JP2012515761A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- CFVLFWGACWTIKA-CQSZACIVSA-N 1-cyclopentyl-6-[(1R)-1-[3-(4-methoxyphenoxy)azetidin-1-yl]ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1OC1CN([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)C1 CFVLFWGACWTIKA-CQSZACIVSA-N 0.000 claims 1
- 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
- ZBSAHMIVDGTYMH-CYBMUJFWSA-N 1-cyclopentyl-6-[(1R)-1-[3-(5-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=C(C)C=N1 ZBSAHMIVDGTYMH-CYBMUJFWSA-N 0.000 claims 1
- UCINOQOQKMLJEM-CYBMUJFWSA-N 1-cyclopentyl-6-[(1R)-1-[3-(pyrimidin-5-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)C2CCCC2)CC1CC1=CN=CN=C1 UCINOQOQKMLJEM-CYBMUJFWSA-N 0.000 claims 1
- MORMQPVGXHXYKO-CQSZACIVSA-N 1-cyclopentyl-6-[(1R)-1-[3-[(3-fluorophenyl)methyl]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)CC1CC1=CC=CC(F)=C1 MORMQPVGXHXYKO-CQSZACIVSA-N 0.000 claims 1
- JFVDBURTBDBXSN-CYBMUJFWSA-N 1-cyclopentyl-6-[(1R)-1-[3-[3-(trifluoromethyl)phenoxy]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(F)(F)F)=C1 JFVDBURTBDBXSN-CYBMUJFWSA-N 0.000 claims 1
- LXXQIXFUWXTRJP-CYBMUJFWSA-N 1-cyclopentyl-6-[(1R)-1-[3-[4-(trifluoromethyl)phenoxy]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(C(F)(F)F)C=C1 LXXQIXFUWXTRJP-CYBMUJFWSA-N 0.000 claims 1
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 1
- XVWLCTVDVAVMEU-CRAIPNDOSA-N 2-[(3R)-1-[(1R)-1-(1-cyclopentyl-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl)ethyl]pyrrolidin-3-yl]oxybenzonitrile Chemical compound O([C@@H]1CCN(C1)[C@H](C)C=1NC(=O)C=2C=NN(C=2N=1)C1CCCC1)C1=CC=CC=C1C#N XVWLCTVDVAVMEU-CRAIPNDOSA-N 0.000 claims 1
- ZLQVCNYZYNKHFY-CQSZACIVSA-N 4-[1-[(1R)-1-(1-cyclopentyl-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl)ethyl]azetidin-3-yl]oxybenzonitrile Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1OC1=CC=C(C#N)C=C1 ZLQVCNYZYNKHFY-CQSZACIVSA-N 0.000 claims 1
- TWNQBWLGAFAMIT-VTBWFHPJSA-N 4-[1-[(1R)-1-(1-cyclopentyl-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl)ethyl]pyrrolidin-3-yl]-N,N-dimethylbenzamide Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CCC1C1=CC=C(C(=O)N(C)C)C=C1 TWNQBWLGAFAMIT-VTBWFHPJSA-N 0.000 claims 1
- BADVCPMBMBUEQL-OAHLLOKOSA-N 6-[(1R)-1-(3-benzylazetidin-1-yl)ethyl]-1-cyclopentyl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1CC1=CC=CC=C1 BADVCPMBMBUEQL-OAHLLOKOSA-N 0.000 claims 1
- OAAGCCBTGKKXDK-GFCCVEGCSA-N 6-[(1R)-1-[3-(2-chloro-5-fluorophenoxy)azetidin-1-yl]ethyl]-1-cyclopentyl-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(F)=CC=C1Cl OAAGCCBTGKKXDK-GFCCVEGCSA-N 0.000 claims 1
- IQRDNJXZWCVKSM-GICMACPYSA-N 6-[(1R)-1-[3-(2-chlorophenyl)pyrrolidin-1-yl]ethyl]-1-cyclopentyl-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=C1Cl IQRDNJXZWCVKSM-GICMACPYSA-N 0.000 claims 1
- IYNWPEUGVKTUQL-GFCCVEGCSA-N 6-[(1R)-1-[3-(2-methylpyrimidin-4-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=NC(C)=N1 IYNWPEUGVKTUQL-GFCCVEGCSA-N 0.000 claims 1
- RWXMPGCFTCWUAG-CYBMUJFWSA-N 6-[(1R)-1-[3-(3-chlorophenoxy)azetidin-1-yl]ethyl]-1-cyclopentyl-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(Cl)=C1 RWXMPGCFTCWUAG-CYBMUJFWSA-N 0.000 claims 1
