JP5656874B2 - Ｐｄｅ９阻害剤として使用されるアミノヘテロ環化合物 - Google Patents

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Publication number

JP5656874B2

JP5656874B2 JP2011547011A JP2011547011A JP5656874B2 JP 5656874 B2 JP5656874 B2 JP 5656874B2 JP 2011547011 A JP2011547011 A JP 2011547011A JP 2011547011 A JP2011547011 A JP 2011547011A JP 5656874 B2 JP5656874 B2 JP 5656874B2

Authority

JP

Japan

Prior art keywords

pyrazolo

dihydro

ethyl

pyrimidin

cyclopentyl

Prior art date

2009-01-26

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.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 175
• 229940076380 PDE9 inhibitor Drugs 0.000 title description 7
• -1 cyano, carboxy Chemical group 0.000 claims description 124
• 239000000203 mixture Substances 0.000 claims description 100
• 150000003839 salts Chemical class 0.000 claims description 44
• 125000005843 halogen group Chemical group 0.000 claims description 43
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 241000124008 Mammalia Species 0.000 claims description 24
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 125000001188 haloalkyl group Chemical group 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 17
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 12
• 150000002431 hydrogen Chemical class 0.000 claims description 12
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 230000004770 neurodegeneration Effects 0.000 claims description 6
• 208000010877 cognitive disease Diseases 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 201000010099 disease Diseases 0.000 claims description 5
• 230000001737 promoting effect Effects 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 238000011084 recovery Methods 0.000 claims description 5
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 208000029028 brain injury Diseases 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 210000005036 nerve Anatomy 0.000 claims description 4
• 230000008439 repair process Effects 0.000 claims description 4
• 208000028698 Cognitive impairment Diseases 0.000 claims description 3
• XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 150000003997 cyclic ketones Chemical class 0.000 claims description 3
• ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 3
• 230000002708 enhancing effect Effects 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 229960004640 memantine Drugs 0.000 claims description 3
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
• 239000008177 pharmaceutical agent Substances 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000002098 pyridazinyl 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
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• YXFFJIRNASUZLY-CQSZACIVSA-N 1-(oxan-4-yl)-6-[(1R)-1-(3-phenylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=CC=CC=C1 YXFFJIRNASUZLY-CQSZACIVSA-N 0.000 claims description 2
• RELOGXSWGZMVBY-GFCCVEGCSA-N 1-(oxan-4-yl)-6-[(1R)-1-(3-pyrazin-2-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=CN=CC=N1 RELOGXSWGZMVBY-GFCCVEGCSA-N 0.000 claims description 2
• RTNBHTRPRSBFON-OAHLLOKOSA-N 1-(oxan-4-yl)-6-[(1R)-1-(3-quinolin-2-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@H](N3CC(C3)C=3N=C4C=CC=CC4=CC=3)C)=NC=2N1C1CCOCC1 RTNBHTRPRSBFON-OAHLLOKOSA-N 0.000 claims description 2
• RWEDODZULSJMIG-LLVKDONJSA-N 1-cyclobutyl-6-[(1R)-1-(3-pyrimidin-2-yloxyazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCC2)CC1OC1=NC=CC=N1 RWEDODZULSJMIG-LLVKDONJSA-N 0.000 claims description 2
