HRP20030533A2 - TRIAZOLO[4,5-d]PYRIMIDINE DERIVATIVES AND THEIR USE AS PURINEGIC RECEPTOR ANTAGONISTS - Google Patents

Info

Publication number

HRP20030533A2

HRP20030533A2 HR20030533A HRP20030533A HRP20030533A2 HR P20030533 A2 HRP20030533 A2 HR P20030533A2 HR 20030533 A HR20030533 A HR 20030533A HR P20030533 A HRP20030533 A HR P20030533A HR P20030533 A2 HRP20030533 A2 HR P20030533A2

Authority

HR

Croatia

Prior art keywords

triazolo

furyl

pyrimidin

amine

amino

Prior art date

2001-01-10

Links

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• GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical class N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 title description 3
• 229940044551 receptor antagonist Drugs 0.000 title description 3
• 239000002464 receptor antagonist Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 190
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 119
• 125000003118 aryl group Chemical group 0.000 claims abstract description 93
• 238000011282 treatment Methods 0.000 claims abstract description 56
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
• 150000002367 halogens Chemical class 0.000 claims abstract description 26
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
• 208000035475 disorder Diseases 0.000 claims abstract description 22
• 102000009346 Adenosine receptors Human genes 0.000 claims abstract description 18
• 108050000203 Adenosine receptors Proteins 0.000 claims abstract description 18
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
• 208000016285 Movement disease Diseases 0.000 claims abstract description 14
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 14
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 13
• 239000000651 prodrug Substances 0.000 claims abstract description 13
• 229940002612 prodrug Drugs 0.000 claims abstract description 13
• 208000002193 Pain Diseases 0.000 claims abstract description 12
• 102000000033 Purinergic Receptors Human genes 0.000 claims abstract description 12
• 108010080192 Purinergic Receptors Proteins 0.000 claims abstract description 12
• 230000000903 blocking effect Effects 0.000 claims abstract description 12
• 230000004112 neuroprotection Effects 0.000 claims abstract description 12
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 10
• 125000005110 aryl thio group Chemical group 0.000 claims abstract description 10
• 101150051188 Adora2a gene Proteins 0.000 claims abstract description 9
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims abstract description 8
• 230000009286 beneficial effect Effects 0.000 claims abstract description 8
• 150000001721 carbon Chemical class 0.000 claims abstract description 5
• 201000003631 narcolepsy Diseases 0.000 claims abstract description 5
• 230000002265 prevention Effects 0.000 claims abstract description 5
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
• 208000000094 Chronic Pain Diseases 0.000 claims abstract description 4
• 230000001154 acute effect Effects 0.000 claims abstract description 4
• 208000005298 acute pain Diseases 0.000 claims abstract description 4
• 238000000034 method Methods 0.000 claims description 117
• -1 2-thiazolyl Chemical group 0.000 claims description 79
• 125000001072 heteroaryl group Chemical group 0.000 claims description 52
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 41
• 239000003814 drug Substances 0.000 claims description 25
• 229940079593 drug Drugs 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• 125000002541 furyl group Chemical group 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
• 125000001544 thienyl group Chemical group 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 15
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 14
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• 208000019430 Motor disease Diseases 0.000 claims description 11
• 125000001188 haloalkyl group Chemical group 0.000 claims description 11
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 9
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
• 125000001041 indolyl group Chemical group 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 125000003107 substituted aryl group Chemical group 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• YHYOCBNJVOUOHL-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound NC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 YHYOCBNJVOUOHL-UHFFFAOYSA-N 0.000 claims description 6
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
• 206010034010 Parkinsonism Diseases 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 230000000750 progressive effect Effects 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 208000012661 Dyskinesia Diseases 0.000 claims description 5
• 208000023105 Huntington disease Diseases 0.000 claims description 5
• 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 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• VNMKHYOSPJVOAG-UHFFFAOYSA-N 2-[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]acetic acid Chemical compound C=12N=NN(CC(O)=O)C2=NC(N)=NC=1C1=CC=CO1 VNMKHYOSPJVOAG-UHFFFAOYSA-N 0.000 claims description 4
• BNLXLVWITDZVIM-UHFFFAOYSA-N 3-[(2-fluorophenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C(=CC=CC=3)F)C2=NC(N)=NC=1C1=CC=CO1 BNLXLVWITDZVIM-UHFFFAOYSA-N 0.000 claims description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
• 208000002972 Hepatolenticular Degeneration Diseases 0.000 claims description 4
• WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 4
• 208000001089 Multiple system atrophy Diseases 0.000 claims description 4
• 208000008238 Muscle Spasticity Diseases 0.000 claims description 4
• 208000027089 Parkinsonian disease Diseases 0.000 claims description 4
• 208000018839 Wilson disease Diseases 0.000 claims description 4
• 125000005002 aryl methyl group Chemical group 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 230000003920 cognitive function Effects 0.000 claims description 4
• 201000010099 disease Diseases 0.000 claims description 4
• 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 208000018198 spasticity Diseases 0.000 claims description 4
• 239000000126 substance Substances 0.000 claims description 4
• 229940124530 sulfonamide Drugs 0.000 claims description 4
• 150000003456 sulfonamides Chemical class 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• OTUALLLJQXQVLY-UHFFFAOYSA-N 2-[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]-1-phenylethanone Chemical compound C=12N=NN(CC(=O)C=3C=CC=CC=3)C2=NC(N)=NC=1C1=CC=CO1 OTUALLLJQXQVLY-UHFFFAOYSA-N 0.000 claims description 3
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• WCWZDKZUOSZJPV-UHFFFAOYSA-N 3-[(2-fluorophenyl)methyl]-7-(2h-triazol-4-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C(=CC=CC=3)F)C2=NC(N)=NC=1C1=CNN=N1 WCWZDKZUOSZJPV-UHFFFAOYSA-N 0.000 claims description 3
• 206010003694 Atrophy Diseases 0.000 claims description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
• 208000011990 Corticobasal Degeneration Diseases 0.000 claims description 3
• LSWFUJBECFGHFC-UHFFFAOYSA-N [6-[[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]methanol;hydrochloride Chemical compound Cl.C=12N=NN(CC=3N=C(CO)C=CC=3)C2=NC(N)=NC=1C1=CC=CO1 LSWFUJBECFGHFC-UHFFFAOYSA-N 0.000 claims description 3
• 230000037444 atrophy Effects 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
• 239000004615 ingredient Substances 0.000 claims description 3
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• JLPAUIGRIPHUJC-UHFFFAOYSA-N 3-(2h-benzotriazol-5-ylmethyl)-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C=C4N=NNC4=CC=3)C2=NC(N)=NC=1C1=CC=CO1 JLPAUIGRIPHUJC-UHFFFAOYSA-N 0.000 claims description 2
• AOXADOPTSUIEGJ-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(3-methoxyphenyl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound COC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 AOXADOPTSUIEGJ-UHFFFAOYSA-N 0.000 claims description 2
• MOGTYIPADGVXJV-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(3-nitrophenyl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C=C(C=CC=3)[N+]([O-])=O)C2=NC(N)=NC=1C1=CC=CO1 MOGTYIPADGVXJV-UHFFFAOYSA-N 0.000 claims description 2
• 208000005374 Poisoning Diseases 0.000 claims description 2
• 208000036757 Postencephalitic parkinsonism Diseases 0.000 claims description 2
• 208000018300 basal ganglia disease Diseases 0.000 claims description 2
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 2
• HVTUPRADYGJDID-UHFFFAOYSA-N n-[4-[[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]-2-methylphenyl]formamide Chemical compound C1=C(NC=O)C(C)=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 HVTUPRADYGJDID-UHFFFAOYSA-N 0.000 claims description 2
• 231100000572 poisoning Toxicity 0.000 claims description 2
• 230000000607 poisoning effect Effects 0.000 claims description 2
• 208000000170 postencephalitic Parkinson disease Diseases 0.000 claims description 2
• 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 2
• FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims 6
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 4
• 230000015654 memory Effects 0.000 claims 2
• YIIMHJRGNKUGSL-UHFFFAOYSA-N 2-[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]-1-(2-nitrophenyl)ethanone Chemical compound C=12N=NN(CC(=O)C=3C(=CC=CC=3)[N+]([O-])=O)C2=NC(N)=NC=1C1=CC=CO1 YIIMHJRGNKUGSL-UHFFFAOYSA-N 0.000 claims 1
• FRLZNBCCRKOBFF-UHFFFAOYSA-N 2-[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]-n-pyridin-2-ylacetamide Chemical compound C=12N=NN(CC(=O)NC=3N=CC=CC=3)C2=NC(N)=NC=1C1=CC=CO1 FRLZNBCCRKOBFF-UHFFFAOYSA-N 0.000 claims 1
• VJCQEPWQSBKWTE-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidin-5-amine Chemical class N1=C(N)N=CC2=NNN=C21 VJCQEPWQSBKWTE-UHFFFAOYSA-N 0.000 claims 1
