JP2008525500A - ホスホジエステラーゼ１０阻害剤としてのチエノピリミジン誘導体 - Google Patents
ホスホジエステラーゼ１０阻害剤としてのチエノピリミジン誘導体 Download PDFInfo
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- JP2008525500A JP2008525500A JP2007548601A JP2007548601A JP2008525500A JP 2008525500 A JP2008525500 A JP 2008525500A JP 2007548601 A JP2007548601 A JP 2007548601A JP 2007548601 A JP2007548601 A JP 2007548601A JP 2008525500 A JP2008525500 A JP 2008525500A
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- Prior art keywords
- alkyl
- substituted
- phenyl
- alkoxy
- pyrimidin
- Prior art date
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- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000003112 inhibitor Substances 0.000 title description 28
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title description 13
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
- 201000010099 disease Diseases 0.000 claims abstract description 29
- 102000004190 Enzymes Human genes 0.000 claims abstract description 20
- 108090000790 Enzymes Proteins 0.000 claims abstract description 20
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 18
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 13
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 12
- 230000005764 inhibitory process Effects 0.000 claims abstract description 12
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 7
- 230000000926 neurological effect Effects 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 519
- -1 cyano, hydroxyl Chemical group 0.000 claims description 448
- 125000003545 alkoxy group Chemical group 0.000 claims description 413
- 125000003282 alkyl amino group Chemical group 0.000 claims description 242
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 199
- 125000001424 substituent group Chemical group 0.000 claims description 196
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 161
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 160
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 143
- 238000000034 method Methods 0.000 claims description 133
- 150000001875 compounds Chemical class 0.000 claims description 103
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 102
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 98
- 125000003118 aryl group Chemical group 0.000 claims description 91
- 239000000126 substance Substances 0.000 claims description 91
- 125000000623 heterocyclic group Chemical group 0.000 claims description 88
- 239000000203 mixture Substances 0.000 claims description 82
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 81
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 81
- 125000004043 oxo group Chemical group O=* 0.000 claims description 80
- 125000004076 pyridyl group Chemical group 0.000 claims description 74
- 125000001072 heteroaryl group Chemical group 0.000 claims description 72
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 60
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 53
- 150000005829 chemical entities Chemical class 0.000 claims description 51
- 125000003342 alkenyl group Chemical group 0.000 claims description 46
- 125000000304 alkynyl group Chemical group 0.000 claims description 46
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 45
- 125000002541 furyl group Chemical group 0.000 claims description 44
- 125000000335 thiazolyl group Chemical group 0.000 claims description 43
- 125000001425 triazolyl group Chemical group 0.000 claims description 41
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 39
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 36
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 35
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims description 31
- 239000004202 carbamide Substances 0.000 claims description 31
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 29
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 29
- 206010012289 Dementia Diseases 0.000 claims description 27
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 208000010877 cognitive disease Diseases 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 206010027175 memory impairment Diseases 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 19
- 201000000980 schizophrenia Diseases 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 17
- 208000028698 Cognitive impairment Diseases 0.000 claims description 17
- 150000001350 alkyl halides Chemical class 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 17
- 125000004423 acyloxy group Chemical group 0.000 claims description 16
- 210000004227 basal ganglia Anatomy 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 208000023105 Huntington disease Diseases 0.000 claims description 15
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 15
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 15
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 15
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 15
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 15
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
- 239000000651 prodrug Substances 0.000 claims description 13
- 229940002612 prodrug Drugs 0.000 claims description 13
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 13
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 12
- 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 description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 12
- 150000003857 carboxamides Chemical class 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 208000020925 Bipolar disease Diseases 0.000 claims description 11
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 10
- 201000006417 multiple sclerosis Diseases 0.000 claims description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 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 description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 230000006870 function Effects 0.000 claims description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 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 description 5
- 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 description 5
- 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 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- FHFJIUXXXLIHCD-UHFFFAOYSA-N n-[4-[3-[[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]amino]propyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CCCNC1=NC=NC2=C1C(C=1C=CC(F)=CC=1)=CS2 FHFJIUXXXLIHCD-UHFFFAOYSA-N 0.000 claims description 5
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 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 description 4
- 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 description 4
- 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 description 4
- 230000006999 cognitive decline Effects 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- REMQACVQKFUNKD-UHFFFAOYSA-N methyl 5-[4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy]pyridine-3-carboxylate Chemical compound COC(=O)C1=CN=CC(OCCCCC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 REMQACVQKFUNKD-UHFFFAOYSA-N 0.000 claims description 4
- LCIUBJUOVIIFTR-UHFFFAOYSA-N n-[(3-nitrophenyl)methyl]-n'-(5-phenylthieno[2,3-d]pyrimidin-4-yl)ethane-1,2-diamine Chemical compound [O-][N+](=O)C1=CC=CC(CNCCNC=2C=3C(C=4C=CC=CC=4)=CSC=3N=CN=2)=C1 LCIUBJUOVIIFTR-UHFFFAOYSA-N 0.000 claims description 4
- LVHUHEUOMRAXBI-UHFFFAOYSA-N n-[3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxyphenoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(OC=2C=C(OC=3C=4C(C=5C=CC(F)=CC=5)=CSC=4N=CN=3)C=CC=2)=C1 LVHUHEUOMRAXBI-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- JAPSOFJPZTZOKU-UHFFFAOYSA-N 2-methoxy-4-[2-[(5-phenylthieno[2,3-d]pyrimidin-4-yl)amino]ethyliminomethyl]phenol Chemical compound C1=C(O)C(OC)=CC(C=NCCNC=2C=3C(C=4C=CC=CC=4)=CSC=3N=CN=2)=C1 JAPSOFJPZTZOKU-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
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Classifications
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63817904P | 2004-12-23 | 2004-12-23 | |
| PCT/US2005/047439 WO2006071988A1 (en) | 2004-12-23 | 2005-12-27 | Thienopyrimidine derivatives as phosphodiesterase 10 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008525500A true JP2008525500A (ja) | 2008-07-17 |
| JP2008525500A5 JP2008525500A5 (enExample) | 2009-03-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2007548601A Pending JP2008525500A (ja) | 2004-12-23 | 2005-12-27 | ホスホジエステラーゼ１０阻害剤としてのチエノピリミジン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7576080B2 (enExample) |
| EP (1) | EP1831229A1 (enExample) |
| JP (1) | JP2008525500A (enExample) |
| AU (1) | AU2005321903A1 (enExample) |
| CA (1) | CA2594676A1 (enExample) |
| MX (1) | MX2007007387A (enExample) |
| WO (1) | WO2006071988A1 (enExample) |
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| CA2754890C (en) | 2009-03-13 | 2018-01-16 | Piet Herdewijn | Bicyclic heterocycles |
| BR112012005616A2 (pt) * | 2009-09-21 | 2016-06-21 | Hoffmann La Roche | compostos antivirais heterocíclicos |
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- 2005-12-27 JP JP2007548601A patent/JP2008525500A/ja active Pending
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