AP953A - Antimalarial organometallic iron complexes. - Google Patents
Antimalarial organometallic iron complexes. Download PDFInfo
- Publication number
- AP953A AP953A APAP/P/1997/001141A AP9701141A AP953A AP 953 A AP953 A AP 953A AP 9701141 A AP9701141 A AP 9701141A AP 953 A AP953 A AP 953A
- Authority
- AP
- ARIPO
- Prior art keywords
- alkyl
- hydrogen
- group
- hydroxyalkyl
- ferrocene
- Prior art date
Links
- 230000000078 anti-malarial effect Effects 0.000 title claims abstract description 15
- -1 organometallic iron complexes Chemical class 0.000 title claims abstract description 12
- 239000003430 antimalarial agent Substances 0.000 title description 10
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical group [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 201000004792 malaria Diseases 0.000 claims description 8
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000001412 amines Chemical group 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 21
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 abstract description 11
- 235000001258 Cinchona calisaya Nutrition 0.000 abstract description 8
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 abstract description 7
- 229960000948 quinine Drugs 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 description 12
- 125000002524 organometallic group Chemical group 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229910052742 iron Inorganic materials 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000157855 Cinchona Species 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
- 230000009471 action Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000224016 Plasmodium Species 0.000 description 6
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 244000045947 parasite Species 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 208000009182 Parasitemia Diseases 0.000 description 5
- 208000030852 Parasitic disease Diseases 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000006683 Mannich reaction Methods 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229960000901 mepacrine Drugs 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- INDBQLZJXZLFIT-UHFFFAOYSA-N primaquine Chemical compound N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 INDBQLZJXZLFIT-UHFFFAOYSA-N 0.000 description 4
- 229960005179 primaquine Drugs 0.000 description 4
- GPKJTRJOBQGKQK-UHFFFAOYSA-N quinacrine Chemical compound C1=C(OC)C=C2C(NC(C)CCCN(CC)CC)=C(C=CC(Cl)=C3)C3=NC2=C1 GPKJTRJOBQGKQK-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229940033495 antimalarials Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000006138 lithiation reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 2
- 241000224017 Plasmodium berghei Species 0.000 description 2
- 241000223830 Plasmodium yoelii Species 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 125000003410 quininyl group Chemical group 0.000 description 2
- MGCGJBXTNWUHQE-UHFFFAOYSA-N quinoline-4-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=NC2=C1 MGCGJBXTNWUHQE-UHFFFAOYSA-N 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- PBBGSZCBWVPOOL-HDICACEKSA-N 4-[(1r,2s)-1-ethyl-2-(4-hydroxyphenyl)butyl]phenol Chemical compound C1([C@H](CC)[C@H](CC)C=2C=CC(O)=CC=2)=CC=C(O)C=C1 PBBGSZCBWVPOOL-HDICACEKSA-N 0.000 description 1
- YGGTVPCTAKYCSQ-UHFFFAOYSA-N 6-methoxyquinolin-8-amine Chemical compound N1=CC=CC2=CC(OC)=CC(N)=C21 YGGTVPCTAKYCSQ-UHFFFAOYSA-N 0.000 description 1
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 206010022971 Iron Deficiencies Diseases 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- 238000005614 Skraup synthesis reaction Methods 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001414 amino alcohols Chemical group 0.000 description 1
- 229960001441 aminoacridine Drugs 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 229950001996 hexestrol Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- VFJKXAYBWDJZAE-UHFFFAOYSA-N sodium;cyclopenta-1,3-diene;2-(cyclopenta-2,4-diene-1-carbonyl)benzoic acid;iron(2+) Chemical compound [Na+].[Fe+2].C1C=CC=C1.OC(=O)C1=CC=CC=C1C(=O)[C-]1C=CC=C1 VFJKXAYBWDJZAE-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 210000003812 trophozoite Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9505532A FR2733985B1 (fr) | 1995-05-10 | 1995-05-10 | Complexes organometalliques du fer antipaludiques |
