CA2319836C - Hydroxylation activated prodrugs - Google Patents
Hydroxylation activated prodrugs Download PDFInfo
- Publication number
- CA2319836C CA2319836C CA2319836A CA2319836A CA2319836C CA 2319836 C CA2319836 C CA 2319836C CA 2319836 A CA2319836 A CA 2319836A CA 2319836 A CA2319836 A CA 2319836A CA 2319836 C CA2319836 C CA 2319836C
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- CA
- Canada
- Prior art keywords
- prodrug
- tumour
- compound
- xii
- treatment
- 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.)
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- 229940002612 prodrug Drugs 0.000 title claims abstract description 61
- 239000000651 prodrug Substances 0.000 title claims abstract description 61
- 230000033444 hydroxylation Effects 0.000 title abstract description 9
- 238000005805 hydroxylation reaction Methods 0.000 title abstract description 9
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 31
- 101000725164 Homo sapiens Cytochrome P450 1B1 Proteins 0.000 claims abstract description 10
- 238000007262 aromatic hydroxylation reaction Methods 0.000 claims abstract description 9
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000002207 metabolite Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
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- 239000003814 drug Substances 0.000 claims description 10
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- 239000003085 diluting agent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
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- 239000000243 solution Substances 0.000 description 14
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- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 8
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- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 7
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- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 2
- KGUGYOFXEFZJMR-VQHVLOKHSA-N (e)-3-(2,4-dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound COC1=CC(OC)=CC=C1\C=C\C(=O)C1=CC(OC)=C(OC)C(OC)=C1 KGUGYOFXEFZJMR-VQHVLOKHSA-N 0.000 description 2
- AYICHAKPDXZAMD-RMKNXTFCSA-N (e)-3-(4-hydroxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound COC1=C(OC)C(OC)=CC(C(=O)\C=C\C=2C=CC(O)=CC=2)=C1 AYICHAKPDXZAMD-RMKNXTFCSA-N 0.000 description 2
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- VSYPHCNZDCVVMG-NTEUORMPSA-N (z)-3-(4-methoxyphenyl)-2-pyridin-3-ylprop-2-enenitrile Chemical compound C1=CC(OC)=CC=C1\C=C(/C#N)C1=CC=CN=C1 VSYPHCNZDCVVMG-NTEUORMPSA-N 0.000 description 2
- GGFQQRXTLIJXNY-AATRIKPKSA-N 1,2,3-trimethoxy-5-[(e)-2-(4-methoxyphenyl)ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC(OC)=C(OC)C(OC)=C1 GGFQQRXTLIJXNY-AATRIKPKSA-N 0.000 description 2
- GGFQQRXTLIJXNY-WAYWQWQTSA-N 1,2,3-trimethoxy-5-[(z)-2-(4-methoxyphenyl)ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 GGFQQRXTLIJXNY-WAYWQWQTSA-N 0.000 description 2
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
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- -1 3,5-dihydroxyphenyl Chemical group 0.000 description 2
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
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- IKMOZUDCUBMIRL-FNORWQNLSA-N (e)-3-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound C1=C(O)C(OC)=CC=C1\C=C\C(=O)C1=CC(OC)=C(OC)C(OC)=C1 IKMOZUDCUBMIRL-FNORWQNLSA-N 0.000 description 1
- NNTQWEXILXMDGK-JLHYYAGUSA-N (e)-3-(4-methoxyphenyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1\C=C(/C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 NNTQWEXILXMDGK-JLHYYAGUSA-N 0.000 description 1
- FNFSOYGIQWSIEX-UHFFFAOYSA-N 1-(3,4,5-trimethoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(OC)=C(OC)C(OC)=C1 FNFSOYGIQWSIEX-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- REFSKZBXDZGOCW-ONEGZZNKSA-N 2-methoxy-5-[(e)-2-(4-methoxyphenyl)ethenyl]phenol Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC=C(OC)C(O)=C1 REFSKZBXDZGOCW-ONEGZZNKSA-N 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000008142 Cytochrome P-450 CYP1A1 Human genes 0.000 description 1
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
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- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
