NO317877B1 - Ftalazindforbindelser og fremstilling og anvendelser derav, profylatiske og terapeutiske midlerfor erektil dysfunksjon og for kvinnelig seksuell dysfunksjon eller dysmerorr±, farmasoytiske preparat - Google Patents
Ftalazindforbindelser og fremstilling og anvendelser derav, profylatiske og terapeutiske midlerfor erektil dysfunksjon og for kvinnelig seksuell dysfunksjon eller dysmerorr±, farmasoytiske preparat Download PDFInfo
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- NO317877B1 NO317877B1 NO20000969A NO20000969A NO317877B1 NO 317877 B1 NO317877 B1 NO 317877B1 NO 20000969 A NO20000969 A NO 20000969A NO 20000969 A NO20000969 A NO 20000969A NO 317877 B1 NO317877 B1 NO 317877B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- amino
- chloro
- methoxybenzyl
- phthalazinecarbonitrile
- Prior art date
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- 239000003814 drug Substances 0.000 title claims description 30
- 201000001881 impotence Diseases 0.000 title claims description 29
- 229940124597 therapeutic agent Drugs 0.000 title claims description 29
- 208000010228 Erectile Dysfunction Diseases 0.000 title claims description 27
- 230000000069 prophylactic effect Effects 0.000 title claims description 16
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 title claims description 14
- 206010057671 Female sexual dysfunction Diseases 0.000 title claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 66
- -1 Phthalazine compound Chemical class 0.000 claims description 137
- 150000001875 compounds Chemical class 0.000 claims description 126
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 89
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 73
- 150000003839 salts Chemical class 0.000 claims description 47
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 125000003277 amino group Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 10
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- BROVXIYHWJSPHN-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(2-hydroxy-7-azaspiro[3.5]nonan-7-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC2(CC(O)C2)CC1 BROVXIYHWJSPHN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- DFLCXMDYMPFHNT-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-[3-(hydroxymethyl)pyrrolidin-1-yl]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CC(CO)CC1 DFLCXMDYMPFHNT-UHFFFAOYSA-N 0.000 claims description 2
- HURWYJRIOYWNLV-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-pyridin-4-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=NC=C1 HURWYJRIOYWNLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- CNDDZEJAONUILG-UHFFFAOYSA-N 1-(3-amino-3-methylbut-1-ynyl)-4-[(3-chloro-4-methoxyphenyl)methylamino]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NN=C(C#CC(C)(C)N)C2=CC=C(C#N)C=C12 CNDDZEJAONUILG-UHFFFAOYSA-N 0.000 claims 2
- IQGQJWWIZWVAJA-UHFFFAOYSA-N 1-[4-fluoro-4-(hydroxymethyl)piperidin-1-yl]-4-[(4-methoxy-3-methylphenyl)methylamino]phthalazine-6-carbonitrile Chemical compound C1=C(C)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(F)(CO)CC1 IQGQJWWIZWVAJA-UHFFFAOYSA-N 0.000 claims 2
- XINHUZZXLNAOEM-UHFFFAOYSA-N 4-[(3-bromo-4-methoxyphenyl)methylamino]-1-(2-hydroxy-7-azaspiro[3.5]nonan-7-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Br)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC2(CC(O)C2)CC1 XINHUZZXLNAOEM-UHFFFAOYSA-N 0.000 claims 2
