ZA200503693B - Hydroxyethylamine derivatives for the treatment of Alzheimer's disease - Google Patents
Hydroxyethylamine derivatives for the treatment of Alzheimer's disease Download PDFInfo
- Publication number
- ZA200503693B ZA200503693B ZA200503693A ZA200503693A ZA200503693B ZA 200503693 B ZA200503693 B ZA 200503693B ZA 200503693 A ZA200503693 A ZA 200503693A ZA 200503693 A ZA200503693 A ZA 200503693A ZA 200503693 B ZA200503693 B ZA 200503693B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydroxy
- benzamide
- propyl
- ethylamino
- benzyl
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract description 16
- 208000024827 Alzheimer disease Diseases 0.000 title abstract description 11
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 155
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 208000037259 Amyloid Plaque Diseases 0.000 claims abstract description 14
- 201000010099 disease Diseases 0.000 claims abstract description 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 304
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 278
- -1 cyano, hydroxy Chemical group 0.000 claims description 244
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 222
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 140
- 150000001875 compounds Chemical class 0.000 claims description 115
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 89
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 50
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 239000005711 Benzoic acid Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 235000010233 benzoic acid Nutrition 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 2
- 125000005217 alkenylheteroaryl group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
- SYPKAYWCBCMIME-IGYGKHONSA-N n-[(2s,3r)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-ethyl-1-methyl-7-(2-oxopyrrolidin-1-yl)indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N(C)C=C(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC=CC=C1 SYPKAYWCBCMIME-IGYGKHONSA-N 0.000 claims 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- QQVAETJEGYOVEJ-BZKUTMRRSA-N 1-butyl-n-[(2s,3r)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-4-(2-oxopyrrolidin-1-yl)indole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=CN(C2=C1)CCCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(OC)C=CC=1)C1=CC=CC=C1 QQVAETJEGYOVEJ-BZKUTMRRSA-N 0.000 claims 1
- 125000006433 1-ethyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- JWSLPJZVLFZEJV-LITSAYRRSA-N 1-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-4-(2-oxopyrrolidin-1-yl)indazole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=NN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 JWSLPJZVLFZEJV-LITSAYRRSA-N 0.000 claims 1
- BJAZGJCGTUFTCO-BHBYDHKZSA-N 1-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-4-(2-oxopyrrolidin-1-yl)indole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=CN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 BJAZGJCGTUFTCO-BHBYDHKZSA-N 0.000 claims 1
- QCJQHYQCGRESHY-BHBYDHKZSA-N 1-ethyl-n-[(2s,3r)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-4-(2-oxopyrrolidin-1-yl)indazole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=NN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(OC)C=CC=1)C1=CC=CC=C1 QCJQHYQCGRESHY-BHBYDHKZSA-N 0.000 claims 1
- BARAICYUEPEIRD-QCENPCRXSA-N 1-ethyl-n-[(2s,3r)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-4-(2-oxopyrrolidin-1-yl)indole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=CN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(OC)C=CC=1)C1=CC=CC=C1 BARAICYUEPEIRD-QCENPCRXSA-N 0.000 claims 1
- KPCQJMOTOVCVKD-BHDXBOSCSA-N 1-ethyl-n-[(2s,3r)-3-hydroxy-4-[2-(3-methoxyphenyl)propan-2-ylamino]-1-phenylbutan-2-yl]-4-(2-oxopyrrolidin-1-yl)indole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=CN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC(C)(C)C=1C=C(OC)C=CC=1)C1=CC=CC=C1 KPCQJMOTOVCVKD-BHDXBOSCSA-N 0.000 claims 1
- SIPVIWVJWIGXCK-FRJUPVQCSA-N 1-n-[(2s,3r)-4-[[(2s)-1-(cyclohexylamino)-1-oxopropan-2-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)C(=O)N(CCC)CCC)N1C(CCC1)=O)[C@H](O)CN[C@@H](C)C(=O)NC1CCCCC1)C1=CC=CC=C1 SIPVIWVJWIGXCK-FRJUPVQCSA-N 0.000 claims 1
- ZPAUMAHWYDRPJY-UHFFFAOYSA-N 2-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C1=C(C(N)=O)C(NCC)=CC=C1N1C(=O)CCC1 ZPAUMAHWYDRPJY-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- ADDFLVAAVKFAIW-LADGPHEKSA-N 2-fluoro-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(propan-2-ylamino)butan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC(C)C)=CC(CCC)=CC=1N1CCCC1=O ADDFLVAAVKFAIW-LADGPHEKSA-N 0.000 claims 1
- YJUMNUUHYAGNMB-XTEPFMGCSA-N 2-fluoro-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(C=CC=2)C(F)(F)F)=CC(CCC)=CC=1N1CCCC1=O YJUMNUUHYAGNMB-XTEPFMGCSA-N 0.000 claims 1
- YYFIBKOIQXAYPN-AZGAKELHSA-N 2-fluoro-n-[(2s,3r)-3-hydroxy-4-(oxan-4-ylamino)-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC2CCOCC2)=CC(CCC)=CC=1N1CCCC1=O YYFIBKOIQXAYPN-AZGAKELHSA-N 0.000 claims 1
- PXFIIQOMCJNZLW-MFMCTBQISA-N 2-fluoro-n-[(2s,3r)-3-hydroxy-4-[2-(3-methoxyphenyl)propan-2-ylamino]-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC(C)(C)C=2C=C(OC)C=CC=2)=CC(CCC)=CC=1N1CCCC1=O PXFIIQOMCJNZLW-MFMCTBQISA-N 0.000 claims 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000006186 3,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C([H])=C1C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
- GJMDCLYCVWPLMB-XTEPFMGCSA-N 3-(1,1-dioxo-1,2-thiazolidin-2-yl)-2-fluoro-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(C=CC=2)C(F)(F)F)=CC(CCC)=CC=1N1CCCS1(=O)=O GJMDCLYCVWPLMB-XTEPFMGCSA-N 0.000 claims 1
- KJADMOJANXVLQR-MFMCTBQISA-N 3-(1,1-dioxo-1,2-thiazolidin-2-yl)-2-fluoro-n-[(2s,3r)-3-hydroxy-4-[2-(3-methoxyphenyl)propan-2-ylamino]-1-phenylbutan-2-yl]-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC(C)(C)C=2C=C(OC)C=CC=2)=CC(CCC)=CC=1N1CCCS1(=O)=O KJADMOJANXVLQR-MFMCTBQISA-N 0.000 claims 1
- AKXKOHRAMSKZTG-WUFINQPMSA-N 3-(1,1-dioxo-1,2-thiazolidin-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethoxy)phenyl]methylamino]butan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCC1)(=O)=O)[C@H](O)CNCC=1C=C(OC(F)(F)F)C=CC=1)C1=CC=CC=C1 AKXKOHRAMSKZTG-WUFINQPMSA-N 0.000 claims 1
- FLQGWSYAWOLJIW-LMSSTIIKSA-N 3-(1,1-dioxo-1,2-thiazolidin-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-4-methylbenzamide Chemical compound CC=1C(NCC)=CC(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(C=CC=2)C(F)(F)F)=CC=1N1CCCS1(=O)=O FLQGWSYAWOLJIW-LMSSTIIKSA-N 0.000 claims 1
- LJBWRMJUJQPODU-URLMMPGGSA-N 3-(1,1-dioxo-1,2-thiazolidin-2-yl)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethoxy)phenyl]methylamino]butan-2-yl]-5-propan-2-yloxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OC(C)C)N1S(CCC1)(=O)=O)[C@H](O)CNCC=1C=C(OC(F)(F)F)C=CC=1)C1=CC=CC=C1 LJBWRMJUJQPODU-URLMMPGGSA-N 0.000 claims 1
- AGHXATULXGHLPJ-XZWHSSHBSA-N 3-(1,1-dioxo-1,2-thiazolidin-2-yl)-n-[(2s,3r)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound COC1=CC=CC(CNC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)C=2C=C(C=C(C=2)N2C(CCC2)=O)N2S(CCC2)(=O)=O)=C1 AGHXATULXGHLPJ-XZWHSSHBSA-N 0.000 claims 1
- SDQPPRXTGYPFMS-AHKZPQOWSA-N 3-(1,1-dioxothiazinan-2-yl)-2-fluoro-n-[(2s,3r)-3-hydroxy-4-(oxan-4-ylamino)-1-phenylbutan-2-yl]-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC2CCOCC2)=CC(CCC)=CC=1N1CCCCS1(=O)=O SDQPPRXTGYPFMS-AHKZPQOWSA-N 0.000 claims 1
- BWSVKUXKPIHNSI-MFMCTBQISA-N 3-(1,1-dioxothiazinan-2-yl)-2-fluoro-n-[(2s,3r)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(OC)C=CC=2)=CC(CCC)=CC=1N1CCCCS1(=O)=O BWSVKUXKPIHNSI-MFMCTBQISA-N 0.000 claims 1
- JUZISPOBCCMPNX-AHKZPQOWSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-2-fluoro-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(2,4,4-trimethylpentan-2-ylamino)butan-2-yl]benzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC(C)(C)CC(C)(C)C)=CC(NCC)=CC=1N1CCCCS1(=O)=O JUZISPOBCCMPNX-AHKZPQOWSA-N 0.000 claims 1
- YFVGAASHIGLTOK-XTEPFMGCSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-2-fluoro-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethoxy)phenyl]methylamino]butan-2-yl]benzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(OC(F)(F)F)C=CC=2)=CC(NCC)=CC=1N1CCCCS1(=O)=O YFVGAASHIGLTOK-XTEPFMGCSA-N 0.000 claims 1
- IDQKLCONYNKVAX-DCRAVRKTSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-2-fluoro-n-[(2s,3r)-3-hydroxy-4-(4-methylpentan-2-ylamino)-1-phenylbutan-2-yl]benzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC(C)CC(C)C)=CC(NCC)=CC=1N1CCCCS1(=O)=O IDQKLCONYNKVAX-DCRAVRKTSA-N 0.000 claims 1
- FIBBMSCTKGVLTM-XTEPFMGCSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-2-fluoro-n-[(2s,3r)-4-[[4-fluoro-3-(trifluoromethyl)phenyl]methylamino]-3-hydroxy-1-phenylbutan-2-yl]benzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(C(F)=CC=2)C(F)(F)F)=CC(NCC)=CC=1N1CCCCS1(=O)=O FIBBMSCTKGVLTM-XTEPFMGCSA-N 0.000 claims 1
- HTSUZHPFNXHAPU-XSJQRQGXSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-1-(3-fluorophenyl)-3-hydroxy-4-(6-methylheptan-2-ylamino)butan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)CCCC(C)C)C1=CC=CC(F)=C1 HTSUZHPFNXHAPU-XSJQRQGXSA-N 0.000 claims 1
- DZDPXRZSBXSGCD-WUFINQPMSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-1-(furan-2-yl)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]butan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(OC)C=CC=1)C1=CC=CO1 DZDPXRZSBXSGCD-WUFINQPMSA-N 0.000 claims 1
- ZGZHPYUBZZKMFV-XZWHSSHBSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(2-phenylethylamino)butan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCCC=1C=CC=CC=1)C1=CC=CC=C1 ZGZHPYUBZZKMFV-XZWHSSHBSA-N 0.000 claims 1
- IYQODVUJOLOIDV-RRPNLBNLSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(thiophen-3-ylmethylamino)butan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC1=CSC=C1)C1=CC=CC=C1 IYQODVUJOLOIDV-RRPNLBNLSA-N 0.000 claims 1
- ZELNVMJIVXANSJ-URLMMPGGSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[(1-propylcyclopentyl)amino]butan-2-yl]benzamide Chemical compound C([C@@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)C=1C=C(C=C(NCC)C=1)N1S(CCCC1)(=O)=O)NC1(CCC)CCCC1 ZELNVMJIVXANSJ-URLMMPGGSA-N 0.000 claims 1
- IQAXRTQZUIWOOW-IZZNHLLZSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(2-methylbutan-2-ylamino)-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)(C)CC)C1=CC=CC=C1 IQAXRTQZUIWOOW-IZZNHLLZSA-N 0.000 claims 1
- HQAHKHNEXXFYJJ-LPRJAOSGSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(6-methylheptan-2-ylamino)-1-thiophen-2-ylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)CCCC(C)C)C1=CC=CS1 HQAHKHNEXXFYJJ-LPRJAOSGSA-N 0.000 claims 1
- ZRYPXEPUVGYRNV-LPRJAOSGSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(6-methylheptan-2-ylamino)-1-thiophen-3-ylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)CCCC(C)C)C=1C=CSC=1 ZRYPXEPUVGYRNV-LPRJAOSGSA-N 0.000 claims 1
- RGVHPEANFGTPJD-XZOQPEGZSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(methylamino)-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC)C1=CC=CC=C1 RGVHPEANFGTPJD-XZOQPEGZSA-N 0.000 claims 1
- GSMXCHRMEXPRGE-RRPNLBNLSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(oxan-4-ylamino)-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CCOCC1)C1=CC=CC=C1 GSMXCHRMEXPRGE-RRPNLBNLSA-N 0.000 claims 1
- MQCJYAKWACWWBW-WUFINQPMSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(1-methylcyclohexyl)amino]-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1(C)CCCCC1)C1=CC=CC=C1 MQCJYAKWACWWBW-WUFINQPMSA-N 0.000 claims 1
