FR2494278A1 - Nouveaux derives de la cephalosporine, leurs preparations et les medicaments qui les contiennent - Google Patents
Nouveaux derives de la cephalosporine, leurs preparations et les medicaments qui les contiennent Download PDFInfo
- Publication number
- FR2494278A1 FR2494278A1 FR8024637A FR8024637A FR2494278A1 FR 2494278 A1 FR2494278 A1 FR 2494278A1 FR 8024637 A FR8024637 A FR 8024637A FR 8024637 A FR8024637 A FR 8024637A FR 2494278 A1 FR2494278 A1 FR 2494278A1
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- Prior art keywords
- radical
- general formula
- amino
- acid
- dioxo
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- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 29
- 229930186147 Cephalosporin Natural products 0.000 title claims abstract description 28
- 150000001780 cephalosporins Chemical class 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 229940126601 medicinal product Drugs 0.000 title abstract 2
- -1 HYDROGEN aTOMS Chemical group 0.000 claims abstract description 89
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 230000001681 protective effect Effects 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 11
- 150000003462 sulfoxides Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000003573 thiols Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052751 metal Chemical class 0.000 claims description 7
- 239000002184 metal Chemical class 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
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- 125000004429 atom Chemical group 0.000 claims description 3
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- 239000003085 diluting agent Substances 0.000 claims description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 230000001012 protector Effects 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000006502 nitrobenzyl group Chemical group 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 61
- 239000000047 product Substances 0.000 description 51
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
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- 239000003960 organic solvent Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical group 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 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 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 150000004820 halides Chemical class 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical group CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
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- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
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- Life Sciences & Earth Sciences (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)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8024637A FR2494278A1 (fr) | 1980-11-20 | 1980-11-20 | Nouveaux derives de la cephalosporine, leurs preparations et les medicaments qui les contiennent |
| EP81401826A EP0053539A1 (fr) | 1980-11-20 | 1981-11-19 | Nouveaux dérivés de la céphalosporine, leur préparation et les compositions pharmaceutiques qui les contiennent |
| JP56185561A JPS57116090A (en) | 1980-11-20 | 1981-11-20 | Novel cephalosporin derivatives, manufacture and drug |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8024637A FR2494278A1 (fr) | 1980-11-20 | 1980-11-20 | Nouveaux derives de la cephalosporine, leurs preparations et les medicaments qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2494278A1 true FR2494278A1 (fr) | 1982-05-21 |
| FR2494278B1 FR2494278B1 (enExample) | 1983-04-15 |
Family
ID=9248171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8024637A Granted FR2494278A1 (fr) | 1980-11-20 | 1980-11-20 | Nouveaux derives de la cephalosporine, leurs preparations et les medicaments qui les contiennent |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0053539A1 (enExample) |
| JP (1) | JPS57116090A (enExample) |
| FR (1) | FR2494278A1 (enExample) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2275215A1 (fr) * | 1974-06-21 | 1976-01-16 | Hoffmann La Roche | Nouveaux derives heterocycliques de desacetoxycephalosporine, procede pour leur preparation et application en tant que medicament |
| FR2280381A1 (fr) * | 1974-08-02 | 1976-02-27 | Lilly Co Eli | Nouveaux derives de cephalosporines |
| EP0002605A1 (en) * | 1977-12-20 | 1979-06-27 | Eli Lilly And Company | Cephalosporin compounds and formulations containing them for use in the treatment of bacterial infections and the preparation of the cephalosporin compounds |
| FR2427337A1 (fr) * | 1978-05-30 | 1979-12-28 | Hoffmann La Roche | Nouveaux derives acyles de la cephalosporine, leur preparation et leurs utilisations therapeutiques |
-
1980
- 1980-11-20 FR FR8024637A patent/FR2494278A1/fr active Granted
-
1981
- 1981-11-19 EP EP81401826A patent/EP0053539A1/fr not_active Withdrawn
- 1981-11-20 JP JP56185561A patent/JPS57116090A/ja active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2275215A1 (fr) * | 1974-06-21 | 1976-01-16 | Hoffmann La Roche | Nouveaux derives heterocycliques de desacetoxycephalosporine, procede pour leur preparation et application en tant que medicament |
| FR2280381A1 (fr) * | 1974-08-02 | 1976-02-27 | Lilly Co Eli | Nouveaux derives de cephalosporines |
| EP0002605A1 (en) * | 1977-12-20 | 1979-06-27 | Eli Lilly And Company | Cephalosporin compounds and formulations containing them for use in the treatment of bacterial infections and the preparation of the cephalosporin compounds |
| FR2427337A1 (fr) * | 1978-05-30 | 1979-12-28 | Hoffmann La Roche | Nouveaux derives acyles de la cephalosporine, leur preparation et leurs utilisations therapeutiques |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2494278B1 (enExample) | 1983-04-15 |
| EP0053539A1 (fr) | 1982-06-09 |
| JPS57116090A (en) | 1982-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |