GB1013904A - Piperazinium salts and compositions containing them - Google Patents
Piperazinium salts and compositions containing themInfo
- Publication number
- GB1013904A GB1013904A GB2785162A GB2785162A GB1013904A GB 1013904 A GB1013904 A GB 1013904A GB 2785162 A GB2785162 A GB 2785162A GB 2785162 A GB2785162 A GB 2785162A GB 1013904 A GB1013904 A GB 1013904A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- acridine
- formula
- reaction
- alkyl
- 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
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
- C07D219/12—Amino-alkylamino radicals attached in position 9
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises pharmaceutically acceptable salts of piperazinium cations of the formula <FORM:1013904/C2/1> or a pharmaceutically acceptable acid addition salt thereof, wherein A represents a straight or branched saturated alkylene chain of 2 to 6 carbon atoms; B represents a group of the formula <FORM:1013904/C2/2> or <FORM:1013904/C2/3> or <FORM:1013904/C2/4> wherein R1 and R2 are the same or different (except that R1 and R2 may not both represent thienyl, naphthyl, phenyl or phenoxyethyl groups) and each represents an alkyl group of 1 to 10 carbon atoms, or a thienyl, naphthyl, phenyl or phenoxyethyl group, optionally attached to the nitrogen atom via a straight or branched saturated alkylene chain of 1 to 5 carbon atoms and optionally carrying in the phenyl ring one or more halogen, methoxy, acetamido or amino substituents; and R3 represents a methyl, ethyl, propyl or benzyl group, and the preparation thereof by reaction of a 9-substituted acridine, wherein the substituent is a reactive hydrogen-accepting atom or group, with a salt of a cation of the formula H2N.A.B; by reaction of a 9-(o -X-alkylamino) acridine or a 9 - (o - X - alkylacylamino) acridine, wherein X is a proton accepting group or atom with a compound of the formula <FORM:1013904/C2/5> or <FORM:1013904/C2/6> and hydrolysing the product to the desired piperazinium cation where a 9-(o -X-alkylocylamino) acridine is used as starting material or by reaction of a 9-[o -(4-R1-piperazin-1-yl)-alkylamino] acridine, a salt of a 4-[o -(acridin- 9 - ylamino) alkyl] - 1 - R1 - 1 - R2 - piperazinium cation or a 4-[o -acridin-9-ylamino)-alkyl]-4-R3-1-R1-piperazinium cation with a quaternizing derivative of the remaining group. When the quaternizing group contains an amino group, said group may be protected by converting it into an acyl derivative, followed by hydrolysing to give the free amino group. N-Substituted-N-aminoalktlpiperazines may be prepared by reacting an N-substituted piperazine with a phthalimido alkyl halide followed by hydrolysis of the phthalimido alkyl piperazine so formed. Compounds of the formula H2N.A.B may be prepared by hydrolysing the corresponding phthalimidoalkylpiperazinium salts which may be prepared by the reaction of a phthalimidoalkyl halide with the corresponding piperazine or by reaction of the corresponding phthalimidoalkyl-piperazine with the appropriate quaternizing agent. 9 - (2 - Chloroethylamino) acridine may be prepared by treating the corresponding hydroxy compound with thionyl chloride. Therapeutic compositions with activity against trypanosomiasis, in the form of solutions, suspensions, tablets, granules or powders for parenteral or oral administration, comprises salts of cations of the Formula I and pharmaceutically acceptable acid addition salts thereof with a suitable pharmaceutical carrier.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2785162A GB1013904A (en) | 1962-07-19 | 1962-07-19 | Piperazinium salts and compositions containing them |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2785162A GB1013904A (en) | 1962-07-19 | 1962-07-19 | Piperazinium salts and compositions containing them |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1013904A true GB1013904A (en) | 1965-12-22 |
Family
ID=10266338
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2785162A Expired GB1013904A (en) | 1962-07-19 | 1962-07-19 | Piperazinium salts and compositions containing them |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1013904A (en) |
-
1962
- 1962-07-19 GB GB2785162A patent/GB1013904A/en not_active Expired
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