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) |
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| 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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| RU2569678C2 (ru) | 2010-04-22 | 2015-11-27 | Вертекс Фармасьютикалз Инкорпорейтед | Способ получения циклоалкилкарбоксамидо-индольных соединений |
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- 2008-11-03 RU RU2010122304/04A patent/RU2501787C2/ru not_active IP Right Cessation
- 2008-11-03 EP EP08845130.7A patent/EP2217588A4/en not_active Withdrawn
- 2008-11-03 JP JP2010531384A patent/JP2011502133A/ja active Pending
- 2008-11-03 WO PCT/CA2008/001911 patent/WO2009055917A1/en not_active Ceased
- 2008-11-03 KR KR1020107012130A patent/KR20100095430A/ko not_active Ceased
- 2008-11-03 CN CN2008801238575A patent/CN101918389A/zh active Pending
- 2008-11-03 CA CA2703718A patent/CA2703718A1/en not_active Abandoned
- 2008-11-03 US US12/740,616 patent/US8673911B2/en active Active
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2013
- 2013-03-14 US US13/829,403 patent/US20140045850A1/en not_active Abandoned
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