WO1990015792A1 - Novel cyclodextrin inclusion complexes - Google Patents
Novel cyclodextrin inclusion complexes Download PDFInfo
- Publication number
- WO1990015792A1 WO1990015792A1 PCT/SE1990/000436 SE9000436W WO9015792A1 WO 1990015792 A1 WO1990015792 A1 WO 1990015792A1 SE 9000436 W SE9000436 W SE 9000436W WO 9015792 A1 WO9015792 A1 WO 9015792A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ethyl
- benzonitrile
- propylsulfinyl
- cyclodextrins
- hydroxypropoxy
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
Definitions
- the invention relates to novel cyclodextrin inclusion complexes, process for their preparation and their use,
- the present invention relates to inclusion complexes of the compound 4-[3-[ ethyl[3-(propylsulfinyl)-propyl]amino]-2-hydroxypropoxy]-benzonitrile with cyclodextrins, their preparation and use.
- the present invention relates to an inclusion complex of the compound of the formula I with one or more cyclodextrins.
- the compound of the formula I is present in the form of a stereoisomeric mixture.
- the compound of the formula I is present in the form of one of the stereoisomers.
- stereoisomers are, in addition to the two stereoisomers mentioned above, the following: 4-[3-[ethyl[3-((R*)-propylsulfinyl)propyl]amino]-2(R)- hydroxypropoxy]-benzonitrile,
- the cyclodextrin may be an unsubstituted cyclodextrin, i.e. ⁇ -, ⁇ - or ⁇ -cyclodextrin, or a substituted cyclodextrin, e.g.
- a substituted cyclodextrin selected from the group consisting of methylcyclodextrins, ethylcyclodextrins, hydroxyethyl cyclodextrins and hydroxypropyl cyclodextrins.
- hydroxyethyl and hydroxypropyl cyclodextrins are hydroxyethyl- ⁇ -cyclodextrin and hydroxypropyl- ⁇ - cyclodextrin, respectively.
- the cyclodextrin is ⁇ -cyclodextrin or ⁇ - cyclodextrin.
- the inclusion complex may be formed with one single cyclodextrin or with a mixture of at least two cyclodextrins such as those mentioned above.
- the molar ratio between the cyclodextrin or mixture of cyclodextrins and the compound of the. formula I will generally be in the range of from 10:1 to 1:10, preferably above or equal to 1:1, such as 1:1 to 5:1.
- the present invention also relates to a process for the preparation of an inclusion complex according to the present invention, which process comprises reacting the compound of the formula I above with a cyclodextrin or a mixture of cyclodextrins.
- the reaction is typically carried out in a suitable solvent such as water.
- the invention further relates to a method of preventing or reducing cardiac arrhythmias in mammals, including man, which comprises administering to a host in need of such treatment an effective amount of an inclusion complex of the compound of the formula I with one or more cyclodextrins.
- the invention yet further relates to an inclusion complex of the compound of the formula I with one or more cyclodextrins for use as a medicament, particularly as an antiarrhythmic agent.
- the invention also relates to the use of an inclusion complex of the compound of the formula I with one or more cyclodextrins for the manufacture of medicaments with action against cardiac arrhythmias.
- Solution 1 was prepared by dissolving 7.53 g 4-[3-[ethyl[3-(propylsulfinyl)propyl]amino]-2-hydroxypropoxy]-benzonitrile, 1.54 g tartaric acid in 5 g deionized water.
- Solution 2 was prepared by dissolving 43.0 g ⁇ -cyclodextrin in 300 g deionized water by agitation at 70°C.
- Solution 1 was prepared by dissolving 0.75 g 4-[3-[ethyl-[3-(propylsulfinyl)propyl]amino]-2-hydroxypropoxy]-benzonitrile, 0.153 g tartaric acid in 2.5 g deionized water.
- Solution 2 was prepared by dissolving 4.3 g ⁇ -cyclodextrin in 30 g water at 25°C.
- Solution 1 was poured
- the total yield was 4 g and the content 4-[3-/ethyl[3-(propylsulfinyl)propyl]amino]-2-hydroxypropoxy]-benzonitrile was assayed spectrophotometrically to 15 % by weight.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nanotechnology (AREA)
- Epidemiology (AREA)
- General Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Medical Informatics (AREA)
- Biotechnology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019910701912A KR920702674A (en) | 1989-06-20 | 1990-06-19 | New Cyclodextrin Inclusion Complexes |
NO91914927A NO914927L (en) | 1989-06-20 | 1991-12-13 | NEW CYCLODE EXTRA INCLUSION COMPLEXS |
FI915935A FI915935A0 (en) | 1989-06-20 | 1991-12-17 | NYA CYKLODEXTRININKLUSIONSKOMPLEXER. |
LV930886A LV10249A (en) | 1989-06-20 | 1993-06-30 | New cyclodextrin inclusions complexity and application |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE8902235A SE8902235D0 (en) | 1989-06-20 | 1989-06-20 | NOVEL CYCLODEXTRIN INCLUSION COMPLEXES |
SE8902235-4 | 1989-06-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1990015792A1 true WO1990015792A1 (en) | 1990-12-27 |
Family
ID=20376340
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/SE1990/000436 WO1990015792A1 (en) | 1989-06-20 | 1990-06-19 | Novel cyclodextrin inclusion complexes |
Country Status (15)
Country | Link |
---|---|
EP (1) | EP0478677A1 (en) |
JP (1) | JPH04506212A (en) |
KR (1) | KR920702674A (en) |
AU (1) | AU641670B2 (en) |
CA (1) | CA2058996A1 (en) |
DD (1) | DD297404A5 (en) |
FI (1) | FI915935A0 (en) |
GR (1) | GR1000747B (en) |
HU (1) | HUT59085A (en) |
IE (1) | IE902162A1 (en) |
LT (1) | LTIP1725A (en) |
LV (1) | LV10249A (en) |
PT (1) | PT94415A (en) |
SE (1) | SE8902235D0 (en) |
WO (1) | WO1990015792A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4207922A1 (en) * | 1992-03-13 | 1993-09-23 | Pharmatech Gmbh | New water-soluble inclusion complexes contg randomly substd. methyl-beta-cyclodextrin - for admin. of substances which are only sparingly soluble in water |
DE4227569C1 (en) * | 1992-08-20 | 1994-06-09 | Inst Chemo Biosensorik | Enzymatic determn. of inorganic phosphate - using combination of di:saccharide phosphorylase, phosphatase or maltose synthase, and glucose oxido-reductase |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE8902236D0 (en) * | 1989-06-20 | 1989-06-20 | Haessle Ab | NOVEL POLYSTYRENESULPHONATE |
US7141555B2 (en) * | 2000-12-19 | 2006-11-28 | Cephalon, Inc. | Modafinil compound and cyclodextrin mixtures |
TWI373473B (en) * | 2005-09-02 | 2012-10-01 | Otsuka Pharma Co Ltd | Anticancer agent |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1433920A (en) * | 1973-10-01 | 1976-04-28 | Ici Ltd | Alkanolamine derivatives |
GB1457876A (en) * | 1972-12-15 | 1976-12-08 | Ici Ltd | Alkanolamine derivatives device for use in |
DE2948869A1 (en) * | 1978-12-12 | 1980-07-03 | Chinoin Gyogyszer Es Vegyeszet | THE INCLUDING COMPLEXES OF THE ALLYCIN FORMED WITH CYCLODEXTRIN, AND METHODS FOR THE PRODUCTION OF THESE COMPLEXES AND MEDICINAL PRODUCTS CONTAINING THEM |
DE3118218A1 (en) * | 1980-05-09 | 1982-04-22 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára RT, 1045 Budapest | Water-soluble inclusion complexes of biologically active organic compounds which are insoluble or have only limited solubility in water, and their aqueous solutions, as well as their preparation and pharmaceutical products containing these compounds |
EP0094157A1 (en) * | 1982-04-30 | 1983-11-16 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition and its use |
EP0322390A2 (en) * | 1987-12-23 | 1989-06-28 | Aktiebolaget Hässle | Novel antiarrhythmic agents I |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5718602A (en) * | 1980-05-28 | 1982-01-30 | Hokko Chem Ind Co Ltd | Herbicide |
