JP2008525500A5 - - Google Patents
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- JP2008525500A5 JP2008525500A5 JP2007548601A JP2007548601A JP2008525500A5 JP 2008525500 A5 JP2008525500 A5 JP 2008525500A5 JP 2007548601 A JP2007548601 A JP 2007548601A JP 2007548601 A JP2007548601 A JP 2007548601A JP 2008525500 A5 JP2008525500 A5 JP 2008525500A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- alkoxy
- pyrimidin
- amino
- 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 148
- 125000003545 alkoxy group Chemical group 0.000 claims 114
- -1 cyano, hydroxyl Chemical group 0.000 claims 100
- 125000003282 alkyl amino group Chemical group 0.000 claims 63
- 125000001475 halogen functional group Chemical group 0.000 claims 59
- 125000001424 substituent group Chemical group 0.000 claims 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 50
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 46
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 30
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 28
- 125000003118 aryl group Chemical group 0.000 claims 27
- 150000005829 chemical entities Chemical class 0.000 claims 27
- 125000000623 heterocyclic group Chemical group 0.000 claims 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 23
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 23
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 23
- 125000004043 oxo group Chemical group O=* 0.000 claims 21
- 239000000126 substance Substances 0.000 claims 19
- 239000008194 pharmaceutical composition Substances 0.000 claims 18
- 125000004076 pyridyl group Chemical group 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 15
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims 10
- 239000004202 carbamide Substances 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000002541 furyl group Chemical group 0.000 claims 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 10
- 125000000335 thiazolyl group Chemical group 0.000 claims 10
- 125000001425 triazolyl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 9
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 9
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims 8
- 208000010877 cognitive disease Diseases 0.000 claims 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 7
- 208000028698 Cognitive impairment Diseases 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 6
- 206010027175 memory impairment Diseases 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 5
- 125000004423 acyloxy group Chemical group 0.000 claims 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 5
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 5
- 150000001350 alkyl halides Chemical class 0.000 claims 5
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 5
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 5
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims 4
- 150000003857 carboxamides Chemical class 0.000 claims 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 102000004190 Enzymes Human genes 0.000 claims 3
- 108090000790 Enzymes Proteins 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- HFFFLSISAQUYCX-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-[3-(3-nitrophenoxy)propoxy]thieno[2,3-d]pyrimidine Chemical compound [O-][N+](=O)C1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 HFFFLSISAQUYCX-UHFFFAOYSA-N 0.000 claims 2
- MUQAAKGTOJWWPL-UHFFFAOYSA-N 5-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 MUQAAKGTOJWWPL-UHFFFAOYSA-N 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- XDPJVACQLSQIPI-UHFFFAOYSA-N n-[3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 XDPJVACQLSQIPI-UHFFFAOYSA-N 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- JXCZNCZXBUPYKF-UHFFFAOYSA-N 1-[3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]phenyl]-3-hydroxyurea Chemical compound ONC(=O)NC1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 JXCZNCZXBUPYKF-UHFFFAOYSA-N 0.000 claims 1
- MELRXBKNVPEXRS-UHFFFAOYSA-N 1-[3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]phenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 MELRXBKNVPEXRS-UHFFFAOYSA-N 0.000 claims 1
- BWOQFALLHSXGCX-UHFFFAOYSA-N 1-[4-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1OCCCOC1=NC=NC2=C1C(C=1C=CC(F)=CC=1)=CS2 BWOQFALLHSXGCX-UHFFFAOYSA-N 0.000 claims 1
- RIMMTXOYGBAVGQ-UHFFFAOYSA-N 1-amino-3-[3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]phenyl]urea Chemical compound NNC(=O)NC1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 RIMMTXOYGBAVGQ-UHFFFAOYSA-N 0.000 claims 1
- VWKXLLWUKHPSEF-UHFFFAOYSA-N 1-amino-3-[4-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]phenyl]urea Chemical compound C1=CC(NC(=O)NN)=CC=C1OCCCOC1=NC=NC2=C1C(C=1C=CC(F)=CC=1)=CS2 VWKXLLWUKHPSEF-UHFFFAOYSA-N 0.000 claims 1
- YAIKPAGNERAPOQ-UHFFFAOYSA-N 1-ethyl-3-[4-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1OCCCOC1=NC=NC2=C1C(C=1C=CC(F)=CC=1)=CS2 YAIKPAGNERAPOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JYSDTQNYAABJEX-UHFFFAOYSA-N 3-[2-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxyethoxy]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(OCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 JYSDTQNYAABJEX-UHFFFAOYSA-N 0.000 claims 1
- ZKDHQCWALNJRAV-UHFFFAOYSA-N 3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 ZKDHQCWALNJRAV-UHFFFAOYSA-N 0.000 claims 1
- ZXZCMQKCBYXJFM-UHFFFAOYSA-N 3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 ZXZCMQKCBYXJFM-UHFFFAOYSA-N 0.000 claims 1
- VRCJHDOBEHWIQN-UHFFFAOYSA-N 3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 VRCJHDOBEHWIQN-UHFFFAOYSA-N 0.000 claims 1
- UKQOFEREGIIHCF-UHFFFAOYSA-N 3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]aniline Chemical compound NC1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 UKQOFEREGIIHCF-UHFFFAOYSA-N 0.000 claims 1
- KMPCEWAWKJUGGR-UHFFFAOYSA-N 3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]benzohydrazide Chemical compound NNC(=O)C1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 KMPCEWAWKJUGGR-UHFFFAOYSA-N 0.000 claims 1
- NYDGMGDUUUCXPO-UHFFFAOYSA-N 3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 NYDGMGDUUUCXPO-UHFFFAOYSA-N 0.000 claims 1
- HDILMKJHAHEKRB-UHFFFAOYSA-N 3-[[2-[(5-phenylthieno[2,3-d]pyrimidin-4-yl)amino]ethylamino]methyl]benzonitrile Chemical compound N#CC1=CC=CC(CNCCNC=2C=3C(C=4C=CC=CC=4)=CSC=3N=CN=2)=C1 HDILMKJHAHEKRB-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- IIONUEOGNZKNAS-UHFFFAOYSA-N 4-[3-(1,2-benzothiazol-3-yloxy)propoxy]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=CSC2=NC=NC(OCCCOC=3C4=CC=CC=C4SN=3)=C12 IIONUEOGNZKNAS-UHFFFAOYSA-N 0.000 claims 1
- POAZBDQRENJPTB-UHFFFAOYSA-N 4-[3-(3,4-dimethoxyphenoxy)propoxy]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine Chemical compound C1=C(OC)C(OC)=CC=C1OCCCOC1=NC=NC2=C1C(C=1C=CC(F)=CC=1)=CS2 POAZBDQRENJPTB-UHFFFAOYSA-N 0.000 claims 1
- KRHWFIKMFNNPLI-UHFFFAOYSA-N 4-[3-(3,5-difluorophenoxy)propoxy]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=CSC2=NC=NC(OCCCOC=3C=C(F)C=C(F)C=3)=C12 KRHWFIKMFNNPLI-UHFFFAOYSA-N 0.000 claims 1
- NAMZLNCGEWXEAY-UHFFFAOYSA-N 4-[3-(3-ethylphenoxy)propoxy]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine Chemical compound CCC1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 NAMZLNCGEWXEAY-UHFFFAOYSA-N 0.000 claims 1
- CIUBDWZQZZSFQF-UHFFFAOYSA-N 4-[3-(4-chlorophenoxy)propoxy]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=CSC2=NC=NC(OCCCOC=3C=CC(Cl)=CC=3)=C12 CIUBDWZQZZSFQF-UHFFFAOYSA-N 0.000 claims 1
- AZHBPFURRAAKBS-UHFFFAOYSA-N 4-[3-(4-fluorophenoxy)propoxy]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1OCCCOC1=NC=NC2=C1C(C=1C=CC(F)=CC=1)=CS2 AZHBPFURRAAKBS-UHFFFAOYSA-N 0.000 claims 1
- SOQXMQDDGANUMN-UHFFFAOYSA-N 4-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OCCCOC1=NC=NC2=C1C(C=1C=CC(F)=CC=1)=CS2 SOQXMQDDGANUMN-UHFFFAOYSA-N 0.000 claims 1
- RCUDCNNBMDZSCL-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butan-1-ol Chemical compound C1=2C(CCCCO)=NC=NC=2SC=C1C1=CC=C(F)C=C1 RCUDCNNBMDZSCL-UHFFFAOYSA-N 0.000 claims 1
- DSQDKPIOTLAMLN-UHFFFAOYSA-N 4-but-3-enyl-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=CSC2=NC=NC(CCC=C)=C12 DSQDKPIOTLAMLN-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- ZRECHBAMRMTXJQ-UHFFFAOYSA-N 5-(2-chlorophenyl)-4-(4-phenylmethoxyphenoxy)thieno[2,3-d]pyrimidine Chemical compound ClC1=CC=CC=C1C1=CSC2=NC=NC(OC=3C=CC(OCC=4C=CC=CC=4)=CC=3)=C12 ZRECHBAMRMTXJQ-UHFFFAOYSA-N 0.000 claims 1
- SXGFENWNHKBEKR-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-(3-phenoxypropoxy)thieno[2,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=CSC2=NC=NC(OCCCOC=3C=CC=CC=3)=C12 SXGFENWNHKBEKR-UHFFFAOYSA-N 0.000 claims 1
- SFJYZAMUKNWMQY-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-[3-(3-methoxyphenoxy)propoxy]thieno[2,3-d]pyrimidine Chemical compound COC1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 SFJYZAMUKNWMQY-UHFFFAOYSA-N 0.000 claims 1
- NIQYCFLTUPCEDK-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-[3-(3-methylphenoxy)propoxy]thieno[2,3-d]pyrimidine Chemical compound CC1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 NIQYCFLTUPCEDK-UHFFFAOYSA-N 0.000 claims 1
- ODSKNVMHALFYOO-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-[3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxypropoxy]thieno[2,3-d]pyrimidine Chemical compound C1=C(C(F)(F)F)N(C)N=C1OCCCOC1=NC=NC2=C1C(C=1C=CC(F)=CC=1)=CS2 ODSKNVMHALFYOO-UHFFFAOYSA-N 0.000 claims 1
- UWJDOKWVDBWQGP-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-[3-[3-(trifluoromethoxy)phenoxy]propoxy]thieno[2,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=CSC2=NC=NC(OCCCOC=3C=C(OC(F)(F)F)C=CC=3)=C12 UWJDOKWVDBWQGP-UHFFFAOYSA-N 0.000 claims 1
- ARJVFLRSXQYBEZ-UHFFFAOYSA-N 5-[3-[(5-pyrazin-2-ylthieno[2,3-d]pyrimidin-4-yl)amino]propoxy]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1OCCCNC1=NC=NC2=C1C(C=1N=CC=NC=1)=CS2 ARJVFLRSXQYBEZ-UHFFFAOYSA-N 0.000 claims 1
- RRUPRJBZJFIANC-UHFFFAOYSA-N 5-[3-[(5-pyridin-3-ylthieno[2,3-d]pyrimidin-4-yl)amino]propoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1OCCCNC1=NC=NC2=C1C(C=1C=NC=CC=1)=CS2 RRUPRJBZJFIANC-UHFFFAOYSA-N 0.000 claims 1
- OGHISBMNUQOXQX-UHFFFAOYSA-N 5-[3-[(5-pyrimidin-2-ylthieno[2,3-d]pyrimidin-4-yl)amino]propoxy]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1OCCCNC1=NC=NC2=C1C(C=1N=CC=CN=1)=CS2 OGHISBMNUQOXQX-UHFFFAOYSA-N 0.000 claims 1
- MOYXPKREYCNMCC-UHFFFAOYSA-N 5-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]-1,3-dihydroindol-2-one Chemical compound C1=CC(F)=CC=C1C1=CSC2=NC=NC(OCCCOC=3C=C4CC(=O)NC4=CC=3)=C12 MOYXPKREYCNMCC-UHFFFAOYSA-N 0.000 claims 1
- VCYBETMPTXCXHV-UHFFFAOYSA-N 5-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1OCCCOC1=NC=NC2=C1C(C=1C=CC(F)=CC=1)=CS2 VCYBETMPTXCXHV-UHFFFAOYSA-N 0.000 claims 1
- QBUYYJUVNBLYDW-UHFFFAOYSA-N 5-[3-[[5-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidin-4-yl]amino]propoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1OCCCNC1=NC=NC2=C1C(C=1SC=CN=1)=CS2 QBUYYJUVNBLYDW-UHFFFAOYSA-N 0.000 claims 1
- LPVSLMINVHGKHN-UHFFFAOYSA-N 5-[3-[[5-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidin-4-yl]amino]propoxy]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1OCCCNC1=NC=NC2=C1C(C=1SC=CN=1)=CS2 LPVSLMINVHGKHN-UHFFFAOYSA-N 0.000 claims 1
- QLNOTABKUOEGRC-UHFFFAOYSA-N 5-[3-[[5-(5-chlorofuran-2-yl)thieno[2,3-d]pyrimidin-4-yl]amino]propoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1OCCCNC1=NC=NC2=C1C(C=1OC(Cl)=CC=1)=CS2 QLNOTABKUOEGRC-UHFFFAOYSA-N 0.000 claims 1
- ZKALPSBKAGJIAF-UHFFFAOYSA-N 5-[4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy]-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CN=CC(OCCCCC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 ZKALPSBKAGJIAF-UHFFFAOYSA-N 0.000 claims 1
- VURCGILSFDTCRK-UHFFFAOYSA-N 5-[4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy]pyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC(OCCCCC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 VURCGILSFDTCRK-UHFFFAOYSA-N 0.000 claims 1
- LVVYRCRSMLLRCI-UHFFFAOYSA-N 5-[4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(OCCCCC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 LVVYRCRSMLLRCI-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
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| CA2827724A1 (en) | 2011-02-18 | 2012-08-23 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinolinol derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| AR090037A1 (es) | 2011-11-15 | 2014-10-15 | Xention Ltd | Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio |
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| CA2910751C (en) | 2013-05-09 | 2021-02-23 | Mitrassist Medical Ltd. | Heart valve assistive prosthesis |
| US10039764B2 (en) | 2013-07-12 | 2018-08-07 | University Of South Alabama | Treatment and diagnosis of cancer and precancerous conditions using PDE10A inhibitors and methods to measure PDE10A expression |
| US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
| FR3015483B1 (fr) * | 2013-12-23 | 2016-01-01 | Servier Lab | Nouveaux derives de thienopyrimidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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| JP4505228B2 (ja) | 2002-01-10 | 2010-07-21 | バイエル・シェーリング・ファルマ・アクチェンゲゼルシャフト | Ｒｈｏ−キナーゼ阻害剤 |
| US6945478B2 (en) * | 2002-03-15 | 2005-09-20 | Siemens Vdo Automotive Corporation | Fuel injector having an orifice plate with offset coining angled orifices |
| US20040138238A1 (en) | 2002-08-08 | 2004-07-15 | Dhanoa Dale S. | Substituted aminopyrimidine compounds as neurokinin antagonists |
| US20050222175A1 (en) * | 2004-03-31 | 2005-10-06 | Dhanoa Dale S | New piperidinylamino-thieno[2,3-D] pyrimidine compounds |
| US7612078B2 (en) * | 2003-03-31 | 2009-11-03 | Epix Delaware, Inc. | Piperidinylamino-thieno[2,3-D] pyrimidine compounds |
| WO2004092123A2 (en) | 2003-04-10 | 2004-10-28 | Microbia, Inc. | Inhibitors of fungal invasion |
| GB0315950D0 (en) * | 2003-06-11 | 2003-08-13 | Xention Discovery Ltd | Compounds |
| ES2324536T7 (es) | 2003-06-11 | 2012-03-16 | Xention Limited | Derivados de tenopirimidina como inhibidores de los canales de potasio. |
| WO2006093518A2 (en) * | 2004-06-25 | 2006-09-08 | Apath, Llc | Thienyl compounds for treating virus-related conditions |
-
2005
- 2005-12-22 US US11/317,907 patent/US7576080B2/en not_active Expired - Fee Related
- 2005-12-27 EP EP05855928A patent/EP1831229A1/en not_active Withdrawn
- 2005-12-27 AU AU2005321903A patent/AU2005321903A1/en not_active Abandoned
- 2005-12-27 MX MX2007007387A patent/MX2007007387A/es not_active Application Discontinuation
- 2005-12-27 CA CA002594676A patent/CA2594676A1/en not_active Abandoned
- 2005-12-27 JP JP2007548601A patent/JP2008525500A/ja active Pending
- 2005-12-27 WO PCT/US2005/047439 patent/WO2006071988A1/en not_active Ceased
-
2009
- 2009-06-29 US US12/494,057 patent/US20100010017A1/en not_active Abandoned
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