JP2004521095A5 - - Google Patents
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- Publication number
- JP2004521095A5 JP2004521095A5 JP2002549637A JP2002549637A JP2004521095A5 JP 2004521095 A5 JP2004521095 A5 JP 2004521095A5 JP 2002549637 A JP2002549637 A JP 2002549637A JP 2002549637 A JP2002549637 A JP 2002549637A JP 2004521095 A5 JP2004521095 A5 JP 2004521095A5
- Authority
- JP
- Japan
- Prior art keywords
- isoindol
- dihydro
- oxo
- propionamide
- cyclohexyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 23
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 150000001721 carbon Chemical group 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- -1 perfluoro Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- AVZFDRVTBXTFED-LJQANCHMSA-N (2r)-n-(5-bromopyridin-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound N1=CC(Br)=CC=C1NC(=O)[C@H](N1C(C2=CC=CC=C2C1)=O)CC1CCCCC1 AVZFDRVTBXTFED-LJQANCHMSA-N 0.000 claims 2
- HAZJQNXTVYBGMP-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound O=C([C@H](CC1CCCCC1)N1C(C2=CC=CC=C2C1)=O)NC1=NC=CS1 HAZJQNXTVYBGMP-KRWDZBQOSA-N 0.000 claims 2
- XVQGNUFYAJIZQR-SFHVURJKSA-N (2s)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)-n-pyrazin-2-ylpropanamide Chemical compound O=C([C@H](CC1CCCCC1)N1C(C2=CC=CC=C2C1)=O)NC1=CN=CC=N1 XVQGNUFYAJIZQR-SFHVURJKSA-N 0.000 claims 2
- VIPWGMMDZOTSGY-IBGZPJMESA-N (2s)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)-n-pyridin-2-ylpropanamide Chemical compound O=C([C@H](CC1CCCCC1)N1C(C2=CC=CC=C2C1)=O)NC1=CC=CC=N1 VIPWGMMDZOTSGY-IBGZPJMESA-N 0.000 claims 2
- GBNHOHZADLLVKN-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(7-fluoro-3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)F)C(=O)NC=1SC=CN=1)C1CCCCC1 GBNHOHZADLLVKN-KRWDZBQOSA-N 0.000 claims 2
- RLBRXNUSTWYTMA-FQEVSTJZSA-N (2s)-3-cyclohexyl-n-(5-methylpyridin-2-yl)-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound N1=CC(C)=CC=C1NC(=O)[C@@H](N1C(C2=CC=CC=C2C1)=O)CC1CCCCC1 RLBRXNUSTWYTMA-FQEVSTJZSA-N 0.000 claims 2
- XDZPUUOXMDFXIF-IBGZPJMESA-N (2s)-n-(5-chloropyridin-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)[C@@H](N1C(C2=CC=CC=C2C1)=O)CC1CCCCC1 XDZPUUOXMDFXIF-IBGZPJMESA-N 0.000 claims 2
- MCSTZKDFCAKYAJ-UHFFFAOYSA-N 3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)-n-pyrimidin-4-ylpropanamide Chemical compound C1CCCCC1CC(N1C(C2=CC=CC=C2C1)=O)C(=O)NC1=CC=NC=N1 MCSTZKDFCAKYAJ-UHFFFAOYSA-N 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- VPMSFNVPKXVXRA-UHFFFAOYSA-N n-(5-chloro-1,3-thiazol-2-yl)-3-cyclopentyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound S1C(Cl)=CN=C1NC(=O)C(N1C(C2=CC=CC=C2C1)=O)CC1CCCC1 VPMSFNVPKXVXRA-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- HAZJQNXTVYBGMP-QGZVFWFLSA-N (2r)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound O=C([C@@H](CC1CCCCC1)N1C(C2=CC=CC=C2C1)=O)NC1=NC=CS1 HAZJQNXTVYBGMP-QGZVFWFLSA-N 0.000 claims 1
