JP2008545780A - 有機化合物 - Google Patents
有機化合物 Download PDFInfo
- Publication number
- JP2008545780A JP2008545780A JP2008515811A JP2008515811A JP2008545780A JP 2008545780 A JP2008545780 A JP 2008545780A JP 2008515811 A JP2008515811 A JP 2008515811A JP 2008515811 A JP2008515811 A JP 2008515811A JP 2008545780 A JP2008545780 A JP 2008545780A
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- methylamino
- oxo
- dihydro
- propionamide
- 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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- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- -1 (S) -1-carbamoyl-2-phenyl-ethylcarbamoyl Chemical group 0.000 claims description 49
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 26
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 25
- 150000001408 amides Chemical class 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 230000002062 proliferating effect Effects 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 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
- 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 5
- 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 5
- 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 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
- DRIIALWPEHYWHX-UHFFFAOYSA-N C1(=CC=CC=C1)CCNC(=O)N1N=CC=CC=C1 Chemical compound C1(=CC=CC=C1)CCNC(=O)N1N=CC=CC=C1 DRIIALWPEHYWHX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000539 amino acid group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl 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
- 125000005346 substituted cycloalkyl group Chemical group 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
- 229940080818 propionamide Drugs 0.000 claims 10
- 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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 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
- 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
- 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
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Classifications
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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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
- C07K5/10—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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68863905P | 2005-06-08 | 2005-06-08 | |
| PCT/US2006/021850 WO2006133147A2 (en) | 2005-06-08 | 2006-06-06 | Organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008545780A true JP2008545780A (ja) | 2008-12-18 |
| JP2008545780A5 JP2008545780A5 (cg-RX-API-DMAC7.html) | 2009-07-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008515811A Pending JP2008545780A (ja) | 2005-06-08 | 2006-06-06 | 有機化合物 |
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) |
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| CN (1) | CN101193908B (cg-RX-API-DMAC7.html) |
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| BR (1) | BRPI0611922A2 (cg-RX-API-DMAC7.html) |
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| MX (1) | MX2007015419A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2007147959A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2006133147A2 (cg-RX-API-DMAC7.html) |
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| JP2015512879A (ja) * | 2012-02-27 | 2015-04-30 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Smacミメチックスとしての6−アルキニルピリジン |
| JP2015527315A (ja) * | 2012-07-13 | 2015-09-17 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | 抗増殖性ベンゾ[b]アゼピン−2−オン |
| JP2015528483A (ja) * | 2012-09-19 | 2015-09-28 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | 2−オキソ−2,3,4,5−テトラヒドロ−1h−ベンゾ[b]ジアゼピン及びがんの治療におけるその使用 |
| JP2018162256A (ja) * | 2012-11-30 | 2018-10-18 | 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 | アポトーシス阻害タンパク質(iap)のアンタゴニスト |
| US10544188B2 (en) | 2012-11-30 | 2020-01-28 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitor of apoptosis protein (IAP) antagonists |
| US11912786B2 (en) | 2012-11-30 | 2024-02-27 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitor of apoptosis protein (IAP) antagonists |
| US11111270B2 (en) | 2012-11-30 | 2021-09-07 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitor of apoptosis protein (IAP) antagonists |
| US10300074B2 (en) | 2014-06-04 | 2019-05-28 | Sanford Burnham Prebys Medical Discovery Institute | Use of inhibitor of apoptosis protein (IAP) antagonists in HIV therapy |
| US10864217B2 (en) | 2014-06-04 | 2020-12-15 | Sanford Burnham Prebys Medical Discovery Institute | Use of inhibitor of apoptosis protein (IAP) antagonists in HIV therapy |
| JP7208137B2 (ja) | 2016-12-09 | 2023-01-18 | デナリ セラピューティクス インコーポレイテッド | 化合物、組成物および方法 |
| JP2020502089A (ja) * | 2016-12-09 | 2020-01-23 | デナリ セラピューティクス インコーポレイテッドDenali Therapeutics Inc. | 化合物、組成物および方法 |
| KR20200006120A (ko) * | 2017-05-17 | 2020-01-17 | 데날리 테라퓨틱스 인크. | 화합물, 조성물 및 방법 |
| JP2022174180A (ja) * | 2017-05-17 | 2022-11-22 | デナリ セラピューティクス インコーポレイテッド | 化合物、組成物および方法 |
| JP7140781B2 (ja) | 2017-05-17 | 2022-09-21 | デナリ セラピューティクス インコーポレイテッド | 化合物、組成物および方法 |
| US11851433B2 (en) | 2017-05-17 | 2023-12-26 | Denali Therapeutics Inc. | Compounds, compositions and methods |
| KR102637541B1 (ko) | 2017-05-17 | 2024-02-15 | 데날리 테라퓨틱스 인크. | 화합물, 조성물 및 방법 |
| JP2020520925A (ja) * | 2017-05-17 | 2020-07-16 | デナリ セラピューティクス インコーポレイテッドDenali Therapeutics Inc. | 化合物、組成物および方法 |
| US12678509B2 (en) | 2019-11-08 | 2026-07-14 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitor of apoptosis (IAP) protein antagonists |
| JP2023541475A (ja) * | 2020-09-17 | 2023-10-02 | ノバルティス アーゲー | Sppl2a阻害剤としての化合物及び組成物 |
| JP7771172B2 (ja) | 2020-09-17 | 2025-11-17 | ノバルティス アーゲー | Sppl2a阻害剤としての化合物及び組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101193908B (zh) | 2012-04-11 |
| WO2006133147A2 (en) | 2006-12-14 |
| 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 |
| CA2610396A1 (en) | 2006-12-14 |
| 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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