NO333805B1 - Anvendelse av 4-hydroxy tamoxifen for fremstilling av et medikament, og farmasoytiske sammensetninger - Google Patents
Anvendelse av 4-hydroxy tamoxifen for fremstilling av et medikament, og farmasoytiske sammensetninger Download PDFInfo
- Publication number
- NO333805B1 NO333805B1 NO20054526A NO20054526A NO333805B1 NO 333805 B1 NO333805 B1 NO 333805B1 NO 20054526 A NO20054526 A NO 20054526A NO 20054526 A NO20054526 A NO 20054526A NO 333805 B1 NO333805 B1 NO 333805B1
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy tamoxifen
- tamoxifen
- weight
- breast
- composition
- Prior art date
Links
- 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 title claims abstract description 143
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
- 229940079593 drug Drugs 0.000 title claims description 25
- 239000003814 drug Substances 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 6
- 210000000481 breast Anatomy 0.000 claims abstract description 53
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 43
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 43
- 238000011282 treatment Methods 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 40
- 102000015694 estrogen receptors Human genes 0.000 claims description 24
- 108010038795 estrogen receptors Proteins 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000003349 gelling agent Substances 0.000 claims description 14
- 235000019441 ethanol Nutrition 0.000 claims description 13
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 12
- 239000008365 aqueous carrier Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 230000003472 neutralizing effect Effects 0.000 claims description 10
- 239000003961 penetration enhancing agent Substances 0.000 claims description 9
- -1 fatty acid ester Chemical class 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 5
- 239000001913 cellulose Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 4
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 4
- 239000008366 buffered solution Substances 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- 239000002674 ointment Substances 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 2
- 229960000281 trometamol Drugs 0.000 claims description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 239000011505 plaster Substances 0.000 claims 1
- 239000004584 polyacrylic acid Substances 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 38
- 230000000694 effects Effects 0.000 abstract description 22
- 230000035755 proliferation Effects 0.000 abstract description 14
- 238000000034 method Methods 0.000 abstract description 12
- 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 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 230000001733 anti-osteogenic effect Effects 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- 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 107
- 210000001519 tissue Anatomy 0.000 description 62
- 229960001603 tamoxifen Drugs 0.000 description 51
- 239000000499 gel Substances 0.000 description 47
- 238000009472 formulation Methods 0.000 description 20
- 230000036470 plasma concentration Effects 0.000 description 19
- 238000001356 surgical procedure Methods 0.000 description 17
- 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 description 14
- 210000004369 blood Anatomy 0.000 description 14
- 239000008280 blood Substances 0.000 description 14
- 108050006400 Cyclin Proteins 0.000 description 13
- 102000009339 Proliferating Cell Nuclear Antigen Human genes 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- 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 12
- 229940011871 estrogen Drugs 0.000 description 12
- 239000000262 estrogen Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 229930182833 estradiol Natural products 0.000 description 11
- 229960005309 estradiol Drugs 0.000 description 11
- 210000003491 skin Anatomy 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 9
- 230000001965 increasing effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000003623 enhancer Substances 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 241000282412 Homo Species 0.000 description 7
- 230000027758 ovulation cycle Effects 0.000 description 7
- 230000035515 penetration Effects 0.000 description 7
- 239000000186 progesterone Substances 0.000 description 7
- 229960003387 progesterone Drugs 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000009885 systemic effect Effects 0.000 description 6
- 102000009875 Ki-67 Antigen Human genes 0.000 description 5
- 108010020437 Ki-67 Antigen Proteins 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000001574 biopsy Methods 0.000 description 5
- 231100000673 dose–response relationship Toxicity 0.000 description 5
