ZA200004850B - Cephalosporines having cyclic aminoguanidine substituents as antibiotics. - Google Patents
Cephalosporines having cyclic aminoguanidine substituents as antibiotics. Download PDFInfo
- Publication number
- ZA200004850B ZA200004850B ZA200004850A ZA200004850A ZA200004850B ZA 200004850 B ZA200004850 B ZA 200004850B ZA 200004850 A ZA200004850 A ZA 200004850A ZA 200004850 A ZA200004850 A ZA 200004850A ZA 200004850 B ZA200004850 B ZA 200004850B
- Authority
- ZA
- South Africa
- Prior art keywords
- denotes
- alkyl
- compound
- formula
- hydrogen
- Prior art date
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- 239000003242 anti bacterial agent Substances 0.000 title description 2
- 229940088710 antibiotic agent Drugs 0.000 title description 2
- 125000001271 cephalosporin group Chemical group 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 50
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- -1 amino, hydroxy Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 150000002148 esters Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 4
- 125000005277 alkyl imino group Chemical group 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 150000001412 amines 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
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 150000004677 hydrates Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 102100028644 Tenascin-R Human genes 0.000 claims 3
- 230000000813 microbial effect Effects 0.000 claims 3
- 108010020387 tenascin R Proteins 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 108090001069 Chymopapain Proteins 0.000 claims 1
- 241000588722 Escherichia Species 0.000 claims 1
- 241000588748 Klebsiella Species 0.000 claims 1
- 241000588621 Moraxella Species 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000003282 alkyl amino group Chemical group 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical group NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229930186147 Cephalosporin Natural products 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000004962 physiological condition Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XBVZOSFPDGRHQN-UHFFFAOYSA-N 3-hydroxy-5-(hydroxymethyl)-2-(morpholin-4-ylmethyl)pyridine-4-carbaldehyde Chemical compound O1CCN(CC1)CC1=NC=C(C(=C1O)C=O)CO XBVZOSFPDGRHQN-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
- 101000825192 Arabidopsis thaliana Arginine decarboxylase 2 Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000005122 aminoalkylamino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000005110 aryl thio group Chemical group 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
- 239000002585 base Substances 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 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
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 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
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| ZA200004850B true ZA200004850B (en) | 2002-02-27 |
Family
ID=3492649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200004850A ZA200004850B (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics. |
Country Status (25)
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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE943408C (de) * | 1953-03-31 | 1956-05-17 | Bayer Ag | Verfahren zur Darstellung von Bisguanylhydrazonen |
| FI851934L (fi) * | 1984-05-30 | 1985-12-01 | Ici Plc | Kefalosporinderivat. |
| GB8721568D0 (en) * | 1987-09-14 | 1987-10-21 | Fujisawa Pharmaceutical Co | Cephem compounds |
| ATE233268T1 (de) * | 1995-05-11 | 2003-03-15 | Biochemie Gmbh | Antibakterielle cephalosporinverbindungen |
| BR9807913A (pt) * | 1997-04-01 | 2000-02-22 | Biochemie Gmbh | 7-acilamino-3-(metilhidrazono)metil cefalosporinas substituìdas antibacterianas e intermediários |
-
1998
- 1998-03-23 AT AT0051598A patent/AT406772B/de not_active IP Right Cessation
-
1999
- 1999-03-19 EP EP07021394A patent/EP1930335A1/en not_active Withdrawn
- 1999-03-19 ID IDW20001853A patent/ID26567A/id unknown
- 1999-03-19 WO PCT/EP1999/001853 patent/WO1999048896A1/en not_active Ceased
- 1999-03-19 IL IL13847799A patent/IL138477A0/xx not_active IP Right Cessation
- 1999-03-19 PL PL99343094A patent/PL343094A1/xx unknown
- 1999-03-19 ZA ZA200004850A patent/ZA200004850B/en unknown
- 1999-03-19 AR ARP990101236A patent/AR015248A1/es not_active Application Discontinuation
- 1999-03-19 JP JP2000537879A patent/JP2002507616A/ja not_active Withdrawn
- 1999-03-19 BR BR9908960-2A patent/BR9908960A/pt not_active Application Discontinuation
- 1999-03-19 TR TR2000/02749T patent/TR200002749T2/xx unknown
- 1999-03-19 EP EP99916839A patent/EP1082326A1/en not_active Withdrawn
- 1999-03-19 HU HU0101603A patent/HUP0101603A3/hu unknown
- 1999-03-19 CO CO99017143A patent/CO5080739A1/es unknown
- 1999-03-19 SK SK1415-2000A patent/SK14152000A3/sk unknown
- 1999-03-19 CA CA002324953A patent/CA2324953C/en not_active Expired - Fee Related
- 1999-03-19 RU RU2000126469/04A patent/RU2245884C2/ru not_active IP Right Cessation
- 1999-03-19 CN CNB998043192A patent/CN1188418C/zh not_active Expired - Fee Related
- 1999-03-19 AU AU35188/99A patent/AU749735B2/en not_active Ceased
- 1999-03-19 NZ NZ506908A patent/NZ506908A/xx unknown
- 1999-03-19 KR KR1020007010434A patent/KR100696422B1/ko not_active Expired - Fee Related
- 1999-03-22 PE PE1999000232A patent/PE20000360A1/es not_active Application Discontinuation
- 1999-03-22 MY MYPI99001068A patent/MY119841A/en unknown
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0101603A3 (en) | 2002-10-28 |
| NO20004760D0 (no) | 2000-09-22 |
| NZ506908A (en) | 2003-04-29 |
| TWI250983B (en) | 2006-03-11 |
| PL343094A1 (en) | 2001-07-30 |
| ATA51598A (de) | 2000-01-15 |
| AU3518899A (en) | 1999-10-18 |
| BR9908960A (pt) | 2000-12-05 |
| IL138477A (en) | 2007-06-17 |
| WO1999048896A1 (en) | 1999-09-30 |
| AR015248A1 (es) | 2001-04-18 |
| AT406772B (de) | 2000-08-25 |
| CN1294593A (zh) | 2001-05-09 |
| MY119841A (en) | 2005-07-29 |
| KR100696422B1 (ko) | 2007-03-20 |
| NO20004760L (no) | 2000-11-21 |
| HUP0101603A2 (hu) | 2001-12-28 |
| EP1930335A1 (en) | 2008-06-11 |
| US6440957B1 (en) | 2002-08-27 |
| CO5080739A1 (es) | 2001-09-25 |
| SK14152000A3 (sk) | 2001-05-10 |
| ID26567A (id) | 2001-01-18 |
| JP2002507616A (ja) | 2002-03-12 |
| AU749735B2 (en) | 2002-07-04 |
| RU2245884C2 (ru) | 2005-02-10 |
| TR200002749T2 (tr) | 2000-12-21 |
| EP1082326A1 (en) | 2001-03-14 |
| PE20000360A1 (es) | 2000-05-17 |
| KR20010074666A (ko) | 2001-08-08 |
| CA2324953C (en) | 2008-05-13 |
| IL138477A0 (en) | 2001-10-31 |
| CA2324953A1 (en) | 1999-09-30 |
| CN1188418C (zh) | 2005-02-09 |
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