CA2610396A1 - Organic compounds - Google Patents
Organic compounds Download PDFInfo
- Publication number
- CA2610396A1 CA2610396A1 CA002610396A CA2610396A CA2610396A1 CA 2610396 A1 CA2610396 A1 CA 2610396A1 CA 002610396 A CA002610396 A CA 002610396A CA 2610396 A CA2610396 A CA 2610396A CA 2610396 A1 CA2610396 A1 CA 2610396A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- methylamino
- oxo
- propionamide
- dihydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 37
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 24
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 230000002062 proliferating effect Effects 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 12
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- DRIZXPSWQXTWQI-FQEVSTJZSA-N (2s)-2-(methylamino)-n-[2-oxo-1-[(3-phenoxyphenyl)methyl]-6-phenylpyridin-3-yl]propanamide Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 DRIZXPSWQXTWQI-FQEVSTJZSA-N 0.000 claims description 7
- SJSDATJXTYSKMH-SFHVURJKSA-N (2s)-2-(methylamino)-n-[2-oxo-1-[2-oxo-2-(2-phenylethylamino)ethyl]-6-phenylpyridin-3-yl]propanamide Chemical compound C=1C=CC=CC=1CCNC(=O)CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 SJSDATJXTYSKMH-SFHVURJKSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- UUGCANYJPKCZRZ-JLHZNFIISA-N (3s,6s,8z,10ar)-6-[[(2s)-2-(methylamino)propanoyl]amino]-5-oxo-n-(2-phenylethyl)-2,3,6,7,10,10a-hexahydro-1h-pyrrolo[1,2-a]azocine-3-carboxamide Chemical compound O=C([C@@H]1CC[C@@H]2C\C=C/C[C@@H](C(N21)=O)NC(=O)[C@H](C)NC)NCCC1=CC=CC=C1 UUGCANYJPKCZRZ-JLHZNFIISA-N 0.000 claims description 5
- CZBWMJLGSLNDIF-FHWLQOOXSA-N (4s,7s)-7-[[(2s)-2-(methylamino)butanoyl]amino]-6,10-dioxo-n-(2-phenylethyl)-2,3,4,7,8,9-hexahydro-1h-pyridazino[1,2-a]diazepine-4-carboxamide Chemical compound O=C([C@@H]1CCCN2C(=O)CC[C@@H](C(N21)=O)NC(=O)[C@@H](NC)CC)NCCC1=CC=CC=C1 CZBWMJLGSLNDIF-FHWLQOOXSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 210000000170 cell membrane Anatomy 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 239000007822 coupling agent Substances 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000005897 peptide coupling reaction Methods 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- HIBBHDISMHRSGO-GZMMRYBBSA-N (2s)-2-[[2-[3-[[(2s)-2-aminopropanoyl]amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]acetyl]amino]-3-phenylpropanamide Chemical compound C([C@H](NC(=O)CN1C2=CC=CC=C2CCC(C1=O)NC(=O)[C@@H](N)C)C(N)=O)C1=CC=CC=C1 HIBBHDISMHRSGO-GZMMRYBBSA-N 0.000 claims 2
- DSWQOVAEVMDMLK-NRFANRHFSA-N (2s)-n-[1-[2-(2,2-diphenylethylamino)-2-oxoethyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CNC(=O)CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 DSWQOVAEVMDMLK-NRFANRHFSA-N 0.000 claims 2
- YLFMKQVOHZWDJR-NDXORKPFSA-N (2S,11S)-11-[[(2S)-2-(methylamino)propanoyl]amino]-12-oxo-N-(2-phenylethyl)-1-azatricyclo[6.4.1.04,13]trideca-4,6,8(13)-triene-2-carboxamide Chemical compound O=C([C@@H]1CC=2C=CC=C3CC[C@@H](C(N1C3=2)=O)NC(=O)[C@H](C)NC)NCCC1=CC=CC=C1 YLFMKQVOHZWDJR-NDXORKPFSA-N 0.000 claims 1
- UKRZDZDSVAEZIB-IBGZPJMESA-N (2s)-2-(ethylamino)-n-[1-[3-(4-fluoroanilino)benzoyl]-2-oxo-6-phenylpyridin-3-yl]propanamide Chemical compound C=1C=CC(NC=2C=CC(F)=CC=2)=CC=1C(=O)N1C(=O)C(NC(=O)[C@H](C)NCC)=CC=C1C1=CC=CC=C1 UKRZDZDSVAEZIB-IBGZPJMESA-N 0.000 claims 1
- HGZJYVOSGZBPLA-FQEVSTJZSA-N (2s)-2-(ethylamino)-n-[1-[[3-(4-fluoroanilino)phenyl]methyl]-2-oxo-6-phenylpyridin-3-yl]propanamide Chemical compound C=1C=CC(NC=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NCC)=CC=C1C1=CC=CC=C1 HGZJYVOSGZBPLA-FQEVSTJZSA-N 0.000 claims 1
- YONXBRUBJWDFNO-SPQDMEGHSA-N (2s)-2-(methylamino)-n-[(3s)-2-oxo-1-[1-oxo-1-(2-phenylethylamino)propan-2-yl]azepan-3-yl]propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)CCCCN1C(C)C(=O)NCCC1=CC=CC=C1 YONXBRUBJWDFNO-SPQDMEGHSA-N 0.000 claims 1
- ZPZWUJHYFIHAHK-RDJZCZTQSA-N (2s)-2-(methylamino)-n-[(3s)-2-oxo-1-[2-oxo-2-(2-phenylethylamino)ethyl]azepan-3-yl]propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)CCCCN1CC(=O)NCCC1=CC=CC=C1 ZPZWUJHYFIHAHK-RDJZCZTQSA-N 0.000 claims 1
- OIMPUPSJBKWJNM-FQEVSTJZSA-N (2s)-2-(methylamino)-n-[2-oxo-1-[(3-phenoxyphenyl)methyl]pyridin-3-yl]butanamide Chemical compound O=C1C(NC(=O)[C@@H](NC)CC)=CC=CN1CC1=CC=CC(OC=2C=CC=CC=2)=C1 OIMPUPSJBKWJNM-FQEVSTJZSA-N 0.000 claims 1