- 238000012744 immunostaining Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 description 4
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 description 4
- 102000009151 Luteinizing Hormone Human genes 0.000 description 4
- 108010073521 Luteinizing Hormone Proteins 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000000328 estrogen antagonist Substances 0.000 description 4
- 229940028334 follicle stimulating hormone Drugs 0.000 description 4
- 230000002055 immunohistochemical effect Effects 0.000 description 4
- 238000002372 labelling Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229940040129 luteinizing hormone Drugs 0.000 description 4
- 230000004060 metabolic process Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 238000002657 hormone replacement therapy Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 239000002207 metabolite Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 102000003998 progesterone receptors Human genes 0.000 description 3
- 108090000468 progesterone receptors Proteins 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- 238000003127 radioimmunoassay Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 210000000434 stratum corneum Anatomy 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- MHJBZVSGOZTKRH-IZHYLOQSSA-N 4-Hydroxy-N-desmethyltamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCNC)=CC=1)/C1=CC=C(O)C=C1 MHJBZVSGOZTKRH-IZHYLOQSSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- 201000000736 Amenorrhea Diseases 0.000 description 2
- 206010001928 Amenorrhoea Diseases 0.000 description 2
- 102000004411 Antithrombin III Human genes 0.000 description 2
- 108090000935 Antithrombin III Proteins 0.000 description 2
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 102100025064 Cellular tumor antigen p53 Human genes 0.000 description 2
- 102100022183 E3 ubiquitin-protein ligase MIB1 Human genes 0.000 description 2
- 102000008946 Fibrinogen Human genes 0.000 description 2
- 108010049003 Fibrinogen Proteins 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 102000015779 HDL Lipoproteins Human genes 0.000 description 2
- 108010010234 HDL Lipoproteins Proteins 0.000 description 2
- 101000973503 Homo sapiens E3 ubiquitin-protein ligase MIB1 Proteins 0.000 description 2
- 206010060800 Hot flush Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 102000003929 Transaminases Human genes 0.000 description 2
- 108090000340 Transaminases Proteins 0.000 description 2
- 206010046914 Vaginal infection Diseases 0.000 description 2
- 201000008100 Vaginitis Diseases 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 231100000540 amenorrhea Toxicity 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- 229940046836 anti-estrogen Drugs 0.000 description 2
- 230000001833 anti-estrogenic effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 229960005348 antithrombin iii Drugs 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000013039 cover film Substances 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 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
- 239000000284 extract Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 229940012952 fibrinogen Drugs 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 238000000670 ligand binding assay Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 150000002634 lipophilic molecules Chemical class 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 210000001165 lymph node Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 206010061289 metastatic neoplasm Diseases 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 238000000053 physical method Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 238000001959 radiotherapy Methods 0.000 description 2
- 239000000333 selective estrogen receptor modulator Substances 0.000 description 2
- 229940095743 selective estrogen receptor modulator Drugs 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
- UHKJKVIZTFFFSB-UHFFFAOYSA-N 1,2-diphenylbutan-1-one Chemical compound C=1C=CC=CC=1C(CC)C(=O)C1=CC=CC=C1 UHKJKVIZTFFFSB-UHFFFAOYSA-N 0.000 description 1
- YOUWVLSTAZVPHM-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2-phenylbutan-1-one Chemical compound C=1C=CC=CC=1C(CC)C(=O)C1=CC=C(O)C=C1 YOUWVLSTAZVPHM-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 102000000872 ATM Human genes 0.000 description 1
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 1
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 108010004586 Ataxia Telangiectasia Mutated Proteins Proteins 0.000 description 1
- 108700020463 BRCA1 Proteins 0.000 description 1
- 102000036365 BRCA1 Human genes 0.000 description 1
- 101150072950 BRCA1 gene Proteins 0.000 description 1
- 108700020462 BRCA2 Proteins 0.000 description 1
