JP2013514995A5 - - Google Patents
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- Publication number
- JP2013514995A5 JP2013514995A5 JP2012544900A JP2012544900A JP2013514995A5 JP 2013514995 A5 JP2013514995 A5 JP 2013514995A5 JP 2012544900 A JP2012544900 A JP 2012544900A JP 2012544900 A JP2012544900 A JP 2012544900A JP 2013514995 A5 JP2013514995 A5 JP 2013514995A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- pyrazolo
- dihydro
- pyrimidin
- composition
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 claims 24
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims 13
- -1 gizadenafil Chemical compound 0.000 claims 10
- 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 claims 9
- 239000002840 nitric oxide donor Substances 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 7
- 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 claims 6
- YPFZMBHKIVDSNR-UHFFFAOYSA-N 5-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylpyridin-3-yl]-3-ethyl-2-(2-methoxyethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound C1=C(C=2NC(=O)C3=NN(CCOC)C(CC)=C3N=2)C(OCC)=NC=C1S(=O)(=O)N1CCN(CC)CC1 YPFZMBHKIVDSNR-UHFFFAOYSA-N 0.000 claims 4
- 239000000674 adrenergic antagonist Substances 0.000 claims 4
- 238000011200 topical administration Methods 0.000 claims 4
- OABVKOFQXWSACK-UHFFFAOYSA-N 3-ethyl-5-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-6-methyl-2-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(=O)(=O)N2CCN(CC)CC2)C=C1C(N(C(=O)C1=N2)C)=NC1=C(CC)N2C1=CC=CC=N1 OABVKOFQXWSACK-UHFFFAOYSA-N 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 3
- 239000003146 anticoagulant agent Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 229960003310 sildenafil Drugs 0.000 claims 3
- LQANGKSBLPMBTJ-BRSNVKEHSA-N (z)-7-[(1s,2s,3r,4r)-3-[(e,3s)-3-hydroxyoct-1-enyl]-5-oxabicyclo[2.2.1]heptan-2-yl]hept-5-enoic acid Chemical compound C1[C@@H]2CO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O LQANGKSBLPMBTJ-BRSNVKEHSA-N 0.000 claims 2
- WJQXYMDJKXVKMF-UHFFFAOYSA-N 3-ethyl-5-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-(2-methoxyethoxy)pyridin-3-yl]-6-methyl-2-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CN=C(OCCOC)C(C=2N(C(=O)C3=NN(C(CC)=C3N=2)C=2N=CC=CC=2)C)=C1 WJQXYMDJKXVKMF-UHFFFAOYSA-N 0.000 claims 2
- SISGKOAGBAJWPA-UHFFFAOYSA-N 3-ethyl-5-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-(2-methylpropoxy)pyridin-3-yl]-2-(1-methylpiperidin-4-yl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CN=C(OCC(C)C)C(C=2NC(=O)C3=NN(C(CC)=C3N=2)C2CCN(C)CC2)=C1 SISGKOAGBAJWPA-UHFFFAOYSA-N 0.000 claims 2
- AANJEOKXWMXQIE-UHFFFAOYSA-N 5-[2-ethoxy-5-(2-morpholin-4-ylacetyl)phenyl]-1-methyl-3-propyl-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1C(=O)CN1CCOCC1 AANJEOKXWMXQIE-UHFFFAOYSA-N 0.000 claims 2
- 239000005541 ACE inhibitor Substances 0.000 claims 2
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 2
- PNDCCASNKRUOMF-AXUFZUPDSA-N CO[C@H]1[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1CO[C@@H](O[C@@H]2[C@@H](O)[C@H](O)CO[C@H]2N2[C@@H](CC(N)=O)C(=O)\C(=C(/O)\C=C\C=C\C=C\C=C\C=C(/Cl)\C=C\C=C(/Cl)[C@H]3O[C@H](C)C[C@@H]3Cl)C2=O)[C@@H](O)[C@@H]1O Chemical compound CO[C@H]1[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1CO[C@@H](O[C@@H]2[C@@H](O)[C@H](O)CO[C@H]2N2[C@@H](CC(N)=O)C(=O)\C(=C(/O)\C=C\C=C\C=C\C=C\C=C(/Cl)\C=C\C=C(/Cl)[C@H]3O[C@H](C)C[C@@H]3Cl)C2=O)[C@@H](O)[C@@H]1O PNDCCASNKRUOMF-AXUFZUPDSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 2
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims 2
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims 2
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- 208000003782 Raynaud disease Diseases 0.000 claims 2
- 102100028255 Renin Human genes 0.000 claims 2
- 108090000783 Renin Proteins 0.000 claims 2
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 2
- 206010042953 Systemic sclerosis Diseases 0.000 claims 2
- SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 claims 2
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 claims 2
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 claims 2
- 229940127282 angiotensin receptor antagonist Drugs 0.000 claims 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 230000001430 anti-depressive effect Effects 0.000 claims 2
- 239000003529 anticholesteremic agent Substances 0.000 claims 2
- 229940127226 anticholesterol agent Drugs 0.000 claims 2
- 229940127219 anticoagulant drug Drugs 0.000 claims 2
- 239000000935 antidepressant agent Substances 0.000 claims 2
- 229940005513 antidepressants Drugs 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- 229960000307 avanafil Drugs 0.000 claims 2
- WEAJZXNPAWBCOA-INIZCTEOSA-N avanafil Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(N2[C@@H](CCC2)CO)=NC=C1C(=O)NCC1=NC=CC=N1 WEAJZXNPAWBCOA-INIZCTEOSA-N 0.000 claims 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229960002173 citrulline Drugs 0.000 claims 2
- 235000013477 citrulline Nutrition 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- FKDHHVKWGRFRTG-UHFFFAOYSA-N linsidomine Chemical compound [N-]1OC(=N)C=[N+]1N1CCOCC1 FKDHHVKWGRFRTG-UHFFFAOYSA-N 0.000 claims 2
- 229960002006 linsidomine Drugs 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 239000006187 pill Substances 0.000 claims 2
- 150000003180 prostaglandins Chemical class 0.000 claims 2
- 239000002891 serotonin 2B antagonist Substances 0.000 claims 2
- 239000002294 steroidal antiinflammatory agent Substances 0.000 claims 2
- 229960000835 tadalafil Drugs 0.000 claims 2
- IEHKWSGCTWLXFU-IIBYNOLFSA-N tadalafil Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C([C]4C=CC=CC4=N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 IEHKWSGCTWLXFU-IIBYNOLFSA-N 0.000 claims 2
- 239000002392 thromboxane A2 receptor stimulating agent Substances 0.000 claims 2
- 229960000438 udenafil Drugs 0.000 claims 2
- IYFNEFQTYQPVOC-UHFFFAOYSA-N udenafil Chemical compound C1=C(C=2NC=3C(CCC)=NN(C)C=3C(=O)N=2)C(OCCC)=CC=C1S(=O)(=O)NCCC1CCCN1C IYFNEFQTYQPVOC-UHFFFAOYSA-N 0.000 claims 2
- 229960002381 vardenafil Drugs 0.000 claims 2
- 229940124549 vasodilator Drugs 0.000 claims 2
- 239000003071 vasodilator agent Substances 0.000 claims 2
- MBKGOQHJIPZMEP-BYPYZUCNSA-N (2s)-2-(dimethylamino)propanamide Chemical compound CN(C)[C@@H](C)C(N)=O MBKGOQHJIPZMEP-BYPYZUCNSA-N 0.000 claims 1
- MTIRIKBRVALRPJ-NTMALXAHSA-N (Z)-[3-aminopropyl(propan-2-yl)amino]-hydroxyimino-oxidoazanium Chemical compound CC(C)N(CCCN)[N+](\[O-])=N\O MTIRIKBRVALRPJ-NTMALXAHSA-N 0.000 claims 1
- YNRCBOXEDICOIX-CLFYSBASSA-N (Z)-[bis(2-aminoethyl)amino]-hydroxyimino-oxidoazanium Chemical compound NCCN(CC[NH3+])[N+](\[O-])=N\[O-] YNRCBOXEDICOIX-CLFYSBASSA-N 0.000 claims 1
- MUMXDRRTIYLYMY-YJKCNMNRSA-N (Z)-[dodecyl-[6-(dodecylazaniumyl)hexyl]amino]-oxido-oxidoiminoazanium Chemical compound CCCCCCCCCCCC[NH2+]CCCCCCN(CCCCCCCCCCCC)[N+](\[O-])=N\[O-] MUMXDRRTIYLYMY-YJKCNMNRSA-N 0.000 claims 1
