JPS6310788A - ３−アミノピラゾロ〔３，４−ｄ〕ピリミジン誘導体 - Google Patents
３−アミノピラゾロ〔３，４−ｄ〕ピリミジン誘導体Info
- Publication number
- JPS6310788A JPS6310788A JP62014627A JP1462787A JPS6310788A JP S6310788 A JPS6310788 A JP S6310788A JP 62014627 A JP62014627 A JP 62014627A JP 1462787 A JP1462787 A JP 1462787A JP S6310788 A JPS6310788 A JP S6310788A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- hours
- dione
- crystals
- pyrimidine
- 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.)
- Pending
Links
- KFVFSHVEAMTYFQ-UHFFFAOYSA-N 2h-pyrazolo[3,4-d]pyrimidin-3-amine Chemical class C1=NC=C2C(N)=NNC2=N1 KFVFSHVEAMTYFQ-UHFFFAOYSA-N 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 50
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
- 208000024891 symptom Diseases 0.000 abstract description 5
- 206010012289 Dementia Diseases 0.000 abstract description 3
- 208000006011 Stroke Diseases 0.000 abstract description 3
- 201000010099 disease Diseases 0.000 abstract description 3
- 208000000044 Amnesia Diseases 0.000 abstract description 2
- 208000031091 Amnestic disease Diseases 0.000 abstract description 2
- 206010008190 Cerebrovascular accident Diseases 0.000 abstract description 2
- 230000006986 amnesia Effects 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 210000004556 brain Anatomy 0.000 abstract description 2
- 230000002490 cerebral effect Effects 0.000 abstract description 2
- 230000003449 preventive effect Effects 0.000 abstract description 2
- CKCLSWQIWDWMCB-UHFFFAOYSA-N 5-ethyl-3-(methylamino)-7-[(4-methylphenyl)methyl]-2h-pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C1=2NN=C(NC)C=2C(=O)N(CC)C(=O)N1CC1=CC=C(C)C=C1 CKCLSWQIWDWMCB-UHFFFAOYSA-N 0.000 abstract 1
- 206010021639 Incontinence Diseases 0.000 abstract 1
- 206010029333 Neurosis Diseases 0.000 abstract 1
- 208000027418 Wounds and injury Diseases 0.000 abstract 1
- 230000006378 damage Effects 0.000 abstract 1
- 208000014674 injury Diseases 0.000 abstract 1
- 230000003340 mental effect Effects 0.000 abstract 1
- 208000015238 neurotic disease Diseases 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 77
- 239000013078 crystal Substances 0.000 description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 42
- 238000002844 melting Methods 0.000 description 37
- 230000008018 melting Effects 0.000 description 37
- 238000000921 elemental analysis Methods 0.000 description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- -1 methoxy, ethoxy Chemical group 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 241000700159 Rattus Species 0.000 description 14
- 230000000694 effects Effects 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 150000003230 pyrimidines Chemical class 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 206010027175 memory impairment Diseases 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 6
- 229960002646 scopolamine Drugs 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 229940035893 uracil Drugs 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006264 debenzylation reaction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000015654 memory Effects 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- 230000006886 spatial memory Effects 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SSORSZACHCNXSJ-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)-3-[2-(2-hydroxypropylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound ClC=1C=C(C=CC=1Cl)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NCC(C)O SSORSZACHCNXSJ-UHFFFAOYSA-N 0.000 description 2
- DILISPNYIVRDBP-UHFFFAOYSA-N 2-[3-[2-(2-hydroxypropylamino)pyrimidin-4-yl]-2-naphthalen-2-ylimidazol-4-yl]acetonitrile Chemical compound OC(CNC1=NC=CC(=N1)N1C(=NC=C1CC#N)C1=CC2=CC=CC=C2C=C1)C DILISPNYIVRDBP-UHFFFAOYSA-N 0.000 description 2
