JP2016511274A5 - - Google Patents
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- Publication number
- JP2016511274A5 JP2016511274A5 JP2015561865A JP2015561865A JP2016511274A5 JP 2016511274 A5 JP2016511274 A5 JP 2016511274A5 JP 2015561865 A JP2015561865 A JP 2015561865A JP 2015561865 A JP2015561865 A JP 2015561865A JP 2016511274 A5 JP2016511274 A5 JP 2016511274A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- unsubstituted
- phenyl
- aryl
- 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.)
- Pending
Links
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000004001 thioalkyl group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 238000008214 LDL Cholesterol Methods 0.000 claims 6
- 108010028554 LDL Cholesterol Proteins 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 4
- -1 2,9,9-trimethyl -3,5-dioxa-4-boratricyclo [6.1.1.0 2,6 ] Decan-4-yl Chemical group 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 3
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 150000002632 lipids Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims 1
- CHJJHGSNNPEDNJ-UHFFFAOYSA-N 3-phenyl-1,2,5-oxadiazole Chemical compound C1=NON=C1C1=CC=CC=C1 CHJJHGSNNPEDNJ-UHFFFAOYSA-N 0.000 claims 1
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000000539 amino acid group Chemical group 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 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
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- CDNZEVWFGTWVJC-UHFFFAOYSA-N pyridine;1,2-thiazole Chemical compound C=1C=NSC=1.C1=CC=NC=C1 CDNZEVWFGTWVJC-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 0 CC(C)[C@](*(N)=O)NC(OC)=O Chemical compound CC(C)[C@](*(N)=O)NC(OC)=O 0.000 description 12
- ORRBBPUNKKCLBX-YZFZWQTPSA-N CC(C)[C@@H](C(N[C@@H](Cc1ccccc1)C(N[C@@H](C)C(NC(CCC(N)=O)C(C(F)(F)F)O)=O)=O)=O)NC(c(cc1)ccc1-c(cc1)ccc1S(C)(O)=O)=O Chemical compound CC(C)[C@@H](C(N[C@@H](Cc1ccccc1)C(N[C@@H](C)C(NC(CCC(N)=O)C(C(F)(F)F)O)=O)=O)=O)NC(c(cc1)ccc1-c(cc1)ccc1S(C)(O)=O)=O ORRBBPUNKKCLBX-YZFZWQTPSA-N 0.000 description 1
- YHSTURPDJSQTJJ-JVHUHPJJSA-N CC(C)[C@@H](C(N[C@@H](Cc1ccccc1)C(N[C@@H](C)C(NC(CCC(N)=O)C(C(F)(F)F)O)=O)=O)=O)NC(c1c[s]c(-c2ccccc2)n1)=O Chemical compound CC(C)[C@@H](C(N[C@@H](Cc1ccccc1)C(N[C@@H](C)C(NC(CCC(N)=O)C(C(F)(F)F)O)=O)=O)=O)NC(c1c[s]c(-c2ccccc2)n1)=O YHSTURPDJSQTJJ-JVHUHPJJSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361792249P | 2013-03-15 | 2013-03-15 | |
| US61/792,249 | 2013-03-15 | ||
| PCT/CA2014/050255 WO2014139008A1 (en) | 2013-03-15 | 2014-03-14 | Small molecule modulators of pcsk9 and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016511274A JP2016511274A (ja) | 2016-04-14 |
| JP2016511274A5 true JP2016511274A5 (https=) | 2017-04-20 |
Family
ID=51535727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015561865A Pending JP2016511274A (ja) | 2013-03-15 | 2014-03-14 | Ｐｃｓｋ９の小分子モジュレータ及びその使用法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20160031935A1 (https=) |
| EP (1) | EP2961765A4 (https=) |
| JP (1) | JP2016511274A (https=) |
| KR (1) | KR20150132362A (https=) |
| CN (1) | CN105431447A (https=) |
| AU (1) | AU2014231330A1 (https=) |
| BR (1) | BR112015023761A2 (https=) |
| CA (1) | CA2905237A1 (https=) |
| HK (1) | HK1222864A1 (https=) |
| WO (1) | WO2014139008A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3160513B1 (en) | 2014-06-30 | 2020-02-12 | Glykos Finland Oy | Saccharide derivative of a toxic payload and antibody conjugates thereof |
| US10034892B2 (en) | 2014-08-21 | 2018-07-31 | Srx Cardio, Llc | Composition and methods of use of small molecules as binding ligands for the modulation of proprotein convertase subtilisin/kexin type 9(PCSK9) protein activity |
| US20170290806A1 (en) * | 2014-09-08 | 2017-10-12 | Temple University-Of The Commonwealth System Of Higher Education | PCSK9 Inhibitors and Methods of Use Thereof |
| EP3973958A3 (en) * | 2015-03-20 | 2022-06-22 | Aarhus Universitet | Inhibitors of pcsk9 for treatment of lipoprotein metabolism disorders |
| EP4067368A1 (en) | 2016-06-01 | 2022-10-05 | Athira Pharma, Inc. | Compounds |
| BR112018076242A2 (pt) | 2016-06-24 | 2019-03-26 | Hoffmann La Roche | inibidores de pcsk9, pcsk9 inibido, composição farmacêutica, métodos para modular a atividade de pcsk9, para inibir a ligação de pcsk9 a ldlr, para aumentar a disponibilidade de ldlr, para reduzir um nível de ldl-c, para reduzir o nível sérico de ldl-c, para o tratamento de um distúrbio relacionado com colesterol, métodos para o tratamento de um distúrbio associado a um nível anormal de ldl-c, de uma condição associada a um nível elevado de ldl-c, de dislipidemia, de hipercolesterolemia, usos de um inibidor de pcsk9 e método para identificar um composto candidato como um inibidor de pcsk9 que liga um epítopo da seq id nº 1 |
| GB2567210B (en) | 2017-10-06 | 2020-01-15 | Rolls Royce Plc | A bladed disk |
| CN109096247A (zh) * | 2018-08-15 | 2018-12-28 | 上海罕道医药科技有限公司 | 一种3h双吖丙啶基双取代吡啶衍生物的制备方法 |
| SG11202107614PA (en) | 2019-01-18 | 2021-08-30 | Astrazeneca Ab | Pcsk9 inhibitors and methods of use thereof |
| LV15544A (lv) * | 2019-07-01 | 2021-01-20 | Latvijas Organiskās Sintēzes Institūts | Jauni borskābi saturoši peptidomimētiķi kā malārijas serīna proteāzes inhibitori |
| WO2024163598A2 (en) * | 2023-01-31 | 2024-08-08 | Brandeis University | Peptides comprising thioester groups, including depsipeptide thioesters, methods of making, and use thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998013461A1 (en) * | 1996-09-24 | 1998-04-02 | The Procter & Gamble Company | Liquid laundry detergent compositions containing proteolytic enzyme and protease inhibitors |
| GB9623908D0 (en) * | 1996-11-18 | 1997-01-08 | Hoffmann La Roche | Amino acid derivatives |
| US6358491B1 (en) * | 1999-08-27 | 2002-03-19 | Berlex Laboratories, Inc. | Somatostatin analogs |
| AU2003228793B2 (en) * | 2002-04-30 | 2008-01-03 | Trustees Of Tufts College | Smart Pro-Drugs of Serine Protease Inhibitors |
| CN101679527A (zh) * | 2007-04-13 | 2010-03-24 | 诺瓦提斯公司 | 用于调节前蛋白转化酶枯草杆菌蛋白酶/kexin9型(pcsk9)的分子和方法 |
| AR079344A1 (es) * | 2009-12-22 | 2012-01-18 | Lilly Co Eli | Analogo peptidico de oxintomodulina, composicion farmaceutica que lo comprende y uso para preparar un medicamento util para tratar diabetes no insulinodependiente y/u obesidad |
| CA2791651C (en) * | 2010-03-01 | 2019-08-20 | Onyx Therapeutics, Inc. | Compounds for immunoproteasome inhibition |
| US8999922B2 (en) * | 2012-02-16 | 2015-04-07 | Rqx Pharmaceuticals, Inc. | Linear peptide antibiotics |
-
2014
- 2014-03-14 CA CA2905237A patent/CA2905237A1/en not_active Abandoned
- 2014-03-14 HK HK16110987.6A patent/HK1222864A1/zh unknown
- 2014-03-14 US US14/776,701 patent/US20160031935A1/en not_active Abandoned
- 2014-03-14 AU AU2014231330A patent/AU2014231330A1/en not_active Abandoned
- 2014-03-14 JP JP2015561865A patent/JP2016511274A/ja active Pending
- 2014-03-14 BR BR112015023761A patent/BR112015023761A2/pt active Search and Examination
- 2014-03-14 KR KR1020157029032A patent/KR20150132362A/ko not_active Withdrawn
- 2014-03-14 EP EP14765405.7A patent/EP2961765A4/en not_active Withdrawn
- 2014-03-14 WO PCT/CA2014/050255 patent/WO2014139008A1/en not_active Ceased
- 2014-03-14 CN CN201480026888.4A patent/CN105431447A/zh active Pending
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