JP2011511089A5 - - Google Patents
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- Publication number
- JP2011511089A5 JP2011511089A5 JP2010545997A JP2010545997A JP2011511089A5 JP 2011511089 A5 JP2011511089 A5 JP 2011511089A5 JP 2010545997 A JP2010545997 A JP 2010545997A JP 2010545997 A JP2010545997 A JP 2010545997A JP 2011511089 A5 JP2011511089 A5 JP 2011511089A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- optionally substituted
- halo
- heteroaryl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 40
- 125000003118 aryl group Chemical group 0.000 claims 40
- -1 Amino, monosubstituted amino Chemical group 0.000 claims 31
- 125000005843 halogen group Chemical group 0.000 claims 27
- 125000000623 heterocyclic group Chemical group 0.000 claims 27
- 125000001072 heteroaryl group Chemical group 0.000 claims 25
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims 19
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 18
- 125000004438 haloalkoxy group Chemical group 0.000 claims 18
- 125000001188 haloalkyl group Chemical group 0.000 claims 18
- 125000002723 alicyclic group Chemical group 0.000 claims 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 14
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000004442 acylamino group Chemical group 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 10
- 125000000304 alkynyl group Chemical group 0.000 claims 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000004414 alkyl thio group Chemical group 0.000 claims 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 8
- 125000004104 aryloxy group Chemical group 0.000 claims 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 125000005110 aryl thio group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000005368 heteroarylthio group Chemical group 0.000 claims 6
- 206010016654 Fibrosis Diseases 0.000 claims 5
- 208000019425 cirrhosis of liver Diseases 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 230000004761 fibrosis Effects 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 4
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims 4
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 4
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Chemical group 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 102000004225 Cathepsin B Human genes 0.000 claims 3
- 108090000712 Cathepsin B Proteins 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000005089 alkenylaminocarbonyl group Chemical group 0.000 claims 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 2
- 229930195729 fatty acid Natural products 0.000 claims 2
- 239000000194 fatty acid Substances 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- 230000003176 fibrotic effect Effects 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- PKBCCOYLTICKIY-SRGWINKKSA-N (2s,4r)-1-[(2s)-2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-n-[(3s)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl]-4-(6-ethoxyisoquinolin-1-yl)oxypyrrolidine-2-carboxamide Chemical compound O=C([C@@H](NC(=O)[C@H]1N(C[C@@H](C1)OC=1C2=CC=C(OCC)C=C2C=CN=1)C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)CCC)C(=O)NC1CC1 PKBCCOYLTICKIY-SRGWINKKSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000000668 Chronic Pancreatitis Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- 206010018341 Gliosis Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 201000011442 Metachromatic leukodystrophy Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 206010033647 Pancreatitis acute Diseases 0.000 claims 1
- 206010033649 Pancreatitis chronic Diseases 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000007135 Retinal Neovascularization Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 206010064390 Tumour invasion Diseases 0.000 claims 1
- 201000003229 acute pancreatitis Diseases 0.000 claims 1
- 208000026594 alcoholic fatty liver disease Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000009400 cancer invasion Effects 0.000 claims 1
- 230000009787 cardiac fibrosis Effects 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 1
- 230000007387 gliosis Effects 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 201000006938 muscular dystrophy Diseases 0.000 claims 1
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 208000028169 periodontal disease Diseases 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000007863 steatosis Effects 0.000 claims 1
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2700708P | 2008-02-07 | 2008-02-07 | |
| US61/027,007 | 2008-02-07 | ||
| PCT/US2009/033229 WO2009100225A1 (en) | 2008-02-07 | 2009-02-05 | Inhibitors of cathepsin b |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014209108A Division JP2015051985A (ja) | 2008-02-07 | 2014-10-10 | カテプシンｂの阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011511089A JP2011511089A (ja) | 2011-04-07 |
| JP2011511089A5 true JP2011511089A5 (enExample) | 2012-03-29 |
| JP5718647B2 JP5718647B2 (ja) | 2015-05-13 |
Family
ID=40939419
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010545997A Active JP5718647B2 (ja) | 2008-02-07 | 2009-02-05 | カテプシンｂの阻害剤 |
| JP2014209108A Withdrawn JP2015051985A (ja) | 2008-02-07 | 2014-10-10 | カテプシンｂの阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014209108A Withdrawn JP2015051985A (ja) | 2008-02-07 | 2014-10-10 | カテプシンｂの阻害剤 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8211897B2 (enExample) |
| EP (1) | EP2237793A4 (enExample) |
| JP (2) | JP5718647B2 (enExample) |
| CN (1) | CN101969973B (enExample) |
| BR (1) | BRPI0907729A2 (enExample) |
| CA (1) | CA2713108A1 (enExample) |
| EA (1) | EA201001262A1 (enExample) |
| MX (1) | MX2010008371A (enExample) |
| WO (1) | WO2009100225A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2008251425A1 (en) | 2007-05-10 | 2008-11-20 | Array Biopharma, Inc. | Novel peptide inhibitors of hepatitis C virus replication |
| MX2010011306A (es) | 2008-04-15 | 2010-11-09 | Intermune Inc | Nuevos inhibidores macrociclicos de la replicacion del virus de la hepatitis c. |
| AR075584A1 (es) | 2009-02-27 | 2011-04-20 | Intermune Inc | COMPOSICIONES TERAPEUTICAS QUE COMPRENDEN beta-D-2'-DESOXI-2'-FLUORO-2'-C-METILCITIDINA Y UN DERIVADO DE ACIDO ISOINDOL CARBOXILICO Y SUS USOS. COMPUESTO. |
| KR20140102253A (ko) * | 2011-11-25 | 2014-08-21 | 에프. 호프만-라 로슈 아게 | 카텝신의 억제제로서의 피롤리딘 유도체 |
| US20140256698A1 (en) * | 2013-03-11 | 2014-09-11 | Virobay, Inc. | Cathepsin inhibitors |
| EP3394056B1 (en) | 2015-12-22 | 2021-04-14 | Shy Therapeutics LLC | Compounds for the treatment of cancer and inflammatory disease |
| WO2017222914A1 (en) | 2016-06-21 | 2017-12-28 | Inception 4, Inc. | Carbocyclic prolinamide derivatives |
| CN109476637B (zh) | 2016-06-21 | 2022-02-01 | 奥瑞恩眼科有限责任公司 | 杂环脯氨酰胺衍生物 |
| CN109661389A (zh) * | 2016-08-23 | 2019-04-19 | 豪夫迈·罗氏有限公司 | 作为htra1抑制剂的新型二氟酮酰胺衍生物 |
| US10834908B2 (en) * | 2017-04-26 | 2020-11-17 | InfiCure Bio AB | Model animal for fibrosis |
| CA3066939A1 (en) | 2017-06-21 | 2018-12-27 | SHY Therapeutics LLC | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| EP3655015B1 (en) * | 2017-07-17 | 2024-02-21 | The Regents of the University of Colorado | Compositions and methods for preventing and treating radiation-induced bystander effects caused by radiation or radiotherapy |
| US12391705B2 (en) | 2018-12-19 | 2025-08-19 | Shy Therapeutics, Llc | Compounds that interact with the Ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ520093A (en) | 1997-11-11 | 2004-03-26 | Pfizer Prod Inc | Thienopyrimidine and thienopyridine derivatives useful as anticancer agents |
| US6323180B1 (en) * | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| US6404397B1 (en) | 1998-08-10 | 2002-06-11 | Raytheon Company | Compact all-weather electromagnetic imaging system |
| US6608027B1 (en) * | 1999-04-06 | 2003-08-19 | Boehringer Ingelheim (Canada) Ltd | Macrocyclic peptides active against the hepatitis C virus |
| EP1254901A4 (en) * | 2000-01-26 | 2003-03-05 | Ono Pharmaceutical Co | 5-CHAIN CYCLIC COMPOUNDS, CONTAINING NITROGEN, AND MEDICINAL PRODUCTS CONTAINING THE SAME AS ACTIVE INGREDIENTS |
| CA2369970A1 (en) * | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| UY28525A1 (es) | 2003-09-22 | 2005-04-29 | Boehringer Ingelheim Int | Péptidos macrociclicos activos contra en virus de la hepatitis c |
| WO2006113942A2 (en) | 2005-04-20 | 2006-10-26 | Schering Corporation | Method of inhibiting cathepsin activity |
| US20060276407A1 (en) * | 2005-06-02 | 2006-12-07 | Schering Corporation | Methods of treating hepatitis C virus |
| US20060276406A1 (en) | 2005-06-02 | 2006-12-07 | Schering Corporation | Methods of treating hepatitis C virus |
| US20060287248A1 (en) | 2005-06-02 | 2006-12-21 | Schering Corporation | Asymmetric dosing methods |
| US7608592B2 (en) * | 2005-06-30 | 2009-10-27 | Virobay, Inc. | HCV inhibitors |
| RU2008152171A (ru) * | 2006-07-05 | 2010-08-10 | Интермьюн, Инк. (Us) | Новые ингибиторы вирусной репликации гепатита с |
| WO2008086053A1 (en) | 2007-01-03 | 2008-07-17 | Virobay, Inc. | Hcv inhibitors |
-
2009
- 2009-02-05 EA EA201001262A patent/EA201001262A1/ru unknown
- 2009-02-05 JP JP2010545997A patent/JP5718647B2/ja active Active
- 2009-02-05 WO PCT/US2009/033229 patent/WO2009100225A1/en not_active Ceased
- 2009-02-05 CN CN200980109079.9A patent/CN101969973B/zh not_active Expired - Fee Related
- 2009-02-05 CA CA2713108A patent/CA2713108A1/en not_active Abandoned
- 2009-02-05 BR BRPI0907729-4A patent/BRPI0907729A2/pt not_active IP Right Cessation
- 2009-02-05 US US12/366,504 patent/US8211897B2/en not_active Expired - Fee Related
- 2009-02-05 EP EP09709414.8A patent/EP2237793A4/en not_active Withdrawn
- 2009-02-05 MX MX2010008371A patent/MX2010008371A/es active IP Right Grant
-
2014
- 2014-10-10 JP JP2014209108A patent/JP2015051985A/ja not_active Withdrawn
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