FI62841C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 7-o-aminometyl- eller metylaminometylfenyl- eller cyklohexa dinyl- eller tienylacetamido)-3-(1-karboximetyl- (eller -et yl eller -propyl-)-tetrazol-5-yltiometyl)-3-cefem-4-karboxy lsror samt deras farmaceutiskt godtagbara salter - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 7-o-aminometyl- eller metylaminometylfenyl- eller cyklohexa dinyl- eller tienylacetamido)-3-(1-karboximetyl- (eller -et yl eller -propyl-)-tetrazol-5-yltiometyl)-3-cefem-4-karboxy lsror samt deras farmaceutiskt godtagbara salter Download PDFInfo
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- FI62841C FI62841C FI752434A FI752434A FI62841C FI 62841 C FI62841 C FI 62841C FI 752434 A FI752434 A FI 752434A FI 752434 A FI752434 A FI 752434A FI 62841 C FI62841 C FI 62841C
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- 241000277284 Salvelinus fontinalis Species 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 68
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- 238000000034 method Methods 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
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- 238000005917 acylation reaction Methods 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
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- FNOMIPYIAJRGIT-JKEGAWOSSA-N NCC1=C(CC(N[S+]2[C@H](CC3=O)N3C(C([O-])=O)=C(CSC3=NN=NN3CC(O)=O)C2)=O)C=CC=C1 Chemical compound NCC1=C(CC(N[S+]2[C@H](CC3=O)N3C(C([O-])=O)=C(CSC3=NN=NN3CC(O)=O)C2)=O)C=CC=C1 FNOMIPYIAJRGIT-JKEGAWOSSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 241000606856 Pasteurella multocida Species 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000588777 Providencia rettgeri Species 0.000 description 1
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- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
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- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 241000607598 Vibrio Species 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002942 anti-growth Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 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
- HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 description 1
- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 239000002245 particle Substances 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- JYXAWTDHRHNTNK-UHFFFAOYSA-M potassium;2-[2-[[(4-methoxy-4-oxobut-2-en-2-yl)amino]methyl]phenyl]acetate Chemical compound [K+].COC(=O)C=C(C)NCC1=CC=CC=C1CC([O-])=O JYXAWTDHRHNTNK-UHFFFAOYSA-M 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI802984A FI63565C (fi) | 1974-09-03 | 1980-09-22 | Saosom mellanprodukt vid framstaellning av 7-acylamido-3-(1-karboxi-laegre-alkyl-tetrazol-5-yltiometyl)-3-cefem-4-karbonsyror och deras salter och laett hydrolyserbara estrar anvaendbara foereningar |
| FI811452A FI63943C (fi) | 1974-09-03 | 1981-05-12 | Vid framstaellning av 7-acylamido-3-(1-karboxi-laegre-alkyl-tetrazol-5-yltiometyl)-3-cefem-4-karboxylsyror och deras salter saosom mellanprodukter anvaendbara foereningar |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50299174A | 1974-09-03 | 1974-09-03 | |
| US50299174 | 1974-09-03 | ||
| US59097175 | 1975-06-27 | ||
| US05/590,971 US4297489A (en) | 1974-09-03 | 1975-06-27 | 7-α-Amino-substituted acylamino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI752434A7 FI752434A7 (en, 2012) | 1976-03-04 |
| FI62841B FI62841B (fi) | 1982-11-30 |
| FI62841C true FI62841C (fi) | 1983-03-10 |
Family
ID=27054342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI752434A FI62841C (fi) | 1974-09-03 | 1975-08-29 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 7-o-aminometyl- eller metylaminometylfenyl- eller cyklohexa dinyl- eller tienylacetamido)-3-(1-karboximetyl- (eller -et yl eller -propyl-)-tetrazol-5-yltiometyl)-3-cefem-4-karboxy lsror samt deras farmaceutiskt godtagbara salter |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4297489A (en, 2012) |
| JP (1) | JPS6150956B2 (en, 2012) |
| AR (1) | AR222771A1 (en, 2012) |
| BG (1) | BG27091A3 (en, 2012) |
| CA (4) | CA1135255A (en, 2012) |
| CH (1) | CH636882A5 (en, 2012) |
| DD (2) | DD123471A5 (en, 2012) |
| DE (2) | DE2560655C2 (en, 2012) |
| DK (4) | DK145262C (en, 2012) |
| ES (2) | ES440707A1 (en, 2012) |
| FI (1) | FI62841C (en, 2012) |
| FR (1) | FR2283686A1 (en, 2012) |
| HU (1) | HU169490B (en, 2012) |
| IE (1) | IE43123B1 (en, 2012) |
| IL (1) | IL48020A (en, 2012) |
| LU (1) | LU73306A1 (en, 2012) |
| NL (1) | NL161758C (en, 2012) |
| NO (1) | NO152509C (en, 2012) |
| OA (1) | OA05096A (en, 2012) |
| SE (3) | SE431548B (en, 2012) |
| YU (5) | YU213275A (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4286089A (en) * | 1974-12-27 | 1981-08-25 | Smithkline Corporation | 7-Acyl-3-(substituted tetrazolyl thiomethyl)cephalosporins |
| US4101656A (en) * | 1976-07-12 | 1978-07-18 | Smithkline Corporation | 7β-Acylamino-3-(alkanesulfonamidoalkyl substituted tetrazolylthiomethyl) cephalosporins, antibacterial compositions containing them and methods of treating bacterial infections with them |
| US4278670A (en) * | 1976-07-12 | 1981-07-14 | Smithkline Corporation | 7-Alpha-oxyiminoacylcephalosporins |
| DE2724092A1 (de) * | 1977-05-27 | 1978-12-07 | Smithkline Corp | Cephalosporine, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| FR2387235A1 (fr) * | 1978-01-23 | 1978-11-10 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 3,7-disubstitue-3-cephem-4-carboxylique et nouveaux produits ainsi obtenus, ayant une forte activite antibacterienne |
| US4374994A (en) * | 1979-07-05 | 1983-02-22 | Bristol-Myers Company | Process for preparation of 5-mercaptotetrazolyl-1-acetic acid |
| US4243803A (en) * | 1979-07-05 | 1981-01-06 | Bristol-Myers Company | Production of 7-(2-aminomethylphenylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
| EP0095029B1 (en) * | 1979-11-30 | 1986-11-05 | Fujisawa Pharmaceutical Co., Ltd. | 5-thio-tetrazol compounds and their preparation |
| JPS56158791A (en) * | 1980-05-10 | 1981-12-07 | Taisho Pharmaceut Co Ltd | Cephalosporin compound |
| IL63767A0 (en) * | 1980-09-17 | 1981-12-31 | Lilly Co Eli | Cephalosporin compounds |
| JPS57188594A (en) * | 1981-05-15 | 1982-11-19 | Eisai Co Ltd | Preparation of 7-(2-amino-2-phenylacetamido)cephem derivative |
| US4448958A (en) * | 1982-10-20 | 1984-05-15 | Bristol-Myers Company | Purification of ceforanide |
| US4749522A (en) * | 1985-10-31 | 1988-06-07 | Angio-Medical Corporation | Supercritical fluid extraction of animal derived materials |
| DE3641822A1 (de) * | 1986-12-06 | 1988-06-16 | Goedecke Ag | Verwendung von dihydrophenylaminosaeurederivaten und diese enthaltende arzneimittel zur immunmodulation und cytostase |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819623A (en) * | 1968-04-12 | 1974-06-25 | Fujisawa Pharmaceutical Co | 3,7-disubstituted cephalosporin compounds |
| DE1953861C2 (de) * | 1969-10-25 | 1982-12-23 | Fujisawa Pharmaceutical Co., Ltd., Osaka | 7-Tetrazolylacetamido-3-thiomethyl-3-cephem-4- carbonsäuren |
| US3814755A (en) * | 1972-08-30 | 1974-06-04 | Bristol Myers Co | 7-(omikron-aminomethylphenylacetamido)-3-(tetrazolo(4,5-b)pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid |
| GB1478055A (en) | 1973-07-27 | 1977-06-29 | Erba Carlo Spa | Cephalosporin compounds |
| US4074929A (en) | 1973-08-29 | 1978-02-21 | Amp Incorporated | Cable card edge connector |
| NL7414119A (nl) * | 1973-10-31 | 1975-05-02 | Fujisawa Pharmaceutical Co | Werkwijze ter bereiding van 1h-tetrazool-5-thiol- derivaten en 1-gesubstitueerde 1h-tetrazool- -5-thiolen. |
| US4205166A (en) * | 1974-02-20 | 1980-05-27 | Fujisawa Pharmaceutical Co., Ltd. | 7-Substituted-3-aminoalkyl-, acylaminoalkyl-, or hydroxyalkyl-substituted heterocyclic thiomethyl-3-cephem-4-carboxylic acid derivatives and preparation thereof |
| US4092476A (en) * | 1974-02-21 | 1978-05-30 | Beecham Group Limited | Phthalidyl esters of 7-[(α amino, 2 substituted acetamido)-3-(heterocyclic-thio methyl)]cephalosporins |
