CA2271885A1 - Benzo[1,4]dioxannes substitues utilises comme agents anti-obesite - Google Patents
Benzo[1,4]dioxannes substitues utilises comme agents anti-obesite Download PDFInfo
- Publication number
- CA2271885A1 CA2271885A1 CA002271885A CA2271885A CA2271885A1 CA 2271885 A1 CA2271885 A1 CA 2271885A1 CA 002271885 A CA002271885 A CA 002271885A CA 2271885 A CA2271885 A CA 2271885A CA 2271885 A1 CA2271885 A1 CA 2271885A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- alkyl
- compound
- benzo
- propyl
- 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.)
- Abandoned
Links
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical class C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000000883 anti-obesity agent Substances 0.000 title description 2
- 229940125710 antiobesity agent Drugs 0.000 title description 2
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 21
- -1 furanylalkyl Chemical group 0.000 claims abstract description 18
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- JUJQMJVYCKPQJW-UHFFFAOYSA-N dimethyl 1,4-dioxane-2,3-dicarboxylate Chemical compound COC(=O)C1OCCOC1C(=O)OC JUJQMJVYCKPQJW-UHFFFAOYSA-N 0.000 claims description 4
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- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 claims description 2
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- 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 claims 8
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- XUZZZKIOMAMVTK-UHFFFAOYSA-N 1,4-dioxane-2,3-dicarboxylic acid Chemical compound OC(=O)C1OCCOC1C(O)=O XUZZZKIOMAMVTK-UHFFFAOYSA-N 0.000 description 9
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- IKRROBBTQAMKIS-UHFFFAOYSA-N dipropan-2-yl 1,4-dioxane-2,3-dicarboxylate Chemical compound C(C)(C)OC(=O)C1OCCOC1C(=O)OC(C)C IKRROBBTQAMKIS-UHFFFAOYSA-N 0.000 description 2
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- 230000001684 chronic effect Effects 0.000 description 1
- YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 description 1
- 229950009226 ciglitazone Drugs 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 230000014101 glucose homeostasis Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 102000055647 human CSF2RB Human genes 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 235000015263 low fat diet Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 102200130520 rs121907896 Human genes 0.000 description 1
- 238000002821 scintillation proximity assay Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 210000000636 white adipocyte Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Abstract
Nouveaux composés 1,4-benzodioxannes substitués présentant des propriétés anti-diabétiques, antihyperglycémiques et anti-obésité, représentés par la formule (II) dans laquelle R?1¿ et R?6¿ représentent indépendamment hydrogène, alkyle C¿1? à C¿6?, trifluorométhyle, cyano, alcoxy C¿1? à C¿6?, ou halogène; R?2¿ représente hydrogène ou trialkylsilyle C¿1? à C¿6?; R?3¿ représente hydrogène ou alcoxycarbonyle C¿1? à C¿6?; ou R?2¿ et R?3¿ sont liés pour former le cycle oxazolidinone (III); R?4¿ et R?5¿ représentent indépendamment hydrogène ou alkyle C¿1? à C¿6?; R?7¿ et R?8¿ sont indépendamment OR?9¿ ou NR?10¿R?11¿; R?9¿ représente hydrogène, alkyle C¿1? à C¿12?, cycloalkyle C¿1? à C¿12?, silylalkyle C¿1? à C¿12?, phényle, naphtyle, phényl-alkyle C¿1? à C¿6?, alcoxy C¿1? à C¿6?