- SRVPZFYYTADCMW-RRPNLBNLSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(1-methylcyclopentyl)amino]-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1(C)CCCC1)C1=CC=CC=C1 SRVPZFYYTADCMW-RRPNLBNLSA-N 0.000 claims 1
- RTPXSXDHPZFEJG-XZWHSSHBSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(3-methoxy-2-methylphenyl)methylamino]-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C(=C(OC)C=CC=1)C)C1=CC=CC=C1 RTPXSXDHPZFEJG-XZWHSSHBSA-N 0.000 claims 1
- GCSNQYRIELZVTI-XZWHSSHBSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(3-methoxy-4-methylphenyl)methylamino]-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(OC)C(C)=CC=1)C1=CC=CC=C1 GCSNQYRIELZVTI-XZWHSSHBSA-N 0.000 claims 1
- WCGDDSQDPPDABN-IOWSJCHKSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(3-methoxy-5-methylphenyl)methylamino]-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(OC)C=C(C)C=1)C1=CC=CC=C1 WCGDDSQDPPDABN-IOWSJCHKSA-N 0.000 claims 1
- QMSVOKHGZZKZKE-URLMMPGGSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(3-nitrophenyl)methylamino]-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(C=CC=1)[N+]([O-])=O)C1=CC=CC=C1 QMSVOKHGZZKZKE-URLMMPGGSA-N 0.000 claims 1
- AZLWHCAOZGWHCN-XXWVNBFBSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(6-methoxy-2,3-dihydro-1h-inden-1-yl)amino]-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1C2=CC(OC)=CC=C2CC1)C1=CC=CC=C1 AZLWHCAOZGWHCN-XXWVNBFBSA-N 0.000 claims 1
- SCULFFZAUHGNCV-IOWSJCHKSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[2-(3-methoxyphenyl)ethylamino]-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCCC=1C=C(OC)C=CC=1)C1=CC=CC=C1 SCULFFZAUHGNCV-IOWSJCHKSA-N 0.000 claims 1
- DYCLSXOQBYRESU-IOWSJCHKSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[2-(4-methoxyphenyl)ethylamino]-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCCC=1C=CC(OC)=CC=1)C1=CC=CC=C1 DYCLSXOQBYRESU-IOWSJCHKSA-N 0.000 claims 1
- OTEAVZQKYHQWBF-XZWHSSHBSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[[2-methyl-5-(trifluoromethyl)phenyl]methylamino]-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C(=CC=C(C=1)C(F)(F)F)C)C1=CC=CC=C1 OTEAVZQKYHQWBF-XZWHSSHBSA-N 0.000 claims 1
- JPKBEKHKAIFUHQ-BJKOFHAPSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-4-(ethylamino)-3-hydroxy-1-phenylbutan-2-yl]benzamide Chemical compound C([C@@H]([C@H](O)CNCC)NC(=O)C=1C=C(C=C(NCC)C=1)N1S(CCCC1)(=O)=O)C1=CC=CC=C1 JPKBEKHKAIFUHQ-BJKOFHAPSA-N 0.000 claims 1
- ALUZEDVQRBRKKR-URLMMPGGSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-4-[(1-ethylcyclohexyl)amino]-3-hydroxy-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1(CC)CCCCC1)C1=CC=CC=C1 ALUZEDVQRBRKKR-URLMMPGGSA-N 0.000 claims 1
- KNUSIDUILOGCPF-AHKZPQOWSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-4-[(1-ethylpyrazol-4-yl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-2-fluorobenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC2=CN(CC)N=C2)=CC(NCC)=CC=1N1CCCCS1(=O)=O KNUSIDUILOGCPF-AHKZPQOWSA-N 0.000 claims 1
- XPNRBKPVBJXZOZ-IOWSJCHKSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-4-[(3-ethylphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(CC)C=CC=1)C1=CC=CC=C1 XPNRBKPVBJXZOZ-IOWSJCHKSA-N 0.000 claims 1
- PLMFJDWENBWGBS-URLMMPGGSA-N 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-n-[(2s,3r)-4-[(4-fluoro-3-methoxyphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(OC)C(F)=CC=1)C1=CC=CC=C1 PLMFJDWENBWGBS-URLMMPGGSA-N 0.000 claims 1
- HMGPEUCCHXJRBB-MFMCTBQISA-N 3-(1,1-dioxothiazinan-2-yl)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-4-methoxy-5-propylbenzamide Chemical compound COC=1C(CCC)=CC(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(C=CC=2)C(F)(F)F)=CC=1N1CCCCS1(=O)=O HMGPEUCCHXJRBB-MFMCTBQISA-N 0.000 claims 1
- OEOSJSMJQUWJGB-IOWSJCHKSA-N 3-(1,1-dioxothiazinan-2-yl)-n-[(2s,3r)-4-[(3-ethenylphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(C=C)C=CC=1)C1=CC=CC=C1 OEOSJSMJQUWJGB-IOWSJCHKSA-N 0.000 claims 1
- JWCSUEMLVWIRAJ-XZWHSSHBSA-N 3-(1,1-dioxothiazinan-2-yl)-n-[(2s,3r)-4-[(3-ethoxy-4-methoxyphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(OCC)C(OC)=CC=1)C1=CC=CC=C1 JWCSUEMLVWIRAJ-XZWHSSHBSA-N 0.000 claims 1
- YDJLRIQMJQEXSV-SDZVROEXSA-N 3-(benzylamino)-n-[(2s,3r)-4-[[(2s)-1-(cyclohexylamino)-1-oxopropan-2-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@@H]([C@H](O)CN[C@@H](C)C(=O)NC1CCCCC1)NC(=O)C=1C=C(C=C(NCC=2C=CC=CC=2)C=1)N1C(CCC1)=O)C1=CC=CC=C1 YDJLRIQMJQEXSV-SDZVROEXSA-N 0.000 claims 1
- GMETUKUQUCDDCD-UHFFFAOYSA-N 3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound NC(=O)C1=CC(NCC)=CC(N2C(CCC2)=O)=C1 GMETUKUQUCDDCD-UHFFFAOYSA-N 0.000 claims 1
- BKAHOOWZHTVMGF-BJKOFHAPSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(1,3-thiazol-2-ylmethylamino)butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1SC=CN=1)C1=CC=CC=C1 BKAHOOWZHTVMGF-BJKOFHAPSA-N 0.000 claims 1
- SRVJEHDGKSXUGW-URLMMPGGSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(2-phenylethylamino)butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCCC=1C=CC=CC=1)C1=CC=CC=C1 SRVJEHDGKSXUGW-URLMMPGGSA-N 0.000 claims 1
- OBHNLKCAHQEKPH-XZWHSSHBSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(2-phenylmethoxyethylamino)butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCCOCC=1C=CC=CC=1)C1=CC=CC=C1 OBHNLKCAHQEKPH-XZWHSSHBSA-N 0.000 claims 1
- IMIIWIPGEWPXLF-VHHLQSIKSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(3-phenylbutylamino)butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCCC(C)C=1C=CC=CC=1)C1=CC=CC=C1 IMIIWIPGEWPXLF-VHHLQSIKSA-N 0.000 claims 1
- VYIXTWLOLWKLIH-BJKOFHAPSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(propan-2-ylamino)butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC(C)C)C1=CC=CC=C1 VYIXTWLOLWKLIH-BJKOFHAPSA-N 0.000 claims 1
- QWIPCSCQSMLYGL-IOWSJCHKSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(quinolin-4-ylmethylamino)butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C2=CC=CC=C2N=CC=1)C1=CC=CC=C1 QWIPCSCQSMLYGL-IOWSJCHKSA-N 0.000 claims 1
- JKMKQSJNAYENGT-IZZNHLLZSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(thian-4-ylamino)butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC1CCSCC1)C1=CC=CC=C1 JKMKQSJNAYENGT-IZZNHLLZSA-N 0.000 claims 1
- OGCSOKYXTKXMQW-IOWSJCHKSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[(3-propoxyphenyl)methylamino]butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound CCCOC1=CC=CC(CNC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)C=2C=C(C=C(NCC)C=2)N2C(CCC2)=O)=C1 OGCSOKYXTKXMQW-IOWSJCHKSA-N 0.000 claims 1
- CQTZHQRZQGDWKL-IOWSJCHKSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[(4-propan-2-yloxyphenyl)methylamino]butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=CC(OC(C)C)=CC=1)C1=CC=CC=C1 CQTZHQRZQGDWKL-IOWSJCHKSA-N 0.000 claims 1
- ZDVISXXOPXEHTP-URLMMPGGSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[2-[3-(trifluoromethyl)phenyl]propan-2-ylamino]butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 ZDVISXXOPXEHTP-URLMMPGGSA-N 0.000 claims 1
- DUSOLAHJRJHBFU-PWUSVURUSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[(1s)-1-phenylethyl]amino]butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CN[C@@H](C)C=1C=CC=CC=1)C1=CC=CC=C1 DUSOLAHJRJHBFU-PWUSVURUSA-N 0.000 claims 1
- FYZYPBQEECJLCM-WUFINQPMSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(2h-tetrazol-5-yl)phenyl]methylamino]butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)C1=NNN=N1)C1=CC=CC=C1 FYZYPBQEECJLCM-WUFINQPMSA-N 0.000 claims 1
- QNEVJIWNSZTEGF-WUFINQPMSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethoxy)phenyl]methylamino]butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(OC(F)(F)F)C=CC=1)C1=CC=CC=C1 QNEVJIWNSZTEGF-WUFINQPMSA-N 0.000 claims 1
- GKNLPEWXTIMDRO-LBNVMWSVSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-4-methoxy-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound COC=1C(NCC)=CC(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(C=CC=2)C(F)(F)F)=CC=1N1CCCC1=O GKNLPEWXTIMDRO-LBNVMWSVSA-N 0.000 claims 1
- NMEDRRPAWMDCAT-URLMMPGGSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-5-(2-oxopiperidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 NMEDRRPAWMDCAT-URLMMPGGSA-N 0.000 claims 1
- RRQHONMNRORVAM-WUFINQPMSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[4-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=CC(=CC=1)C(F)(F)F)C1=CC=CC=C1 RRQHONMNRORVAM-WUFINQPMSA-N 0.000 claims 1
- NRFBZNIVALKTCV-FCHUYYIVSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(2,2,3,3,3-pentafluoropropylamino)-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC(F)(F)C(F)(F)F)C1=CC=CC=C1 NRFBZNIVALKTCV-FCHUYYIVSA-N 0.000 claims 1
- WRTZJQHJMVHLQC-JHOUSYSJSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(2-naphthalen-1-ylethylamino)-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCCC=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 WRTZJQHJMVHLQC-JHOUSYSJSA-N 0.000 claims 1
- UZIUDZHMORUFMT-WUFINQPMSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(3-methoxyanilino)-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC=1C=C(OC)C=CC=1)C1=CC=CC=C1 UZIUDZHMORUFMT-WUFINQPMSA-N 0.000 claims 1
- JVJDEKCDTCHBTL-LOSJGSFVSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(3-methylsulfanylpropylamino)-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCCCSC)C1=CC=CC=C1 JVJDEKCDTCHBTL-LOSJGSFVSA-N 0.000 claims 1
- FIFBFWIOEWWLTB-RRPNLBNLSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(4-methylpentylamino)-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCCCC(C)C)C1=CC=CC=C1 FIFBFWIOEWWLTB-RRPNLBNLSA-N 0.000 claims 1
- KDFMFNIYGTUGIZ-WUFINQPMSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(5-methylhexylamino)-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCCCCC(C)C)C1=CC=CC=C1 KDFMFNIYGTUGIZ-WUFINQPMSA-N 0.000 claims 1
- KEYMCXPYOIICBR-DBUNYZNWSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-(6-methylheptan-2-ylamino)-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC(C)CCCC(C)C)C1=CC=CC=C1 KEYMCXPYOIICBR-DBUNYZNWSA-N 0.000 claims 1
- XGYLKXTYMODLAQ-URLMMPGGSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(2-methoxy-5-methylphenyl)methylamino]-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C(=CC=C(C)C=1)OC)C1=CC=CC=C1 XGYLKXTYMODLAQ-URLMMPGGSA-N 0.000 claims 1
- PTIGXNFGODXOBH-WUFINQPMSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(2-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C(=CC=CC=1)OC)C1=CC=CC=C1 PTIGXNFGODXOBH-WUFINQPMSA-N 0.000 claims 1
- GFHGBUJQGLDRAP-XZWHSSHBSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(2-methyl-1-phenoxypropan-2-yl)amino]-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC(C)(C)COC=1C=CC=CC=1)C1=CC=CC=C1 GFHGBUJQGLDRAP-XZWHSSHBSA-N 0.000 claims 1
- UQCJNRMZQGSPNS-XZWHSSHBSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(2-methyl-1-phenylpropan-2-yl)amino]-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC(C)(C)CC=1C=CC=CC=1)C1=CC=CC=C1 UQCJNRMZQGSPNS-XZWHSSHBSA-N 0.000 claims 1
- MVUHWBURYANNRQ-VHHLQSIKSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(2-methyl-3-phenylpropyl)amino]-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC(C)CC=1C=CC=CC=1)C1=CC=CC=C1 MVUHWBURYANNRQ-VHHLQSIKSA-N 0.000 claims 1
- WDTKIUXCXWINCE-WUFINQPMSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(3-hydroxyphenyl)methylamino]-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(O)C=CC=1)C1=CC=CC=C1 WDTKIUXCXWINCE-WUFINQPMSA-N 0.000 claims 1
- DYNJADDGMXZVGJ-IOWSJCHKSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(3-imidazol-1-ylphenyl)methylamino]-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)N1C=NC=C1)C1=CC=CC=C1 DYNJADDGMXZVGJ-IOWSJCHKSA-N 0.000 claims 1
- LOSXHSZFMDFLCU-WUFINQPMSA-N 3-(ethylamino)-n-[(2s,3r)-3-hydroxy-4-[(3-nitrophenyl)methylamino]-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)[N+]([O-])=O)C1=CC=CC=C1 LOSXHSZFMDFLCU-WUFINQPMSA-N 0.000 claims 1
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- HIEQBPWNVRUPBB-SZAHLOSFSA-N 3-cyclopentyl-n-[(2s,3r)-4-[(3,5-dimethoxyphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-5-(1,1-dioxothiazinan-2-yl)benzamide Chemical compound COC1=CC(OC)=CC(CNC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)C=2C=C(C=C(C=2)C2CCCC2)N2S(CCCC2)(=O)=O)=C1 HIEQBPWNVRUPBB-SZAHLOSFSA-N 0.000 claims 1
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- WQMGFDHBHFQICH-WUFINQPMSA-N 3-ethoxy-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethoxy)phenyl]methylamino]butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(OC(F)(F)F)C=CC=1)C1=CC=CC=C1 WQMGFDHBHFQICH-WUFINQPMSA-N 0.000 claims 1
- IKDGJGJMOPEBOW-UHFFFAOYSA-N 3-ethoxy-n-[3-hydroxy-4-(6-methylheptan-2-ylamino)-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C=1C(OCC)=CC(N2C(CCC2)=O)=CC=1C(=O)NC(C(O)CNC(C)CCCC(C)C)CC1=CC=CC=C1 IKDGJGJMOPEBOW-UHFFFAOYSA-N 0.000 claims 1
- NPUCTBVIUUVEMU-UHFFFAOYSA-N 3-ethoxy-n-[3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C=1C(OCC)=CC(N2C(CCC2)=O)=CC=1C(=O)NC(C(O)CNCC=1C=C(OC)C=CC=1)CC1=CC=CC=C1 NPUCTBVIUUVEMU-UHFFFAOYSA-N 0.000 claims 1
- PDSQRRHTCBEYNZ-UKILVPOCSA-N 3-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(propan-2-ylamino)butan-2-yl]-7-(2-oxopyrrolidin-1-yl)-1h-indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2NC=C(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC(C)C)C1=CC=CC=C1 PDSQRRHTCBEYNZ-UKILVPOCSA-N 0.000 claims 1
- IQAAGQVGHVNJOR-IGYGKHONSA-N 3-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[2-[3-(trifluoromethyl)phenyl]propan-2-ylamino]butan-2-yl]-1-methyl-7-(2-oxopyrrolidin-1-yl)indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N(C)C=C(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 IQAAGQVGHVNJOR-IGYGKHONSA-N 0.000 claims 1
- JWKNCOPNSMONKG-LITSAYRRSA-N 3-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[2-[3-(trifluoromethyl)phenyl]propan-2-ylamino]butan-2-yl]-7-(2-oxopyrrolidin-1-yl)benzimidazole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N=CN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 JWKNCOPNSMONKG-LITSAYRRSA-N 0.000 claims 1
- JTMOMHWUYKYKBN-LBNVMWSVSA-N 3-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-7-(2-oxopyrrolidin-1-yl)benzimidazole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N=CN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 JTMOMHWUYKYKBN-LBNVMWSVSA-N 0.000 claims 1
- WJVIKTWKVRMSDW-RPLLCQBOSA-N 3-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-7-(2-oxopyrrolidin-1-yl)benzotriazole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N=NN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 WJVIKTWKVRMSDW-RPLLCQBOSA-N 0.000 claims 1
- AKBSTNSSUJWIKM-LITSAYRRSA-N 3-ethyl-n-[(2s,3r)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-7-(2-oxopyrrolidin-1-yl)benzimidazole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N=CN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(OC)C=CC=1)C1=CC=CC=C1 AKBSTNSSUJWIKM-LITSAYRRSA-N 0.000 claims 1
- CSUBIWBZHJEABL-BHBYDHKZSA-N 3-ethyl-n-[(2s,3r)-3-hydroxy-4-[2-(3-methoxyphenyl)propan-2-ylamino]-1-phenylbutan-2-yl]-7-(2-oxopyrrolidin-1-yl)benzimidazole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N=CN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC(C)(C)C=1C=C(OC)C=CC=1)C1=CC=CC=C1 CSUBIWBZHJEABL-BHBYDHKZSA-N 0.000 claims 1
- VJAKDEGRIZMQQX-UHFFFAOYSA-N 3-ethylsulfonyl-n-[3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C=1C(S(=O)(=O)CC)=CC(N2C(CCC2)=O)=CC=1C(=O)NC(C(O)CNCC=1C=C(C=CC=1)C(F)(F)F)CC1=CC=CC=C1 VJAKDEGRIZMQQX-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- ZHXOMJZWSXGMIO-YNOBPPCASA-N 3-n-[(2s,3r)-4-[[(2s)-1-(cyclohexylamino)-1-oxopropan-2-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-1-n-methyl-5-(2-oxopyrrolidin-1-yl)benzene-1,3-dicarboxamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)C(=O)NC)N1C(CCC1)=O)[C@H](O)CN[C@@H](C)C(=O)NC1CCCCC1)C1=CC=CC=C1 ZHXOMJZWSXGMIO-YNOBPPCASA-N 0.000 claims 1
- IRTAWXCZUBAASL-KEPSJGTLSA-N 3-n-[(2s,3r)-4-[[(2s)-1-(cyclohexylamino)-1-oxopropan-2-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-5-(2-oxopyrrolidin-1-yl)-1-n-propylbenzene-1,3-dicarboxamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)C(=O)NCCC)N1C(CCC1)=O)[C@H](O)CN[C@@H](C)C(=O)NC1CCCCC1)C1=CC=CC=C1 IRTAWXCZUBAASL-KEPSJGTLSA-N 0.000 claims 1
- MCAKXURUTPYGPS-BHBYDHKZSA-N 4-(1,1-dioxo-1,2-thiazolidin-2-yl)-1-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[2-[3-(trifluoromethyl)phenyl]propan-2-ylamino]butan-2-yl]indazole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=NN(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 MCAKXURUTPYGPS-BHBYDHKZSA-N 0.000 claims 1
- RNOBDNXPAPRBOD-QCENPCRXSA-N 4-(1,1-dioxo-1,2-thiazolidin-2-yl)-1-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[2-[3-(trifluoromethyl)phenyl]propan-2-ylamino]butan-2-yl]indole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=CN(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 RNOBDNXPAPRBOD-QCENPCRXSA-N 0.000 claims 1
- HVNQGEMQCNRHHN-QCENPCRXSA-N 4-(1,1-dioxothiazinan-2-yl)-1-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]indole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=CN(C2=C1)CC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 HVNQGEMQCNRHHN-QCENPCRXSA-N 0.000 claims 1
- LEBXOHJXAKSRNH-ALYLKEMTSA-N 4-chloro-n-[(2s,3r)-4-[[(2s)-1-(cyclohexylamino)-1-oxopropan-2-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-3,5-bis(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@@H]([C@H](O)CN[C@@H](C)C(=O)NC1CCCCC1)NC(=O)C=1C=C(C(Cl)=C(N2C(CCC2)=O)C=1)N1C(CCC1)=O)C1=CC=CC=C1 LEBXOHJXAKSRNH-ALYLKEMTSA-N 0.000 claims 1
- ASAJVNGIJZCMAM-SZAHLOSFSA-N 5-(1,1-dioxothiazinan-2-yl)-1-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[2-[3-(trifluoromethyl)phenyl]propan-2-ylamino]butan-2-yl]-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)C(=O)N(CCC)CCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 ASAJVNGIJZCMAM-SZAHLOSFSA-N 0.000 claims 1
- KCQAMDDVQXZDMS-OIDHKYIRSA-N 5-(1,1-dioxothiazinan-2-yl)-1-n-[(2s,3r)-3-hydroxy-4-[2-(3-methoxyphenyl)propan-2-ylamino]-1-phenylbutan-2-yl]-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)C(=O)N(CCC)CCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)(C)C=1C=C(OC)C=CC=1)C1=CC=CC=C1 KCQAMDDVQXZDMS-OIDHKYIRSA-N 0.000 claims 1
- ACKOAYZBYSHTNV-JTHBVZDNSA-N 5-(ethylamino)-2-fluoro-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(propan-2-ylamino)butan-2-yl]-3-(2-oxopyrrolidin-1-yl)benzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC(C)C)=CC(NCC)=CC=1N1CCCC1=O ACKOAYZBYSHTNV-JTHBVZDNSA-N 0.000 claims 1
- WUVGWKWYMZATJQ-XTEPFMGCSA-N 5-(ethylamino)-2-fluoro-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[2-[3-(trifluoromethyl)phenyl]propan-2-ylamino]butan-2-yl]-3-(2-oxopyrrolidin-1-yl)benzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC(C)(C)C=2C=C(C=CC=2)C(F)(F)F)=CC(NCC)=CC=1N1CCCC1=O WUVGWKWYMZATJQ-XTEPFMGCSA-N 0.000 claims 1
- RQXGWBAZTYRGOW-AHKZPQOWSA-N 5-(ethylamino)-2-fluoro-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-3-(2-oxopyrrolidin-1-yl)benzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(C=CC=2)C(F)(F)F)=CC(NCC)=CC=1N1CCCC1=O RQXGWBAZTYRGOW-AHKZPQOWSA-N 0.000 claims 1
- PWLOLQHFEGCIPB-UKILVPOCSA-N 7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-(propan-2-ylamino)butan-2-yl]-1h-indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2NC=C(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNC(C)C)C1=CC=CC=C1 PWLOLQHFEGCIPB-UKILVPOCSA-N 0.000 claims 1
- QQKOTWMTJZYNCP-MFMCTBQISA-N 7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[2-[3-(trifluoromethyl)phenyl]propan-2-ylamino]butan-2-yl]-1h-indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2NC=C(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 QQKOTWMTJZYNCP-MFMCTBQISA-N 0.000 claims 1
- KRVYEWUDVIFUNR-LITSAYRRSA-N 7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[2-[3-(trifluoromethyl)phenyl]propan-2-ylamino]butan-2-yl]benzimidazole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N=CN(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 KRVYEWUDVIFUNR-LITSAYRRSA-N 0.000 claims 1
- KYKIPCVEBMYXGT-MFMCTBQISA-N 7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-1-methylindole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N(C)C=C(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 KYKIPCVEBMYXGT-MFMCTBQISA-N 0.000 claims 1
- AIFQQZHBKWWCQW-LMSSTIIKSA-N 7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-1h-indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2NC=C(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 AIFQQZHBKWWCQW-LMSSTIIKSA-N 0.000 claims 1
- RNWHKLASIGYSPH-LITSAYRRSA-N 8-(1,1-dioxo-1,2-thiazolidin-2-yl)-4-ethyl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-2,3-dihydro-1h-quinoxaline-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2NCCN(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 RNWHKLASIGYSPH-LITSAYRRSA-N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- LCYLAVXFYMFSRB-UHFFFAOYSA-N formic acid;n-[3-hydroxy-4-(6-methylheptan-2-ylamino)-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-propylbenzamide Chemical compound OC=O.C=1C(CCC)=CC(N2C(CCC2)=O)=CC=1C(=O)NC(C(O)CNC(C)CCCC(C)C)CC1=CC=CC=C1 LCYLAVXFYMFSRB-UHFFFAOYSA-N 0.000 claims 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- KLBNNHSLQHMKOE-YNOBPPCASA-N methyl 3-[[(2s,3r)-4-[[(2s)-1-(cyclohexylamino)-1-oxopropan-2-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]carbamoyl]-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)C(=O)OC)N1C(CCC1)=O)[C@H](O)CN[C@@H](C)C(=O)NC1CCCCC1)C1=CC=CC=C1 KLBNNHSLQHMKOE-YNOBPPCASA-N 0.000 claims 1
- FTEWGZRSZVOFRL-XSJQRQGXSA-N n-[(2s,3r)-1-(2-chlorophenyl)-3-hydroxy-4-(6-methylheptan-2-ylamino)butan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)CCCC(C)C)C1=CC=CC=C1Cl FTEWGZRSZVOFRL-XSJQRQGXSA-N 0.000 claims 1
- SQBZRULONFPLOQ-WUFINQPMSA-N n-[(2s,3r)-1-(2-chlorophenyl)-4-(cyclohexylamino)-3-hydroxybutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1Cl SQBZRULONFPLOQ-WUFINQPMSA-N 0.000 claims 1
- VTZBQYCIEZAXRO-XZWHSSHBSA-N n-[(2s,3r)-1-(3,4-difluorophenyl)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxybutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC=C(F)C(F)=C1 VTZBQYCIEZAXRO-XZWHSSHBSA-N 0.000 claims 1
- RJLWZHPXWCHBSI-CTIJWOEKSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-(6-methylheptan-2-ylamino)butan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)CCCC(C)C)C1=CC(F)=CC(F)=C1 RJLWZHPXWCHBSI-CTIJWOEKSA-N 0.000 claims 1
- OYRJVJLVRLQYHL-XZWHSSHBSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]butan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(OC)C=CC=1)C1=CC(F)=CC(F)=C1 OYRJVJLVRLQYHL-XZWHSSHBSA-N 0.000 claims 1
- KRONARNUBZQJAK-URLMMPGGSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC(F)=CC(F)=C1 KRONARNUBZQJAK-URLMMPGGSA-N 0.000 claims 1
- VLPDHNKKYKMGKW-XZWHSSHBSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxybutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC(F)=CC(F)=C1 VLPDHNKKYKMGKW-XZWHSSHBSA-N 0.000 claims 1
- SNJHTFZUNBOZOI-XSJQRQGXSA-N n-[(2s,3r)-1-(3-chlorophenyl)-3-hydroxy-4-(6-methylheptan-2-ylamino)butan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)CCCC(C)C)C1=CC=CC(Cl)=C1 SNJHTFZUNBOZOI-XSJQRQGXSA-N 0.000 claims 1
