JP2012526810A5 - - Google Patents
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- JP2012526810A5 JP2012526810A5 JP2012510800A JP2012510800A JP2012526810A5 JP 2012526810 A5 JP2012526810 A5 JP 2012526810A5 JP 2012510800 A JP2012510800 A JP 2012510800A JP 2012510800 A JP2012510800 A JP 2012510800A JP 2012526810 A5 JP2012526810 A5 JP 2012526810A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- cycloalkyl
- imidazo
- phenylmethyl
- 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.)
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- -1 N-dialkylamino Inorganic materials 0.000 claims description 111
- 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 claims description 32
- 208000028017 Psychotic disease Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 208000024254 Delusional disease Diseases 0.000 claims description 4
- 208000002851 paranoid schizophrenia Diseases 0.000 claims description 4
- 206010026749 Mania Diseases 0.000 claims description 3
- 239000003693 atypical antipsychotic agent Substances 0.000 claims description 3
- 229940127236 atypical antipsychotics Drugs 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 2
- 208000020016 psychiatric disease Diseases 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 150
- 125000003118 aryl group Chemical group 0.000 claims 70
- 125000001072 heteroaryl group Chemical group 0.000 claims 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims 55
- 229910052799 carbon Inorganic materials 0.000 claims 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 34
- 125000005843 halogen group Chemical group 0.000 claims 32
- 229910052739 hydrogen Inorganic materials 0.000 claims 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 31
- 239000003795 chemical substances by application Substances 0.000 claims 29
- 125000003545 alkoxy group Chemical group 0.000 claims 28
- 229910052757 nitrogen Inorganic materials 0.000 claims 28
- 150000003839 salts Chemical group 0.000 claims 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 27
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000001188 haloalkyl group Chemical group 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 19
- 125000004076 pyridyl group Chemical group 0.000 claims 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 17
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 15
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 14
- 229910052801 chlorine Inorganic materials 0.000 claims 14
- 229910052731 fluorine Inorganic materials 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 12
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 239000000651 prodrug Chemical group 0.000 claims 11
- 229940002612 prodrug Drugs 0.000 claims 11
- 150000001721 carbon Chemical group 0.000 claims 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 10
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 9
- 125000002947 alkylene group Chemical group 0.000 claims 9
- 125000000732 arylene group Chemical group 0.000 claims 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 9
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 7
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims 7
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000002720 diazolyl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims 6
- 125000001425 triazolyl group Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 208000020925 Bipolar disease Diseases 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- OSXKHFTZRHDUJN-UHFFFAOYSA-N N(2),3-ethenoguanine Chemical compound O=C1NC2=NC=CN2C2=C1NC=N2 OSXKHFTZRHDUJN-UHFFFAOYSA-N 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 4
