JP2003519657A - プロスタグランジン組成物および男性勃起機能障害の処置法 - Google Patents
プロスタグランジン組成物および男性勃起機能障害の処置法Info
- Publication number
- JP2003519657A JP2003519657A JP2001551477A JP2001551477A JP2003519657A JP 2003519657 A JP2003519657 A JP 2003519657A JP 2001551477 A JP2001551477 A JP 2001551477A JP 2001551477 A JP2001551477 A JP 2001551477A JP 2003519657 A JP2003519657 A JP 2003519657A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- group
- prostaglandin
- mixtures
- alkyl
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 218
- 201000001881 impotence Diseases 0.000 title claims abstract description 50
- 208000010228 Erectile Dysfunction Diseases 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 59
- 150000003180 prostaglandins Chemical class 0.000 title claims description 16
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 claims abstract description 92
- -1 N, N-disubstituted amino Chemical group 0.000 claims abstract description 63
- 150000002634 lipophilic molecules Chemical class 0.000 claims abstract description 29
- 150000002148 esters Chemical class 0.000 claims abstract description 27
- 239000003961 penetration enhancing agent Substances 0.000 claims abstract description 25
- 239000007853 buffer solution Substances 0.000 claims abstract description 23
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 22
- 150000004676 glycans Chemical class 0.000 claims abstract description 21
- 239000005017 polysaccharide Substances 0.000 claims abstract description 21
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 17
- 230000002378 acidificating effect Effects 0.000 claims abstract description 10
- 150000001298 alcohols Chemical class 0.000 claims abstract description 8
- 230000001939 inductive effect Effects 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 230000035515 penetration Effects 0.000 claims description 25
- 239000003995 emulsifying agent Substances 0.000 claims description 21
- 210000003899 penis Anatomy 0.000 claims description 21
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 claims description 13
- 229920002125 Sokalan® Polymers 0.000 claims description 13
- 229960000711 alprostadil Drugs 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000003623 enhancer Substances 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 claims description 10
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 10
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 claims description 9
- 229920000926 Galactomannan Polymers 0.000 claims description 8
- 229920000161 Locust bean gum Polymers 0.000 claims description 8
- 125000005908 glyceryl ester group Chemical group 0.000 claims description 8
- 235000010420 locust bean gum Nutrition 0.000 claims description 8
- 239000000711 locust bean gum Substances 0.000 claims description 8
- 239000003755 preservative agent Substances 0.000 claims description 7
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- SZYSLWCAWVWFLT-UTGHZIEOSA-N [(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl octadecanoate Chemical group O([C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@]1(COC(=O)CCCCCCCCCCCCCCCCC)O[C@H](CO)[C@@H](O)[C@@H]1O SZYSLWCAWVWFLT-UTGHZIEOSA-N 0.000 claims description 6
- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- HSMMSDWNEJLVRY-INIZCTEOSA-N dodecyl (2s)-2-(dimethylamino)propanoate Chemical compound CCCCCCCCCCCCOC(=O)[C@H](C)N(C)C HSMMSDWNEJLVRY-INIZCTEOSA-N 0.000 claims description 5
