JP2002523449A5 - - Google Patents
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- JP2002523449A5 JP2002523449A5 JP2000567193A JP2000567193A JP2002523449A5 JP 2002523449 A5 JP2002523449 A5 JP 2002523449A5 JP 2000567193 A JP2000567193 A JP 2000567193A JP 2000567193 A JP2000567193 A JP 2000567193A JP 2002523449 A5 JP2002523449 A5 JP 2002523449A5
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- JP
- Japan
- Prior art keywords
- compound
- nitric oxide
- group
- composition
- independently
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 60
- 150000001875 compounds Chemical class 0.000 description 44
- 239000000203 mixture Substances 0.000 description 37
- 125000003118 aryl group Chemical group 0.000 description 33
- 239000002253 acid Substances 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 18
- 229920000272 Oligonucleotide Polymers 0.000 description 16
- 125000001931 aliphatic group Chemical group 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 16
- 229920001184 polypeptide Polymers 0.000 description 16
- -1 alkoxyhaloalkyl Chemical group 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 239000000066 endothelium dependent relaxing factor Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 11
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 11
- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 150000002431 hydrogen Chemical class 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 11
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- 239000000674 adrenergic antagonist Substances 0.000 description 10
- 125000002877 alkyl aryl group Chemical group 0.000 description 10
- 125000004438 haloalkoxy group Chemical group 0.000 description 9
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 102000004305 alpha adrenergic receptors Human genes 0.000 description 8
- 108090000861 alpha adrenergic receptors Proteins 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 229940079593 drugs Drugs 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 7
- 239000002550 vasoactive agent Substances 0.000 description 7
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 125000005431 alkyl carboxamide group Chemical group 0.000 description 6
- 125000004103 aminoalkyl group Chemical group 0.000 description 6
- 150000003857 carboxamides Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229960001663 sulfanilamide Drugs 0.000 description 6
- ICRHORQIUXBEPA-UHFFFAOYSA-N thionitrous acid Chemical group SN=O ICRHORQIUXBEPA-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 150000001767 cationic compounds Chemical class 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910001411 inorganic cation Inorganic materials 0.000 description 5
- 0 *C(C1=C*CC(CCCC2CC3)C1CC2c1c3c(cccc2)c2[n]1*)=O Chemical compound *C(C1=C*CC(CCCC2CC3)C1CC2c1c3c(cccc2)c2[n]1*)=O 0.000 description 4
- OIRDTQYFTABQOQ-GAWUUDPSSA-N 9-β-D-XYLOFURANOSYL-ADENINE Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@H](O)[C@H]1O OIRDTQYFTABQOQ-GAWUUDPSSA-N 0.000 description 4
- OIRDTQYFTABQOQ-SXVXDFOESA-N Adenosine Natural products Nc1ncnc2c1ncn2[C@@H]3O[C@@H](CO)[C@H](O)[C@@H]3O OIRDTQYFTABQOQ-SXVXDFOESA-N 0.000 description 4
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 4
- 229940052760 Dopamine agonists Drugs 0.000 description 4
- 102000002045 Endothelin Human genes 0.000 description 4
- 108050009340 Endothelin Proteins 0.000 description 4
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N Endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 description 4
- 229940083253 Ergot alkaloid peripheral vasodilators Drugs 0.000 description 4
- 235000014852 L-arginine Nutrition 0.000 description 4
- QUOGESRFPZDMMT-YFKPBYRVSA-N L-homoarginine Chemical compound OC(=O)[C@@H](N)CCCCNC(N)=N QUOGESRFPZDMMT-YFKPBYRVSA-N 0.000 description 4
- 229940082622 Prostaglandin cardiac therapy preparations Drugs 0.000 description 4
- 229940077717 Prostaglandin drugs for peptic ulcer and gastro-oesophageal reflux disease (GORD) Drugs 0.000 description 4
- 102100015313 VIP Human genes 0.000 description 4
- 101700003320 VIP Proteins 0.000 description 4
- 229960005305 adenosine Drugs 0.000 description 4
- 229930013930 alkaloids Natural products 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 230000003042 antagnostic Effects 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 229940051869 antimigraine Ergot alkaloids Drugs 0.000 description 4
- 239000002876 beta blocker Substances 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- 229940082638 cardiac stimulant Phosphodiesterase inhibitors Drugs 0.000 description 4
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 4
- 229960003133 ergot alkaloids Drugs 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 239000003887 narcotic antagonist Substances 0.000 description 4
- 229940094443 oxytocics Prostaglandins Drugs 0.000 description 4
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 4
- 239000004036 potassium channel stimulating agent Substances 0.000 description 4
- 150000003180 prostaglandins Chemical class 0.000 description 4
- 230000002227 vasoactive Effects 0.000 description 4
- MTNDZQHUAFNZQY-UHFFFAOYSA-N 2-Imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
- 150000003797 alkaloid derivatives Chemical class 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000000747 amidyl group Chemical group [H][N-]* 0.000 description 3
- 125000005001 aminoaryl group Chemical group 0.000 description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- MIUYYRGOYGWVDO-JHZUCGOESA-N methyl (1S,15R,18S,19R,20S)-6,18-dihydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate Chemical compound OC1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 MIUYYRGOYGWVDO-JHZUCGOESA-N 0.000 description 3
- XKJJSWXADRRQKQ-HRHDOCNUSA-N methyl (1S,15R,18S,19R,20S)-7,18-dihydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate Chemical compound C1=C(O)C=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 XKJJSWXADRRQKQ-HRHDOCNUSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- QTJKCQPXTOYYHJ-BYPYZUCNSA-N (2R)-2-acetamido-3-nitrososulfanylpropanoic acid Chemical compound CC(=O)N[C@H](C(O)=O)CSN=O QTJKCQPXTOYYHJ-BYPYZUCNSA-N 0.000 description 2
- HNIULCDUASSKOM-RQJHMYQMSA-N (2S)-1-[(2S)-2-methyl-3-nitrososulfanylpropanoyl]pyrrolidine-2-carboxylic acid Chemical compound O=NSC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O HNIULCDUASSKOM-RQJHMYQMSA-N 0.000 description 2
- QWPCKAAAWDCDCW-VKHMYHEASA-N (2S)-2-amino-4-nitrososulfanylbutanoic acid Chemical compound OC(=O)[C@@H](N)CCSN=O QWPCKAAAWDCDCW-VKHMYHEASA-N 0.000 description 2
- PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 2
- TXQAZWIBPGKHOX-UHFFFAOYSA-N 1H-indol-3-amine Chemical group C1=CC=C2C(N)=CNC2=C1 TXQAZWIBPGKHOX-UHFFFAOYSA-N 0.000 description 2
- XOWVFANEOZMPKG-UHFFFAOYSA-N 2-amino-3-nitrososulfanylpropanoic acid Chemical compound OC(=O)C(N)CSN=O XOWVFANEOZMPKG-UHFFFAOYSA-N 0.000 description 2
- HSVZQQYIMKLNLN-UHFFFAOYSA-N 4-imino-1-(2-phenylphenoxy)-4-piperidin-1-ylbutan-2-ol Chemical compound C1CCCCN1C(=N)CC(O)COC1=CC=CC=C1C1=CC=CC=C1 HSVZQQYIMKLNLN-UHFFFAOYSA-N 0.000 description 2
- BDFFOEAQENGFSK-UHFFFAOYSA-N 5-[cyano(nitroso)amino]-2-hydroxypentanamide Chemical compound NC(=O)C(O)CCCN(N=O)C#N BDFFOEAQENGFSK-UHFFFAOYSA-N 0.000 description 2
- HIHZDNKKIUQQSC-UHFFFAOYSA-N 6-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino]-1,3,5-trimethylpyrimidine-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2N(C(=O)N(C)C(=O)C=2C)C)CC1 HIHZDNKKIUQQSC-UHFFFAOYSA-N 0.000 description 2
- HSWPZIDYAHLZDD-UHFFFAOYSA-N Atipamezole Chemical compound C1C2=CC=CC=C2CC1(CC)C1=CN=CN1 HSWPZIDYAHLZDD-UHFFFAOYSA-N 0.000 description 2
- 229960003002 Atipamezole Drugs 0.000 description 2
- AYYCFGDXLUPJAQ-UHFFFAOYSA-N BMY-7,378 Chemical compound COC1=CC=CC=C1N1CCN(CCN2C(CC3(CCCC3)CC2=O)=O)CC1 AYYCFGDXLUPJAQ-UHFFFAOYSA-N 0.000 description 2
- SGOFAUSEYBZKDQ-UHFFFAOYSA-N BRL-44408 Chemical compound C1C2=CC=CC=C2C(C)N1CC1=NCCN1 SGOFAUSEYBZKDQ-UHFFFAOYSA-N 0.000 description 2
- 229960002743 Glutamine Drugs 0.000 description 2
- 229950001476 IDAZOXAN Drugs 0.000 description 2
- HPMRFMKYPGXPEP-UHFFFAOYSA-N Idazoxan Chemical compound N1CCN=C1C1OC2=CC=CC=C2OC1 HPMRFMKYPGXPEP-UHFFFAOYSA-N 0.000 description 2
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline zwitterion Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 2
- XFDVJGKSQRUEEM-UHFFFAOYSA-N N-(2,6-Dichloro-4-(((2-chloroethyl)methylamino)methyl)phenyl)-4,5-dihydro-1H-imidazol-2-amine Chemical compound ClC1=CC(CN(CCCl)C)=CC(Cl)=C1NC1=NCCN1 XFDVJGKSQRUEEM-UHFFFAOYSA-N 0.000 description 2
- 229960003104 Ornithine Drugs 0.000 description 2
- 229960001999 Phentolamine Drugs 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N Quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- ZIIQCSMRQKCOCT-YFKPBYRVSA-N S-Nitroso-N-acetylpenicillamine Chemical compound CC(=O)N[C@@H](C(O)=O)C(C)(C)SN=O ZIIQCSMRQKCOCT-YFKPBYRVSA-N 0.000 description 2
- 108010001742 S-Nitrosoglutathione Proteins 0.000 description 2
- HYHSBSXUHZOYLX-WDSKDSINSA-N S-nitrosoglutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O HYHSBSXUHZOYLX-WDSKDSINSA-N 0.000 description 2
- GVPIXRLYKVFFMK-UHFFFAOYSA-N Setiptiline Chemical compound C12=CC=CC=C2CC2=CC=CC=C2C2=C1CN(C)CC2 GVPIXRLYKVFFMK-UHFFFAOYSA-N 0.000 description 2
- PNCPYILNMDWPEY-QGZVFWFLSA-N Silodosin Chemical compound N([C@@H](CC=1C=C(C=2N(CCCO)CCC=2C=1)C(N)=O)C)CCOC1=CC=CC=C1OCC(F)(F)F PNCPYILNMDWPEY-QGZVFWFLSA-N 0.000 description 2
- DKGZKTPJOSAWFA-UHFFFAOYSA-N Spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 2
- 229950001675 Spiperone Drugs 0.000 description 2
- DRHKJLXJIQTDTD-OAHLLOKOSA-N Tamsulosine Chemical compound CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-OAHLLOKOSA-N 0.000 description 2
- 229960002926 Tedisamil Drugs 0.000 description 2
- JIVZKJJQOZQXQB-UHFFFAOYSA-N Tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 2
- PHLBKPHSAVXXEF-UHFFFAOYSA-N Trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 2
- 229960003991 Trazodone Drugs 0.000 description 2
- ICMGLRUYEQNHPF-UHFFFAOYSA-N Uraprene Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2N(C(=O)N(C)C(=O)C=2)C)CC1 ICMGLRUYEQNHPF-UHFFFAOYSA-N 0.000 description 2
- CTIRHWCPXYGDGF-HDICACEKSA-N [H][C@]12CN(CC3CC3)C[C@]([H])(CN(CC3CC3)C1)C21CCCC1 Chemical compound [H][C@]12CN(CC3CC3)C[C@]([H])(CN(CC3CC3)C1)C21CCCC1 CTIRHWCPXYGDGF-HDICACEKSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 229960002173 citrulline Drugs 0.000 description 2
- 235000013477 citrulline Nutrition 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- BLGXFZZNTVWLAY-MQPLHJKPSA-N methyl (1S,15R,18R,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-MQPLHJKPSA-N 0.000 description 2
- DFDNBRUSLQYVNA-IXDGSTSKSA-N methyl (1S,15R,20S)-1,3,11,12,14,15,16,17,20,21-decahydroyohimban-19-carboxylate Chemical compound C1=CC=C2C(CCN3C[C@@H]4CCC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 DFDNBRUSLQYVNA-IXDGSTSKSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical group C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 2
- 229950002275 setiptiline Drugs 0.000 description 2
- 229960002613 tamsulosin Drugs 0.000 description 2
- 229960002312 tolazoline Drugs 0.000 description 2
- 229960001130 urapidil Drugs 0.000 description 2
- KLEKLDFUYOZELG-UHFFFAOYSA-N 5-[4-[2-hydroxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]phenyl]-6-methyl-2-oxo-1H-pyridine-3-carbonitrile Chemical compound COC1=CC=CC=C1N1CCN(CC(O)COC=2C=CC(=CC=2)C2=C(NC(=O)C(C#N)=C2)C)CC1 KLEKLDFUYOZELG-UHFFFAOYSA-N 0.000 description 1
- WNMJYKCGWZFFKR-UHFFFAOYSA-N Alfuzosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C)CCCNC(=O)C1CCCO1 WNMJYKCGWZFFKR-UHFFFAOYSA-N 0.000 description 1
- RHLJLALHBZGAFM-UHFFFAOYSA-N Bunazosinum Chemical compound C1CN(C(=O)CCC)CCCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 RHLJLALHBZGAFM-UHFFFAOYSA-N 0.000 description 1
- NPAKNKYSJIDKMW-UHFFFAOYSA-N Carvedilol Chemical group COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N Chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N Doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
- 229960001389 Doxazosin Drugs 0.000 description 1
- XLMJRFCCCWFQRE-SJRQCXNHSA-N Ecboline Chemical compound C([C@H]1[C@]2(O)O3)CCN1C(=O)CN2C(=O)[C@]3(C(C)C)NC(=O)[C@@H](CN(C)[C@@H]1C2)C=C1C1=C3C2=CNC3=CC=C1 XLMJRFCCCWFQRE-SJRQCXNHSA-N 0.000 description 1
- OWEUDBYTKOYTAD-MKTPKCENSA-N Ergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@@H]1C=C2C3=CC=CC4=NC=C([C]34)C[C@H]2N(C)C1)C(C)C)C1=CC=CC=C1 OWEUDBYTKOYTAD-MKTPKCENSA-N 0.000 description 1
- UYNVMODNBIQBMV-UHFFFAOYSA-N Ifenprodil Chemical compound C1CC(CC=2C=CC=CC=2)CCN1C(C)C(O)C1=CC=C(O)C=C1 UYNVMODNBIQBMV-UHFFFAOYSA-N 0.000 description 1
- FPCCSQOGAWCVBH-UHFFFAOYSA-N Ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 1
- SGUAFYQXFOLMHL-UHFFFAOYSA-N Labetalol Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 description 1
- RONZAEMNMFQXRA-UHFFFAOYSA-N Mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 description 1
- 229960001785 Mirtazapine Drugs 0.000 description 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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| PCT/US1999/020023 WO2000012075A1 (en) | 1998-09-01 | 1999-09-01 | Nitrosated and nitrosylated alpha-adrenergic receptor antagonists, compositions and methods of use |
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| FR2786101B1 (fr) * | 1998-11-24 | 2002-07-05 | Aventis Laboratoire | Utilisation de la nicergoline dans le traitement de la spasticite |
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| KR20100036390A (ko) | 2001-03-06 | 2010-04-07 | 셀러지 파마세우티칼스, 인크 | 비뇨생식기 장애 치료용 화합물 및 그 방법 |
| US6627602B2 (en) * | 2001-11-13 | 2003-09-30 | Duke University | Preventing desensitization of receptors |
| US20030158184A1 (en) * | 2001-12-21 | 2003-08-21 | Garvey David S. | Nitrosated and nitrosylated phosphodiesterase inhibitor compounds, compositions and their uses |
| CA2480832A1 (en) * | 2002-04-05 | 2003-10-23 | Nitromed, Inc. | Nitric oxide donors, compositions and methods of use |
| GB0225908D0 (en) * | 2002-11-06 | 2002-12-11 | Pfizer Ltd | Treatment of female sexual dysfunction |
| US7323462B2 (en) | 2002-12-10 | 2008-01-29 | Pfizer Inc. | Morpholine dopamine agonists |
| WO2004071437A2 (en) * | 2003-02-07 | 2004-08-26 | Barmensen, Inc. | Compositions for enhancing sexual responsiveness |
| WO2004071533A1 (ja) * | 2003-02-14 | 2004-08-26 | Takeda Pharmaceutical Company Limited | 局所投与用製剤 |
| EP1471066A1 (en) * | 2003-04-24 | 2004-10-27 | Aventis Pharma Deutschland GmbH | Triaza- and tetraaza-anthracenedione derivates, their preparation and their use as pharmaceuticals |
| US7169805B2 (en) * | 2003-05-28 | 2007-01-30 | Nicox S.A. | Captopril derivatives |
| FR2856592B1 (fr) * | 2003-06-27 | 2008-04-25 | Oreal | Composition cosmetique a base de percuseur(s) de radical thiyl pour la deformation permanente des fibres keratiniques |
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| JP5004215B2 (ja) * | 2004-03-05 | 2012-08-22 | キッセイ薬品工業株式会社 | 神経障害に伴う過活動膀胱の予防または治療用医薬組成物 |
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| WO2006124770A2 (en) * | 2005-05-13 | 2006-11-23 | The Feinstein Institute For Medical Research | Treatment of sepsis and inflammation with alpha2a adrenergic antagonists |
| EP3556401A1 (en) | 2005-05-27 | 2019-10-23 | The University of North Carolina at Chapel Hill | Nitric oxide-releasing particles for nitric oxide therapeutics and biomedical applications |
| US9045505B2 (en) | 2006-09-28 | 2015-06-02 | University Of Otago | Nitric oxide donors |
| US7807716B2 (en) * | 2008-09-24 | 2010-10-05 | Oral Delivery Technology Ltd. | Nitric oxide amino acid ester compound, compositions for increasing nitric oxide levels and method of use |
| EP2334279A4 (en) * | 2008-10-16 | 2013-03-20 | Novan Inc | STAIN OXIDE RELEASING PARTICLES FOR MOUTH CARE APPLICATIONS |
| WO2010110684A1 (en) * | 2009-03-27 | 2010-09-30 | Robin Andrew James Smith | Nitric oxide donors |
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| BR112012003804B1 (pt) | 2009-08-21 | 2019-02-19 | Novan, Inc. | Curativo para ferimentos, método para formar um curativo para ferimentos, e, kit de curativo para ferimento |
| WO2011047013A1 (en) * | 2009-10-13 | 2011-04-21 | Novan, Inc. | Nitric oxide-releasing coatings |
| US8591876B2 (en) | 2010-12-15 | 2013-11-26 | Novan, Inc. | Methods of decreasing sebum production in the skin |
| WO2012118829A2 (en) | 2011-02-28 | 2012-09-07 | Novan, Inc. | Tertiary s-nitrosothiol-modified nitricoxide-releasing xerogels and methods of using the same |
| JOP20200052A1 (ar) * | 2013-12-19 | 2017-06-16 | Bayer Pharma AG | بيبريدينيل تتراهيدرو كوينولينات مستبدلة واستخدامها كمعضدات مستقبل أدريني ألفا- 2c |
| BR112017009980A2 (pt) | 2014-11-14 | 2018-02-14 | Follea Int | ?sistema e método para prevenção de alopecia?. |
| WO2016201286A1 (en) | 2015-06-11 | 2016-12-15 | Applied Biology, Inc. | Treatment of sexual dysfunction |
| WO2018026371A1 (en) * | 2016-08-04 | 2018-02-08 | Sunovion Pharmaceuticals Inc. | Dual nav1.2/5ht2a inhibitors for treating cns disorders |
| WO2018073821A1 (en) * | 2016-10-18 | 2018-04-26 | Vasolead (2012) Ltd. | Compositions and methods for treating erectile dysfunction |
| CN108464971A (zh) * | 2018-07-02 | 2018-08-31 | 福州脉趣恒生科技有限公司 | 一种含有斯诺普利的抗高血压口服片剂及其制备方法 |
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| US4127118B1 (en) | 1977-03-16 | 1995-12-19 | Alvaro Latorre | Method of effecting and enhancing an erection |
| FR2547501A1 (fr) | 1983-06-15 | 1984-12-21 | Opochimiotherapie Lab | Excipient effervescent, sans alcalino-terreux, contenant des composes carbonates de l'arginine et un acide, et comprimes effervescents correspondants |
| US4885173A (en) | 1985-05-01 | 1989-12-05 | University Of Utah | Methods and compositions for noninvasive dose-to-effect administration of drugs with cardiovascular or renal vascular activities |
| US4801587A (en) | 1987-03-02 | 1989-01-31 | Gene Voss | Impotence ointment |
| US5256652A (en) | 1987-11-12 | 1993-10-26 | Pharmedic Co. | Topical compositions and methods for treatment of male impotence |
| IT1221826B (it) | 1988-06-08 | 1990-07-12 | Medico Harvey Srl Centro | Preparato per uso topico per il trattamento terapeutico dell impotentia coeundi |
| SE463851B (sv) | 1988-09-02 | 1991-02-04 | Amsu Ltd | Komposition foer behandling av erektil dysfunktion via uretra |
| US5059603A (en) | 1989-06-12 | 1991-10-22 | Centuries Laboratories, Inc. | Method and composition for treating impotence |
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| US5447912A (en) | 1989-09-18 | 1995-09-05 | Senetek, Plc | Erection-inducing methods and compositions |
| US5236904A (en) | 1989-09-18 | 1993-08-17 | Senetek, Plc | Erection-inducing methods and compositions |
| US5242391A (en) | 1990-04-25 | 1993-09-07 | Alza Corporation | Urethral insert for treatment of erectile dysfunction |
| GB9012469D0 (en) | 1990-06-05 | 1990-07-25 | Glaxo Group Ltd | Medicaments |
| US5399581A (en) | 1990-12-26 | 1995-03-21 | Laragh; John H. | Method and compositions for treatment of sexual impotence |
| US5380758A (en) | 1991-03-29 | 1995-01-10 | Brigham And Women's Hospital | S-nitrosothiols as smooth muscle relaxants and therapeutic uses thereof |
| DE4117249C2 (de) | 1991-05-27 | 1998-05-14 | Christian Dr Stief | Linsidomin zur Behandlung erektiler Dysfunktionen |
| EP1025853A3 (en) | 1991-11-14 | 2000-11-08 | Brigham And Women's Hospital | Pharmaceutical composition containing S-nitroso-heme proteins and use thereof |
| WO1993012068A1 (en) | 1991-12-11 | 1993-06-24 | Brigham And Women's Hospital | S-nitrosothiols as smooth muscle relaxants and therapeutic uses thereof |
| US5607691A (en) | 1992-06-12 | 1997-03-04 | Affymax Technologies N.V. | Compositions and methods for enhanced drug delivery |
| US5646181A (en) | 1992-07-02 | 1997-07-08 | Research Foundation Of State University Of New York | Method and compositions for treating impotence |
| US5773457A (en) * | 1995-02-15 | 1998-06-30 | Cesar Roberto Dias Nahoum | Compositions |
| US5910316A (en) | 1992-08-24 | 1999-06-08 | The United States Of America, As Represented By The Department Of Health And Human Services | Use of nitric oxide-releasing agents to treat impotency |
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| US5439938A (en) | 1993-04-07 | 1995-08-08 | The Johns Hopkins University | Treatments for male sexual dysfunction |
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| FR2774593B1 (fr) | 1998-02-12 | 2000-05-05 | Philippe Gorny | Obtention d'un medicament destine a combattre les dysfonctions sexuelles feminines |
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-
1998
- 1998-09-01 US US09/145,143 patent/US6294517B1/en not_active Expired - Fee Related
-
1999
- 1999-03-30 US US09/280,540 patent/US6514934B1/en not_active Expired - Fee Related
- 1999-05-07 US US09/306,805 patent/US6433182B1/en not_active Expired - Fee Related
- 1999-05-07 US US09/306,809 patent/US6417162B1/en not_active Expired - Fee Related
- 1999-09-01 EP EP99944040A patent/EP1109542A4/en not_active Withdrawn
- 1999-09-01 JP JP2000567193A patent/JP2002523449A/ja active Pending
- 1999-09-01 WO PCT/US1999/020023 patent/WO2000012075A1/en active IP Right Grant
- 1999-09-01 CA CA002339145A patent/CA2339145A1/en not_active Abandoned
- 1999-09-01 AU AU57016/99A patent/AU770414B2/en not_active Ceased
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