CA2766618A1 - Polymorphic form d of bazedoxifene acetate and methods of preparing same - Google Patents
Polymorphic form d of bazedoxifene acetate and methods of preparing same Download PDFInfo
- Publication number
- CA2766618A1 CA2766618A1 CA2766618A CA2766618A CA2766618A1 CA 2766618 A1 CA2766618 A1 CA 2766618A1 CA 2766618 A CA2766618 A CA 2766618A CA 2766618 A CA2766618 A CA 2766618A CA 2766618 A1 CA2766618 A1 CA 2766618A1
- Authority
- CA
- Canada
- Prior art keywords
- bazedoxifene acetate
- composition
- polymorph
- catalyst
- bazedoxifene
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 120
- OMZAMQFQZMUNTP-UHFFFAOYSA-N acetic acid;1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol Chemical compound CC(O)=O.C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 OMZAMQFQZMUNTP-UHFFFAOYSA-N 0.000 title claims abstract description 118
- 229960003713 bazedoxifene acetate Drugs 0.000 title claims abstract description 99
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 59
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 238000001035 drying Methods 0.000 claims description 26
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 19
- 206010027304 Menopausal symptoms Diseases 0.000 claims description 15
- 208000035475 disorder Diseases 0.000 claims description 15
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 14
- GNVYSOYFHQFUMV-UHFFFAOYSA-N 3-(azepan-1-yl)-2-phenylmethoxy-1h-indole Chemical compound C=1C=CC=CC=1COC=1NC2=CC=CC=C2C=1N1CCCCCC1 GNVYSOYFHQFUMV-UHFFFAOYSA-N 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 11
- 210000001519 tissue Anatomy 0.000 claims description 11
- 229960005070 ascorbic acid Drugs 0.000 claims description 10
- 235000010323 ascorbic acid Nutrition 0.000 claims description 10
- 239000011668 ascorbic acid Substances 0.000 claims description 10
- UCJGJABZCDBEDK-UHFFFAOYSA-N bazedoxifene Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 UCJGJABZCDBEDK-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 206010065687 Bone loss Diseases 0.000 claims description 8
- 206010030247 Oestrogen deficiency Diseases 0.000 claims description 8
- 238000001237 Raman spectrum Methods 0.000 claims description 8
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 230000003078 antioxidant effect Effects 0.000 claims description 8
- 235000006708 antioxidants Nutrition 0.000 claims description 8
- 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 claims description 8
- 230000002357 endometrial effect Effects 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 7
- 208000026310 Breast neoplasm Diseases 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 230000002159 abnormal effect Effects 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- 238000011161 development Methods 0.000 claims description 7
- 201000006564 estrogen excess Diseases 0.000 claims description 7
- 238000010899 nucleation Methods 0.000 claims description 7
- 230000035755 proliferation Effects 0.000 claims description 7
- 206010014733 Endometrial cancer Diseases 0.000 claims description 6
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 6
- 201000009273 Endometriosis Diseases 0.000 claims description 6
- 208000001132 Osteoporosis Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 208000016018 endometrial polyp Diseases 0.000 claims description 6
- 206010046811 uterine polyp Diseases 0.000 claims description 6
- 208000029725 Metabolic bone disease Diseases 0.000 claims description 5
- 206010049088 Osteopenia Diseases 0.000 claims description 5
- 239000012298 atmosphere Substances 0.000 claims description 5
- 230000036961 partial effect Effects 0.000 claims description 5
- 235000012000 cholesterol Nutrition 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 230000001457 vasomotor Effects 0.000 claims description 4
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 3
- 208000005641 Adenomyosis Diseases 0.000 claims description 3
- 201000004384 Alopecia Diseases 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 206010013908 Dysfunctional uterine bleeding Diseases 0.000 claims description 3
- 206010060800 Hot flush Diseases 0.000 claims description 3
- 208000037147 Hypercalcaemia Diseases 0.000 claims description 3
- 208000013038 Hypocalcemia Diseases 0.000 claims description 3
- 206010027514 Metrorrhagia Diseases 0.000 claims description 3
- 208000034578 Multiple myelomas Diseases 0.000 claims description 3
- 208000010191 Osteitis Deformans Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 208000027868 Paget disease Diseases 0.000 claims description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 206010040799 Skin atrophy Diseases 0.000 claims description 3
