AT406772B - Antibakterielle 7-acylamino-3-iminomethyl- cephalosporine und verfahren zu deren herstellung - Google Patents
Antibakterielle 7-acylamino-3-iminomethyl- cephalosporine und verfahren zu deren herstellung Download PDFInfo
- Publication number
- AT406772B AT406772B AT0051598A AT51598A AT406772B AT 406772 B AT406772 B AT 406772B AT 0051598 A AT0051598 A AT 0051598A AT 51598 A AT51598 A AT 51598A AT 406772 B AT406772 B AT 406772B
- Authority
- AT
- Austria
- Prior art keywords
- formula
- hydrogen
- lactam
- sep
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 230000000844 anti-bacterial effect Effects 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- -1 amino, hydroxy Chemical group 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- 150000004677 hydrates Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- NKLKVJINWGZXEO-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydroimidazol-1-amine Chemical compound CSC1=NCCN1N NKLKVJINWGZXEO-UHFFFAOYSA-N 0.000 description 2
- GPLPAXVMGVVCOU-UHFFFAOYSA-N 4,5-dihydroimidazole-1,2-diamine Chemical class NN1CCN=C1N GPLPAXVMGVVCOU-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- GPRBEKHLDVQUJE-VINNURBNSA-N cefotaxime Chemical compound N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C(O)=O)=O)C(=O)/C(=N/OC)C1=CSC(N)=N1 GPRBEKHLDVQUJE-VINNURBNSA-N 0.000 description 2
- 229960004261 cefotaxime Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AGZRADXSTWCBLN-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-nitrosoimidazolidine-2-thione Chemical compound OCCN1CCN(N=O)C1=S AGZRADXSTWCBLN-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- IRFKRJKLIWTTEH-UHFFFAOYSA-N 4,5-dihydroimidazole-1,2-diamine dihydrochloride Chemical compound C1CN(C(=N1)N)N.Cl.Cl IRFKRJKLIWTTEH-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- FEGHQAIRHGMSIU-KTAJNNJTSA-N FCO\N=C/C(=O)O Chemical compound FCO\N=C/C(=O)O FEGHQAIRHGMSIU-KTAJNNJTSA-N 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000588655 Moraxella catarrhalis Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 description 1
- 125000005277 alkyl imino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 102000038379 digestive enzymes Human genes 0.000 description 1
- 108091007734 digestive enzymes Proteins 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (27)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0051598A AT406772B (de) | 1998-03-23 | 1998-03-23 | Antibakterielle 7-acylamino-3-iminomethyl- cephalosporine und verfahren zu deren herstellung |
| ARP990101236A AR015248A1 (es) | 1998-03-23 | 1999-03-19 | Aminoguanidinas ciclicas, un proceso para su produccion, compuesto de partida,una composicion farmaceutica que las comprende y el uso de los mismos parala preparacion de un medicamento |
| CO99017143A CO5080739A1 (es) | 1998-03-23 | 1999-03-19 | Compuestos antibacterianos de cefalosporinas de 7-acilamino- 3-(amino-guanidina ciclica) metileno utiles como productos farmaceuticos y procesos para su produccion |
| EP99916839A EP1082326A1 (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics |
| SK1415-2000A SK14152000A3 (sk) | 1998-03-23 | 1999-03-19 | Cefalosporíny obsahujúce cyklické aminoguanidíny ako substituenty, spôsob ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje |
| CNB998043192A CN1188418C (zh) | 1998-03-23 | 1999-03-19 | 用作抗生素的具有环状氨基胍取代基的头孢菌素 |
| CA002324953A CA2324953C (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics |
| TR2000/02749T TR200002749T2 (tr) | 1998-03-23 | 1999-03-19 | Antibiyotikler olarak siklik aminoguanidin substitüentlerine sahip sefalosporinler. |
| RU2000126469/04A RU2245884C2 (ru) | 1998-03-23 | 1999-03-19 | 7-ациламиноцефалоспорины, замещенные в положении 3 циклическими аминогуанидиновыми группами |
| PCT/EP1999/001853 WO1999048896A1 (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics |
| PL99343094A PL343094A1 (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics |
| IL13847799A IL138477A0 (en) | 1998-03-23 | 1999-03-19 | Cyclic aminoguanidines |
| HU0101603A HUP0101603A3 (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents, process for their preparation, pharmaceutical compositions thereof and intermediates |
| AU35188/99A AU749735B2 (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics |
| EP07021394A EP1930335A1 (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents as Antibiotics |
| JP2000537879A JP2002507616A (ja) | 1998-03-23 | 1999-03-19 | 抗生物質としての環状アミノグアニジン置換基を有するセファロスポリン |
| BR9908960-2A BR9908960A (pt) | 1998-03-23 | 1999-03-19 | Amino guanidinas cìclicas |
| IDW20001853A ID26567A (id) | 1998-03-23 | 1999-03-19 | Cepalosporin yang memiliki substituen aminoguanidin siklik sebagai antibiotik |
| KR1020007010434A KR100696422B1 (ko) | 1998-03-23 | 1999-03-19 | 항생물질로서 사이클릭 아미노구아니딘 치환체를 가진세팔로스포린 |
| ZA200004850A ZA200004850B (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics. |
| NZ506908A NZ506908A (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics |
| MYPI99001068A MY119841A (en) | 1998-03-23 | 1999-03-22 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics. |
| PE1999000232A PE20000360A1 (es) | 1998-03-23 | 1999-03-22 | Aminoguanidinas ciclicas |
| TW088107541A TWI250983B (en) | 1998-03-23 | 1999-05-10 | Cyclic aminoguanidines |
| IL138477A IL138477A (en) | 1998-03-23 | 2000-09-14 | 7 - acylamino - 3 - (cyclic aminoguanidines) methylene cephalosporins, their preparation and pharmaceutical compositions comprising them |
| US09/667,075 US6440957B1 (en) | 1998-03-23 | 2000-09-21 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics |
| NO20004760A NO20004760L (no) | 1998-03-23 | 2000-09-22 | Cefalosporiner med cykliske aminoguanidinsubstituenter som antibiotika |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0051598A AT406772B (de) | 1998-03-23 | 1998-03-23 | Antibakterielle 7-acylamino-3-iminomethyl- cephalosporine und verfahren zu deren herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA51598A ATA51598A (de) | 2000-01-15 |
| AT406772B true AT406772B (de) | 2000-08-25 |
Family
ID=3492649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0051598A AT406772B (de) | 1998-03-23 | 1998-03-23 | Antibakterielle 7-acylamino-3-iminomethyl- cephalosporine und verfahren zu deren herstellung |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6440957B1 (enExample) |
| EP (2) | EP1930335A1 (enExample) |
| JP (1) | JP2002507616A (enExample) |
| KR (1) | KR100696422B1 (enExample) |
| CN (1) | CN1188418C (enExample) |
| AR (1) | AR015248A1 (enExample) |
| AT (1) | AT406772B (enExample) |
| AU (1) | AU749735B2 (enExample) |
| BR (1) | BR9908960A (enExample) |
| CA (1) | CA2324953C (enExample) |
| CO (1) | CO5080739A1 (enExample) |
| HU (1) | HUP0101603A3 (enExample) |
| ID (1) | ID26567A (enExample) |
| IL (2) | IL138477A0 (enExample) |
| MY (1) | MY119841A (enExample) |
| NO (1) | NO20004760L (enExample) |
| NZ (1) | NZ506908A (enExample) |
| PE (1) | PE20000360A1 (enExample) |
| PL (1) | PL343094A1 (enExample) |
| RU (1) | RU2245884C2 (enExample) |
| SK (1) | SK14152000A3 (enExample) |
| TR (1) | TR200002749T2 (enExample) |
| TW (1) | TWI250983B (enExample) |
| WO (1) | WO1999048896A1 (enExample) |
| ZA (1) | ZA200004850B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6693095B2 (en) * | 1997-04-01 | 2004-02-17 | Biochemie Gesellschaft M.B.H. | Antibacterial substituted 7-acylamino-3-(methylhydrazono) methyl-cephalosporins and intermediates |
| DE102007052891A1 (de) | 2007-11-02 | 2009-05-07 | Evonik Degussa Gmbh | Verfahren zur Stabilisierung von olefinisch ungesättigten Monomeren |
| DE102013204950A1 (de) | 2013-03-20 | 2014-09-25 | Evonik Industries Ag | Verfahren und Zusammensetzung zur Inhibierung der Polymerisation von Cyclopentadienverbindungen |
| ES2624415T3 (es) | 2014-09-08 | 2017-07-14 | Evonik Degussa Gmbh | (Tio)acetales fenólicos como agentes inhibidores de la polimerización de monómeros olefínicamente insaturados |
| TWI669317B (zh) | 2014-09-22 | 2019-08-21 | 德商贏創德固賽有限責任公司 | 反應性單體的改良製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996035692A1 (en) * | 1995-05-11 | 1996-11-14 | Biochemie Gesellschaft Mbh | Antibacterial cephalosporins |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE943408C (de) * | 1953-03-31 | 1956-05-17 | Bayer Ag | Verfahren zur Darstellung von Bisguanylhydrazonen |
| FI851934A7 (fi) * | 1984-05-30 | 1985-12-01 | Ici Plc | Kefalosporiinijohdannaisia. |
| GB8721568D0 (en) * | 1987-09-14 | 1987-10-21 | Fujisawa Pharmaceutical Co | Cephem compounds |
| NZ337732A (en) * | 1997-04-01 | 2001-09-28 | Biochemie Gmbh | Antibacterial substituted 7-acylamino -3-(methylhydrazono) methyl-cephalosporins and intermediates |
-
1998
- 1998-03-23 AT AT0051598A patent/AT406772B/de not_active IP Right Cessation
-
1999
- 1999-03-19 AR ARP990101236A patent/AR015248A1/es not_active Application Discontinuation
- 1999-03-19 EP EP07021394A patent/EP1930335A1/en not_active Withdrawn
- 1999-03-19 RU RU2000126469/04A patent/RU2245884C2/ru not_active IP Right Cessation
- 1999-03-19 AU AU35188/99A patent/AU749735B2/en not_active Ceased
- 1999-03-19 IL IL13847799A patent/IL138477A0/xx not_active IP Right Cessation
- 1999-03-19 SK SK1415-2000A patent/SK14152000A3/sk unknown
- 1999-03-19 ID IDW20001853A patent/ID26567A/id unknown
- 1999-03-19 EP EP99916839A patent/EP1082326A1/en not_active Withdrawn
- 1999-03-19 CA CA002324953A patent/CA2324953C/en not_active Expired - Fee Related
- 1999-03-19 CO CO99017143A patent/CO5080739A1/es unknown
- 1999-03-19 BR BR9908960-2A patent/BR9908960A/pt not_active Application Discontinuation
- 1999-03-19 HU HU0101603A patent/HUP0101603A3/hu unknown
- 1999-03-19 TR TR2000/02749T patent/TR200002749T2/xx unknown
- 1999-03-19 CN CNB998043192A patent/CN1188418C/zh not_active Expired - Fee Related
- 1999-03-19 WO PCT/EP1999/001853 patent/WO1999048896A1/en not_active Ceased
- 1999-03-19 ZA ZA200004850A patent/ZA200004850B/en unknown
- 1999-03-19 JP JP2000537879A patent/JP2002507616A/ja not_active Withdrawn
- 1999-03-19 NZ NZ506908A patent/NZ506908A/xx unknown
- 1999-03-19 PL PL99343094A patent/PL343094A1/xx unknown
- 1999-03-19 KR KR1020007010434A patent/KR100696422B1/ko not_active Expired - Fee Related
- 1999-03-22 MY MYPI99001068A patent/MY119841A/en unknown
- 1999-03-22 PE PE1999000232A patent/PE20000360A1/es not_active Application Discontinuation
- 1999-05-10 TW TW088107541A patent/TWI250983B/zh not_active IP Right Cessation
-
2000
- 2000-09-14 IL IL138477A patent/IL138477A/en unknown
- 2000-09-21 US US09/667,075 patent/US6440957B1/en not_active Expired - Fee Related
- 2000-09-22 NO NO20004760A patent/NO20004760L/no not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996035692A1 (en) * | 1995-05-11 | 1996-11-14 | Biochemie Gesellschaft Mbh | Antibacterial cephalosporins |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1082326A1 (en) | 2001-03-14 |
| ZA200004850B (en) | 2002-02-27 |
| JP2002507616A (ja) | 2002-03-12 |
| ID26567A (id) | 2001-01-18 |
| KR100696422B1 (ko) | 2007-03-20 |
| WO1999048896A1 (en) | 1999-09-30 |
| AR015248A1 (es) | 2001-04-18 |
| TR200002749T2 (tr) | 2000-12-21 |
