JP2004509895A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2004509895A5 JP2004509895A5 JP2002529112A JP2002529112A JP2004509895A5 JP 2004509895 A5 JP2004509895 A5 JP 2004509895A5 JP 2002529112 A JP2002529112 A JP 2002529112A JP 2002529112 A JP2002529112 A JP 2002529112A JP 2004509895 A5 JP2004509895 A5 JP 2004509895A5
- Authority
- JP
- Japan
- Prior art keywords
- epoxy
- isoindole
- methyl
- dioxo
- octahydro
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 description 58
- -1 Nitro, amino Chemical group 0.000 description 50
- 125000000392 cycloalkenyl group Chemical group 0.000 description 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 22
- 125000000547 substituted alkyl group Chemical group 0.000 description 20
- 125000000753 cycloalkyl group Chemical group 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 125000003710 aryl alkyl group Chemical group 0.000 description 16
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 12
- 125000003107 substituted aryl group Chemical group 0.000 description 10
- 125000004494 ethyl ester group Chemical group 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000005017 substituted alkenyl group Chemical group 0.000 description 6
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- OFDPXZJYBJAYBI-UHFFFAOYSA-N 7H-isoindole-1,6-dione Chemical compound C1=NC(C=2CC(C=CC1=2)=O)=O OFDPXZJYBJAYBI-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000651 prodrug Substances 0.000 description 4
- 229940002612 prodrug Drugs 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- VKWSKNKAHKHDRI-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1CC2C3C(=O)NC(=O)C3C1O2 VKWSKNKAHKHDRI-UHFFFAOYSA-N 0.000 description 2
- YZMDGZBUENPPLI-UHFFFAOYSA-N C1(=CC=CC=C1)COC(=O)C1=CC=CC2=CNC=C12 Chemical compound C1(=CC=CC=C1)COC(=O)C1=CC=CC2=CNC=C12 YZMDGZBUENPPLI-UHFFFAOYSA-N 0.000 description 2
- XGKWFBNMVXZCPT-UHFFFAOYSA-N O=C1NC(=O)C2C1C1(C)OC2(C)CC1 Chemical compound O=C1NC(=O)C2C1C1(C)OC2(C)CC1 XGKWFBNMVXZCPT-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000008359 benzonitriles Chemical class 0.000 description 2
- 239000004202 carbamide Chemical class 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- KPWKPGFLZGMMFX-UHFFFAOYSA-N (1S)-(-)-Camphanic acid Chemical compound C1CC2(C(O)=O)OC(=O)C1(C)C2(C)C KPWKPGFLZGMMFX-UHFFFAOYSA-N 0.000 description 1
- QVVJZHVEBUNKBZ-UHFFFAOYSA-N (4-fluorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(F)C=C1 QVVJZHVEBUNKBZ-UHFFFAOYSA-N 0.000 description 1
- UJAXTLJBSXCUOU-UHFFFAOYSA-N 2,2-dimethyl-n-[[2-(2,4,6-trimethylphenyl)-3,3a,7,7a-tetrahydro-1h-octahydro-1h-4,7-epoxyisoindol-4-yl]methyl]propanamide Chemical compound CC1=CC(C)=CC(C)=C1N1CC2C(CNC(=O)C(C)(C)C)(C=C3)OC3C2C1 UJAXTLJBSXCUOU-UHFFFAOYSA-N 0.000 description 1
- WCFFSIHYUQAEPU-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-7-methyl-4,7a-dihydro-3ah-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=C2OCOC2=CC(N2C(=O)C3C(C2=O)C2OC3(C=C2)C)=C1 WCFFSIHYUQAEPU-UHFFFAOYSA-N 0.000 description 1
- GWFFJZWFYFIQSS-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-7-(hydroxymethyl)-4,7a-dihydro-3ah-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound CC1=CC(C)=CC=C1N1C(=O)C2C(CO)(C=C3)OC3C2C1=O GWFFJZWFYFIQSS-UHFFFAOYSA-N 0.000 description 1
- CDSYMSDMOYPWNG-UHFFFAOYSA-N 2-(2-benzylsulfanylphenyl)-3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound O=C1C2C(C=C3)OC3C2C(=O)N1C1=CC=CC=C1SCC1=CC=CC=C1 CDSYMSDMOYPWNG-UHFFFAOYSA-N 0.000 description 1
- VRFNMNVGEUOPSJ-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4,7-dimethyl-3a,7a-dihydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound COC1=CC=CC=C1N1C(=O)C(C2(C)C=CC3(C)O2)C3C1=O VRFNMNVGEUOPSJ-UHFFFAOYSA-N 0.000 description 1
- VSCVBCWTGSNQHH-UHFFFAOYSA-N 2-(2-sulfanylphenyl)-3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound SC1=CC=CC=C1N1C(=O)C2C(C=C3)OC3C2C1=O VSCVBCWTGSNQHH-UHFFFAOYSA-N 0.000 description 1
- DLHQKRZBSZZUDC-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-methyl-4,7a-dihydro-3ah-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=CC2(C)OC1C(C1=O)C2C(=O)N1C1=CC=C(F)C=C1 DLHQKRZBSZZUDC-UHFFFAOYSA-N 0.000 description 1
- MGKPFALCNDRSQD-UHFFFAOYSA-N 2-(4-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C=C1 MGKPFALCNDRSQD-UHFFFAOYSA-N 0.000 description 1
- GNPDWQROHXKKPD-UHFFFAOYSA-N 2-(7-methyl-3,3a,4,7a-tetrahydro-1h-octahydro-1h-4,7-epoxyisoindol-2-yl)benzonitrile Chemical compound C1=CC(C)(C2C3)OC1C2CN3C1=CC=CC=C1C#N GNPDWQROHXKKPD-UHFFFAOYSA-N 0.000 description 1
- CLCOFUGODOHTRU-UHFFFAOYSA-N 2-[2-chloro-5-(trifluoromethyl)phenyl]-7-methyl-4,7a-dihydro-3ah-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=CC2(C)OC1C(C1=O)C2C(=O)N1C1=CC(C(F)(F)F)=CC=C1Cl CLCOFUGODOHTRU-UHFFFAOYSA-N 0.000 description 1
- DJIQRZCQQIYFET-UHFFFAOYSA-N 2-[4-(4-bromophenoxy)phenyl]-4,7-dimethyl-3a,7a-dihydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=CC2(C)OC1(C)C(C1=O)C2C(=O)N1C(C=C1)=CC=C1OC1=CC=C(Br)C=C1 DJIQRZCQQIYFET-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- QINBNTXGPXHWJL-UHFFFAOYSA-N 2-chloro-5-[7-(hydroxymethyl)-3,3a,4,7a-tetrahydro-1h-octahydro-1h-4,7-epoxyisoindol-2-yl]benzoic acid Chemical compound C1=CC(CO)(C2C3)OC1C2CN3C1=CC=C(Cl)C(C(O)=O)=C1 QINBNTXGPXHWJL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- SYYIHPNBWLVXRP-UHFFFAOYSA-N 2-methylpropyl n-[[2-(4-chlorophenyl)-3,3a,7,7a-tetrahydro-1h-octahydro-1h-4,7-epoxyisoindol-4-yl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OCC(C)C)(C2C3)OC1C2CN3C1=CC=C(Cl)C=C1 SYYIHPNBWLVXRP-UHFFFAOYSA-N 0.000 description 1
- OYBKKUASLYVUCF-UHFFFAOYSA-N 2-phenoxy-n-[(2-phenyl-3,3a,7,7a-tetrahydro-1h-octahydro-1h-4,7-epoxyisoindol-4-yl)methyl]acetamide Chemical compound O1C(C2C3CN(C2)C=2C=CC=CC=2)C=CC13CNC(=O)COC1=CC=CC=C1 OYBKKUASLYVUCF-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- HETXNXPTSBVRNA-UHFFFAOYSA-N 3-(5-hydroxy-4,7-dimethyl-1,3-dioxo-3a,5,6,7a-tetrahydro-4,7-epoxyisoindol-2-yl)-2-(trifluoromethyl)benzonitrile Chemical compound OC1C2(C3C(N(C(C3C(C1)(O2)C)=O)C=2C(=C(C#N)C=CC2)C(F)(F)F)=O)C HETXNXPTSBVRNA-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- MAVQGQJZTWZOMB-UHFFFAOYSA-N 4,7-dimethyl-2-(4-methyl-3-nitrophenyl)-3a,7a-dihydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1N1C(=O)C(C2(C)C=CC3(C)O2)C3C1=O MAVQGQJZTWZOMB-UHFFFAOYSA-N 0.000 description 1
- KSFCXQHZDYXHJQ-UHFFFAOYSA-N 4,7-dimethyl-2-(4-nitrophenyl)-3a,7a-dihydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=CC2(C)OC1(C)C(C1=O)C2C(=O)N1C1=CC=C([N+]([O-])=O)C=C1 KSFCXQHZDYXHJQ-UHFFFAOYSA-N 0.000 description 1
- QTKXTZWQWPVZCJ-UHFFFAOYSA-N 4-(1,3,3a,4,7,7a-hexahydro-4,6,7-trimethyl-1,3-dioxo-4,7-epoxy-2h-pyrrolo[3,4-c]pyridin-2-yl)-2-(trifluoromethyl)benzonitrile Chemical compound CC1=NC2(C)OC1(C)C(C1=O)C2C(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 QTKXTZWQWPVZCJ-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- JFEOWXDXUYFUQE-UHFFFAOYSA-N 7-(hydroxymethyl)-2-[2-(trifluoromethyl)phenyl]-4,7a-dihydro-3ah-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=CC2(CO)OC1C(C1=O)C2C(=O)N1C1=CC=CC=C1C(F)(F)F JFEOWXDXUYFUQE-UHFFFAOYSA-N 0.000 description 1
- MAZNKLATDRBDTB-UHFFFAOYSA-N 7-(hydroxymethyl)-2-naphthalen-1-yl-4,7a-dihydro-3ah-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=CC=C2C(N3C(=O)C4C(C3=O)C3OC4(C=C3)CO)=CC=CC2=C1 MAZNKLATDRBDTB-UHFFFAOYSA-N 0.000 description 1
- HAOQAKSTJMZPAN-UHFFFAOYSA-N 7-methyl-2-(4-methyl-3-nitrophenyl)-4,7a-dihydro-3ah-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1N1C(=O)C2C(C)(C=C3)OC3C2C1=O HAOQAKSTJMZPAN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000005973 Carvone Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- IZSPADOKCWJBKM-UHFFFAOYSA-N [acetyloxy-[2-(3-bromophenyl)-1,3-dioxo-7,7a-dihydro-3ah-octahydro-1h-4,7-epoxyisoindol-4-yl]methyl] acetate Chemical compound C1=CC2(C(OC(C)=O)OC(=O)C)OC1C(C1=O)C2C(=O)N1C1=CC=CC(Br)=C1 IZSPADOKCWJBKM-UHFFFAOYSA-N 0.000 description 1
- HXZSKXIMDVXOCI-UHFFFAOYSA-N [acetyloxy-[2-(4-bromo-2-nitrophenyl)-1,3-dioxo-7,7a-dihydro-3ah-octahydro-1h-4,7-epoxyisoindol-4-yl]methyl] acetate Chemical compound C1=CC2(C(OC(C)=O)OC(=O)C)OC1C(C1=O)C2C(=O)N1C1=CC=C(Br)C=C1[N+]([O-])=O HXZSKXIMDVXOCI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 description 1
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AKZUFFRDHREDIE-UHFFFAOYSA-N methyl 2-chloro-5-(4,7-dimethyl-1,3,3a,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindol-2-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC)=CC(N2CC3C(C4(C)OC3(C)C=C4)C2)=C1 AKZUFFRDHREDIE-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- NARPWIVFKMJTKV-UHFFFAOYSA-N n-[[2-(4-chlorophenyl)-3,3a,7,7a-tetrahydro-1h-octahydro-1h-4,7-epoxyisoindol-4-yl]methyl]-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NCC1(C2CN(CC22)C=3C=CC(Cl)=CC=3)C=CC2O1 NARPWIVFKMJTKV-UHFFFAOYSA-N 0.000 description 1
- HCOOITFQWWQPOV-UHFFFAOYSA-N n-[[2-(4-chlorophenyl)-3,3a,7,7a-tetrahydro-1h-octahydro-1h-4,7-epoxyisoindol-4-yl]methyl]-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)NCC1(C2CN(CC22)C=3C=CC(Cl)=CC=3)C=CC2O1 HCOOITFQWWQPOV-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- SVTZSSXWMLWISG-UHFFFAOYSA-N tert-butyl n-[(2-phenyl-3,3a,7,7a-tetrahydro-1h-octahydro-1h-4,7-epoxyisoindol-4-yl)methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)(C2C3)OC1C2CN3C1=CC=CC=C1 SVTZSSXWMLWISG-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23351900P | 2000-09-19 | 2000-09-19 | |
| US60/233,519 | 2000-09-19 | ||
| US28473001P | 2001-04-18 | 2001-04-18 | |
| US28443801P | 2001-04-18 | 2001-04-18 | |
| US60/284,438 | 2001-04-18 | ||
| US60/284,730 | 2001-04-18 | ||
| PCT/US2001/019655 WO2002024702A1 (en) | 2000-09-19 | 2001-06-20 | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004509895A JP2004509895A (ja) | 2004-04-02 |
| JP2004509895A5 true JP2004509895A5 (https=) | 2008-08-21 |
| JP4966477B2 JP4966477B2 (ja) | 2012-07-04 |
Family
ID=27398441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002529112A Expired - Fee Related JP4966477B2 (ja) | 2000-09-19 | 2001-06-20 | 核ホルモン・レセプタ機能のモジュレーターである、縮合複素環式スクシンイミド化合物およびその類縁体 |
Country Status (36)
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040077605A1 (en) | 2001-06-20 | 2004-04-22 | Salvati Mark E. | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| BR0111298A (pt) * | 2000-06-28 | 2005-05-10 | Bristol Myers Squibb Co | Moduladores seletivos dos receptores de andrógenos e métodos para identificação, projeto e uso dos mesmos |
| US7001911B2 (en) | 2000-06-28 | 2006-02-21 | Bristol-Myers Squibb Company | Fused cyclic modulators of nuclear hormone receptor function |
| EP1854798A3 (en) * | 2000-09-19 | 2007-11-28 | Bristol-Myers Squibb Company | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| US6953679B2 (en) | 2000-09-19 | 2005-10-11 | Bristol-Myers Squibb Company | Method for the preparation of fused heterocyclic succinimide compounds and analogs thereof |
| US20040087548A1 (en) | 2001-02-27 | 2004-05-06 | Salvati Mark E. | Fused cyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| DE60228330D1 (de) | 2001-12-19 | 2008-09-25 | Bristol Myers Squibb Co | Kondensierte heterocyclische verbindungen und deren analoga; modulatoren der funktion von nukleären hormonrezeptoren |
| TWI263640B (en) * | 2001-12-19 | 2006-10-11 | Bristol Myers Squibb Co | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| AU2002950217A0 (en) | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
| BR0313405A (pt) | 2002-08-12 | 2005-07-12 | Takeda Pharmaceutical | Compostos, métodos para preparar um composto e para prevenir e/ou tratar câncer, prodroga, medicamento, modulador do receptor de androgênio, agente para prevenir e/ou tratar hipogonadismo ou pertubação climatérica masculina, osteoporose e câncer, e, uso de um composto |
| US20060142387A1 (en) * | 2003-06-10 | 2006-06-29 | Rodolfo Cadilla | Chemical compounds |
| US7378426B2 (en) | 2004-03-01 | 2008-05-27 | Bristol-Myers Squibb Company | Fused heterotricyclic compounds as inhibitors of 17β-hydroxysteroid dehydrogenase 3 |
| US7417040B2 (en) * | 2004-03-01 | 2008-08-26 | Bristol-Myers Squibb Company | Fused tricyclic compounds as inhibitors of 17β-hydroxysteroid dehydrogenase 3 |
| US7709516B2 (en) | 2005-06-17 | 2010-05-04 | Endorecherche, Inc. | Helix 12 directed non-steroidal antiandrogens |
| EP1911743B8 (en) * | 2005-08-01 | 2013-01-16 | Takeda Pharmaceutical Company Limited | Cyclic amine compound |
| EP2039695A4 (en) * | 2006-07-11 | 2010-09-15 | Takeda Pharmaceutical | BICYCLIC HETEROCYLIC COMPOUND AND ITS USE |
| US9284345B2 (en) | 2007-04-12 | 2016-03-15 | Endorecherche, Inc. | 17alpha-substituted steroids as systemic antiandrogens and selective androgen receptor modulators |
| JPWO2011007819A1 (ja) | 2009-07-17 | 2012-12-27 | 塩野義製薬株式会社 | ラクタムまたはベンゼンスルホンアミド化合物を含有する医薬 |
| BR112014012444B1 (pt) | 2011-11-23 | 2021-12-14 | Therapeuticsmd, Inc | Composição farmacêutica compreendendo estradiol solubilizado, progesterona e um agente de solubilização, bem como usos desta para tratar um sintoma relacionado à menopausa em uma mulher |
| US9301920B2 (en) | 2012-06-18 | 2016-04-05 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US10806697B2 (en) | 2012-12-21 | 2020-10-20 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US20150196640A1 (en) | 2012-06-18 | 2015-07-16 | Therapeuticsmd, Inc. | Progesterone formulations having a desirable pk profile |
| US10806740B2 (en) | 2012-06-18 | 2020-10-20 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US20130338122A1 (en) | 2012-06-18 | 2013-12-19 | Therapeuticsmd, Inc. | Transdermal hormone replacement therapies |
| US10471072B2 (en) | 2012-12-21 | 2019-11-12 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10568891B2 (en) | 2012-12-21 | 2020-02-25 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10537581B2 (en) | 2012-12-21 | 2020-01-21 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US9180091B2 (en) | 2012-12-21 | 2015-11-10 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US11246875B2 (en) | 2012-12-21 | 2022-02-15 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11266661B2 (en) | 2012-12-21 | 2022-03-08 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US9682960B2 (en) | 2013-12-19 | 2017-06-20 | Endorecherche, Inc. | Non-steroidal antiandrogens and selective androgen receptor modulators with a pyridyl moiety |
| RU2016143081A (ru) | 2014-05-22 | 2018-06-26 | Терапьютиксмд, Инк. | Натуральные комбинированные гормонозаместительные составы и терапии |
| US10328087B2 (en) | 2015-07-23 | 2019-06-25 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
| US10286077B2 (en) | 2016-04-01 | 2019-05-14 | Therapeuticsmd, Inc. | Steroid hormone compositions in medium chain oils |
| US9931349B2 (en) | 2016-04-01 | 2018-04-03 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical composition |
| CA3103144C (en) | 2018-06-14 | 2023-09-26 | The Scripps Research Institute | Nonmuscle myosin ii inhibitors for substance use relapse |
| US11633405B2 (en) | 2020-02-07 | 2023-04-25 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical formulations |
| WO2022061226A1 (en) * | 2020-09-19 | 2022-03-24 | Augusta University Research Institute, Inc. | Compositions and methods for inhibiting trem-1 |
| CN115340483A (zh) * | 2022-08-31 | 2022-11-15 | 南京吉星生物技术开发有限公司 | 一种萘基吡咯啉二酮化合物及其制备方法与它的用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3261845A (en) * | 1964-07-14 | 1966-07-19 | Dow Chemical Co | N-phenyl derivatives of 3,6-epoxyhexahydrophthalimide |
| JPS5046697A (https=) * | 1973-08-20 | 1975-04-25 | ||
| US5539126A (en) * | 1994-04-20 | 1996-07-23 | Bristol-Myers Squibb Company | Method for preparing homochiral maleimide intermediates, via silylation techniques |
| EP1043325B1 (en) * | 1994-12-22 | 2004-06-16 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
| JP2000513362A (ja) * | 1996-06-27 | 2000-10-10 | リガンド・ファーマスーティカルス・インコーポレーテッド | アンドロゲン受容体モジュレーター化合物及び方法 |
| CA2288978A1 (en) * | 1997-04-29 | 1998-11-05 | The Salk Institute For Biological Studies | Methods for identifying ligands for nuclear hormone receptors |
| US7101681B1 (en) * | 1997-11-21 | 2006-09-05 | Amgen, Inc. | Nuclear hormone receptor drug screens |
| AU6985300A (en) * | 1999-09-10 | 2001-04-17 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| BR0111298A (pt) * | 2000-06-28 | 2005-05-10 | Bristol Myers Squibb Co | Moduladores seletivos dos receptores de andrógenos e métodos para identificação, projeto e uso dos mesmos |
-
2001
- 2001-06-20 KR KR1020037004018A patent/KR100765670B1/ko not_active Expired - Fee Related
- 2001-06-20 YU YU20003A patent/YU20003A/sh unknown
- 2001-06-20 PT PT01948503T patent/PT1319007E/pt unknown
- 2001-06-20 WO PCT/US2001/019655 patent/WO2002024702A1/en not_active Ceased
- 2001-06-20 AU AU2001269943A patent/AU2001269943B2/en not_active Ceased
- 2001-06-20 MX MXPA03002412A patent/MXPA03002412A/es active IP Right Grant
- 2001-06-20 HR HR20030305A patent/HRP20030305B9/xx not_active IP Right Cessation
- 2001-06-20 EP EP01948503A patent/EP1319007B9/en not_active Expired - Lifetime
- 2001-06-20 UA UA2003043564A patent/UA78686C2/uk unknown
- 2001-06-20 GE GE5206A patent/GEP20074144B/en unknown
- 2001-06-20 HU HU0400455A patent/HUP0400455A3/hu unknown
- 2001-06-20 JP JP2002529112A patent/JP4966477B2/ja not_active Expired - Fee Related
- 2001-06-20 AU AU6994301A patent/AU6994301A/xx active Pending
- 2001-06-20 HK HK03106433.9A patent/HK1054230B/en not_active IP Right Cessation
- 2001-06-20 CA CA002423071A patent/CA2423071A1/en not_active Abandoned
- 2001-06-20 NZ NZ524803A patent/NZ524803A/en unknown
- 2001-06-20 AT AT01948503T patent/ATE318822T1/de active
- 2001-06-20 CN CNA200710006341XA patent/CN1995039A/zh active Pending
- 2001-06-20 PL PL36170701A patent/PL361707A1/xx unknown
- 2001-06-20 CZ CZ2003780A patent/CZ2003780A3/cs unknown
- 2001-06-20 SK SK498-2003A patent/SK4982003A3/sk unknown
- 2001-06-20 DK DK01948503T patent/DK1319007T3/da active
- 2001-06-20 CN CNB018189350A patent/CN1307181C/zh not_active Expired - Fee Related
- 2001-06-20 US US09/885,381 patent/US20040176324A1/en not_active Abandoned
- 2001-06-20 DE DE60117551T patent/DE60117551T2/de not_active Expired - Lifetime
- 2001-06-20 BR BR0113980-0A patent/BR0113980A/pt not_active IP Right Cessation
- 2001-06-20 IL IL15501901A patent/IL155019A0/xx unknown
- 2001-06-20 ES ES01948503T patent/ES2260244T3/es not_active Expired - Lifetime
- 2001-06-20 EE EEP200300108A patent/EE200300108A/xx unknown
- 2001-06-27 TW TW090115632A patent/TWI305208B/zh not_active IP Right Cessation
- 2001-06-28 MY MYPI20013097A patent/MY138531A/en unknown
- 2001-06-28 AR ARP010103101A patent/AR035340A1/es unknown
- 2001-06-28 UY UY26808A patent/UY26808A1/es not_active Application Discontinuation
- 2001-08-22 PE PE2001000656A patent/PE20020729A1/es not_active Application Discontinuation
-
2003
- 2003-03-18 IS IS6750A patent/IS6750A/is unknown
- 2003-03-19 NO NO20031266A patent/NO329931B1/no not_active IP Right Cessation
- 2003-03-26 BG BG107675A patent/BG107675A/bg unknown
- 2003-04-15 ZA ZA200302963A patent/ZA200302963B/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2004509895A5 (https=) | ||
| KR100765670B1 (ko) | 융합된 헤테로시클릭 숙신이미드 화합물 및 그의 유사체,핵 호르몬 수용체 기능의 조절제 | |
| JP2021011495A5 (https=) | ||
| ES2534392T3 (es) | Inhibidores de la proteína tirosina fosfatasa humana y métodos de uso | |
| JP2007505877A5 (https=) | ||
| RU2402553C2 (ru) | ПРОИЗВОДНЫЕ ПИРАЗОЛ-ПИРИМИДИНА В КАЧЕСТВЕ АНТАГОНИСТОВ mGluR2 | |
| CA2651363A1 (en) | Triazolopyrazine derivatives useful as anti-cancer agents | |
| JP2008526999A5 (https=) | ||
| ME00586B (me) | Fungicidni azociklični amidi | |
| JP2007538092A5 (https=) | ||
| JP2005518382A5 (https=) | ||
| CA2737999A1 (en) | Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines for the treatment of myeloma | |
| HUP0303281A2 (hu) | Benzodiazepinszármazékok, mint GABA A receptor modulátorok, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények | |
| JP2003528096A5 (https=) | ||
| KR890011591A (ko) | 제약학적 제제 | |
| HK1079998A1 (zh) | 埃坡霉素在与增殖过程有关的脑病的治疗中的用途 | |
| CN1774253A (zh) | 用环氧丙酯酮衍生物治疗顽固性肿瘤 | |
| RU2016111138A (ru) | Гетероциклические соединения и способы их применения | |
| MXPA06000191A (es) | Combinacion de los inhibidores de src cinasa y agentes quimioterapeuticos para el tratamiento de enfermedades proliferativas. | |
| RU2008110917A (ru) | ПРОИЗВОДНЫЕ 7-(2-АМИНО-1-ГИДРОКСИ-ЭТИЛ)-4-ГИДРОКСИБЕНЗОТИАЗОЛ-2(3Н)-ОНА В КАЧЕСТВЕ АГОНИСТОВ β2-АДРЕНЕРГИЧЕСКИХ РЕЦЕПТОРОВ | |
| JP2006512366A5 (https=) | ||
| JP2005521676A5 (https=) | ||
| JP2006516626A5 (https=) | ||
| RU2009101299A (ru) | Трициклическое соединение и его фармацевтическое применение | |
| RU2378278C2 (ru) | ЗАМЕЩЕННЫЕ 3-СУЛЬФОНИЛ-[1,2,3]ТРИАЗОЛО[1,5-a]ПИРИМИДИНЫ-АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЕ |