RU2249594C2 - Пиразоло[4,3-d] пиримидины - Google Patents
Пиразоло[4,3-d] пиримидины Download PDFInfo
- Publication number
- RU2249594C2 RU2249594C2 RU2002107453/04A RU2002107453A RU2249594C2 RU 2249594 C2 RU2249594 C2 RU 2249594C2 RU 2002107453/04 A RU2002107453/04 A RU 2002107453/04A RU 2002107453 A RU2002107453 A RU 2002107453A RU 2249594 C2 RU2249594 C2 RU 2249594C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- pyrazolo
- pyrimidin
- propyl
- formula
- Prior art date
Links
- DSKLYHDHQJANOE-UHFFFAOYSA-N pyrazolo[4,3-d]pyrimidine Chemical compound C1=NC=N[C]2C=NN=C21 DSKLYHDHQJANOE-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- -1 COOA Chemical group 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 239000012453 solvate Substances 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 210000000748 cardiovascular system Anatomy 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- LIFZVJKHTQXNLW-UHFFFAOYSA-N 2-[[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]methoxy]acetic acid Chemical compound N1=C(COCC(O)=O)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 LIFZVJKHTQXNLW-UHFFFAOYSA-N 0.000 claims description 2
- FSROZMKGWKKLCJ-UHFFFAOYSA-N 4-[7-(1,3-benzodioxol-5-ylmethylamino)-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(CNC2=C3N(C)N=C(C3=NC(CCCC(O)=O)=N2)CCC)=C1 FSROZMKGWKKLCJ-UHFFFAOYSA-N 0.000 claims description 2
- DRZWRYBYLHEFQV-UHFFFAOYSA-N 4-[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]benzoic acid Chemical compound N1=C(C=2C=CC(=CC=2)C(O)=O)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 DRZWRYBYLHEFQV-UHFFFAOYSA-N 0.000 claims description 2
- OTFCTERWNNKKLG-UHFFFAOYSA-N 5-[7-(benzylamino)-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]pentanoic acid Chemical compound N1=C(CCCCC(O)=O)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=CC=C1 OTFCTERWNNKKLG-UHFFFAOYSA-N 0.000 claims description 2
- JGIJIXPDDMRERS-UHFFFAOYSA-N 5-[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]pentanoic acid Chemical compound N1=C(CCCCC(O)=O)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 JGIJIXPDDMRERS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 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 claims description 2
- 102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims 2
- 108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 208000030499 combat disease Diseases 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 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
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000004809 1-methylpropylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
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- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- OCNMSDZALRAYEX-UHFFFAOYSA-N (3-chloro-4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1Cl OCNMSDZALRAYEX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- LELLVPBOWTZSJT-UHFFFAOYSA-N 3-[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]propanoic acid Chemical compound N1=C(CCC(O)=O)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 LELLVPBOWTZSJT-UHFFFAOYSA-N 0.000 description 2
- APPWKPUSFVSTAH-UHFFFAOYSA-N 4-[7-(2,3-dihydro-1,4-benzodioxin-6-ylmethylamino)-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]benzoic acid Chemical compound N1=C2C(CCC)=NN(C)C2=C(NCC=2C=C3OCCOC3=CC=2)N=C1C1=CC=C(C(O)=O)C=C1 APPWKPUSFVSTAH-UHFFFAOYSA-N 0.000 description 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 2
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
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- 230000000699 topical effect Effects 0.000 description 2
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- DOTPSQVYOBAWPQ-UHFFFAOYSA-N pyrazolo[4,3-d]pyrimidin-3-one Chemical class N1=CN=C2C(=O)N=NC2=C1 DOTPSQVYOBAWPQ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 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
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19942474A DE19942474A1 (de) | 1999-09-06 | 1999-09-06 | Pyrazolo[4,3-d]pyrimidine |
