JP2013506637A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013506637A5 JP2013506637A5 JP2012531445A JP2012531445A JP2013506637A5 JP 2013506637 A5 JP2013506637 A5 JP 2013506637A5 JP 2012531445 A JP2012531445 A JP 2012531445A JP 2012531445 A JP2012531445 A JP 2012531445A JP 2013506637 A5 JP2013506637 A5 JP 2013506637A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbonyl
- carboxamide
- pyrrole
- following structural
- 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
- IQKQZJZTRCSTJI-UHFFFAOYSA-N 3-(3-bromophenyl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=C(Br)C=CC=2)C=C(C=2C=CC=CC=2)N1 IQKQZJZTRCSTJI-UHFFFAOYSA-N 0.000 claims description 2
- JLNSWVQTKSDVIG-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5-phenyl-n-[[4-(pyrimidin-2-ylcarbamoyl)phenyl]methyl]-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NCC=2C=CC(=CC=2)C(=O)NC=2N=CC=CN=2)NC(C=2C=CC=CC=2)=C1 JLNSWVQTKSDVIG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 30
- 238000000034 method Methods 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 5
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 5
- 125000003368 amide group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- 150000003512 tertiary amines Chemical class 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 230000003213 activating effect Effects 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- PQCVYHSKABCYON-UHFFFAOYSA-N 2-oxo-1h-pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1O PQCVYHSKABCYON-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- IQFBZKXJEKXMQP-UHFFFAOYSA-N 3,5-bis(4-fluorophenyl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(F)=CC=2)C=C(C=2C=CC(F)=CC=2)N1 IQFBZKXJEKXMQP-UHFFFAOYSA-N 0.000 claims 1
- AKCXYHNDQWTRCG-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=C(Cl)C(Cl)=CC=2)C=C(C=2C=CC=CC=2)N1 AKCXYHNDQWTRCG-UHFFFAOYSA-N 0.000 claims 1
- CWLLRSZGVIEFEZ-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=C(F)C(F)=CC=2)C=C(C=2C=CC=CC=2)N1 CWLLRSZGVIEFEZ-UHFFFAOYSA-N 0.000 claims 1
- YRGZORLGDNCGTO-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C(=O)NCC=2C=CC(=CC=2)C(=O)NO)NC(C=2C=CC=CC=2)=C1 YRGZORLGDNCGTO-UHFFFAOYSA-N 0.000 claims 1
- DWSXNNRHIJVFDN-UHFFFAOYSA-N 3-(4-bromophenyl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(Br)=CC=2)C=C(C=2C=CC=CC=2)N1 DWSXNNRHIJVFDN-UHFFFAOYSA-N 0.000 claims 1
- CNOWOXXSYNLOJR-UHFFFAOYSA-N 3-(4-fluorophenyl)-5-(furan-3-yl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(F)=CC=2)C=C(C2=COC=C2)N1 CNOWOXXSYNLOJR-UHFFFAOYSA-N 0.000 claims 1
- ACXOXTKDFUCKDF-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-(4-methylphenyl)-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC(C=2C=CC(F)=CC=2)=C(C(=O)NCC=2C=CC(=CC=2)C(=O)NO)N1 ACXOXTKDFUCKDF-UHFFFAOYSA-N 0.000 claims 1
- RQZINTJHTVOSPD-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(F)=CC=2)C=C(C=2C=CC=CC=2)N1 RQZINTJHTVOSPD-UHFFFAOYSA-N 0.000 claims 1
- NCZPVKGOUNBDSF-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-pyridin-3-yl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(F)=CC=2)C=C(C=2C=NC=CC=2)N1 NCZPVKGOUNBDSF-UHFFFAOYSA-N 0.000 claims 1
- MVONLXWBEZHRPQ-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-thiophen-2-yl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(F)=CC=2)C=C(C=2SC=CC=2)N1 MVONLXWBEZHRPQ-UHFFFAOYSA-N 0.000 claims 1
- BUXPYIKGVMPYJG-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5-phenyl-n-[[4-(2-sulfanylethylcarbamoyl)phenyl]methyl]-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NCC=2C=CC(=CC=2)C(=O)NCCS)NC(C=2C=CC=CC=2)=C1 BUXPYIKGVMPYJG-UHFFFAOYSA-N 0.000 claims 1
- CJPQHCIMSKHOBF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5-phenyl-n-[[4-(pyridin-2-ylcarbamoyl)phenyl]methyl]-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NCC=2C=CC(=CC=2)C(=O)NC=2N=CC=CC=2)NC(C=2C=CC=CC=2)=C1 CJPQHCIMSKHOBF-UHFFFAOYSA-N 0.000 claims 1
- DPKPNPAZPYFQLM-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5-phenyl-n-[[4-[(2-sulfanylphenyl)carbamoyl]phenyl]methyl]-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NCC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2)S)NC(C=2C=CC=CC=2)=C1 DPKPNPAZPYFQLM-UHFFFAOYSA-N 0.000 claims 1
- OUFJXJJAONPLLU-UHFFFAOYSA-N 3-(furan-3-yl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-(4-hydroxyphenyl)-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C2=COC=C2)C=C(C=2C=CC(O)=CC=2)N1 OUFJXJJAONPLLU-UHFFFAOYSA-N 0.000 claims 1
- VWPYPJQYNJIVCP-UHFFFAOYSA-N 3-(furan-3-yl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-(4-methoxyphenyl)-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC(C2=COC=C2)=C(C(=O)NCC=2C=CC(=CC=2)C(=O)NO)N1 VWPYPJQYNJIVCP-UHFFFAOYSA-N 0.000 claims 1
- QTDGOLQQCBXUSF-UHFFFAOYSA-N 5-(furan-3-yl)-n-[[4-(hydroxycarbamoyl)phenyl]methyl]-3-(4-hydroxyphenyl)-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(O)=CC=2)C=C(C2=COC=C2)N1 QTDGOLQQCBXUSF-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 150000002240 furans Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- IRPKGHDXTSHWAC-UHFFFAOYSA-N n-[3-[2-(hydroxyamino)-2-oxoethyl]phenyl]-3-(4-methoxyphenyl)-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NC=2C=C(CC(=O)NO)C=CC=2)NC(C=2C=CC=CC=2)=C1 IRPKGHDXTSHWAC-UHFFFAOYSA-N 0.000 claims 1
- NZQURHGJPWLUTR-UHFFFAOYSA-N n-[4-(hydroxycarbamoyl)phenyl]-3-(4-methoxyphenyl)-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NC=2C=CC(=CC=2)C(=O)NO)NC(C=2C=CC=CC=2)=C1 NZQURHGJPWLUTR-UHFFFAOYSA-N 0.000 claims 1
- ZDHSUDUPVXTZHM-UHFFFAOYSA-N n-[5-(hydroxycarbamoyl)furan-2-yl]-3-(4-methoxyphenyl)-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NC=2OC(=CC=2)C(=O)NO)NC(C=2C=CC=CC=2)=C1 ZDHSUDUPVXTZHM-UHFFFAOYSA-N 0.000 claims 1
- XITXYBKGWMUUIQ-UHFFFAOYSA-N n-[[4-(hydroxycarbamoyl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(O)=CC=2)C=C(C=2C=CC=CC=2)N1 XITXYBKGWMUUIQ-UHFFFAOYSA-N 0.000 claims 1
- LFEKORZSWOREFY-UHFFFAOYSA-N n-[[4-(hydroxycarbamoyl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-thiophen-2-yl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(O)=CC=2)C=C(C=2SC=CC=2)N1 LFEKORZSWOREFY-UHFFFAOYSA-N 0.000 claims 1
- GKOHMYMZELMTOH-UHFFFAOYSA-N n-[[4-(hydroxycarbamoyl)phenyl]methyl]-3-(4-methoxyphenyl)-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NCC=2C=CC(=CC=2)C(=O)NO)NC(C=2C=CC=CC=2)=C1 GKOHMYMZELMTOH-UHFFFAOYSA-N 0.000 claims 1
- XVHHIOCDPITYJW-UHFFFAOYSA-N n-[[4-(hydroxycarbamoyl)phenyl]methyl]-3-(4-nitrophenyl)-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(=CC=2)[N+]([O-])=O)C=C(C=2C=CC=CC=2)N1 XVHHIOCDPITYJW-UHFFFAOYSA-N 0.000 claims 1
- GPGGCNQZIWRUGW-UHFFFAOYSA-N n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-(4-hydroxyphenyl)-3-thiophen-3-yl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C2=CSC=C2)C=C(C=2C=CC(O)=CC=2)N1 GPGGCNQZIWRUGW-UHFFFAOYSA-N 0.000 claims 1
- OUQUPVCKTGEABI-UHFFFAOYSA-N n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-(4-methoxyphenyl)-3-thiophen-3-yl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC(C2=CSC=C2)=C(C(=O)NCC=2C=CC(=CC=2)C(=O)NO)N1 OUQUPVCKTGEABI-UHFFFAOYSA-N 0.000 claims 1
- JKLOVHJBPLAOIQ-UHFFFAOYSA-N n-[[4-(hydroxycarbamoyl)phenyl]methyl]-5-phenyl-3-[4-(trifluoromethyl)phenyl]-1h-pyrrole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(=O)C1=C(C=2C=CC(=CC=2)C(F)(F)F)C=C(C=2C=CC=CC=2)N1 JKLOVHJBPLAOIQ-UHFFFAOYSA-N 0.000 claims 1
- HXVFEQPXJNUVNL-UHFFFAOYSA-N n-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]-3-(4-methoxyphenyl)-5-phenyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NCC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2)N)NC(C=2C=CC=CC=2)=C1 HXVFEQPXJNUVNL-UHFFFAOYSA-N 0.000 claims 1
- JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- -1 {[3- (4-Fluorophenyl) -5- (2-thienyl) -1H-pyrrol-2-yl] carbonyl} amino Chemical group 0.000 claims 1
- 0 CC1C(**)=*C=C(*C(C)=O)N(C)C1 Chemical compound CC1C(**)=*C=C(*C(C)=O)N(C)C1 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09382193.2 | 2009-10-02 | ||
| EP09382193A EP2305643A1 (en) | 2009-10-02 | 2009-10-02 | New histone deacetylase inhibitors based simultaneously on trisubstituted 1h-pyrroles and aromatic and heteroaromatic spacers |
| PCT/EP2010/064653 WO2011039353A1 (en) | 2009-10-02 | 2010-10-01 | New histone deacetylase inhibitors based simultaneously on trisubstituted 1h-pyrroles and aromatic and heteroaromatic spacers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013506637A JP2013506637A (ja) | 2013-02-28 |
| JP2013506637A5 true JP2013506637A5 (https=) | 2013-11-07 |
| JP5746185B2 JP5746185B2 (ja) | 2015-07-08 |
Family
ID=41716282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012531445A Active JP5746185B2 (ja) | 2009-10-02 | 2010-10-01 | 三置換１ｈ−ピロール類と、芳香族スペーサーおよびヘテロ芳香族スペーサーとに同時に基づく新規ヒストンデアセチラーゼ阻害剤 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8685992B2 (https=) |
| EP (2) | EP2305643A1 (https=) |
| JP (1) | JP5746185B2 (https=) |
| KR (1) | KR101754940B1 (https=) |
| CN (1) | CN102648177B (https=) |
| AU (1) | AU2010302572B2 (https=) |
| BR (1) | BR112012007411B8 (https=) |
| CA (1) | CA2776351C (https=) |
| ES (1) | ES2452868T3 (https=) |
| IL (1) | IL218995A (https=) |
| IN (1) | IN2012DN03129A (https=) |
| MX (1) | MX2012003988A (https=) |
| PL (1) | PL2483242T3 (https=) |
| PT (1) | PT2483242E (https=) |
| RU (1) | RU2549885C2 (https=) |
| WO (1) | WO2011039353A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2627324A4 (en) * | 2010-10-11 | 2014-05-07 | Univ Leland Stanford Junior | SUBSTITUTED BENZAMIDES AND USES THEREOF |
| US9878986B2 (en) | 2013-04-29 | 2018-01-30 | Chong Kun Dang Pharmaceutical Corp. | Compounds for selective histone deacetylase inhibitors, and pharmaceutical composition comprising the same |
| SG11201708622UA (en) | 2015-02-02 | 2017-11-29 | Forma Therapeutics Inc | 3-aryl-4-amido-bicyclic [4,5,0] hydroxamic acids as hdac inhibitors |
| WO2016126726A1 (en) | 2015-02-02 | 2016-08-11 | Forma Therapeutics, Inc. | Bicyclic [4,6,0] hydroxamic acids as hdac6 inhibitors |
| US20180251425A1 (en) * | 2015-08-17 | 2018-09-06 | University Of Mysore | 2,3,5 trisubstituted pyrrole derivatives as topoisomerase inhibitors and therapeutic uses thereof |
| EP3472131B1 (en) | 2016-06-17 | 2020-02-19 | Forma Therapeutics, Inc. | 2-spiro-5- and 6-hydroxamic acid indanes as hdac inhibitors |
| CN107793375A (zh) * | 2016-08-31 | 2018-03-13 | 中国科学院上海药物研究所 | 一类芳基2,2’‑串联双噻唑类化合物及其制备方法和用途 |
| EP3318256A1 (en) * | 2016-11-08 | 2018-05-09 | Quimatryx, S.L | Compounds for the treatment of autoimmune diseases |
| GB201708457D0 (en) | 2017-05-26 | 2017-07-12 | Univ Oxford Innovation Ltd | Inhibitors of metallo-beta-lactamases |
| CN110938055A (zh) * | 2018-09-21 | 2020-03-31 | 华东师范大学 | 六元环甲酰胺类化合物及其合成方法和应用 |
| KR20220012243A (ko) | 2019-04-17 | 2022-02-03 | 퀴마트리스 에스.엘. | 히스톤 디아세틸라제 억제제로서의 1,3,4-옥사디아졸 유도체 |
| CN112225737B (zh) * | 2020-12-11 | 2021-04-09 | 北京鑫开元医药科技有限公司 | 具有hdac抑制活性的化合物、制备方法、组合物及用途 |
| CN112516142B (zh) * | 2020-12-11 | 2021-10-15 | 北京华氏精恒医药科技有限公司 | 一种具有hdac抑制活性的药物组合物、制备方法及其用途 |
| CN116813560A (zh) * | 2022-03-28 | 2023-09-29 | 上海科技大学 | 三唑酰胺类化合物及其制备方法和用途 |
| CN114558004B (zh) * | 2022-03-29 | 2023-08-11 | 奎马特里克斯有限公司 | Qtx125药物制剂 |
| CN114634489B (zh) * | 2022-04-19 | 2023-07-04 | 奎马特里克斯有限公司 | 结晶形式 |
| CN114652715B (zh) | 2022-04-29 | 2023-04-25 | 奎马特里克斯有限公司 | 联合疗法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA76977C2 (en) * | 2001-03-02 | 2006-10-16 | Icos Corp | Aryl- and heteroaryl substituted chk1 inhibitors and their use as radiosensitizers and chemosensitizers |
| PT1673349E (pt) | 2003-09-22 | 2010-09-28 | S Bio Pte Ltd | Derivados benzimidazole: preparação e aplicações farmacêuticas |
| MXPA06005915A (es) * | 2003-12-05 | 2006-06-27 | Warner Lambert Co | N-alquil pirroles como inhibidores de la hmg-coa reductasa. |
| EP1874723A2 (en) * | 2005-04-15 | 2008-01-09 | Dominion Pharmakine S.L. | New nitrogenated trans-stilbene analogs, method for the obtention and medical applications thereof |
| US7754717B2 (en) * | 2005-08-15 | 2010-07-13 | Amgen Inc. | Bis-aryl amide compounds and methods of use |
| PT1975158E (pt) * | 2005-12-27 | 2011-09-23 | Ct Nac Investigaciones Oncologicas Cnio | Novos derivados de pirrole com actividade inibidora de histona desacetilase |
| BRPI0817897A2 (pt) * | 2007-11-02 | 2019-09-24 | Methylgene Inc | composto, composição, e, métodos de inibição da atividade hdac, e de tratamento de uma doença responsiva a um inibidor de atividade hdac |
-
2009
- 2009-10-02 EP EP09382193A patent/EP2305643A1/en not_active Withdrawn
-
2010
- 2010-10-01 BR BR112012007411A patent/BR112012007411B8/pt active IP Right Grant
- 2010-10-01 PL PL10763676T patent/PL2483242T3/pl unknown
- 2010-10-01 PT PT107636763T patent/PT2483242E/pt unknown
- 2010-10-01 RU RU2012117885/04A patent/RU2549885C2/ru not_active IP Right Cessation
- 2010-10-01 ES ES10763676.3T patent/ES2452868T3/es active Active
- 2010-10-01 WO PCT/EP2010/064653 patent/WO2011039353A1/en not_active Ceased
- 2010-10-01 JP JP2012531445A patent/JP5746185B2/ja active Active
- 2010-10-01 EP EP10763676.3A patent/EP2483242B1/en active Active
- 2010-10-01 CA CA2776351A patent/CA2776351C/en active Active
- 2010-10-01 AU AU2010302572A patent/AU2010302572B2/en active Active
- 2010-10-01 IN IN3129DEN2012 patent/IN2012DN03129A/en unknown
- 2010-10-01 CN CN201080052814.XA patent/CN102648177B/zh active Active
- 2010-10-01 MX MX2012003988A patent/MX2012003988A/es active IP Right Grant
- 2010-10-01 US US13/499,839 patent/US8685992B2/en active Active
- 2010-10-01 KR KR1020127011407A patent/KR101754940B1/ko active Active
-
2012
- 2012-04-02 IL IL218995A patent/IL218995A/en not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013506637A5 (https=) | ||
| RU2012117885A (ru) | 2,3,5-тризамещенные пирролы, фармацевтическая композиция и лекарственное средство (варианты) на их основе, способ получения соединений (варианты) | |
| AU2002342607B2 (en) | Aminoisoxazole derivatives active as kinase inhibitors | |
| RU2462454C2 (ru) | Новое сульфонамидное производное малоновой кислоты и его фармацевтическое применение | |
| JP2007523905A5 (https=) | ||
| JP2008509982A5 (https=) | ||
| KR101781663B1 (ko) | 히스톤 데아세틸라제 효소를 억제하기 위한 화합물 및 이를 제조하는 방법 | |
| JP5040656B2 (ja) | トリアリールカルボン酸誘導体 | |
| CA2396824A1 (en) | Heteroaromatic carboxamide derivatives and their use as inhibitors of the enzyme ikk-2 | |
| JP2010501587A5 (https=) | ||
| JP2010540462A5 (https=) | ||
| JPH11193281A (ja) | アデノシンａ３受容体拮抗剤およびチアゾール化合物 | |
| RU2010120682A (ru) | Ингибиторы гистондезацетилазы | |
| JP2004521908A5 (https=) | ||
| JP2014511869A5 (https=) | ||
| CA2558585A1 (en) | Compounds, pharmaceutical compositions and methods for use in treating metabolic disorders | |
| JP2008500336A5 (https=) | ||
| NZ589504A (en) | Substituted carbinol compound having cyclic linker | |
| JP2005514432A5 (https=) | ||
| JP2011500679A5 (https=) | ||
| JP2009517368A5 (https=) | ||
| JP2005526732A5 (https=) | ||
| JP2005526815A5 (https=) | ||
| RU2004129285A (ru) | Производные тиазола в качестве антагонистов рецептора npy | |
| JP2005504725A5 (https=) |