JP2013515040A5 - - Google Patents
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- Publication number
- JP2013515040A5 JP2013515040A5 JP2012545305A JP2012545305A JP2013515040A5 JP 2013515040 A5 JP2013515040 A5 JP 2013515040A5 JP 2012545305 A JP2012545305 A JP 2012545305A JP 2012545305 A JP2012545305 A JP 2012545305A JP 2013515040 A5 JP2013515040 A5 JP 2013515040A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- dioxo
- pyrazol
- nicotinamide
- 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
- -1 carboxamide compound Chemical class 0.000 claims 89
- 125000001072 heteroaryl group Chemical group 0.000 claims 33
- 125000003118 aryl group Chemical group 0.000 claims 28
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 25
- 125000001424 substituent group Chemical group 0.000 claims 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 9
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000000651 prodrug Substances 0.000 claims 7
- 229940002612 prodrug Drugs 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 150000004677 hydrates Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 208000014674 injury Diseases 0.000 claims 4
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 3
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims 3
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 230000008733 trauma Effects 0.000 claims 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 235000005152 nicotinamide Nutrition 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- VLSSILIYHTYHQV-BPGUCPLFSA-N (2r)-n-[4-(cyclopropylamino)-3,4-dioxo-1-phenylbutan-2-yl]-1-[(2-fluorophenyl)methyl]-5-oxopyrrolidine-2-carboxamide Chemical compound FC1=CC=CC=C1CN1C(=O)CC[C@@H]1C(=O)NC(C(=O)C(=O)NC1CC1)CC1=CC=CC=C1 VLSSILIYHTYHQV-BPGUCPLFSA-N 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000004227 1,3-benzoxazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)OC2=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010003225 Arteriospasm coronary Diseases 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
- 208000002177 Cataract Diseases 0.000 claims 1
- 208000003890 Coronary Vasospasm Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102000000589 Interleukin-1 Human genes 0.000 claims 1
- 108010002352 Interleukin-1 Proteins 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 201000005485 Toxoplasmosis Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 238000002399 angioplasty Methods 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 210000004556 brain Anatomy 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
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 230000003683 cardiac damage Effects 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 201000011634 coronary artery vasospasm Diseases 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 230000008717 functional decline Effects 0.000 claims 1
- 208000014617 hemorrhoid Diseases 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000001286 intracranial vasospasm Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 201000006938 muscular dystrophy Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 210000002027 skeletal muscle Anatomy 0.000 claims 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28891809P | 2009-12-22 | 2009-12-22 | |
| US61/288,918 | 2009-12-22 | ||
| US41047610P | 2010-11-05 | 2010-11-05 | |
| US61/410,476 | 2010-11-05 | ||
| PCT/EP2010/070420 WO2011076812A1 (en) | 2009-12-22 | 2010-12-21 | Carboxamide compounds and their use as calpain inhibitors iv |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015214532A Division JP2016065071A (ja) | 2009-12-22 | 2015-10-30 | カルボキサミド化合物類およびカルパイン阻害剤ｉｖとしてのこれらの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013515040A JP2013515040A (ja) | 2013-05-02 |
| JP2013515040A5 true JP2013515040A5 (enExample) | 2014-02-06 |
| JP5913125B2 JP5913125B2 (ja) | 2016-04-27 |
Family
ID=43707825
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012545305A Expired - Fee Related JP5913125B2 (ja) | 2009-12-22 | 2010-12-21 | カルボキサミド化合物類およびカルパイン阻害剤ｉｖとしてのこれらの使用 |
| JP2015214532A Pending JP2016065071A (ja) | 2009-12-22 | 2015-10-30 | カルボキサミド化合物類およびカルパイン阻害剤ｉｖとしてのこれらの使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015214532A Pending JP2016065071A (ja) | 2009-12-22 | 2015-10-30 | カルボキサミド化合物類およびカルパイン阻害剤ｉｖとしてのこれらの使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8598211B2 (enExample) |
| EP (1) | EP2516415B1 (enExample) |
| JP (2) | JP5913125B2 (enExample) |
| CN (2) | CN105732581A (enExample) |
| AR (1) | AR079665A1 (enExample) |
| CA (1) | CA2783714A1 (enExample) |
| ES (1) | ES2477583T3 (enExample) |
| MX (1) | MX2012007322A (enExample) |
| TW (1) | TW201132632A (enExample) |
| UY (1) | UY33149A (enExample) |
| WO (1) | WO2011076812A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8236798B2 (en) * | 2009-05-07 | 2012-08-07 | Abbott Gmbh & Co. Kg | Carboxamide compounds and their use as calpain inhibitors |
| US8598211B2 (en) * | 2009-12-22 | 2013-12-03 | Abbvie Inc. | Carboxamide compounds and their use as calpain inhibitors IV |
| EP2648731B1 (en) | 2010-12-09 | 2017-01-25 | Abbvie Deutschland GmbH & Co. KG | Carboxamide compounds and their use as calpain inhibitors v |
| CA2867210A1 (en) * | 2012-04-03 | 2013-10-10 | AbbVie Deutschland GmbH & Co. KG | Carboxamide compounds and their use as calpain inhibitors v |
| EP3763367A1 (en) | 2012-12-06 | 2021-01-13 | Celgene Quanticel Research, Inc. | Pyridine-pyrazole derivatives as histone demethylase inhibitors |
| EP3426674A4 (en) | 2016-03-09 | 2019-08-14 | Blade Therapeutics, Inc. | CYCLIC KETO AMID COMPOUNDS AS CALPAIN MODULATORS AND METHOD FOR THE PRODUCTION AND USE THEREOF |
| AU2017292646A1 (en) | 2016-07-05 | 2019-02-07 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| KR20190063473A (ko) | 2016-09-28 | 2019-06-07 | 블레이드 테라퓨틱스, 인크. | 칼페인 조정자 및 그 치료학적 용도 |
| EP4488264A1 (en) * | 2022-03-01 | 2025-01-08 | WestVac Biopharma Co., Ltd. | Keto amide derivatives and pharmaceutical use thereof |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4826835A (en) | 1985-10-23 | 1989-05-02 | Rorer Pharmaceutical Corporation | Pyridyl-pyridazinone and pyridyl-pyrazolinone compounds and their use in the treatment of congestive heart failure |
| US4743608A (en) | 1986-07-15 | 1988-05-10 | Rorer Pharmaceutical Corporation | Pyridone-pyridyl-imidazolyl and triazolyl compounds and their use as cardiotonic agents |
| DE19642591A1 (de) | 1996-10-15 | 1998-04-16 | Basf Ag | Neue Piperidin-Ketocarbonsäure-Derivate, deren Herstellung und Anwendung |
| DE19650975A1 (de) | 1996-12-09 | 1998-06-10 | Basf Ag | Neue heterocyclisch substituierte Benzamide und deren Anwendung |
| EP0944582B1 (de) | 1996-12-11 | 2003-07-02 | Abbott GmbH & Co. KG | Ketobenzamide als calpain-inhibitoren |
| US6083944A (en) | 1997-10-07 | 2000-07-04 | Cephalon, Inc. | Quinoline-containing α-ketoamide cysteine and serine protease inhibitors |
| DE19817459A1 (de) | 1998-04-20 | 1999-10-21 | Basf Ag | Neue heterozyklische substituierte Amide, Herstellung und Anwendung |
| WO1999054320A1 (de) | 1998-04-20 | 1999-10-28 | Basf Aktiengesellschaft | Neue heterocyclisch substituierte amide mit cystein-protease hemmender wirkung |
| JP4621351B2 (ja) | 1998-04-20 | 2011-01-26 | アボット ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | カルパインインヒビターとしての複素環式的に置換されたアミド |
| DE19818614A1 (de) | 1998-04-20 | 1999-10-21 | Basf Ag | Neue substituierte Amide, deren Herstellung und Anwendung |
| AU3927699A (en) | 1998-04-20 | 1999-11-08 | Basf Aktiengesellschaft | New substituted amides, their production and their use |
| ES2277439T3 (es) | 1998-05-25 | 2007-07-01 | ABBOTT GMBH & CO. KG | Amidas heterociclicas sustituidas, su produccion y su uso. |
| DE10114762A1 (de) | 2001-03-26 | 2002-10-02 | Knoll Gmbh | Verwendung von Cysteinprotease-Inhibitoren |
| WO2007016589A2 (en) | 2005-08-02 | 2007-02-08 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
| DK2439205T3 (da) * | 2006-12-29 | 2015-06-22 | Abbvie Deutschland | Carboxamidforbindelser og deres anvendelse som calpaininhibitorer |
| EP2495249A1 (en) | 2007-02-26 | 2012-09-05 | Achillion Pharmaceuticals, Inc. | Tertiary amine substituted peptides useful as inhibitors of HCV replication |
| TWI453019B (zh) * | 2007-12-28 | 2014-09-21 | Abbvie Deutschland | 甲醯胺化合物 |
| US8598211B2 (en) * | 2009-12-22 | 2013-12-03 | Abbvie Inc. | Carboxamide compounds and their use as calpain inhibitors IV |
-
2010
- 2010-12-20 US US12/972,679 patent/US8598211B2/en active Active
- 2010-12-21 CA CA2783714A patent/CA2783714A1/en not_active Abandoned
- 2010-12-21 AR ARP100104829A patent/AR079665A1/es unknown
- 2010-12-21 CN CN201610152369.3A patent/CN105732581A/zh active Pending
- 2010-12-21 EP EP10798323.1A patent/EP2516415B1/en not_active Not-in-force
- 2010-12-21 MX MX2012007322A patent/MX2012007322A/es active IP Right Grant
- 2010-12-21 CN CN2010800640243A patent/CN102753541A/zh active Pending
- 2010-12-21 JP JP2012545305A patent/JP5913125B2/ja not_active Expired - Fee Related
- 2010-12-21 ES ES10798323.1T patent/ES2477583T3/es active Active
- 2010-12-21 WO PCT/EP2010/070420 patent/WO2011076812A1/en not_active Ceased
- 2010-12-22 UY UY0001033149A patent/UY33149A/es not_active Application Discontinuation
- 2010-12-22 TW TW099145352A patent/TW201132632A/zh unknown
-
2013
- 2013-10-15 US US14/054,460 patent/US20140179702A1/en not_active Abandoned
-
2015
- 2015-10-30 JP JP2015214532A patent/JP2016065071A/ja active Pending
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