JP2011502172A5 - - Google Patents
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- Publication number
- JP2011502172A5 JP2011502172A5 JP2010532376A JP2010532376A JP2011502172A5 JP 2011502172 A5 JP2011502172 A5 JP 2011502172A5 JP 2010532376 A JP2010532376 A JP 2010532376A JP 2010532376 A JP2010532376 A JP 2010532376A JP 2011502172 A5 JP2011502172 A5 JP 2011502172A5
- Authority
- JP
- Japan
- Prior art keywords
- acetate
- delivery system
- transdermal delivery
- sodium
- pharmacological agent
- 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.)
- Ceased
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- 230000037317 transdermal delivery Effects 0.000 claims 17
- 239000000203 mixture Substances 0.000 claims 13
- 239000002831 pharmacologic agent Substances 0.000 claims 8
- 229940088597 hormone Drugs 0.000 claims 7
- 239000005556 hormone Substances 0.000 claims 7
- 150000003431 steroids Chemical class 0.000 claims 7
- 239000002202 Polyethylene glycol Substances 0.000 claims 6
- 229920001223 polyethylene glycol Polymers 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims 4
- 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 3
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 claims 3
- 230000035515 penetration Effects 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 239000007921 spray Substances 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 claims 2
- IMONTRJLAWHYGT-ZCPXKWAGSA-N Norethindrone Acetate Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@](C#C)(OC(=O)C)[C@@]1(C)CC2 IMONTRJLAWHYGT-ZCPXKWAGSA-N 0.000 claims 2
- LRJOMUJRLNCICJ-JZYPGELDSA-N Prednisolone acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O LRJOMUJRLNCICJ-JZYPGELDSA-N 0.000 claims 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims 2
- LTXUBHXFNYNXJW-NGOGOHBQSA-N acetic acid (8S,9S,10R,13S,14S,17S)-17-acetyl-16-(hydroxymethyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound CC(O)=O.C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(CO)[C@H](C(=O)C)[C@@]1(C)CC2 LTXUBHXFNYNXJW-NGOGOHBQSA-N 0.000 claims 2
- 239000003098 androgen Substances 0.000 claims 2
- FFIAPLNALYDYQK-UHFFFAOYSA-L barium(2+);[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl phosphate Chemical compound [Ba+2].OCC1OC(O)(COP([O-])([O-])=O)C(O)C1O FFIAPLNALYDYQK-UHFFFAOYSA-L 0.000 claims 2
- 229960002537 betamethasone Drugs 0.000 claims 2
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims 2
- VQODGRNSFPNSQE-DVTGEIKXSA-N betamethasone phosphate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COP(O)(O)=O)(O)[C@@]1(C)C[C@@H]2O VQODGRNSFPNSQE-DVTGEIKXSA-N 0.000 claims 2
- 229950006991 betamethasone phosphate Drugs 0.000 claims 2
- -1 desoxymeta Zon Chemical compound 0.000 claims 2
- 239000003623 enhancer Substances 0.000 claims 2
- 229940011871 estrogen Drugs 0.000 claims 2
- 239000000262 estrogen Substances 0.000 claims 2
- 229960000890 hydrocortisone Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229960000334 methylprednisolone sodium succinate Drugs 0.000 claims 2
- 229960001652 norethindrone acetate Drugs 0.000 claims 2
- 229960002800 prednisolone acetate Drugs 0.000 claims 2
- JDOZJEUDSLGTLU-VWUMJDOOSA-N prednisolone phosphate Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 JDOZJEUDSLGTLU-VWUMJDOOSA-N 0.000 claims 2
- 229960002943 prednisolone sodium phosphate Drugs 0.000 claims 2
- 229960003604 testosterone Drugs 0.000 claims 2
- 229960005294 triamcinolone Drugs 0.000 claims 2
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims 2
- 229960002117 triamcinolone acetonide Drugs 0.000 claims 2
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims 1
- PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 claims 1
- ZKFNOUUKULVDOB-UHFFFAOYSA-N 1-amino-1-phenylmethyl phosphonic acid Chemical compound OP(=O)(O)C(N)C1=CC=CC=C1 ZKFNOUUKULVDOB-UHFFFAOYSA-N 0.000 claims 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims 1
- VVOIQBFMTVCINR-WWMZEODYSA-N 11-deoxycorticosterone pivalate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C(C)(C)C)[C@@]1(C)CC2 VVOIQBFMTVCINR-WWMZEODYSA-N 0.000 claims 1
- VTHUYJIXSMGYOQ-KOORYGTMSA-N 17-hydroxyprogesterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 VTHUYJIXSMGYOQ-KOORYGTMSA-N 0.000 claims 1
- BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 claims 1
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 claims 1
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 claims 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims 1
- QTQGHKVYLQBJLO-UHFFFAOYSA-N 4-methylbenzenesulfonate;(4-methyl-1-oxo-1-phenylmethoxypentan-2-yl)azanium Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC(C)CC(N)C(=O)OCC1=CC=CC=C1 QTQGHKVYLQBJLO-UHFFFAOYSA-N 0.000 claims 1
- QGXBDMJGAMFCBF-HLUDHZFRSA-N 5α-Androsterone Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-HLUDHZFRSA-N 0.000 claims 1
- MEZCUMCMVYZPAH-UHFFFAOYSA-N 6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1CCC2(C)C3C(O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CC(F)C2=C1 MEZCUMCMVYZPAH-UHFFFAOYSA-N 0.000 claims 1
- MYYIMZRZXIQBGI-HVIRSNARSA-N 6alpha-Fluoroprednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3C[C@H](F)C2=C1 MYYIMZRZXIQBGI-HVIRSNARSA-N 0.000 claims 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 claims 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 claims 1
- UYIFTLBWAOGQBI-BZDYCCQFSA-N Benzhormovarine Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@H]4O)C)CC2=CC=3OC(=O)C1=CC=CC=C1 UYIFTLBWAOGQBI-BZDYCCQFSA-N 0.000 claims 1
- 229920006051 Capron® Polymers 0.000 claims 1
- QMBJSIBWORFWQT-DFXBJWIESA-N Chlormadinone acetate Chemical compound C1=C(Cl)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 QMBJSIBWORFWQT-DFXBJWIESA-N 0.000 claims 1
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 claims 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims 1
- ITRJWOMZKQRYTA-RFZYENFJSA-N Cortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O ITRJWOMZKQRYTA-RFZYENFJSA-N 0.000 claims 1
- LVHOURKCKUYIGK-RGUJTQARSA-N Dimethisterone Chemical compound C1([C@@H](C)C2)=CC(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@](C#CC)(O)[C@@]2(C)CC1 LVHOURKCKUYIGK-RGUJTQARSA-N 0.000 claims 1
- UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 claims 1
- JQIYNMYZKRGDFK-RUFWAXPRSA-N Estradiol dipropionate Chemical compound C1CC2=CC(OC(=O)CC)=CC=C2[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 JQIYNMYZKRGDFK-RUFWAXPRSA-N 0.000 claims 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims 1
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims 1
- QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 claims 1
- WRWBCPJQPDHXTJ-DTMQFJJTSA-N Methandriol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 WRWBCPJQPDHXTJ-DTMQFJJTSA-N 0.000 claims 1
- XWALNWXLMVGSFR-HLXURNFRSA-N Methandrostenolone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 XWALNWXLMVGSFR-HLXURNFRSA-N 0.000 claims 1
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 claims 1
- ICTXHFFSOAJUMG-SLHNCBLASA-N Norethynodrel Chemical compound C1CC(=O)CC2=C1[C@H]1CC[C@](C)([C@](CC3)(O)C#C)[C@@H]3[C@@H]1CC2 ICTXHFFSOAJUMG-SLHNCBLASA-N 0.000 claims 1
- QSLJIVKCVHQPLV-PEMPUTJUSA-N Oxandrin Chemical compound C([C@@H]1CC2)C(=O)OC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@](C)(O)[C@@]2(C)CC1 QSLJIVKCVHQPLV-PEMPUTJUSA-N 0.000 claims 1
- HUMXXHTVHHLNRO-KAJVQRHHSA-N Prednisolone tebutate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)CC(C)(C)C)(O)[C@@]1(C)C[C@@H]2O HUMXXHTVHHLNRO-KAJVQRHHSA-N 0.000 claims 1
- ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 claims 1
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 claims 1
- XGMPVBXKDAHORN-RBWIMXSLSA-N Triamcinolone diacetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](OC(C)=O)[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O XGMPVBXKDAHORN-RBWIMXSLSA-N 0.000 claims 1
- HKUKRSLIEVXDMS-APDHKMKFSA-N [(8r,9s,13s,14s)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-yl] benzoate Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CCC4=O)C)CC2=CC=3OC(=O)C1=CC=CC=C1 HKUKRSLIEVXDMS-APDHKMKFSA-N 0.000 claims 1
- FPVRUILUEYSIMD-RPRRAYFGSA-N [(8s,9r,10s,11s,13s,14s,16r,17r)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(OC(C)=O)[C@@]1(C)C[C@@H]2O FPVRUILUEYSIMD-RPRRAYFGSA-N 0.000 claims 1
- RACDDTQBAFEERP-PLTZVPCUSA-N [2-[(6s,8s,9s,10r,13s,14s,17r)-6-chloro-17-hydroxy-10,13-dimethyl-3,11-dioxo-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1([C@@H](Cl)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@](C(=O)COC(=O)C)(O)[C@@]2(C)CC1=O RACDDTQBAFEERP-PLTZVPCUSA-N 0.000 claims 1
