CH652406A5 - Esteri delle desacetossi cefalosporine loro sali e procedimenti per il loro ottenimento. - Google Patents
Esteri delle desacetossi cefalosporine loro sali e procedimenti per il loro ottenimento. Download PDFInfo
- Publication number
- CH652406A5 CH652406A5 CH1982/81A CH198281A CH652406A5 CH 652406 A5 CH652406 A5 CH 652406A5 CH 1982/81 A CH1982/81 A CH 1982/81A CH 198281 A CH198281 A CH 198281A CH 652406 A5 CH652406 A5 CH 652406A5
- Authority
- CH
- Switzerland
- Prior art keywords
- mole
- hydrochloride
- cefadroxil
- ester
- added
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 10
- 150000003839 salts Chemical class 0.000 title description 10
- 229930186147 Cephalosporin Natural products 0.000 title description 3
- 229940124587 cephalosporin Drugs 0.000 title description 3
- 150000001780 cephalosporins Chemical class 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- -1 cephalosporin esters Chemical class 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 239000012071 phase Substances 0.000 description 24
- BOEGTKLJZSQCCD-UEKVPHQBSA-N cefadroxil Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 BOEGTKLJZSQCCD-UEKVPHQBSA-N 0.000 description 20
- 229960002588 cefradine Drugs 0.000 description 20
- RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 18
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 18
- 229910001868 water Inorganic materials 0.000 description 16
- 229960004841 cefadroxil Drugs 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- NVIAYEIXYQCDAN-UHFFFAOYSA-N 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)C12 NVIAYEIXYQCDAN-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 230000002906 microbiologic effect Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229940113088 dimethylacetamide Drugs 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229950006327 napsilate Drugs 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- CLMSHAWYULIVFQ-UHFFFAOYSA-N 3-bromo-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Br)OC(=O)C2=C1 CLMSHAWYULIVFQ-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229950004288 tosilate Drugs 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KKLMJYDGZSAIQX-UHFFFAOYSA-N 2-(n-hydroxyanilino)acetic acid Chemical compound OC(=O)CN(O)C1=CC=CC=C1 KKLMJYDGZSAIQX-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- MRFJAULKKHVIGF-UHFFFAOYSA-N 2-amino-2-(4-hydroxyphenyl)acetyl chloride;hydrochloride Chemical compound [Cl-].ClC(=O)C([NH3+])C1=CC=C(O)C=C1 MRFJAULKKHVIGF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 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
- 239000007832 Na2SO4 Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 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
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
-
- 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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21463/80A IT1141286B (it) | 1980-04-17 | 1980-04-17 | Esteri delle desacetossi cefalosporine loro sali e procedimenti per il loro ottenimento |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH652406A5 true CH652406A5 (it) | 1985-11-15 |
Family
ID=11182169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1982/81A CH652406A5 (it) | 1980-04-17 | 1981-03-24 | Esteri delle desacetossi cefalosporine loro sali e procedimenti per il loro ottenimento. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4388460A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS56147789A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1171405A (cg-RX-API-DMAC7.html) |
| CH (1) | CH652406A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3115244A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2480753A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2074157B (cg-RX-API-DMAC7.html) |
| IL (1) | IL62376A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1141286B (cg-RX-API-DMAC7.html) |
| NL (1) | NL8101482A (cg-RX-API-DMAC7.html) |
| YU (1) | YU101681A (cg-RX-API-DMAC7.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0562527A (ja) * | 1991-09-04 | 1993-03-12 | Sanyo Kogyo Kk | 平形配線ケーブル |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3485812A (en) * | 1966-08-30 | 1969-12-23 | Gulf Research Development Co | Processes for preparing ethylene polymers |
| GB1355804A (en) * | 1970-12-04 | 1974-06-05 | Beecham Group Ltd | Penicillins and cephalosporinesters |
| US3985741A (en) * | 1972-09-15 | 1976-10-12 | Bristol-Myers Company | Production of p-hydroxycephalexin |
| 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 |
| GB1492393A (en) * | 1974-02-21 | 1977-11-16 | Beecham Group Ltd | Cephalosporin esters |
| JPS597717B2 (ja) * | 1976-09-08 | 1984-02-20 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| CH634848A5 (de) * | 1976-08-17 | 1983-02-28 | Fujisawa Pharmaceutical Co | Verfahren zur herstellung neuer 7-(n-substituierter 2-phenylglycinamido)-3-substituierte-3-cephem-4-carbonsaeuren. |
| JPS6011713B2 (ja) * | 1976-09-08 | 1985-03-27 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| DE2716677C2 (de) * | 1977-04-15 | 1985-10-10 | Hoechst Ag, 6230 Frankfurt | Cephemderivate und Verfahren zu ihrer Herstellung |
-
1980
- 1980-04-17 IT IT21463/80A patent/IT1141286B/it active
-
1981
- 1981-03-04 US US06/240,309 patent/US4388460A/en not_active Expired - Lifetime
- 1981-03-09 CA CA000372576A patent/CA1171405A/en not_active Expired
- 1981-03-16 IL IL62376A patent/IL62376A/xx unknown
- 1981-03-16 JP JP3666981A patent/JPS56147789A/ja active Granted
- 1981-03-24 CH CH1982/81A patent/CH652406A5/it not_active IP Right Cessation
- 1981-03-25 NL NL8101482A patent/NL8101482A/xx not_active Application Discontinuation
- 1981-03-31 GB GB8109979A patent/GB2074157B/en not_active Expired
- 1981-04-07 FR FR8106971A patent/FR2480753A1/fr active Granted
- 1981-04-15 DE DE19813115244 patent/DE3115244A1/de not_active Ceased
- 1981-04-17 YU YU01016/81A patent/YU101681A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT8021463A0 (it) | 1980-04-17 |
| GB2074157B (en) | 1984-02-29 |
| FR2480753B1 (cg-RX-API-DMAC7.html) | 1984-12-14 |
| US4388460A (en) | 1983-06-14 |
| IL62376A (en) | 1984-07-31 |
| NL8101482A (nl) | 1981-11-16 |
| JPH0250916B2 (cg-RX-API-DMAC7.html) | 1990-11-05 |
| JPS56147789A (en) | 1981-11-16 |
| GB2074157A (en) | 1981-10-28 |
| FR2480753A1 (fr) | 1981-10-23 |
| CA1171405A (en) | 1984-07-24 |
| YU101681A (en) | 1983-12-31 |
| DE3115244A1 (de) | 1982-05-13 |
| IT1141286B (it) | 1986-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |