NO328475B1 - Triazol [4,5-d]pyrimidinderivater og anvendelse derav - Google Patents

Info

Publication number

NO328475B1

NO328475B1 NO20033146A NO20033146A NO328475B1 NO 328475 B1 NO328475 B1 NO 328475B1 NO 20033146 A NO20033146 A NO 20033146A NO 20033146 A NO20033146 A NO 20033146A NO 328475 B1 NO328475 B1 NO 328475B1

Authority

NO

Norway

Prior art keywords

furyl

pyrimidin

amine

triazolo

triazol

Prior art date

2001-01-10

Links

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• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
• 150000003230 pyrimidines Chemical class 0.000 title 1
• 150000003852 triazoles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 183
• 238000011282 treatment Methods 0.000 claims abstract description 47
• 125000003118 aryl group Chemical group 0.000 claims abstract description 37
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
• 208000035475 disorder Diseases 0.000 claims abstract description 23
• 208000016285 Movement disease Diseases 0.000 claims abstract description 22
• 208000002193 Pain Diseases 0.000 claims abstract description 17
• 102000009346 Adenosine receptors Human genes 0.000 claims abstract description 15
• 108050000203 Adenosine receptors Proteins 0.000 claims abstract description 15
• 150000003839 salts Chemical class 0.000 claims abstract description 13
• 230000009286 beneficial effect Effects 0.000 claims abstract description 12
• 102000000033 Purinergic Receptors Human genes 0.000 claims abstract description 11
• 108010080192 Purinergic Receptors Proteins 0.000 claims abstract description 11
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 10
• 208000010877 cognitive disease Diseases 0.000 claims abstract description 10
• 230000004112 neuroprotection Effects 0.000 claims abstract description 10
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
• 150000002367 halogens Chemical class 0.000 claims abstract description 9
• 101150051188 Adora2a gene Proteins 0.000 claims abstract description 8
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims abstract description 8
• 230000000903 blocking effect Effects 0.000 claims abstract description 8
• 208000028698 Cognitive impairment Diseases 0.000 claims abstract description 7
• 208000000094 Chronic Pain Diseases 0.000 claims abstract description 6
• 230000001154 acute effect Effects 0.000 claims abstract description 6
• 208000005298 acute pain Diseases 0.000 claims abstract description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 6
• 206010027175 memory impairment Diseases 0.000 claims abstract description 5
• 201000003631 narcolepsy Diseases 0.000 claims abstract description 5
• 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims abstract description 3
• 230000002265 prevention Effects 0.000 claims abstract description 3
• 229910052739 hydrogen Inorganic materials 0.000 claims description 302
• FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims description 137
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 107
• -1 NHOH Chemical group 0.000 claims description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
• 239000003814 drug Substances 0.000 claims description 19
• 229940079593 drug Drugs 0.000 claims description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 210000003169 central nervous system Anatomy 0.000 claims description 11
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 7
• 206010034010 Parkinsonism Diseases 0.000 claims description 7
• 229910052786 argon Inorganic materials 0.000 claims description 7
• 201000006474 Brain Ischemia Diseases 0.000 claims description 6
• 206010008120 Cerebral ischaemia Diseases 0.000 claims description 6
• 208000012661 Dyskinesia Diseases 0.000 claims description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
• 206010008118 cerebral infarction Diseases 0.000 claims description 6
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 208000023105 Huntington disease Diseases 0.000 claims description 5
• 208000027089 Parkinsonian disease Diseases 0.000 claims description 5
• 230000003542 behavioural effect Effects 0.000 claims description 5
• 230000006378 damage Effects 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 230000000750 progressive effect Effects 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 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 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
