JP2012526082A5 - - Google Patents
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- JP2012526082A5 JP2012526082A5 JP2012509039A JP2012509039A JP2012526082A5 JP 2012526082 A5 JP2012526082 A5 JP 2012526082A5 JP 2012509039 A JP2012509039 A JP 2012509039A JP 2012509039 A JP2012509039 A JP 2012509039A JP 2012526082 A5 JP2012526082 A5 JP 2012526082A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- carboxamide
- aryl
- hetaryl
- 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.)
- Granted
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- -1 Carboxamide compounds Chemical class 0.000 claims 62
- 125000001072 heteroaryl group Chemical group 0.000 claims 56
- 125000003118 aryl group Chemical group 0.000 claims 49
- 125000001424 substituent group Chemical group 0.000 claims 43
- 229910052799 carbon Inorganic materials 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 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 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 230000004064 dysfunction Effects 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 238000011282 treatment Methods 0.000 claims 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 230000006378 damage Effects 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 208000014674 injury Diseases 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 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
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- WSTJWENSQYSZMZ-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]-n-[4-(ethylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C(=CC=CC=2Cl)Cl)C1C(=O)NC(C(=O)C(=O)NCC)CC1=CC=CC=C1 WSTJWENSQYSZMZ-UHFFFAOYSA-N 0.000 claims 1
- LSMCQDFEVHRJHU-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-n-[4-(ethylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C(=CC=CC=2F)F)C1C(=O)NC(C(=O)C(=O)NCC)CC1=CC=CC=C1 LSMCQDFEVHRJHU-UHFFFAOYSA-N 0.000 claims 1
- MIZVOFRATSXZHW-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-n-[4-(cyclopropylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound ClC1=CC=CC=C1CN1C(=O)CCC1C(=O)NC(C(=O)C(=O)NC1CC1)CC1=CC=CC=C1 MIZVOFRATSXZHW-UHFFFAOYSA-N 0.000 claims 1
- OQNWFNALLVYVNV-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-n-[4-(ethylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C(=CC=CC=2)Cl)C1C(=O)NC(C(=O)C(=O)NCC)CC1=CC=CC=C1 OQNWFNALLVYVNV-UHFFFAOYSA-N 0.000 claims 1
- HBBYZISRTFASTH-UHFFFAOYSA-N 1-benzyl-n-(4-morpholin-4-yl-3,4-dioxo-1-phenylbutan-2-yl)-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)N1CCOCC1)CC1=CC=CC=C1 HBBYZISRTFASTH-UHFFFAOYSA-N 0.000 claims 1
- GBOMVKGJCSCUHP-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(1,3-thiazol-2-ylmethylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCC=1SC=CN=1)CC1=CC=CC=C1 GBOMVKGJCSCUHP-UHFFFAOYSA-N 0.000 claims 1
- AIIJYZLDZIOHBJ-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(1,3-thiazol-5-ylmethylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCC=1SC=NC=1)CC1=CC=CC=C1 AIIJYZLDZIOHBJ-UHFFFAOYSA-N 0.000 claims 1
- NYPGCRIFFQSPDW-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(2-phenylethylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCCC=1C=CC=CC=1)CC1=CC=CC=C1 NYPGCRIFFQSPDW-UHFFFAOYSA-N 0.000 claims 1
- CJJUCPWHVGWRGP-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(2-pyridin-2-ylethylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCCC=1N=CC=CC=1)CC1=CC=CC=C1 CJJUCPWHVGWRGP-UHFFFAOYSA-N 0.000 claims 1
- UNQYDRYDCQAIAV-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(2-thiophen-3-ylethylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCCC1=CSC=C1)CC1=CC=CC=C1 UNQYDRYDCQAIAV-UHFFFAOYSA-N 0.000 claims 1
- KRASOZPDWRHNQV-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(3-phenylpropylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCCCC=1C=CC=CC=1)CC1=CC=CC=C1 KRASOZPDWRHNQV-UHFFFAOYSA-N 0.000 claims 1
- SVEDZUZEJCFLQV-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(3-pyridin-2-ylpropylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCCCC=1N=CC=CC=1)CC1=CC=CC=C1 SVEDZUZEJCFLQV-UHFFFAOYSA-N 0.000 claims 1
- URPUXEXXHQEYQM-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(propylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCCC)CC1=CC=CC=C1 URPUXEXXHQEYQM-UHFFFAOYSA-N 0.000 claims 1
- VBRYNLHJJUQPDB-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(pyridin-2-ylmethylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCC=1N=CC=CC=1)CC1=CC=CC=C1 VBRYNLHJJUQPDB-UHFFFAOYSA-N 0.000 claims 1
- BIWZDZJPEBSMCY-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(pyridin-4-ylmethylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCC=1C=CN=CC=1)CC1=CC=CC=C1 BIWZDZJPEBSMCY-UHFFFAOYSA-N 0.000 claims 1
- UPPCNQCJVACHNK-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-(thiophen-2-ylmethylamino)butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCC=1SC=CC=1)CC1=CC=CC=C1 UPPCNQCJVACHNK-UHFFFAOYSA-N 0.000 claims 1
- FJHDYCQBVUODRG-UHFFFAOYSA-N 1-benzyl-n-[3,4-dioxo-1-phenyl-4-[[4-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC(=O)C(=O)C(NC(=O)C1N(C(=O)CC1)CC=1C=CC=CC=1)CC1=CC=CC=C1 FJHDYCQBVUODRG-UHFFFAOYSA-N 0.000 claims 1
- HICQIEYSKZBOSG-DDRJZQQSSA-N 1-benzyl-n-[3,4-dioxo-4-[[(2r)-oxolan-2-yl]methylamino]-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NC[C@@H]1OCCC1)CC1=CC=CC=C1 HICQIEYSKZBOSG-DDRJZQQSSA-N 0.000 claims 1
- HICQIEYSKZBOSG-UVKLAMSESA-N 1-benzyl-n-[3,4-dioxo-4-[[(2s)-oxolan-2-yl]methylamino]-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NC[C@H]1OCCC1)CC1=CC=CC=C1 HICQIEYSKZBOSG-UVKLAMSESA-N 0.000 claims 1
- NCWOPWPBIXZIDB-UHFFFAOYSA-N 1-benzyl-n-[4-(1,3-oxazol-2-ylmethylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCC=1OC=CN=1)CC1=CC=CC=C1 NCWOPWPBIXZIDB-UHFFFAOYSA-N 0.000 claims 1
- JKDDPXUFPWJSNT-UHFFFAOYSA-N 1-benzyl-n-[4-(2-benzylhydrazinyl)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NNCC=1C=CC=CC=1)CC1=CC=CC=C1 JKDDPXUFPWJSNT-UHFFFAOYSA-N 0.000 claims 1
- ZEHXNLYWGYPINF-UHFFFAOYSA-N 1-benzyl-n-[4-(2-methylpropylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCC(C)C)CC1=CC=CC=C1 ZEHXNLYWGYPINF-UHFFFAOYSA-N 0.000 claims 1
- DXXMJCZGYYBPTF-UHFFFAOYSA-N 1-benzyl-n-[4-(cyclobutylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NC1CCC1)CC1=CC=CC=C1 DXXMJCZGYYBPTF-UHFFFAOYSA-N 0.000 claims 1
- AZQZXXOXIORVDG-UHFFFAOYSA-N 1-benzyl-n-[4-(cyclohexylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NC1CCCCC1)CC1=CC=CC=C1 AZQZXXOXIORVDG-UHFFFAOYSA-N 0.000 claims 1
- MMLDHJRGTZHNHV-UHFFFAOYSA-N 1-benzyl-n-[4-(cyclopropylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NC1CC1)CC1=CC=CC=C1 MMLDHJRGTZHNHV-UHFFFAOYSA-N 0.000 claims 1
- ATHQZOFAXUBFPV-UHFFFAOYSA-N 1-benzyl-n-[4-(ethylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCC)CC1=CC=CC=C1 ATHQZOFAXUBFPV-UHFFFAOYSA-N 0.000 claims 1
- ZNQBQPHYWUHFDJ-UHFFFAOYSA-N 1-benzyl-n-[4-(furan-2-ylmethylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NCC=1OC=CC=1)CC1=CC=CC=C1 ZNQBQPHYWUHFDJ-UHFFFAOYSA-N 0.000 claims 1
- TZBYOYZAEWCZKP-UHFFFAOYSA-N 1-benzyl-n-[4-(methoxyamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NOC)CC1=CC=CC=C1 TZBYOYZAEWCZKP-UHFFFAOYSA-N 0.000 claims 1
- XFEHUMNNTJCUSO-UHFFFAOYSA-N 1-benzyl-n-[4-(methylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)NC)CC1=CC=CC=C1 XFEHUMNNTJCUSO-UHFFFAOYSA-N 0.000 claims 1
- PVJVVKLMFLGUNI-UHFFFAOYSA-N 1-benzyl-n-[4-[(2-chlorophenyl)methylamino]-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound ClC1=CC=CC=C1CNC(=O)C(=O)C(NC(=O)C1N(C(=O)CC1)CC=1C=CC=CC=1)CC1=CC=CC=C1 PVJVVKLMFLGUNI-UHFFFAOYSA-N 0.000 claims 1
- UIINIJSKKDIMRX-UHFFFAOYSA-N 1-benzyl-n-[4-[(4-fluorophenyl)methylamino]-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C(=O)C(NC(=O)C1N(C(=O)CC1)CC=1C=CC=CC=1)CC1=CC=CC=C1 UIINIJSKKDIMRX-UHFFFAOYSA-N 0.000 claims 1
- MKLXKMGPODVWPL-UHFFFAOYSA-N 1-benzyl-n-[4-[ethyl(methyl)amino]-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC=CC=2)C1C(=O)NC(C(=O)C(=O)N(C)CC)CC1=CC=CC=C1 MKLXKMGPODVWPL-UHFFFAOYSA-N 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
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- 102000007590 Calpain Human genes 0.000 claims 1
- 108010032088 Calpain Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000002177 Cataract Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000004117 Congenital Myasthenic Syndromes Diseases 0.000 claims 1
- 208000003890 Coronary Vasospasm Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 206010018364 Glomerulonephritis 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
- 241000124008 Mammalia Species 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 208000029549 Muscle injury Diseases 0.000 claims 1
- 206010028851 Necrosis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010063897 Renal ischaemia Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 238000002399 angioplasty Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 210000004556 brain Anatomy 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
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 201000011634 coronary artery vasospasm Diseases 0.000 claims 1
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- 231100000318 excitotoxic Toxicity 0.000 claims 1
- 230000003492 excitotoxic effect Effects 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000013467 fragmentation Methods 0.000 claims 1
- 238000006062 fragmentation reaction Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
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- 210000003734 kidney Anatomy 0.000 claims 1
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- 208000002780 macular degeneration Diseases 0.000 claims 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000006667 mitochondrial pathway Effects 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 201000006938 muscular dystrophy Diseases 0.000 claims 1
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- QKEJGTKDYHFOPQ-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-1-(naphthalen-1-ylmethyl)-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C3=CC=CC=C3C=CC=2)C1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 QKEJGTKDYHFOPQ-UHFFFAOYSA-N 0.000 claims 1
- FHWLGJKJGCLEON-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-1-(naphthalen-2-ylmethyl)-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=C3C=CC=CC3=CC=2)C1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 FHWLGJKJGCLEON-UHFFFAOYSA-N 0.000 claims 1
- NGOBYTQBLPWLPL-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-1-[(3,5-difluorophenyl)methyl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=C(F)C=C(F)C=2)C1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 NGOBYTQBLPWLPL-UHFFFAOYSA-N 0.000 claims 1
- NUXJKNJOOMVHOZ-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-1-[(3,5-dimethoxyphenyl)methyl]-5-oxopyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC(CN2C(CCC2C(=O)NC(CC=2C=CC=CC=2)C(=O)C(N)=O)=O)=C1 NUXJKNJOOMVHOZ-UHFFFAOYSA-N 0.000 claims 1
- WDFWVAHHFZEAHP-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-1-[(3-chlorophenyl)methyl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=C(Cl)C=CC=2)C1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 WDFWVAHHFZEAHP-UHFFFAOYSA-N 0.000 claims 1
- WVHILXVQDUOWQO-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-1-[(3-cyanophenyl)methyl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=C(C=CC=2)C#N)C1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 WVHILXVQDUOWQO-UHFFFAOYSA-N 0.000 claims 1
- MWOITWISKVFINN-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-1-[(3-fluorophenyl)methyl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=C(F)C=CC=2)C1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 MWOITWISKVFINN-UHFFFAOYSA-N 0.000 claims 1
- DSRDBNLUPKIIPI-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-1-[(3-methoxyphenyl)methyl]-5-oxopyrrolidine-2-carboxamide Chemical compound COC1=CC=CC(CN2C(CCC2C(=O)NC(CC=2C=CC=CC=2)C(=O)C(N)=O)=O)=C1 DSRDBNLUPKIIPI-UHFFFAOYSA-N 0.000 claims 1
- MGBXEZSMVFCAQQ-UHFFFAOYSA-N n-(4-amino-3,4-dioxo-1-phenylbutan-2-yl)-1-[(4-fluorophenyl)methyl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)N(CC=2C=CC(F)=CC=2)C1C(=O)NC(C(=O)C(=O)N)CC1=CC=CC=C1 MGBXEZSMVFCAQQ-UHFFFAOYSA-N 0.000 claims 1
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- GWWFHNFABUBUDH-UHFFFAOYSA-N n-[4-(benzylamino)-3,4-dioxo-1-phenylbutan-2-yl]-1-[[2-methoxy-6-(trifluoromethyl)phenyl]methyl]-5-oxopyrrolidine-2-carboxamide Chemical compound COC1=CC=CC(C(F)(F)F)=C1CN1C(=O)CCC1C(=O)NC(C(=O)C(=O)NCC=1C=CC=CC=1)CC1=CC=CC=C1 GWWFHNFABUBUDH-UHFFFAOYSA-N 0.000 claims 1
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| JP5959075B2 (ja) * | 2011-05-31 | 2016-08-02 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | ネプリライシン阻害剤 |
| ITMI20121668A1 (it) * | 2012-10-05 | 2014-04-06 | Dipharma Francis Srl | Sintesi di un intermedio di un composto antivirale |
| CN104458709A (zh) * | 2013-09-12 | 2015-03-25 | 中国药科大学 | 一种筛选钙激活中性蛋白酶-1抑制剂高通量筛选方法 |
| DE102014110782A1 (de) * | 2014-07-30 | 2016-02-04 | Eberhard Karls Universität Tübingen Medizinische Fakultät | Herstellung von Pyrrolidinderivaten |
| WO2017156071A1 (en) | 2016-03-09 | 2017-09-14 | Blade Therapeutics, Inc. | Cyclic keto-amide compounds as calpain modulators and methods of production and use thereof |
| EP3481835A4 (en) | 2016-07-05 | 2020-02-26 | Blade Therapeutics, Inc. | CALPAIN MODULATORS AND THERAPEUTIC USE THEREOF |
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| BR112019006110A2 (pt) | 2016-09-28 | 2019-09-10 | Blade Therapeutics Inc | moduladores de calpaína e usos terapêuticos dos mesmos |
| EP4488264A4 (en) * | 2022-03-01 | 2026-03-04 | Westvac Biopharma Co Ltd | CETO AMIDE DERIVATIVES AND THEIR PHARMACEUTICAL USE |
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- 2010-05-06 WO PCT/EP2010/056166 patent/WO2010128102A1/en not_active Ceased
- 2010-05-07 AR ARP100101566 patent/AR076755A1/es unknown
- 2010-11-05 US US12/940,339 patent/US8283363B2/en not_active Expired - Fee Related
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2011
- 2011-10-23 IL IL215835A patent/IL215835A/en not_active IP Right Cessation
- 2011-11-04 CL CL2011002766A patent/CL2011002766A1/es unknown
- 2011-11-07 DO DO2011000338A patent/DOP2011000338A/es unknown
- 2011-11-21 CR CR20110630A patent/CR20110630A/es unknown
- 2011-12-05 CO CO11167060A patent/CO6470862A2/es active IP Right Grant
- 2011-12-05 EC ECSP11011503 patent/ECSP11011503A/es unknown
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2012
- 2012-07-26 DO DO2012000210A patent/DOP2012000210A/es unknown
- 2012-09-12 US US13/610,975 patent/US9018206B2/en not_active Expired - Fee Related
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2013
- 2013-11-15 PH PH12013502359A patent/PH12013502359A1/en unknown
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2014
- 2014-12-15 US US14/570,996 patent/US9527811B2/en not_active Expired - Fee Related
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