| PE20000360A1 (es) | 2000-05-17 |
| CO5080739A1 (es) | 2001-09-25 |
| SK14152000A3 (sk) | 2001-05-10 |
| CA2324953C (en) | 2008-05-13 |
| AU749735B2 (en) | 2002-07-04 |
| CN1294593A (zh) | 2001-05-09 |
| NO20004760L (no) | 2000-11-21 |
| KR20010074666A (ko) | 2001-08-08 |
| IL138477A (en) | 2007-06-17 |
| NZ506908A (en) | 2003-04-29 |
| RU2245884C2 (ru) | 2005-02-10 |
| CN1188418C (zh) | 2005-02-09 |
| PL343094A1 (en) | 2001-07-30 |
| MY119841A (en) | 2005-07-29 |
| ATA51598A (de) | 2000-01-15 |
| US6440957B1 (en) | 2002-08-27 |
| AU3518899A (en) | 1999-10-18 |
| HUP0101603A2 (hu) | 2001-12-28 |
| IL138477A0 (en) | 2001-10-31 |
| HUP0101603A3 (en) | 2002-10-28 |
| NO20004760D0 (no) | 2000-09-22 |
| TWI250983B (en) | 2006-03-11 |
| CA2324953A1 (en) | 1999-09-30 |
| EP1930335A1 (en) | 2008-06-11 |
| BR9908960A (pt) | 2000-12-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69924751T2 (de) | Cephemverbindungen mit einem imidazo[4,5-b]pyridiniummethyl-rest, die ein breites antibakterielles wirkungsspektrum haben | |
| DE69209615T2 (de) | Aromatische Amidinderivate und ihre Salze | |
| DE3750443T2 (de) | Cephalosporinverbindungen, Verfahren zu ihrer Herstellung und antibakterielle Mittel. | |
| DE60111757T2 (de) | 3-(Heteroarylacetamido)-2-oxoazetidin-1-sulfonsäure-derivate als antibakterielle Mittel | |
| DE2332878C2 (de) | Salze von Cephalosporinen mit Arginin und Lysin, ihre Herstellung und injizierbare pharmazeutische Zubereitungen | |
| DE69736775T2 (de) | Cephemverbindungen und medikamente die diese verbindungen enthalten | |
| DE2415402C2 (de) | Cephalosporansäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel | |
| DE3789466T2 (de) | 3,7-Disubstituierte-3-Cephemverbindungen und Verfahren zu ihrer Herstellung. | |
| AT406772B (de) | Antibakterielle 7-acylamino-3-iminomethyl- cephalosporine und verfahren zu deren herstellung | |
| DE3885031T2 (de) | Wasserlösliches antibiotisches Präparat und wasserlösliche Salze von Cephem-Verbindungen. | |
| DE69131753T2 (de) | Antibakterielle penem-esterderivate | |
| DE2446901A1 (de) | 7-acetoacetamidocephemverbindungen, verfahren zur herstellung derselben und diese enthaltende pharmazeutische mittel | |
| DE2739448A1 (de) | 7-substituierte aminoacetamido- oxadethiacephalosporine, verfahren zu deren herstellung und deren verwendung bei der behandlung bakterieller erkrankungen | |
| DE3041160C2 (enExample) | ||
| CH647524A5 (de) | 7alpha-methoxycephalosporine und verfahren zur herstellung derselben. | |
| DE69816057T2 (de) | Antibakterielle substituierte 7-acylamino-3-(methylhydrazono)methyl-cephalosporine und zwischenprodukte | |
| DE2234280B2 (de) | Cephalosporinverbindungen und Verfahren zu deren Herstellung | |
| DE69736233T2 (de) | Pyridobenzoxazinderivate | |
| AT405180B (de) | Neue derivate von substituierten 3-cephem-4-carbonsäurederivaten und verfahren zu deren herstellung | |
| DE1670788C3 (de) | 3-Dithiocarbamat-Derivate von Cephalosporinen und Verfahren zu ihrer Herstellung | |
| DE2852745A1 (de) | Neue penicillin- und cephalosporinderivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| AT403283B (de) | 3-methylimino-3-cephemderivate | |
| EP1945304A2 (de) | Imidazo-pyridin-haltige beta-agonisten, verfahren zu deren herstellung und deren verwendung als arzneimittel | |
| EP0390099B1 (de) | Polare Cephalosporinderivate und Verfahren zu ihrer Herstellung | |
| AT371472B (de) | Verfahren zur herstellung von neuen oximderivaten der 7-aminothiazolylacetamidocephalosporansaeure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EIH | Change in the person of patent owner | ||
| EFA | Change in the company name | ||
| ELJ | Ceased due to non-payment of the annual fee |