JP2013517279A5 - - Google Patents
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- Publication number
- JP2013517279A5 JP2013517279A5 JP2012549065A JP2012549065A JP2013517279A5 JP 2013517279 A5 JP2013517279 A5 JP 2013517279A5 JP 2012549065 A JP2012549065 A JP 2012549065A JP 2012549065 A JP2012549065 A JP 2012549065A JP 2013517279 A5 JP2013517279 A5 JP 2013517279A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- fluorophenyl
- methyl
- butanamide
- trifluoromethyl
- 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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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 69
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
- -1 2,3-dihydro-1 , 4-benzodioxinyl Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- WIKJTMAEMSPOBF-UHFFFAOYSA-N 1-[5-[[benzyl(methyl)amino]methyl]thiophen-2-yl]-2,2,2-trifluoroethanone Chemical compound C=1C=CC=CC=1CN(C)CC1=CC=C(C(=O)C(F)(F)F)S1 WIKJTMAEMSPOBF-UHFFFAOYSA-N 0.000 claims 1
- HOQCLVYPIMJKLY-UHFFFAOYSA-N 1-phenyl-n-[[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]methyl]methanamine Chemical compound O1C(C(F)(F)F)=NC(CNCC=2C=CC=CC=2)=N1 HOQCLVYPIMJKLY-UHFFFAOYSA-N 0.000 claims 1
- MSNGIONWKLINQX-SNVBAGLBSA-N 2,2,2-trifluoro-1-[5-[[[(1r)-1-phenylethyl]amino]methyl]thiophen-2-yl]ethanone Chemical compound N([C@H](C)C=1C=CC=CC=1)CC1=CC=C(C(=O)C(F)(F)F)S1 MSNGIONWKLINQX-SNVBAGLBSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 1
- ORCQMPRYDXBXAM-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=NOC(C(F)(F)F)=N1 ORCQMPRYDXBXAM-UHFFFAOYSA-N 0.000 claims 1
- LREHVFULWDBNQV-UHFFFAOYSA-N n-[2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]ethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]butanamide Chemical compound C1=CC(F)=CC=C1C1=NC(CCNC(=O)CCCC=2N=C(ON=2)C(F)(F)F)=CO1 LREHVFULWDBNQV-UHFFFAOYSA-N 0.000 claims 1
- NMHXABRCWZHFSR-UHFFFAOYSA-N n-[[4-[2-(4-chlorophenyl)-1,3-thiazol-4-yl]-1-methylpiperidin-4-yl]methyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]butanamide Chemical compound C1CN(C)CCC1(C=1N=C(SC=1)C=1C=CC(Cl)=CC=1)CNC(=O)CCCC1=NOC(C(F)(F)F)=N1 NMHXABRCWZHFSR-UHFFFAOYSA-N 0.000 claims 1
- HARSKGDAVSHQLX-UHFFFAOYSA-N n-[[4-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]-1-methylpiperidin-4-yl]methyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]butanamide Chemical compound C1CN(C)CCC1(C=1N=C(OC=1)C=1C=CC(F)=CC=1)CNC(=O)CCCC1=NOC(C(F)(F)F)=N1 HARSKGDAVSHQLX-UHFFFAOYSA-N 0.000 claims 1
- OEAKBYCYTSSDAB-UHFFFAOYSA-N n-methyl-2-phenyl-n-[2-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]ethyl]acetamide Chemical compound C=1C=CC=CC=1CC(=O)N(C)CCC1=NOC(C(F)(F)F)=N1 OEAKBYCYTSSDAB-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 102000003964 Histone deacetylase Human genes 0.000 description 3
- 108090000353 Histone deacetylase Proteins 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003276 histone deacetylase inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29464310P | 2010-01-13 | 2010-01-13 | |
| US61/294,643 | 2010-01-13 | ||
| PCT/US2011/021099 WO2011088187A1 (en) | 2010-01-13 | 2011-01-13 | Compounds and methods |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013517279A JP2013517279A (ja) | 2013-05-16 |
| JP2013517279A5 true JP2013517279A5 (enExample) | 2014-02-27 |
Family
ID=44304636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012549065A Pending JP2013517279A (ja) | 2010-01-13 | 2011-01-13 | 化合物及び方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20120322827A1 (enExample) |
| EP (1) | EP2523560A4 (enExample) |
| JP (1) | JP2013517279A (enExample) |
| WO (1) | WO2011088187A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101781663B1 (ko) | 2010-01-13 | 2017-09-25 | 템페로 파마슈티칼즈, 인크. | 히스톤 데아세틸라제 효소를 억제하기 위한 화합물 및 이를 제조하는 방법 |
| WO2011088192A1 (en) | 2010-01-13 | 2011-07-21 | Tempero Pharmaceuticals, Inc. | Compounds and methods |
| CN103764635B (zh) | 2011-07-08 | 2016-01-20 | 诺华股份有限公司 | 新的三氟甲基-噁二唑衍生物及其在疾病治疗中的用途 |
| WO2013009830A1 (en) * | 2011-07-13 | 2013-01-17 | Tempero Pharmaceuticals, Inc. | Methods of treatment |
| WO2013009812A1 (en) * | 2011-07-13 | 2013-01-17 | Tempero Pharmaceuticals, Inc | Methods of treatment |
| WO2013009827A1 (en) * | 2011-07-13 | 2013-01-17 | Tempero Pharmaceuticals, Inc. | Methods of treatment |
| WO2013009810A1 (en) * | 2011-07-13 | 2013-01-17 | Tempero Pharmaceuticals, Inc. | Methods of treatment |
| WO2013066832A1 (en) * | 2011-10-31 | 2013-05-10 | Glaxosmithkline Llc | Compounds and methods |
| WO2013066836A1 (en) * | 2011-10-31 | 2013-05-10 | Glaxosmithkline Llc | Compounds and methods |
| WO2013066834A1 (en) * | 2011-10-31 | 2013-05-10 | Glaxosmithkline Llc | Compounds and methods |
| WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
| WO2021021979A2 (en) | 2019-07-30 | 2021-02-04 | Eikonizo Therapapeutics, Inc. | Hdac6 inhibitors and uses thereof |
| EP4504190A4 (en) | 2022-04-08 | 2026-03-25 | Eikonizo Therapeutics Inc | OXADIAZOLE HDAC6 INHIBITORS AND THEIR USES |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001018045A1 (en) * | 1999-09-08 | 2001-03-15 | Sloan-Kettering Institute For Cancer Research | Crystal structure of a deacetylase and inhibitors thereof |
| US7935724B2 (en) * | 2003-10-09 | 2011-05-03 | Merck Hdac Research, Llc | Thiophene and benzothiophene hydroxamic acid derivatives |
| AU2005313108B2 (en) * | 2004-12-10 | 2011-05-26 | Msd Italia S.R.L. | Heterocycle derivatives as histone deacetylase (HDAC) inhibitors |
| EP1841747B1 (en) * | 2005-01-14 | 2012-09-05 | SK Biopharmaceuticals Co., Ltd. | Oxazole hydroxamic acid derivatives and use thereof |
| KR101327323B1 (ko) * | 2005-01-14 | 2013-11-11 | 에스케이바이오팜 주식회사 | 옥사졸 하이드록삼산 유도체 및 이들의 용도 |
| GB0518237D0 (en) * | 2005-09-07 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| GB0603041D0 (en) * | 2006-02-15 | 2006-03-29 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
-
2011
- 2011-01-13 US US13/522,051 patent/US20120322827A1/en not_active Abandoned
- 2011-01-13 WO PCT/US2011/021099 patent/WO2011088187A1/en not_active Ceased
- 2011-01-13 JP JP2012549065A patent/JP2013517279A/ja active Pending
- 2011-01-13 EP EP11733358.3A patent/EP2523560A4/en not_active Withdrawn