JP2008543781A5 - - Google Patents
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- JP2008543781A5 JP2008543781A5 JP2008515998A JP2008515998A JP2008543781A5 JP 2008543781 A5 JP2008543781 A5 JP 2008543781A5 JP 2008515998 A JP2008515998 A JP 2008515998A JP 2008515998 A JP2008515998 A JP 2008515998A JP 2008543781 A5 JP2008543781 A5 JP 2008543781A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- unsubstituted
- halogen
- alkoxy
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 249
- 229910052736 halogen Inorganic materials 0.000 claims 119
- -1 nitro, amino Chemical group 0.000 claims 99
- 125000003545 alkoxy group Chemical group 0.000 claims 93
- 150000002367 halogens Chemical class 0.000 claims 92
- 125000004432 carbon atom Chemical group C* 0.000 claims 89
- 125000004093 cyano group Chemical group *C#N 0.000 claims 84
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 65
- 125000003118 aryl group Chemical group 0.000 claims 64
- 125000000623 heterocyclic group Chemical group 0.000 claims 56
- 150000001875 compounds Chemical class 0.000 claims 51
- 125000004043 oxo group Chemical group O=* 0.000 claims 50
- 125000006413 ring segment Chemical group 0.000 claims 50
- 125000004663 dialkyl amino group Chemical group 0.000 claims 46
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 44
- 229920006395 saturated elastomer Polymers 0.000 claims 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims 36
- 125000005843 halogen group Chemical group 0.000 claims 32
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 28
- 239000002253 acid Substances 0.000 claims 27
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 27
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 27
- 125000001072 heteroaryl group Chemical group 0.000 claims 27
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 27
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims 26
- 125000002252 acyl group Chemical group 0.000 claims 26
- 125000004414 alkyl thio group Chemical group 0.000 claims 26
- 125000004103 aminoalkyl group Chemical group 0.000 claims 25
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 24
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 24
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 23
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 22
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 21
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 20
- 125000003282 alkyl amino group Chemical group 0.000 claims 19
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 125000003386 piperidinyl group Chemical group 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims 16
- 239000012453 solvate Substances 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 150000001350 alkyl halides Chemical class 0.000 claims 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 11
- 125000004434 sulfur atom Chemical group 0.000 claims 11
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims 10
- 125000002837 carbocyclic group Chemical group 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical group O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- QRNCCTIIOZVCIA-UHFFFAOYSA-N 4-(3-chloro-4-methoxy-n-(1-propylpiperidin-4-yl)anilino)-n,n-diethylbenzamide Chemical compound C1CN(CCC)CCC1N(C=1C=C(Cl)C(OC)=CC=1)C1=CC=C(C(=O)N(CC)CC)C=C1 QRNCCTIIOZVCIA-UHFFFAOYSA-N 0.000 claims 1
- JGJDLFLIGNFPAC-UHFFFAOYSA-N 4-[(6-ethoxy-5-methoxypyridin-2-yl)-(1,3-oxazol-5-ylmethyl)amino]benzoic acid Chemical compound C1=C(OC)C(OCC)=NC(N(CC=2OC=NC=2)C=2C=CC(=CC=2)C(O)=O)=C1 JGJDLFLIGNFPAC-UHFFFAOYSA-N 0.000 claims 1
- WJACOBKRQKVCJM-UHFFFAOYSA-N 4-[(6-ethoxy-5-methoxypyridin-2-yl)-(1,3-thiazol-5-ylmethyl)amino]benzoic acid Chemical compound C1=C(OC)C(OCC)=NC(N(CC=2SC=NC=2)C=2C=CC(=CC=2)C(O)=O)=C1 WJACOBKRQKVCJM-UHFFFAOYSA-N 0.000 claims 1
- FWSWTFHBBJPTQK-UHFFFAOYSA-N 4-[(6-ethoxy-5-methoxypyridin-2-yl)-(pyrimidin-5-ylmethyl)amino]benzoic acid Chemical compound C1=C(OC)C(OCC)=NC(N(CC=2C=NC=NC=2)C=2C=CC(=CC=2)C(O)=O)=C1 FWSWTFHBBJPTQK-UHFFFAOYSA-N 0.000 claims 1
- ONHUVOIDNIWKMR-UHFFFAOYSA-N 4-[(6-ethoxy-5-methoxypyridin-2-yl)-piperidin-4-ylamino]benzonitrile Chemical compound C1=C(OC)C(OCC)=NC(N(C2CCNCC2)C=2C=CC(=CC=2)C#N)=C1 ONHUVOIDNIWKMR-UHFFFAOYSA-N 0.000 claims 1
- HGSXTMKEBSCTAC-UHFFFAOYSA-N 4-[[5-(difluoromethoxy)-6-ethoxypyridin-2-yl]-(1,3-oxazol-5-ylmethyl)amino]benzoic acid Chemical compound C1=C(OC(F)F)C(OCC)=NC(N(CC=2OC=NC=2)C=2C=CC(=CC=2)C(O)=O)=C1 HGSXTMKEBSCTAC-UHFFFAOYSA-N 0.000 claims 1
- CRMGQNUEIZIEDJ-UHFFFAOYSA-N 4-[[5-(difluoromethoxy)-6-ethoxypyridin-2-yl]-(1,3-thiazol-5-ylmethyl)amino]benzoic acid Chemical compound C1=C(OC(F)F)C(OCC)=NC(N(CC=2SC=NC=2)C=2C=CC(=CC=2)C(O)=O)=C1 CRMGQNUEIZIEDJ-UHFFFAOYSA-N 0.000 claims 1
- PHEUKIVYGKGGGN-UHFFFAOYSA-N 4-[[5-(difluoromethoxy)-6-ethoxypyridin-2-yl]-(pyrimidin-5-ylmethyl)amino]benzoic acid Chemical compound C1=C(OC(F)F)C(OCC)=NC(N(CC=2C=NC=NC=2)C=2C=CC(=CC=2)C(O)=O)=C1 PHEUKIVYGKGGGN-UHFFFAOYSA-N 0.000 claims 1
- IFRFJSBDHAWWRV-UHFFFAOYSA-N 4-[[5-(difluoromethoxy)-6-methoxypyridin-2-yl]-(1,3-thiazol-5-ylmethyl)amino]benzoic acid Chemical compound C1=C(OC(F)F)C(OC)=NC(N(CC=2SC=NC=2)C=2C=CC(=CC=2)C(O)=O)=C1 IFRFJSBDHAWWRV-UHFFFAOYSA-N 0.000 claims 1
- VQNNHIBWFITRAW-UHFFFAOYSA-N 4-[[6-(cyclopropylmethoxy)-5-(difluoromethoxy)pyridin-2-yl]-(1,3-thiazol-5-ylmethyl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N(C=1N=C(OCC2CC2)C(OC(F)F)=CC=1)CC1=CN=CS1 VQNNHIBWFITRAW-UHFFFAOYSA-N 0.000 claims 1
- IVZGMNUKKUFAJD-UHFFFAOYSA-N 4-[[6-(cyclopropylmethoxy)-5-methoxypyridin-2-yl]-(1,3-thiazol-5-ylmethyl)amino]benzoic acid Chemical compound COC1=CC=C(N(CC=2SC=NC=2)C=2C=CC(=CC=2)C(O)=O)N=C1OCC1CC1 IVZGMNUKKUFAJD-UHFFFAOYSA-N 0.000 claims 1
- GZHLGTXHZCTPOH-UHFFFAOYSA-N 4-n-[5-methoxy-6-(2-methylpropoxy)pyridin-2-yl]-1-n,1-n-dimethyl-4-n-piperidin-4-ylbenzene-1,4-diamine Chemical compound N1=C(OCC(C)C)C(OC)=CC=C1N(C=1C=CC(=CC=1)N(C)C)C1CCNCC1 GZHLGTXHZCTPOH-UHFFFAOYSA-N 0.000 claims 1
- IVAGFHVEUSPJHQ-UHFFFAOYSA-N 5-(difluoromethoxy)-6-methoxy-n-(4-methoxyphenyl)-n-piperidin-4-ylpyridin-2-amine Chemical compound C1=CC(OC)=CC=C1N(C=1N=C(OC)C(OC(F)F)=CC=1)C1CCNCC1 IVAGFHVEUSPJHQ-UHFFFAOYSA-N 0.000 claims 1
- QFGMCTRUGUQECK-UHFFFAOYSA-N 5-chloro-n-(3-chlorophenyl)-4,6-difluoro-n-[(4-methoxyphenyl)methyl]pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1CN(C=1N=C(F)C(Cl)=C(F)N=1)C1=CC=CC(Cl)=C1 QFGMCTRUGUQECK-UHFFFAOYSA-N 0.000 claims 1
- XHZJNOIVHDBTFH-UHFFFAOYSA-N 5-methoxy-6-(oxolan-3-yloxy)-n-(piperidin-4-ylmethyl)-n-(pyridin-3-ylmethyl)pyridin-2-amine Chemical compound COC1=CC=C(N(CC2CCNCC2)CC=2C=NC=CC=2)N=C1OC1CCOC1 XHZJNOIVHDBTFH-UHFFFAOYSA-N 0.000 claims 1
- ATYXQKUQUJMFTE-UHFFFAOYSA-N 5-methoxy-n-piperidin-4-yl-6-propan-2-yloxy-n-(1,3-thiazol-5-ylmethyl)pyridin-2-amine Chemical compound N1=C(OC(C)C)C(OC)=CC=C1N(C1CCNCC1)CC1=CN=CS1 ATYXQKUQUJMFTE-UHFFFAOYSA-N 0.000 claims 1
- ZDTXVUGPITYZFU-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-5-methoxy-n-phenyl-n-piperidin-3-ylpyridin-2-amine Chemical compound COC1=CC=C(N(C2CNCCC2)C=2C=CC=CC=2)N=C1OCC1CC1 ZDTXVUGPITYZFU-UHFFFAOYSA-N 0.000 claims 1
- LSXRAIWEOCHNPW-UHFFFAOYSA-N 6-[n-(furan-2-ylmethyl)-3,4-dimethoxyanilino]-2h-1,2,4-triazine-3,5-dione Chemical compound C1=C(OC)C(OC)=CC=C1N(C=1C(NC(=O)NN=1)=O)CC1=CC=CO1 LSXRAIWEOCHNPW-UHFFFAOYSA-N 0.000 claims 1
- GVOJEZJTSPUATE-UHFFFAOYSA-N 6-cyclopentyloxy-5-methoxy-n-phenyl-n-piperidin-4-ylpyridin-2-amine Chemical compound COC1=CC=C(N(C2CCNCC2)C=2C=CC=CC=2)N=C1OC1CCCC1 GVOJEZJTSPUATE-UHFFFAOYSA-N 0.000 claims 1
- GJGXLZONUINJQI-UHFFFAOYSA-N 6-cyclopentyloxy-5-methoxy-n-piperidin-4-yl-n-(pyrimidin-5-ylmethyl)pyridin-2-amine Chemical compound COC1=CC=C(N(CC=2C=NC=NC=2)C2CCNCC2)N=C1OC1CCCC1 GJGXLZONUINJQI-UHFFFAOYSA-N 0.000 claims 1
- URQPJYUZFLFRSA-UHFFFAOYSA-N 6-ethoxy-5-methoxy-n-(4-methylphenyl)-n-pyrrolidin-3-ylpyridin-2-amine Chemical compound C1=C(OC)C(OCC)=NC(N(C2CNCC2)C=2C=CC(C)=CC=2)=C1 URQPJYUZFLFRSA-UHFFFAOYSA-N 0.000 claims 1
- WVDVBXCDCBPOFB-UHFFFAOYSA-N 6-ethoxy-5-methoxy-n-piperidin-4-yl-n-thiophen-3-ylpyridin-2-amine Chemical compound C1=C(OC)C(OCC)=NC(N(C2CCNCC2)C2=CSC=C2)=C1 WVDVBXCDCBPOFB-UHFFFAOYSA-N 0.000 claims 1
- 102000009346 Adenosine receptors Human genes 0.000 claims 1
- 108050000203 Adenosine receptors Proteins 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 claims 1
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 claims 1
- 229910014284 N-O Inorganic materials 0.000 claims 1
- 229910014335 N—O Inorganic materials 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 230000001713 cholinergic effect Effects 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 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
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 1
- 229960003530 donepezil Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical class OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- UHRHFLSWCCNPKQ-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-n-piperidin-1-ylpiperidin-1-amine Chemical compound C1=C(C)C(C)=CC=C1N(N1CCCCC1)N1CCCCC1 UHRHFLSWCCNPKQ-UHFFFAOYSA-N 0.000 claims 1
- BRJKPRMJJIQLMA-UHFFFAOYSA-N n-(3-chlorophenyl)-5-(difluoromethoxy)-6-ethoxy-n-piperidin-4-ylpyridin-2-amine Chemical compound C1=C(OC(F)F)C(OCC)=NC(N(C2CCNCC2)C=2C=C(Cl)C=CC=2)=C1 BRJKPRMJJIQLMA-UHFFFAOYSA-N 0.000 claims 1
- SKIYCDXYLAFQOH-UHFFFAOYSA-N n-(3-chlorophenyl)-5-methoxy-n-piperidin-4-yl-6-propan-2-yloxypyridin-2-amine Chemical compound N1=C(OC(C)C)C(OC)=CC=C1N(C=1C=C(Cl)C=CC=1)C1CCNCC1 SKIYCDXYLAFQOH-UHFFFAOYSA-N 0.000 claims 1
- WIQUTMONCRGWPL-UHFFFAOYSA-N n-(3-chlorophenyl)-n-[4-(difluoromethoxy)-3-methoxyphenyl]piperidin-4-amine Chemical compound C1=C(OC(F)F)C(OC)=CC(N(C2CCNCC2)C=2C=C(Cl)C=CC=2)=C1 WIQUTMONCRGWPL-UHFFFAOYSA-N 0.000 claims 1
- POZILCYGNZWHNW-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-methoxy-n-piperidin-4-yl-6-propan-2-yloxypyridin-2-amine Chemical compound N1=C(OC(C)C)C(OC)=CC=C1N(C1CCNCC1)CC1=CC=C(F)C=C1 POZILCYGNZWHNW-UHFFFAOYSA-N 0.000 claims 1
- ZTMDVJTUYYKKJV-UHFFFAOYSA-N n-benzyl-6-cyclopentyloxy-5-methoxy-n-piperidin-4-ylpyridin-2-amine Chemical compound COC1=CC=C(N(CC=2C=CC=CC=2)C2CCNCC2)N=C1OC1CCCC1 ZTMDVJTUYYKKJV-UHFFFAOYSA-N 0.000 claims 1
- INOVPKZAEASFME-UHFFFAOYSA-N n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC=C1 INOVPKZAEASFME-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68906005P | 2005-06-10 | 2005-06-10 | |
| PCT/US2006/022655 WO2006135828A2 (en) | 2005-06-10 | 2006-06-09 | Trisubstituted amines as phosphodiesterase 4 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008543781A JP2008543781A (ja) | 2008-12-04 |
| JP2008543781A5 true JP2008543781A5 (enExample) | 2009-07-02 |
Family
ID=37075617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008515998A Pending JP2008543781A (ja) | 2005-06-10 | 2006-06-09 | ホスフオジエステラーゼ４阻害剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20070049611A1 (enExample) |
| EP (1) | EP1888528A2 (enExample) |
| JP (1) | JP2008543781A (enExample) |
| AU (1) | AU2006257863A1 (enExample) |
| CA (1) | CA2611562A1 (enExample) |
| WO (1) | WO2006135828A2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5219465B2 (ja) * | 2006-11-10 | 2013-06-26 | 大塚製薬株式会社 | 医薬 |
| KR101507717B1 (ko) | 2006-12-22 | 2015-04-08 | 레오 파마 에이/에스 | Ｐｄｅ4 억제제로서 유용한 치환된 아세토페논 |
| CN101611005B (zh) * | 2006-12-22 | 2013-11-06 | 利奥制药有限公司 | 用作pde4抑制剂的取代的苯乙酮类 |
| WO2008105386A1 (ja) * | 2007-02-27 | 2008-09-04 | National University Corporation Okayama University | アルコキシ基を有するレキシノイド化合物 |
| FR2915098B1 (fr) * | 2007-04-19 | 2009-06-05 | Sanofi Aventis Sa | Utilisation du 4-cyclopropylmethoxy-n-(3,5-dichloro-1-oxydo- pyridin-4-yl)-5-(methoxy)pyridine-2-carboxamide pour le traitement des traumatismes de la moelle epiniere |
| FR2915100B1 (fr) * | 2007-04-19 | 2009-06-05 | Sanofi Aventis Sa | Utilisation du 4-cyclopropylmethoxy-n-(3,5-dichloro-1-oxydo- pyridin-4-yl)-5-(methoxy)pyridine-2-carboxalide pour le traitement des desordres moteurs lies a la maladie de parkinson |
| FR2915099B1 (fr) * | 2007-04-19 | 2009-06-05 | Sanofi Aventis Sa | Utilisation du 4-cyclopropylmethoxy-n-(3,5-dichloro-1-oxydo- pyridin-4-yl)-5-(methoxy)pyridine-2-carboxamide pour le traitement des traumatismes craniens |
| EP2110375A1 (en) * | 2008-04-14 | 2009-10-21 | CHIESI FARMACEUTICI S.p.A. | Phosphodiesterase-4 inhibitors belonging to the tertiary amine class |
| WO2010041449A1 (ja) * | 2008-10-09 | 2010-04-15 | 国立大学法人 岡山大学 | Rxr作動性物質を有効成分とする抗アレルギー剤 |
| WO2010059372A2 (en) * | 2008-10-30 | 2010-05-27 | Herbalscience Group, Llc | Tryptase enzyme inhibiting aminopyridines |
| WO2010053902A2 (en) * | 2008-11-04 | 2010-05-14 | Herbalscience Group, Llc | Tryptase enzyme inhibiting aminothiophenols |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| JP6169492B2 (ja) | 2011-11-15 | 2017-07-26 | 武田薬品工業株式会社 | ジヒドロキシ芳香族へテロ環化合物 |
| GB201222711D0 (en) | 2012-12-17 | 2013-01-30 | Takeda Pharmaceutical | Novel compounds |
| WO2015022418A1 (en) * | 2013-08-16 | 2015-02-19 | Takeda Gmbh | Treatment of cognitive impairment with pde4 inhibitor |
| TW201534301A (zh) * | 2013-08-16 | 2015-09-16 | Takeda Gmbh | 以組合療法治療認知損傷 |
| US20170119775A1 (en) * | 2014-03-28 | 2017-05-04 | Algiax Pharmaceuticals Gmbh | Treatment of cognitive disorders |
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| FR2244520B1 (enExample) * | 1973-07-06 | 1977-02-04 | Ugine Kuhlmann | |
| US4524373A (en) * | 1982-02-24 | 1985-06-18 | Kanzaki Paper Manufacturing Co., Ltd. | Fluoran derivatives as new compounds, process for preparing the same and recording system utilizing the same as colorless chromogenic material |
| US5204226A (en) * | 1991-03-04 | 1993-04-20 | International Business Machines Corporation | Photosensitizers for polysilanes |
| GB9401460D0 (en) * | 1994-01-26 | 1994-03-23 | Rhone Poulenc Rorer Ltd | Compositions of matter |
| US5935966A (en) * | 1995-09-01 | 1999-08-10 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions |
| JPH1072415A (ja) * | 1996-06-26 | 1998-03-17 | Nikken Chem Co Ltd | ３−アニリノ−２−シクロアルケノン誘導体 |
| US6235736B1 (en) * | 1997-06-24 | 2001-05-22 | Nikken Chemicals Co., Ltd. | 3-anilino-2-cycloalkenone derivatives |
| US7205320B2 (en) * | 2001-01-22 | 2007-04-17 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| WO2002074726A2 (en) * | 2001-01-22 | 2002-09-26 | Memory Pharmaceuticals Corporation | Aniline derivatives useful as phosphodiesterase 4 inhibitors |
| WO2002064096A2 (en) * | 2001-02-16 | 2002-08-22 | Tularik Inc. | Methods of using pyrimidine-based antiviral agents |
| US6986126B2 (en) * | 2001-04-13 | 2006-01-10 | Sun Microsystems, Inc. | Method and apparatus for detecting violations of type rules in a computer program |
| US20030149052A1 (en) * | 2002-01-22 | 2003-08-07 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| RU2368604C2 (ru) * | 2002-07-19 | 2009-09-27 | Мемори Фармасьютиклз Корпорейшн | Ингибиторы фосфодиэстеразы 4, включающие n-замещенные аналоги анилина и дифениламина |
| KR20050075430A (ko) * | 2002-11-19 | 2005-07-20 | 메모리 파마슈티칼스 코포레이션 | 포스포디에스테라제 4 억제제 |
| MY141255A (en) * | 2003-12-11 | 2010-03-31 | Memory Pharm Corp | Phosphodiesterase 4 inhibitors, including n-substituted diarylamine analogs |
-
2006
- 2006-06-09 AU AU2006257863A patent/AU2006257863A1/en not_active Abandoned
- 2006-06-09 CA CA002611562A patent/CA2611562A1/en not_active Abandoned
- 2006-06-09 JP JP2008515998A patent/JP2008543781A/ja active Pending
- 2006-06-09 WO PCT/US2006/022655 patent/WO2006135828A2/en not_active Ceased
- 2006-06-09 US US11/449,868 patent/US20070049611A1/en not_active Abandoned
- 2006-06-09 EP EP06784743A patent/EP1888528A2/en not_active Withdrawn
-
2008
- 2008-12-05 US US12/329,214 patent/US20090118270A1/en not_active Abandoned
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