JP2008509950A5 - - Google Patents
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- Publication number
- JP2008509950A5 JP2008509950A5 JP2007526351A JP2007526351A JP2008509950A5 JP 2008509950 A5 JP2008509950 A5 JP 2008509950A5 JP 2007526351 A JP2007526351 A JP 2007526351A JP 2007526351 A JP2007526351 A JP 2007526351A JP 2008509950 A5 JP2008509950 A5 JP 2008509950A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- dioxo
- imidazolidin
- thiazol
- butyramide
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- -1 2,3-dihydro-benzo [1,4] dioxin-6-yl Chemical group 0.000 claims 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- RJZPPHJGWOCMBW-MUEKUWCCSA-N (2s,3s)-2-[(4r)-4-[4-(2-ethoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound C1=CC(OCCOCC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(=O)CC)C(=O)N1 RJZPPHJGWOCMBW-MUEKUWCCSA-N 0.000 claims 2
- UMXZLBLGVVFRBS-AJHZIAPWSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-[4-[2-(2-methoxyethylamino)-2-oxoethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC(OCC(=O)NCCOC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)C(=O)N1 UMXZLBLGVVFRBS-AJHZIAPWSA-N 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- GKDVIQCISXZIDJ-XYHYBEPMSA-N (2s,3r)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylmethoxy-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)OCC=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCCOC)=CC=2)=O)=N1 GKDVIQCISXZIDJ-XYHYBEPMSA-N 0.000 claims 1
- UWIMTNBKRFQIBP-PIVNMMCNSA-N (2s,3s)-2-[(4r)-2,5-dioxo-4-[4-(2-oxo-2-pyrrolidin-1-ylethoxy)phenyl]imidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCC(=O)N3CCCC3)=CC=2)=O)=N1 UWIMTNBKRFQIBP-PIVNMMCNSA-N 0.000 claims 1
- FAOHSPUFQXWJSD-RVHYNSKXSA-N (2s,3s)-2-[(4r)-2,5-dioxo-4-phenylimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC=CC=2)=O)=N1 FAOHSPUFQXWJSD-RVHYNSKXSA-N 0.000 claims 1
- MYZYOAYFZLVXEM-BJQRDSPESA-N (2s,3s)-2-[(4r)-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=C3OCCOC3=CC=2)=O)=N1 MYZYOAYFZLVXEM-BJQRDSPESA-N 0.000 claims 1
- ZVJVPWWPRFINEV-IPVSCWGHSA-N (2s,3s)-2-[(4r)-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2,5-dioxoimidazolidin-1-yl]-n-[4-(1-hydroxypropyl)-1,3-thiazol-2-yl]-3-phenylbutanamide Chemical compound CCC(O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=C3OCCOC3=CC=2)=O)=N1 ZVJVPWWPRFINEV-IPVSCWGHSA-N 0.000 claims 1
- HAZKEOXELTWJOJ-FNVCAUGXSA-N (2s,3s)-2-[(4r)-4-(4-ethoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound C1=CC(OCC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(=O)CC)C(=O)N1 HAZKEOXELTWJOJ-FNVCAUGXSA-N 0.000 claims 1
- RTIYENHYKKZGAW-DLPLYFIVSA-N (2s,3s)-2-[(4r)-4-(4-hydroxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(O)=CC=2)=O)=N1 RTIYENHYKKZGAW-DLPLYFIVSA-N 0.000 claims 1
- LJFHMSZDUOLYML-FNVCAUGXSA-N (2s,3s)-2-[(4r)-4-(4-methoxy-3-methylphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=C(C)C(OC)=CC=2)=O)=N1 LJFHMSZDUOLYML-FNVCAUGXSA-N 0.000 claims 1
- IMAFKJGJDAVAAF-ARBPTSGCSA-N (2s,3s)-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OC)=CC=2)=O)=N1 IMAFKJGJDAVAAF-ARBPTSGCSA-N 0.000 claims 1
- BJJARBIKZKHELT-USCONSEESA-N (2s,3s)-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-n-[4-(2-methylpropanoyl)-1,3-thiazol-2-yl]-3-phenylbutanamide Chemical compound C1=CC(OC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(=O)C(C)C)C(=O)N1 BJJARBIKZKHELT-USCONSEESA-N 0.000 claims 1
- BGIUACCETCLDJH-VWMXVWASSA-N (2s,3s)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCCOC)=CC=2)=O)=N1 BGIUACCETCLDJH-VWMXVWASSA-N 0.000 claims 1
- FEBIHWITJUHRRD-PIVNMMCNSA-N (2s,3s)-2-[(4r)-4-[4-(2-morpholin-4-yl-2-oxoethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCC(=O)N3CCOCC3)=CC=2)=O)=N1 FEBIHWITJUHRRD-PIVNMMCNSA-N 0.000 claims 1
- RKSDGUHTDQMJOZ-VWMXVWASSA-N (2s,3s)-2-[(4r)-4-[4-(dimethoxyphosphorylmethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCP(=O)(OC)OC)=CC=2)=O)=N1 RKSDGUHTDQMJOZ-VWMXVWASSA-N 0.000 claims 1
- AMPKJLPGYRHJKY-YZYNAAERSA-N (2s,3s)-2-[(4r)-4-[4-[2-(2-methoxyethoxy)ethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCCOCCOC)=CC=2)=O)=N1 AMPKJLPGYRHJKY-YZYNAAERSA-N 0.000 claims 1
- IAUOMVZXRVQRFV-IMDCKVJKSA-N (2s,3s)-2-[(4r)-4-[4-[2-(2-methoxyethylamino)-2-oxoethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCC(=O)NCCOC)=CC=2)=O)=N1 IAUOMVZXRVQRFV-IMDCKVJKSA-N 0.000 claims 1
- VDVGIQBCLJZKGN-IMDCKVJKSA-N (2s,3s)-2-[(4r)-4-[4-[2-(azetidin-1-yl)-2-oxoethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCC(=O)N3CCC3)=CC=2)=O)=N1 VDVGIQBCLJZKGN-IMDCKVJKSA-N 0.000 claims 1
- CAMWINXAXRFDEZ-AJHZIAPWSA-N (2s,3s)-2-[(4r)-4-[4-[2-(dimethylamino)-2-oxoethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCC(=O)N(C)C)=CC=2)=O)=N1 CAMWINXAXRFDEZ-AJHZIAPWSA-N 0.000 claims 1
- MZUVQFITLDJWGN-GHEQTVGYSA-N (2s,3s)-2-[(4r)-4-[4-[2-(methylamino)-2-oxoethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCC(=O)NC)=CC=2)=O)=N1 MZUVQFITLDJWGN-GHEQTVGYSA-N 0.000 claims 1
- RKKBPPTYPGTSEA-GMWOSMDTSA-N (2s,3s)-2-[(4s)-4-[4-(2-hydroxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@@H](NC2=O)C=2C=CC(OCCO)=CC=2)=O)=N1 RKKBPPTYPGTSEA-GMWOSMDTSA-N 0.000 claims 1
- BGIUACCETCLDJH-DPSWKAHMSA-N (2s,3s)-2-[(4s)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@@H](NC2=O)C=2C=CC(OCCOC)=CC=2)=O)=N1 BGIUACCETCLDJH-DPSWKAHMSA-N 0.000 claims 1
- WQDCOBMQXXDLQY-GHSRMECKSA-N (2s,3s)-2-[2,5-dioxo-4-[4-(2-piperidin-1-ylethoxy)phenyl]imidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C(C(NC2=O)C=2C=CC(OCCN3CCCCC3)=CC=2)=O)=N1 WQDCOBMQXXDLQY-GHSRMECKSA-N 0.000 claims 1
- OEJOYGTVAKZGIC-VNYPPZAHSA-N (2s,3s)-2-[4-(4-morpholin-4-ylphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C(C(NC2=O)C=2C=CC(=CC=2)N2CCOCC2)=O)=N1 OEJOYGTVAKZGIC-VNYPPZAHSA-N 0.000 claims 1
- XLUICOHNWYWEFQ-JUJMCKSGSA-N (2s,3s)-2-[4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-methyl-n-(4-propanoyl-1,3-thiazol-2-yl)pentanamide Chemical compound O=C1N([C@@H]([C@@H](C)CC)C(=O)NC=2SC=C(N=2)C(=O)CC)C(=O)NC1C1=CC=C(OCCOC)C=C1 XLUICOHNWYWEFQ-JUJMCKSGSA-N 0.000 claims 1
- VKWWTAMMAHEBEQ-AXFKQKATSA-N (2s,3s)-2-[4-[4-(2-morpholin-4-ylethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C(C(NC2=O)C=2C=CC(OCCN3CCOCC3)=CC=2)=O)=N1 VKWWTAMMAHEBEQ-AXFKQKATSA-N 0.000 claims 1
- NYPKIANNZDNFPU-XLXODUMSSA-N (2s,3s)-2-[4-[4-(4-hydroxypiperidin-1-yl)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C(C(NC2=O)C=2C=CC(=CC=2)N2CCC(O)CC2)=O)=N1 NYPKIANNZDNFPU-XLXODUMSSA-N 0.000 claims 1
- PZDHZYLTWQSYHM-VNYPPZAHSA-N (2s,3s)-2-[4-[4-[2-methoxyethyl(methyl)amino]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenyl-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C(C(NC2=O)C=2C=CC(=CC=2)N(C)CCOC)=O)=N1 PZDHZYLTWQSYHM-VNYPPZAHSA-N 0.000 claims 1
- VAAZPRCSKQZJQC-GHEQTVGYSA-N (2s,3s)-3-(3-fluorophenyl)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-n-(4-propanoyl-1,3-thiazol-2-yl)butanamide Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=C(F)C=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCCOC)=CC=2)=O)=N1 VAAZPRCSKQZJQC-GHEQTVGYSA-N 0.000 claims 1
- ZLLIAKYXUIPBIT-ARBPTSGCSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-(4-ethoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC(OCC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)C(=O)N1 ZLLIAKYXUIPBIT-ARBPTSGCSA-N 0.000 claims 1
- CWBSOUADJQDOSQ-SVIJTADQSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-(4-hydroxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1([C@H]2NC(=O)N(C2=O)[C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)=CC=C(O)C=C1 CWBSOUADJQDOSQ-SVIJTADQSA-N 0.000 claims 1
- VKJCLKODXRCZBO-DLPLYFIVSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC(OC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)C(=O)N1 VKJCLKODXRCZBO-DLPLYFIVSA-N 0.000 claims 1
- KVKDDSXNZUDXOA-NNWRFLSQSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylpentanamide Chemical compound C1([C@H]2NC(=O)N(C2=O)[C@@H]([C@@H](CC)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)=CC=C(OC)C=C1 KVKDDSXNZUDXOA-NNWRFLSQSA-N 0.000 claims 1
- AYTSWSRJBHEGRA-CUJSYCCXSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-[4-(2-amino-2-oxoethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1([C@H]2NC(=O)N(C2=O)[C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)=CC=C(OCC(N)=O)C=C1 AYTSWSRJBHEGRA-CUJSYCCXSA-N 0.000 claims 1
- NTHXESUFIMQJEQ-IMDCKVJKSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-[4-(2-morpholin-4-yl-2-oxoethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC([C@H]2NC(=O)N(C2=O)[C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)=CC=C1OCC(=O)N1CCOCC1 NTHXESUFIMQJEQ-IMDCKVJKSA-N 0.000 claims 1
- IVEOUGNWZPSZFV-MUEKUWCCSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-[4-[2-(2-methoxyethoxy)ethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC(OCCOCCOC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)C(=O)N1 IVEOUGNWZPSZFV-MUEKUWCCSA-N 0.000 claims 1
- PWLYBDLYHRZXGA-GHEQTVGYSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-[4-[2-(dimethylamino)-2-oxoethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1([C@H]2NC(=O)N(C2=O)[C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)=CC=C(OCC(=O)N(C)C)C=C1 PWLYBDLYHRZXGA-GHEQTVGYSA-N 0.000 claims 1
- JSYKNZZNYKBHEK-BZRZBQBMSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-[4-[2-(dimethylamino)ethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1([C@H]2NC(=O)N(C2=O)[C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)=CC=C(OCCN(C)C)C=C1 JSYKNZZNYKBHEK-BZRZBQBMSA-N 0.000 claims 1
- COENBVRHWRZWRY-BJQRDSPESA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[(4r)-4-[4-[2-(methylamino)-2-oxoethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC(OCC(=O)NC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)C(=O)N1 COENBVRHWRZWRY-BJQRDSPESA-N 0.000 claims 1
- TYDPBHFDHQJMBG-LZCUNHEZSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[4-(4-diethoxyphosphorylphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC(P(=O)(OCC)OCC)=CC=C1C1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)C(=O)N1 TYDPBHFDHQJMBG-LZCUNHEZSA-N 0.000 claims 1
- BRTXZYZIRRXRIJ-QEKIYOMCSA-N (2s,3s)-n-(4-acetyl-1,3-thiazol-2-yl)-2-[4-[4-(dimethylamino)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound O=C1N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)=O)C(=O)NC1C1=CC=C(N(C)C)C=C1 BRTXZYZIRRXRIJ-QEKIYOMCSA-N 0.000 claims 1
- BNBBUNOMDOUOGX-IMRHEYAYSA-N (2s,3s)-n-(4-ethylsulfanyl-1,3-thiazol-2-yl)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound CCSC1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCCOC)=CC=2)=O)=N1 BNBBUNOMDOUOGX-IMRHEYAYSA-N 0.000 claims 1
- UOTMFRIADITBII-IPAURDGOSA-N (2s,3s)-n-(4-ethylsulfinyl-1,3-thiazol-2-yl)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound CCS(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCCOC)=CC=2)=O)=N1 UOTMFRIADITBII-IPAURDGOSA-N 0.000 claims 1
- BGAGIUFVXNPXBW-IMRHEYAYSA-N (2s,3s)-n-(4-ethylsulfonyl-1,3-thiazol-2-yl)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound CCS(=O)(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCCOC)=CC=2)=O)=N1 BGAGIUFVXNPXBW-IMRHEYAYSA-N 0.000 claims 1
- CSXJWCCKICAWRW-FNVCAUGXSA-N (2s,3s)-n-[4-(2-hydroxyacetyl)-1,3-thiazol-2-yl]-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC(OCCOC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(=O)CO)C(=O)N1 CSXJWCCKICAWRW-FNVCAUGXSA-N 0.000 claims 1
- FYAINSINUCXREV-VWMXVWASSA-N (2s,3s)-n-[4-(cyclopropanecarbonyl)-1,3-thiazol-2-yl]-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC(OCCOC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(=O)C2CC2)C(=O)N1 FYAINSINUCXREV-VWMXVWASSA-N 0.000 claims 1
- WZYXLAVDBCMKRS-GHEQTVGYSA-N (2s,3s)-n-[4-(cyclopropanecarbonyl)-1,3-thiazol-2-yl]-2-[(4r)-4-[4-[2-(methylamino)-2-oxoethoxy]phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC(OCC(=O)NC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(=O)C2CC2)C(=O)N1 WZYXLAVDBCMKRS-GHEQTVGYSA-N 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims 1
- XFQXSMXNNQHINY-OPILKIMUSA-N 2-[4-[2,5-dioxo-1-[(2s,3s)-1-oxo-3-phenyl-1-[(4-propanoyl-1,3-thiazol-2-yl)amino]butan-2-yl]imidazolidin-4-yl]phenoxy]acetic acid Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C(C(NC2=O)C=2C=CC(OCC(O)=O)=CC=2)=O)=N1 XFQXSMXNNQHINY-OPILKIMUSA-N 0.000 claims 1
- YHFQRWKRHLCXJR-RVHYNSKXSA-N 2-[[(2s,3s)-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanoyl]amino]-n,n-dimethyl-1,3-thiazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(=O)N(C)C)C(=O)N1 YHFQRWKRHLCXJR-RVHYNSKXSA-N 0.000 claims 1
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- RKKBPPTYPGTSEA-FNVCAUGXSA-N RO4927350 Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCCO)=CC=2)=O)=N1 RKKBPPTYPGTSEA-FNVCAUGXSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YDQDLFQOHXRYFT-GHEQTVGYSA-N methyl 2-[4-[(4r)-2,5-dioxo-1-[(2s,3s)-1-oxo-3-phenyl-1-[(4-propanoyl-1,3-thiazol-2-yl)amino]butan-2-yl]imidazolidin-4-yl]phenoxy]acetate Chemical compound CCC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCC(=O)OC)=CC=2)=O)=N1 YDQDLFQOHXRYFT-GHEQTVGYSA-N 0.000 claims 1
- PPMXETHXODZNIC-WOJBJXKFSA-N methyl 2-[[(2s)-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-methyl-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@@H](N2C([C@H](NC2=O)C=2C=CC(OC)=CC=2)=O)C(C)(C)C=2C=CC=CC=2)=N1 PPMXETHXODZNIC-WOJBJXKFSA-N 0.000 claims 1
- CUQZQHVLJVTAOI-IFZYUDKTSA-N methyl 2-[[(2s,3r)-2-[(4r)-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=C3OCCOC3=CC=2)=O)=N1 CUQZQHVLJVTAOI-IFZYUDKTSA-N 0.000 claims 1
- RQRLHETVEAMLLF-LYRGGWFBSA-N methyl 2-[[(2s,3r)-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-methylpentanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1([C@H]2NC(=O)N(C2=O)[C@@H]([C@H](C)CC)C(=O)NC=2SC=C(N=2)C(=O)OC)=CC=C(OC)C=C1 RQRLHETVEAMLLF-LYRGGWFBSA-N 0.000 claims 1
- YUHMIVPGCKUVSN-ZMYBRWDISA-N methyl 2-[[(2s,3r)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-[(2-methylpropan-2-yl)oxy]butanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1=CC(OCCOC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)OC(C)(C)C)C(=O)NC=2SC=C(N=2)C(=O)OC)C(=O)N1 YUHMIVPGCKUVSN-ZMYBRWDISA-N 0.000 claims 1
- UWQOCAVQZYAIFW-XWIAVFTESA-N methyl 2-[[(2s,3r)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-methylpentanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1([C@H]2NC(=O)N(C2=O)[C@@H]([C@H](C)CC)C(=O)NC=2SC=C(N=2)C(=O)OC)=CC=C(OCCOC)C=C1 UWQOCAVQZYAIFW-XWIAVFTESA-N 0.000 claims 1
- WGDWYZSBVAQWQN-ZQMYSKGWSA-N methyl 2-[[(2s,3r)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylmethoxybutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1=CC(OCCOC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)OCC=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(=O)OC)C(=O)N1 WGDWYZSBVAQWQN-ZQMYSKGWSA-N 0.000 claims 1
- HVAHSGWGDBJCHI-FZQKWOKYSA-N methyl 2-[[(2s,3r)-3-hydroxy-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]butanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)O)N2C([C@H](NC2=O)C=2C=CC(OC)=CC=2)=O)=N1 HVAHSGWGDBJCHI-FZQKWOKYSA-N 0.000 claims 1
- JJUBLXHBGVUHGS-LYRGGWFBSA-N methyl 2-[[(2s,3r)-3-hydroxy-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]butanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1=CC(OCCOC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)O)C(=O)NC=2SC=C(N=2)C(=O)OC)C(=O)N1 JJUBLXHBGVUHGS-LYRGGWFBSA-N 0.000 claims 1
- JDIUNKBCVACKEH-KMUNFCNLSA-N methyl 2-[[(2s,3r)-3-methoxy-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]butanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1([C@H]2NC(=O)N(C2=O)[C@@H]([C@@H](C)OC)C(=O)NC=2SC=C(N=2)C(=O)OC)=CC=C(OC)C=C1 JDIUNKBCVACKEH-KMUNFCNLSA-N 0.000 claims 1
- CMPBBNZVDPTSJX-JLZZUVOBSA-N methyl 2-[[(2s,3r)-3-methoxy-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]butanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1=CC(OCCOC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)OC)C(=O)NC=2SC=C(N=2)C(=O)OC)C(=O)N1 CMPBBNZVDPTSJX-JLZZUVOBSA-N 0.000 claims 1
- PGXLBJUAUFKALR-USCONSEESA-N methyl 2-[[(2s,3s)-2-[(4r)-2,5-dioxo-4-(4-propan-2-yloxyphenyl)imidazolidin-1-yl]-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OC(C)C)=CC=2)=O)=N1 PGXLBJUAUFKALR-USCONSEESA-N 0.000 claims 1
- CUQZQHVLJVTAOI-DLPLYFIVSA-N methyl 2-[[(2s,3s)-2-[(4r)-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=C3OCCOC3=CC=2)=O)=N1 CUQZQHVLJVTAOI-DLPLYFIVSA-N 0.000 claims 1
- HWEQFBVEAVUCCM-DLPLYFIVSA-N methyl 2-[[(2s,3s)-2-[(4r)-4-(4-acetamidophenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(NC(C)=O)=CC=2)=O)=N1 HWEQFBVEAVUCCM-DLPLYFIVSA-N 0.000 claims 1
- GUVRHNNNBJYKSK-BKTGTZMESA-N methyl 2-[[(2s,3s)-2-[(4r)-4-(4-hydroxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(O)=CC=2)=O)=N1 GUVRHNNNBJYKSK-BKTGTZMESA-N 0.000 claims 1
- WLQJWIUIHWHAAT-RVHYNSKXSA-N methyl 2-[[(2s,3s)-2-[(4r)-4-(4-methoxy-3-methylphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=C(C)C(OC)=CC=2)=O)=N1 WLQJWIUIHWHAAT-RVHYNSKXSA-N 0.000 claims 1
- RQRLHETVEAMLLF-XZJROXQQSA-N methyl 2-[[(2s,3s)-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-methylpentanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1([C@H]2NC(=O)N(C2=O)[C@@H]([C@@H](C)CC)C(=O)NC=2SC=C(N=2)C(=O)OC)=CC=C(OC)C=C1 RQRLHETVEAMLLF-XZJROXQQSA-N 0.000 claims 1
- RNQOXMDLWNHJTE-KPOBHBOGSA-N methyl 2-[[(2s,3s)-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OC)=CC=2)=O)=N1 RNQOXMDLWNHJTE-KPOBHBOGSA-N 0.000 claims 1
- NINQMMPLKCFPKC-RVHYNSKXSA-N methyl 2-[[(2s,3s)-2-[(4r)-4-[4-(2-hydroxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCCO)=CC=2)=O)=N1 NINQMMPLKCFPKC-RVHYNSKXSA-N 0.000 claims 1
- UWQOCAVQZYAIFW-VHSSKADRSA-N methyl 2-[[(2s,3s)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-methylpentanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1([C@H]2NC(=O)N(C2=O)[C@@H]([C@@H](C)CC)C(=O)NC=2SC=C(N=2)C(=O)OC)=CC=C(OCCOC)C=C1 UWQOCAVQZYAIFW-VHSSKADRSA-N 0.000 claims 1
- GYOZDUDRHGPQBS-USCONSEESA-N methyl 2-[[(2s,3s)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1=CC(OCCOC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(=O)OC)C(=O)N1 GYOZDUDRHGPQBS-USCONSEESA-N 0.000 claims 1
- FTSHKUAMSVGXLP-USCONSEESA-N methyl 2-[[(2s,3s)-2-[(4r)-4-[4-(dimethoxyphosphorylmethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C=CC=CC=2)N2C([C@H](NC2=O)C=2C=CC(OCP(=O)(OC)OC)=CC=2)=O)=N1 FTSHKUAMSVGXLP-USCONSEESA-N 0.000 claims 1
- AAEDIUPCKIHNOW-YZIZEKMBSA-N methyl 2-[[(2s,3s)-3-(2-methoxyphenyl)-2-[4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]butanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)[C@H]([C@@H](C)C=2C(=CC=CC=2)OC)N2C(C(NC2=O)C=2C=CC(OC)=CC=2)=O)=N1 AAEDIUPCKIHNOW-YZIZEKMBSA-N 0.000 claims 1
- BBUCEHDVMJNHMU-ARBPTSGCSA-N methyl 2-[[(2s,3s)-3-(4-fluorophenyl)-2-[(4r)-4-[4-(2-methoxyethoxy)phenyl]-2,5-dioxoimidazolidin-1-yl]butanoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound C1=CC(OCCOC)=CC=C1[C@@H]1C(=O)N([C@@H]([C@@H](C)C=2C=CC(F)=CC=2)C(=O)NC=2SC=C(N=2)C(=O)OC)C(=O)N1 BBUCEHDVMJNHMU-ARBPTSGCSA-N 0.000 claims 1
- CLCDQYYRHRVFEF-VZDHWGDASA-N n-[4-(2-hydroxypropan-2-yl)-1,3-thiazol-2-yl]-2-[(4r)-4-(4-methoxyphenyl)-2,5-dioxoimidazolidin-1-yl]-3-phenylbutanamide Chemical compound C1=CC(OC)=CC=C1[C@@H]1C(=O)N(C(C(C)C=2C=CC=CC=2)C(=O)NC=2SC=C(N=2)C(C)(C)O)C(=O)N1 CLCDQYYRHRVFEF-VZDHWGDASA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical group CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
Applications Claiming Priority (5)
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| US60217504P | 2004-08-17 | 2004-08-17 | |
| US60/602,175 | 2004-08-17 | ||
| US68299705P | 2005-05-20 | 2005-05-20 | |
| US60/682,997 | 2005-05-20 | ||
| PCT/EP2005/008633 WO2006018188A2 (en) | 2004-08-17 | 2005-08-09 | Substituted hydantoins |
Publications (3)
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| JP2008509950A JP2008509950A (ja) | 2008-04-03 |
| JP2008509950A5 true JP2008509950A5 (enExample) | 2012-01-05 |
| JP4927733B2 JP4927733B2 (ja) | 2012-05-09 |
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| JP2007526351A Expired - Fee Related JP4927733B2 (ja) | 2004-08-17 | 2005-08-09 | 置換ヒダントイン |
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|---|---|
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| EP (1) | EP1781649B1 (enExample) |
| JP (1) | JP4927733B2 (enExample) |
| KR (2) | KR100889721B1 (enExample) |
| AR (1) | AR050297A1 (enExample) |
| AT (1) | ATE404556T1 (enExample) |
| AU (1) | AU2005274390B2 (enExample) |
| BR (1) | BRPI0514515A (enExample) |
| CA (1) | CA2576599A1 (enExample) |
| DE (1) | DE602005008986D1 (enExample) |
| ES (1) | ES2313389T3 (enExample) |
| MX (1) | MX2007001846A (enExample) |
| PL (1) | PL1781649T3 (enExample) |
| RU (1) | RU2383542C2 (enExample) |
| TW (1) | TW200621764A (enExample) |
| WO (1) | WO2006018188A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200621766A (en) * | 2004-09-17 | 2006-07-01 | Hoffmann La Roche | Substituted hydantoins |
| US7612212B2 (en) * | 2006-02-22 | 2009-11-03 | Hoffmann-La Roche Inc. | Substituted hydantoins |
| CN101702878B (zh) * | 2007-05-11 | 2012-11-28 | 弗·哈夫曼-拉罗切有限公司 | 可溶性差的药物的药物组合物 |
| EP2188276B1 (en) | 2007-08-16 | 2012-03-28 | F. Hoffmann-La Roche AG | Substituted hydantoins |
| KR20100086503A (ko) * | 2007-12-20 | 2010-07-30 | 에프. 호프만-라 로슈 아게 | Ｍｅｋ 키나아제 저해제로서의 치환된 히단토인 |
| US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
| US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
| MX2010014066A (es) | 2008-06-16 | 2011-06-01 | Univ Tennessee Res Foundation | Compuestos para el tratamiento del cancer. |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| WO2010068738A1 (en) | 2008-12-10 | 2010-06-17 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| WO2011000945A2 (en) * | 2009-07-03 | 2011-01-06 | Nensius Research A/S | Aminoalkamides for use in the treatment of inflammatory, degenerative or demyelinating diseases of the cns |