GB8506792D0 (en) * | 1985-03-15 | 1985-04-17 | Janssen Pharmaceutica Nv | Derivatives of y-cyclodextrin |
SE8902237D0 (en) * | 1989-06-20 | 1989-06-20 | Haessle Ab | NOVEL STEREOISOMERS |
SE8902236D0 (en) * | 1989-06-20 | 1989-06-20 | Haessle Ab | NOVEL POLYSTYRENESULPHONATE |
-
1989
- 1989-06-20 SE SE8902235A patent/SE8902235D0/en unknown
-
1990
- 1990-06-15 IE IE216290A patent/IE902162A1/en unknown
- 1990-06-16 DD DD90341729A patent/DD297404A5/en not_active IP Right Cessation
- 1990-06-18 GR GR900100458A patent/GR1000747B/en unknown
- 1990-06-19 EP EP90910159A patent/EP0478677A1/en not_active Ceased
- 1990-06-19 WO PCT/SE1990/000436 patent/WO1990015792A1/en not_active Application Discontinuation
- 1990-06-19 CA CA002058996A patent/CA2058996A1/en not_active Abandoned
- 1990-06-19 PT PT94415A patent/PT94415A/en not_active Application Discontinuation
- 1990-06-19 AU AU59374/90A patent/AU641670B2/en not_active Ceased
- 1990-06-19 JP JP2509477A patent/JPH04506212A/en active Pending
- 1990-06-19 HU HU905542A patent/HUT59085A/en unknown
- 1990-06-19 KR KR1019910701912A patent/KR920702674A/en not_active Application Discontinuation
-
1991
- 1991-12-17 FI FI915935A patent/FI915935A0/en not_active Application Discontinuation
-
1993
- 1993-06-30 LV LV930886A patent/LV10249A/en unknown
- 1993-12-30 LT LTIP1725A patent/LTIP1725A/en not_active Application Discontinuation
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1457876A (en) * | 1972-12-15 | 1976-12-08 | Ici Ltd | Alkanolamine derivatives device for use in |
GB1433920A (en) * | 1973-10-01 | 1976-04-28 | Ici Ltd | Alkanolamine derivatives |
DE2948869A1 (en) * | 1978-12-12 | 1980-07-03 | Chinoin Gyogyszer Es Vegyeszet | THE INCLUDING COMPLEXES OF THE ALLYCIN FORMED WITH CYCLODEXTRIN, AND METHODS FOR THE PRODUCTION OF THESE COMPLEXES AND MEDICINAL PRODUCTS CONTAINING THEM |
DE3118218A1 (en) * | 1980-05-09 | 1982-04-22 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára RT, 1045 Budapest | Water-soluble inclusion complexes of biologically active organic compounds which are insoluble or have only limited solubility in water, and their aqueous solutions, as well as their preparation and pharmaceutical products containing these compounds |
EP0094157A1 (en) * | 1982-04-30 | 1983-11-16 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition and its use |
EP0322390A2 (en) * | 1987-12-23 | 1989-06-28 | Aktiebolaget Hässle | Novel antiarrhythmic agents I |
WO1989005794A1 (en) * | 1987-12-23 | 1989-06-29 | Aktiebolaget Hässle | Novel antiarrhythmic agents i |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4207922A1 (en) * | 1992-03-13 | 1993-09-23 | Pharmatech Gmbh | New water-soluble inclusion complexes contg randomly substd. methyl-beta-cyclodextrin - for admin. of substances which are only sparingly soluble in water |
DE4227569C1 (en) * | 1992-08-20 | 1994-06-09 | Inst Chemo Biosensorik | Enzymatic determn. of inorganic phosphate - using combination of di:saccharide phosphorylase, phosphatase or maltose synthase, and glucose oxido-reductase |
Also Published As
Publication number | Publication date |
---|---|
SE8902235D0 (en) | 1989-06-20 |
EP0478677A1 (en) | 1992-04-08 |
IE902162A1 (en) | 1991-01-02 |
LV10249A (en) | 1994-10-20 |
KR920702674A (en) | 1992-10-06 |
PT94415A (en) | 1991-02-08 |
AU5937490A (en) | 1991-01-08 |
LTIP1725A (en) | 1995-07-25 |
AU641670B2 (en) | 1993-09-30 |
DD297404A5 (en) | 1992-01-09 |
IE902162L (en) | 1990-12-20 |
JPH04506212A (en) | 1992-10-29 |
CA2058996A1 (en) | 1990-12-21 |
GR1000747B (en) | 1992-12-30 |
HUT59085A (en) | 1992-04-28 |
GR900100458A (en) | 1991-11-15 |
FI915935A0 (en) | 1991-12-17 |
HU905542D0 (en) | 1992-03-30 |
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