• MGJXGMPVRNWYLJ-UHFFFAOYSA-N 3-(5-fluoro-1h-indol-2-yl)-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(C=3NC4=CC=C(F)C=C4C=3)C2=NC(N)=NC=1C1=CC=CO1 MGJXGMPVRNWYLJ-UHFFFAOYSA-N 0.000 claims 1
• WJZTUUMKNHVWFW-UHFFFAOYSA-N 3-[(2-aminophenyl)methyl]-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-5-amine;hydrochloride Chemical compound Cl.O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC=C1N WJZTUUMKNHVWFW-UHFFFAOYSA-N 0.000 claims 1
• PEIDZPBLLQLXTN-UHFFFAOYSA-N 3-[(2-aminophenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C(=CC=CC=3)N)C2=NC(N)=NC=1C1=CC=CO1 PEIDZPBLLQLXTN-UHFFFAOYSA-N 0.000 claims 1
• PWJAQAICRHCZCI-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine;methyl 3-[[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]benzoate Chemical compound NC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1.COC(=O)C1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 PWJAQAICRHCZCI-UHFFFAOYSA-N 0.000 claims 1
• OLKVHRMNAHVKBP-UHFFFAOYSA-N 3-[(3-chlorophenyl)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(Cl)=C1 OLKVHRMNAHVKBP-UHFFFAOYSA-N 0.000 claims 1
• ORDXMWHLTPOXPM-UHFFFAOYSA-N 3-[(6-ethylpyridin-2-yl)methyl]-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound CCC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC(C)=CC=2)=N1 ORDXMWHLTPOXPM-UHFFFAOYSA-N 0.000 claims 1
• LMKCBJGIOMTJNM-UHFFFAOYSA-N 3-[[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]benzonitrile Chemical compound C=12N=NN(CC=3C=C(C=CC=3)C#N)C2=NC(N)=NC=1C1=CC=CO1 LMKCBJGIOMTJNM-UHFFFAOYSA-N 0.000 claims 1
• VIEICOVVDQTVSP-UHFFFAOYSA-N 6-[[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridine-2-carbaldehyde;tert-butyl 2-[[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]indole-1-carboxylate Chemical compound C=12N=NN(CC=3N=C(C=O)C=CC=3)C2=NC(N)=NC=1C1=CC=CO1.C=1C2=CC=CC=C2N(C(=O)OC(C)(C)C)C=1CN(C1=NC(N)=N2)N=NC1=C2C1=CC=CO1 VIEICOVVDQTVSP-UHFFFAOYSA-N 0.000 claims 1
• ZMMHNZZGJSYCCJ-UHFFFAOYSA-N 7-(5-methylfuran-2-yl)-3-[(6-phenylpyridin-2-yl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(C=2C=CC=CC=2)=N1 ZMMHNZZGJSYCCJ-UHFFFAOYSA-N 0.000 claims 1
• RFIZNJCBCQRDNC-UHFFFAOYSA-N 7-(furan-2-yl)-3-(3-methylthiophen-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C1=CSC(N2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1C RFIZNJCBCQRDNC-UHFFFAOYSA-N 0.000 claims 1
• JTNOAURKLNDJRN-UHFFFAOYSA-N 7-(furan-2-yl)-3-(quinolin-8-ylmethyl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C4=NC=CC=C4C=CC=3)C2=NC(N)=NC=1C1=CC=CO1 JTNOAURKLNDJRN-UHFFFAOYSA-N 0.000 claims 1
• ZCXRBVUSBULVFV-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(2,3,5-trifluorophenyl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C(=C(F)C=C(F)C=3)F)C2=NC(N)=NC=1C1=CC=CO1 ZCXRBVUSBULVFV-UHFFFAOYSA-N 0.000 claims 1
• RPESVFFSTNXZGQ-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(2-nitrophenyl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C(=CC=CC=3)[N+]([O-])=O)C2=NC(N)=NC=1C1=CC=CO1 RPESVFFSTNXZGQ-UHFFFAOYSA-N 0.000 claims 1
• LBMIGLSDJJWEKO-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(6-propan-2-ylpyridin-2-yl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound CC(C)C1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=N1 LBMIGLSDJJWEKO-UHFFFAOYSA-N 0.000 claims 1
• TZOOGRJBPCSUNY-UHFFFAOYSA-N 7-(furan-2-yl)-3-[[4-(methylamino)phenyl]methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound C1=CC(NC)=CC=C1CN1C2=NC(N)=NC(C=3OC=CC=3)=C2N=N1 TZOOGRJBPCSUNY-UHFFFAOYSA-N 0.000 claims 1
• RWVRMQZJPABIPN-UHFFFAOYSA-N 7-(furan-2-yl)-3-[[6-(methylsulfonylmethyl)pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound CS(=O)(=O)CC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=N1 RWVRMQZJPABIPN-UHFFFAOYSA-N 0.000 claims 1
• PNXWTQATHDXZGC-UHFFFAOYSA-N C(#N)C1=CC=C(CN2N=NC3=C2N=C(N=C3C=3OC=CC3)N)C=C1.NC1=C(CN3N=NC2=C3N=C(N=C2C=2OC=CC2)N)C=CC(=C1)Cl Chemical compound C(#N)C1=CC=C(CN2N=NC3=C2N=C(N=C3C=3OC=CC3)N)C=C1.NC1=C(CN3N=NC2=C3N=C(N=C2C=2OC=CC2)N)C=CC(=C1)Cl PNXWTQATHDXZGC-UHFFFAOYSA-N 0.000 claims 1
• KRZLRAQJFUZOOA-UHFFFAOYSA-N C(#N)C=1C=C(CN2N=NC3=C2N=C(N=C3C=3OC=CC3)N)C=CC1.NC=1N=C(C3=C(N1)N(N=N3)CC(=O)OCC)C=3OC=CC3 Chemical compound C(#N)C=1C=C(CN2N=NC3=C2N=C(N=C3C=3OC=CC3)N)C=CC1.NC=1N=C(C3=C(N1)N(N=N3)CC(=O)OCC)C=3OC=CC3 KRZLRAQJFUZOOA-UHFFFAOYSA-N 0.000 claims 1
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• BCFGJIJLDDGBBF-UHFFFAOYSA-N C(C)OC1=CC=CC(=N1)CN1N=NC2=C1N=C(N=C2C=2OC=CC2)N.FC2=CC=C(CNC=1C=C(CN3N=NC4=C3N=C(N=C4C=4OC=CC4)N)C=CC1)C=C2 Chemical compound C(C)OC1=CC=CC(=N1)CN1N=NC2=C1N=C(N=C2C=2OC=CC2)N.FC2=CC=C(CNC=1C=C(CN3N=NC4=C3N=C(N=C4C=4OC=CC4)N)C=CC1)C=C2 BCFGJIJLDDGBBF-UHFFFAOYSA-N 0.000 claims 1
• KXHXFECRBIFYEY-UHFFFAOYSA-N CC1=CC=C(O1)C=1C2=C(N=C(N1)N)N(N=N2)CC2=C(C(=CC=C2)[N+](=O)[O-])C.Cl.[N+](=O)([O-])C=2C=C(CN1N=NC3=C1N=C(N=C3C3=NNC=C3)N)C=CC2 Chemical compound CC1=CC=C(O1)C=1C2=C(N=C(N1)N)N(N=N2)CC2=C(C(=CC=C2)[N+](=O)[O-])C.Cl.[N+](=O)([O-])C=2C=C(CN1N=NC3=C1N=C(N=C3C3=NNC=C3)N)C=CC2 KXHXFECRBIFYEY-UHFFFAOYSA-N 0.000 claims 1
• ALKRPOLWSBTTSU-UHFFFAOYSA-N CC1=CC=C(O1)C=1C2=C(N=C(N1)N)N(N=N2)CC2=NC(=CC=C2)C.FC2=C(CN1N=NC3=C1N=C(N=C3C=3OC=CC3)N)C=CC(=C2)F Chemical compound CC1=CC=C(O1)C=1C2=C(N=C(N1)N)N(N=N2)CC2=NC(=CC=C2)C.FC2=C(CN1N=NC3=C1N=C(N=C3C=3OC=CC3)N)C=CC(=C2)F ALKRPOLWSBTTSU-UHFFFAOYSA-N 0.000 claims 1
• DYXGMUGIARPKSN-UHFFFAOYSA-N CC1=CC=C(O1)C=1C2=C(N=C(N1)N)N(N=N2)CC=2SC=CC2.FC2=C(CN1N=NC3=C1N=C(N=C3C=3OC(=CC3)C)N)C(=CC=C2)F Chemical compound CC1=CC=C(O1)C=1C2=C(N=C(N1)N)N(N=N2)CC=2SC=CC2.FC2=C(CN1N=NC3=C1N=C(N=C3C=3OC(=CC3)C)N)C(=CC=C2)F DYXGMUGIARPKSN-UHFFFAOYSA-N 0.000 claims 1
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• PRYXAMWAFCNUHA-UHFFFAOYSA-N ClC1=CC(=C(CN2N=NC3=C2N=C(N=C3C=3OC=CC3)N)C=C1)[N+](=O)[O-].O1C(=CC=C1)C=1C3=C(N=C(N1)N)N(N=N3)CC3=NC(=CC(=C3)NO)C Chemical compound ClC1=CC(=C(CN2N=NC3=C2N=C(N=C3C=3OC=CC3)N)C=C1)[N+](=O)[O-].O1C(=CC=C1)C=1C3=C(N=C(N1)N)N(N=N3)CC3=NC(=CC(=C3)NO)C PRYXAMWAFCNUHA-UHFFFAOYSA-N 0.000 claims 1
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• 208000002603 Dopa-responsive dystonia Diseases 0.000 claims 1
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• PMUOSBGFTIVVJB-UHFFFAOYSA-N FC1=C(CN2N=NC3=C2N=C(N=C3C=3OC=CC3)N)C=C(C=C1)OC.NC=1C=C(CN3N=NC2=C3N=C(N=C2C2=CN=CS2)N)C=CC1 Chemical compound FC1=C(CN2N=NC3=C2N=C(N=C3C=3OC=CC3)N)C=C(C=C1)OC.NC=1C=C(CN3N=NC2=C3N=C(N=C2C2=CN=CS2)N)C=CC1 PMUOSBGFTIVVJB-UHFFFAOYSA-N 0.000 claims 1
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