FI57111C - Foerfarande foer framstaellning av antibakteriella 7-(o-aminometylfenylacetamido- och -propionamido)-3-(tetrazolo(4,5-b)pyridazin-6-yltiometyl)-3-cefem-4-karboxylsyror - Google Patents
Foerfarande foer framstaellning av antibakteriella 7-(o-aminometylfenylacetamido- och -propionamido)-3-(tetrazolo(4,5-b)pyridazin-6-yltiometyl)-3-cefem-4-karboxylsyror Download PDFInfo
- Publication number
- FI57111C FI57111C FI2670/73A FI267073A FI57111C FI 57111 C FI57111 C FI 57111C FI 2670/73 A FI2670/73 A FI 2670/73A FI 267073 A FI267073 A FI 267073A FI 57111 C FI57111 C FI 57111C
- Authority
- FI
- Finland
- Prior art keywords
- sodium
- ylthiomethyl
- cephem
- tetrazolo
- pyridazin
- Prior art date
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- -1 PYRIDAZIN-6-YLTHIOMETHYL Chemical class 0.000 title claims description 100
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 12
- 231100000252 nontoxic Toxicity 0.000 claims description 10
- 230000003000 nontoxic effect Effects 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- 239000000243 solution Substances 0.000 description 66
- 239000000047 product Substances 0.000 description 43
- 239000011734 sodium Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 37
- 229910052708 sodium Inorganic materials 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 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 27
- 235000019441 ethanol Nutrition 0.000 description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 20
- 238000001914 filtration Methods 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
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- 239000002244 precipitate Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000003242 anti bacterial agent Substances 0.000 description 9
- 229940088710 antibiotic agent Drugs 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
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- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical class CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 7
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 7
- 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 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 6
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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- 239000005909 Kieselgur Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical class O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 5
- 229960003866 cefaloridine Drugs 0.000 description 5
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- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
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- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CGPQRFCFBISLKF-UHFFFAOYSA-N 2-[2-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]acetic acid Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC=C1CC(O)=O CGPQRFCFBISLKF-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 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 4
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- 125000001424 substituent group Chemical group 0.000 description 4
- TYUABEAJISXFLD-YLJYHZDGSA-N (6r,7r)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-8-oxo-3-(tetrazolo[1,5-b]pyridazin-6-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NCC1=CC=CC=C1CC(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC3=NN4N=NN=C4C=C3)CS[C@@H]21 TYUABEAJISXFLD-YLJYHZDGSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
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- 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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI792534A FI60211C (fi) | 1972-08-30 | 1979-08-15 | 7-amino-3-(tetrazolo(4,5-b)pyridazin-6-yltiometyl)-3-cefem-4-karboxylsyra till anvaendning saosom mellanprodukt vid framstaellning av antibakteriella 3-tiolerade 7-acylaminocefalosporansyraderivat |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00284792A US3814755A (en) | 1972-08-30 | 1972-08-30 | 7-(omikron-aminomethylphenylacetamido)-3-(tetrazolo(4,5-b)pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid |
| US28479272 | 1972-08-30 | ||
| US28679372 | 1972-09-06 | ||
| US00286793A US3813391A (en) | 1972-09-06 | 1972-09-06 | 7-(beta-(o-aminomethylphenyl)propion-amido)-3-(tetrazolo(4,5-b)pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI57111B FI57111B (fi) | 1980-02-29 |
| FI57111C true FI57111C (fi) | 1980-06-10 |
Family
ID=26962815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2670/73A FI57111C (fi) | 1972-08-30 | 1973-08-27 | Foerfarande foer framstaellning av antibakteriella 7-(o-aminometylfenylacetamido- och -propionamido)-3-(tetrazolo(4,5-b)pyridazin-6-yltiometyl)-3-cefem-4-karboxylsyror |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5727116B2 (en, 2012) |
| DE (1) | DE2343827A1 (en, 2012) |
| FI (1) | FI57111C (en, 2012) |
| FR (1) | FR2197575B1 (en, 2012) |
| GB (1) | GB1406204A (en, 2012) |
| NL (1) | NL7311757A (en, 2012) |
| SE (1) | SE415979B (en, 2012) |
| YU (1) | YU39712B (en, 2012) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3382241A (en) * | 1967-02-27 | 1968-05-07 | Lilly Co Eli | Certain orally active cephalosporin antibiotics |
| IE36346B1 (en) * | 1971-05-11 | 1976-10-13 | R & L Molecular Research Ltd | Antibacterial agents and a process for the preparation thereof |
-
1973
- 1973-08-27 NL NL7311757A patent/NL7311757A/xx not_active Application Discontinuation
- 1973-08-27 FI FI2670/73A patent/FI57111C/fi active
- 1973-08-28 SE SE7311702A patent/SE415979B/xx unknown
- 1973-08-29 JP JP9624173A patent/JPS5727116B2/ja not_active Expired
- 1973-08-29 GB GB4074073A patent/GB1406204A/en not_active Expired
- 1973-08-30 DE DE19732343827 patent/DE2343827A1/de not_active Ceased
- 1973-08-30 FR FR7331463A patent/FR2197575B1/fr not_active Expired
- 1973-09-05 YU YU2361/73A patent/YU39712B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE415979B (sv) | 1980-11-17 |
| FR2197575A1 (en, 2012) | 1974-03-29 |
| FI57111B (fi) | 1980-02-29 |
| JPS5727116B2 (en, 2012) | 1982-06-08 |
| DE2343827A1 (de) | 1974-04-25 |
| YU236173A (en) | 1982-02-28 |
| JPS49132099A (en, 2012) | 1974-12-18 |
| AU5943273A (en) | 1975-02-27 |
| GB1406204A (en) | 1975-09-17 |
| FR2197575B1 (en, 2012) | 1979-02-23 |
| YU39712B (en) | 1985-04-30 |
| NL7311757A (en, 2012) | 1974-03-04 |
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