ZA200307793B - Tricyclic alkylhydroxamates, their preparation and their use as cell proliferation inhibitors. - Google Patents
Tricyclic alkylhydroxamates, their preparation and their use as cell proliferation inhibitors. Download PDFInfo
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- ZA200307793B ZA200307793B ZA200307793A ZA200307793A ZA200307793B ZA 200307793 B ZA200307793 B ZA 200307793B ZA 200307793 A ZA200307793 A ZA 200307793A ZA 200307793 A ZA200307793 A ZA 200307793A ZA 200307793 B ZA200307793 B ZA 200307793B
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- ZA
- South Africa
- Prior art keywords
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- formula
- yloxy
- compound
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- 238000002360 preparation method Methods 0.000 title claims description 8
- 230000004663 cell proliferation Effects 0.000 title claims description 6
- 239000003112 inhibitor Substances 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 57
- -1 nitro, amino Chemical group 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 102000003964 Histone deacetylase Human genes 0.000 claims description 9
- 108090000353 Histone deacetylase Proteins 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
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- 239000002253 acid Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
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- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
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- 239000003054 catalyst Substances 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- AKVLPQQYGLOPQN-UHFFFAOYSA-N 8-bromo-n-phenylmethoxyoctanamide Chemical compound BrCCCCCCCC(=O)NOCC1=CC=CC=C1 AKVLPQQYGLOPQN-UHFFFAOYSA-N 0.000 description 4
- GWPGDZPXOZATKL-UHFFFAOYSA-N 9h-carbazol-2-ol Chemical compound C1=CC=C2C3=CC=C(O)C=C3NC2=C1 GWPGDZPXOZATKL-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 230000006907 apoptotic process Effects 0.000 description 4
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- 239000002184 metal Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000013518 transcription Methods 0.000 description 4
- 230000035897 transcription Effects 0.000 description 4
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- HBCJSPZAXFAJLO-UHFFFAOYSA-N 6-(9h-carbazol-2-yloxy)hexanoic acid Chemical compound C1=CC=C2C3=CC=C(OCCCCCC(=O)O)C=C3NC2=C1 HBCJSPZAXFAJLO-UHFFFAOYSA-N 0.000 description 2
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- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000007423 screening 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
- 239000002002 slurry Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Pyrane Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01109428 | 2001-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200307793B true ZA200307793B (en) | 2005-01-06 |
Family
ID=8177162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200307793A ZA200307793B (en) | 2001-04-23 | 2003-10-06 | Tricyclic alkylhydroxamates, their preparation and their use as cell proliferation inhibitors. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6512123B2 (ko) |
| EP (1) | EP1385837B1 (ko) |
| JP (1) | JP4142453B2 (ko) |
| KR (1) | KR100591501B1 (ko) |
| CN (1) | CN1310904C (ko) |
| AR (1) | AR035455A1 (ko) |
| AT (1) | ATE306480T1 (ko) |
| AU (1) | AU2002254991B2 (ko) |
| BR (1) | BR0209064A (ko) |
| CA (1) | CA2442994A1 (ko) |
| CR (1) | CR9430A (ko) |
| DE (1) | DE60206616T2 (ko) |
| ES (1) | ES2249572T3 (ko) |
| MX (1) | MXPA03009132A (ko) |
| WO (1) | WO2002085883A1 (ko) |