- MJHHVYGUXBJBHB-IURRXHLWSA-N 6-[(1R)-1-[3-(3-chlorophenyl)pyrrolidin-1-yl]ethyl]-1-cyclopentyl-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(Cl)=C1 MJHHVYGUXBJBHB-IURRXHLWSA-N 0.000 claims 1
- NGXJCCRRROOSBL-CQSZACIVSA-N 6-[(1R)-1-[3-(4,6-dimethylpyrimidin-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)=CC(C)=N1 NGXJCCRRROOSBL-CQSZACIVSA-N 0.000 claims 1
- BSHCSDIWTCHFSE-CYBMUJFWSA-N 6-[(1R)-1-[3-(4-chlorophenoxy)azetidin-1-yl]ethyl]-1-cyclopentyl-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(Cl)C=C1 BSHCSDIWTCHFSE-CYBMUJFWSA-N 0.000 claims 1
- 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 1
- 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 1
- MSKLKBGHUUNXFW-CYBMUJFWSA-N 6-[(1R)-1-[3-(4-methylpyrimidin-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=CC(C)=N1 MSKLKBGHUUNXFW-CYBMUJFWSA-N 0.000 claims 1
- 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 1
- BAOGADIPJRLJQE-MRXNPFEDSA-N 6-[(1R)-1-[3-(5-chloropyrimidin-2-yl)azetidin-1-yl]propyl]-1-(oxan-4-yl)-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=NC=C(Cl)C=N1 BAOGADIPJRLJQE-MRXNPFEDSA-N 0.000 claims 1
- OYSKWFHGPUOALP-CYBMUJFWSA-N 6-[(1R)-1-[3-(5-methylpyrimidin-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(C)C=N1 OYSKWFHGPUOALP-CYBMUJFWSA-N 0.000 claims 1
- FBFNPBJYMDPIDC-QGZVFWFLSA-N 6-[(1R)-1-[3-(5-methylpyrimidin-2-yl)azetidin-1-yl]propyl]-1-(oxan-4-yl)-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=NC=C(C)C=N1 FBFNPBJYMDPIDC-QGZVFWFLSA-N 0.000 claims 1
- ASUDFHRCWAIRQN-KWCCSABGSA-N 6-[(1R)-1-[3-(6-bromopyridin-2-yl)pyrrolidin-1-yl]ethyl]-1-cyclopentyl-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(Br)=N1 ASUDFHRCWAIRQN-KWCCSABGSA-N 0.000 claims 1
- 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 1
- GLPWRUQSVIEUHA-LJQANCHMSA-N 6-[(1R)-1-[3-(6-methylpyridin-2-yl)azetidin-1-yl]propyl]-1-(oxan-4-yl)-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(C)=N1 GLPWRUQSVIEUHA-LJQANCHMSA-N 0.000 claims 1
- BCTYJKPLCGAGFI-CQSZACIVSA-N 6-[(1R)-1-[3-[(3-fluorophenyl)methyl]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)CC1CC1=CC=CC(F)=C1 BCTYJKPLCGAGFI-CQSZACIVSA-N 0.000 claims 1
- DXLLBBOOAFAHQM-GOEBONIOSA-N 6-[(1S)-1-[(3R)-3-(2-chlorophenoxy)pyrrolidin-1-yl]ethyl]-1-cyclopentyl-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=C1Cl DXLLBBOOAFAHQM-GOEBONIOSA-N 0.000 claims 1
- 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 1
- 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 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 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 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 230000006931 brain damage Effects 0.000 claims 1
- 231100000874 brain damage Toxicity 0.000 claims 1
- 208000029028 brain injury Diseases 0.000 claims 1
- DXZBQYCXLSGSRO-LDCVWXEPSA-N chembl2177503 Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CCC1C1=CC=CC=C1 DXZBQYCXLSGSRO-LDCVWXEPSA-N 0.000 claims 1
- 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 1
- 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 1
- FHBANDDJQJAZOQ-CQSZACIVSA-N chembl2180073 Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC1OC1=CC=CC=C1 FHBANDDJQJAZOQ-CQSZACIVSA-N 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims 1
