JP2019507176A5 - - Google Patents
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- JP2019507176A5 JP2019507176A5 JP2018546501A JP2018546501A JP2019507176A5 JP 2019507176 A5 JP2019507176 A5 JP 2019507176A5 JP 2018546501 A JP2018546501 A JP 2018546501A JP 2018546501 A JP2018546501 A JP 2018546501A JP 2019507176 A5 JP2019507176 A5 JP 2019507176A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- difluoro
- methyl
- methoxyphenyl
- substituted
- 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.)
- Ceased
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 180
- -1 C 1-6 -alkyl Chemical group 0.000 claims 83
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 68
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 50
- 150000001875 compounds Chemical class 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 21
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 125000001475 halogen functional group Chemical group 0.000 claims 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 206010064930 age-related macular degeneration Diseases 0.000 claims 8
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 8
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 7
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 4
- 208000008069 Geographic Atrophy Diseases 0.000 claims 4
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 208000002780 macular degeneration Diseases 0.000 claims 4
- 230000007170 pathology Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- VNTGSQXECMTAGV-DCYPJBMNSA-N COC1=CC=C(C=C1)[C@H](NC(=O)C(CC1=CC(Cl)=CC=C1)NC(=O)C1=CC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)C(F)(F)C(=O)NCC(F)(F)F Chemical compound COC1=CC=C(C=C1)[C@H](NC(=O)C(CC1=CC(Cl)=CC=C1)NC(=O)C1=CC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)C(F)(F)C(=O)NCC(F)(F)F VNTGSQXECMTAGV-DCYPJBMNSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- PTXSOBQFCNCQCT-NDXORKPFSA-N COC1=CC=C(C=C1)[C@H](NC(=O)[C@H](C)NC(=O)C1=CC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)C(F)(F)C(=O)NCC(F)(F)F Chemical compound COC1=CC=C(C=C1)[C@H](NC(=O)[C@H](C)NC(=O)C1=CC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)C(F)(F)C(=O)NCC(F)(F)F PTXSOBQFCNCQCT-NDXORKPFSA-N 0.000 claims 1
- HMCIUNLYHJKMCX-AWCRTANDSA-N COC1=CC=C(C=C1)[C@H](NC(=O)[C@H](CC1=CC(=CC=C1)C#N)NC(=O)C1=CC=CC=C1)C(=O)N[C@@H](C1CCC1)C(=O)C(F)(F)C(=O)NCC(F)(F)F Chemical compound COC1=CC=C(C=C1)[C@H](NC(=O)[C@H](CC1=CC(=CC=C1)C#N)NC(=O)C1=CC=CC=C1)C(=O)N[C@@H](C1CCC1)C(=O)C(F)(F)C(=O)NCC(F)(F)F HMCIUNLYHJKMCX-AWCRTANDSA-N 0.000 claims 1
- MZVZDZPAFCGSHR-ACRUOGEOSA-N COC1=CC=C(C=C1)[C@H](NC(=O)[C@H](CO)NC(=O)C1=CC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)C(F)(F)C(=O)NCC(F)(F)F Chemical compound COC1=CC=C(C=C1)[C@H](NC(=O)[C@H](CO)NC(=O)C1=CC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)C(F)(F)C(=O)NCC(F)(F)F MZVZDZPAFCGSHR-ACRUOGEOSA-N 0.000 claims 1
- XRKIYGNXBIUZOX-ACRUOGEOSA-N FC(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(C(C(=O)NCC(F)(F)F)(F)F)=O)C(C)C)C1=CC=C(C=C1)OC)CO)(C1=CC(=CC=C1)F)F Chemical compound FC(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(C(C(=O)NCC(F)(F)F)(F)F)=O)C(C)C)C1=CC=C(C=C1)OC)CO)(C1=CC(=CC=C1)F)F XRKIYGNXBIUZOX-ACRUOGEOSA-N 0.000 claims 1
- ZRKJAZPFZJNNBE-FKBYEOEOSA-N FC(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(C(C(=O)NCC(F)(F)F)(F)F)=O)C(C)C)C1=CC=C(C=C1)OC)COC)(C1=CC(=CC=C1)F)F Chemical compound FC(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(C(C(=O)NCC(F)(F)F)(F)F)=O)C(C)C)C1=CC=C(C=C1)OC)COC)(C1=CC(=CC=C1)F)F ZRKJAZPFZJNNBE-FKBYEOEOSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 210000003161 choroid Anatomy 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 1
