JP2018515492A5 - - Google Patents
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- Publication number
- JP2018515492A5 JP2018515492A5 JP2017557413A JP2017557413A JP2018515492A5 JP 2018515492 A5 JP2018515492 A5 JP 2018515492A5 JP 2017557413 A JP2017557413 A JP 2017557413A JP 2017557413 A JP2017557413 A JP 2017557413A JP 2018515492 A5 JP2018515492 A5 JP 2018515492A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- alkyl
- acceptable salt
- membered
- compound according
- 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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- 150000001875 compounds Chemical class 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 55
- 125000005843 halogen group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- -1 -C 1 -C 4 - alkyl Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
- 102000003964 Histone deacetylase Human genes 0.000 claims description 6
- 108090000353 Histone deacetylase Proteins 0.000 claims description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 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 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl 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
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 230000000626 neurodegenerative effect Effects 0.000 claims description 2
- 230000007170 pathology Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 description 12
- UWBSPFFYHKFGOE-UHFFFAOYSA-N N-[1-[(3,3-dimethylpiperidin-1-yl)methyl]cyclopropyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound CC1(CN(CCC1)CC1(CC1)NC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O)C UWBSPFFYHKFGOE-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 0 *C(N(*)C(c1c(*)c(*)c(-c2n[o]c(C(F)(F)F)n2)c(*)c1*)=O)=* Chemical compound *C(N(*)C(c1c(*)c(*)c(-c2n[o]c(C(F)(F)F)n2)c(*)c1*)=O)=* 0.000 description 1
- APPYRJBKNMMYBG-UHFFFAOYSA-N N-[1-(2-oxa-5-azaspiro[3.4]octan-5-ylmethyl)cyclobutyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound FC(F)(F)C1=NC(=NO1)C1=CC=C(C=C1)C(=O)NC1(CN2CCCC22COC2)CCC1 APPYRJBKNMMYBG-UHFFFAOYSA-N 0.000 description 1
- XXRQRMAWAPFYPS-UHFFFAOYSA-N N-[1-(2-oxa-5-azaspiro[3.4]octan-5-ylmethyl)cyclopropyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound FC(F)(F)C1=NC(=NO1)C1=CC=C(C=C1)C(=O)NC1(CN2CCCC22COC2)CC1 XXRQRMAWAPFYPS-UHFFFAOYSA-N 0.000 description 1
- RIXICKUDZTYFDS-UHFFFAOYSA-N N-[1-(2-oxa-7-azaspiro[3.5]nonan-7-ylmethyl)cyclopropyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound FC(F)(F)C1=NC(=NO1)C1=CC=C(C=C1)C(=O)NC1(CN2CCC3(COC3)CC2)CC1 RIXICKUDZTYFDS-UHFFFAOYSA-N 0.000 description 1
- JOAQFUQHIMMIMB-UHFFFAOYSA-N N-[1-(3-azabicyclo[3.2.1]octan-3-ylmethyl)cyclopropyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C12CN(CC(CC1)C2)CC1(CC1)NC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O JOAQFUQHIMMIMB-UHFFFAOYSA-N 0.000 description 1
- KDTCSZKKTPRSAS-UHFFFAOYSA-N N-[1-(5-azaspiro[2.4]heptan-5-ylmethyl)cyclobutyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound FC(F)(F)C1=NC(=NO1)C1=CC=C(C=C1)C(=O)NC1(CN2CCC3(CC3)C2)CCC1 KDTCSZKKTPRSAS-UHFFFAOYSA-N 0.000 description 1
- SOUBSJUNNDFMBE-UHFFFAOYSA-N N-[1-(5-azaspiro[2.5]octan-5-ylmethyl)cyclopropyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C1CC11CN(CCC1)CC1(CC1)NC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O SOUBSJUNNDFMBE-UHFFFAOYSA-N 0.000 description 1
