ES8308571A1 - Inclusion complexes of steroids with delta -cyclodextrin - Google Patents
Inclusion complexes of steroids with delta -cyclodextrinInfo
- Publication number
- ES8308571A1 ES8308571A1 ES516840A ES516840A ES8308571A1 ES 8308571 A1 ES8308571 A1 ES 8308571A1 ES 516840 A ES516840 A ES 516840A ES 516840 A ES516840 A ES 516840A ES 8308571 A1 ES8308571 A1 ES 8308571A1
- Authority
- ES
- Spain
- Prior art keywords
- cyclodextrin
- steroids
- delta
- reichstein
- complexes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920000858 Cyclodextrin Polymers 0.000 title abstract 2
- 150000003431 steroids Chemical class 0.000 title abstract 2
- 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 abstract 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 abstract 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 abstract 1
- BTTWKVFKBPAFDK-UHFFFAOYSA-N (9beta,10alpha)-Androst-4-ene-3,17-dione Natural products OC1CCC2(C)C3CCC(C)(C(CC4)O)C4C3CCC2=C1 BTTWKVFKBPAFDK-UHFFFAOYSA-N 0.000 abstract 1
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 abstract 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 abstract 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 abstract 1
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 abstract 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-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)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 HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 abstract 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 abstract 1
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 abstract 1
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 abstract 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class 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 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 229960003957 dexamethasone Drugs 0.000 abstract 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 229960003399 estrone Drugs 0.000 abstract 1
- 229960000890 hydrocortisone Drugs 0.000 abstract 1
- 229960001566 methyltestosterone Drugs 0.000 abstract 1
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 abstract 1
- 229960004719 nandrolone Drugs 0.000 abstract 1
- 230000003589 nefrotoxic effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229960005205 prednisolone Drugs 0.000 abstract 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 abstract 1
- 229960003387 progesterone Drugs 0.000 abstract 1
- 239000000186 progesterone Substances 0.000 abstract 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 abstract 1
- 229960002256 spironolactone Drugs 0.000 abstract 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 abstract 1
- 229960005294 triamcinolone Drugs 0.000 abstract 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nanotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The title complexes have 3-100 times the water-solubility of the uncomplexed steroids, e.g. spironolactone, nortestosterone, methyltestosterone, androst-4-ene- 3,17-dione, progesterone, Reichstein S, Reichstein S aceate, 16-methyl- Reichstein S, Hydrocortisone, estrone, dexamethasone, prednisolone, triamcinolone, pregnenetriolone triacetate. Pharmaceutical compositions containing the title complexes are free from the nephrotoxic effects of the corresponding alpha - and beta -cyclodextrin complexes owing to the faster enzymatic decomposition of delta -cyclodextrin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU813147A HU190356B (en) | 1981-10-27 | 1981-10-27 | Process for preparing steroid-gamma-cyclodextrin inclusion complexes with high water-solubility |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES8308571A1 true ES8308571A1 (en) | 1983-09-16 |
| ES516840A0 ES516840A0 (en) | 1983-09-16 |
Family
ID=10962794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES516840A Granted ES516840A0 (en) | 1981-10-27 | 1982-10-26 | PROCEDURE TO PREPARE INCLUSION COMPLEXES OF POORLY SOLUBLE STEROIDS IN WATER WITH -CYCLODEXTRIN. |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5883699A (en) |
| BE (1) | BE894825A (en) |
| DD (1) | DD208549A5 (en) |
| DE (1) | DE3238800A1 (en) |
| DK (1) | DK474782A (en) |
| ES (1) | ES516840A0 (en) |
| FR (1) | FR2515187A1 (en) |
| GB (1) | GB2109381A (en) |
| HU (1) | HU190356B (en) |
| IT (1) | IT1191049B (en) |
| NL (1) | NL8204122A (en) |
| SE (1) | SE8206055L (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU196230B (en) * | 1983-12-29 | 1988-10-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing water-soluble forms of polyene antibiotics and pharmaceutics comprising such active ingredient and plant protective with antifungal effect |
| GB2162529B (en) * | 1984-06-08 | 1988-03-02 | Nitrokemia Ipartelepek | B-cyclodextrin complex of benzene sulphonyl urea derivatives |
| US5223295A (en) * | 1988-01-22 | 1993-06-29 | Asterol International | Process for the elimination of steroid compounds contained in substance of biological origin |
| WO1990001320A1 (en) * | 1988-08-15 | 1990-02-22 | American Maize-Products Company | Water soluble branched beta cyclodextrin steroid complex |
| US5229370A (en) * | 1988-08-15 | 1993-07-20 | Ammeraal Robert N | Water soluble branched beta cyclodextrin steroid complex |
| CA2087452A1 (en) * | 1991-05-20 | 1992-11-21 | Toshiro Tsuda | Steriod compound combined with polysaccharide |
| US20040152664A1 (en) * | 1998-09-02 | 2004-08-05 | Allergan, Inc. | Prednisolone compositions |
| EP1629845A3 (en) * | 2000-11-02 | 2006-03-22 | Akzo Nobel N.V. | Use of cortisol-sequestering agents for the treatment of hypercortisolaemia related disorders |
| EP1216713A1 (en) | 2000-12-20 | 2002-06-26 | Schering Aktiengesellschaft | Compositions of estrogen-cyclodextrin complexes |
| WO2002049674A1 (en) * | 2000-12-20 | 2002-06-27 | Schering Aktiengesellschaft | Cyclodextrin-drospirenone inclusion complexes |
| EP1216712A1 (en) * | 2000-12-20 | 2002-06-26 | Schering Aktiengesellschaft | Cyclodextrin-drospirenone inclusion complexes |
| US20070020298A1 (en) * | 2003-12-31 | 2007-01-25 | Pipkin James D | Inhalant formulation containing sulfoalkyl ether gamma-cyclodextrin and corticosteroid |
| US20070020299A1 (en) | 2003-12-31 | 2007-01-25 | Pipkin James D | Inhalant formulation containing sulfoalkyl ether cyclodextrin and corticosteroid |
| EP2825567A2 (en) * | 2012-03-13 | 2015-01-21 | Amphidex A/S | Production of stabilized channel type cyclodextrin crystals |
-
1981
- 1981-10-27 HU HU813147A patent/HU190356B/en not_active IP Right Cessation
-
1982
- 1982-10-20 DE DE19823238800 patent/DE3238800A1/en not_active Withdrawn
- 1982-10-25 SE SE8206055A patent/SE8206055L/en not_active Application Discontinuation
- 1982-10-26 ES ES516840A patent/ES516840A0/en active Granted
- 1982-10-26 NL NL8204122A patent/NL8204122A/en not_active Application Discontinuation
- 1982-10-26 FR FR8217943A patent/FR2515187A1/en not_active Withdrawn
- 1982-10-26 DD DD82244272A patent/DD208549A5/en unknown
- 1982-10-26 IT IT23942/82A patent/IT1191049B/en active
- 1982-10-26 GB GB08230513A patent/GB2109381A/en not_active Withdrawn
- 1982-10-26 DK DK474782A patent/DK474782A/en not_active Application Discontinuation
- 1982-10-27 BE BE0/209341A patent/BE894825A/en not_active IP Right Cessation
- 1982-10-27 JP JP57187658A patent/JPS5883699A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HU190356B (en) | 1986-08-28 |
| NL8204122A (en) | 1983-05-16 |
| JPS5883699A (en) | 1983-05-19 |
| IT1191049B (en) | 1988-02-24 |
| SE8206055L (en) | 1983-04-28 |
| BE894825A (en) | 1983-02-14 |
| DK474782A (en) | 1983-04-28 |
| DE3238800A1 (en) | 1983-05-05 |
| SE8206055D0 (en) | 1982-10-25 |
| GB2109381A (en) | 1983-06-02 |
| IT8223942A0 (en) | 1982-10-26 |
| DD208549A5 (en) | 1984-04-04 |
| ES516840A0 (en) | 1983-09-16 |
| FR2515187A1 (en) | 1983-04-29 |
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