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- 231100000065 noncytotoxic Toxicity 0.000 description 1
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- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/36—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9802522.4A GB9802522D0 (en) | 1998-02-06 | 1998-02-06 | Hydroxylation activated prodrugs |
| GB9802522.4 | 1998-02-06 | ||
| US09/115,015 US6214886B1 (en) | 1998-02-06 | 1998-07-14 | Hydroxylation activated prodrugs |
| US09/115,015 | 1998-07-14 | ||
| PCT/GB1999/000155 WO1999040056A1 (en) | 1998-02-06 | 1999-02-02 | Hydroxylation activated prodrugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2319836A1 CA2319836A1 (en) | 1999-08-12 |
| CA2319836C true CA2319836C (en) | 2010-11-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2319836A Expired - Fee Related CA2319836C (en) | 1998-02-06 | 1999-02-02 | Hydroxylation activated prodrugs |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6677383B1 (enExample) |
| EP (1) | EP1051383B1 (enExample) |
| JP (1) | JP4642226B2 (enExample) |
| AT (1) | ATE272040T1 (enExample) |
| AU (1) | AU2173899A (enExample) |
| CA (1) | CA2319836C (enExample) |
| DE (1) | DE69918950T2 (enExample) |
| ES (1) | ES2226332T3 (enExample) |
| WO (1) | WO1999040056A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2319836C (en) | 1998-02-06 | 2010-11-23 | De Montfort University | Hydroxylation activated prodrugs |
| GB2334256A (en) | 1998-02-12 | 1999-08-18 | Univ Montfort | Hydroxylation activated prodrugs |
| US7321050B2 (en) | 1999-12-06 | 2008-01-22 | Welichem Biotech Inc. | Anti-inflammatory and psoriasis treatment and protein kinase inhibition by hydroxy stilbenes and novel stilbene derivatives and analogues |
| US20030171429A1 (en) * | 1999-12-06 | 2003-09-11 | Genhui Chen | Anti-inflammatory and psoriasis treatment and protein kinase inhibition by hydroxyltilbenes and novel stilbene derivatives and analogues |
| GB0007401D0 (en) | 2000-03-27 | 2000-05-17 | Cancer Res Campaign Tech | Substituted chalcones as therapeeutic compounds |
| WO2001079158A2 (en) * | 2000-04-13 | 2001-10-25 | Hsc Research And Development Limited Partnership | Compounds for modulating cell proliferation |
| US7192977B2 (en) | 2001-02-22 | 2007-03-20 | School Of Pharmacy | Benz-indole and benzo-quinoline derivatives as prodrugs for tumor treatment |
| ES2299560T3 (es) | 2001-02-22 | 2008-06-01 | University Of Bradford | Derivados de pirrolindol y de pirroloquinolina como profarmacos para el tratamiento de tumores. |
| US6589997B2 (en) * | 2001-06-29 | 2003-07-08 | North Shore-Long Island Jewish Health System | Small-molecule modulators of hepatocyte growth factor/scatter factor activities |
| GB0123780D0 (en) * | 2001-10-03 | 2001-11-21 | Cancer Res Ventures Ltd | Substituted chalcones as therapeutic agents |
| GB0123777D0 (en) | 2001-10-03 | 2001-11-21 | Cancer Res Ventures Ltd | Substituted chalcones as therapeutic agents |
| US6919324B2 (en) * | 2001-10-26 | 2005-07-19 | Oxigene, Inc. | Functionalized stilbene derivatives as improved vascular targeting agents |
| GB0126889D0 (en) * | 2001-11-08 | 2002-01-02 | Paterson Inst For Cancer Res | Compounds and their uses |
| EP1542989B1 (en) * | 2002-07-31 | 2007-04-18 | Critical Outcome Technologies, Inc. | Protein tyrosine kinase inhibitors |
| EP1551824B1 (en) * | 2002-10-09 | 2007-12-12 | Critical Outcome Technologies, Inc. | Protein tyrosine kinase inhibitors |
| CA2515174A1 (en) * | 2003-02-04 | 2004-08-19 | Kabushiki Kaisha Yakult Honsha | Breast cancer resistance protein (bcrp) inhibitor |
| WO2005092904A1 (en) * | 2004-03-26 | 2005-10-06 | Hsc Research And Development Limited Partnership | Novel compounds for modulating cell proliferation |
| NZ562143A (en) | 2005-03-30 | 2010-12-24 | Yakult Honsha Kk | Dimethoxyphenyl-acrylonitrile derivatives and uses thereof in the treatment of cancer |
| CA2673683C (en) | 2007-01-11 | 2014-07-29 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| US8138191B2 (en) * | 2007-01-11 | 2012-03-20 | Critical Outcome Technologies Inc. | Inhibitor compounds and cancer treatment methods |
| US7784455B1 (en) * | 2007-09-18 | 2010-08-31 | Chong Carlton Le Loong | Reusable pellet shooting grenade |
