SE448238B - Nya 1-oxadetiacefalosporinderivat, forfarande for framstellning derav, antibakteriell komposition innehallande dem samt anvendning av dem for att hemma bakterietillvext in vitro - Google Patents
Nya 1-oxadetiacefalosporinderivat, forfarande for framstellning derav, antibakteriell komposition innehallande dem samt anvendning av dem for att hemma bakterietillvext in vitroInfo
- Publication number
- SE448238B SE448238B SE8007403A SE8007403A SE448238B SE 448238 B SE448238 B SE 448238B SE 8007403 A SE8007403 A SE 8007403A SE 8007403 A SE8007403 A SE 8007403A SE 448238 B SE448238 B SE 448238B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- methyl
- tetrazol
- amino
- pharmaceutically acceptable
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 239000000203 mixture Substances 0.000 title claims description 11
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 10
- 238000000338 in vitro Methods 0.000 title claims description 5
- -1 (1-methyl-1H-tetrazol-5-yl) thio group Chemical group 0.000 claims description 83
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000007859 condensation product Substances 0.000 claims description 9
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- 230000001580 bacterial effect Effects 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004149 thio group Chemical group *S* 0.000 claims description 7
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical group NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
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- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- VFQXVTODMYMSMJ-UHFFFAOYSA-O pyridin-1-ium-4-carboxamide Chemical compound NC(=O)C1=CC=[NH+]C=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-O 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- GRWAIJBHBCCLGS-UHFFFAOYSA-N 2-(tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1C=NN=N1 GRWAIJBHBCCLGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 4
- OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 claims 1
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- PWEFRKZZBVCRQB-ZCFIWIBFSA-N (6r)-5-oxa-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class O1CC=CN2C(=O)C[C@H]21 PWEFRKZZBVCRQB-ZCFIWIBFSA-N 0.000 description 4
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XUJNEKJLAYXESH-UWTATZPHSA-N D-Cysteine Chemical compound SC[C@@H](N)C(O)=O XUJNEKJLAYXESH-UWTATZPHSA-N 0.000 description 3
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- 241000588724 Escherichia coli Species 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
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- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- GRIXGZQULWMCLU-HUTAOCTPSA-L disodium;(6r,7r)-7-[[2-carboxylato-2-(4-hydroxyphenyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].[Na+].N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CO[C@@H]21)C([O-])=O)=O)C(=O)C(C([O-])=O)C1=CC=C(O)C=C1 GRIXGZQULWMCLU-HUTAOCTPSA-L 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- IFQSXNOEEPCSLW-HSHFZTNMSA-N (2s)-2-amino-3-sulfanylpropanoic acid;hydron;chloride Chemical compound Cl.SC[C@@H](N)C(O)=O IFQSXNOEEPCSLW-HSHFZTNMSA-N 0.000 description 2
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 description 2
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14129779A JPS5690088A (en) | 1979-11-02 | 1979-11-02 | Novel cephalosporin analog compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8007403L SE8007403L (sv) | 1981-05-03 |
| SE448238B true SE448238B (sv) | 1987-02-02 |
Family
ID=15288600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8007403A SE448238B (sv) | 1979-11-02 | 1980-10-22 | Nya 1-oxadetiacefalosporinderivat, forfarande for framstellning derav, antibakteriell komposition innehallande dem samt anvendning av dem for att hemma bakterietillvext in vitro |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4325951A (en, 2012) |
| JP (1) | JPS5690088A (en, 2012) |
| AT (1) | AT373259B (en, 2012) |
| AU (1) | AU538028B2 (en, 2012) |
| BE (1) | BE885999A (en, 2012) |
| CA (1) | CA1148949A (en, 2012) |
| CH (1) | CH654311A5 (en, 2012) |
| DE (1) | DE3041160A1 (en, 2012) |
| ES (1) | ES496480A0 (en, 2012) |
| FR (1) | FR2468608A1 (en, 2012) |
| GB (1) | GB2061945B (en, 2012) |
| GR (1) | GR70222B (en, 2012) |
| IL (1) | IL61335A (en, 2012) |
| IT (2) | IT1154884B (en, 2012) |
| NL (1) | NL8005992A (en, 2012) |
| PT (1) | PT72001B (en, 2012) |
| SE (1) | SE448238B (en, 2012) |
| YU (1) | YU42987B (en, 2012) |
| ZA (1) | ZA806526B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK163000C (da) * | 1982-09-30 | 1992-06-01 | Shionogi & Co | Analogifremgangsmaade til fremstilling af vinylthioacetamido-1-dethia-1-oxa-cephalosporinderivater |
