JP2008545780A5 - - Google Patents
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- JP2008545780A5 JP2008545780A5 JP2008515811A JP2008515811A JP2008545780A5 JP 2008545780 A5 JP2008545780 A5 JP 2008545780A5 JP 2008515811 A JP2008515811 A JP 2008515811A JP 2008515811 A JP2008515811 A JP 2008515811A JP 2008545780 A5 JP2008545780 A5 JP 2008545780A5
- Authority
- JP
- Japan
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 150000001408 amides Chemical class 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000000539 amino acid group Chemical group 0.000 claims description 2
- 210000000170 cell membrane Anatomy 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- -1 (S) -1-carbamoyl-2-phenyl-ethylcarbamoyl Chemical group 0.000 claims 31
- 229940080818 propionamide Drugs 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 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 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
- 241000124008 Mammalia Species 0.000 claims 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000007822 coupling agent Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 230000002062 proliferating effect Effects 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
- 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 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
- 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
- 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
- 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
- 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
- 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
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- 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
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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
- SVUWENNYDNCSJC-PDDQFZCSSA-N n-[(4s,7s)-6,10-dioxo-4-(2-phenylethylsulfinylmethyl)-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)S(=O)CCC1=CC=CC=C1 SVUWENNYDNCSJC-PDDQFZCSSA-N 0.000 claims 1
- ORFAJNZPFVYADB-KOEFYFSJSA-N n-[(4s,7s)-6,10-dioxo-4-(2-phenylethylsulfinylmethyl)-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)S(=O)CCC1=CC=CC=C1 ORFAJNZPFVYADB-KOEFYFSJSA-N 0.000 claims 1
- QTBCWNLVCCSPAG-WMEOFMBSSA-N n-[(4s,7s)-6,10-dioxo-4-(2-phenylethylsulfonylmethyl)-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)S(=O)(=O)CCC1=CC=CC=C1 QTBCWNLVCCSPAG-WMEOFMBSSA-N 0.000 claims 1
- NHSIQVDIFCJCPO-MSYFUGIWSA-N n-[(4s,7s)-6,10-dioxo-4-(2-phenylethylsulfonylmethyl)-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)S(=O)(=O)CCC1=CC=CC=C1 NHSIQVDIFCJCPO-MSYFUGIWSA-N 0.000 claims 1
- 238000005897 peptide coupling reaction Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 0 CC(C)C(C*C1(CC(C)(C)CC2NC(C)=*=C)N)N1C2=* Chemical compound CC(C)C(C*C1(CC(C)(C)CC2NC(C)=*=C)N)N1C2=* 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- YHSZOGHQVSNJTP-UHFFFAOYSA-N CCCNC(CC(c1cccc(C2)c1NC2NC)=O)C(C)=O Chemical compound CCCNC(CC(c1cccc(C2)c1NC2NC)=O)C(C)=O YHSZOGHQVSNJTP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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| 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 |
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| 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 |
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| US20100317593A1 (en) * | 2009-06-12 | 2010-12-16 | Astrazeneca Ab | 2,3-dihydro-1h-indene compounds |
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| 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 |
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| US5521179A (en) * | 1991-04-18 | 1996-05-28 | Zeneca Limited | Heterocyclic amides |
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| 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 |
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| 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
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- 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
-
2011
- 2011-06-15 US US13/161,166 patent/US20110281845A1/en not_active Abandoned
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