- UEZDDCHBHHGSTE-INIZCTEOSA-N (2s)-2-(methylamino)-n-[2-oxo-1-[(3-phenoxyphenyl)methyl]pyridin-3-yl]propanamide Chemical compound O=C1C(NC(=O)[C@H](C)NC)=CC=CN1CC1=CC=CC(OC=2C=CC=CC=2)=C1 UEZDDCHBHHGSTE-INIZCTEOSA-N 0.000 claims 1
- UMKCCJAVQJDHTR-HXBUSHRASA-N (2s)-2-(methylamino)-n-[2-oxo-1-[2-oxo-2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)ethyl]-6-phenylpyridin-3-yl]propanamide Chemical compound C1CCC2=CC=CC=C2C1NC(=O)CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 UMKCCJAVQJDHTR-HXBUSHRASA-N 0.000 claims 1
- PFBMDJWNEQNGJC-AWEZNQCLSA-N (2s)-2-(methylamino)-n-[2-oxo-1-[2-oxo-2-(2-phenylethylamino)ethyl]pyridin-3-yl]propanamide Chemical compound O=C1C(NC(=O)[C@H](C)NC)=CC=CN1CC(=O)NCCC1=CC=CC=C1 PFBMDJWNEQNGJC-AWEZNQCLSA-N 0.000 claims 1
- QTPWSSZPLGGEFQ-FQEVSTJZSA-N (2s)-2-(methylamino)-n-[2-oxo-6-phenyl-1-(5-phenylpentyl)pyridin-3-yl]propanamide Chemical compound C=1C=CC=CC=1CCCCCN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 QTPWSSZPLGGEFQ-FQEVSTJZSA-N 0.000 claims 1
- JIMQPCJSXRNTDN-IBGZPJMESA-N (2s)-2-(methylamino)-n-[2-oxo-6-phenyl-1-[2-(2-phenylethylsulfanyl)ethyl]pyridin-3-yl]propanamide Chemical compound C=1C=CC=CC=1CCSCCN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 JIMQPCJSXRNTDN-IBGZPJMESA-N 0.000 claims 1
- ZIRVTKGJZRUKQL-QFIPXVFZSA-N (2s)-2-(methylamino)-n-[2-oxo-6-phenyl-1-[2-(2-phenylethylsulfonyl)ethyl]pyridin-3-yl]butanamide Chemical compound C=1C=CC=CC=1CCS(=O)(=O)CCN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=CC=C1 ZIRVTKGJZRUKQL-QFIPXVFZSA-N 0.000 claims 1
- PVPRFXTYPXMQRR-IBGZPJMESA-N (2s)-2-(methylamino)-n-[2-oxo-6-phenyl-1-[2-(2-phenylethylsulfonyl)ethyl]pyridin-3-yl]propanamide Chemical compound C=1C=CC=CC=1CCS(=O)(=O)CCN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 PVPRFXTYPXMQRR-IBGZPJMESA-N 0.000 claims 1
- QDZMWCXGXWQKLW-KRWDZBQOSA-N (2s)-2-(methylamino)-n-[6-methyl-2-oxo-1-[(3-phenoxyphenyl)methyl]pyridin-3-yl]propanamide Chemical compound O=C1C(NC(=O)[C@H](C)NC)=CC=C(C)N1CC1=CC=CC(OC=2C=CC=CC=2)=C1 QDZMWCXGXWQKLW-KRWDZBQOSA-N 0.000 claims 1
- QRAOJRVXRGMWJF-BPUTZDHNSA-N (2s)-2-[[2-[(3s)-3-[[(2s)-2-aminopropanoyl]amino]-2-oxoazepan-1-yl]acetyl]amino]-3-phenylpropanamide Chemical compound O=C1[C@@H](NC(=O)[C@@H](N)C)CCCCN1CC(=O)N[C@H](C(N)=O)CC1=CC=CC=C1 QRAOJRVXRGMWJF-BPUTZDHNSA-N 0.000 claims 1
- NMXIJQQFEIVHQV-WFASDCNBSA-N (2s)-2-[[2-[3-[[(2s)-2-aminopropanoyl]amino]-2-oxopyridin-1-yl]acetyl]amino]-3-phenylpropanamide Chemical compound O=C1C(NC(=O)[C@@H](N)C)=CC=CN1CC(=O)N[C@H](C(N)=O)CC1=CC=CC=C1 NMXIJQQFEIVHQV-WFASDCNBSA-N 0.000 claims 1
- UFSQVPXRLDGSJZ-NRFANRHFSA-N (2s)-n-[1-[2-(1,3-dihydroisoindol-2-yl)-2-oxoethyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)butanamide Chemical compound C1C2=CC=CC=C2CN1C(=O)CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=CC=C1 UFSQVPXRLDGSJZ-NRFANRHFSA-N 0.000 claims 1
- MKVKWNPWVAMZHR-KRWDZBQOSA-N (2s)-n-[1-[2-(1,3-dihydroisoindol-2-yl)-2-oxoethyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C1C2=CC=CC=C2CN1C(=O)CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 MKVKWNPWVAMZHR-KRWDZBQOSA-N 0.000 claims 1
- ZUFVEZUNZINJOH-QHCPKHFHSA-N (2s)-n-[1-[2-(2,3-dihydro-1h-inden-2-yloxy)ethyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)butanamide Chemical compound C1C2=CC=CC=C2CC1OCCN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=CC=C1 ZUFVEZUNZINJOH-QHCPKHFHSA-N 0.000 claims 1
- JMOAVXGTFIDXSI-SFHVURJKSA-N (2s)-n-[1-[2-(2,3-dihydro-1h-inden-2-yloxy)ethyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C1C2=CC=CC=C2CC1OCCN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 JMOAVXGTFIDXSI-SFHVURJKSA-N 0.000 claims 1
- RBYJKUIGAQLBMH-INIZCTEOSA-N (2s)-n-[1-[2-[(4-fluorophenyl)methylamino]-2-oxoethyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=C(F)C=CC=1CNC(=O)CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 RBYJKUIGAQLBMH-INIZCTEOSA-N 0.000 claims 1
- GTOMYMCZBPZBLS-BXXZMZEQSA-N (2s)-n-[1-[2-[ethyl(1,2,3,4-tetrahydronaphthalen-1-yl)amino]-2-oxoethyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)butanamide Chemical compound C1CCC2=CC=CC=C2C1N(CC)C(=O)CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=C(F)C=C1 GTOMYMCZBPZBLS-BXXZMZEQSA-N 0.000 claims 1
- NHSQWHIHHMEKPI-SXMXNQBWSA-N (2s)-n-[1-[2-[ethyl(1,2,3,4-tetrahydronaphthalen-1-yl)amino]-2-oxoethyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C1CCC2=CC=CC=C2C1N(CC)C(=O)CN(C(C(NC(=O)[C@H](C)NC)=CC=1)=O)C=1C1=CC=C(F)C=C1 NHSQWHIHHMEKPI-SXMXNQBWSA-N 0.000 claims 1
- IVIBCTPZKXRZTA-SXMXNQBWSA-N (2s)-n-[1-[2-[ethyl(1,2,3,4-tetrahydronaphthalen-1-yl)amino]acetyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C1CCC2=CC=CC=C2C1N(CC)CC(=O)N(C(C(NC(=O)[C@H](C)NC)=CC=1)=O)C=1C1=CC=C(F)C=C1 IVIBCTPZKXRZTA-SXMXNQBWSA-N 0.000 claims 1
- CMESKYBIBNHDTA-SVQMELKDSA-N (2s)-n-[1-[2-[ethyl(1,2,3,4-tetrahydronaphthalen-1-yl)amino]ethyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C1CCC2=CC=CC=C2C1N(CC)CCN(C(C(NC(=O)[C@H](C)NC)=CC=1)=O)C=1C1=CC=C(F)C=C1 CMESKYBIBNHDTA-SVQMELKDSA-N 0.000 claims 1
- YTUMXTFLWANXIS-QFIPXVFZSA-N (2s)-n-[1-[2-[ethyl-[(4-fluorophenyl)methyl]amino]-2-oxoethyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=C(F)C=CC=1CN(CC)C(=O)CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=C(F)C=C1 YTUMXTFLWANXIS-QFIPXVFZSA-N 0.000 claims 1
- RJJDVYGXIQJCBR-KRWDZBQOSA-N (2s)-n-[1-[2-[ethyl-[(4-fluorophenyl)methyl]amino]-2-oxoethyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=C(F)C=CC=1C1=CC=C(NC(=O)[C@H](C)NC)C(=O)N1CC(=O)N(CC)CC1=CC=C(F)C=C1 RJJDVYGXIQJCBR-KRWDZBQOSA-N 0.000 claims 1
- FWYIGTLXAWSBBC-SFHVURJKSA-N (2s)-n-[1-[2-[ethyl-[(4-fluorophenyl)methyl]amino]ethyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=C(F)C=CC=1CN(CC)CCN(C(C(NC(=O)[C@H](C)NC)=CC=1)=O)C=1C1=CC=C(F)C=C1 FWYIGTLXAWSBBC-SFHVURJKSA-N 0.000 claims 1
- OQDDLVFZUVIZST-IBGZPJMESA-N (2s)-n-[1-[3-(4-fluoro-n-methylanilino)benzoyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(N(C)C=2C=CC(F)=CC=2)=CC=1C(=O)N1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 OQDDLVFZUVIZST-IBGZPJMESA-N 0.000 claims 1
- PVVAIJHFANOEDG-DEOSSOPVSA-N (2s)-n-[1-[3-(4-fluorobenzoyl)benzoyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=CC(C(=O)C=2C=CC(F)=CC=2)=CC=1C(=O)N1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=CC=C1 PVVAIJHFANOEDG-DEOSSOPVSA-N 0.000 claims 1
- JTPXRKBISRDJAM-SFHVURJKSA-N (2s)-n-[1-[3-(4-fluorobenzoyl)benzoyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC(F)=CC=2)=CC=1C(=O)N1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 JTPXRKBISRDJAM-SFHVURJKSA-N 0.000 claims 1
- DXKGERZQZOHAAR-SFHVURJKSA-N (2s)-n-[1-[3-(4-fluorophenoxy)benzoyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(OC=2C=CC(F)=CC=2)=CC=1C(=O)N1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 DXKGERZQZOHAAR-SFHVURJKSA-N 0.000 claims 1
- XOUBNNDYHJEUDL-SFHVURJKSA-N (2s)-n-[1-[3-(4-fluorophenyl)sulfanylbenzoyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(SC=2C=CC(F)=CC=2)=CC=1C(=O)N1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 XOUBNNDYHJEUDL-SFHVURJKSA-N 0.000 claims 1
- VMSPUECDJZCSTJ-SFHVURJKSA-N (2s)-n-[1-[3-(4-fluorophenyl)sulfonylbenzoyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(S(=O)(=O)C=2C=CC(F)=CC=2)=CC=1C(=O)N1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 VMSPUECDJZCSTJ-SFHVURJKSA-N 0.000 claims 1
- DYWSZHQKRXSMGZ-SANMLTNESA-N (2s)-n-[1-[[3-(4-fluoro-n-methylanilino)phenyl]methyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=CC(N(C)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=CC=C1 DYWSZHQKRXSMGZ-SANMLTNESA-N 0.000 claims 1
- KKGFIXANZMACQL-FQEVSTJZSA-N (2s)-n-[1-[[3-(4-fluoro-n-methylanilino)phenyl]methyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(N(C)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 KKGFIXANZMACQL-FQEVSTJZSA-N 0.000 claims 1
- ZGSDFIXETSEZTL-SANMLTNESA-N (2s)-n-[1-[[3-(4-fluoro-n-methylanilino)phenyl]methyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=CC(N(C)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=C(F)C=C1 ZGSDFIXETSEZTL-SANMLTNESA-N 0.000 claims 1
- BSZOHGUODMNRKA-IBGZPJMESA-N (2s)-n-[1-[[3-(4-fluoro-n-methylanilino)phenyl]methyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(N(C)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 BSZOHGUODMNRKA-IBGZPJMESA-N 0.000 claims 1
- IXGRPXIBRPJNKB-VWLOTQADSA-N (2s)-n-[1-[[3-(4-fluoroanilino)phenyl]methyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=CC(NC=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=CC=C1 IXGRPXIBRPJNKB-VWLOTQADSA-N 0.000 claims 1
- ZAKUXESMRJSKER-SFHVURJKSA-N (2s)-n-[1-[[3-(4-fluoroanilino)phenyl]methyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(NC=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 ZAKUXESMRJSKER-SFHVURJKSA-N 0.000 claims 1
