CA1032157A - Derives de la cephalosporine, leur preparation et les compositions medicinales qui les contiennent - Google Patents
Derives de la cephalosporine, leur preparation et les compositions medicinales qui les contiennentInfo
- 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)
Abstract
PRECIS DE LA DIVULGATION:
Nouveaux dérivés de la céphalosporine de formule généra-le (I) dans laquelle: R représente un radical alcoyle ou phényl-alcoyle, n est un nombre entier égal à zéro, 1 ou 2, R1 représen-te un atome d'hydrogène ou un radical acétoxy, (méthyl-5 thiadia-zol-1,3,4 yl-2) thio, (méthyl-1 tétrazol-1,2,3,4 yl-5) thio et R2 représente le radical carboxy ou un radical de formule générale (II) dans laquelle R3 représente un atome d'hydrogène ou un radical alcoyle, phényle ou phénylalcoyle et R4 représente un radical alcoy-le, alcoyloxyle, cyclohexyle, phényle ou phénylalcoyle, ou bien R2 représente le radical pyridinio et R2 représente l'ion carboxylato, sous la réserve que lorsque simultanément R représente un radical alcoyle, R1 représente un atome d'hydrogène ou le radical acétoxy et R2 représente le radical carboxy ou R1 représente le radical pyridinio et R2 représente l'ion carboxylato, n est obligatoirement un nombre entier égal à 1 ou 2, ainsi que leurs sels métalliques, leurs sels d'addition avec les bases azotées, non toxiques et phar-maceutiquement acceptables, leur préparation et les compositions médicinales qui les contiennent. Ces compositions sont particuliè-rement utiles dans le traitement des infections bactériennes.
(I) (II)
Nouveaux dérivés de la céphalosporine de formule généra-le (I) dans laquelle: R représente un radical alcoyle ou phényl-alcoyle, n est un nombre entier égal à zéro, 1 ou 2, R1 représen-te un atome d'hydrogène ou un radical acétoxy, (méthyl-5 thiadia-zol-1,3,4 yl-2) thio, (méthyl-1 tétrazol-1,2,3,4 yl-5) thio et R2 représente le radical carboxy ou un radical de formule générale (II) dans laquelle R3 représente un atome d'hydrogène ou un radical alcoyle, phényle ou phénylalcoyle et R4 représente un radical alcoy-le, alcoyloxyle, cyclohexyle, phényle ou phénylalcoyle, ou bien R2 représente le radical pyridinio et R2 représente l'ion carboxylato, sous la réserve que lorsque simultanément R représente un radical alcoyle, R1 représente un atome d'hydrogène ou le radical acétoxy et R2 représente le radical carboxy ou R1 représente le radical pyridinio et R2 représente l'ion carboxylato, n est obligatoirement un nombre entier égal à 1 ou 2, ainsi que leurs sels métalliques, leurs sels d'addition avec les bases azotées, non toxiques et phar-maceutiquement acceptables, leur préparation et les compositions médicinales qui les contiennent. Ces compositions sont particuliè-rement utiles dans le traitement des infections bactériennes.
(I) (II)
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 (fr) | 1978-05-30 |
Family
ID=26218312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA226,045A Expired CA1032157A (fr) | 1974-05-02 | 1975-05-01 | Derives de la cephalosporine, leur preparation et les compositions medicinales qui les contiennent |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4034088A (fr) |
| JP (1) | JPS50154283A (fr) |
| AR (2) | AR207148A1 (fr) |
| AU (1) | AU497840B2 (fr) |
| CA (1) | CA1032157A (fr) |
| CH (1) | CH602753A5 (fr) |
| DE (1) | DE2519503A1 (fr) |
| DK (1) | DK188375A (fr) |
| ES (2) | ES437383A1 (fr) |
| FI (1) | FI751296A7 (fr) |
| GB (1) | GB1459370A (fr) |
| HU (1) | HU171666B (fr) |
| IL (1) | IL47212A0 (fr) |
| LU (1) | LU72391A1 (fr) |
| NL (1) | NL7504869A (fr) |
| NO (1) | NO751551L (fr) |
| SE (1) | SE7505066L (fr) |
| SU (1) | SU589920A3 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1094545A (fr) * | 1976-02-16 | 1981-01-27 | Michael Gregson | Traduction non-disponible |
| 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 HU HU75RO00000839A patent/HU171666B/hu unknown
- 1975-04-30 SE SE7505066A patent/SE7505066L/xx unknown
- 1975-04-30 IL IL47212A patent/IL47212A0/xx unknown
- 1975-04-30 US US05/573,110 patent/US4034088A/en not_active Expired - Lifetime
- 1975-04-30 DK DK188375A patent/DK188375A/da unknown
- 1975-04-30 FI FI751296A patent/FI751296A7/fi not_active Application Discontinuation
- 1975-04-30 NO NO751551A patent/NO751551L/no unknown
- 1975-04-30 LU LU72391A patent/LU72391A1/xx unknown
- 1975-04-30 SU SU752133307A patent/SU589920A3/ru active
- 1975-05-01 CA CA226,045A patent/CA1032157A/fr not_active Expired
- 1975-05-01 CH CH559575A patent/CH602753A5/xx not_active IP Right Cessation
- 1975-05-01 GB GB1830575A patent/GB1459370A/en not_active Expired
- 1975-05-02 ES ES437383A patent/ES437383A1/es not_active Expired
- 1975-05-02 DE DE19752519503 patent/DE2519503A1/de active Pending
- 1975-05-02 AU AU80790/75A patent/AU497840B2/en not_active Expired
- 1975-05-02 JP JP50052628A patent/JPS50154283A/ja active Pending
- 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 |
|---|---|
| HU171666B (hu) | 1978-02-28 |
| JPS50154283A (fr) | 1975-12-12 |
| NL7504869A (nl) | 1975-11-04 |
| AU8079075A (en) | 1976-11-04 |
| NO751551L (fr) | 1975-11-04 |
| AR207148A1 (es) | 1976-09-15 |
| IL47212A0 (en) | 1975-06-25 |
| AR208736A1 (es) | 1977-02-28 |
| US4034088A (en) | 1977-07-05 |
| AU497840B2 (en) | 1979-01-11 |
| DE2519503A1 (de) | 1975-11-13 |
| SE7505066L (sv) | 1975-11-03 |
| ES437383A1 (es) | 1976-12-01 |
| GB1459370A (en) | 1976-12-22 |
| SU589920A3 (ru) | 1978-01-25 |
| DK188375A (da) | 1975-11-03 |
| FI751296A7 (fr) | 1975-11-03 |
| ES441744A1 (es) | 1977-03-16 |
| CH602753A5 (fr) | 1978-07-31 |
| LU72391A1 (fr) | 1976-03-17 |
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