- NOHJJASTBHVIBA-KRWDZBQOSA-N (2s)-2-(4-chloro-3-oxo-1h-isoindol-2-yl)-3-cyclohexyl-n-pyrazin-2-ylpropanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)Cl)C(=O)NC=1N=CC=NC=1)C1CCCCC1 NOHJJASTBHVIBA-KRWDZBQOSA-N 0.000 claims 1
- IMQABFYLCVJPJC-SFHVURJKSA-N (2s)-2-(4-chloro-3-oxo-1h-isoindol-2-yl)-3-cyclohexyl-n-pyridin-2-ylpropanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)Cl)C(=O)NC=1N=CC=CC=1)C1CCCCC1 IMQABFYLCVJPJC-SFHVURJKSA-N 0.000 claims 1
- FOBTWFHCMITRKD-HNNXBMFYSA-N (2s)-2-(4-chloro-3-oxo-1h-isoindol-2-yl)-n-(5-chloro-1,3-thiazol-2-yl)-3-cyclohexylpropanamide Chemical compound S1C(Cl)=CN=C1NC(=O)[C@@H](N1C(C2=C(Cl)C=CC=C2C1)=O)CC1CCCCC1 FOBTWFHCMITRKD-HNNXBMFYSA-N 0.000 claims 1
- BMJGFYCEVPVPNV-KRWDZBQOSA-N (2s)-2-(7-chloro-3-oxo-1h-isoindol-2-yl)-3-cyclohexyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)Cl)C(=O)NC=1SC=CN=1)C1CCCCC1 BMJGFYCEVPVPNV-KRWDZBQOSA-N 0.000 claims 1
- GBFOLYLWHXRFRM-SFHVURJKSA-N (2s)-2-(7-chloro-3-oxo-1h-isoindol-2-yl)-3-cyclohexyl-n-pyrazin-2-ylpropanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)Cl)C(=O)NC=1N=CC=NC=1)C1CCCCC1 GBFOLYLWHXRFRM-SFHVURJKSA-N 0.000 claims 1
- ADKARQQIMWDUGM-IBGZPJMESA-N (2s)-2-(7-chloro-3-oxo-1h-isoindol-2-yl)-3-cyclohexyl-n-pyridin-2-ylpropanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)Cl)C(=O)NC=1N=CC=CC=1)C1CCCCC1 ADKARQQIMWDUGM-IBGZPJMESA-N 0.000 claims 1
- VFFPWUGCWCCOLR-INIZCTEOSA-N (2s)-2-(7-chloro-3-oxo-1h-isoindol-2-yl)-n-(5-chloro-1,3-thiazol-2-yl)-3-cyclohexylpropanamide Chemical compound S1C(Cl)=CN=C1NC(=O)[C@@H](N1C(C2=C(C(=CC=C2)Cl)C1)=O)CC1CCCCC1 VFFPWUGCWCCOLR-INIZCTEOSA-N 0.000 claims 1
- VEMZDALOYZQAEW-QHCPKHFHSA-N (2s)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)-n-quinolin-2-ylpropanamide Chemical compound C([C@@H](C(NC=1N=C2C=CC=CC2=CC=1)=O)N1C(C2=CC=CC=C2C1)=O)C1CCCCC1 VEMZDALOYZQAEW-QHCPKHFHSA-N 0.000 claims 1
- MOTYSUWGCCIXCJ-INIZCTEOSA-N (2s)-3-cyclohexyl-2-(4-fluoro-3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)F)C(=O)NC=1SC=CN=1)C1CCCCC1 MOTYSUWGCCIXCJ-INIZCTEOSA-N 0.000 claims 1
- AESJIZQMLZJCIX-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(4-fluoro-3-oxo-1h-isoindol-2-yl)-n-pyrazin-2-ylpropanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)F)C(=O)NC=1N=CC=NC=1)C1CCCCC1 AESJIZQMLZJCIX-KRWDZBQOSA-N 0.000 claims 1
- HEANFYSBOROOGI-SFHVURJKSA-N (2s)-3-cyclohexyl-2-(4-fluoro-3-oxo-1h-isoindol-2-yl)-n-pyridin-2-ylpropanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)F)C(=O)NC=1N=CC=CC=1)C1CCCCC1 HEANFYSBOROOGI-SFHVURJKSA-N 0.000 claims 1
