GB777209A - Improvements in or relating to piperazine derivatives - Google Patents
Improvements in or relating to piperazine derivativesInfo
- Publication number
- GB777209A GB777209A GB36197/55A GB3619755A GB777209A GB 777209 A GB777209 A GB 777209A GB 36197/55 A GB36197/55 A GB 36197/55A GB 3619755 A GB3619755 A GB 3619755A GB 777209 A GB777209 A GB 777209A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amide
- carboxylic acid
- xanthene
- chloride
- methylpiperazine
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
The invention comprises substituted piperazines of the general formula <FORM:0777209/IV(b)/1> wherein R represents a 9-xanthenyl or 1-phenyl-cyclohexyl radical, R1 and R11 represent lower alkyl radicals having between them 3 or 4 carbon atoms, and X- is the anion of an acid, and the preparation thereof by reacting a compound of the general formula <FORM:0777209/IV(b)/2> with a quaternizing reagent of the general formula R11X, wherein R, R1, R11 and X have the above significance. The preferred compounds are the etho-quaternary salts of the N1-ethylpiperazine amide of xanthene-9-carboxylic acid, the metho-quaternary salts of the N1-isopropylpiperazine amide of xanthene - 9 - carboxylic acid, and the metho-quaternary salts of the N1-isopropylpiperazine amide of 1-phenylcyclohexane carboxylic acid. The anion may be chloride, bromide, iodide, methanesulphonate, ethanesulphonate or a toluenesulphonate. The anion may be varied by exchange reactions to form, for example, malate, succinate, fumarate, tartrate and oleate salts. In the examples, the ethiodide, ethobromide and isopropiodide of the N1-methylpiperazine amide of xanthene-9-carboxylic acid, the quaternary-p-toluenesulphonate of the N1-ethylpiperazine amide of xanthene-9-carboxylic acid, and the ethiodide, ethochloride, isopropiodide and the ethyl ethane sulphonate salt of the N1-methylpiperazine amide of 1-phenylcyclohexane carboxylic acid are prepared. Starting materials. Piperazine compounds of the general formula <FORM:0777209/IV(b)/3> wherein R and R1 have the significance indicated above, are prepared by reacting an acid chloride of the formula ROCl with the required R1 substituted piperazine. In the examples: (1) 1-phenylcyclohexane carboxylic acid is treated with thionyl chloride to form the corresponding acid chloride which is then reacted with N-methylpiperazine to form an amide; (2) xanthene-9-carboxylic acid is treated with thionyl chloride to form the corresponding acid chloride which is then reacted with N-methylpiperazine to form an amide; (3) xanthene-9-carboxylic acid chloride is reacted with N-ethylpiperazine to form an amide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US777209XA | 1954-12-28 | 1954-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB777209A true GB777209A (en) | 1957-06-19 |
Family
ID=22139673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36197/55A Expired GB777209A (en) | 1954-12-28 | 1955-12-16 | Improvements in or relating to piperazine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB777209A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11084807B2 (en) | 2016-08-18 | 2021-08-10 | Vidac Pharama Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
-
1955
- 1955-12-16 GB GB36197/55A patent/GB777209A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11084807B2 (en) | 2016-08-18 | 2021-08-10 | Vidac Pharama Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
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