| DE19942474.8 | 1999-09-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2002107453A RU2002107453A (ru) | 2003-11-10 |
| RU2249594C2 true RU2249594C2 (ru) | 2005-04-10 |
Family
ID=7920966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2002107453/04A RU2249594C2 (ru) | 1999-09-06 | 2000-08-24 | Пиразоло[4,3-d] пиримидины |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6777419B1 (enExample) |
| EP (1) | EP1210349B1 (enExample) |
| JP (1) | JP4975921B2 (enExample) |
| KR (1) | KR20020025253A (enExample) |
| CN (1) | CN1145627C (enExample) |
| AR (1) | AR025569A1 (enExample) |
| AT (1) | ATE231866T1 (enExample) |
| AU (1) | AU773878B2 (enExample) |
| BR (1) | BR0013781A (enExample) |
| CA (1) | CA2384037C (enExample) |
| CZ (1) | CZ294587B6 (enExample) |
| DE (2) | DE19942474A1 (enExample) |
| DK (1) | DK1210349T3 (enExample) |
| ES (1) | ES2189766T3 (enExample) |
| HU (1) | HUP0202624A3 (enExample) |
| MX (1) | MXPA02002383A (enExample) |
| NO (1) | NO20021083D0 (enExample) |
| PL (1) | PL353366A1 (enExample) |
| PT (1) | PT1210349E (enExample) |
| RU (1) | RU2249594C2 (enExample) |
| SK (1) | SK3132002A3 (enExample) |
| WO (1) | WO2001018004A2 (enExample) |
| ZA (1) | ZA200202653B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10031584A1 (de) | 2000-06-29 | 2002-01-10 | Merck Patent Gmbh | 5-Aminoalkyl-pyrazolo[4,3-d]pyrimidine |
| DE10058662A1 (de) * | 2000-11-25 | 2002-05-29 | Merck Patent Gmbh | Verwendung von Pyrazolo[4,3-d]pyrimidinen |
| PL362513A1 (en) * | 2000-12-19 | 2004-11-02 | Merck Patent Gmbh | Pharmaceutical formulation containing pyrazolo[4,3-d]pyrimidines and antithrombotic agents, calcium-antagonists, prostaglandins or prostaglandin derivatives |
| DE10103647A1 (de) * | 2001-01-27 | 2002-08-01 | Merck Patent Gmbh | Verfahren zur Herstellung eines Pyrazolo (4,3-d) pyrimidinderivates |
| DE10148883A1 (de) * | 2001-10-04 | 2003-04-10 | Merck Patent Gmbh | Pyrimidinderivate |
| EP1620437B1 (en) | 2003-04-29 | 2009-06-17 | Pfizer Limited | 5,7-diaminopyrazolo¬4,3-d pyrimidines useful in the traetment of hypertension |
| US7572799B2 (en) * | 2003-11-24 | 2009-08-11 | Pfizer Inc | Pyrazolo[4,3-d]pyrimidines as Phosphodiesterase Inhibitors |
| GB0327323D0 (en) * | 2003-11-24 | 2003-12-31 | Pfizer Ltd | Novel pharmaceuticals |
| ATE417849T1 (de) * | 2004-04-07 | 2009-01-15 | Pfizer | Pyrazoloä4,3-düpyrimidine |
| EP1881985B1 (en) | 2005-05-12 | 2010-12-29 | Pfizer, Inc. | Anhydrous crystalline forms of n-ý1-(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. |
| CA2831634C (en) * | 2011-04-21 | 2019-11-12 | Origenis Gmbh | Pyrazolo [4,3-d] pyrimidines useful as kinase inhibitors |
| CZ308056B6 (cs) * | 2015-07-20 | 2019-11-27 | Ustav Experimentalni Botaniky Av Cr V V I | 5-Substituované-7-[4-(substituované)benzyl]amino-3-isopropylpyrazolo[4,3-d]pyrimidiny, jejich použití jako antirevmatika, a farmaceutické přípravky |
| US10034861B2 (en) | 2016-07-04 | 2018-07-31 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| AR113926A1 (es) | 2017-12-14 | 2020-07-01 | H Lundbeck As | Derivados de 1h-pirazolo[4,3-b]piridinas |
| RU2020118913A (ru) | 2017-12-14 | 2022-01-14 | Х. Лундбекк А/С (H. Lundbeck A/S) | Виды комбинированного лечения, предусматривающего введение 1h-пиразолo[4,3-b]пиридинов |
| US11535611B2 (en) | 2017-12-20 | 2022-12-27 | H. Lundbeck A/S | Pyrazolo[3,4-B]pyridines and imidazo[1,5-B]pyridazines as PDE1 inhibitors |
| US10766893B2 (en) * | 2017-12-20 | 2020-09-08 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2114113C1 (ru) * | 1991-07-09 | 1998-06-27 | Пфайзер Инк. | Пиразолопиримидиноны, фармацевтическая композиция и способ ингибирования фосфодиэстеразы циклического гуанозин-3',5'-монофосфата |
| WO1998049166A1 (en) * | 1997-04-25 | 1998-11-05 | Pfizer Limited | PYRAZOLOPYRIMIDINONES WHICH INHIBIT TYPE 5 CYCLIC GUANOSINE 3',5'-MONOPHOSPHATE PHOSPHODIESTERASE (cGMP PDE5) FOR THE TREATMENT OF SEXUAL DYSFUNCTION |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5256650A (en) * | 1989-03-29 | 1993-10-26 | Merrell Dow Pharmaceuticals Inc. | Selective adenosine receptor agents |
| DE19644228A1 (de) * | 1996-10-24 | 1998-04-30 | Merck Patent Gmbh | Thienopyrimidine |
| DE19752952A1 (de) * | 1997-11-28 | 1999-06-02 | Merck Patent Gmbh | Thienopyrimidine |
| DE10031584A1 (de) * | 2000-06-29 | 2002-01-10 | Merck Patent Gmbh | 5-Aminoalkyl-pyrazolo[4,3-d]pyrimidine |
| DE10058662A1 (de) * | 2000-11-25 | 2002-05-29 | Merck Patent Gmbh | Verwendung von Pyrazolo[4,3-d]pyrimidinen |
| DE10060388A1 (de) * | 2000-12-05 | 2002-06-06 | Merck Patent Gmbh | Verwendung von Pyrazolo [4,3-d]pyrimidinen |
| DE10103647A1 (de) * | 2001-01-27 | 2002-08-01 | Merck Patent Gmbh | Verfahren zur Herstellung eines Pyrazolo (4,3-d) pyrimidinderivates |
-
1999
- 1999-09-06 DE DE19942474A patent/DE19942474A1/de not_active Withdrawn
-
2000
- 2000-08-24 DE DE50001191T patent/DE50001191D1/de not_active Expired - Lifetime
- 2000-08-24 AU AU72793/00A patent/AU773878B2/en not_active Ceased
- 2000-08-24 DK DK00960511T patent/DK1210349T3/da active
- 2000-08-24 EP EP00960511A patent/EP1210349B1/de not_active Expired - Lifetime
- 2000-08-24 KR KR1020027002893A patent/KR20020025253A/ko not_active Ceased
- 2000-08-24 ES ES00960511T patent/ES2189766T3/es not_active Expired - Lifetime
- 2000-08-24 CN CNB008137366A patent/CN1145627C/zh not_active Expired - Fee Related
- 2000-08-24 PT PT00960511T patent/PT1210349E/pt unknown
- 2000-08-24 WO PCT/EP2000/008257 patent/WO2001018004A2/de not_active Ceased
- 2000-08-24 RU RU2002107453/04A patent/RU2249594C2/ru not_active IP Right Cessation
- 2000-08-24 MX MXPA02002383A patent/MXPA02002383A/es active IP Right Grant
- 2000-08-24 CZ CZ2002736A patent/CZ294587B6/cs not_active IP Right Cessation
- 2000-08-24 HU HU0202624A patent/HUP0202624A3/hu unknown
- 2000-08-24 CA CA002384037A patent/CA2384037C/en not_active Expired - Fee Related
- 2000-08-24 JP JP2001522227A patent/JP4975921B2/ja not_active Expired - Fee Related
- 2000-08-24 BR BR0013781-2A patent/BR0013781A/pt not_active IP Right Cessation
- 2000-08-24 SK SK313-2002A patent/SK3132002A3/sk unknown
- 2000-08-24 US US10/070,305 patent/US6777419B1/en not_active Expired - Fee Related
- 2000-08-24 AT AT00960511T patent/ATE231866T1/de not_active IP Right Cessation
- 2000-08-24 PL PL00353366A patent/PL353366A1/xx unknown
- 2000-09-06 AR ARP000104648A patent/AR025569A1/es unknown
-
2002
- 2002-03-05 NO NO20021083A patent/NO20021083D0/no not_active Application Discontinuation
- 2002-04-04 ZA ZA200202653A patent/ZA200202653B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2114113C1 (ru) * | 1991-07-09 | 1998-06-27 | Пфайзер Инк. | Пиразолопиримидиноны, фармацевтическая композиция и способ ингибирования фосфодиэстеразы циклического гуанозин-3',5'-монофосфата |
| WO1998049166A1 (en) * | 1997-04-25 | 1998-11-05 | Pfizer Limited | PYRAZOLOPYRIMIDINONES WHICH INHIBIT TYPE 5 CYCLIC GUANOSINE 3',5'-MONOPHOSPHATE PHOSPHODIESTERASE (cGMP PDE5) FOR THE TREATMENT OF SEXUAL DYSFUNCTION |
Non-Patent Citations (2)
| Title |
|---|
| п.1, 10, 12. * |
| реферат, формула. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1377357A (zh) | 2002-10-30 |
| DE50001191D1 (de) | 2003-03-06 |
| AR025569A1 (es) | 2002-12-04 |
| BR0013781A (pt) | 2002-05-14 |
| DE19942474A1 (de) | 2001-03-15 |
| PT1210349E (pt) | 2003-06-30 |
| PL353366A1 (en) | 2003-11-17 |
| HUP0202624A3 (en) | 2004-11-29 |
| CZ294587B6 (cs) | 2005-02-16 |
| JP2003508534A (ja) | 2003-03-04 |
| HUP0202624A2 (hu) | 2002-12-28 |
| ZA200202653B (en) | 2003-09-23 |
| DK1210349T3 (da) | 2003-05-19 |
| EP1210349B1 (de) | 2003-01-29 |
| CA2384037C (en) | 2009-10-13 |
| CN1145627C (zh) | 2004-04-14 |
| MXPA02002383A (es) | 2002-09-02 |
| KR20020025253A (ko) | 2002-04-03 |
| AU7279300A (en) | 2001-04-10 |
| WO2001018004A2 (de) | 2001-03-15 |
| EP1210349A2 (de) | 2002-06-05 |
| CA2384037A1 (en) | 2001-03-15 |
| ATE231866T1 (de) | 2003-02-15 |
| NO20021083L (no) | 2002-03-05 |
| WO2001018004A3 (de) | 2001-08-09 |
| AU773878B2 (en) | 2004-06-10 |
| NO20021083D0 (no) | 2002-03-05 |
| CZ2002736A3 (cs) | 2002-05-15 |
| JP4975921B2 (ja) | 2012-07-11 |
| ES2189766T3 (es) | 2003-07-16 |
| US6777419B1 (en) | 2004-08-17 |
| SK3132002A3 (en) | 2002-07-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20060825 |