GB959313A - Diphenylalkane derivatives and process for their manufacture - Google Patents
Diphenylalkane derivatives and process for their manufactureInfo
- Publication number
- GB959313A GB959313A GB3512/61A GB351261A GB959313A GB 959313 A GB959313 A GB 959313A GB 3512/61 A GB3512/61 A GB 3512/61A GB 351261 A GB351261 A GB 351261A GB 959313 A GB959313 A GB 959313A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- methoxyphenyl
- phenyl
- compound
- prepared
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises substituted diphenylalkanes of the general formula: <FORM:0959313/C2/1> wherein R1 represents a hydrogen atom or a hydroxy or methoxy group and R2 represents a hydroxy or methoxy group, and acid addition salts thereof, and the preparation of the above diphenylalkanes and the salts by any of the following methods:-(a) phenylacetone is hydrogenated in the presence of an amine of the general formula: <FORM:0959313/C2/2> wherein R1 and R2 have the above significance; (b) an amine of the general formula in the previous method is reacted with a 1-phenyl-2-halogeno-propane or a 1-phenyl-2-halogeno-propene in the presence of an agent binding hydrogen halide, and when the reaction is carried out with a 1-phenyl-2-halogeno-propene hydrogenating the compounds so obtained which are of the general formula: <FORM:0959313/C2/3> <FORM:0959313/C2/4> wherein R1 and R2 have the above significance; (3) an aldehyde of the general formula: <FORM:0959313/C2/5> wherein R1 and R2 have the above significance, is hydrogenated in the presence of 1-phenol-2-amino-propane; (4) a compound of the general formula: <FORM:0959313/C2/6> wherein R1 and R2 have the above significance, is hydrogenated; (5) a suitably substituted diphenyl methane or diphenyl acetonitrile is condensed in the presence of agents capable of splitting off hydrogen halide with an amine of the formula: <FORM:0959313/C2/7> wherein R3 represents a hydrogen atom or a benzyl group and Hal represents a halogen atom and, when a substituted diphenyl acetonitrile is used, a hydrogen atom is substituted for the nitrile group in the cyano compound produced by reaction with sodamide or by hydrolysis of the nitrile group to form a carboxyl group with subsequent decarboxylation and, when R3 represents a benzyl group, the benzyl group is split off from the N-benzyl compound by catalytic hydrogenation; (6) a b ,b diphenyl propionic acid amide of the formula: <FORM:0959313/C2/8> wherein R1 and R2 have the above significance, is reduced to the corresponding amine; (7) a compound of the first general formula above wherein R1 and/or R2 represent hydroxy groups is methylated; (8) a compound of the first general formula above wherein R1 and/or R2 represent methoxy groups is demethylated; and (9) a salt prepared by any of the above methods is converted to the corresponding free base, or a free base prepared by the said methods is converted into an acid addition salt. Therapeutic compositions having activity on cardiac and blood vascular circulation contain as the active ingredient substituted diphenyl alkanes of the first general formula above or a salt thereof. The compositions may be administered parenterally or orally. b ,b -Diphenyl-propionic acid amides of the previous general formula above wherein R1 and R2 have the above significance, are prepared by reacting 1-phenyl-2-amino-propane with the required carboxylic acid chlorides. 1-(m-Methoxyphenyl)-1-phenyl-3-aminopropane is prepared by condensing the methyl ester of cyanoacetic acid with m-methoxybenzaldehyde to form a -cyano-b -(m-methoxyphenyl)-acrylic acid methyl ester, reacting this compound with phenylmagnesium bromide, alkaline hydrolysing the resulting ester, decarboxylating the resulting carboxylic acid to form b -(m-methoxyphenyl)-b -phenyl-propionitrile and hydrogenating this compound. By a similar method 1-(m-methoxyphenyl) -1-(p-methoxyphenyl)-3-aminopropane is prepared via b -(m-methoxyphenyl)-b -(p-methoxyphenyl)-propionitrile. 1 - Phenyl - 2 - [31 - (m - methoxyphenyl) -31-phenylpropene-(31)-yl-(11) ]-amino-propane is prepared by dehydrating 1-phenyl-2-[31-(m-methoxyphenyl) - 31 - phenyl - 31 - hydroxy-propyl-(11)]-amino-propane with p-toluenesulphonic acid.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF30422A DE1242632B (en) | 1960-01-30 | 1960-01-30 | Process for the preparation of alkoxy- or hydroxy-substituted diphenylalkane derivatives and their non-toxic acid addition salts |
Publications (1)
Publication Number | Publication Date |
---|---|
GB959313A true GB959313A (en) | 1964-05-27 |
Family
ID=7093758
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3512/61A Expired GB959313A (en) | 1960-01-30 | 1961-01-30 | Diphenylalkane derivatives and process for their manufacture |
Country Status (7)
Country | Link |
---|---|
BE (1) | BE599660A (en) |
BR (1) | BR6126216D0 (en) |
CH (6) | CH406237A (en) |
DE (1) | DE1242632B (en) |
FR (2) | FR1274M (en) |
GB (1) | GB959313A (en) |
OA (1) | OA01976A (en) |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1110706A (en) * | 1953-05-18 | 1956-02-16 | Laboratoires Labaz Soc D | Process for the preparation of 2-butylamines disubstituted in position 4 by hydroxylated aromatic radicals |
-
1960
- 1960-01-30 DE DEF30422A patent/DE1242632B/en active Pending
-
1961
- 1961-01-26 CH CH89861A patent/CH406237A/en unknown
- 1961-01-26 CH CH1597165A patent/CH407153A/en unknown
- 1961-01-26 CH CH1597465A patent/CH407150A/en unknown
- 1961-01-26 CH CH1597265A patent/CH407151A/en unknown
- 1961-01-26 CH CH1597565A patent/CH407152A/en unknown
- 1961-01-26 CH CH1597365A patent/CH407149A/en unknown
- 1961-01-30 GB GB3512/61A patent/GB959313A/en not_active Expired
- 1961-01-30 BE BE599660A patent/BE599660A/en unknown
- 1961-01-30 BR BR126216/61A patent/BR6126216D0/en unknown
- 1961-04-29 FR FR860358A patent/FR1274M/en active Active
- 1961-04-29 FR FR860357A patent/FR1126M/en active Active
-
1964
- 1964-12-31 OA OA51807A patent/OA01976A/en unknown
Also Published As
Publication number | Publication date |
---|---|
CH406237A (en) | 1966-01-31 |
CH407152A (en) | 1966-02-15 |
CH407149A (en) | 1966-02-15 |
CH407151A (en) | 1966-02-15 |
BE599660A (en) | 1961-07-31 |
DE1242632B (en) | 1967-06-22 |
CH407153A (en) | 1966-02-15 |
FR1126M (en) | 1962-02-12 |
OA01976A (en) | 1970-05-05 |
FR1274M (en) | 1962-05-02 |
CH407150A (en) | 1966-02-15 |
BR6126216D0 (en) | 1973-05-17 |
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