JP2008537960A5 - - Google Patents
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- Publication number
- JP2008537960A5 JP2008537960A5 JP2008506780A JP2008506780A JP2008537960A5 JP 2008537960 A5 JP2008537960 A5 JP 2008537960A5 JP 2008506780 A JP2008506780 A JP 2008506780A JP 2008506780 A JP2008506780 A JP 2008506780A JP 2008537960 A5 JP2008537960 A5 JP 2008537960A5
- Authority
- JP
- Japan
- Prior art keywords
- testosterone
- pharmaceutical composition
- composition according
- lipid component
- ester
- 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
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testosterone Natural products 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 27
- 150000002632 lipids Chemical class 0.000 claims 24
- 239000008194 pharmaceutical composition Substances 0.000 claims 22
- 229960003604 testosterone Drugs 0.000 claims 17
- 238000000034 method Methods 0.000 claims 14
- VOCBWIIFXDYGNZ-IXKNJLPQSA-N testosterone enanthate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCC)[C@@]1(C)CC2 VOCBWIIFXDYGNZ-IXKNJLPQSA-N 0.000 claims 10
- 229960003484 testosterone enanthate Drugs 0.000 claims 10
- 229960000746 testosterone undecanoate Drugs 0.000 claims 10
- UDSFVOAUHKGBEK-CNQKSJKFSA-N testosterone undecanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCCCCCC)[C@@]1(C)CC2 UDSFVOAUHKGBEK-CNQKSJKFSA-N 0.000 claims 10
- 239000004094 surface-active agent Substances 0.000 claims 6
- -1 testosterone ester Chemical class 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 4
- 235000006679 Mentha X verticillata Nutrition 0.000 claims 4
- 235000002899 Mentha suaveolens Nutrition 0.000 claims 4
- 235000001636 Mentha x rotundifolia Nutrition 0.000 claims 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 4
- 239000005642 Oleic acid Substances 0.000 claims 4
- 235000021324 borage oil Nutrition 0.000 claims 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 4
- 150000002646 long chain fatty acid esters Chemical class 0.000 claims 4
- 235000019198 oils Nutrition 0.000 claims 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 4
- 229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 210000002966 serum Anatomy 0.000 claims 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class 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
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims 2
- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 claims 2
- 239000003963 antioxidant agent Substances 0.000 claims 2
- 230000003078 antioxidant effect Effects 0.000 claims 2
- 235000006708 antioxidants Nutrition 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 239000000583 progesterone congener Substances 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- JMNCUXPHXKHBPY-UHFFFAOYSA-N 1,3-dichloropropan-2-yl carbamate Chemical compound NC(=O)OC(CCl)CCl JMNCUXPHXKHBPY-UHFFFAOYSA-N 0.000 claims 1
- ORGPUALGNXTPAW-UHFFFAOYSA-N 2,6-dichloro-n-(1-cyanocycloheptyl)benzamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1(C#N)CCCCCC1 ORGPUALGNXTPAW-UHFFFAOYSA-N 0.000 claims 1
- 102100033875 3-oxo-5-alpha-steroid 4-dehydrogenase 2 Human genes 0.000 claims 1
- 206010002261 Androgen deficiency Diseases 0.000 claims 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims 1
- 102000006771 Gonadotropins Human genes 0.000 claims 1
- 108010086677 Gonadotropins Proteins 0.000 claims 1
- 101000640851 Homo sapiens 3-oxo-5-alpha-steroid 4-dehydrogenase 2 Proteins 0.000 claims 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims 1
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 claims 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 claims 1
