JP2017526701A5 - - Google Patents
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- Publication number
- JP2017526701A5 JP2017526701A5 JP2017513052A JP2017513052A JP2017526701A5 JP 2017526701 A5 JP2017526701 A5 JP 2017526701A5 JP 2017513052 A JP2017513052 A JP 2017513052A JP 2017513052 A JP2017513052 A JP 2017513052A JP 2017526701 A5 JP2017526701 A5 JP 2017526701A5
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- chlorine
- hydrogen
- formula
- trifluoromethyl
- 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
Links
- 229910052731 fluorine Inorganic materials 0.000 claims description 36
- 239000011737 fluorine Substances 0.000 claims description 36
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
- 238000006467 substitution reaction Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- -1 pentafluorosulfanyl Chemical group 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 9
- 230000003176 fibrotic effect Effects 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 4
- 206010006448 Bronchiolitis Diseases 0.000 claims 3
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 208000030533 eye disease Diseases 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 3
- 230000000414 obstructive effect Effects 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 208000002815 pulmonary hypertension Diseases 0.000 claims 3
- 208000017520 skin disease Diseases 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 230000009278 visceral effect Effects 0.000 claims 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 claims 1
- 108091006335 Prostaglandin I receptors Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000002308 endothelin receptor antagonist Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims 1
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims 1
- 229960003073 pirfenidone Drugs 0.000 claims 1
- 150000003815 prostacyclins Chemical class 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 229940125526 sGC activator Drugs 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
- 229940127296 soluble guanylate cyclase stimulator Drugs 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14184040.5 | 2014-09-09 | ||
| EP14184040 | 2014-09-09 | ||
| PCT/EP2015/070318 WO2016037954A1 (de) | 2014-09-09 | 2015-09-07 | Substituierte n,2-diarylchinolin-4-carboxamide und ihre anti-inflammatorische verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017526701A JP2017526701A (ja) | 2017-09-14 |
| JP2017526701A5 true JP2017526701A5 (enExample) | 2019-09-12 |
| JP6618530B2 JP6618530B2 (ja) | 2019-12-11 |
Family
ID=51492240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017513052A Expired - Fee Related JP6618530B2 (ja) | 2014-09-09 | 2015-09-07 | 置換ｎ，２−ジアリールキノリン−４−カルボキサミドおよび抗炎症剤としてのその使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US10189788B2 (enExample) |
| EP (1) | EP3191452A1 (enExample) |
| JP (1) | JP6618530B2 (enExample) |
| CN (1) | CN107074773A (enExample) |
| CA (1) | CA2960324A1 (enExample) |
| WO (1) | WO2016037954A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10189788B2 (en) * | 2014-09-09 | 2019-01-29 | Bayer Pharma Aktiengesellschaft | Substituted N,2-diarylquinoline-4-carboxamides and the use thereof as anti-inflammatory agents |
| CA2979926A1 (en) * | 2015-03-18 | 2016-09-22 | Bayer Pharma Aktiengesellschaft | Substituted n-bicyclo-2-aryl-quinolin-4-carboxamides and use thereof |
| BR112019021136A2 (pt) | 2017-04-10 | 2020-07-21 | Bayer Aktiengesellschaft | n-ariletil-2-arilquinolina-4-carboxamidas substituídas e uso das mesmas |
| TWI770157B (zh) * | 2017-04-10 | 2022-07-11 | 德商拜耳廠股份有限公司 | 經取代之n-芳基乙基-2-胺基喹啉-4-甲醯胺及其用途 |
| WO2022053651A2 (en) | 2020-09-10 | 2022-03-17 | Precirix N.V. | Antibody fragment against fap |
| WO2023203135A1 (en) | 2022-04-22 | 2023-10-26 | Precirix N.V. | Improved radiolabelled antibody |
| WO2023213801A1 (en) | 2022-05-02 | 2023-11-09 | Precirix N.V. | Pre-targeting |
| WO2025021913A1 (en) | 2023-07-26 | 2025-01-30 | Ferring B.V. | Small molecule prostaglandin f receptor antagonists |
| WO2025189066A1 (en) * | 2024-03-08 | 2025-09-12 | Athira Pharma, Inc. | Modulators of g protein-coupled receptor 55 (gpr55) |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU699319B2 (en) | 1994-05-27 | 1998-12-03 | Smithkline Beecham Farmaceutici S.P.A. | Quinoline derivatives as tachykinin nk3 receptor antagonists |
| IT1270615B (it) * | 1994-07-14 | 1997-05-07 | Smithkline Beecham Farma | Uso di derivati di chinolina |
| AR004735A1 (es) | 1995-11-24 | 1999-03-10 | Smithkline Beecham Spa | Quinoleina 4-amido sustituida, un procedimiento para su preparacion, una composicion farmaceutica que los contiene y el uso de los mismos para lapreparacion de un medicamento. |
| DE19834047A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Substituierte Pyrazolderivate |
| DE19834044A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Neue substituierte Pyrazolderivate |
| DE19943635A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943639A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Dicarbonsäurederivate mit neuartigen pharmazeutischen Eigenschaften |
| DE19943636A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943634A1 (de) | 1999-09-13 | 2001-04-12 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| AR031176A1 (es) | 2000-11-22 | 2003-09-10 | Bayer Ag | Nuevos derivados de pirazolpiridina sustituidos con piridina |
| DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| CN1660811A (zh) * | 2004-02-27 | 2005-08-31 | 中国科学院上海药物研究所 | 1，4－二取代苯类化合物及其制备方法和用途 |
| US20090069301A1 (en) * | 2005-03-03 | 2009-03-12 | Sirtris Pharmaceuticals, Inc. | Acridine and Quinoline Derivatives as Sirtuin Modulators |
| EP2297117B1 (en) | 2008-05-19 | 2012-10-31 | Merck Sharp & Dohme Corp. | Bicyclic heterocycle derivatives and use thereof as gpr119 modulators |
| ES2874063T3 (es) | 2009-03-31 | 2021-11-04 | Renascience Inc | Inhibidor del inhibidor-1 del activador del plasminógeno |
| JP2011042643A (ja) | 2009-07-24 | 2011-03-03 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| WO2011153553A2 (en) | 2010-06-04 | 2011-12-08 | The Regents Of The University Of California | Methods and compositions for kinase inhibition |
| PE20130779A1 (es) | 2010-07-09 | 2013-06-21 | Bayer Ip Gmbh | Pirimidinas y triazinas condensadas y su uso |
| DE102010040233A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Bicyclische Aza-Heterocyclen und ihre Verwendung |
| DE102010043379A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 6-Fluor-1H-Pyrazolo[4,3-b]pyridine und ihre Verwendung |
| WO2013074059A2 (en) | 2010-11-05 | 2013-05-23 | Regents Of The University Of Minnesota | Cytosine deaminase modulators for enhancement of dna transfection |
| CA2867527A1 (en) | 2012-05-03 | 2013-11-07 | Takeda Gmbh | Novel ep2 receptor agonists |
| TWI572597B (zh) * | 2012-06-29 | 2017-03-01 | 美國禮來大藥廠 | 二甲基－苯甲酸化合物 |
| WO2014117090A1 (en) | 2013-01-28 | 2014-07-31 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| AU2014366371B2 (en) | 2013-12-17 | 2017-02-16 | Eli Lilly And Company | Dimethylbenzoic acid compounds |
| US10189788B2 (en) * | 2014-09-09 | 2019-01-29 | Bayer Pharma Aktiengesellschaft | Substituted N,2-diarylquinoline-4-carboxamides and the use thereof as anti-inflammatory agents |
-
2015
- 2015-09-07 US US15/509,600 patent/US10189788B2/en not_active Expired - Fee Related
- 2015-09-07 JP JP2017513052A patent/JP6618530B2/ja not_active Expired - Fee Related
- 2015-09-07 WO PCT/EP2015/070318 patent/WO2016037954A1/de not_active Ceased
- 2015-09-07 CA CA2960324A patent/CA2960324A1/en not_active Abandoned
- 2015-09-07 EP EP15757299.1A patent/EP3191452A1/de not_active Withdrawn
- 2015-09-07 CN CN201580060830.6A patent/CN107074773A/zh active Pending
-
2018
- 2018-09-07 US US16/125,645 patent/US10479765B2/en not_active Expired - Fee Related