- NZJXADCEESMBPW-UHFFFAOYSA-N 1-methylsulfinyldecane Chemical compound CCCCCCCCCCS(C)=O NZJXADCEESMBPW-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims 1
- PMYJGTWUVVVOFO-UHFFFAOYSA-N 4-phenyl-3-furoxancarbonitrile Chemical compound N#CC1=[N+]([O-])ON=C1C1=CC=CC=C1 PMYJGTWUVVVOFO-UHFFFAOYSA-N 0.000 claims 1
- INLBUQIADGPECI-UHFFFAOYSA-N 5-(5-acetyl-2-butoxypyridin-3-yl)-3-ethyl-2-(1-ethylazetidin-3-yl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCCOC1=NC=C(C(C)=O)C=C1C1=NC2=C(CC)N(C3CN(CC)C3)N=C2C(=O)N1 INLBUQIADGPECI-UHFFFAOYSA-N 0.000 claims 1
- YJMYSLFFZJUXOA-UHFFFAOYSA-N 5-bromo-3-[3-(4-chlorophenyl)propoxy]-4-(pyridin-3-ylmethylamino)-1h-pyridazin-6-one Chemical compound C1=CC(Cl)=CC=C1CCCOC1=NNC(=O)C(Br)=C1NCC1=CC=CN=C1 YJMYSLFFZJUXOA-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 206010002153 Anal fissure Diseases 0.000 claims 1
- 208000016583 Anus disease Diseases 0.000 claims 1
- 206010061666 Autonomic neuropathy Diseases 0.000 claims 1
- 201000002829 CREST Syndrome Diseases 0.000 claims 1
- 108090000312 Calcium Channels Proteins 0.000 claims 1
- 102000003922 Calcium Channels Human genes 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- 206010011985 Decubitus ulcer Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 208000009531 Fissure in Ano Diseases 0.000 claims 1
- 208000001034 Frostbite Diseases 0.000 claims 1
- 206010017711 Gangrene Diseases 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 claims 1
- 239000000006 Nitroglycerin Substances 0.000 claims 1
- 208000004210 Pressure Ulcer Diseases 0.000 claims 1
- 208000025747 Rheumatic disease Diseases 0.000 claims 1
- ZIIQCSMRQKCOCT-YFKPBYRVSA-N S-nitroso-N-acetyl-D-penicillamine Chemical compound CC(=O)N[C@@H](C(O)=O)C(C)(C)SN=O ZIIQCSMRQKCOCT-YFKPBYRVSA-N 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 229920002125 Sokalan® Polymers 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- YWXYYJSYQOXTPL-JGWLITMVSA-N [(3r,3ar,6s,6as)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] nitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-JGWLITMVSA-N 0.000 claims 1
- 229960003116 amyl nitrite Drugs 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- 230000002785 anti-thrombosis Effects 0.000 claims 1
- 229940125708 antidiabetic agent Drugs 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 229960003121 arginine Drugs 0.000 claims 1
- 239000002981 blocking agent Substances 0.000 claims 1
- 239000000872 buffer Substances 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- HSMMSDWNEJLVRY-INIZCTEOSA-N dodecyl (2s)-2-(dimethylamino)propanoate Chemical compound CCCCCCCCCCCCOC(=O)[C@H](C)N(C)C HSMMSDWNEJLVRY-INIZCTEOSA-N 0.000 claims 1
- IHSPMDXQWYKHOA-UHFFFAOYSA-N dodecyl 2-(dimethylamino)acetate Chemical compound CCCCCCCCCCCCOC(=O)CN(C)C IHSPMDXQWYKHOA-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 239000003623 enhancer Substances 0.000 claims 1
- 210000003195 fascia Anatomy 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 229960003180 glutathione Drugs 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 claims 1
- 229960003711 glyceryl trinitrate Drugs 0.000 claims 1
- MVJUVYOAWZQQTL-UHFFFAOYSA-N hydroxyimino-oxido-sulfoazanium Chemical compound ON=[N+]([O-])S(O)(=O)=O MVJUVYOAWZQQTL-UHFFFAOYSA-N 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims 1
- 239000006210 lotion Substances 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- 150000004667 medium chain fatty acids Chemical class 0.000 claims 1
- MIJFNYMSCFYZNY-UHFFFAOYSA-N mirodenafil Chemical compound C1=C(C=2NC=3C(CCC)=CN(CC)C=3C(=O)N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCO)CC1 MIJFNYMSCFYZNY-UHFFFAOYSA-N 0.000 claims 1
- 229950002245 mirodenafil Drugs 0.000 claims 1
- XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 claims 1
- 229960004027 molsidomine Drugs 0.000 claims 1
- UOWHQKQTGZCVNP-UHFFFAOYSA-N n-ethylethanamine;nitroxyl Chemical compound O=N.CCNCC UOWHQKQTGZCVNP-UHFFFAOYSA-N 0.000 claims 1
- DLBKWJOHNPIHQO-UHFFFAOYSA-N n-hydroxy-n-[methyl-[6-(methylamino)hexyl]amino]nitrous amide Chemical compound CNCCCCCCN(C)N(O)N=O DLBKWJOHNPIHQO-UHFFFAOYSA-N 0.000 claims 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 claims 1
- 150000002826 nitrites Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002674 ointment Substances 0.000 claims 1
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 claims 1
- 229950010649 parogrelil Drugs 0.000 claims 1
- 239000003961 penetration enhancing agent Substances 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 claims 1
- 239000005017 polysaccharide Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N salicylic acid phenyl ester Natural products OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 claims 1
- 239000002453 shampoo Substances 0.000 claims 1
- 230000009759 skin aging Effects 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 229940083542 sodium Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 239000000375 suspending agent Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 claims 1
- 230000001732 thrombotic effect Effects 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 239000000080 wetting agent Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28796709P | 2009-12-18 | 2009-12-18 | |
| US61/287,967 | 2009-12-18 | ||
| PCT/US2010/061054 WO2011075655A1 (en) | 2009-12-18 | 2010-12-17 | Methods and compositions for treating peripheral vascular disease |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016029675A Division JP2016166178A (ja) | 2009-12-18 | 2016-02-19 | 末梢血管疾患を治療するための方法および組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013514995A JP2013514995A (ja) | 2013-05-02 |
| JP2013514995A5 true JP2013514995A5 (https=) | 2014-02-06 |
| JP5960061B2 JP5960061B2 (ja) | 2016-08-02 |
Family
ID=44167718
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012544900A Expired - Fee Related JP5960061B2 (ja) | 2009-12-18 | 2010-12-17 | 末梢血管疾患を治療するための方法および組成物 |
| JP2016029675A Pending JP2016166178A (ja) | 2009-12-18 | 2016-02-19 | 末梢血管疾患を治療するための方法および組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016029675A Pending JP2016166178A (ja) | 2009-12-18 | 2016-02-19 | 末梢血管疾患を治療するための方法および組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US20130053393A1 (https=) |
| EP (1) | EP2512479B1 (https=) |
| JP (2) | JP5960061B2 (https=) |
| AU (1) | AU2010330813B2 (https=) |
| CA (1) | CA2784788A1 (https=) |
| DK (1) | DK2512479T3 (https=) |
| WO (1) | WO2011075655A1 (https=) |
Families Citing this family (31)
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| WO2011075691A1 (en) | 2009-12-18 | 2011-06-23 | Exodos Life Sciences Limited Partnership | Methods and compositions for stable liquid drug formulations |
| HRP20150987T1 (hr) * | 2010-05-26 | 2015-10-23 | Adverio Pharma Gmbh | UPORABA sGC STIMULATORA, sGC AKTIVATORA, SAMOSTALNO I U KOMBINACIJAMA S INHIBITORIMA PDE5 ZA LIJEÄŚENJE SISTEMSKE SKLEROZE (SSc) |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| JP2014526461A (ja) * | 2011-09-09 | 2014-10-06 | エスケー ケミカルズ カンパニー，リミテッド | Ｐｄｅ５抑制剤を含む皮膚しわ改善用組成物 |