| WO2009079797A1 (en) | 2007-12-26 | 2009-07-02 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| GB0803071D0 (en) * | 2008-02-20 | 2008-03-26 | Care Technologies Inc | Cancer detection methods and techniques |
| GB0907551D0 (en) | 2009-05-01 | 2009-06-10 | Univ Dundee | Treatment or prophylaxis of proliferative conditions |
| CA2794952C (en) | 2010-04-01 | 2018-05-15 | Critical Outcome Technologies Inc. | Compounds and method for treatment of hiv |
| CA3091027A1 (en) | 2018-02-02 | 2019-08-08 | Maverix Oncology, Inc. | Small molecule drug conjugates of gemcitabine monophosphate |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6176433A (ja) * | 1984-09-21 | 1986-04-18 | Toyobo Co Ltd | 新規なカルコン誘導体 |
| US5773435A (en) | 1987-08-04 | 1998-06-30 | Bristol-Myers Squibb Company | Prodrugs for β-lactamase and uses thereof |
| AU632992B2 (en) * | 1987-12-24 | 1993-01-21 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Pharmaceutical compositions comprising benzylidene- and cinnamylidene-malononitrile derivatives for the inhibition of proliferative processes in mammalian cells, certain such novel compounds and their preparation |
| US5287386A (en) | 1991-03-27 | 1994-02-15 | Thinking Machines Corporation | Differential driver/receiver circuit |
| US5430062A (en) * | 1992-05-21 | 1995-07-04 | Research Corporation Technologies, Inc. | Stilbene derivatives as anticancer agents |
| DE4236237A1 (de) | 1992-10-27 | 1994-04-28 | Behringwerke Ag | Prodrugs, ihre Herstellung und Verwendung als Arzneimittel |
| DE4309344A1 (de) | 1993-03-23 | 1994-09-29 | Gerhard Prof Dr Eisenbrand | Antineoplastische Mittel mit verstärkter Wirksamkeit |
| US5276058A (en) * | 1993-06-09 | 1994-01-04 | Nippon Hypox Laboratories Incorporated | 3,4-dihydroxychalcone derivatives |
| EP0647450A1 (en) | 1993-09-09 | 1995-04-12 | BEHRINGWERKE Aktiengesellschaft | Improved prodrugs for enzyme mediated activation |
| FR2710798B1 (fr) | 1993-09-27 | 1995-11-10 | Alcatel Mobile Comm France | Chaîne d'amplification en mode de courant, amplificateur opérationnel, cellule de gain et élément d'amplification correspondants. |
| JPH08188546A (ja) * | 1995-01-04 | 1996-07-23 | Kyowa Hakko Kogyo Co Ltd | カルコン誘導体 |
| GB9519490D0 (en) | 1995-09-25 | 1995-11-29 | Melvin William T | Use of a cytochrome P450 enzyme in tumour cells as a marker and target |
| US5966032A (en) | 1996-09-27 | 1999-10-12 | Northern Telecom Limited | BiCMOS transceiver (driver and receiver) for gigahertz operation |
| GB9802522D0 (en) | 1998-02-06 | 1998-04-01 | Montford University De | Hydroxylation activated prodrugs |
| CA2319836C (en) | 1998-02-06 | 2010-11-23 | De Montfort University | Hydroxylation activated prodrugs |
| GB2334256A (en) | 1998-02-12 | 1999-08-18 | Univ Montfort | Hydroxylation activated prodrugs |
| WO1999040944A2 (en) | 1998-02-12 | 1999-08-19 | De Montfort University | Hydroxylation activated drug release |
-
1999
- 1999-02-02 CA CA2319836A patent/CA2319836C/en not_active Expired - Fee Related
- 1999-02-02 ES ES99901732T patent/ES2226332T3/es not_active Expired - Lifetime
- 1999-02-02 EP EP99901732A patent/EP1051383B1/en not_active Expired - Lifetime
- 1999-02-02 AU AU21738/99A patent/AU2173899A/en not_active Abandoned
- 1999-02-02 WO PCT/GB1999/000155 patent/WO1999040056A1/en not_active Ceased
- 1999-02-02 DE DE69918950T patent/DE69918950T2/de not_active Expired - Lifetime
- 1999-02-02 AT AT99901732T patent/ATE272040T1/de active
- 1999-02-02 JP JP2000530488A patent/JP4642226B2/ja not_active Expired - Fee Related
-
2000
- 2000-08-07 US US09/633,699 patent/US6677383B1/en not_active Expired - Lifetime
-
2001
- 2001-01-19 US US09/765,861 patent/US6346550B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6677383B1 (en) | 2004-01-13 |
| WO1999040056A1 (en) | 1999-08-12 |
| ES2226332T3 (es) | 2005-03-16 |
| EP1051383B1 (en) | 2004-07-28 |
| DE69918950D1 (de) | 2004-09-02 |
| DE69918950T2 (de) | 2005-07-28 |
| AU2173899A (en) | 1999-08-23 |
| JP4642226B2 (ja) | 2011-03-02 |
| ATE272040T1 (de) | 2004-08-15 |
| EP1051383A1 (en) | 2000-11-15 |
| US6346550B2 (en) | 2002-02-12 |
| JP2002502836A (ja) | 2002-01-29 |
| US20010021717A1 (en) | 2001-09-13 |
| CA2319836A1 (en) | 1999-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170202 |