- LWOJHQVHMZGKHF-WUFINQPMSA-N n-[(2s,3r)-1-(4-chlorophenyl)-4-(cyclohexylamino)-3-hydroxybutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CCCCC1)C1=CC=C(Cl)C=C1 LWOJHQVHMZGKHF-WUFINQPMSA-N 0.000 claims 1
- SQBBRVNOCUZMBH-AJQTZOPKSA-N n-[(2s,3r)-3-hydroxy-1-phenyl-4-(2-phenylethylamino)butan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-pentoxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCCCCC)N1C(CCC1)=O)[C@H](O)CNCCC=1C=CC=CC=1)C1=CC=CC=C1 SQBBRVNOCUZMBH-AJQTZOPKSA-N 0.000 claims 1
- QYPTWQUCAZWPFW-AOKUBALNSA-N n-[(2s,3r)-3-hydroxy-1-phenyl-4-(2-phenylpropylamino)butan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-pentoxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCCCCC)N1C(CCC1)=O)[C@H](O)CNCC(C)C=1C=CC=CC=1)C1=CC=CC=C1 QYPTWQUCAZWPFW-AOKUBALNSA-N 0.000 claims 1
- COHMAUZKJVHAMG-VICIGFPDSA-N n-[(2s,3r)-3-hydroxy-1-phenyl-4-(propan-2-ylamino)butan-2-yl]-3-(2-oxo-5-phenylpiperidin-1-yl)-5-propylbenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)CCC)N1C(CCC(C1)C=1C=CC=CC=1)=O)[C@H](O)CNC(C)C)C1=CC=CC=C1 COHMAUZKJVHAMG-VICIGFPDSA-N 0.000 claims 1
- SMFYBMGVWLCZID-XZWHSSHBSA-N n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-3-(2-oxopiperidin-1-yl)-5-propylbenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)CCC)N1C(CCCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 SMFYBMGVWLCZID-XZWHSSHBSA-N 0.000 claims 1
- GWUHITMXWHPEMO-XTEPFMGCSA-N n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-3-methyl-7-(2-oxopyrrolidin-1-yl)-1h-indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2NC=C(C2=C1)C)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 GWUHITMXWHPEMO-XTEPFMGCSA-N 0.000 claims 1
- IEOGEMZAEVYXDA-PJGYDLQESA-N n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-4-methyl-8-(2-oxopyrrolidin-1-yl)-3,4-dihydro-2h-chromene-6-carboxamide Chemical compound CC1CCOC2=C1C=C(C(=O)N[C@@H](CC=1C=CC=CC=1)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C=C2N1CCCC1=O IEOGEMZAEVYXDA-PJGYDLQESA-N 0.000 claims 1
- XKOSWBGITYDBGI-URLMMPGGSA-N n-[(2s,3r)-3-hydroxy-4-(3-methylbutylamino)-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-pentoxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCCCCC)N1C(CCC1)=O)[C@H](O)CNCCC(C)C)C1=CC=CC=C1 XKOSWBGITYDBGI-URLMMPGGSA-N 0.000 claims 1
- AINUPDUGUKELCP-DFCNTKNDSA-N n-[(2s,3r)-3-hydroxy-4-(6-methylheptan-2-ylamino)-1-phenylbutan-2-yl]-3-(2-oxopiperidin-1-yl)-5-propylbenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)CCC)N1C(CCCC1)=O)[C@H](O)CNC(C)CCCC(C)C)C1=CC=CC=C1 AINUPDUGUKELCP-DFCNTKNDSA-N 0.000 claims 1
- YXEQYNMFUVOHPB-ZWBSKDEBSA-N n-[(2s,3r)-3-hydroxy-4-(6-methylheptan-2-ylamino)-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-(propan-2-ylamino)benzamide Chemical compound C([C@@H]([C@H](O)CNC(C)CCCC(C)C)NC(=O)C=1C=C(C=C(NC(C)C)C=1)N1C(CCC1)=O)C1=CC=CC=C1 YXEQYNMFUVOHPB-ZWBSKDEBSA-N 0.000 claims 1
- JCCCVCZRHCGQNB-ZWBSKDEBSA-N n-[(2s,3r)-3-hydroxy-4-(6-methylheptan-2-ylamino)-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-propan-2-yloxybenzamide Chemical compound C([C@@H]([C@H](O)CNC(C)CCCC(C)C)NC(=O)C=1C=C(C=C(OC(C)C)C=1)N1C(CCC1)=O)C1=CC=CC=C1 JCCCVCZRHCGQNB-ZWBSKDEBSA-N 0.000 claims 1
- AROCXDVRQJFXHU-XZWHSSHBSA-N n-[(2s,3r)-3-hydroxy-4-[(1-methylpiperidin-4-yl)amino]-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-pentoxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCCCCC)N1C(CCC1)=O)[C@H](O)CNC1CCN(C)CC1)C1=CC=CC=C1 AROCXDVRQJFXHU-XZWHSSHBSA-N 0.000 claims 1
- XCGBSFGZWYRSQF-BJKOFHAPSA-N n-[(2s,3r)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC(CNC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)C=2C(=CC=CC=2)OC)=C1 XCGBSFGZWYRSQF-BJKOFHAPSA-N 0.000 claims 1
- ZLCZIJWEFXBPOV-OIDHKYIRSA-N n-[(2s,3r)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-(2-phenylethyl)benzamide Chemical compound COC1=CC=CC(CNC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)C=2C=C(C=C(CCC=3C=CC=CC=3)C=2)N2C(CCC2)=O)=C1 ZLCZIJWEFXBPOV-OIDHKYIRSA-N 0.000 claims 1
- SNSVARXQNVKEFP-CJDDIQBSSA-N n-[(2s,3r)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-[(e)-2-phenylethenyl]benzamide Chemical compound COC1=CC=CC(CNC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)C=2C=C(C=C(\C=C\C=3C=CC=CC=3)C=2)N2C(CCC2)=O)=C1 SNSVARXQNVKEFP-CJDDIQBSSA-N 0.000 claims 1
- XUCNHWJHINCOPO-URLMMPGGSA-N n-[(2s,3r)-4-(1-benzofuran-2-ylmethylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1OC2=CC=CC=C2C=1)C1=CC=CC=C1 XUCNHWJHINCOPO-URLMMPGGSA-N 0.000 claims 1
- QJUQXPAEJUQELG-URLMMPGGSA-N n-[(2s,3r)-4-(2,3-dihydro-1,4-benzodioxin-6-ylmethylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C2OCCOC2=CC=1)C1=CC=CC=C1 QJUQXPAEJUQELG-URLMMPGGSA-N 0.000 claims 1
- UUPXDMVPWUQXFY-XZWHSSHBSA-N n-[(2s,3r)-4-(2,3-dihydro-1-benzofuran-6-ylmethylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C2OCCC2=CC=1)C1=CC=CC=C1 UUPXDMVPWUQXFY-XZWHSSHBSA-N 0.000 claims 1
- QBDFDJUMTZXSNV-IOWSJCHKSA-N n-[(2s,3r)-4-(2,3-dihydro-1h-inden-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CC2=CC=CC=C2C1)C1=CC=CC=C1 QBDFDJUMTZXSNV-IOWSJCHKSA-N 0.000 claims 1
- WWKMZFIDBRXHFT-LMSSTIIKSA-N n-[(2s,3r)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-2-fluoro-3-(2-oxopyrrolidin-1-yl)-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC(C)(C)CCCC(C)C)=CC(CCC)=CC=1N1CCCC1=O WWKMZFIDBRXHFT-LMSSTIIKSA-N 0.000 claims 1
- SVJMEICVWIBOPZ-LMSSTIIKSA-N n-[(2s,3r)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxo-1,2-thiazolidin-2-yl)-2-fluoro-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC(C)(C)CCCC(C)C)=CC(CCC)=CC=1N1CCCS1(=O)=O SVJMEICVWIBOPZ-LMSSTIIKSA-N 0.000 claims 1
- BPJPAMRGQLPTLT-URLMMPGGSA-N n-[(2s,3r)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxo-1,2-thiazolidin-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCC1)(=O)=O)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC=CC=C1 BPJPAMRGQLPTLT-URLMMPGGSA-N 0.000 claims 1
- HTVIBPYYVYUSBD-XZWHSSHBSA-N n-[(2s,3r)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC=CC=C1 HTVIBPYYVYUSBD-XZWHSSHBSA-N 0.000 claims 1
- QUTJAEIUCNMDGD-MFMCTBQISA-N n-[(2s,3r)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-ethyl-7-(2-oxopyrrolidin-1-yl)-1h-indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2NC=C(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC=CC=C1 QUTJAEIUCNMDGD-MFMCTBQISA-N 0.000 claims 1
- KNXAJYQOTQRTED-BHBYDHKZSA-N n-[(2s,3r)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-4-(1,1-dioxo-1,2-thiazolidin-2-yl)-1-ethylindazole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=NN(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC=CC=C1 KNXAJYQOTQRTED-BHBYDHKZSA-N 0.000 claims 1
- MKWJJODNIZEOMQ-XTEPFMGCSA-N n-[(2s,3r)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-5-(ethylamino)-2-fluoro-3-(2-oxopyrrolidin-1-yl)benzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC(C)(C)CCCC(C)C)=CC(NCC)=CC=1N1CCCC1=O MKWJJODNIZEOMQ-XTEPFMGCSA-N 0.000 claims 1
- HQPHCWVOHJLJRI-IGYGKHONSA-N n-[(2s,3r)-4-(2,6-dimethylheptan-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethyl-1-methylindole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N(C)C=C(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC=CC=C1 HQPHCWVOHJLJRI-IGYGKHONSA-N 0.000 claims 1
- BFANCPGKMNFWRL-AZGAKELHSA-N n-[(2s,3r)-4-(3,3-dimethylbutylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-2-fluorobenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCCC(C)(C)C)=CC(NCC)=CC=1N1CCCCS1(=O)=O BFANCPGKMNFWRL-AZGAKELHSA-N 0.000 claims 1
- ICHYDDOSEMZNKC-RRPNLBNLSA-N n-[(2s,3r)-4-(3,3-dimethylbutylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCCC(C)(C)C)C1=CC=CC=C1 ICHYDDOSEMZNKC-RRPNLBNLSA-N 0.000 claims 1
- OCHRGIYSHSUUFY-ROPDQJSTSA-N n-[(2s,3r)-4-(4-bicyclo[2.2.2]octanylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC12CCC(CC1)CC2)C1=CC=CC=C1 OCHRGIYSHSUUFY-ROPDQJSTSA-N 0.000 claims 1
- WUYOJSGIKRCAKP-URLMMPGGSA-N n-[(2s,3r)-4-(benzylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=CC=CC=1)C1=CC=CC=C1 WUYOJSGIKRCAKP-URLMMPGGSA-N 0.000 claims 1
- HNUARHGVGKDEPI-IOWSJCHKSA-N n-[(2s,3r)-4-(benzylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-pentoxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCCCCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=CC=CC=1)C1=CC=CC=C1 HNUARHGVGKDEPI-IOWSJCHKSA-N 0.000 claims 1
- UPUUBLADZSTGOB-FQHCJVPLSA-N n-[(2s,3r)-4-(butan-2-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC(C)CC)C1=CC=CC=C1 UPUUBLADZSTGOB-FQHCJVPLSA-N 0.000 claims 1
- HJAZGBGAUPRYOP-IZZNHLLZSA-N n-[(2s,3r)-4-(butylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@@H]([C@H](O)CNCCCC)NC(=O)C=1C=C(C=C(NCC)C=1)N1S(CCCC1)(=O)=O)C1=CC=CC=C1 HJAZGBGAUPRYOP-IZZNHLLZSA-N 0.000 claims 1
- PUWUFZIQBYDCRP-WHWDJVTISA-N n-[(2s,3r)-4-(cyclohex-3-en-1-ylmethylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC1CC=CCC1)C1=CC=CC=C1 PUWUFZIQBYDCRP-WHWDJVTISA-N 0.000 claims 1
- PIIHALVZODZOBH-WUFINQPMSA-N n-[(2s,3r)-4-(cyclohexylamino)-1-(3,4-difluorophenyl)-3-hydroxybutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CCCCC1)C1=CC=C(F)C(F)=C1 PIIHALVZODZOBH-WUFINQPMSA-N 0.000 claims 1
- CKVZQVXZQCBZLH-WUFINQPMSA-N n-[(2s,3r)-4-(cyclohexylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CCCCC1)C1=CC(F)=CC(F)=C1 CKVZQVXZQCBZLH-WUFINQPMSA-N 0.000 claims 1
- WGTPDGWMVISXRN-IZZNHLLZSA-N n-[(2s,3r)-4-(cyclohexylamino)-1-(furan-2-yl)-3-hydroxybutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CCCCC1)C1=CC=CO1 WGTPDGWMVISXRN-IZZNHLLZSA-N 0.000 claims 1
- NJPXIXZEWFGYGP-LITSAYRRSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-1-ethyl-4-(2-oxopyrrolidin-1-yl)indole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=CN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 NJPXIXZEWFGYGP-LITSAYRRSA-N 0.000 claims 1
- YVQXNNJBRPXHHZ-AZGAKELHSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxo-1,2-thiazolidin-2-yl)-5-(ethylamino)-2-fluorobenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC2CCCCC2)=CC(NCC)=CC=1N1CCCS1(=O)=O YVQXNNJBRPXHHZ-AZGAKELHSA-N 0.000 claims 1
- NDVLPZJRVOKBCU-GLGVHQJESA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxo-4-phenylthiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCC(C1)C=1C=CC=CC=1)(=O)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 NDVLPZJRVOKBCU-GLGVHQJESA-N 0.000 claims 1
- PKMPPUBHPJPCRL-WUFINQPMSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 PKMPPUBHPJPCRL-WUFINQPMSA-N 0.000 claims 1
- MPOCRKFHDRGMLZ-XZWHSSHBSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-pentoxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCCCCC)N1C(CCC1)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 MPOCRKFHDRGMLZ-XZWHSSHBSA-N 0.000 claims 1
- PVDHVIVUNLQJLY-RRPNLBNLSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 PVDHVIVUNLQJLY-RRPNLBNLSA-N 0.000 claims 1
- CXVKJSFSPHXTJR-IOWSJCHKSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-cyclopentyl-5-(1,1-dioxothiazinan-2-yl)benzamide Chemical compound C([C@@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)C=1C=C(C=C(C=1)C1CCCC1)N1S(CCCC1)(=O)=O)NC1CCCCC1 CXVKJSFSPHXTJR-IOWSJCHKSA-N 0.000 claims 1
- FKGDTRXCZHZVFH-LMSSTIIKSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-ethyl-1-methyl-7-(2-oxopyrrolidin-1-yl)indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N(C)C=C(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 FKGDTRXCZHZVFH-LMSSTIIKSA-N 0.000 claims 1
- ZSCPPZIRNSFDCQ-XTEPFMGCSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-ethyl-7-(2-oxopyrrolidin-1-yl)-1h-indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2NC=C(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 ZSCPPZIRNSFDCQ-XTEPFMGCSA-N 0.000 claims 1
