-tetrazol-5-tiol till anvendning for framstellning av cefalosporinforeningar med antibakteriell aktivitet

Country Status (17)

Country	Link
JP (1)	JPS6053026B2 (fr)
AT (1)	AT353957B (fr)
AU (1)	AU505141B2 (fr)
CA (1)	CA1071188A (fr)
CH (1)	CH627757A5 (fr)
DE (1)	DE2649545A1 (fr)
DK (1)	DK463176A (fr)
ES (1)	ES452769A1 (fr)
FI (1)	FI60868C (fr)
FR (3)	FR2361896A1 (fr)
GB (3)	GB1570094A (fr)
GR (1)	GR61667B (fr)
IE (1)	IE44393B1 (fr)
IL (3)	IL50546A (fr)
LU (1)	LU76092A1 (fr)
NL (1)	NL7612010A (fr)
SE (3)	SE435291B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4117123A (en) *	1977-06-09	1978-09-26	Smithkline Corporation	7-Acylamino-3-[1-(2-sulfamidoethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acids
AT383811B (de) *	1983-09-22	1987-08-25	Biochemie Gmbh	Verfahren zur herstellung von monoalkalisalzen von 7-amino-3-cephem-4-carbonsaeurederivaten
US4717531A (en) *	1983-09-23	1988-01-05	Westinghouse Electric Corp.	Fuel transfer system upender using translation drive

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR207752A1 (es) *	1973-03-30	1976-10-29	Fujisawa Pharmaceutical Co	Procedimiento para obtener acidos 7-amino-sustituido-3-tiometilsustituido-3-cefem-4-carboxilicos
US4110338A (en) *	1973-10-31	1978-08-29	Fujisawa Pharmaceutical Co., Ltd.	Product and preparation of 1H-tetrazole-5-thiol derivatives
GB1449420A (en) *	1973-11-26	1976-09-15	Sankyo Co	7alpha-methoxycephalosporing derivatives
NZ176206A (en) *	1973-12-25	1978-03-06	Takeda Chemical Industries Ltd	Cephalosporins
US4066762A (en) *	1976-07-12	1978-01-03	Smithkline Corporation	Derivatives of 7-(2-substituted-2-hydroxyiminoacetamido)-3-(1-substituted tetrazol-5-ylthiomethyl-3-cephem-4-carboxylic acid

1976
- 1976-09-23 IL IL50546A patent/IL50546A/xx unknown
- 1976-09-28 SE SE7610722A patent/SE435291B/xx not_active IP Right Cessation
- 1976-09-28 SE SE8006413A patent/SE452621B/sv not_active IP Right Cessation
- 1976-09-30 CA CA262,347A patent/CA1071188A/fr not_active Expired
- 1976-10-14 AU AU18702/76A patent/AU505141B2/en not_active Ceased
- 1976-10-14 DK DK463176A patent/DK463176A/da not_active Application Discontinuation
- 1976-10-21 FR FR7631723A patent/FR2361896A1/fr active Granted
- 1976-10-26 GB GB19786/79A patent/GB1570094A/en not_active Expired
- 1976-10-26 GB GB19863/79A patent/GB1570095A/en not_active Expired
- 1976-10-26 FI FI763044A patent/FI60868C/fi not_active IP Right Cessation
- 1976-10-26 GB GB44441/76A patent/GB1570093A/en not_active Expired
- 1976-10-27 IE IE2377/76A patent/IE44393B1/en unknown
- 1976-10-27 ES ES452769A patent/ES452769A1/es not_active Expired
- 1976-10-28 LU LU76092A patent/LU76092A1/xx unknown
- 1976-10-29 JP JP51131157A patent/JPS6053026B2/ja not_active Expired
- 1976-10-29 DE DE19762649545 patent/DE2649545A1/de not_active Ceased
- 1976-10-29 GR GR52030A patent/GR61667B/el unknown
- 1976-10-29 NL NL7612010A patent/NL7612010A/xx not_active Application Discontinuation
- 1976-10-29 CH CH1369576A patent/CH627757A5/de not_active IP Right Cessation
- 1976-10-29 AT AT807276A patent/AT353957B/de not_active IP Right Cessation
1977
- 1977-03-22 FR FR7708504A patent/FR2351982A1/fr active Granted
- 1977-03-22 FR FR7708505A patent/FR2337720A1/fr active Granted
1979
- 1979-02-28 IL IL56757A patent/IL56757A0/xx unknown
- 1979-02-28 IL IL56758A patent/IL56758A0/xx unknown
1980
- 1980-09-12 SE SE8006414A patent/SE437025B/sv not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK463176A (da)	1977-05-01
NL7612010A (nl)	1977-05-03
SE8006413L (sv)	1980-09-12
SE437025B (sv)	1985-02-04
FR2361896B1 (fr)	1979-02-23
IL50546A (en)	1980-07-31
IE44393B1 (en)	1981-11-18
CH627757A5 (en)	1982-01-29
IL50546A0 (en)	1976-11-30
FR2337720A1 (fr)	1977-08-05
FR2361896A1 (fr)	1978-03-17
CA1071188A (fr)	1980-02-05
JPS6053026B2 (ja)	1985-11-22
AT353957B (de)	1979-12-10
DE2649545A1 (de)	1977-05-12
FI763044A7 (fr)	1977-05-01
ATA807276A (de)	1979-05-15
JPS5257191A (en)	1977-05-11
GB1570093A (en)	1980-06-25
LU76092A1 (fr)	1977-05-17
GB1570095A (en)	1980-06-25
FI60868C (fi)	1982-04-13
SE435291B (sv)	1984-09-17
GB1570094A (en)	1980-06-25
SE8006414L (sv)	1980-09-12
ES452769A1 (es)	1978-01-16
FI60868B (fi)	1981-12-31
SE7610722L (sv)	1977-05-01
AU505141B2 (en)	1979-11-08
GR61667B (en)	1978-12-05
FR2337720B1 (fr)	1981-07-10
AU1870276A (en)	1978-04-20
FR2351982A1 (fr)	1977-12-16
IL56758A0 (en)	1979-05-31
IL56757A0 (en)	1979-05-31
FR2351982B1 (fr)	1981-07-03
IE44393L (en)	1977-09-11

