CZ20024054A3 - Derivát 5-aminoalkylpyrazolo[4,3-d]pyrimidinu, způsob jeho přípravy, jeho použití a léčivo, které ho obsahuje - Google Patents
Derivát 5-aminoalkylpyrazolo[4,3-d]pyrimidinu, způsob jeho přípravy, jeho použití a léčivo, které ho obsahuje Download PDFInfo
- Publication number
- CZ20024054A3 CZ20024054A3 CZ20024054A CZ20024054A CZ20024054A3 CZ 20024054 A3 CZ20024054 A3 CZ 20024054A3 CZ 20024054 A CZ20024054 A CZ 20024054A CZ 20024054 A CZ20024054 A CZ 20024054A CZ 20024054 A3 CZ20024054 A3 CZ 20024054A3
- Authority
- CZ
- Czechia
- Prior art keywords
- methyl
- chloro
- propyl
- methoxybenzylamino
- pyrazolo
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 12
- 239000003814 drug Substances 0.000 title claims description 11
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
- -1 3-chloro-4-methoxybenzylamino Chemical group 0.000 claims description 79
- 150000003839 salts Chemical class 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- RQJONRSGCKELHP-UHFFFAOYSA-N n-[(3-chloro-4-methoxyphenyl)methyl]-5-[(3-methoxypropylamino)methyl]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(CNCCCOC)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 RQJONRSGCKELHP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- OKGNMRKOGWTADH-UHFFFAOYSA-N 1,4-dihydropyrimidine Chemical compound C1C=CNC=N1 OKGNMRKOGWTADH-UHFFFAOYSA-N 0.000 claims 1
- NIPDFWTURVJIEA-UHFFFAOYSA-N 1-piperazin-1-ylpropane-1,2-diol Chemical compound CC(O)C(O)N1CCNCC1 NIPDFWTURVJIEA-UHFFFAOYSA-N 0.000 claims 1
- 102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 abstract description 2
- 108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 abstract description 2
- 201000010099 disease Diseases 0.000 abstract description 2
- AEUWLJSEFXGQHI-UHFFFAOYSA-N 1h-pyrazolo[4,3-d]pyrimidin-5-ylmethanamine Chemical class NCC1=NC=C2NN=CC2=N1 AEUWLJSEFXGQHI-UHFFFAOYSA-N 0.000 abstract 1
- 210000000748 cardiovascular system Anatomy 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
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- 208000035475 disorder Diseases 0.000 description 4
- 150000002431 hydrogen Chemical class 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
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- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
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- 239000000829 suppository Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
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- OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 description 1
- XFTJDNXIIXRJCY-UHFFFAOYSA-N 1-[[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]methyl]piperidin-4-ol Chemical compound N1=C(CN2CCC(O)CC2)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 XFTJDNXIIXRJCY-UHFFFAOYSA-N 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- SKVKUFJIZDSVQE-UHFFFAOYSA-N n,n-dimethylformamide;1-methylpyrrolidine Chemical compound CN(C)C=O.CN1CCCC1 SKVKUFJIZDSVQE-UHFFFAOYSA-N 0.000 description 1
- GTJFHWRLDZJNEA-UHFFFAOYSA-N n-[(3-chloro-4-methoxyphenyl)methyl]-5-(chloromethyl)-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(CCl)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 GTJFHWRLDZJNEA-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 230000018791 negative regulation of catalytic activity Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 150000004713 phosphodiesters Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000005229 pyrazolopyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10031584A DE10031584A1 (de) | 2000-06-29 | 2000-06-29 | 5-Aminoalkyl-pyrazolo[4,3-d]pyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ20024054A3 true CZ20024054A3 (cs) | 2003-04-16 |
Family
ID=7647151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20024054A CZ20024054A3 (cs) | 2000-06-29 | 2001-06-28 | Derivát 5-aminoalkylpyrazolo[4,3-d]pyrimidinu, způsob jeho přípravy, jeho použití a léčivo, které ho obsahuje |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7060823B2 (enExample) |
| EP (1) | EP1296986B1 (enExample) |
| JP (1) | JP4964388B2 (enExample) |
| KR (1) | KR20030017558A (enExample) |
| CN (1) | CN1439011A (enExample) |
| AR (1) | AR028772A1 (enExample) |
| AT (1) | ATE519761T1 (enExample) |
| AU (2) | AU7970001A (enExample) |
| BR (1) | BR0111915A (enExample) |
| CA (1) | CA2410399C (enExample) |
| CZ (1) | CZ20024054A3 (enExample) |
| DE (1) | DE10031584A1 (enExample) |
| ES (1) | ES2367704T3 (enExample) |
| HU (1) | HUP0301587A3 (enExample) |
| MX (1) | MXPA02012263A (enExample) |
| NO (1) | NO20026247L (enExample) |
| PL (1) | PL358551A1 (enExample) |
| RU (1) | RU2271359C2 (enExample) |
| SK (1) | SK17632002A3 (enExample) |
| WO (1) | WO2002000660A1 (enExample) |
| ZA (1) | ZA200209728B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19942474A1 (de) * | 1999-09-06 | 2001-03-15 | Merck Patent Gmbh | Pyrazolo[4,3-d]pyrimidine |
| DE10031585A1 (de) * | 2000-06-29 | 2002-01-10 | Merck Patent Gmbh | 2-Aminoalkyl-thieno[2,3-d]pyrimidine |
| DE10058662A1 (de) * | 2000-11-25 | 2002-05-29 | Merck Patent Gmbh | Verwendung von Pyrazolo[4,3-d]pyrimidinen |
| EA008596B1 (ru) | 2003-04-29 | 2007-06-29 | Пфайзер Инк. | 5,7-ДИАМИНОПИРАЗОЛО[4,3-d]ПИРИМИДИНЫ, ПОЛЕЗНЫЕ ПРИ ЛЕЧЕНИИ ГИПЕРТЕНЗИИ |
| UA80871C2 (en) * | 2003-04-29 | 2007-11-12 | Pfizer Ltd | 5,7-diaminopyrazolo[4,3-d]pyrimidines useful in the treatment of hypertension |
| GB0327323D0 (en) * | 2003-11-24 | 2003-12-31 | Pfizer Ltd | Novel pharmaceuticals |
| US7572799B2 (en) * | 2003-11-24 | 2009-08-11 | Pfizer Inc | Pyrazolo[4,3-d]pyrimidines as Phosphodiesterase Inhibitors |
| GB0327319D0 (en) * | 2003-11-24 | 2003-12-24 | Pfizer Ltd | Novel pharmaceuticals |
| JP2007532526A (ja) * | 2004-04-07 | 2007-11-15 | ファイザー・インク | ピラゾロ［４，３−ｄ］ピリミジン類 |
| JP2008517994A (ja) * | 2004-10-28 | 2008-05-29 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 新規医薬品 |
| US8227475B2 (en) * | 2005-05-12 | 2012-07-24 | Pfizer Inc. | Anhydrous crystalline forms of N-[1-(2-ethoxyethyl)-5-(N-ethyl-N-methylamino)-7-(4-methylpyridin-2-yl-amino)-1H-pyrazolo[4,3-d]pyrimidine-3-carbonyl]methanesulfonamide |
| NL2000291C2 (nl) | 2005-11-10 | 2009-02-17 | Pfizer Prod Inc | 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H- pyrazool(4,3-d)pyrimidine-5-yl)piperidine-4-carbonzuur en zouten daarvan. |
| DE102012200360A1 (de) * | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte Triazine und ihre Verwendung |
| CA2782774A1 (en) * | 2012-07-06 | 2014-01-06 | Pharmascience Inc. | Protein kinase inhibitors |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1739850A3 (ru) * | 1987-08-31 | 1992-06-07 | Такеда Кемикал Индастриз, Лтд (Фирма) | Способ получени конденсированных производных пиразоло[3,4- @ ]пиримидина |
| US5075310A (en) | 1988-07-01 | 1991-12-24 | Smith Kline & French Laboratories, Ltd. | Pyrimidone derivatives as bronchodilators |
| GB9119704D0 (en) * | 1991-09-14 | 1991-10-30 | Pfizer Ltd | Therapeutic agents |
| JP2657760B2 (ja) | 1992-07-15 | 1997-09-24 | 小野薬品工業株式会社 | ４−アミノキナゾリン誘導体およびそれを含有する医薬品 |
| GB9311920D0 (en) | 1993-06-09 | 1993-07-28 | Pfizer Ltd | Therapeutic agents |
| GB9423911D0 (en) * | 1994-11-26 | 1995-01-11 | Pfizer Ltd | Therapeutic agents |
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| DE19644228A1 (de) * | 1996-10-24 | 1998-04-30 | Merck Patent Gmbh | Thienopyrimidine |
| DE19752952A1 (de) * | 1997-11-28 | 1999-06-02 | Merck Patent Gmbh | Thienopyrimidine |
| DE19942474A1 (de) | 1999-09-06 | 2001-03-15 | Merck Patent Gmbh | Pyrazolo[4,3-d]pyrimidine |
-
2000
- 2000-06-29 DE DE10031584A patent/DE10031584A1/de not_active Withdrawn
-
2001
- 2001-06-28 RU RU2003100508/04A patent/RU2271359C2/ru not_active IP Right Cessation
- 2001-06-28 HU HU0301587A patent/HUP0301587A3/hu unknown
- 2001-06-28 CA CA2410399A patent/CA2410399C/en not_active Expired - Fee Related
- 2001-06-28 KR KR1020027017571A patent/KR20030017558A/ko not_active Withdrawn
- 2001-06-28 JP JP2002505784A patent/JP4964388B2/ja not_active Expired - Fee Related
- 2001-06-28 AT AT01957901T patent/ATE519761T1/de active
- 2001-06-28 US US10/312,766 patent/US7060823B2/en not_active Expired - Fee Related
- 2001-06-28 SK SK1763-2002A patent/SK17632002A3/sk unknown
- 2001-06-28 AU AU7970001A patent/AU7970001A/xx active Pending
- 2001-06-28 ES ES01957901T patent/ES2367704T3/es not_active Expired - Lifetime
- 2001-06-28 BR BR0111915-0A patent/BR0111915A/pt not_active IP Right Cessation
- 2001-06-28 CZ CZ20024054A patent/CZ20024054A3/cs unknown
- 2001-06-28 EP EP01957901A patent/EP1296986B1/de not_active Expired - Lifetime
- 2001-06-28 PL PL01358551A patent/PL358551A1/xx unknown
- 2001-06-28 MX MXPA02012263A patent/MXPA02012263A/es unknown
- 2001-06-28 AU AU2001279700A patent/AU2001279700B2/en not_active Ceased
- 2001-06-28 WO PCT/EP2001/007378 patent/WO2002000660A1/de not_active Ceased
- 2001-06-28 CN CN01811801A patent/CN1439011A/zh active Pending
- 2001-06-29 AR ARP010103144A patent/AR028772A1/es unknown
-
2002
- 2002-11-29 ZA ZA200209728A patent/ZA200209728B/en unknown
- 2002-12-27 NO NO20026247A patent/NO20026247L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL358551A1 (en) | 2004-08-09 |
| AU7970001A (en) | 2002-01-08 |
| AU2001279700B2 (en) | 2006-08-24 |
| CA2410399A1 (en) | 2002-01-03 |
| JP2004501921A (ja) | 2004-01-22 |
| DE10031584A1 (de) | 2002-01-10 |
| ATE519761T1 (de) | 2011-08-15 |
| US20040029900A1 (en) | 2004-02-12 |
| RU2271359C2 (ru) | 2006-03-10 |
| KR20030017558A (ko) | 2003-03-03 |
| NO20026247D0 (no) | 2002-12-27 |
| AR028772A1 (es) | 2003-05-21 |
| ZA200209728B (en) | 2004-03-12 |
| BR0111915A (pt) | 2003-05-13 |
| ES2367704T3 (es) | 2011-11-07 |
| EP1296986B1 (de) | 2011-08-10 |
| JP4964388B2 (ja) | 2012-06-27 |
| US7060823B2 (en) | 2006-06-13 |
| HUP0301587A3 (en) | 2005-11-28 |
| NO20026247L (no) | 2002-12-27 |
| EP1296986A1 (de) | 2003-04-02 |
| CN1439011A (zh) | 2003-08-27 |
| SK17632002A3 (sk) | 2003-05-02 |
| MXPA02012263A (es) | 2003-04-25 |
| CA2410399C (en) | 2010-02-16 |
| WO2002000660A1 (de) | 2002-01-03 |
| HUP0301587A2 (hu) | 2003-09-29 |
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