| PCT/FR1996/000721 WO1996035698A1 (fr) | 1995-05-10 | 1996-05-10 | Complexes organometalliques du fer antipaludiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9701141A0 AP9701141A0 (en) | 1998-01-31 |
| AP953A true AP953A (en) | 2001-04-02 |
Family
ID=9478836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1997/001141A AP953A (en) | 1995-05-10 | 1996-05-10 | Antimalarial organometallic iron complexes. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6127543A (fr) |
| EP (1) | EP0824536B1 (fr) |
| JP (1) | JP4394163B2 (fr) |
| AP (1) | AP953A (fr) |
| AT (1) | ATE204581T1 (fr) |
| AU (1) | AU718946B2 (fr) |
| BR (1) | BR9608473A (fr) |
| DE (1) | DE69614679T2 (fr) |
| DK (1) | DK0824536T3 (fr) |
| ES (1) | ES2163022T3 (fr) |
| FR (1) | FR2733985B1 (fr) |
| OA (1) | OA10535A (fr) |
| PT (1) | PT824536E (fr) |
| WO (1) | WO1996035698A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0205455D0 (en) | 2002-03-07 | 2002-04-24 | Molecular Sensing Plc | Nucleic acid probes, their synthesis and use |
| FR2952823B1 (fr) | 2009-10-30 | 2012-04-20 | Sanofi Aventis | Utilisation de la ferroquine dans le traitement ou la prevention du paludisme |
| FR2951945B1 (fr) | 2009-11-05 | 2013-08-09 | Sanofi Aventis | Composition pharmaceutique |
| FR2961209B1 (fr) * | 2010-06-11 | 2013-03-01 | Sanofi Aventis | Procede de synthese de la ferroquine par amination reductrice convergente. |
| WO2012104204A1 (fr) | 2011-01-31 | 2012-08-09 | Vifor (International) Ag | Composés à base d'un complexe de fer-hydrate de carbone pour la thérapie intraveineuse du paludisme |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1470210A (en) * | 1974-10-30 | 1977-04-14 | Edwards E | Organometallic derivatives of penicillin |
| EP0004894A1 (fr) * | 1978-04-13 | 1979-10-31 | Bayer Ag | Engrais destiné à apporter du fer aux plantes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0214933A3 (fr) * | 1985-09-03 | 1989-05-24 | Ciba-Geigy Ag | Préparations à base de mélanges pour le traitement de la malaria |
-
1995
- 1995-05-10 FR FR9505532A patent/FR2733985B1/fr not_active Expired - Lifetime
-
1996
- 1996-05-10 DE DE69614679T patent/DE69614679T2/de not_active Expired - Lifetime
- 1996-05-10 AP APAP/P/1997/001141A patent/AP953A/en active
- 1996-05-10 EP EP96916196A patent/EP0824536B1/fr not_active Expired - Lifetime
- 1996-05-10 BR BR9608473-1A patent/BR9608473A/pt not_active IP Right Cessation
- 1996-05-10 US US08/952,093 patent/US6127543A/en not_active Expired - Lifetime
- 1996-05-10 AU AU59037/96A patent/AU718946B2/en not_active Expired
- 1996-05-10 AT AT96916196T patent/ATE204581T1/de active
- 1996-05-10 DK DK96916196T patent/DK0824536T3/da active
- 1996-05-10 ES ES96916196T patent/ES2163022T3/es not_active Expired - Lifetime
- 1996-05-10 PT PT96916196T patent/PT824536E/pt unknown
- 1996-05-10 JP JP53384296A patent/JP4394163B2/ja not_active Expired - Lifetime
- 1996-05-10 WO PCT/FR1996/000721 patent/WO1996035698A1/fr not_active Ceased
-
1997
- 1997-11-10 OA OA70125A patent/OA10535A/fr unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1470210A (en) * | 1974-10-30 | 1977-04-14 | Edwards E | Organometallic derivatives of penicillin |
| EP0004894A1 (fr) * | 1978-04-13 | 1979-10-31 | Bayer Ag | Engrais destiné à apporter du fer aux plantes |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5903796A (en) | 1996-11-29 |
| EP0824536B1 (fr) | 2001-08-22 |
| ES2163022T3 (es) | 2002-01-16 |
| EP0824536A1 (fr) | 1998-02-25 |
| FR2733985B1 (fr) | 1997-07-18 |
| AP9701141A0 (en) | 1998-01-31 |
| AU718946B2 (en) | 2000-05-04 |
| JP4394163B2 (ja) | 2010-01-06 |
| ATE204581T1 (de) | 2001-09-15 |
| FR2733985A1 (fr) | 1996-11-15 |
| JPH11511738A (ja) | 1999-10-12 |
| DK0824536T3 (da) | 2001-12-17 |
| BR9608473A (pt) | 1999-11-30 |
| PT824536E (pt) | 2002-02-28 |
| US6127543A (en) | 2000-10-03 |
| DE69614679T2 (de) | 2002-06-27 |
| OA10535A (fr) | 2002-04-26 |
| WO1996035698A1 (fr) | 1996-11-14 |
| DE69614679D1 (de) | 2001-09-27 |
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