- 102000052609 BRCA2 Human genes 0.000 description 1
- 101150008921 Brca2 gene Proteins 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 229920001661 Chitosan Polymers 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
- 206010051055 Deep vein thrombosis Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 229920002307 Dextran Polymers 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
- 108010085330 Estradiol Receptors Proteins 0.000 description 1
- 102100038595 Estrogen receptor Human genes 0.000 description 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 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 238000000729 Fisher's exact test Methods 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 101600111816 Homo sapiens Sex hormone-binding globulin (isoform 1) Proteins 0.000 description 1
- 208000033830 Hot Flashes Diseases 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 238000012313 Kruskal-Wallis test Methods 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 102000019040 Nuclear Antigens Human genes 0.000 description 1
- 108010051791 Nuclear Antigens Proteins 0.000 description 1
- 206010061137 Ocular toxicity Diseases 0.000 description 1
- 208000035327 Oestrogen receptor positive breast cancer Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 102300044179 Sex hormone-binding globulin isoform 1 Human genes 0.000 description 1
- 102100038021 Steryl-sulfatase Human genes 0.000 description 1
- 206010044245 Toxic optic neuropathy Diseases 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000011256 aggressive treatment Methods 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000069 breast epithelial cell Anatomy 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000009702 cancer cell proliferation Effects 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 230000005773 cancer-related death Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 150000001746 carotenes Chemical class 0.000 description 1
- 235000005473 carotenes Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000003588 centroblast Anatomy 0.000 description 1
- 210000003756 cervix mucus Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011970 concomitant therapy Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000013399 early diagnosis Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 201000006828 endometrial hyperplasia Diseases 0.000 description 1
- 208000016018 endometrial polyp Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 201000007281 estrogen-receptor positive breast cancer Diseases 0.000 description 1
- 108020004067 estrogen-related receptors Proteins 0.000 description 1
- 229960003399 estrone Drugs 0.000 description 1
- 108010005041 estrone sulfatase Proteins 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 210000001723 extracellular space Anatomy 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 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 1
- 150000002334 glycols Chemical class 0.000 description 1
- 210000003780 hair follicle Anatomy 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 238000003505 heat denaturation Methods 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 230000010224 hepatic metabolism Effects 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 238000001794 hormone therapy Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000030776 invasive breast carcinoma Diseases 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- JNWNAQZSBRFGPC-UHFFFAOYSA-M magnesium;2-(phenoxy)oxane;bromide Chemical compound [Mg+2].[Br-].O1CCCCC1OC1=CC=[C-]C=C1 JNWNAQZSBRFGPC-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000327 ocular toxicity Toxicity 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001987 poloxamine Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene 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
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 208000035803 proliferative type breast fibrocystic change Diseases 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000037067 skin hydration Effects 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Chemical class 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 201000005060 thrombophlebitis Diseases 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 239000000439 tumor marker Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 206010046811 uterine polyp Diseases 0.000 description 1
- 206010046901 vaginal discharge Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 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
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- 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
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US45896303P | 2003-04-01 | 2003-04-01 | |
