JP2006506340A5 - - Google Patents
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- Publication number
- JP2006506340A5 JP2006506340A5 JP2004527912A JP2004527912A JP2006506340A5 JP 2006506340 A5 JP2006506340 A5 JP 2006506340A5 JP 2004527912 A JP2004527912 A JP 2004527912A JP 2004527912 A JP2004527912 A JP 2004527912A JP 2006506340 A5 JP2006506340 A5 JP 2006506340A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- piperazine
- phenyl
- carboxylic acid
- ethyl ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 81
- 150000001875 compounds Chemical class 0.000 claims 17
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims 11
- -1 10Hphenothiazin-2-yl Chemical group 0.000 claims 10
- 230000002265 prevention Effects 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims 5
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- CJJMZZQGSJKNJH-AWEZNQCLSA-N ethyl 4-[(1s)-1-[5-(3-methylphenyl)-1,2,4-oxadiazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1[C@@H](C)C1=NOC(C=2C=C(C)C=CC=2)=N1 CJJMZZQGSJKNJH-AWEZNQCLSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 241000894007 species Species 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- XCARGDPHZYJCMU-UHFFFAOYSA-N 2-chloro-n'-hydroxyethanimidamide Chemical compound ClCC(N)=NO XCARGDPHZYJCMU-UHFFFAOYSA-N 0.000 claims 1
- GQQFUTKBTHSWPE-UHFFFAOYSA-N 2-nitro-N,N-bis[2-(trifluoromethylsulfonyl)ethyl]benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)N(CCS(=O)(=O)C(F)(F)F)CCS(=O)(=O)C(F)(F)F GQQFUTKBTHSWPE-UHFFFAOYSA-N 0.000 claims 1
- TUDMJGXXGOORCD-UHFFFAOYSA-N 3-(chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound ClCC1=NOC(C=2C=C(Cl)C=CC=2)=N1 TUDMJGXXGOORCD-UHFFFAOYSA-N 0.000 claims 1
- YCOKTYBAJSXBTK-UHFFFAOYSA-N 3-(chloromethyl)-5-(3-fluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=CC=CC(C=2ON=C(CCl)N=2)=C1 YCOKTYBAJSXBTK-UHFFFAOYSA-N 0.000 claims 1
- XQUARYVCTXYWLA-UHFFFAOYSA-N 3-(chloromethyl)-5-(3-iodophenyl)-1,2,4-oxadiazole Chemical compound ClCC1=NOC(C=2C=C(I)C=CC=2)=N1 XQUARYVCTXYWLA-UHFFFAOYSA-N 0.000 claims 1
- PHKTWKSTBQFLSM-UHFFFAOYSA-N 3-(chloromethyl)-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CCl)N=2)=C1 PHKTWKSTBQFLSM-UHFFFAOYSA-N 0.000 claims 1
- MYZBONNONJUNGO-UHFFFAOYSA-N 3-(chloromethyl)-5-[3-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)OC1=CC=CC(C=2ON=C(CCl)N=2)=C1 MYZBONNONJUNGO-UHFFFAOYSA-N 0.000 claims 1
- RUTZHBJOSPBPDQ-UHFFFAOYSA-N 3-[3-(chloromethyl)-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound ClCC1=NOC(C=2C=C(C=CC=2)C#N)=N1 RUTZHBJOSPBPDQ-UHFFFAOYSA-N 0.000 claims 1
- XNUULFUAZWVWPM-UHFFFAOYSA-N 5-(3-bromophenyl)-3-(chloromethyl)-1,2,4-oxadiazole Chemical compound ClCC1=NOC(C=2C=C(Br)C=CC=2)=N1 XNUULFUAZWVWPM-UHFFFAOYSA-N 0.000 claims 1
- LFXFXJCRXBYQSX-UHFFFAOYSA-N 5-(3-methylphenyl)-3-(1-piperazin-1-ylethyl)-1,2,4-oxadiazole Chemical compound N=1OC(C=2C=C(C)C=CC=2)=NC=1C(C)N1CCNCC1 LFXFXJCRXBYQSX-UHFFFAOYSA-N 0.000 claims 1
- ITHLUXJRCDKRBP-UHFFFAOYSA-N 5-(3-methylphenyl)-3-(piperazin-1-ylmethyl)-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CN3CCNCC3)N=2)=C1 ITHLUXJRCDKRBP-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- DJYGESKMYWBXKH-KWCCSABGSA-N ethyl (2r)-4-[1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethyl]-2-methylpiperazine-1-carboxylate Chemical compound C1[C@@H](C)N(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(Cl)C=CC=2)=C1 DJYGESKMYWBXKH-KWCCSABGSA-N 0.000 claims 1
- PKACWWXDUYKBBS-WPZCJLIBSA-N ethyl (2s)-2-[1-[5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNC[C@@H]1C(C)C1=NOC(C=2C(=CC=C(C)C=2)F)=N1 PKACWWXDUYKBBS-WPZCJLIBSA-N 0.000 claims 1
- DJYGESKMYWBXKH-LSLKUGRBSA-N ethyl (2s)-4-[1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethyl]-2-methylpiperazine-1-carboxylate Chemical compound C1[C@H](C)N(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(Cl)C=CC=2)=C1 DJYGESKMYWBXKH-LSLKUGRBSA-N 0.000 claims 1
- BRRUUPUPNMUJFF-GICMACPYSA-N ethyl (3r)-4-[1-[5-(2-fluoro-5-methylphenyl)-1,2-oxazol-3-yl]ethyl]-3-methylpiperazine-1-carboxylate Chemical compound C[C@@H]1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C(=CC=C(C)C=2)F)=C1 BRRUUPUPNMUJFF-GICMACPYSA-N 0.000 claims 1
- GMEYEVZHGHWAFT-KWCCSABGSA-N ethyl (3r)-4-[1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethyl]-3-methylpiperazine-1-carboxylate Chemical compound C[C@@H]1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(Cl)C=CC=2)=C1 GMEYEVZHGHWAFT-KWCCSABGSA-N 0.000 claims 1
- KIPKEJJKDSVXJN-CQSZACIVSA-N ethyl (3r)-4-[[5-(2-fluoro-5-methylphenyl)-1,2-oxazol-3-yl]methyl]-3-methylpiperazine-1-carboxylate Chemical compound C[C@@H]1CN(C(=O)OCC)CCN1CC1=NOC(C=2C(=CC=C(C)C=2)F)=C1 KIPKEJJKDSVXJN-CQSZACIVSA-N 0.000 claims 1
- QJRYHAKNFSAEOU-CYBMUJFWSA-N ethyl (3r)-4-[[5-(3-chlorophenyl)-1,2-oxazol-3-yl]methyl]-3-methylpiperazine-1-carboxylate Chemical compound C[C@@H]1CN(C(=O)OCC)CCN1CC1=NOC(C=2C=C(Cl)C=CC=2)=C1 QJRYHAKNFSAEOU-CYBMUJFWSA-N 0.000 claims 1
- BRRUUPUPNMUJFF-MLCCFXAWSA-N ethyl (3s)-4-[1-[5-(2-fluoro-5-methylphenyl)-1,2-oxazol-3-yl]ethyl]-3-methylpiperazine-1-carboxylate Chemical compound C[C@H]1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C(=CC=C(C)C=2)F)=C1 BRRUUPUPNMUJFF-MLCCFXAWSA-N 0.000 claims 1
- GMEYEVZHGHWAFT-LSLKUGRBSA-N ethyl (3s)-4-[1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethyl]-3-methylpiperazine-1-carboxylate Chemical compound C[C@H]1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(Cl)C=CC=2)=C1 GMEYEVZHGHWAFT-LSLKUGRBSA-N 0.000 claims 1
- KIPKEJJKDSVXJN-AWEZNQCLSA-N ethyl (3s)-4-[[5-(2-fluoro-5-methylphenyl)-1,2-oxazol-3-yl]methyl]-3-methylpiperazine-1-carboxylate Chemical compound C[C@H]1CN(C(=O)OCC)CCN1CC1=NOC(C=2C(=CC=C(C)C=2)F)=C1 KIPKEJJKDSVXJN-AWEZNQCLSA-N 0.000 claims 1
- QJRYHAKNFSAEOU-ZDUSSCGKSA-N ethyl (3s)-4-[[5-(3-chlorophenyl)-1,2-oxazol-3-yl]methyl]-3-methylpiperazine-1-carboxylate Chemical compound C[C@H]1CN(C(=O)OCC)CCN1CC1=NOC(C=2C=C(Cl)C=CC=2)=C1 QJRYHAKNFSAEOU-ZDUSSCGKSA-N 0.000 claims 1
- XJGMYSIYTZWUDO-AWEZNQCLSA-N ethyl 4-[(1s)-1-[5-(2-fluoro-5-methylphenyl)-1,2-oxazol-3-yl]ethyl]piperazine-1-carboxylate Chemical class C1CN(C(=O)OCC)CCN1[C@@H](C)C1=NOC(C=2C(=CC=C(C)C=2)F)=C1 XJGMYSIYTZWUDO-AWEZNQCLSA-N 0.000 claims 1
- WHCYACFFGSYKAE-LBPRGKRZSA-N ethyl 4-[(1s)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1[C@@H](C)C1=NOC(C=2C=C(Cl)C=CC=2)=N1 WHCYACFFGSYKAE-LBPRGKRZSA-N 0.000 claims 1
- GYSVRLVQQRALNR-NSHDSACASA-N ethyl 4-[(1s)-1-[5-(5-chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1[C@@H](C)C1=NOC(C=2C(=CC=C(Cl)C=2)F)=N1 GYSVRLVQQRALNR-NSHDSACASA-N 0.000 claims 1
- QFQMLVLMUNAWJF-UHFFFAOYSA-N ethyl 4-[(5-thiophen-3-yl-1,2-oxazol-3-yl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C2=CSC=C2)=C1 QFQMLVLMUNAWJF-UHFFFAOYSA-N 0.000 claims 1
- XJGMYSIYTZWUDO-UHFFFAOYSA-N ethyl 4-[1-[5-(2-fluoro-5-methylphenyl)-1,2-oxazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C(=CC=C(C)C=2)F)=C1 XJGMYSIYTZWUDO-UHFFFAOYSA-N 0.000 claims 1
- CUESYULYMVMUNX-UHFFFAOYSA-N ethyl 4-[1-[5-(2-fluoro-5-methylphenyl)-1,2-oxazol-3-yl]propyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(CC)C1=NOC(C=2C(=CC=C(C)C=2)F)=C1 CUESYULYMVMUNX-UHFFFAOYSA-N 0.000 claims 1
- RULBZEBXILBXCM-UHFFFAOYSA-N ethyl 4-[1-[5-(2-methylpyridin-4-yl)-1,2-oxazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(C)N=CC=2)=C1 RULBZEBXILBXCM-UHFFFAOYSA-N 0.000 claims 1
- WHCYACFFGSYKAE-UHFFFAOYSA-N ethyl 4-[1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(Cl)C=CC=2)=N1 WHCYACFFGSYKAE-UHFFFAOYSA-N 0.000 claims 1
- QZSLJGWQMVXKEF-UHFFFAOYSA-N ethyl 4-[1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]propyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(CC)C1=NOC(C=2C=C(Cl)C=CC=2)=N1 QZSLJGWQMVXKEF-UHFFFAOYSA-N 0.000 claims 1
- WIDUGTXIAKIYIC-UHFFFAOYSA-N ethyl 4-[1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(Cl)C=CC=2)=C1 WIDUGTXIAKIYIC-UHFFFAOYSA-N 0.000 claims 1
- JHJHWLKJFNLKCV-UHFFFAOYSA-N ethyl 4-[1-[5-(3-cyanophenyl)-1,2-oxazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(C=CC=2)C#N)=C1 JHJHWLKJFNLKCV-UHFFFAOYSA-N 0.000 claims 1
- SCBLKCVDRCMQAA-UHFFFAOYSA-N ethyl 4-[1-[5-(3-methoxyphenyl)-1,2-oxazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(OC)C=CC=2)=C1 SCBLKCVDRCMQAA-UHFFFAOYSA-N 0.000 claims 1
- CJJMZZQGSJKNJH-UHFFFAOYSA-N ethyl 4-[1-[5-(3-methylphenyl)-1,2,4-oxadiazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(C)C=CC=2)=N1 CJJMZZQGSJKNJH-UHFFFAOYSA-N 0.000 claims 1
- SZBWDTUBTCZQFP-UHFFFAOYSA-N ethyl 4-[1-[5-(3-methylphenyl)-1,2-oxazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C=C(C)C=CC=2)=C1 SZBWDTUBTCZQFP-UHFFFAOYSA-N 0.000 claims 1
- CQVOHVHGPUIFHE-UHFFFAOYSA-N ethyl 4-[1-[5-(5-chloro-2-fluorophenyl)-1,2-oxazol-3-yl]-2,2,2-trifluoroethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C(F)(F)F)C1=NOC(C=2C(=CC=C(Cl)C=2)F)=C1 CQVOHVHGPUIFHE-UHFFFAOYSA-N 0.000 claims 1
- XGOMKSDLZRCUOT-UHFFFAOYSA-N ethyl 4-[1-[5-(5-chloro-2-fluorophenyl)-1,2-oxazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C(=CC=C(Cl)C=2)F)=C1 XGOMKSDLZRCUOT-UHFFFAOYSA-N 0.000 claims 1
- OEWXQDIIHFAANU-UHFFFAOYSA-N ethyl 4-[1-[5-(5-chloro-2-fluorophenyl)-1,3,4-oxadiazol-2-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NN=C(C=2C(=CC=C(Cl)C=2)F)O1 OEWXQDIIHFAANU-UHFFFAOYSA-N 0.000 claims 1
- RHEXYHNUYASTJR-UHFFFAOYSA-N ethyl 4-[1-[5-(5-cyano-2-fluorophenyl)-1,2-oxazol-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NOC(C=2C(=CC=C(C=2)C#N)F)=C1 RHEXYHNUYASTJR-UHFFFAOYSA-N 0.000 claims 1
- VVDMVOBRMDPESL-UHFFFAOYSA-N ethyl 4-[[5-(2-chloro-5-methylphenyl)-1,2,4-oxadiazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C(=CC=C(C)C=2)Cl)=N1 VVDMVOBRMDPESL-UHFFFAOYSA-N 0.000 claims 1
- WYSWFJQHNVTKIX-UHFFFAOYSA-N ethyl 4-[[5-(2-fluoro-5-methylphenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C(=CC=C(C)C=2)F)=C1 WYSWFJQHNVTKIX-UHFFFAOYSA-N 0.000 claims 1
- YLMZLRDYBCNQOB-UHFFFAOYSA-N ethyl 4-[[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methyl]-2-oxopiperazine-1-carboxylate Chemical compound C1C(=O)N(C(=O)OCC)CCN1CC1=NOC(C=2C=C(Cl)C=CC=2)=N1 YLMZLRDYBCNQOB-UHFFFAOYSA-N 0.000 claims 1
- MSZXEGISWRVEJL-UHFFFAOYSA-N ethyl 4-[[5-(3-chlorophenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C=C(Cl)C=CC=2)=C1 MSZXEGISWRVEJL-UHFFFAOYSA-N 0.000 claims 1
- WCOPPSVBQXBIFX-UHFFFAOYSA-N ethyl 4-[[5-(3-chlorophenyl)-1,3-oxazol-2-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NC=C(C=2C=C(Cl)C=CC=2)O1 WCOPPSVBQXBIFX-UHFFFAOYSA-N 0.000 claims 1
- MKHBQSTYABOSJJ-UHFFFAOYSA-N ethyl 4-[[5-(3-cyanophenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C=C(C=CC=2)C#N)=C1 MKHBQSTYABOSJJ-UHFFFAOYSA-N 0.000 claims 1
- YJRQONRACZKXAR-UHFFFAOYSA-N ethyl 4-[[5-(3-formylphenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C=C(C=O)C=CC=2)=C1 YJRQONRACZKXAR-UHFFFAOYSA-N 0.000 claims 1
- MKVHQMLKKPKZSY-UHFFFAOYSA-N ethyl 4-[[5-(3-iodophenyl)-1,2,4-oxadiazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C=C(I)C=CC=2)=N1 MKVHQMLKKPKZSY-UHFFFAOYSA-N 0.000 claims 1
- HVHGZCLMBPGBGL-UHFFFAOYSA-N ethyl 4-[[5-(3-methoxyphenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C=C(OC)C=CC=2)=C1 HVHGZCLMBPGBGL-UHFFFAOYSA-N 0.000 claims 1
- FBCKIMBFWRQSPQ-UHFFFAOYSA-N ethyl 4-[[5-(3-methylphenyl)-1,2,4-oxadiazol-3-yl]methyl]piperazine-1-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C=C(C)C=CC=2)=N1 FBCKIMBFWRQSPQ-UHFFFAOYSA-N 0.000 claims 1
- YLURYVCWGQYISZ-UHFFFAOYSA-N ethyl 4-[[5-(3-methylphenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C=C(C)C=CC=2)=C1 YLURYVCWGQYISZ-UHFFFAOYSA-N 0.000 claims 1
- NIZQRVXFJWKOGJ-UHFFFAOYSA-N ethyl 4-[[5-(5-chloro-2-fluorophenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C(=CC=C(Cl)C=2)F)=C1 NIZQRVXFJWKOGJ-UHFFFAOYSA-N 0.000 claims 1
- AJRYAYKEPOOUBW-UHFFFAOYSA-N ethyl 4-[[5-(5-cyano-2-fluorophenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C(=CC=C(C=2)C#N)F)=C1 AJRYAYKEPOOUBW-UHFFFAOYSA-N 0.000 claims 1
- YRVPVVHDTIPMCI-UHFFFAOYSA-N ethyl 4-[[5-[3-(furan-3-yl)phenyl]-1,2,4-oxadiazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NOC(C=2C=C(C=CC=2)C2=COC=C2)=N1 YRVPVVHDTIPMCI-UHFFFAOYSA-N 0.000 claims 1
- BZKHJSXSSOTBDW-UHFFFAOYSA-N ethyl 4-[cyano-[5-(2-fluoro-5-methylphenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C#N)C1=NOC(C=2C(=CC=C(C)C=2)F)=C1 BZKHJSXSSOTBDW-UHFFFAOYSA-N 0.000 claims 1
- ORTUJEIVHBSTKT-UHFFFAOYSA-N ethyl 4-[cyclopropyl-[5-(2-fluoro-5-methylphenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C1=NOC(=C1)C=1C(=CC=C(C)C=1)F)C1CC1 ORTUJEIVHBSTKT-UHFFFAOYSA-N 0.000 claims 1
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- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- XLYFXQIHPNLPCB-UHFFFAOYSA-N methyl 4-[[5-(3-methylphenyl)-1,2,4-oxadiazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCN1CC1=NOC(C=2C=C(C)C=CC=2)=N1 XLYFXQIHPNLPCB-UHFFFAOYSA-N 0.000 claims 1
- LINCJASNHHSKBX-UHFFFAOYSA-N n-ethyl-n-methyl-4-[1-[5-(3-methylphenyl)-1,2,4-oxadiazol-3-yl]ethyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)CC)CCN1C(C)C1=NOC(C=2C=C(C)C=CC=2)=N1 LINCJASNHHSKBX-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- RPKPFOKNXKRFTD-UHFFFAOYSA-N tert-butyl n-(1-cyanoethyl)carbamate Chemical compound N#CC(C)NC(=O)OC(C)(C)C RPKPFOKNXKRFTD-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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Families Citing this family (105)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3345895B1 (en) | 2003-04-11 | 2019-12-04 | PTC Therapeutics, Inc. | 1,2,4-oxadiazole benzoic acid compound and its use for nonsense suppression and the treatment of disease |
| US7932272B2 (en) | 2003-09-30 | 2011-04-26 | Eisai R&D Management Co., Ltd. | Antifungal agent containing heterocyclic compound |
| WO2005077373A2 (en) * | 2004-02-03 | 2005-08-25 | Astrazeneca Ab | Treatment of gastro-esophageal reflux disease (gerd) |
| KR20070026382A (ko) * | 2004-02-18 | 2007-03-08 | 아스트라제네카 아베 | 아세틸린성 피페라진 화합물 및 대사성 글루타메이트수용체 길항제로서 이들의 용도 |
| US7585881B2 (en) | 2004-02-18 | 2009-09-08 | Astrazeneca Ab | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| AU2005214380A1 (en) | 2004-02-18 | 2005-09-01 | Astrazeneca Ab | Fused hetrocyclic compounds and their use as metabotropic receptor antagonists for the treatment of gastrointestinal disorders |
| CA2563615A1 (en) * | 2004-04-20 | 2005-11-03 | Merck & Co., Inc. | 1,3,5-substituted phenyl derivative compounds useful as beta-secretase inhibitors for the treatment of alzheimer's disease |
| CA2570318A1 (en) * | 2004-06-30 | 2006-01-12 | Banyu Pharmaceutical Co., Ltd. | Biaryl derivatives |
| JP4557685B2 (ja) | 2004-11-15 | 2010-10-06 | 独立行政法人理化学研究所 | 蛍光蛋白質 |
| WO2006089076A2 (en) | 2005-02-18 | 2006-08-24 | Neurogen Corporation | Thiazole amides, imidazole amides and related analogues |
| AU2006235759B2 (en) * | 2005-04-06 | 2011-07-28 | Msd K.K. | 1,4-substituted piperazine derivative |
| CA2603402C (en) * | 2005-04-08 | 2017-10-31 | Ptc Therapeutics, Inc. | Compositions of an orally active 1,2,4-oxadiazole for nonsense mutation suppression therapy |
| JP3789465B1 (ja) | 2005-04-28 | 2006-06-21 | 学校法人立教学院 | イソオキサゾール誘導体又はジヒドロイソオキサゾール誘導体の製造方法 |
| GB0510139D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B1 |
| GB0510140D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B2 |
| KR20080027463A (ko) * | 2005-05-18 | 2008-03-27 | 아덱스 파마 에스에이 | 대사성 글루타메이트 수용체의 양성 알로스테릭조절자로서의 치환된 옥사디아졸 유도체 |
| TW200800204A (en) * | 2005-08-15 | 2008-01-01 | Astrazeneca Ab | Bicyclic piperazines as metabotropic glutatmate receptor antagonists |
| TW200800946A (en) * | 2005-08-15 | 2008-01-01 | Astrazeneca Ab | Substituted piperazines as metabotropic glutamate receptor antagonists |
| AR058807A1 (es) | 2005-09-29 | 2008-02-27 | Astrazeneca Ab | 5-(fenilisoxazoletoxi)-triazol-3-il piridinas sustituidas, para el tratamiento de trastornos mediados por el receptor mglur5 |
| TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| RU2462246C2 (ru) | 2006-03-30 | 2012-09-27 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы получения функционального белка из днк, имеющей нонсенс-мутацию, и лечения нарушений, ассоциированных с ней |
| TW200811179A (en) * | 2006-05-05 | 2008-03-01 | Astrazeneca Ab | mGluR5 modulators VI |
| TW200808800A (en) * | 2006-05-05 | 2008-02-16 | Astrazeneca Ab | MGluR5 modulators V |
| TW200811157A (en) | 2006-05-05 | 2008-03-01 | Astrazeneca Ab | mGluR5 modulators I |
| US7943622B2 (en) | 2006-06-06 | 2011-05-17 | Cornerstone Therapeutics, Inc. | Piperazines, pharmaceutical compositions and methods of use thereof |
| CA2657247A1 (en) | 2006-07-28 | 2008-01-31 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| ES2404348T3 (es) * | 2006-09-08 | 2013-05-27 | Ptc Therapeutics, Inc. | Procedimiento para la preparación de ácidos 1, 2, 4-oxadiazol-benzoicos |
| WO2008035726A1 (en) | 2006-09-21 | 2008-03-27 | Eisai R & D Management Co., Ltd. | Pyridine derivative substituted by heteroaryl ring, and antifungal agent comprising the same |
| CL2007002743A1 (es) | 2006-09-25 | 2008-07-11 | Pct Therapeutics Inc Soc Organ | Forma cristalina del acido 3-[5-(2-fluorofenil)-[1,2,4]oxadiazol-3-il]-benzoico; composicion farmaceutica que comprende a dicha forma cristalina; y su uso para modular la terminacion prematura de traslado o decaimiento de marn, tales como carcicoma. |
| EP2068871B1 (en) * | 2006-09-25 | 2013-12-25 | PTC Therapeutics, Inc. | Hydroxylated 1,2,4-oxadiazole benzoic acid compounds, compositions thereof and the use for nonsense suppression |
| SI2073805T1 (sl) * | 2006-10-12 | 2015-10-30 | Ptc Therapeutics, Inc. | Postopki za odmerjanje peroralno aktivnega 1,2,4-oksadiazola za zdravljenje supresije nesmiselnih mutacij |
| WO2008050200A1 (en) * | 2006-10-24 | 2008-05-02 | Pfizer Products Inc. | Oxadiazole compounds as calcium channel antagonists |
| UY30892A1 (es) * | 2007-02-07 | 2008-09-02 | Smithkline Beckman Corp | Inhibidores de la actividad akt |
| WO2008117148A1 (en) * | 2007-03-23 | 2008-10-02 | Pfizer Products Inc. | Substituted oxadiazole analogs as calcium channel antagonists |
| TW200841879A (en) | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
| CN101679191B (zh) * | 2007-06-05 | 2014-03-12 | 塞诺菲-安万特股份有限公司 | 二杂芳基环己烷衍生物、其制备方法、用途及含有它们的药用组合物 |
| ES2393824T3 (es) * | 2007-09-21 | 2012-12-28 | Array Biopharma, Inc. | Derivados de piridin-2-il-amino-1,2,4-tiadiazol como activadores de glucoquinasa para el tratamiento de diabetes mellitus |
| CA2704684A1 (en) | 2007-11-07 | 2009-05-14 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
| WO2009147189A1 (en) | 2008-06-05 | 2009-12-10 | Glaxo Group Limited | Novel compounds |
| JP5502077B2 (ja) | 2008-06-05 | 2014-05-28 | グラクソ グループ リミテッド | 新規な化合物 |
| ES2445199T3 (es) | 2008-06-05 | 2014-02-28 | Glaxo Group Limited | Derivados de benzpirazol como inhibidores de PI3-quinasas |
| CA2730037A1 (en) | 2008-07-10 | 2010-01-14 | Boehringer Ingelheim International Gmbh | Sulfone compounds which modulate the cb2 receptor |
| KR20110063485A (ko) | 2008-09-25 | 2011-06-10 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｃｂ2 수용체를 선택적으로 조절하는 설포닐 화합물 |
| US8188119B2 (en) | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
| DE102009041241A1 (de) | 2009-09-11 | 2011-08-04 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057364A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057343A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102009041242A1 (de) | 2009-09-11 | 2011-12-15 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057344A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Aminoalkyl-substituierte Aryl-Verbindungen und ihre Verwendung |
| EA020460B1 (ru) | 2009-01-12 | 2014-11-28 | Пфайзер Лимитед | Производные сульфонамида |
| MY161598A (en) * | 2009-01-30 | 2017-04-28 | Glaxosmithkline Llc | Crystalline n-{ (1s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl} -5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride |
| JP5705748B2 (ja) | 2009-02-18 | 2015-04-22 | 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 | Ｃｂ２受容体を変調する複素環化合物 |
| US8524751B2 (en) | 2009-03-09 | 2013-09-03 | GlaxoSmithKline Intellecutual Property Development | 4-oxadiazol-2-YL-indazoles as inhibitors of P13 kinases |
| CN102459253B (zh) | 2009-04-30 | 2015-03-25 | 葛兰素集团有限公司 | 作为pi3-激酶抑制剂的*唑取代的吲唑化合物 |
| CA2764387A1 (en) | 2009-06-05 | 2010-12-09 | Link Medicine Corporation | Aminopyrrolidinone derivatives and uses thereof |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| JP5756800B2 (ja) | 2009-06-16 | 2015-07-29 | 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 | Ｃｂ２受容体を調節するアゼチジン２−カルボキサミド誘導体 |
| WO2011037795A1 (en) | 2009-09-22 | 2011-03-31 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the cb2 receptor |
| WO2011088015A1 (en) | 2010-01-15 | 2011-07-21 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| JP5746228B2 (ja) | 2010-03-05 | 2015-07-08 | 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 | Ｃｂ２受容体を選択的に調節するテトラゾール化合物 |
| EP2560966B1 (en) | 2010-03-30 | 2021-01-06 | Verseon International Corporation | Multisubstituted aromatic compounds as inhibitors of thrombin |
| ES2532356T3 (es) | 2010-07-09 | 2015-03-26 | Pfizer Limited | N-sulfonilbenzamidas como inhibidores de los canales de sodio dependientes de voltaje |
| US8846936B2 (en) | 2010-07-22 | 2014-09-30 | Boehringer Ingelheim International Gmbh | Sulfonyl compounds which modulate the CB2 receptor |
| GB201018124D0 (en) | 2010-10-27 | 2010-12-08 | Glaxo Group Ltd | Polymorphs and salts |
| AR086113A1 (es) | 2011-04-30 | 2013-11-20 | Abbott Lab | Isoxazolinas como agentes terapeuticos |
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| JP2013028559A (ja) * | 2011-07-28 | 2013-02-07 | Nippon Light Metal Co Ltd | ３−クロロ−４−メチル安息香酸イソプロピル及びその製造方法 |
| US8729263B2 (en) | 2012-08-13 | 2014-05-20 | Novartis Ag | 1,4-disubstituted pyridazine analogs there of and methods for treating SMN-deficiency-related conditions |
| US9040712B2 (en) | 2013-01-23 | 2015-05-26 | Novartis Ag | Thiadiazole analogs thereof and methods for treating SMN-deficiency-related-conditions |
| EP3587406B1 (en) | 2013-03-13 | 2021-01-27 | Forma Therapeutics, Inc. | 2-hydroxy-1-{4-[(4-phenylphenyl)carbonyl]piperazin-1-yl}ethan-1-one derivatives and related compounds as fatty acid synthase (fasn) inhibitors for the treatment of cancer |
| EP2970141B1 (en) | 2013-03-15 | 2020-02-26 | Verseon Corporation | Halogenopyrazoles as inhibitors of thrombin |
| ES2853483T3 (es) | 2013-03-15 | 2021-09-16 | Verseon Int Corporation | Compuestos aromáticos multisustituidos como inhibidores de la serina proteasa |
| CN112500338A (zh) | 2013-03-15 | 2021-03-16 | 全球血液疗法股份有限公司 | 化合物及其用于调节血红蛋白的用途 |
| EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
| TW201506024A (zh) | 2013-07-02 | 2015-02-16 | 必治妥美雅史谷比公司 | 作為有效ｒｏｃｋ抑制劑的三環甲醯胺衍生物 |
| JP6522602B2 (ja) | 2013-07-02 | 2019-05-29 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｒｏｃｋ阻害剤としての三環式ピリド−カルボキサミド誘導体 |
| EA030631B1 (ru) | 2013-07-31 | 2018-09-28 | Новартис Аг | 1,4-дизамещенные аналоги пиридазинхинолина и способы лечения состояний, связанных с smn-дефицитом |
| EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| GB201402277D0 (en) | 2014-02-10 | 2014-03-26 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| EP2907806A1 (en) * | 2014-02-14 | 2015-08-19 | Universita Degli Studi Di Genova | New compounds as selective PDE4D inhibitors |
| JP6946001B2 (ja) | 2014-03-06 | 2021-10-06 | ピーティーシー セラピューティクス， インコーポレイテッド | 薬学的組成物、および１，２，４−オキサジアゾール安息香酸の塩 |
| CA2954060A1 (en) | 2014-07-03 | 2016-01-07 | Celgene Quanticel Research, Inc. | Inhibitors of lysine specific demethylase-1 |
| BR112017004704A2 (pt) * | 2014-09-17 | 2018-01-23 | Verseon Corp | composto, composição farmacêutica, e, método para tratar uma doença ou distúrbio em um indivíduo |
| ES2929355T3 (es) | 2015-02-24 | 2022-11-28 | Bayer Cropscience Ag | Procedimiento para la preparación de triazoles |
| US10532995B2 (en) | 2015-02-27 | 2020-01-14 | Verseon Corporation | Substituted pyrazole compounds as serine protease inhibitors |
| JP2018531924A (ja) | 2015-09-24 | 2018-11-01 | ファイザー・インク | テトラヒドロピラノ［３，４−ｄ］［１，３］オキサジン誘導体、およびｂａｃｅ阻害剤としてのその使用 |
| HK1251965A1 (zh) | 2015-10-30 | 2019-05-10 | Ptc医疗公司 | 用於治疗癫痫的方法 |
| CA2968836C (en) | 2016-06-13 | 2025-09-02 | Gilead Sciences, Inc. | FXR MODULATING COMPOUNDS (NR1H4) |
| ES2921432T3 (es) | 2016-06-13 | 2022-08-25 | Gilead Sciences Inc | Derivados de azetidina como moduladores de FXR (NR1H4) |
| US11008325B2 (en) | 2016-11-14 | 2021-05-18 | Virginia Commonwealth University | Inhibitors of cancer invasion, attachment, and/or metastasis |
| EP4424364B1 (en) | 2017-03-28 | 2026-01-21 | Gilead Sciences, Inc. | Combinations for use in the treatment of cirrhosis and liver fibrosis |
| CN107382990B (zh) * | 2017-08-09 | 2020-08-04 | 济南大学 | 一种具有1,2,4-恶二唑结构片段的化合物及其制备方法和应用 |
| WO2019071073A1 (en) | 2017-10-06 | 2019-04-11 | Forma Therapeutics, Inc. | INHIBITION OF THE SPECIFIC PEPTIDASE OF UBIQUITIN |
| ES2988920T3 (es) | 2018-05-17 | 2024-11-22 | Forma Therapeutics Inc | Compuestos bicíclicos fusionados útiles como inhibidores de la peptidasa 30 específica de ubiquitina |
| AU2019356011B2 (en) | 2018-10-05 | 2025-02-06 | Forma Therapeutics, Inc. | Fused pyrrolines which act as Ubiquitin-Specific Protease 30 (USP30) inhibitors |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| CN113382633A (zh) | 2018-10-29 | 2021-09-10 | 福马治疗股份有限公司 | (4-(2-氟-4-(1-甲基-1H-苯并[d]咪唑-5-基)苯甲酰基)哌嗪-1-基)(1-羟基环丙基)甲酮的固体形式 |
| PE20211907A1 (es) | 2019-01-15 | 2021-09-28 | Gilead Sciences Inc | Compuestos moduladores de fxr (nr1h4) |
| JP7094456B2 (ja) | 2019-01-31 | 2022-07-01 | ファイザー・インク | Ｃｄｋ２阻害剤 |
| KR102725082B1 (ko) | 2019-02-19 | 2024-11-04 | 길리애드 사이언시즈, 인코포레이티드 | Fxr 효능제의 고체 형태 |
| US11932630B2 (en) | 2021-04-16 | 2024-03-19 | Novartis Ag | Heteroaryl aminopropanol derivatives |
| CN113248455A (zh) * | 2021-05-25 | 2021-08-13 | 湖北科技学院 | 一种3,5-二取代异噁唑类衍生物及其合成方法 |
| DK4514782T3 (da) | 2022-05-19 | 2025-12-15 | Astrazeneca Ab | Heteroaromatiske amidoforbindelser, der er nyttige ved behandling af leversygdomme |
| US12565492B2 (en) | 2024-08-09 | 2026-03-03 | Triana Biomedicines, Inc. | Anaplastic Lymphoma Kinase (ALK) degraders and uses thereof |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3740434A (en) * | 1966-12-23 | 1973-06-19 | American Cyanamid Co | Substituted nitroimidazolylthiadiazoles and oxadiazoles as antiprotozoal agents |
| US3816426A (en) * | 1970-10-27 | 1974-06-11 | Abbott Lab | 1-(5-phenyl-4-oxo-2-oxazolin-2-yl)piperazines |
| JPS56127364A (en) * | 1980-03-01 | 1981-10-06 | Mitsui Toatsu Chem Inc | Novel piperazine compound, its preparation and utilization |
| JP3003148B2 (ja) * | 1989-01-05 | 2000-01-24 | 藤沢薬品工業株式会社 | チアゾール化合物、その製造法およびそれを含有する医薬組成物 |
| IL96891A0 (en) * | 1990-01-17 | 1992-03-29 | Merck Sharp & Dohme | Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them |
| CA2146019A1 (en) * | 1992-10-23 | 1994-05-11 | Howard B. Broughton | Dopamine receptor subtype ligands |
| DE19858191A1 (de) * | 1998-12-17 | 2000-06-21 | Aventis Cropscience Gmbh | 4-Haloalkyl-3-heterocyclylpyridine und 4-Haloalkyl-5-heterocyclyl-pyrimidine und ihre Verwendung als Repellentien |
| CO5170501A1 (es) * | 1999-04-14 | 2002-06-27 | Novartis Ag | AZOLES SUSTITUIDOS UTILES PARA EL TRATAMIENTO DE ENFERMEDADES MEDIADAS POR TNFa eIL-1 Y ENFERMEDADES DEL METABOLISMO OSEO |
| SK2512002A3 (en) * | 1999-08-19 | 2002-07-02 | Nps Pharma Inc | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| TWI292316B (en) * | 1999-10-11 | 2008-01-11 | Sod Conseils Rech Applic | Pharmaceutical composition of thiazole derivatives intended to inhibit mao and/or lipidic peroxidation and/or to act as modulators of sodium channels and the use thereof |
| EP1318992B1 (en) * | 2000-09-21 | 2005-07-27 | Smithkline Beecham Plc | Imidazole derivatives as raf kinase inhibitors |
| ATE288898T1 (de) * | 2000-12-04 | 2005-02-15 | Hoffmann La Roche | Phenylethenyl- oder phenylethinylderivate als glutamatrezeptorantagonisten |
| WO2003008411A1 (en) * | 2001-07-19 | 2003-01-30 | Cv Therapeutics, Inc. | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
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2003
- 2003-08-08 AU AU2003268064A patent/AU2003268064A1/en not_active Abandoned
- 2003-08-08 KR KR1020057002200A patent/KR20050039846A/ko not_active Withdrawn
- 2003-08-08 JP JP2004527912A patent/JP2006506340A/ja active Pending
- 2003-08-08 TW TW092121861A patent/TW200424183A/zh unknown
- 2003-08-08 NZ NZ538339A patent/NZ538339A/en unknown
- 2003-08-08 WO PCT/US2003/024912 patent/WO2004014370A2/en not_active Ceased
- 2003-08-08 US US10/636,965 patent/US20040132726A1/en not_active Abandoned
- 2003-08-08 EP EP03749015A patent/EP1536790A2/en not_active Withdrawn
- 2003-08-08 CA CA002495120A patent/CA2495120A1/en not_active Abandoned
- 2003-08-08 MX MXPA05001592A patent/MXPA05001592A/es unknown
- 2003-08-08 BR BR0313266-8A patent/BR0313266A/pt not_active IP Right Cessation
- 2003-08-08 AR ARP030102892A patent/AR041508A1/es unknown
- 2003-08-08 TW TW096135411A patent/TW200812986A/zh unknown
- 2003-08-08 CN CNA038238594A patent/CN1691944A/zh active Pending
-
2005
- 2005-02-02 IL IL16665005A patent/IL166650A0/xx unknown
- 2005-02-07 ZA ZA200501101A patent/ZA200501101B/xx unknown
- 2005-03-09 NO NO20051223A patent/NO20051223L/no not_active Application Discontinuation
- 2005-11-10 US US11/270,617 patent/US20060063772A1/en not_active Abandoned
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