ZA200600225B - Thienopyrimidine derivatives as potassium channel inhibitors - Google Patents

Info

Publication number

ZA200600225B

ZA200600225B ZA200600225A ZA200600225A ZA200600225B ZA 200600225 B ZA200600225 B ZA 200600225B ZA 200600225 A ZA200600225 A ZA 200600225A ZA 200600225 A ZA200600225 A ZA 200600225A ZA 200600225 B ZA200600225 B ZA 200600225B

Authority

ZA

South Africa

Prior art keywords

pyrimidin

thieno

phenyl

ylmethyl

pyridin

Prior art date

2003-06-11

Links

• Espacenet
• Global Dossier
• Discuss

• 102000004257 Potassium Channel Human genes 0.000 title claims description 21
• 108020001213 potassium channel Proteins 0.000 title claims description 21
• 239000003112 inhibitor Substances 0.000 title abstract description 8
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 179
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
• 206010003119 arrhythmia Diseases 0.000 claims abstract description 14
• 230000006793 arrhythmia Effects 0.000 claims abstract description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 149
• 125000000217 alkyl group Chemical group 0.000 claims description 87
• 239000002904 solvent Substances 0.000 claims description 63
• -1 NR9R10 Chemical group 0.000 claims description 61
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 49
• 125000003118 aryl group Chemical group 0.000 claims description 48
• 239000000203 mixture Substances 0.000 claims description 48
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 45
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• 125000005843 halogen group Chemical group 0.000 claims description 27
• 229920006395 saturated elastomer Polymers 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 238000000034 method Methods 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 150000002825 nitriles Chemical class 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 239000012038 nucleophile Substances 0.000 claims description 9
• 230000005764 inhibitory process Effects 0.000 claims description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• DYTQGJLVGDSCLF-UHFFFAOYSA-N thieno[2,3-d]pyrimidin-4-amine Chemical compound NC1=NC=NC2=C1C=CS2 DYTQGJLVGDSCLF-UHFFFAOYSA-N 0.000 claims description 6
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• WMDRWYGURIUQLW-UHFFFAOYSA-N 2-methyl-5-phenyl-n-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C=3C=CC=CC=3)=CSC2=NC(C)=NC=1NCC1=CC=CC=N1 WMDRWYGURIUQLW-UHFFFAOYSA-N 0.000 claims description 4
• 239000000969 carrier Substances 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• BXCISUYDQYKNDD-UHFFFAOYSA-N n-(furan-2-ylmethyl)-5-phenylthieno[2,3-d]pyrimidin-4-amine Chemical compound C=1C=COC=1CNC(C1=2)=NC=NC=2SC=C1C1=CC=CC=C1 BXCISUYDQYKNDD-UHFFFAOYSA-N 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• AUUVHAGXRMINSY-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(furan-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1C1=CSC2=NC=NC(NCC=3OC=CC=3)=C12 AUUVHAGXRMINSY-UHFFFAOYSA-N 0.000 claims description 3
• JZBUVSQMZBERPX-UHFFFAOYSA-N 5-(4-methylphenyl)-n-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CSC2=NC=NC(NCC=3N=CC=CC=3)=C12 JZBUVSQMZBERPX-UHFFFAOYSA-N 0.000 claims description 3
• 201000010099 disease Diseases 0.000 claims description 3
• 238000006073 displacement reaction Methods 0.000 claims description 3
• SVJQOANWTBBFRN-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-5-phenylthieno[2,3-d]pyrimidin-4-amine Chemical compound C1=CN=CN1CCCNC(C1=2)=NC=NC=2SC=C1C1=CC=CC=C1 SVJQOANWTBBFRN-UHFFFAOYSA-N 0.000 claims description 3
• PDFZABVJVSYZBB-UHFFFAOYSA-N n-methyl-2-[5-phenyl-4-(pyridin-2-ylmethylamino)thieno[2,3-d]pyrimidin-2-yl]acetamide Chemical compound C=12C(C=3C=CC=CC=3)=CSC2=NC(CC(=O)NC)=NC=1NCC1=CC=CC=N1 PDFZABVJVSYZBB-UHFFFAOYSA-N 0.000 claims description 3
• 230000000269 nucleophilic effect Effects 0.000 claims description 3
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
• PVHNQHVWWHWGCV-UHFFFAOYSA-N 2-(2-methoxyethoxy)-5-phenyl-n-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C=3C=CC=CC=3)=CSC2=NC(OCCOC)=NC=1NCC1=CC=CC=N1 PVHNQHVWWHWGCV-UHFFFAOYSA-N 0.000 claims description 2
• SJEIRQJDDUIYHD-UHFFFAOYSA-N 2-[5-phenyl-4-(pyridin-2-ylmethylamino)thieno[2,3-d]pyrimidin-2-yl]propane-1,3-diol Chemical compound C=12C(C=3C=CC=CC=3)=CSC2=NC(C(CO)CO)=NC=1NCC1=CC=CC=N1 SJEIRQJDDUIYHD-UHFFFAOYSA-N 0.000 claims description 2
• ONHCMJRVDBBBLF-UHFFFAOYSA-N 2-[[5-phenyl-4-(pyridin-2-ylmethylamino)thieno[2,3-d]pyrimidin-2-yl]amino]ethanol Chemical compound C=12C(C=3C=CC=CC=3)=CSC2=NC(NCCO)=NC=1NCC1=CC=CC=N1 ONHCMJRVDBBBLF-UHFFFAOYSA-N 0.000 claims description 2
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• BODCPCLWQFAAFK-UHFFFAOYSA-N 2-methoxy-5-phenyl-n-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C=3C=CC=CC=3)=CSC2=NC(OC)=NC=1NCC1=CC=CC=N1 BODCPCLWQFAAFK-UHFFFAOYSA-N 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• PYEJUVCDHKWJIC-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-n-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2SC=C(C=3C=C4OCOC4=CC=3)C=2C=1NCC1=CC=CC=N1 PYEJUVCDHKWJIC-UHFFFAOYSA-N 0.000 claims description 2
• RZRDIQDWBUHDGK-UHFFFAOYSA-N 5-(4-bromophenyl)-n-(pyridin-3-ylmethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(Br)=CC=C1C1=CSC2=NC=NC(NCC=3C=NC=CC=3)=C12 RZRDIQDWBUHDGK-UHFFFAOYSA-N 0.000 claims description 2
• DCTBGQVNCFASQK-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[2-(cyclohexen-1-yl)ethyl]thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1C1=CSC2=NC=NC(NCCC=3CCCCC=3)=C12 DCTBGQVNCFASQK-UHFFFAOYSA-N 0.000 claims description 2
• ZUFHIKDAKAEAGI-UHFFFAOYSA-N 6-methyl-n-[(6-methylpyridin-2-yl)methyl]-5-phenylthieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C=3C=CC=CC=3)=C(C)SC2=NC=NC=1NCC1=CC=CC(C)=N1 ZUFHIKDAKAEAGI-UHFFFAOYSA-N 0.000 claims description 2
• 239000004146 Propane-1,2-diol Substances 0.000 claims description 2
• 239000003054 catalyst Substances 0.000 claims description 2
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 2
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• LGPOTAKTUOUAGL-UHFFFAOYSA-N n-(furan-2-ylmethyl)-5-(4-methylphenyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CSC2=NC=NC(NCC=3OC=CC=3)=C12 LGPOTAKTUOUAGL-UHFFFAOYSA-N 0.000 claims description 2
• IOXJOMMRNNLOKQ-UHFFFAOYSA-N n-butyl-5-phenylthieno[2,3-d]pyrimidin-4-amine Chemical compound C1=2C(NCCCC)=NC=NC=2SC=C1C1=CC=CC=C1 IOXJOMMRNNLOKQ-UHFFFAOYSA-N 0.000 claims description 2
• 229910052763 palladium Inorganic materials 0.000 claims description 2
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• 239000000126 substance Substances 0.000 claims 9
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• CLRCOKAAZFPYMZ-UHFFFAOYSA-N 2-[[5-phenyl-4-(pyridin-2-ylmethylamino)thieno[2,3-d]pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C=12C(C=3C=CC=CC=3)=CSC2=NC(NC(CO)CO)=NC=1NCC1=CC=CC=N1 CLRCOKAAZFPYMZ-UHFFFAOYSA-N 0.000 claims 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
• YPZLFVHHKLJPQY-UHFFFAOYSA-N 5-(1h-indol-6-yl)-n-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2SC=C(C=3C=C4NC=CC4=CC=3)C=2C=1NCC1=CC=CC=N1 YPZLFVHHKLJPQY-UHFFFAOYSA-N 0.000 claims 1
• ZOZYMGVYOPMWAF-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(pyridin-3-ylmethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(F)=CC=C1C1=CSC2=NC=NC(NCC=3C=NC=CC=3)=C12 ZOZYMGVYOPMWAF-UHFFFAOYSA-N 0.000 claims 1
• XQKAKLIVYKKYQL-UHFFFAOYSA-N 5-(4-methylphenyl)-n-(2-thiophen-2-ylethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CSC2=NC=NC(NCCC=3SC=CC=3)=C12 XQKAKLIVYKKYQL-UHFFFAOYSA-N 0.000 claims 1
• XDXNOOKTIMFRIX-UHFFFAOYSA-N 5-[4-(dimethylamino)phenyl]-n-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=CSC2=NC=NC(NCC=3N=CC=CC=3)=C12 XDXNOOKTIMFRIX-UHFFFAOYSA-N 0.000 claims 1
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• 238000002560 therapeutic procedure Methods 0.000 claims 1
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