JP2012519162A5 - - Google Patents
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- Publication number
- JP2012519162A5 JP2012519162A5 JP2011551519A JP2011551519A JP2012519162A5 JP 2012519162 A5 JP2012519162 A5 JP 2012519162A5 JP 2011551519 A JP2011551519 A JP 2011551519A JP 2011551519 A JP2011551519 A JP 2011551519A JP 2012519162 A5 JP2012519162 A5 JP 2012519162A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyamino
- cyclopentyl
- methyl
- benzyl
- oxoprop
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 23
- -1 bicyclo [2.2.1] hept-2-yl Chemical group 0.000 claims 17
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
- 125000004185 ester group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000006413 ring segment Chemical group 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 102000003964 Histone deacetylase Human genes 0.000 claims 2
- 108090000353 Histone deacetylase Proteins 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 2
- RPEQENHLPUXYRG-CMDGGOBGSA-N cyclopentyl 1-[[6-[(e)-3-(hydroxyamino)-3-oxoprop-1-enyl]pyridin-3-yl]methylamino]cyclobutane-1-carboxylate Chemical compound C1=NC(/C=C/C(=O)NO)=CC=C1CNC1(C(=O)OC2CCCC2)CCC1 RPEQENHLPUXYRG-CMDGGOBGSA-N 0.000 claims 2
- QVVDZHCGJWXPCJ-VAWYXSNFSA-N cyclopentyl 2-[[4-[(e)-3-(hydroxyamino)-3-oxoprop-1-enyl]phenyl]methylamino]-2-methylpropanoate Chemical compound C1CCCC1OC(=O)C(C)(C)NCC1=CC=C(\C=C\C(=O)NO)C=C1 QVVDZHCGJWXPCJ-VAWYXSNFSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 1
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- FAMYWUCPHSGCPD-BQYQJAHWSA-N 1-[[4-[(e)-3-(hydroxyamino)-3-oxoprop-1-enyl]phenyl]methylamino]cyclopentane-1-carboxylic acid Chemical compound C1=CC(/C=C/C(=O)NO)=CC=C1CNC1(C(O)=O)CCCC1 FAMYWUCPHSGCPD-BQYQJAHWSA-N 0.000 claims 1
- OEUNTOUUBAGWBJ-UHFFFAOYSA-N 1-[[4-[3-(hydroxyamino)-3-oxopropyl]phenyl]methylamino]cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCC(=O)NO)=CC=C1CNC1(C(O)=O)CCCC1 OEUNTOUUBAGWBJ-UHFFFAOYSA-N 0.000 claims 1
- SMLDBQBHWOSMFD-SNAWJCMRSA-N 1-[[6-[(e)-3-(hydroxyamino)-3-oxoprop-1-enyl]pyridin-3-yl]methylamino]cyclobutane-1-carboxylic acid Chemical compound C1=NC(/C=C/C(=O)NO)=CC=C1CNC1(C(O)=O)CCC1 SMLDBQBHWOSMFD-SNAWJCMRSA-N 0.000 claims 1
- WRJQBKHUICFVCZ-AATRIKPKSA-N 1-[[6-[(e)-3-(hydroxyamino)-3-oxoprop-1-enyl]pyridin-3-yl]methylamino]cyclopentane-1-carboxylic acid Chemical compound C1=NC(/C=C/C(=O)NO)=CC=C1CNC1(C(O)=O)CCCC1 WRJQBKHUICFVCZ-AATRIKPKSA-N 0.000 claims 1
- NWXSADISNKTOGI-UHFFFAOYSA-N 2-[[4-[3-(hydroxyamino)-3-oxopropyl]phenyl]methylamino]-2,4-dimethylpentanoic acid Chemical compound CC(C)CC(C)(C(O)=O)NCC1=CC=C(CCC(=O)NO)C=C1 NWXSADISNKTOGI-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000019838 Blood disease Diseases 0.000 claims 1
- 102000013392 Carboxylesterase Human genes 0.000 claims 1
- 108010051152 Carboxylesterase Proteins 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 1
- 235000008206 alpha-amino acids Nutrition 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 230000009702 cancer cell proliferation Effects 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- FATPDRBNZFXZJL-CHHLAKQQSA-N cyclopentyl (2r)-2-[[4-[(e)-3-(hydroxyamino)-3-oxoprop-1-enyl]phenyl]methylamino]-2,4-dimethylpentanoate Chemical compound N([C@](C)(CC(C)C)C(=O)OC1CCCC1)CC1=CC=C(\C=C\C(=O)NO)C=C1 FATPDRBNZFXZJL-CHHLAKQQSA-N 0.000 claims 1
- JDDHPJBPJXWWLZ-UHFFFAOYSA-N cyclopentyl 2-[[4-[3-(hydroxyamino)-3-oxopropyl]phenyl]methylamino]-2,4-dimethylpentanoate Chemical compound C1CCCC1OC(=O)C(C)(CC(C)C)NCC1=CC=C(CCC(=O)NO)C=C1 JDDHPJBPJXWWLZ-UHFFFAOYSA-N 0.000 claims 1
- ZYAAARPUWDNNLE-UHFFFAOYSA-N cyclopentyl 2-[[4-[3-(hydroxyamino)-3-oxopropyl]phenyl]methylamino]-2-methylpropanoate Chemical compound C1CCCC1OC(=O)C(C)(C)NCC1=CC=C(CCC(=O)NO)C=C1 ZYAAARPUWDNNLE-UHFFFAOYSA-N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 208000014951 hematologic disease Diseases 0.000 claims 1
- 208000018706 hematopoietic system disease Diseases 0.000 claims 1
- 230000002458 infectious effect Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229920000155 polyglutamine Polymers 0.000 claims 1
- 108010040003 polyglutamine Proteins 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0903480.2 | 2009-02-27 | ||
| GBGB0903480.2A GB0903480D0 (en) | 2009-02-27 | 2009-02-27 | Enzyme Inhibitors |
| PCT/GB2010/000337 WO2010097586A1 (en) | 2009-02-27 | 2010-02-25 | Enzyme inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012519162A JP2012519162A (ja) | 2012-08-23 |
| JP2012519162A5 true JP2012519162A5 (https=) | 2013-03-21 |
| JP5732408B2 JP5732408B2 (ja) | 2015-06-10 |
Family
ID=40565933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011551519A Expired - Fee Related JP5732408B2 (ja) | 2009-02-27 | 2010-02-25 | 酵素阻害剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US20120149736A1 (https=) |
| EP (1) | EP2401257A1 (https=) |
| JP (1) | JP5732408B2 (https=) |
| GB (1) | GB0903480D0 (https=) |
| WO (1) | WO2010097586A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0803747D0 (en) | 2008-02-29 | 2008-04-09 | Martin | Enzyme and receptor modulation |
| WO2012025701A1 (en) * | 2010-08-25 | 2012-03-01 | Chroma Therapeutics Ltd. | Alpha, alpha - di substituted glycine ester derivatives and their use as hdac inhibitors |
| HK1200809A1 (en) * | 2011-12-29 | 2015-08-14 | 药品循环有限责任公司 | Cinnamic acid hydroxyamides as inhibitors of histone deacetylase 8 |
| GB201211310D0 (en) | 2012-06-26 | 2012-08-08 | Chroma Therapeutics Ltd | CSF-1R kinase inhibitors |
| PL3222616T3 (pl) | 2012-10-17 | 2019-12-31 | Macrophage Pharma Limited | N-[2-{4-[6-amino-5-(2,4-difluorobenzoilo)-2-oksopirydyn-1(2h)-ylo]-3,5-difluorofenylo}etylo)-L-alaninian tert-butylu lub jego sól, hydrat lub solwat |
| US9745253B2 (en) | 2015-03-13 | 2017-08-29 | Forma Therapeutics, Inc. | Alpha-cinnamide compounds and compositions as HDAC8 inhibitors |
| WO2017216297A1 (en) | 2016-06-16 | 2017-12-21 | Glaxosmithkline Intellectual Property Development Limited | Dosage regimen |
| GB201713975D0 (en) | 2017-08-31 | 2017-10-18 | Macrophage Pharma Ltd | Medical use |
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| AU650953B2 (en) | 1991-03-21 | 1994-07-07 | Novartis Ag | Inhaler |
| US5369108A (en) | 1991-10-04 | 1994-11-29 | Sloan-Kettering Institute For Cancer Research | Potent inducers of terminal differentiation and methods of use thereof |
| NZ517613A (en) | 1999-09-08 | 2004-01-30 | Sloan Kettering Inst Cancer | Novel class of cytodifferentiating agents and histone deacetylase inhibitors, and methods of use thereof |
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| GB0003476D0 (en) | 2000-02-16 | 2000-04-05 | British Biotech Pharm | Acetal Hydroxylamine compounds |
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| JP4790594B2 (ja) | 2003-02-25 | 2011-10-12 | トポターゲット ユーケー リミテッド | Ｈｄａｃインヒビターとしての、二環式ヘテロアリール基を含むヒドロキサム酸化合物 |
| BRPI0409227C1 (pt) | 2003-04-07 | 2021-05-25 | Axys Pharm Inc | composto, composição farmacêutica, uso de um composto e processo para a preparação de um composto de fórmula (i) |
| WO2004110989A1 (en) | 2003-05-14 | 2004-12-23 | Bayer Pharmaceuticals Corporation | N-hydroxy-7-(arylamino)heptanamide derivatives useful for treating hyper-proliferative disorders |
| WO2005007091A2 (en) | 2003-07-07 | 2005-01-27 | Georgetown University | Histone deacetylase inhibitors and methods of use thereof |
| EP1663201A4 (en) | 2003-07-15 | 2009-10-28 | Korea Res Inst Of Bioscience | USE OF NOVEL 2-OXO-HETEROCYCLIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME |
| WO2005014588A1 (en) | 2003-08-01 | 2005-02-17 | Argenta Discovery Limited | Substituted thienyl-hydroxamic acids having histone deacetylase activity |
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| CN1795175A (zh) | 2003-08-20 | 2006-06-28 | Axys药物公司 | 作为组蛋白脱乙酰基酶抑制剂的乙炔衍生物 |
| SI1663194T1 (sl) | 2003-08-26 | 2010-08-31 | Merck Hdac Res Llc | Uporaba SAHA za zdravljenje mezotelioma |
| WO2005028447A1 (en) | 2003-09-22 | 2005-03-31 | S*Bio Pte Ltd | Benzimidazole derivates: preparation and pharmaceutical applications |
| WO2005030705A1 (en) | 2003-09-24 | 2005-04-07 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| DK1696898T3 (en) * | 2003-12-02 | 2016-02-22 | Univ Ohio State Res Found | ZN2 + -CHELATING DESIGN-BASED SHORT-CHAIN FAT ACIDS AS AN UNKNOWN CLASS OF HISTONDEACETYLASE INHIBITORS |
| MX2007001550A (es) | 2004-08-09 | 2007-04-10 | Astellas Pharma Inc | Compuestos de hidroxiamida que tienen actividad como inhibidores de histona desacetilasa (hdac). |
| GB0509223D0 (en) | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Enzyme inhibitors |
| GB0509225D0 (en) | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Inhibitors of enzymatic activity |
| GB0509224D0 (en) | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Inhibitors of intracellular enzymatic activity |
| GB0509227D0 (en) | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Intracellular enzyme inhibitors |
| AU2006243000B2 (en) | 2005-05-05 | 2011-05-26 | Macrophage Pharma Limited | Alpha aminoacid ester-drug conjugates hydrolysable by carboxylesterase |
| EP2013175B9 (en) | 2006-05-04 | 2020-11-11 | Macrophage Pharma Limited | p38 MAP KINASE INHIBITORS |
| GB0608821D0 (en) | 2006-05-04 | 2006-06-14 | Chroma Therapeutics Ltd | DHFR enzyme inhibitors |
| GB0608822D0 (en) | 2006-05-04 | 2006-06-14 | Chroma Therapeutics Ltd | Inhibitors of DHFR |
| GB0608823D0 (en) | 2006-05-04 | 2006-06-14 | Chroma Therapeutics Ltd | Inhibitors of P13 kinase |
| GB0608854D0 (en) | 2006-05-04 | 2006-06-14 | Chroma Therapeutics Ltd | P13 kinase inhibitors |
| GB0608837D0 (en) | 2006-05-04 | 2006-06-14 | Chroma Therapeutics Ltd | Inhibitors of MAP kinase |
| GB0619753D0 (en) | 2006-10-06 | 2006-11-15 | Chroma Therapeutics Ltd | Enzyme inhibitors |
| EA200900593A1 (ru) | 2006-10-25 | 2010-06-30 | Хрома Терапьютикс Лтд. | Производные птеридина как ингибиторы polo-подобной киназы, применяющиеся при лечении рака |
| GB0621203D0 (en) | 2006-10-25 | 2006-12-06 | Chroma Therapeutics Ltd | PLK inhibitors |
| WO2008053131A1 (en) | 2006-10-30 | 2008-05-08 | Chroma Therapeutics Ltd. | Hydroxamates as inhibitors of histone deacetylase |
| GB0621607D0 (en) | 2006-10-31 | 2006-12-06 | Chroma Therapeutics Ltd | Inhibitors of c-Met |
| WO2008053182A1 (en) | 2006-11-01 | 2008-05-08 | Chroma Therapeutics Ltd. | IKK-β SERINE-THREONINE PROTEIN KINASE INHIBITORS |
| JP2010508337A (ja) | 2006-11-01 | 2010-03-18 | クロマ セラピューティクス リミテッド | Ｉｋｋ−ベータセリン−スレオニンプロテインキナーゼの阻害剤 |
| GB0621830D0 (en) | 2006-11-02 | 2006-12-13 | Chroma Therapeutics Ltd | Inhibitors of p38 mitogen-activated protein kinase |
| GB0621978D0 (en) | 2006-11-03 | 2006-12-13 | Chroma Therapeutics Ltd | Inhibitors of p38 mitogen-activated protein kinase |
| US20100267774A1 (en) | 2007-11-07 | 2010-10-21 | Chroma Therapeutics Ltd. | P38 map kinase inhibitors |
| GB0803747D0 (en) * | 2008-02-29 | 2008-04-09 | Martin | Enzyme and receptor modulation |
| JP5555186B2 (ja) | 2008-02-29 | 2014-07-23 | クロマ セラピューティクス リミテッド | ｐ３８ＭＡＰキナーゼ阻害剤 |
| GB0807451D0 (en) | 2008-04-24 | 2008-05-28 | Chroma Therapeutics Ltd | Inhibitors of PLK |
-
2009
- 2009-02-27 GB GBGB0903480.2A patent/GB0903480D0/en not_active Ceased
-
2010
- 2010-02-25 WO PCT/GB2010/000337 patent/WO2010097586A1/en not_active Ceased
- 2010-02-25 EP EP10706033A patent/EP2401257A1/en not_active Withdrawn
- 2010-02-25 JP JP2011551519A patent/JP5732408B2/ja not_active Expired - Fee Related
- 2010-02-25 US US13/202,105 patent/US20120149736A1/en not_active Abandoned
-
2013
- 2013-07-19 US US13/946,488 patent/US20130303576A1/en not_active Abandoned
-
2014
- 2014-02-07 US US14/175,072 patent/US20140155439A1/en not_active Abandoned
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