- 239000003589 local anesthetic agent Substances 0.000 claims description 5
- 229920000136 polysorbate Polymers 0.000 claims description 5
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 claims description 5
- 229960001289 prazosin Drugs 0.000 claims description 5
- RXBQNMWIQKOSCS-UHFFFAOYSA-N (7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)methanol Chemical compound C1C2C(C)(C)C1CC=C2CO RXBQNMWIQKOSCS-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003205 fragrance Substances 0.000 claims description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 3
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 claims description 3
- GJGOEPNSCVWOLP-UHFFFAOYSA-N C(CC)(=O)OCC(CCCCCCCCCC)N(C)C Chemical group C(CC)(=O)OCC(CCCCCCCCCC)N(C)C GJGOEPNSCVWOLP-UHFFFAOYSA-N 0.000 claims description 3
- 229920002907 Guar gum Polymers 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- QZVCTJOXCFMACW-UHFFFAOYSA-N Phenoxybenzamine Chemical compound C=1C=CC=CC=1CN(CCCl)C(C)COC1=CC=CC=C1 QZVCTJOXCFMACW-UHFFFAOYSA-N 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229960004042 diazoxide Drugs 0.000 claims description 3
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 claims description 3
- XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 claims description 3
- 229940091854 dodecyl propionate Drugs 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000665 guar gum Substances 0.000 claims description 3
- 235000010417 guar gum Nutrition 0.000 claims description 3
- 229960002154 guar gum Drugs 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 229960003418 phenoxybenzamine Drugs 0.000 claims description 3
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 claims description 3
- 229960001999 phentolamine Drugs 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000002335 preservative effect Effects 0.000 claims description 3
- 230000000717 retained effect Effects 0.000 claims description 3
- 229940083618 sodium nitroprusside Drugs 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- XUKAVPATXGYVKJ-WPKBUWHJSA-N (6ar,9r)-n-[(2s)-1-hydroxypropan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CN(C)C3=C1 XUKAVPATXGYVKJ-WPKBUWHJSA-N 0.000 claims description 2
- KIPQYJOLEGBNHQ-UHFFFAOYSA-N 1-(dimethylamino)propan-2-yl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(C)CN(C)C KIPQYJOLEGBNHQ-UHFFFAOYSA-N 0.000 claims description 2
- IVVNZDGDKPTYHK-JTQLQIEISA-N 1-cyano-2-[(2s)-3,3-dimethylbutan-2-yl]-3-pyridin-4-ylguanidine Chemical compound CC(C)(C)[C@H](C)N=C(NC#N)NC1=CC=NC=C1 IVVNZDGDKPTYHK-JTQLQIEISA-N 0.000 claims description 2
- AMEMLELAMQEAIA-UHFFFAOYSA-N 6-(tert-butyl)thieno[3,2-d]pyrimidin-4(3H)-one Chemical compound N1C=NC(=O)C2=C1C=C(C(C)(C)C)S2 AMEMLELAMQEAIA-UHFFFAOYSA-N 0.000 claims description 2
- VCCNKWWXYVWTLT-CYZBKYQRSA-N 7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one Chemical compound C1=C(O)C(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(O)C=C2O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 VCCNKWWXYVWTLT-CYZBKYQRSA-N 0.000 claims description 2
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 claims description 2
- RXBQNMWIQKOSCS-RKDXNWHRSA-N Myrtenol Natural products C1[C@H]2C(C)(C)[C@@H]1CC=C2CO RXBQNMWIQKOSCS-RKDXNWHRSA-N 0.000 claims description 2
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000006 Nitroglycerin Substances 0.000 claims description 2
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 claims description 2
- 229960004607 alfuzosin Drugs 0.000 claims description 2
- 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 claims description 2
- 229960003116 amyl nitrite Drugs 0.000 claims description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 2
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 claims description 2
- 229960001076 chlorpromazine Drugs 0.000 claims description 2
- 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 claims description 2
- 229960002768 dipyridamole Drugs 0.000 claims description 2
- 229960001389 doxazosin Drugs 0.000 claims description 2
- 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 claims description 2
- YREISLCRUMOYAY-IIPCNOPRSA-N ergometrine maleate Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 YREISLCRUMOYAY-IIPCNOPRSA-N 0.000 claims description 2
- 229940030804 ergonovine maleate Drugs 0.000 claims description 2
- 229960001903 ergotamine tartrate Drugs 0.000 claims description 2
- 229960003711 glyceryl trinitrate Drugs 0.000 claims description 2
- 229960003878 haloperidol Drugs 0.000 claims description 2
- 229940033357 isopropyl laurate Drugs 0.000 claims description 2
- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 claims description 2
- 229960000201 isosorbide dinitrate Drugs 0.000 claims description 2
- WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 claims description 2
- 229960004650 metergoline Drugs 0.000 claims description 2
- SZUQJDJBJHBVBO-CTTKVJGISA-N metergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C=3C=CC=C4N(C)C=C(C=34)C2)=C1)C)C1=CC=CC=C1 SZUQJDJBJHBVBO-CTTKVJGISA-N 0.000 claims description 2
- 229950004958 metergotamine Drugs 0.000 claims description 2
- XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 claims description 2
- 229960004027 molsidomine Drugs 0.000 claims description 2
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 claims description 2
- 229940049964 oleate Drugs 0.000 claims description 2
- YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 claims description 2
- 229960004851 pergolide Drugs 0.000 claims description 2
- 229960002310 pinacidil Drugs 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 229950004866 propisergide Drugs 0.000 claims description 2
- 239000008247 solid mixture Substances 0.000 claims description 2
- 229960001693 terazosin Drugs 0.000 claims description 2
- VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 229960003991 trazodone Drugs 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- 229960002906 trimazosin Drugs 0.000 claims description 2
- YNZXWQJZEDLQEG-UHFFFAOYSA-N trimazosin Chemical compound N1=C2C(OC)=C(OC)C(OC)=CC2=C(N)N=C1N1CCN(C(=O)OCC(C)(C)O)CC1 YNZXWQJZEDLQEG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002550 vasoactive agent Substances 0.000 claims description 2
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine 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-SCYLSFHTSA-N 0.000 claims description 2
- 229960000317 yohimbine Drugs 0.000 claims description 2
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 claims description 2
- FVGJPCFYGPKBKJ-UHFFFAOYSA-N Dodecyl propionate Chemical compound CCCCCCCCCCCCOC(=O)CC FVGJPCFYGPKBKJ-UHFFFAOYSA-N 0.000 claims 2
- XMCXTGRBAIZQCC-AATRIKPKSA-N (e)-3-[2-[n-acetyl-3-(trifluoromethyl)anilino]-1,3-thiazol-4-yl]prop-2-enoic acid Chemical compound C=1C=CC(C(F)(F)F)=CC=1N(C(=O)C)C1=NC(\C=C\C(O)=O)=CS1 XMCXTGRBAIZQCC-AATRIKPKSA-N 0.000 claims 1
