GB593499A - New pyrimidine compounds - Google Patents
New pyrimidine compoundsInfo
- Publication number
- GB593499A GB593499A GB869945A GB869945A GB593499A GB 593499 A GB593499 A GB 593499A GB 869945 A GB869945 A GB 869945A GB 869945 A GB869945 A GB 869945A GB 593499 A GB593499 A GB 593499A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- group
- nrr1
- benziminazolyl
- methylpyrimidine
- 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
- 150000003230 pyrimidines Chemical class 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 5
- -1 hydrocarbon radicals Chemical group 0.000 abstract 5
- 125000005647 linker group Chemical group 0.000 abstract 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 230000000875 corresponding Effects 0.000 abstract 3
- 150000004985 diamines Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 230000003993 interaction Effects 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000002723 alicyclic group Chemical group 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000005084 alkoxyalkylaminoalkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000004429 atoms Chemical group 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000005181 hydroxyalkylaminoalkyl group Chemical group 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000006011 modification reaction Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000000101 thioether group Chemical group 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Pyrimidine compounds, useful as chemotherapeutic agents, and of the general formula <FORM:0593499/IV/1> wherein X and Y, which are not necessarily alike, each represent hydrogen or a hydrocarbon radical or jointly represent a divalent aliphatic hydrocarbon radical which forms with the 5- and 6-carbon atoms an alicyclic ring, R11 represents hydrogen or an alkyl or substituted alkyl (e.g. alkoxyalkyl or dialkylaminoalkyl) group, A represents an aliphatic, alicyclic or aliphatic-carbocyclic linking group which may be substituted by hydrocarbon radicals or hydroxy, alkoxy or dialkylaminoalkyl groups and, when wholly or partly an aliphatic chain, may be interrupted by oxygen, sulphur or nitrogen 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, and wherein the Bz ring of the benziminazolyl group may be unsubstituted or may bear one or more non-acidic substituents, e.g. hydrocarbon radicals (which themselves may bear substituents and which may be attached to the Bz ring directly or indirectly, e.g. through an oxygen, sulphur or nitrogen atom, or may be fused thereto as in the case of a naphthiminazolyl radical), halogen atoms or nitro or cyano groups, are manufactured by the interaction of a diamine NHR11-A-NRR1 with an appropriate 2-benziminazolyl-(21)-aminopyrimidine bearing in the 5- and 6-positions the atoms or groups Y and X respectively and in the 4-position a labile substituent such as a halogen atom or a hydrocarbon radical attached by an ether or thioether linkage, e.g. an alkoxy, aryloxy or alkylmercapto group. The reaction may be effected by heating the reactants together, optionally in the presence of a solvent or diluent. One or other of the reactants may be in the form of a salt, e.g. hydrochloride or acetate, and an acid-binding agent, e.g. sodium hydroxide, may be present if desired. When R1 in the general formula above represents hydrogen, the diamine may be replaced by its acyl derivative, the acyl group being subsequently removed by hydrolysis. A further modification consists in introducing the basic substituent-NR11-A-NRR1 in stages by reacting the benziminazolylamino-pyrimidine compound, carrying a labile substituent in the 4-position, with an amino compound NHR11-A1-B, wherein A1 represents the whole or a part of the linking group A and B represents a reactive group which is then converted, directly or indirectly, by methods involving reaction with ammonia or a compound containing an amino group, into the group NRR1 or into a group A11-NRR1 such that A and A11 together constitute the linking group A. Thus, B may represent a hydroxy group or a derivative thereof which is, or is readily convertible to, a reactive ester thereof, e.g. a halide, this then being brought into reaction with an amine NHRR1 or an amino-, hydroxy-or mercapto-substituted amine NH2-A111-NRR1, HO-A111-NRR1 or HS-A111-NRR1 (or an alkali metal derivative of the hydroxy or mercapto compound) such that A1-NH-A111, A1-O-A111 or A1-S-A111 constitutes the linking group A. The terminal amino group, when unsubstituted, may be subsequently modified, e.g. by alkylation, conversion into a heterocyclic group such as piperidino or by bringing it into reaction with a halogen-substituted amine Hal-A111-NRR1 so as to extend the linking group A to A-NH-A111. In examples, the following compounds are prepared by heating the appropriate 2-benziminazolyl-(21)-amino-4-chloro-6-methylpyrimidine (or its hydrochloride) with the appropriate diamine in the presence of potassium iodide: 4-b -diethylaminoethylamino-2-benziminazolyl-(21) -amino-6-methylpyrimidine and its 51-(61)-chloro- and -methyl-derivatives; 4-g -diethyl-, -dimethyl- and -dibutyl-aminopropylamino-, 4 - g - (N - methyl - N - isopropylamino) - propyl - amino-, 4-b -piperidinoethylamino- and 4-g -(b 1-diethylaminoethoxy) - propylamino - 2 - (51 - (61) - chlorobenziminazolyl - (21) - amino) - 6 - methyl - pyrimidine; 4-g -diethyl- and -dibutyl-amino-propylamino-2-(51-(61) -methoxybenziminazolyl-(21)-amino)-6-methylpyrimidine; 4-b -diethylaminoethylamino-2-(naphtho-111 : 211 : 41 : 51-iminazolyl - (21) - amino) - 6 - methylpyrimidine; 4-g -diethylaminopropylamino - 2 - (51 - methyl - benziminazolyl - (21) - amino) - 6 - methylpyrimidine; and 4 - g - dibutylaminopropylamino - 2 - benziminazolyl-(21)-amino-6-methylpyrimidine. 4 - Halogeno - 2 - benziminazolyl - (21) - amino - pyrimidines are obtainable by the action of phosphorus pentahalides or oxyhalides on the corresponding 4-hydroxy-compounds, themselves obtainable by interaction of the corresponding 2 - cyanamino - 4 - hydroxypyrimidines with an o-phenylenediamine or by interaction of the corresponding benziminazolylguanidines with an appropriate formylacetic ester. 2-Benziminazolyl-(21)-aminopyrimidines containing ether or thioether groups in the 4-position are obtainable by treating the 4-halogen-derivatives with appropriate hydroxy or mercapto compounds or with their alkali metal derivatives.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US701092A US2460409A (en) | 1945-10-09 | 1946-10-04 | 2-benziminazoyl-amino pyrimidines |
CH258456D CH258456A (en) | 1945-10-09 | 1946-11-16 | Process for the preparation of a new pyrimidine compound. |
Publications (1)
Publication Number | Publication Date |
---|---|
GB593499A true GB593499A (en) | 1947-10-17 |
Family
ID=1629450
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB869945A Expired GB593499A (en) | 1945-10-09 | 1945-10-09 | New pyrimidine compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB593499A (en) |
-
1945
- 1945-10-09 GB GB869945A patent/GB593499A/en not_active Expired
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