| EP3024455A1 (en) | 2013-07-25 | 2016-06-01 | Bayer Pharma Aktiengesellschaft | Sgc stimulators or sgc activators and pde5 inhibitors in combination with additional treatment for the therapy of cystic fibrosis |
| CN104644579A (zh) * | 2013-11-25 | 2015-05-27 | 天津市汉康医药生物技术有限公司 | 一种阿伐那非药物组合物 |
| JP6211406B2 (ja) * | 2013-12-04 | 2017-10-11 | ライオン株式会社 | ムスカリン受容体活性化剤及び唾液分泌促進剤 |
| JP6236304B2 (ja) * | 2013-12-04 | 2017-11-22 | ライオン株式会社 | 涙液分泌促進剤 |
| US20160317542A1 (en) | 2013-12-09 | 2016-11-03 | Respira Therapeutics, Inc. | Pde5 inhibitor powder formulations and methods relating thereto |
| TN2017000029A1 (en) | 2014-08-12 | 2018-07-04 | Mezzion Pharma Co Ltd | Methods of improving myocardial performance in fontan patients using udenafil compositions |
| WO2016089893A1 (en) | 2014-12-01 | 2016-06-09 | Achelios Therapeutics Inc. | Methods and compositions for treating migraine and conditions associated with pain |
| MX2017014057A (es) * | 2015-05-06 | 2018-04-10 | Bayer Pharma AG | El uso de estimuladores sgc, activadores gc, solos y combinaciones con inhibidores pde5 para el tratamiento de ulceras digitales (du) concomitante con esclerosis sistemica (ssc). |
| US9993447B2 (en) * | 2015-09-14 | 2018-06-12 | JW Nutritional, LLC | Systems and methods for increasing agmatine cellular uptake by oral administration |
| SMT202200190T1 (it) | 2015-11-16 | 2022-07-21 | Topadur Pharma Ag | Derivati del 2-fenil-3,4-diidropirrolo[2,1-f] [1,2,4]triazinone come inibitori della fosfodesterasi e loro usi |
| EP4166129A1 (en) | 2017-03-14 | 2023-04-19 | Atir Holding S.A. | Use of heterocyclic compounds in the treatment of aged skin |
| CA3055882A1 (en) | 2017-03-14 | 2018-09-20 | Atir Holding S.A. | Topical formulation for the treatment of pigmented skin |
| MX2019013626A (es) | 2017-05-22 | 2020-01-13 | Topadur Pharma Ag | Modo de accion dual novedoso de activadores de guanilato ciclasa solubles e inhibidores de fosfodiesterasa y usos de los mismos. |
| US11117808B2 (en) * | 2017-08-01 | 2021-09-14 | University Of Georgia Research Foundation, Inc. | Mesoporous nitric oxide-releasing silica particles, methods of making, and uses thereof |
| KR20190043369A (ko) * | 2017-10-18 | 2019-04-26 | 주식회사 코아팜바이오 | 유데나필의 신규한 반고형 제제 |
| MX2017016930A (es) * | 2017-12-19 | 2019-06-20 | Malesil Research & Tech Llc | Uso del maleato de sildenafil en el tratamiento de ulceras de pie diabetico. |
| CR20200630A (es) | 2018-06-01 | 2021-05-26 | Tavanta Therapeutics Hungary Incorporated | Sales tópicas de amlodipino para el tratamiento de enfermedades anorrectales |
| EP3833395A1 (en) * | 2018-08-06 | 2021-06-16 | Nicox S.A. | Nitric oxide releasing phosphodiesterase type 5 inhibitor |
| BR112021009958A2 (pt) | 2018-11-28 | 2021-08-17 | Topadur Pharma Ag | modo duplo de ação de ativadores de guanilato ciclase solúveis e inibidores de fosfodiesterase e seus usos |
| WO2020123312A1 (en) | 2018-12-09 | 2020-06-18 | Weinberg Assa | Method to prevent and treat macular degeneration by vasodilators |
| AU2020356193A1 (en) | 2019-09-24 | 2022-05-19 | Children's Hospital Of Philadelphia | Methods of improving exercise performance, single ventricular performance, and myocardial performance index (MPI) in single ventricle heart disease, using udenafil compositions |
| WO2021245192A1 (en) | 2020-06-04 | 2021-12-09 | Topadur Pharma Ag | Novel dual mode of action soluble guanylate cyclase activators and phosphodiesterase inhibitors and uses thereof |