- ZIIQCSMRQKCOCT-UHFFFAOYSA-N 2-acetamido-3-methyl-3-nitrososulfanylbutanoic acid Chemical compound CC(=O)NC(C(O)=O)C(C)(C)SN=O ZIIQCSMRQKCOCT-UHFFFAOYSA-N 0.000 claims 1
- JXZZEXZZKAWDSP-UHFFFAOYSA-N 3-(2-(4-Benzamidopiperid-1-yl)ethyl)indole Chemical compound C1CN(CCC=2C3=CC=CC=C3NC=2)CCC1NC(=O)C1=CC=CC=C1 JXZZEXZZKAWDSP-UHFFFAOYSA-N 0.000 claims 1
- BMUKKTUHUDJSNZ-UHFFFAOYSA-N 4-[1-hydroxy-2-(1-phenoxypropan-2-ylamino)propyl]phenol Chemical compound C=1C=C(O)C=CC=1C(O)C(C)NC(C)COC1=CC=CC=C1 BMUKKTUHUDJSNZ-UHFFFAOYSA-N 0.000 claims 1
- IQNPKRUTUGGDEQ-UHFFFAOYSA-N CN(C)CCCCCCCCCCCCOC(C)=O Chemical compound CN(C)CCCCCCCCCCCCOC(C)=O IQNPKRUTUGGDEQ-UHFFFAOYSA-N 0.000 claims 1
- YSEXMKHXIOCEJA-FVFQAYNVSA-N Nicergoline Chemical compound C([C@@H]1C[C@]2([C@H](N(C)C1)CC=1C3=C2C=CC=C3N(C)C=1)OC)OC(=O)C1=CN=CC(Br)=C1 YSEXMKHXIOCEJA-FVFQAYNVSA-N 0.000 claims 1
- 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 claims 1
- VPXSOMITANBBPE-XGWLTEMNSA-N acetergamine Chemical compound C1=CC=C2[C@H]3C[C@@H](CNC(C)=O)CN(C)[C@@H]3CC3=CN=C1[C]32 VPXSOMITANBBPE-XGWLTEMNSA-N 0.000 claims 1
- 229950004701 acetergamine Drugs 0.000 claims 1
- 229960001631 carbomer Drugs 0.000 claims 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims 1
- 229960005450 eritrityl tetranitrate Drugs 0.000 claims 1
- SNFOERUNNSHUGP-ZXZARUISSA-N erythrityl tetranitrate Chemical compound [O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@@H](O[N+]([O-])=O)CO[N+]([O-])=O SNFOERUNNSHUGP-ZXZARUISSA-N 0.000 claims 1
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Gynecology & Obstetrics (AREA)
- Reproductive Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/480,738 | 2000-01-10 | ||
| US09/480,738 US6323241B1 (en) | 2000-01-10 | 2000-01-10 | Prostaglandin compositions and methods of treatment for male erectile dysfunction |
| PCT/US2001/000852 WO2001051053A1 (en) | 2000-01-10 | 2001-01-10 | Prostaglandin compositions and methods of treatment for male erectile dysfunction |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007186380A Division JP2007302690A (ja) | 2000-01-10 | 2007-07-18 | プロスタグランジン組成物および男性勃起機能障害の処置法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2003519657A true JP2003519657A (ja) | 2003-06-24 |
Family
ID=23909154
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001551477A Pending JP2003519657A (ja) | 2000-01-10 | 2001-01-10 | プロスタグランジン組成物および男性勃起機能障害の処置法 |
| JP2007186380A Pending JP2007302690A (ja) | 2000-01-10 | 2007-07-18 | プロスタグランジン組成物および男性勃起機能障害の処置法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007186380A Pending JP2007302690A (ja) | 2000-01-10 | 2007-07-18 | プロスタグランジン組成物および男性勃起機能障害の処置法 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6323241B1 (https=) |
| EP (1) | EP1255552B1 (https=) |
| JP (2) | JP2003519657A (https=) |
| KR (1) | KR100614361B1 (https=) |
| CN (1) | CN1394140A (https=) |
| AT (1) | ATE290383T1 (https=) |
| AU (1) | AU760576C (https=) |
| BE (1) | BE2014C001I2 (https=) |
| BR (1) | BR0107478A (https=) |
| CA (1) | CA2395217C (https=) |
| DE (1) | DE60109274T2 (https=) |
| ES (1) | ES2236245T3 (https=) |
| HK (1) | HK1047700B (https=) |
| HU (1) | HUP0204159A3 (https=) |
| IL (2) | IL150306A0 (https=) |
| MX (1) | MXPA02006758A (https=) |
| PT (1) | PT1255552E (https=) |
| TR (1) | TR200201769T2 (https=) |
| WO (1) | WO2001051053A1 (https=) |
