KR20010071673A - 항-에이치아이브이 활성을 갖는 디4티의 아릴포스페이트유도체 - Google Patents
항-에이치아이브이 활성을 갖는 디4티의 아릴포스페이트유도체 Download PDFInfo
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- KR20010071673A KR20010071673A KR1020007014949A KR20007014949A KR20010071673A KR 20010071673 A KR20010071673 A KR 20010071673A KR 1020007014949 A KR1020007014949 A KR 1020007014949A KR 20007014949 A KR20007014949 A KR 20007014949A KR 20010071673 A KR20010071673 A KR 20010071673A
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- Prior art keywords
- hiv
- host cell
- compound
- inhibiting
- hiv replication
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- 230000000694 effects Effects 0.000 title abstract description 55
- 230000036436 anti-hiv Effects 0.000 title description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
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- 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
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- 125000000539 amino acid group Chemical group 0.000 claims abstract description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
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- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 7
- NXZJIBSMLSVUEL-ZETCQYMHSA-N phosphono (2S)-2-[(4-bromophenyl)methoxyamino]propanoate Chemical compound OP(=O)(O)OC(=O)[C@H](C)NOCC1=CC=C(Br)C=C1 NXZJIBSMLSVUEL-ZETCQYMHSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 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 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 description 6
- 229940124411 anti-hiv antiviral agent Drugs 0.000 description 6
- 230000003834 intracellular effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 5
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 230000001939 inductive effect Effects 0.000 description 5
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- 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
- 235000021317 phosphate Nutrition 0.000 description 5
- JDFADOFJMLEJSU-QMMMGPOBSA-N phosphono (2S)-2-(phenylmethoxyamino)propanoate Chemical class OP(=O)(O)OC(=O)[C@H](C)NOCC1=CC=CC=C1 JDFADOFJMLEJSU-QMMMGPOBSA-N 0.000 description 5
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- A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
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| US09/107,716 US6030957A (en) | 1998-06-29 | 1998-06-29 | Aryl phosphate derivatives of d4T having anti-HIV activity |
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| PCT/US1999/014774 WO2000000501A1 (en) | 1998-06-29 | 1999-06-29 | ARYL PHOSPHATE DERIVATIVES OF d4T HAVING ANTI-HIV ACTIVITY |
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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 |
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| 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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| 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 |
| AU4846999A (en) | 2000-01-17 |
| 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 |
| 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
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| PA0105 | International application |
Patent event date: 20001228 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |