JP2017532358A5 - - Google Patents
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- JP2017532358A5 JP2017532358A5 JP2017522845A JP2017522845A JP2017532358A5 JP 2017532358 A5 JP2017532358 A5 JP 2017532358A5 JP 2017522845 A JP2017522845 A JP 2017522845A JP 2017522845 A JP2017522845 A JP 2017522845A JP 2017532358 A5 JP2017532358 A5 JP 2017532358A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- alkyl
- compound
- halogen
- 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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- 150000001875 compounds Chemical class 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 102000003964 Histone deacetylase Human genes 0.000 claims description 18
- 108090000353 Histone deacetylase Proteins 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 230000004968 inflammatory condition Effects 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- -1 C 1 -C 3 alkoxy Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 206010007558 Cardiac failure chronic Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 230000004572 zinc-binding Effects 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000006697 (C1-C3) aminoalkyl group Chemical group 0.000 claims description 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 2
- MWHBLJSFTJJAJE-UHFFFAOYSA-N 4-[[[5-(2-aminopyridin-4-yl)pyridin-2-yl]-pyrazin-2-ylamino]methyl]-N-hydroxybenzamide Chemical compound Nc1cc(ccn1)-c1ccc(nc1)N(Cc1ccc(cc1)C(=O)NO)c1cnccn1 MWHBLJSFTJJAJE-UHFFFAOYSA-N 0.000 claims description 2
- IGGATYAYFIGECV-UHFFFAOYSA-N 4-[[[5-(6-aminopyridin-3-yl)pyridin-2-yl]-pyrazin-2-ylamino]methyl]-N-hydroxybenzamide Chemical compound Nc1ccc(cn1)-c1ccc(nc1)N(Cc1ccc(cc1)C(=O)NO)c1cnccn1 IGGATYAYFIGECV-UHFFFAOYSA-N 0.000 claims description 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 2
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 2
- 208000006029 Cardiomegaly Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 201000004624 Dermatitis Diseases 0.000 claims description 2
- 208000001914 Fragile X syndrome Diseases 0.000 claims description 2
- 206010020880 Hypertrophy Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims description 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
- 206010027406 Mesothelioma Diseases 0.000 claims description 2
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 2
- 208000004179 Oral Leukoplakia Diseases 0.000 claims description 2
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010042971 T-cell lymphoma Diseases 0.000 claims description 2
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 2
- 208000002903 Thalassemia Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 208000006682 alpha 1-Antitrypsin Deficiency Diseases 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 229940034982 antineoplastic agent Drugs 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 208000015114 central nervous system disease Diseases 0.000 claims description 2
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 2
- 208000019069 chronic childhood arthritis Diseases 0.000 claims description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 2
- 210000003780 hair follicle Anatomy 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 2
- 230000001861 immunosuppressant effect Effects 0.000 claims description 2
- 239000003018 immunosuppressive agent Substances 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 201000004990 juvenile ankylosing spondylitis Diseases 0.000 claims description 2
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims description 2
- 208000030159 metabolic disease Diseases 0.000 claims description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 201000008557 oral mucosa leukoplakia Diseases 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 208000007056 sickle cell anemia Diseases 0.000 claims description 2
- 210000003491 skin Anatomy 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 230000029663 wound healing Effects 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 150000002366 halogen compounds Chemical group 0.000 claims 1
- 239000012528 membrane Substances 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- MORLMWOGSGAGJR-UHFFFAOYSA-N Nc1ccc(CN(c2nccc(N)c2)c2nccnc2)c(F)c1 Chemical compound Nc1ccc(CN(c2nccc(N)c2)c2nccnc2)c(F)c1 MORLMWOGSGAGJR-UHFFFAOYSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1419264.5 | 2014-10-29 | ||
| GBGB1419264.5A GB201419264D0 (en) | 2014-10-29 | 2014-10-29 | Compounds |
| PCT/GB2015/053256 WO2016067038A1 (en) | 2014-10-29 | 2015-10-29 | Polyheteroaryl histone deacetylase inhibitors and their use in therapy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017532358A JP2017532358A (ja) | 2017-11-02 |
| JP2017532358A5 true JP2017532358A5 (https=) | 2018-08-30 |
Family
ID=52103592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017522845A Pending JP2017532358A (ja) | 2014-10-29 | 2015-10-29 | ポリヘテロアリールヒストンデアセチラーゼインヒビターおよび治療におけるその使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10533003B2 (https=) |
| EP (1) | EP3212632A1 (https=) |
| JP (1) | JP2017532358A (https=) |
| CN (1) | CN107001333A (https=) |
| AU (1) | AU2015340303B2 (https=) |
| CA (1) | CA2966070A1 (https=) |
| GB (1) | GB201419264D0 (https=) |
| IL (1) | IL251861A0 (https=) |
| MX (1) | MX2017005423A (https=) |
| WO (1) | WO2016067038A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6329958B2 (ja) * | 2012-11-07 | 2018-05-23 | カルス セラピューティクス リミテッド | 新規ヒストンデアセチラーゼインヒビターおよび治療におけるその使用 |
| NZ714283A (en) | 2013-05-10 | 2020-04-24 | Karus Therapeutics Ltd | Novel histone deacetylase inhibitors |
| GB201419264D0 (en) | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
| GB201419228D0 (en) | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
| GB201609786D0 (en) * | 2016-06-03 | 2016-07-20 | Karus Therapeutics Ltd | Compounds and method of use |
| WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
| CN109096272B (zh) * | 2018-09-27 | 2021-04-02 | 沈阳药科大学 | 一种具有抗肿瘤活性的吲哚异羟肟酸类化合物及其应用 |
| CN115443329A (zh) | 2019-06-27 | 2022-12-06 | 乔治华盛顿大学国会特许非营利公司 | Hdac6激活的巨噬细胞、其组合物及用途 |
| AU2020321955A1 (en) | 2019-07-30 | 2022-03-17 | Eikonizo Therapapeutics, Inc. | HDAC6 inhibitors and uses thereof |
| IL316201A (en) | 2022-04-08 | 2024-12-01 | Eikonizo Therapeutics Inc | Oxadiazole HDAC6 inhibitors and their uses |
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| EP2508510A1 (en) | 2011-04-06 | 2012-10-10 | Ikerchem, S.L. | Hydroxyphenyl pyrrole compounds containing an hydroxamic acid as hdac inhibitors and medicinal applications thereof |
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| WO2013052110A1 (en) | 2011-10-03 | 2013-04-11 | The Trustees Of Columbia University In The City Of New York | Novel molecules that selectively inhibit histone deacetylase 6 relative to histone deacetylase 1 |
| KR20140071472A (ko) | 2011-10-04 | 2014-06-11 | 인스티튜트 포 헤퍼타이티스 앤드 바이러스 리서치 | 간세포 암종을 포함하는 암의 저해제로서 그리고 간염 바이러스 복제의 저해제로서의 치환된 아미노티아졸 |
| UA111754C2 (uk) * | 2011-10-06 | 2016-06-10 | Байєр Фарма Акцієнгезелльшафт | Заміщені бензиліндазоли для застосування як інгібіторів bub1-кінази для лікування гіперпроліферативних захворювань |
| DK2790705T3 (en) | 2011-12-15 | 2018-03-12 | Novartis Ag | Use of inhibitors of the activity or function of PI3K |
| KR101415742B1 (ko) | 2011-12-21 | 2014-07-04 | 영남대학교 산학협력단 | 6―아미노피리딘―3―올 유도체 또는 이의 약제학적 허용가능한 염 및 이를 유효성분으로 함유하는 혈관신생으로 인한 질환의 예방 또는 치료용 약학조성물 |
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| US9695108B2 (en) | 2012-08-23 | 2017-07-04 | Georgetown University | Compounds and methods of use thereof for treating tumors |
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| US9169214B2 (en) | 2012-12-21 | 2015-10-27 | The Board Of Trustees Of The Leland Stanford Junior University | Compounds and compositions that bind and stabilize transthyretin and their use for inhibiting transthyretin amyloidosis and protein-protein interactions |
| US20160052926A1 (en) | 2013-03-15 | 2016-02-25 | Hutchison Medipharma Limited | Novel pyrimidine and pyridine compounds and usage thereof |
| WO2014153280A1 (en) | 2013-03-22 | 2014-09-25 | Merck Sharp & Dohme Corp. | 2-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
| NZ714283A (en) * | 2013-05-10 | 2020-04-24 | Karus Therapeutics Ltd | Novel histone deacetylase inhibitors |
| GB201402431D0 (en) | 2014-02-12 | 2014-03-26 | Karus Therapeutics Ltd | Compounds |
| US10081624B2 (en) | 2014-08-26 | 2018-09-25 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| GB201419264D0 (en) | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
| GB201419228D0 (en) | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
| GB201609786D0 (en) | 2016-06-03 | 2016-07-20 | Karus Therapeutics Ltd | Compounds and method of use |
| WO2017222950A1 (en) | 2016-06-23 | 2017-12-28 | Merck Sharp & Dohme Corp. | 3-heterocyclyl substituted 5-trifluoromethyl oxadiazoles as histone deacetylase 6 (hdac6) inhibitors |
| US11066396B2 (en) | 2016-06-23 | 2021-07-20 | Merck Sharp & Dohme Corp. | 3-aryl- heteroaryl substituted 5-trifluoromethyl oxadiazoles as histonedeacetylase 6 (HDAC6) inhibitors |
| WO2017222952A1 (en) | 2016-06-23 | 2017-12-28 | Merck Sharp & Dohme Corp. | 3- heteroaryl substituted 5-trifluoromethyl oxadiazoles as histone deacetylase 6 (hdac6) inhibitors |
-
2014
- 2014-10-29 GB GBGB1419264.5A patent/GB201419264D0/en not_active Ceased
-
2015
- 2015-10-29 CN CN201580066141.6A patent/CN107001333A/zh active Pending
- 2015-10-29 MX MX2017005423A patent/MX2017005423A/es unknown
- 2015-10-29 CA CA2966070A patent/CA2966070A1/en not_active Abandoned
- 2015-10-29 JP JP2017522845A patent/JP2017532358A/ja active Pending
- 2015-10-29 AU AU2015340303A patent/AU2015340303B2/en not_active Withdrawn - After Issue
- 2015-10-29 US US15/522,191 patent/US10533003B2/en not_active Expired - Fee Related
- 2015-10-29 WO PCT/GB2015/053256 patent/WO2016067038A1/en not_active Ceased
- 2015-10-29 EP EP15790222.2A patent/EP3212632A1/en not_active Withdrawn
-
2017
- 2017-04-23 IL IL251861A patent/IL251861A0/en unknown
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