CA2680075A1 - Adenosine a2a receptor antagonists - Google Patents

Info

Publication number

CA2680075A1

CA2680075A1 CA002680075A CA2680075A CA2680075A1 CA 2680075 A1 CA2680075 A1 CA 2680075A1 CA 002680075 A CA002680075 A CA 002680075A CA 2680075 A CA2680075 A CA 2680075A CA 2680075 A1 CA2680075 A1 CA 2680075A1

Authority

CA

Canada

Prior art keywords

pyrrolo

pyrimidin

triazolo

furan

ethyl

Prior art date

2007-03-30

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
• CIPO
• Discuss

• 229940123702 Adenosine A2a receptor antagonist Drugs 0.000 title abstract description 5
• 239000002467 adenosine A2a receptor antagonist Substances 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 241
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 27
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 27
• 208000005793 Restless legs syndrome Diseases 0.000 claims abstract description 27
• 206010016654 Fibrosis Diseases 0.000 claims abstract description 25
• 230000004761 fibrosis Effects 0.000 claims abstract description 22
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 19
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims abstract description 19
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims abstract description 19
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims abstract description 19
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 18
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 18
• 230000000694 effects Effects 0.000 claims abstract description 16
• 230000001404 mediated effect Effects 0.000 claims abstract description 16
• 230000007882 cirrhosis Effects 0.000 claims abstract description 14
• 208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 14
• 230000006399 behavior Effects 0.000 claims abstract description 12
• 230000000737 periodic effect Effects 0.000 claims abstract description 12
• 208000014094 Dystonic disease Diseases 0.000 claims abstract description 11
• 208000027776 Extrapyramidal disease Diseases 0.000 claims abstract description 11
• 208000004930 Fatty Liver Diseases 0.000 claims abstract description 11
• 206010019668 Hepatic fibrosis Diseases 0.000 claims abstract description 11
• 206010019708 Hepatic steatosis Diseases 0.000 claims abstract description 11
• 208000028017 Psychotic disease Diseases 0.000 claims abstract description 11
• 206010039966 Senile dementia Diseases 0.000 claims abstract description 11
• 208000010118 dystonia Diseases 0.000 claims abstract description 11
• 230000002500 effect on skin Effects 0.000 claims abstract description 11
• 208000010706 fatty liver disease Diseases 0.000 claims abstract description 11
• 231100000240 steatosis hepatitis Toxicity 0.000 claims abstract description 11
• 238000000034 method Methods 0.000 claims description 78
• 150000003839 salts Chemical class 0.000 claims description 57
• 229910052739 hydrogen Inorganic materials 0.000 claims description 42
• 239000001257 hydrogen Substances 0.000 claims description 40
• 239000008194 pharmaceutical composition Substances 0.000 claims description 30
• 125000002252 acyl group Chemical group 0.000 claims description 23
• WLMIXIOSYFFELW-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound NC1=NC=CC2=NC=NN12 WLMIXIOSYFFELW-UHFFFAOYSA-N 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 101150051188 Adora2a gene Proteins 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 11
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 8
• 150000001721 carbon Chemical group 0.000 claims description 8
