JP2013545718A5 - - Google Patents
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- JP2013545718A5 JP2013545718A5 JP2013524677A JP2013524677A JP2013545718A5 JP 2013545718 A5 JP2013545718 A5 JP 2013545718A5 JP 2013524677 A JP2013524677 A JP 2013524677A JP 2013524677 A JP2013524677 A JP 2013524677A JP 2013545718 A5 JP2013545718 A5 JP 2013545718A5
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- JP
- Japan
- Prior art keywords
- ring
- substituted
- optionally substituted
- salt
- group
- 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 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 230000000069 prophylactic effect Effects 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 229940121373 acetyl-coa carboxylase inhibitor Drugs 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- ADHDEZRLSWZHKE-LBPRGKRZSA-N n-[(2s)-1-[6-(6-ethoxy-1,3-benzoxazol-2-yl)pyridin-3-yl]oxypropan-2-yl]acetamide Chemical compound O1C2=CC(OCC)=CC=C2N=C1C1=CC=C(OC[C@H](C)NC(C)=O)C=N1 ADHDEZRLSWZHKE-LBPRGKRZSA-N 0.000 claims 1
- CBRJFLKXQUUGQV-LBPRGKRZSA-N n-[(2s)-1-[6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-5-fluoropyridin-3-yl]oxypropan-2-yl]acetamide Chemical compound FC1=CC(OC[C@H](C)NC(C)=O)=CN=C1C(OC1=C2)=NC1=CC=C2OCC1CC1 CBRJFLKXQUUGQV-LBPRGKRZSA-N 0.000 claims 1
- ZAAOFSTVMJFFPI-ZDUSSCGKSA-N n-[(2s)-1-[6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl]oxypropan-2-yl]acetamide Chemical compound N1=CC(OC[C@H](C)NC(C)=O)=CC=C1C(OC1=C2)=NC1=CC=C2OCC1CC1 ZAAOFSTVMJFFPI-ZDUSSCGKSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 0 CC*=N*(C)C Chemical compound CC*=N*(C)C 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- -1 5 - {[ (2S) -2- aminopropyl] oxy} pyridin-2-yl Chemical group 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ALJQVIZVWCKBIQ-UHFFFAOYSA-N 6-[6-(methoxymethoxy)-2-methyl-3h-1-benzofuran-2-yl]pyridin-3-ol Chemical compound O1C2=CC(OCOC)=CC=C2CC1(C)C1=CC=C(O)C=N1 ALJQVIZVWCKBIQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- CZZPSVORNFBYEX-UHFFFAOYSA-N 3,3-diethylpentan-1-amine Chemical compound CCC(CC)(CC)CCN CZZPSVORNFBYEX-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- IBKFLJRJFOGTOQ-UHFFFAOYSA-N C(C)(=O)N.BrCC1CC1 Chemical compound C(C)(=O)N.BrCC1CC1 IBKFLJRJFOGTOQ-UHFFFAOYSA-N 0.000 description 1
- OAYCSWBEXSUQAY-UHFFFAOYSA-N C(C)(=O)OC(C)=O.C(C)(=O)N Chemical compound C(C)(=O)OC(C)=O.C(C)(=O)N OAYCSWBEXSUQAY-UHFFFAOYSA-N 0.000 description 1
- CSWGKBFMCBXHNL-UHFFFAOYSA-N CC1NN(C=CC(C)=C2)C2=C1 Chemical compound CC1NN(C=CC(C)=C2)C2=C1 CSWGKBFMCBXHNL-UHFFFAOYSA-N 0.000 description 1
- DVZVWYAUBOMCJA-UHFFFAOYSA-N CC1Oc2ccc(C)cc2N1 Chemical compound CC1Oc2ccc(C)cc2N1 DVZVWYAUBOMCJA-UHFFFAOYSA-N 0.000 description 1
- GYCGFNPVXKJNTL-UHFFFAOYSA-N Cc1c[n](ccc(C)c2)c2n1 Chemical compound Cc1c[n](ccc(C)c2)c2n1 GYCGFNPVXKJNTL-UHFFFAOYSA-N 0.000 description 1
- HMMPHXCOTBASBC-UHFFFAOYSA-N Cc1cc2n[nH]cc2cc1 Chemical compound Cc1cc2n[nH]cc2cc1 HMMPHXCOTBASBC-UHFFFAOYSA-N 0.000 description 1
- DDJNVLANJKUROF-UHFFFAOYSA-N Cc1n[n](CCC(C)=C2)c2c1 Chemical compound Cc1n[n](CCC(C)=C2)c2c1 DDJNVLANJKUROF-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- OKMJCVKFQXNEDD-AWEZNQCLSA-N tert-butyl n-[(2s)-1-[4-(6-ethoxy-3-fluoropyrazolo[1,5-a]pyridin-2-yl)-3-fluorophenoxy]propan-2-yl]carbamate Chemical compound N=1N2C=C(OCC)C=CC2=C(F)C=1C1=CC=C(OC[C@H](C)NC(=O)OC(C)(C)C)C=C1F OKMJCVKFQXNEDD-AWEZNQCLSA-N 0.000 description 1
- MHAQEPQMTBZZKV-FXIRQEPWSA-N tert-butyl n-[(2s)-1-[6-[6-(methoxymethoxy)-2-methyl-3h-1-benzofuran-2-yl]pyridin-3-yl]oxypropan-2-yl]carbamate Chemical compound O1C2=CC(OCOC)=CC=C2CC1(C)C1=CC=C(OC[C@H](C)NC(=O)OC(C)(C)C)C=N1 MHAQEPQMTBZZKV-FXIRQEPWSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013524677A JP5824517B2 (ja) | 2010-11-30 | 2011-11-29 | 二環性化合物 |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010266097 | 2010-11-30 | ||
| JP2010266097 | 2010-11-30 | ||
| JP2011175330 | 2011-08-10 | ||
| JP2011175330 | 2011-08-10 | ||
| JP2013524677A JP5824517B2 (ja) | 2010-11-30 | 2011-11-29 | 二環性化合物 |
| PCT/JP2011/078010 WO2012074126A1 (en) | 2010-11-30 | 2011-11-29 | Bicyclic compound |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013545718A JP2013545718A (ja) | 2013-12-26 |
| JP2013545718A5 true JP2013545718A5 (cg-RX-API-DMAC7.html) | 2014-08-21 |
| JP5824517B2 JP5824517B2 (ja) | 2015-11-25 |
Family
ID=45418740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013524677A Expired - Fee Related JP5824517B2 (ja) | 2010-11-30 | 2011-11-29 | 二環性化合物 |
Country Status (24)
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2011246004A1 (en) | 2010-04-27 | 2012-11-29 | Takeda Pharmaceutical Company Limited | Bicyclic compound derivatives and their use as ACC inhibitors. |
| WO2013061962A1 (ja) | 2011-10-24 | 2013-05-02 | 武田薬品工業株式会社 | 二環性化合物 |
| WO2014088983A1 (en) | 2012-12-07 | 2014-06-12 | Merck Sharp & Dohme Corp. | Regioselective n-2 arylation of indazoles |
| PL403149A1 (pl) * | 2013-03-14 | 2014-09-15 | Celon Pharma Spółka Akcyjna | Nowe związki pochodne pirazolilobenzo[d]imidazolu |
| CN105358143B (zh) | 2013-05-10 | 2019-01-22 | 吉利德阿波罗公司 | Acc抑制剂和其用途 |
| US10208044B2 (en) | 2013-05-10 | 2019-02-19 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| HK1221661A1 (zh) * | 2013-05-10 | 2017-06-09 | Gilead Apollo, Llc | Acc抑制剂和其用途 |
| KR20160007598A (ko) | 2013-05-10 | 2016-01-20 | 님버스 아폴로, 인코포레이티드 | Acc 억제제 및 이의 용도 |
| BR112016004118A2 (pt) | 2013-09-12 | 2017-10-17 | Pfizer | uso de inibidores da acetil-coa carboxilase para tratamento de acne vulgar |
| JP6352415B2 (ja) | 2013-11-14 | 2018-07-04 | カディラ・ヘルスケア・リミテッド | 新規なヘテロ環化合物 |
| US10689383B2 (en) | 2014-08-04 | 2020-06-23 | Nuevolution A/S | Optionally fused heterocyclyl-substituted derivatives of pyrimidine useful for the treatment of inflammatory, metabolic, oncologic and autoimmune diseases |
| CN104193731B (zh) * | 2014-08-27 | 2017-03-15 | 广东东阳光药业有限公司 | 一种脲取代联苯类化合物及其组合物及用途 |
| CN107108534B (zh) * | 2014-08-29 | 2023-05-09 | Chdi基金会股份有限公司 | 用于成像亨廷顿蛋白的探针 |
| JP2016079168A (ja) * | 2014-10-17 | 2016-05-16 | 塩野義製薬株式会社 | ９員縮合環誘導体 |
| CN104447725B (zh) * | 2014-10-22 | 2018-02-02 | 浙江大学 | 一种手性含亚胺吡啶噁唑啉的化合物及其制备方法 |
| WO2016130501A1 (en) | 2015-02-09 | 2016-08-18 | Incyte Corporation | Aza-heteroaryl compounds as pi3k-gamma inhibitors |
| AU2016332021A1 (en) * | 2015-09-29 | 2018-04-19 | Oncotherapy Science, Inc. | Bicyclic compound and use thereof for inhibiting SUV39H2 |
| CN105601626A (zh) * | 2015-11-04 | 2016-05-25 | 浙江大学 | 一种含2-取代噁唑啉衍生物的制备方法 |
| PT3371190T (pt) | 2015-11-06 | 2022-07-08 | Incyte Corp | Compostos heterocíclicos como inibidores de pi3k-gamma |
| US20170190689A1 (en) | 2016-01-05 | 2017-07-06 | Incyte Corporation | Pyridine and pyridimine compounds as pi3k-gamma inhibitors |
