GB891413A - Tris-(dialkylaminoalkyl) phosphates and a method for their preparation - Google Patents
Tris-(dialkylaminoalkyl) phosphates and a method for their preparationInfo
- Publication number
- GB891413A GB891413A GB31600/59A GB3160059A GB891413A GB 891413 A GB891413 A GB 891413A GB 31600/59 A GB31600/59 A GB 31600/59A GB 3160059 A GB3160059 A GB 3160059A GB 891413 A GB891413 A GB 891413A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tris
- phosphate
- carbon atoms
- acid addition
- sulphonic
- 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
- 229910019142 PO4 Inorganic materials 0.000 title abstract 7
- 235000021317 phosphate Nutrition 0.000 title abstract 7
- 150000003013 phosphoric acid derivatives Chemical class 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 5
- 239000010452 phosphate Substances 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000007983 Tris buffer Substances 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 abstract 2
- 229920001817 Agar Polymers 0.000 abstract 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 abstract 1
- 108010010803 Gelatin Proteins 0.000 abstract 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 abstract 1
- 240000007472 Leucaena leucocephala Species 0.000 abstract 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 abstract 1
- 235000019483 Peanut oil Nutrition 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract 1
- 229930006000 Sucrose Natural products 0.000 abstract 1
- 230000002745 absorbent Effects 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000008272 agar Substances 0.000 abstract 1
- 235000010419 agar Nutrition 0.000 abstract 1
- 230000000326 anti-hypercholesterolaemic effect Effects 0.000 abstract 1
- 239000003529 anticholesteremic agent Substances 0.000 abstract 1
- 239000000378 calcium silicate Substances 0.000 abstract 1
- 229910052918 calcium silicate Inorganic materials 0.000 abstract 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 abstract 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 abstract 1
- 150000001860 citric acid derivatives Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- -1 e.g. Substances 0.000 abstract 1
- 239000008273 gelatin Substances 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 239000007903 gelatin capsule Substances 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 235000011852 gelatine desserts Nutrition 0.000 abstract 1
- 239000008101 lactose Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000007937 lozenge Substances 0.000 abstract 1
- 235000019359 magnesium stearate Nutrition 0.000 abstract 1
- 150000002688 maleic acid derivatives Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004006 olive oil Substances 0.000 abstract 1
- 235000008390 olive oil Nutrition 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000312 peanut oil Substances 0.000 abstract 1
- 239000001814 pectin Substances 0.000 abstract 1
- 235000010987 pectin Nutrition 0.000 abstract 1
- 229920001277 pectin Polymers 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008159 sesame oil Substances 0.000 abstract 1
- 235000011803 sesame oil Nutrition 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- 239000005720 sucrose Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 235000012222 talc Nutrition 0.000 abstract 1
- PJGBDAXHQYTCOA-UHFFFAOYSA-N tris[2-(dimethylamino)ethyl] phosphate Chemical group CN(C)CCOP(=O)(OCCN(C)C)OCCN(C)C PJGBDAXHQYTCOA-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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 Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention comprises tris(dialkylaminoalkyl) phosphates having the general formula <FORM:0891413/IV (b)/1> in which R1 and R2 are C1-C4 alkyl groups, A is a divalent saturated alkylene chain having 2 to 6 carbon atoms, the nitrogen and oxygen atoms being separated by a chain of at least 2 carbon atoms, and non-toxic acid addition salts thereof. The free bases may be obtained by reacting one molecular proportion of phosphorus oxychloride with at least 6 molecular proportions of an alkanolamine (R1)(R2)N.A.OH in solution in an organic solvent. The phosphorus oxychloride is suitably added to the alkanolamine, with cooling, at such a rate so as to maintain the temperature at 0 DEG C.-10 DEG C. and the solution is then stirred at about 20 DEG C. to 50 DEG C. and allowed to stand until reaction is complete. The acid addition salts may be obtained by reacting the base with a stoichiometric amount of a suitable organic or inorganic acid in an aqueous miscible solvent, e.g., acetone or ethanol, or with an excess of the acid in an aqueous immiscible solvent such as ethyl ether or chloroform. Specified acids are maleic, fumaric, benzoic, ethanedisulphonic, citric, lactic, benzene sulphonic, methane sulphonic, acetic, tartaric, succinic, hydrochloric, hydrobromic, sulphuric, nitric, phosphoric, and sulphamic acids. Examples are given for the preparation of tris(b -dimethyl-aminoethyl) phosphate and its trihydrochloride, tris-(b -dimethylaminoisopropyl) phosphate and its maleate salt, tris-(b -di-methylaminohexyl) phosphate and its citrate salt, and tris-(b -dibutylaminoethyl) phosphate and its tri-hydrobromide. The products are useful as anti-hypercholester olemic agents (see Group VI].ALSO:A pharmaceutical composition having antihypercholesterolemic activity comprises a tris(dialkylaminoalkyl) phosphate having the formula <FORM:0891413/VI/1> in which R1 and R2 are C1-C4 alkyl groups and A is a divalent saturated alkylene chain containing 2 to 6 carbon atoms, the nitrogen and oxygen atoms being separated by a chain of at least two carbon atoms, or a non-toxic acid addition salt thereof (see Group IV (b)) and a pharmaceutical carrier. The carrier may be a solid or liquid, e.g. lactose, magnesium stearate, terra alba, sucrose, talc, stearic acid, gelatin, agar, pectin, acacia, peanut oil, olive oil, sesame oil or water. The composition may be in the form of a tablet, troche or lozenge or hard or soft gelatin capsule. Absorbent materials such as silica gel or synthetic calcium silicate may also be present. The preferred organophosphate is tris(dimethylaminoethyl) phosphate. Suitable acid addition salts are those derived from maleic, fumaric, benzoic, ethanedisulphonic, citric, lactic, benzene-sulphonic, methane sulphonic, acetic, tartaric, succinic, hydrochloric, hydrobromic, sulphuric, nitric, phosphoric and sulphamic acids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US891413XA | 1958-10-06 | 1958-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB891413A true GB891413A (en) | 1962-03-14 |
Family
ID=22215913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31600/59A Expired GB891413A (en) | 1958-10-06 | 1959-09-16 | Tris-(dialkylaminoalkyl) phosphates and a method for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB891413A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7989639B2 (en) | 2006-06-12 | 2011-08-02 | Novartis Ag | Process for making salts of N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide |
-
1959
- 1959-09-16 GB GB31600/59A patent/GB891413A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7989639B2 (en) | 2006-06-12 | 2011-08-02 | Novartis Ag | Process for making salts of N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide |
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