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• 125000002950 monocyclic group Chemical group 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• HSYFUEQSHLHOCJ-UHFFFAOYSA-N 10-[2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethyl]-4-phenyl-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4C=CC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1F HSYFUEQSHLHOCJ-UHFFFAOYSA-N 0.000 claims description 5
• HXIZVRUQWBTVGJ-UHFFFAOYSA-N 2-(furan-2-yl)-7-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound COC1=CC=CC=C1N1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=C2)CC1 HXIZVRUQWBTVGJ-UHFFFAOYSA-N 0.000 claims description 5
• WYRJNBSXZOPCCY-UHFFFAOYSA-N 7-(2-(4-(2,4-difluorophenyl)-1,4-diazepan-1-yl)ethyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCCN1C1=CC=C(F)C=C1F WYRJNBSXZOPCCY-UHFFFAOYSA-N 0.000 claims description 5
• ONNBHVCWHUPRGG-UHFFFAOYSA-N 7-(2-(4-(3-(2,4-difluorophenyl)propyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1CCCC1=CC=C(F)C=C1F ONNBHVCWHUPRGG-UHFFFAOYSA-N 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• XMCSYJUNUWNRRB-UHFFFAOYSA-N (4-(2-(5-amino-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)piperazin-1-yl)(2,4-difluorophenyl)methanone Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C(=O)C1=CC=C(F)C=C1F XMCSYJUNUWNRRB-UHFFFAOYSA-N 0.000 claims description 4
• YAVWCXAJPFHLCF-UHFFFAOYSA-N 2-(furan-2-yl)-7-(2-(4-((3-methylbenzo[b]thiophen-2-yl)methyl)piperazin-1-yl)ethyl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound S1C2=CC=CC=C2C(C)=C1CN(CC1)CCN1CCN1C=CC(C2=N3)=C1N=C(N)N2N=C3C1=CC=CO1 YAVWCXAJPFHLCF-UHFFFAOYSA-N 0.000 claims description 4
• KGQZTTJVXWSUBU-UHFFFAOYSA-N 7-(2-(2,4-difluorophenoxy)ethyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCOC1=CC=C(F)C=C1F KGQZTTJVXWSUBU-UHFFFAOYSA-N 0.000 claims description 4
• WNVTXROKYDDCJG-UHFFFAOYSA-N 7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1F WNVTXROKYDDCJG-UHFFFAOYSA-N 0.000 claims description 4
• HTEJUZKHVAJTIW-UHFFFAOYSA-N 7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)propyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1CN(C=2C(=CC(F)=CC=2)F)CCN1C(C)CN1C=CC(C2=N3)=C1N=C(N)N2N=C3C1=CC=CO1 HTEJUZKHVAJTIW-UHFFFAOYSA-N 0.000 claims description 4
• DKDLRLPQPKOMGX-UHFFFAOYSA-N 7-(2-(4-(2,4-difluorophenyl)piperidin-1-yl)ethyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCC1C1=CC=C(F)C=C1F DKDLRLPQPKOMGX-UHFFFAOYSA-N 0.000 claims description 4
• PWOCORAGTLBVIX-UHFFFAOYSA-N 7-(2-(4-(2,5-difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC(F)=CC=C1F PWOCORAGTLBVIX-UHFFFAOYSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• KIWUTIOBEOOYCL-UHFFFAOYSA-N 1-(4-(2-(5-amino-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)piperazin-1-yl)-2-(2,4-difluorophenyl)ethanone Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C(=O)CC1=CC=C(F)C=C1F KIWUTIOBEOOYCL-UHFFFAOYSA-N 0.000 claims description 3
• SAZVPRJQFZGTQN-UHFFFAOYSA-N 1-(4-(2-(5-amino-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)piperazin-1-yl)-3-(2,4-difluorophenyl)propan-1-one Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C(=O)CCC1=CC=C(F)C=C1F SAZVPRJQFZGTQN-UHFFFAOYSA-N 0.000 claims description 3
• LIQSFTSKJLKXMC-UHFFFAOYSA-N 10-[1-[4-(2,4-difluorophenyl)piperazin-1-yl]propan-2-yl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC(C2=NC(=NN2C(N)=N2)C=3OC=CC=3)=C2N1C(C)CN(CC1)CCN1C1=CC=C(F)C=C1F LIQSFTSKJLKXMC-UHFFFAOYSA-N 0.000 claims description 3
• MXNDVZOOAYJVPY-UHFFFAOYSA-N 10-[2-(4-fluorophenoxy)ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCOC1=CC=C(F)C=C1 MXNDVZOOAYJVPY-UHFFFAOYSA-N 0.000 claims description 3
• IQLHNKNTMNYJAH-UHFFFAOYSA-N 10-[3-[4-(2,4-difluorophenyl)piperazin-1-yl]-2-methylpropyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC(C2=NC(=NN2C(N)=N2)C=3OC=CC=3)=C2N1CC(C)CN(CC1)CCN1C1=CC=C(F)C=C1F IQLHNKNTMNYJAH-UHFFFAOYSA-N 0.000 claims description 3
• NJKDPGKGXHAHAX-UHFFFAOYSA-N 10-[3-[4-(2,4-difluorophenyl)piperazin-1-yl]butyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1CN(C=2C(=CC(F)=CC=2)F)CCN1C(C)CCN1C=CC(C2=N3)=C1N=C(N)N2N=C3C1=CC=CO1 NJKDPGKGXHAHAX-UHFFFAOYSA-N 0.000 claims description 3
• URBCSJNYQOTKKQ-UHFFFAOYSA-N 10-[3-[4-(2,4-difluorophenyl)piperazin-1-yl]propyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCCN(CC1)CCN1C1=CC=C(F)C=C1F URBCSJNYQOTKKQ-UHFFFAOYSA-N 0.000 claims description 3
• YRFNESLBISEHBS-UHFFFAOYSA-N 10-[4-[4-(2,4-difluorophenyl)piperazin-1-yl]but-2-ynyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CC#CCN(CC1)CCN1C1=CC=C(F)C=C1F YRFNESLBISEHBS-UHFFFAOYSA-N 0.000 claims description 3
• NEVFFONHCGOSOR-UHFFFAOYSA-N 10-[4-[4-(2,4-difluorophenyl)piperazin-1-yl]butan-2-yl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC(C2=NC(=NN2C(N)=N2)C=3OC=CC=3)=C2N1C(C)CCN(CC1)CCN1C1=CC=C(F)C=C1F NEVFFONHCGOSOR-UHFFFAOYSA-N 0.000 claims description 3
• MXGKRPMAVDOONN-UHFFFAOYSA-N 7-(2-(2,4-difluorophenylthio)ethyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCSC1=CC=C(F)C=C1F MXGKRPMAVDOONN-UHFFFAOYSA-N 0.000 claims description 3
• GLTJVTUDCDTGKF-UHFFFAOYSA-N 7-(2-(4-(2,4-difluorobenzyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1CC1=CC=C(F)C=C1F GLTJVTUDCDTGKF-UHFFFAOYSA-N 0.000 claims description 3
• RVEINCWSWSAJBJ-UHFFFAOYSA-N 7-(2-(4-(2,4-difluorophenethyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1CCC1=CC=C(F)C=C1F RVEINCWSWSAJBJ-UHFFFAOYSA-N 0.000 claims description 3
• KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
• SUXJAEXJMDFYGV-UPHRSURJSA-N 10-[(Z)-4-[4-(2,4-difluorophenyl)piperazin-1-yl]but-2-enyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1C\C=C/CN(CC1)CCN1C1=CC=C(F)C=C1F SUXJAEXJMDFYGV-UPHRSURJSA-N 0.000 claims description 2
• IRCKPDVMHQTZMA-UHFFFAOYSA-N 10-[2-(4-cycloheptylpiperazin-1-yl)ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1CCCCCC1 IRCKPDVMHQTZMA-UHFFFAOYSA-N 0.000 claims description 2
• MSBYEOPUCDGXGE-UHFFFAOYSA-N 10-[2-(4-cyclohexylpiperazin-1-yl)ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1CCCCC1 MSBYEOPUCDGXGE-UHFFFAOYSA-N 0.000 claims description 2
• IOTPMBVAQNXYEF-UHFFFAOYSA-N 10-[2-(4-cyclooctylpiperazin-1-yl)ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1CCCCCCC1 IOTPMBVAQNXYEF-UHFFFAOYSA-N 0.000 claims description 2
• DWFIYYONFDTSJT-UHFFFAOYSA-N 10-[2-(4-cyclopentylpiperazin-1-yl)ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1CCCC1 DWFIYYONFDTSJT-UHFFFAOYSA-N 0.000 claims description 2
• MJGOGDCGQKRHTN-UHFFFAOYSA-N 10-[2-[2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethoxy]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCOCCN(CC1)CCN1C1=CC=C(F)C=C1F MJGOGDCGQKRHTN-UHFFFAOYSA-N 0.000 claims description 2
• DWFWRCIHDDLGBT-UHFFFAOYSA-N 10-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound N=1N2C(N)=NC=3N(CCN4CCN(CC4)C=4C5=CC=CC=C5SN=4)C=CC=3C2=NC=1C1=CC=CO1 DWFWRCIHDDLGBT-UHFFFAOYSA-N 0.000 claims description 2
• FPHALYCALIDHOM-UHFFFAOYSA-N 10-[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound N=1N2C(N)=NC=3N(CCN4CCN(CC=5C=C6OCOC6=CC=5)CC4)C=CC=3C2=NC=1C1=CC=CO1 FPHALYCALIDHOM-UHFFFAOYSA-N 0.000 claims description 2