- NJZNFKXZYGYLHJ-INIZCTEOSA-N (2s)-3-cyclohexyl-2-(4-methylsulfonyl-3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)S(=O)(=O)C)C(=O)NC=1SC=CN=1)C1CCCCC1 NJZNFKXZYGYLHJ-INIZCTEOSA-N 0.000 claims 1
- BVNOVXGXNDLFON-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(4-methylsulfonyl-3-oxo-1h-isoindol-2-yl)-n-pyrazin-2-ylpropanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)S(=O)(=O)C)C(=O)NC=1N=CC=NC=1)C1CCCCC1 BVNOVXGXNDLFON-KRWDZBQOSA-N 0.000 claims 1
- FXJNEBZFBPOSTM-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(4-methylsulfonyl-3-oxo-1h-isoindol-2-yl)-n-pyrimidin-4-ylpropanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)S(=O)(=O)C)C(=O)NC=1N=CN=CC=1)C1CCCCC1 FXJNEBZFBPOSTM-KRWDZBQOSA-N 0.000 claims 1
- IVCSEFFRVLCXQL-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(5,6-dichloro-3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1CC=2C=C(C(=CC=2C1=O)Cl)Cl)C(=O)NC=1SC=CN=1)C1CCCCC1 IVCSEFFRVLCXQL-KRWDZBQOSA-N 0.000 claims 1
- KDUXDFOIUUGGRR-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(5-nitro-3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1CC2=CC=C(C=C2C1=O)[N+](=O)[O-])C(=O)NC=1SC=CN=1)C1CCCCC1 KDUXDFOIUUGGRR-KRWDZBQOSA-N 0.000 claims 1
- DQKKRPDGDNRFGW-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(6-nitro-3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1C(=O)C2=CC=C(C=C2C1)[N+](=O)[O-])C(=O)NC=1SC=CN=1)C1CCCCC1 DQKKRPDGDNRFGW-KRWDZBQOSA-N 0.000 claims 1
- CAFYGEUIKNMVSG-SFHVURJKSA-N (2s)-3-cyclohexyl-2-(7-fluoro-3-oxo-1h-isoindol-2-yl)-n-pyrazin-2-ylpropanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)F)C(=O)NC=1N=CC=NC=1)C1CCCCC1 CAFYGEUIKNMVSG-SFHVURJKSA-N 0.000 claims 1
- FHBWVXBMWRLART-IBGZPJMESA-N (2s)-3-cyclohexyl-2-(7-fluoro-3-oxo-1h-isoindol-2-yl)-n-pyridin-2-ylpropanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)F)C(=O)NC=1N=CC=CC=1)C1CCCCC1 FHBWVXBMWRLART-IBGZPJMESA-N 0.000 claims 1
- AMYSZDQNPNHAGO-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(7-methylsulfonyl-3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)S(=O)(=O)C)C(=O)NC=1SC=CN=1)C1CCCCC1 AMYSZDQNPNHAGO-KRWDZBQOSA-N 0.000 claims 1
- FSHQEAUMFQXYOM-SFHVURJKSA-N (2s)-3-cyclohexyl-2-(7-methylsulfonyl-3-oxo-1h-isoindol-2-yl)-n-pyrazin-2-ylpropanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)S(=O)(=O)C)C(=O)NC=1N=CC=NC=1)C1CCCCC1 FSHQEAUMFQXYOM-SFHVURJKSA-N 0.000 claims 1
- ABUMTHLKVAXGJG-SFHVURJKSA-N (2s)-3-cyclohexyl-2-(7-methylsulfonyl-3-oxo-1h-isoindol-2-yl)-n-pyrimidin-4-ylpropanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)S(=O)(=O)C)C(=O)NC=1N=CN=CC=1)C1CCCCC1 ABUMTHLKVAXGJG-SFHVURJKSA-N 0.000 claims 1
- RXKUQKUECLOWDJ-KRWDZBQOSA-N (2s)-3-cyclohexyl-n-(1h-imidazol-2-yl)-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound O=C([C@H](CC1CCCCC1)N1C(C2=CC=CC=C2C1)=O)NC1=NC=CN1 RXKUQKUECLOWDJ-KRWDZBQOSA-N 0.000 claims 1
- HSVROUFTDPBEOI-FQEVSTJZSA-N (2s)-3-cyclohexyl-n-(4-methylpyridin-2-yl)-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound CC1=CC=NC(NC(=O)[C@H](CC2CCCCC2)N2C(C3=CC=CC=C3C2)=O)=C1 HSVROUFTDPBEOI-FQEVSTJZSA-N 0.000 claims 1
- JKHHPJPIEXQNBA-FQEVSTJZSA-N (2s)-n-(1,3-benzothiazol-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@@H](C(NC=1SC2=CC=CC=C2N=1)=O)N1C(C2=CC=CC=C2C1)=O)C1CCCCC1 JKHHPJPIEXQNBA-FQEVSTJZSA-N 0.000 claims 1
- HEMJGYNZNHUXMQ-FQEVSTJZSA-N (2s)-n-(1,3-benzoxazol-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@@H](C(NC=1OC2=CC=CC=C2N=1)=O)N1C(C2=CC=CC=C2C1)=O)C1CCCCC1 HEMJGYNZNHUXMQ-FQEVSTJZSA-N 0.000 claims 1
- JRASWERIVQXADO-NRFANRHFSA-N (2s)-n-(1h-benzimidazol-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@@H](C(NC=1NC2=CC=CC=C2N=1)=O)N1C(C2=CC=CC=C2C1)=O)C1CCCCC1 JRASWERIVQXADO-NRFANRHFSA-N 0.000 claims 1
- UYCVBXJBAQSWQH-INIZCTEOSA-N (2s)-n-(5-bromo-1,3-thiazol-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound S1C(Br)=CN=C1NC(=O)[C@@H](N1C(C2=CC=CC=C2C1)=O)CC1CCCCC1 UYCVBXJBAQSWQH-INIZCTEOSA-N 0.000 claims 1
- QJCZYKAVUAOAOA-INIZCTEOSA-N (2s)-n-(5-bromo-1,3-thiazol-2-yl)-3-cyclohexyl-2-(5,6-dichloro-3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@H](N1CC=2C=C(C(=CC=2C1=O)Cl)Cl)C(=O)NC=1SC(Br)=CN=1)C1CCCCC1 QJCZYKAVUAOAOA-INIZCTEOSA-N 0.000 claims 1
- NUKAOIIENHSHHP-INIZCTEOSA-N (2s)-n-(5-chloro-1,3-thiazol-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound S1C(Cl)=CN=C1NC(=O)[C@@H](N1C(C2=CC=CC=C2C1)=O)CC1CCCCC1 NUKAOIIENHSHHP-INIZCTEOSA-N 0.000 claims 1
- JFZLHUCEJYRSNM-HNNXBMFYSA-N (2s)-n-(5-chloro-1,3-thiazol-2-yl)-3-cyclohexyl-2-(4-fluoro-3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)F)C(=O)NC=1SC(Cl)=CN=1)C1CCCCC1 JFZLHUCEJYRSNM-HNNXBMFYSA-N 0.000 claims 1
- SLCOTHPFAXVLDC-INIZCTEOSA-N (2s)-n-(5-chloro-1,3-thiazol-2-yl)-3-cyclohexyl-2-(5,6-dichloro-3-oxo-1h-isoindol-2-yl)propanamide Chemical compound S1C(Cl)=CN=C1NC(=O)[C@@H](N1C(C2=CC(Cl)=C(Cl)C=C2C1)=O)CC1CCCCC1 SLCOTHPFAXVLDC-INIZCTEOSA-N 0.000 claims 1
- SZDIMEPRHLQIJE-INIZCTEOSA-N (2s)-n-(5-chloro-1,3-thiazol-2-yl)-3-cyclohexyl-2-(5-nitro-3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@H](N1CC2=CC=C(C=C2C1=O)[N+](=O)[O-])C(=O)NC=1SC(Cl)=CN=1)C1CCCCC1 SZDIMEPRHLQIJE-INIZCTEOSA-N 0.000 claims 1
- CLICAWXVUGZAHG-INIZCTEOSA-N (2s)-n-(5-chloro-1,3-thiazol-2-yl)-3-cyclohexyl-2-(6-nitro-3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@H](N1C(=O)C2=CC=C(C=C2C1)[N+](=O)[O-])C(=O)NC=1SC(Cl)=CN=1)C1CCCCC1 CLICAWXVUGZAHG-INIZCTEOSA-N 0.000 claims 1
- MVWXBJNCJHLRBQ-INIZCTEOSA-N (2s)-n-(5-chloro-1,3-thiazol-2-yl)-3-cyclohexyl-2-(7-fluoro-3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)F)C(=O)NC=1SC(Cl)=CN=1)C1CCCCC1 MVWXBJNCJHLRBQ-INIZCTEOSA-N 0.000 claims 1
- PLENEAJJYFHWBP-HNNXBMFYSA-N (2s)-n-cyclohexyl-n-(2-methylpyrimidin-4-yl)-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound O=C([C@@H](N1C(C2=CC=CC=C2C1)=O)C)N(C=1N=C(C)N=CC=1)C1CCCCC1 PLENEAJJYFHWBP-HNNXBMFYSA-N 0.000 claims 1
- CRJFRTOZGDAQPG-UHFFFAOYSA-N 3-cycloheptyl-2-(3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1CCCCCC1CC(N1C(C2=CC=CC=C2C1)=O)C(=O)NC1=NC=CS1 CRJFRTOZGDAQPG-UHFFFAOYSA-N 0.000 claims 1
- BHGICAYVWJMPOK-UHFFFAOYSA-N 3-cyclooctyl-2-(3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1CCCCCCC1CC(N1C(C2=CC=CC=C2C1)=O)C(=O)NC1=NC=CS1 BHGICAYVWJMPOK-UHFFFAOYSA-N 0.000 claims 1
- PWPUNWJDAFANEV-UHFFFAOYSA-N 3-cyclopentyl-2-(3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1CCCC1CC(N1C(C2=CC=CC=C2C1)=O)C(=O)NC1=NC=CS1 PWPUNWJDAFANEV-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 238000010976 amide bond formation reaction Methods 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- NSCIJCDEXRVCMK-UHFFFAOYSA-N n-(5-chloro-1,3-thiazol-2-yl)-3-cycloheptyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound S1C(Cl)=CN=C1NC(=O)C(N1C(C2=CC=CC=C2C1)=O)CC1CCCCCC1 NSCIJCDEXRVCMK-UHFFFAOYSA-N 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25527300P | 2000-12-13 | 2000-12-13 | |
| US31871501P | 2001-09-13 | 2001-09-13 | |
| PCT/EP2001/014404 WO2002048106A2 (en) | 2000-12-13 | 2001-12-07 | Isoindolin-1-one glucokinase activators |
Publications (3)
| Publication Number | Publication Date |
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| JP2004521095A JP2004521095A (ja) | 2004-07-15 |
| JP2004521095A5 true JP2004521095A5 (enExample) | 2005-05-26 |
| JP4021766B2 JP4021766B2 (ja) | 2007-12-12 |
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| SE0102299D0 (sv) | 2001-06-26 | 2001-06-26 | Astrazeneca Ab | Compounds |
| SE0102764D0 (sv) | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
| CA2499329C (en) | 2002-10-03 | 2009-04-21 | F. Hoffmann-La Roche Ag | Indole-3-carboxamides as glucokinase (gk) activators |
| JP2006509774A (ja) | 2002-10-03 | 2006-03-23 | ノバルティス アクチエンゲゼルシャフト | ２型糖尿病の処置において有用なグルコキナーゼアクチベーターとしての置換（チアゾール−２−イル）−アミドまたはスルホンアミド |
| GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| WO2004063194A1 (en) * | 2003-01-06 | 2004-07-29 | Eli Lilly And Company | Heteroaryl compounds |
| JP4621198B2 (ja) * | 2003-02-11 | 2011-01-26 | プロシディオン・リミテッド | トリ（シクロ）置換アミドグルコキナーゼ活性化化合物 |
| PL378117A1 (pl) * | 2003-02-11 | 2006-03-06 | Prosidion Limited | Tricyklopodstawione związki amidowe |
| US7320992B2 (en) * | 2003-08-25 | 2008-01-22 | Amgen Inc. | Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use |
| CN1960995B (zh) | 2004-04-02 | 2010-12-08 | 诺瓦提斯公司 | 作为葡糖激酶活化剂、可用于治疗ⅱ型糖尿病的磺酰胺-噻唑并吡啶衍生物 |
| EP1737870A1 (en) * | 2004-04-02 | 2007-01-03 | Novartis AG | Thiazolopyridine derivates, pharmaceutical conditions containing them and methods of treating glucokinase mediated conditions |
| US7642259B2 (en) | 2005-07-09 | 2010-01-05 | Astrazeneca Ab | Heteroaryl benzamide derivatives for use as GLK activators in the treatment of diabetes |
| RU2008112184A (ru) * | 2005-08-31 | 2009-10-10 | Астеллас Фарма Инк. (Jp) | Производное тиазола |
| JP2007063225A (ja) | 2005-09-01 | 2007-03-15 | Takeda Chem Ind Ltd | イミダゾピリジン化合物 |
| JP2009509988A (ja) | 2005-09-29 | 2009-03-12 | サノフィ−アベンティス | フェニル−及びピリジニル−１，２，４−オキサジアゾロン誘導体、その製造方法、及び医薬品としてのその使用 |
| GT200600428A (es) * | 2005-09-30 | 2007-05-21 | Compuestos organicos | |
| GT200600429A (es) * | 2005-09-30 | 2007-04-30 | Compuestos organicos | |
| EP1951707A1 (en) | 2005-11-01 | 2008-08-06 | Janssen Pharmaceutica N.V. | Substituted pyrrolones as allosteric modulators of glucokinase |
| US8796313B2 (en) | 2005-11-01 | 2014-08-05 | Janssen Pharmaceutica N.V. | Substituted dihydroisoindolones as allosteric modulators of glucokinase |
| WO2007053765A2 (en) * | 2005-11-01 | 2007-05-10 | Janssen Pharmaceutica N.V. | Substituted cycloalkylpyrrolones as allosteric modulators of glucokinase |
| EP1951706A1 (en) * | 2005-11-01 | 2008-08-06 | Janssen Pharmaceutica N.V. | Dihydroisoindolones as allosteric modulators of glucokinase |
| CA2626475A1 (en) * | 2005-11-03 | 2007-05-10 | Prosidion Limited | Tricyclo substituted amides |
| WO2007061923A2 (en) * | 2005-11-18 | 2007-05-31 | Takeda San Diego, Inc. | Glucokinase activators |
| US8034822B2 (en) | 2006-03-08 | 2011-10-11 | Takeda San Diego, Inc. | Glucokinase activators |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| US8008332B2 (en) | 2006-05-31 | 2011-08-30 | Takeda San Diego, Inc. | Substituted indazoles as glucokinase activators |
| WO2008079787A2 (en) | 2006-12-20 | 2008-07-03 | Takeda San Diego, Inc. | Glucokinase activators |
| WO2008074694A1 (en) * | 2006-12-20 | 2008-06-26 | F. Hoffmann-La Roche Ag | Crystallization of glucokinase activators |
| TW200831081A (en) * | 2006-12-25 | 2008-08-01 | Kyorin Seiyaku Kk | Glucokinase activator |
| CN101687800B (zh) | 2007-03-07 | 2012-03-21 | 杏林制药株式会社 | 葡糖激酶活化物质 |
| US8173645B2 (en) | 2007-03-21 | 2012-05-08 | Takeda San Diego, Inc. | Glucokinase activators |
| CL2009000004A1 (es) * | 2008-01-15 | 2010-02-19 | Lilly Co Eli | Forma cristalina de r-2-(4-ciclopropansulfonil-fenil)-n-pirazin-2-il-3-(tetrahidropiran-4-il)-propionamida; composicion farmaceutica que comprende a dicha forma cristalina; y uso para el tratamiento de diabetes o hiperglicemia. |
| PT2231640E (pt) * | 2008-01-24 | 2012-08-23 | Merck Patent Gmbh | Derivados beta-aminoácido para o tratamento de diabetes |
| MY163114A (en) * | 2008-04-28 | 2017-08-15 | Kyorin Seiyaku Kk | Cyclopentylacrylamide derivative |
| TWI445707B (zh) * | 2008-05-16 | 2014-07-21 | Takeda California Inc | 葡萄糖激酶活化劑 |
| GEP20135793B (en) * | 2008-09-11 | 2013-03-25 | Pfizer | Heteroaryls amide derivatives and their use as glucokinase activators |
| JP5909482B2 (ja) | 2010-03-31 | 2016-04-26 | ザ スクリプス リサーチ インスティテュート | 細胞の再プログラム |
| US8178689B2 (en) * | 2010-06-17 | 2012-05-15 | Hoffman-La Roche Inc. | Tricyclic compounds |
| WO2012027331A1 (en) | 2010-08-27 | 2012-03-01 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| EA201391254A1 (ru) | 2011-03-01 | 2014-02-28 | Синерджи Фармасьютикалз Инк. | Способ получения агонистов гуанилатциклазы c |
| US8470866B2 (en) * | 2011-05-03 | 2013-06-25 | Hoffmann-La Roche Inc. | Isoindolinone derivatives |
| RU2693698C2 (ru) * | 2013-05-27 | 2019-07-04 | Ф. Хоффманн-Ля Рош Аг | Новые соединения 3,4-дигидро-2н-изохинолин-1-она и 2,3-дигидроизоиндол-1-она |
| CN105764916B (zh) | 2013-06-05 | 2021-05-18 | 博士医疗爱尔兰有限公司 | 鸟苷酸环化酶c的超纯激动剂、制备和使用所述激动剂的方法 |
| MX389591B (es) | 2014-08-29 | 2025-03-20 | Tes Pharma S R L | INHIBIDORES DE ACIDO A-AMINO-ß-CARBOXIMUCONICO SEMIALDEHIDO DESCARBOXILASA |
| MX2019004321A (es) | 2016-10-14 | 2019-06-12 | Tes Pharma S R L | Inhibidores de la acido alfa-amino-beta-carboximuconico semialdehido descarboxilasa. |
| CN118496217A (zh) | 2018-11-20 | 2024-08-16 | Tes制药有限责任公司 | α-氨基-β-羧基己二烯二酸半醛去羧酶的抑制剂 |
| CN116283717B (zh) * | 2023-01-06 | 2025-04-08 | 暨南大学 | 一种藁本内酯衍生物及其制备方法和应用 |
| WO2024229228A2 (en) * | 2023-05-02 | 2024-11-07 | The Rockefeller University | 1-oxoisoindolin-2-yl amide activators of vcp and derivatives thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2687147A1 (fr) * | 1992-02-11 | 1993-08-13 | Union Pharma Scient Appl | Nouveaux derives d'alpha-amino n-pyridyl benzene propanamide, leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| CA2342471C (en) * | 1995-06-06 | 2002-10-29 | Judith L. Treadway | Heterocyclecarbonylmethyl amine intermediates |
| HRP20010688B1 (en) | 1999-03-29 | 2008-10-31 | F. Hoffmann - La Roche Ag | Glucokinase activators |
| CN1209361C (zh) | 2000-05-03 | 2005-07-06 | 霍夫曼-拉罗奇有限公司 | 含乙内酰脲的葡糖激酶激活剂 |
| JP3839723B2 (ja) | 2000-05-08 | 2006-11-01 | エフ．ホフマン−ラ ロシュ アーゲー | 置換フェニルアセトアミドおよびグルコキナーゼ活性化剤としてのその使用 |
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- 2001-12-07 AU AU3841502A patent/AU3841502A/xx active Pending
- 2001-12-07 BR BR0116169-5A patent/BR0116169A/pt not_active Application Discontinuation
- 2001-12-07 CA CA2430579A patent/CA2430579C/en not_active Expired - Fee Related
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- 2001-12-07 MX MXPA03005170A patent/MXPA03005170A/es active IP Right Grant
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