ZA200609596B - Crystalline and amorphous forms of smilagenin - Google Patents
Crystalline and amorphous forms of smilagenin Download PDFInfo
- Publication number
- ZA200609596B ZA200609596B ZA200609596A ZA200609596A ZA200609596B ZA 200609596 B ZA200609596 B ZA 200609596B ZA 200609596 A ZA200609596 A ZA 200609596A ZA 200609596 A ZA200609596 A ZA 200609596A ZA 200609596 B ZA200609596 B ZA 200609596B
- Authority
- ZA
- South Africa
- Prior art keywords
- smilagenin
- crystalline
- crystalline form
- examples
- accompanying drawings
- Prior art date
Links
- GMBQZIIUCVWOCD-UQHLGXRBSA-N (25R)-5beta-spirostan-3beta-ol Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 GMBQZIIUCVWOCD-UQHLGXRBSA-N 0.000 title claims description 427
- RTMWIZOXNKJHRE-UHFFFAOYSA-N Tigogenin Natural products CC1COC2CC(C)(OC12)C3CCC4C5CCC6CC(O)CCC6(C)C5CCC34C RTMWIZOXNKJHRE-UHFFFAOYSA-N 0.000 title claims description 216
- 229950002323 smilagenin Drugs 0.000 title claims description 214
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 92
- 239000000463 material Substances 0.000 claims description 70
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 56
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- 239000013078 crystal Substances 0.000 claims description 26
- 239000003814 drug Substances 0.000 claims description 16
- -1 Smilagenin monohydrate Chemical class 0.000 claims description 15
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- 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
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- INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 claims description 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- GMBQZIIUCVWOCD-WWASVFFGSA-N Sarsapogenine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 GMBQZIIUCVWOCD-WWASVFFGSA-N 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- 238000007416 differential thermogravimetric analysis Methods 0.000 description 2
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
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- 239000012535 impurity Substances 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
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- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 description 1
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- 239000003981 vehicle Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Psychology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0409567.5A GB0409567D0 (en) | 2004-04-28 | 2004-04-28 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200609596B true ZA200609596B (en) | 2008-01-30 |
Family
ID=32408243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200609596A ZA200609596B (en) | 2004-04-28 | 2006-11-17 | Crystalline and amorphous forms of smilagenin |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US20080004249A1 (fr) |
| EP (2) | EP1742960A2 (fr) |
| JP (1) | JP2007534736A (fr) |
| KR (1) | KR20070028387A (fr) |
| CN (2) | CN101076539A (fr) |
| AU (1) | AU2005238274A1 (fr) |
| BR (1) | BRPI0510458A (fr) |
| CA (1) | CA2564368A1 (fr) |
| GB (1) | GB0409567D0 (fr) |
| IL (1) | IL178870A0 (fr) |
| MX (1) | MXPA06012641A (fr) |
| NO (1) | NO20065485L (fr) |
| RU (1) | RU2006141389A (fr) |
| SG (1) | SG155165A1 (fr) |
| TW (1) | TW200538145A (fr) |
| WO (1) | WO2005105825A2 (fr) |
| ZA (1) | ZA200609596B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110115589A (ko) | 2009-01-24 | 2011-10-21 | 파이토팜 피엘씨 | 신경영양인자가 매개된 장애의 치료 |
| EP2595621A1 (fr) | 2010-07-20 | 2013-05-29 | Phytopharm PLC | Traitement de troubles induits par la l-dopa, un agoniste de dopamine et/ou un activateur de dopamine |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL292786A (fr) * | 1962-05-15 | |||
| US3169959A (en) * | 1963-07-23 | 1965-02-16 | Intermediates Inc | Method of obtaining smilagenin |
| CA985172A (en) | 1972-10-06 | 1976-03-09 | Dushan M. Dvornik | Compositions and methods for reducing blood cholesterol |
| US4602003A (en) * | 1982-05-17 | 1986-07-22 | Medical Research Foundation Of Oregon | Synthetic compounds to inhibit intestinal absorption of cholesterol in the treatment of hypercholesterolemia |
| US4680289A (en) * | 1985-06-05 | 1987-07-14 | Progenics, Inc. | Treatment of obesity and diabetes using sapogenins |
| US5017562A (en) | 1987-02-11 | 1991-05-21 | Regents Of The University Of Minnesota | Crystalline saponin-containing complex |
| PL207723B1 (pl) * | 1998-03-26 | 2011-01-31 | Phytopharm Plc | Zastosowanie smilageniny do leczenia choroby Parkinsona |
| GB9905275D0 (en) | 1999-03-08 | 1999-04-28 | Phytopharm Ltd | Treatment of conditions associated with membrane-bound receptors and their function |
| GB9923076D0 (en) | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| GB9923078D0 (en) | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| GB9923077D0 (en) | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| GB0000228D0 (en) | 2000-01-06 | 2000-03-01 | Phytopharm Plc | Fluoro substituted sapogenins and their use |
| AT409100B (de) | 2000-07-24 | 2002-05-27 | Evg Entwicklung Verwert Ges | Vorrichtung zum schweissen einer drahtgittermatte |
| GB0107822D0 (en) | 2001-03-28 | 2001-05-23 | Phytopharm Plc | Sapogenin derivatives their synthesis and use methods based upon their use |
| IL164161A0 (en) | 2002-03-27 | 2005-12-18 | Phytopharm Plc | Therapeutic methods and uses of sapogenins and their derivatives |
| TWI334781B (en) | 2002-10-28 | 2010-12-21 | Phytopharm Plc | Stereospecific synthesis of sapogenins |
-
2004
- 2004-04-28 GB GBGB0409567.5A patent/GB0409567D0/en not_active Ceased
-
2005
- 2005-04-28 EP EP05738225A patent/EP1742960A2/fr not_active Withdrawn
- 2005-04-28 JP JP2007510116A patent/JP2007534736A/ja active Pending
- 2005-04-28 KR KR1020067024949A patent/KR20070028387A/ko not_active Application Discontinuation
- 2005-04-28 BR BRPI0510458-0A patent/BRPI0510458A/pt not_active IP Right Cessation
- 2005-04-28 CN CNA2005800133676A patent/CN101076539A/zh active Pending
- 2005-04-28 CA CA002564368A patent/CA2564368A1/fr not_active Abandoned
- 2005-04-28 MX MXPA06012641A patent/MXPA06012641A/es unknown
- 2005-04-28 WO PCT/GB2005/001635 patent/WO2005105825A2/fr active Application Filing
- 2005-04-28 US US11/587,738 patent/US20080004249A1/en not_active Abandoned
- 2005-04-28 SG SG200905023-8A patent/SG155165A1/en unknown
- 2005-04-28 TW TW094113668A patent/TW200538145A/zh unknown
- 2005-04-28 RU RU2006141389/04A patent/RU2006141389A/ru not_active Application Discontinuation
- 2005-04-28 AU AU2005238274A patent/AU2005238274A1/en not_active Abandoned
- 2005-04-28 CN CN2011103029008A patent/CN102516352A/zh active Pending
- 2005-04-28 EP EP11155898A patent/EP2402362A2/fr not_active Withdrawn
-
2006
- 2006-10-26 IL IL178870A patent/IL178870A0/en unknown
- 2006-11-17 ZA ZA200609596A patent/ZA200609596B/en unknown
- 2006-11-28 NO NO20065485A patent/NO20065485L/no not_active Application Discontinuation
-
2011
- 2011-02-22 US US13/032,548 patent/US20110144323A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20080004249A1 (en) | 2008-01-03 |
| SG155165A1 (en) | 2009-09-30 |
| KR20070028387A (ko) | 2007-03-12 |
| TW200538145A (en) | 2005-12-01 |
| IL178870A0 (en) | 2007-03-08 |
| MXPA06012641A (es) | 2006-12-15 |
| RU2006141389A (ru) | 2008-06-10 |
| WO2005105825A3 (fr) | 2006-02-23 |
| JP2007534736A (ja) | 2007-11-29 |
| NO20065485L (no) | 2007-01-29 |
| CA2564368A1 (fr) | 2005-11-10 |
| GB0409567D0 (en) | 2004-06-02 |
| CN102516352A (zh) | 2012-06-27 |
| EP2402362A2 (fr) | 2012-01-04 |
| BRPI0510458A (pt) | 2007-10-30 |
| WO2005105825A2 (fr) | 2005-11-10 |
| AU2005238274A1 (en) | 2005-11-10 |
| US20110144323A1 (en) | 2011-06-16 |
| CN101076539A (zh) | 2007-11-21 |
| EP1742960A2 (fr) | 2007-01-17 |
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