- 206010046798 Uterine leiomyoma Diseases 0.000 claims description 3
- 206010000496 acne Diseases 0.000 claims description 3
- 206010068168 androgenetic alopecia Diseases 0.000 claims description 3
- 208000011803 breast fibrocystic disease Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 201000007455 central nervous system cancer Diseases 0.000 claims description 3
- 230000006999 cognitive decline Effects 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 210000001072 colon Anatomy 0.000 claims description 3
- 208000029742 colonic neoplasm Diseases 0.000 claims description 3
- 201000009274 endometriosis of uterus Diseases 0.000 claims description 3
- 230000000148 hypercalcaemia Effects 0.000 claims description 3
- 208000030915 hypercalcemia disease Diseases 0.000 claims description 3
- 230000000705 hypocalcaemia Effects 0.000 claims description 3
- 208000000509 infertility Diseases 0.000 claims description 3
- 230000036512 infertility Effects 0.000 claims description 3
- 231100000535 infertility Toxicity 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 201000010260 leiomyoma Diseases 0.000 claims description 3
- 208000027202 mammary Paget disease Diseases 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 208000005368 osteomalacia Diseases 0.000 claims description 3
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 3
- 201000004240 prostatic hypertrophy Diseases 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 201000007954 uterine fibroid Diseases 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000006186 oral dosage form Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
- 238000011282 treatment Methods 0.000 abstract description 6
- 238000002425 crystallisation Methods 0.000 description 21
- 230000008025 crystallization Effects 0.000 description 21
- 239000007787 solid Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 210000000988 bone and bone Anatomy 0.000 description 9
- 230000008859 change Effects 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 238000002955 isolation Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011877 solvent mixture Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229940011871 estrogen Drugs 0.000 description 6
- 239000000262 estrogen Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000003442 weekly effect Effects 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 230000003321 amplification Effects 0.000 description 4
- 229960000817 bazedoxifene Drugs 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 102000015694 estrogen receptors Human genes 0.000 description 4
- 108010038795 estrogen receptors Proteins 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003199 nucleic acid amplification method Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000328 estrogen antagonist Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 238000001069 Raman spectroscopy Methods 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001833 anti-estrogenic effect Effects 0.000 description 2
- -1 but not limited to Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000005056 compaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000037765 diseases and disorders Diseases 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001076 estrogenic effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 229940095743 selective estrogen receptor modulator Drugs 0.000 description 2
- 239000000333 selective estrogen receptor modulator Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 208000010392 Bone Fractures Diseases 0.000 description 1
- 208000014311 Cushing syndrome Diseases 0.000 description 1
- 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 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 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 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 238000005079 FT-Raman Methods 0.000 description 1
- MBHNWCYEGXQEIT-UHFFFAOYSA-N Fluphenazine hydrochloride Chemical compound Cl.Cl.C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 MBHNWCYEGXQEIT-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000721701 Lynx Species 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 206010067572 Oestrogenic effect Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 238000002679 ablation Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 238000004164 analytical calibration Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012512 bulk drug substance Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- ZUGCTMPRAOKPHT-UHFFFAOYSA-N cyclohexane;ethanol;methanol Chemical compound OC.CCO.C1CCCCC1 ZUGCTMPRAOKPHT-UHFFFAOYSA-N 0.000 description 1
- YPDUMMPMXFQVGG-UHFFFAOYSA-N cyclohexane;ethanol;propan-2-one Chemical compound CCO.CC(C)=O.C1CCCCC1 YPDUMMPMXFQVGG-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 210000003278 egg shell Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 208000002566 gonadal dysgenesis Diseases 0.000 description 1
- 238000002657 hormone replacement therapy Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 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
- 238000009806 oophorectomy Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 208000001685 postmenopausal osteoporosis Diseases 0.000 description 1
- 238000001144 powder X-ray diffraction data Methods 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000010942 self-nucleation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride 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
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- 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
-
- 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
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
-
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- 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
- A61P15/14—Drugs for genital or sexual disorders; Contraceptives for lactation disorders, e.g. galactorrhoea
-
- 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
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
- 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
- A61P5/30—Oestrogens
-
- 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
- A61P5/32—Antioestrogens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Reproductive Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Pregnancy & Childbirth (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT001109A ITMI20091109A1 (it) | 2009-06-23 | 2009-06-23 | Forma polimorfa d di bazedoxifene acetato e metodi per la sua preparazione |
| ITMI2009A001109 | 2009-06-23 | ||
| US24496109P | 2009-09-23 | 2009-09-23 | |
| US61/244,961 | 2009-09-23 | ||
| PCT/US2010/039488 WO2010151541A1 (en) | 2009-06-23 | 2010-06-22 | Polymorphic form d of bazedoxifene acetate and methods of preparing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2766618A1 true CA2766618A1 (en) | 2010-12-29 |
Family
ID=42035899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2766618A Abandoned CA2766618A1 (en) | 2009-06-23 | 2010-06-22 | Polymorphic form d of bazedoxifene acetate and methods of preparing same |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8063041B2 (enExample) |
| EP (1) | EP2445876A1 (enExample) |
| JP (4) | JP2011037832A (enExample) |
| AR (1) | AR077203A1 (enExample) |
| CA (1) | CA2766618A1 (enExample) |
| IT (1) | ITMI20091109A1 (enExample) |
| TW (1) | TW201102378A (enExample) |
| WO (1) | WO2010151541A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2655466T3 (es) | 2007-08-13 | 2018-02-20 | Monsanto Technology Llc | Composiciones y procedimientos de control de nematodos |
| US9212172B2 (en) * | 2010-09-14 | 2015-12-15 | Dr. Reddy's Laboratories Limited | Preparation of crystalline bazedoxifene and its salts |
| WO2013182169A1 (en) | 2012-06-07 | 2013-12-12 | Zentiva, K. S. | Process of preparation of an antioxidant-free polymorphically and chemically stable formulation of bazedoxifene acetate |
| WO2013182170A1 (en) | 2012-06-07 | 2013-12-12 | Zentiva, K. S. | Enhancement of dissolution rate from pharmaceutical composition comprising bazedoxifene acetate |
| UA118254C2 (uk) | 2012-12-04 | 2018-12-26 | Монсанто Текнолоджи Ллс | Нематоцидні водні композиції концентрату суспензії |
| CN103864664A (zh) * | 2012-12-18 | 2014-06-18 | 江苏柯菲平医药有限公司 | 巴多昔芬乙酸盐新晶型及其制备方法 |
| CN103864665B (zh) * | 2014-03-04 | 2016-03-02 | 苏州特瑞药业有限公司 | 醋酸巴多昔芬的制备方法 |
| CN104370796B (zh) * | 2014-11-21 | 2016-09-14 | 扬子江药业集团有限公司 | 一种醋酸巴多昔芬多晶型b的制备方法 |
| CU24523B1 (es) | 2015-06-18 | 2021-06-08 | Estetra Sprl | Unidad de dosificación orodispersable que contiene un componente estetrol |
| EP3701944B1 (en) | 2015-06-18 | 2021-12-08 | Estetra SRL | Orodispersible dosage unit containing an estetrol component |
| CA3178291A1 (en) | 2016-08-05 | 2018-04-12 | Estetra Srl | Method for the management of dysmenorrhea and menstrual pain |
| KR20190096462A (ko) | 2018-01-08 | 2019-08-20 | (주)휴온스 | 바제독시펜 아세테이트 결정형 d형을 포함하는 안정성이 증가된 약제학적 조성물 및 그 제조방법 |
| TWI801561B (zh) | 2018-04-19 | 2023-05-11 | 比利時商依思特拉私人有限責任公司 | 化合物及其用於緩解絕經相關症狀的用途 |
| EP3781171B1 (en) * | 2018-04-19 | 2022-02-09 | Estetra SRL | Compounds and their uses for alleviating menopause-associated symptoms |
| CN109851547B (zh) * | 2018-12-27 | 2020-09-08 | 北京鑫开元医药科技有限公司 | 一种醋酸巴多昔芬晶型d的制备方法及用途 |
| KR20190132311A (ko) | 2019-11-15 | 2019-11-27 | (주)휴온스 | 바제독시펜 아세테이트 결정형 d형을 포함하는 안정성이 증가된 약제학적 조성물 및 그 제조방법 |
