RU2708238C2 - Стабильные составы тестостерона ундеканоата - Google Patents
Стабильные составы тестостерона ундеканоата Download PDFInfo
- Publication number
- RU2708238C2 RU2708238C2 RU2017101240A RU2017101240A RU2708238C2 RU 2708238 C2 RU2708238 C2 RU 2708238C2 RU 2017101240 A RU2017101240 A RU 2017101240A RU 2017101240 A RU2017101240 A RU 2017101240A RU 2708238 C2 RU2708238 C2 RU 2708238C2
- Authority
- RU
- Russia
- Prior art keywords
- composition
- water
- testosterone undecanoate
- surfactant
- propylene glycol
- Prior art date
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- 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 title abstract description 66
- 229960003604 testosterone Drugs 0.000 title abstract description 15
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 title description 7
- 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 abstract description 89
- 229960000746 testosterone undecanoate Drugs 0.000 claims abstract description 88
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 29
- 239000008389 polyethoxylated castor oil Substances 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 150000004668 long chain fatty acids Chemical class 0.000 claims abstract description 9
- 206010058359 Hypogonadism Diseases 0.000 claims abstract description 7
- GHHURQMJLARIDK-UHFFFAOYSA-N 2-hydroxypropyl octanoate Chemical compound CCCCCCCC(=O)OCC(C)O GHHURQMJLARIDK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 198
- 239000004094 surface-active agent Substances 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000002736 nonionic surfactant Substances 0.000 claims description 18
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 12
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 11
- 229940093471 ethyl oleate Drugs 0.000 claims description 11
- 150000002646 long chain fatty acid esters Chemical class 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 4
- 229920000053 polysorbate 80 Polymers 0.000 claims description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
- 229940068968 polysorbate 80 Drugs 0.000 claims description 2
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 claims 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims 1
- OVYMWJFNQQOJBU-UHFFFAOYSA-N 1-octanoyloxypropan-2-yl octanoate Chemical compound CCCCCCCC(=O)OCC(C)OC(=O)CCCCCCC OVYMWJFNQQOJBU-UHFFFAOYSA-N 0.000 claims 1
- 239000001593 sorbitan monooleate Substances 0.000 claims 1
- 235000011069 sorbitan monooleate Nutrition 0.000 claims 1
- 229940035049 sorbitan monooleate Drugs 0.000 claims 1
- 229940117972 triolein Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
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- XLMXUUQMSMKFMH-UZRURVBFSA-N 2-hydroxyethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCO XLMXUUQMSMKFMH-UZRURVBFSA-N 0.000 description 5
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 5
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000007908 nanoemulsion Substances 0.000 description 5
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007963 capsule composition Substances 0.000 description 4
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- 238000012377 drug delivery Methods 0.000 description 4
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- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- 108010004103 Chylomicrons Proteins 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
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- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
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- 229940079593 drug Drugs 0.000 description 3
- 238000002296 dynamic light scattering Methods 0.000 description 3
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 2
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- 230000006399 behavior Effects 0.000 description 2
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- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 235000004213 low-fat Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- 229920001983 poloxamer Polymers 0.000 description 2
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- 150000003077 polyols Chemical class 0.000 description 2