| US4068074A (en) * | 1974-04-05 | 1978-01-10 | Yamanouchi Pharmaceutical Co., Ltd. | Cephalosporin derivatives having at the 3-position of the cephem ring a heterocyclic thiomethyl group with a carboxy or sulfo group and at the 7-position of the cephem ring an α-heterocylic acylaminophenyl-acetamide group |
| US4160086A (en) * | 1974-04-27 | 1979-07-03 | Beecham Group Limited | 3-Heterocyclicthio-7-α-carboxy 2-aryl acetamido cephalosporanic acid |
| JPS612674B2 (en, 2012) * | 1974-06-20 | 1986-01-27 | Meiji Seika Co | |
| US4172196A (en) * | 1974-09-03 | 1979-10-23 | Bristol-Myers Company | Certain 7-α-substituted-α-hydroxyacetamido-3-(1-carboxymethyltetrazol-5-yl-thiomethyl)-3-cephem-4-carboxylic acids |
| US4182863A (en) * | 1974-09-03 | 1980-01-08 | Bristol-Myers Company | 7-Amino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| US4286089A (en) * | 1974-12-27 | 1981-08-25 | Smithkline Corporation | 7-Acyl-3-(substituted tetrazolyl thiomethyl)cephalosporins |
| US4183925A (en) * | 1975-03-27 | 1980-01-15 | Pfizer Inc. | 7-Aminophenylacetamido-Δ3 -cephem antibacterial agents and method of use |
| JPS525787A (en) * | 1975-06-27 | 1977-01-17 | Bristol Myers Co | Antiibacterial agent |
| US4013648A (en) * | 1975-07-23 | 1977-03-22 | Bristol-Myers Company | Δ2,3 -0-2-Isocephem-4-carboxylic acid and derivatives as antibacterial agents |
| US4220644A (en) * | 1976-05-03 | 1980-09-02 | Smithkline Corporation | 7-Acylamino-3-(substituted tetrazolyl thiomethyl) cephalosporins |
| US4118563A (en) * | 1977-11-25 | 1978-10-03 | Bristol-Myers Company | Production of 7-(2-aminomethylphenylacetamido-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
-
1975
- 1975-06-27 US US05/590,971 patent/US4297489A/en not_active Expired - Lifetime
- 1975-08-21 YU YU02132/75A patent/YU213275A/xx unknown
- 1975-08-27 CA CA000234276A patent/CA1135255A/en not_active Expired
- 1975-08-29 FI FI752434A patent/FI62841C/fi not_active IP Right Cessation
- 1975-08-29 DK DK391075A patent/DK145262C/da not_active IP Right Cessation
- 1975-09-01 DE DE2560655A patent/DE2560655C2/de not_active Expired
- 1975-09-01 BG BG030902A patent/BG27091A3/xx unknown
- 1975-09-01 IL IL48020A patent/IL48020A/xx unknown
- 1975-09-01 SE SE7509702A patent/SE431548B/xx not_active IP Right Cessation
- 1975-09-01 NO NO752983A patent/NO152509C/no unknown
- 1975-09-01 DE DE2538804A patent/DE2538804C2/de not_active Expired
- 1975-09-02 LU LU73306A patent/LU73306A1/xx unknown
- 1975-09-02 FR FR7526936A patent/FR2283686A1/fr active Granted
- 1975-09-02 HU HUBI521A patent/HU169490B/hu unknown
- 1975-09-02 OA OA55597A patent/OA05096A/xx unknown
- 1975-09-03 ES ES440707A patent/ES440707A1/es not_active Expired
- 1975-09-03 IE IE1916/75A patent/IE43123B1/en unknown
- 1975-09-03 NL NL7510391.A patent/NL161758C/xx active
- 1975-09-03 JP JP50106106A patent/JPS6150956B2/ja not_active Expired
- 1975-09-03 AR AR260237A patent/AR222771A1/es active
- 1975-09-03 DD DD188166A patent/DD123471A5/xx unknown
- 1975-09-03 DD DD7500196946A patent/DD130787A5/xx unknown
-
1977
- 1977-04-20 ES ES457998A patent/ES457998A1/es not_active Expired
-
1979
- 1979-08-31 DK DK367279A patent/DK147483C/da active
- 1979-09-14 SE SE7907672A patent/SE435279B/sv not_active IP Right Cessation
-
1980
- 1980-12-02 CH CH890980A patent/CH636882A5/de not_active IP Right Cessation
-
1981
- 1981-03-12 CA CA372,810A patent/CA1123840A/en not_active Expired
- 1981-03-12 CA CA000372811A patent/CA1135254A/en not_active Expired
- 1981-08-24 CA CA000384513A patent/CA1135256A/en not_active Expired
- 1981-09-16 YU YU2231/81A patent/YU44964B/xx unknown
- 1981-09-16 YU YU02230/81A patent/YU223081A/xx unknown
- 1981-09-16 YU YU2232/81A patent/YU44669B/xx unknown
- 1981-09-16 YU YU2233/81A patent/YU44833B/xx unknown
-
1982
- 1982-05-27 DK DK240582A patent/DK148796C/da not_active IP Right Cessation
-
1983
- 1983-09-16 DK DK423383A patent/DK162388C/da active
- 1983-10-07 SE SE8305539A patent/SE453507B/sv not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
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| MA | Patent expired | ||
| MA | Patent expired |
Owner name: BRISTOL-MYERS CO |