- HPWMHTLTWHIJTH-UHFFFAOYSA-N 4-[(3-bromo-4-methoxyphenyl)methylamino]-1-(4-hydroxypiperidin-1-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Br)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(O)CC1 HPWMHTLTWHIJTH-UHFFFAOYSA-N 0.000 claims 2
- RNCJDMPPAXNRMU-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(2-hydroxy-6-azaspiro[3.4]octan-6-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CC2(CC(O)C2)CC1 RNCJDMPPAXNRMU-UHFFFAOYSA-N 0.000 claims 2
- CAWZLXORMBSHNP-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(4-cyanophenyl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=C(C#N)C=C1 CAWZLXORMBSHNP-UHFFFAOYSA-N 0.000 claims 2
- HYPDTWBJSGTQAB-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(4-cyanopiperidin-1-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(C#N)CC1 HYPDTWBJSGTQAB-UHFFFAOYSA-N 0.000 claims 2
- NOERFQUYGAGSLE-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-[4-(1-fluoro-2-hydroxyethyl)piperidin-1-yl]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(C(F)CO)CC1 NOERFQUYGAGSLE-UHFFFAOYSA-N 0.000 claims 2
- HVQOLJYRKSKADA-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-[4-(2-hydroxyethoxy)piperidin-1-yl]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(OCCO)CC1 HVQOLJYRKSKADA-UHFFFAOYSA-N 0.000 claims 2
- WGJBIYILKRYNIM-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-[4-(fluoromethyl)-4-hydroxypiperidin-1-yl]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(O)(CF)CC1 WGJBIYILKRYNIM-UHFFFAOYSA-N 0.000 claims 2
- PUQVMTLDRWLBIH-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-[4-(hydroxymethyl)-4-methoxypiperidin-1-yl]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(CO)(OC)CC1 PUQVMTLDRWLBIH-UHFFFAOYSA-N 0.000 claims 2
- ILVMMBZGHATNGI-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-[4-fluoro-4-(hydroxymethyl)piperidin-1-yl]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(F)(CO)CC1 ILVMMBZGHATNGI-UHFFFAOYSA-N 0.000 claims 2
- PSYHZFILEOSBMA-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-pyridin-2-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=CC=N1 PSYHZFILEOSBMA-UHFFFAOYSA-N 0.000 claims 2
- FCPMNYWZCNEYLH-UHFFFAOYSA-N 4-[(3-cyano-4-methoxyphenyl)methylamino]-1-(4-hydroxypiperidin-1-yl)phthalazine-6-carbonitrile Chemical compound C1=C(C#N)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(O)CC1 FCPMNYWZCNEYLH-UHFFFAOYSA-N 0.000 claims 2
- YGZTXMYZZAMDIE-UHFFFAOYSA-N 4-[2-(3-chloro-4-methoxyphenyl)ethylamino]-1-(2-hydroxy-7-azaspiro[3.5]nonan-7-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CCNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC2(CC(O)C2)CC1 YGZTXMYZZAMDIE-UHFFFAOYSA-N 0.000 claims 2
- XUHUZBRFBQUGIT-UHFFFAOYSA-N 4-[2-(3-chloro-4-methoxyphenyl)ethylamino]-1-(4-cyanopiperidin-1-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CCNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(C#N)CC1 XUHUZBRFBQUGIT-UHFFFAOYSA-N 0.000 claims 2
- PBLBLVDBIDUWDT-UHFFFAOYSA-N 4-[2-(3-chloro-4-methoxyphenyl)ethylamino]-1-pyridin-2-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CCNC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=CC=N1 PBLBLVDBIDUWDT-UHFFFAOYSA-N 0.000 claims 2
- BXZAUYONBJBDKL-UHFFFAOYSA-N 4-[2-(3-chloro-4-methoxyphenyl)ethylamino]-1-pyridin-4-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CCNC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=NC=C1 BXZAUYONBJBDKL-UHFFFAOYSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- IPMHCHZUEAMTHL-UHFFFAOYSA-N 1-(4-aminopiperidin-1-yl)-4-[(3-chloro-4-methoxyphenyl)methylamino]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(N)CC1 IPMHCHZUEAMTHL-UHFFFAOYSA-N 0.000 claims 1
- ZRVRDBARXBNJKD-UHFFFAOYSA-N 1-(4-hydroxypiperidin-1-yl)-4-[(4-methoxy-3-methylphenyl)methylamino]phthalazine-6-carbonitrile Chemical compound C1=C(C)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(O)CC1 ZRVRDBARXBNJKD-UHFFFAOYSA-N 0.000 claims 1
- GGNKQKZLUXYQAA-UHFFFAOYSA-N 1-[4,4-bis(hydroxymethyl)piperidin-1-yl]-4-[(3-chloro-4-methoxyphenyl)methylamino]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(CO)(CO)CC1 GGNKQKZLUXYQAA-UHFFFAOYSA-N 0.000 claims 1
- YVDFTIWFZDYQSL-UHFFFAOYSA-N 1-[4-[(3-chloro-4-methoxyphenyl)methylamino]-6-pyrazol-1-ylphthalazin-1-yl]piperidin-4-ol Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)N2N=CC=C2)=NN=C1N1CCC(O)CC1 YVDFTIWFZDYQSL-UHFFFAOYSA-N 0.000 claims 1
- CFQOXGKVNOTCMK-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-1-[(3-chloro-4-methoxyphenyl)methylamino]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC=C(C=C11)C#N)=NN=C1N1CCC(N)CC1 CFQOXGKVNOTCMK-UHFFFAOYSA-N 0.000 claims 1
- NARSLTFPFSPHTL-UHFFFAOYSA-N 4-[(3-bromo-4-methoxyphenyl)methylamino]-1-[4-(hydroxymethyl)piperidin-1-yl]phthalazine-6-carbonitrile Chemical compound C1=C(Br)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(CO)CC1 NARSLTFPFSPHTL-UHFFFAOYSA-N 0.000 claims 1
- HNBGIJSGGYFPIM-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methyl]-1-pyridin-2-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=CC=N1 HNBGIJSGGYFPIM-UHFFFAOYSA-N 0.000 claims 1
- YINYHELQWPHKLA-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methyl]-1-pyridin-3-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=CN=C1 YINYHELQWPHKLA-UHFFFAOYSA-N 0.000 claims 1
- FZMXIWVDQXMUJH-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methyl]-1-pyridin-4-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=NC=C1 FZMXIWVDQXMUJH-UHFFFAOYSA-N 0.000 claims 1
- PMIPYHOVBZCQEC-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(1-oxo-1,4-thiazinan-4-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCS(=O)CC1 PMIPYHOVBZCQEC-UHFFFAOYSA-N 0.000 claims 1
- RRULPKINSZJVOH-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(3,4-dihydroxypiperidin-1-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CC(O)C(O)CC1 RRULPKINSZJVOH-UHFFFAOYSA-N 0.000 claims 1
- CFORGCIZUVDGEF-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(3,4-dihydroxypyrrolidin-1-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CC(O)C(O)C1 CFORGCIZUVDGEF-UHFFFAOYSA-N 0.000 claims 1
- HOOREWBFHCOUDI-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(3-hydroxy-3-methylbutyl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NN=C(CCC(C)(C)O)C2=CC=C(C#N)C=C12 HOOREWBFHCOUDI-UHFFFAOYSA-N 0.000 claims 1
- UQQYBRALVPOLHC-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(4-hydroxyiminopiperidin-1-yl)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(=NO)CC1 UQQYBRALVPOLHC-UHFFFAOYSA-N 0.000 claims 1
- GGGLDMKJPXQHHL-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(4-methoxyphenyl)phthalazine-6-carbonitrile Chemical compound C1=CC(OC)=CC=C1C(C1=CC=C(C=C11)C#N)=NN=C1NCC1=CC=C(OC)C(Cl)=C1 GGGLDMKJPXQHHL-UHFFFAOYSA-N 0.000 claims 1
- MIABHIVQMMZCQM-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(4-methoxypiperidin-1-yl)phthalazine-6-carbonitrile Chemical compound C1CC(OC)CCN1C(C1=CC=C(C=C11)C#N)=NN=C1NCC1=CC=C(OC)C(Cl)=C1 MIABHIVQMMZCQM-UHFFFAOYSA-N 0.000 claims 1
- LQFHWQJCBHTIMP-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-(pyridin-2-ylmethylamino)phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1NCC1=CC=CC=N1 LQFHWQJCBHTIMP-UHFFFAOYSA-N 0.000 claims 1
- QIJVWQPYIXRYOL-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-[2-(methoxymethyl)pyrrolidin-1-yl]phthalazine-6-carbonitrile Chemical compound COCC1CCCN1C(C1=CC=C(C=C11)C#N)=NN=C1NCC1=CC=C(OC)C(Cl)=C1 QIJVWQPYIXRYOL-UHFFFAOYSA-N 0.000 claims 1
- TTXNTKBRKRNFJE-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N1CCC(O)(CO)CC1 TTXNTKBRKRNFJE-UHFFFAOYSA-N 0.000 claims 1
- YVHINMOXNQZJFL-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-[methyl(pyridin-2-ylmethyl)amino]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1N(C)CC1=CC=CC=N1 YVHINMOXNQZJFL-UHFFFAOYSA-N 0.000 claims 1
- ZICUZYIXIWINPB-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-phenylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=CC=C1 ZICUZYIXIWINPB-UHFFFAOYSA-N 0.000 claims 1
- KIJDJIHZXXZSQQ-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)methylamino]-1-pyridin-3-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CNC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=CN=C1 KIJDJIHZXXZSQQ-UHFFFAOYSA-N 0.000 claims 1
- MBTYRSJSOHVMBF-UHFFFAOYSA-N 4-[2-(3-chloro-4-methoxyphenyl)ethyl]-1-pyridin-2-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CCC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=CC=N1 MBTYRSJSOHVMBF-UHFFFAOYSA-N 0.000 claims 1
- ZXFZZSYNVLAQRX-UHFFFAOYSA-N 4-[2-(3-chloro-4-methoxyphenyl)ethyl]-1-pyridin-3-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CCC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=CN=C1 ZXFZZSYNVLAQRX-UHFFFAOYSA-N 0.000 claims 1
- CEQJRIWCRAEXJR-UHFFFAOYSA-N 4-[2-(3-chloro-4-methoxyphenyl)ethyl]-1-pyridin-4-ylphthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CCC(C1=CC(=CC=C11)C#N)=NN=C1C1=CC=NC=C1 CEQJRIWCRAEXJR-UHFFFAOYSA-N 0.000 claims 1
- NDPOVCRBKLFHJW-UHFFFAOYSA-N 4-[2-(3-chloro-4-methoxyphenyl)ethylamino]-1-[3-(hydroxymethyl)piperidin-1-yl]phthalazine-6-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1CCNC(C1=CC(=CC=C11)C#N)=NN=C1N1CC(CO)CCC1 NDPOVCRBKLFHJW-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
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PCT/JP1999/000688 WO1999042452A1 (fr) | 1998-02-19 | 1999-02-17 | Derives de phtalazine et remedes contre la dyserection |
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ATE343388T1 (de) | 2000-04-19 | 2006-11-15 | Lilly Icos Llc | Pde-v hemmer zur behandlung von morbus parkinson |
US6803906B1 (en) * | 2000-07-05 | 2004-10-12 | Smart Technologies, Inc. | Passive touch system and method of detecting user input |
US6821978B2 (en) | 2000-09-19 | 2004-11-23 | Schering Corporation | Xanthine phosphodiesterase V inhibitors |
EP1442042A1 (fr) | 2001-11-09 | 2004-08-04 | Schering Corporation | Inhibiteurs de la phosphodiesterase v de derives polycycliques de guanine |
EP1710235A4 (fr) * | 2004-01-30 | 2008-12-17 | Beijing Tuolin Medicine Scienc | Extraits de marasmines androsaceus l.es, derives de piperdinone et utilisations de ceux-ci en tant qu'agents hypertensifs |
AU2005277384B2 (en) | 2004-08-17 | 2011-11-17 | The Johns Hopkins University | PDE5 inhibitor compositions and methods for treating cardiac indications |
WO2006074223A2 (fr) * | 2005-01-03 | 2006-07-13 | Myriad Genetics, Inc. | Composes pharmaceutiques constituant des activateurs de caspases et des inducteurs d'apoptose et utilisation de ces composes |
US7759337B2 (en) | 2005-03-03 | 2010-07-20 | Amgen Inc. | Phthalazine compounds and methods of use |
US8772481B2 (en) | 2008-10-10 | 2014-07-08 | Amgen Inc. | Aza- and diaza-phthalazine compounds as P38 map kinase modulators and methods of use thereof |
WO2010042649A2 (fr) | 2008-10-10 | 2010-04-15 | Amgen Inc. | Composés de phtalazine en tant que modulateurs de map kinase p38 et procédés pour les utiliser |
FR2941696B1 (fr) | 2009-02-05 | 2011-04-15 | Sanofi Aventis | Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique |
CN102060749B (zh) * | 2009-11-12 | 2013-07-10 | 上海药明康德新药开发有限公司 | 2-氰基-7-氮杂-螺[3,5]壬烷衍生物的制备方法 |
WO2014100733A1 (fr) | 2012-12-21 | 2014-06-26 | Mayo Foundation For Medical Education And Research | Procédés et matériaux pour le traitement de la sténose valvulaire aortique calcifiée |
CN109912586A (zh) * | 2013-09-06 | 2019-06-21 | 日本曹达株式会社 | 内型-9-氮杂双环[3.3.1]壬烷-3-醇衍生物的制造方法 |
CN108395377A (zh) * | 2018-01-16 | 2018-08-14 | 吴江信凯医药科技有限公司 | 一种3-氯-4-甲氧基苄胺盐酸盐的制备方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4754091A (en) * | 1985-02-28 | 1988-06-28 | Amoco Corporation | Conversion of a lower alkane |
MY104343A (en) | 1987-11-23 | 1994-03-31 | Janssen Pharmaceutica Nv | Novel pyridizinamine deravatives |
TW279162B (fr) * | 1991-09-26 | 1996-06-21 | Mitsubishi Chem Corp | |
JP3919835B2 (ja) | 1994-08-09 | 2007-05-30 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 縮合ピリダジン系化合物 |
ES2224130T3 (es) * | 1994-08-09 | 2005-03-01 | Eisai Co., Ltd. | Compuesto de piridazina condensada. |
JPH09135938A (ja) | 1995-11-16 | 1997-05-27 | Toyota Motor Corp | 水陸両用ボ−ト |
WO1998007430A1 (fr) * | 1996-08-20 | 1998-02-26 | Eisai Co., Ltd. | Medicament contre les defaillances de l'erection, renfermant un compose a base de pyridazine fondue |
-
1999
- 1999-02-17 US US09/508,197 patent/US6498159B1/en not_active Expired - Fee Related
- 1999-02-17 AU AU25470/99A patent/AU755361B2/en not_active Ceased
- 1999-02-17 EP EP99905213A patent/EP1057819A4/fr not_active Withdrawn
- 1999-02-17 NZ NZ503399A patent/NZ503399A/xx unknown
- 1999-02-17 KR KR1020007002378A patent/KR20010023724A/ko not_active Application Discontinuation
- 1999-02-17 RU RU2000104870/04A patent/RU2229476C2/ru not_active IP Right Cessation
- 1999-02-17 WO PCT/JP1999/000688 patent/WO1999042452A1/fr not_active Application Discontinuation
- 1999-02-17 CA CA002302943A patent/CA2302943C/fr not_active Expired - Fee Related
- 1999-02-17 PL PL99339836A patent/PL339836A1/xx unknown
- 1999-02-17 CN CNB998014729A patent/CN1210265C/zh not_active Expired - Fee Related
- 1999-02-17 HU HU0003219A patent/HUP0003219A3/hu unknown
- 1999-02-17 BR BR9909369-3A patent/BR9909369A/pt not_active IP Right Cessation
-
2000
- 2000-02-25 NO NO20000969A patent/NO317877B1/no unknown
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2002
- 2002-10-28 US US10/281,194 patent/US6699870B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
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HUP0003219A2 (hu) | 2001-05-28 |
US6498159B1 (en) | 2002-12-24 |
RU2229476C2 (ru) | 2004-05-27 |
WO1999042452A1 (fr) | 1999-08-26 |
KR20010023724A (ko) | 2001-03-26 |
CA2302943C (fr) | 2007-08-07 |
AU755361B2 (en) | 2002-12-12 |
AU2547099A (en) | 1999-09-06 |
BR9909369A (pt) | 2000-11-28 |
NO20000969L (no) | 2000-08-11 |
EP1057819A1 (fr) | 2000-12-06 |
CA2302943A1 (fr) | 1999-08-26 |
EP1057819A4 (fr) | 2003-02-05 |
CN1275124A (zh) | 2000-11-29 |
US6699870B2 (en) | 2004-03-02 |
HUP0003219A3 (en) | 2001-07-30 |
US20030105074A1 (en) | 2003-06-05 |
PL339836A1 (en) | 2001-01-02 |
NO20000969D0 (no) | 2000-02-25 |
NZ503399A (en) | 2003-01-31 |
CN1210265C (zh) | 2005-07-13 |
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