- LBERVHLCXUMDOT-MPZZESAYSA-N Testosterone decanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCCCCC)[C@@]1(C)CC2 LBERVHLCXUMDOT-MPZZESAYSA-N 0.000 claims 1
- FHJSGESOWQSDBH-MXFPRFFXSA-N [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] octadecanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@@]1(C)CC2 FHJSGESOWQSDBH-MXFPRFFXSA-N 0.000 claims 1
- KTROUBQZLCALOQ-DQUDHZTESA-N [(8r,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] dodecanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCCCCCCC)[C@@]1(C)CC2 KTROUBQZLCALOQ-DQUDHZTESA-N 0.000 claims 1
- OKFBXYQPCPWWRP-SHDAAXGTSA-N [(8r,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] hexadecanoate Chemical group C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCCCCCCCCCCC)[C@@]1(C)CC2 OKFBXYQPCPWWRP-SHDAAXGTSA-N 0.000 claims 1
- WIGTZVOQGIFMAV-BKWLFHPQSA-N [(8r,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] hexanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCC)[C@@]1(C)CC2 WIGTZVOQGIFMAV-BKWLFHPQSA-N 0.000 claims 1
- MOFKIKISDIQWLD-NQPKZJONSA-N [(8r,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] tridecanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCCCCCCCC)[C@@]1(C)CC2 MOFKIKISDIQWLD-NQPKZJONSA-N 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 claims 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 1
- 230000002950 deficient Effects 0.000 claims 1
- 229960004199 dutasteride Drugs 0.000 claims 1
- JWJOTENAMICLJG-QWBYCMEYSA-N dutasteride Chemical compound O=C([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)N[C@@H]4CC3)C)CC[C@@]21C)NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F JWJOTENAMICLJG-QWBYCMEYSA-N 0.000 claims 1
- 230000003028 elevating effect Effects 0.000 claims 1
- 229960004039 finasteride Drugs 0.000 claims 1
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 claims 1
- 239000007903 gelatin capsule Substances 0.000 claims 1
- FETSQPAGYOVAQU-UHFFFAOYSA-N glyceryl palmitostearate Chemical group OCC(O)CO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O FETSQPAGYOVAQU-UHFFFAOYSA-N 0.000 claims 1
- 229940046813 glyceryl palmitostearate Drugs 0.000 claims 1
- 239000002622 gonadotropin Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 150000004668 long chain fatty acids Chemical group 0.000 claims 1
- 150000002711 medium chain fatty acid esters Chemical class 0.000 claims 1
- 150000004667 medium chain fatty acids Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 229940105132 myristate Drugs 0.000 claims 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 claims 1
- 235000021313 oleic acid Nutrition 0.000 claims 1
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical group C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-M pentadecanoate Chemical compound CCCCCCCCCCCCCCC([O-])=O WQEPLUUGTLDZJY-UHFFFAOYSA-M 0.000 claims 1
- 239000008389 polyethoxylated castor oil Substances 0.000 claims 1
- 235000010388 propyl gallate Nutrition 0.000 claims 1
- 239000000473 propyl gallate Substances 0.000 claims 1
- 229940075579 propyl gallate Drugs 0.000 claims 1
- 235000019172 retinyl palmitate Nutrition 0.000 claims 1
- 229940108325 retinyl palmitate Drugs 0.000 claims 1
- 239000011769 retinyl palmitate Substances 0.000 claims 1
- 230000003381 solubilizing effect Effects 0.000 claims 1
- 229950003429 sorbitan palmitate Drugs 0.000 claims 1
- 238000013268 sustained release Methods 0.000 claims 1
- 239000012730 sustained-release form Substances 0.000 claims 1
- 229960003410 testosterone decanoate Drugs 0.000 claims 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims 1
- 235000010384 tocopherol Nutrition 0.000 claims 1