- BIULWZLYCZLVJY-UHFFFAOYSA-N N-[1-(6-azaspiro[2.5]octan-6-ylmethyl)cyclopropyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C1CC11CCN(CC1)CC1(CC1)NC(C1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F)=O BIULWZLYCZLVJY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562158379P | 2015-05-07 | 2015-05-07 | |
| US62/158,379 | 2015-05-07 | ||
| PCT/US2016/031329 WO2016179550A1 (en) | 2015-05-07 | 2016-05-06 | Histone deacetylase inhibitors and compositions and methods of use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018515492A JP2018515492A (ja) | 2018-06-14 |
| JP2018515492A5 true JP2018515492A5 (https=) | 2019-06-13 |
| JP6782255B2 JP6782255B2 (ja) | 2020-11-11 |
Family
ID=57218066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017557413A Active JP6782255B2 (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 (12)
| Country | Link |
|---|---|
| US (2) | US10047073B2 (https=) |
| EP (1) | EP3291809B1 (https=) |
| JP (1) | JP6782255B2 (https=) |
| KR (1) | KR20180002730A (https=) |
| CN (1) | CN107735087B (https=) |
| AU (1) | AU2016256917B2 (https=) |
| BR (1) | BR112017023710B1 (https=) |
| CA (1) | CA2984621C (https=) |
| EA (1) | EA035592B1 (https=) |
| IL (1) | IL255449B2 (https=) |
| MX (1) | MX379817B (https=) |
| WO (1) | WO2016179550A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2016256917B2 (en) * | 2015-05-07 | 2021-08-26 | Chdi Foundation, Inc. | Histone deacetylase inhibitors and compositions and methods of use thereof |
| MX378983B (es) | 2015-05-07 | 2025-03-10 | Chdi Foundation Inc | Inhibidores de histona deacetilasa y composiciones y metodos para el uso de los mismos. |
| WO2017211650A1 (en) * | 2016-06-09 | 2017-12-14 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| BR112019001229B1 (pt) * | 2016-07-22 | 2022-11-16 | Syngenta Participations Ag | Composto derivado de oxadiazol, composição agroquímica compreendendo o mesmo, método para controlar ou impedir infestação de plantas úteis por microrganismos fitopatogênicos e uso do referido composto como fungicida |
| WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
| WO2019219464A1 (en) | 2018-05-15 | 2019-11-21 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
| KR102052844B1 (ko) | 2019-01-31 | 2019-12-05 | 주식회사 아이스크림에듀 | 학습 분석 방법 및 시스템 |
| KR102009034B1 (ko) | 2019-01-31 | 2019-08-08 | 주식회사 아이스크림에듀 | 학습 분석을 기초로 정보를 제공하는 방법 및 시스템 |
| AU2020321955A1 (en) | 2019-07-30 | 2022-03-17 | Eikonizo Therapapeutics, Inc. | HDAC6 inhibitors and uses thereof |
| KR102232343B1 (ko) | 2019-12-11 | 2021-03-26 | 주식회사 아이스크림에듀 | 인공지능 기반 맞춤형 학습 방법 및 시스템 |
| KR102191672B1 (ko) | 2019-12-20 | 2020-12-16 | 주식회사 아이스크림에듀 | 학습 분석 및 인공지능 기반 맞춤형 학습 방법 및 시스템 |
| KR102191671B1 (ko) | 2019-12-20 | 2020-12-16 | 주식회사 아이스크림에듀 | 소셜 러닝 및 e포트폴리오 기반 맞춤형 학습 방법 및 시스템 |
| KR102197752B1 (ko) | 2019-12-20 | 2021-01-04 | 주식회사 아이스크림에듀 | 맞춤형 자동 문항 생성을 통한 인공지능 기반 학습 방법 및 시스템 |
| KR102191670B1 (ko) | 2019-12-20 | 2020-12-16 | 주식회사 아이스크림에듀 | 문제은행 및 지식맵 기반 맞춤형 학습 방법 및 시스템 |
| KR102258234B1 (ko) | 2020-02-27 | 2021-05-31 | 주식회사 아이스크림에듀 | 인공지능 가정교사 인터페이스가 적용된 맞춤형 학습 방법 및 시스템 |
| KR102258235B1 (ko) | 2020-02-27 | 2021-05-31 | 주식회사 아이스크림에듀 | 실감 콘텐츠가 적용된 인공지능 기반의 맞춤형 학습 방법 및 시스템 |
| KR102232344B1 (ko) | 2020-02-27 | 2021-03-26 | 주식회사 아이스크림에듀 | 빅데이터 및 인공지능 기반의 맞춤형 학습 방법 및 시스템 |
| CN111190006A (zh) * | 2020-03-09 | 2020-05-22 | 上海市东方医院（同济大学附属东方医院） | 组蛋白去乙酰化酶6在制备用于评估维持性腹膜透析患者腹膜功能的标志物中的用途 |