- 125000005605 benzo group Chemical group 0.000 claims 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
- 125000006682 monohaloalkyl group Chemical group 0.000 claims 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000006684 polyhaloalkyl group Polymers 0.000 claims 4
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000004419 alkynylene group Chemical group 0.000 claims 3
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 3
- 125000001769 aryl amino group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 claims 3
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 3
- 125000005551 pyridylene group Chemical group 0.000 claims 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 3
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 2
- VILOVKQUBCFZCP-UHFFFAOYSA-N 2,5,7,7,8-pentamethyl-3,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound N=1C(C)(C)C(C)N2C=1N(C)C(=O)C1=C2N=C(C)N1 VILOVKQUBCFZCP-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 208000020186 Schizophreniform disease Diseases 0.000 claims 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 2
- 125000006294 amino alkylene group Chemical group 0.000 claims 2
- 125000005122 aminoalkylamino group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 208000022610 schizoaffective disease Diseases 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- ZFIXLLHBDJAIIF-VAJTXYMYSA-N (4R)-5-benzyl-4,8-dimethyl-1,3,5,8,10-pentazatetracyclo[7.6.0.02,6.011,15]pentadeca-12,14-dien-7-one Chemical compound C[C@@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=O)C)NC1C3=CC=C1 ZFIXLLHBDJAIIF-VAJTXYMYSA-N 0.000 claims 1
- LMKVVNSEQFWADD-IKLZKGPXSA-N (4S)-5-benzyl-4,8-dimethyl-1,3,5,8,10-pentazatetracyclo[7.6.0.02,6.011,15]pentadeca-12,14-diene-7-thione Chemical compound C[C@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=S)C)NC1C3=CC=C1 LMKVVNSEQFWADD-IKLZKGPXSA-N 0.000 claims 1
- HTTROEILAAXBHH-QMMMGPOBSA-N (7r)-2,5-dimethyl-7-propan-2-yl-7,8-dihydro-3h-imidazo[2,1-b]purin-4-one Chemical compound C([C@H](N=1)C(C)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1 HTTROEILAAXBHH-QMMMGPOBSA-N 0.000 claims 1
- NVRVNEBAXHEDFJ-LJQANCHMSA-N (7r)-3,7-dibenzyl-2,5-dimethyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@H]1N=C2N(C(C=3N(CC=4C=CC=CC=4)C(C)=NC=3N2C1)=O)C)C1=CC=CC=C1 NVRVNEBAXHEDFJ-LJQANCHMSA-N 0.000 claims 1
- IEPMPAZHBXLCOP-LLVKDONJSA-N (7r)-3-benzyl-2,5,7-trimethyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@H](N=1)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 IEPMPAZHBXLCOP-LLVKDONJSA-N 0.000 claims 1
- UGTHPHLZFMDADA-MRXNPFEDSA-N (7r)-3-benzyl-2,5-dimethyl-7-(2-methylpropyl)-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@H](N=1)CC(C)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 UGTHPHLZFMDADA-MRXNPFEDSA-N 0.000 claims 1
- UKYVGPSNGAZSMN-SFHVURJKSA-N (7r)-3-benzyl-2,5-dimethyl-7-phenyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@H](N=C1N(C(C=23)=O)C)C=4C=CC=CC=4)N1C=2N=C(C)N3CC1=CC=CC=C1 UKYVGPSNGAZSMN-SFHVURJKSA-N 0.000 claims 1
- LPWLBWDFJZDWEX-HNNXBMFYSA-N (7r)-3-benzyl-2,5-dimethyl-7-propan-2-yl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@H](N=1)C(C)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 LPWLBWDFJZDWEX-HNNXBMFYSA-N 0.000 claims 1
- HTTROEILAAXBHH-MRVPVSSYSA-N (7s)-2,5-dimethyl-7-propan-2-yl-7,8-dihydro-3h-imidazo[2,1-b]purin-4-one Chemical compound C([C@@H](N=1)C(C)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1 HTTROEILAAXBHH-MRVPVSSYSA-N 0.000 claims 1
- LPWLBWDFJZDWEX-OAHLLOKOSA-N (7s)-3-benzyl-2,5-dimethyl-7-propan-2-yl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@@H](N=1)C(C)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 LPWLBWDFJZDWEX-OAHLLOKOSA-N 0.000 claims 1
- DOWZFRHFNTWIRI-FQNRMIAFSA-N (7s)-3-benzyl-7-butan-2-yl-2,5-dimethyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@@H](N=1)C(C)CC)N2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 DOWZFRHFNTWIRI-FQNRMIAFSA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- AVUXINBHZQJDEL-UHFFFAOYSA-N 2,5,7,7-tetramethyl-3,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound O=C1N(C)C2=NC(C)(C)CN2C2=C1NC(C)=N2 AVUXINBHZQJDEL-UHFFFAOYSA-N 0.000 claims 1
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims 1
- YYYNZFNCEJVVKL-UHFFFAOYSA-N 3-benzyl-2,5-dimethyl-7-propyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound N=1C(CCC)CN2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 YYYNZFNCEJVVKL-UHFFFAOYSA-N 0.000 claims 1
- WRIUADNGMJXJRO-UHFFFAOYSA-N 3-benzyl-5,7,7-trimethyl-2-(trifluoromethyl)-8h-imidazo[2,1-b]purin-4-one Chemical compound C1=2C(=O)N(C)C3=NC(C)(C)CN3C=2N=C(C(F)(F)F)N1CC1=CC=CC=C1 WRIUADNGMJXJRO-UHFFFAOYSA-N 0.000 claims 1
- WFJGMVOWVZKNLA-UHFFFAOYSA-N 3-benzyl-5-methyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C1=2C(=O)N(C)C3=NCCN3C=2N=CN1CC1=CC=CC=C1 WFJGMVOWVZKNLA-UHFFFAOYSA-N 0.000 claims 1
- PAIMQQBUPHMLIS-UHFFFAOYSA-N 3-benzyl-5-methyl-8,9-dihydro-7h-pyrimido[2,1-b]purin-4-one Chemical compound N12CCCN=C2N(C)C(=O)C2=C1N=CN2CC1=CC=CC=C1 PAIMQQBUPHMLIS-UHFFFAOYSA-N 0.000 claims 1
- PNWOWTKHERLXTQ-UHFFFAOYSA-N 3-benzyl-5-methyl-8-phenyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C1=2C(=O)N(C)C3=NCC(C=4C=CC=CC=4)N3C=2N=CN1CC1=CC=CC=C1 PNWOWTKHERLXTQ-UHFFFAOYSA-N 0.000 claims 1
- DCFKJGKOPGOTIK-UHFFFAOYSA-N 3-benzyl-5-methylspiro[7h-imidazo[2,1-b]purine-8,1'-cyclohexane]-4-one Chemical compound N12C=3N=CN(CC=4C=CC=CC=4)C=3C(=O)N(C)C2=NCC21CCCCC2 DCFKJGKOPGOTIK-UHFFFAOYSA-N 0.000 claims 1
- VPTYAXRMVTVLAL-UHFFFAOYSA-N 3-benzyl-7-ethyl-2,5-dimethyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound N=1C(CC)CN2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 VPTYAXRMVTVLAL-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- VMYIZJTYOYPOCT-UHFFFAOYSA-N 5-benzyl-4,8,11-trimethyl-1,3,5,8,10-pentazatetracyclo[7.6.0.02,6.011,15]pentadeca-2(6),3,9-trien-7-one Chemical compound C1=2C(=O)N(C)C3=NC4(C)CCCC4N3C=2N=C(C)N1CC1=CC=CC=C1 VMYIZJTYOYPOCT-UHFFFAOYSA-N 0.000 claims 1
- 241000180579 Arca Species 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
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| JP2013507360A (ja) | 2009-10-08 | 2013-03-04 | イントラ−セルラー・セラピーズ・インコーポレイテッド | ホスホジエステラーゼ１−標的トレーサーおよび方法 |
| MX339805B (es) | 2010-04-22 | 2016-06-10 | Intra Cellular Therapies Inc | Compuestos organicos. |
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| US10285992B2 (en) | 2014-08-07 | 2019-05-14 | Intra-Cellular Therapies, Inc. | Combinations of PDE1 inhibitors and NEP inhibitors and associated methods |
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2010
- 2010-05-13 US US13/319,807 patent/US9468637B2/en active Active
- 2010-05-13 JP JP2012510800A patent/JP2012526810A/ja not_active Withdrawn
- 2010-05-13 EP EP10775209.9A patent/EP2434895A4/en not_active Ceased
- 2010-05-13 WO PCT/US2010/001444 patent/WO2010132127A1/en not_active Ceased
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2015
- 2015-08-06 JP JP2015156355A patent/JP6038250B2/ja active Active
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2016
- 2016-09-12 US US15/263,256 patent/US10010553B2/en active Active
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2018
- 2018-06-04 US US15/997,438 patent/US10238660B2/en active Active
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