JP2011525898A5 - - Google Patents
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- Publication number
- JP2011525898A5 JP2011525898A5 JP2011515594A JP2011515594A JP2011525898A5 JP 2011525898 A5 JP2011525898 A5 JP 2011525898A5 JP 2011515594 A JP2011515594 A JP 2011515594A JP 2011515594 A JP2011515594 A JP 2011515594A JP 2011525898 A5 JP2011525898 A5 JP 2011525898A5
- Authority
- JP
- Japan
- Prior art keywords
- ylmethyl
- triazolo
- amine
- pyrid
- pyrimidine
- 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.)
- Granted
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- -1 5-methyl-furan-2-yl Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 13
- 208000016285 Movement disease Diseases 0.000 claims description 12
- 208000018737 Parkinson disease Diseases 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 206010034010 Parkinsonism Diseases 0.000 claims description 9
- 102000005962 receptors Human genes 0.000 claims description 9
- 108020003175 receptors Proteins 0.000 claims description 9
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 8
- 229960005305 adenosine Drugs 0.000 claims description 8
- 208000026139 Memory disease Diseases 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- 208000027089 Parkinsonian disease Diseases 0.000 claims description 6
- 102000000033 Purinergic Receptors Human genes 0.000 claims description 6
- 108010080192 Purinergic Receptors Proteins 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010003694 Atrophy Diseases 0.000 claims description 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 102000012437 Copper-Transporting ATPases Human genes 0.000 claims description 3
- 206010012335 Dependence Diseases 0.000 claims description 3
- 208000002603 Dopa-responsive dystonia Diseases 0.000 claims description 3
- 208000002972 Hepatolenticular Degeneration Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical group OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 3
- 208000001089 Multiple system atrophy Diseases 0.000 claims description 3
- 208000008238 Muscle Spasticity Diseases 0.000 claims description 3
- 208000002033 Myoclonus Diseases 0.000 claims description 3
- 208000036757 Postencephalitic parkinsonism Diseases 0.000 claims description 3
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 3
- 208000018839 Wilson disease Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000037444 atrophy Effects 0.000 claims description 3
- 210000004227 basal ganglia Anatomy 0.000 claims description 3
- 230000000903 blocking effect Effects 0.000 claims description 3
- 210000000133 brain stem Anatomy 0.000 claims description 3
- 230000007850 degeneration Effects 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 3
- 210000000609 ganglia Anatomy 0.000 claims description 3
- 201000003631 narcolepsy Diseases 0.000 claims description 3
- 230000001898 pallidal effect Effects 0.000 claims description 3
- 208000023515 periodic limb movement disease Diseases 0.000 claims description 3
- 208000000170 postencephalitic Parkinson disease Diseases 0.000 claims description 3
- 230000000750 progressive effect Effects 0.000 claims description 3
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 208000018198 spasticity Diseases 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- SRRFCARXXFSCSB-UHFFFAOYSA-N 1-[6-[(5-amino-7-phenyltriazolo[4,5-d]pyrimidin-3-yl)methyl]pyridin-2-yl]cyclobutan-1-ol Chemical compound C=12N=NN(CC=3N=C(C=CC=3)C3(O)CCC3)C2=NC(N)=NC=1C1=CC=CC=C1 SRRFCARXXFSCSB-UHFFFAOYSA-N 0.000 claims description 2
- XNXGMIGCARIDKO-UHFFFAOYSA-N 1-[6-[(5-amino-7-phenyltriazolo[4,5-d]pyrimidin-3-yl)methyl]pyridin-2-yl]cyclopentan-1-ol Chemical compound C=12N=NN(CC=3N=C(C=CC=3)C3(O)CCCC3)C2=NC(N)=NC=1C1=CC=CC=C1 XNXGMIGCARIDKO-UHFFFAOYSA-N 0.000 claims description 2
- ZCIMLPGZYISKTM-UHFFFAOYSA-N 1-[6-[[5-amino-7-(3-methoxyphenyl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]cyclobutan-1-ol Chemical compound COC1=CC=CC(C=2C=3N=NN(CC=4N=C(C=CC=4)C4(O)CCC4)C=3N=C(N)N=2)=C1 ZCIMLPGZYISKTM-UHFFFAOYSA-N 0.000 claims description 2
- NCBRBZZVSUEOFQ-UHFFFAOYSA-N 1-[6-[[5-amino-7-(4-methyl-1,3-thiazol-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]cyclopentan-1-ol Chemical compound CC1=CSC(C=2C=3N=NN(CC=4N=C(C=CC=4)C4(O)CCCC4)C=3N=C(N)N=2)=N1 NCBRBZZVSUEOFQ-UHFFFAOYSA-N 0.000 claims description 2
- PGCTZXXIHHZPHM-UHFFFAOYSA-N 1-[6-[[5-amino-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]cyclobutan-1-ol Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(C2(O)CCC2)=N1 PGCTZXXIHHZPHM-UHFFFAOYSA-N 0.000 claims description 2
- MSIICSVPSIMRKM-UHFFFAOYSA-N 1-[6-[[5-amino-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]cyclohexan-1-ol Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(C2(O)CCCCC2)=N1 MSIICSVPSIMRKM-UHFFFAOYSA-N 0.000 claims description 2
- WRQYDKYVNGEQCW-UHFFFAOYSA-N 1-[6-[[5-amino-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]cyclopentan-1-ol Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(C2(O)CCCC2)=N1 WRQYDKYVNGEQCW-UHFFFAOYSA-N 0.000 claims description 2
- XXDKXHMRTBKSFA-UHFFFAOYSA-N 2-[6-[(5-amino-7-phenyltriazolo[4,5-d]pyrimidin-3-yl)methyl]pyridin-2-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2C=CC=CC=2)=N1 XXDKXHMRTBKSFA-UHFFFAOYSA-N 0.000 claims description 2
- WBQDITDDICQDQQ-UHFFFAOYSA-N 2-[6-[[5-amino-7-(3-methoxyphenyl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]propan-2-ol Chemical compound COC1=CC=CC(C=2C=3N=NN(CC=4N=C(C=CC=4)C(C)(C)O)C=3N=C(N)N=2)=C1 WBQDITDDICQDQQ-UHFFFAOYSA-N 0.000 claims description 2
- YQYKENUCSZTMJE-UHFFFAOYSA-N 2-[6-[[5-amino-7-(4-methyl-1,3-thiazol-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]propan-2-ol Chemical compound CC1=CSC(C=2C=3N=NN(CC=4N=C(C=CC=4)C(C)(C)O)C=3N=C(N)N=2)=N1 YQYKENUCSZTMJE-UHFFFAOYSA-N 0.000 claims description 2
- XPZYUVLLSFGKPS-UHFFFAOYSA-N 2-[6-[[5-amino-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]propan-2-ol Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(C(C)(C)O)=N1 XPZYUVLLSFGKPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- LLBYTELQINWZIJ-UHFFFAOYSA-N 3-[5-amino-3-[[6-(1-hydroxycyclobutyl)pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-7-yl]benzonitrile Chemical compound C=12N=NN(CC=3N=C(C=CC=3)C3(O)CCC3)C2=NC(N)=NC=1C1=CC=CC(C#N)=C1 LLBYTELQINWZIJ-UHFFFAOYSA-N 0.000 claims description 2
- ONCBSTLSMMBXHX-UHFFFAOYSA-N 3-[5-amino-3-[[6-(1-hydroxycyclopentyl)pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-7-yl]benzonitrile Chemical class C=12N=NN(CC=3N=C(C=CC=3)C3(O)CCCC3)C2=NC(N)=NC=1C1=CC=CC(C#N)=C1 ONCBSTLSMMBXHX-UHFFFAOYSA-N 0.000 claims description 2
- BCQRGFUTGJBNKT-UHFFFAOYSA-N 3-[5-amino-3-[[6-(2-hydroxypropan-2-yl)pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-7-yl]benzonitrile Chemical compound CC(C)(O)C1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2C=C(C=CC=2)C#N)=N1 BCQRGFUTGJBNKT-UHFFFAOYSA-N 0.000 claims description 2
- VAYVTDPINUWJKZ-UHFFFAOYSA-N 3-[5-amino-3-[[6-(4-hydroxyoxan-4-yl)pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-7-yl]benzonitrile Chemical compound C=12N=NN(CC=3N=C(C=CC=3)C3(O)CCOCC3)C2=NC(N)=NC=1C1=CC=CC(C#N)=C1 VAYVTDPINUWJKZ-UHFFFAOYSA-N 0.000 claims description 2
- IJPKWTVYFLHMFF-UHFFFAOYSA-N 3-[5-amino-3-[[6-(methoxymethyl)pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-7-yl]benzonitrile Chemical compound COCC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2C=C(C=CC=2)C#N)=N1 IJPKWTVYFLHMFF-UHFFFAOYSA-N 0.000 claims description 2
- ZOHVFUHFROEVQT-UHFFFAOYSA-N 3-[[6-(2-ethoxyethoxymethyl)pyridin-2-yl]methyl]-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound CCOCCOCC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC(C)=CC=2)=N1 ZOHVFUHFROEVQT-UHFFFAOYSA-N 0.000 claims description 2
- WYPAOIKIACVSIU-UHFFFAOYSA-N 3-[[6-(2-methoxypropan-2-yloxymethyl)pyridin-2-yl]methyl]-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound COC(C)(C)OCC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC(C)=CC=2)=N1 WYPAOIKIACVSIU-UHFFFAOYSA-N 0.000 claims description 2
- UXNXXNBJQBWBBC-UHFFFAOYSA-N 3-[[6-(difluoromethoxymethyl)pyridin-2-yl]methyl]-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(COC(F)F)=N1 UXNXXNBJQBWBBC-UHFFFAOYSA-N 0.000 claims description 2
- UESWRCOBJTWHIX-UHFFFAOYSA-N 3-[[6-(methoxymethyl)pyridin-2-yl]methyl]-7-(3-methoxyphenyl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound COCC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2C=C(OC)C=CC=2)=N1 UESWRCOBJTWHIX-UHFFFAOYSA-N 0.000 claims description 2
- LZJBVOMKJQWHML-UHFFFAOYSA-N 3-[[6-(methoxymethyl)pyridin-2-yl]methyl]-7-phenyltriazolo[4,5-d]pyrimidin-5-amine Chemical compound COCC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2C=CC=CC=2)=N1 LZJBVOMKJQWHML-UHFFFAOYSA-N 0.000 claims description 2
- YNRLREZIGIVCIG-UHFFFAOYSA-N 4-[6-[(5-amino-7-phenyltriazolo[4,5-d]pyrimidin-3-yl)methyl]pyridin-2-yl]oxan-4-ol Chemical compound C=12N=NN(CC=3N=C(C=CC=3)C3(O)CCOCC3)C2=NC(N)=NC=1C1=CC=CC=C1 YNRLREZIGIVCIG-UHFFFAOYSA-N 0.000 claims description 2
- DLIYMAPNSDNKEQ-UHFFFAOYSA-N 4-[6-[[5-amino-7-(3-methoxyphenyl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]oxan-4-ol Chemical compound COC1=CC=CC(C=2C=3N=NN(CC=4N=C(C=CC=4)C4(O)CCOCC4)C=3N=C(N)N=2)=C1 DLIYMAPNSDNKEQ-UHFFFAOYSA-N 0.000 claims description 2
- JHHCMMVKLXZUPL-UHFFFAOYSA-N 4-[6-[[5-amino-7-(4-methyl-1,3-thiazol-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]oxan-4-ol Chemical compound CC1=CSC(C=2C=3N=NN(CC=4N=C(C=CC=4)C4(O)CCOCC4)C=3N=C(N)N=2)=N1 JHHCMMVKLXZUPL-UHFFFAOYSA-N 0.000 claims description 2
- COENJCHOYLKDNG-UHFFFAOYSA-N 4-[6-[[5-amino-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]oxan-4-ol Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(C2(O)CCOCC2)=N1 COENJCHOYLKDNG-UHFFFAOYSA-N 0.000 claims description 2
- QOASHFYQMZOHPI-UHFFFAOYSA-N 7-(5-methylfuran-2-yl)-3-[[6-(2,2,2-trifluoroethoxymethyl)pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(COCC(F)(F)F)=N1 QOASHFYQMZOHPI-UHFFFAOYSA-N 0.000 claims description 2
- XPZHJACMHBMAMG-UHFFFAOYSA-N 7-(5-methylfuran-2-yl)-3-[[6-(2-propan-2-yloxyethylperoxymethyl)pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound CC1=CC=C(O1)C=1C2=C(N=C(N=1)N)N(N=N2)CC1=NC(=CC=C1)COOCCOC(C)C XPZHJACMHBMAMG-UHFFFAOYSA-N 0.000 claims description 2
- KCILAWKAHWFBDN-UHFFFAOYSA-N 7-(5-methylfuran-2-yl)-3-[[6-(oxolan-2-ylmethoxymethyl)pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(COCC2OCCC2)=N1 KCILAWKAHWFBDN-UHFFFAOYSA-N 0.000 claims description 2
- VEDXQMZUZASSKU-UHFFFAOYSA-N 7-(5-methylfuran-2-yl)-3-[[6-(oxolan-3-ylmethoxymethyl)pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(COCC2COCC2)=N1 VEDXQMZUZASSKU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 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 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 11
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000001149 cognitive effect Effects 0.000 claims 2
- NNIXXMBWAIAPPE-UHFFFAOYSA-N 1-[6-[[5-amino-7-(4-methyl-1,3-thiazol-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]cyclobutan-1-ol Chemical compound CC1=CSC(C=2C=3N=NN(CC=4N=C(C=CC=4)C4(O)CCC4)C=3N=C(N)N=2)=N1 NNIXXMBWAIAPPE-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 9
- XPQLAYQODILNNG-UHFFFAOYSA-N 1-[6-[[5-amino-7-(3-methoxyphenyl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]cyclopentan-1-ol Chemical class COC1=CC=CC(C=2C=3N=NN(CC=4N=C(C=CC=4)C4(O)CCCC4)C=3N=C(N)N=2)=C1 XPQLAYQODILNNG-UHFFFAOYSA-N 0.000 description 1
- 102000009346 Adenosine receptors Human genes 0.000 description 1
- 108050000203 Adenosine receptors Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002467 adenosine A2a receptor antagonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7553808P | 2008-06-25 | 2008-06-25 | |
| US61/075,538 | 2008-06-25 | ||
| GB0906579.8 | 2009-04-16 | ||
| GBGB0906579.8A GB0906579D0 (en) | 2009-04-16 | 2009-04-16 | Pharmaceuticals, compositions and methods of making and using the same |
| PCT/GB2009/001605 WO2009156737A1 (en) | 2008-06-25 | 2009-06-25 | Triazolo [4, 5-d] pyramidine derivatives and their use as purine receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011525898A JP2011525898A (ja) | 2011-09-29 |
| JP2011525898A5 true JP2011525898A5 (https=) | 2013-04-11 |
| JP5559162B2 JP5559162B2 (ja) | 2014-07-23 |
Family
ID=40750727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011515594A Active JP5559162B2 (ja) | 2008-06-25 | 2009-06-25 | プリン受容体アンタゴニストとしてのトリアゾロ［４，５−ｄ］ピリミジン誘導体およびその使用 |
Country Status (20)
| Country | Link |
|---|---|
| US (9) | US8450328B2 (https=) |
| EP (1) | EP2321321B1 (https=) |
| JP (1) | JP5559162B2 (https=) |
| KR (3) | KR101680390B1 (https=) |
| CN (1) | CN102076692B (https=) |
| AT (1) | ATE544767T1 (https=) |
| AU (1) | AU2009263976B2 (https=) |
| BR (1) | BRPI0910182B8 (https=) |
| CA (1) | CA2727444C (https=) |
| DK (1) | DK2321321T3 (https=) |
| EA (1) | EA018803B1 (https=) |
| ES (1) | ES2382154T3 (https=) |
| GB (1) | GB0906579D0 (https=) |
| IL (2) | IL210071A (https=) |
| MX (1) | MX2010013841A (https=) |
| NZ (1) | NZ590590A (https=) |
| PL (1) | PL2321321T3 (https=) |
| PT (1) | PT2321321E (https=) |
| WO (1) | WO2009156737A1 (https=) |
| ZA (1) | ZA201100526B (https=) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0906579D0 (en) * | 2009-04-16 | 2009-05-20 | Vernalis R&D Ltd | Pharmaceuticals, compositions and methods of making and using the same |
| JP5765239B2 (ja) | 2009-03-13 | 2015-08-19 | アドヴィナス・セラピューティックス・リミテッド | 置換縮合ピリミジン化合物 |
| WO2011101861A1 (en) | 2010-01-29 | 2011-08-25 | Msn Laboratories Limited | Process for preparation of dpp-iv inhibitors |
| RU2014150494A (ru) * | 2012-05-30 | 2016-07-20 | Ф. Хоффманн-Ля Рош Аг | Пирролидиногетероциклы |
| US10781178B2 (en) | 2015-08-12 | 2020-09-22 | The General Hospital Corporation | 8-hydroxyquinoline derivatives as diagnostic and therapeutic agents |
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