PCT/EP2003/015029 WO2004087123A1 (en) | 2003-04-01 | 2003-12-15 | Prevention and treatment of breast cancer with 4-hydroxy tamoxifen |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20054526L NO20054526L (no) | 2005-09-30 |
NO333805B1 true NO333805B1 (no) | 2013-09-16 |
Family
ID=33131847
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20054526A NO333805B1 (no) | 2003-04-01 | 2005-09-30 | Anvendelse av 4-hydroxy tamoxifen for fremstilling av et medikament, og farmasoytiske sammensetninger |
Country Status (12)
Country | Link |
---|---|
US (2) | US7704516B2 (zh) |
EP (3) | EP1941871B1 (zh) |
JP (1) | JP5490346B2 (zh) |
AU (1) | AU2003294973B2 (zh) |
CA (1) | CA2519980C (zh) |
ES (3) | ES2456958T3 (zh) |
HK (2) | HK1086193A1 (zh) |
IL (1) | IL170807A (zh) |
MX (1) | MXPA05010597A (zh) |
NO (1) | NO333805B1 (zh) |
NZ (1) | NZ542499A (zh) |
WO (1) | WO2004087123A1 (zh) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE60305068T2 (de) * | 2002-12-18 | 2007-01-11 | Laboratoires Besins International | Behandlung von mastalgie mit 4-hydroxy-tamoxifen |
EP2050443B1 (en) * | 2002-12-18 | 2017-05-24 | Besins Healthcare Luxembourg SARL | Reduction of breast density with 4-hydroxy tamoxifen |
EP1941871B1 (en) * | 2003-04-01 | 2014-01-08 | Besins Healthcare Luxembourg SARL | Formulations for 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 |
DE602005005986T2 (de) * | 2004-03-22 | 2009-06-04 | Laboratoires Besins International | 4-hydroxytamoxifen zur behandlung und prophylaxe von benignen brusterkrankungen |
EP1579856A1 (en) * | 2004-03-22 | 2005-09-28 | Laboratoires Besins International | Treatment and prevention of benign breast disease 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 |
EP1579857A1 (en) * | 2004-03-22 | 2005-09-28 | Laboratoires Besins International | Chemically stable compositions of 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 |
EP2147674A1 (en) * | 2008-07-24 | 2010-01-27 | Besins Healthcare | Transdermal pharmaceutical compositions comprising danazol |
US10080760B2 (en) | 2009-10-27 | 2018-09-25 | Besins Healthcare Luxembourg Sarl | Transdermal pharmaceutical compositions comprising active agents |
CN110044998B (zh) | 2014-05-12 | 2021-12-14 | 奎斯特诊断投资公司 | 通过质谱法定量他莫昔芬及其代谢物 |
KR101571098B1 (ko) | 2014-07-16 | 2015-11-23 | 건국대학교 산학협력단 | 타목시펜 및 메틸설포닐메탄을 유효성분으로 포함하는 암 질환 예방 또는 치료용 약학 조성물 |
CN106459704B (zh) * | 2014-08-27 | 2020-08-25 | 东洋纺株式会社 | 低介电性粘合剂组合物 |
US10278976B2 (en) | 2014-12-12 | 2019-05-07 | Mira Dx, Inc. | Methods for treating or preventing cancer in a KRAS-variant patient and for diagnosing risk of developing multiple primary breast tumors |
BR112018072286A2 (pt) | 2016-04-29 | 2019-02-12 | Yale University | medida direcionada de atividade transcricional relacionada a receptores de hormônios |
SG11202002105WA (en) | 2017-09-11 | 2020-04-29 | Atossa Therapeutics Inc | Methods for making and using endoxifen |
WO2019172109A1 (ja) | 2018-03-07 | 2019-09-12 | 東亞合成株式会社 | 接着剤組成物及びこれを用いた接着剤層付き積層体 |
WO2020023616A1 (en) * | 2018-07-24 | 2020-01-30 | Cornell University | Methods of upregulating tiparp as anticancer strategies |
Family Cites Families (27)
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 |
EP0287690B1 (de) | 1987-04-21 | 1992-09-02 | HEUMANN PHARMA GMBH & CO | Stabile Lösungsmitteladdukte von Z-1-(p-beta-Dimethylamino-ethoxyphenyl)-1-(p-hydroxyphenyl)-2-phenylbut-1-en |
US5045553A (en) | 1987-06-24 | 1991-09-03 | Fujisawa Pharmaceutical Company, Ltd. | Pharmaceutical composition for percutaneous drug absorption and percutaneous drug absorption promoter |
DE3836862A1 (de) | 1988-10-27 | 1990-05-03 | Schering Ag | Mittel zur transdermalen applikation von steroidhormonen |
US5189212A (en) | 1990-09-07 | 1993-02-23 | University Of Georgia Research Foundation, Inc. | Triarylethylene carboxylic acids with estrogenic activity |
TW218849B (zh) * | 1991-05-17 | 1994-01-11 | Bristol Myers Squibb Co | |
US5613958A (en) | 1993-05-12 | 1997-03-25 | Pp Holdings Inc. | Transdermal delivery systems for the modulated administration of drugs |
DE4407742C1 (de) * | 1994-03-08 | 1995-06-22 | Hexal Pharma Gmbh | Transdermales System in Form eines Pflasters mit einem Tamoxifen-Derivat |
US5720963A (en) * | 1994-08-26 | 1998-02-24 | Mary Kay Inc. | Barrier disruption treatments for structurally deteriorated skin |
DE59703511D1 (de) | 1996-03-29 | 2001-06-13 | S W Patentverwaltungs Ges M B | Kosmetikum bzw. kosmetikzusammensetzung zur glättung und straffung der haut bei gestörtem unterhaut-binde-fettgewebe, insbesondere bei der "cellulite" |
AU2513899A (en) | 1997-12-23 | 1999-07-19 | Hexal Ag | Mixture and pharmaceutical composition comprising z-4-hydroxytamoxifen and cyclodextrin |
US6013270A (en) * | 1998-04-20 | 2000-01-11 | The Procter & Gamble Company | Skin care kit |
MXPA02006055A (es) | 1999-12-16 | 2004-08-23 | Dermatrends Inc | Agentes liberadores de hidroxido como incrementadores de penetracion en la piel. |
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 |
AU2002340120A1 (en) | 2001-10-04 | 2003-04-14 | 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 |
DE60305068T2 (de) * | 2002-12-18 | 2007-01-11 | Laboratoires Besins International | Behandlung von mastalgie mit 4-hydroxy-tamoxifen |
EP2050443B1 (en) * | 2002-12-18 | 2017-05-24 | Besins Healthcare Luxembourg SARL | Reduction of breast density with 4-hydroxy tamoxifen |
EP1941871B1 (en) | 2003-04-01 | 2014-01-08 | Besins Healthcare Luxembourg SARL | Formulations for 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 |
EP1579856A1 (en) | 2004-03-22 | 2005-09-28 | Laboratoires Besins International | Treatment and prevention of benign breast disease 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 |
EP1579857A1 (en) | 2004-03-22 | 2005-09-28 | Laboratoires Besins International | Chemically stable compositions of 4-hydroxy tamoxifen |
EP1647271A1 (en) | 2004-10-14 | 2006-04-19 | Laboratoires Besins International | 4-Hydroxy tamoxifen gel formulations |
-
2003
- 2003-12-15 EP EP08103014.0A patent/EP1941871B1/en not_active Expired - Lifetime
- 2003-12-15 EP EP03785958.4A patent/EP1608353B1/en not_active Expired - Lifetime
- 2003-12-15 AU AU2003294973A patent/AU2003294973B2/en not_active Expired
- 2003-12-15 US US10/734,638 patent/US7704516B2/en not_active Expired - Lifetime
- 2003-12-15 NZ NZ542499A patent/NZ542499A/en not_active IP Right Cessation
- 2003-12-15 JP JP2004570040A patent/JP5490346B2/ja not_active Expired - Lifetime
- 2003-12-15 WO PCT/EP2003/015029 patent/WO2004087123A1/en active Application Filing
- 2003-12-15 ES ES08103014.0T patent/ES2456958T3/es not_active Expired - Lifetime
- 2003-12-15 CA CA2519980A patent/CA2519980C/en not_active Expired - Lifetime
- 2003-12-15 ES ES08103007.4T patent/ES2456957T3/es not_active Expired - Lifetime
- 2003-12-15 EP EP08103007.4A patent/EP1952810B1/en not_active Expired - Lifetime
- 2003-12-15 MX MXPA05010597A patent/MXPA05010597A/es active IP Right Grant
- 2003-12-15 ES ES03785958.4T patent/ES2483896T3/es not_active Expired - Lifetime
-
2005
- 2005-09-12 IL IL170807A patent/IL170807A/en active IP Right Grant
- 2005-09-30 NO NO20054526A patent/NO333805B1/no not_active IP Right Cessation
-
2006
- 2006-06-28 HK HK06107310.2A patent/HK1086193A1/zh not_active IP Right Cessation
- 2006-06-28 HK HK08113909.5A patent/HK1119950A1/zh not_active IP Right Cessation
-
2009
- 2009-01-14 US US12/353,890 patent/US8475814B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP1952810A1 (en) | 2008-08-06 |
US20050031695A1 (en) | 2005-02-10 |
EP1941871B1 (en) | 2014-01-08 |
ES2456957T3 (es) | 2014-04-24 |
HK1119950A1 (zh) | 2009-03-20 |
JP5490346B2 (ja) | 2014-05-14 |
WO2004087123A1 (en) | 2004-10-14 |
US8475814B2 (en) | 2013-07-02 |
EP1941871A1 (en) | 2008-07-09 |
CA2519980C (en) | 2012-04-10 |
AU2003294973B2 (en) | 2010-05-13 |
EP1952810B1 (en) | 2014-01-08 |
CA2519980A1 (en) | 2004-10-14 |
JP2006514967A (ja) | 2006-05-18 |
US20090186944A1 (en) | 2009-07-23 |
HK1086193A1 (zh) | 2006-09-15 |
ES2456958T3 (es) | 2014-04-24 |
MXPA05010597A (es) | 2006-03-09 |
NO20054526L (no) | 2005-09-30 |
EP1608353A1 (en) | 2005-12-28 |
US7704516B2 (en) | 2010-04-27 |
AU2003294973A1 (en) | 2004-10-25 |
NZ542499A (en) | 2008-10-31 |
ES2483896T3 (es) | 2014-08-08 |
EP1608353B1 (en) | 2014-04-30 |
IL170807A (en) | 2014-08-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8475814B2 (en) | Prevention and treatment of breast cancer with 4-hydroxy tamoxifen | |
US8048927B2 (en) | Treatment and prevention of benign breast disease with 4-hydroxy tamoxifen | |
EP2050443B1 (en) | Reduction of breast density with 4-hydroxy tamoxifen | |
CA2509660C (en) | Treatment of mastalgia with 4-hydroxy tamoxifen | |
US7968532B2 (en) | Treatment of gynecomastia with 4-hydroxy tamoxifen | |
EP1579856A1 (en) | Treatment and prevention of benign breast disease with 4-hydroxy tamoxifen | |
NO336463B1 (no) | Anvendelse av 4-hydroksytamoxifen for fremstilling av et medikament for behandling av gynekomasti | |
AU2005227072B2 (en) | Treatment and prevention of benign breast disease with 4-hydroxy tamoxifen | |
EP1550440A1 (en) | Use of 4-hydroxytamoxifen for the preparation of a medicament for the treatment of gynecomastia |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: BESINS HEALTHCARE LUXEMBOURG, LU |
|
CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: BENSINS HEALTHCARE LUXEMBOURG SARL, LU |
|
CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: BESINS HEALTHCARE LUXEMBOURG SARL, LU |
|
MK1K | Patent expired |