| ZA (1) | ZA200307793B (ko) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6777217B1 (en) | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
| US6822267B1 (en) * | 1997-08-20 | 2004-11-23 | Advantest Corporation | Signal transmission circuit, CMOS semiconductor device, and circuit board |
| US20030129724A1 (en) | 2000-03-03 | 2003-07-10 | Grozinger Christina M. | Class II human histone deacetylases, and uses related thereto |
| US7244853B2 (en) | 2001-05-09 | 2007-07-17 | President And Fellows Of Harvard College | Dioxanes and uses thereof |
| US7154002B1 (en) | 2002-10-08 | 2006-12-26 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| US7250514B1 (en) | 2002-10-21 | 2007-07-31 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| WO2004067480A2 (en) * | 2003-01-25 | 2004-08-12 | Oxford Glycosciences (Uk) Ltd | Substituted phenylurea derivatives as hdac inhibitors |
| US7381825B2 (en) * | 2003-03-17 | 2008-06-03 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| DK2238982T3 (da) | 2003-06-27 | 2013-01-28 | Astellas Pharma Inc | Terapeutisk middel til blødt væv-sarcom |
| WO2005058298A2 (en) * | 2003-12-10 | 2005-06-30 | Wisconsin Alumni Research Foundation | Fk228 analogs and their use as hdac-inhibitors |
| WO2005066151A2 (en) * | 2003-12-19 | 2005-07-21 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| WO2005065681A1 (en) * | 2003-12-19 | 2005-07-21 | Takeda San Diego, Inc. | N- hydroxy-3-(3-(1h-imidazol-2-yl)-phenyl)-acrylamide derivatives and related compounds as histone deacetylase (hdac) inhibitors for the treatment of cancer |
| US20060128660A1 (en) * | 2004-12-10 | 2006-06-15 | Wisconsin Alumni Research Foundation | FK228 analogs and methods of making and using the same |
| WO2006066133A2 (en) * | 2004-12-16 | 2006-06-22 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| IT1362675B (it) * | 2005-03-15 | 2009-06-25 | Menarini Internat Operations Luxembourg Sa | N-idrossiammidi -sostituiti con gruppi triciclici come inibitori dell'istone deacelitasi,loro preparazione ed impiego in formulazioni farmaceutiche |
| CA2937005A1 (en) | 2005-03-22 | 2006-09-28 | President And Fellows Of Harvard College | Treatment of protein degradation disorders |
| WO2006122319A2 (en) * | 2005-05-11 | 2006-11-16 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| PL1901729T3 (pl) * | 2005-05-13 | 2012-07-31 | Topotarget Uk Ltd | Formulacje farmaceutyczne inhibitorów hdac |
| BRPI0613429A2 (pt) * | 2005-07-14 | 2009-02-10 | Takeda San Diego Inc | inibidores de histona desacetilase |
| WO2007077111A1 (en) * | 2005-12-30 | 2007-07-12 | F. Hoffmann-La Roche Ag | Compounds and methods for carbazole synthesis |
| JP2009525955A (ja) * | 2006-01-13 | 2009-07-16 | タケダ サン ディエゴ インコーポレイテッド | ヒストンデアセチラーゼ阻害剤 |
| BRPI0707826B1 (pt) | 2006-02-14 | 2022-04-19 | Dana-Farber Cancer Institute, Inc. | Compostos inibidores de histona desacetilase, composição farmacêutica e uso dos referidos compostos |
| AU2007345292B2 (en) | 2006-02-14 | 2013-10-31 | Dana-Farber Cancer Institute, Inc. | Bifunctional histone deacetylase inhibitors |
| US8304451B2 (en) * | 2006-05-03 | 2012-11-06 | President And Fellows Of Harvard College | Histone deacetylase and tubulin deacetylase inhibitors |
| ES2288803B1 (es) * | 2006-07-07 | 2008-12-16 | Universidad De Granada | Derivados de benzo(d)isotiazoles como inhibidores de las histonas desacetilasas. |
| JP5583406B2 (ja) * | 2006-10-28 | 2014-09-03 | メチルジーン インコーポレイテッド | ヒストンデアセチラーゼの阻害剤 |
| AU2013205135B2 (en) * | 2006-10-28 | 2015-11-05 | Forum Pharmaceuticals Inc. | Inhibitors of histone deacetylase |
| CA2731730C (en) | 2008-07-23 | 2017-06-13 | President And Fellows Of Harvard College | Deacetylase inhibitors and uses thereof |
