GB581334A - New pyrimidine compounds - Google Patents
New pyrimidine compoundsInfo
- Publication number
- GB581334A GB581334A GB1597243A GB1597243A GB581334A GB 581334 A GB581334 A GB 581334A GB 1597243 A GB1597243 A GB 1597243A GB 1597243 A GB1597243 A GB 1597243A GB 581334 A GB581334 A GB 581334A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- pyrimidine
- hydrogen
- amino
- hydrocarbon
- 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
Abstract
2 - p - Nitrophenylguanidino-4-b -diethylamino-ethylamino-6 -methylpyrimidine is reduced with hydrogen in methanol in the presence of a Raney nickel catalyst to yield the corresponding amino compound.ALSO:Pyrimidine compounds, useful as chemotherapeutic agents, of the general formula <FORM:0581334/IV/1> wherein Ar represents an aryl group optionally bearing one or more non-acidic substituents such as hydrocarbon radicles (which themselves may bear substituents and which may be attached to the aryl group directly or through an oxygen, nitrogen or sulphur atom or a sulphonyl or carbonyl group), halogen atoms or cyano, nitro, amino, acylamino or esterified carboxyl groups, X and Y each represent hydrogen or a hydrocarbon radicle or together represent a divalent aliphatic hydrocarbon radicle forming with the 5- and 6-carbon atoms an alicylic ring, R11 is hydrogen or an alkyl or substituted alkyl (e.g. alkoxyalkyl or dialkylaminoalkyl) group, A represents a linking group which is aliphatic, alicyclic or aliphatic-carbo-cyclic and may be substituted (e.g. by hydrocarbon radicles, hydroxy, alkoxy or dialkylaminoalkyl groups), and which, when wholly or partly an aliphatic chain, may be interrupted by oxygen, nitrogen or sulphur atoms, and NRR1 represents a strongly basic amino or substituted amino group such as alkylamino, dialkylamino or piperidino or other strongly basic nitrogen-containing heterocyclic group, are manufactured by the interaction of a diamine NHR11-A-NRR1 with an appropriate 2 - arylguanidinopyrimidine - bearing groups Y and X in the 5- and 6-positions respectively and a labile group such as a halogen atom or a hydrocarbon radicle which is attached by means of an ether or thioether linkage (e.g. an alkoxy, aryloxy or alkylmercapto group) in the 4-position. Alternatively, when NRR1 is a primary amino group, this is protected by acylation and the acyl group is split off after condensation with the pyrimidine compound, this precaution being essential when introducing a substituent of the type -N(Alkyl)-A-NH2. The reaction is effected by heating the reagents together, optionally in the presence of a solvent or diluent. Either of the reagents may be used in the form of a salt, e.g. hydrochloride or acetate, and, if desired, an acid-binding agent such as sodium hydroxide may be present. The products form salts with mineral and organic acids, e.g. hydrogen halides, sulphuric, phosphoric, acetic, lactic, tartaric, methanesulphonic, methylene-bis-2 : 3-hydroxynaphthoic and methylene-bis-salicylic acids. In some cases, the substituent on the aryl radicle of the product may be chemically modified, e.g. 2 - p - nitrophenylananidino - 4 - b - diethylaminoethylamino - 6 - methylpyrimidine may be reduced with hydrogen in methanol in the presence of a Raney nickel catalyst to yield the corresponding amino compound. Also the terminal amino group of the 4-substituent may be modified, e.g. a primary amino group may be mono- or di-alkylated or converted to piperidino, pyrrolidino or other strongly basic nitrogen-containing heterocyclic group, or a monoalkylamino group may be converted to a dialkylamino group. Many examples are given. Specification 581,347 is referred to. A sample has been furnished under Sect. 2 (5) of 2 - p - chlorophenylguanidino - 6 - methyl - 4 - (b - aminoethylamino) - pyrimidine, prepared by heating 2 - p - chlorophenylguanidino - 4-chloro - 6 - methylpyrimidine with b - acetylaminoethyl - amine in glacial acetic acid and hydrolysing the product by refluxing with dilute hydrochloric acid. According to the Provisional Specifications, the linking group may be carbocyclic (not restricted to alicyclic). The first Provisional Specification contains an additional example of the preparation of 2-p-methoxyphenylguanidino-4-(g -diethylaminopropylamino) -pyrimidine, the second Provisional Specification one of the preparation of 2-p-acetylaminophenylguanidino-6-methyl-4-(b -diethylaminoethylamino)-pyrimidine and the fourth Provisional Specification one of the preparation of 2-p-chlorophenylguanidino - 6 - methyl - 4 - (b - diethylaminoethyl - methylamino)-pyrimidine, in each case from the corresponding 4-chloro-compound. 2-Arylguanidinopyrimidines containing an ether or thioether group in the 4-position are obtainable by interaction of the 4-halogen derivatives with appropriate hydroxy or mercapto compounds or alkali metal derivatives thereof.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1597243A GB581334A (en) | 1943-09-29 | 1943-09-29 | New pyrimidine compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1597243A GB581334A (en) | 1943-09-29 | 1943-09-29 | New pyrimidine compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB581334A true GB581334A (en) | 1946-10-09 |
Family
ID=10068902
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1597243A Expired GB581334A (en) | 1943-09-29 | 1943-09-29 | New pyrimidine compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB581334A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006514118A (en) * | 2002-11-21 | 2006-04-27 | カイロン コーポレイション | 2,4,6-Trisubstituted pyrimidines as phosphotidylinositol (PI) 3-kinase inhibitors and their use in the treatment of cancer |
US8563549B2 (en) | 2006-01-20 | 2013-10-22 | Novartis Ag | Pyrimidine derivatives used as PI-3 kinase inhibitors |
US8865894B2 (en) | 2012-02-24 | 2014-10-21 | Novartis Ag | Oxazolidin-2-one compounds and uses thereof |
US8957068B2 (en) | 2011-09-27 | 2015-02-17 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant IDH |
US9296733B2 (en) | 2012-11-12 | 2016-03-29 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases |
US9434719B2 (en) | 2013-03-14 | 2016-09-06 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant IDH |
-
1943
- 1943-09-29 GB GB1597243A patent/GB581334A/en not_active Expired
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006514118A (en) * | 2002-11-21 | 2006-04-27 | カイロン コーポレイション | 2,4,6-Trisubstituted pyrimidines as phosphotidylinositol (PI) 3-kinase inhibitors and their use in the treatment of cancer |
US8563549B2 (en) | 2006-01-20 | 2013-10-22 | Novartis Ag | Pyrimidine derivatives used as PI-3 kinase inhibitors |
US8957068B2 (en) | 2011-09-27 | 2015-02-17 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant IDH |
US8865894B2 (en) | 2012-02-24 | 2014-10-21 | Novartis Ag | Oxazolidin-2-one compounds and uses thereof |
US9458177B2 (en) | 2012-02-24 | 2016-10-04 | Novartis Ag | Oxazolidin-2-one compounds and uses thereof |
US9296733B2 (en) | 2012-11-12 | 2016-03-29 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases |
US10202371B2 (en) | 2012-11-12 | 2019-02-12 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivatives and the use thereof as phosphatidylinositol-3-kinase inhibitors |
US9434719B2 (en) | 2013-03-14 | 2016-09-06 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant IDH |
US9688672B2 (en) | 2013-03-14 | 2017-06-27 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant IDH |
US10112931B2 (en) | 2013-03-14 | 2018-10-30 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant IDH |
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