ES2337069T3 - Composiciones quimicamente estables de 4-hidroxitamoxifeno. - Google Patents
Composiciones quimicamente estables de 4-hidroxitamoxifeno. Download PDFInfo
- Publication number
- ES2337069T3 ES2337069T3 ES05735277T ES05735277T ES2337069T3 ES 2337069 T3 ES2337069 T3 ES 2337069T3 ES 05735277 T ES05735277 T ES 05735277T ES 05735277 T ES05735277 T ES 05735277T ES 2337069 T3 ES2337069 T3 ES 2337069T3
- Authority
- ES
- Spain
- Prior art keywords
- hydroxy tamoxifen
- approximately
- pharmaceutical composition
- isomeric
- tamoxifen
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 61
- DODQJNMQWMSYGS-QPLCGJKRSA-N 4-[(z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-phenylbut-1-en-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 DODQJNMQWMSYGS-QPLCGJKRSA-N 0.000 claims abstract description 132
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003623 enhancer Substances 0.000 claims description 10
- 230000035515 penetration Effects 0.000 claims description 9
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229940105132 myristate Drugs 0.000 claims description 4
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 239000003961 penetration enhancing agent Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- 238000006317 isomerization reaction Methods 0.000 description 36
- 230000008569 process Effects 0.000 description 20
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 238000009472 formulation Methods 0.000 description 14
- 239000008135 aqueous vehicle Substances 0.000 description 13
- 210000000481 breast Anatomy 0.000 description 13
- 229940079593 drug Drugs 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 210000001519 tissue Anatomy 0.000 description 12
- 208000026310 Breast neoplasm Diseases 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 229960001603 tamoxifen Drugs 0.000 description 9
- 239000007853 buffer solution Substances 0.000 description 8
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 8
- 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 description 7
- 206010006187 Breast cancer Diseases 0.000 description 7
- 230000001476 alcoholic effect Effects 0.000 description 7
- 229960005309 estradiol Drugs 0.000 description 7
- 229930182833 estradiol Natural products 0.000 description 7
- 102000015694 estrogen receptors Human genes 0.000 description 7
- 108010038795 estrogen receptors Proteins 0.000 description 7
- 230000002441 reversible effect Effects 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- TXUZVZSFRXZGTL-QPLCGJKRSA-N afimoxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=C(O)C=C1 TXUZVZSFRXZGTL-QPLCGJKRSA-N 0.000 description 6
- 239000008055 phosphate buffer solution Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 206010016654 Fibrosis Diseases 0.000 description 5
- 230000004761 fibrosis Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
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- 239000003981 vehicle Substances 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 229940011871 estrogen Drugs 0.000 description 4
- 239000000262 estrogen Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000002687 nonaqueous vehicle Substances 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- TXUZVZSFRXZGTL-OCEACIFDSA-N 4-[(e)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)\C1=CC=C(O)C=C1 TXUZVZSFRXZGTL-OCEACIFDSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010006298 Breast pain Diseases 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 208000006662 Mastodynia Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
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- 229930195729 fatty acid Natural products 0.000 description 3
- 201000000079 gynecomastia Diseases 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000036470 plasma concentration Effects 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 210000000434 stratum corneum Anatomy 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 108010011485 Aspartame Proteins 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 125000002009 alkene group Chemical group 0.000 description 2
- 239000000605 aspartame Substances 0.000 description 2
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 2