- 235000002316 solid fats Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- 238000005809 transesterification reaction Methods 0.000 description 2
- 238000011179 visual inspection Methods 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
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- 150000001720 carbohydrates Chemical class 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
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- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- QCTVGFNUKWXQNN-UHFFFAOYSA-N n-(2-hydroxypropyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCC(C)O QCTVGFNUKWXQNN-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- A—HUMAN NECESSITIES
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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
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- 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
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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
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dispersion Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Pregnancy & Childbirth (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14172805 | 2014-06-17 | ||
| EP14172805.5 | 2014-06-17 | ||
| PCT/EP2015/063292 WO2015193224A1 (en) | 2014-06-17 | 2015-06-15 | Stable formulations of testosterone undecanoate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2017101240A RU2017101240A (ru) | 2018-07-17 |
| RU2017101240A3 RU2017101240A3 (enExample) | 2019-02-22 |
| RU2708238C2 true RU2708238C2 (ru) | 2019-12-05 |
Family
ID=50980940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017101240A RU2708238C2 (ru) | 2014-06-17 | 2015-06-15 | Стабильные составы тестостерона ундеканоата |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9925200B2 (enExample) |
| EP (1) | EP3157505B1 (enExample) |
| JP (1) | JP6618488B2 (enExample) |
| KR (1) | KR20170020779A (enExample) |
| CN (1) | CN106456782B (enExample) |
| AU (1) | AU2015276321B2 (enExample) |
| BR (1) | BR112016028192A2 (enExample) |
| CA (1) | CA2950670A1 (enExample) |
| ES (1) | ES2749008T3 (enExample) |
| MX (1) | MX373197B (enExample) |
| RU (1) | RU2708238C2 (enExample) |
| WO (1) | WO2015193224A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110160168A1 (en) | 2009-12-31 | 2011-06-30 | Differential Drug Development Associates, Llc | Modulation of solubility, stability, absorption, metabolism, and pharmacokinetic profile of lipophilic drugs by sterols |
| ES2907284T3 (es) | 2013-03-15 | 2022-04-22 | Marius Pharmaceuticals Llc | Formulaciones de emulsión |
| MX391097B (es) | 2017-11-27 | 2025-03-21 | Umecrine Cognition Ab | FORMULACIÓN FARMACÉUTICA DE 3A-ETINIL-3ß-HIDROXIANDROSTAN-17-ONA OXIMA. |
| AU2019308326B2 (en) | 2018-07-20 | 2025-07-31 | Lipocine Inc. | Liver disease |
| US12403146B2 (en) | 2019-10-30 | 2025-09-02 | Marius Pharmaceuticals, Inc. | Preferred oral testosterone undecanoate therapy to achieve testosterone replacement treatment |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997040823A1 (en) * | 1996-04-26 | 1997-11-06 | R.P. Scherer Limited | Oral pharmaceutical compositions containing sex hormones |
| US6652880B1 (en) * | 1999-04-01 | 2003-11-25 | R.P. Scherer Technologies, Inc. | Oral pharmaceutical compositions containing long-chain triglycerides and liphophilic surfactants |
| RU2303981C2 (ru) * | 2000-11-01 | 2007-08-10 | Юнимед Фармасьютикалс, Инк. | Способ лечения эректильной дисфункции и повышения либидо у мужчин |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098802A (en) | 1975-02-18 | 1978-07-04 | Akzona Incorporated | Oral pharmaceutical preparation having androgenic activity |
| US4147783A (en) | 1974-02-28 | 1979-04-03 | Akzona Incorporated | Oral pharmaceutical preparation |
| NL189235C (nl) | 1974-02-28 | 1993-02-16 | Akzo Nv | Werkwijze voor de bereiding van een oraal toe te dienen farmaceutisch preparaat met androgene werking. |
| NL7510104A (nl) | 1975-08-27 | 1977-03-01 | Akzo Nv | Werkwijze ter bereiding van een oraal werkzaam farmaceutisch preparaat. |
| AU633959B2 (en) | 1989-08-17 | 1993-02-11 | Cortecs Limited | Pharmaceutical formulations |
| US5532002A (en) | 1989-08-17 | 1996-07-02 | Cortecs Limited | Gelatin pharmaceutical formulations |
