GB866409A - Improvements in or relating to organic phosphorus compounds containing tertiary amino groups - Google Patents
Improvements in or relating to organic phosphorus compounds containing tertiary amino groupsInfo
- Publication number
- GB866409A GB866409A GB31232/58A GB3123258A GB866409A GB 866409 A GB866409 A GB 866409A GB 31232/58 A GB31232/58 A GB 31232/58A GB 3123258 A GB3123258 A GB 3123258A GB 866409 A GB866409 A GB 866409A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- compounds
- bromine
- chlorine
- hydroxy
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
- C07F9/3882—Arylalkanephosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
- C07F9/3834—Aromatic acids (P-C aromatic linkage)
Abstract
The invention comprises compounds of the general formula: <FORM:0866409/IV (b)/1> in which X is chlorine, bromine, iodine, hydroxy, or the group R1-SO2-O- wherein R1 is a C1-C4 alkyl group, p-tolyl, p-bromophenyl, phenyl, or benzyl group, n is an integer from zero to eight, and R is a hydrogen atom, a C1-C4 alkyl group or a pharmacologically acceptable cation, e.g. sodium, potassium, lithium, calcium, strontium, magnesium, aluminium, ammonium, substituted ammonium e.g. methylammonium, diethylammonium, trimethylammonium, diethanolammonium, or piperidinium. The two R groups may be like or unlike, thus one of the groups R may be a hydrogen atom or a pharmacologically acceptable cation, and the other a C1-C4 alkyl radical. The compounds in which X is hydroxy may be obtained by alkylating a compound of the formula: <FORM:0866409/IV (b)/2> with a 2-hydroxyethylating agent, e.g. ethylene oxide, or ethylene chlorohydrin or bromohydrin. The resulting N, N-bis-(2-hydroxyethyl) derivatives may be hydrolysed with acids to give the free dibasic acids or may be treated with alkali followed by acidification to give the acid esters, also the free hydroxy groups may be replaced by chlorine, bromine or iodine by known methods. Thus, the compounds in which X is chlorine or bromine can be obtained by treating the hydroxy compound with a mixture of chloroform, pyridine hydrochloride or hydrobromide, dry pyridine and thionyl chloride or bromide. The compounds in which X is R1SO2O- may be obtained by condensing the N,N-bis (2-hydroxyethyl) derivatives with an R1 sulphonyl chloride or bromide in which R1 is as defined above. The compounds in which X is iodine may be obtained by reacting a compound in which X is chlorine or bromine or a R1SO2.O- group as defined above with an alkali metal iodide, e.g. sodium, potassium or lithium iodide. Several examples are given for the production of each type of product including diesters, mono-esters, ester salts and sodium and calcium salts. The products are useful as antifungal and antibacterial agents and the N,N-bis-(2-haloethyl) compounds have cytostatic activity against animal tumours and are also active against yeast organisms and may be used for inducing mutations in microorganisms (see Group VI). Compounds in which R1 is CH3SO2.O possess cytotoxic activity. The products are also useful as textile chemicals, as adhesives, and for the treatment of leather and may be polymerised to yield new plastics. The compounds of the general formula: <FORM:0866409/IV (b)/3> in which the amino group is in the para position and n is an integer from 1 to 8 can be obtained by condensing a phenylalkyl halide with a trialkyl phosphite followed by nitration and reduction of the nitro group to an amino group. The ortho- and meta isomers can be obtained by condensing an ortho- or metaacylamidophenylalkyl halide with a trialkyl phosphite to produce the phosphonate and then removing the acyl group by hydrolysis with a strong acid to form the acid addition salts of the ortho- and meta-aminophenylalkylphosphonic acids which are then reesterified with a lower alkanol in the presence of an acid catalyst and then neutralised with alkali to give the dialkyl ortho- or metaaminophenylalkyl phosphonate.ALSO:Compounds of the general formula <FORM:0866409/VI/1> in which X is chlorine, bromine, iodine, hydroxy, or the group R1SO2.O-, wherein R1 is a C1-C4 alkyl group, p-tolyl, p-bromophenyl, phenyl, or benzyl, n is an integer from zero to eight, and R is a hydrogen atom, a C1-C4 alkyl group or a pharmacologically acceptable cation, e.g. Na, K, Li, Ca, Sr, Mg, Al, NH4 or substituted ammonium, e.g. methyl-, diethyl-, trimethyl- or diethanol-ammonium or piperidinium (see Group IV (b)) have the property of inducing mutations in micro-organisms, e.g. antibiotic-producing or acid-producing organisms such as Streptomyces, Penicillium, and Aspergillae. They also exhibit cytostatic activity against several forms of animal tumours and have antifungal and antibacterial properties.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US866409XA | 1957-10-21 | 1957-10-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB866409A true GB866409A (en) | 1961-04-26 |
Family
ID=22199899
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB31232/58A Expired GB866409A (en) | 1957-10-21 | 1958-09-30 | Improvements in or relating to organic phosphorus compounds containing tertiary amino groups |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB866409A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4029697A (en) * | 1975-04-30 | 1977-06-14 | Joh. A. Benckiser Gmbh | N-acyl-1-amino alkane-1,1-diphosphonic acid compounds, process of making same, and compositions for and method of using same |
US4094782A (en) * | 1975-04-30 | 1978-06-13 | Joh. A. Benckiser | N-acyl-1-amino alkane-1,1-diphosphonic acid compounds and compositions for and method of using same |
-
1958
- 1958-09-30 GB GB31232/58A patent/GB866409A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4029697A (en) * | 1975-04-30 | 1977-06-14 | Joh. A. Benckiser Gmbh | N-acyl-1-amino alkane-1,1-diphosphonic acid compounds, process of making same, and compositions for and method of using same |
US4094782A (en) * | 1975-04-30 | 1978-06-13 | Joh. A. Benckiser | N-acyl-1-amino alkane-1,1-diphosphonic acid compounds and compositions for and method of using same |
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