| ZA (1) | ZA200205433B (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR1002847B (el) | 1997-05-06 | 1998-01-27 | Χρηση της μισοπροστολης ή/και της μισοπροστολης οξυ για την παρασκευη φαρμακευτικου προιοντος για τη θεραπευτικη αντιμετωπιση των δυσλειτουργιων της στυσεως | |
| US6414028B1 (en) * | 1997-11-05 | 2002-07-02 | Nexmed Holdings, Inc. | Topical compositions containing prostaglandin E1 |
| US6825234B2 (en) | 1998-12-10 | 2004-11-30 | Nexmed (Holdings) , Inc. | Compositions and methods for amelioration of human female sexual dysfunction |
| US20050004226A1 (en) * | 1998-12-10 | 2005-01-06 | Nexmed (Holdings), Inc. | Compositions and methods for amelioration of human female sexual dysfunction |
| EA008720B1 (ru) * | 1998-12-10 | 2007-06-29 | Нексмед (Холдингс), Инк. | Применение композиции на основе простагландина для лечения расстройства сексуального возбуждения у женщин |
| US7105571B2 (en) * | 2000-01-10 | 2006-09-12 | Nexmed Holdings, Inc. | Prostaglandin compositions and methods of treatment for male erectile dysfunction |
| US20040110843A1 (en) * | 2000-01-10 | 2004-06-10 | Nexmed (Holdings), Inc. | Methods of treatment of male erectile dysfunction |
| US6693135B2 (en) * | 2000-01-10 | 2004-02-17 | Nexmed (Holdings) Incorporated | Prostaglandin compositions and methods of treatment for male erectile dysfunction |
| US6503894B1 (en) | 2000-08-30 | 2003-01-07 | Unimed Pharmaceuticals, Inc. | Pharmaceutical composition and method for treating hypogonadism |
| US20090257956A1 (en) * | 2002-01-25 | 2009-10-15 | Ramsey Sallis | Treatment Method for Treatment of Erectile Dysfunction and Premature Ejaculation |
| DK1474143T3 (da) | 2002-01-25 | 2009-01-26 | Modular Properties Ltd | Fremgangsmåder og sammensætninger til bahandling af mandlig erektil dysfunktion |
| US20090035221A1 (en) * | 2002-01-25 | 2009-02-05 | Ramsey Sallis | Methods and Compositions for Treatment of Erectile Dysfunction |
| MXPA04007828A (es) * | 2002-02-15 | 2004-10-15 | Nexmed Holdings Inc | Composicion de prostaglandina para eltratamiento de la disfuncion erectil. |
| CA2493723A1 (en) * | 2002-09-06 | 2004-03-18 | Nexmed Holdings, Inc. | Methods of treatment of male erectile dysfunction |
| GB0222522D0 (en) | 2002-09-27 | 2002-11-06 | Controlled Therapeutics Sct | Water-swellable polymers |
| US6841574B2 (en) * | 2003-01-03 | 2005-01-11 | Nexmed Holdings, Inc. | Topical stabilized prostaglandin E compound dosage forms |
| BRPI0408454A (pt) | 2003-03-21 | 2006-04-04 | Nexmed Holdings Inc | composição tópica, método de tratar a ejaculação precoce, e, uso da composição |
| KR20050119134A (ko) * | 2003-03-21 | 2005-12-20 | 넥스메드 홀딩스 인코포레이티드 | 발기 부전 치료용 프로스타글란딘 조성물 |
| JP2006520788A (ja) * | 2003-03-21 | 2006-09-14 | ネックスメド ホールディングス インコーポレイテッド | プロスタグランジン組成物による血管形成促進および方法 |
| AU2004227853A1 (en) * | 2003-04-02 | 2004-10-21 | Nexmed (Holdings), Inc. | Prostaglandin compositions and their use for the treatment of vasospasm |
| US20050159985A1 (en) * | 2003-11-21 | 2005-07-21 | Bertram Carl T. | System and method of stratifying intervention groups and comparison groups based on disease severity index scores and ranges |
| GB0417401D0 (en) | 2004-08-05 | 2004-09-08 | Controlled Therapeutics Sct | Stabilised prostaglandin composition |
| EP1784225B1 (en) * | 2004-08-19 | 2016-10-05 | Applied Genetics Incorporated Dermatics | Biomimetic of evodia rutaecarpa fruit extract for amelioration of inflammation |
| GB0613333D0 (en) | 2006-07-05 | 2006-08-16 | Controlled Therapeutics Sct | Hydrophilic polyurethane compositions |
| GB0613638D0 (en) | 2006-07-08 | 2006-08-16 | Controlled Therapeutics Sct | Polyurethane elastomers |
| GB0620685D0 (en) | 2006-10-18 | 2006-11-29 | Controlled Therapeutics Sct | Bioresorbable polymers |
| US9005183B2 (en) * | 2007-05-16 | 2015-04-14 | Health Knight, Llc | System and method for treating erectile dysfunction |
| EP2646015B1 (en) * | 2010-12-02 | 2020-04-22 | Ferring International Center S.A. | Active enantiomer of dodecyl 2-(n,n-dimethylamino)-propionate |
| WO2012139033A1 (en) | 2011-04-07 | 2012-10-11 | Nexmed Holdings, Inc. | Methods and compositions for treating raynaud's disease |
| US10226418B2 (en) | 2014-05-12 | 2019-03-12 | Susie Q, Ltd. | Arginine-containing topical composition |
| JP6856532B2 (ja) | 2015-01-20 | 2021-04-07 | エックスオーシー ファーマシューティカルズ インコーポレイテッドＸｏｃ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ | エルゴリン化合物およびその使用 |
| JP2018502889A (ja) | 2015-01-20 | 2018-02-01 | エックスオーシー ファーマシューティカルズ インコーポレイテッドＸｏｃ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ | イソエルゴリン化合物およびその使用 |
| EP3266458A1 (en) | 2016-07-05 | 2018-01-10 | Fagron B.V. | Method and composition and kit for treating erectile dysfunction |
| EP3630758A1 (en) | 2017-06-01 | 2020-04-08 | Xoc Pharmaceuticals, Inc | Ergoline derivatives for use in medicine |
| USD1122263S1 (en) * | 2023-02-15 | 2026-04-14 | Amadeus S.A.S. | Display screen with animated graphical user interface |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2818855A (en) | 1954-02-11 | 1958-01-07 | Anthony P Miller | Surgical device |
| BE790840A (fr) | 1971-11-01 | 1973-04-30 | Upjohn Co | Solutions de medicaments instables et leur preparation |
| US4127118B1 (en) | 1977-03-16 | 1995-12-19 | Alvaro Latorre | Method of effecting and enhancing an erection |
| US4254145A (en) | 1978-08-16 | 1981-03-03 | American Cyanamid Company | Topical application of prostaglandin hypotensive agents |
| US4311707A (en) | 1979-02-12 | 1982-01-19 | American Cyanamid Company | Process for topically producing cutaneous vasodilation for the treatment of vasospastic or ischemic conditions |
| 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 |
| US4980378A (en) | 1988-06-01 | 1990-12-25 | Odontex, Inc. | Biodegradable absorption enhancers |
| SE463851B (sv) | 1988-09-02 | 1991-02-04 | Amsu Ltd | Komposition foer behandling av erektil dysfunktion via uretra |
| PT97441B (pt) | 1990-04-25 | 1998-08-31 | Alza Corp | Processo para a preparacao de composicoes farmaceuticas que compreendem agentes vasodilatadores, nomeadamente, nitratos, alcaloides ergoticos ou prostaglandinas, ou agentes vasoconstritores, nomeadamente, alcoois benzilicos ou benzenodiois substituidos ou ainda agentes antiflamatorios esteroides e nao esteroides e dispositivos para a sua administracao transuretral |
| US5242391A (en) | 1990-04-25 | 1993-09-07 | Alza Corporation | Urethral insert for treatment of erectile dysfunction |
| US5380760A (en) | 1993-11-19 | 1995-01-10 | Minnesota Mining And Manufacturing Company | Transdermal prostaglandin composition |
| NZ305560A (en) | 1995-03-14 | 1998-11-25 | Vivus Inc | Method for preventing erectile dysfunction by administering vasoactive agent, particularly a prostaglandin, kit therefor |
| AU742787B2 (en) * | 1997-07-09 | 2002-01-10 | Androsolutions, Inc. | Improved methods and compositions for treating male erectile dysfunction |