| KR102222533B1 (ko) | 2020-06-25 | 2021-03-05 | 주식회사 아이스크림미디어 | 고정형 웹 콘텐츠를 반응형 콘텐츠로 자동 변환하는 시스템 및 그 제어방법 |
| KR20230049675A (ko) * | 2020-08-07 | 2023-04-13 | 이탈파마코 에스.피.에이. | 신규한 옥사디아졸-기반 선택적 hdac6 억제제 |
| KR102248960B1 (ko) | 2020-08-19 | 2021-05-07 | 주식회사 아이스크림에듀 | 인공지능 학습 플랫폼을 이용한 비즈니스 방법 및 시스템 |
| TW202345813A (zh) | 2022-04-08 | 2023-12-01 | 美商艾科尼佐療法股份有限公司 | 㗁二唑ｈｄａｃ６抑制劑及其用途 |
| CN117430513A (zh) * | 2023-10-27 | 2024-01-23 | 中昊(大连)化工研究设计院有限公司 | 环丙基胺的合成新方法 |
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 |
| GB0427138D0 (en) * | 2004-12-10 | 2005-01-12 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US8981084B2 (en) * | 2010-01-13 | 2015-03-17 | Tempero Pharmaceuticals, Inc. | Oxadiazole HDAC inhibitors |
| AU2011205283B2 (en) | 2010-01-13 | 2014-07-10 | Tempero Pharmaceuticals, Inc. | Compounds and methods |
| WO2013006408A1 (en) | 2011-07-01 | 2013-01-10 | Tempero Pharmaceuticals, Inc. | Compounds and methods |
| EA201490228A1 (ru) * | 2011-07-08 | 2014-08-29 | Новартис Аг | Новые производные трифторметилоксадиазола и их применение для лечения заболевания |
| WO2013009830A1 (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 |
| SI2750677T1 (sl) * | 2011-08-30 | 2017-10-30 | Chdi Foundation, Inc. | Inhibitorji kinurenin-3-monooksigenaze, farmacevtski sestavki in postopki njihove uporabe |
| BR112014012815A8 (pt) | 2011-11-28 | 2017-06-20 | Novartis Ag | derivados de trifluormetil-oxadiazol e uso dos mesmos no tratamento de doença |
| KR20150000882A (ko) * | 2012-04-05 | 2015-01-05 | 씨에이치디아이 파운데이션, 인코포레이티드 | 키뉴레닌-3-모노산소첨가효소 억제제들, 약학 조성물들 및 이의 사용 방법 |
| AU2016256917B2 (en) * | 2015-05-07 | 2021-08-26 | Chdi Foundation, Inc. | Histone deacetylase inhibitors and compositions and methods of use thereof |
| MX378983B (es) | 2015-05-07 | 2025-03-10 | Chdi Foundation Inc | Inhibidores de histona deacetilasa y composiciones y metodos para el uso de los mismos. |
| PL3328843T3 (pl) | 2015-07-27 | 2023-02-27 | Chong Kun Dang Pharmaceutical Corp. | Związki będące pochodnymi 1,3,4 oksadiazolosulfonamidów jako inhibitor deacetylazy histonowej 6, oraz kompozycja farmaceutyczna je zawierająca |
| RU2695227C9 (ru) | 2015-07-27 | 2020-03-04 | Чонг Кун Данг Фармасьютикал Корп. | Производные 1,3,4-оксадиазолсульфамида в качестве ингибитора гистондеацетилазы 6 и содержащая их фармацевтическая композиция |
| JP6491393B2 (ja) | 2015-08-04 | 2019-03-27 | チョン クン ダン ファーマシューティカル コーポレーション | ヒストン脱アセチル化酵素６阻害剤としての１，３，４−オキサジアゾール誘導体化合物及びこれを含有する薬剤学的組成物 |
-
2016
- 2016-05-06 AU AU2016256917A patent/AU2016256917B2/en active Active
- 2016-05-06 EA EA201792255A patent/EA035592B1/ru not_active IP Right Cessation
- 2016-05-06 CA CA2984621A patent/CA2984621C/en active Active
- 2016-05-06 EP EP16790199.0A patent/EP3291809B1/en active Active
- 2016-05-06 US US15/148,884 patent/US10047073B2/en active Active
- 2016-05-06 BR BR112017023710-5A patent/BR112017023710B1/pt active IP Right Grant
- 2016-05-06 MX MX2017014299A patent/MX379817B/es unknown
- 2016-05-06 JP JP2017557413A patent/JP6782255B2/ja active Active
- 2016-05-06 CN CN201680040059.0A patent/CN107735087B/zh active Active
- 2016-05-06 WO PCT/US2016/031329 patent/WO2016179550A1/en not_active Ceased
- 2016-05-06 KR KR1020177034473A patent/KR20180002730A/ko not_active Withdrawn
-
2017
- 2017-11-06 IL IL255449A patent/IL255449B2/en unknown
-
2018
- 2018-07-26 US US16/046,268 patent/US20190185463A1/en not_active Abandoned
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