- 229960003438 aspartame Drugs 0.000 description 2
- 235000010357 aspartame Nutrition 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000328 estrogen antagonist Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- -1 fatty acid esters Chemical class 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000012088 reference solution Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 101100111810 Aquifex aeolicus (strain VF5) suhB gene Proteins 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010014733 Endometrial cancer Diseases 0.000 description 1
- 206010014759 Endometrial neoplasm Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000033830 Hot Flashes Diseases 0.000 description 1
- 206010060800 Hot flush Diseases 0.000 description 1
- 101150018873 IMP1 gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 229940061607 dibasic sodium phosphate Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 201000006828 endometrial hyperplasia Diseases 0.000 description 1
- 208000016018 endometrial polyp Diseases 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 108020004067 estrogen-related receptors Proteins 0.000 description 1
- 210000001723 extracellular space Anatomy 0.000 description 1
- 230000007684 eye toxicity Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 210000003780 hair follicle Anatomy 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 230000010224 hepatic metabolism Effects 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007056 liver toxicity Effects 0.000 description 1
- 238000009607 mammography Methods 0.000 description 1
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000327 ocular toxicity Toxicity 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 239000000333 selective estrogen receptor modulator Substances 0.000 description 1
- 229940095743 selective estrogen receptor modulator Drugs 0.000 description 1
- 230000037067 skin hydration Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 206010046811 uterine polyp Diseases 0.000 description 1
- 206010046901 vaginal discharge Diseases 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
-
- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- 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
- A61K47/02—Inorganic compounds
-
- 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
- A61K47/06—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
-
- 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
- A61K47/06—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
- A61K47/38—Cellulose; Derivatives thereof
-
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US805530 | 1985-12-06 | ||
| EP04290762 | 2004-03-22 | ||
| US10/805,530 US20050208139A1 (en) | 2004-03-22 | 2004-03-22 | Chemically stable compositions of 4-hydroxy tamoxifen |
| EP04290762A EP1579857A1 (en) | 2004-03-22 | 2004-03-22 | Chemically stable compositions of 4-hydroxy tamoxifen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2337069T3 true ES2337069T3 (es) | 2010-04-20 |
Family
ID=34854723
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES05735277T Expired - Lifetime ES2337069T3 (es) | 2004-03-22 | 2005-03-18 | Composiciones quimicamente estables de 4-hidroxitamoxifeno. |
| ES09175781.5T Expired - Lifetime ES2517894T3 (es) | 2004-03-22 | 2005-03-18 | Composiciones químicamente estables de 4-hidroxi tamoxifen |
| ES10180921T Expired - Lifetime ES2402921T3 (es) | 2004-03-22 | 2005-03-18 | Composiciones químicamente estables de 4-hidroxi-tamoxifeno y sus aplicaciones terapéuticas |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09175781.5T Expired - Lifetime ES2517894T3 (es) | 2004-03-22 | 2005-03-18 | Composiciones químicamente estables de 4-hidroxi tamoxifen |
| ES10180921T Expired - Lifetime ES2402921T3 (es) | 2004-03-22 | 2005-03-18 | Composiciones químicamente estables de 4-hidroxi-tamoxifeno y sus aplicaciones terapéuticas |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20050208139A1 (enExample) |
| EP (4) | EP1579857A1 (enExample) |
| JP (1) | JP5489407B2 (enExample) |
| CN (1) | CN101080222B (enExample) |
| AR (1) | AR048587A1 (enExample) |
| AT (1) | ATE453387T1 (enExample) |
| AU (1) | AU2005227073B2 (enExample) |
| CA (1) | CA2557806C (enExample) |
| DE (1) | DE602005018613D1 (enExample) |
| DK (1) | DK1727532T3 (enExample) |
| ES (3) | ES2337069T3 (enExample) |
| IL (2) | IL177778A (enExample) |
| MX (1) | MXPA06010928A (enExample) |
| NO (1) | NO337298B1 (enExample) |
| NZ (1) | NZ549664A (enExample) |
| PL (1) | PL1727532T3 (enExample) |
| PT (1) | PT1727532E (enExample) |
| RU (1) | RU2389483C2 (enExample) |
| TW (1) | TWI401078B (enExample) |
| WO (1) | WO2005092310A2 (enExample) |
| ZA (1) | ZA200607291B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004054557A2 (en) * | 2002-12-18 | 2004-07-01 | Laboratoires Besins International | Treatment of mastalgia with 4-hydroxy tamoxifen |
| JP4684655B2 (ja) * | 2002-12-18 | 2011-05-18 | ラボラトワール ブザン アンテルナスィヨナル | ４−ヒドロキシタモキシフェンによる乳房密度低下 |
| CA2519980C (en) * | 2003-04-01 | 2012-04-10 | Laboratoires Besins International | Prevention and treatment of breast cancer with 4-hydroxy tamoxifen |
| US7767717B2 (en) | 2003-06-09 | 2010-08-03 | Ascend Therapeutics, Inc. | Treatment and prevention of excessive scarring with 4-hydroxy tamoxifen |
| US7968532B2 (en) | 2003-12-15 | 2011-06-28 | Besins Healthcare Luxembourg | Treatment of gynecomastia with 4-hydroxy tamoxifen |
| US7507769B2 (en) * | 2004-03-22 | 2009-03-24 | Laboratoires Besins International | Treatment and prevention of benign breast disease with 4-hydroxy tamoxifen |
| EP1799201B1 (en) * | 2004-10-14 | 2008-11-26 | Laboratoires Besins International | 4-hydroxy tamoxifen gel formulations |
| EP1647271A1 (en) * | 2004-10-14 | 2006-04-19 | Laboratoires Besins International | 4-Hydroxy tamoxifen gel formulations |
| WO2011046596A2 (en) * | 2009-10-13 | 2011-04-21 | Duquesne University Of The Holy Spirit, A Nonprofit Corporation Organized Under The Laws Of The Commonwealth Of Pennsylvania | Anti-cancer tamoxifen-melatonin hybrid ligand |
| CA2878866C (en) * | 2011-07-14 | 2021-02-23 | Able Cerebral, Llc | A composition, device and method for delayed and sustained release of brain energy molecules |
| US20230026978A1 (en) * | 2021-07-07 | 2023-01-26 | Ohio State Innovation Foundation | Photoisomerized compositions of anthocyanins and methods of making and use thereof |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2558373B1 (fr) * | 1984-01-20 | 1987-07-03 | Mauvais Jarvis Pierre | Medicament antioestrogene a base de 4-hydroxytamoxifene pour administration percutanee |
| US5475851A (en) * | 1986-04-14 | 1995-12-12 | National Instruments Corporation | Method and apparatus for improved local and global variable capabilities in a graphical data flow program |
| US5002938A (en) * | 1988-03-21 | 1991-03-26 | Bristol-Myers Squibb Company | Antifungal gel formulations |
| CA2032695A1 (en) | 1989-12-20 | 1991-06-21 | Hiroshi Akimoto | Condensed heterocyclic compounds, their production and use |
| DE4407742C1 (de) * | 1994-03-08 | 1995-06-22 | Hexal Pharma Gmbh | Transdermales System in Form eines Pflasters mit einem Tamoxifen-Derivat |
| US6160549A (en) * | 1994-07-29 | 2000-12-12 | Oracle Corporation | Method and apparatus for generating reports using declarative tools |
| DE4435784C2 (de) * | 1994-10-06 | 1998-10-29 | Heraeus Electro Nite Int | Elektrisch beheizbarer Starterkat |
| US5777621A (en) * | 1994-12-22 | 1998-07-07 | Apple Computer, Inc. | Quality control mechanism for three-dimensional graphics rendering |
| AU725286B2 (en) * | 1996-01-20 | 2000-10-12 | Bradford University | Tamoxifen and analogues thereof |
| ES2156361T5 (es) * | 1996-03-29 | 2012-12-26 | Keyvest Gmbh | Cosmético o bien composición cosmética para el alisado y la tersura de la piel en el caso de tejido adiposo afectado, en especial en el caso de la "celulitis" |
| US6083996A (en) * | 1997-11-05 | 2000-07-04 | Nexmed Holdings, Inc. | Topical compositions for NSAI drug delivery |
| EP1043986B1 (en) * | 1997-12-23 | 2003-04-16 | Hexal Ag | Mixture and pharmaceutical composition comprising z-4-hydroxytamoxifen and cyclodextrin |
| JP2000038335A (ja) * | 1998-07-22 | 2000-02-08 | Kanebo Ltd | 皮膚化粧料 |
| AU6890800A (en) | 1999-08-23 | 2001-03-19 | Eli Lilly And Company | A novel crystalline form of disodium n-[4-[2-(2-amino-4,7-dihydro-4-oxo-3h-pyrrolo[2,3-D]- pyrimidin-5-yl)ethyl]benzoyl]-l-glutamic acid salt and processes therefor |
| DE10033853A1 (de) * | 2000-07-12 | 2002-01-31 | Hexal Ag | Transdermales therapeutisches System mit hochdispersem Siliziumdioxid |
| US20040198706A1 (en) * | 2003-03-11 | 2004-10-07 | Carrara Dario Norberto R. | Methods and formulations for transdermal or transmucosal application of active agents |
| US6503894B1 (en) * | 2000-08-30 | 2003-01-07 | Unimed Pharmaceuticals, Inc. | Pharmaceutical composition and method for treating hypogonadism |
| US20030175329A1 (en) * | 2001-10-04 | 2003-09-18 | Cellegy Pharmaceuticals, Inc. | Semisolid topical hormonal compositions and methods for treatment |
| PT1317921E (pt) * | 2001-12-07 | 2009-11-06 | Besins Mfg Belgium | Composição farmacêutica sob a forma de gel ou de solução à base de di-hidrotestosterona, seu processo de preparação e suas utilizações |
| US6695171B2 (en) * | 2002-02-12 | 2004-02-24 | Seaquistperfect Dispensing Foreign, Inc. | Pump dispenser |
| JP4684655B2 (ja) * | 2002-12-18 | 2011-05-18 | ラボラトワール ブザン アンテルナスィヨナル | ４−ヒドロキシタモキシフェンによる乳房密度低下 |
| WO2004054557A2 (en) * | 2002-12-18 | 2004-07-01 | Laboratoires Besins International | Treatment of mastalgia with 4-hydroxy tamoxifen |
| CA2519980C (en) * | 2003-04-01 | 2012-04-10 | Laboratoires Besins International | Prevention and treatment of breast cancer with 4-hydroxy tamoxifen |
| US7767717B2 (en) * | 2003-06-09 | 2010-08-03 | Ascend Therapeutics, Inc. | Treatment and prevention of excessive scarring with 4-hydroxy tamoxifen |
| PL1694319T3 (pl) * | 2003-12-15 | 2009-01-30 | Besins Healthcare Lu Sarl | Zastosowanie 4-hydroksytamoksyfenu do wytwarzania leku do leczenia ginekomastii |
| US7968532B2 (en) * | 2003-12-15 | 2011-06-28 | Besins Healthcare Luxembourg | Treatment of gynecomastia with 4-hydroxy tamoxifen |
| US7507769B2 (en) * | 2004-03-22 | 2009-03-24 | Laboratoires Besins International | Treatment and prevention of benign breast disease with 4-hydroxy tamoxifen |
| EP1647271A1 (en) * | 2004-10-14 | 2006-04-19 | Laboratoires Besins International | 4-Hydroxy tamoxifen gel formulations |
-
2004
- 2004-03-22 EP EP04290762A patent/EP1579857A1/en not_active Withdrawn
- 2004-03-22 US US10/805,530 patent/US20050208139A1/en not_active Abandoned
-
2005
- 2005-03-18 DE DE602005018613T patent/DE602005018613D1/de not_active Expired - Lifetime
- 2005-03-18 NZ NZ549664A patent/NZ549664A/en not_active IP Right Cessation
- 2005-03-18 EP EP09175781.5A patent/EP2147670B1/en not_active Expired - Lifetime
- 2005-03-18 PL PL05735277T patent/PL1727532T3/pl unknown
- 2005-03-18 MX MXPA06010928A patent/MXPA06010928A/es active IP Right Grant
- 2005-03-18 CN CN200580009171XA patent/CN101080222B/zh not_active Expired - Lifetime
- 2005-03-18 ES ES05735277T patent/ES2337069T3/es not_active Expired - Lifetime
- 2005-03-18 WO PCT/EP2005/003455 patent/WO2005092310A2/en not_active Ceased
- 2005-03-18 DK DK05735277.5T patent/DK1727532T3/da active
- 2005-03-18 AU AU2005227073A patent/AU2005227073B2/en not_active Expired
- 2005-03-18 RU RU2006137282/15A patent/RU2389483C2/ru active
- 2005-03-18 ES ES09175781.5T patent/ES2517894T3/es not_active Expired - Lifetime
- 2005-03-18 EP EP10180921A patent/EP2269599B1/en not_active Expired - Lifetime
- 2005-03-18 AT AT05735277T patent/ATE453387T1/de active
- 2005-03-18 JP JP2007504378A patent/JP5489407B2/ja not_active Expired - Lifetime
- 2005-03-18 EP EP05735277A patent/EP1727532B1/en not_active Expired - Lifetime
- 2005-03-18 ES ES10180921T patent/ES2402921T3/es not_active Expired - Lifetime
- 2005-03-18 CA CA2557806A patent/CA2557806C/en not_active Expired - Lifetime
- 2005-03-18 PT PT05735277T patent/PT1727532E/pt unknown
- 2005-03-21 TW TW094108588A patent/TWI401078B/zh not_active IP Right Cessation
- 2005-03-22 AR ARP050101125A patent/AR048587A1/es unknown
-
2006
- 2006-08-30 IL IL177778A patent/IL177778A/en active IP Right Grant
- 2006-08-31 ZA ZA2006/07291A patent/ZA200607291B/en unknown
- 2006-10-20 NO NO20064765A patent/NO337298B1/no unknown
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2011
- 2011-10-25 IL IL215897A patent/IL215897A/en active IP Right Grant
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