ZA200905145B - Inclusion complex of raloxifene hydrochloride and ß-cyclodextrin - Google Patents
Inclusion complex of raloxifene hydrochloride and ß-cyclodextrin Download PDFInfo
- Publication number
- ZA200905145B ZA200905145B ZA200905145A ZA200905145A ZA200905145B ZA 200905145 B ZA200905145 B ZA 200905145B ZA 200905145 A ZA200905145 A ZA 200905145A ZA 200905145 A ZA200905145 A ZA 200905145A ZA 200905145 B ZA200905145 B ZA 200905145B
- Authority
- ZA
- South Africa
- Prior art keywords
- cyclodextrin
- inclusion complex
- raloxifene hydrochloride
- complex according
- inclusion
- Prior art date
Links
- BKXVVCILCIUCLG-UHFFFAOYSA-N raloxifene hydrochloride Chemical compound [H+].[Cl-].C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 BKXVVCILCIUCLG-UHFFFAOYSA-N 0.000 title claims description 34
- 229960002119 raloxifene hydrochloride Drugs 0.000 title claims description 29
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 title claims description 15
- 239000001116 FEMA 4028 Substances 0.000 title 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 title 1
- 229960004853 betadex Drugs 0.000 title 1
- 229960004622 raloxifene Drugs 0.000 claims description 12
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 238000001228 spectrum Methods 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
- 208000001685 postmenopausal osteoporosis Diseases 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 238000004566 IR spectroscopy Methods 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- -1 raloxifene compound Chemical class 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 101000878595 Arabidopsis thaliana Squalene synthase 1 Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000037058 blood plasma level Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- ODLHGICHYURWBS-FOSILIAISA-N molport-023-220-444 Chemical compound CC(O)COC[C@@H]([C@@H]([C@H]([C@@H]1O)O)O[C@@H]2O[C@H]([C@H](O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O3)[C@@H](O)[C@@H]2O)COCC(O)C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@H]3O[C@H]1COCC(C)O ODLHGICHYURWBS-FOSILIAISA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
-
- 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
- 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
- A61P19/08—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (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)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09425196A EP2253627A1 (en) | 2009-05-21 | 2009-05-21 | Inclusion complex of raloxifene hydrochloride and beta-cyclodextrin. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200905145B true ZA200905145B (en) | 2010-04-28 |
Family
ID=41011803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200905145A ZA200905145B (en) | 2009-05-21 | 2009-07-22 | Inclusion complex of raloxifene hydrochloride and ß-cyclodextrin |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20100298265A1 (zh) |
| EP (1) | EP2253627A1 (zh) |
| JP (1) | JP2010270100A (zh) |
| KR (1) | KR20100126146A (zh) |
| CN (1) | CN101890171A (zh) |
| AR (1) | AR072561A1 (zh) |
| AU (1) | AU2009202887A1 (zh) |
| BR (1) | BRPI0902387A2 (zh) |
| CA (1) | CA2671921A1 (zh) |
| IL (1) | IL199883A0 (zh) |
| MX (1) | MX2009007785A (zh) |
| NZ (1) | NZ578451A (zh) |
| RU (1) | RU2009127394A (zh) |
| TW (1) | TW201041878A (zh) |
| ZA (1) | ZA200905145B (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102198274B (zh) * | 2011-03-30 | 2013-04-24 | 天津红日药业股份有限公司 | 雷洛昔芬的环糊精包合物及其制剂的制备方法 |
| ITMI20121821A1 (it) * | 2012-10-25 | 2014-04-26 | Erregierre Spa | Composizione farmaceutica solubile in acqua a base di un sale di raloxifene |
| DK3565602T3 (da) * | 2017-01-09 | 2021-06-07 | Scipharm S A R L | Hidtil ukendt fremgangsmåde til fremstilling af vandopløselig forskolin |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2135176C1 (ru) | 1993-12-14 | 1999-08-27 | Эли Лилли Энд Компани | Водорастворенный комплекс включения соединений бензотиофена с водорастворимым циклодекстрином, способ его получения и фармацевтическая композиция |
| US6713494B1 (en) * | 1996-08-28 | 2004-03-30 | Eli Lilly And Company | Amorphous benzothiophenes, methods of preparation and methods of use |
| US20030130316A1 (en) * | 2000-03-20 | 2003-07-10 | Steiner Mitchell S. | Method for chemoprevention of prostate cancer |
| CN1210079C (zh) * | 2001-04-25 | 2005-07-13 | 上海市计划生育科学研究所 | 阴道环制剂及其应用 |
| US20060105045A1 (en) | 2004-11-08 | 2006-05-18 | Buchanan Charles M | Cyclodextrin solubilizers for liquid and semi-solid formulations |
| US20060270641A1 (en) * | 2005-05-31 | 2006-11-30 | Steiner Mitchell S | Method for chemoprevention of prostate cancer |
| US20110159084A1 (en) * | 2008-04-02 | 2011-06-30 | Dr. Reddy's Laboratories Ltd. | Raloxifene pharmaceutical formulations |
-
2009
- 2009-05-21 EP EP09425196A patent/EP2253627A1/en not_active Withdrawn
- 2009-07-14 AR ARP090102669A patent/AR072561A1/es unknown
- 2009-07-15 IL IL199883A patent/IL199883A0/en unknown
- 2009-07-15 BR BRPI0902387-9A patent/BRPI0902387A2/pt not_active Application Discontinuation
- 2009-07-15 CA CA2671921A patent/CA2671921A1/en not_active Abandoned
- 2009-07-15 US US12/460,236 patent/US20100298265A1/en not_active Abandoned
- 2009-07-16 NZ NZ578451A patent/NZ578451A/en not_active IP Right Cessation
- 2009-07-16 RU RU2009127394/04A patent/RU2009127394A/ru not_active Application Discontinuation
- 2009-07-16 TW TW098124060A patent/TW201041878A/zh unknown
- 2009-07-16 KR KR1020090064925A patent/KR20100126146A/ko not_active Application Discontinuation
- 2009-07-16 AU AU2009202887A patent/AU2009202887A1/en not_active Abandoned
- 2009-07-17 CN CN2009101591633A patent/CN101890171A/zh active Pending
- 2009-07-17 JP JP2009169465A patent/JP2010270100A/ja not_active Withdrawn
- 2009-07-21 MX MX2009007785A patent/MX2009007785A/es not_active Application Discontinuation
- 2009-07-22 ZA ZA200905145A patent/ZA200905145B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR072561A1 (es) | 2010-09-08 |
| CN101890171A (zh) | 2010-11-24 |
| NZ578451A (en) | 2010-09-30 |
| MX2009007785A (es) | 2010-11-22 |
| US20100298265A1 (en) | 2010-11-25 |
| BRPI0902387A2 (pt) | 2011-02-01 |
| IL199883A0 (en) | 2010-05-17 |
| KR20100126146A (ko) | 2010-12-01 |
| JP2010270100A (ja) | 2010-12-02 |
| EP2253627A1 (en) | 2010-11-24 |
| TW201041878A (en) | 2010-12-01 |
| CA2671921A1 (en) | 2010-11-21 |
| RU2009127394A (ru) | 2011-01-27 |
| AU2009202887A1 (en) | 2010-12-09 |
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