| JPS59139385A (ja) * | 1982-12-23 | 1984-08-10 | Shionogi & Co Ltd | フルオロメチルチオオキサセフアロスポリン |
| JPS59231090A (ja) * | 1983-06-14 | 1984-12-25 | Shionogi & Co Ltd | フルオロメチルチオオキサセフアロスポリン |
| DE3329427A1 (de) * | 1983-08-13 | 1985-02-21 | Bayer Ag, 5090 Leverkusen | 7-amino-3(1-pyridiniomethyl)-8-oxo-5-oxa-1-azabicyclo(4.2.0)oct-2-en-2-carboxylate, verfahren zu ihrer herstellung und ihre verwendung als zwischenprodukte zur synthese von ss-lactam-antibiotika |
| DE3404906A1 (de) * | 1984-02-11 | 1985-08-14 | Bayer Ag, 5090 Leverkusen | 1-oxadethiacephalosporinderivate sowie verfahren zu ihrer herstellung |
| JP5889590B2 (ja) * | 2011-10-05 | 2016-03-22 | 東ソー株式会社 | タンパク質の分析、分離・精製用吸着剤 |
| KR102115644B1 (ko) * | 2017-09-13 | 2020-05-27 | 주식회사 동도물산 | 7α-알콕시옥사세펨 중간체의 제조방법 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226866A (en) * | 1972-11-06 | 1980-10-07 | Merck & Co., Inc. | Novel antibiotic analogues of cephalosporins |
| GB1510794A (en) * | 1974-08-06 | 1978-05-17 | Univ Kingston | 1-oxacephems and intermediates therefor |
| US4011216A (en) * | 1975-04-11 | 1977-03-08 | Bristol-Myers Company | Δ2,3-0-2-Isocephem-4-carboxylic acid and derivatives thereof as antibacterial agents |
| US4013648A (en) * | 1975-07-23 | 1977-03-22 | Bristol-Myers Company | Δ2,3 -0-2-Isocephem-4-carboxylic acid and derivatives as antibacterial agents |
| US4045438A (en) * | 1975-10-24 | 1977-08-30 | Yeda Research And Development Co. Ltd. | Cephalosporin antibiotics |
| US4031083A (en) * | 1975-10-24 | 1977-06-21 | Yeda Research And Development Co., Ltd. | Cephalosporin antibiotics |
| US4180571A (en) * | 1976-03-25 | 1979-12-25 | Shionogi & Co., Ltd. | Arylmalonamido-1-oxadethiacephalosporins |
| CA1085392A (en) * | 1976-03-25 | 1980-09-09 | Masayuki Narisada | Arylmalonamido-1-oxadethiacephalosporins |
| JPS5331690A (en) * | 1976-09-01 | 1978-03-25 | Shionogi & Co Ltd | Oxadithiacephalosporins |
| JPS5419990A (en) * | 1977-07-14 | 1979-02-15 | Shionogi & Co Ltd | Dihydrotriazinylthioxacephalosporin |
-
1979
- 1979-11-02 JP JP14129779A patent/JPS5690088A/ja active Granted
-
1980
- 1980-10-22 SE SE8007403A patent/SE448238B/sv not_active IP Right Cessation
- 1980-10-23 IL IL61335A patent/IL61335A/xx unknown
- 1980-10-23 GR GR63206A patent/GR70222B/el unknown
- 1980-10-23 ZA ZA00806526A patent/ZA806526B/xx unknown
- 1980-10-24 US US06/200,410 patent/US4325951A/en not_active Expired - Lifetime
- 1980-10-27 AT AT0528480A patent/AT373259B/de not_active IP Right Cessation
- 1980-10-30 CH CH8078/80A patent/CH654311A5/de not_active IP Right Cessation
- 1980-10-30 YU YU2785/80A patent/YU42987B/xx unknown
- 1980-10-30 AU AU63872/80A patent/AU538028B2/en not_active Ceased
- 1980-10-30 GB GB8035014A patent/GB2061945B/en not_active Expired
- 1980-10-30 CA CA000363652A patent/CA1148949A/en not_active Expired
- 1980-10-31 DE DE19803041160 patent/DE3041160A1/de active Granted
- 1980-10-31 ES ES496480A patent/ES496480A0/es active Granted
- 1980-10-31 PT PT72001A patent/PT72001B/pt unknown
- 1980-10-31 NL NL8005992A patent/NL8005992A/nl not_active Application Discontinuation
- 1980-10-31 BE BE0/202682A patent/BE885999A/fr not_active IP Right Cessation
- 1980-11-03 IT IT09577/80A patent/IT1154884B/it active
- 1980-11-03 IT IT1980A09577A patent/IT8009577A1/it unknown
- 1980-11-03 FR FR8023664A patent/FR2468608A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2061945B (en) | 1984-05-31 |
| ZA806526B (en) | 1982-02-24 |
| IL61335A0 (en) | 1980-12-31 |
| AU6387280A (en) | 1981-05-07 |
| ES8107238A1 (es) | 1981-10-01 |
| GR70222B (en, 2012) | 1982-08-31 |
| US4325951A (en) | 1982-04-20 |
| ES496480A0 (es) | 1981-10-01 |
| GB2061945A (en) | 1981-05-20 |
| IT8009577A1 (it) | 1982-05-03 |
| DE3041160A1 (de) | 1981-05-21 |
| NL8005992A (nl) | 1981-06-01 |
| YU42987B (en) | 1989-02-28 |
| PT72001B (en) | 1981-08-31 |
| AT373259B (de) | 1984-01-10 |
| IT1154884B (it) | 1987-01-21 |
| CA1148949A (en) | 1983-06-28 |
| SE8007403L (sv) | 1981-05-03 |
| YU278580A (en) | 1983-04-30 |
| JPH0120156B2 (en, 2012) | 1989-04-14 |
| ATA528480A (de) | 1983-05-15 |
| FR2468608B1 (en, 2012) | 1983-06-24 |
| DE3041160C2 (en, 2012) | 1987-08-27 |
| PT72001A (en) | 1980-11-01 |
| JPS5690088A (en) | 1981-07-21 |
| IL61335A (en) | 1983-11-30 |
| AU538028B2 (en) | 1984-07-26 |
| BE885999A (fr) | 1981-02-16 |
| IT8009577A0 (it) | 1980-11-03 |
| CH654311A5 (de) | 1986-02-14 |
| FR2468608A1 (fr) | 1981-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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