AU4846999A - Aryl phosphate derivatives of d4t having anti-hiv activity - Google Patents
Aryl phosphate derivatives of d4t having anti-hiv activity Download PDFInfo
- Publication number
- AU4846999A AU4846999A AU48469/99A AU4846999A AU4846999A AU 4846999 A AU4846999 A AU 4846999A AU 48469/99 A AU48469/99 A AU 48469/99A AU 4846999 A AU4846999 A AU 4846999A AU 4846999 A AU4846999 A AU 4846999A
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- Prior art keywords
- compound
- composition
- cells
- bromo
- electron
- Prior art date
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- -1 Aryl phosphate derivatives Chemical class 0.000 title abstract description 30
- 230000000694 effects Effects 0.000 title description 50
- 230000036436 anti-hiv Effects 0.000 title description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims abstract description 8
- 125000000539 amino acid group Chemical group 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 102
- 238000000034 method Methods 0.000 claims description 39
- 230000002401 inhibitory effect Effects 0.000 claims description 31
- 230000010076 replication Effects 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 26
- 125000001246 bromo group Chemical group Br* 0.000 claims description 14
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000002777 nucleoside Substances 0.000 claims description 10
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 9
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229940024606 amino acid Drugs 0.000 claims description 5
- 235000001014 amino acid Nutrition 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 4
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 4
- 235000004279 alanine Nutrition 0.000 claims description 4
- 125000004799 bromophenyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229940113082 thymine Drugs 0.000 claims description 4
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical group O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 3
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229940104302 cytosine Drugs 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 229940035893 uracil Drugs 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 229940037201 oris Drugs 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 abstract description 27
- 238000006467 substitution reaction Methods 0.000 abstract description 17
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 abstract description 8
- 229940124411 anti-hiv antiviral agent Drugs 0.000 abstract description 8
- 239000003112 inhibitor Substances 0.000 abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 4
- 230000001472 cytotoxic effect Effects 0.000 abstract description 4
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 4
- 239000011574 phosphorus Substances 0.000 abstract description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 abstract description 2
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 74
- 102000006601 Thymidine Kinase Human genes 0.000 description 51
- 108020004440 Thymidine kinase Proteins 0.000 description 51
- 238000005481 NMR spectroscopy Methods 0.000 description 50
- 210000004027 cell Anatomy 0.000 description 49
- 230000002950 deficient Effects 0.000 description 44
- 229960002555 zidovudine Drugs 0.000 description 44
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 40
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 39
- 238000004128 high performance liquid chromatography Methods 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000006460 hydrolysis reaction Methods 0.000 description 24
- 230000007062 hydrolysis Effects 0.000 description 23
- 210000001744 T-lymphocyte Anatomy 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 16
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 16
- 230000014759 maintenance of location Effects 0.000 description 16
- 230000000840 anti-viral effect Effects 0.000 description 15
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 15
- 239000002207 metabolite Substances 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 208000031886 HIV Infections Diseases 0.000 description 13
- 229910019142 PO4 Inorganic materials 0.000 description 13
- 239000010452 phosphate Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 11
- PAAOCMOWNQETER-QMMMGPOBSA-N [hydroxy(phenoxy)phosphoryl] (2S)-2-(methoxyamino)propanoate Chemical class CON[C@@H](C)C(=O)OP(O)(=O)OC1=CC=CC=C1 PAAOCMOWNQETER-QMMMGPOBSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000003013 cytotoxicity Effects 0.000 description 10
- 231100000135 cytotoxicity Toxicity 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229940104230 thymidine Drugs 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 7
- 230000004060 metabolic process Effects 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 7
- VGNCBRNRHXEODV-XXVHXNRLSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-6-dodecoxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@H](O)[C@H](C(O2)(C(O)=O)C(O)(C(O1)C(O)=O)C(O)=O)OCCCCCCCCCCCC)C1=CC=CC=C1 VGNCBRNRHXEODV-XXVHXNRLSA-N 0.000 description 6
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 6
- 108010051152 Carboxylesterase Proteins 0.000 description 6
- 102000013392 Carboxylesterase Human genes 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- 230000003834 intracellular effect Effects 0.000 description 6
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- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WKMSVJAOGVVHFO-RFXRWSEHSA-N [chloro(phenoxy)phosphoryl] (2s)-2-(methoxyamino)propanoate Chemical class CON[C@@H](C)C(=O)OP(Cl)(=O)OC1=CC=CC=C1 WKMSVJAOGVVHFO-RFXRWSEHSA-N 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 230000037353 metabolic pathway Effects 0.000 description 5
- 150000004712 monophosphates Chemical class 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- MWDVCHRYCKXEBY-LBPRGKRZSA-N 3-chloro-n-[2-oxo-2-[[(1s)-1-phenylethyl]amino]ethyl]benzamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)CNC(=O)C1=CC=CC(Cl)=C1 MWDVCHRYCKXEBY-LBPRGKRZSA-N 0.000 description 4
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- 210000004185 liver Anatomy 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000001226 triphosphate Substances 0.000 description 4
- 230000029812 viral genome replication Effects 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 238000013461 design Methods 0.000 description 3
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- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 235000011178 triphosphate Nutrition 0.000 description 3
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical class OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 3
- KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 description 2
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| US09/107,716 US6030957A (en) | 1998-06-29 | 1998-06-29 | Aryl phosphate derivatives of d4T having anti-HIV activity |
| US09107716 | 1998-06-30 | ||
| PCT/US1999/014774 WO2000000501A1 (en) | 1998-06-29 | 1999-06-29 | ARYL PHOSPHATE DERIVATIVES OF d4T HAVING ANTI-HIV ACTIVITY |
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| AU4846999A true AU4846999A (en) | 2000-01-17 |
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| US20070015733A1 (en) * | 1998-06-29 | 2007-01-18 | Parker Hughes Institute | Aryl Phosphate Derivatives of d4T having Activity Against Resistant HIV Strains |
| US7144874B2 (en) * | 2002-10-25 | 2006-12-05 | Parker Hughes Institute | Aryl phosphate derivatives of d4T having activity against resistant HIV strains |
| WO2000056750A1 (en) * | 1999-03-19 | 2000-09-28 | Parker Hughes Institute | One pot synthesis of 5'-hydroxy phosphorylated nucleoside derivatives, and compounds formed thereby |
| US6825177B2 (en) * | 2000-10-30 | 2004-11-30 | Parker Hughes Institute | Aryl phosphate derivatives of d4T with potent anti-viral activity |
| ATE297940T1 (de) * | 2000-11-13 | 2005-07-15 | Parker Hughes Inst | Arylphosphatderivate von d4t |
| AU2003239901A1 (en) * | 2002-05-28 | 2003-12-12 | Kathy M. Ensrud | Crisp polypeptides as contraceptives and inhibitors of sperm capacitation |
| US20030236218A1 (en) * | 2002-06-12 | 2003-12-25 | Uckun Fatih M. | Aryl phosphate derivatives of d4T with selective activity against adenovirus and HIV |
| US20040076931A1 (en) * | 2002-10-18 | 2004-04-22 | Cashflow Technologies, Inc. | Educational interactive games |
| US20040077607A1 (en) * | 2002-10-21 | 2004-04-22 | Uckun Fatih M. | Aryl phosphate derivatives of d4T with potent anti-viral activity against hemorrhagic fever viruses |
| GB0401088D0 (en) | 2004-01-19 | 2004-02-18 | Univ Cardiff | Phosphoramidate derivatives |
| EP1773355B1 (en) * | 2004-06-24 | 2014-06-25 | Merck Sharp & Dohme Corp. | Nucleoside aryl phosphoramidates for the treatment of rna-dependent rna viral infection |
| WO2006026656A1 (en) * | 2004-08-31 | 2006-03-09 | Parker Hughes Institute | Cytotoxic nucleoside analog compound 003 for treating cancer |
| EP1827460A4 (en) * | 2004-12-09 | 2012-03-14 | Univ Minnesota | NUCLEOSIDE WITH ANTIVIRAL AND ANTI-CANCER EFFECT |
| US10618013B2 (en) * | 2005-03-09 | 2020-04-14 | The Regents Of The University Of California | Nanocomposite membranes and methods of making and using same |
| US7892618B2 (en) * | 2005-03-21 | 2011-02-22 | Sony Corporation | Deterring theft of optical media |
| GB0623493D0 (en) * | 2006-11-24 | 2007-01-03 | Univ Cardiff | Chemical compounds |
| EP2623104A1 (en) * | 2009-03-20 | 2013-08-07 | Alios Biopharma, Inc. | Substituted nucleoside and nucleotide analogs |
| CA2810928A1 (en) | 2010-09-22 | 2012-03-29 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| US9095599B2 (en) | 2011-01-03 | 2015-08-04 | Nanjing Molecular Research, Inc. | O-(substituted benzyl) phosphoramidate compounds and therapeutic use |
| CA2860234A1 (en) | 2011-12-22 | 2013-06-27 | Alios Biopharma, Inc. | Substituted phosphorothioate nucleotide analogs |
| HK1206362A1 (zh) | 2012-03-21 | 2016-01-08 | Alios Biopharma, Inc. | 硫代氨基磷酸酯核苷酸前藥的固體形式 |
| US9012427B2 (en) | 2012-03-22 | 2015-04-21 | Alios Biopharma, Inc. | Pharmaceutical combinations comprising a thionucleotide analog |
| CN105705511A (zh) | 2013-04-12 | 2016-06-22 | 艾其林医药公司 | 用于治疗hcv的氘化核苷前药 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4707362A (en) | 1985-02-15 | 1987-11-17 | Biotek, Inc. | Sustained release composition |
| US4841039A (en) | 1986-05-01 | 1989-06-20 | Emory University | 2',3'-dideoxy-5-substituted uridines and related compounds as antiviral agents |
| US4983393A (en) | 1987-07-21 | 1991-01-08 | Maximed Corporation | Intra-vaginal device and method for sustained drug release |
| JPH06189998A (ja) | 1992-11-06 | 1994-07-12 | C & Co:Yugen | コンド―ム |
| CA2130265A1 (en) | 1992-12-18 | 1994-07-07 | Edward E. Knaus | Dihydropyrimidine nucleosides with antiviral properties |
| ZA947572B (en) | 1993-09-29 | 1995-09-28 | Hampton Roads Medical College | Contraceptive compositions |
| US5672698A (en) * | 1993-11-15 | 1997-09-30 | Bristol-Myers Squibb Co. | Preparation of 2',3'-didehydro-3'-deoxythymidine from 5-methyluridine |
| US5659023A (en) * | 1995-02-01 | 1997-08-19 | Gilead Sciences, Inc. | Nucleotide analogues |
| GB9505025D0 (en) * | 1995-03-13 | 1995-05-03 | Medical Res Council | Chemical compounds |
| IL126804A0 (en) | 1996-05-09 | 1999-08-17 | Bergeron Michel G | Formulation for use in the prevention of pathogen induced diseases including hiv and hsv |
| US6030957A (en) | 1998-06-29 | 2000-02-29 | Wayne Hughes Institute | Aryl phosphate derivatives of d4T having anti-HIV activity |
-
1998
- 1998-06-29 US US09/107,716 patent/US6030957A/en not_active Expired - Fee Related
-
1999
- 1999-06-29 CA CA002336285A patent/CA2336285A1/en not_active Abandoned
- 1999-06-29 AT AT99932080T patent/ATE277940T1/de not_active IP Right Cessation
- 1999-06-29 EP EP99932080A patent/EP1090018B1/en not_active Expired - Lifetime
- 1999-06-29 WO PCT/US1999/014774 patent/WO2000000501A1/en not_active Ceased
- 1999-06-29 DE DE69920696T patent/DE69920696T2/de not_active Expired - Fee Related
- 1999-06-29 HU HU0102527A patent/HUP0102527A3/hu unknown
- 1999-06-29 AU AU48469/99A patent/AU4846999A/en not_active Abandoned
- 1999-06-29 IL IL14038899A patent/IL140388A0/xx unknown
- 1999-06-29 KR KR1020007014949A patent/KR20010071673A/ko not_active Withdrawn
- 1999-06-29 BR BR9911685-5A patent/BR9911685A/pt not_active Application Discontinuation
- 1999-06-29 JP JP2000557262A patent/JP2002519355A/ja active Pending
- 1999-06-29 CN CN99810072A patent/CN1314909A/zh active Pending
- 1999-11-29 US US09/450,082 patent/US6503890B1/en not_active Expired - Fee Related
- 1999-12-15 US US09/464,516 patent/US6350736B1/en not_active Expired - Fee Related
-
2000
- 2000-04-13 US US09/548,492 patent/US6528495B1/en not_active Expired - Fee Related
- 2000-04-13 US US09/548,494 patent/US6670336B1/en not_active Expired - Fee Related
- 2000-04-13 US US09/548,496 patent/US6537975B1/en not_active Expired - Fee Related
- 2000-12-28 NO NO20006685A patent/NO20006685L/no not_active Application Discontinuation
-
2003
- 2003-12-01 US US10/726,073 patent/US7071176B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0102527A3 (en) | 2002-04-29 |
| US6030957A (en) | 2000-02-29 |
| EP1090018A1 (en) | 2001-04-11 |
| BR9911685A (pt) | 2001-12-18 |
| ATE277940T1 (de) | 2004-10-15 |
| US6350736B1 (en) | 2002-02-26 |
| EP1090018B1 (en) | 2004-09-29 |
| US7071176B2 (en) | 2006-07-04 |
| HUP0102527A2 (hu) | 2001-12-28 |
| JP2002519355A (ja) | 2002-07-02 |
| US6503890B1 (en) | 2003-01-07 |
| NO20006685D0 (no) | 2000-12-28 |
| CN1314909A (zh) | 2001-09-26 |
| DE69920696D1 (de) | 2004-11-04 |
| NO20006685L (no) | 2001-02-28 |
| KR20010071673A (ko) | 2001-07-31 |
| US6528495B1 (en) | 2003-03-04 |
| CA2336285A1 (en) | 2000-01-06 |
| US6670336B1 (en) | 2003-12-30 |
| WO2000000501A1 (en) | 2000-01-06 |
| IL140388A0 (en) | 2002-02-10 |
| US6537975B1 (en) | 2003-03-25 |
| US20040171577A1 (en) | 2004-09-02 |
| DE69920696T2 (de) | 2006-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |