JP2018536015A5 - - Google Patents
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- JP2018536015A5 JP2018536015A5 JP2018534463A JP2018534463A JP2018536015A5 JP 2018536015 A5 JP2018536015 A5 JP 2018536015A5 JP 2018534463 A JP2018534463 A JP 2018534463A JP 2018534463 A JP2018534463 A JP 2018534463A JP 2018536015 A5 JP2018536015 A5 JP 2018536015A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- methyl
- phenyl
- biphenyl
- 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 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- -1 triazolylen Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims 20
- 239000012453 solvate Substances 0.000 claims 20
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 7
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 229910052805 deuterium Inorganic materials 0.000 claims 4
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 210000000941 bile Anatomy 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 1
- 125000006747 (C2-C10) heterocycloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- 206010019708 Hepatic steatosis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000006193 alkinyl group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- TXWOGHSRPAYOML-UHFFFAOYSA-M cyclobutanecarboxylate Chemical compound [O-]C(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-M 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 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 1
- 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 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 208000010706 fatty liver disease Diseases 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000004474 heteroalkylene group Chemical group 0.000 claims 1
- 125000005549 heteroarylene group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims 1
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- BYABCGOPKZDENF-UHFFFAOYSA-N CN(C)C(C=C1)=CC=C1C1=CC=C(CNC(C2CCCCC2)=O)C=C1 Chemical compound CN(C)C(C=C1)=CC=C1C1=CC=C(CNC(C2CCCCC2)=O)C=C1 BYABCGOPKZDENF-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004172 nitrogen cycle Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562219430P | 2015-09-16 | 2015-09-16 | |
| US62/219,430 | 2015-09-16 | ||
| PCT/US2016/052270 WO2017049173A1 (en) | 2015-09-16 | 2016-09-16 | Farnesoid x receptor agonists and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018536015A JP2018536015A (ja) | 2018-12-06 |
| JP2018536015A5 true JP2018536015A5 (enExample) | 2021-01-14 |
| JP6905530B2 JP6905530B2 (ja) | 2021-07-21 |
Family
ID=58289678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018534463A Active JP6905530B2 (ja) | 2015-09-16 | 2016-09-16 | ファルネソイドｘ受容体アゴニストとその使用 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US10703712B2 (enExample) |
| EP (1) | EP3350165B1 (enExample) |
| JP (1) | JP6905530B2 (enExample) |
| KR (1) | KR20180052678A (enExample) |
| CN (1) | CN108349893B (enExample) |
| AU (1) | AU2016323992B2 (enExample) |
| CA (1) | CA2998493A1 (enExample) |
| DK (1) | DK3350165T3 (enExample) |
| EA (1) | EA201890725A1 (enExample) |
| IL (1) | IL258011B2 (enExample) |
| MX (1) | MX386752B (enExample) |
| PH (1) | PH12018500586B1 (enExample) |
| SG (1) | SG10202110242YA (enExample) |
| WO (1) | WO2017049173A1 (enExample) |
| ZA (1) | ZA201801750B (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3350166A4 (en) | 2015-09-16 | 2019-05-01 | Metacrine, Inc. | FARNESOID-X RECEPTOR AGONISTS AND USES THEREOF |
| EP3350165B1 (en) | 2015-09-16 | 2023-07-26 | Organovo, Inc. | Farnesoid x receptor agonists and uses thereof |
| US10626081B2 (en) | 2015-09-16 | 2020-04-21 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
| WO2018170165A1 (en) * | 2017-03-15 | 2018-09-20 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| DK3596053T3 (da) * | 2017-03-15 | 2023-09-25 | Organovo Inc | Farnesoid-x-receptoragonister og anvendelser deraf |
| AU2018236275B2 (en) | 2017-03-15 | 2022-05-12 | Eli Lilly And Company | Farnesoid X receptor agonists and uses thereof |
| WO2018170173A1 (en) * | 2017-03-15 | 2018-09-20 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| CN110251498A (zh) * | 2018-03-12 | 2019-09-20 | 厦门大学 | 一类调节法尼醇受体活性的化合物及其用途 |
| KR102731925B1 (ko) | 2017-11-01 | 2024-11-18 | 브리스톨-마이어스 스큅 컴퍼니 | 파르네소이드 x 수용체 조정제로서의 멀티시클릭 화합물 |
| US11286252B2 (en) | 2017-11-01 | 2022-03-29 | Bristol-Myers Squibb Company | Alkene spirocyclic compounds as farnesoid X receptor modulators |
| JP2021501785A (ja) | 2017-11-02 | 2021-01-21 | カリコ ライフ サイエンシーズ エルエルシー | 統合的ストレス経路の調節剤 |
| WO2020061117A1 (en) * | 2018-09-18 | 2020-03-26 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| CN113056264A (zh) * | 2018-09-18 | 2021-06-29 | 梅塔科林公司 | 法尼醇x受体激动剂及其用途 |
| WO2020061118A1 (en) * | 2018-09-18 | 2020-03-26 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| EP3852748B1 (en) * | 2018-09-18 | 2025-09-03 | Eli Lilly and Company | Farnesoid x receptor agonists and uses thereof |
| BR112021004931A2 (pt) * | 2018-09-18 | 2021-06-01 | Metacrine, Inc. | formas cristalinas de um agonista de receptor farnesoide x |
| US20220047553A1 (en) * | 2018-09-18 | 2022-02-17 | Metacrine, Inc. | Farnesoid x receptor agonists for the treatment of disease |
| WO2020061116A1 (en) * | 2018-09-18 | 2020-03-26 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| EP3870162A4 (en) * | 2018-10-24 | 2022-08-24 | Metacrine, Inc. | SSAO INHIBITORS AND USES THEREOF |
| JP7449300B2 (ja) * | 2019-02-15 | 2024-03-13 | ブリストル－マイヤーズ スクイブ カンパニー | ファルネソイドｘ受容体モジュレータとして有用な置換アミド化合物 |
| AR118050A1 (es) * | 2019-02-15 | 2021-09-15 | Bristol Myers Squibb Co | Compuestos bicíclicos sustituidos como moduladores del receptor farnesoide x |
| US12319676B2 (en) | 2019-02-15 | 2025-06-03 | Bristol-Myers Squibb Company | Substituted amide compounds useful as farnesoid X receptor modulators |
| JP7465883B2 (ja) * | 2019-02-15 | 2024-04-11 | ブリストル－マイヤーズ スクイブ カンパニー | ファルネソイドｘ受容体モジュレータとしての置換二環式化合物 |
| WO2021009332A1 (en) | 2019-07-18 | 2021-01-21 | Enyo Pharma | Method for decreasing adverse-effects of interferon |
| KR20220119653A (ko) | 2019-12-20 | 2022-08-30 | 테나야 테라퓨틱스, 인코포레이티드 | 플루오로알킬-옥사디아졸 및 이의 용도 |
| IL293892A (en) | 2020-01-15 | 2022-08-01 | Inserm Institut National De La Sant? Et De La Rech M?Dicale | Use of fxr agonists for treating an infection by hepatitis d virus |
| KR20220154801A (ko) * | 2020-03-18 | 2022-11-22 | 메타크린, 인크. | 질환의 치료를 위한 파르네소이드 x 수용체 작용제 |
| CN120227340A (zh) * | 2020-03-18 | 2025-07-01 | 伊莱利利公司 | 法尼醇x受体激动剂的制剂 |
| JP7664278B2 (ja) | 2020-03-18 | 2025-04-17 | オルガノボ，インク． | ファルネソイドｘ受容体アゴニストの結晶質形態 |
| WO2021188690A1 (en) * | 2020-03-18 | 2021-09-23 | Metacrine, Inc. | Farnesoid x receptor agonists for the treatment of disease |
| US20230201222A1 (en) * | 2020-05-13 | 2023-06-29 | Children's Hospital Medical Center | Alleviation of liver injury by activating the signaling pathway mediated by farnesoid x receptor |
| JP2023554524A (ja) * | 2020-12-22 | 2023-12-27 | ノースシー セラピューティクス ベスローテン フェンノートシャップ | 非アルコール性脂肪性肝炎の治療のための酸素含有構造強化脂肪酸を含む組合せ療法 |
| MX2023008365A (es) | 2021-01-14 | 2023-10-04 | Enyo Pharma | Efecto sinérgico de un agonista de fxr e ifn para el tratamiento de infección por hbv. |
| TW202308629A (zh) | 2021-04-28 | 2023-03-01 | 法商Ｅｎｙｏ製藥公司 | 使用fxr激動劑作為組合治療以增強tlr3激動劑之療效 |
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-
2016
- 2016-09-16 EP EP16847452.6A patent/EP3350165B1/en active Active
- 2016-09-16 CA CA2998493A patent/CA2998493A1/en active Pending
- 2016-09-16 WO PCT/US2016/052270 patent/WO2017049173A1/en not_active Ceased
- 2016-09-16 CN CN201680066917.9A patent/CN108349893B/zh active Active
- 2016-09-16 JP JP2018534463A patent/JP6905530B2/ja active Active
- 2016-09-16 EA EA201890725A patent/EA201890725A1/ru unknown
- 2016-09-16 DK DK16847452.6T patent/DK3350165T3/da active
- 2016-09-16 KR KR1020187009912A patent/KR20180052678A/ko not_active Ceased
- 2016-09-16 US US15/758,707 patent/US10703712B2/en active Active
- 2016-09-16 SG SG10202110242Y patent/SG10202110242YA/en unknown
- 2016-09-16 AU AU2016323992A patent/AU2016323992B2/en active Active
- 2016-09-16 MX MX2018003388A patent/MX386752B/es unknown
- 2016-09-16 PH PH1/2018/500586A patent/PH12018500586B1/en unknown
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2018
- 2018-03-11 IL IL258011A patent/IL258011B2/en unknown
- 2018-03-14 ZA ZA2018/01750A patent/ZA201801750B/en unknown
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2020
- 2020-05-12 US US16/872,985 patent/US11214538B2/en active Active
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2021
- 2021-11-22 US US17/532,618 patent/US20220081390A1/en not_active Abandoned
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