- QSYMNHIIAPEVHN-RPLLCQBOSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-ethyl-7-(2-oxopyrrolidin-1-yl)benzimidazole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N=CN(C2=C1)CC)N1C(CCC1)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 QSYMNHIIAPEVHN-RPLLCQBOSA-N 0.000 claims 1
- PXVJZKXAKZWKGT-LITSAYRRSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-4-(1,1-dioxo-1,2-thiazolidin-2-yl)-1-ethylindole-6-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2C=CN(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 PXVJZKXAKZWKGT-LITSAYRRSA-N 0.000 claims 1
- MAGLKXUHYIZQNZ-AZGAKELHSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-5-(ethylamino)-2-fluoro-3-(2-oxopyrrolidin-1-yl)benzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNC2CCCCC2)=CC(NCC)=CC=1N1CCCC1=O MAGLKXUHYIZQNZ-AZGAKELHSA-N 0.000 claims 1
- FOGJOTGKRPWNHV-LMSSTIIKSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethyl-1-methylindole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2N(C)C=C(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 FOGJOTGKRPWNHV-LMSSTIIKSA-N 0.000 claims 1
- MTIZZECUOUZVLK-XTEPFMGCSA-N n-[(2s,3r)-4-(cyclohexylamino)-3-hydroxy-1-phenylbutan-2-yl]-7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethyl-1h-indole-5-carboxamide Chemical compound C([C@H](NC(=O)C1=CC(=C2NC=C(C2=C1)CC)N1S(CCC1)(=O)=O)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 MTIZZECUOUZVLK-XTEPFMGCSA-N 0.000 claims 1
- AMVDNFIQANYLEW-LOSJGSFVSA-N n-[(2s,3r)-4-(cyclopropylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CC1)C1=CC=CC=C1 AMVDNFIQANYLEW-LOSJGSFVSA-N 0.000 claims 1
- WVACRJFVEXCPRY-BJKOFHAPSA-N n-[(2s,3r)-4-(cyclopropylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC1CC1)C1=CC=CC=C1 WVACRJFVEXCPRY-BJKOFHAPSA-N 0.000 claims 1
- RVVGLWQADLAQEY-IZZNHLLZSA-N n-[(2s,3r)-4-(cyclopropylmethylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC1CC1)C1=CC=CC=C1 RVVGLWQADLAQEY-IZZNHLLZSA-N 0.000 claims 1
- OVKSOEUSFYCBPB-IOWSJCHKSA-N n-[(2s,3r)-4-(heptan-4-ylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-pentoxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCCCCC)N1C(CCC1)=O)[C@H](O)CNC(CCC)CCC)C1=CC=CC=C1 OVKSOEUSFYCBPB-IOWSJCHKSA-N 0.000 claims 1
- UUOVJAYEOKOKAN-BJKOFHAPSA-N n-[(2s,3r)-4-(tert-butylamino)-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC(C)(C)C)C1=CC=CC=C1 UUOVJAYEOKOKAN-BJKOFHAPSA-N 0.000 claims 1
- DXLBVPMQAKQBFX-POZJPKTBSA-N n-[(2s,3r)-4-[(2,2-dimethylcyclohexyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1C(CCCC1)(C)C)C1=CC=CC=C1 DXLBVPMQAKQBFX-POZJPKTBSA-N 0.000 claims 1
- CDUJEPFJCHHNBZ-RRPNLBNLSA-N n-[(2s,3r)-4-[(2,3-dichlorophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C(=C(Cl)C=CC=1)Cl)C1=CC=CC=C1 CDUJEPFJCHHNBZ-RRPNLBNLSA-N 0.000 claims 1
- SBMWXKFHNABHGF-SCXVOSTRSA-N n-[(2s,3r)-4-[(3,3-dimethylcyclopentyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CC(C)(C)CC1)C1=CC=CC=C1 SBMWXKFHNABHGF-SCXVOSTRSA-N 0.000 claims 1
- LKZPLXPNMZWKSU-WUFINQPMSA-N n-[(2s,3r)-4-[(3,4-difluorophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(F)C(F)=CC=1)C1=CC=CC=C1 LKZPLXPNMZWKSU-WUFINQPMSA-N 0.000 claims 1
- WYSLSXXQLKMNFW-XTEPFMGCSA-N n-[(2s,3r)-4-[(3,4-dimethoxyphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-2-fluoro-3-(2-oxopyrrolidin-1-yl)-5-propylbenzamide Chemical compound FC=1C(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(OC)C(OC)=CC=2)=CC(CCC)=CC=1N1CCCC1=O WYSLSXXQLKMNFW-XTEPFMGCSA-N 0.000 claims 1
- MSFAEPQUPNQOJO-WUFINQPMSA-N n-[(2s,3r)-4-[(3,5-dichlorophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxo-1,2-thiazolidin-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCC1)(=O)=O)[C@H](O)CNCC=1C=C(Cl)C=C(Cl)C=1)C1=CC=CC=C1 MSFAEPQUPNQOJO-WUFINQPMSA-N 0.000 claims 1
- NNDZRQQBRKYZEI-URLMMPGGSA-N n-[(2s,3r)-4-[(3,5-dichlorophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxo-1,2-thiazolidin-2-yl)-5-propan-2-yloxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OC(C)C)N1S(CCC1)(=O)=O)[C@H](O)CNCC=1C=C(Cl)C=C(Cl)C=1)C1=CC=CC=C1 NNDZRQQBRKYZEI-URLMMPGGSA-N 0.000 claims 1
- PKWQZSLPPXHBOP-URLMMPGGSA-N n-[(2s,3r)-4-[(3,5-dichlorophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(Cl)C=C(Cl)C=1)C1=CC=CC=C1 PKWQZSLPPXHBOP-URLMMPGGSA-N 0.000 claims 1
- DGPOHRWSIWOZRZ-URLMMPGGSA-N n-[(2s,3r)-4-[(3,5-dichlorophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-ethoxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(Cl)C=C(Cl)C=1)C1=CC=CC=C1 DGPOHRWSIWOZRZ-URLMMPGGSA-N 0.000 claims 1
- HHDGZIIKNIWBJV-IOWSJCHKSA-N n-[(2s,3r)-4-[(3,5-dimethoxyphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(OC)C=C(OC)C=1)C1=CC=CC=C1 HHDGZIIKNIWBJV-IOWSJCHKSA-N 0.000 claims 1
- SSZNOTKRMCHVHJ-XZWHSSHBSA-N n-[(2s,3r)-4-[(3,5-dimethoxyphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-ethoxy-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(OC)C=C(OC)C=1)C1=CC=CC=C1 SSZNOTKRMCHVHJ-XZWHSSHBSA-N 0.000 claims 1
- GJBUTYGJNROAPX-OIDHKYIRSA-N n-[(2s,3r)-4-[(3,5-ditert-butylphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(C=C(C=1)C(C)(C)C)C(C)(C)C)C1=CC=CC=C1 GJBUTYGJNROAPX-OIDHKYIRSA-N 0.000 claims 1
- UIUFIMWUHRZRKT-XZWHSSHBSA-N n-[(2s,3r)-4-[(3-acetamidophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(NC(C)=O)C=CC=1)C1=CC=CC=C1 UIUFIMWUHRZRKT-XZWHSSHBSA-N 0.000 claims 1
- AQFSTPXMWGRDCW-URLMMPGGSA-N n-[(2s,3r)-4-[(3-bromo-5-fluorophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCC=1C=C(Br)C=C(F)C=1)C1=CC=CC=C1 AQFSTPXMWGRDCW-URLMMPGGSA-N 0.000 claims 1
- WIKWZMDBKJAZHP-WUFINQPMSA-N n-[(2s,3r)-4-[(3-chloro-4-methoxyphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(Cl)C(OC)=CC=1)C1=CC=CC=C1 WIKWZMDBKJAZHP-WUFINQPMSA-N 0.000 claims 1
- ZYPHKMBWKDJJOF-WUFINQPMSA-N n-[(2s,3r)-4-[(3-chlorophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(Cl)C=CC=1)C1=CC=CC=C1 ZYPHKMBWKDJJOF-WUFINQPMSA-N 0.000 claims 1
- YSKNEAKLJOQLNF-URLMMPGGSA-N n-[(2s,3r)-4-[(3-cyanophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(C=CC=1)C#N)C1=CC=CC=C1 YSKNEAKLJOQLNF-URLMMPGGSA-N 0.000 claims 1
- VCPODXFSTGVZKS-XZWHSSHBSA-N n-[(2s,3r)-4-[(3-ethoxyphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(OCC)C=CC=1)C1=CC=CC=C1 VCPODXFSTGVZKS-XZWHSSHBSA-N 0.000 claims 1
- UYOGGJKAEZTQOH-URLMMPGGSA-N n-[(2s,3r)-4-[(4,4-dimethylcyclohexyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNC1CCC(C)(C)CC1)C1=CC=CC=C1 UYOGGJKAEZTQOH-URLMMPGGSA-N 0.000 claims 1
- OOJQBKYYQBPNKC-URLMMPGGSA-N n-[(2s,3r)-4-[(4-cyanophenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=CC(=CC=1)C#N)C1=CC=CC=C1 OOJQBKYYQBPNKC-URLMMPGGSA-N 0.000 claims 1
- WDXGIHFSFHNRIL-HVTPQOKGSA-N n-[(2s,3r)-4-[(4-tert-butylcyclohexyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNC1CCC(CC1)C(C)(C)C)C1=CC=CC=C1 WDXGIHFSFHNRIL-HVTPQOKGSA-N 0.000 claims 1
- YRFCEWYLHZYHCN-LOSJGSFVSA-N n-[(2s,3r)-4-[(5-chlorothiophen-2-yl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1SC(Cl)=CC=1)C1=CC=CC=C1 YRFCEWYLHZYHCN-LOSJGSFVSA-N 0.000 claims 1
- NFIRRAPGUKKIIJ-URLMMPGGSA-N n-[(2s,3r)-4-[(5-cyano-2-methoxyphenyl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C(=CC=C(C=1)C#N)OC)C1=CC=CC=C1 NFIRRAPGUKKIIJ-URLMMPGGSA-N 0.000 claims 1
- SJJPZYZNDZVTPY-XZWHSSHBSA-N n-[(2s,3r)-4-[2-(2,3-dimethoxyphenyl)ethylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCCC=1C(=C(OC)C=CC=1)OC)C1=CC=CC=C1 SJJPZYZNDZVTPY-XZWHSSHBSA-N 0.000 claims 1
- CNOBMBLVDAVMGT-XZWHSSHBSA-N n-[(2s,3r)-4-[2-(2,4-dichlorophenyl)ethylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCCC=1C(=CC(Cl)=CC=1)Cl)C1=CC=CC=C1 CNOBMBLVDAVMGT-XZWHSSHBSA-N 0.000 claims 1
- PGBASESNJDGYEA-XZWHSSHBSA-N n-[(2s,3r)-4-[2-(3,4-dichlorophenyl)ethylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCCC=1C=C(Cl)C(Cl)=CC=1)C1=CC=CC=C1 PGBASESNJDGYEA-XZWHSSHBSA-N 0.000 claims 1
- RGYFDPJTWYLUFE-XZWHSSHBSA-N n-[(2s,3r)-4-[2-(4-chlorophenyl)ethylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CNCCC=1C=CC(Cl)=CC=1)C1=CC=CC=C1 RGYFDPJTWYLUFE-XZWHSSHBSA-N 0.000 claims 1
- PRQFEELAHDKHBV-MJSOWUPRSA-N n-[(2s,3r)-4-[[(1r)-2,3-dihydro-1h-inden-1-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CN[C@H]1C2=CC=CC=C2CC1)C1=CC=CC=C1 PRQFEELAHDKHBV-MJSOWUPRSA-N 0.000 claims 1
- NLSNSOOHLJWWBV-DYIKCSJPSA-N n-[(2s,3r)-4-[[(1r)-2,3-dihydro-1h-inden-1-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CN[C@H]1C2=CC=CC=C2CC1)C1=CC=CC=C1 NLSNSOOHLJWWBV-DYIKCSJPSA-N 0.000 claims 1
- NJTWLCCJRPWKES-YOENNBKZSA-N n-[(2s,3r)-4-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@@H]([C@H](O)CN[C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])NC(=O)C=1C=C(C=C(NCC)C=1)N1S(CCCC1)(=O)=O)C1=CC=CC=C1 NJTWLCCJRPWKES-YOENNBKZSA-N 0.000 claims 1
- PRQFEELAHDKHBV-RWSKJCERSA-N n-[(2s,3r)-4-[[(1s)-2,3-dihydro-1h-inden-1-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CN[C@@H]1C2=CC=CC=C2CC1)C1=CC=CC=C1 PRQFEELAHDKHBV-RWSKJCERSA-N 0.000 claims 1
- MQRBWEORQKOSPA-COFKYPDJSA-N n-[(2s,3r)-4-[[(2r)-3,3-dimethylbutan-2-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1S(CCCC1)(=O)=O)[C@H](O)CN[C@H](C)C(C)(C)C)C1=CC=CC=C1 MQRBWEORQKOSPA-COFKYPDJSA-N 0.000 claims 1
- UNEAIWHLVVYBCM-RJSONGRPSA-N n-[(2s,3r)-4-[[(2s)-1-(cyclohexylamino)-1-oxopropan-2-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(2,2-dimethylpropylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@@H]([C@H](O)CN[C@@H](C)C(=O)NC1CCCCC1)NC(=O)C=1C=C(C=C(NCC(C)(C)C)C=1)N1C(CCC1)=O)C1=CC=CC=C1 UNEAIWHLVVYBCM-RJSONGRPSA-N 0.000 claims 1
- ZQPHLZSMHOLSCJ-RJSONGRPSA-N n-[(2s,3r)-4-[[(2s)-1-(cyclohexylamino)-1-oxopropan-2-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-3-(2-methylpropylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC(C)C)N1C(CCC1)=O)[C@H](O)CN[C@@H](C)C(=O)NC1CCCCC1)C1=CC=CC=C1 ZQPHLZSMHOLSCJ-RJSONGRPSA-N 0.000 claims 1
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- YKMMXLMMBQRWEF-WUFINQPMSA-N n-[(2s,3r)-4-[[3,5-bis(trifluoromethyl)phenyl]methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(1,1-dioxo-1,2-thiazolidin-2-yl)-5-ethoxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCC)N1S(CCC1)(=O)=O)[C@H](O)CNCC=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1 YKMMXLMMBQRWEF-WUFINQPMSA-N 0.000 claims 1
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- JGGFUWRXYJTILX-WUFINQPMSA-N n-[(2s,3r)-4-[[3,5-bis(trifluoromethyl)phenyl]methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-(ethylamino)-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NCC)N1C(CCC1)=O)[C@H](O)CNCC=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1 JGGFUWRXYJTILX-WUFINQPMSA-N 0.000 claims 1
- PEBMRMNRSFWMSS-IOWSJCHKSA-N n-[(2s,3r)-4-[[3,5-bis(trifluoromethyl)phenyl]methylamino]-3-hydroxy-1-phenylbutan-2-yl]-3-cyclopentyl-5-(1,1-dioxo-1,2-thiazolidin-2-yl)benzamide Chemical compound C([C@@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)C=1C=C(C=C(C=1)C1CCCC1)N1S(CCC1)(=O)=O)NCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 PEBMRMNRSFWMSS-IOWSJCHKSA-N 0.000 claims 1
- ILIYXNPRPVPHPS-FCHUYYIVSA-N n-[(2s,3r)-4-amino-3-hydroxy-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-(propan-2-ylamino)benzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)NC(C)C)N1C(CCC1)=O)[C@H](O)CN)C1=CC=CC=C1 ILIYXNPRPVPHPS-FCHUYYIVSA-N 0.000 claims 1
- RNCASDNMISAZAV-BJKOFHAPSA-N n-[(2s,3r)-4-amino-3-hydroxy-1-phenylbutan-2-yl]-3-(2-oxopyrrolidin-1-yl)-5-pentoxybenzamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)OCCCCC)N1C(CCC1)=O)[C@H](O)CN)C1=CC=CC=C1 RNCASDNMISAZAV-BJKOFHAPSA-N 0.000 claims 1
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- 238000010511 deprotection reaction Methods 0.000 description 6
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- DAPPFDNZRGTFMR-UHFFFAOYSA-N ethyl 3-(3-chloropropylsulfonylamino)-5-ethylsulfanylbenzoate Chemical compound CCOC(=O)C1=CC(NS(=O)(=O)CCCCl)=CC(SCC)=C1 DAPPFDNZRGTFMR-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
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- SDIHQIIUJCVOFS-UHFFFAOYSA-N methyl 3-(3-chloropropylsulfonylamino)-5-ethoxybenzoate Chemical compound CCOC1=CC(NS(=O)(=O)CCCCl)=CC(C(=O)OC)=C1 SDIHQIIUJCVOFS-UHFFFAOYSA-N 0.000 description 6
- MBDLJSOITBEJMM-UHFFFAOYSA-N methyl 3-(3-chloropropylsulfonylamino)-5-phenylmethoxybenzoate Chemical compound COC(=O)C1=CC(NS(=O)(=O)CCCCl)=CC(OCC=2C=CC=CC=2)=C1 MBDLJSOITBEJMM-UHFFFAOYSA-N 0.000 description 6
- ZFZFCTRIFSHEJP-UHFFFAOYSA-N methyl 3-(3-hydroxypropoxy)-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound COC(=O)C1=CC(OCCCO)=CC(N2C(CCC2)=O)=C1 ZFZFCTRIFSHEJP-UHFFFAOYSA-N 0.000 description 6
- QXBPSRMQYUGKRG-UHFFFAOYSA-N methyl 3-(4-chlorobutanoylamino)-5-ethoxybenzoate Chemical compound CCOC1=CC(NC(=O)CCCCl)=CC(C(=O)OC)=C1 QXBPSRMQYUGKRG-UHFFFAOYSA-N 0.000 description 6
- QSNBPPFQQGICAX-UHFFFAOYSA-N methyl 3-(5-chloropentanoylamino)-5-nitrobenzoate Chemical compound COC(=O)C1=CC(NC(=O)CCCCCl)=CC([N+]([O-])=O)=C1 QSNBPPFQQGICAX-UHFFFAOYSA-N 0.000 description 6
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- CHZIKDPNKBBWCW-UHFFFAOYSA-N methyl 3-bromo-5-(4-chlorobutanoylamino)benzoate Chemical compound COC(=O)C1=CC(Br)=CC(NC(=O)CCCCl)=C1 CHZIKDPNKBBWCW-UHFFFAOYSA-N 0.000 description 6
- CZTAENQWUIGGTE-UHFFFAOYSA-N methyl 3-ethoxy-5-(phenylmethoxycarbonylamino)benzoate Chemical compound COC(=O)C1=CC(OCC)=CC(NC(=O)OCC=2C=CC=CC=2)=C1 CZTAENQWUIGGTE-UHFFFAOYSA-N 0.000 description 6
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- OEVBZFLQEMIXOS-UHFFFAOYSA-N methyl 4-methoxy-3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=C(OC)C([N+]([O-])=O)=C1 OEVBZFLQEMIXOS-UHFFFAOYSA-N 0.000 description 6
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- PCTFIHOVQYYAMH-UHFFFAOYSA-N 3,5-dinitro-4-chlorobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 PCTFIHOVQYYAMH-UHFFFAOYSA-N 0.000 description 5
- KXMVETMOLJBYFI-UHFFFAOYSA-N 3-(dimethylcarbamoylsulfanyl)-5-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC(SC(=O)N(C)C)=CC(C(O)=O)=C1 KXMVETMOLJBYFI-UHFFFAOYSA-N 0.000 description 5
- ZCRNIIJXDRYWDU-UHFFFAOYSA-N 3-(methoxycarbonyl)-5-nitrobenzoic acid Chemical compound COC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 ZCRNIIJXDRYWDU-UHFFFAOYSA-N 0.000 description 5
- QMDJKFOKWXQLFB-UHFFFAOYSA-N 3-ethoxy-5-methoxycarbonylbenzoic acid Chemical compound CCOC1=CC(C(O)=O)=CC(C(=O)OC)=C1 QMDJKFOKWXQLFB-UHFFFAOYSA-N 0.000 description 5
- FXAAMCKIUPNXCO-UHFFFAOYSA-N 3-o-tert-butyl 1-o-methyl 5-(4-chlorobutanoylamino)benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(NC(=O)CCCCl)=CC(C(=O)OC(C)(C)C)=C1 FXAAMCKIUPNXCO-UHFFFAOYSA-N 0.000 description 5
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 5
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- 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- LFBGZTDKGYEQLH-UHFFFAOYSA-N butan-2-ol;dihydrochloride Chemical compound Cl.Cl.CCC(C)O LFBGZTDKGYEQLH-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- IHLXUGJTIUZJBQ-UHFFFAOYSA-N dimethyl 5-(dimethylcarbamoylsulfanyl)benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(SC(=O)N(C)C)=CC(C(=O)OC)=C1 IHLXUGJTIUZJBQ-UHFFFAOYSA-N 0.000 description 5
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- 239000000284 extract Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
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- MJWIOEAIUKGAGU-UHFFFAOYSA-N methyl 3-(3-chloropropylsulfonylamino)-5-nitrobenzoate Chemical compound COC(=O)C1=CC(NS(=O)(=O)CCCCl)=CC([N+]([O-])=O)=C1 MJWIOEAIUKGAGU-UHFFFAOYSA-N 0.000 description 5
- GZZNNLWEALUGCN-UHFFFAOYSA-N methyl 3-(4-chlorobutanoylamino)-5-nitrobenzoate Chemical compound COC(=O)C1=CC(NC(=O)CCCCl)=CC([N+]([O-])=O)=C1 GZZNNLWEALUGCN-UHFFFAOYSA-N 0.000 description 5
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- YJJKLUFXSOIDKD-UHFFFAOYSA-N methyl 7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethylbenzimidazole-5-carboxylate Chemical compound C1=C(C(=O)OC)C=C2N(CC)C=NC2=C1N1CCCS1(=O)=O YJJKLUFXSOIDKD-UHFFFAOYSA-N 0.000 description 5
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- XVZQKVKVDOXQJG-UHFFFAOYSA-N 7-methoxy-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1CCC(N)C2=CC(OC)=CC=C21 XVZQKVKVDOXQJG-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 102100021277 Beta-secretase 2 Human genes 0.000 description 4
- 101710150190 Beta-secretase 2 Proteins 0.000 description 4
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- 125000006242 amine protecting group Chemical group 0.000 description 4
- 150000001499 aryl bromides Chemical class 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- BOQCORYQJJYJTF-UHFFFAOYSA-N dimethyl 5-phenylmethoxybenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(OCC=2C=CC=CC=2)=C1 BOQCORYQJJYJTF-UHFFFAOYSA-N 0.000 description 4
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- WUVKCZITSPJWCD-UHFFFAOYSA-N ethyl 3-(4-chlorobutanoylamino)-5-ethylsulfanylbenzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCl)=CC(SCC)=C1 WUVKCZITSPJWCD-UHFFFAOYSA-N 0.000 description 4
- WPIHJUFBRLRKIV-UHFFFAOYSA-N ethyl 3-ethyl-1-methyl-7-(2-oxopyrrolidin-1-yl)indole-5-carboxylate Chemical compound C=12N(C)C=C(CC)C2=CC(C(=O)OCC)=CC=1N1CCCC1=O WPIHJUFBRLRKIV-UHFFFAOYSA-N 0.000 description 4
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- KYXHNNWAMJCPBK-UHFFFAOYSA-N ethyl 7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethyl-1-methylindole-5-carboxylate Chemical compound C=12N(C)C=C(CC)C2=CC(C(=O)OCC)=CC=1N1CCCS1(=O)=O KYXHNNWAMJCPBK-UHFFFAOYSA-N 0.000 description 4
- IZCWYQJMGGJTFP-UHFFFAOYSA-N ethyl 7-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-ethyl-1h-indole-5-carboxylate Chemical compound C=12NC=C(CC)C2=CC(C(=O)OCC)=CC=1N1CCCS1(=O)=O IZCWYQJMGGJTFP-UHFFFAOYSA-N 0.000 description 4
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
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- KBKGLYGOJKRGDI-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylsulfanyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]benzoate Chemical compound COC(=O)C1=CC=CC(NC(=O)OC(C)(C)C)=C1SC(=O)N(C)C KBKGLYGOJKRGDI-UHFFFAOYSA-N 0.000 description 4
- CUYAUGFMEUEWQZ-UHFFFAOYSA-N methyl 3-(2-oxopyrrolidin-1-yl)-5-(3-phenylmethoxypropoxy)benzoate Chemical compound C=1C(N2C(CCC2)=O)=CC(C(=O)OC)=CC=1OCCCOCC1=CC=CC=C1 CUYAUGFMEUEWQZ-UHFFFAOYSA-N 0.000 description 4
- PLTSKTSHDBFTRT-UHFFFAOYSA-N methyl 3-(2-oxopyrrolidin-1-yl)-5-(pentan-3-ylamino)benzoate Chemical compound COC(=O)C1=CC(NC(CC)CC)=CC(N2C(CCC2)=O)=C1 PLTSKTSHDBFTRT-UHFFFAOYSA-N 0.000 description 4
- NEFSQRDMMZIRSX-UHFFFAOYSA-N methyl 3-(2-oxopyrrolidin-1-yl)-5-(propylcarbamoyl)benzoate Chemical compound COC(=O)C1=CC(C(=O)NCCC)=CC(N2C(CCC2)=O)=C1 NEFSQRDMMZIRSX-UHFFFAOYSA-N 0.000 description 4
- GPBPSFQFHGPIOY-UHFFFAOYSA-N methyl 3-(3-chloropropylsulfonylamino)-5-methylsulfanylbenzoate Chemical compound COC(=O)C1=CC(NS(=O)(=O)CCCCl)=CC(SC)=C1 GPBPSFQFHGPIOY-UHFFFAOYSA-N 0.000 description 4
- IBPKMNNVMGMNCU-UHFFFAOYSA-N methyl 3-(4-chlorobutanoylamino)-5-(dipropylcarbamoyl)benzoate Chemical compound CCCN(CCC)C(=O)C1=CC(NC(=O)CCCCl)=CC(C(=O)OC)=C1 IBPKMNNVMGMNCU-UHFFFAOYSA-N 0.000 description 4
- QZJYKIDUJOZULP-UHFFFAOYSA-N methyl 3-(cyclohexen-1-yl)-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(N2C(CCC2)=O)=CC=1C1=CCCCC1 QZJYKIDUJOZULP-UHFFFAOYSA-N 0.000 description 4
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- PXQMSTLNSHMSJB-UHFFFAOYSA-N 4,4-dimethylcyclohexan-1-one Chemical compound CC1(C)CCC(=O)CC1 PXQMSTLNSHMSJB-UHFFFAOYSA-N 0.000 description 3
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
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- 244000309464 bull Species 0.000 description 3
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
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- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 3
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 3
- GAZIAEBIYGYIQP-UHFFFAOYSA-N ethyl 3-bromo-4-[3-methylbut-2-enyl-(2,2,2-trifluoroacetyl)amino]-5-nitrobenzoate Chemical compound CCOC(=O)C1=CC(Br)=C(N(CC=C(C)C)C(=O)C(F)(F)F)C([N+]([O-])=O)=C1 GAZIAEBIYGYIQP-UHFFFAOYSA-N 0.000 description 3
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- SQLXYZBPMRXJCY-UHFFFAOYSA-N ethyl 3-ethylsulfanyl-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound CCOC(=O)C1=CC(SCC)=CC(N2C(CCC2)=O)=C1 SQLXYZBPMRXJCY-UHFFFAOYSA-N 0.000 description 3
- RYZBUWKGJKKEDC-UHFFFAOYSA-N ethyl 3-ethylsulfanyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)OC(C)(C)C)=CC(SCC)=C1 RYZBUWKGJKKEDC-UHFFFAOYSA-N 0.000 description 3
- QANVLXVFIRTXFG-UHFFFAOYSA-N ethyl 4-amino-3-bromo-5-nitrobenzoate Chemical compound CCOC(=O)C1=CC(Br)=C(N)C([N+]([O-])=O)=C1 QANVLXVFIRTXFG-UHFFFAOYSA-N 0.000 description 3
- HPCYANYWTUCLMH-UHFFFAOYSA-N ethyl 4-amino-3-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 HPCYANYWTUCLMH-UHFFFAOYSA-N 0.000 description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 3
- IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- ANPZXWWIJXYAGV-UHFFFAOYSA-N methyl 1-ethyl-4-nitroindazole-6-carboxylate Chemical compound C1=C(C(=O)OC)C=C2N(CC)N=CC2=C1[N+]([O-])=O ANPZXWWIJXYAGV-UHFFFAOYSA-N 0.000 description 3
- DRYBMFJLYYEOBZ-UHFFFAOYSA-N methyl 1h-indole-5-carboxylate Chemical compound COC(=O)C1=CC=C2NC=CC2=C1 DRYBMFJLYYEOBZ-UHFFFAOYSA-N 0.000 description 3
- AYYOZKHMSABVRP-UHFFFAOYSA-N methyl 1h-indole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CNC2=C1 AYYOZKHMSABVRP-UHFFFAOYSA-N 0.000 description 3
- RJCTUPZUVYYPGV-UHFFFAOYSA-N methyl 3,5-bis(2-oxopyrrolidin-1-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(N2C(CCC2)=O)=CC=1N1CCCC1=O RJCTUPZUVYYPGV-UHFFFAOYSA-N 0.000 description 3
- AHYAIXUNKFDLRG-UHFFFAOYSA-N methyl 3-(1,1-dioxo-1,2-thiazolidin-2-yl)-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(N2C(CCC2)=O)=CC=1N1CCCS1(=O)=O AHYAIXUNKFDLRG-UHFFFAOYSA-N 0.000 description 3
- NCJBEYPINIITMO-UHFFFAOYSA-N methyl 3-(1,1-dioxo-4-phenylthiazinan-2-yl)-5-(ethylamino)benzoate Chemical compound COC(=O)C1=CC(NCC)=CC(N2S(CCC(C2)C=2C=CC=CC=2)(=O)=O)=C1 NCJBEYPINIITMO-UHFFFAOYSA-N 0.000 description 3
- QHPDPMTUBQVPKE-UHFFFAOYSA-N methyl 3-(1,1-dioxothiazinan-2-yl)-5-propan-2-yloxybenzoate Chemical compound COC(=O)C1=CC(OC(C)C)=CC(N2S(CCCC2)(=O)=O)=C1 QHPDPMTUBQVPKE-UHFFFAOYSA-N 0.000 description 3
- LDYIYVVTEDMLCO-UHFFFAOYSA-N methyl 3-(diethylamino)-2-(2-oxopyrrolidin-1-yl)benzoate Chemical compound CCN(CC)C1=CC=CC(C(=O)OC)=C1N1C(=O)CCC1 LDYIYVVTEDMLCO-UHFFFAOYSA-N 0.000 description 3
- MGIBHBWBGQVHLS-UHFFFAOYSA-N methyl 3-(dipropylcarbamoyl)-5-nitrobenzoate Chemical compound CCCN(CCC)C(=O)C1=CC(C(=O)OC)=CC([N+]([O-])=O)=C1 MGIBHBWBGQVHLS-UHFFFAOYSA-N 0.000 description 3
- SRGFIPHVRUCGOP-UHFFFAOYSA-N methyl 3-(hydroxymethyl)-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound COC(=O)C1=CC(CO)=CC(N2C(CCC2)=O)=C1 SRGFIPHVRUCGOP-UHFFFAOYSA-N 0.000 description 3
- NQJNEBQTJXTNJF-UHFFFAOYSA-N methyl 3-amino-4-methyl-5-nitrobenzoate Chemical compound COC(=O)C1=CC(N)=C(C)C([N+]([O-])=O)=C1 NQJNEBQTJXTNJF-UHFFFAOYSA-N 0.000 description 3
- LHWFYHJRAUJCBS-UHFFFAOYSA-N methyl 3-amino-5-propylbenzoate Chemical compound CCCC1=CC(N)=CC(C(=O)OC)=C1 LHWFYHJRAUJCBS-UHFFFAOYSA-N 0.000 description 3
