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 |
| US8048862B2 (en) | 2008-04-15 | 2011-11-01 | Intermune, Inc. | Macrocyclic inhibitors of hepatitis C virus replication |
| 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 |
| WO2014164844A1 (en) * | 2013-03-11 | 2014-10-09 | Virobay, Inc. | Cathepsin inhibitors |
| WO2017112777A1 (en) | 2015-12-22 | 2017-06-29 | SHY Therapeutics LLC | Compounds for the treatment of cancer and inflammatory disease |
| EA201990069A1 (ru) | 2016-06-21 | 2019-06-28 | ОРИОН ОФТАЛМОЛОДЖИ ЭлЭлСи | Производные гетероциклического пролинамида |
| WO2017222914A1 (en) | 2016-06-21 | 2017-12-28 | Inception 4, Inc. | Carbocyclic prolinamide derivatives |
| WO2018036942A1 (en) * | 2016-08-23 | 2018-03-01 | F. Hoffmann-La Roche Ag | New difluoroketamide derivatives as htra1 inhibitors |
| US10834908B2 (en) * | 2017-04-26 | 2020-11-17 | InfiCure Bio AB | Model animal for fibrosis |
| BR112019027640A2 (pt) | 2017-06-21 | 2020-07-07 | SHY Therapeutics LLC | composto, método para testar a capacidade de um ou mais compostos, método para inibir a função de ras, método para inibir a função de rho, método para inibir a função de rac, composição farmacêutica |
| CN111447940A (zh) * | 2017-07-17 | 2020-07-24 | 科罗拉多大学评议会 | 预防或治疗由辐射或放射疗法引起的辐射诱发的旁观者效应的组合物和方法 |
| WO2020132071A1 (en) | 2018-12-19 | 2020-06-25 | Shy Therapeutics. Llc | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and f1brotic disease |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA005889B1 (ru) | 1997-11-11 | 2005-06-30 | Пфайзер Продактс Инк. | Производные тиенопиримидина и тиенопиридина, полезные в качестве противораковых агентов |
| 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 |
| KR20020067702A (ko) * | 2000-01-26 | 2002-08-23 | 오노 야꾸힝 고교 가부시키가이샤 | 질소 함유 5원환 화합물 및 이러한 화합물을 유효성분으로서 함유하는 약제 |
| CA2369970A1 (en) * | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| ATE500264T1 (de) | 2003-09-22 | 2011-03-15 | Boehringer Ingelheim Int | Makrozyklische peptide mit wirkung gegen das hepatitis-c-virus |
| WO2006113942A2 (en) | 2005-04-20 | 2006-10-26 | Schering Corporation | Method of inhibiting cathepsin activity |
| US20060276406A1 (en) | 2005-06-02 | 2006-12-07 | Schering Corporation | Methods of treating hepatitis C virus |
| WO2006130554A2 (en) | 2005-06-02 | 2006-12-07 | Schering Corporation | Methods of treating hepatitis c virus |
| WO2006130688A2 (en) | 2005-06-02 | 2006-12-07 | Schering Corporation | Compounds for inhibiting cathepsin activity |
| US7608592B2 (en) | 2005-06-30 | 2009-10-27 | Virobay, Inc. | HCV inhibitors |
| KR20090024834A (ko) * | 2006-07-05 | 2009-03-09 | 인터뮨, 인크. | Ｃ형 간염 바이러스 복제의 신규 억제제 |
| US20080161254A1 (en) | 2007-01-03 | 2008-07-03 | Virobay, Inc. | Hcv inhibitors |
-
2009
- 2009-02-05 EA EA201001262A patent/EA201001262A1/ru unknown
- 2009-02-05 CA CA2713108A patent/CA2713108A1/en not_active Abandoned
- 2009-02-05 CN CN200980109079.9A patent/CN101969973B/zh not_active Expired - Fee Related
- 2009-02-05 US US12/366,504 patent/US8211897B2/en not_active Expired - Fee Related
- 2009-02-05 BR BRPI0907729-4A patent/BRPI0907729A2/pt not_active IP Right Cessation
- 2009-02-05 MX MX2010008371A patent/MX2010008371A/es active IP Right Grant
- 2009-02-05 EP EP09709414.8A patent/EP2237793A4/en not_active Withdrawn
- 2009-02-05 JP JP2010545997A patent/JP5718647B2/ja active Active
- 2009-02-05 WO PCT/US2009/033229 patent/WO2009100225A1/en not_active Ceased
-
2014
- 2014-10-10 JP JP2014209108A patent/JP2015051985A/ja not_active Withdrawn
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