AU2005321903A1 - Thienopyrimidine derivatives as phosphodiesterase 10 inhibitors - Google Patents

Info

Publication number

AU2005321903A1

AU2005321903A1 AU2005321903A AU2005321903A AU2005321903A1 AU 2005321903 A1 AU2005321903 A1 AU 2005321903A1 AU 2005321903 A AU2005321903 A AU 2005321903A AU 2005321903 A AU2005321903 A AU 2005321903A AU 2005321903 A1 AU2005321903 A1 AU 2005321903A1

Authority

AU

Australia

Prior art keywords

alkyl

chosen

substituted

alkoxy

phenyl

Prior art date

2004-12-23

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 239000003112 inhibitor Substances 0.000 title description 30
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title description 29
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title description 27
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 557
• 125000003545 alkoxy group Chemical group 0.000 claims description 396
• -1 cyano, hydroxyl Chemical group 0.000 claims description 388
• 125000003282 alkyl amino group Chemical group 0.000 claims description 239
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 199
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 185
• 125000001424 substituent group Chemical group 0.000 claims description 179
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 145
• 150000005829 chemical entities Chemical class 0.000 claims description 137
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 130
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 121
• 238000000034 method Methods 0.000 claims description 121
• 150000001875 compounds Chemical class 0.000 claims description 102
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 96
• 125000003118 aryl group Chemical group 0.000 claims description 95
• 125000000623 heterocyclic group Chemical group 0.000 claims description 89
• 239000000203 mixture Substances 0.000 claims description 84
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 81
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 77
• 125000001072 heteroaryl group Chemical group 0.000 claims description 72
• 125000004076 pyridyl group Chemical group 0.000 claims description 72
• 125000004043 oxo group Chemical group O=* 0.000 claims description 68
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 65
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 62
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 50
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 49
• 125000003342 alkenyl 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
• 125000001425 triazolyl group Chemical group 0.000 claims description 44
• 125000000335 thiazolyl group Chemical group 0.000 claims description 41
• 125000000304 alkynyl group Chemical group 0.000 claims description 40
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 36
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 32
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 31
• VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims description 30
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
• 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 24
• 201000010099 disease Diseases 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 24
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 20
• 102000004190 Enzymes Human genes 0.000 claims description 19
• 108090000790 Enzymes Proteins 0.000 claims description 19
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
• 201000000980 schizophrenia Diseases 0.000 claims description 19
• 239000004202 carbamide Substances 0.000 claims description 18
• 206010027175 memory impairment Diseases 0.000 claims description 18
• 125000004414 alkyl thio group Chemical group 0.000 claims description 17
• 208000010877 cognitive disease Diseases 0.000 claims description 17
• 230000015654 memory Effects 0.000 claims description 17
• 208000023105 Huntington disease Diseases 0.000 claims description 16
• 208000018737 Parkinson disease Diseases 0.000 claims description 16
• 125000004423 acyloxy group Chemical group 0.000 claims description 16
• 210000004227 basal ganglia Anatomy 0.000 claims description 16
• 208000028698 Cognitive impairment 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
• 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
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
• 230000005764 inhibitory process Effects 0.000 claims description 14
• 239000012453 solvate Substances 0.000 claims description 14
• 206010012289 Dementia Diseases 0.000 claims description 13
• 239000000651 prodrug Substances 0.000 claims description 13
• 229940002612 prodrug Drugs 0.000 claims description 13
• 208000028017 Psychotic disease Diseases 0.000 claims description 12
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 125000005518 carboxamido group Chemical group 0.000 claims description 12
• 208000035475 disorder Diseases 0.000 claims description 12
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 11
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 11
• DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 claims description 11
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 208000020925 Bipolar disease Diseases 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 201000006417 multiple sclerosis Diseases 0.000 claims description 10
• 125000003107 substituted aryl group Chemical group 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• 208000024827 Alzheimer disease Diseases 0.000 claims description 8
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
• 108010011222 cyclo(Arg-Pro) Proteins 0.000 claims description 8
• 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 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
• 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 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
• 230000006870 function Effects 0.000 claims description 7
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• IXWXTWGLCRWKKZ-UHFFFAOYSA-N 5-[3-(5-pyridin-3-ylthieno[2,3-d]pyrimidin-4-yl)oxypropoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1OCCCOC1=NC=NC2=C1C(C=1C=NC=CC=1)=CS2 IXWXTWGLCRWKKZ-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 206010015037 epilepsy Diseases 0.000 claims description 6
• 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 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 208000011580 syndromic disease Diseases 0.000 claims description 6
• 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
• 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 5
• 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 5
• 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 description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• XRAXXDWVUJXZFW-UHFFFAOYSA-N n-[3-[3-(5-phenylthieno[2,3-d]pyrimidin-4-yl)oxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(OCCCOC=2C=3C(C=4C=CC=CC=4)=CSC=3N=CN=2)=C1 XRAXXDWVUJXZFW-UHFFFAOYSA-N 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
• 230000000926 neurological effect Effects 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 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
• 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 4
• 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 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
• 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 description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• NLAOSJVZPMMESW-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]benzamide Chemical compound NC(=O)CNC(=O)C1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 NLAOSJVZPMMESW-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
• WHDNBSIDACHXCK-UHFFFAOYSA-N n-[3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]phenyl]cyclopropanecarboxamide Chemical compound C1=CC(F)=CC=C1C1=CSC2=NC=NC(OCCCOC=3C=C(NC(=O)C4CC4)C=CC=3)=C12 WHDNBSIDACHXCK-UHFFFAOYSA-N 0.000 claims description 4
• XLQQLGJETPKPAO-UHFFFAOYSA-N n-[3-[3-[[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]amino]propoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(OCCCNC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 XLQQLGJETPKPAO-UHFFFAOYSA-N 0.000 claims description 4
• MNIIDDOWIUUAJI-UHFFFAOYSA-N n-methyl-5-[3-(5-pyridin-4-ylthieno[2,3-d]pyrimidin-4-yl)oxypropoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1OCCCOC1=NC=NC2=C1C(C=1C=CN=CC=1)=CS2 MNIIDDOWIUUAJI-UHFFFAOYSA-N 0.000 claims description 4
• BPVMRJCSUDXZED-UHFFFAOYSA-N n-methyl-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)NC)=CC=C1OCCCNC1=NC=NC2=C1C(C=1SC=CN=1)=CS2 BPVMRJCSUDXZED-UHFFFAOYSA-N 0.000 claims description 4
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 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
• 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
• TWJGYGYNKFOOCV-UHFFFAOYSA-N 2-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]benzamide Chemical compound NC(=O)C1=CC=CC=C1OCCCOC1=NC=NC2=C1C(C=1C=CC(F)=CC=1)=CS2 TWJGYGYNKFOOCV-UHFFFAOYSA-N 0.000 claims description 3
• PTKJPWHXLWIUJV-UHFFFAOYSA-N 3-[2-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxyethoxy]benzamide Chemical compound NC(=O)C1=CC=CC(OCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 PTKJPWHXLWIUJV-UHFFFAOYSA-N 0.000 claims description 3
• LVZKDUQAELSLAX-UHFFFAOYSA-N 3-[3-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxypropoxy]benzamide Chemical compound NC(=O)C1=CC=CC(OCCCOC=2C=3C(C=4C=CC(F)=CC=4)=CSC=3N=CN=2)=C1 LVZKDUQAELSLAX-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
• 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
• 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
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
• 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
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