| WO2011106298A1 (en) | 2010-02-25 | 2011-09-01 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| RU2581367C2 (ru) | 2010-03-01 | 2016-04-20 | Джи Ти Икс, ИНК. | Соединения для лечения рака |
| CN103038364A (zh) | 2010-03-09 | 2013-04-10 | 达纳－法伯癌症研究所公司 | 诊断和治疗具有或发展对于第一种癌症治疗的抗性的患者中的癌症的方法 |
| EP2563786B1 (de) | 2010-04-28 | 2016-11-02 | Bayer Intellectual Property GmbH | Ketoheteroarylpiperidin und -piperazin Derivate als Fungizide |
| US20150141470A1 (en) | 2012-05-08 | 2015-05-21 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| MX2021002456A (es) * | 2018-09-17 | 2021-06-15 | Yungjin Pharmaceutical Co Ltd | Nuevos derivados de tiazol y sus sales farmaceuticamente aceptables. |
| KR102335637B1 (ko) * | 2020-03-13 | 2021-12-06 | 영진약품 주식회사 | 신규한 cdk7 억제 화합물 및 이의 약제학적으로 허용가능한 염 |
| KR20210116325A (ko) * | 2020-03-13 | 2021-09-27 | 영진약품 주식회사 | 티아졸 유도체 또는 이의 약제학적으로 허용가능한 염을 포함하는 암의 예방 또는 치료용 약학 조성물 |
| KR20210146144A (ko) | 2020-05-26 | 2021-12-03 | 엘지전자 주식회사 | 카트부 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5770573A (en) * | 1993-12-06 | 1998-06-23 | Cytel Corporation | CS-1 peptidomimetics, compositions and methods of using the same |
| CA2290506C (en) | 1997-07-01 | 2005-12-27 | Warner-Lambert Company | 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as mek inhibitors |
| ATE304011T1 (de) * | 2000-05-03 | 2005-09-15 | Hoffmann La Roche | Hydantoin-enthaltende glucokinase aktivatoren |
| US20040235919A1 (en) * | 2001-07-19 | 2004-11-25 | Paolo Pevarello | Phenylacetamido-thiazole derivatives, process for the preparation and their use as antitumor agents |
-
2005
- 2005-08-09 PL PL05771890T patent/PL1781649T3/pl unknown
- 2005-08-09 KR KR1020077004075A patent/KR100889721B1/ko not_active Expired - Fee Related
- 2005-08-09 DE DE602005008986T patent/DE602005008986D1/de not_active Expired - Lifetime
- 2005-08-09 AU AU2005274390A patent/AU2005274390B2/en not_active Ceased
- 2005-08-09 MX MX2007001846A patent/MX2007001846A/es active IP Right Grant
- 2005-08-09 WO PCT/EP2005/008633 patent/WO2006018188A2/en not_active Ceased
- 2005-08-09 EP EP05771890A patent/EP1781649B1/en not_active Expired - Lifetime
- 2005-08-09 BR BRPI0514515-5A patent/BRPI0514515A/pt not_active IP Right Cessation
- 2005-08-09 RU RU2007109651/04A patent/RU2383542C2/ru not_active IP Right Cessation
- 2005-08-09 KR KR1020087032084A patent/KR20090006885A/ko not_active Ceased
- 2005-08-09 ES ES05771890T patent/ES2313389T3/es not_active Expired - Lifetime
- 2005-08-09 AT AT05771890T patent/ATE404556T1/de active
- 2005-08-09 JP JP2007526351A patent/JP4927733B2/ja not_active Expired - Fee Related
- 2005-08-09 CA CA002576599A patent/CA2576599A1/en not_active Abandoned
- 2005-08-11 US US11/202,299 patent/US7427635B2/en not_active Expired - Fee Related
- 2005-08-15 TW TW094127672A patent/TW200621764A/zh unknown
- 2005-08-16 AR ARP050103440A patent/AR050297A1/es unknown