HRP20120105T1 - Aminoheterociklički spojevi - Google Patents
Aminoheterociklički spojevi Download PDFInfo
- Publication number
- HRP20120105T1 HRP20120105T1 HR20120105T HRP20120105T HRP20120105T1 HR P20120105 T1 HRP20120105 T1 HR P20120105T1 HR 20120105 T HR20120105 T HR 20120105T HR P20120105 T HRP20120105 T HR P20120105T HR P20120105 T1 HRP20120105 T1 HR P20120105T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- pyrazolo
- dihydro
- pyrimidin
- tetrahydro
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 150000003839 salts Chemical class 0.000 claims abstract 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract 8
- 125000001424 substituent group Chemical group 0.000 claims abstract 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
- 239000001257 hydrogen Substances 0.000 claims abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims abstract 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract 2
- -1 cyano, phenyl Chemical group 0.000 claims 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 241000124008 Mammalia Species 0.000 claims 5
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- IWXUVYOOUMLUTQ-CZUORRHYSA-N chembl2179105 Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=NC=CC=N1 IWXUVYOOUMLUTQ-CZUORRHYSA-N 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 239000008177 pharmaceutical agent Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- NLUPGGKMPPBLIC-RDTXWAMCSA-N 1-cyclopentyl-6-[(3S,4S)-1-[[2-(dimethylamino)pyrimidin-4-yl]methyl]-4-methylpyrrolidin-3-yl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)C)N1CC1=CC=NC(N(C)C)=N1 NLUPGGKMPPBLIC-RDTXWAMCSA-N 0.000 claims 1
- JNHYUKOWUXVAAK-DNVCBOLYSA-N 1-cyclopentyl-6-[(3S,4S)-4-methyl-1-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-ylmethyl)pyrrolidin-3-yl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@@H]3CN(CC4=C5CCCCN5N=C4)C[C@H]3C)=NC=2N1C1CCCC1 JNHYUKOWUXVAAK-DNVCBOLYSA-N 0.000 claims 1
- IEAYERCWSQIPRD-CRAIPNDOSA-N 1-cyclopentyl-6-[(3S,4S)-4-methyl-1-[(1-methylbenzimidazol-2-yl)methyl]pyrrolidin-3-yl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@@H]3CN(CC=4N(C5=CC=CC=C5N=4)C)C[C@H]3C)=NC=2N1C1CCCC1 IEAYERCWSQIPRD-CRAIPNDOSA-N 0.000 claims 1
- CBGWGZGLFRSMHQ-FZKQIMNGSA-N 1-cyclopentyl-6-[(3S,4S)-4-methyl-1-[(2-methylpyrimidin-4-yl)methyl]pyrrolidin-3-yl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)C)N1CC1=CC=NC(C)=N1 CBGWGZGLFRSMHQ-FZKQIMNGSA-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
- XEJPARKQHKXBCG-IIBYNOLFSA-N 2-[[(3S,4S)-3-ethyl-4-[1-(oxan-4-yl)-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl]pyrrolidin-1-yl]methyl]benzonitrile Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC)N1CC1=CC=CC=C1C#N XEJPARKQHKXBCG-IIBYNOLFSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- GZGBCGXDIZKDDD-WIYYLYMNSA-N 3-[[(3S,4S)-3-ethyl-4-[1-(oxan-4-yl)-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl]pyrrolidin-1-yl]methyl]benzonitrile Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC)N1CC1=CC=CC(C#N)=C1 GZGBCGXDIZKDDD-WIYYLYMNSA-N 0.000 claims 1
- MEFHCSDCLCCZEX-RDTXWAMCSA-N 3-methyl-6-[(3S,4S)-4-methyl-1-(pyridin-3-ylmethyl)pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C(C)=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC=CN=C1 MEFHCSDCLCCZEX-RDTXWAMCSA-N 0.000 claims 1