• 206010003694 Atrophy Diseases 0.000 claims description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 4
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
• 208000002972 Hepatolenticular Degeneration Diseases 0.000 claims description 4
• 208000001089 Multiple system atrophy Diseases 0.000 claims description 4
• 208000008238 Muscle Spasticity Diseases 0.000 claims description 4
• 208000018839 Wilson disease Diseases 0.000 claims description 4
• 230000037444 atrophy Effects 0.000 claims description 4
• 201000010099 disease Diseases 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 208000019116 sleep disease Diseases 0.000 claims description 4
• 208000018198 spasticity Diseases 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 239000005711 Benzoic acid Substances 0.000 claims description 3
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
• 208000011990 Corticobasal Degeneration Diseases 0.000 claims description 3
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 3
• 208000028017 Psychotic disease Diseases 0.000 claims description 3
• 206010063837 Reperfusion injury Diseases 0.000 claims description 3
• 208000018300 basal ganglia disease Diseases 0.000 claims description 3
• 235000010233 benzoic acid Nutrition 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 208000030533 eye disease Diseases 0.000 claims description 3
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 208000028867 ischemia Diseases 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 210000003205 muscle Anatomy 0.000 claims description 3
• 208000031225 myocardial ischemia Diseases 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 230000001898 pallidal effect Effects 0.000 claims description 3
• 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 208000032253 retinal ischemia Diseases 0.000 claims description 3
• 201000000980 schizophrenia Diseases 0.000 claims description 3
• 125000001424 substituent group Chemical group 0.000 claims description 3
• CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 2
• HQSBCDPYXDGTCL-UHFFFAOYSA-N 3-[(4-amino-3-methylphenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C1=C(N)C(C)=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 HQSBCDPYXDGTCL-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
• 208000002603 Dopa-responsive dystonia Diseases 0.000 claims description 2
• 208000036757 Postencephalitic parkinsonism Diseases 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 229910052757 nitrogen Inorganic materials 0.000 claims description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
• 208000000170 postencephalitic Parkinson disease Diseases 0.000 claims description 2
• DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims description 2
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
• 229940124530 sulfonamide Drugs 0.000 claims description 2
• 150000003456 sulfonamides Chemical class 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
• 125000003107 substituted aryl group Chemical group 0.000 claims 5
• VJCQEPWQSBKWTE-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidin-5-amine Chemical compound N1=C(N)N=CC2=NNN=C21 VJCQEPWQSBKWTE-UHFFFAOYSA-N 0.000 claims 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
• LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• HPEHTWROERTIMH-UHFFFAOYSA-N 2-[6-[[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]pyridin-2-yl]acetonitrile Chemical compound C=12N=NN(CC=3N=C(CC#N)C=CC=3)C2=NC(N)=NC=1C1=CC=CO1 HPEHTWROERTIMH-UHFFFAOYSA-N 0.000 claims 1
• QTWZRFYFVZATOS-UHFFFAOYSA-N 2-amino-5-[[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]phenol Chemical compound C=12N=NN(CC=3C=C(O)C(N)=CC=3)C2=NC(N)=NC=1C1=CC=CO1 QTWZRFYFVZATOS-UHFFFAOYSA-N 0.000 claims 1
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• QBMWFHAVZLTULQ-UHFFFAOYSA-N 3-[(2,5-dimethoxyphenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound COC1=CC=C(OC)C(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 QBMWFHAVZLTULQ-UHFFFAOYSA-N 0.000 claims 1
• PWFVBCACZKZXFV-UHFFFAOYSA-N 3-[(2-ethylpyridin-4-yl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C1=NC(CC)=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 PWFVBCACZKZXFV-UHFFFAOYSA-N 0.000 claims 1
• FJQLLAZROAQIDK-UHFFFAOYSA-N 3-[(2-fluoro-4-nitrophenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C(=CC(=CC=3)[N+]([O-])=O)F)C2=NC(N)=NC=1C1=CC=CO1 FJQLLAZROAQIDK-UHFFFAOYSA-N 0.000 claims 1
• DFKSOEGEFMEXMH-UHFFFAOYSA-N 3-[(2-fluoro-5-methoxyphenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound COC1=CC=C(F)C(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 DFKSOEGEFMEXMH-UHFFFAOYSA-N 0.000 claims 1
• GOWVUTAYJUJMJP-UHFFFAOYSA-N 3-[(2-fluorophenyl)methyl]-7-(1h-pyrazol-5-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C(=CC=CC=3)F)C2=NC(N)=NC=1C=1C=CNN=1 GOWVUTAYJUJMJP-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• YSVWVOXTRYQTHL-UHFFFAOYSA-N 3-[(4-amino-2-fluorophenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound FC1=CC(N)=CC=C1CN1C2=NC(N)=NC(C=3OC=CC=3)=C2N=N1 YSVWVOXTRYQTHL-UHFFFAOYSA-N 0.000 claims 1
• HQQSMDYDRILQNC-UHFFFAOYSA-N 3-[(4-amino-3-fluorophenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C=C(F)C(N)=CC=3)C2=NC(N)=NC=1C1=CC=CO1 HQQSMDYDRILQNC-UHFFFAOYSA-N 0.000 claims 1
• YVVHVOOLQSYNGM-UHFFFAOYSA-N 3-[(4-aminophenyl)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=C(N)C=C1 YVVHVOOLQSYNGM-UHFFFAOYSA-N 0.000 claims 1
• PLFGEAYNLHZLDP-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C1=CC(N)=CC=C1CN1C2=NC(N)=NC(C=3OC=CC=3)=C2N=N1 PLFGEAYNLHZLDP-UHFFFAOYSA-N 0.000 claims 1
• ADMIHLIYFBCXRQ-UHFFFAOYSA-N 3-[(4-chloro-2-nitrophenyl)methyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C(=CC(Cl)=CC=3)[N+]([O-])=O)C2=NC(N)=NC=1C1=CC=CO1 ADMIHLIYFBCXRQ-UHFFFAOYSA-N 0.000 claims 1
• IKLYQSGSLDHSCM-UHFFFAOYSA-N 3-[(5-amino-2-fluorophenyl)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(N)=CC=C1F IKLYQSGSLDHSCM-UHFFFAOYSA-N 0.000 claims 1
• MJKKLGOUDLZKMB-UHFFFAOYSA-N 3-[(6-ethoxypyridin-2-yl)methyl]-7-(5-methylfuran-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound CCOC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC(C)=CC=2)=N1 MJKKLGOUDLZKMB-UHFFFAOYSA-N 0.000 claims 1
• FLVQPENVZWXBIF-UHFFFAOYSA-N 3-[1-(3-fluorophenyl)ethyl]-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound N1=NC2=C(C=3OC=CC=3)N=C(N)N=C2N1C(C)C1=CC=CC(F)=C1 FLVQPENVZWXBIF-UHFFFAOYSA-N 0.000 claims 1
• BDXGFFQYGDFTOE-UHFFFAOYSA-N 3-[[5-amino-7-(furan-2-yl)triazolo[4,5-d]pyrimidin-3-yl]methyl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 BDXGFFQYGDFTOE-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
• RKRRAEYZSWYXHM-UHFFFAOYSA-N 7-(5-methylfuran-2-yl)-3-(thiophen-2-ylmethyl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CS1 RKRRAEYZSWYXHM-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
• MREDYECZESEXSX-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(2-methoxy-4-nitrophenyl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound COC1=CC([N+]([O-])=O)=CC=C1CN1C2=NC(N)=NC(C=3OC=CC=3)=C2N=N1 MREDYECZESEXSX-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
• YDLSSNAJGCDZIY-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(3-methyl-4-nitrophenyl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound C1=C([N+]([O-])=O)C(C)=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 YDLSSNAJGCDZIY-UHFFFAOYSA-N 0.000 claims 1
• WCUNHKUZDFUTSU-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(3-methylphenyl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound CC1=CC=CC(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 WCUNHKUZDFUTSU-UHFFFAOYSA-N 0.000 claims 1
• JJUHZCBRPRLIKT-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(5-methyl-1h-indol-7-yl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12NC=CC2=CC(C)=CC=1CN(C1=NC(N)=N2)N=NC1=C2C1=CC=CO1 JJUHZCBRPRLIKT-UHFFFAOYSA-N 0.000 claims 1
• ZNIAVGMHCQYFOZ-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(5-methyl-2-nitrophenyl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound CC1=CC=C([N+]([O-])=O)C(CN2C3=NC(N)=NC(=C3N=N2)C=2OC=CC=2)=C1 ZNIAVGMHCQYFOZ-UHFFFAOYSA-N 0.000 claims 1
• DQDQWCBQRVSZEI-UHFFFAOYSA-N 7-(furan-2-yl)-3-[(6-propan-2-ylpyridin-3-yl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound C1=NC(C(C)C)=CC=C1CN1C2=NC(N)=NC(C=3OC=CC=3)=C2N=N1 DQDQWCBQRVSZEI-UHFFFAOYSA-N 0.000 claims 1
• UXIUTMGDEVKDJT-UHFFFAOYSA-N 7-(furan-2-yl)-3-[[3-(trifluoromethyl)phenyl]methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound C=12N=NN(CC=3C=C(C=CC=3)C(F)(F)F)C2=NC(N)=NC=1C1=CC=CO1 UXIUTMGDEVKDJT-UHFFFAOYSA-N 0.000 claims 1
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