| CN1102095A (zh) | 1993-10-30 | 1995-05-03 | 浙江医科大学 | 长效雄激素类制剂——十一酸睾丸注射液 |
| GB9405304D0 (en) | 1994-03-16 | 1994-04-27 | Scherer Ltd R P | Delivery systems for hydrophobic drugs |
| SE9700642D0 (sv) | 1997-02-24 | 1997-02-24 | Kronvall Stefan Med Ab | Medel och sätt för förebyggande och behandling av det metabola syndromet |
| PT999826E (pt) | 1997-07-29 | 2004-09-30 | Upjohn Co | Formulacao auto-emulsionante para compostos lipofilos |
| US7396526B1 (en) * | 1998-11-12 | 2008-07-08 | Johnson & Johnson Consumer Companies, Inc. | Skin care composition |
| GB9907715D0 (en) * | 1999-04-01 | 1999-05-26 | Scherer Corp R P | Pharmaceutical compositions |
| WO2000059512A1 (en) | 1999-04-01 | 2000-10-12 | Akzo Nobel N.V. | Formulation comprising testosteron undecanoate and castor oil |
| EP1817012A2 (en) * | 2004-11-24 | 2007-08-15 | Merck & Co., Inc. | Liquid and semi-solid pharmaceutical formulations for oral administration of a substituted amide |
| US8241664B2 (en) | 2005-04-15 | 2012-08-14 | Clarus Therapeutics, Inc | Pharmaceutical delivery systems for hydrophobic drugs and compositions comprising same |
| US8492369B2 (en) | 2010-04-12 | 2013-07-23 | Clarus Therapeutics Inc | Oral testosterone ester formulations and methods of treating testosterone deficiency comprising same |
| US20110160168A1 (en) * | 2009-12-31 | 2011-06-30 | 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 |
| PH12012502016A1 (en) * | 2010-04-12 | 2013-01-21 | Clarus Therapeutics Inc | Oral testosterone ester formulations and methods of treating testosterone deficiency comprising same |
| US20120135074A1 (en) | 2010-11-30 | 2012-05-31 | Chandrashekar Giliyar | High-Strength Testosterone Undecanoate Compositions |
| US9034858B2 (en) * | 2010-11-30 | 2015-05-19 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| EP4234015A3 (en) | 2013-03-15 | 2023-11-22 | Tolmar, Inc. | Methods of treating testosterone deficiency |
| WO2015100406A1 (en) | 2013-12-26 | 2015-07-02 | Clarus Therapeutics, Inc. | Use of oral pharmaceutical products combining testosterone esters with hypolipidemic agents |
-
2015
- 2015-06-15 EP EP15728552.9A patent/EP3157505B1/en active Active
- 2015-06-15 ES ES15728552T patent/ES2749008T3/es active Active
- 2015-06-15 CA CA2950670A patent/CA2950670A1/en not_active Abandoned
- 2015-06-15 WO PCT/EP2015/063292 patent/WO2015193224A1/en not_active Ceased
- 2015-06-15 BR BR112016028192A patent/BR112016028192A2/pt not_active Application Discontinuation
- 2015-06-15 KR KR1020167035025A patent/KR20170020779A/ko not_active Withdrawn
- 2015-06-15 MX MX2016016612A patent/MX373197B/es active IP Right Grant
- 2015-06-15 AU AU2015276321A patent/AU2015276321B2/en not_active Ceased
- 2015-06-15 CN CN201580032121.7A patent/CN106456782B/zh not_active Expired - Fee Related
- 2015-06-15 US US15/317,132 patent/US9925200B2/en active Active
- 2015-06-15 JP JP2016572477A patent/JP6618488B2/ja not_active Expired - Fee Related
- 2015-06-15 RU RU2017101240A patent/RU2708238C2/ru active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997040823A1 (en) * | 1996-04-26 | 1997-11-06 | R.P. Scherer Limited | Oral pharmaceutical compositions containing sex hormones |
| US6652880B1 (en) * | 1999-04-01 | 2003-11-25 | R.P. Scherer Technologies, Inc. | Oral pharmaceutical compositions containing long-chain triglycerides and liphophilic surfactants |
| RU2303981C2 (ru) * | 2000-11-01 | 2007-08-10 | Юнимед Фармасьютикалс, Инк. | Способ лечения эректильной дисфункции и повышения либидо у мужчин |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106456782B (zh) | 2020-02-18 |
| EP3157505A1 (en) | 2017-04-26 |
| RU2017101240A3 (enExample) | 2019-02-22 |
| MX373197B (es) | 2020-05-12 |
| EP3157505B1 (en) | 2019-07-24 |
| AU2015276321A1 (en) | 2016-11-10 |
| BR112016028192A2 (pt) | 2017-08-22 |
| JP2017522283A (ja) | 2017-08-10 |
| CN106456782A (zh) | 2017-02-22 |
| RU2017101240A (ru) | 2018-07-17 |
| KR20170020779A (ko) | 2017-02-24 |
| US9925200B2 (en) | 2018-03-27 |
| ES2749008T3 (es) | 2020-03-18 |
| US20170136033A1 (en) | 2017-05-18 |
| AU2015276321B2 (en) | 2019-10-24 |
| CA2950670A1 (en) | 2015-12-23 |
| WO2015193224A1 (en) | 2015-12-23 |
| MX2016016612A (es) | 2017-03-20 |
| JP6618488B2 (ja) | 2019-12-11 |
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