- 229960001295 tocopherol Drugs 0.000 claims 1
- 229930003799 tocopherol Natural products 0.000 claims 1
- 239000011732 tocopherol Substances 0.000 claims 1
- 229940042585 tocopherol acetate Drugs 0.000 claims 1
- 125000002640 tocopherol group Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67145405P | 2005-04-15 | 2005-04-15 | |
| US60/671,454 | 2005-04-15 | ||
| US72197105P | 2005-09-30 | 2005-09-30 | |
| US60/721,971 | 2005-09-30 | ||
| PCT/US2006/014207 WO2006113505A2 (en) | 2005-04-15 | 2006-04-14 | Pharmaceutical delivery systems for hydrophobic drugs and compositions comprising same |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013026993A Division JP5778705B2 (ja) | 2005-04-15 | 2013-02-14 | 疎水性薬物のドラッグデリバリーシステムとその組成物 |
| JP2015216911A Division JP6251713B2 (ja) | 2005-04-15 | 2015-11-04 | 疎水性薬物のドラッグデリバリーシステムとその組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008537960A JP2008537960A (ja) | 2008-10-02 |
| JP2008537960A5 true JP2008537960A5 (enExample) | 2009-04-23 |
| JP5887044B2 JP5887044B2 (ja) | 2016-03-16 |
Family
ID=37115755
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008506780A Active JP5887044B2 (ja) | 2005-04-15 | 2006-04-14 | 疎水性薬物のドラッグデリバリーシステムとその組成物 |
| JP2013026993A Active JP5778705B2 (ja) | 2005-04-15 | 2013-02-14 | 疎水性薬物のドラッグデリバリーシステムとその組成物 |
| JP2015216911A Active JP6251713B2 (ja) | 2005-04-15 | 2015-11-04 | 疎水性薬物のドラッグデリバリーシステムとその組成物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013026993A Active JP5778705B2 (ja) | 2005-04-15 | 2013-02-14 | 疎水性薬物のドラッグデリバリーシステムとその組成物 |
| JP2015216911A Active JP6251713B2 (ja) | 2005-04-15 | 2015-11-04 | 疎水性薬物のドラッグデリバリーシステムとその組成物 |
Country Status (14)
| Country | Link |
|---|---|
| US (18) | US8241664B2 (enExample) |
| EP (3) | EP2985026B1 (enExample) |
| JP (3) | JP5887044B2 (enExample) |
| KR (3) | KR20080009201A (enExample) |
| AU (2) | AU2006236564B2 (enExample) |
| BR (1) | BRPI0607549A2 (enExample) |
| CA (1) | CA2604943C (enExample) |
| DK (1) | DK2985026T3 (enExample) |
| ES (1) | ES2930658T3 (enExample) |
| HU (1) | HUE061300T2 (enExample) |
| PL (1) | PL2985026T3 (enExample) |
| PT (1) | PT2985026T (enExample) |
| RU (2) | RU2623206C2 (enExample) |
| WO (1) | WO2006113505A2 (enExample) |
Families Citing this family (96)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6503894B1 (en) | 2000-08-30 | 2003-01-07 | Unimed Pharmaceuticals, Inc. | Pharmaceutical composition and method for treating hypogonadism |
| US8883769B2 (en) | 2003-06-18 | 2014-11-11 | White Mountain Pharma, Inc. | Methods for the treatment of fibromyalgia and chronic fatigue syndrome |
| US20040259852A1 (en) | 2003-06-18 | 2004-12-23 | White Hillary D. | Trandsdermal compositions and methods for treatment of fibromyalgia and chronic fatigue syndrome |
| RU2623206C2 (ru) | 2005-04-15 | 2017-06-22 | Кларус Терапьютикс, Инк. | Фармацевтические системы доставки для гидрофобных лекарственных средств и композиций, их содержащих |
| US8492369B2 (en) | 2010-04-12 | 2013-07-23 | Clarus Therapeutics Inc | Oral testosterone ester formulations and methods of treating testosterone deficiency comprising same |
| JP5584415B2 (ja) | 2005-10-12 | 2014-09-03 | ユニメッド・ファーマシューティカルズ・エルエルシー | 改良したテストステロンゲル製剤及び使用の方法 |
| SI1993559T1 (sl) | 2006-02-03 | 2017-01-31 | Opko Renal, Llc | Zdravljenje nezadostnosti in pomanjkanja vitamina D s 25-hidroksivitaminon D2 in 25-hidroksivitaminom D3 |
| PT2679228T (pt) | 2006-06-21 | 2018-04-16 | Opko Ireland Global Holdings Ltd | Terapia utilizando um agente de repleção de vitamina d e um agente de substituição hormonal de vitamina d |
| KR101959952B1 (ko) | 2007-04-25 | 2019-03-19 | 사이토크로마 인코포레이티드 | 비타민 ｄ 화합물과 밀랍성 담체를 포함하는 경구 조절성 방출 조성물 |
