FR2485540A1 - Nouveaux derives antibiotiques des cephalosporines, leur procede de preparation et les medicaments en contenant - Google Patents
Nouveaux derives antibiotiques des cephalosporines, leur procede de preparation et les medicaments en contenant Download PDFInfo
- Publication number
- FR2485540A1 FR2485540A1 FR8014512A FR8014512A FR2485540A1 FR 2485540 A1 FR2485540 A1 FR 2485540A1 FR 8014512 A FR8014512 A FR 8014512A FR 8014512 A FR8014512 A FR 8014512A FR 2485540 A1 FR2485540 A1 FR 2485540A1
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- Prior art keywords
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- sep
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- hydroxy
- amino
- 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.)
- Granted
Links
- 150000001780 cephalosporins Chemical class 0.000 title claims description 4
- 241000894006 Bacteria Species 0.000 title abstract description 3
- 229930186147 Cephalosporin Natural products 0.000 title description 2
- 229940124587 cephalosporin Drugs 0.000 title description 2
- -1 5-hydroxy -1,2,4-triazin-3-yl Chemical group 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 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 4
- 150000001412 amines Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 230000003385 bacteriostatic effect Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002169 ethanolamines Chemical class 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 230000001143 conditioned effect Effects 0.000 claims 1
- 150000001451 organic peroxides Chemical class 0.000 claims 1
- 241000588748 Klebsiella Species 0.000 abstract description 4
- 102000006635 beta-lactamase Human genes 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract description 2
- 229940088710 antibiotic agent Drugs 0.000 abstract description 2
- 108090000204 Dipeptidase 1 Proteins 0.000 abstract 1
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- 241000589516 Pseudomonas Species 0.000 abstract 1
- 241000607720 Serratia Species 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 150000002373 hemiacetals Chemical class 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 33
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 5
- 108020004256 Beta-lactamase Proteins 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
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- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
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- 159000000000 sodium salts Chemical class 0.000 description 3
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- 150000003462 sulfoxides Chemical class 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- NIVMSOGXYLPBDB-HCCKASOXSA-N (6R)-4-(furan-2-carbonylsulfanylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-3-carboxylic acid Chemical compound O1C(=CC=C1)C(=O)SCC1S[C@H]2N(C=C1C(=O)O)C(C2)=O NIVMSOGXYLPBDB-HCCKASOXSA-N 0.000 description 1
- IXJJELULBDAIMY-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazine Chemical compound C1CC=NNN1 IXJJELULBDAIMY-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-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
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 0 CCC(*)C(*)N(C(C1NC(CC)=O)SO)C1=O Chemical compound CCC(*)C(*)N(C(C1NC(CC)=O)SO)C1=O 0.000 description 1
- 241001532039 Camassia Species 0.000 description 1
- 235000000459 Camassia leichtlinii Nutrition 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
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- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