- CUFUGIFIDDHNAY-VWLOTQADSA-N (2s)-n-[1-[[3-(4-fluorobenzoyl)phenyl]methyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=CC(C(=O)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=CC=C1 CUFUGIFIDDHNAY-VWLOTQADSA-N 0.000 claims 1
- HYUUDCAZTPMEMW-VWLOTQADSA-N (2s)-n-[1-[[3-(4-fluorobenzoyl)phenyl]methyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=CC(C(=O)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=C(F)C=C1 HYUUDCAZTPMEMW-VWLOTQADSA-N 0.000 claims 1
- XTWORBQLYLGZOJ-SFHVURJKSA-N (2s)-n-[1-[[3-(4-fluorobenzoyl)phenyl]methyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 XTWORBQLYLGZOJ-SFHVURJKSA-N 0.000 claims 1
- VLFJFYXYZQIBCT-VWLOTQADSA-N (2s)-n-[1-[[3-(4-fluorophenoxy)phenyl]methyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=CC(OC=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=CC=C1 VLFJFYXYZQIBCT-VWLOTQADSA-N 0.000 claims 1
- VVFYZPVNTDMBKC-IBGZPJMESA-N (2s)-n-[1-[[3-(4-fluorophenoxy)phenyl]methyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(OC=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 VVFYZPVNTDMBKC-IBGZPJMESA-N 0.000 claims 1
- BCEYTJDBPKAJAY-VWLOTQADSA-N (2s)-n-[1-[[3-(4-fluorophenoxy)phenyl]methyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=CC(OC=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=C(F)C=C1 BCEYTJDBPKAJAY-VWLOTQADSA-N 0.000 claims 1
- NXVFMDFTMJCMRW-SFHVURJKSA-N (2s)-n-[1-[[3-(4-fluorophenoxy)phenyl]methyl]-6-(4-fluorophenyl)-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(OC=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 NXVFMDFTMJCMRW-SFHVURJKSA-N 0.000 claims 1
- DMVWTUFMNOJQJN-IBGZPJMESA-N (2s)-n-[1-[[3-(4-fluorophenyl)sulfanylphenyl]methyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(SC=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 DMVWTUFMNOJQJN-IBGZPJMESA-N 0.000 claims 1
- AYNHTWSWUQVRMQ-VWLOTQADSA-N (2s)-n-[1-[[3-(4-fluorophenyl)sulfonylphenyl]methyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=CC(S(=O)(=O)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=CC=C1 AYNHTWSWUQVRMQ-VWLOTQADSA-N 0.000 claims 1
- MEZFCJCDQYQNCR-IBGZPJMESA-N (2s)-n-[1-[[3-(4-fluorophenyl)sulfonylphenyl]methyl]-2-oxo-6-phenylpyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(S(=O)(=O)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=CC=C1 MEZFCJCDQYQNCR-IBGZPJMESA-N 0.000 claims 1
- PAFBFPBLROZSBY-FQEVSTJZSA-N (2s)-n-[6-(4-fluorophenyl)-1-[2-[(4-fluorophenyl)methylamino]-2-oxoethyl]-2-oxopyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=C(F)C=CC=1CNC(=O)CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=C(F)C=C1 PAFBFPBLROZSBY-FQEVSTJZSA-N 0.000 claims 1
- VOMHICCAKBNGMC-HNNXBMFYSA-N (2s)-n-[6-(4-fluorophenyl)-1-[2-[(4-fluorophenyl)methylamino]-2-oxoethyl]-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=C(F)C=CC=1CNC(=O)CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 VOMHICCAKBNGMC-HNNXBMFYSA-N 0.000 claims 1
- FACGLOMYPPLPLQ-SFHVURJKSA-N (2s)-n-[6-(4-fluorophenyl)-1-[[3-(4-fluorophenyl)sulfanylphenyl]methyl]-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(SC=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 FACGLOMYPPLPLQ-SFHVURJKSA-N 0.000 claims 1
- NKPVOQWPPJVFKQ-VWLOTQADSA-N (2s)-n-[6-(4-fluorophenyl)-1-[[3-(4-fluorophenyl)sulfonylphenyl]methyl]-2-oxopyridin-3-yl]-2-(methylamino)butanamide Chemical compound C=1C=CC(S(=O)(=O)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=C(F)C=C1 NKPVOQWPPJVFKQ-VWLOTQADSA-N 0.000 claims 1
- FKOMSOIJGLVTLS-SFHVURJKSA-N (2s)-n-[6-(4-fluorophenyl)-1-[[3-(4-fluorophenyl)sulfonylphenyl]methyl]-2-oxopyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC(S(=O)(=O)C=2C=CC(F)=CC=2)=CC=1CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 FKOMSOIJGLVTLS-SFHVURJKSA-N 0.000 claims 1
- WYQOPBSVYFQWAD-NQCNTLBGSA-N (2s)-n-[6-(4-fluorophenyl)-2-oxo-1-[2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)acetyl]pyridin-3-yl]-2-(methylamino)butanamide Chemical compound C1CCC2=CC=CC=C2C1NCC(=O)N1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=C(F)C=C1 WYQOPBSVYFQWAD-NQCNTLBGSA-N 0.000 claims 1
- NEXILQFCJFSNQK-LBOXEOMUSA-N (2s)-n-[6-(4-fluorophenyl)-2-oxo-1-[2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)acetyl]pyridin-3-yl]-2-(methylamino)propanamide Chemical compound C1CCC2=CC=CC=C2C1NCC(=O)N1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 NEXILQFCJFSNQK-LBOXEOMUSA-N 0.000 claims 1
- XXQNJNPEENSMCS-XNUZUHMRSA-N (2s)-n-[6-(4-fluorophenyl)-2-oxo-1-[2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)ethyl]pyridin-3-yl]-2-(methylamino)propanamide Chemical compound C1CCC2=CC=CC=C2C1NCCN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 XXQNJNPEENSMCS-XNUZUHMRSA-N 0.000 claims 1
- ZKHAGSIZBVLPDA-NQCNTLBGSA-N (2s)-n-[6-(4-fluorophenyl)-2-oxo-1-[2-oxo-2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)ethyl]pyridin-3-yl]-2-(methylamino)butanamide Chemical compound C1CCC2=CC=CC=C2C1NC(=O)CN1C(=O)C(NC(=O)[C@@H](NC)CC)=CC=C1C1=CC=C(F)C=C1 ZKHAGSIZBVLPDA-NQCNTLBGSA-N 0.000 claims 1
- OUVQBOSBRWVKPE-LBOXEOMUSA-N (2s)-n-[6-(4-fluorophenyl)-2-oxo-1-[2-oxo-2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)ethyl]pyridin-3-yl]-2-(methylamino)propanamide Chemical compound C1CCC2=CC=CC=C2C1NC(=O)CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1C1=CC=C(F)C=C1 OUVQBOSBRWVKPE-LBOXEOMUSA-N 0.000 claims 1
- HPDYXFRQDGGEIU-IBGZPJMESA-N (2s)-n-[6-benzyl-2-oxo-1-[2-oxo-2-(2-phenylethylamino)ethyl]pyridin-3-yl]-2-(methylamino)propanamide Chemical compound C=1C=CC=CC=1CCNC(=O)CN1C(=O)C(NC(=O)[C@H](C)NC)=CC=C1CC1=CC=CC=C1 HPDYXFRQDGGEIU-IBGZPJMESA-N 0.000 claims 1
- RMJZRXGIWODYQW-KRWDZBQOSA-N (2s)-n-[6-butyl-2-oxo-1-[2-oxo-2-(2-phenylethylamino)ethyl]pyridin-3-yl]-2-(methylamino)propanamide Chemical compound CCCCC1=CC=C(NC(=O)[C@H](C)NC)C(=O)N1CC(=O)NCCC1=CC=CC=C1 RMJZRXGIWODYQW-KRWDZBQOSA-N 0.000 claims 1
- UEURTFRTZAGRJH-HJWJTTGWSA-N (3r,6s,8as)-6-[[(2s)-2-(methylamino)propanoyl]amino]-5-oxo-n-(2-phenylethyl)-2,3,6,7,8,8a-hexahydro-[1,3]thiazolo[3,2-a]pyridine-3-carboxamide Chemical compound O=C([C@@H]1CS[C@H]2CC[C@@H](C(N21)=O)NC(=O)[C@H](C)NC)NCCC1=CC=CC=C1 UEURTFRTZAGRJH-HJWJTTGWSA-N 0.000 claims 1
- HAFNXRMVEZQARL-HKUYNNGSSA-N (3s)-6-[[(2s)-2-(methylamino)butanoyl]amino]-5-oxo-n-(2-phenylethyl)-2,3-dihydro-1h-indolizine-3-carboxamide Chemical compound O=C([C@@H]1CCC2=CC=C(C(N21)=O)NC(=O)[C@@H](NC)CC)NCCC1=CC=CC=C1 HAFNXRMVEZQARL-HKUYNNGSSA-N 0.000 claims 1
- FLFFACIONBCEJL-KSSFIOAISA-N (3s)-6-[[(2s)-2-(methylamino)propanoyl]amino]-5-oxo-n-(2-phenylethyl)-2,3-dihydro-1h-indolizine-3-carboxamide Chemical compound O=C([C@@H]1CCC2=CC=C(C(N21)=O)NC(=O)[C@H](C)NC)NCCC1=CC=CC=C1 FLFFACIONBCEJL-KSSFIOAISA-N 0.000 claims 1
- POFQUMDARHAMGM-KSSFIOAISA-N (3s)-n-(2-cyclohexylethyl)-6-[[(2s)-2-(methylamino)propanoyl]amino]-5-oxo-2,3-dihydro-1h-indolizine-3-carboxamide Chemical compound O=C([C@@H]1CCC2=CC=C(C(N21)=O)NC(=O)[C@H](C)NC)NCCC1CCCCC1 POFQUMDARHAMGM-KSSFIOAISA-N 0.000 claims 1
- HZVMFNCNTRPVJU-BZSNNMDCSA-N (3s,6s)-6-[[(2s)-2-(methylamino)butanoyl]amino]-5,9-dioxo-n-(2-phenylethyl)-1,2,3,6,7,8-hexahydropyrazolo[1,2-a]diazepine-3-carboxamide Chemical compound O=C([C@@H]1CCN2C(=O)CC[C@@H](C(N21)=O)NC(=O)[C@@H](NC)CC)NCCC1=CC=CC=C1 HZVMFNCNTRPVJU-BZSNNMDCSA-N 0.000 claims 1
- QTUCSIGLHWTDLP-FHWLQOOXSA-N (3s,6s)-6-[[(2s)-2-(methylamino)butanoyl]amino]-5-oxo-n-(2-phenylethyl)-2,3,6,7,8,9-hexahydro-1h-pyrazolo[1,2-a]diazepine-3-carboxamide Chemical compound O=C([C@@H]1CCN2CCC[C@@H](C(N21)=O)NC(=O)[C@@H](NC)CC)NCCC1=CC=CC=C1 QTUCSIGLHWTDLP-FHWLQOOXSA-N 0.000 claims 1
- KJKVVRHRZCWHGY-XIRDDKMYSA-N (3s,6s)-6-[[(2s)-2-(methylamino)propanoyl]amino]-5,9-dioxo-n-(2-phenylethyl)-1,2,3,6,7,8-hexahydropyrazolo[1,2-a]diazepine-3-carboxamide Chemical compound O=C([C@@H]1CCN2C(=O)CC[C@@H](C(N21)=O)NC(=O)[C@H](C)NC)NCCC1=CC=CC=C1 KJKVVRHRZCWHGY-XIRDDKMYSA-N 0.000 claims 1
- OWWSPUUIHIVPLB-SZMVWBNQSA-N (3s,6s)-6-[[(2s)-2-(methylamino)propanoyl]amino]-5-oxo-n-(2-phenylethyl)-2,3,6,7,8,9-hexahydro-1h-pyrazolo[1,2-a]diazepine-3-carboxamide Chemical compound O=C([C@@H]1CCN2CCC[C@@H](C(N21)=O)NC(=O)[C@H](C)NC)NCCC1=CC=CC=C1 OWWSPUUIHIVPLB-SZMVWBNQSA-N 0.000 claims 1
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- OZNVFPRSQNJWBR-SWYNNERLSA-N (6s,10as)-6-[[(2s)-2-(methylamino)propanoyl]amino]-5-oxo-n-(2-phenylethyl)-2,3,6,7,8,9,10,10a-octahydro-1h-pyrrolo[1,2-a]azocine-3-carboxamide Chemical compound C([C@@H]1CCCC[C@@H](C(N11)=O)NC(=O)[C@H](C)NC)CC1C(=O)NCCC1=CC=CC=C1 OZNVFPRSQNJWBR-SWYNNERLSA-N 0.000 claims 1
- QGQIOQOZCBKVTE-SXMXJJAMSA-N 2-(methylamino)-n-[(2s)-1-oxo-1-[(2s,5s)-2-(2-phenylethylsulfinylmethyl)-5-propylpyrrolidin-1-yl]butan-2-yl]butanamide Chemical compound CCC(NC)C(=O)N[C@@H](CC)C(=O)N1[C@@H](CCC)CC[C@H]1CS(=O)CCC1=CC=CC=C1 QGQIOQOZCBKVTE-SXMXJJAMSA-N 0.000 claims 1