| AU2021388141A1 (en) * | 2020-11-25 | 2023-06-22 | Aisa Pharma, Inc. | Treatment of raynaud's disease |
| US11185513B1 (en) * | 2021-05-07 | 2021-11-30 | King Abdulaziz University | Transfersome-containing transdermal film formulations and methods of use |
| AU2022354094A1 (en) | 2021-09-29 | 2024-02-15 | Topadur Pharma Ag | Topical compositions of 2-phenyl-3,4-dihydropyrrolo[2,l-f] [1,2,4]triazinone derivatives and uses thereof |
| EP4486349A1 (en) | 2022-03-02 | 2025-01-08 | Topadur Pharma AG | Topical compositions and uses therof |
| KR20230129639A (ko) | 2022-03-02 | 2023-09-11 | 연세대학교 산학협력단 | 이중작용 pde5 억제제/질산유기에스터의 국소 혈류 증진을 위한 경피 투약 형태 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7914814B2 (en) * | 1997-09-17 | 2011-03-29 | Strategic Science & Technologies, Llc | Topical delivery of arginine of cause beneficial effects |
| BR9916162A (pt) * | 1998-12-14 | 2001-09-04 | Cellegy Pharma Inc | Composição e método para o tratamento de um distúrbio anorretal e para controlar a dor associada com o mesmo |
| US20040110843A1 (en) * | 2000-01-10 | 2004-06-10 | Nexmed (Holdings), Inc. | Methods of treatment of male erectile dysfunction |
| US20030105108A1 (en) * | 2002-12-19 | 2003-06-05 | Wood Ralph E. | Method of treating peripheral vascular diseases, peripheral neuropathies, and autonomic neuropathies |
| US7737147B2 (en) * | 2000-07-27 | 2010-06-15 | Thomas Nadackal Thomas | Methods and compositions to enhance the efficacy of phosphodiesterase inhibitors |
| US6538033B2 (en) | 2000-08-29 | 2003-03-25 | Huntington Medical Research Institutes | Nitric oxide donor compounds |
| AU2003221636B2 (en) * | 2002-05-09 | 2009-11-12 | Baker Idi Heart And Diabetes Institute Holdings Limited | Amino acid analogues |
| US20020168424A1 (en) * | 2002-07-31 | 2002-11-14 | Dr. Mohsen Shahinpoor | Nitric oxide (NO) donor+cGMP-PDE5 inhibitor as a topical drug for glaucoma |
| US20020182162A1 (en) * | 2002-08-07 | 2002-12-05 | Mohsen Shahinpoor | Nitric oxide (NO) donor+cGMP-PDE5 inhibitor as a topical drug for enhanced hair growth |
| CA2557814A1 (en) * | 2004-03-01 | 2005-09-15 | Lumen Therapeutics, Llc | Compositions and methods for treating diseases |
| HUP0401422A2 (en) * | 2004-07-15 | 2006-04-28 | G Laszlo Meszaros | Use of l-arginine as vasoaktive ingredient absorbing through skin for external application |
| RU2435578C2 (ru) * | 2005-06-29 | 2011-12-10 | Марс, Инкорпорейтед | Возбуждение вазодилатации периферических кровеносных сосудов |
| US20120065165A1 (en) * | 2008-10-31 | 2012-03-15 | Arginetix, Inc | Compositions and methods of treating endothelial disorders |
-
2010
- 2010-12-17 CA CA2784788A patent/CA2784788A1/en not_active Abandoned
- 2010-12-17 WO PCT/US2010/061054 patent/WO2011075655A1/en not_active Ceased
- 2010-12-17 EP EP10838297.9A patent/EP2512479B1/en not_active Not-in-force
- 2010-12-17 DK DK10838297.9T patent/DK2512479T3/en active
- 2010-12-17 AU AU2010330813A patent/AU2010330813B2/en not_active Ceased
- 2010-12-17 US US13/517,010 patent/US20130053393A1/en not_active Abandoned
- 2010-12-17 JP JP2012544900A patent/JP5960061B2/ja not_active Expired - Fee Related
-
2014
- 2014-10-03 US US14/506,172 patent/US20150031704A1/en not_active Abandoned
-
2016
- 2016-02-19 JP JP2016029675A patent/JP2016166178A/ja active Pending
-
2017
- 2017-10-12 US US15/782,538 patent/US20180036314A1/en not_active Abandoned
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