- VUTIRRLSIFXEKB-WIYYLYMNSA-N 4-[[(3S,4S)-3-ethyl-4-[1-(oxan-4-yl)-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl]pyrrolidin-1-yl]methyl]benzonitrile Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC)N1CC1=CC=C(C#N)C=C1 VUTIRRLSIFXEKB-WIYYLYMNSA-N 0.000 claims 1
- YCQQZAGLYABFOH-CXAGYDPISA-N 6-[(3S,4S)-1-(2,1,3-benzothiadiazol-5-ylmethyl)-4-methylpyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@@H]3CN(CC4=CC5=NSN=C5C=C4)C[C@H]3C)=NC=2N1C1CCOCC1 YCQQZAGLYABFOH-CXAGYDPISA-N 0.000 claims 1
- VAWDYFGPRUIGMP-FZKQIMNGSA-N 6-[(3S,4S)-1-[(2,4-difluorophenyl)methyl]-4-methylpyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC=C(F)C=C1F VAWDYFGPRUIGMP-FZKQIMNGSA-N 0.000 claims 1
- KLPDTSPVILLXEK-FZKQIMNGSA-N 6-[(3S,4S)-1-[(2,5-dimethylpyrazol-3-yl)methyl]-4-methylpyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC(C)=NN1C KLPDTSPVILLXEK-FZKQIMNGSA-N 0.000 claims 1
- BLOGHUMTHBKIEO-CZUORRHYSA-N 6-[(3S,4S)-1-[(2,6-difluorophenyl)methyl]-4-methylpyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=C(F)C=CC=C1F BLOGHUMTHBKIEO-CZUORRHYSA-N 0.000 claims 1
- KPBYJLQSWDRHOS-DNVCBOLYSA-N 6-[(3S,4S)-1-[(2-methoxyphenyl)methyl]-4-methylpyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1CN1C[C@@H](C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)[C@H](C)C1 KPBYJLQSWDRHOS-DNVCBOLYSA-N 0.000 claims 1
- LLJMHXXSTMJWPI-BFUOFWGJSA-N 6-[(3S,4S)-1-[(3,5-difluorophenyl)methyl]-4-methylpyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC(F)=CC(F)=C1 LLJMHXXSTMJWPI-BFUOFWGJSA-N 0.000 claims 1
- DIWYKXFHEOYCND-FOIQADDNSA-N 6-[(3S,4S)-1-[(3-methoxyphenyl)methyl]-4-methylpyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC(CN2C[C@H]([C@H](C)C2)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)=C1 DIWYKXFHEOYCND-FOIQADDNSA-N 0.000 claims 1
- VGIIPBKPGAQRKL-RDTXWAMCSA-N 6-[(3S,4S)-1-[(6-methoxypyridin-3-yl)methyl]-4-methylpyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC(OC)=CC=C1CN1C[C@@H](C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)[C@H](C)C1 VGIIPBKPGAQRKL-RDTXWAMCSA-N 0.000 claims 1
- LRGHVSPRGNVCGJ-CZUORRHYSA-N 6-[(3S,4S)-1-[(6-methoxypyridin-3-yl)methyl]-4-methylpyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC(OC)=CC=C1CN1C[C@@H](C=2NC(=O)C=3C=NN(C=3N=2)C(C)C)[C@H](C)C1 LRGHVSPRGNVCGJ-CZUORRHYSA-N 0.000 claims 1
- NEBURINZSCMMMG-RDTXWAMCSA-N 6-[(3S,4S)-1-[(6-methoxypyridin-3-yl)methyl]-4-methylpyrrolidin-3-yl]-3-methyl-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC(OC)=CC=C1CN1C[C@@H](C=2NC(=O)C=3C(C)=NN(C=3N=2)C2CCOCC2)[C@H](C)C1 NEBURINZSCMMMG-RDTXWAMCSA-N 0.000 claims 1
- GASDKPVJCSBXQB-SJLPKXTDSA-N 6-[(3S,4S)-1-benzyl-4-ethylpyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C(C)C)CC)N1CC1=CC=CC=C1 GASDKPVJCSBXQB-SJLPKXTDSA-N 0.000 claims 1
- PJEOWYGQYLUFJR-DNVCBOLYSA-N 6-[(3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl]-1-(thian-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCSCC2)C)N1CC1=CC=CC=C1 PJEOWYGQYLUFJR-DNVCBOLYSA-N 0.000 claims 1
- VUUDXZONVIKTJB-DNVCBOLYSA-N 6-[(3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl]-3-methyl-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C(C)=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC=CC=C1 VUUDXZONVIKTJB-DNVCBOLYSA-N 0.000 claims 1
- HVNWRVFQXJXFHM-DNVCBOLYSA-N 6-[(3S,4S)-4-ethyl-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC)N1CC1=CC=CC=N1 HVNWRVFQXJXFHM-DNVCBOLYSA-N 0.000 claims 1
- FDIGKEKPSMDSFM-CRAIPNDOSA-N 6-[(3S,4S)-4-ethyl-1-(quinoxaline-2-carbonyl)pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@@H]3CN(C[C@H]3CC)C(=O)C=3N=C4C=CC=CC4=NC=3)=NC=2N1C1CCOCC1 FDIGKEKPSMDSFM-CRAIPNDOSA-N 0.000 claims 1
- XQZJOMSMPDUGCE-DNVCBOLYSA-N 6-[(3S,4S)-4-ethyl-1-[(5-methylpyrazin-2-yl)methyl]pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC)N1CC1=CN=C(C)C=N1 XQZJOMSMPDUGCE-DNVCBOLYSA-N 0.000 claims 1
- RVXPQIRDRIYNDK-VQIMIIECSA-N 6-[(3S,4S)-4-ethyl-1-[(6-methoxypyridin-3-yl)methyl]pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC)N1CC1=CC=C(OC)N=C1 RVXPQIRDRIYNDK-VQIMIIECSA-N 0.000 claims 1
- BORPFOUKOGKLRD-RHSMWYFYSA-N 6-[(3S,4S)-4-methyl-1-(1,5-naphthyridin-4-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CN=C2C(CN3C[C@H]([C@@H](C3)C)C3=NC4=C(C(N3)=O)C=NN4C(C)C)=CC=NC2=C1 BORPFOUKOGKLRD-RHSMWYFYSA-N 0.000 claims 1
- PAOXLSJYEIANQB-RDTXWAMCSA-N 6-[(3S,4S)-4-methyl-1-(1,8-naphthyridin-4-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC=C2C(CN3C[C@H]([C@@H](C3)C)C3=NC4=C(C(N3)=O)C=NN4C(C)C)=CC=NC2=N1 PAOXLSJYEIANQB-RDTXWAMCSA-N 0.000 claims 1
- RNKURPCGQFLEQJ-CZUORRHYSA-N 6-[(3S,4S)-4-methyl-1-(pyrido[2,3-b]pyrazin-8-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CN=C2C(CN3C[C@H]([C@@H](C3)C)C3=NC4=C(C(N3)=O)C=NN4C(C)C)=CC=NC2=N1 RNKURPCGQFLEQJ-CZUORRHYSA-N 0.000 claims 1
- MFQBAEUQGYUGHW-IIBYNOLFSA-N 6-[(3S,4S)-4-methyl-1-(quinolin-3-ylmethyl)pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@@H]3CN(CC=4C=C5C=CC=CC5=NC=4)C[C@H]3C)=NC=2N1C1CCOCC1 MFQBAEUQGYUGHW-IIBYNOLFSA-N 0.000 claims 1
- JYKMFUMGSVKAKI-DNVCBOLYSA-N 6-[(3S,4S)-4-methyl-1-(quinolin-3-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC=CC2=CC(CN3C[C@H]([C@@H](C3)C)C3=NC4=C(C(N3)=O)C=NN4C(C)C)=CN=C21 JYKMFUMGSVKAKI-DNVCBOLYSA-N 0.000 claims 1
- JYSXRGNFAPSHSO-IIBYNOLFSA-N 6-[(3S,4S)-4-methyl-1-(quinolin-4-ylmethyl)pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@@H]3CN(CC=4C5=CC=CC=C5N=CC=4)C[C@H]3C)=NC=2N1C1CCOCC1 JYSXRGNFAPSHSO-IIBYNOLFSA-N 0.000 claims 1
- WPXPCWPERGOSHY-DNVCBOLYSA-N 6-[(3S,4S)-4-methyl-1-(quinolin-4-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC(C)N1N=CC2=C1N=C(NC2=O)[C@@H]1CN(CC2=CC=NC3=CC=CC=C23)C[C@H]1C WPXPCWPERGOSHY-DNVCBOLYSA-N 0.000 claims 1
- XXHSSBCYDWYHOM-DNVCBOLYSA-N 6-[(3S,4S)-4-methyl-1-(quinoxalin-2-ylmethyl)pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@@H]3CN(CC=4N=C5C=CC=CC5=NC=4)C[C@H]3C)=NC=2N1C1CCOCC1 XXHSSBCYDWYHOM-DNVCBOLYSA-N 0.000 claims 1
- ZAOLCNVFLBSPTP-RHSMWYFYSA-N 6-[(3S,4S)-4-methyl-1-(quinoxalin-6-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=NC2=CC(CN3C[C@H]([C@@H](C3)C)C3=NC4=C(C(N3)=O)C=NN4C(C)C)=CC=C21 ZAOLCNVFLBSPTP-RHSMWYFYSA-N 0.000 claims 1
- SOANHBRUVOKFSR-RHSMWYFYSA-N 6-[(3S,4S)-4-methyl-1-[(1-methylimidazo[4,5-c]pyridin-2-yl)methyl]pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@@H]3CN(CC=4N(C5=CC=NC=C5N=4)C)C[C@H]3C)=NC=2N1C1CCOCC1 SOANHBRUVOKFSR-RHSMWYFYSA-N 0.000 claims 1
- PILHFFXOPXWOSH-FZKQIMNGSA-N 6-[(3S,4S)-4-methyl-1-[(2-methylpyrimidin-4-yl)methyl]pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC=NC(C)=N1 PILHFFXOPXWOSH-FZKQIMNGSA-N 0.000 claims 1
- VMSUDAYERLIVLB-MLGOLLRUSA-N 6-[(3S,4S)-4-methyl-1-[(5-methylpyrazin-2-yl)methyl]pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C)C2=NC3=C(C(N2)=O)C=NN3C(C)C)N1CC1=CN=C(C)C=N1 VMSUDAYERLIVLB-MLGOLLRUSA-N 0.000 claims 1
- CIJFCCFFVJESHK-AUUYWEPGSA-N 6-[(3S,4S)-4-methyl-1-[(6-methylpyridin-2-yl)methyl]pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC=CC(C)=N1 CIJFCCFFVJESHK-AUUYWEPGSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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US91733307P | 2007-05-11 | 2007-05-11 | |
PCT/IB2008/001125 WO2008139293A1 (fr) | 2007-05-11 | 2008-05-05 | Composés amino-hétérocycliques |
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HR20120105T HRP20120105T1 (hr) | 2007-05-11 | 2012-02-01 | Aminoheterociklički spojevi |
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DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
JP5498392B2 (ja) | 2007-11-30 | 2014-05-21 | 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 | 1,5−ジヒドロ−ピラゾロ[3,4−d]ピリミジン−4−オン誘導体及びcns障害の治療のためのpde9aモジュレーターとしてのそれらの使用 |
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 |
WO2010026214A1 (fr) | 2008-09-08 | 2010-03-11 | Boehringer Ingelheim International Gmbh | Pyrazolopyrimidines et leur utilisation pour le traitement de troubles du snc |
PE20110711A1 (es) | 2008-11-19 | 2011-10-11 | Envivo Pharmaceuticals Inc | Tratamiento de trastornos cognitivos con (r)-7-cloro-n-(quinuclidin-3-il)benzo[b]tiofeno-2-carboxamida y sales farmaceuticamente aceptables de la misma |
TWI404721B (zh) * | 2009-01-26 | 2013-08-11 | Pfizer | 胺基-雜環化合物 |
PL2414363T3 (pl) | 2009-03-31 | 2014-06-30 | Boehringer Ingelheim Int | Pochodne 1-heterocyklilo-1,5-dihydro-pirazolo[3,4-d]pirymidyn-4-onu i ich zastosowanie jako modulatorów PDE9A |
MX2011011972A (es) * | 2009-05-11 | 2011-12-08 | Envivo Pharmaceuticals Inc | Tratamiento de trastornos cognitivos con determinados receptores de acido nicotinico alfa-7 en combinacion con inhibidores de acetilcolinesterasa. |
WO2010132127A1 (fr) | 2009-05-13 | 2010-11-18 | Intra-Cellular Therapies, Inc. | Composés organiques |
US8858911B2 (en) * | 2009-10-08 | 2014-10-14 | Intra-Cellular Therapies, Inc. | Phosphodiesterase 1-targeting tracers and methods |
DK2571874T3 (en) | 2010-05-17 | 2016-05-17 | Forum Pharmaceuticals Inc | A crystalline form of (R) -7-chloro-N- (quinuclidin-3-yl) benzo [b] thiophene-2-carboxamide hydrochloride monohydrate |
UA110347C2 (uk) | 2010-08-12 | 2015-12-25 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | ПОХІДНІ 6-ЦИКЛОАЛКІЛ-1,5-ДИГІДРОПІРАЗОЛО[3,4-d]ПІРИМІДИН-4-ОНУ І ЇХ ЗАСТОСУВАННЯ ЯК ІНГІБІТОРІВ PDE9A |
CN103097383B (zh) | 2010-09-07 | 2015-09-16 | 安斯泰来制药株式会社 | 吡唑并喹啉化合物 |
RU2603140C2 (ru) * | 2010-09-20 | 2016-11-20 | Айронвуд Фармасьютикалз, Инк. | Соединения имидазотриазинона |
US20130040971A1 (en) * | 2011-02-14 | 2013-02-14 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of cns disorders |
US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
AU2012319549B2 (en) | 2011-10-07 | 2016-07-28 | Eisai R&D Management Co., Ltd. | Pyrazoloquinoline derivative |
IN2015DN02829A (fr) * | 2011-10-10 | 2015-09-11 | Lundbeck & Co As H | |
AU2013213603B2 (en) * | 2012-01-26 | 2017-02-02 | H. Lundbeck A/S | PDE9 inhibitors with imidazo triazinone backbone |
WO2013142269A1 (fr) | 2012-03-19 | 2013-09-26 | Envivo Pharmaceuticals, Inc. | Composés d'imidazotriazinone |
CA2872005A1 (fr) | 2012-05-08 | 2013-11-14 | Forum Pharmaceuticals, Inc. | Procedes de maintien, de traitement ou d'amelioration de la fonction cognitive |
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