JPWO2020081257A5 - - Google Patents
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- JPWO2020081257A5 JPWO2020081257A5 JP2021518181A JP2021518181A JPWO2020081257A5 JP WO2020081257 A5 JPWO2020081257 A5 JP WO2020081257A5 JP 2021518181 A JP2021518181 A JP 2021518181A JP 2021518181 A JP2021518181 A JP 2021518181A JP WO2020081257 A5 JPWO2020081257 A5 JP WO2020081257A5
- Authority
- JP
- Japan
- Prior art keywords
- branched
- compound
- cyclic
- groups
- straight chain
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 176
- 125000004122 cyclic group Chemical group 0.000 claims description 137
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 116
- 229910052736 halogen Inorganic materials 0.000 claims description 94
- 150000002367 halogens Chemical class 0.000 claims description 94
- 150000003839 salts Chemical class 0.000 claims description 83
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 70
- 125000003545 alkoxy group Chemical group 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 34
- -1 cyano, hydroxy Chemical group 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 12
- 125000004001 thioalkyl group Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 10
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 7
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000001010 sulfinic acid amide group Chemical group 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- USCSRAJGJYMJFZ-UHFFFAOYSA-N 3-methyl-1-butyne Chemical compound CC(C)C#C USCSRAJGJYMJFZ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 102000015395 alpha 1-Antitrypsin Human genes 0.000 claims description 4
- 108010050122 alpha 1-Antitrypsin Proteins 0.000 claims description 4
- 229940024142 alpha 1-antitrypsin Drugs 0.000 claims description 4
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 208000006682 alpha 1-Antitrypsin Deficiency Diseases 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- SMCVPMKCDDNUCQ-UHFFFAOYSA-N methyl 3,3-dimethoxypropanoate Chemical compound COC(OC)CC(=O)OC SMCVPMKCDDNUCQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000012041 precatalyst Substances 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 15
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 35
- 150000002431 hydrogen Chemical class 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000009256 replacement therapy Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862742148P | 2018-10-05 | 2018-10-05 | |
| US62/742,148 | 2018-10-05 | ||
| US201862768662P | 2018-11-16 | 2018-11-16 | |
| US62/768,662 | 2018-11-16 | ||
| PCT/US2019/054681 WO2020081257A1 (en) | 2018-10-05 | 2019-10-04 | Modulators of alpha-1 antitrypsin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2022512588A JP2022512588A (ja) | 2022-02-07 |
| JPWO2020081257A5 true JPWO2020081257A5 (pl) | 2024-03-12 |
Family
ID=69467663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021518181A Pending JP2022512588A (ja) | 2018-10-05 | 2019-10-04 | アルファ１アンチトリプシンのモジュレーター |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US11623924B2 (pl) |
| EP (1) | EP3860712A1 (pl) |
| JP (1) | JP2022512588A (pl) |
| KR (1) | KR20210089656A (pl) |
| CN (1) | CN113164761A (pl) |
| AU (1) | AU2019362753A1 (pl) |
| BR (1) | BR112021006392A2 (pl) |
| CA (1) | CA3114672A1 (pl) |
| CO (1) | CO2021005884A2 (pl) |
| IL (1) | IL281884A (pl) |
| JO (1) | JOP20210060A1 (pl) |
| MA (1) | MA53827A (pl) |
| MX (1) | MX2021003819A (pl) |
| TW (1) | TW202024091A (pl) |
| UY (1) | UY38403A (pl) |
| WO (1) | WO2020081257A1 (pl) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20210089656A (ko) | 2018-10-05 | 2021-07-16 | 버텍스 파마슈티칼스 인코포레이티드 | 알파-1 항트립신 조절제 |
| UY38696A (es) | 2019-05-14 | 2020-11-30 | Vertex Pharma | Moduladores de alfa-1 antitripsina |
| TW202116303A (zh) * | 2019-10-02 | 2021-05-01 | 美商維泰克斯製藥公司 | α—１抗胰蛋白酶缺乏症之治療方法 |
| GB201918416D0 (en) | 2019-12-13 | 2020-01-29 | Z Factor Ltd | Compounds and their use for the treatment of Alpha1-Antitrypsin deficiency |
| GB201918414D0 (en) | 2019-12-13 | 2020-01-29 | Z Factor Ltd | Compounds and their use for the treatment of Alpha1-Antitrypsin deficiency |
| GB201918413D0 (en) | 2019-12-13 | 2020-01-29 | Z Factor Ltd | Compounds and their use for the treatment of alpha1-antitrypsin deficiency |
| GB201918410D0 (en) | 2019-12-13 | 2020-01-29 | Z Factor Ltd | Compounds and their use for the treatment of alpha1-antitrypsin deficiency |
| GB201918404D0 (en) | 2019-12-13 | 2020-01-29 | Z Factor Ltd | Compounds and their use for the treatment of aplha1-antitrypsin deficiency |
| CN115776984A (zh) * | 2020-04-03 | 2023-03-10 | 弗特克斯药品有限公司 | 作为用于治疗α-1抗胰蛋白酶缺乏症(AATD)的α-1-抗胰蛋白酶调节剂的吡咯并[2,3-f]吲唑和2,4,5,10-四氮杂三环[7.3.0.03,7]十二碳-1,3(7),5,8,11-五烯衍生物 |
| GB202009074D0 (en) | 2020-06-15 | 2020-07-29 | Z Factor Ltd | Compound |
| EP4188931A2 (en) | 2020-07-27 | 2023-06-07 | Vertex Pharmaceuticals Incorporated | Processes for preparing modulators of alpha-1 antitrypsin |
| US20240012010A1 (en) | 2020-11-12 | 2024-01-11 | Vertex Pharmaceuticals Incorporated | Methods of monitoring alpha-1 antitrypsin (aat) deficiency by measuring polymerised aat |
| KR20230110313A (ko) * | 2020-11-17 | 2023-07-21 | 버텍스 파마슈티칼스 인코포레이티드 | 4-(5-(4-플루오로페닐)-6-(테트라하이드로-2H-피란-4-일)-1,5-디하이드로피롤로[2,3-f]인다졸-7-일)벤조산의 고형분 형태 |
| GB202108523D0 (en) | 2021-06-15 | 2021-07-28 | Z Factor Ltd | Compositions and their use for the treatment of alpha1-antitrypsin deficiency |
| CN114605385B (zh) * | 2022-03-25 | 2023-09-08 | 河南大学 | 吲哚哌啶脲类trpv1拮抗/faah抑制双靶点药物及制备方法和应用 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790679A (fr) * | 1971-11-03 | 1973-04-27 | Ici Ltd | Derives de l'indole |
| DK158590D0 (da) | 1990-07-02 | 1990-07-02 | Lundbeck & Co As H | Indolderivater |
| JP2000072751A (ja) | 1998-08-26 | 2000-03-07 | Tanabe Seiyaku Co Ltd | イソキノリノン誘導体 |
| JP2000281654A (ja) | 1999-03-26 | 2000-10-10 | Tanabe Seiyaku Co Ltd | イソキノリン誘導体 |
| GB9913083D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| FR2802532A1 (fr) | 1999-12-17 | 2001-06-22 | Sanofi Synthelabo | Derives de 2-phenyl-quinoleine, leur preparation et leur application en therapeutique |
| US6638929B2 (en) | 1999-12-29 | 2003-10-28 | Wyeth | Tricyclic protein kinase inhibitors |
| US6962917B2 (en) | 2000-07-26 | 2005-11-08 | Smithkline Beecham P.L.C. | Aminopiperidine quinolines and their azaisosteric analogues with antibacterical activity |
| EP1396488A1 (en) | 2001-05-23 | 2004-03-10 | Mitsubishi Pharma Corporation | Fused heterocyclic compound and medicinal use thereof |
| EP1458693A4 (en) | 2001-11-14 | 2005-02-09 | Teva Pharma | Amorphous and crystalline forms of losartan potassium and method for making same |
| US7208601B2 (en) | 2003-08-08 | 2007-04-24 | Mjalli Adnan M M | Aryl and heteroaryl compounds, compositions, and methods of use |
| WO2011056222A1 (en) | 2009-11-05 | 2011-05-12 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Methods of treating disorders associated with protein aggregation |
| WO2011110852A1 (en) | 2010-03-10 | 2011-09-15 | Astrazeneca Ab | Polymorphic forms of 6- [2- (4 -cyanophenyl) - 2h - pyrazol - 3 - yl] - 5 -methyl - 3 - oxo - 4 - (trifluoromethyl - phenyl) 3,4-dihydropyrazine-2-carboxylic acid ethylamide |
| US9572794B2 (en) | 2014-08-06 | 2017-02-21 | Vanderbilt University | Substituted indoles as selective protease activated receptor 4 (PAR-4) antagonists |
| WO2016154051A1 (en) | 2015-03-20 | 2016-09-29 | University Of Florida Research Foundation, Inc. | Combination therapy for treating infections diseases |
| CA3024556A1 (en) | 2016-05-12 | 2017-11-16 | The Regents Of The University Of Michigan | Ash1l inhibitors and methods of treatment therewith |