- IJZZMZOQPHYOFC-UHFFFAOYSA-N methyl 3-bromo-5-(1,1-dioxothiazinan-2-yl)benzoate Chemical compound COC(=O)C1=CC(Br)=CC(N2S(CCCC2)(=O)=O)=C1 IJZZMZOQPHYOFC-UHFFFAOYSA-N 0.000 description 3
- IQCROPNUEYOSNU-UHFFFAOYSA-N methyl 3-cyclopent-2-en-1-yl-5-(1,1-dioxo-1,2-thiazolidin-2-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(C2C=CCC2)=CC=1N1CCCS1(=O)=O IQCROPNUEYOSNU-UHFFFAOYSA-N 0.000 description 3
- FBJWQYQVGFUULD-UHFFFAOYSA-N methyl 3-cyclopentyl-5-(1,1-dioxothiazinan-2-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(C2CCCC2)=CC=1N1CCCCS1(=O)=O FBJWQYQVGFUULD-UHFFFAOYSA-N 0.000 description 3
- LSHWJNAFQHWOIO-UHFFFAOYSA-N methyl 3-ethyl-7-(2-oxopyrrolidin-1-yl)-1-benzofuran-5-carboxylate Chemical compound C1=C(C(=O)OC)C=C2C(CC)=COC2=C1N1CCCC1=O LSHWJNAFQHWOIO-UHFFFAOYSA-N 0.000 description 3
- FGOZWDICHQDFOZ-UHFFFAOYSA-N methyl 3-ethyl-7-nitrobenzimidazole-5-carboxylate Chemical compound C1=C(C(=O)OC)C=C2N(CC)C=NC2=C1[N+]([O-])=O FGOZWDICHQDFOZ-UHFFFAOYSA-N 0.000 description 3
- PWTQRQHGGYSNNW-UHFFFAOYSA-N methyl 3-iodo-4-methoxy-5-nitrobenzoate Chemical compound COC(=O)C1=CC(I)=C(OC)C([N+]([O-])=O)=C1 PWTQRQHGGYSNNW-UHFFFAOYSA-N 0.000 description 3
- WOIFJWTYGGTGST-UHFFFAOYSA-N methyl 4-(1,1-dioxothiazinan-2-yl)-1h-indole-6-carboxylate Chemical compound C=12C=CNC2=CC(C(=O)OC)=CC=1N1CCCCS1(=O)=O WOIFJWTYGGTGST-UHFFFAOYSA-N 0.000 description 3
- HKMDTHJBKQKWKD-UHFFFAOYSA-N methyl 4-(1,1-dioxothiazinan-2-yl)-2,3-dihydro-1h-indole-6-carboxylate;hydrochloride Chemical compound Cl.C=1C(C(=O)OC)=CC=2NCCC=2C=1N1CCCCS1(=O)=O HKMDTHJBKQKWKD-UHFFFAOYSA-N 0.000 description 3
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- KLQZDSIKRJOWJJ-UHFFFAOYSA-N methyl 1-ethyl-4-(2-oxopyrrolidin-1-yl)indole-6-carboxylate Chemical compound C1=C(C(=O)OC)C=C2N(CC)C=CC2=C1N1CCCC1=O KLQZDSIKRJOWJJ-UHFFFAOYSA-N 0.000 description 2
- ONWYSHWKVSVXQQ-UHFFFAOYSA-N methyl 2-fluoro-3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1F ONWYSHWKVSVXQQ-UHFFFAOYSA-N 0.000 description 2
- JQPZGYMYHZYPFZ-UHFFFAOYSA-N methyl 2-fluoro-5-nitro-3-(2-oxopyrrolidin-1-yl)benzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC(N2C(CCC2)=O)=C1F JQPZGYMYHZYPFZ-UHFFFAOYSA-N 0.000 description 2
- QSBFYMBFQLOZNZ-UHFFFAOYSA-N methyl 3,5-diamino-4-chlorobenzoate Chemical compound COC(=O)C1=CC(N)=C(Cl)C(N)=C1 QSBFYMBFQLOZNZ-UHFFFAOYSA-N 0.000 description 2
- VWPQIIANKVRARB-UHFFFAOYSA-N methyl 3,5-diiodo-4-prop-2-enoxybenzoate Chemical compound COC(=O)C1=CC(I)=C(OCC=C)C(I)=C1 VWPQIIANKVRARB-UHFFFAOYSA-N 0.000 description 2
- VSEONSAQELBHFL-UHFFFAOYSA-N methyl 3-(1,1-dioxo-1,2-thiazolidin-2-yl)-2-fluoro-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC(N2S(CCC2)(=O)=O)=C1F VSEONSAQELBHFL-UHFFFAOYSA-N 0.000 description 2
- XTOVECGJSQVZRE-UHFFFAOYSA-N methyl 3-(1,1-dioxo-4-phenylthiazinan-2-yl)-5-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC(N2S(CCC(C2)C=2C=CC=CC=2)(=O)=O)=C1 XTOVECGJSQVZRE-UHFFFAOYSA-N 0.000 description 2
- SPPSDSIWOQFDPY-UHFFFAOYSA-N methyl 3-(1,1-dioxothiazinan-2-yl)-2-fluoro-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC(N2S(CCCC2)(=O)=O)=C1F SPPSDSIWOQFDPY-UHFFFAOYSA-N 0.000 description 2
- SBTWBLZBJWMZGU-UHFFFAOYSA-N methyl 3-(1,1-dioxothiazinan-2-yl)-2-methoxy-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC(N2S(CCCC2)(=O)=O)=C1OC SBTWBLZBJWMZGU-UHFFFAOYSA-N 0.000 description 2
- SVKZWOHTPRAMKJ-UHFFFAOYSA-N methyl 3-(1,1-dioxothiazinan-2-yl)-5-(ethylamino)-4-methylbenzoate Chemical compound CCNC1=CC(C(=O)OC)=CC(N2S(CCCC2)(=O)=O)=C1C SVKZWOHTPRAMKJ-UHFFFAOYSA-N 0.000 description 2
- IGCVHZXMKBXUDE-UHFFFAOYSA-N methyl 3-(1,1-dioxothiazinan-2-yl)-5-(propan-2-ylamino)benzoate Chemical compound COC(=O)C1=CC(NC(C)C)=CC(N2S(CCCC2)(=O)=O)=C1 IGCVHZXMKBXUDE-UHFFFAOYSA-N 0.000 description 2
- OMVIGLJWGDSMQP-UHFFFAOYSA-N methyl 3-(1,1-dioxothiazinan-2-yl)-5-hydroxybenzoate Chemical compound COC(=O)C1=CC(O)=CC(N2S(CCCC2)(=O)=O)=C1 OMVIGLJWGDSMQP-UHFFFAOYSA-N 0.000 description 2
- WUVTVLWFHRCPTN-UHFFFAOYSA-N methyl 3-(1,1-dioxothiazinan-2-yl)-5-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC(N2S(CCCC2)(=O)=O)=C1 WUVTVLWFHRCPTN-UHFFFAOYSA-N 0.000 description 2
- ORVLNXWRKNANDU-UHFFFAOYSA-N methyl 3-(3-methoxypropoxy)-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound COC(=O)C1=CC(OCCCOC)=CC(N2C(CCC2)=O)=C1 ORVLNXWRKNANDU-UHFFFAOYSA-N 0.000 description 2
- MGDPBJBUMAJVLY-UHFFFAOYSA-N methyl 3-(4-chlorobutanoylamino)-5-(1,1-dioxo-1,2-thiazolidin-2-yl)benzoate Chemical compound COC(=O)C1=CC(NC(=O)CCCCl)=CC(N2S(CCC2)(=O)=O)=C1 MGDPBJBUMAJVLY-UHFFFAOYSA-N 0.000 description 2
- MNNQBOQCGDZPPP-UHFFFAOYSA-N methyl 3-(4-methylpiperazin-1-yl)-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(N2C(CCC2)=O)=CC=1N1CCN(C)CC1 MNNQBOQCGDZPPP-UHFFFAOYSA-N 0.000 description 2
- LMFHDZVSQQPDFH-UHFFFAOYSA-N methyl 3-(diethylamino)-5-(1,1-dioxothiazinan-2-yl)-4-methylbenzoate Chemical compound CCN(CC)C1=CC(C(=O)OC)=CC(N2S(CCCC2)(=O)=O)=C1C LMFHDZVSQQPDFH-UHFFFAOYSA-N 0.000 description 2
- ANRXZTNRUXAXQP-UHFFFAOYSA-N methyl 3-(dipropylcarbamoyl)benzoate Chemical compound CCCN(CCC)C(=O)C1=CC=CC(C(=O)OC)=C1 ANRXZTNRUXAXQP-UHFFFAOYSA-N 0.000 description 2
- GLGKDMVSCSESFP-UHFFFAOYSA-N methyl 3-[but-3-enylsulfonyl(prop-2-enyl)amino]-5-propylbenzoate Chemical compound CCCC1=CC(N(CC=C)S(=O)(=O)CCC=C)=CC(C(=O)OC)=C1 GLGKDMVSCSESFP-UHFFFAOYSA-N 0.000 description 2
- YIHDXANSZWQXKZ-UHFFFAOYSA-N methyl 3-[methylsulfonyl(propyl)amino]-2-(2-oxopyrrolidin-1-yl)benzoate Chemical compound CCCN(S(C)(=O)=O)C1=CC=CC(C(=O)OC)=C1N1C(=O)CCC1 YIHDXANSZWQXKZ-UHFFFAOYSA-N 0.000 description 2
- XAQAXKUSSSZKMD-UHFFFAOYSA-N methyl 3-bromo-5-(1,1-dioxo-1,2-thiazolidin-2-yl)benzoate Chemical compound COC(=O)C1=CC(Br)=CC(N2S(CCC2)(=O)=O)=C1 XAQAXKUSSSZKMD-UHFFFAOYSA-N 0.000 description 2
- IUOMXCAHMVRGIW-UHFFFAOYSA-N methyl 3-cyclohex-3-en-1-yl-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(C2CC=CCC2)=CC=1N1CCCC1=O IUOMXCAHMVRGIW-UHFFFAOYSA-N 0.000 description 2
- JQMBVKOXOABREB-UHFFFAOYSA-N methyl 3-cyclopent-2-en-1-yl-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(C2C=CCC2)=CC=1N1CCCC1=O JQMBVKOXOABREB-UHFFFAOYSA-N 0.000 description 2
- XHJLQGNRCMZJTJ-UHFFFAOYSA-N methyl 3-cyclopent-3-en-1-yl-5-(1,1-dioxothiazinan-2-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(C2CC=CC2)=CC=1N1CCCCS1(=O)=O XHJLQGNRCMZJTJ-UHFFFAOYSA-N 0.000 description 2
- WMAZADNNESKMMN-UHFFFAOYSA-N methyl 3-cyclopent-3-en-1-yl-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(C2CC=CC2)=CC=1N1CCCC1=O WMAZADNNESKMMN-UHFFFAOYSA-N 0.000 description 2
- HLEDJIJOLJIRKO-UHFFFAOYSA-N methyl 3-ethyl-7-(2-oxopyrrolidin-1-yl)benzotriazole-5-carboxylate Chemical compound C1=C(C(=O)OC)C=C2N(CC)N=NC2=C1N1CCCC1=O HLEDJIJOLJIRKO-UHFFFAOYSA-N 0.000 description 2
- JRUVOAVPJJOGKD-UHFFFAOYSA-N methyl 3-iodo-5-(2-oxopyrrolidin-1-yl)-4-prop-2-enoxybenzoate Chemical compound COC(=O)C1=CC(I)=C(OCC=C)C(N2C(CCC2)=O)=C1 JRUVOAVPJJOGKD-UHFFFAOYSA-N 0.000 description 2
- JGDCUZJGFHIZEM-UHFFFAOYSA-N methyl 3-methyl-7-(2-oxopyrrolidin-1-yl)-1-benzofuran-5-carboxylate Chemical compound C=12OC=C(C)C2=CC(C(=O)OC)=CC=1N1CCCC1=O JGDCUZJGFHIZEM-UHFFFAOYSA-N 0.000 description 2
- LFLQBBCNMCQNKJ-UHFFFAOYSA-N methyl 4-(1,1-dioxo-1,2-thiazolidin-2-yl)-1-ethylindole-6-carboxylate Chemical compound C1=C(C(=O)OC)C=C2N(CC)C=CC2=C1N1CCCS1(=O)=O LFLQBBCNMCQNKJ-UHFFFAOYSA-N 0.000 description 2
- IZANRPNXIOQDRS-UHFFFAOYSA-N methyl 4-(1,1-dioxothiazinan-2-yl)-1-ethylindole-6-carboxylate Chemical compound C1=C(C(=O)OC)C=C2N(CC)C=CC2=C1N1CCCCS1(=O)=O IZANRPNXIOQDRS-UHFFFAOYSA-N 0.000 description 2
- KMUGVCJKEJEUES-UHFFFAOYSA-N methyl 4-(2-oxopyrrolidin-1-yl)-1h-indole-6-carboxylate Chemical compound C=12C=CNC2=CC(C(=O)OC)=CC=1N1CCCC1=O KMUGVCJKEJEUES-UHFFFAOYSA-N 0.000 description 2
- OTLSMMGWGYHNTP-UHFFFAOYSA-N methyl 4-amino-1-ethylindole-6-carboxylate;hydrochloride Chemical compound Cl.C1=C(C(=O)OC)C=C2N(CC)C=CC2=C1N OTLSMMGWGYHNTP-UHFFFAOYSA-N 0.000 description 2
- PXMURBICUSFNIK-UHFFFAOYSA-N methyl 4-amino-3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=C(N)C([N+]([O-])=O)=C1 PXMURBICUSFNIK-UHFFFAOYSA-N 0.000 description 2
- QXJDEHRKKPICAT-UHFFFAOYSA-N methyl 4-amino-3-(ethylamino)-5-nitrobenzoate Chemical compound CCNC1=CC(C(=O)OC)=CC([N+]([O-])=O)=C1N QXJDEHRKKPICAT-UHFFFAOYSA-N 0.000 description 2
- KFCWCWBZLGOBTB-UHFFFAOYSA-N methyl 4-but-3-enoxy-3-iodo-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound COC(=O)C1=CC(I)=C(OCCC=C)C(N2C(CCC2)=O)=C1 KFCWCWBZLGOBTB-UHFFFAOYSA-N 0.000 description 2
- MFABUTNRZJMBOK-UHFFFAOYSA-N methyl 4-chloro-3-(4-chlorobutanoylamino)benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(NC(=O)CCCCl)=C1 MFABUTNRZJMBOK-UHFFFAOYSA-N 0.000 description 2
- JVIFWAPBBVTTHS-UHFFFAOYSA-N methyl 4-ethoxy-3-[ethyl(propanoyl)amino]-5-prop-1-en-2-ylbenzoate Chemical compound CCOC1=C(N(CC)C(=O)CC)C=C(C(=O)OC)C=C1C(C)=C JVIFWAPBBVTTHS-UHFFFAOYSA-N 0.000 description 2
- SSHGMNJBSVASRR-UHFFFAOYSA-N methyl 4-ethyl-8-nitro-2,3-dihydro-1h-quinoxaline-6-carboxylate Chemical compound C1=C(C(=O)OC)C=C([N+]([O-])=O)C2=C1N(CC)CCN2 SSHGMNJBSVASRR-UHFFFAOYSA-N 0.000 description 2
- HBUZFVRDRDBPMT-UHFFFAOYSA-N methyl 4-methyl-8-(2-oxopyrrolidin-1-yl)-2h-chromene-6-carboxylate Chemical compound C=12OCC=C(C)C2=CC(C(=O)OC)=CC=1N1CCCC1=O HBUZFVRDRDBPMT-UHFFFAOYSA-N 0.000 description 2
- WVIKLZCQIUXZJT-UHFFFAOYSA-N methyl 5-bromo-2-fluoro-3-(2-oxopyrrolidin-1-yl)benzoate Chemical compound COC(=O)C1=CC(Br)=CC(N2C(CCC2)=O)=C1F WVIKLZCQIUXZJT-UHFFFAOYSA-N 0.000 description 2
- MCMQBDBKQSJUCH-UHFFFAOYSA-N methyl 5-cyclopent-2-en-1-yl-3-(1,1-dioxothiazinan-2-yl)-2-fluorobenzoate Chemical compound FC=1C(C(=O)OC)=CC(C2C=CCC2)=CC=1N1CCCCS1(=O)=O MCMQBDBKQSJUCH-UHFFFAOYSA-N 0.000 description 2
- BUWYKRSGSCYXTI-UHFFFAOYSA-N methyl 7-(2-oxopyrrolidin-1-yl)-2h-benzotriazole-5-carboxylate Chemical compound C=12N=NNC2=CC(C(=O)OC)=CC=1N1CCCC1=O BUWYKRSGSCYXTI-UHFFFAOYSA-N 0.000 description 2
- MHBDZVONDKMJSQ-UHFFFAOYSA-N methyl 8-(1,1-dioxo-1,2-thiazolidin-2-yl)-4-ethyl-2,3-dihydro-1h-quinoxaline-6-carboxylate Chemical compound C1=C(C(=O)OC)C=C2N(CC)CCNC2=C1N1CCCS1(=O)=O MHBDZVONDKMJSQ-UHFFFAOYSA-N 0.000 description 2
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 2
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 2
- 125000004999 nitroaryl group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000002687 nonaqueous vehicle Substances 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- MQVMKACHZJFJNQ-UHFFFAOYSA-N tert-butyl 3-morpholin-4-yl-5-(2-oxopiperidin-1-yl)benzoate Chemical compound C=1C(C(=O)OC(C)(C)C)=CC(N2CCOCC2)=CC=1N1CCCCC1=O MQVMKACHZJFJNQ-UHFFFAOYSA-N 0.000 description 2
- OWELBZTXHNMEKC-UHFFFAOYSA-N tert-butyl n-(4,4-difluorocyclohexyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(F)(F)CC1 OWELBZTXHNMEKC-UHFFFAOYSA-N 0.000 description 2
- NVPOUMXZERMIJK-QWHCGFSZSA-N tert-butyl n-[(1s)-1-[(2s)-oxiran-2-yl]-2-phenylethyl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)[C@@H]1OC1)C1=CC=CC=C1 NVPOUMXZERMIJK-QWHCGFSZSA-N 0.000 description 2
- PDLATMBIYFQTOJ-QWHCGFSZSA-N tert-butyl n-[(2s,3r)-4-amino-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]([C@H](O)CN)CC1=CC=CC=C1 PDLATMBIYFQTOJ-QWHCGFSZSA-N 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ODJXGMKEZSSRMK-JKSUJKDBSA-N (2r,3s)-3-amino-1-(cyclohexylamino)-4-phenylbutan-2-ol Chemical compound C([C@H](N)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 ODJXGMKEZSSRMK-JKSUJKDBSA-N 0.000 description 1
- OGUWKZXLZMYUKV-OAMYOWMRSA-N (2r,3s)-3-amino-4-(2-chlorophenyl)-1-[(3-methoxyphenyl)methylamino]butan-2-ol;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC(CNC[C@@H](O)[C@@H](N)CC=2C(=CC=CC=2)Cl)=C1 OGUWKZXLZMYUKV-OAMYOWMRSA-N 0.000 description 1
- FCFWEOGTZZPCTO-QMMMGPOBSA-N (2s)-3,6-dimethoxy-2-propan-2-yl-2,5-dihydropyrazine Chemical compound COC1=N[C@@H](C(C)C)C(OC)=NC1 FCFWEOGTZZPCTO-QMMMGPOBSA-N 0.000 description 1
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 description 1
- VDMKJSJJXQDICL-ZXVJYWQYSA-N 1,7-dipyridin-3-ylheptan-4-yl (2s)-1-[2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl]piperidine-2-carboxylate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O.COC1=C(OC)C(OC)=CC(C(=O)C(=O)N2[C@@H](CCCC2)C(=O)OC(CCCC=2C=NC=CC=2)CCCC=2C=NC=CC=2)=C1 VDMKJSJJXQDICL-ZXVJYWQYSA-N 0.000 description 1
- IMQJINOQJDHNBA-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]cyclobutan-1-amine Chemical compound C=1C=CC(Cl)=CC=1CC1(N)CCC1 IMQJINOQJDHNBA-UHFFFAOYSA-N 0.000 description 1
- GUTSGUHZRDJWRH-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]cyclobutane-1-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1CC1(C(=O)O)CCC1 GUTSGUHZRDJWRH-UHFFFAOYSA-N 0.000 description 1
- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 1
- XGXNQIUNHHNDAQ-UHFFFAOYSA-N 1-ethylcyclobutan-1-amine Chemical compound CCC1(N)CCC1 XGXNQIUNHHNDAQ-UHFFFAOYSA-N 0.000 description 1
- YRVOGOXCQNXNRS-UHFFFAOYSA-N 1-ethylindole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2N(CC)C=CC2=C1 YRVOGOXCQNXNRS-UHFFFAOYSA-N 0.000 description 1
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical class C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- GGTVKLOZXHKJRZ-UHFFFAOYSA-N 1-o-tert-butyl 6-o-methyl 4-(1,1-dioxothiazinan-2-yl)indole-1,6-dicarboxylate Chemical compound C=12C=CN(C(=O)OC(C)(C)C)C2=CC(C(=O)OC)=CC=1N1CCCCS1(=O)=O GGTVKLOZXHKJRZ-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- IFWPNPCKPRWDMX-UHFFFAOYSA-N 1-phenylbutan-2-ol;dihydrochloride Chemical compound Cl.Cl.CCC(O)CC1=CC=CC=C1 IFWPNPCKPRWDMX-UHFFFAOYSA-N 0.000 description 1
- WFQKWBZAISFMEP-UHFFFAOYSA-N 1-propylcyclobutan-1-amine Chemical compound CCCC1(N)CCC1 WFQKWBZAISFMEP-UHFFFAOYSA-N 0.000 description 1
- ZLTWIJREHQCJJL-UHFFFAOYSA-N 1-trimethylsilylethanol Chemical compound CC(O)[Si](C)(C)C ZLTWIJREHQCJJL-UHFFFAOYSA-N 0.000 description 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
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- UIVJCXJWVPGGDP-UHFFFAOYSA-N methyl 3-(3-chloropropylsulfonylamino)-2-fluoro-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC(NS(=O)(=O)CCCCl)=C1F UIVJCXJWVPGGDP-UHFFFAOYSA-N 0.000 description 1
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- UQMLJYJDQDLQSG-UHFFFAOYSA-N methyl 3-(cyclopenten-1-yl)-5-(1,1-dioxo-1,2-thiazolidin-2-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(N2S(CCC2)(=O)=O)=CC=1C1=CCCC1 UQMLJYJDQDLQSG-UHFFFAOYSA-N 0.000 description 1
- NPNMKGHHWPDWSR-UHFFFAOYSA-N methyl 3-[bis(4-chlorobutylsulfonyl)amino]-2-fluoro-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC(N(S(=O)(=O)CCCCCl)S(=O)(=O)CCCCCl)=C1F NPNMKGHHWPDWSR-UHFFFAOYSA-N 0.000 description 1
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- RJNKFQYUDHQOFR-UHFFFAOYSA-N methyl 3-amino-5-(1,1-dioxo-1,2-thiazolidin-2-yl)benzoate Chemical compound COC(=O)C1=CC(N)=CC(N2S(CCC2)(=O)=O)=C1 RJNKFQYUDHQOFR-UHFFFAOYSA-N 0.000 description 1
- PQUYUYFXVDVECC-UHFFFAOYSA-N methyl 3-amino-5-(1,1-dioxo-4-phenylthiazinan-2-yl)benzoate Chemical compound COC(=O)C1=CC(N)=CC(N2S(CCC(C2)C=2C=CC=CC=2)(=O)=O)=C1 PQUYUYFXVDVECC-UHFFFAOYSA-N 0.000 description 1
- ZBDBMFRQOZLUSZ-UHFFFAOYSA-N methyl 3-amino-5-(1,1-dioxothiazinan-2-yl)-4-methylbenzoate Chemical compound COC(=O)C1=CC(N)=C(C)C(N2S(CCCC2)(=O)=O)=C1 ZBDBMFRQOZLUSZ-UHFFFAOYSA-N 0.000 description 1
- INQSYHWGCUWEGB-UHFFFAOYSA-N methyl 3-amino-5-(2-oxopiperidin-1-yl)benzoate Chemical compound COC(=O)C1=CC(N)=CC(N2C(CCCC2)=O)=C1 INQSYHWGCUWEGB-UHFFFAOYSA-N 0.000 description 1
- UAWUPZNDBKVMGQ-UHFFFAOYSA-N methyl 3-bromo-2-fluoro-5-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC(C(F)(F)F)=CC(Br)=C1F UAWUPZNDBKVMGQ-UHFFFAOYSA-N 0.000 description 1
- KKSZNQLETUXESZ-UHFFFAOYSA-N methyl 3-cyclohex-2-en-1-yl-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(C2C=CCCC2)=CC=1N1CCCC1=O KKSZNQLETUXESZ-UHFFFAOYSA-N 0.000 description 1
- GLYQNCGZIMIPIB-UHFFFAOYSA-N methyl 3-cyclopent-2-en-1-yl-5-(1,1-dioxothiazinan-2-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(C2C=CCC2)=CC=1N1CCCCS1(=O)=O GLYQNCGZIMIPIB-UHFFFAOYSA-N 0.000 description 1
- WZQLSFYPAZWVJC-UHFFFAOYSA-N methyl 3-cyclopent-3-en-1-yl-5-(1,1-dioxo-1,2-thiazolidin-2-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(C2CC=CC2)=CC=1N1CCCS1(=O)=O WZQLSFYPAZWVJC-UHFFFAOYSA-N 0.000 description 1
- OUEIPOJKOMABIU-UHFFFAOYSA-N methyl 3-methylsulfanyl-5-(2-oxopyrrolidin-1-yl)benzoate Chemical compound COC(=O)C1=CC(SC)=CC(N2C(CCC2)=O)=C1 OUEIPOJKOMABIU-UHFFFAOYSA-N 0.000 description 1
- XQXLEMPTISWGMH-SNAWJCMRSA-N methyl 4-[(e)-2-(dimethylamino)ethenyl]-3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=C(\C=C\N(C)C)C([N+]([O-])=O)=C1 XQXLEMPTISWGMH-SNAWJCMRSA-N 0.000 description 1
- LKMXNRDSTKMXFF-UHFFFAOYSA-N methyl 4-[bis(3-chloropropylsulfonyl)amino]-1-ethylindole-6-carboxylate Chemical compound C1=C(C(=O)OC)C=C2N(CC)C=CC2=C1N(S(=O)(=O)CCCCl)S(=O)(=O)CCCCl LKMXNRDSTKMXFF-UHFFFAOYSA-N 0.000 description 1
- DCOLPKXFSSVZEW-UHFFFAOYSA-N methyl 4-amino-1-ethylindole-6-carboxylate Chemical compound C1=C(C(=O)OC)C=C2N(CC)C=CC2=C1N DCOLPKXFSSVZEW-UHFFFAOYSA-N 0.000 description 1
- YJUFTUQWRBJBJN-UHFFFAOYSA-N methyl 4-chloro-3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 YJUFTUQWRBJBJN-UHFFFAOYSA-N 0.000 description 1
- IHCKIQSJPGDPET-UHFFFAOYSA-N methyl 5-(cyclopenten-1-yl)-3-(1,1-dioxothiazinan-2-yl)-2-fluorobenzoate Chemical compound FC=1C(C(=O)OC)=CC(C=2CCCC=2)=CC=1N1CCCCS1(=O)=O IHCKIQSJPGDPET-UHFFFAOYSA-N 0.000 description 1
- FWNZUGHBDOWWEI-UHFFFAOYSA-N methyl 5-[ethyl-[(4-methoxyphenyl)methyl]amino]-2-fluoro-3-(2-oxopyrrolidin-1-yl)benzoate Chemical compound C=1C(N2C(CCC2)=O)=C(F)C(C(=O)OC)=CC=1N(CC)CC1=CC=C(OC)C=C1 FWNZUGHBDOWWEI-UHFFFAOYSA-N 0.000 description 1
- BVAFWUSBMURRDS-UHFFFAOYSA-N methyl 7-(4-chlorobutanoylamino)-2h-benzotriazole-5-carboxylate Chemical compound COC(=O)C1=CC(NC(=O)CCCCl)=C2N=NNC2=C1 BVAFWUSBMURRDS-UHFFFAOYSA-N 0.000 description 1
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- WYVFPGFWUKBXPZ-UHFFFAOYSA-N tert-butyl n-(4-oxocyclohexyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(=O)CC1 WYVFPGFWUKBXPZ-UHFFFAOYSA-N 0.000 description 1
- NTJRUECYWQYXPU-RBUKOAKNSA-N tert-butyl n-[(2s,3r)-4-[(3-ethyl-1,2-oxazol-5-yl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound O1N=C(CC)C=C1CNC[C@@H](O)[C@@H](NC(=O)OC(C)(C)C)CC1=CC=CC=C1 NTJRUECYWQYXPU-RBUKOAKNSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- IHOVFYSQUDPMCN-QKUIIBHLSA-N zosuquidar Chemical compound C([C@H](COC=1C2=CC=CN=C2C=CC=1)O)N(CC1)CCN1C1C2=CC=CC=C2C2C(F)(F)C2C2=CC=CC=C12 IHOVFYSQUDPMCN-QKUIIBHLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
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- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings 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
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- 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
- C07D401/12—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 chain containing hetero atoms as chain links
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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DE19818614A1 (de) | 1998-04-20 | 1999-10-21 | Basf Ag | Neue substituierte Amide, deren Herstellung und Anwendung |
US6562827B1 (en) | 1998-04-20 | 2003-05-13 | Abbott Laboratories | Heterocyclically substituted amides used as calpain inhibitors |
SE9801901L (sv) | 1998-05-29 | 1999-08-02 | Bone Support Ab | Förfarande för framställning av pulverkomponent till cement för medicinskt bruk, användning av sådan pulverkomponent samt sådan pulverkomponent |
SE9904652D0 (sv) | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
US7119085B2 (en) | 2000-03-23 | 2006-10-10 | Elan Pharmaceuticals, Inc. | Methods to treat alzheimer's disease |
PE20020276A1 (es) | 2000-06-30 | 2002-04-06 | Elan Pharm Inc | COMPUESTOS DE AMINA SUSTITUIDA COMO INHIBIDORES DE ß-SECRETASA PARA EL TRATAMIENTO DE ALZHEIMER |
DE60116313T2 (de) | 2000-06-30 | 2006-08-31 | Elan Pharmaceuticals, Inc., San Francisco | Verbindungen zur behandlung der alzheimerischen krankheit |
AR035960A1 (es) | 2001-04-23 | 2004-07-28 | Elan Pharm Inc | Epoxidos sustituidos y procesos para prepararlos |
NZ533107A (en) | 2001-11-08 | 2007-04-27 | Upjohn Co | N, N'-substituted-1,3-diamino-2-hydroxypropane derivatives |
-
2002
- 2002-12-05 GB GBGB0228410.7A patent/GB0228410D0/en not_active Ceased
-
2003
- 2003-12-03 CA CA002508325A patent/CA2508325A1/en not_active Abandoned
- 2003-12-03 BR BR0317020-9A patent/BR0317020A/pt unknown
- 2003-12-03 AU AU2003292198A patent/AU2003292198B2/en not_active Ceased
- 2003-12-03 DE DE60312031T patent/DE60312031T2/de not_active Expired - Fee Related
- 2003-12-03 NZ NZ539841A patent/NZ539841A/xx unknown
- 2003-12-03 WO PCT/EP2003/013806 patent/WO2004050619A1/en active IP Right Grant
- 2003-12-03 EP EP03767756A patent/EP1567488B1/en not_active Expired - Lifetime
- 2003-12-03 PT PT03767756T patent/PT1567488E/pt unknown
- 2003-12-03 ES ES03767756T patent/ES2282685T3/es not_active Expired - Lifetime
- 2003-12-03 AT AT03767756T patent/ATE354565T1/de not_active IP Right Cessation
- 2003-12-03 CN CNA2003801085153A patent/CN1735592A/zh active Pending
- 2003-12-03 US US10/536,303 patent/US7253198B2/en not_active Expired - Fee Related
- 2003-12-03 PL PL377587A patent/PL377587A1/pl not_active Application Discontinuation
- 2003-12-03 MX MXPA05006088A patent/MXPA05006088A/es active IP Right Grant
- 2003-12-03 SI SI200330793T patent/SI1567488T1/sl unknown
- 2003-12-03 DK DK03767756T patent/DK1567488T3/da active
- 2003-12-03 RU RU2005121146/04A patent/RU2005121146A/ru not_active Application Discontinuation
- 2003-12-03 KR KR1020057010104A patent/KR20050084143A/ko not_active Application Discontinuation
- 2003-12-03 JP JP2004556305A patent/JP2006514634A/ja not_active Withdrawn
-
2005
- 2005-05-09 ZA ZA200503693A patent/ZA200503693B/en unknown
- 2005-06-30 IS IS7925A patent/IS7925A/is unknown
- 2005-07-01 MA MA28368A patent/MA27608A1/fr unknown
- 2005-07-04 NO NO20053263A patent/NO20053263L/no not_active Application Discontinuation
-
2006
- 2006-02-17 HK HK06102182A patent/HK1083624A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
GB0228410D0 (en) | 2003-01-08 |
CN1735592A (zh) | 2006-02-15 |
ATE354565T1 (de) | 2007-03-15 |
DK1567488T3 (da) | 2007-06-18 |
PL377587A1 (pl) | 2006-02-06 |
PT1567488E (pt) | 2007-05-31 |
US7253198B2 (en) | 2007-08-07 |
EP1567488B1 (en) | 2007-02-21 |
HK1083624A1 (en) | 2006-07-07 |
CA2508325A1 (en) | 2004-06-17 |
MXPA05006088A (es) | 2005-08-16 |
AU2003292198A1 (en) | 2004-06-23 |
DE60312031D1 (de) | 2007-04-05 |
EP1567488A1 (en) | 2005-08-31 |
BR0317020A (pt) | 2005-10-25 |
ES2282685T3 (es) | 2007-10-16 |
NO20053263L (no) | 2005-08-31 |
DE60312031T2 (de) | 2007-11-22 |
SI1567488T1 (sl) | 2007-08-31 |
WO2004050619A1 (en) | 2004-06-17 |
NO20053263D0 (no) | 2005-07-04 |
US20060025459A1 (en) | 2006-02-02 |
IS7925A (is) | 2005-06-30 |
AU2003292198B2 (en) | 2007-09-06 |
JP2006514634A (ja) | 2006-05-11 |
NZ539841A (en) | 2007-11-30 |
RU2005121146A (ru) | 2006-01-20 |
MA27608A1 (fr) | 2005-11-01 |
KR20050084143A (ko) | 2005-08-26 |
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