-alkyle C¿1? à C¿6?, pyridyle, thiophényle, furanyle, imidazolyle, oxazolyle, -CHR?12¿COOR?13¿, -CHR?12¿C(O)R?13¿, -CHR?12¿CONR?10¿R?11¿, -CHR?12¿OCOOR?13¿, ou -CHR?12¿OC(O)R?13¿; R?10¿ et R?11¿ représentent indépendamment hydrogène, alkyle C¿1? à C¿12?, phényle, naphtyle, phényl-alkyle C¿1? à C¿6?, furanylalkyle, ou alcoxycarbonylalkyle; R?12¿ et R?13¿ représentent indépendamment hydrogène, alkyle C¿1? à C¿12?, phényle, naphtyle ou phényl-alkyle C¿1? à C¿6?; et les sels pharmaceutiquement acceptables de ces composés, un sel de ceux-ci; un énantiomère, les conglomérats racémiques et les mélanges diastéréoisomères de ces composés.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77474996A | 1996-12-30 | 1996-12-30 | |
| US08/774,749 | 1996-12-30 | ||
| PCT/US1997/024019 WO1998029405A1 (fr) | 1996-12-30 | 1997-12-18 | Benzo[1,4]dioxannes substitues utilises comme agents anti-obesite |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2271885A1 true CA2271885A1 (fr) | 1998-07-09 |
Family
ID=25102168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002271885A Abandoned CA2271885A1 (fr) | 1996-12-30 | 1997-12-18 | Benzo[1,4]dioxannes substitues utilises comme agents anti-obesite |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0948494A1 (fr) |
| JP (1) | JP2001507704A (fr) |
| KR (1) | KR20000062404A (fr) |
| AU (1) | AU5723098A (fr) |
| BR (1) | BR9714109A (fr) |
| CA (1) | CA2271885A1 (fr) |
| HU (1) | HUP0000768A2 (fr) |
| IL (1) | IL129715A0 (fr) |
| NZ (1) | NZ336235A (fr) |
| WO (1) | WO1998029405A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2303195C (fr) | 1998-07-31 | 2008-01-15 | Nisshin Flour Milling Co., Ltd. | Derives d'acide 1,4-benzodioxine-2-carboxylique optiquement actifs et procede de production |
| WO2004037807A2 (fr) * | 2002-10-22 | 2004-05-06 | Glaxo Group Limited | Composes medicinaux |
| NZ539676A (en) | 2002-10-28 | 2006-10-27 | Glaxo Group Ltd | Phenethanolamine derivative for the treatment of respiratory diseases |
| AR057218A1 (es) * | 2005-12-15 | 2007-11-21 | Astra Ab | Compuestos de oxazolidinona y su uso como pontenciadores del receptor metabotropico de glutamato |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061727A (en) * | 1990-05-04 | 1991-10-29 | American Cyanamid Company | Substituted 5-(2-((2-aryl-2-hydroxyethyl)amino)propyl)-1,3-benzodioxoles |
| US5482971A (en) * | 1993-10-01 | 1996-01-09 | American Cyanamid Company | Beta3 -adrenergic agents and their use in pharmaceutical compositions |
| CA2220759C (fr) * | 1995-05-12 | 2009-01-20 | Nisshin Flour Milling Co. Ltd. | Derives de 1,4-benzodioxine |
-
1997
- 1997-12-18 AU AU57230/98A patent/AU5723098A/en not_active Abandoned
- 1997-12-18 HU HU0000768A patent/HUP0000768A2/hu unknown
- 1997-12-18 BR BR9714109A patent/BR9714109A/pt not_active Application Discontinuation
- 1997-12-18 KR KR1019997005997A patent/KR20000062404A/ko not_active Withdrawn
- 1997-12-18 EP EP97953494A patent/EP0948494A1/fr not_active Withdrawn
- 1997-12-18 NZ NZ336235A patent/NZ336235A/xx unknown
- 1997-12-18 CA CA002271885A patent/CA2271885A1/fr not_active Abandoned
- 1997-12-18 WO PCT/US1997/024019 patent/WO1998029405A1/fr not_active Ceased
- 1997-12-18 JP JP53026098A patent/JP2001507704A/ja active Pending
- 1997-12-18 IL IL12971597A patent/IL129715A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ336235A (en) | 2000-11-24 |
| BR9714109A (pt) | 2000-03-21 |
| IL129715A0 (en) | 2000-02-29 |
| WO1998029405A1 (fr) | 1998-07-09 |
| AU5723098A (en) | 1998-07-31 |
| HUP0000768A2 (hu) | 2001-05-28 |
| EP0948494A1 (fr) | 1999-10-13 |
| JP2001507704A (ja) | 2001-06-12 |
| KR20000062404A (ko) | 2000-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |