GB898010A - Process for the preparation of basic substituted carbinols - Google Patents
Process for the preparation of basic substituted carbinolsInfo
- Publication number
- GB898010A GB898010A GB9986/60A GB998660A GB898010A GB 898010 A GB898010 A GB 898010A GB 9986/60 A GB9986/60 A GB 9986/60A GB 998660 A GB998660 A GB 998660A GB 898010 A GB898010 A GB 898010A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- basic
- alkyl radical
- hydrogen atom
- carbinols
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises basic carbinols of the general formula <FORM:0898010/IV (b)/1> (wherein R1 represents a C1-4 alkyl radical, R2 represents a hydrogen atom, a C1-4 alkyl radical or an alkenyl or aralkyl radical, R3 and R4 may be identical or different and each represent a hydrogen atom, a C1-4 alkyl radical or a halogen atom, R5 and R6 represent identical or different C1-4 alkyl radicals or jointly form with the nitrogen atom a pyrrolidine or piperidine ring, and n is 1 or 2) and their addition salts with physiologically acceptable acids; the preparation of the basic carbinols by (a) reacting a ketone of the formula <FORM:0898010/IV (b)/2> or <FORM:0898010/IV (b)/3> with a Grignard compound of the formula <FORM:0898010/IV (b)/4> or R1MgX(V) respectively (wherein X represents a halogen atom), or (b) reacting a basic propionic acid ester of the general formula <FORM:0898010/IV (b)/5> (wherein R7 represents a C1-4 alkyl radical)¦with two Grignard compounds of the general formula III and V above, in either order or simultaneously, or (c) reducing the -CN group in a hydroxynitrile of the general formula <FORM:0898010/IV (b)/6> to -CH2NH2 and subjecting the NH2 group to alkylation or conversion to a pyrrolidino or piperidino group; and pharmaceutical preparations containing the basic carbinols or their salts (see Group VI). Basic ketones of the general formulae II and IV above are prepared from the corresponding simple ketones by Mannich reaction with formaldehyde and the appropriate secondary amines. Basic propionic acid esters of the general formula VI above are prepared by addition of amines R5R6NH (XI) to acrylic esters of the general formula <FORM:0898010/IV (b)/7> Hydroxynitriles of the general formula IX above are prepared by reacting a ketone of the general formula <FORM:0898010/IV (b)/8> with a nitrile of the general formula R2CH2CN (VIII).ALSO:Anti-tussive compositions contain a basic carbinol (or an addition salt thereof with an inorganic or organic acid) of the general formula <FORM:0898010/VI/1> (wherein R1 represents a C1-4 alkyl radical, R2 represents a hydrogen atom, a C1-4 alkyl radical or an alkenyl, aryl or aralkyl radical, R3 and R4 may be identical or different and each represent a hydrogen atom, a C1-4 alkyl radical or a halogen atom, R5 and R6 represent identical or different C1-4 alkyl radicals or jointly form with the nitrogen atom a pyrrolidine or piperidine ring, and n is 1 or 2) together with a pharmaceutically acceptable carrier. Examples are given of the formulation of 1-p-chlorophenyl - 2,3 - dimethyl - 4 - dimethylaminobutanol-(2) in drops (also containing aniseed oil and menthol), a cough syrup (also containing eucalyptus-menthol essence), tablets, dragees, suppositories and an injection solution. Suspensions are also referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET16442A DE1146068B (en) | 1959-03-21 | 1959-03-21 | Process for the preparation of basic substituted carbinols |
| DET16720A DE1153380B (en) | 1959-05-21 | 1959-05-21 | Process for the preparation of basic substituted carbinols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB898010A true GB898010A (en) | 1962-06-06 |
Family
ID=25999309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9986/60A Expired GB898010A (en) | 1959-03-21 | 1960-03-21 | Process for the preparation of basic substituted carbinols |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE588825A (en) |
| CH (1) | CH396942A (en) |
| DK (1) | DK107034C (en) |
| GB (1) | GB898010A (en) |
| OA (1) | OA01023A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4177291A (en) * | 1976-08-25 | 1979-12-04 | Astra Lakemedel Aktiebolag | Compounds having antidepressive activity |
| CZ300744B6 (en) * | 1999-07-09 | 2009-07-29 | Sanofi-Aventis | Preparation process of 2-(2-arylmorpholin-2-yl)ethanol derivatives and intermediates thereof |
-
1960
- 1960-03-14 CH CH285760A patent/CH396942A/en unknown
- 1960-03-18 BE BE588825A patent/BE588825A/en unknown
- 1960-03-19 DK DK106660AA patent/DK107034C/en active
- 1960-03-21 GB GB9986/60A patent/GB898010A/en not_active Expired
-
1964
- 1964-12-30 OA OA51181A patent/OA01023A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4177291A (en) * | 1976-08-25 | 1979-12-04 | Astra Lakemedel Aktiebolag | Compounds having antidepressive activity |
| CZ300744B6 (en) * | 1999-07-09 | 2009-07-29 | Sanofi-Aventis | Preparation process of 2-(2-arylmorpholin-2-yl)ethanol derivatives and intermediates thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DK107034C (en) | 1967-04-17 |
| BE588825A (en) | 1960-09-19 |
| CH396942A (en) | 1965-08-15 |
| OA01023A (en) | 1968-08-07 |
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