JP2018515489A5 - - Google Patents
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- Publication number
- JP2018515489A5 JP2018515489A5 JP2017557324A JP2017557324A JP2018515489A5 JP 2018515489 A5 JP2018515489 A5 JP 2018515489A5 JP 2017557324 A JP2017557324 A JP 2017557324A JP 2017557324 A JP2017557324 A JP 2017557324A JP 2018515489 A5 JP2018515489 A5 JP 2018515489A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- membered
- compound according
- alkyl
- 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
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- -1 3-phenylazetidin-1-yl Chemical group 0.000 claims description 107
- 150000001875 compounds Chemical class 0.000 claims description 100
- 150000003839 salts Chemical class 0.000 claims description 93
- 125000001424 substituent group Chemical group 0.000 claims description 81
- 229910052757 nitrogen Inorganic materials 0.000 claims description 67
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 59
- 125000005843 halogen group Chemical group 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 20
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 12
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 12
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 8
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 102000003964 Histone deacetylase Human genes 0.000 claims description 5
- 108090000353 Histone deacetylase Proteins 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000001627 3 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 2
- 102100021454 Histone deacetylase 4 Human genes 0.000 claims description 2
- 101000899259 Homo sapiens Histone deacetylase 4 Proteins 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 230000000626 neurodegenerative effect Effects 0.000 claims description 2
- 230000007170 pathology Effects 0.000 claims description 2
- 108010033040 Histones Proteins 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- VZNPNWZRFNGPCD-DHXVBOOMSA-N 3-fluoro-N-[(2R)-1-[(2S)-2-methylpyrrolidin-1-ium-1-yl]propan-2-yl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide formate Chemical compound [O-]C=O.C[C@H](C[NH+]1CCC[C@@H]1C)NC(=O)c1ccc(-c2noc(n2)C(F)(F)F)c(F)c1 VZNPNWZRFNGPCD-DHXVBOOMSA-N 0.000 description 1
- UHNTVGGNBPFNBL-HNNXBMFYSA-N N-[(1R)-1-cyclopropyl-2-pyrrolidin-1-ylethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C1(CC1)[C@H](CN1CCCC1)NC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O UHNTVGGNBPFNBL-HNNXBMFYSA-N 0.000 description 1
- UHNTVGGNBPFNBL-OAHLLOKOSA-N N-[(1S)-1-cyclopropyl-2-pyrrolidin-1-ylethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C1(CC1)[C@@H](CN1CCCC1)NC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O UHNTVGGNBPFNBL-OAHLLOKOSA-N 0.000 description 1
- FJDBAYCKADCQBQ-XNOZTZMFSA-N N-[(2R)-1-(1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-2-ium-2-yl)propan-2-yl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide formate Chemical compound [O-]C=O.C[C@H](C[NH+]1CC2CCCC2C1)NC(=O)c1ccc(cc1)-c1noc(n1)C(F)(F)F FJDBAYCKADCQBQ-XNOZTZMFSA-N 0.000 description 1
- ZHVSKKPOSCSUPK-CYBMUJFWSA-N N-[(2R)-1-(3,4-dihydro-1H-2,7-naphthyridin-2-yl)propan-2-yl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C1N(CCC2=CC=NC=C12)C[C@@H](C)NC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O ZHVSKKPOSCSUPK-CYBMUJFWSA-N 0.000 description 1
- IPGUFGHVOXYGBE-VCANKDNSSA-N N-[(2R)-1-(6,6-dimethyl-3-azabicyclo[3.1.0]hexan-3-yl)propan-2-yl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound CC1(C2CN(CC12)C[C@@H](C)NC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O)C IPGUFGHVOXYGBE-VCANKDNSSA-N 0.000 description 1
- IZFWXPXCTQFPQU-CYBMUJFWSA-N N-[(2R)-1-(azepan-1-yl)propan-2-yl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound N1(CCCCCC1)C[C@@H](C)NC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O IZFWXPXCTQFPQU-CYBMUJFWSA-N 0.000 description 1
- HMUGKBRTVPNJFM-UHFFFAOYSA-N N-[2-(3-azabicyclo[3.2.1]octan-3-yl)ethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C12CN(CC(CC1)C2)CCNC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O HMUGKBRTVPNJFM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XAXGLDHLTLQVOD-UHFFFAOYSA-N pyrrolidin-1-ium;formate Chemical compound [O-]C=O.C1CC[NH2+]C1 XAXGLDHLTLQVOD-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562158363P | 2015-05-07 | 2015-05-07 | |
| US62/158,363 | 2015-05-07 | ||
| PCT/US2016/031335 WO2016179554A1 (en) | 2015-05-07 | 2016-05-06 | Histone deacetylase inhibitors and compositions and methods of use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018515489A JP2018515489A (ja) | 2018-06-14 |
| JP2018515489A5 true JP2018515489A5 (https=) | 2019-06-13 |
| JP6805172B2 JP6805172B2 (ja) | 2020-12-23 |
Family
ID=57218014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017557324A Active JP6805172B2 (ja) | 2015-05-07 | 2016-05-06 | ヒストンデアセチラーゼ阻害薬及び組成物並びにそれらの使用の方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10053434B2 (https=) |
| EP (1) | EP3291810B1 (https=) |
| JP (1) | JP6805172B2 (https=) |
| KR (1) | KR20180002729A (https=) |
| CN (1) | CN107735088B (https=) |
| AU (1) | AU2016258188B2 (https=) |
| CA (1) | CA2984618C (https=) |
| EA (1) | EA036965B1 (https=) |
| IL (1) | IL255448B2 (https=) |
| MX (1) | MX378983B (https=) |
| WO (1) | WO2016179554A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180002729A (ko) * | 2015-05-07 | 2018-01-08 | 씨에이치디아이 파운데이션, 인코포레이티드 | 히스톤 탈아세틸효소 억제제 및 그것의 조성물 및 사용 방법 |
| EA035592B1 (ru) | 2015-05-07 | 2020-07-13 | Сиэйчдиай Фаундэйшн, Инк. | Ингибиторы деацетилаз гистонов и композиции и способы их применения |
| US10757941B2 (en) * | 2016-07-22 | 2020-09-01 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
| CN109627207A (zh) * | 2018-12-17 | 2019-04-16 | 天津药明康德新药开发有限公司 | 一种3-(二氟甲氧基)哌啶盐酸盐的制备方法 |
| AU2020321955A1 (en) | 2019-07-30 | 2022-03-17 | Eikonizo Therapapeutics, Inc. | HDAC6 inhibitors and uses thereof |
| US20240327361A1 (en) * | 2021-02-15 | 2024-10-03 | The Research Foundation For The State University Of New York | Radiolabeled compositions and methods of use thereof |
| IL316201A (en) | 2022-04-08 | 2024-12-01 | Eikonizo Therapeutics Inc | Oxadiazole HDAC6 inhibitors and their uses |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1828171B1 (en) | 2004-12-10 | 2014-03-12 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Heterocycle derivatives as histone deacetylase (hdac) inhibitors |
| CN103221047B (zh) | 2010-01-13 | 2014-12-17 | 坦颇罗制药股份有限公司 | 化合物和方法 |
| WO2013006408A1 (en) * | 2011-07-01 | 2013-01-10 | 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 |
| WO2013009810A1 (en) | 2011-07-13 | 2013-01-17 | Tempero Pharmaceuticals, Inc. | Methods of treatment |
| WO2013009830A1 (en) * | 2011-07-13 | 2013-01-17 | Tempero Pharmaceuticals, Inc. | Methods of treatment |
| SI2750677T1 (sl) | 2011-08-30 | 2017-10-30 | Chdi Foundation, Inc. | Inhibitorji kinurenin-3-monooksigenaze, farmacevtski sestavki in postopki njihove uporabe |
| WO2013066835A2 (en) * | 2011-10-31 | 2013-05-10 | Glaxosmithkline Llc | Compounds and methods |
| WO2013066833A1 (en) * | 2011-10-31 | 2013-05-10 | Glaxosmithkline Llc | Compounds and methods to inhibit histone deacetylase (hdac) enzymes |
| CA2856334A1 (en) * | 2011-11-28 | 2013-06-06 | Christina Hebach | Novel trifluoromethyl-oxadiazole derivatives and their use in the treatment of disease |
| EP3130583B1 (en) * | 2012-04-05 | 2024-01-03 | CHDI Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| EA035592B1 (ru) | 2015-05-07 | 2020-07-13 | Сиэйчдиай Фаундэйшн, Инк. | Ингибиторы деацетилаз гистонов и композиции и способы их применения |
| KR20180002729A (ko) * | 2015-05-07 | 2018-01-08 | 씨에이치디아이 파운데이션, 인코포레이티드 | 히스톤 탈아세틸효소 억제제 및 그것의 조성물 및 사용 방법 |
| ES2774510T3 (es) | 2015-07-27 | 2020-07-21 | Chong Kun Dang Pharmaceutical Corp | Derivados de 1,3,4-oxadiazol sulfamida como inhibidores de histona desacetilasa 6 y composición farmacéutica que comprende los mismos |
| FI3328843T3 (fi) | 2015-07-27 | 2023-01-31 | 1,3,4-oksadiatsolisulfonamidijohdannaisyhdisteitä histonideasetylaasi-6:n inhibiittoreina ja samaa käsittävä farmaseuttinen koostumus | |
| RU2709207C2 (ru) | 2015-08-04 | 2019-12-17 | Чонг Кун Данг Фармасьютикал Корп. | 1,3,4-оксадиазольные производные соединения в качестве ингибитора гистондеацетилазы 6 и фармацевтическая композиция, содержащая их |
-
2016
- 2016-05-06 KR KR1020177034461A patent/KR20180002729A/ko not_active Withdrawn
- 2016-05-06 MX MX2017014300A patent/MX378983B/es unknown
- 2016-05-06 EA EA201792247A patent/EA036965B1/ru not_active IP Right Cessation
- 2016-05-06 CN CN201680040061.8A patent/CN107735088B/zh active Active
- 2016-05-06 AU AU2016258188A patent/AU2016258188B2/en active Active
- 2016-05-06 JP JP2017557324A patent/JP6805172B2/ja active Active
- 2016-05-06 US US15/148,907 patent/US10053434B2/en active Active
- 2016-05-06 CA CA2984618A patent/CA2984618C/en active Active
- 2016-05-06 EP EP16790203.0A patent/EP3291810B1/en active Active
- 2016-05-06 WO PCT/US2016/031335 patent/WO2016179554A1/en not_active Ceased
-
2017
- 2017-11-06 IL IL255448A patent/IL255448B2/en unknown
-
2018
- 2018-07-26 US US16/046,254 patent/US20190202795A1/en not_active Abandoned
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