JP2012515761A5 - - Google Patents
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- Publication number
- JP2012515761A5 JP2012515761A5 JP2011547011A JP2011547011A JP2012515761A5 JP 2012515761 A5 JP2012515761 A5 JP 2012515761A5 JP 2011547011 A JP2011547011 A JP 2011547011A JP 2011547011 A JP2011547011 A JP 2011547011A JP 2012515761 A5 JP2012515761 A5 JP 2012515761A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- dihydro
- ethyl
- pyrimidin
- cyclopentyl
- 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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- 125000005843 halogen group Chemical group 0.000 claims 22
- -1 cyano, carboxy Chemical group 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 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 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 2
- 239000008177 pharmaceutical agent Substances 0.000 claims 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
- 230000001737 promoting effect Effects 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=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
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 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 1
- 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 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
- 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 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
- 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 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
- 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 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
- ZEZNUIVVJLKEHG-WBVHZDCISA-N 1-cyclopentyl-6-[(1R)-1-[(3S)-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-WBVHZDCISA-N 0.000 claims 1
- GMXXJPOWTNNBRW-AAFJCEBUSA-N 1-cyclopentyl-6-[(1R)-1-[3-(2,3-dimethoxyphenyl)pyrrolidin-1-yl]ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC(C2CN(CC2)[C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)=C1OC GMXXJPOWTNNBRW-AAFJCEBUSA-N 0.000 claims 1
- LQVQFLVRGFFRQS-GFCCVEGCSA-N 1-cyclopentyl-6-[(1R)-1-[3-(2,5-dichlorophenoxy)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)C2CCCC2)CC1OC1=CC(Cl)=CC=C1Cl LQVQFLVRGFFRQS-GFCCVEGCSA-N 0.000 claims 1
- PTFRIDOVQHEPEL-AAFJCEBUSA-N 1-cyclopentyl-6-[(1R)-1-[3-(2,5-dimethoxyphenyl)pyrrolidin-1-yl]ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=C(OC)C(C2CN(CC2)[C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)=C1 PTFRIDOVQHEPEL-AAFJCEBUSA-N 0.000 claims 1
- PPECTGCFLSGBEM-GICMACPYSA-N 1-cyclopentyl-6-[(1R)-1-[3-(2-fluorophenyl)pyrrolidin-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=CC=C1F PPECTGCFLSGBEM-GICMACPYSA-N 0.000 claims 1
- JZIFWHUNGDCOGI-GFCCVEGCSA-N 1-cyclopentyl-6-[(1R)-1-[3-(2-methylpyrimidin-4-yl)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)C2CCCC2)CC1C1=CC=NC(C)=N1 JZIFWHUNGDCOGI-GFCCVEGCSA-N 0.000 claims 1
- XVIVDIQGMNARSU-GFCCVEGCSA-N 1-cyclopentyl-6-[(1R)-1-[3-(3,4-difluorophenoxy)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)C2CCCC2)CC1OC1=CC=C(F)C(F)=C1 XVIVDIQGMNARSU-GFCCVEGCSA-N 0.000 claims 1
- KQKSCUBNEPYAIR-YAOANENCSA-N 1-cyclopentyl-6-[(1R)-1-[3-(3-methoxyphenyl)-3-methylpyrrolidin-1-yl]ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC(C2(C)CN(CC2)[C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)=C1 KQKSCUBNEPYAIR-YAOANENCSA-N 0.000 claims 1
- AVCZTAZZAIMTDD-OAHLLOKOSA-N 1-cyclopentyl-6-[(1R)-1-[3-(3-methylphenoxy)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)C2CCCC2)CC1OC1=CC=CC(C)=C1 AVCZTAZZAIMTDD-OAHLLOKOSA-N 0.000 claims 1
- UZRHCNUDVUCVJT-CQSZACIVSA-N 1-cyclopentyl-6-[(1R)-1-[3-(4,6-dimethylpyrimidin-2-yl)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)C2CCCC2)CC1C1=NC(C)=CC(C)=N1 UZRHCNUDVUCVJT-CQSZACIVSA-N 0.000 claims 1
- QAEVQXQXFWVYDP-CYBMUJFWSA-N 1-cyclopentyl-6-[(1R)-1-[3-(4-fluorophenoxy)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)C2CCCC2)CC1OC1=CC=C(F)C=C1 QAEVQXQXFWVYDP-CYBMUJFWSA-N 0.000 claims 1
- KHQDLQQDGGVJAZ-IURRXHLWSA-N 1-cyclopentyl-6-[(1R)-1-[3-(4-fluorophenyl)pyrrolidin-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=C(F)C=C1 KHQDLQQDGGVJAZ-IURRXHLWSA-N 0.000 claims 1
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- VFQBJSVQLWNMPH-CYBMUJFWSA-N 1-cyclopentyl-6-[(1R)-1-[3-(4-methylpyrimidin-2-yl)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)C2CCCC2)CC1C1=NC=CC(C)=N1 VFQBJSVQLWNMPH-CYBMUJFWSA-N 0.000 claims 1
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| CN102786525B (zh) * | 2012-08-08 | 2014-12-17 | 中山大学 | N-取代吡唑并[3,4-d]嘧啶酮类化合物、其制备方法及其应用 |
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2009
- 2009-12-31 TW TW098146481A patent/TWI404721B/zh not_active IP Right Cessation
-
2010
- 2010-01-13 SI SI201030250T patent/SI2389382T1/sl unknown
- 2010-01-13 PL PL10701921T patent/PL2389382T3/pl unknown
- 2010-01-13 CA CA2748864A patent/CA2748864C/en not_active Expired - Fee Related
- 2010-01-13 PT PT107019218T patent/PT2389382E/pt unknown
- 2010-01-13 HR HRP20130530AT patent/HRP20130530T1/hr unknown
- 2010-01-13 DK DK10701921.8T patent/DK2389382T3/da active
- 2010-01-13 JP JP2011547011A patent/JP5656874B2/ja not_active Expired - Fee Related
- 2010-01-13 AU AU2010207507A patent/AU2010207507B2/en not_active Ceased
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- 2010-01-13 WO PCT/IB2010/050133 patent/WO2010084438A1/en not_active Ceased
- 2010-01-13 ES ES10701921T patent/ES2420860T3/es active Active
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- 2010-01-25 UY UY0001032391A patent/UY32391A/es not_active Application Discontinuation
- 2010-01-25 AR ARP100100153A patent/AR074966A1/es unknown
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