JP2011502133A5 - - Google Patents
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- JP2011502133A5 JP2011502133A5 JP2010531384A JP2010531384A JP2011502133A5 JP 2011502133 A5 JP2011502133 A5 JP 2011502133A5 JP 2010531384 A JP2010531384 A JP 2010531384A JP 2010531384 A JP2010531384 A JP 2010531384A JP 2011502133 A5 JP2011502133 A5 JP 2011502133A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- heteroaryl
- heterocyclyl
- phenyl
- 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.)
- Pending
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- 125000003118 aryl group Chemical group 0.000 claims 135
- 125000001072 heteroaryl group Chemical group 0.000 claims 117
- 125000000623 heterocyclic group Chemical group 0.000 claims 97
- 125000000753 cycloalkyl group Chemical group 0.000 claims 51
- 125000000217 alkyl group Chemical group 0.000 claims 50
- 150000001875 compounds Chemical class 0.000 claims 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 41
- 125000001544 thienyl group Chemical group 0.000 claims 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 26
- 229920006395 saturated elastomer Polymers 0.000 claims 19
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000005843 halogen group Chemical group 0.000 claims 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 12
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims 11
- 239000000126 substance Substances 0.000 claims 11
- 125000000335 thiazolyl group Chemical group 0.000 claims 11
- 102100038720 Histone deacetylase 9 Human genes 0.000 claims 9
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- -1 spiroheterocyclyl Chemical group 0.000 claims 9
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- 108090000353 Histone deacetylase Proteins 0.000 claims 5
- NPUACKRELIJTFM-UHFFFAOYSA-N cr gas Chemical compound C1=NC2=CC=CC=C2OC2=CC=CC=C21 NPUACKRELIJTFM-UHFFFAOYSA-N 0.000 claims 5
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 4
- UCFKRCOAJVNWLW-UHFFFAOYSA-N 2-benzyl-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=CC=C1CC1=CC=CC=C1 UCFKRCOAJVNWLW-UHFFFAOYSA-N 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- BAVHJZLGCYAXHZ-UHFFFAOYSA-N n-hydroxy-2-phenoxybenzamide Chemical compound ONC(=O)C1=CC=CC=C1OC1=CC=CC=C1 BAVHJZLGCYAXHZ-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- VVTCLTONLVZMDI-UHFFFAOYSA-N 2-anilino-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=CC=C1NC1=CC=CC=C1 VVTCLTONLVZMDI-UHFFFAOYSA-N 0.000 claims 3
- 238000000338 in vitro Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- HCUOEKSZWPGJIM-IYNMRSRQSA-N (e,2z)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N\O)\C(N)=O HCUOEKSZWPGJIM-IYNMRSRQSA-N 0.000 claims 2
- FTBBGQKRYUTLMP-UHFFFAOYSA-N 2-nitro-1h-pyrrole Chemical group [O-][N+](=O)C1=CC=CN1 FTBBGQKRYUTLMP-UHFFFAOYSA-N 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- OXMPDOZBQGHTGH-UHFFFAOYSA-N 5h-benzo[b][1,4]benzoxazepin-6-one Chemical compound O=C1NC2=CC=CC=C2OC2=CC=CC=C12 OXMPDOZBQGHTGH-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 108091005772 HDAC11 Proteins 0.000 claims 2
- 102100039385 Histone deacetylase 11 Human genes 0.000 claims 2
- 102100021454 Histone deacetylase 4 Human genes 0.000 claims 2
- 102100021453 Histone deacetylase 5 Human genes 0.000 claims 2
- 102100022537 Histone deacetylase 6 Human genes 0.000 claims 2
- 102100038715 Histone deacetylase 8 Human genes 0.000 claims 2
- 101000899259 Homo sapiens Histone deacetylase 4 Proteins 0.000 claims 2
- 101000899255 Homo sapiens Histone deacetylase 5 Proteins 0.000 claims 2
- 101000899330 Homo sapiens Histone deacetylase 6 Proteins 0.000 claims 2
- 101001032113 Homo sapiens Histone deacetylase 7 Proteins 0.000 claims 2
- 101001032118 Homo sapiens Histone deacetylase 8 Proteins 0.000 claims 2
- 101001032092 Homo sapiens Histone deacetylase 9 Proteins 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- WWGBHDIHIVGYLZ-UHFFFAOYSA-N N-[4-[3-[[[7-(hydroxyamino)-7-oxoheptyl]amino]-oxomethyl]-5-isoxazolyl]phenyl]carbamic acid tert-butyl ester Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C1=CC(C(=O)NCCCCCCC(=O)NO)=NO1 WWGBHDIHIVGYLZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- ZHSDLNXUORTYIN-UHFFFAOYSA-N n-hydroxy-2-phenylbenzamide Chemical compound ONC(=O)C1=CC=CC=C1C1=CC=CC=C1 ZHSDLNXUORTYIN-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- WGIAUTGOUJDVEI-UHFFFAOYSA-N 2-phenylpiperidine Chemical compound N1CCCCC1C1=CC=CC=C1 WGIAUTGOUJDVEI-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- QNISXNPVLHARBE-UHFFFAOYSA-N n-hydroxy-4-naphthalen-1-yl-1h-pyrrole-3-carboxamide Chemical compound ONC(=O)C1=CNC=C1C1=CC=CC2=CC=CC=C12 QNISXNPVLHARBE-UHFFFAOYSA-N 0.000 claims 1
- BRFCXCIMFPFJPQ-UHFFFAOYSA-N n-hydroxy-4-naphthalen-2-yl-1h-pyrrole-3-carboxamide Chemical compound ONC(=O)C1=CNC=C1C1=CC=C(C=CC=C2)C2=C1 BRFCXCIMFPFJPQ-UHFFFAOYSA-N 0.000 claims 1
- UUZPASUWMAPZET-UHFFFAOYSA-N n-hydroxy-4-phenyl-1h-pyrrole-3-carboxamide Chemical compound ONC(=O)C1=CNC=C1C1=CC=CC=C1 UUZPASUWMAPZET-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 0 *c1nc(I)c(N)[s]1 Chemical compound *c1nc(I)c(N)[s]1 0.000 description 4
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98506007P | 2007-11-02 | 2007-11-02 | |
| PCT/CA2008/001911 WO2009055917A1 (en) | 2007-11-02 | 2008-11-03 | Inhibitors of histone deacetylase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011502133A JP2011502133A (ja) | 2011-01-20 |
| JP2011502133A5 true JP2011502133A5 (enExample) | 2011-12-08 |
Family
ID=40590486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010531384A Pending JP2011502133A (ja) | 2007-11-02 | 2008-11-03 | ヒストンデアセチラーゼの阻害剤 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8673911B2 (enExample) |
| EP (1) | EP2217588A4 (enExample) |
| JP (1) | JP2011502133A (enExample) |
| KR (1) | KR20100095430A (enExample) |
| CN (1) | CN101918389A (enExample) |
| BR (1) | BRPI0817897A2 (enExample) |
| CA (1) | CA2703718A1 (enExample) |
| RU (1) | RU2501787C2 (enExample) |
| WO (1) | WO2009055917A1 (enExample) |
Families Citing this family (94)
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| US9187485B2 (en) | 2007-02-02 | 2015-11-17 | Baylor College Of Medicine | Methods and compositions for the treatment of cancer and related hyperproliferative disorders |
| JP5753844B2 (ja) | 2009-07-08 | 2015-07-22 | ダーミラ（カナダ），インコーポレーテッド | 皮膚疾患または病変の治療に有用なｔｏｆａ類似体 |
| EP2305643A1 (en) * | 2009-10-02 | 2011-04-06 | Ikerchem, S.L. | New histone deacetylase inhibitors based simultaneously on trisubstituted 1h-pyrroles and aromatic and heteroaromatic spacers |
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| KR20190061096A (ko) | 2010-04-22 | 2019-06-04 | 버텍스 파마슈티칼스 인코포레이티드 | 시클로알킬카르복스아미도-인돌 화합물의 제조 방법 |
| WO2011145669A1 (ja) * | 2010-05-19 | 2011-11-24 | 大日本住友製薬株式会社 | アミド誘導体 |
| WO2011161645A1 (en) | 2010-06-25 | 2011-12-29 | Ranbaxy Laboratories Limited | 5-lipoxygenase inhibitors |
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| JP6041808B2 (ja) * | 2010-11-16 | 2016-12-14 | アセチロン ファーマシューティカルズ インコーポレイテッドＡｃｅｔｙｌｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｉｎｃ． | 蛋白質脱アセチル化酵素抑制剤としてのピリミジン水酸基アミド化合物およびその利用方法 |
| US9249087B2 (en) * | 2011-02-01 | 2016-02-02 | The Board Of Trustees Of The University Of Illinois | HDAC inhibitors and therapeutic methods using the same |
| WO2012112447A2 (en) * | 2011-02-14 | 2012-08-23 | Dana-Farber Cancer Institute, Inc. | Histone deacetylase inhibitors and methods of use thereof |
| EP2712655B1 (en) | 2011-04-28 | 2019-12-18 | The Broad Institute, Inc. | Inhibitors of histone deacetylase |
| CN102775368B (zh) * | 2011-05-10 | 2016-08-17 | 上海驺虞医药科技有限公司 | 一类噻唑类化合物及其制备方法和用途 |
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| US9345905B2 (en) * | 2011-11-29 | 2016-05-24 | Nanjing Allgen Pharma Co. Ltd. | Heterocyclic amides compounds which are HDAC6 inhibitors and used as anti-tumoral agents |
| US20130267517A1 (en) | 2012-03-31 | 2013-10-10 | Hoffmann-La Roche Inc. | Novel 4-methyl-dihydropyrimidines for the treatment and prophylaxis of hepatitis b virus infection |
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| EP2892893B2 (en) | 2012-09-10 | 2019-10-16 | F.Hoffmann-La Roche Ag | 6-amino acid heteroaryldihydropyrimidines for the treatment and prophylaxis of hepatitis b virus infection |
| WO2014100438A1 (en) * | 2012-12-20 | 2014-06-26 | The Broad Institute, Inc. | Cycloalkenyl hydroxamic acid derivatives and their use as histone deacetylase inhibitors |
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- 2008-11-03 US US12/740,616 patent/US8673911B2/en active Active
- 2008-11-03 RU RU2010122304/04A patent/RU2501787C2/ru not_active IP Right Cessation
- 2008-11-03 WO PCT/CA2008/001911 patent/WO2009055917A1/en not_active Ceased
- 2008-11-03 BR BRPI0817897A patent/BRPI0817897A2/pt not_active IP Right Cessation
- 2008-11-03 EP EP08845130.7A patent/EP2217588A4/en not_active Withdrawn
- 2008-11-03 CA CA2703718A patent/CA2703718A1/en not_active Abandoned
- 2008-11-03 KR KR1020107012130A patent/KR20100095430A/ko not_active Ceased
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2013
- 2013-03-14 US US13/829,403 patent/US20140045850A1/en not_active Abandoned
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