JP2002523450A5 - - Google Patents
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- JP2002523450A5 JP2002523450A5 JP2000567194A JP2000567194A JP2002523450A5 JP 2002523450 A5 JP2002523450 A5 JP 2002523450A5 JP 2000567194 A JP2000567194 A JP 2000567194A JP 2000567194 A JP2000567194 A JP 2000567194A JP 2002523450 A5 JP2002523450 A5 JP 2002523450A5
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- 150000001875 compounds Chemical class 0.000 description 45
- 125000003118 aryl group Chemical group 0.000 description 36
- 239000000203 mixture Substances 0.000 description 33
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 32
- 125000000217 alkyl group Chemical group 0.000 description 32
- 229910052739 hydrogen Inorganic materials 0.000 description 32
- 239000001257 hydrogen Substances 0.000 description 32
- -1 alkoxyhaloalkyl Chemical group 0.000 description 29
- 150000002431 hydrogen Chemical class 0.000 description 25
- 239000002253 acid Substances 0.000 description 23
- 125000001931 aliphatic group Chemical group 0.000 description 18
- 229940024606 amino acid Drugs 0.000 description 18
- 229920001184 polypeptide Polymers 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 16
- 125000002877 alkyl aryl group Chemical group 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 229910052736 halogen Inorganic materials 0.000 description 13
- 150000002367 halogens Chemical class 0.000 description 13
- 125000004438 haloalkoxy group Chemical group 0.000 description 12
- 150000003857 carboxamides Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 9
- 125000005431 alkyl carboxamide group Chemical group 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 229940124530 sulfonamide Drugs 0.000 description 9
- 150000003456 sulfonamides Chemical class 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 8
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 8
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 210000002889 endothelial cell Anatomy 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 8
- 230000002040 relaxant effect Effects 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 7
- 125000004103 aminoalkyl group Chemical group 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- 235000001014 amino acid Nutrition 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 150000001733 carboxylic acid esters Chemical class 0.000 description 6
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 description 6
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 6
- ICRHORQIUXBEPA-UHFFFAOYSA-N thionitrous acid Chemical group SN=O ICRHORQIUXBEPA-UHFFFAOYSA-N 0.000 description 6
- 239000002550 vasoactive agent Substances 0.000 description 6
- 0 CCCc1n[n]c2c1N(C)C(C(C)C)N(*)C2=O Chemical compound CCCc1n[n]c2c1N(C)C(C(C)C)N(*)C2=O 0.000 description 5
- 150000001767 cationic compounds Chemical class 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 229910001411 inorganic cation Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000002892 organic cations Chemical class 0.000 description 5
- 229960001789 papaverine Drugs 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 102000002045 Endothelin Human genes 0.000 description 4
- 108050009340 Endothelin Proteins 0.000 description 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 4
- 229930064664 L-arginine Natural products 0.000 description 4
- 235000014852 L-arginine Nutrition 0.000 description 4
- FQWRAVYMZULPNK-UHFFFAOYSA-N N(5)-[(Z)-amino(hydroxyimino)methyl]ornithine Chemical compound OC(=O)C(N)CCCNC(N)=NO FQWRAVYMZULPNK-UHFFFAOYSA-N 0.000 description 4
- 108091034117 Oligonucleotide Proteins 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 108010003205 Vasoactive Intestinal Peptide Proteins 0.000 description 4
- 102400000015 Vasoactive intestinal peptide Human genes 0.000 description 4
- 229960005305 adenosine Drugs 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 239000002160 alpha blocker Substances 0.000 description 4
- 229940124308 alpha-adrenoreceptor antagonist Drugs 0.000 description 4
- 125000000747 amidyl group Chemical group [H][N-]* 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- 239000002876 beta blocker Substances 0.000 description 4
- 229940097320 beta blocking agent Drugs 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 4
- KWDSFGYQALRPMG-UHFFFAOYSA-N delta-N-Hydroxy-L-orginin Natural products OC(=O)C(N)CCCN(O)C(N)=N KWDSFGYQALRPMG-UHFFFAOYSA-N 0.000 description 4
- 229940052760 dopamine agonists Drugs 0.000 description 4
- 239000003136 dopamine receptor stimulating agent Substances 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
- 229960003133 ergot alkaloid Drugs 0.000 description 4
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 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
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 150000003180 prostaglandins Chemical class 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 3
- RMWVZGDJPAKBDE-UHFFFAOYSA-N 2-acetyloxy-4-(trifluoromethyl)benzoic acid Chemical compound CC(=O)OC1=CC(C(F)(F)F)=CC=C1C(O)=O RMWVZGDJPAKBDE-UHFFFAOYSA-N 0.000 description 3
- AEZZPAQOEUQNBB-UHFFFAOYSA-N 3-(4-imidazol-1-ylphenyl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(N2C=NC=C2)C=C1 AEZZPAQOEUQNBB-UHFFFAOYSA-N 0.000 description 3
- NPFVRBCDMFKOPY-UHFFFAOYSA-N 3-(4-imidazol-1-ylthiophen-2-yl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC(N2C=NC=C2)=CS1 NPFVRBCDMFKOPY-UHFFFAOYSA-N 0.000 description 3
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical class N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- MIXLZCYFMQNQDD-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-N'-hydroxy-1,3-thiazole-2-carboximidamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CSC(C(N)=NO)=N1 MIXLZCYFMQNQDD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- FFCZQVKVWGGQFB-UHFFFAOYSA-N 9h-pyrido[3,4-b]indole-1,4-dione Chemical class N1C2=CC=CC=C2C2=C1C(=O)N=CC2=O FFCZQVKVWGGQFB-UHFFFAOYSA-N 0.000 description 3
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 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
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000005001 aminoaryl group Chemical group 0.000 description 3
- 229960002105 amrinone Drugs 0.000 description 3
- RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 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
- RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 description 3
- 229960004588 cilostazol Drugs 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
- 229960002768 dipyridamole Drugs 0.000 description 3
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 3
- STTRYQAGHGJXJJ-LICLKQGHSA-N filaminast Chemical compound COC1=CC=C(C(\C)=N\OC(N)=O)C=C1OC1CCCC1 STTRYQAGHGJXJJ-LICLKQGHSA-N 0.000 description 3
- 229950006884 filaminast Drugs 0.000 description 3
- NYQCKFLLTCINSJ-UHFFFAOYSA-N hydron;3-[4-(pyridin-4-ylamino)phenyl]-4,5-dihydro-1h-pyridazin-6-one;chloride Chemical compound Cl.N1C(=O)CCC(C=2C=CC(NC=3C=CN=CC=3)=CC=2)=N1 NYQCKFLLTCINSJ-UHFFFAOYSA-N 0.000 description 3
- 229960003574 milrinone Drugs 0.000 description 3
- PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 description 3
- 229950002910 motapizone Drugs 0.000 description 3
- 229960002164 pimobendan Drugs 0.000 description 3
- GLBJJMFZWDBELO-UHFFFAOYSA-N pimobendane Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=C(C=3C(CC(=O)NN=3)C)C=C2N1 GLBJJMFZWDBELO-UHFFFAOYSA-N 0.000 description 3
- 150000004892 pyridazines Chemical class 0.000 description 3
- 150000003246 quinazolines Chemical class 0.000 description 3
- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 description 3
- 229960002586 roflumilast Drugs 0.000 description 3
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 3
- 229950005741 rolipram Drugs 0.000 description 3
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- 229960003310 sildenafil Drugs 0.000 description 3
- LDYABEHPDDRNAF-UHFFFAOYSA-M sodium;1-[4-(1,3-benzodioxol-5-ylmethylamino)-6-chloroquinazolin-2-yl]piperidine-4-carboxylate Chemical compound [Na+].C1CC(C(=O)[O-])CCN1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C=C(Cl)C=C2)C2=N1 LDYABEHPDDRNAF-UHFFFAOYSA-M 0.000 description 3
- WOXKDUGGOYFFRN-IIBYNOLFSA-N tadalafil Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C(C4=CC=CC=C4N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 WOXKDUGGOYFFRN-IIBYNOLFSA-N 0.000 description 3
- 229960000278 theophylline Drugs 0.000 description 3
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- REZGGXNDEMKIQB-UHFFFAOYSA-N zaprinast Chemical compound CCCOC1=CC=CC=C1C1=NC(=O)C2=NNNC2=N1 REZGGXNDEMKIQB-UHFFFAOYSA-N 0.000 description 3
- 229950005371 zaprinast Drugs 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
- 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
- NMNXBEXPAHSXOK-UHFFFAOYSA-N 6-(2,4-dimethylimidazol-1-yl)-8-methyl-1h-quinolin-2-one Chemical compound CC1=NC(C)=CN1C1=CC(C)=C(NC(=O)C=C2)C2=C1 NMNXBEXPAHSXOK-UHFFFAOYSA-N 0.000 description 2
- QUOGESRFPZDMMT-UHFFFAOYSA-N L-Homoarginine Natural products OC(=O)C(N)CCCCNC(N)=N QUOGESRFPZDMMT-UHFFFAOYSA-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
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline 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
- QUOGESRFPZDMMT-YFKPBYRVSA-N L-homoarginine Chemical compound OC(=O)[C@@H](N)CCCCNC(N)=N QUOGESRFPZDMMT-YFKPBYRVSA-N 0.000 description 2
- UIAYVIIHMORPSJ-UHFFFAOYSA-N N-cyclohexyl-N-methyl-4-[(2-oxo-1H-quinolin-6-yl)oxy]butanamide Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCC(=O)N(C)C1CCCCC1 UIAYVIIHMORPSJ-UHFFFAOYSA-N 0.000 description 2
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 2
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 2
- 108010001742 S-Nitrosoglutathione Proteins 0.000 description 2
- XOWVFANEOZMPKG-REOHCLBHSA-N S-nitroso-L-cysteine Chemical compound OC(=O)[C@@H](N)CSN=O XOWVFANEOZMPKG-REOHCLBHSA-N 0.000 description 2
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-
1998
- 1998-09-01 US US09/145,142 patent/US5958926A/en not_active Ceased
-
1999
- 1999-02-01 US US09/241,281 patent/US6133272A/en not_active Expired - Fee Related
- 1999-02-10 US US09/247,321 patent/US6177428B1/en not_active Expired - Fee Related
- 1999-02-10 US US09/247,293 patent/US6232321B1/en not_active Expired - Fee Related
- 1999-02-10 US US09/247,323 patent/US6316457B1/en not_active Expired - Fee Related
- 1999-02-10 US US09/247,295 patent/US6197782B1/en not_active Expired - Fee Related
- 1999-02-10 US US09/247,322 patent/US6172068B1/en not_active Expired - Fee Related
- 1999-02-10 US US09/247,292 patent/US6221881B1/en not_active Expired - Fee Related
- 1999-02-10 US US09/247,320 patent/US6197778B1/en not_active Expired - Fee Related
- 1999-02-10 US US09/247,296 patent/US6172060B1/en not_active Expired - Fee Related
- 1999-07-06 US US09/347,426 patent/US6211179B1/en not_active Expired - Fee Related
- 1999-09-01 WO PCT/US1999/020024 patent/WO2000012076A1/en not_active Ceased
- 1999-09-01 JP JP2000567194A patent/JP2002523450A/ja active Pending
- 1999-09-01 EP EP99948093A patent/EP1109543A4/en not_active Withdrawn
- 1999-09-01 CA CA002339189A patent/CA2339189A1/en not_active Abandoned
- 1999-09-01 AU AU61334/99A patent/AU773269B2/en not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11905293B2 (en) | 2017-05-22 | 2024-02-20 | Topadur Pharma Ag | Dual mode of action soluble guanylate cyclase activators and phosphodiesterase inhibitors and uses thereof |
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