Publication	Publication Date	Title
JPS6150955B2 (fr)	1986-11-06
CH622262A5 (fr)	1981-03-31
US4066762A (en)	1978-01-03	Derivatives of 7-(2-substituted-2-hydroxyiminoacetamido)-3-(1-substituted tetrazol-5-ylthiomethyl-3-cephem-4-carboxylic acid
US4068073A (en)	1978-01-10	7-Amino intermediates for preparing 7-acyl-3-(ureidoalkyl substituted tetrazolylthiomethyl)-cephalosporins
JPS6153359B2 (fr)	1986-11-17
US4220644A (en)	1980-09-02	7-Acylamino-3-(substituted tetrazolyl thiomethyl) cephalosporins
SE452621B (sv)	1987-12-07	7-amino cefalosporinderivat till anvendning som mellanprodukt for framstellning av motsvarande 7-substituerade cefalosporinderivat
US4018921A (en)	1977-04-19	Substituted phenylglycylcephalosporins
US4101656A (en)	1978-07-18	7β-Acylamino-3-(alkanesulfonamidoalkyl substituted tetrazolylthiomethyl) cephalosporins, antibacterial compositions containing them and methods of treating bacterial infections with them
US4138556A (en)	1979-02-06	7-Amino-3-(sulfoalkyl substituted oxadiazolylthiomethyl) cephalosporins
EP0000272B1 (fr)	1982-05-05	Acides 7-acylamino-3-substitués-3-cephem-4-carboxyliques, procédé pour leur préparation, compositions pharmaceutiques les contenant
EP0000100B1 (fr)	1982-02-03	Acides 7-acylamino-3-(1-(2-sulfamylaminoéthyl)-tétrazole-5-ylthiométhyl)-3-céphem-4-carboxyliques, un procédé pour leur préparation et leurs compositions pharmaceutiques
US3953439A (en)	1976-04-27	Substituted phenylglycylcephalosporins
US4126682A (en)	1978-11-21	7-acyl-3-(carboxyalkyl and carbamoylalkyl substituted oxadiazolylthiomethyl) cephalosporins and antibacterial compositions and methods employing them
US4064242A (en)	1977-12-20	7-Acylamino-3-[1-(2,3-dihydroxypropyl)tetrazole-5-ylthiomethyl]-3-cephem-4-carboxylic acids
CA1104560A (fr)	1981-07-07	Traduction non-disponible
EP0000285B1 (fr)	1982-02-17	Dérivés des acides 7-acylamino-3-((3-(carboxyméthyl-) thio-1 H-1,2,4-triazol-5-yl) thiométhyl)-3-céphem-4 carboxyliques, procédés pour leur préparation et leurs compositions
US4144241A (en)	1979-03-13	5-Sulfomethyl-1,3,4-thiadiazole-2-thiol
US4111981A (en)	1978-09-05	Intermediates for preparing substituted phenylglycylcephalosporins
US4174323A (en)	1979-11-13	1-(2-Sulfamidoethyl)-1,4-dihydro-5H-tetrazole-5-thione
IE45758B1 (en)	1982-11-17	7- -oxyiminoacylaminocephalosporins
US4171362A (en)	1979-10-16	7-Acylamino-3-(sulfaminoalkyl substituted tetrazolylthiomethyl)cephalosporins antibacterial compositions containing them and methods of treating bacterial infections with them
US4118491A (en)	1978-10-03	7-Acyl-3-(sulfaminoalkyl substituted tetrazolylthiomethyl)cephalosporins, antibacterial compositions containing them and methods of treating bacterial infections with them
US4044047A (en)	1977-08-23	Intermediates for preparing substituted phenylglycylcephalosporins
US4013764A (en)	1977-03-22	Pharmaceutical compositions comprising substituted phenylglycylcephalosporins and methods of treating bacterial infections

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