- 150000003997 cyclic ketones Chemical class 0.000 claims 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 1
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims 1
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229960003530 donepezil Drugs 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229960003980 galantamine Drugs 0.000 claims 1
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000010348 incorporation Methods 0.000 claims 1
- 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 1
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims 1
- 229960004640 memantine Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 229960004136 rivastigmine Drugs 0.000 claims 1
- FSXOWOYOGDSZJW-UHFFFAOYSA-N spiro[3h-chromene-2,3'-azetidine]-4-one Chemical compound O1C2=CC=CC=C2C(=O)CC21CNC2 FSXOWOYOGDSZJW-UHFFFAOYSA-N 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229960001685 tacrine Drugs 0.000 claims 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20609209P | 2009-01-26 | 2009-01-26 | |
| US61/206,092 | 2009-01-26 | ||
| PCT/IB2010/050133 WO2010084438A1 (en) | 2009-01-26 | 2010-01-13 | Amino-heterocyclic compounds used as pde9 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012515761A JP2012515761A (ja) | 2012-07-12 |
| JP2012515761A5 true JP2012515761A5 (https=) | 2013-02-14 |
| JP5656874B2 JP5656874B2 (ja) | 2015-01-21 |
Family
ID=42062324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011547011A Expired - Fee Related JP5656874B2 (ja) | 2009-01-26 | 2010-01-13 | Ｐｄｅ９阻害剤として使用されるアミノヘテロ環化合物 |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US8278295B2 (https=) |
| EP (1) | EP2389382B1 (https=) |
| JP (1) | JP5656874B2 (https=) |
| KR (1) | KR101417237B1 (https=) |
| CN (1) | CN102292340B (https=) |
| AR (1) | AR074966A1 (https=) |
| AU (1) | AU2010207507B2 (https=) |
| CA (1) | CA2748864C (https=) |
| DK (1) | DK2389382T3 (https=) |
| ES (1) | ES2420860T3 (https=) |
| HR (1) | HRP20130530T1 (https=) |
| IL (2) | IL213923A (https=) |
| MX (1) | MX2011007862A (https=) |
| PL (1) | PL2389382T3 (https=) |
| PT (1) | PT2389382E (https=) |
| SG (1) | SG172805A1 (https=) |
| SI (1) | SI2389382T1 (https=) |
| TW (1) | TWI404721B (https=) |
| UY (1) | UY32391A (https=) |
| WO (1) | WO2010084438A1 (https=) |
| ZA (1) | ZA201105931B (https=) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| LT2889033T (lt) | 2008-11-19 | 2018-07-10 | Forum Pharmaceuticals Inc. | Šizofrenijos negatyvių simptomų gydymas (r)-7-chlor-n-(chinuklidin-3-il)benzo[b]tiofen-2-karboksamidu ir jo farmaciniu požiūriu priimtinomis druskomis |
| JP5808319B2 (ja) * | 2009-05-11 | 2015-11-10 | フォルム ファーマシューティカルズ、インコーポレイテッド | アセチルコリンエステラーゼ阻害剤と組み合わせた特定のα７ニコチン酸受容体を用いた認知障害の治療 |
| PE20170923A1 (es) | 2010-05-17 | 2017-07-12 | Forum Pharmaceuticals Inc | Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin-3-il)benzo[b]tiofeno-2-carboxamida monohidratado |
| KR20130097178A (ko) | 2010-09-07 | 2013-09-02 | 아스텔라스세이야쿠 가부시키가이샤 | 퀴녹살린 화합물 |
| RS54834B1 (sr) | 2010-09-07 | 2016-10-31 | Astellas Pharma Inc | Jedinjenja pirazolokvinolina |
| BR112015007731B1 (pt) | 2011-10-10 | 2022-05-31 | H. Lundbeck A/S | Composto, composição farmacêutica que o compreende e uso do mesmo |
| BR112014018199A8 (pt) | 2012-01-26 | 2021-03-02 | H Lundbeck As | inibidores da pde9 com cadeia principal imidazo triazinona, composição farmacêutica que os compreende, uso dos referidos inibidores e processo para sua preparação |
| CN104093310A (zh) | 2012-02-03 | 2014-10-08 | 泰华制药工业有限公司 | 拉喹莫德用于治疗一线抗TNFα疗法失败的克罗恩氏病患者的用途 |
| EP3461481A1 (en) | 2012-05-08 | 2019-04-03 | Forum Pharmaceuticals Inc. | Methods of maintaining, treating or improving cognitive function |
| 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 |
| WO2014024125A1 (en) | 2012-08-08 | 2014-02-13 | Celon Pharma S.A. | Pyrazolo[4,3-d]pyrimidin-7(6h)-one derivatives as pde9 inhibitors |
| TW201410244A (zh) * | 2012-08-13 | 2014-03-16 | Teva Pharma | 用於治療ｇａｂａ媒介之疾病之拉喹莫德（ｌａｑｕｉｎｉｍｏｄ） |
| WO2014063105A1 (en) * | 2012-10-19 | 2014-04-24 | Celus Pharmaceuticals, Inc. | Vitamin d analogues for the treatment of a neurological disorder |
| CN103207246B (zh) * | 2012-12-21 | 2017-10-10 | 北京万全德众医药生物技术有限公司 | 一种用液相色谱法分离测定鲁拉西酮及其光学异构体的方法 |
| EP3139924A4 (en) * | 2014-05-06 | 2018-03-07 | Anthony G. Visco | Methods of treating or preventing preterm labor |
| RU2017107521A (ru) | 2014-08-27 | 2018-10-01 | Ф. Хоффманн-Ля Рош Аг | Замещенные производные азетидина в качестве лигандов рецепторов следовых аминов taar |
| TW201629064A (zh) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之三唑並吡酮 |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| PT3865484T (pt) | 2015-07-07 | 2024-01-30 | H Lundbeck As | Inibidor da pde9 com esqueleto de imidazo pirazinona para tratamento de doenças periféricas |
| US10376504B2 (en) | 2015-07-29 | 2019-08-13 | Merck, Sharp & Dohme Corp. | Substituted quinolinones as PDE9 inhibitors |
| WO2017019724A1 (en) * | 2015-07-29 | 2017-02-02 | Merck Sharp & Dohme Corp. | Phenyl-cyanoquinolinone pde9 inhibitors |
| WO2017019726A1 (en) * | 2015-07-29 | 2017-02-02 | Merck Sharp & Dohme Corp. | Oxy-cyanoquinolinone pde9 inhibitors |
| JP6983161B2 (ja) | 2015-09-15 | 2021-12-17 | プラクシス・バイオリサーチ・エルエルシー | フェンカンファミンのプロドラッグ |
| CN105467028A (zh) * | 2015-11-18 | 2016-04-06 | 北京万全德众医药生物技术有限公司 | 气相色谱法分离测定鲁拉西酮中间体光学异构体的方法 |
| CN105669680B (zh) * | 2016-03-24 | 2018-02-23 | 南京药捷安康生物科技有限公司 | 吡咯并[2,1‑f][1,2,4]三嗪‑4(1H)‑酮衍生物类PDE9A抑制剂 |
| TWI729109B (zh) | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 作爲PDE1抑制劑的1,5-二氫-4H-吡唑并[3,4-d]嘧啶-4-酮和1,5-二氫-4H-吡唑并[4,3-c]吡啶-4-酮 |
| MX2018016127A (es) | 2016-07-06 | 2019-05-30 | Imara Inc | Inhibidores de pde9 para el tratamiento de enfermedades perifericas. |
| WO2018073251A1 (en) * | 2016-10-18 | 2018-04-26 | H. Lundbeck A/S | Imidazopyrazinones, pyrazolopyrimidinones and pyrazolopyridinones as pde1 inhibitors |
| WO2018078042A1 (en) | 2016-10-28 | 2018-05-03 | H. Lundbeck A/S | Combination treatments comprising administration of imidazopyrazinones |
| AU2017350473A1 (en) | 2016-10-28 | 2019-04-18 | H. Lundbeck A/S | Combination treatments comprising imidazopyrazinones for the treatment of psychiatric and/or cognitive disorders |
| EP3541784B1 (en) | 2016-11-18 | 2023-09-13 | Integrative Research Laboratories Sweden AB | Novel azetidine derivatives useful as modulators of cortical catecholaminergic neurotransmission |
| KR102590848B1 (ko) | 2016-12-28 | 2023-10-19 | 다트 뉴로사이언스, 엘엘씨 | Pde2 억제제로서 치환된 피라졸로피리미디논 화합물 |
| JP7053645B2 (ja) * | 2017-02-23 | 2022-04-12 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 化合物ｉｉｉの新しい医学的使用 |
| CN106957300A (zh) * | 2017-04-12 | 2017-07-18 | 苏州汉德创宏生化科技有限公司 | 抗肿瘤杂环药物中间体2‑(3‑氮杂环丁基）吡啶二盐酸盐的合成方法 |
| MX2019013626A (es) | 2017-05-22 | 2020-01-13 | Topadur Pharma Ag | Modo de accion dual novedoso de activadores de guanilato ciclasa solubles e inhibidores de fosfodiesterasa y usos de los mismos. |
| CN115746003B (zh) * | 2017-05-26 | 2024-08-09 | 卡都瑞恩医药公司 | 制备和使用pde9抑制剂的方法 |
| KR20200010211A (ko) | 2017-06-01 | 2020-01-30 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | Pde9 저해제를 포함하는 약제학적 조성물 |
| KR20200010220A (ko) | 2017-06-01 | 2020-01-30 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 피라졸로퀴놀린 유도체를 함유하는 루이소체 질병 치료제 |
| RU2019135834A (ru) | 2017-06-01 | 2021-07-13 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Терапевтическое средство для лечения деменции, представляющее собой комбинацию производного пиразолохинолина и донепезила |
| SG10202113199RA (en) * | 2017-06-01 | 2021-12-30 | Eisai R&D Man Co Ltd | Dementia therapeutic agent combining pyrazoloquinoline derivative and memantine |
| AU2018281131B2 (en) | 2017-06-08 | 2022-01-20 | Merck Sharp & Dohme Corp. | Pyrazolopyrimidine PDE9 inhibitors |
| DK3717488T3 (da) | 2017-11-27 | 2021-12-13 | Dart Neuroscience Llc | Substituerede furanopyrimidinforbindelser som pde1-inhibitorer |
| CA3100988A1 (en) | 2018-05-25 | 2019-11-28 | Imara Inc. | Monohydrate and crystalline forms of 6-[(3s,4s)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-3-tetrahydropyran-4-yl-7h-imidazo[1,5-a]pyrazin-8-one |
| CA3110680A1 (en) | 2018-08-31 | 2020-03-05 | Imara Inc. | Pde9 inhibitors for treating sickle cell disease |
| WO2020182076A1 (zh) * | 2019-03-08 | 2020-09-17 | 南京药捷安康生物科技有限公司 | 磷酸二酯酶抑制剂的用途 |
| EP4003342A1 (en) * | 2019-07-29 | 2022-06-01 | Constellation Pharmaceuticals, Inc. | Compounds for use in treating neurological disorders |
| CN120897742A (zh) * | 2022-11-15 | 2025-11-04 | 福睿德姆生物科学公司 | 通过抑制9型磷酸二酯酶增强血清素能致幻药物在治疗或预防某些神经精神障碍中的功效 |
| AU2024326748A1 (en) * | 2023-08-18 | 2026-04-02 | Katholieke Universiteit Leuven | 1,3-dihydro-2h-pyrrolo[3,4-c]quinoline derivatives as cgas inhibitors for the treatment of inflammatory and/or autoimmune diseases |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1177960A (zh) * | 1995-03-10 | 1998-04-01 | 圣诺菲药品有限公司 | 6－取代的吡唑并[3,4－d]嘧啶－4－酮及其组合物和使用方法 |
| GB9722520D0 (en) * | 1997-10-24 | 1997-12-24 | Pfizer Ltd | Compounds |
| JP2005508978A (ja) | 2001-11-02 | 2005-04-07 | ファイザー・プロダクツ・インク | Ｐｄｅ９阻害薬によるインスリン抵抗性症候群及び２型糖尿病の治療 |
| US20030195205A1 (en) * | 2001-11-02 | 2003-10-16 | Pfizer Inc. | PDE9 inhibitors for treating cardiovascular disorders |
| SE0103795D0 (sv) | 2001-11-02 | 2001-11-02 | Astrazeneca Ab | Compounds and method for the treatment of överactive bladder |
| HN2002000317A (es) * | 2001-11-02 | 2003-05-21 | Pfizer | Inhibidores de pde9 para tratamiento de trastornos cardiovasculares |
| WO2003049527A2 (en) * | 2001-12-06 | 2003-06-19 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| RS52166B (sr) * | 2007-05-11 | 2012-08-31 | Pfizer Inc. | Amino-heterociklična jedinjenja |
| UA105362C2 (en) * | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
-
2009
- 2009-12-31 TW TW098146481A patent/TWI404721B/zh not_active IP Right Cessation
-
2010
- 2010-01-13 KR KR1020117019758A patent/KR101417237B1/ko not_active Expired - Fee Related
- 2010-01-13 EP EP10701921.8A patent/EP2389382B1/en not_active Not-in-force
- 2010-01-13 JP JP2011547011A patent/JP5656874B2/ja not_active Expired - Fee Related
- 2010-01-13 AU AU2010207507A patent/AU2010207507B2/en not_active Ceased
- 2010-01-13 DK DK10701921.8T patent/DK2389382T3/da active
- 2010-01-13 SG SG2011047594A patent/SG172805A1/en unknown
- 2010-01-13 CN CN201080005394.XA patent/CN102292340B/zh not_active Expired - Fee Related
- 2010-01-13 SI SI201030250T patent/SI2389382T1/sl unknown
- 2010-01-13 PL PL10701921T patent/PL2389382T3/pl unknown
- 2010-01-13 HR HRP20130530AT patent/HRP20130530T1/hr 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 ES ES10701921T patent/ES2420860T3/es active Active
- 2010-01-13 MX MX2011007862A patent/MX2011007862A/es active IP Right Grant
- 2010-01-13 WO PCT/IB2010/050133 patent/WO2010084438A1/en not_active Ceased
- 2010-01-25 UY UY0001032391A patent/UY32391A/es not_active Application Discontinuation
- 2010-01-25 AR ARP100100153A patent/AR074966A1/es unknown
- 2010-01-26 US US12/693,480 patent/US8278295B2/en not_active Expired - Fee Related
-
2011
- 2011-07-04 IL IL213923A patent/IL213923A/en not_active IP Right Cessation
- 2011-08-12 ZA ZA2011/05931A patent/ZA201105931B/en unknown
-
2012
- 2012-08-31 US US13/600,522 patent/US8618117B2/en not_active Expired - Fee Related
-
2013
- 2013-11-27 US US14/091,404 patent/US20140088081A1/en not_active Abandoned
-
2016
- 2016-07-21 IL IL246882A patent/IL246882A0/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012515761A5 (https=) | ||
| JP5656874B2 (ja) | Ｐｄｅ９阻害剤として使用されるアミノヘテロ環化合物 | |
| US20250026764A1 (en) | Positive allosteric modulators of the muscarinic acetylcholine receptor m4 | |
| CN104093720B (zh) | 具有咪唑并三嗪酮骨架的pde9抑制剂 | |
| JP6229042B2 (ja) | ビヘテロアリール化合物及びその使用 | |
| JP2019523233A5 (https=) | ||
| RU2014139601A (ru) | Ингибиторы серин/треониновых киназ | |
| JP2017510554A5 (https=) | ||
| JP2012501312A5 (https=) | ||
| JP2011519891A5 (https=) | ||
| JP2017524007A5 (https=) | ||
| JP2009507758A5 (https=) | ||
| RU2010106974A (ru) | Ариловые эфиры пирролидина в качестве антагонистов рецепторов nk3 | |
| JP2017531672A5 (https=) | ||
| EA031201B1 (ru) | Соединения имидазопиридазина | |
| RU2012141607A (ru) | Производные аминоинданов, их получение и применение в терапии | |
| CA3106470A1 (en) | T-type calcium channel blocker | |
| US9226916B2 (en) | Pyrrolidine derivatives | |
| EP3950059A1 (en) | Use of t-type calcium channel blocker for treating pruritus | |
| RU2006128613A (ru) | Производные диазаспиропиперидина | |
| CN101365678A (zh) | 可用于治疗h3受体相关病症的h3受体调节剂 | |
| RU2021113492A (ru) | Новые аминопиримидонилпиперидинильные производные, способ их получения и содержащие их фармацевтические композиции |