| TW201803871A (zh) | 2016-06-24 | 2018-02-01 | 英塞特公司 | 作為ＰＩ３Ｋ-γ抑制劑之雜環化合物 |
| JP7179014B2 (ja) | 2017-04-24 | 2022-11-28 | テサロ， インコーポレイテッド | ニラパリブの製造方法 |
| CN118063470A (zh) | 2017-10-18 | 2024-05-24 | 因赛特公司 | 作为PI3K-γ抑制剂的由叔羟基取代的缩合咪唑衍生物 |
| CR20250050A (es) | 2018-09-05 | 2025-03-19 | Incyte Corp | Formas cristalinas de un inhibidor de fosfoinositida 3–quinasa (pi3k) (divisional 2021-0165) |
| MX2022007265A (es) | 2019-12-20 | 2022-09-09 | Nuevolution As | Compuestos activos frente a receptores nucleares. |
| PE20230240A1 (es) | 2019-12-20 | 2023-02-07 | Nuevolution As | Compuestos activos frente a receptores nucleares |
| JP7713954B2 (ja) | 2020-03-31 | 2025-07-28 | ヌエヴォリューション・アクティーゼルスカブ | 核内受容体に対して活性な化合物 |
| AU2021245397A1 (en) | 2020-03-31 | 2022-10-20 | Nuevolution A/S | Compounds active towards nuclear receptors |
| EP4434520A4 (en) | 2021-11-19 | 2025-10-29 | Shionogi & Co | PHARMACEUTICAL PRODUCT FOR THE TREATMENT OF HEART DISEASE OR SKELETAL MUSCLE DISEASE |
| AR129265A1 (es) | 2022-05-12 | 2024-08-07 | Syngenta Crop Protection Ag | Compuestos de alcoxi-heteroaril-carboxamida o tioamida |
| WO2024033374A1 (en) | 2022-08-11 | 2024-02-15 | Syngenta Crop Protection Ag | Novel arylcarboxamide or arylthioamide compounds |
| WO2024126650A1 (en) | 2022-12-15 | 2024-06-20 | Syngenta Crop Protection Ag | Novel bicyclic-carboxamide compounds useful as pesticides |
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-
2011
- 2011-11-29 KR KR1020137016850A patent/KR20140001965A/ko not_active Withdrawn
- 2011-11-29 JP JP2013524677A patent/JP5824517B2/ja not_active Expired - Fee Related
- 2011-11-29 PH PH1/2013/501099A patent/PH12013501099A1/en unknown
- 2011-11-29 CA CA2819400A patent/CA2819400A1/en not_active Abandoned
- 2011-11-29 EA EA201390794A patent/EA201390794A1/ru unknown
- 2011-11-29 MX MX2013006113A patent/MX2013006113A/es not_active Application Discontinuation
- 2011-11-29 WO PCT/JP2011/078010 patent/WO2012074126A1/en not_active Ceased
- 2011-11-29 UY UY0001033756A patent/UY33756A/es not_active Application Discontinuation
- 2011-11-29 BR BR112013013417A patent/BR112013013417A2/pt not_active IP Right Cessation
- 2011-11-29 TW TW100143674A patent/TW201242951A/zh unknown
- 2011-11-29 CN CN201180066388.XA patent/CN103347872B/zh not_active Expired - Fee Related
- 2011-11-29 US US13/306,069 patent/US8729102B2/en not_active Expired - Fee Related
- 2011-11-29 EP EP11802168.2A patent/EP2649062B1/en active Active
- 2011-11-29 AU AU2011337565A patent/AU2011337565A1/en not_active Abandoned
- 2011-11-29 AR ARP110104436A patent/AR084032A1/es not_active Application Discontinuation
- 2011-11-29 PE PE2013001328A patent/PE20140161A1/es not_active Application Discontinuation
- 2011-11-29 SG SG2013041546A patent/SG190925A1/en unknown
- 2011-11-29 ES ES11802168.2T patent/ES2536319T3/es active Active
-
2013
- 2013-05-29 DO DO2013000118A patent/DOP2013000118A/es unknown
- 2013-05-29 CL CL2013001520A patent/CL2013001520A1/es unknown
- 2013-06-05 MA MA35965A patent/MA34713B1/fr unknown
- 2013-06-11 CR CR20130281A patent/CR20130281A/es not_active Application Discontinuation
- 2013-06-24 CO CO13149620A patent/CO6751239A2/es not_active Application Discontinuation
- 2013-06-25 EC ECSP13012719 patent/ECSP13012719A/es unknown
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