| CN111004165A (zh) * | 2019-12-03 | 2020-04-14 | 南京正济医药研究有限公司 | 一种醋酸巴多昔芬晶型a的制备方法 |
| TWI893101B (zh) | 2020-04-16 | 2025-08-11 | 比利時商埃斯特拉有限責任公司 | 具有降低之副作用之避孕組成物 |
| US11246874B1 (en) | 2021-04-20 | 2022-02-15 | Oxygen Biotech LLC | Treatment of COVID-19 |
| CN113244240A (zh) * | 2021-05-26 | 2021-08-13 | 深圳市人民医院 | 醋酸巴多昔芬在治疗急性髓系白血病药物中的应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2772508A (en) | 1954-04-28 | 1956-12-04 | Claude A Greenlee | Fish line pullaway sinker |
| US5998402A (en) * | 1996-04-19 | 1999-12-07 | American Home Products Corporation | 2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indoles as estrogenic agents |
| SK281737B6 (sk) | 1996-04-19 | 2001-07-10 | American Home Products Corporation | 2-fenylindolové zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie |
| US6479535B1 (en) | 1998-05-15 | 2002-11-12 | Wyeth | 2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indole and estrogen formulations |
| AR029538A1 (es) | 2000-07-06 | 2003-07-02 | Wyeth Corp | Composiciones farmaceuticas de agentes estrogenicos |
| RU2355397C2 (ru) | 2002-06-13 | 2009-05-20 | Уайт | Режимы лечения базедоксифеном |
| RU2006132180A (ru) * | 2004-04-07 | 2008-05-20 | Вайет (Us) | Кристаллический полиморф базедоксифен ацетата |
| TW200536845A (en) * | 2004-04-07 | 2005-11-16 | Wyeth Corp | Crystalline polymorph of bazedoxifene acetate |
| GT200500083A (es) * | 2004-04-08 | 2005-10-31 | Formulaciones de acetato de bazedoxifeno | |
| CN101304731B (zh) | 2005-08-24 | 2012-06-20 | 惠氏公司 | 醋酸苯卓昔芬制剂及其生产方法 |
| CZ302358B6 (cs) * | 2007-07-25 | 2011-03-30 | Zentiva, A. S. | Nové soli bazedoxifenu |
-
2009
- 2009-06-23 IT IT001109A patent/ITMI20091109A1/it unknown
-
2010
- 2010-06-22 WO PCT/US2010/039488 patent/WO2010151541A1/en not_active Ceased
- 2010-06-22 CA CA2766618A patent/CA2766618A1/en not_active Abandoned
- 2010-06-22 EP EP10728533A patent/EP2445876A1/en not_active Withdrawn
- 2010-06-22 US US12/820,593 patent/US8063041B2/en active Active
- 2010-06-22 TW TW099120246A patent/TW201102378A/zh unknown
- 2010-06-22 JP JP2010141370A patent/JP2011037832A/ja active Pending
- 2010-06-23 AR ARP100102214A patent/AR077203A1/es not_active Application Discontinuation
-
2015
- 2015-12-04 JP JP2015237242A patent/JP2016033165A/ja active Pending
-
2017
- 2017-05-22 JP JP2017100527A patent/JP2017137360A/ja active Pending
-
2018
- 2018-07-30 JP JP2018142063A patent/JP2018162327A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010151541A8 (en) | 2011-05-12 |
| JP2011037832A (ja) | 2011-02-24 |
| JP2016033165A (ja) | 2016-03-10 |
| JP2018162327A (ja) | 2018-10-18 |
| EP2445876A1 (en) | 2012-05-02 |
| JP2017137360A (ja) | 2017-08-10 |
| US8063041B2 (en) | 2011-11-22 |
| TW201102378A (en) | 2011-01-16 |
| US20110021504A1 (en) | 2011-01-27 |
| AR077203A1 (es) | 2011-08-10 |
| WO2010151541A1 (en) | 2010-12-29 |
| ITMI20091109A1 (it) | 2010-12-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8063041B2 (en) | Polymorphic Form D of bazedoxifene acetate and methods of preparing same | |
| US8183367B2 (en) | Methods of preparing polymorphic form A of bazedoxifene acetate | |
| PT1667682E (pt) | Formas polimórficas de 3-(4-amino-1-oxo-1,3-di-hidroisoindol- 2-il)-piperidina-2,6-diona | |
| US7683051B2 (en) | Crystalline polymorph of bazedoxifene acetate | |
| JP2009007361A (ja) | バゼドキシフェンアセテートの結晶質多形体 | |
| JP2018510179A (ja) | イブルチニブとカルボン酸との共結晶 | |
| WO2007146717A2 (en) | Process for making salts of n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl)ethyl]amino]methyl]phenyl]-2e-2-propenamide | |
| JP5160892B2 (ja) | （３−シアノ−１ｈ−インドール−７−イル）−［４−（４−フルオロフェネチル）ピペラジン−１−イル］メタノン塩酸塩の新規な結晶形 | |
| US20100016582A1 (en) | Methods of converting polymorphic form b of bazedoxifene acetate to polymorphic form a of bazedoxifene acetate | |
| WO2009102778A1 (en) | Amorphous polymorph of bazedoxifene acetate | |
| CA2949155C (en) | Allisartan isoproxil polymorph, its preparation method and pharmaceutical | |
| JP2009538904A (ja) | 新規結晶形 | |
| CN114456109A (zh) | 一种高纯度卡博替尼苹果酸盐的制备方法及其应用 | |
| MXPA06011717A (en) | Crystalline polymorph of bazedoxifene acetate | |
| MXPA06011716A (en) | Crystalline polymorph of a bazedoxifene acetate | |
| HK1233247A1 (en) | Allisartan isoproxil polymorph, its preparation method and pharmaceutical composition containing the polymorph | |
| SK51062005A3 (sk) | Spôsob prípravy farmaceuticky akceptovateľných solí 2-[(5-metoxy- 1H-indol-3-yl)metylén]-N-pentylkarbazimidamidu (tegaserodu) | |
| HK1149010A (en) | Methods of preparing polymorphic form a of bazedoxifene acetate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140603 |