• HTHUKCOOPOMEOR-UHFFFAOYSA-N 10-[2-[4-(2,3-difluorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=CC(F)=C1F HTHUKCOOPOMEOR-UHFFFAOYSA-N 0.000 claims description 2
• SZFRMCIACDDYJQ-UHFFFAOYSA-N 10-[2-[4-(2,4-dichlorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(Cl)C=C1Cl SZFRMCIACDDYJQ-UHFFFAOYSA-N 0.000 claims description 2
• RRHOWPQYYQJSRQ-UHFFFAOYSA-N 10-[2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethyl]-4-(furan-3-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C4=COC=C4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1F RRHOWPQYYQJSRQ-UHFFFAOYSA-N 0.000 claims description 2
• FLSPKTITXNHGAO-UHFFFAOYSA-N 10-[2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethyl]-4-(oxolan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C4OCCC4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1F FLSPKTITXNHGAO-UHFFFAOYSA-N 0.000 claims description 2
• NNEHROSLTNKVRJ-UHFFFAOYSA-N 10-[2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethyl]-4-pyridin-2-yl-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4N=CC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1F NNEHROSLTNKVRJ-UHFFFAOYSA-N 0.000 claims description 2
• JEDNSFYBMMBWPL-UHFFFAOYSA-N 10-[2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethyl]-4-pyridin-3-yl-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4C=NC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1F JEDNSFYBMMBWPL-UHFFFAOYSA-N 0.000 claims description 2
• XNVDXHDOLXFPQR-UHFFFAOYSA-N 10-[2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethyl]-4-thiophen-2-yl-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4SC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1F XNVDXHDOLXFPQR-UHFFFAOYSA-N 0.000 claims description 2
• HHGGAAOMMYXTRS-UHFFFAOYSA-N 10-[2-[4-(2,6-difluorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=C(F)C=CC=C1F HHGGAAOMMYXTRS-UHFFFAOYSA-N 0.000 claims description 2
• IEZYIZXAYDJLML-UHFFFAOYSA-N 10-[2-[4-(2-bromo-4-fluorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1Br IEZYIZXAYDJLML-UHFFFAOYSA-N 0.000 claims description 2
• QGBVYNMZLFIHQY-UHFFFAOYSA-N 10-[2-[4-(2-chloro-4-fluorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1Cl QGBVYNMZLFIHQY-UHFFFAOYSA-N 0.000 claims description 2
• GXPNUTKYDYBHQI-UHFFFAOYSA-N 10-[2-[4-(2-fluorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=CC=C1F GXPNUTKYDYBHQI-UHFFFAOYSA-N 0.000 claims description 2
• AIKKRALLNLZKMQ-UHFFFAOYSA-N 10-[2-[4-(3,4-dichlorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(Cl)C(Cl)=C1 AIKKRALLNLZKMQ-UHFFFAOYSA-N 0.000 claims description 2
• UJSSLIODXFQHNJ-UHFFFAOYSA-N 10-[2-[4-(3-fluorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=CC(F)=C1 UJSSLIODXFQHNJ-UHFFFAOYSA-N 0.000 claims description 2
• RJYCFISDHHISRU-UHFFFAOYSA-N 10-[2-[4-(4-bromo-2-fluorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(Br)C=C1F RJYCFISDHHISRU-UHFFFAOYSA-N 0.000 claims description 2
• VCZPZKALWXJGTE-UHFFFAOYSA-N 10-[2-[4-(4-butylphenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC(CCCC)=CC=C1N1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=C2)CC1 VCZPZKALWXJGTE-UHFFFAOYSA-N 0.000 claims description 2
• XZJLFPNEPHNDMM-UHFFFAOYSA-N 10-[2-[4-(4-chloro-2-fluorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(Cl)C=C1F XZJLFPNEPHNDMM-UHFFFAOYSA-N 0.000 claims description 2
• HTVJCCFBMMUIMO-UHFFFAOYSA-N 10-[2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(Cl)C=C1 HTVJCCFBMMUIMO-UHFFFAOYSA-N 0.000 claims description 2
• QYZAANOQDKEEIH-UHFFFAOYSA-N 10-[2-[4-(4-fluorophenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1 QYZAANOQDKEEIH-UHFFFAOYSA-N 0.000 claims description 2
• HJXQBLUFRHTHEQ-UHFFFAOYSA-N 10-[2-[4-(4-tert-butylphenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1N1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=C2)CC1 HJXQBLUFRHTHEQ-UHFFFAOYSA-N 0.000 claims description 2
• SSNBPHJYFGNLNA-UHFFFAOYSA-N 10-[2-[4-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound CC1=NN(C=2C=CC=CC=2)C(C)=C1CN(CC1)CCN1CCN1C=CC(C2=N3)=C1N=C(N)N2N=C3C1=CC=CO1 SSNBPHJYFGNLNA-UHFFFAOYSA-N 0.000 claims description 2
• VLYCUUHUFDQLRI-UHFFFAOYSA-N 10-[2-[4-[3,5-bis(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VLYCUUHUFDQLRI-UHFFFAOYSA-N 0.000 claims description 2
• GCMCZTTWLJNZPU-UHFFFAOYSA-N 10-[2-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=NC=C(C(F)(F)F)C=C1Cl GCMCZTTWLJNZPU-UHFFFAOYSA-N 0.000 claims description 2
• PEPWWNBNOMRVMT-UHFFFAOYSA-N 10-[4-[4-(2,4-difluorophenyl)piperazin-1-yl]butyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCCCN(CC1)CCN1C1=CC=C(F)C=C1F PEPWWNBNOMRVMT-UHFFFAOYSA-N 0.000 claims description 2
• MNWVHONRFSXXBY-UHFFFAOYSA-N 2-[7-amino-10-[2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-4-yl]phenol Chemical compound C1=CC=2C3=NC(C=4C(=CC=CC=4)O)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1F MNWVHONRFSXXBY-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
• ALMZIESAKNVVJQ-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-10-[2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC5=CC=CC=C5C=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=C(F)C=C1F ALMZIESAKNVVJQ-UHFFFAOYSA-N 0.000 claims description 2
• LVWIQSQUYCAVAK-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-(4-methylpiperazin-1-yl)ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1CN(C)CCN1CCN1C(N=C(N)N2N=C(N=C22)C=3OC=CC=3)=C2C=C1 LVWIQSQUYCAVAK-UHFFFAOYSA-N 0.000 claims description 2
• WNQMZJFAEKXVOT-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-(4-phenylpiperazin-1-yl)ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=CC=C1 WNQMZJFAEKXVOT-UHFFFAOYSA-N 0.000 claims description 2
• BBGRIMIANULUMK-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-(4-propan-2-ylpiperazin-1-yl)ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1CN(C(C)C)CCN1CCN1C(N=C(N)N2N=C(N=C22)C=3OC=CC=3)=C2C=C1 BBGRIMIANULUMK-UHFFFAOYSA-N 0.000 claims description 2
• QWJHVKSXEBTEEK-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-[4-(1H-indol-4-yl)piperazin-1-yl]ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound N=1N2C(N)=NC=3N(CCN4CCN(CC4)C=4C=5C=CNC=5C=CC=4)C=CC=3C2=NC=1C1=CC=CO1 QWJHVKSXEBTEEK-UHFFFAOYSA-N 0.000 claims description 2
• ACQKOVNMVIXINM-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-[4-(2,4,6-trifluorophenyl)piperazin-1-yl]ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=C(F)C=C(F)C=C1F ACQKOVNMVIXINM-UHFFFAOYSA-N 0.000 claims description 2
• SFXZETCRYLQSCA-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-[4-(2-methylsulfanylphenyl)piperazin-1-yl]ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound CSC1=CC=CC=C1N1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=C2)CC1 SFXZETCRYLQSCA-UHFFFAOYSA-N 0.000 claims description 2
• ILXBTVBHYZOTGJ-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-[4-(3-methylsulfanylphenyl)piperazin-1-yl]ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound CSC1=CC=CC(N2CCN(CCN3C4=C(C5=NC(=NN5C(N)=N4)C=4OC=CC=4)C=C3)CC2)=C1 ILXBTVBHYZOTGJ-UHFFFAOYSA-N 0.000 claims description 2
• RZFPDBWDAHWKRC-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-[4-(4-methoxyphenyl)piperazin-1-yl]ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC(OC)=CC=C1N1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=C2)CC1 RZFPDBWDAHWKRC-UHFFFAOYSA-N 0.000 claims description 2
• OYMXCISTTLZINL-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC(C)=CC=C1N1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=C2)CC1 OYMXCISTTLZINL-UHFFFAOYSA-N 0.000 claims description 2
• MXHWNZOWRPRKDY-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-[4-(4-propan-2-ylphenyl)piperazin-1-yl]ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC(C(C)C)=CC=C1N1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=C2)CC1 MXHWNZOWRPRKDY-UHFFFAOYSA-N 0.000 claims description 2
• VUELIVXTMITQGP-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-[4-[3-methoxy-5-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound FC(F)(F)C1=CC(OC)=CC(N2CCN(CCN3C4=C(C5=NC(=NN5C(N)=N4)C=4OC=CC=4)C=C3)CC2)=C1 VUELIVXTMITQGP-UHFFFAOYSA-N 0.000 claims description 2
• AGYYQGZJGGODGW-UHFFFAOYSA-N 5-[4-[2-[7-amino-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]ethyl]piperazin-1-yl]-4-nitrothiophene-2-sulfonamide Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C=1SC(S(N)(=O)=O)=CC=1[N+]([O-])=O AGYYQGZJGGODGW-UHFFFAOYSA-N 0.000 claims description 2
• ZLFGTCSTGXETMD-UHFFFAOYSA-N 5-[[4-[2-[7-amino-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]ethyl]piperazin-1-yl]methyl]-1,3-dimethylpyrimidine-2,4-dione Chemical compound O=C1N(C)C(=O)N(C)C=C1CN1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=C2)CC1 ZLFGTCSTGXETMD-UHFFFAOYSA-N 0.000 claims description 2
• YPVVSKDADFMISS-UHFFFAOYSA-N 7-(2-(2,4-difluorophenylamino)ethyl)-2-(furan-2-yl)-7h-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCNC1=CC=C(F)C=C1F YPVVSKDADFMISS-UHFFFAOYSA-N 0.000 claims description 2
• 208000010877 cognitive disease Diseases 0.000 claims 3
• SUXJAEXJMDFYGV-OWOJBTEDSA-N 10-[(E)-4-[4-(2,4-difluorophenyl)piperazin-1-yl]but-2-enyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1C\C=C\CN(CC1)CCN1C1=CC=C(F)C=C1F SUXJAEXJMDFYGV-OWOJBTEDSA-N 0.000 claims 1
• FJKBOCHEFJCZFL-UHFFFAOYSA-N 10-[2-[4-(2,4-dimethylphenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound CC1=CC(C)=CC=C1N1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=C2)CC1 FJKBOCHEFJCZFL-UHFFFAOYSA-N 0.000 claims 1
• HLGDACJOMIQDPH-UHFFFAOYSA-N 10-[2-[4-(3,4-dimethoxyphenyl)piperazin-1-yl]ethyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1N1CCN(CCN2C3=C(C4=NC(=NN4C(N)=N3)C=3OC=CC=3)C=C2)CC1 HLGDACJOMIQDPH-UHFFFAOYSA-N 0.000 claims 1
• BSNSYNOHDOOAHQ-UHFFFAOYSA-N 10-[5-[4-(2,4-difluorophenyl)piperazin-1-yl]pentyl]-4-(furan-2-yl)-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCCCCN(CC1)CCN1C1=CC=C(F)C=C1F BSNSYNOHDOOAHQ-UHFFFAOYSA-N 0.000 claims 1
• DCFRAPHSNSCGKD-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-(4-pyridin-2-ylpiperazin-1-yl)ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=CC=N1 DCFRAPHSNSCGKD-UHFFFAOYSA-N 0.000 claims 1
• KLFCPCCZTOLRNS-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-(4-pyridin-3-ylpiperazin-1-yl)ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=CN=C1 KLFCPCCZTOLRNS-UHFFFAOYSA-N 0.000 claims 1
• VRLVUFOTTPHJHV-UHFFFAOYSA-N 4-(furan-2-yl)-10-[2-(4-pyridin-4-ylpiperazin-1-yl)ethyl]-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine Chemical compound C1=CC=2C3=NC(C=4OC=CC=4)=NN3C(N)=NC=2N1CCN(CC1)CCN1C1=CC=NC=C1 VRLVUFOTTPHJHV-UHFFFAOYSA-N 0.000 claims 1
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