• YFLRWBCQIACXIL-GFCCVEGCSA-N 1-cyclopentyl-6-[(1R)-1-(3-pyrimidin-2-yloxyazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1OC1=NC=CC=N1 YFLRWBCQIACXIL-GFCCVEGCSA-N 0.000 claims description 2
• XYRJHICAYZEKEV-CYBMUJFWSA-N 6-[(1R)-1-[3-(4-fluorophenoxy)azetidin-1-yl]ethyl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1OC1=CC=C(F)C=C1 XYRJHICAYZEKEV-CYBMUJFWSA-N 0.000 claims description 2
• CKDFSQLRMILYEF-CQSZACIVSA-N 6-[(1R)-1-[3-(4-methylpyridin-2-yl)azetidin-1-yl]ethyl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=CC(C)=CC=N1 CKDFSQLRMILYEF-CQSZACIVSA-N 0.000 claims description 2
• CFRCSPOWERHXIS-LLVKDONJSA-N 6-[(1R)-1-[3-(5-chloropyrimidin-2-yl)azetidin-1-yl]ethyl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=NC=C(Cl)C=N1 CFRCSPOWERHXIS-LLVKDONJSA-N 0.000 claims description 2
• ZMJGKMRHKFVVGS-CQSZACIVSA-N 6-[(1R)-1-[3-(6-methylpyridin-2-yl)azetidin-1-yl]ethyl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=CC=CC(C)=N1 ZMJGKMRHKFVVGS-CQSZACIVSA-N 0.000 claims description 2
• ACGQEEIBQUHXCU-UHFFFAOYSA-N 6-[1-(3-phenoxyazetidin-1-yl)ethyl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC(C)N1N=CC(C(N2)=O)=C1N=C2C(C)N(C1)CC1OC1=CC=CC=C1 ACGQEEIBQUHXCU-UHFFFAOYSA-N 0.000 claims description 2
• XDDLNUXMSGCHOO-UHFFFAOYSA-N 6-[cyclopropyl-(3-phenoxyazetidin-1-yl)methyl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC(C(C3CC3)N3CC(C3)OC=3C=CC=CC=3)=NC=2N1C1CCOCC1 XDDLNUXMSGCHOO-UHFFFAOYSA-N 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 230000006931 brain damage Effects 0.000 claims description 2
• 231100000874 brain damage Toxicity 0.000 claims description 2
• DNRDSQSNTVMZSL-UHFFFAOYSA-N chembl2180067 Chemical compound N=1C=2N(C3CCOCC3)N=CC=2C(=O)NC=1C(C)N(C1)CC1OC1=CC=C(F)C(C#N)=C1 DNRDSQSNTVMZSL-UHFFFAOYSA-N 0.000 claims description 2
• HJXAXXUTIBEZHT-GFCCVEGCSA-N chembl2180070 Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1C1=NC=CC=N1 HJXAXXUTIBEZHT-GFCCVEGCSA-N 0.000 claims description 2
• 230000001149 cognitive effect Effects 0.000 claims description 2
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 2
• 238000010348 incorporation Methods 0.000 claims description 2
• JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 claims description 2
• 229960004136 rivastigmine Drugs 0.000 claims description 2
• 229960001685 tacrine Drugs 0.000 claims description 2
• YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
• ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims 2
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
• DWZDUFGEUGAAQS-BVGQSLNGSA-N (3aR,9bR)-2-[(1R)-1-(1-cyclopentyl-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl)ethyl]-3,3a,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinolin-4-one Chemical compound N1=CC=2C(=O)NC([C@H](N3C[C@@H]4[C@@H](C(NC5=CC=CC=C54)=O)C3)C)=NC=2N1C1CCCC1 DWZDUFGEUGAAQS-BVGQSLNGSA-N 0.000 claims 1
• MCYVOYCFFITAAD-UUWFMWQGSA-N (3aR,9bR)-8-chloro-2-[(1R)-1-(1-cyclopentyl-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl)ethyl]-3,3a,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinolin-4-one Chemical compound N1=CC=2C(=O)NC([C@H](N3C[C@@H]4[C@@H](C(NC5=CC=C(Cl)C=C54)=O)C3)C)=NC=2N1C1CCCC1 MCYVOYCFFITAAD-UUWFMWQGSA-N 0.000 claims 1
• JCZXZSYXYZCZII-GFCCVEGCSA-N 1-(oxan-4-yl)-6-[(1R)-1-(3-pyridazin-3-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=CC=CN=N1 JCZXZSYXYZCZII-GFCCVEGCSA-N 0.000 claims 1
• GOACIOJCSGPOHS-CYBMUJFWSA-N 1-(oxan-4-yl)-6-[(1R)-1-(3-pyridin-2-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=CC=CC=N1 GOACIOJCSGPOHS-CYBMUJFWSA-N 0.000 claims 1
• COKQFQABDOCGAG-GOSISDBHSA-N 1-(oxan-4-yl)-6-[(1R)-1-(3-pyridin-2-ylazetidin-1-yl)propyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](CC)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=CC=CC=N1 COKQFQABDOCGAG-GOSISDBHSA-N 0.000 claims 1
• JSLVZYPNFZWWKI-CYBMUJFWSA-N 1-(oxan-4-yl)-6-[(1R)-1-(3-pyridin-3-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=CC=CN=C1 JSLVZYPNFZWWKI-CYBMUJFWSA-N 0.000 claims 1
• WFLIGVUCLCPZPL-CYBMUJFWSA-N 1-(oxan-4-yl)-6-[(1R)-1-(3-pyridin-4-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=CC=NC=C1 WFLIGVUCLCPZPL-CYBMUJFWSA-N 0.000 claims 1
• ISJQRAORYKTTJZ-GFCCVEGCSA-N 1-(oxan-4-yl)-6-[(1R)-1-(3-pyrimidin-2-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=NC=CC=N1 ISJQRAORYKTTJZ-GFCCVEGCSA-N 0.000 claims 1
• WRNMMAKGEZGGFH-GFCCVEGCSA-N 1-(oxan-4-yl)-6-[(1R)-1-(3-pyrimidin-5-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1C1=CN=CN=C1 WRNMMAKGEZGGFH-GFCCVEGCSA-N 0.000 claims 1
• OVHFNCGGAUKBHK-CYBMUJFWSA-N 1-(oxan-4-yl)-6-[(1R)-1-[3-(pyrimidin-2-ylmethyl)azetidin-1-yl]ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1CC1=NC=CC=N1 OVHFNCGGAUKBHK-CYBMUJFWSA-N 0.000 claims 1
• DCRBUTIWSGKJCC-GFCCVEGCSA-N 1-cyclopentyl-6-[(1R)-1-(3-pyridazin-3-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1C1=CC=CN=N1 DCRBUTIWSGKJCC-GFCCVEGCSA-N 0.000 claims 1
• AVFLLFMZYVULBF-CYBMUJFWSA-N 1-cyclopentyl-6-[(1R)-1-(3-pyridin-2-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1C1=CC=CC=N1 AVFLLFMZYVULBF-CYBMUJFWSA-N 0.000 claims 1
• SBHALWAIZVZOLF-CYBMUJFWSA-N 1-cyclopentyl-6-[(1R)-1-(3-pyridin-3-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1C1=CC=CN=C1 SBHALWAIZVZOLF-CYBMUJFWSA-N 0.000 claims 1
• AGVGRWHSTZUYHG-CYBMUJFWSA-N 1-cyclopentyl-6-[(1R)-1-(3-pyridin-3-yloxyazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1OC1=CC=CN=C1 AGVGRWHSTZUYHG-CYBMUJFWSA-N 0.000 claims 1
• ODRVYHSPGHESOR-CYBMUJFWSA-N 1-cyclopentyl-6-[(1R)-1-(3-pyridin-4-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1C1=CC=NC=C1 ODRVYHSPGHESOR-CYBMUJFWSA-N 0.000 claims 1
• KDKCYBNYZLSUIH-IURRXHLWSA-N 1-cyclopentyl-6-[(1R)-1-(3-pyridin-4-ylpyrrolidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CCC1C1=CC=NC=C1 KDKCYBNYZLSUIH-IURRXHLWSA-N 0.000 claims 1
• MUIRDYRQXQZONR-KWCCSABGSA-N 1-cyclopentyl-6-[(1R)-1-(3-pyrimidin-2-ylpyrrolidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CCC1C1=NC=CC=N1 MUIRDYRQXQZONR-KWCCSABGSA-N 0.000 claims 1
• DVOSIFDHHXDFHZ-GFCCVEGCSA-N 1-cyclopentyl-6-[(1R)-1-(3-pyrimidin-4-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1C1=CC=NC=N1 DVOSIFDHHXDFHZ-GFCCVEGCSA-N 0.000 claims 1
• VZTGHOXKKCCFNO-GFCCVEGCSA-N 1-cyclopentyl-6-[(1R)-1-(3-pyrimidin-5-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1C1=CN=CN=C1 VZTGHOXKKCCFNO-GFCCVEGCSA-N 0.000 claims 1
• RUAXDPKWKKZUQZ-OAHLLOKOSA-N 1-cyclopentyl-6-[(1R)-1-(3-quinolin-2-ylazetidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@H](N3CC(C3)C=3N=C4C=CC=CC4=CC=3)C)=NC=2N1C1CCCC1 RUAXDPKWKKZUQZ-OAHLLOKOSA-N 0.000 claims 1
• ZEZNUIVVJLKEHG-NVXWUHKLSA-N 1-cyclopentyl-6-[(1R)-1-[(3R)-3-(2-methoxyphenoxy)pyrrolidin-1-yl]ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1O[C@H]1CN([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1 ZEZNUIVVJLKEHG-NVXWUHKLSA-N 0.000 claims 1
• WACOUQHGZIVPDS-SJLPKXTDSA-N 1-cyclopentyl-6-[(1R)-1-[(3R)-3-(2-methylphenoxy)pyrrolidin-1-yl]ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound O([C@@H]1CCN(C1)[C@H](C)C=1NC(=O)C=2C=NN(C=2N=1)C1CCCC1)C1=CC=CC=C1C WACOUQHGZIVPDS-SJLPKXTDSA-N 0.000 claims 1
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