- PHEOVVDXTQVHAZ-XDANTLIUSA-N [2-[(8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2,2-dimethylpropanoate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C(C)(C)C)(O)[C@@]1(C)C[C@@H]2O PHEOVVDXTQVHAZ-XDANTLIUSA-N 0.000 claims 1
- 229940022663 acetate Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229960002478 aldosterone Drugs 0.000 claims 1
- 230000001195 anabolic effect Effects 0.000 claims 1
- 238000009165 androgen replacement therapy Methods 0.000 claims 1
- 229940061641 androsterone Drugs 0.000 claims 1
- 229960004648 betamethasone acetate Drugs 0.000 claims 1
- AKUJBENLRBOFTD-QZIXMDIESA-N betamethasone acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]1(C)C[C@@H]2O AKUJBENLRBOFTD-QZIXMDIESA-N 0.000 claims 1
- 229960001616 chlormadinone acetate Drugs 0.000 claims 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 claims 1
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 claims 1
- BGSOJVFOEQLVMH-VWUMJDOOSA-N cortisol phosphate Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 BGSOJVFOEQLVMH-VWUMJDOOSA-N 0.000 claims 1
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| EP2782584B1 (en) | 2011-11-23 | 2021-06-09 | TherapeuticsMD, Inc. | Natural combination hormone replacement formulations and therapies |
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2008
- 2008-10-31 KR KR1020107012100A patent/KR101662186B1/ko not_active Expired - Fee Related
- 2008-10-31 CN CN2008801187624A patent/CN101888830B/zh not_active Expired - Fee Related
- 2008-10-31 EP EP08845600.9A patent/EP2219603B1/en not_active Not-in-force
- 2008-10-31 PL PL08845547T patent/PL2214643T3/pl unknown
- 2008-10-31 EA EA201000746A patent/EA019760B1/ru not_active IP Right Cessation
- 2008-10-31 NZ NZ585034A patent/NZ585034A/en not_active IP Right Cessation
- 2008-10-31 AU AU2008318284A patent/AU2008318284B2/en not_active Ceased
- 2008-10-31 JP JP2010532376A patent/JP2011502172A/ja not_active Ceased
- 2008-10-31 BR BRPI0819235A patent/BRPI0819235A2/pt not_active IP Right Cessation
- 2008-10-31 PT PT88456009T patent/PT2219603E/pt unknown
- 2008-10-31 CA CA2704117A patent/CA2704117C/en not_active Expired - Fee Related
- 2008-10-31 ES ES08845600.9T patent/ES2494853T3/es active Active
- 2008-10-31 CA CA2704116A patent/CA2704116A1/en not_active Abandoned
- 2008-10-31 EP EP08845547.2A patent/EP2214643B1/en not_active Not-in-force
- 2008-10-31 DK DK08845547.2T patent/DK2214643T3/da active
- 2008-10-31 CN CN2008801187639A patent/CN101883556B/zh not_active Expired - Fee Related
- 2008-10-31 NZ NZ585033A patent/NZ585033A/en not_active IP Right Cessation
- 2008-10-31 MX MX2010004788A patent/MX2010004788A/es active IP Right Grant
- 2008-10-31 PL PL08845600T patent/PL2219603T3/pl unknown
- 2008-10-31 EA EA201000747A patent/EA201000747A1/ru unknown
- 2008-10-31 US US12/740,666 patent/US20100279988A1/en not_active Abandoned
- 2008-10-31 KR KR1020107012099A patent/KR20100094495A/ko not_active Ceased
- 2008-10-31 WO PCT/AU2008/001614 patent/WO2009055860A1/en not_active Ceased
- 2008-10-31 JP JP2010532377A patent/JP5737942B2/ja not_active Expired - Fee Related
- 2008-10-31 DK DK08845600.9T patent/DK2219603T3/da active
- 2008-10-31 BR BRPI0819245A patent/BRPI0819245A2/pt not_active IP Right Cessation
- 2008-10-31 US US12/740,663 patent/US20100297032A1/en not_active Abandoned
- 2008-10-31 AU AU2008318283A patent/AU2008318283B2/en not_active Ceased
- 2008-10-31 MX MX2010004789A patent/MX2010004789A/es active IP Right Grant
- 2008-10-31 ES ES08845547.2T patent/ES2466676T3/es active Active
- 2008-10-31 PT PT88455472T patent/PT2214643E/pt unknown
- 2008-10-31 WO PCT/AU2008/001613 patent/WO2009055859A1/en not_active Ceased
-
2010
- 2010-05-19 ZA ZA2010/03553A patent/ZA201003553B/en unknown
-
2013
- 2013-05-06 US US13/887,758 patent/US9078810B2/en not_active Expired - Fee Related
- 2013-05-06 US US13/887,719 patent/US20130317462A1/en not_active Abandoned
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2015
- 2015-06-10 US US14/735,428 patent/US20160022820A1/en not_active Abandoned
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