CA2203379C - Inhibiteurs de cgmp-pde destines au traitement du dysfonctionnement erectile - Google Patents
Inhibiteurs de cgmp-pde destines au traitement du dysfonctionnement erectile Download PDFInfo
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- CA2203379C CA2203379C CA 2203379 CA2203379A CA2203379C CA 2203379 C CA2203379 C CA 2203379C CA 2203379 CA2203379 CA 2203379 CA 2203379 A CA2203379 A CA 2203379A CA 2203379 C CA2203379 C CA 2203379C
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- alkyl
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- 201000001881 impotence Diseases 0.000 title claims abstract description 28
- 208000010228 Erectile Dysfunction Diseases 0.000 title claims abstract description 24
- 238000011282 treatment Methods 0.000 title claims abstract description 21
- 239000003112 inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 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 abstract description 18
- 241001465754 Metazoa Species 0.000 claims abstract description 15
- -1 nitro, amino Chemical group 0.000 claims description 348
- 125000000217 alkyl group Chemical group 0.000 claims description 300
- 229910052739 hydrogen Inorganic materials 0.000 claims description 250
- 239000001257 hydrogen Substances 0.000 claims description 250
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 243
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 125
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 117
- 229910052757 nitrogen Inorganic materials 0.000 claims description 115
- 150000003254 radicals Chemical class 0.000 claims description 102
- 125000003118 aryl group Chemical group 0.000 claims description 96
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 92
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 89
- 229910052736 halogen Inorganic materials 0.000 claims description 85
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 81
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 80
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 79
- 150000002367 halogens Chemical class 0.000 claims description 79
- 125000003545 alkoxy group Chemical group 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 69
- 125000005843 halogen group Chemical group 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 52
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 50
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 46
- 229920006395 saturated elastomer Polymers 0.000 claims description 46
- 125000005842 heteroatom Chemical group 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 32
- 238000006467 substitution reaction Methods 0.000 claims description 32
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 239000005864 Sulphur Substances 0.000 claims description 23
- UUXLGTAOQFJWNK-UHFFFAOYSA-N NNS(=O)(=O)[N+]([O-])=O Chemical class NNS(=O)(=O)[N+]([O-])=O UUXLGTAOQFJWNK-UHFFFAOYSA-N 0.000 claims description 20
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
- 150000001721 carbon Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 9
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 8
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 8
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 8
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- BYKFPARGCLDSFK-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethylamino)-6-nitroquinazolin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C=C(C=C2)[N+]([O-])=O)C2=N1 BYKFPARGCLDSFK-UHFFFAOYSA-N 0.000 claims description 6
- OULXFNCZTZKFKS-UHFFFAOYSA-N 4-ethoxy-2-phenylcyclohepta[d]imidazole Chemical compound N1=C2C(OCC)=CC=CC=C2N=C1C1=CC=CC=C1 OULXFNCZTZKFKS-UHFFFAOYSA-N 0.000 claims description 6
- QSLLFYVBWXWUQT-UHFFFAOYSA-N 7-Azaindolizine Chemical compound C1=NC=CN2C=CC=C21 QSLLFYVBWXWUQT-UHFFFAOYSA-N 0.000 claims description 6
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 6
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 6
- 206010057671 Female sexual dysfunction Diseases 0.000 claims description 6
- 206010036600 Premature labour Diseases 0.000 claims description 6
- HZRNGLPDDYCHGF-UHFFFAOYSA-N [4-(benzylamino)-6-chloroquinazolin-2-yl]-imidazol-1-ylmethanone Chemical compound C12=CC(Cl)=CC=C2N=C(C(=O)N2C=NC=C2)N=C1NCC1=CC=CC=C1 HZRNGLPDDYCHGF-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 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 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 6
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 5
- GODZWYONGRENHA-UHFFFAOYSA-N 1-cyclopentyl-3-methyl-6-pyridin-4-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=2N=C(C=3C=CN=CC=3)NC(=O)C=2C(C)=NN1C1CCCC1 GODZWYONGRENHA-UHFFFAOYSA-N 0.000 claims description 5
- OITYPBKBSWVLGP-UHFFFAOYSA-N 3-benzyl-1-tert-butyl-6-pyridin-4-yl-2h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=NC(=O)C=2C=1N(C(C)(C)C)NC=2CC1=CC=CC=C1 OITYPBKBSWVLGP-UHFFFAOYSA-N 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- JOSMPBVYYKRYLG-OLZOCXBDSA-N sch-51866 Chemical compound N1([C@H]2CCC[C@H]2N=C1N(C(C=1N2)=O)C)C=1N=C2CC1=CC=C(C(F)(F)F)C=C1 JOSMPBVYYKRYLG-OLZOCXBDSA-N 0.000 claims description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005002 aryl methyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- PBRFQQAUEOPPGQ-UHFFFAOYSA-N 1-ethyl-3-methyl-5h-imidazo[1,5-a]quinoxalin-4-one Chemical compound C1=CC=C2NC(=O)C3=C(C)N=C(CC)N3C2=C1 PBRFQQAUEOPPGQ-UHFFFAOYSA-N 0.000 claims description 3
- PQTJTRTXCNZDFT-UHFFFAOYSA-N 2-(2-propoxyphenyl)-3,7-dihydropurin-6-one Chemical compound CCCOC1=CC=CC=C1C(N1)=NC(=O)C2=C1N=CN2 PQTJTRTXCNZDFT-UHFFFAOYSA-N 0.000 claims description 3
- VWHURTSQUBIHDW-UHFFFAOYSA-N 2-methylsulfanyl-7-(2-propoxyphenyl)-8h-pyrimido[4,5-d]pyrimidin-5-one Chemical compound CCCOC1=CC=CC=C1C1=NC2=NC(SC)=NC=C2C(=O)N1 VWHURTSQUBIHDW-UHFFFAOYSA-N 0.000 claims description 3
- WNRKQRDTOFFQAM-UHFFFAOYSA-N 2-oxo-6-(2-propoxyphenyl)-1h-pyridine-3-carboxamide Chemical compound CCCOC1=CC=CC=C1C1=CC=C(C(N)=O)C(=O)N1 WNRKQRDTOFFQAM-UHFFFAOYSA-N 0.000 claims description 3
- GPCIGOMWSAEZKY-UHFFFAOYSA-N 4-oxo-2-(2-propoxyphenyl)-1h-pyrimidine-6-carboxamide Chemical compound CCCOC1=CC=CC=C1C1=NC(O)=CC(C(N)=O)=N1 GPCIGOMWSAEZKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- VFHGGXLXVCGUHU-UHFFFAOYSA-N ethyl 2-butyl-3-[(2-chlorophenyl)methyl]benzimidazole-5-carboxylate Chemical compound CCCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=CC=C1Cl VFHGGXLXVCGUHU-UHFFFAOYSA-N 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- XOAKQCOPHMCADA-UHFFFAOYSA-N 4,8-dioxatricyclo[5.1.0.03,5]octane Chemical compound C1C2OC2CC2OC12 XOAKQCOPHMCADA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
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- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- LSTFJJYBBWBCAR-UHFFFAOYSA-N 2-(2-propoxyphenyl)-1h-pyrido[2,3-d]pyrimidin-4-one Chemical compound CCCOC1=CC=CC=C1C1=NC2=NC=CC=C2C(=O)N1 LSTFJJYBBWBCAR-UHFFFAOYSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 108091008642 NR6A Proteins 0.000 claims 1
- 101100212791 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YBL068W-A gene Proteins 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 238000009109 curative therapy Methods 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229940124639 Selective inhibitor Drugs 0.000 abstract description 5
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 11
- 229940124530 sulfonamide Drugs 0.000 description 8
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 208000006673 asthma Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000018052 penile erection Effects 0.000 description 3
- 210000003899 penis Anatomy 0.000 description 3
- WJSVJNDMOQTICG-UHFFFAOYSA-N 2-amino-1-[(2-methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-7h-purin-6-one Chemical compound NC1=NC=2N=CNC=2C(=O)N1CC1(C)CC(=C)C(=O)O1 WJSVJNDMOQTICG-UHFFFAOYSA-N 0.000 description 2
- KJMFQJFNQYWQAV-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinazoline Chemical class C1=NC=NC2=C(NC=N3)C3=CC=C21 KJMFQJFNQYWQAV-UHFFFAOYSA-N 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 description 2
- 208000010412 Glaucoma Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Ces composés qui sont des inhibiteurs sélectifs des cGMP PDE (guanosine 3',5'-monophosphate cyclique phosphodiestérase) sont utiles dans le traitement du dysfonctionnement érectile (impuissance) chez les animaux mâles, notamment chez l'homme.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9423910A GB9423910D0 (en) | 1994-11-26 | 1994-11-26 | Therapeutic agents |
| GB9423910.0 | 1994-11-26 | ||
| PCT/EP1995/004066 WO1996016644A1 (fr) | 1994-11-26 | 1995-10-16 | INHIBITEURS DE cGMP-PDE DESTINES AU TRAITEMENT DU DYSFONCTIONNEMENT ERECTILE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2203379A1 CA2203379A1 (fr) | 1996-06-06 |
| CA2203379C true CA2203379C (fr) | 2006-01-03 |
Family
ID=29403918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2203379 Expired - Fee Related CA2203379C (fr) | 1994-11-26 | 1995-10-16 | Inhibiteurs de cgmp-pde destines au traitement du dysfonctionnement erectile |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2203379C (fr) |
-
1995
- 1995-10-16 CA CA 2203379 patent/CA2203379C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2203379A1 (fr) | 1996-06-06 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |