HRP990246A2 - Succinoylamino benzodiazepines as inhibitors of a beta protein production - Google Patents
Succinoylamino benzodiazepines as inhibitors of a beta protein production Download PDFInfo
- Publication number
- HRP990246A2 HRP990246A2 HR990246A HRP990246A HRP990246A2 HR P990246 A2 HRP990246 A2 HR P990246A2 HR 990246 A HR990246 A HR 990246A HR P990246 A HRP990246 A HR P990246A HR P990246 A2 HRP990246 A2 HR P990246A2
- Authority
- HR
- Croatia
- Prior art keywords
- butanediamide
- oxo
- phenyl
- benzyl
- azepin
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 36
- 229940049706 benzodiazepine Drugs 0.000 title description 9
- 239000003112 inhibitor Substances 0.000 title description 5
- 230000006269 (delayed) early viral mRNA transcription Effects 0.000 title 1
- 150000001557 benzodiazepines Chemical class 0.000 title 1
- -1 phenoxy, benzyloxy Chemical group 0.000 claims description 252
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 244
- 229910052731 fluorine Inorganic materials 0.000 claims description 227
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 208
- 229910052801 chlorine Inorganic materials 0.000 claims description 207
- 150000001875 compounds Chemical class 0.000 claims description 187
- 125000000623 heterocyclic group Chemical group 0.000 claims description 171
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 163
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 145
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 138
- 229910052794 bromium Inorganic materials 0.000 claims description 136
- 229910052740 iodine Inorganic materials 0.000 claims description 135
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 123
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 109
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 105
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 100
- 238000000034 method Methods 0.000 claims description 98
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 92
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 92
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 85
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 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 description 68
- 125000001188 haloalkyl group Chemical group 0.000 claims description 61
- 150000003951 lactams Chemical class 0.000 claims description 61
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 60
- 229910052799 carbon Inorganic materials 0.000 claims description 60
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 58
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 56
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 54
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 54
- 229910052760 oxygen Inorganic materials 0.000 claims description 44
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 33
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 29
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000000651 prodrug Substances 0.000 claims description 28
- 229940002612 prodrug Drugs 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 208000024827 Alzheimer disease Diseases 0.000 claims description 26
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 19
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 17
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- 125000005605 benzo group Chemical group 0.000 claims description 16
- 238000012360 testing method Methods 0.000 claims description 16
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 208000012902 Nervous system disease Diseases 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 208000025966 Neurological disease Diseases 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000002971 oxazolyl group Chemical group 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 238000001114 immunoprecipitation Methods 0.000 claims description 7
- 239000003475 metalloproteinase inhibitor Substances 0.000 claims description 7
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical group C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 6
- 101000998548 Yersinia ruckeri Alkaline proteinase inhibitor Proteins 0.000 claims description 6
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 4
- ZQDLBYQRPAVQKO-RCSZBHJWSA-N 3-(2-methylpropyl)-n'-[(3s)-2-oxo-1-[(3-phenoxyphenyl)methyl]azepan-3-yl]-2-propylbutanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCC)C(N)=O)CCCCN1CC1=CC=CC(OC=2C=CC=CC=2)=C1 ZQDLBYQRPAVQKO-RCSZBHJWSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 4
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 4
- WKOVQMBIGQHIFN-RCSZBHJWSA-N 2-(2-methylpropyl)-n'-[(3s)-2-oxo-1-[(3-phenoxyphenyl)methyl]azepan-3-yl]-3-propylbutanediamide Chemical compound O=C1[C@@H](NC(=O)C(C(CC(C)C)C(N)=O)CCC)CCCCN1CC1=CC=CC(OC=2C=CC=CC=2)=C1 WKOVQMBIGQHIFN-RCSZBHJWSA-N 0.000 claims description 3
- TYIKDNXILKREJN-FHZUCYEKSA-N 2-(2-methylpropyl)-n-[(3s)-2-oxo-1-[(3-phenoxyphenyl)methyl]azepan-3-yl]butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(N)=O)CC(C)C)CCCCN1CC1=CC=CC(OC=2C=CC=CC=2)=C1 TYIKDNXILKREJN-FHZUCYEKSA-N 0.000 claims description 3
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 3
- WOHDRVIYZQAFNT-NXCFDTQHSA-N (2s,3r)-3-(2-methylpropyl)-n'-[(3s)-2-oxo-1-[[5-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methyl]azepan-3-yl]-2-propylbutanediamide Chemical compound O=C1[C@@H](NC(=O)[C@H](CC(C)C)[C@H](CCC)C(N)=O)CCCCN1CC1=CN=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 WOHDRVIYZQAFNT-NXCFDTQHSA-N 0.000 claims description 2
- NPPDLXRHPIHQTR-VJGNERBWSA-N (2s,3r)-n'-[(3s)-1-[[5-(4-methoxyphenyl)pyridin-3-yl]methyl]-2-oxoazepan-3-yl]-3-(2-methylpropyl)-2-propylbutanediamide Chemical compound O=C1[C@@H](NC(=O)[C@H](CC(C)C)[C@H](CCC)C(N)=O)CCCCN1CC1=CN=CC(C=2C=CC(OC)=CC=2)=C1 NPPDLXRHPIHQTR-VJGNERBWSA-N 0.000 claims description 2
- FOMISRCNJZNGTG-ONHAVXAHSA-N 2-(2-methylpropyl)-n-[(3s)-2-oxo-1-[(3-phenoxyphenyl)methyl]azepan-3-yl]-n'-(3-phenylprop-2-enyl)-3-propylbutanediamide Chemical compound C([C@@H](C1=O)NC(=O)C(CC(C)C)C(CCC)C(=O)NCC=CC=2C=CC=CC=2)CCCN1CC(C=1)=CC=CC=1OC1=CC=CC=C1 FOMISRCNJZNGTG-ONHAVXAHSA-N 0.000 claims description 2
- GTUTWYAKNHAAJZ-PDZHLSQESA-N 2-butyl-3-(2-methylpropyl)-n'-[(3s)-1-[(3-naphthalen-2-ylphenyl)methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1=CC=CC(C=2C=C3C=CC=CC3=CC=2)=C1 GTUTWYAKNHAAJZ-PDZHLSQESA-N 0.000 claims description 2
- NXQOMXPDZQZOFF-VNXZQDSDSA-N 2-butyl-3-(2-methylpropyl)-n'-[(3s)-2-oxo-1-(2-phenylethyl)azepan-3-yl]butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CCC1=CC=CC=C1 NXQOMXPDZQZOFF-VNXZQDSDSA-N 0.000 claims description 2
- AGHFNSOZVBICLL-LADMEODRSA-N 2-butyl-3-(2-methylpropyl)-n'-[(3s)-2-oxo-1-[(3-phenoxyphenyl)methyl]azepan-3-yl]butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1=CC=CC(OC=2C=CC=CC=2)=C1 AGHFNSOZVBICLL-LADMEODRSA-N 0.000 claims description 2
- ZVPRXYMUVSCSGP-LADMEODRSA-N 2-butyl-3-(2-methylpropyl)-n'-[(3s)-2-oxo-1-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]azepan-3-yl]butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 ZVPRXYMUVSCSGP-LADMEODRSA-N 0.000 claims description 2
- GAFDXRLHTNUGFQ-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[1-[(3-naphthalen-2-ylphenyl)methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound C12=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)N=C1C1=CC=CC=C1 GAFDXRLHTNUGFQ-UHFFFAOYSA-N 0.000 claims description 2
- LKIOGYJIRMYYHA-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[2-oxo-1-[(3-phenoxyphenyl)methyl]-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound C12=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)N=C1C1=CC=CC=C1 LKIOGYJIRMYYHA-UHFFFAOYSA-N 0.000 claims description 2
- JAPNXBGCOXIDQL-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[2-oxo-5-phenyl-1-(2-phenylethyl)-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound C12=CC=CC=C2N(CCC=2C=CC=CC=2)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)N=C1C1=CC=CC=C1 JAPNXBGCOXIDQL-UHFFFAOYSA-N 0.000 claims description 2
- DEIUHFYFANTAIQ-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[2-oxo-5-phenyl-1-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound C12=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)N=C1C1=CC=CC=C1 DEIUHFYFANTAIQ-UHFFFAOYSA-N 0.000 claims description 2
- MZGWJMRHOQOLTM-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[4-oxo-1-phenyl-5-(2-phenylethyl)-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C12=CC=CC=C2N(CCC=2C=CC=CC=2)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CN1C1=CC=CC=C1 MZGWJMRHOQOLTM-UHFFFAOYSA-N 0.000 claims description 2
- JNNKGXBKTSFZEA-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[4-oxo-1-phenyl-5-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C12=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CN1C1=CC=CC=C1 JNNKGXBKTSFZEA-UHFFFAOYSA-N 0.000 claims description 2
- PLKCURMAARKLCU-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[4-oxo-5-[(3-phenoxyphenyl)methyl]-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C12=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CN1C1=CC=CC=C1 PLKCURMAARKLCU-UHFFFAOYSA-N 0.000 claims description 2
- AWQUUUHVQUXWSG-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[5-[(3-naphthalen-2-ylphenyl)methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C12=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CN1C1=CC=CC=C1 AWQUUUHVQUXWSG-UHFFFAOYSA-N 0.000 claims description 2
- SYISGWHRMKOJAQ-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[5-[(3-naphthalen-2-ylphenyl)methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound O=C1C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)C2=CC=CC=C2C2=CC=CC=C2N1CC1=CC=CC(C=2C=C3C=CC=CC3=CC=2)=C1 SYISGWHRMKOJAQ-UHFFFAOYSA-N 0.000 claims description 2
- DNRIBMVNRFZYTQ-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[6-oxo-5-(2-phenylethyl)-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound O=C1C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)C2=CC=CC=C2C2=CC=CC=C2N1CCC1=CC=CC=C1 DNRIBMVNRFZYTQ-UHFFFAOYSA-N 0.000 claims description 2
- UCVQESXCBQCSIS-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[6-oxo-5-[(3-phenoxyphenyl)methyl]-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound O=C1C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)C2=CC=CC=C2C2=CC=CC=C2N1CC(C=1)=CC=CC=1OC1=CC=CC=C1 UCVQESXCBQCSIS-UHFFFAOYSA-N 0.000 claims description 2
- IMMUOILNTLRIHE-UHFFFAOYSA-N 2-butyl-3-(2-methylpropyl)-n'-[6-oxo-5-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound O=C1C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)C2=CC=CC=C2C2=CC=CC=C2N1CC(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 IMMUOILNTLRIHE-UHFFFAOYSA-N 0.000 claims description 2
- PDIKDHFTCYMOCI-PJUZOBRJSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[(3s)-1-[(3-naphthalen-2-ylphenyl)methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCC1 PDIKDHFTCYMOCI-PJUZOBRJSA-N 0.000 claims description 2
- LFWMVEZBALBRKP-DMVZSUBZSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[(3s)-1-[[3-(2,4-dichlorophenyl)phenyl]methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCC1 LFWMVEZBALBRKP-DMVZSUBZSA-N 0.000 claims description 2
- UMJQLNXLASXOJC-DSNFFHCTSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[(3s)-1-[[3-(4-methylphenyl)phenyl]methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCC1 UMJQLNXLASXOJC-DSNFFHCTSA-N 0.000 claims description 2
- CTZUJIHOOBTPOY-PPUMFKDSSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[(3s)-2-oxo-1-[(3-phenoxyphenyl)methyl]azepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCC1 CTZUJIHOOBTPOY-PPUMFKDSSA-N 0.000 claims description 2
- RVFYQMQXSSEKRK-PPUMFKDSSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[(3s)-2-oxo-1-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]azepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCC1 RVFYQMQXSSEKRK-PPUMFKDSSA-N 0.000 claims description 2
- XSGSWVJRIOXTQX-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[1-[(3-naphthalen-2-ylphenyl)methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 XSGSWVJRIOXTQX-UHFFFAOYSA-N 0.000 claims description 2
- KQJGKUWRAANYEX-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[1-[[3-(2,4-dichlorophenyl)phenyl]methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 KQJGKUWRAANYEX-UHFFFAOYSA-N 0.000 claims description 2
- SRWWBWZMYFZCNS-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[1-[[3-(4-methoxyphenyl)phenyl]methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 SRWWBWZMYFZCNS-UHFFFAOYSA-N 0.000 claims description 2
- HSXPOZNAXRXMTL-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[1-[[3-(4-methylphenyl)phenyl]methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 HSXPOZNAXRXMTL-UHFFFAOYSA-N 0.000 claims description 2
- KUEBFZCVWBWYLM-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[2-oxo-1-[(3-phenoxyphenyl)methyl]-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 KUEBFZCVWBWYLM-UHFFFAOYSA-N 0.000 claims description 2
- FDGGTRCOUMMBQY-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[2-oxo-5-phenyl-1-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 FDGGTRCOUMMBQY-UHFFFAOYSA-N 0.000 claims description 2
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- QBAJESMOJCSZLA-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[4-oxo-5-[(3-phenoxyphenyl)methyl]-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 QBAJESMOJCSZLA-UHFFFAOYSA-N 0.000 claims description 2
- YLIGJCYYTYZASR-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[5-[(3-naphthalen-2-ylphenyl)methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 YLIGJCYYTYZASR-UHFFFAOYSA-N 0.000 claims description 2
- OVUNVQGZMNUEJS-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[5-[(3-naphthalen-2-ylphenyl)methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 OVUNVQGZMNUEJS-UHFFFAOYSA-N 0.000 claims description 2
- RPSTVQMENBDQAX-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[5-[[3-(2,4-dichlorophenyl)phenyl]methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 RPSTVQMENBDQAX-UHFFFAOYSA-N 0.000 claims description 2
- AFRKEQPPZNCNPY-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[5-[[3-(2,4-dichlorophenyl)phenyl]methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 AFRKEQPPZNCNPY-UHFFFAOYSA-N 0.000 claims description 2
- GPQGOODWGVYUOL-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[5-[[3-(4-methoxyphenyl)phenyl]methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 GPQGOODWGVYUOL-UHFFFAOYSA-N 0.000 claims description 2
- NCQAAQCIDIFRIE-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[5-[[3-(4-methoxyphenyl)phenyl]methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 NCQAAQCIDIFRIE-UHFFFAOYSA-N 0.000 claims description 2
- VTDLXCMHVIQFKJ-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[5-[[3-(4-methylphenyl)phenyl]methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 VTDLXCMHVIQFKJ-UHFFFAOYSA-N 0.000 claims description 2
- AMQLYPJSELWZCJ-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[5-[[3-(4-methylphenyl)phenyl]methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 AMQLYPJSELWZCJ-UHFFFAOYSA-N 0.000 claims description 2
- FALALMCOKUBWNM-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[6-oxo-5-[(3-phenoxyphenyl)methyl]-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 FALALMCOKUBWNM-UHFFFAOYSA-N 0.000 claims description 2
- RLGIZKMATOEFCF-UHFFFAOYSA-N 2-butyl-3-(cyclobutylmethyl)-n'-[6-oxo-5-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCC1 RLGIZKMATOEFCF-UHFFFAOYSA-N 0.000 claims description 2
- UZSCJBPGHFTFHT-PZIMRNDGSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[(3s)-1-[(3-naphthalen-2-ylphenyl)methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCCC1 UZSCJBPGHFTFHT-PZIMRNDGSA-N 0.000 claims description 2
- YTYXFVVNBZWIDZ-UEYYRQBOSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[(3s)-1-[[3-(2,4-dichlorophenyl)phenyl]methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCCC1 YTYXFVVNBZWIDZ-UEYYRQBOSA-N 0.000 claims description 2
- CEEHXVTWVANKAA-VCBVRPFLSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[(3s)-1-[[3-(4-methoxyphenyl)phenyl]methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCCC1 CEEHXVTWVANKAA-VCBVRPFLSA-N 0.000 claims description 2
- KBGBQRRBJVXLCB-VCBVRPFLSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[(3s)-1-[[3-(4-methylphenyl)phenyl]methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCCC1 KBGBQRRBJVXLCB-VCBVRPFLSA-N 0.000 claims description 2
- HHRLXVJGLORWHX-DSNFFHCTSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[(3s)-2-oxo-1-[(3-phenoxyphenyl)methyl]azepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCCC1 HHRLXVJGLORWHX-DSNFFHCTSA-N 0.000 claims description 2
- YRNFCALLWMZHCT-DSNFFHCTSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[(3s)-2-oxo-1-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]azepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCCC1 YRNFCALLWMZHCT-DSNFFHCTSA-N 0.000 claims description 2
- ZVVWSBPHQVLQTA-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[1-[[3-(2,4-dichlorophenyl)phenyl]methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 ZVVWSBPHQVLQTA-UHFFFAOYSA-N 0.000 claims description 2
- GCAZKDSPQRIJFJ-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[1-[[3-(4-methoxyphenyl)phenyl]methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 GCAZKDSPQRIJFJ-UHFFFAOYSA-N 0.000 claims description 2
- BZSREFJMNUQVHX-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[1-[[3-(4-methylphenyl)phenyl]methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 BZSREFJMNUQVHX-UHFFFAOYSA-N 0.000 claims description 2
- CHOKMQARSYARNA-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[2-oxo-1-[(3-phenoxyphenyl)methyl]-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 CHOKMQARSYARNA-UHFFFAOYSA-N 0.000 claims description 2
- ZSMQWNBULGQYIT-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[2-oxo-5-phenyl-1-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 ZSMQWNBULGQYIT-UHFFFAOYSA-N 0.000 claims description 2
- CEDJVLWEWHWSRQ-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[4-oxo-1-phenyl-5-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 CEDJVLWEWHWSRQ-UHFFFAOYSA-N 0.000 claims description 2
- BRWFYQGSZIPKAR-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[4-oxo-5-[(3-phenoxyphenyl)methyl]-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 BRWFYQGSZIPKAR-UHFFFAOYSA-N 0.000 claims description 2
- HJVUXHMPNNEUMW-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[5-[(3-naphthalen-2-ylphenyl)methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 HJVUXHMPNNEUMW-UHFFFAOYSA-N 0.000 claims description 2
- IPWWZPXKZPQNPK-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[5-[(3-naphthalen-2-ylphenyl)methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 IPWWZPXKZPQNPK-UHFFFAOYSA-N 0.000 claims description 2
- NESQSCGQZSELJH-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[5-[[3-(2,4-dichlorophenyl)phenyl]methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 NESQSCGQZSELJH-UHFFFAOYSA-N 0.000 claims description 2
- VVQMTHNFOPMZMD-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[5-[[3-(2,4-dichlorophenyl)phenyl]methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 VVQMTHNFOPMZMD-UHFFFAOYSA-N 0.000 claims description 2
- SOFHPAARSPCLKG-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[5-[[3-(4-methoxyphenyl)phenyl]methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 SOFHPAARSPCLKG-UHFFFAOYSA-N 0.000 claims description 2
- ZXAQQPFKYVVFHN-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[5-[[3-(4-methoxyphenyl)phenyl]methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 ZXAQQPFKYVVFHN-UHFFFAOYSA-N 0.000 claims description 2
- HXWLOIUNMJXGJP-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[5-[[3-(4-methylphenyl)phenyl]methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 HXWLOIUNMJXGJP-UHFFFAOYSA-N 0.000 claims description 2
- OJJPEQJSLKEBMY-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[5-[[3-(4-methylphenyl)phenyl]methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 OJJPEQJSLKEBMY-UHFFFAOYSA-N 0.000 claims description 2
- KNBIMTBWICOKLW-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[6-oxo-5-[(3-phenoxyphenyl)methyl]-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 KNBIMTBWICOKLW-UHFFFAOYSA-N 0.000 claims description 2
- OTFLUWASUZJHTK-UHFFFAOYSA-N 2-butyl-3-(cyclopentylmethyl)-n'-[6-oxo-5-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CCCC1 OTFLUWASUZJHTK-UHFFFAOYSA-N 0.000 claims description 2
- BYJUXNMJEZXZJY-PDZHLSQESA-N 2-butyl-3-(cyclopropylmethyl)-n'-[(3s)-1-[(3-naphthalen-2-ylphenyl)methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CC1 BYJUXNMJEZXZJY-PDZHLSQESA-N 0.000 claims description 2
- SJDRDNZZFSRDAB-ZRZZZMTFSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[(3s)-1-[[3-(2,4-dichlorophenyl)phenyl]methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CC1 SJDRDNZZFSRDAB-ZRZZZMTFSA-N 0.000 claims description 2
- WRPXLXXDWJSLQC-PPUMFKDSSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[(3s)-1-[[3-(4-methoxyphenyl)phenyl]methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CC1 WRPXLXXDWJSLQC-PPUMFKDSSA-N 0.000 claims description 2
- VSRKFSLCLZGCIE-PPUMFKDSSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[(3s)-1-[[3-(4-methylphenyl)phenyl]methyl]-2-oxoazepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CC1 VSRKFSLCLZGCIE-PPUMFKDSSA-N 0.000 claims description 2
- WVOVICZOBDCHCW-LADMEODRSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[(3s)-2-oxo-1-[(3-phenoxyphenyl)methyl]azepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CC1 WVOVICZOBDCHCW-LADMEODRSA-N 0.000 claims description 2
- PIQZLKFXLPKGBQ-LADMEODRSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[(3s)-2-oxo-1-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]azepan-3-yl]butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CC1 PIQZLKFXLPKGBQ-LADMEODRSA-N 0.000 claims description 2
- VVRUDIKOFWLGKE-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[1-[(3-naphthalen-2-ylphenyl)methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 VVRUDIKOFWLGKE-UHFFFAOYSA-N 0.000 claims description 2
- SMNJBKFESMKMNK-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[1-[[3-(2,4-dichlorophenyl)phenyl]methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 SMNJBKFESMKMNK-UHFFFAOYSA-N 0.000 claims description 2
- BQJRFXDZZBFLET-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[1-[[3-(4-methoxyphenyl)phenyl]methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 BQJRFXDZZBFLET-UHFFFAOYSA-N 0.000 claims description 2
- TVTOHKVMQFFEAC-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[1-[[3-(4-methylphenyl)phenyl]methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 TVTOHKVMQFFEAC-UHFFFAOYSA-N 0.000 claims description 2
- XNHHRSUPNUMGMM-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[2-oxo-1-[(3-phenoxyphenyl)methyl]-5-phenyl-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 XNHHRSUPNUMGMM-UHFFFAOYSA-N 0.000 claims description 2
- QVLAKDLUSTXMNU-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[2-oxo-5-phenyl-1-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-3h-1,4-benzodiazepin-3-yl]butanediamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 QVLAKDLUSTXMNU-UHFFFAOYSA-N 0.000 claims description 2
- DPMCSHZAOOUDDI-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[4-oxo-1-phenyl-5-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 DPMCSHZAOOUDDI-UHFFFAOYSA-N 0.000 claims description 2
- CVKUQIQEYKULCY-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[4-oxo-5-[(3-phenoxyphenyl)methyl]-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 CVKUQIQEYKULCY-UHFFFAOYSA-N 0.000 claims description 2
- BDOYFSRMMWBSOM-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[5-[(3-naphthalen-2-ylphenyl)methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 BDOYFSRMMWBSOM-UHFFFAOYSA-N 0.000 claims description 2
- PNCLOSAEGBYVMA-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[5-[(3-naphthalen-2-ylphenyl)methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=C3C=CC=CC3=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 PNCLOSAEGBYVMA-UHFFFAOYSA-N 0.000 claims description 2
- ORXKKXAEOJXCIK-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[5-[[3-(2,4-dichlorophenyl)phenyl]methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 ORXKKXAEOJXCIK-UHFFFAOYSA-N 0.000 claims description 2
- LEQKYDIGMMGNBP-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[5-[[3-(2,4-dichlorophenyl)phenyl]methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C(=CC(Cl)=CC=2)Cl)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 LEQKYDIGMMGNBP-UHFFFAOYSA-N 0.000 claims description 2
- OUVBYIAYRYLXEE-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[5-[[3-(4-methoxyphenyl)phenyl]methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 OUVBYIAYRYLXEE-UHFFFAOYSA-N 0.000 claims description 2
- HLVMBIISRJVGSJ-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[5-[[3-(4-methoxyphenyl)phenyl]methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(OC)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 HLVMBIISRJVGSJ-UHFFFAOYSA-N 0.000 claims description 2
- KFYAFFBONWPJKR-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[5-[[3-(4-methylphenyl)phenyl]methyl]-4-oxo-1-phenyl-2,3-dihydro-1,5-benzodiazepin-3-yl]butanediamide Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 KFYAFFBONWPJKR-UHFFFAOYSA-N 0.000 claims description 2
- PLAXRHXCWILAHI-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[5-[[3-(4-methylphenyl)phenyl]methyl]-6-oxo-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(C)=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 PLAXRHXCWILAHI-UHFFFAOYSA-N 0.000 claims description 2
- WPOTVUOFRPZJJK-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[6-oxo-5-[(3-phenoxyphenyl)methyl]-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 WPOTVUOFRPZJJK-UHFFFAOYSA-N 0.000 claims description 2
- QADQEUKQUBVDQR-UHFFFAOYSA-N 2-butyl-3-(cyclopropylmethyl)-n'-[6-oxo-5-[[3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-7h-benzo[d][1]benzazepin-7-yl]butanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)C1NC(=O)C(C(CCCC)C(N)=O)CC1CC1 QADQEUKQUBVDQR-UHFFFAOYSA-N 0.000 claims description 2
- UAMMIPBSZHJOLN-CBNMVNINSA-N 2-butyl-n'-[(3s)-1-(2-cyclobutylethyl)-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CCC1CCC1 UAMMIPBSZHJOLN-CBNMVNINSA-N 0.000 claims description 2
- RWXWOSMZVFUDHX-VNXZQDSDSA-N 2-butyl-n'-[(3s)-1-(2-cyclohexylethyl)-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CCC1CCCCC1 RWXWOSMZVFUDHX-VNXZQDSDSA-N 0.000 claims description 2
- IKCDZTSNNTVKPR-HRTMPFAESA-N 2-butyl-n'-[(3s)-1-(2-cyclopentylethyl)-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CCC1CCCC1 IKCDZTSNNTVKPR-HRTMPFAESA-N 0.000 claims description 2
- CHVSIBROCBPLOR-MHJFOBGBSA-N 2-butyl-n'-[(3s)-1-(2-cyclopropylethyl)-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CCC1CC1 CHVSIBROCBPLOR-MHJFOBGBSA-N 0.000 claims description 2
- VJRQKUNLXDCNRS-MHJFOBGBSA-N 2-butyl-n'-[(3s)-1-(cyclobutylmethyl)-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1CCC1 VJRQKUNLXDCNRS-MHJFOBGBSA-N 0.000 claims description 2
- YYTAMSBQWVJYIG-HRTMPFAESA-N 2-butyl-n'-[(3s)-1-(cyclohexylmethyl)-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1CCCCC1 YYTAMSBQWVJYIG-HRTMPFAESA-N 0.000 claims description 2
- IXBRRGYLKDBTCR-CBNMVNINSA-N 2-butyl-n'-[(3s)-1-(cyclopentylmethyl)-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1CCCC1 IXBRRGYLKDBTCR-CBNMVNINSA-N 0.000 claims description 2
- AKPJCLOMWPCDCI-ACBHZAAOSA-N 2-butyl-n'-[(3s)-1-(cyclopropylmethyl)-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1CC1 AKPJCLOMWPCDCI-ACBHZAAOSA-N 0.000 claims description 2
- QFGBLDDFCSBKNJ-HRTMPFAESA-N 2-butyl-n'-[(3s)-1-[(4-fluorophenyl)methyl]-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1=CC=C(F)C=C1 QFGBLDDFCSBKNJ-HRTMPFAESA-N 0.000 claims description 2
- LTFKQWMYFBXAEP-ZRZZZMTFSA-N 2-butyl-n'-[(3s)-1-[[3-(2,4-dichlorophenyl)phenyl]methyl]-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1=CC=CC(C=2C(=CC(Cl)=CC=2)Cl)=C1 LTFKQWMYFBXAEP-ZRZZZMTFSA-N 0.000 claims description 2
- MDPMGHZTMRKZKI-KBMIILLGSA-N 2-butyl-n'-[(3s)-1-[[3-(3-chloro-4-fluorophenyl)phenyl]methyl]-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1=CC=CC(C=2C=C(Cl)C(F)=CC=2)=C1 MDPMGHZTMRKZKI-KBMIILLGSA-N 0.000 claims description 2
- JZVHTIUDIDIXQD-XSLSENLXSA-N 2-butyl-n'-[(3s)-1-[[3-(3-chloro-4-fluorophenyl)phenyl]methyl]-2-oxoazepan-3-yl]-3-(cyclobutylmethyl)butanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=C(Cl)C(F)=CC=2)CCCC1)=O)C(=O)C(C(CCCC)C(N)=O)CC1CCC1 JZVHTIUDIDIXQD-XSLSENLXSA-N 0.000 claims description 2
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- QVYKPHMYGAYJMU-PPUMFKDSSA-N 2-butyl-n'-[(3s)-1-[[3-(4-methylphenyl)phenyl]methyl]-2-oxoazepan-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCCC)C(N)=O)CCCCN1CC1=CC=CC(C=2C=CC(C)=CC=2)=C1 QVYKPHMYGAYJMU-PPUMFKDSSA-N 0.000 claims description 2
- CVKYVZHNONJXKQ-UHFFFAOYSA-N 2-butyl-n'-[1-(2-cyclobutylethyl)-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound C12=CC=CC=C2N(CCC2CCC2)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)N=C1C1=CC=CC=C1 CVKYVZHNONJXKQ-UHFFFAOYSA-N 0.000 claims description 2
- WFLAYEILNLGCJV-UHFFFAOYSA-N 2-butyl-n'-[1-(2-cyclohexylethyl)-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound C12=CC=CC=C2N(CCC2CCCCC2)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)N=C1C1=CC=CC=C1 WFLAYEILNLGCJV-UHFFFAOYSA-N 0.000 claims description 2
- VRDXYGKKXQRMSY-UHFFFAOYSA-N 2-butyl-n'-[1-(2-cyclopentylethyl)-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound C12=CC=CC=C2N(CCC2CCCC2)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)N=C1C1=CC=CC=C1 VRDXYGKKXQRMSY-UHFFFAOYSA-N 0.000 claims description 2
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- SSCMGYJHJNEMFW-UHFFFAOYSA-N 2-butyl-n'-[1-[(4-fluorophenyl)methyl]-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]-3-(2-methylpropyl)butanediamide Chemical compound C12=CC=CC=C2N(CC=2C=CC(F)=CC=2)C(=O)C(NC(=O)C(CC(C)C)C(CCCC)C(N)=O)N=C1C1=CC=CC=C1 SSCMGYJHJNEMFW-UHFFFAOYSA-N 0.000 claims description 2
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- ZLTSSJNNNGSVEG-UHFFFAOYSA-N 3-(cyclopentylmethyl)-n'-[6-oxo-5-[(3-phenoxyphenyl)methyl]-7h-benzo[d][1]benzazepin-7-yl]-2-propylbutanediamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2N(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)C(=O)C1NC(=O)C(C(CCC)C(N)=O)CC1CCCC1 ZLTSSJNNNGSVEG-UHFFFAOYSA-N 0.000 claims description 2
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- GCJHRGSBHDJDMS-CXTIUDGFSA-N n'-[(3s)-1-[[3-(3-chloro-4-fluorophenyl)phenyl]methyl]-2-oxoazepan-3-yl]-3-(2-methylpropyl)-2-propylbutanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCC)C(N)=O)CCCCN1CC1=CC=CC(C=2C=C(Cl)C(F)=CC=2)=C1 GCJHRGSBHDJDMS-CXTIUDGFSA-N 0.000 claims description 2
- RVJURKMHVXNMKQ-KBMIILLGSA-N n'-[(3s)-1-[[3-(3-chloro-4-fluorophenyl)phenyl]methyl]-2-oxoazepan-3-yl]-3-(cyclobutylmethyl)-2-propylbutanediamide Chemical compound N([C@@H]1C(N(CC=2C=C(C=CC=2)C=2C=C(Cl)C(F)=CC=2)CCCC1)=O)C(=O)C(C(CCC)C(N)=O)CC1CCC1 RVJURKMHVXNMKQ-KBMIILLGSA-N 0.000 claims description 2
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- DXAMIGRAGGVLFS-RCSZBHJWSA-N n'-[(3s)-1-[[3-(3-fluorophenyl)phenyl]methyl]-2-oxoazepan-3-yl]-3-(2-methylpropyl)-2-propylbutanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCC)C(N)=O)CCCCN1CC1=CC=CC(C=2C=C(F)C=CC=2)=C1 DXAMIGRAGGVLFS-RCSZBHJWSA-N 0.000 claims description 2
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- MVUCGZSBMJTQTB-LADMEODRSA-N n'-[(3s)-1-[[3-(4-methylphenyl)phenyl]methyl]-2-oxoazepan-3-yl]-3-(2-methylpropyl)-2-propylbutanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCC)C(N)=O)CCCCN1CC1=CC=CC(C=2C=CC(C)=CC=2)=C1 MVUCGZSBMJTQTB-LADMEODRSA-N 0.000 claims description 2
- MUVFESNOIMFTNV-JGZAQREWSA-N n'-[(3s)-1-[[5-(3-chloro-4-fluorophenyl)pyridin-3-yl]methyl]-2-oxoazepan-3-yl]-3-(2-methylpropyl)-2-propylbutanediamide Chemical compound O=C1[C@@H](NC(=O)C(CC(C)C)C(CCC)C(N)=O)CCCCN1CC1=CN=CC(C=2C=C(Cl)C(F)=CC=2)=C1 MUVFESNOIMFTNV-JGZAQREWSA-N 0.000 claims description 2
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- QFMBUGLDMHFIFQ-UHFFFAOYSA-N n'-[1-(2-cyclobutylethyl)-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]-3-(2-methylpropyl)-2-propylbutanediamide Chemical compound C12=CC=CC=C2N(CCC2CCC2)C(=O)C(NC(=O)C(CC(C)C)C(CCC)C(N)=O)N=C1C1=CC=CC=C1 QFMBUGLDMHFIFQ-UHFFFAOYSA-N 0.000 claims description 2
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- VCKWIMURNOYHTD-UHFFFAOYSA-N n'-[1-(cyclohexylmethyl)-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]-3-(2-methylpropyl)-2-propylbutanediamide Chemical compound C12=CC=CC=C2N(CC2CCCCC2)C(=O)C(NC(=O)C(CC(C)C)C(CCC)C(N)=O)N=C1C1=CC=CC=C1 VCKWIMURNOYHTD-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
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HRP990246A2 true HRP990246A2 (en) | 2000-06-30 |
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HR (1) | HRP990246A2 (es) |
TR (1) | TR200100377T2 (es) |
WO (1) | WO2000007995A1 (es) |
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CA2377221A1 (en) | 1999-09-13 | 2001-03-22 | Bristol-Myers Squibb Pharma Company | Hydroxyalkanoyl aminolactams and related structures as inhibitors of a.beta. protein production |
US6960576B2 (en) | 1999-09-13 | 2005-11-01 | Bristol-Myers Squibb Pharma Company | Hydroxyalkanoylaminolactams and related structures as inhibitors of Aβ protein production |
US6503902B2 (en) | 1999-09-13 | 2003-01-07 | Bristol-Myers Squibb Pharma Company | Hydroxyalkanoylaminolactams and related structures as inhibitors of a β protein production |
WO2001027108A1 (en) * | 1999-10-08 | 2001-04-19 | Bristol-Myers Squibb Pharma Company | AMINO LACTAM SULFONAMIDES AS INHIBITORS OF Aβ PROTEIN PRODUCTION |
WO2001060826A2 (en) * | 2000-02-17 | 2001-08-23 | Bristol-Myers Squibb Pharma Company | SUCCINOYLAMINO CARBOCYCLES AND HETEROCYCLES AS INHIBITORS OF Aβ PROTEIN PRODUCTION |
CA2401120A1 (en) * | 2000-03-28 | 2001-10-04 | Dupont Pharmaceuticals Company | Lactams as inhibitors of a-beta protein production |
US6495540B2 (en) | 2000-03-28 | 2002-12-17 | Bristol - Myers Squibb Pharma Company | Lactams as inhibitors of A-β protein production |
BR0110051A (pt) * | 2000-04-03 | 2004-12-07 | Bristol Myers Squibb Pharma Co | Composto, uso do composto, composição farmacêutica e método de tratamento do mal de alzheimer |
CA2404273A1 (en) | 2000-04-11 | 2001-10-18 | Bristol-Myers Squibb Pharma Company | Substituted lactams as inhibitors of a.beta. protein production |
AU2001261728A1 (en) | 2000-05-17 | 2001-11-26 | Bristol-Myers Squibb Pharma Company | Use of small molecule radioligands for diagnostic imaging |
CN1251671C (zh) * | 2000-05-19 | 2006-04-19 | 武田药品工业株式会社 | β分泌酶抑制剂 |
GB0012671D0 (en) * | 2000-05-24 | 2000-07-19 | Merck Sharp & Dohme | Therapeutic agents |
EP1268450A1 (en) | 2000-06-01 | 2003-01-02 | Bristol-Myers Squibb Pharma Company | Lactams substituted by cyclic succinates as inhibitors of a-beta protein production |
DE10043282A1 (de) * | 2000-09-02 | 2002-03-28 | Kurt Heininger | Verwendung von Inhibitoren der Amyloid-beta-Protein-Bildung |
US7001901B2 (en) | 2002-08-27 | 2006-02-21 | Bristol-Myers Squibb Company | Tetrazolylpropionamides as inhibitors of Aβ protein production |
TW200502221A (en) | 2002-10-03 | 2005-01-16 | Astrazeneca Ab | Novel lactams and uses thereof |
GB0223039D0 (en) * | 2002-10-04 | 2002-11-13 | Merck Sharp & Dohme | Therapeutic compounds |
GB0223038D0 (en) * | 2002-10-04 | 2002-11-13 | Merck Sharp & Dohme | Therapeutic compounds |
US7342007B2 (en) | 2003-03-14 | 2008-03-11 | Astrazeneca Ab | Lactams and uses thereof |
EP1660443B1 (en) | 2003-08-08 | 2009-03-04 | Schering Corporation | Cyclic amine bace-1 inhibitors having a benzamide substituent |
TW200524910A (en) | 2003-08-08 | 2005-08-01 | Schering Corp | Cyclic amine BACE-1 inhibitors having a heterocyclic substituent |
WO2005019227A1 (en) * | 2003-08-22 | 2005-03-03 | Orchid Chemicals & Pharmaceuticals Ltd | Process for the preparation of cephalosporin antibiotic |
WO2005053702A2 (en) * | 2003-12-01 | 2005-06-16 | Cambridge University Technical Services Limited | Anti-inflammatory agents |
BRPI0510746A (pt) | 2004-06-10 | 2007-11-20 | Univ Michigan State | sìntese de caprolactama a partir de lisina |
MX2007000760A (es) | 2004-07-22 | 2007-04-09 | Schering Corp | Amida sustituida inhibidora de b secretasa. |
JP2008528448A (ja) * | 2005-01-03 | 2008-07-31 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 新規化合物に関連する組成物および方法、ならびにその標的 |
AU2008215948A1 (en) | 2007-02-12 | 2008-08-21 | Merck & Co., Inc. | Piperazine derivatives for treatment of AD and related conditions |
BRPI0804506A2 (pt) * | 2007-02-20 | 2011-08-30 | Univ Michigan State | processos para preparar caprolactama ou um derivado da mesma e ácido pipecolìnico, caprolactama ou um derivado da mesma, e, ácido pipecolìnico ou um derivado do mesmo |
CA2709677C (en) | 2007-12-21 | 2017-03-14 | Lin Zhi | Selective androgen receptor modulators (sarms) and uses thereof |
EP2291181B9 (en) | 2008-04-18 | 2013-09-11 | University College Dublin National University Of Ireland, Dublin | Captodiamine for the treatment of depression symptoms |
JP2011529087A (ja) * | 2008-07-24 | 2011-12-01 | ドラス コーポレイション | 環状アミドモノマーを作製する方法、ならびに関連する誘導体および方法 |
GB201101331D0 (en) * | 2011-01-26 | 2011-03-09 | Glaxosmithkline Biolog Sa | Compositions and uses |
US9309307B2 (en) * | 2011-01-07 | 2016-04-12 | Seiko Epson Corporation | Antibody against amyloid precursor protein signal peptide |
TWI530489B (zh) | 2011-03-22 | 2016-04-21 | 必治妥美雅史谷比公司 | 雙(氟烷基)-1,4-苯二氮呯酮化合物 |
EP2897960B1 (en) | 2012-09-21 | 2016-08-03 | Bristol-Myers Squibb Company | Tricyclic heterocyclic compounds as notch inhibitors |
WO2014047397A1 (en) * | 2012-09-21 | 2014-03-27 | Bristol-Myers Squibb Company | Fluoroalkyl and fluorocycloalkyl 1,4-benzodiazepinone compounds as notch|inhibitors |
WO2014047369A1 (en) * | 2012-09-21 | 2014-03-27 | Bristol-Myers Squibb Company | Substituted 1,5-benzodiazepinone compounds |
CN104822677A (zh) | 2012-09-21 | 2015-08-05 | 百时美施贵宝公司 | 氟烷基-1,4-苯并二氮杂*酮化合物 |
CN104854097A (zh) * | 2012-09-21 | 2015-08-19 | 百时美施贵宝公司 | N-取代的二(氟烷基)-1,4-苯并二氮杂*酮化合物 |
CN104854094A (zh) * | 2012-09-21 | 2015-08-19 | 百时美施贵宝公司 | 氟烷基二苯并二氮杂*酮化合物 |
US9273075B2 (en) | 2012-09-21 | 2016-03-01 | Bristol-Myers Squibb Company | Prodrugs of 1,4-benzodiazepinone compounds |
US9242941B2 (en) | 2012-09-21 | 2016-01-26 | Bristol-Myers Squibb Company | Alkyl, fluoroalkyl-1,4-benzodiazepinone compounds |
TWI614238B (zh) | 2012-09-21 | 2018-02-11 | 必治妥美雅史谷比公司 | 雙(氟烷基)-1,4-苯并二氮呯酮化合物及其前藥 |
JP2016515625A (ja) | 2013-04-04 | 2016-05-30 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | 増殖性疾患を治療するための併用療法 |
EP3613418A1 (en) | 2014-01-17 | 2020-02-26 | Ligand Pharmaceuticals, Inc. | Methods and compositions for modulating hormone levels |
Family Cites Families (90)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US552419A (en) * | 1895-12-31 | Gas generator and burner | ||
US4666829A (en) * | 1985-05-15 | 1987-05-19 | University Of California | Polypeptide marker for Alzheimer's disease and its use for diagnosis |
ZW23187A1 (en) | 1986-12-15 | 1988-06-29 | Hoffmann La Roche | Phosphinic acid derivatives |
FR2630440B1 (fr) * | 1988-04-25 | 1991-09-20 | Jouveinal Sa | Benzodiazepines, leur procede et intermediaires de preparation et leurs applications en therapeutique |
JPH0374328A (ja) * | 1989-08-04 | 1991-03-28 | Warner Lambert Co | 薬学的活性を有する中枢コレシストキニン拮抗剤 |
US5175159A (en) * | 1989-10-05 | 1992-12-29 | Merck & Co., Inc. | 3-substituted-1,4-benzodiazepines as oxytocin antagonists |
CA2026856A1 (en) | 1989-10-05 | 1991-04-06 | Mark G. Bock | 3-substituted-1,4-benzodiazepines useful as oxytocin |
IE904560A1 (en) | 1989-12-18 | 1991-06-19 | Merck & Co Inc | New benzodiazepine analogs |
US5019724A (en) | 1989-12-20 | 1991-05-28 | Sgs-Thomson Microelectronics, Inc. | Noise tolerant input buffer |
US5252463A (en) | 1990-06-22 | 1993-10-12 | The Du Pont Merck Pharmaceutical Company | Clipsin, a chymotrypsin-like protease and method of using same |
GB9022117D0 (en) | 1990-10-11 | 1990-11-21 | Beecham Group Plc | Novel compounds |
GB9107368D0 (en) | 1991-04-08 | 1991-05-22 | Smithkline Beecham Plc | Novel compounds |
US5538845A (en) * | 1992-02-05 | 1996-07-23 | Athena Neurosciences, Inc. | Beta-amyloid peptide production inhibitors and methods for their identification |
US5766846A (en) * | 1992-07-10 | 1998-06-16 | Athena Neurosciences | Methods of screening for compounds which inhibit soluble β-amyloid peptide production |
US5618812A (en) | 1992-07-29 | 1997-04-08 | Merck Sharp & Dohme, Ltd. | Benzodiazepine derivatives |
US5283241A (en) | 1992-08-28 | 1994-02-01 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
DE69332860T2 (de) | 1992-12-21 | 2004-03-11 | Smithkline Beecham Corp. | Bicyklische fibrinogen antagoniste |
MX9308016A (es) * | 1992-12-22 | 1994-08-31 | Lilly Co Eli | Compuestos inhibidores de la proteasa del virus de la inmunodeficiencia humana, procedimiento para su preparacion y formulacion farmaceutica que los contiene. |
US5506242A (en) * | 1993-01-06 | 1996-04-09 | Ciba-Geigy Corporation | Arylsufonamido-substituted hydroxamic acids |
US5552419A (en) * | 1993-01-06 | 1996-09-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
US5455258A (en) | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
US5594006A (en) * | 1993-03-18 | 1997-01-14 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives as matrix metalloproteinases inhibitors |
JPH07157470A (ja) * | 1993-03-18 | 1995-06-20 | Otsuka Pharmaceut Co Ltd | カルボスチリル誘導体 |
EP0698015A1 (en) * | 1993-05-14 | 1996-02-28 | Genentech, Inc. | Preparation of n-cyanodithioimino-carbonates and 3-mercapto-5-amino-1h-1,2,4-triazole |
WO1994029273A1 (en) * | 1993-06-09 | 1994-12-22 | Smithkline Beecham Corporation | Bicyclic fibrinogen antagonists |
CZ184194A3 (en) * | 1993-08-09 | 1995-03-15 | Lilly Co Eli | Aspartylprotease inhibitor and method of identifying thereof |
US5602156A (en) * | 1993-09-17 | 1997-02-11 | The United States Of America As Represented By The Department Of Health And Human Services | Method for inhibiting metalloproteinase expression |
US5545735A (en) * | 1993-10-04 | 1996-08-13 | Merck & Co., Inc. | Benzo-Fused Lactams promote release of growth hormone |
US5426185A (en) * | 1993-11-22 | 1995-06-20 | Merck & Co., Inc. | Antiarrhythmic benzodiazepines |
US5770573A (en) * | 1993-12-06 | 1998-06-23 | Cytel Corporation | CS-1 peptidomimetics, compositions and methods of using the same |
GB9401919D0 (en) * | 1994-02-01 | 1994-03-30 | Bridport Aviat Prod | Luggage bins for the cabins of passenger aircraft |
US5514716A (en) | 1994-02-25 | 1996-05-07 | Sterling Winthrop, Inc. | Hydroxamic acid and carboxylic acid derivatives, process for their preparation and use thereof |
CA2196062A1 (en) * | 1994-07-29 | 1996-02-15 | Yoshinari Sato | Benzodiazepine derivatives |
US5661161A (en) * | 1994-09-29 | 1997-08-26 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
JPH11505509A (ja) | 1994-12-09 | 1999-05-21 | スミスクライン・ビーチャム・コーポレイション | 二環式フィブリノーゲン拮抗薬 |
WO1996018602A1 (en) | 1994-12-13 | 1996-06-20 | Smithkline Beecham Corporation | Bicyclic fibrinogen antagonists |
US5639746A (en) * | 1994-12-29 | 1997-06-17 | The Procter & Gamble Company | Hydroxamic acid-containing inhibitors of matrix metalloproteases |
US5672598A (en) * | 1995-03-21 | 1997-09-30 | The Procter & Gamble Company | Lactam-containing hydroxamic acids |
US5578629A (en) * | 1995-03-29 | 1996-11-26 | Merck & Co., Inc. | Benzamide-containing inhibitors of farnesyl-protein transferase |
US5856326A (en) * | 1995-03-29 | 1999-01-05 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
GB9507799D0 (en) | 1995-04-18 | 1995-05-31 | British Biotech Pharm | Metalloproteinase inhibitors |
US5710171A (en) * | 1995-05-24 | 1998-01-20 | Merck & Co., Inc. | Bisphenyl inhibitors of farnesyl-protein transferase |
EP0828754B1 (en) * | 1995-05-29 | 2005-02-02 | Pfizer Inc. | Dipeptides which promote release of growth hormone |
US5756528A (en) * | 1995-06-06 | 1998-05-26 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
DE19522899C1 (de) * | 1995-06-23 | 1996-12-19 | Hexal Pharmaforschung Gmbh | Verfahren zum kontinuierlichen Ersintern eines Granulats |
JPH09188631A (ja) * | 1995-09-08 | 1997-07-22 | Kanebo Ltd | Fasリガンド可溶化抑制薬 |
EP0761680A3 (en) * | 1995-09-12 | 1999-05-06 | Ono Pharmaceutical Co., Ltd. | Tetrazole compounds having Interleukin-1beta converting enzyme inhibitory activity |
AU7139996A (en) | 1995-10-05 | 1997-04-28 | Chiroscience Limited | Mercaptoamide derivatives and their therapeutic use |
SI9620120A (sl) | 1995-11-14 | 1999-06-30 | Dupont Pharmaceuticals Company | Nove makrociklične spojine kot metaloproteazni inhibitorji |
EP0873304B1 (en) * | 1995-11-23 | 2001-09-05 | British Biotech Pharmaceuticals Limited | Metalloproteinase inhibitors |
US5968965A (en) * | 1996-01-30 | 1999-10-19 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
AU703203B2 (en) * | 1996-01-30 | 1999-03-18 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
US5891889A (en) * | 1996-04-03 | 1999-04-06 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
US5965578A (en) * | 1996-04-03 | 1999-10-12 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
CA2250353A1 (en) | 1996-04-03 | 1997-10-09 | Christopher J. Dinsmore | Inhibitors of farnesyl-protein transferase |
US5869682A (en) * | 1996-04-03 | 1999-02-09 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
US5885995A (en) * | 1996-04-03 | 1999-03-23 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
WO1997036879A1 (en) | 1996-04-03 | 1997-10-09 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
US5859012A (en) * | 1996-04-03 | 1999-01-12 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
US5852010A (en) * | 1996-04-03 | 1998-12-22 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
JP2000507589A (ja) | 1996-04-03 | 2000-06-20 | メルク エンド カンパニー インコーポレーテッド | ファルネシル―タンパク質転移酵素の阻害剤 |
US5919785A (en) * | 1996-04-03 | 1999-07-06 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
US6001835A (en) * | 1996-04-03 | 1999-12-14 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
DE19614100C2 (de) * | 1996-04-10 | 2000-12-07 | Bosch Gmbh Robert | Vorrichtung zur Ermittlung des Zustandes eines Wischerblattes |
WO1997038664A2 (en) | 1996-04-18 | 1997-10-23 | Merck & Co., Inc. | A method of treating cancer |
JP2000508335A (ja) | 1996-05-30 | 2000-07-04 | メルク エンド カンパニー インコーポレーテッド | 癌の治療方法 |
US5703129A (en) * | 1996-09-30 | 1997-12-30 | Bristol-Myers Squibb Company | 5-amino-6-cyclohexyl-4-hydroxy-hexanamide derivatives as inhibitors of β-amyloid protein production |
WO1998015828A1 (en) | 1996-10-07 | 1998-04-16 | Scios Inc. | Method to identify direct inhibitors of the beta-amyloid forming enzyme gamma-secretase |
US6262047B1 (en) * | 1996-10-11 | 2001-07-17 | Cor Therapeutics, Inc. | Selective factor Xa inhibitors |
CA2268281A1 (en) | 1996-10-11 | 1998-04-23 | Cor Therapeutics, Inc. | Selective factor xa inhibitors |
US5734054A (en) * | 1996-11-05 | 1998-03-31 | Pharmacopeia, Inc. | Hydroxy-amino acid amides |
PL323130A1 (en) * | 1996-11-15 | 1998-05-25 | Hoechst Ag | Application of heterocyclic compounds in production of a pharmaceutic agent, novel heterocyclic compounds and pharmaceutic agent as such |
WO1998022441A2 (en) | 1996-11-22 | 1998-05-28 | Elan Pharmaceuticals, Inc. | N-(aryl/heteroaryl) amino acid esters, pharmaceutical compositions, and methods for inhibiting beta-amyloid peptide and/or its synthesis |
KR20000069075A (ko) | 1996-11-22 | 2000-11-25 | 진 엠. 듀발 | N-(아릴/헤테로아릴/알킬아세틸)아미노산 아미드, 이들을 함유하는 제약 조성물, 및 이들 화합물을 사용하여 베타-아밀로이드 펩티드의 방출 및(또는) 합성의 억제 방법 |
HUP0000492A3 (en) | 1996-11-22 | 2000-06-28 | Lilly Co Eli | N-(aryl/heteroarylacetyl) amino acid esters, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds |
EP0942923A2 (en) | 1996-11-22 | 1999-09-22 | Elan Pharmaceuticals, Inc. | N-(ARYL/HETEROARYL) AMINO ACID DERIVATIVES, PHARMACEUTICAL COMPOSITIONS COMPRISING SAME, AND METHODS FOR INHIBITING $g(b)-AMYLOID PEPTIDE RELEASE AND/OR ITS SYNTHESIS BY USE OF SUCH COMPOUNDS |
TW523506B (en) | 1996-12-18 | 2003-03-11 | Ono Pharmaceutical Co | Sulfonamide or carbamide derivatives and drugs containing the same as active ingredients |
ES2319239T3 (es) * | 1996-12-23 | 2009-05-05 | Elan Pharmaceuticals, Inc. | Cicloalquilo, lactama, lactona y compuestos relacionados, composiciones farmaceuticas que comprenden los mismos y procedimientos para inhibir la liberacion del peptido beta-amiloide y/o sintesis mediante el uso de tales compuestos. |
US6093737A (en) * | 1996-12-30 | 2000-07-25 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
AU6013998A (en) | 1996-12-30 | 1998-07-31 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
JP2002241368A (ja) * | 1997-02-18 | 2002-08-28 | Shionogi & Co Ltd | 新規ベンゾラクタム誘導体およびそれを含有する医薬組成物 |
US6432947B1 (en) * | 1997-02-19 | 2002-08-13 | Berlex Laboratories, Inc. | N-heterocyclic derivatives as NOS inhibitors |
US5985900A (en) * | 1997-04-01 | 1999-11-16 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
US6060038A (en) * | 1997-05-15 | 2000-05-09 | Merck & Co., Inc. | Radiolabeled farnesyl-protein transferase inhibitors |
DE19726427A1 (de) * | 1997-06-23 | 1998-12-24 | Boehringer Mannheim Gmbh | Pyrimidin-2,4,6-trion-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
GB9715030D0 (en) * | 1997-07-18 | 1997-09-24 | British Biotech Pharm | Metalloproteinase inhibitors |
US6228854B1 (en) * | 1997-08-11 | 2001-05-08 | Cor Therapeutics, Inc. | Selective factor Xa inhibitors |
US6333321B1 (en) * | 1997-08-11 | 2001-12-25 | Cor Therapeutics, Inc. | Selective factor Xa inhibitors |
US6297239B1 (en) * | 1997-10-08 | 2001-10-02 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
US6440965B1 (en) * | 1997-10-15 | 2002-08-27 | Krenitsky Pharmaceuticals, Inc. | Substituted pyrimidine derivatives, their preparation and their use in the treatment of neurodegenerative or neurological disorders of the central nervous system |
-
1999
- 1999-08-06 HR HR990246A patent/HRP990246A2/hr not_active Application Discontinuation
- 1999-08-07 AT AT99939010T patent/ATE307117T1/de not_active IP Right Cessation
- 1999-08-07 CN CN99809366A patent/CN1311779A/zh active Pending
- 1999-08-07 WO PCT/US1999/017717 patent/WO2000007995A1/en active IP Right Grant
- 1999-08-07 CA CA002338944A patent/CA2338944A1/en not_active Abandoned
- 1999-08-07 EP EP99939010A patent/EP1102752B1/en not_active Expired - Lifetime
- 1999-08-07 ES ES99939010T patent/ES2251838T3/es not_active Expired - Lifetime
- 1999-08-07 BR BR9912969-8A patent/BR9912969A/pt not_active IP Right Cessation
- 1999-08-07 DE DE69927827T patent/DE69927827T2/de not_active Expired - Lifetime
- 1999-08-07 AU AU53378/99A patent/AU756830B2/en not_active Ceased
- 1999-08-07 TR TR2001/00377T patent/TR200100377T2/xx unknown
- 1999-08-07 JP JP2000563629A patent/JP2003526603A/ja not_active Ceased
- 1999-08-09 AR ARP990103962A patent/AR024197A1/es not_active Application Discontinuation
-
2006
- 2006-07-25 US US11/492,593 patent/US7304055B2/en not_active Expired - Lifetime
- 2006-07-26 US US11/493,156 patent/US7304056B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
ES2251838T3 (es) | 2006-05-01 |
AU756830B2 (en) | 2003-01-23 |
WO2000007995A1 (en) | 2000-02-17 |
EP1102752A1 (en) | 2001-05-30 |
JP2003526603A (ja) | 2003-09-09 |
DE69927827T2 (de) | 2006-07-06 |
CN1311779A (zh) | 2001-09-05 |
AR024197A1 (es) | 2002-09-25 |
BR9912969A (pt) | 2001-09-25 |
TR200100377T2 (tr) | 2001-06-21 |
US20060264417A1 (en) | 2006-11-23 |
AU5337899A (en) | 2000-02-28 |
US20060258638A1 (en) | 2006-11-16 |
US7304056B2 (en) | 2007-12-04 |
US7304055B2 (en) | 2007-12-04 |
ATE307117T1 (de) | 2005-11-15 |
CA2338944A1 (en) | 2000-02-17 |
DE69927827D1 (de) | 2006-03-02 |
EP1102752B1 (en) | 2005-10-19 |
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