GB871856A - Pyrimidine derivatives - Google Patents
Pyrimidine derivativesInfo
- Publication number
- GB871856A GB871856A GB43407/59A GB4340759A GB871856A GB 871856 A GB871856 A GB 871856A GB 43407/59 A GB43407/59 A GB 43407/59A GB 4340759 A GB4340759 A GB 4340759A GB 871856 A GB871856 A GB 871856A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tertiary
- group
- hydroxypyrimidines
- mercapto
- alkoxy
- 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
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- 150000008081 1H-pyrimidin-4-ones Chemical class 0.000 abstract 1
- LTQWTYKQCZSHGX-UHFFFAOYSA-N 6-(4-chlorophenyl)-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1C1=CC(=O)NC(=S)N1 LTQWTYKQCZSHGX-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 238000007281 aminoalkylation reaction Methods 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000000824 cytostatic agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- DGCZHKABHPDNCC-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(Cl)C=C1 DGCZHKABHPDNCC-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- -1 isothiourea ethers Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical class O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0871856/IV (b)/1> (wherein R1 and R2 each represent a hydrogen atom or an alkyl, aryl or haloaryl radical, R3 represents an alkyl, cycloalkyl, alkoxyalkyl or alkenyl radical, R4 represents an alkylene radical and X represents a tertiary or quaternary basic nitrogen-containing group), and the preparation thereof by the p processes of the examples, which may be summarized as follows (a): (when X is tertiary) subjecting 2-mercapto-4-hydroxypyrimidines to aminoalkylation at the sulphur atom followed by etherification of the hydroxy group to an alkoxy or alkoxyalkoxy group; (b) (when X is tertiary and R1 is other than hydrogen) condensing basic-substituted isothiourea ethers with b -ketocarboxylic acid esters to form 4-hydroxypyrimidines, and replacing the hydroxy group by a halogen atom and the latter by an alkoxy or alkoxyalkoxy group; (c) (when X is quaternary) quaternating the products of (a) or (b). The products are useful as cytostatic agents. 2 - Mercapto - 4 - hydroxy - 6 - p - chloro - phenylpyrimidine is prepared by condensing ethyl p-chlorobenzoylacetate with thiourea in the presence of sodium methoxide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE871856X | 1958-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB871856A true GB871856A (en) | 1961-07-05 |
Family
ID=6815793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43407/59A Expired GB871856A (en) | 1958-12-31 | 1959-12-21 | Pyrimidine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB871856A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150152077A1 (en) * | 2012-06-07 | 2015-06-04 | Georgia State University Research Foundation, Inc. | SecA Inhibitors and Methods of Making and Using Thereof |
-
1959
- 1959-12-21 GB GB43407/59A patent/GB871856A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150152077A1 (en) * | 2012-06-07 | 2015-06-04 | Georgia State University Research Foundation, Inc. | SecA Inhibitors and Methods of Making and Using Thereof |
| US9957247B2 (en) * | 2012-06-07 | 2018-05-01 | Georgia State University Research Foundation, Inc. | SecA inhibitors and methods of making and using thereof |
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