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- YRNXZRCCGIJIDR-PWXVBYBUSA-N n-[(3s,6s,10as)-3-(2,3-dihydro-1h-inden-2-yloxymethyl)-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1h-pyrrolo[1,2-a]azocin-6-yl]-2-(methylamino)propanamide Chemical compound N12C(=O)[C@@H](NC(=O)C(C)NC)CCCC[C@H]2CC[C@H]1COC1CC2=CC=CC=C2C1 YRNXZRCCGIJIDR-PWXVBYBUSA-N 0.000 claims 1
- CPGPLTHYRBJHDC-MHKFTUFMSA-N n-[(3s,6s,10as)-3-(3-benzoylphenyl)-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1h-pyrrolo[1,2-a]azocin-6-yl]-2-(methylamino)butanamide Chemical compound C=1C([C@@H]2CC[C@@H]3CCCC[C@@H](C(N32)=O)NC(=O)C(NC)CC)=CC=CC=1C(=O)C1=CC=CC=C1 CPGPLTHYRBJHDC-MHKFTUFMSA-N 0.000 claims 1
- JOCKQFOYJUFLBZ-DJVBROGYSA-N n-[(3s,6s,10as)-3-(3-benzoylphenyl)-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1h-pyrrolo[1,2-a]azocin-6-yl]-2-(methylamino)propanamide Chemical compound C=1C([C@@H]2CC[C@@H]3CCCC[C@@H](C(N32)=O)NC(=O)C(C)NC)=CC=CC=1C(=O)C1=CC=CC=C1 JOCKQFOYJUFLBZ-DJVBROGYSA-N 0.000 claims 1
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- UQADYRAXYQCECI-JGDOXLDRSA-N n-[(3s,6s,10as)-3-[3-(4-fluorophenoxy)phenyl]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1h-pyrrolo[1,2-a]azocin-6-yl]-2-(methylamino)propanamide Chemical compound C=1C([C@@H]2CC[C@@H]3CCCC[C@@H](C(N32)=O)NC(=O)C(C)NC)=CC=CC=1OC1=CC=C(F)C=C1 UQADYRAXYQCECI-JGDOXLDRSA-N 0.000 claims 1
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- LOYFGWYUFNSQCE-DKUSXUSTSA-N n-[(3s,6s,10as)-5-oxo-3-(2-phenylethylsulfinylmethyl)-2,3,6,7,8,9,10,10a-octahydro-1h-pyrrolo[1,2-a]azocin-6-yl]-2-(methylamino)propanamide Chemical compound C([C@@H]1CC[C@@H]2CCCC[C@@H](C(N21)=O)NC(=O)C(C)NC)S(=O)CCC1=CC=CC=C1 LOYFGWYUFNSQCE-DKUSXUSTSA-N 0.000 claims 1
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- CIIJYLFLIOWUOD-PZFMYPBSSA-N n-[(3s,6s,10as)-5-oxo-3-(3-phenoxyphenyl)-2,3,6,7,8,9,10,10a-octahydro-1h-pyrrolo[1,2-a]azocin-6-yl]-2-(methylamino)butanamide Chemical compound C=1C([C@@H]2CC[C@@H]3CCCC[C@@H](C(N32)=O)NC(=O)C(NC)CC)=CC=CC=1OC1=CC=CC=C1 CIIJYLFLIOWUOD-PZFMYPBSSA-N 0.000 claims 1
- JHRDJWIZWQHTDJ-YIWLPCTASA-N n-[(3s,6s,10as)-5-oxo-3-(3-phenoxyphenyl)-2,3,6,7,8,9,10,10a-octahydro-1h-pyrrolo[1,2-a]azocin-6-yl]-2-(methylamino)propanamide Chemical compound C=1C([C@@H]2CC[C@@H]3CCCC[C@@H](C(N32)=O)NC(=O)C(C)NC)=CC=CC=1OC1=CC=CC=C1 JHRDJWIZWQHTDJ-YIWLPCTASA-N 0.000 claims 1
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- KBCVOQKYEAFAIG-WMEOFMBSSA-N n-[(4s,7s)-6,10-dioxo-4-(2-phenylethylsulfanylmethyl)-2,3,4,7,8,9-hexahydro-1h-pyridazino[1,2-a]diazepin-7-yl]-2-(methylamino)butanamide Chemical compound C([C@@H]1CCCN2C(=O)CC[C@@H](C(N21)=O)NC(=O)C(NC)CC)SCCC1=CC=CC=C1 KBCVOQKYEAFAIG-WMEOFMBSSA-N 0.000 claims 1
- BXQUHCKQEAELBU-MSYFUGIWSA-N n-[(4s,7s)-6,10-dioxo-4-(2-phenylethylsulfanylmethyl)-2,3,4,7,8,9-hexahydro-1h-pyridazino[1,2-a]diazepin-7-yl]-2-(methylamino)propanamide Chemical compound C([C@@H]1CCCN2C(=O)CC[C@@H](C(N21)=O)NC(=O)C(C)NC)SCCC1=CC=CC=C1 BXQUHCKQEAELBU-MSYFUGIWSA-N 0.000 claims 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68863905P | 2005-06-08 | 2005-06-08 | |
| US60/688,639 | 2005-06-08 | ||
| PCT/US2006/021850 WO2006133147A2 (en) | 2005-06-08 | 2006-06-06 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2610396A1 true CA2610396A1 (en) | 2006-12-14 |
Family
ID=37052743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002610396A Abandoned CA2610396A1 (en) | 2005-06-08 | 2006-06-06 | Organic compounds |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US7989441B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1902065A2 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2008545780A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20080022092A (cg-RX-API-DMAC7.html) |
| CN (1) | CN101193908B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2006255084A1 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0611922A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2610396A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2007015419A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2007147959A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2006133147A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5230865B2 (ja) | 2004-07-15 | 2013-07-10 | テトラロジック ファーマシューティカルズ コーポレーション | Iap結合性化合物 |
| EA012810B1 (ru) | 2005-02-25 | 2009-12-30 | Тетралоджик Фармасеутикалс | Димерные ингибиторы ингибиторов белков апоптоза (iap) |