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
- NVZQPSWVZKVJJE-UHFFFAOYSA-N 7-[(3-chlorophenyl)methyl]-3-(methylamino)-5-propyl-2h-pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C1=2NN=C(NC)C=2C(=O)N(CCC)C(=O)N1CC1=CC=CC(Cl)=C1 NVZQPSWVZKVJJE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 206010019196 Head injury Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000003542 behavioural effect Effects 0.000 description 2
- 230000003925 brain function Effects 0.000 description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- KNZYMKYLCIPERV-UHFFFAOYSA-N dichloromethanimine;hydrochloride Chemical compound [Cl-].ClC(Cl)=[NH2+] KNZYMKYLCIPERV-UHFFFAOYSA-N 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- KEEKMOIRJUWKNK-CABZTGNLSA-N (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(SC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F KEEKMOIRJUWKNK-CABZTGNLSA-N 0.000 description 1
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- NYNZQNWKBKUAII-KBXCAEBGSA-N (3s)-n-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide Chemical compound C1[C@@H](O)CCN1C(=O)NC1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 NYNZQNWKBKUAII-KBXCAEBGSA-N 0.000 description 1
- LCFFREMLXLZNHE-GBOLQPHISA-N (e)-2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile Chemical compound C12=C(N)N=CN=C2N([C@@H]2CCCN(C2)C(=O)C(/C#N)=C/C(C)(C)N2CCN(CC2)C2COC2)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 LCFFREMLXLZNHE-GBOLQPHISA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- PCRIYZBBHYNGDG-UHFFFAOYSA-N 1-[(4-bromophenyl)methyl]-6-hydrazinyl-3-propylpyrimidine-2,4-dione Chemical compound O=C1N(CCC)C(=O)C=C(NN)N1CC1=CC=C(Br)C=C1 PCRIYZBBHYNGDG-UHFFFAOYSA-N 0.000 description 1
- XNLZUSOCLKDYHJ-UHFFFAOYSA-N 1-[[3-[(3-chlorophenyl)methyl]-2,6-dioxo-1-propylpyrimidin-4-yl]amino]-3-methylthiourea Chemical compound O=C1N(CCC)C(=O)C=C(NNC(=S)NC)N1CC1=CC=CC(Cl)=C1 XNLZUSOCLKDYHJ-UHFFFAOYSA-N 0.000 description 1
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 1
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- KDDPNNXAZURUGP-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)-3-[2-(piperidin-3-ylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound ClC=1C=C(C=CC=1Cl)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NC1CNCCC1 KDDPNNXAZURUGP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP87301950A EP0237289A3 (en) | 1986-03-14 | 1987-03-06 | Pyrazolo [3,4-d] pyrimidine derivatives, their production and use |
| DK122587A DK122587A (da) | 1986-03-14 | 1987-03-10 | Pyrazolo(3,4-d)pyrimidinderivater og fremstilling og anvendelse deraf |
| NO871024A NO164542C (no) | 1986-03-14 | 1987-03-12 | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrazolo(3,4-d)-pyrimidinderivater. |
| FI871123A FI871123A (fi) | 1986-03-14 | 1987-03-13 | Pyrazolo/3,4-d/pyrimidinderivat, deras framstaellning och anvaendning. |
| KR870002276A KR870008882A (ko) | 1986-03-14 | 1987-03-13 | 피라졸로[3,4-d] 피리미딘 유도체, 그의 제조방법 및 용도 |
| US07/025,622 US4824848A (en) | 1986-03-14 | 1987-03-13 | Pyrazolo[3,4-d]pyrimidine derivatives, their production and use |
| HU871116A HU197749B (en) | 1986-03-14 | 1987-03-13 | Process for producing /3,4-d/pyrimidine derivatives and pharmaceutical compositions comprising these compounds as active ingredient |
| PT84478A PT84478B (pt) | 1986-03-14 | 1987-03-13 | Processo para a preparacao de derivados de pirazolo-{3,4-d}-pirimidina e de composicoes farmaceuticas que os contem |
| CN198787101864A CN87101864A (zh) | 1986-03-14 | 1987-03-13 | 吡唑并[3，4-d]嘧啶衍生物及其生产和用途 |
| KR1019870006921A KR880009021A (ko) | 1986-03-14 | 1987-07-01 | 피라졸로[3,4-d]피리미딘 유도체, 그의 조성물 및 용도 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61-57920 | 1986-03-14 | ||
| JP5792086 | 1986-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6310788A true JPS6310788A (ja) | 1988-01-18 |
Family
ID=13069433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62014627A Pending JPS6310788A (ja) | 1986-03-14 | 1987-01-23 | ３−アミノピラゾロ〔３，４−ｄ〕ピリミジン誘導体 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS6310788A (ko) |
| KR (2) | KR870008882A (ko) |
| SU (1) | SU1591811A3 (ko) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5652214A (en) * | 1989-06-05 | 1997-07-29 | Cephalon, Inc. | Treating disorders by application of insulin-like growth factors and analogs |
| JP2009539872A (ja) * | 2006-06-06 | 2009-11-19 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| US8697710B2 (en) | 2008-12-06 | 2014-04-15 | Intra-Cellular Therapies, Inc. | Optionally substituted 3-amino-4-(thioxo or imino)-4,5-dihydro-2H-pyrazolo [3,4-d]pyrimidin-6(7H)-ones |
| US8846693B2 (en) | 2007-12-06 | 2014-09-30 | Intra-Cellular Therapies, Inc. | Optionally substituted pyrazolo[3,4-d]pyrimidine-4,6-diones |
| US8859564B2 (en) | 2008-12-06 | 2014-10-14 | Intra-Cellular Therapies, Inc. | Pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione derivatives useful as inhibitors of phosphodiesterase 1 |
| US8927556B2 (en) | 2008-12-06 | 2015-01-06 | Intra-Cellular Therapies, Inc. | 1H-pyrrolo[3,4-D]pyrimidin-2(6H)-one compounds |
| US9371327B2 (en) | 2010-05-31 | 2016-06-21 | Intra-Cellular Therapies, Inc. | PDE1 inhibitor compounds |
| US9434730B2 (en) | 2010-05-31 | 2016-09-06 | Intra-Cellular Therapies, Inc. | PDE1 inhibitor compounds |
| US9546175B2 (en) | 2014-08-07 | 2017-01-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
-
1987
- 1987-01-23 JP JP62014627A patent/JPS6310788A/ja active Pending
- 1987-03-13 SU SU874202196A patent/SU1591811A3/ru active
- 1987-03-13 KR KR870002276A patent/KR870008882A/ko not_active Application Discontinuation
- 1987-07-01 KR KR1019870006921A patent/KR880009021A/ko not_active Application Discontinuation
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5652214A (en) * | 1989-06-05 | 1997-07-29 | Cephalon, Inc. | Treating disorders by application of insulin-like growth factors and analogs |
| JP2009539872A (ja) * | 2006-06-06 | 2009-11-19 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| JP2014012729A (ja) * | 2006-06-06 | 2014-01-23 | Intra-Cellular Therapies Inc | 有機化合物 |
| US8846693B2 (en) | 2007-12-06 | 2014-09-30 | Intra-Cellular Therapies, Inc. | Optionally substituted pyrazolo[3,4-d]pyrimidine-4,6-diones |
| US8697710B2 (en) | 2008-12-06 | 2014-04-15 | Intra-Cellular Therapies, Inc. | Optionally substituted 3-amino-4-(thioxo or imino)-4,5-dihydro-2H-pyrazolo [3,4-d]pyrimidin-6(7H)-ones |
| US8859564B2 (en) | 2008-12-06 | 2014-10-14 | Intra-Cellular Therapies, Inc. | Pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione derivatives useful as inhibitors of phosphodiesterase 1 |
| US8927556B2 (en) | 2008-12-06 | 2015-01-06 | Intra-Cellular Therapies, Inc. | 1H-pyrrolo[3,4-D]pyrimidin-2(6H)-one compounds |
| US9487527B2 (en) | 2008-12-06 | 2016-11-08 | Intra-Cellular Therapies, Inc. | Pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione derivatives useful as inhibitors of phosphodiesterase I |
| US9371327B2 (en) | 2010-05-31 | 2016-06-21 | Intra-Cellular Therapies, Inc. | PDE1 inhibitor compounds |
| US9434730B2 (en) | 2010-05-31 | 2016-09-06 | Intra-Cellular Therapies, Inc. | PDE1 inhibitor compounds |
| US9546175B2 (en) | 2014-08-07 | 2017-01-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| KR880009021A (ko) | 1988-09-13 |
| KR870008882A (ko) | 1987-10-21 |
| SU1591811A3 (ru) | 1990-09-07 |
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