CA1032157A - Cephalosporin derivatives, preparation thereof and pharmaceutical compounds containing same - Google Patents
Cephalosporin derivatives, preparation thereof and pharmaceutical compounds containing sameInfo
- Publication number
- CA1032157A CA1032157A CA226,045A CA226045A CA1032157A CA 1032157 A CA1032157 A CA 1032157A CA 226045 A CA226045 A CA 226045A CA 1032157 A CA1032157 A CA 1032157A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- représente
- carbone
- atomes
- alcoyle
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- 150000001780 cephalosporins Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title 1
- -1 radical pyridinio Chemical class 0.000 claims abstract description 25
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 27
- 150000003254 radicals Chemical class 0.000 description 25
- 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 21
- 229910052708 sodium Inorganic materials 0.000 description 21
- 239000011734 sodium Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 20
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 17
- 238000001914 filtration Methods 0.000 description 15
- 238000007792 addition Methods 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000009471 action Effects 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 206010001497 Agitation Diseases 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000037656 Respiratory Sounds Diseases 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 206010037833 rales Diseases 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 229910052601 baryte Inorganic materials 0.000 description 2
- 239000010428 baryte Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
- RHAXKFFKGZJUOE-UHFFFAOYSA-N 7-acetyl-6-ethyl-3,5,8-trihydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid Chemical compound O=C1C2=CC(O)=C(C(O)=O)C(C(O)=O)=C2C(=O)C2=C1C(O)=C(CC)C(C(C)=O)=C2O RHAXKFFKGZJUOE-UHFFFAOYSA-N 0.000 description 1
- 208000001992 Autosomal Dominant Optic Atrophy Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 101100001347 Mus musculus Akt1s1 gene Proteins 0.000 description 1
- 101100289867 Mus musculus Lyl1 gene Proteins 0.000 description 1
- LYAVXWPXKIFHBU-UHFFFAOYSA-N N-{2-[(1,2-diphenylhydrazinyl)carbonyl]-2-hydroxyhexanoyl}-6-aminohexanoic acid Chemical compound C=1C=CC=CC=1N(C(=O)C(O)(C(=O)NCCCCCC(O)=O)CCCC)NC1=CC=CC=C1 LYAVXWPXKIFHBU-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241001080024 Telles Species 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 230000004224 protection Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7415226A FR2269348A1 (en) | 1974-05-02 | 1974-05-02 | 7-Acylamino cephalosporin derivs - antibacterials active against Gram positive and Gram negative bacteria |
| FR7509517A FR2305185A2 (fr) | 1975-03-26 | 1975-03-26 | Nouveaux derives de la cephalospo |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1032157A true CA1032157A (en) | 1978-05-30 |
Family
ID=26218312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA226,045A Expired CA1032157A (en) | 1974-05-02 | 1975-05-01 | Cephalosporin derivatives, preparation thereof and pharmaceutical compounds containing same |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4034088A (en, 2012) |
| JP (1) | JPS50154283A (en, 2012) |
| AR (2) | AR207148A1 (en, 2012) |
| AU (1) | AU497840B2 (en, 2012) |
| CA (1) | CA1032157A (en, 2012) |
| CH (1) | CH602753A5 (en, 2012) |
| DE (1) | DE2519503A1 (en, 2012) |
| DK (1) | DK188375A (en, 2012) |
| ES (2) | ES437383A1 (en, 2012) |
| FI (1) | FI751296A7 (en, 2012) |
| GB (1) | GB1459370A (en, 2012) |
| HU (1) | HU171666B (en, 2012) |
| IL (1) | IL47212A0 (en, 2012) |
| LU (1) | LU72391A1 (en, 2012) |
| NL (1) | NL7504869A (en, 2012) |
| NO (1) | NO751551L (en, 2012) |
| SE (1) | SE7505066L (en, 2012) |
| SU (1) | SU589920A3 (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1094545A (en) * | 1976-02-16 | 1981-01-27 | Michael Gregson | Cephalosporin antibiotics |
| JPS59112990A (ja) * | 1982-12-21 | 1984-06-29 | Asahi Chem Ind Co Ltd | 新規セフアロスポリン類 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU468437B2 (en) * | 1971-03-09 | 1976-01-15 | Takeda Chemical Industries, Ltd | Cephalosporin derivatives |
| US3907787A (en) * | 1974-02-22 | 1975-09-23 | American Home Prod | 7-(2-Thioxo-4-thiazolidinecarboxamido)cephalosporanic acids and the corresponding S-ethers |
-
1975
- 1975-01-01 AR AR258603A patent/AR207148A1/es active
- 1975-04-24 NL NL7504869A patent/NL7504869A/xx not_active Application Discontinuation
- 1975-04-30 NO NO751551A patent/NO751551L/no unknown
- 1975-04-30 SU SU752133307A patent/SU589920A3/ru active
- 1975-04-30 SE SE7505066A patent/SE7505066L/xx unknown
- 1975-04-30 HU HU75RO00000839A patent/HU171666B/hu unknown
- 1975-04-30 FI FI751296A patent/FI751296A7/fi not_active Application Discontinuation
- 1975-04-30 LU LU72391A patent/LU72391A1/xx unknown
- 1975-04-30 IL IL47212A patent/IL47212A0/xx unknown
- 1975-04-30 DK DK188375A patent/DK188375A/da unknown
- 1975-04-30 US US05/573,110 patent/US4034088A/en not_active Expired - Lifetime
- 1975-05-01 CH CH559575A patent/CH602753A5/xx not_active IP Right Cessation
- 1975-05-01 CA CA226,045A patent/CA1032157A/en not_active Expired
- 1975-05-01 GB GB1830575A patent/GB1459370A/en not_active Expired
- 1975-05-02 JP JP50052628A patent/JPS50154283A/ja active Pending
- 1975-05-02 DE DE19752519503 patent/DE2519503A1/de active Pending
- 1975-05-02 ES ES437383A patent/ES437383A1/es not_active Expired
- 1975-05-02 AU AU80790/75A patent/AU497840B2/en not_active Expired
- 1975-10-13 ES ES441744A patent/ES441744A1/es not_active Expired
- 1975-12-09 AR AR208736A patent/AR208736A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| AU497840B2 (en) | 1979-01-11 |
| ES441744A1 (es) | 1977-03-16 |
| US4034088A (en) | 1977-07-05 |
| IL47212A0 (en) | 1975-06-25 |
| AR208736A1 (es) | 1977-02-28 |
| FI751296A7 (en, 2012) | 1975-11-03 |
| AU8079075A (en) | 1976-11-04 |
| HU171666B (hu) | 1978-02-28 |
| CH602753A5 (en, 2012) | 1978-07-31 |
| ES437383A1 (es) | 1976-12-01 |
| NL7504869A (nl) | 1975-11-04 |
| JPS50154283A (en, 2012) | 1975-12-12 |
| NO751551L (en, 2012) | 1975-11-04 |
| LU72391A1 (en, 2012) | 1976-03-17 |
| SU589920A3 (ru) | 1978-01-25 |
| AR207148A1 (es) | 1976-09-15 |
| DE2519503A1 (de) | 1975-11-13 |
| SE7505066L (sv) | 1975-11-03 |
| GB1459370A (en) | 1976-12-22 |
| DK188375A (da) | 1975-11-03 |
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