JP2018522925A5 - - Google Patents
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- Publication number
- JP2018522925A5 JP2018522925A5 JP2018506999A JP2018506999A JP2018522925A5 JP 2018522925 A5 JP2018522925 A5 JP 2018522925A5 JP 2018506999 A JP2018506999 A JP 2018506999A JP 2018506999 A JP2018506999 A JP 2018506999A JP 2018522925 A5 JP2018522925 A5 JP 2018522925A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cancer
- substituted
- propyl
- unsubstituted
- 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 26
- -1 n- propyl Chemical group 0.000 claims 21
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000000651 prodrug Substances 0.000 claims 5
- 229940002612 prodrug Drugs 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 206010009944 Colon cancer Diseases 0.000 claims 3
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- 208000029742 colonic neoplasm Diseases 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 206010027406 Mesothelioma Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 208000035269 cancer or benign tumor Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 206010061187 Haematopoietic neoplasm Diseases 0.000 claims 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 229940125763 bromodomain inhibitor Drugs 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000005879 dioxolanyl group Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000005787 hematologic cancer Diseases 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BFPHOHPRIISKIB-UHFFFAOYSA-N 6-bromo-2-cyclopropyl-1-[2-(trifluoromethoxy)ethyl]benzimidazole Chemical compound BrC=1C=CC2=C(N(C(=N2)C2CC2)CCOC(F)(F)F)C=1 BFPHOHPRIISKIB-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562204178P | 2015-08-12 | 2015-08-12 | |
| US62/204,178 | 2015-08-12 | ||
| US201662358101P | 2016-07-04 | 2016-07-04 | |
| US62/358,101 | 2016-07-04 | ||
| PCT/CA2016/050952 WO2017024412A1 (en) | 2015-08-12 | 2016-08-12 | Substituted benzimidazoles, their preparation and their use as pharmaceuticals |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018522925A JP2018522925A (ja) | 2018-08-16 |
| JP2018522925A5 true JP2018522925A5 (https=) | 2019-09-26 |
| JP6912039B2 JP6912039B2 (ja) | 2021-07-28 |
Family
ID=57982882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018506999A Active JP6912039B2 (ja) | 2015-08-12 | 2016-08-12 | 置換ベンゾイミダゾール、それらの調製及び医薬品としてのそれらの使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US10703740B2 (https=) |
| EP (1) | EP3334719B1 (https=) |
| JP (1) | JP6912039B2 (https=) |
| KR (1) | KR102784592B1 (https=) |
| CN (2) | CN108137539B (https=) |
| AU (2) | AU2016305515A1 (https=) |
| CA (1) | CA2994478C (https=) |
| ES (1) | ES2904258T3 (https=) |
| IL (1) | IL257340B2 (https=) |
| MX (1) | MX382832B (https=) |
| WO (1) | WO2017024412A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108137539B (zh) * | 2015-08-12 | 2022-01-11 | 尼奥迈德研究所 | 取代的苯并咪唑、它们的制备和它们作为药物的用途 |
| GB201617627D0 (en) | 2016-10-18 | 2016-11-30 | Cellcentric Ltd | Pharmaceutical compounds |
| GB201617630D0 (en) | 2016-10-18 | 2016-11-30 | Cellcentric Ltd | Pharmaceutical compounds |
| JP7165501B2 (ja) * | 2017-03-15 | 2022-11-04 | 住友ファーマ株式会社 | 新規ベンズイミダゾール化合物からなる医薬 |
| WO2018207882A1 (ja) * | 2017-05-12 | 2018-11-15 | 武田薬品工業株式会社 | 複素環化合物 |
| GB201806320D0 (en) | 2018-04-18 | 2018-05-30 | Cellcentric Ltd | Process |
| WO2020093162A1 (en) * | 2018-11-07 | 2020-05-14 | Neomed Institute | Treatment of bet inhibitor-resistant cancers and other diseases responsive to dual bet and cbp/ep300 inhibition therapy |
| JP2022053557A (ja) * | 2019-02-08 | 2022-04-06 | マルホ株式会社 | ピリドン誘導体 |
| CN112174945B (zh) * | 2019-07-02 | 2022-06-07 | 四川大学 | 具有抗癌作用的吲唑类化合物及其制备方法和用途 |
| CN115232074A (zh) * | 2022-08-22 | 2022-10-25 | 湖南复瑞生物医药技术有限责任公司 | 一种1-烷基取代-2-甲基-5-溴苯并咪唑的合成方法 |
| WO2024249796A2 (en) * | 2023-06-02 | 2024-12-05 | Epigenetix, Inc. | Extended and delayed release compositions of substituted benzimidazoles |
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| DE4237656A1 (de) * | 1992-06-13 | 1993-12-16 | Merck Patent Gmbh | Benzimidazolderivate |
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| WO2008078091A1 (en) | 2006-12-22 | 2008-07-03 | Astex Therapeutics Limited | Bicyclic heterocyclic compounds as fgfr inhibitors |
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| AR104259A1 (es) * | 2015-04-15 | 2017-07-05 | Celgene Quanticel Res Inc | Inhibidores de bromodominio |
| GB201506660D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| GB201506658D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| CN108137539B (zh) * | 2015-08-12 | 2022-01-11 | 尼奥迈德研究所 | 取代的苯并咪唑、它们的制备和它们作为药物的用途 |
-
2016
- 2016-08-12 CN CN201680059249.7A patent/CN108137539B/zh active Active
- 2016-08-12 JP JP2018506999A patent/JP6912039B2/ja active Active
- 2016-08-12 CA CA2994478A patent/CA2994478C/en active Active
- 2016-08-12 AU AU2016305515A patent/AU2016305515A1/en not_active Abandoned
- 2016-08-12 IL IL257340A patent/IL257340B2/en unknown
- 2016-08-12 KR KR1020187006581A patent/KR102784592B1/ko active Active
- 2016-08-12 ES ES16834372T patent/ES2904258T3/es active Active
- 2016-08-12 US US15/751,801 patent/US10703740B2/en active Active
- 2016-08-12 CN CN202111621671.6A patent/CN114605387A/zh active Pending
- 2016-08-12 WO PCT/CA2016/050952 patent/WO2017024412A1/en not_active Ceased
- 2016-08-12 MX MX2018001756A patent/MX382832B/es unknown
- 2016-08-12 EP EP16834372.1A patent/EP3334719B1/en active Active
-
2020
- 2020-05-22 US US16/881,803 patent/US11365186B2/en active Active
-
2021
- 2021-01-12 AU AU2021200147A patent/AU2021200147B2/en active Active
-
2022
- 2022-05-13 US US17/743,792 patent/US11981657B2/en active Active
-
2024
- 2024-04-08 US US18/629,321 patent/US20240425481A1/en active Pending
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