JP2019517996A5 - - Google Patents
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- JP2019517996A5 JP2019517996A5 JP2018550733A JP2018550733A JP2019517996A5 JP 2019517996 A5 JP2019517996 A5 JP 2019517996A5 JP 2018550733 A JP2018550733 A JP 2018550733A JP 2018550733 A JP2018550733 A JP 2018550733A JP 2019517996 A5 JP2019517996 A5 JP 2019517996A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrazolo
- pyridin
- tetrahydropyran
- group
- 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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- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003566 oxetanyl group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- LWAQPJWARNOJEY-UHFFFAOYSA-N COC1=CC=C(CN2C(C3=C(C=C2C)N(N=C3)C2CCOCC2)=O)C=C1 Chemical compound COC1=CC=C(CN2C(C3=C(C=C2C)N(N=C3)C2CCOCC2)=O)C=C1 LWAQPJWARNOJEY-UHFFFAOYSA-N 0.000 claims description 4
- 208000028698 Cognitive impairment Diseases 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229920006395 saturated elastomer Chemical group 0.000 claims description 3
- TXMZJMRBPNQFRI-UHFFFAOYSA-N 5-[(2-fluorophenyl)methyl]-6-methyl-1-(oxan-4-yl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=NC2=C(C=NN2C2CCOCC2)C(=O)N1CC1=C(F)C=CC=C1 TXMZJMRBPNQFRI-UHFFFAOYSA-N 0.000 claims description 2
- VACQVANOFNLZEL-UHFFFAOYSA-N 5-[(3-fluorophenyl)methyl]-6-methyl-1-(oxan-4-yl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=NC2=C(C=NN2C2CCOCC2)C(=O)N1CC1=CC(F)=CC=C1 VACQVANOFNLZEL-UHFFFAOYSA-N 0.000 claims description 2
- WRYMSMMHCLFPFM-UHFFFAOYSA-N 5-benzyl-6-methyl-1-(oxan-4-yl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=NC2=C(C=NN2C2CCOCC2)C(=O)N1CC1=CC=CC=C1 WRYMSMMHCLFPFM-UHFFFAOYSA-N 0.000 claims description 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 2
- 208000014644 Brain disease Diseases 0.000 claims description 2
- IVICMAQJTMYPDI-UHFFFAOYSA-N C(C)(C)C=1N(C(C2=C(N=1)N(N=C2)C1CCOCC1)=O)CC1=CC=C(C=C1)OC Chemical compound C(C)(C)C=1N(C(C2=C(N=1)N(N=C2)C1CCOCC1)=O)CC1=CC=C(C=C1)OC IVICMAQJTMYPDI-UHFFFAOYSA-N 0.000 claims description 2
- LCELOTJXOWMXKN-UHFFFAOYSA-N C(C)(C)N1N=CC=2C(N(C(=CC=21)C)CC1=CC=C(C=C1)OC)=O Chemical compound C(C)(C)N1N=CC=2C(N(C(=CC=21)C)CC1=CC=C(C=C1)OC)=O LCELOTJXOWMXKN-UHFFFAOYSA-N 0.000 claims description 2
- LZTQRMBMZGEDRE-UHFFFAOYSA-N C(C)N1N=CC=2C(N(C(=CC=21)C)CC1=CC=C(C=C1)OC)=O Chemical compound C(C)N1N=CC=2C(N(C(=CC=21)C)CC1=CC=C(C=C1)OC)=O LZTQRMBMZGEDRE-UHFFFAOYSA-N 0.000 claims description 2
- YXOLEIZBMQWRJW-UHFFFAOYSA-N C(C1=CC=CC=C1)C=1N(C(C2=C(N=1)N(N=C2)C1CCOCC1)=O)CC1CCCCC1 Chemical compound C(C1=CC=CC=C1)C=1N(C(C2=C(N=1)N(N=C2)C1CCOCC1)=O)CC1CCCCC1 YXOLEIZBMQWRJW-UHFFFAOYSA-N 0.000 claims description 2
- RQVFLKLHPKLTIO-UHFFFAOYSA-N C1(CC1)N1N=CC=2C(N(C(=CC=21)C)CC1=CC=C(C=C1)OC)=O Chemical compound C1(CC1)N1N=CC=2C(N(C(=CC=21)C)CC1=CC=C(C=C1)OC)=O RQVFLKLHPKLTIO-UHFFFAOYSA-N 0.000 claims description 2
- CXGGCYJPLGSTBH-UHFFFAOYSA-N CC1=CC2=C(C(N1CC1=CC=C(C=C1)C)=O)C=NN2C1CCOCC1 Chemical compound CC1=CC2=C(C(N1CC1=CC=C(C=C1)C)=O)C=NN2C1CCOCC1 CXGGCYJPLGSTBH-UHFFFAOYSA-N 0.000 claims description 2
- MWPSAGRFLKLXIM-UHFFFAOYSA-N COC1=CC=C(C=C1)CN1C(=NC2=C(C1=O)C=NN2C1CCOCC1)CC1COC1 Chemical compound COC1=CC=C(C=C1)CN1C(=NC2=C(C1=O)C=NN2C1CCOCC1)CC1COC1 MWPSAGRFLKLXIM-UHFFFAOYSA-N 0.000 claims description 2
- OHTPHQPYCOLWAE-UHFFFAOYSA-N COC1=CC=C(C=C1)CN1C(C2=C(C=C1C)N(N=C2)C1COC1)=O Chemical compound COC1=CC=C(C=C1)CN1C(C2=C(C=C1C)N(N=C2)C1COC1)=O OHTPHQPYCOLWAE-UHFFFAOYSA-N 0.000 claims description 2
- VJXIKYZGNVVTHA-UHFFFAOYSA-N COC1=CC=C(C=C1)CN1C(C2=C(C=C1C)N(N=C2)C1COCC1)=O Chemical compound COC1=CC=C(C=C1)CN1C(C2=C(C=C1C)N(N=C2)C1COCC1)=O VJXIKYZGNVVTHA-UHFFFAOYSA-N 0.000 claims description 2
- XNNVZFHRPHCGHM-UHFFFAOYSA-N COC1=CC=C(C=C1)CN1C(C2=C(C=C1C)N(N=C2)C1COCCC1)=O Chemical compound COC1=CC=C(C=C1)CN1C(C2=C(C=C1C)N(N=C2)C1COCCC1)=O XNNVZFHRPHCGHM-UHFFFAOYSA-N 0.000 claims description 2
- IAAHGVIRZIKPHA-UHFFFAOYSA-N COC1=CC=C(CN2C(=NC3=C(C2=O)C=NN3C2CCOCC2)C)C=C1 Chemical compound COC1=CC=C(CN2C(=NC3=C(C2=O)C=NN3C2CCOCC2)C)C=C1 IAAHGVIRZIKPHA-UHFFFAOYSA-N 0.000 claims description 2
- GMPCYHZOARRAOF-UHFFFAOYSA-N COC1=CC=C(CN2C(C3=C(C=C2C)N(N=C3)CCC)=O)C=C1 Chemical compound COC1=CC=C(CN2C(C3=C(C=C2C)N(N=C3)CCC)=O)C=C1 GMPCYHZOARRAOF-UHFFFAOYSA-N 0.000 claims description 2
- LUDIBRFXTWLUSU-UHFFFAOYSA-N FC1=CC=C(C=C1)CN1C(C2=C(C=C1C)N(N=C2)C1CCOCC1)=O Chemical compound FC1=CC=C(C=C1)CN1C(C2=C(C=C1C)N(N=C2)C1CCOCC1)=O LUDIBRFXTWLUSU-UHFFFAOYSA-N 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- APQLMNUUGPWXRZ-UHFFFAOYSA-N O1COC2=C1C=CC(=C2)CN1C(C2=C(C=C1C)N(N=C2)C1CCOCC1)=O Chemical compound O1COC2=C1C=CC(=C2)CN1C(C2=C(C=C1C)N(N=C2)C1CCOCC1)=O APQLMNUUGPWXRZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 201000003631 narcolepsy Diseases 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 208000020016 psychiatric disease Diseases 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- ZILNXTHNKXUETP-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-6-methyl-1-(oxan-4-yl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=NC2=C(C=NN2C2CCOCC2)C(=O)N1CC1=CC=C(Cl)C=C1 ZILNXTHNKXUETP-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- -1 C 1 -C 3 alkoxy Chemical group 0.000 claims 1
- FKFYCHHMKLLPQY-UHFFFAOYSA-N C1(CCCCC1)CN1C(=NC2=C(C1=O)C=NN2C1CCOCC1)C Chemical compound C1(CCCCC1)CN1C(=NC2=C(C1=O)C=NN2C1CCOCC1)C FKFYCHHMKLLPQY-UHFFFAOYSA-N 0.000 claims 1
- TYMBPQQASYCWEH-UHFFFAOYSA-N C1(CCCCC1)CN1C(=NC2=C(C1=O)C=NN2CCC)C Chemical compound C1(CCCCC1)CN1C(=NC2=C(C1=O)C=NN2CCC)C TYMBPQQASYCWEH-UHFFFAOYSA-N 0.000 claims 1
- PBXYUGSYGCBAKT-UHFFFAOYSA-N COC1=CC=C(C=C1)CN1C(=NC2=C(C1=O)C=NN2CCC)C Chemical compound COC1=CC=C(C=C1)CN1C(=NC2=C(C1=O)C=NN2CCC)C PBXYUGSYGCBAKT-UHFFFAOYSA-N 0.000 claims 1
- VWDZYEFJJSYZME-UHFFFAOYSA-N COC1=CC=C(CN2C(C3=C(C=C2C)N(N=C3)C2(CCOCC2)C)=O)C=C1 Chemical compound COC1=CC=C(CN2C(C3=C(C=C2C)N(N=C3)C2(CCOCC2)C)=O)C=C1 VWDZYEFJJSYZME-UHFFFAOYSA-N 0.000 claims 1
- DVUJDBKFPXPEMT-UHFFFAOYSA-N COCC=1N(C(C2=C(N1)N(N=C2)C2CCOCC2)=O)CC2=CC=C(C=C2)OC.C(C)C=2N(C(C1=C(N2)N(N=C1)C1CCOCC1)=O)CC1=CC=C(C=C1)OC Chemical compound COCC=1N(C(C2=C(N1)N(N=C2)C2CCOCC2)=O)CC2=CC=C(C=C2)OC.C(C)C=2N(C(C1=C(N2)N(N=C1)C1CCOCC1)=O)CC1=CC=C(C=C1)OC DVUJDBKFPXPEMT-UHFFFAOYSA-N 0.000 claims 1
- SBPLRPBAFIENJD-IKJXHCRLSA-N COc1ccc(Cn2c(C)cc3n(ncc3c2=O)C2CCO[C@@H]2C)cc1 Chemical compound COc1ccc(Cn2c(C)cc3n(ncc3c2=O)C2CCO[C@@H]2C)cc1 SBPLRPBAFIENJD-IKJXHCRLSA-N 0.000 claims 1
- SBPLRPBAFIENJD-PIVQAISJSA-N COc1ccc(Cn2c(C)cc3n(ncc3c2=O)C2CCO[C@H]2C)cc1 Chemical compound COc1ccc(Cn2c(C)cc3n(ncc3c2=O)C2CCO[C@H]2C)cc1 SBPLRPBAFIENJD-PIVQAISJSA-N 0.000 claims 1
- FZRPHLODQVQNHB-UHFFFAOYSA-N ClC=1C=C(C=CC=1)CN1C(C2=C(C=C1C)N(N=C2)C1CCOCC1)=O Chemical compound ClC=1C=C(C=CC=1)CN1C(C2=C(C=C1C)N(N=C2)C1CCOCC1)=O FZRPHLODQVQNHB-UHFFFAOYSA-N 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- ZJNKQHWMEGCHOV-UHFFFAOYSA-N pyrazolo[4,3-c]pyridin-4-one Chemical compound O=C1N=CC=C2N=NC=C12 ZJNKQHWMEGCHOV-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical compound O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 101100407341 Drosophila melanogaster Pde9 gene Proteins 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- XJWOWXZSFTXJEX-UHFFFAOYSA-N phenylsilicon Chemical compound [Si]C1=CC=CC=C1 XJWOWXZSFTXJEX-UHFFFAOYSA-N 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA201600221 | 2016-04-12 | ||
| DKPA201600221 | 2016-04-12 | ||
| PCT/EP2017/058332 WO2017178350A1 (en) | 2016-04-12 | 2017-04-07 | 1,5-dihydro-4h-pyrazolo[3,4-d]pyrimidin-4-ones and 1,5-dihydro-4h-pyrazolo[4,3-c]pyridin-4-ones as pde1 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019517996A JP2019517996A (ja) | 2019-06-27 |
| JP2019517996A5 true JP2019517996A5 (enExample) | 2020-05-07 |
| JP7093306B2 JP7093306B2 (ja) | 2022-06-29 |
Family
ID=58489694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018550733A Active JP7093306B2 (ja) | 2016-04-12 | 2017-04-07 | ＰＤＥ１阻害剤としての１，５－ジヒドロ－４Ｈ－ピラゾロ［３，４－ｄ］ピリミジン－４－オン及び１，５－ジヒドロ－４Ｈ－ピラゾロ［４，３－ｃ］ピリジン－４－オン |
Country Status (43)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| ES2967489T3 (es) | 2016-10-18 | 2024-04-30 | H Lundbeck As | Imidazopirazinonas, pirazolopirimidinonas y pirazolopiridinonas como inhibidores de PDE1 |
| HUE050403T2 (hu) | 2016-10-28 | 2020-12-28 | H Lundbeck As | Imidazopirazinonokkal végzett kombinációs kezelések pszichiátriai és/vagy kognitív betegségek kezelésére |
| BR112018013084A2 (pt) | 2016-10-28 | 2018-12-11 | H Lundbeck As | tratamentos de combinação compreendendo a administração de imidazopirazinonas |
| AU2017388054B2 (en) | 2016-12-28 | 2022-03-24 | Dart Neuroscience, Llc | Substituted pyrazolopyrimidinone compounds as PDE2 inhibitors |
| CA3120971A1 (en) * | 2017-11-27 | 2019-05-31 | Dart Neuroscience, Llc | Substituted furanopyrimidine compounds as pde1 inhibitors |
| CN112189013A (zh) | 2018-05-25 | 2021-01-05 | 细胞内治疗公司 | 有机化合物 |
| CN115304607B (zh) * | 2022-07-06 | 2023-06-27 | 华南农业大学 | 吡唑并嘧啶衍生物的制备方法 |
Family Cites Families (42)
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|---|---|---|---|---|
| GB973361A (en) * | 1960-05-11 | 1964-10-28 | Ciba Ltd | Pyrazolo-pyrimidines and process for their manufacture |
| DE19709877A1 (de) | 1997-03-11 | 1998-09-17 | Bayer Ag | 1,5-Dihydro-pyrazolo[3,4-d]-pyrimidinon-derivate |
| DE10238724A1 (de) * | 2002-08-23 | 2004-03-04 | Bayer Ag | Alkyl-substituierte Pyrazolpyrimidine |
| DE10238723A1 (de) * | 2002-08-23 | 2004-03-11 | Bayer Ag | Phenyl-substituierte Pyrazolyprimidine |
| DE10238722A1 (de) * | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| EP1626971B1 (de) * | 2003-05-09 | 2011-08-10 | Boehringer Ingelheim International Gmbh | 6-cyclylmethyl- und 6-alkylmethyl-substituierte pyrazolopyrimidine |
| EP1828192B1 (en) | 2004-12-21 | 2014-12-03 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| EP1919287A4 (en) | 2005-08-23 | 2010-04-28 | Intra Cellular Therapies Inc | ORGANIC COMPOUNDS FOR TREATING A REDUCED DOPAMINE RECEPTOR SIGNALING ACTIVITY |
| US8012936B2 (en) | 2006-03-29 | 2011-09-06 | New York University | Tau fragments for immunotherapy |
| US9006258B2 (en) | 2006-12-05 | 2015-04-14 | Intra-Cellular Therapies, Inc. | Method of treating female sexual dysfunction with a PDE1 inhibitor |
| DK2152712T3 (da) * | 2007-05-11 | 2012-03-26 | Pfizer | Aminoheterocykliske fobindelser |
| WO2009068320A1 (en) | 2007-11-30 | 2009-06-04 | Elbion Gmbh | Aryl and heteroaryl fused imidazo (1,5-a) pyrazines as inhibitors of phosphodiesterase 10 |
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