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 0 CCC**C(C(*)(C(C(C)(*)N(*)C(C(*)(*)N)=O)O)F)=O Chemical compound CCC**C(C(*)(C(C(C)(*)N(*)C(C(*)(*)N)=O)O)F)=O 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16158644.1 | 2016-03-04 | ||
| EP16158644 | 2016-03-04 | ||
| PCT/EP2017/054682 WO2017148967A1 (en) | 2016-03-04 | 2017-03-01 | New difluoroketamide derivatives as htra1 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2019507176A JP2019507176A (ja) | 2019-03-14 |
| JP2019507176A5 true JP2019507176A5 (https=) | 2020-04-09 |
Family
ID=55456685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018546501A Ceased JP2019507176A (ja) | 2016-03-04 | 2017-03-01 | Ｈｔｒａ１阻害剤としての新規ジフルオロケタミド誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11059858B2 (https=) |
| EP (1) | EP3423467B1 (https=) |
| JP (1) | JP2019507176A (https=) |
| CN (1) | CN108699105A (https=) |
| HK (1) | HK1257567A1 (https=) |
| WO (1) | WO2017148967A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE064412T2 (hu) | 2016-06-21 | 2024-03-28 | Orion Ophthalmology LLC | Heterociklusos prolinamid-származékok |
| JP7164521B2 (ja) | 2016-06-21 | 2022-11-01 | オリオン・オフサルモロジー・エルエルシー | 炭素環式プロリンアミド誘導体 |
| CN109709227B (zh) * | 2018-12-30 | 2021-09-24 | 中国水产科学研究院长江水产研究所 | 高效液相色谱-串联质谱测定水产品中盐酸氯苯胍及其代谢物残留量的方法 |
| TW202128664A (zh) | 2019-10-09 | 2021-08-01 | 德商拜耳廠股份有限公司 | 作為除害劑之新穎雜芳基三唑化合物 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986006379A1 (en) * | 1985-04-19 | 1986-11-06 | The Upjohn Company | Dihalo-statine substituted renin inhibitors |
| JPH10505582A (ja) | 1994-07-15 | 1998-06-02 | メリル・フアーマシユウテイカルズ・インコーポレイテツド | ジフルオロスタトン抗ウイルス剤 |
| EP1012180B1 (en) | 1997-08-11 | 2004-12-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor peptide analogues |
| CN1176941C (zh) | 1999-04-09 | 2004-11-24 | 西托维亚公司 | Caspase抑制剂及其应用 |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| US7244815B2 (en) | 2001-05-23 | 2007-07-17 | The Curators Of The University Of Missouri | Attachment and elaboration strategies for inverse peptide synthesis |
| UY28500A1 (es) | 2003-09-05 | 2005-04-29 | Vertex Pharma | Inhibidores de proteasas de serina, en particular proteasa ns3-ns4a del vhc. |
| WO2006050862A1 (en) * | 2004-11-10 | 2006-05-18 | Boehringer Ingelheim International Gmbh | Statine derivatives for the treatment of alzheimer's disease |
| US20110207704A1 (en) | 2006-12-15 | 2011-08-25 | Abbott Laboratories | Novel Oxadiazole Compounds |
| PE20081795A1 (es) * | 2007-02-16 | 2009-01-08 | Genentech Inc | Moduladores de htra1-pdz y htra3-pdz |
| US8377886B2 (en) * | 2007-09-14 | 2013-02-19 | Albert Einstein College Of Medicine Of Yeshiva University | Use of gamma secretase inhibitors and notch pathway inhibitors for treatment and prevention of renal disease |
| EP2661433B1 (en) | 2011-01-04 | 2017-08-16 | Novartis AG | Indole compounds or analogues thereof useful for the treatment of age-related macular degeneration (amd) |
| ES2644700T3 (es) | 2012-06-28 | 2017-11-30 | Novartis Ag | Derivados de pirrolidina y su uso como moduladores de la ruta del complemento |
| WO2016100555A1 (en) | 2014-12-18 | 2016-06-23 | Inception 4, Inc. | Boronic acid derivatives and uses thereof |
| EP3262026B1 (en) * | 2015-02-25 | 2020-03-18 | H. Hoffnabb-La Roche Ag | New trifluoromethylpropanamide derivatives |
| TW201713613A (zh) * | 2015-05-11 | 2017-04-16 | 赫孚孟拉羅股份公司 | 新二氟酮醯胺衍生物 |
-
2017
- 2017-03-01 EP EP17707875.5A patent/EP3423467B1/en active Active
- 2017-03-01 HK HK18116652.5A patent/HK1257567A1/zh unknown
- 2017-03-01 WO PCT/EP2017/054682 patent/WO2017148967A1/en not_active Ceased
- 2017-03-01 CN CN201780012559.8A patent/CN108699105A/zh active Pending
- 2017-03-01 JP JP2018546501A patent/JP2019507176A/ja not_active Ceased
-
2018
- 2018-09-04 US US16/121,244 patent/US11059858B2/en not_active Expired - Fee Related
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