| CN104257667B (zh) | 2007-04-25 | 2019-06-04 | 欧普科Ip 控股Ii 有限公司 | 治疗维生素d不足和缺乏、继发性甲状旁腺功能亢进症和维生素d-响应疾病的方法和组合物 |
| EP3225243B1 (en) | 2007-04-25 | 2025-09-03 | Opko Renal, LLC | Method of safely and effectively treating and preventing secondary hyperparathyroidism in chronic kidney disease |
| WO2008144888A1 (en) | 2007-05-25 | 2008-12-04 | The University Of British Columbia | Formulations for the oral administration of therapeutic agents and related methods |
| EP2200613B1 (en) | 2007-09-21 | 2018-09-05 | The Johns Hopkins University | Phenazine derivatives and uses thereof |
| CN106853250A (zh) | 2008-04-02 | 2017-06-16 | 赛特克罗公司 | 用于维生素d缺乏症和相关障碍的方法、组合物、用途和试剂盒 |
| GB0807605D0 (en) | 2008-04-28 | 2008-06-04 | Diurnal Ltd | Lipid composition |
| US11304960B2 (en) | 2009-01-08 | 2022-04-19 | Chandrashekar Giliyar | Steroidal compositions |
| US20140288039A1 (en) * | 2009-01-08 | 2014-09-25 | Lipocine Inc. | Lipobalanced long chain testosterone prodrugs for oral delivery |
| US20130225544A1 (en) * | 2009-01-08 | 2013-08-29 | Lipocine Inc. | Lipobalanced long chain testosterone esters for oral delivery |
| WO2011050457A1 (en) | 2009-10-26 | 2011-05-05 | The University Of British Columbia | Stabilized formulation for oral administration of therapeutic agents and related methods |
| CA2779005A1 (en) * | 2009-11-09 | 2011-05-12 | Capsugel Belgium Nv | Delivery carrier |
| WO2011087867A1 (en) * | 2009-12-22 | 2011-07-21 | Talima Therapeutics, Inc. | Antifungal therapy |
| EP2682111A1 (en) * | 2009-12-31 | 2014-01-08 | Differential Drug Development Associates LLC | Modulation of solubility, stability, absorption, metabolism, and pharmacokinetic profile of lipophilic drugs by sterols |
| US20130303495A1 (en) * | 2009-12-31 | 2013-11-14 | Sov Therapeutics | Emulsion formulations |
| ES2783980T3 (es) | 2010-03-29 | 2020-09-21 | Opko Ireland Global Holdings Ltd | Métodos y composiciones para la reducción de niveles de paratiroides |
| MX2012011952A (es) * | 2010-04-12 | 2013-02-07 | Clarus Therapeutics Inc | Formulaciones orales de ester de testosterona y metodos para el tratamiento de la deficiencia de testosterona que comprende estos. |
| AU2014265072B2 (en) * | 2010-04-12 | 2016-09-15 | Besins Healthcare Luxembourg S.A.R.L. | Oral testosterone ester formulations and methods of treating testoterone deficiency comprising same |
| RU2642244C2 (ru) * | 2010-04-12 | 2018-01-24 | Кларус Терапеутикс, Инк. | Оральные фармацевтические композиции сложных эфиров тестостерона и способы лечения недостатка тестостерона с их использованием |
| EP2640398A4 (en) | 2010-11-18 | 2014-05-14 | White Mountain Pharma Inc | METHOD FOR TREATING CHRONIC OR BZW. NON-RELIABLE PAIN AND / OR INCREASE OF PATIENT PAIN THRESHOLD AND PHARMACEUTICAL COMPOSITION FOR USE THEREOF |
| US20180153904A1 (en) | 2010-11-30 | 2018-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US9358241B2 (en) * | 2010-11-30 | 2016-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US9034858B2 (en) | 2010-11-30 | 2015-05-19 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US20120135074A1 (en) * | 2010-11-30 | 2012-05-31 | Chandrashekar Giliyar | High-Strength Testosterone Undecanoate Compositions |
| US20120148675A1 (en) * | 2010-12-10 | 2012-06-14 | Basawaraj Chickmath | Testosterone undecanoate compositions |
| WO2012104240A2 (de) * | 2011-01-31 | 2012-08-09 | LUCOLAS-M.D. Ltd | Kosmetische verwendung |
| US11850451B2 (en) | 2011-01-31 | 2023-12-26 | Lucolas-M.D. Ltd. | Cosmetic compositions and methods for improving skin conditions |
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