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- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/55—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound the modifying agent being also a pharmacologically or therapeutically active agent, i.e. the entire conjugate being a codrug, i.e. a dimer, oligomer or polymer of pharmacologically or therapeutically active compounds
- A61K47/552—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound the modifying agent being also a pharmacologically or therapeutically active agent, i.e. the entire conjugate being a codrug, i.e. a dimer, oligomer or polymer of pharmacologically or therapeutically active compounds one of the codrug's components being an antibiotic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/555—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound pre-targeting systems involving an organic compound, other than a peptide, protein or antibody, for targeting specific cells
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (31)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8014512A FR2485540A1 (fr) | 1980-06-30 | 1980-06-30 | Nouveaux derives antibiotiques des cephalosporines, leur procede de preparation et les medicaments en contenant |
| GR65352A GR75711B (enrdf_load_stackoverflow) | 1980-06-30 | 1981-06-25 | |
| GR65351A GR75706B (enrdf_load_stackoverflow) | 1980-06-30 | 1981-06-25 | |
| DK283281A DK283281A (da) | 1980-06-30 | 1981-06-26 | Fremgangsmaade til fremstilling af sulfoxidderivater af cephalosporiner |
| EP81401027A EP0044238B1 (fr) | 1980-06-30 | 1981-06-26 | Dérivés de céphalosporines sulfoxydes, procédé de préparation et compositions pharmaceutiques en contenant |
| DE8181401027T DE3162109D1 (en) | 1980-06-30 | 1981-06-26 | Cephalosporin sulfoxides, process for their preparation and pharmaceutical compositions containing them |
| EP81401028A EP0043756B1 (fr) | 1980-06-30 | 1981-06-26 | 1,2,4-Triazinylthiométhyl-3-céphèmes sulfoxydes, procédé de préparation et compositions pharmaceutiques en contenant |
| AT81401028T ATE7394T1 (de) | 1980-06-30 | 1981-06-26 | 1,2,4-triazinylthiomethyl-3-cephem-sulfoxyde, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate. |
| DK283381A DK283381A (da) | 1980-06-30 | 1981-06-26 | Fremgangsmaade til fremstilling af 1,2,4-triazinylthiomethyl-3-cephem-sulfoxid |
| DE8181401028T DE3163490D1 (en) | 1980-06-30 | 1981-06-26 | 1,2,4-triazinylthiomethyl-3-cephem sulfoxides, process for their preparation and pharmaceutical compositions containing them |
| AT81401027T ATE6066T1 (de) | 1980-06-30 | 1981-06-26 | Cephalosporinsulfoxyd-verbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate. |
| PT73283A PT73283B (fr) | 1980-06-30 | 1981-06-29 | Procede de preparation d'oxides de cephalosporines |
| IE1452/81A IE51358B1 (en) | 1980-06-30 | 1981-06-29 | 1,2,4-triazinylthiomethyl-3-cephem sulfoxides,process for their preparation and pharmaceutical compositions containing them |
| NO812215A NO159798C (no) | 1980-06-30 | 1981-06-29 | Analogifremgangsmaate for fremstilling av terapeutisk aktive cefalosporin-oksyder. |
| NZ197563A NZ197563A (en) | 1980-06-30 | 1981-06-29 | 3-(1,2,4-triazinylthiomethyl)-3-cephem-1-sulphoxide derivatives |
| ZA814392A ZA814392B (en) | 1980-06-30 | 1981-06-29 | 1,2,4-triazinylthiomethyl-3-cepheme sulfoxide procedure for preparation and deledic forms |
| NZ197564A NZ197564A (en) | 1980-06-30 | 1981-06-29 | Cephalosporin sulphoxide derivatives and pharmaceutical compositions |
| PT73284A PT73284A (fr) | 1980-06-30 | 1981-06-29 | Procede de preparation de derives de cephalosporines sulfoxides |
| IE1453/81A IE51359B1 (en) | 1980-06-30 | 1981-06-29 | Derivatives of cephalosporin sulphoxides,process for their preparation and pharmaceutical compositions containing them |
| NO812214A NO812214L (no) | 1980-06-30 | 1981-06-29 | Fremgangsmaate for fremstilling av 3-(hydroksy-1,2,4-triazinyl)tiometyl-cefalosporiner |
| ZA814394A ZA814394B (en) | 1980-06-30 | 1981-06-29 | Derivatives of cephalosporine sulphoxides:preparation and pharmaceutical composition |
| CA000380872A CA1173434A (en) | 1980-06-30 | 1981-06-30 | 1,2,4-triazinylthiomethyl-3-cepheme sulfoxide procedure for preparation and deledic forms |
| ES503563A ES503563A0 (es) | 1980-06-30 | 1981-06-30 | Procedimiento de preparacion de cefalosporinas oxidas |
| ES503562A ES503562A0 (es) | 1980-06-30 | 1981-06-30 | Procedimiento de preparacion de 3-(1,2,4-hidroxitriazinil) tiometil cefalosporinas |
| AU72410/81A AU7241081A (en) | 1980-06-30 | 1981-06-30 | Cephalosporins |
| MX10176881U MX6880E (es) | 1980-06-30 | 1981-06-30 | Procedimiento de preparacion de 1,2,4-triaziniltiometil-3-cefem sulfoxidos |
| JP10076481A JPS5738785A (en) | 1980-06-30 | 1981-06-30 | 3-(hydroxy-1,2,4-triazinyl)thiomethylcephalosporin , manufacture and drug composition containing same |
| AU72411/81A AU543165B2 (en) | 1980-06-30 | 1981-06-30 | Cephalosporins |
| CA000380874A CA1175806A (en) | 1980-06-30 | 1981-06-30 | Derivatives of cephalosporine sulphoxides : preparation and pharmaceutical composition |
| JP10076581A JPS5738786A (en) | 1980-06-30 | 1981-06-30 | Cephalosporin sulfoxide derivative, manufacture and drug composition containing it |
| US06/525,797 US4604387A (en) | 1980-06-30 | 1983-08-23 | 1,2,4-triazinylthiomethyl-3-cephem sulfoxides, and a procedure for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8014512A FR2485540A1 (fr) | 1980-06-30 | 1980-06-30 | Nouveaux derives antibiotiques des cephalosporines, leur procede de preparation et les medicaments en contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2485540A1 true FR2485540A1 (fr) | 1981-12-31 |
| FR2485540B1 FR2485540B1 (enrdf_load_stackoverflow) | 1984-02-24 |
Family
ID=9243670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8014512A Granted FR2485540A1 (fr) | 1980-06-30 | 1980-06-30 | Nouveaux derives antibiotiques des cephalosporines, leur procede de preparation et les medicaments en contenant |
Country Status (4)
| Country | Link |
|---|---|
| JP (2) | JPS5738785A (enrdf_load_stackoverflow) |
| AU (1) | AU7241081A (enrdf_load_stackoverflow) |
| FR (1) | FR2485540A1 (enrdf_load_stackoverflow) |
| ZA (2) | ZA814394B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656166A (en) * | 1983-05-27 | 1987-04-07 | Sanofi | Antibiotic compounds derived from cephalosporins, process for their production and pharmaceutical compositions |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4367228A (en) * | 1980-10-29 | 1983-01-04 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compound and composition |
| DE3207840A1 (de) * | 1982-03-04 | 1983-09-15 | Hoechst Ag, 6230 Frankfurt | "cephalosporinderivate und verfahren zu ihrer herstellung" |
| EP1660506A4 (en) * | 2003-08-25 | 2009-02-25 | Revaax Pharmaceuticals Llc | ORAL NEUROTHERAPEUTIC CEFAZOLINE COMPOSITIONS |
-
1980
- 1980-06-30 FR FR8014512A patent/FR2485540A1/fr active Granted
-
1981
- 1981-06-29 ZA ZA814394A patent/ZA814394B/xx unknown
- 1981-06-29 ZA ZA814392A patent/ZA814392B/xx unknown
- 1981-06-30 JP JP10076481A patent/JPS5738785A/ja active Pending
- 1981-06-30 JP JP10076581A patent/JPS5738786A/ja active Pending
- 1981-06-30 AU AU72410/81A patent/AU7241081A/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656166A (en) * | 1983-05-27 | 1987-04-07 | Sanofi | Antibiotic compounds derived from cephalosporins, process for their production and pharmaceutical compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5738785A (en) | 1982-03-03 |
| ZA814392B (en) | 1982-07-28 |
| JPS5738786A (en) | 1982-03-03 |
| ZA814394B (en) | 1982-09-29 |
| AU7241081A (en) | 1982-01-07 |
| FR2485540B1 (enrdf_load_stackoverflow) | 1984-02-24 |
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