| CN110546150B (zh) | 2017-10-19 | 2021-12-21 | 江苏豪森药业集团有限公司 | 含吡唑基的三并环类衍生物、其制备方法和应用 |
| EA202091063A1 (ru) | 2017-11-01 | 2020-09-18 | Бристол-Маерс Сквибб Компани | Мостиковые бициклические соединения в качестве модуляторов фарнезоидного х-рецептора |
| CN107698505A (zh) | 2017-11-20 | 2018-02-16 | 孙婷婷 | 一种诺得司他的制备方法 |
| AU2018385664B2 (en) | 2017-12-13 | 2022-06-02 | Lupin Limited | Substituted bicyclic heterocyclic compounds as PRMT5 inhibitors |
| AU2019215598B2 (en) | 2018-01-31 | 2023-12-21 | Merck Patent Gmbh | Quinoline compounds as IRAK inhibitors and uses thereof |
| BR112020026314A2 (pt) | 2018-06-22 | 2021-03-30 | Ucl Business Ltd | Novos compostos |
| AU2019317549A1 (en) | 2018-08-07 | 2021-02-25 | Msd International Gmbh | PRMT5 inhibitors |
| KR20210089656A (ko) | 2018-10-05 | 2021-07-16 | 버텍스 파마슈티칼스 인코포레이티드 | 알파-1 항트립신 조절제 |
| CN110776459B (zh) | 2019-03-19 | 2023-01-24 | 江苏知原药业股份有限公司 | 7-羟基-2-喹诺酮-二硫代氨基甲酸酯类胆碱酯酶抑制剂 |
| UY38696A (es) | 2019-05-14 | 2020-11-30 | Vertex Pharma | Moduladores de alfa-1 antitripsina |
| TW202116303A (zh) | 2019-10-02 | 2021-05-01 | 美商維泰克斯製藥公司 | α—１抗胰蛋白酶缺乏症之治療方法 |
| MX2022009197A (es) | 2020-01-30 | 2022-10-13 | Vertex Pharma | Metodos de tratamiento para deficiencia de alfa-1 antitripsina. |
| WO2021203028A1 (en) | 2020-04-03 | 2021-10-07 | Vertex Pharmaceuticals Incorporated | 7- or 8-hydroxy-isoquinoline and 7- or 8-hydroxy-quinoline derivatives as alpha-1 -antitrypsin modulators for treating alpha-1 -antitrypsin deficiency (aatd) |
| CN115776984A (zh) | 2020-04-03 | 2023-03-10 | 弗特克斯药品有限公司 | 作为用于治疗α-1抗胰蛋白酶缺乏症(AATD)的α-1-抗胰蛋白酶调节剂的吡咯并[2,3-f]吲唑和2,4,5,10-四氮杂三环[7.3.0.03,7]十二碳-1,3(7),5,8,11-五烯衍生物 |
| IL296920A (en) | 2020-04-03 | 2022-12-01 | Vertex Pharma | Indole derivatives as alpha-1-antitrypsin modulators for the treatment of alpha-1-antitrypsin deficiency (aatd) |
| US20230157999A1 (en) | 2020-04-03 | 2023-05-25 | Vertex Pharmaceuticals Incorporated | Pyrano[4,3-b]indole derivatives as alpha-1-antitrypsin modulators for treating alpha-1-antitrypsin deficiency (aatd) |
| CA3177524A1 (en) | 2020-04-03 | 2021-10-07 | Vertex Pharmaceuticals Incorporated | Modulators of alpha-1 antitrypsin |
| WO2021203025A1 (en) | 2020-04-03 | 2021-10-07 | Vertex Pharmaceuticals Incorporated | 1 h-pyrazolo[4,3-g]isoquinoline and 1 h-pyrazolo[4,3-g]quinoline derivatives as alpha-1 -antitrypsin modulators for treating alpha-1 -antitrypsin deficiency (aatd) |
| EP4188931A2 (en) | 2020-07-27 | 2023-06-07 | Vertex Pharmaceuticals Incorporated | Processes for preparing modulators of alpha-1 antitrypsin |
-
2019
- 2019-10-04 KR KR1020217013514A patent/KR20210089656A/ko active Search and Examination
- 2019-10-04 US US16/593,118 patent/US11623924B2/en active Active
- 2019-10-04 MA MA053827A patent/MA53827A/fr unknown
- 2019-10-04 CN CN201980078980.8A patent/CN113164761A/zh active Pending
- 2019-10-04 BR BR112021006392A patent/BR112021006392A2/pt unknown
- 2019-10-04 JO JOP/2021/0060A patent/JOP20210060A1/ar unknown
- 2019-10-04 AU AU2019362753A patent/AU2019362753A1/en active Pending
- 2019-10-04 EP EP19848828.0A patent/EP3860712A1/en active Pending
- 2019-10-04 WO PCT/US2019/054681 patent/WO2020081257A1/en active Application Filing
- 2019-10-04 JP JP2021518181A patent/JP2022512588A/ja active Pending
- 2019-10-04 CA CA3114672A patent/CA3114672A1/en active Pending
- 2019-10-04 MX MX2021003819A patent/MX2021003819A/es unknown
- 2019-10-05 TW TW108136173A patent/TW202024091A/zh unknown
- 2019-10-07 UY UY0001038403A patent/UY38403A/es unknown
-
2021
- 2021-03-29 IL IL281884A patent/IL281884A/en unknown
- 2021-05-05 CO CONC2021/0005884A patent/CO2021005884A2/es unknown
-
2023
- 2023-02-09 US US18/107,786 patent/US20230265080A1/en active Pending
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