| EP1027054A4 (en) * | 1997-10-28 | 2002-11-04 | Vivus Inc | LOCAL CONTRIBUTION OF PHOSPHODIESTERASE INHIBITORS IN THE TREATMENT OF ERECTILE DYSFUNCTION |
| US6046244A (en) * | 1997-11-05 | 2000-04-04 | Nexmed Holdings, Inc. | Topical compositions for prostaglandin E1 delivery |
| US5942545A (en) | 1998-06-15 | 1999-08-24 | Macrochem Corporation | Composition and method for treating penile erectile dysfunction |
| US6486207B2 (en) | 1998-12-10 | 2002-11-26 | Nexmed (Holdings), Inc. | Compositions and methods for amelioration of human female sexual dysfunction |
| US6102849A (en) | 1999-04-03 | 2000-08-15 | Hakac; John R. | Non-surgical penile prosthesis |
-
2000
- 2000-01-10 US US09/480,738 patent/US6323241B1/en not_active Expired - Lifetime
-
2001
- 2001-01-10 JP JP2001551477A patent/JP2003519657A/ja active Pending
- 2001-01-10 HK HK02109079.3A patent/HK1047700B/en not_active IP Right Cessation
- 2001-01-10 CA CA002395217A patent/CA2395217C/en not_active Expired - Lifetime
- 2001-01-10 HU HU0204159A patent/HUP0204159A3/hu active IP Right Revival
- 2001-01-10 DE DE60109274T patent/DE60109274T2/de not_active Expired - Lifetime
- 2001-01-10 AU AU29349/01A patent/AU760576C/en not_active Expired
- 2001-01-10 WO PCT/US2001/000852 patent/WO2001051053A1/en not_active Ceased
- 2001-01-10 PT PT01942300T patent/PT1255552E/pt unknown
- 2001-01-10 BR BR0107478-4A patent/BR0107478A/pt not_active Application Discontinuation
- 2001-01-10 ES ES01942300T patent/ES2236245T3/es not_active Expired - Lifetime
- 2001-01-10 EP EP01942300A patent/EP1255552B1/en not_active Expired - Lifetime
- 2001-01-10 KR KR1020027008845A patent/KR100614361B1/ko not_active Expired - Lifetime
- 2001-01-10 AT AT01942300T patent/ATE290383T1/de active
- 2001-01-10 CN CN01803447A patent/CN1394140A/zh active Pending
- 2001-01-10 MX MXPA02006758A patent/MXPA02006758A/es active IP Right Grant
- 2001-01-10 IL IL15030601A patent/IL150306A0/xx active IP Right Grant
- 2001-01-10 TR TR2002/01769T patent/TR200201769T2/xx unknown
-
2002
- 2002-06-18 IL IL150306A patent/IL150306A/en unknown
- 2002-07-08 ZA ZA200205433A patent/ZA200205433B/xx unknown
-
2007
- 2007-07-18 JP JP2007186380A patent/JP2007302690A/ja active Pending
-
2014
- 2014-01-06 BE BE2014C001C patent/BE2014C001I2/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007302690A (ja) | 2007-11-22 |
| IL150306A0 (en) | 2002-12-01 |
| AU760576B2 (en) | 2003-05-15 |
| EP1255552B1 (en) | 2005-03-09 |
| BE2014C001I2 (https=) | 2020-01-30 |
| IL150306A (en) | 2007-06-03 |
| PT1255552E (pt) | 2005-06-30 |
| HK1047700B (en) | 2005-05-27 |
| DE60109274D1 (de) | 2005-04-14 |
| ZA200205433B (en) | 2003-11-26 |
| US6323241B1 (en) | 2001-11-27 |
| CA2395217C (en) | 2004-10-26 |
| TR200201769T2 (tr) | 2002-11-21 |
| EP1255552A1 (en) | 2002-11-13 |
| HUP0204159A3 (en) | 2005-03-29 |
| HK1047700A1 (en) | 2003-03-07 |
| CN1394140A (zh) | 2003-01-29 |
| AU2934901A (en) | 2001-07-24 |
| BR0107478A (pt) | 2002-09-03 |
| KR20020073498A (ko) | 2002-09-26 |
| DE60109274T2 (de) | 2006-02-09 |
| CA2395217A1 (en) | 2001-07-19 |
| HUP0204159A2 (hu) | 2003-04-28 |
| WO2001051053A1 (en) | 2001-07-19 |
| AU760576C (en) | 2004-04-08 |
| MXPA02006758A (es) | 2008-09-12 |
| ES2236245T3 (es) | 2005-07-16 |
| KR100614361B1 (ko) | 2006-08-18 |
| ATE290383T1 (de) | 2005-03-15 |
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