| AP2007004244A0 (en) | 2005-05-10 | 2007-12-31 | Intermune Inc | Method of modulating stress-activated protein kinase system |
| WO2006122408A1 (en) | 2005-05-18 | 2006-11-23 | Aegera Therapeutics Inc. | Bir domain binding compounds |
| AU2006308453B9 (en) | 2005-10-25 | 2011-12-01 | Pharmascience Inc. | IAP BIR domain binding compounds |
| WO2007101347A1 (en) * | 2006-03-07 | 2007-09-13 | Aegera Therapeutics Inc. | Bir domain binding compounds |
| TWI504597B (zh) | 2006-03-16 | 2015-10-21 | Pharmascience Inc | 結合於細胞凋亡抑制蛋白(iap)之桿狀病毒iap重複序列(bir)區域之化合物 |
| BRPI0711591A2 (pt) | 2006-05-16 | 2011-11-16 | Aegera Therapeutics, Inc. | composto de ligação de domìnio bir da iap |
| WO2008014229A2 (en) * | 2006-07-24 | 2008-01-31 | Tetralogic Pharmaceuticals Corporation | Dimeric iap inhibitors |
| JP5452223B2 (ja) | 2006-07-24 | 2014-03-26 | テトラロジック ファーマシューティカルズ コーポレーション | Iap阻害剤 |
| MX2009000824A (es) | 2006-07-24 | 2009-02-04 | Tetralogic Pharmaceuticals Cor | Antagonistas dimericos de las proteinas inhibidoras de la apoptosis. |
| US20100056495A1 (en) * | 2006-07-24 | 2010-03-04 | Tetralogic Pharmaceuticals Corporation | Dimeric iap inhibitors |
| CA2670726A1 (en) | 2006-12-07 | 2008-06-19 | Novartis Ag | 6-oxo-1, 6-dihydropyrimidin-2-yls in the treatment of proliferative diseases |
| BRPI0720049A2 (pt) * | 2006-12-07 | 2014-01-07 | Novartis Ag | Derivados de piridina utilizados como inibidores de xiap |
| JP2010528587A (ja) * | 2007-05-07 | 2010-08-26 | テトラロジック ファーマシューティカルズ コーポレーション | アポトーシス阻害タンパク質のアンタゴニストに対する感受性のバイオマーカーとしてTNFα遺伝子の発現を用いる方法 |
| US8871111B2 (en) * | 2008-03-18 | 2014-10-28 | Ngk Insulators, Ltd. | Piezoelectric/electrostrictive ceramic composition |
| EP2296653B1 (en) | 2008-06-03 | 2016-01-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| US20100317593A1 (en) * | 2009-06-12 | 2010-12-16 | Astrazeneca Ab | 2,3-dihydro-1h-indene compounds |
| US8283372B2 (en) | 2009-07-02 | 2012-10-09 | Tetralogic Pharmaceuticals Corp. | 2-(1H-indol-3-ylmethyl)-pyrrolidine dimer as a SMAC mimetic |
| NZ602368A (en) | 2010-02-12 | 2014-10-31 | Pharmascience Inc | Iap bir domain binding compounds |
| TW201249824A (en) | 2011-03-09 | 2012-12-16 | Glaxosmithkline Llc | Peptide deformylase inhibitors |
| JP2014528409A (ja) | 2011-09-30 | 2014-10-27 | テトラロジック ファーマシューティカルズ コーポレーション | 増殖性疾患(がん)の治療において使用するためのSMAC模倣体(ビリナパント(birinapant)) |
| US8859541B2 (en) * | 2012-02-27 | 2014-10-14 | Boehringer Ingelheim International Gmbh | 6-alkynylpyridines |
| MX2015000362A (es) * | 2012-07-13 | 2015-04-14 | Hoffmann La Roche | Benzo(b)-azepin-2-onas antiproliferativas. |
| RU2015105561A (ru) | 2012-08-09 | 2016-09-27 | Ф. Хоффманн-Ля Рош Аг | Замещенные гетероазепиноны |
| BR112015004547A8 (pt) * | 2012-09-19 | 2018-01-23 | Hoffmann La Roche | compostos, composição farmacêutica, uso de um composto e método para o tratamento ou melhoria do cãncer |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| CA2896577C (en) | 2012-11-30 | 2024-01-23 | Sanford-Burnham Medical Research Institute | Inhibitor of apoptosis protein (iap) antagonists |
| KR20160030099A (ko) | 2013-06-25 | 2016-03-16 | 더 월터 앤드 엘리자 홀 인스티튜트 오브 메디컬 리서치 | 세포내 감염의 치료 방법 |
| CA2925084A1 (en) * | 2013-11-18 | 2015-05-21 | F. Hoffmann-La Roche Ag | Tetrahydro-benzodiazepinones |
| WO2015109391A1 (en) | 2014-01-24 | 2015-07-30 | Children's Hospital Of Eastern Ontario Research Institute Inc. | Smc combination therapy for the treatment of cancer |
| RU2692485C2 (ru) | 2014-04-02 | 2019-06-25 | Интермьюн, Инк. | Противофиброзные пиридиноны |
| JP6768522B2 (ja) | 2014-06-04 | 2020-10-14 | サンフォード−バーンハム メディカル リサーチ インスティテュート | Hiv治療におけるアポトーシスタンパク質阻害剤(iap)のアンタゴニストの使用 |
| AR101479A1 (es) | 2014-08-11 | 2016-12-21 | Boehringer Ingelheim Int | Derivados de 6-alquinil-piridina |
| WO2016079527A1 (en) | 2014-11-19 | 2016-05-26 | Tetralogic Birinapant Uk Ltd | Combination therapy |
| WO2016097773A1 (en) | 2014-12-19 | 2016-06-23 | Children's Cancer Institute | Therapeutic iap antagonists for treating proliferative disorders |
| EA038950B1 (ru) | 2016-05-19 | 2021-11-12 | Бёрингер Ингельхайм Интернациональ Гмбх | Способ получения производных 6-алкинил-пиридина |
| LT3552017T (lt) * | 2016-12-09 | 2022-05-10 | Denali Therapeutics Inc. | Junginiai, naudotini kaip ripk1 inhibitoriai |
| CN106674228B (zh) * | 2016-12-09 | 2018-12-04 | 河南农业大学 | 多元杂环化合物及其制备方法和用途 |
| CA3063938A1 (en) * | 2017-05-17 | 2018-11-22 | Denali Therapeutics Inc. | Compounds, compositions and methods |
| US12678509B2 (en) | 2019-11-08 | 2026-07-14 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitor of apoptosis (IAP) protein antagonists |
| US20230056604A1 (en) | 2020-01-20 | 2023-02-23 | Astrazeneca Ab | Epidermal growth factor receptor tyrosine kinase inhibitors for the treatment of cancer |
| RS66874B1 (sr) * | 2020-09-17 | 2025-06-30 | Novartis Ag | Jedinjenja i kompozicije kao inhibitori sppl2a |
| KR20230153387A (ko) | 2021-02-02 | 2023-11-06 | 리미널 바이오사이언시스 리미티드 | Gpr84 길항제 및 이의 용도 |
| JP2024506858A (ja) | 2021-02-02 | 2024-02-15 | リミナル・バイオサイエンシーズ・リミテッド | Gpr84アンタゴニストおよびその使用 |
| WO2025061058A1 (en) * | 2023-09-18 | 2025-03-27 | Ascentage Pharma (Suzhou) Co., Ltd. | Novel compounds as iap antagonists |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US5521179A (en) * | 1991-04-18 | 1996-05-28 | Zeneca Limited | Heterocyclic amides |
| GB9207145D0 (en) * | 1991-04-18 | 1992-05-13 | Ici Plc | Heterocyclic amides |
| US5283241A (en) * | 1992-08-28 | 1994-02-01 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
| US5434261A (en) * | 1993-07-26 | 1995-07-18 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
| JPH08225586A (ja) * | 1995-02-22 | 1996-09-03 | Fujisawa Pharmaceut Co Ltd | 新規リン酸誘導体、その製造法およびそれを含有する医薬組成物 |
| ATE310528T1 (de) * | 1996-09-12 | 2005-12-15 | Idun Pharmaceuticals Inc | Hemmung der apoptose unter verwendung von inhibitoren der interleukin-1 beta converting enzym (ice)/ced-3 familie |
| US6423519B1 (en) * | 1998-07-15 | 2002-07-23 | Gpc Biotech Inc. | Compositions and methods for inhibiting fungal growth |
| JP2005522430A (ja) | 2002-02-04 | 2005-07-28 | メルク エンド カムパニー インコーポレーテッド | グランザイムb阻害剤 |
| ATE400812T1 (de) * | 2003-02-07 | 2008-07-15 | Genentech Inc | Zusammensetzungen und verfahren für verstärkte apoptose |
| PE20050159A1 (es) * | 2003-05-27 | 2005-04-19 | Vertex Pharma | Derivados de acido 3-[2-(3-amino-2-oxo-2h-piridin-1-il)-acetilamino]-4-oxo-pentanoico como inhibidores de caspasa |
| BRPI0506883A (pt) * | 2004-01-16 | 2007-05-29 | Univ Michigan | miméticos de smac conformacionalmente comprimidos e seus usos |
| WO2006010118A2 (en) | 2004-07-09 | 2006-01-26 | The Regents Of The University Of Michigan | Conformationally constrained smac mimetics and the uses thereof |
| BRPI0513310A (pt) | 2004-07-12 | 2008-05-06 | Idun Pharmaceuticals Inc | análogos de tetrapeptìdeo |
| US7652703B2 (en) * | 2004-07-12 | 2010-01-26 | Micron Technology, Inc. | Dual panel pixel readout in an imager |
| WO2006122408A1 (en) * | 2005-05-18 | 2006-11-23 | Aegera Therapeutics Inc. | Bir domain binding compounds |
-
2006
- 2006-06-06 AU AU2006255084A patent/AU2006255084A1/en not_active Abandoned
- 2006-06-06 EP EP06760702A patent/EP1902065A2/en not_active Withdrawn
- 2006-06-06 KR KR1020077028586A patent/KR20080022092A/ko not_active Withdrawn
- 2006-06-06 US US11/916,887 patent/US7989441B2/en not_active Expired - Fee Related
- 2006-06-06 BR BRPI0611922-0A patent/BRPI0611922A2/pt not_active IP Right Cessation
- 2006-06-06 JP JP2008515811A patent/JP2008545780A/ja active Pending
- 2006-06-06 WO PCT/US2006/021850 patent/WO2006133147A2/en not_active Ceased
- 2006-06-06 MX MX2007015419A patent/MX2007015419A/es not_active Application Discontinuation
- 2006-06-06 RU RU2007147959/04A patent/RU2007147959A/ru not_active Application Discontinuation
- 2006-06-06 CA CA002610396A patent/CA2610396A1/en not_active Abandoned
- 2006-06-06 CN CN2006800202223A patent/CN101193908B/zh not_active Expired - Fee Related
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2011
- 2011-06-15 US US13/161,166 patent/US20110281845A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN101193908B (zh) | 2012-04-11 |
| WO2006133147A2 (en) | 2006-12-14 |
| JP2008545780A (ja) | 2008-12-18 |
| WO2006133147A3 (en) | 2007-05-03 |
| RU2007147959A (ru) | 2009-07-20 |
| US20090069294A1 (en) | 2009-03-12 |
| CN101193908A (zh) | 2008-06-04 |
| EP1902065A2 (en) | 2008-03-26 |
| US7989441B2 (en) | 2011-08-02 |
| BRPI0611922A2 (pt) | 2010-10-05 |
| US20110281845A1 (en) | 2011-11-17 |
| AU2006255084A1 (en) | 2006-12-14 |
| MX2007015419A (es) | 2008-02-21 |
| KR20080022092A (ko) | 2008-03-10 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |