JP2015512427A5 - - Google Patents
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- Publication number
- JP2015512427A5 JP2015512427A5 JP2015503800A JP2015503800A JP2015512427A5 JP 2015512427 A5 JP2015512427 A5 JP 2015512427A5 JP 2015503800 A JP2015503800 A JP 2015503800A JP 2015503800 A JP2015503800 A JP 2015503800A JP 2015512427 A5 JP2015512427 A5 JP 2015512427A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- amino
- group
- dioxo
- 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.)
- Pending
Links
- -1 Carboxamide compounds Chemical class 0.000 claims description 165
- 125000001424 substituent group Chemical group 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 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 description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 16
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 11
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 15
- 238000011282 treatment Methods 0.000 claims 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 12
- 230000004064 dysfunction Effects 0.000 claims 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 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 3
- 230000006378 damage Effects 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 229960003966 nicotinamide Drugs 0.000 claims 3
- 235000005152 nicotinamide Nutrition 0.000 claims 3
- 239000011570 nicotinamide Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004562 2,3-dihydroindol-1-yl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 102000007590 Calpain Human genes 0.000 claims 1
- 108010032088 Calpain Proteins 0.000 claims 1
- 208000002177 Cataract Diseases 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- 208000003890 Coronary Vasospasm Diseases 0.000 claims 1
- 208000013875 Heart injury Diseases 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 102000000589 Interleukin-1 Human genes 0.000 claims 1
- 108010002352 Interleukin-1 Proteins 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 208000029549 Muscle injury Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 201000005485 Toxoplasmosis Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 238000002399 angioplasty Methods 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 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
- 230000007812 deficiency Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000014674 injury 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
- 208000017169 kidney disease Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 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
- BNYTUBFUVIYKJH-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-2-(5-benzyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-2-yl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(N2N=C3CCN(CC=4C=CC=CC=4)CC3=C2)C=1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 BNYTUBFUVIYKJH-UHFFFAOYSA-N 0.000 claims 1
- YDYBYGOVADVOLI-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-2-[3-(2,3-dihydro-1,4-benzoxazin-4-ylmethyl)pyrazol-1-yl]pyridine-3-carboxamide Chemical compound C=1C=CN=C(N2N=C(CN3C4=CC=CC=C4OCC3)C=C2)C=1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 YDYBYGOVADVOLI-UHFFFAOYSA-N 0.000 claims 1
- LNYKWHMNUSKRNS-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-2-[3-(morpholin-4-ylmethyl)pyrazol-1-yl]pyridine-3-carboxamide Chemical compound C=1C=CN=C(N2N=C(CN3CCOCC3)C=C2)C=1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 LNYKWHMNUSKRNS-UHFFFAOYSA-N 0.000 claims 1
- AFGCGCDUITVJBY-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-2-[3-[(4-phenylpiperidin-1-yl)methyl]pyrazol-1-yl]pyridine-3-carboxamide Chemical compound C=1C=CN=C(N2N=C(CN3CCC(CC3)C=3C=CC=CC=3)C=C2)C=1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 AFGCGCDUITVJBY-UHFFFAOYSA-N 0.000 claims 1
- 210000000653 nervous system Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 208000028172 protozoa infectious disease Diseases 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
- KNLKRAUJQBLECR-UHFFFAOYSA-N tert-butyl pyridine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=N1 KNLKRAUJQBLECR-UHFFFAOYSA-N 0.000 claims 1
- ZXAPIQZSJHLLDS-UHFFFAOYSA-N tert-butyl pyridine-4-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=NC=C1 ZXAPIQZSJHLLDS-UHFFFAOYSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261619590P | 2012-04-03 | 2012-04-03 | |
| US61/619,590 | 2012-04-03 | ||
| PCT/EP2013/055291 WO2013149800A1 (en) | 2012-04-03 | 2013-03-14 | Carboxamide compounds and their use as calpain inhibitors v |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015512427A JP2015512427A (ja) | 2015-04-27 |
| JP2015512427A5 true JP2015512427A5 (enExample) | 2016-03-03 |
Family
ID=47878073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015503800A Pending JP2015512427A (ja) | 2012-04-03 | 2013-03-14 | カルボキサミド化合物およびそれのカルパイン阻害薬ｖとしての使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9150545B2 (enExample) |
| EP (1) | EP2834230A1 (enExample) |
| JP (1) | JP2015512427A (enExample) |
| CN (1) | CN104364247A (enExample) |
| CA (1) | CA2867210A1 (enExample) |
| MX (1) | MX2014011998A (enExample) |
| RU (1) | RU2014144285A (enExample) |
| SG (1) | SG11201406345XA (enExample) |
| WO (1) | WO2013149800A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10590084B2 (en) | 2016-03-09 | 2020-03-17 | Blade Therapeutics, Inc. | Cyclic keto-amide compounds as calpain modulators and methods of production and use thereof |
| WO2018009417A1 (en) | 2016-07-05 | 2018-01-11 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| MX2019003425A (es) | 2016-09-28 | 2019-08-16 | Blade Therapeutics Inc | Moduladores de calpainas y usos terapeuticos de los mismos. |
| AU2019242595A1 (en) * | 2018-03-28 | 2020-11-19 | Blade Therapeutics, Inc. | Method of treating fibrotic disease |
Family Cites Families (23)
| 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 |
| IL130124A0 (en) | 1996-12-11 | 2000-06-01 | Basf Ag | Ketobenzamides as calpain inhibitors |
| US6083944A (en) | 1997-10-07 | 2000-07-04 | Cephalon, Inc. | Quinoline-containing α-ketoamide cysteine and serine protease inhibitors |
| DE19818614A1 (de) | 1998-04-20 | 1999-10-21 | Basf Ag | Neue substituierte Amide, deren Herstellung und Anwendung |
| DE19817459A1 (de) | 1998-04-20 | 1999-10-21 | Basf Ag | Neue heterozyklische substituierte Amide, Herstellung und Anwendung |
| DE59914996D1 (en) | 1998-04-20 | 2009-05-14 | Abbott Gmbh & Co Kg | Heterocyclisch substituierte amide als calpainhemmer |
| DE19817461A1 (de) | 1998-04-20 | 1999-10-21 | Basf Ag | Neue substituierte Benzamide, deren Herstellung und Anwendung |
| KR20010042839A (ko) | 1998-04-20 | 2001-05-25 | 스타르크, 카르크 | 시스테인 프로테아제를 억제하는 효과를 나타내고헤테로시클릭 치환체가 있는 신규 아미드 |
| HUP0102732A3 (en) | 1998-04-20 | 2002-12-28 | Basf Ag | Substituted amids, their use for producing pharmaceutical compositions and pharmaceutical compositions containing them |
| JP4700192B2 (ja) | 1998-05-25 | 2011-06-15 | 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 | 新規の複素環式の置換されたアミド、その製造および使用 |
| 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 |
| NZ577719A (en) | 2006-12-29 | 2012-06-29 | Abbott Gmbh & Co Kg | Pyrazol-1-yl-aryl amides and their analogues and their pharmaceutical uses |
| EP2125113A2 (en) | 2007-02-26 | 2009-12-02 | 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 |
| TWI519530B (zh) * | 2009-02-20 | 2016-02-01 | 艾伯維德國有限及兩合公司 | 羰醯胺化合物及其作為鈣蛋白酶（ｃａｌｐａｉｎ）抑制劑之用途 |
| CN102652418B (zh) * | 2009-12-09 | 2015-11-25 | 马维尔国际贸易有限公司 | 用于无线通信的帧填充 |
| US8430139B2 (en) * | 2009-12-11 | 2013-04-30 | Agco Corporation | Automated refilling connection for a liquid material container of an applicator |
| US9051304B2 (en) | 2009-12-22 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Carboxamide compounds and their use as calpain inhibitors V |
| US8598211B2 (en) * | 2009-12-22 | 2013-12-03 | Abbvie Inc. | Carboxamide compounds and their use as calpain inhibitors IV |
-
2013
- 2013-03-14 CN CN201380017722.1A patent/CN104364247A/zh active Pending
- 2013-03-14 JP JP2015503800A patent/JP2015512427A/ja active Pending
- 2013-03-14 MX MX2014011998A patent/MX2014011998A/es unknown
- 2013-03-14 SG SG11201406345XA patent/SG11201406345XA/en unknown
- 2013-03-14 US US14/390,381 patent/US9150545B2/en not_active Expired - Fee Related
- 2013-03-14 EP EP13709139.3A patent/EP2834230A1/en not_active Withdrawn
- 2013-03-14 RU RU2014144285A patent/RU2014144285A/ru not_active Application Discontinuation
- 2013-03-14 WO PCT/EP2013/055291 patent/WO2013149800A1/en not_active Ceased
- 2013-03-14 CA CA 2867210 patent/CA2867210A1/en not_active Abandoned