| JP2012051804A (ja) * | 2008-12-26 | 2012-03-15 | Kyoto Univ | Ｅｇ５阻害剤 |
| WO2011019393A2 (en) | 2009-08-11 | 2011-02-17 | President And Fellows Of Harvard College | Class- and isoform-specific hdac inhibitors and uses thereof |
| WO2015115410A1 (ja) * | 2014-01-28 | 2015-08-06 | 株式会社日本触媒 | 水素化反応方法 |
| US10011611B2 (en) | 2015-08-14 | 2018-07-03 | Reaction Biology Corp. | Histone deacetylase inhibitors and methods for use thereof |
| WO2023020416A1 (zh) * | 2021-08-16 | 2023-02-23 | 勤浩医药（苏州）有限公司 | 三环化合物、包含其的药物组合物及其用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2208893A1 (de) | 1972-02-25 | 1973-08-30 | Boehringer Mannheim Gmbh | Tricyclische alpha-oxy-carbonsaeurederivate und verfahren zur herstellung derselben |
| US5369108A (en) * | 1991-10-04 | 1994-11-29 | Sloan-Kettering Institute For Cancer Research | Potent inducers of terminal differentiation and methods of use thereof |
| ZA938897B (en) * | 1992-12-01 | 1994-08-01 | Smithkline Beecham Corp | Antioxidant neuroprotective use of and method of treatment using hydroxycarbazole compounds |
| EP0931045A1 (en) * | 1996-09-04 | 1999-07-28 | Warner-Lambert Company | Matrix metalloproteinase inhibitors and their therapeutic uses |
| AUPO721997A0 (en) * | 1997-06-06 | 1997-07-03 | Queensland Institute Of Medical Research, The | Anticancer compounds |
| AU7320100A (en) * | 1999-09-24 | 2001-04-24 | Ono Pharmaceutical Co. Ltd. | Hydroxamic acid derivatives, process for the production thereof and drugs containing the same as the active ingredient |
-
2002
- 2002-04-08 AR ARP020101282A patent/AR035455A1/es not_active Application Discontinuation
- 2002-04-19 CA CA002442994A patent/CA2442994A1/en not_active Abandoned
- 2002-04-19 CN CNB028086546A patent/CN1310904C/zh not_active Expired - Fee Related
- 2002-04-19 AT AT02724292T patent/ATE306480T1/de not_active IP Right Cessation
- 2002-04-19 MX MXPA03009132A patent/MXPA03009132A/es active IP Right Grant
- 2002-04-19 AU AU2002254991A patent/AU2002254991B2/en not_active Ceased
- 2002-04-19 EP EP02724292A patent/EP1385837B1/en not_active Expired - Lifetime
- 2002-04-19 BR BR0209064-3A patent/BR0209064A/pt not_active IP Right Cessation
- 2002-04-19 KR KR1020037013744A patent/KR100591501B1/ko not_active IP Right Cessation
- 2002-04-19 ES ES02724292T patent/ES2249572T3/es not_active Expired - Lifetime
- 2002-04-19 DE DE60206616T patent/DE60206616T2/de not_active Expired - Fee Related
- 2002-04-19 JP JP2002583410A patent/JP4142453B2/ja not_active Expired - Fee Related
- 2002-04-19 WO PCT/EP2002/004349 patent/WO2002085883A1/en active IP Right Grant
- 2002-04-22 US US10/127,100 patent/US6512123B2/en not_active Expired - Fee Related
-
2003
- 2003-10-06 ZA ZA200307793A patent/ZA200307793B/en unknown
-
2007
- 2007-10-11 CR CR9430A patent/CR9430A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR035455A1 (es) | 2004-05-26 |
| EP1385837B1 (en) | 2005-10-12 |
| CA2442994A1 (en) | 2002-10-31 |
| CR9430A (es) | 2008-04-25 |
| EP1385837A1 (en) | 2004-02-04 |
| BR0209064A (pt) | 2004-08-10 |
| MXPA03009132A (es) | 2004-02-12 |
| DE60206616D1 (de) | 2006-02-23 |
| KR20030090771A (ko) | 2003-11-28 |
| ATE306480T1 (de) | 2005-10-15 |
| JP4142453B2 (ja) | 2008-09-03 |
| US20020183513A1 (en) | 2002-12-05 |
| WO2002085883A1 (en) | 2002-10-31 |
| CN1310904C (zh) | 2007-04-18 |
| DE60206616T2 (de) | 2006-07-13 |
| JP2005503341A (ja) | 2005-02-03 |
| CN1507441A (zh) | 2004-06-23 |
| AU2002254991B2 (en) | 2007-07-19 |
| KR100591501B1 (ko) | 2006-06-19 |
| US6512123B2 (en) | 2003-01-28 |
| ES2249572T3 (es) | 2006-04-01 |
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