JP2012530703A5 - - Google Patents
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- Publication number
- JP2012530703A5 JP2012530703A5 JP2012516072A JP2012516072A JP2012530703A5 JP 2012530703 A5 JP2012530703 A5 JP 2012530703A5 JP 2012516072 A JP2012516072 A JP 2012516072A JP 2012516072 A JP2012516072 A JP 2012516072A JP 2012530703 A5 JP2012530703 A5 JP 2012530703A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- nhc
- present
- membered
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 369
- 150000001875 compounds Chemical class 0.000 claims description 162
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 138
- 229910052757 nitrogen Inorganic materials 0.000 claims description 130
- 125000001931 aliphatic group Chemical group 0.000 claims description 115
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 114
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 114
- 125000005842 heteroatom Chemical group 0.000 claims description 114
- 229910052760 oxygen Inorganic materials 0.000 claims description 114
- 239000001301 oxygen Chemical group 0.000 claims description 114
- 229910052717 sulfur Chemical group 0.000 claims description 114
- 239000011593 sulfur Chemical group 0.000 claims description 114
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 94
- -1 —O—C 1-3 haloalkyl Chemical group 0.000 claims description 90
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 80
- 125000001153 fluoro group Chemical group F* 0.000 claims description 74
- 125000002723 alicyclic group Chemical group 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 35
- 150000002431 hydrogen Chemical group 0.000 claims description 33
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 32
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 26
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 26
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 230000002062 proliferating effect Effects 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 150000001721 carbon Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 10
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 10
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 10
- 208000034578 Multiple myelomas Diseases 0.000 claims description 10
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 10
- 206010033128 Ovarian cancer Diseases 0.000 claims description 10
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 10
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 10
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 10
- 206010006187 Breast cancer Diseases 0.000 claims description 8
- 208000026310 Breast neoplasm Diseases 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 8
- 201000005202 lung cancer Diseases 0.000 claims description 8
- 208000020816 lung neoplasm Diseases 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 102100022537 Histone deacetylase 6 Human genes 0.000 claims description 4
- 101000899330 Homo sapiens Histone deacetylase 6 Proteins 0.000 claims description 4
- 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 description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 4
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims description 2
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 210000000481 breast Anatomy 0.000 claims 2
- 210000004072 lung Anatomy 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 0 CC(C(NO)=O)=CC(CCN(*)C1)=C1C=C Chemical compound CC(C(NO)=O)=CC(CCN(*)C1)=C1C=C 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21909609P | 2009-06-22 | 2009-06-22 | |
| US61/219,096 | 2009-06-22 | ||
| PCT/US2010/001801 WO2010151318A1 (en) | 2009-06-22 | 2010-06-21 | Substituted hydroxamic acids and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015012045A Division JP2015078237A (ja) | 2009-06-22 | 2015-01-26 | 置換ヒドロキサム酸およびその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012530703A JP2012530703A (ja) | 2012-12-06 |
| JP2012530703A5 true JP2012530703A5 (enExample) | 2013-08-08 |
| JP5798115B2 JP5798115B2 (ja) | 2015-10-21 |
Family
ID=43386815
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012516072A Expired - Fee Related JP5798115B2 (ja) | 2009-06-22 | 2010-06-21 | 置換ヒドロキサム酸およびその使用 |
| JP2015012045A Pending JP2015078237A (ja) | 2009-06-22 | 2015-01-26 | 置換ヒドロキサム酸およびその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015012045A Pending JP2015078237A (ja) | 2009-06-22 | 2015-01-26 | 置換ヒドロキサム酸およびその使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9096518B2 (enExample) |
| EP (1) | EP2445340B1 (enExample) |
| JP (2) | JP5798115B2 (enExample) |
| CA (1) | CA2765678A1 (enExample) |
| WO (1) | WO2010151318A1 (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050089559A1 (en) * | 2003-10-23 | 2005-04-28 | Istvan Szelenyi | Combinations of potassium channel openers and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains |
| US8722929B2 (en) * | 2006-10-10 | 2014-05-13 | Valeant Pharmaceuticals International | N-[2-amino-4-(phenylmethoxy)phenyl] amides and related compounds as potassium channel modulators |
| US8367684B2 (en) * | 2007-06-13 | 2013-02-05 | Valeant Pharmaceuticals International | Derivatives of 4-(N-azacycloalkyl) anilides as potassium channel modulators |
| US8563566B2 (en) * | 2007-08-01 | 2013-10-22 | Valeant Pharmaceuticals International | Naphthyridine derivatives as potassium channel modulators |
| US7786146B2 (en) * | 2007-08-13 | 2010-08-31 | Valeant Pharmaceuticals International | Derivatives of 5-amino-4,6-disubstituted indole and 5-amino-4,6-disubstituted indoline as potassium channel modulators |
| CA2765678A1 (en) * | 2009-06-22 | 2010-12-29 | Christopher Blackburn | Substituted hydroxamic acids and uses thereof |
| WO2010151317A1 (en) | 2009-06-22 | 2010-12-29 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2011106627A1 (en) * | 2010-02-26 | 2011-09-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2011106632A1 (en) * | 2010-02-26 | 2011-09-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2011130163A1 (en) | 2010-04-12 | 2011-10-20 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| US8513421B2 (en) | 2010-05-19 | 2013-08-20 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2012027564A1 (en) | 2010-08-26 | 2012-03-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| JP5815033B2 (ja) | 2010-09-09 | 2015-11-17 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | 癌治療用新規ｎ−ヒドロキシ−ベンズアミド |
| WO2012054332A1 (en) | 2010-10-18 | 2012-04-26 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2012088015A2 (en) | 2010-12-22 | 2012-06-28 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2012117421A1 (en) | 2011-03-02 | 2012-09-07 | Orchid Research Laboratories Ltd | Histone deacetylase inhibitors |
| WO2013041407A1 (en) * | 2011-09-19 | 2013-03-28 | Cellzome Ag | Hydroxamic acids as hdac6 inhibitors |
| BR112017003658B1 (pt) | 2014-08-28 | 2022-12-06 | Asceneuron Sa | Composto, mistura, método para inibição de uma glicosidase, e, composição farmacêutica |
| WO2016126726A1 (en) * | 2015-02-02 | 2016-08-11 | Forma Therapeutics, Inc. | Bicyclic [4,6,0] hydroxamic acids as hdac6 inhibitors |
| WO2016126721A1 (en) | 2015-02-02 | 2016-08-11 | Forma Therapeutics, Inc. | 3-aryl-bicyclic [4,5,0] hydroxamic acids as hdac inhibitors |
| AU2017222964B2 (en) | 2016-02-25 | 2020-01-02 | Asceneuron S. A. | Glycosidase inhibitors |
| EP3585783A2 (en) | 2016-02-25 | 2020-01-01 | Asceneuron SA | Sulfoximine glycosidase inhibitors |
| US11612599B2 (en) | 2016-02-25 | 2023-03-28 | Asceneuron Sa | Glycosidase inhibitors |
| EP3419976B1 (en) | 2016-02-25 | 2021-04-07 | Asceneuron SA | Acid addition salts of piperazine derivatives |
| EP3472131B1 (en) | 2016-06-17 | 2020-02-19 | Forma Therapeutics, Inc. | 2-spiro-5- and 6-hydroxamic acid indanes as hdac inhibitors |
| WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
| IT201700041723A1 (it) | 2017-04-14 | 2018-10-14 | Italfarmaco Spa | Nuovi inibitori selettivi di HDAC6 |
| EP3672958B1 (en) | 2017-08-24 | 2023-08-02 | Asceneuron SA | Annulated glycosidase inhibitors |
| EP3672959A1 (en) | 2017-08-24 | 2020-07-01 | Asceneuron SA | Linear glycosidase inhibitors |
| US12016852B2 (en) | 2018-08-22 | 2024-06-25 | Asceneuron Sa | Pyrrolidine glycosidase inhibitors |
| WO2020039028A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Tetrahydro-benzoazepine glycosidase inhibitors |
| EP3841093B1 (en) | 2018-08-22 | 2023-06-21 | Asceneuron SA | Succinate and fumarate acid addition salts of piperazine derivatives useful as glycosidase inhibitors |
| US11731972B2 (en) | 2018-08-22 | 2023-08-22 | Asceneuron Sa | Spiro compounds as glycosidase inhibitors |
| ES2939730T3 (es) | 2019-01-17 | 2023-04-26 | Univ Lille | Compuestos de heteroarilo de 5 miembros que contienen un resto hidroxamato y su uso |
| WO2021021979A2 (en) * | 2019-07-30 | 2021-02-04 | Eikonizo Therapapeutics, Inc. | Hdac6 inhibitors and uses thereof |
| CN114980887A (zh) | 2019-12-20 | 2022-08-30 | 特纳亚治疗股份有限公司 | 氟代烷基-噁二唑及其用途 |
| IL307883A (en) | 2021-04-23 | 2023-12-01 | Tenaya Therapeutics Inc | HDAC6 inhibitors for use in the treatment of dilated myocardial disease |
| WO2022235842A1 (en) | 2021-05-04 | 2022-11-10 | Tenaya Therapeutics, Inc. | 2-fluoroalkyl-1,3,4-oxadiazol-5-yl-thiazol, hdac6 inhibitors for use in the treatment of metabolic disease and hfpef |
| EP4504190A4 (en) | 2022-04-08 | 2026-03-25 | Eikonizo Therapeutics Inc | OXADIAZOLE HDAC6 INHIBITORS AND THEIR USES |
| WO2025215092A1 (en) | 2024-04-10 | 2025-10-16 | Institut National de la Santé et de la Recherche Médicale | Selective hdac6 inhibitors for use in the treatment of myotonic dystrophy type 1 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6232320B1 (en) * | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| KR20010052570A (ko) | 1998-06-04 | 2001-06-25 | 스티븐 에프. 웨인스톡 | 세포 유착을 억제하는 소염성 화합물 |
| HK1045306A1 (zh) | 1999-06-03 | 2002-11-22 | Abbott Laboratories | 抑制细胞黏附的抗炎化合物 |
| CA2391952C (en) * | 1999-11-23 | 2012-01-31 | Methylgene Inc. | Inhibitors of histone deacetylase |
| EP1359146B1 (en) * | 2000-10-31 | 2008-04-09 | Rensselaer Polytechnic Institute | 4-aryl piperidines as opioid receptor binding agents |
| WO2003066889A2 (en) * | 2002-02-07 | 2003-08-14 | Axys Pharmaceuticals, Inc. | Assay for acytyltransferase or deacetylase activity |
| CA2476067C (en) * | 2002-03-13 | 2011-09-20 | Janssen Pharmaceutica N.V. | Carbonylamino-derivatives as novel inhibitors of histone deacetylase |
| US7250514B1 (en) * | 2002-10-21 | 2007-07-31 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| KR20050122210A (ko) | 2003-03-17 | 2005-12-28 | 다케다 샌디에고, 인코포레이티드 | 히스톤 탈아세틸화 효소 억제제 |
| US7935724B2 (en) * | 2003-10-09 | 2011-05-03 | Merck Hdac Research, Llc | Thiophene and benzothiophene hydroxamic acid derivatives |
| TW201245229A (en) | 2003-10-14 | 2012-11-16 | Hoffmann La Roche | Macrocyclic carboxylic acids and acylsulfonamides as inhibitors of HCV replication |
| US20070167499A1 (en) | 2003-10-27 | 2007-07-19 | A*Bio Pte Ltd. | Biaryl linked hydroxamates: preparation and pharmaceutical applications |
| WO2005108367A1 (en) * | 2004-05-03 | 2005-11-17 | Envivo Pharmaceuticals, Inc. | Compounds for treatment of neurodegenerative diseases |
| US20080004282A1 (en) | 2006-04-10 | 2008-01-03 | Painceptor Pharma Corporation | Compositions and methods for modulating gated ion channels |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| MX2009006327A (es) * | 2006-12-15 | 2009-06-23 | Novartis Ag | Compuestos heterociclicos y metodos de uso de los mismos. |
| CA2700058A1 (en) | 2007-09-19 | 2009-03-26 | 4Sc Ag | Novel tetrahydrofusedpyridines |
| EP2100879A1 (en) | 2008-03-13 | 2009-09-16 | 4Sc Ag | Novel N-substituted tetrahydroisoquinoline/isoindoline hydroxamic acid compounds |
| EP2265590B8 (en) | 2008-04-15 | 2016-07-27 | Pharmacyclics LLC | Selective inhibitors of histone deacetylase |
| CA2765678A1 (en) | 2009-06-22 | 2010-12-29 | Christopher Blackburn | Substituted hydroxamic acids and uses thereof |
| WO2010151317A1 (en) | 2009-06-22 | 2010-12-29 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2012027564A1 (en) | 2010-08-26 | 2012-03-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2012088015A2 (en) | 2010-12-22 | 2012-06-28 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
-
2010
- 2010-06-21 CA CA2765678A patent/CA2765678A1/en not_active Abandoned
- 2010-06-21 JP JP2012516072A patent/JP5798115B2/ja not_active Expired - Fee Related
- 2010-06-21 US US12/803,169 patent/US9096518B2/en not_active Expired - Fee Related
- 2010-06-21 EP EP10792446.6A patent/EP2445340B1/en active Active
- 2010-06-21 WO PCT/US2010/001801 patent/WO2010151318A1/en not_active Ceased
-
2015
- 2015-01-26 JP JP2015012045A patent/JP2015078237A/ja active Pending
- 2015-07-07 US US14/792,762 patent/US9321731B2/en not_active Expired - Fee Related
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