NZ196162A - 2-(2-(1,4-benzodioxanyl))-2-imidazoline and pharmaceutical compositions - Google Patents
2-(2-(1,4-benzodioxanyl))-2-imidazoline and pharmaceutical compositionsInfo
- Publication number
- NZ196162A NZ196162A NZ196162A NZ19616281A NZ196162A NZ 196162 A NZ196162 A NZ 196162A NZ 196162 A NZ196162 A NZ 196162A NZ 19616281 A NZ19616281 A NZ 19616281A NZ 196162 A NZ196162 A NZ 196162A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- formula
- imidazoline
- salt
- toxic salt
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 77
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 27
- 231100000252 nontoxic Toxicity 0.000 claims description 27
- 230000003000 nontoxic effect Effects 0.000 claims description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 15
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 3
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- 230000001430 anti-depressive effect Effects 0.000 description 1
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- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8003636 | 1980-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ196162A true NZ196162A (en) | 1983-06-17 |
Family
ID=10511105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ196162A NZ196162A (en) | 1980-02-04 | 1981-02-02 | 2-(2-(1,4-benzodioxanyl))-2-imidazoline and pharmaceutical compositions |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4818764A (en, 2012) |
| EP (1) | EP0033655B1 (en, 2012) |
| JP (1) | JPS56122378A (en, 2012) |
| AR (1) | AR225794A1 (en, 2012) |
| AT (1) | ATE7228T1 (en, 2012) |
| AU (1) | AU535320B2 (en, 2012) |
| CA (1) | CA1156241A (en, 2012) |
| CS (1) | CS254956B2 (en, 2012) |
| DD (1) | DD155991A5 (en, 2012) |
| DE (1) | DE3163256D1 (en, 2012) |
| DK (1) | DK160092C (en, 2012) |
| ES (1) | ES8202553A1 (en, 2012) |
| FI (1) | FI67543C (en, 2012) |
| GB (1) | GB2068376B (en, 2012) |
| GR (1) | GR73853B (en, 2012) |
| HU (1) | HU187295B (en, 2012) |
| IE (1) | IE51736B1 (en, 2012) |
| IL (1) | IL62039A (en, 2012) |
| NO (1) | NO154882C (en, 2012) |
| NZ (1) | NZ196162A (en, 2012) |
| PH (1) | PH16249A (en, 2012) |
| PL (1) | PL128368B1 (en, 2012) |
| PT (1) | PT72435B (en, 2012) |
| SU (1) | SU1128837A3 (en, 2012) |
| ZA (1) | ZA81666B (en, 2012) |
| ZW (1) | ZW2381A1 (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ199469A (en) * | 1981-01-30 | 1984-03-16 | Reckitt & Colmann Prod Ltd | Benzodioxanyl-2-imidazoline derivatives and pharmaceutical compositions |
| US4436914A (en) | 1981-08-03 | 1984-03-13 | Kluge Arthur F | Benzodioxane-imidazoline compounds as antihypertensives |
| NZ203680A (en) * | 1982-04-17 | 1985-08-16 | Reckitt & Colmann Prod Ltd | Imidazolines and pharmaceutical compositions |
| FR2527208B1 (fr) * | 1982-05-19 | 1985-07-19 | Inst Nat Sante Rech Med | Isomeres optiques de la (benzodioxanne-1,4 yl-2)-2d-2 imidazoline, leur preparation et leur application en therapeutique |
| EP0115142B1 (en) * | 1982-12-23 | 1986-11-05 | Ici Americas Inc. | Chroman compounds |
| US4634714A (en) * | 1983-12-01 | 1987-01-06 | American Home Products Corporation | Inhibition of prolactin release by a benzodioxinylimidazoline derivative |
| US4882343A (en) * | 1987-08-28 | 1989-11-21 | G. D. Searle & Co. | Biarylalkylimidazole derivatives as anti-depressants |
| GB8720600D0 (en) * | 1987-09-02 | 1987-10-07 | Saad Al Damluji | Pharmaceutical compositions |
| US5240930A (en) * | 1987-09-02 | 1993-08-31 | National Research Development Corporation | Pharmaceutical compositions for treatment of depression and low blood pressure |
| FR2698789B1 (fr) * | 1992-12-07 | 1995-03-03 | Pf Medicament | Utilisation de l'idazoxan et ses dérivés pour la préparation d'un médicament destiné au traitement de la maladie de Parkinson et de son évolution. |
| FR2700113B1 (fr) * | 1993-01-07 | 1995-03-24 | Pf Medicament | Utilisation de l'Idazoxan et ses dérivés pour la fabrication de médicaments destinés au traitement des maladies neurodégénératives et en particulier l'évolution de la maladie d'Alzheimer. |
| US5574059A (en) * | 1995-10-27 | 1996-11-12 | Cornell Research Foundation, Inc. | Treating disorders mediated by vascular smooth muscle cell proliferation |
| FR2795727B1 (fr) * | 1999-06-29 | 2001-09-21 | Pf Medicament | Nouveaux derives benzodioxanne imidazolines fluores, leur preparation et leurs applications en therapeutique |
| FR2801786B1 (fr) * | 1999-12-01 | 2002-03-01 | Fabre Pierre Cosmetique | Nouvelles compositions topiques a base d'idazoxan et de cafeine ou de ses derives solubles et leur utilisation comme amincissant et/ou dans le traitement de la cellulite |
| US20030022814A1 (en) * | 2000-02-29 | 2003-01-30 | Reines Scott A | Method for treating or preventing depression |
| US8476307B2 (en) * | 2003-10-28 | 2013-07-02 | Pierre Fabre Medicament | Pharmaceutical composition based on idazoxan, salts, hydrates or polymorphs thereof |
| US7595335B2 (en) * | 2003-10-28 | 2009-09-29 | Pierre Fabre Medicament | Pharmaceutical composition based on idazoxan, salts, hydrates or polymorphs thereof |
| FR2861299B1 (fr) * | 2003-10-28 | 2006-01-27 | Pf Medicament | Compositions pharmaceutiques a base de derives d'idasoxan sous formes polymorphes |
| US20250195477A1 (en) * | 2022-02-16 | 2025-06-19 | Terran Biosciences Inc. | Deuterated idazoxan and methods of use thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2641601A (en) * | 1950-11-24 | 1953-06-09 | Hoffmann La Roche | Furans and method of preparation |
| US2979511A (en) * | 1959-03-25 | 1961-04-11 | Olin Mathieson | Certain 1, 4-benzodioxanyl imidazolines and corresponding pyrimidines and process |
| EP0003732B1 (en) * | 1978-02-01 | 1983-10-19 | The Wellcome Foundation Limited | Imidazole derivatives and salts thereof, their synthesis, and pharmaceutical formulations thereof |
| US4302469A (en) * | 1980-09-10 | 1981-11-24 | Syntex (U.S.A.) Inc. | 2-(1,4-Benzodioxan-2-ylalkyl)imidazoles useful as antidepressants |
| US4301171A (en) * | 1980-12-03 | 1981-11-17 | Syntex (U.S.A.) Inc. | 2-(1,4-Benzodioxan-2-ylalkyl)benzimidazoles useful as anti-depressants |
| US4315021A (en) * | 1980-12-03 | 1982-02-09 | Syntex (U.S.A.) Inc. | 2-(1,4-Benzodioxan-2-ylalkyl)imidazoles |
| US4436914A (en) * | 1981-08-03 | 1984-03-13 | Kluge Arthur F | Benzodioxane-imidazoline compounds as antihypertensives |
| US4352809A (en) * | 1981-09-04 | 1982-10-05 | Smithkline Corporation | Method of producing alpha2 antagonism |
-
1981
- 1981-01-22 PH PH25123A patent/PH16249A/en unknown
- 1981-01-30 AU AU66758/81A patent/AU535320B2/en not_active Ceased
- 1981-02-01 IL IL62039A patent/IL62039A/xx not_active IP Right Cessation
- 1981-02-02 EP EP81300427A patent/EP0033655B1/en not_active Expired
- 1981-02-02 AT AT81300427T patent/ATE7228T1/de not_active IP Right Cessation
- 1981-02-02 IE IE199/81A patent/IE51736B1/en not_active IP Right Cessation
- 1981-02-02 PL PL1981229488A patent/PL128368B1/pl unknown
- 1981-02-02 DK DK045081A patent/DK160092C/da not_active IP Right Cessation
- 1981-02-02 GR GR64021A patent/GR73853B/el unknown
- 1981-02-02 HU HU81233A patent/HU187295B/hu not_active IP Right Cessation
- 1981-02-02 NZ NZ196162A patent/NZ196162A/en unknown
- 1981-02-02 PT PT72435A patent/PT72435B/pt not_active IP Right Cessation
- 1981-02-02 GB GB8103150A patent/GB2068376B/en not_active Expired
- 1981-02-02 ES ES499034A patent/ES8202553A1/es not_active Expired
- 1981-02-02 DD DD81227377A patent/DD155991A5/de unknown
- 1981-02-02 US US06/230,195 patent/US4818764A/en not_active Expired - Fee Related
- 1981-02-02 SU SU813241694A patent/SU1128837A3/ru active
- 1981-02-02 CA CA000369899A patent/CA1156241A/en not_active Expired
- 1981-02-02 FI FI810288A patent/FI67543C/fi not_active IP Right Cessation
- 1981-02-02 DE DE8181300427T patent/DE3163256D1/de not_active Expired
- 1981-02-02 NO NO810351A patent/NO154882C/no unknown
- 1981-02-02 JP JP1420281A patent/JPS56122378A/ja active Granted
- 1981-02-02 AR AR284181A patent/AR225794A1/es active
- 1981-02-02 CS CS81738A patent/CS254956B2/cs unknown
- 1981-02-02 ZW ZW23/81A patent/ZW2381A1/xx unknown
- 1981-02-02 ZA ZA00810666A patent/ZA81666B/xx unknown
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